data_2008358
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  678
_journal_page_last  680
_publ_section_title
;
A flavone 1,4-dihydropyridine calcium antagonist
;
loop_
_publ_author_name
  '\"Ozbey, S\"uheyla'
  'Kendi, Engin'
  'K\?ilc\?igil Ayhan, G\"ulg\"un'
  'Ertan, Rahmiye'
_chemical_formula_moiety  'C28 H27 N O6'
_chemical_formula_sum  'C28 H27 N O6'
_chemical_formula_weight  473.52
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,-y,-z'
_cell_length_a  9.9152(6)
_cell_length_b  11.0521(7)
_cell_length_c  13.7630(10)
_cell_angle_alpha  69.600(5)
_cell_angle_beta  73.969(6)
_cell_angle_gamma  65.035(5)
_cell_volume  1266.7(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  295
_exptl_crystal_density_diffrn  1.242
_refine_ls_R_factor_obs  0.047
_refine_ls_wR_factor_obs  0.054
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
  O1 0.1893(2) 0.34070(10)
  0.55860(10)
  0.0463(6) Ueq . . O
  O2 -0.0615(2) 0.4402(2) 0.82800(10)
  0.0723(10) Ueq . . O
  O32 0.4726(2) 0.7177(2) 0.64430(10)
  0.0711(7) Ueq . . O
  O33 0.3160(2) 0.8644(2) 0.73950(10)
  0.0644(7) Ueq . . O
  O52 0.6908(2) 0.2284(2) 0.80980(10)
  0.0693(8) Ueq . . O
  O53 0.6138(2) 0.1312(2) 0.97520(10)
  0.0629(7) Ueq . . O
  N1 0.2746(2) 0.5220(2) 0.98690(10)
  0.0503(8) Ueq . . N
  C2' 0.0511(2) 0.3305(2) 0.5933(2) 0.0441(8) Ueq . . C
  C2 0.2733(2) 0.6384(2) 0.9060(2) 0.0467(9) Ueq . . C
  C3 0.3685(2) 0.6237(2) 0.8150(2) 0.0422(8) Ueq . . C
  C3' -0.0339(3) 0.3628(2) 0.6821(2) 0.0536(8) Ueq . . C
  C4' 0.0162(2) 0.4089(2) 0.7467(2) 0.0504(8) Ueq . . C
  C4 0.4571(2) 0.4806(2) 0.7975(2) 0.0410(8) Ueq . . C
  C5 0.4791(2) 0.3692(2) 0.9011(2) 0.0423(7) Ueq . . C
  C5' 0.2364(2) 0.4488(2) 0.7664(2) 0.0447(8) Ueq . . C
  C6 0.3828(2) 0.3920(2) 0.9897(2) 0.0444(7) Ueq . . C
  C6' 0.3812(2) 0.4480(2) 0.7327(2) 0.0397(7) Ueq . . C
  C7' 0.4575(2) 0.4129(2) 0.6386(2) 0.0444(8) Ueq . . C
  C8' 0.3923(2) 0.3788(2) 0.5807(2) 0.0466(8) Ueq . . C
  C9' 0.2479(2) 0.3790(2) 0.6178(2) 0.0305(8) Ueq . . C
  C10' 0.1671(2) 0.4134(2) 0.7104(2) 0.0413(7) Ueq . . C
  C20 0.0128(2) 0.2798(2) 0.5228(2) 0.0474(8) Ueq . . C
  C21 0.1608(3) 0.7698(2) 0.9319(2) 0.0681(11) Ueq . . C
  C30 -0.1136(3) 0.2436(3) 0.5513(2) 0.0695(9) Ueq . . C
  C31 0.3909(3) 0.7367(2) 0.7250(2) 0.0486(8) Ueq . . C
  C34 0.3360(3) 0.9788(3) 0.6533(2) 0.0816(14) Ueq . . C
