#------------------------------------------------------------------------------
#$Date: 2009-11-16 02:43:51 +0100 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012770.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2012770
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o362
_journal_page_last  o364
_publ_section_title
;
(1R)-2-[(3R,4S)-3-Methyl-4-(N-phenyl-N-propionylamino)pyridyl]-1-
phenylethyl p-bromobenzoate and
N-{(3R,4S)1-[(2S)-2-(4-bromophenyl)-2-hydroxyethyl]-3-methyl-4-pyridyl}-
N-phenylpropenamide
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_[local]_cod_cif_authors_sg_H-M  'P 21'
loop_
_publ_author_name
  'Deschamps, Jeffrey R.'
  'George, Clifford'
  'Flippen-Anderson, Judith L.'
_chemical_formula_moiety  'C30 H33 Br N2 O3'
_chemical_formula_sum  'C30 H33 Br N2 O3'
_chemical_formula_iupac  'C30 H33 Br N2 O3'
_chemical_formula_weight  549.49
_symmetry_cell_setting  Monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  10.8806(2)
_cell_length_b  22.4670(5)
_cell_length_c  11.5313(3)
_cell_angle_alpha  90.00
_cell_angle_beta  92.2080(10)
_cell_angle_gamma  90.00
_cell_volume  2816.78(11)
_cell_formula_units_Z  4
_cell_measurement_temperature  153(2)
_exptl_crystal_density_diffrn  1.296
_diffrn_ambient_temperature  153(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  Br1 1.31391(4) 0.70497(3) 0.08320(8) 0.1492(3) Uani d . 1 . . Br
  N1 0.6620(2) 0.53291(11) 0.2724(2) 0.0698(5) Uani d . 1 . . N
  C2 0.6512(3) 0.46973(14) 0.3022(3) 0.0754(7) Uani d . 1 . . C
  H2A 0.6698 0.4457 0.2351 0.090 Uiso calc R 1 . . H
  H2B 0.5673 0.4613 0.3223 0.090 Uiso calc R 1 . . H
  C3 0.7381(3) 0.45283(14) 0.4034(3) 0.0733(7) Uani d . 1 . . C
  H3A 0.7203 0.4114 0.4237 0.088 Uiso calc R 1 . . H
  C4 0.7076(3) 0.49106(13) 0.5071(2) 0.0696(6) Uani d . 1 . . C
  H4A 0.6219 0.4823 0.5241 0.083 Uiso calc R 1 . . H
  C5 0.7123(4) 0.55663(14) 0.4767(3) 0.0832(8) Uani d . 1 . . C
  H5A 0.7960 0.5679 0.4604 0.100 Uiso calc R 1 . . H
  H5B 0.6862 0.5802 0.5418 0.100 Uiso calc R 1 . . H
  C6 0.6281(4) 0.56853(16) 0.3709(3) 0.0856(9) Uani d . 1 . . C
  H6A 0.5439 0.5596 0.3896 0.103 Uiso calc R 1 . . H
  H6B 0.6324 0.6104 0.3507 0.103 Uiso calc R 1 . . H
  N7 0.7828(2) 0.47563(11) 0.6141(2) 0.0719(6) Uani d . 1 . . N
