#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2003382.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2003382
loop_
_publ_author_name
'Didierjean, C.'
'Aubry, A.'
'Zouikri, M.'
'Boussard, G.'
'Marraud, M.'
_publ_section_title
;
 Z-AzPro-AzPro-OBzl
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              688
_journal_page_last               690
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C23 H26 N4 O5'
_chemical_formula_sum            'C23 H26 N4 O5'
_chemical_formula_weight         438.48
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2c'
_symmetry_space_group_name_H-M   'P 1 1 21'
_atom_type_scat_source           'SHELX76 (Sheldrick, 1976)'
_cell_angle_alpha                90
_cell_angle_beta                 115.27(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3860(10)
_cell_length_b                   27.912(3)
_cell_length_c                   9.4630(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      30
_cell_measurement_theta_min      20
_cell_volume                     2241.9(6)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4602
_diffrn_reflns_theta_max         70
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.68
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.30
_exptl_crystal_description       parallelepiped
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.37
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4239
_refine_ls_R_factor_obs          0.031
_refine_ls_shift/esd_max         0.21
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 0.0316/[\s^2^(F) + 0.00013F^2^]'
_refine_ls_wR_factor_obs         0.035
_reflns_number_observed          4239
_reflns_number_total             4509
_reflns_observed_criterion       I>3\s(I)
_[local]_cod_data_source_file    na1107.cif
_[local]_cod_data_source_block   na1107a
_[local]_cod_cif_authors_sg_H-M  'P1 21 1'
_[local]_cod_cif_authors_sg_Hall 'P 2y1'
_cod_original_cell_volume        2242
_cod_database_code               2003382
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C(1A) .2514(3) .177 -.3442(4)
C(2A) .2868(3) .22330(10) -.2975(4)
C(3A) .4273(3) .23500(10) -.1729(3)
C(4A) .5341(3) .19979(9) -.0942(3)
C(5A) .4969(3) .15340(10) -.1444(4)
C(6A) .3581(4) .14190(10) -.2660(4)
C(7A) .6874(3) .21170(10) .0406(3)
O(1A) .6545(2) .21786(7) .1755(2)
C(8A) .7810(3) .22897(9) .3088(3)
O(2A) .9150(2) .22918(7) .3247(2)
N(1A) .7377(2) .23986(8) .4243(2)
C(9A) .8499(3) .24100(10) .5903(3)
C(10A) .7474(3) .22880(10) .6730(3)
C(11A) .6011(3) .20620(10) .5487(3)
N(2A) .5824(2) .23035(8) .4052(2)