  C8 0.7520(3) 0.42505(14) 0.6712(3) 0.0760(7) Uani d . 1 . . C
  O8 0.6656(2) 0.39404(11) 0.6390(2) 0.0890(6) Uani d . 1 . . O
  C9 0.8341(4) 0.40870(17) 0.7771(3) 0.0928(10) Uani d . 1 . . C
  H9A 0.9170 0.4013 0.7524 0.111 Uiso calc R 1 . . H
  H9B 0.8373 0.4420 0.8306 0.111 Uiso calc R 1 . . H
  C10 0.7883(5) 0.3544(2) 0.8388(4) 0.1120(13) Uani d . 1 . . C
  H10A 0.8422 0.3457 0.9045 0.168 Uiso calc R 1 . . H
  H10B 0.7865 0.3211 0.7866 0.168 Uiso calc R 1 . . H
  H10C 0.7069 0.3618 0.8647 0.168 Uiso calc R 1 . . H
  C1A 0.8760(3) 0.51521(15) 0.6590(3) 0.0808(8) Uani d . 1 . . C
  C6A 0.8415(5) 0.56342(17) 0.7281(3) 0.0957(11) Uani d . 1 . . C
  H6AA 0.7594 0.5694 0.7444 0.115 Uiso calc R 1 . . H
  C5A 0.9312(8) 0.6020(2) 0.7715(4) 0.131(2) Uani d . 1 . . C
  H5AA 0.9093 0.6348 0.8152 0.157 Uiso calc R 1 . . H
  C4A 1.0528(8) 0.5916(3) 0.7498(6) 0.148(3) Uani d . 1 . . C
  H4AA 1.1130 0.6175 0.7793 0.177 Uiso calc R 1 . . H
  C3A 1.0859(6) 0.5439(3) 0.6855(6) 0.142(2) Uani d . 1 . . C
  H3AA 1.1688 0.5372 0.6732 0.170 Uiso calc R 1 . . H
  C2A 0.9984(4) 0.5050(2) 0.6379(4) 0.1019(11) Uani d . 1 . . C
  H2AA 1.0217 0.4729 0.5928 0.122 Uiso calc R 1 . . H
  C1' 0.5864(3) 0.54758(16) 0.1685(3) 0.0750(7) Uani d . 1 . . C
  H1'A 0.5699 0.5900 0.1675 0.090 Uiso calc R 1 . . H
  H1'B 0.5082 0.5270 0.1716 0.090 Uiso calc R 1 . . H
  C2' 0.6476(3) 0.53051(14) 0.0583(2) 0.0703(7) Uani d . 1 . . C
  H2'A 0.6703 0.4883 0.0623 0.084 Uiso calc R 1 . . H
  C1B 0.5714(3) 0.54131(14) -0.0503(2) 0.0708(7) Uani d . 1 . . C
  C6B 0.5606(4) 0.49751(19) -0.1339(3) 0.0934(9) Uani d . 1 . . C
  H6BA 0.6003 0.4613 -0.1214 0.112 Uiso calc R 1 . . H
  C5B 0.4918(4) 0.5063(2) -0.2364(4) 0.1066(13) Uani d . 1 . . C
  H5BA 0.4868 0.4765 -0.2924 0.128 Uiso calc R 1 . . H
  C4B 0.4314(4) 0.5591(3) -0.2544(4) 0.1085(14) Uani d . 1 . . C
  H4BA 0.3856 0.5654 -0.3231 0.130 Uiso calc R 1 . . H
  C3B 0.4383(4) 0.6027(2) -0.1714(4) 0.1123(14) Uani d . 1 . . C
  H3BA 0.3946 0.6379 -0.1826 0.135 Uiso calc R 1 . . H
  C2B 0.5105(4) 0.59443(19) -0.0703(3) 0.0940(10) Uani d . 1 . . C
  H2BA 0.5177 0.6249 -0.0158 0.113 Uiso calc R 1 . . H
  O11 0.75949(19) 0.56638(9) 0.05400(19) 0.0746(5) Uani d . 1 . . O
  C12X 0.8672(3) 0.53824(14) 0.0593(3) 0.0737(7) Uani d . 1 . . C
  O12 0.8776(2) 0.48459(11) 0.0566(3) 0.0994(7) Uani d . 1 . . O
  C1C 0.9738(3) 0.57982(14) 0.0691(3) 0.0714(7) Uani d . 1 . . C
  C6C 0.9585(3) 0.64092(18) 0.0714(3) 0.0909(9) Uani d . 1 . . C
  H6CA 0.8796 0.6570 0.0709 0.109 Uiso calc R 1 . . H
  C5C 1.0593(4) 0.67826(19) 0.0746(5) 0.1072(13) Uani d . 1 . . C
  H5CA 1.0495 0.7194 0.0736 0.129 Uiso calc R 1 . . H
  C4C 1.1755(3) 0.65304(19) 0.0794(4) 0.0977(11) Uani d . 1 . . C
  C3C 1.1926(3) 0.59317(19) 0.0764(4) 0.0977(10) Uani d . 1 . . C
  H3CA 1.2715 0.5772 0.0775 0.117 Uiso calc R 1 . . H
  C2C 1.0909(3) 0.55651(18) 0.0714(3) 0.0902(9) Uani d . 1 . . C
  H2CA 1.1015 0.5155 0.0697 0.108 Uiso calc R 1 . . H
  C3' 0.8706(4) 0.4553(2) 0.3692(3) 0.0980(11) Uani d . 1 . . C
  H3'A 0.9233 0.4445 0.4345 0.147 Uiso calc R 1 . . H
  H3'B 0.8900 0.4950 0.3449 0.147 Uiso calc R 1 . . H
  H3'C 0.8828 0.4281 0.3065 0.147 Uiso calc R 1 . . H
  N11 0.3408(2) 0.30120(12) 0.8114(2) 0.0780(6) Uani d . 1 . . N
  Br11 -0.34520(5) 0.14363(3) 0.57529(8) 0.1575(3) Uani d . 1 . . Br
  C12 0.3757(4) 0.36120(19) 0.8462(3) 0.0946(10) Uani d . 1 . . C
  H12A 0.3732 0.3869 0.7786 0.114 Uiso calc R 1 . . H
  H12B 0.4593 0.3609 0.8785 0.114 Uiso calc R 1 . . H
  C13 0.2903(4) 0.38568(16) 0.9356(3) 0.0877(9) Uani d . 1 . . C
  H13A 0.3238 0.4242 0.9613 0.105 Uiso calc R 1 . . H
  C14 0.2958(3) 0.34423(16) 1.0410(3) 0.0763(7) Uani d . 1 . . C
  H14A 0.3813 0.3443 1.0709 0.092 Uiso calc R 1 . . H
  C15 0.2663(3) 0.28030(15) 1.0042(3) 0.0835(8) Uani d . 1 . . C
  H15A 0.2770 0.2540 1.0705 0.100 Uiso calc R 1 . . H
  H15B 0.1813 0.2777 0.9760 0.100 Uiso calc R 1 . . H
  C16 0.3508(3) 0.26102(18) 0.9093(3) 0.0874(9) Uani d . 1 . . C
  H16A 0.4351 0.2604 0.9397 0.105 Uiso calc R 1 . . H
  H16B 0.3291 0.2211 0.8840 0.105 Uiso calc R 1 . . H
  N17 0.2197(2) 0.36480(12) 1.1372(2) 0.0737(6) Uani d . 1 . . N
  C18 0.2643(3) 0.41108(18) 1.2029(3) 0.0845(8) Uani d . 1 . . C
  O18 0.3590(2) 0.43685(15) 1.1791(2) 0.1107(9) Uani d . 1 . . O
  C19 0.1906(4) 0.4295(2) 1.3054(4) 0.0988(11) Uani d . 1 . . C
  H19A 0.1094 0.4420 1.2776 0.119 Uiso calc R 1 . . H
  H19B 0.1806 0.3953 1.3556 0.119 Uiso calc R 1 . . H
  C20 0.2490(6) 0.4787(3) 1.3742(6) 0.148(3) Uani d . 1 . . C