C(12A) .4804(3) .26941(9) .3465(3)
O(3A) .5184(2) .30823(7) .3189(2)
N(3A) .3301(2) .25790(7) .3258(2)
C(13A) .2547(3) .21220(10) .2589(3)
C(14A) .1456(3) .22490(10) .0919(3)
C(15A) .0951(3) .27600(10) .0995(3)
N(4A) .2148(2) .29336(7) .2502(2)
C(16A) .1817(3) .32696(9) .3335(3)
O(4A) .0692(2) .35323(7) .2794(2)
O(5A) .2942(2) .32891(6) .4810(2)
C(17A) .2881(5) .36900(10) .5725(4)
C(18A) .4236(3) .36426(9) .7286(3)
C(19A) .5745(4) .35770(10) .7452(4)
C(20A) .6967(4) .35090(10) .8900(4)
C(21A) .6694(4) .35240(10) 1.0197(4)
C(22A) .5214(4) .35890(10) 1.0065(4)
C(23A) .3984(4) .36470(10) .8605(4)
C(1B) -.4687(5) .5192(3) -.2082(5)
C(2B) -.4520(5) .5671(3) -.2053(5)
C(3B) -.3214(4) .5892(2) -.0862(4)
C(4B) -.2087(3) .56170(10) .0249(3)
C(5B) -.2270(4) .51260(10) .0186(5)
C(6B) -.3570(5) .4917(2) -.0975(6)
C(7B) -.0662(4) .58450(10) .1512(4)
O(1B) -.0559(2) .56790(7) .3003(2)
C(8B) .0516(3) .59030(9) .4248(3)
O(2B) .1380(2) .62172(7) .4218(3)
N(1B) .0573(3) .57240(8) .5602(3)
C(9B) .1309(4) .59670(10) .7092(4)
C(10B) .0187(5) .5899(2) .7818(5)
C(11B) -.1170(4) .56120(10) .6682(4)
N(2B) -.0592(3) .54041(7) .5586(2)
C(12B) -.0079(3) .49275(9) .5778(3)
O(3B) .1196(2) .47992(7) .5904(3)
N(3B) -.1223(2) .46290(7) .5828(2)
C(13B) -.2900(3) .46640(10) .4782(4)
C(14B) -.3253(5) .42160(10) .3845(5)
C(15B) -.1930(3) .38760(10) .4633(3)
N(4B) -.0841(2) .41396(7) .6011(2)
C(16B) -.0203(3) .39530(9) .7467(3)
O(4B) -.0077(2) .35270(6) .7734(2)
O(5B) .0337(2) .42984(6) .8550(2)
C(17B) .1140(4) .41440(10) 1.0160(3)
C(18B) .2059(3) .45686(9) 1.1075(3)
C(19B) .2992(4) .48330(10) 1.0558(3)
C(20B) .3838(4) .52220(10) 1.1417(4)
C(21B) .3745(4) .53500(10) 1.2783(4)
C(22B) .2840(3) .50840(10) 1.3312(3)
C(23B) .1995(3) .46960(10) 1.2465(3)
H(C1A) .154(3) .1673(9) -.424(3)
H(C2A) .217(3) .2429(9) -.342(3)
H(C3A) .449(3) .2670(10) -.125(3)
H(C5A) .569(3) .1329(9) -.096(3)
H(C6A) .339(3) .1110(10) -.306(3)
H(C7A) .771(3) .1850(9) .060(3)
H'(C7A) .733(3) .2409(9) .025(3)
H(C9A) .942(3) .2167(9) .606(3)
H'(C9A) .902(3) .2710(10) .617(3)
H(C10A) .714(3) .2550(10) .715(3)
H'(C10A) .803(3) .2101(9) .764(3)
H(C11A) .504(3) .2117(9) .560(3)
H'(C11A) .615(3) .1700(10) .536(3)
H(C13A) .191(3) .2003(9) .323(3)
H'(C13A) .335(3) .1890(10) .267(3)
H(C14A) .207(3) .2280(10) .031(3)
H'(C14A) .059(3) .2049(9) .046(3)
H(C15A) -.009(3) .2776(9) .107(3)
H'(C15A) .095(3) .2939(9) .010(3)
H(C17A) .200(3) .3790(10) .558(3)
H'(C17A) .312(3) .3990(10) .518(3)
H(C19A) .583(3) .3540(10) .662(3)
H(C20A) .804(3) .3447(9) .912(3)
H(C21A) .760(3) .3471(9) 1.119(3)
H(C22A) .492(3) .3581(9) 1.092(3)
H(C23A) .293(3) .3676(9) .850(3)
H(C1B) -.564(4) .4980(10) -.295(4)
H(C2B) -.521(4) .5870(10) -.275(4)
H(C3B) -.315(4) .6200(10) -.069(4)
H(C5B) -.156(4) .4920(10) .103(4)
H(C6B) -.369(4) .4610(10) -.110(4)
H(C7B) -.072(4) .6200(10) .156(4)
H'(C7B) .032(4) .5780(10) .144(4)
H(C9B) .228(4) .5800(10) .785(4)
H'(C9B) .150(4) .6220(10) .701(4)
H(C10B) -.007(4) .6100(10) .834(4)
H'(C10B) .088(4) .5670(10) .884(4)
H(C11B) -.150(3) .5340(10) .714(4)
H'(C11B) -.208(4) .5810(10) .599(4)
H(C13B) -.305(4) .4960(10) .424(4)
H'(C13B) -.353(3) .4620(10) .545(3)
H(C14B) -.420(4) .4090(10) .338(4)
H'(C14B) -.314(4) .4290(10) .304(4)
H(C15B) -.137(4) .3800(10) .409(4)
H'(C15B) -.228(3) .3590(10) .500(4)
H(C17B) .192(4) .3860(10) 1.021(4)
H'(C17B) .028(4) .4080(10) 1.048(4)
H(C19B) .295(3) .4730(10) .960(4)
H(C20B) .445(4) .5390(10) 1.102(4)
H(C21B) .431(3) .5650(10) 1.346(4)
H(C22B) .271(3) .5170(10) 1.424(4)
H(C23B) .136(3) .4530(10) 1.276(4)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2A) C(1A) C(6A) 118.9(2) yes
C(1A) C(2A) C(3A) 121.0(3) yes
C(2A) C(3A) C(4A) 120.2(3) yes
C(3A) C(4A) C(5A) 117.9(2) yes
C(3A) C(4A) C(7A) 121.1(2) yes
C(5A) C(4A) C(7A) 120.9(2) yes
C(4A) C(5A) C(6A) 121.7(3) yes
C(1A) C(6A) C(5A) 120.2(3) yes
C(4A) C(7A) O(1A) 106.8(2) yes
C(7A) O(1A) C(8A) 114.7(2) yes
O(1A) C(8A) O(2A) 125.1(3) yes
O(1A) C(8A) N(1A) 111.1(2) yes
O(2A) C(8A) N(1A) 123.8(2) yes
C(8A) N(1A) C(9A) 122.9(2) yes
C(8A) N(1A) N(2A) 120.2(2) yes
C(9A) N(1A) N(2A) 111.6(2) yes
N(1A) C(9A) C(10A) 102.9(2) yes
O(3A) C(12A) N(3A) 124.0(2) yes
C(12A) N(3A) C(13A) 122.7(2) yes
C(12A) N(3A) N(4A) 115.1(2) yes
C(13A) N(3A) N(4A) 105.4(2) yes
N(3A) C(13A) C(14A) 103.6(2) yes
C(13A) C(14A) C(15A) 104.9(2) yes
C(14A) C(15A) N(4A) 103.4(2) yes
N(3A) N(4A) C(15A) 111.2(2) yes
N(3A) N(4A) C(16A) 120.6(2) yes
C(15A) N(4A) C(16A) 121.8(2) yes
N(4A) C(16A) O(4A) 123.7(2) yes
N(4A) C(16A) O(5A) 111.2(2) yes
O(4A) C(16A) O(5A) 125.0(2) yes
C(16A) O(5A) C(17A) 116.3(2) yes
O(5A) C(17A) C(18A) 107.0(3) yes
C(17A) C(18A) C(19A) 122.0(3) yes
C(17A) C(18A) C(23A) 119.9(3) yes
C(9A) C(10A) C(11A) 105.0(2) yes
C(10A) C(11A) N(2A) 103.8(2) yes
N(1A) N(2A) C(11A) 105.1(2) yes
N(1A) N(2A) C(12A) 113.4(2) yes
C(11A) N(2A) C(12A) 121.3(2) yes
N(2A) C(12A) O(3A) 124.8(2) yes
N(2A) C(12A) N(3A) 111.1(2) yes
C(19A) C(18A) C(23A) 118.0(2) yes
C(18A) C(19A) C(20A) 121.0(4) yes
C(19A) C(20A) C(21A) 119.9(3) yes
C(20A) C(21A) C(22A) 120.2(3) yes
C(21A) C(22A) C(23A) 119.7(4) yes
C(18A) C(23A) C(22A) 121.1(3) yes