  H20A 0.1985 0.4886 1.4379 0.223 Uiso calc R 1 . . H
  H20B 0.2575 0.5130 1.3255 0.223 Uiso calc R 1 . . H
  H20C 0.3287 0.4663 1.4035 0.223 Uiso calc R 1 . . H
  C11A 0.1114(3) 0.33283(14) 1.1701(2) 0.0707(7) Uani d . 1 . . C
  C12A 0.1226(4) 0.28576(18) 1.2477(3) 0.0918(10) Uani d . 1 . . C
  H12C 0.1995 0.2745 1.2781 0.110 Uiso calc R 1 . . H
  C13A 0.0174(6) 0.25561(19) 1.2794(4) 0.1134(15) Uani d . 1 . . C
  H13B 0.0240 0.2235 1.3301 0.136 Uiso calc R 1 . . H
  C14A -0.0949(5) 0.2729(3) 1.2367(4) 0.1196(16) Uani d . 1 . . C
  H14B -0.1647 0.2528 1.2595 0.143 Uiso calc R 1 . . H
  C15A -0.1070(4) 0.3191(3) 1.1611(4) 0.1117(14) Uani d . 1 . . C
  H15C -0.1844 0.3303 1.1317 0.134 Uiso calc R 1 . . H
  C16A -0.0040(3) 0.34938(18) 1.1285(3) 0.0869(8) Uani d . 1 . . C
  H16C -0.0123 0.3814 1.0777 0.104 Uiso calc R 1 . . H
  C11' 0.4041(3) 0.28139(17) 0.7090(3) 0.0802(8) Uani d . 1 . . C
  H11A 0.4110 0.2383 0.7098 0.096 Uiso calc R 1 . . H
  H11B 0.4865 0.2979 0.7104 0.096 Uiso calc R 1 . . H
  C12' 0.3342(3) 0.30112(16) 0.5995(3) 0.0778(7) Uani d . 1 . . C
  H12D 0.3202 0.3442 0.6021 0.093 Uiso calc R 1 . . H
  C11B 0.3966(3) 0.28517(14) 0.4889(3) 0.0743(7) Uani d . 1 . . C
  C16B 0.4690(4) 0.32519(19) 0.4352(3) 0.0980(11) Uani d . 1 . . C
  H1CA 0.4820 0.3625 0.4685 0.118 Uiso calc R 1 . . H
  C15B 0.5236(5) 0.3117(2) 0.3325(4) 0.1121(13) Uani d . 1 . . C
  H15D 0.5720 0.3399 0.2969 0.135 Uiso calc R 1 . . H
  C14B 0.5067(4) 0.2573(2) 0.2833(3) 0.1044(12) Uani d . 1 . . C
  H14C 0.5443 0.2480 0.2146 0.125 Uiso calc R 1 . . H
  C13B 0.4333(5) 0.2159(2) 0.3356(4) 0.1095(12) Uani d . 1 . . C
  H13C 0.4200 0.1788 0.3014 0.131 Uiso calc R 1 . . H
  C12B 0.3797(4) 0.22966(17) 0.4394(4) 0.0973(10) Uani d . 1 . . C
  H12E 0.3322 0.2014 0.4759 0.117 Uiso calc R 1 . . H
  O21 0.21741(19) 0.27019(11) 0.5997(2) 0.0810(5) Uani d . 1 . . O
  C22 0.1136(3) 0.30167(15) 0.5851(2) 0.0734(7) Uani d . 1 . . C
  O22 0.1111(3) 0.35448(13) 0.5727(3) 0.1037(7) Uani d . 1 . . O
  C11C 0.0040(3) 0.26211(15) 0.5863(2) 0.0714(7) Uani d . 1 . . C
  C16C -0.1106(3) 0.28650(18) 0.5620(3) 0.0918(9) Uani d . 1 . . C
  H16D -0.1178 0.3271 0.5479 0.110 Uiso calc R 1 . . H
  C15C -0.2147(4) 0.2513(2) 0.5585(4) 0.0977(10) Uani d . 1 . . C
  H15E -0.2918 0.2676 0.5415 0.117 Uiso calc R 1 . . H
  C14C -0.2014(3) 0.1925(2) 0.5803(4) 0.0990(11) Uani d . 1 . . C
  C13C -0.0908(4) 0.1661(2) 0.6040(5) 0.1201(15) Uani d . 1 . . C
  H13D -0.0851 0.1253 0.6173 0.144 Uiso calc R 1 . . H
  C12C 0.0137(3) 0.20201(19) 0.6078(4) 0.0959(10) Uani d . 1 . . C
  H12F 0.0904 0.1853 0.6250 0.115 Uiso calc R 1 . . H
  C13' 0.1613(5) 0.3970(2) 0.8846(3) 0.1101(13) Uani d . 1 . . C
  H13E 0.1658 0.4233 0.8192 0.165 Uiso calc R 1 . . H
  H13F 0.1120 0.4150 0.9423 0.165 Uiso calc R 1 . . H
  H13G 0.1249 0.3600 0.8600 0.165 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  Br1 0.0749(3) 0.1135(4) 0.2608(7) -0.0262(3) 0.0293(3) -0.0646(4)
  N1 0.0604(13) 0.0668(13) 0.0818(13) 0.0044(10) -0.0032(10) 0.0024(10)
  C2 0.0724(19) 0.0672(16) 0.0857(17) -0.0001(13) -0.0079(13) -0.0013(12)
  C3 0.0710(18) 0.0626(15) 0.0857(17) 0.0045(13) -0.0054(13) 0.0009(12)
  C4 0.0559(14) 0.0713(16) 0.0811(16) 0.0021(12) -0.0015(11) 0.0027(12)
  C5 0.097(2) 0.0644(16) 0.0871(18) 0.0093(16) -0.0042(15) -0.0071(13)
  C6 0.088(2) 0.0750(19) 0.0931(19) 0.0225(17) -0.0008(15) 0.0028(14)
  N7 0.0673(14) 0.0659(13) 0.0818(13) -0.0046(11) -0.0047(10) 0.0025(10)
  C8 0.0732(19) 0.0656(16) 0.0885(17) 0.0001(14) -0.0041(13) 0.0021(12)
  O8 0.0803(15) 0.0799(14) 0.1052(14) -0.0178(12) -0.0160(11) 0.0117(11)
  C9 0.095(3) 0.080(2) 0.101(2) -0.0075(19) -0.0230(17) 0.0151(16)
  C10 0.123(4) 0.094(3) 0.116(3) -0.015(2) -0.023(2) 0.033(2)
  C1A 0.081(2) 0.0761(18) 0.0840(17) -0.0162(16) -0.0081(13) 0.0053(13)
  C6A 0.119(3) 0.075(2) 0.092(2) -0.019(2) -0.0059(18) 0.0027(15)
  C5A 0.200(7) 0.088(3) 0.101(3) -0.044(4) -0.029(3) 0.001(2)
  C4A 0.164(6) 0.137(5) 0.137(4) -0.079(5) -0.053(4) 0.016(3)
  C3A 0.096(3) 0.159(5) 0.168(4) -0.053(4) -0.034(3) 0.014(4)
  C2A 0.074(2) 0.107(3) 0.123(3) -0.018(2) -0.0201(18) 0.004(2)
  C1' 0.0546(15) 0.0824(18) 0.0877(17) 0.0011(13) 0.0003(12) 0.0108(14)
  C2' 0.0570(16) 0.0635(15) 0.0905(17) -0.0030(12) 0.0035(12) 0.0089(12)
  C1B 0.0603(15) 0.0707(16) 0.0819(16) -0.0092(13) 0.0093(11) 0.0079(12)
  C6B 0.090(2) 0.087(2) 0.102(2) -0.0160(19) -0.0004(17) 0.0041(17)
  C5B 0.103(3) 0.123(3) 0.094(2) -0.034(3) -0.0028(19) 0.003(2)
  C4B 0.084(3) 0.145(4) 0.096(2) -0.030(3) -0.0089(17) 0.039(3)