C(2B) C(1B) C(6B) 120.0(4) yes
C(1B) C(2B) C(3B) 120.4(4) yes
C(2B) C(3B) C(4B) 119.8(4) yes
C(3B) C(4B) C(5B) 118.9(3) yes
C(3B) C(4B) C(7B) 120.7(3) yes
C(5B) C(4B) C(7B) 120.4(3) yes
C(4B) C(5B) C(6B) 120.5(3) yes
C(1B) C(6B) C(5B) 120.4(5) yes
C(4B) C(7B) O(1B) 107.9(3) yes
C(7B) O(1B) C(8B) 114.9(2) yes
O(1B) C(8B) O(2B) 125.7(3) yes
O(1B) C(8B) N(1B) 111.8(2) yes
O(2B) C(8B) N(1B) 122.4(2) yes
C(8B) N(1B) C(9B) 124.0(3) yes
C(8B) N(1B) N(2B) 120.5(2) yes
C(9B) N(1B) N(2B) 110.7(3) yes
N(1B) C(9B) C(10B) 104.6(3) yes
O(3B) C(12B) N(3B) 125.0(2) yes
C(12B) N(3B) C(13B) 124.5(2) yes
C(12B) N(3B) N(4B) 115.5(2) yes
C(13B) N(3B) N(4B) 107.1(2) yes
N(3B) C(13B) C(14B) 104.4(3) yes
C(13B) C(14B) C(15B) 108.3(3) yes
C(14B) C(15B) N(14B) 103.9(3) yes
N(3B) N(4B) C(15B) 109.5(2) yes
N(3B) N(4B) C(16B) 118.7(2) yes
C(15B) N(4B) C(16B) 123.4(2) yes
N(4B) C(16B) O(4B) 123.6(2) yes
N(4B) C(16B) O(5B) 111.2(2) yes
O(4B) C(16B) O(5B) 125.2(2) yes
C(16B) O(5B) C(17B) 116.7(2) yes
O(5B) C(17B) C(18B) 106.6(2) yes
C(17B) C(18B) C(19B) 120.7(3) yes
C(17B) C(18B) C(23B) 120.1(3) yes
C(9B) C(10B) C(11B) 106.7(3) yes
C(10B) C(11B) N(2B) 105.0(3) yes
N(1B) N(2B) C(11B) 105.1(2) yes
N(1B) N(2B) C(12B) 112.3(2) yes
C(11B) N(2B) C(12B) 119.4(2) yes
N(2B) C(12B) O(3B) 124.6(3) yes
N(2B) C(12B) N(3B) 110.4(2) yes
C(19B) C(18B) C(23B) 119.2(2) yes
C(18B) C(19B) C(20B) 120.0(3) yes
C(19B) C(20B) C(21B) 120.2(3) yes
C(20B) C(21B) C(22B) 119.9(3) yes
C(21B) C(22B) C(23B) 120.2(3) yes
C(18B) C(23B) C(22B) 120.4(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1A) C(2A) 1.355(3) yes
C(1A) C(6A) 1.373(4) yes
C(2A) C(3A) 1.381(3) yes
C(3A) C(4A) 1.374(4) yes
C(4A) C(5A) 1.372(4) yes
C(4A) C(7A) 1.497(3) yes
C(5A) C(6A) 1.358(4) yes
C(7A) O(1A) 1.446(4) yes
O(1A) C(8A) 1.348(2) yes
C(8A) O(2A) 1.201(3) yes
C(8A) N(1A) 1.353(4) yes
N(1A) C(9A) 1.471(3) yes
N(1A) N(2A) 1.416(3) yes
C(9A) C(10A) 1.515(5) yes
C(10A) C(11A) 1.513(4) yes
C(11A) N(2A) 1.458(4) yes
N(2A) C(12A) 1.400(3) yes
C(12A) O(3A) 1.204(3) yes
C(12A) N(3A) 1.377(3) yes
N(3A) C(13A) 1.464(3) yes
N(3A) N(4A) 1.415(3) yes
C(13A) C(14A) 1.513(4) yes
C(14A) C(15A) 1.513(4) yes
C(15A) N(4A) 1.471(3) yes
N(4A) C(16A) 1.344(4) yes
C(16A) O(4A) 1.206(3) yes
C(16A) O(5A) 1.344(2) yes
O(5A) C(17A) 1.431(4) yes
C(17A) C(18A) 1.487(4) yes
C(18A) C(19A) 1.369(5) yes
C(18A) C(23A) 1.366(5) yes
C(19A) C(20A) 1.374(4) yes
C(20A) C(21A) 1.357(6) yes
C(21A) C(22A) 1.353(6) yes
C(22A) C(23A) 1.380(4) yes
C(1B) C(2B) 1.350(10) yes
C(1B) C(6B) 1.358(7) yes
C(2B) C(3B) 1.404(5) yes