  C3B 0.106(3) 0.123(4) 0.108(3) 0.020(3) 0.003(2) 0.040(3)
  C2B 0.100(3) 0.088(2) 0.094(2) 0.009(2) 0.0027(17) 0.0181(16)
  O11 0.0551(11) 0.0634(11) 0.1057(13) 0.0011(9) 0.0069(9) 0.0063(9)
  C12X 0.0610(17) 0.0709(18) 0.0894(17) 0.0042(13) 0.0050(12) 0.0015(13)
  O12 0.0695(14) 0.0673(14) 0.162(2) 0.0058(11) 0.0090(13) -0.0056(13)
  C1C 0.0576(16) 0.0703(16) 0.0866(17) 0.0007(13) 0.0064(12) -0.0025(12)
  C6C 0.0621(17) 0.080(2) 0.131(3) 0.0064(16) 0.0093(16) -0.0160(18)
  C5C 0.076(2) 0.074(2) 0.172(4) -0.0079(18) 0.017(2) -0.027(2)
  C4C 0.0645(19) 0.091(3) 0.139(3) -0.0130(19) 0.0135(18) -0.028(2)
  C3C 0.0538(17) 0.095(3) 0.145(3) 0.0040(17) 0.0056(17) -0.015(2)
  C2C 0.0646(19) 0.080(2) 0.126(3) 0.0069(16) 0.0069(16) -0.0047(18)
  C3' 0.075(2) 0.121(3) 0.097(2) 0.029(2) 0.0014(15) -0.0101(19)
  N11 0.0698(15) 0.0767(15) 0.0883(15) 0.0014(12) 0.0144(11) -0.0065(12)
  Br11 0.0800(3) 0.1343(5) 0.2563(8) -0.0328(3) -0.0163(4) 0.0087(5)
  C12 0.091(2) 0.097(2) 0.097(2) -0.018(2) 0.0196(16) -0.0066(17)
  C13 0.101(3) 0.0740(19) 0.0894(19) -0.0136(18) 0.0190(16) -0.0082(15)
  C14 0.0542(16) 0.088(2) 0.0868(17) -0.0005(14) 0.0050(12) -0.0068(14)
  C15 0.085(2) 0.0739(19) 0.0921(19) 0.0067(16) 0.0124(15) 0.0005(14)
  C16 0.075(2) 0.087(2) 0.100(2) 0.0170(17) 0.0107(15) -0.0034(16)
  N17 0.0587(14) 0.0781(15) 0.0844(14) -0.0034(11) 0.0035(10) -0.0064(11)
  C18 0.0661(18) 0.096(2) 0.0909(19) -0.0073(17) 0.0008(13) -0.0165(15)
  O18 0.0795(16) 0.137(3) 0.1162(17) -0.0384(17) 0.0149(13) -0.0342(16)
  C19 0.081(2) 0.102(3) 0.115(2) -0.016(2) 0.0187(18) -0.026(2)
  C20 0.128(4) 0.148(5) 0.173(5) -0.051(4) 0.047(4) -0.080(4)
  C11A 0.0641(17) 0.0712(16) 0.0773(15) -0.0046(13) 0.0085(11) -0.0068(12)
  C12A 0.108(3) 0.086(2) 0.0824(19) 0.0041(19) 0.0099(16) 0.0024(15)
  C13A 0.161(5) 0.079(2) 0.103(3) -0.019(3) 0.036(3) 0.0011(18)
  C14A 0.113(4) 0.132(4) 0.116(3) -0.045(3) 0.033(3) -0.017(3)
  C15A 0.071(2) 0.138(4) 0.127(3) -0.015(2) 0.0160(19) -0.019(3)
  C16A 0.0631(18) 0.094(2) 0.104(2) 0.0001(16) 0.0087(14) -0.0016(17)
  C11' 0.0574(16) 0.097(2) 0.0872(18) 0.0035(15) 0.0081(12) -0.0079(15)
  C12' 0.0597(17) 0.0765(18) 0.0975(19) 0.0023(14) 0.0089(13) -0.0039(14)
  C11B 0.0641(17) 0.0761(18) 0.0825(16) 0.0046(14) 0.0027(12) -0.0004(13)
  C16B 0.094(3) 0.093(2) 0.108(2) -0.021(2) 0.0153(18) -0.0162(19)
  C15B 0.115(3) 0.115(3) 0.109(3) -0.027(3) 0.034(2) -0.006(2)
  C14B 0.112(3) 0.109(3) 0.093(2) 0.011(3) 0.0194(19) -0.001(2)
  C13B 0.125(3) 0.083(2) 0.121(3) 0.005(2) 0.027(2) -0.014(2)
  C12B 0.106(3) 0.0714(19) 0.116(3) 0.0064(19) 0.029(2) 0.0006(17)
  O21 0.0558(11) 0.0744(12) 0.1130(14) 0.0037(10) 0.0044(9) -0.0033(10)
  C22 0.0621(17) 0.0809(19) 0.0775(16) 0.0022(14) 0.0056(11) 0.0009(13)
  O22 0.0746(16) 0.0792(16) 0.157(2) 0.0061(13) 0.0019(13) 0.0134(14)
  C11C 0.0583(15) 0.0794(18) 0.0766(15) 0.0036(13) 0.0049(11) 0.0011(12)
  C16C 0.0647(19) 0.085(2) 0.125(3) 0.0086(16) 0.0065(17) 0.0013(18)
  C15C 0.0611(19) 0.105(3) 0.127(3) 0.0067(18) -0.0015(17) 0.000(2)
  C14C 0.0606(19) 0.107(3) 0.129(3) -0.0085(19) -0.0020(17) 0.003(2)
  C13C 0.084(3) 0.094(3) 0.181(4) -0.012(2) -0.009(3) 0.029(3)
  C12C 0.0625(18) 0.094(2) 0.131(3) -0.0025(18) -0.0054(16) 0.023(2)
  C13' 0.122(3) 0.113(3) 0.095(2) 0.038(3) -0.003(2) 0.010(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Br1 C4C . 1.904(4) yes
  N1 C6 . 1.449(4) yes
  N1 C1' . 1.465(4) yes
  N1 C2 . 1.466(4) yes
  C2 C3 . 1.522(4) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 C3' . 1.510(5) ?
  C3 C4 . 1.520(4) ?
  C3 H3A . 0.9800 ?
  C4 N7 . 1.494(3) yes
  C4 C5 . 1.515(4) ?
  C4 H4A . 0.9800 ?
  C5 C6 . 1.521(5) ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  N7 C8 . 1.362(4) yes
  N7 C1A . 1.431(4) yes
  C8 O8 . 1.217(4) ?
  C8 C9 . 1.530(4) ?
  C9 C10 . 1.507(6) ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C10 H10A . 0.9600 ?
  C10 H10B . 0.9600 ?
  C10 H10C . 0.9600 ?
  C1A C2A . 1.382(6) ?
  C1A C6A . 1.404(6) ?
  C6A C5A . 1.384(7) ?
  C6A H6AA . 0.9300 ?
  C5A C4A . 1.376(10) ?
  C5A H5AA . 0.9300 ?
  C4A C3A . 1.359(11) ?
  C4A H4AA . 0.9300 ?
  C3A C2A . 1.390(7) ?
  C3A H3AA . 0.9300 ?
  C2A H2AA . 0.9300 ?
  C1' C2' . 1.506(4) ?
  C1' H1'A . 0.9700 ?
  C1' H1'B . 0.9700 ?
  C2' O11 . 1.463(4) ?
  C2' C1B . 1.495(4) ?
  C2' H2'A . 0.9800 ?
  C1B C6B . 1.379(5) ?
  C1B C2B . 1.380(5) ?
  C6B C5B . 1.389(6) ?
  C6B H6BA . 0.9300 ?
  C5B C4B . 1.368(7) ?
  C5B H5BA . 0.9300 ?
  C4B C3B . 1.369(8) ?
  C4B H4BA . 0.9300 ?