C(3B) C(4B) 1.364(4) yes
C(4B) C(5B) 1.380(5) yes
C(4B) C(7B) 1.502(4) yes
C(5B) C(6B) 1.376(5) yes
C(7B) O(1B) 1.448(4) yes
O(1B) C(8B) 1.335(3) yes
C(8B) O(2B) 1.203(4) yes
C(8B) N(1B) 1.355(4) yes
N(1B) C(9B) 1.447(4) yes
N(1B) N(2B) 1.406(3) yes
C(9B) C(10B) 1.494(7) yes
C(10B) C(11B) 1.501(5) yes
C(11B) N(2B) 1.478(5) yes
N(2B) C(12B) 1.400(3) yes
C(12B) O(3B) 1.205(4) yes
C(12B) N(3B) 1.376(3) yes
N(3B) C(13B) 1.461(3) yes
N(3B) N(4B) 1.404(3) yes
C(13B) C(14B) 1.486(5) yes
C(14B) C(15B) 1.487(5) yes
C(15B) N(4B) 1.467(3) yes
N(4B) C(16B) 1.351(3) yes
C(16B) O(4B) 1.211(3) yes
C(16B) O(5B) 1.339(3) yes
O(5B) C(17B) 1.447(3) yes
C(17B) C(18B) 1.502(4) yes
C(18B) C(19B) 1.386(5) yes
C(18B) C(23B) 1.388(4) yes
C(19B) C(20B) 1.384(4) yes
C(20B) C(21B) 1.379(6) yes
C(21B) C(22B) 1.373(5) yes
C(22B) C(23B) 1.380(4) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C(4A) C(7A) O(1A) C(8A) -179.8(2) yes
C(7A) O(1A) C(8A) N(1A) 172.5(2) yes
O(1A) C(8A) N(1A) N(2A) 11.4(3) yes
O(1A) C(8A) N(1A) C(9A) 163.5(2) yes
C(8A) N(1A) N(2A) C(12A) -93.2(3) yes
N(1A) N(2A) C(11A) C(10A) 33.4(3) yes
N(2A) C(11A) C(10A) C(9A) -32.0(3) yes
C(11A) C(10A) C(9A) N(1A) 18.1(3) yes
C(10A) C(9A) N(1A) N(2A) 2.5(3) yes
C(9A) N(1A) N(2A) C(11A) -22.9(3) yes
N(1A) N(2A) C(12A) N(3A) 178.2(2) yes
N(2A) C(12A) N(3A) N(4A) -173.0(2) yes
N(2A) C(12A) N(3A) C(13A) -42.4(3) yes
C(12A) N(3A) N(4A) C(16A) -91.2(3) yes
N(3A) N(4A) C(15A) C(14A) 1.9(3) yes
N(4A) C(15A) C(14A) C13(A) 18.5(3) yes
C(15A) C(14A) C(13A) N(3A) -31.9(3) yes
C(14A) C(13A) N(3A) N(4A) 33.0(3) yes
C(13A) N(3A) N(4A) C(15A) -22.3(3) yes
N(3A) N(4A) C(16A) O(5A) 15.5(3) yes
N(4A) C(16A) O(5A) C(17A) 168.6(3) yes
C(16A) O(5A) C(17A) C(18A) -179.1(3) yes
C(4B) C(7B) O(1B) C(8B) -170.7(2) yes
C(7B) O(1B) C(8B) N(1B) -178.8(3) yes
O(1B) C(8B) N(1B) N(2B) -10.5(4) yes
O(1B) C(8B) N(1B) C(9B) -163.5(3) yes
C(8B) N(1B) N(2B) C(12B) 101.1(3) yes
N(1B) N(2B) C(11B) C(10B) -26.8(3) yes
N(2B) C(11B) C(10B) C(9B) 16.1(4) yes
C(11B) C(10B) C(9B) N(1B) 0.1(4) yes
C(10B) C(9B) N(1B) N(2B) -18.0(3) yes
C(9B) N(1B) N(2B) C(11B) 28.5(3) yes
N(1B) N(2B) C(12B) N(3B) 177.2(2) yes
N(2B) C(12B) N(3B) N(4B) 179.7(2) yes
N(2B) C(12B) N(3B) C(13B) 43.4(3) yes
C(12B) N(3B) N(4B) C(16B) 93.6(4) yes
N(3B) N(4B) C(15B) C(14B) -16.0(4) yes
N(4B) C(15B) C(14B) C(13B) -.1(3) yes
C(15B) C(14B) C(13B) N(3B) 15.2(5) yes
C(14B) C(13B) N(3B) N(4B) -25.2(4) yes
C(13B) N(3B) N(4B) C(15B) 26.4(3) yes
N(3B) N(4B) C(16B) O(5B) -16.1(3) yes
N(4B) C(16B) O(5B) C(17B) -176.2(3) yes
C(16B) O(5B) C(17B) C(18B) 162.5(3) yes