  C3B C2B . 1.394(6) ?
  C3B H3BA . 0.9300 ?
  C2B H2BA . 0.9300 ?
  O11 C12X . 1.331(4) ?
  C12X O12 . 1.211(4) ?
  C12X C1C . 1.490(4) ?
  C1C C2C . 1.376(5) ?
  C1C C6C . 1.383(5) ?
  C6C C5C . 1.381(6) ?
  C6C H6CA . 0.9300 ?
  C5C C4C . 1.385(6) ?
  C5C H5CA . 0.9300 ?
  C4C C3C . 1.358(6) ?
  C3C C2C . 1.379(6) ?
  C3C H3CA . 0.9300 ?
  C2C H2CA . 0.9300 ?
  C3' H3'A . 0.9600 ?
  C3' H3'B . 0.9600 ?
  C3' H3'C . 0.9600 ?
  N11 C16 . 1.446(5) yes
  N11 C12 . 1.453(5) yes
  N11 C11' . 1.459(4) yes
  Br11 C14C . 1.910(4) yes
  C12 C13 . 1.518(5) ?
  C12 H12A . 0.9700 ?
  C12 H12B . 0.9700 ?
  C13 C13' . 1.522(6) ?
  C13 C14 . 1.530(5) ?
  C13 H13A . 0.9800 ?
  C14 N17 . 1.483(4) yes
  C14 C15 . 1.528(5) ?
  C14 H14A . 0.9800 ?
  C15 C16 . 1.520(5) ?
  C15 H15A . 0.9700 ?
  C15 H15B . 0.9700 ?
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  N17 C18 . 1.364(4) yes
  N17 C11A . 1.444(4) yes
  C18 O18 . 1.222(4) ?
  C18 C19 . 1.511(5) ?
  C19 C20 . 1.489(6) ?
  C19 H19A . 0.9700 ?
  C19 H19B . 0.9700 ?
  C20 H20A . 0.9600 ?
  C20 H20B . 0.9600 ?
  C20 H20C . 0.9600 ?
  C11A C16A . 1.377(5) ?
  C11A C12A . 1.388(5) ?
  C12A C13A . 1.392(7) ?
  C12A H12C . 0.9300 ?
  C13A C14A . 1.356(8) ?
  C13A H13B . 0.9300 ?
  C14A C15A . 1.359(8) ?
  C14A H14B . 0.9300 ?
  C15A C16A . 1.376(6) ?
  C15A H15C . 0.9300 ?
  C16A H16C . 0.9300 ?
  C11' C12' . 1.516(5) ?
  C11' H11A . 0.9700 ?
  C11' H11B . 0.9700 ?
  C12' O21 . 1.448(4) ?
  C12' C11B . 1.510(4) ?
  C12' H12D . 0.9800 ?
  C11B C16B . 1.361(5) ?
  C11B C12B . 1.381(5) ?
  C16B C15B . 1.378(6) ?
  C16B H1CA . 0.9300 ?
  C15B C14B . 1.356(7) ?
  C15B H15D . 0.9300 ?
  C14B C13B . 1.381(7) ?
  C14B H14C . 0.9300 ?
  C13B C12B . 1.386(6) ?
  C13B H13C . 0.9300 ?
  C12B H12E . 0.9300 ?
  O21 C22 . 1.338(4) ?
  C22 O22 . 1.195(4) ?
  C22 C11C . 1.488(5) ?
  C11C C12C . 1.376(5) ?
  C11C C16C . 1.381(5) ?
  C16C C15C . 1.380(6) ?
  C16C H16D . 0.9300 ?
  C15C C14C . 1.352(7) ?
  C15C H15E . 0.9300 ?
  C14C C13C . 1.359(6) ?
  C13C C12C . 1.393(6) ?
  C13C H13D . 0.9300 ?
  C12C H12F . 0.9300 ?
  C13' H13E . 0.9600 ?
  C13' H13F . 0.9600 ?
  C13' H13G . 0.9600 ?