  C35 0.4742(4) 1.0000(3) 0.6488(3) 0.0980(14) Ueq . . C
  C40 -0.1502(3) 0.1970(3) 0.4849(2) 0.0877(14) Ueq . . C
  C50 -0.0611(3) 0.1852(3) 0.3902(2) 0.0784(9) Ueq . . C
  C51 0.6033(2) 0.2394(2) 0.8901(2) 0.0489(9) Ueq . . C
  C54 0.7348(3) 0.0026(3) 0.9639(2) 0.0791(14) Ueq . . C
  C55 0.7317(4) -0.1018(3) 1.0669(3) 0.0969(16) Ueq . . C
  C60 0.0647(3) 0.2189(3) 0.3618(2) 0.0747(12) Ueq . . C
  C61 0.3749(3) 0.2919(3) 1.0961(2) 0.0604(9) Ueq . . C
  C70 0.1020(3) 0.2664(3) 0.4270(2) 0.0603(9) Ueq . . C
  H30 -0.175 0.252 0.617 0.088 Ueq . . H
  H40 -0.237 0.173 0.505 0.109 Ueq . . H
  H50 -0.085 0.152 0.345 0.099 Ueq . . H
  H60 0.126 0.211 0.296 0.097 Ueq . . H
  H70 0.188 0.292 0.407 0.080 Ueq . . H
  H3' -0.130 0.354 0.703 0.068 Ueq . . H
  H5' 0.183 0.474 0.830 0.052 Ueq . . H
  H7' 0.558 0.411 0.615 0.058 Ueq . . H
  H8' 0.444 0.358 0.516 0.061 Ueq . . H
  H1 0.196 0.532 1.045 0.062 Ueq . . H
  H4 0.556 0.478 0.761 0.071 Ueq . . H
  H211 0.110 0.749 1.002 0.096 Ueq . . H
  H212 0.212 0.829 0.925 0.096 Ueq . . H
  H213 0.089 0.815 0.885 0.096 Ueq . . H
  H611 0.296 0.337 1.143 0.077 Ueq . . H
  H612 0.357 0.217 1.091 0.077 Ueq . . H
  H613 0.468 0.258 1.121 0.077 Ueq . . H
  H351 0.485 1.075 0.591 0.123 Ueq . . H
  H352 0.469 1.019 0.712 0.123 Ueq . . H
  H353 0.558 0.918 0.642 0.123 Ueq . . H
  H541 0.828 0.015 0.945 0.101 Ueq . . H
  H542 0.721 -0.027 0.911 0.101 Ueq . . H
  H551 0.810 -0.187 1.062 0.124 Ueq . . H
  H552 0.745 -0.071 1.119 0.124 Ueq . . H
  H553 0.638 -0.114 1.085 0.124 Ueq . . H
  H341 0.252 1.061 0.660 0.108 Ueq . . H
  H342 0.341 0.961 0.589 0.108 Ueq . . 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
_atom_site_aniso_type_symbol
  O1 0.0451(7) 0.0565(7) 0.0375(6) -0.0191(5) 0.0003(6) -0.0169(5) O
  O2 0.0562(9) 0.1110(10)
  0.0562(8) -0.0359(7) 0.0212(7) -0.0458(7) O
  O32 0.1060(10)
  0.0629(8) 0.0420(8) -0.0401(7) 0.0134(8) -0.0182(6) O
  O33 0.0780(10)
  0.0403(7) 0.0554(9) -0.0135(7) -0.0029(8) -0.0056(7) O
  O52 0.0590(10)
  0.0606(9) 0.0590(9) -0.0047(8) 0.0090(8) -0.0171(7) O
  O53 0.0634(9) 0.0477(8) 0.0563(9) -0.0074(7) -0.0060(8) -0.0074(7) O
  N1 0.0496(9) 0.0541(9) 0.0384(8) -0.0179(7) 0.0092(7) -0.0154(7) N
  C2' 0.0390(10)
  0.0416(9) 0.0430(10)
  -0.0101(7) -0.0047(8) -0.0078(8) C
  C2 0.0480(10)
  0.0481(9) 0.0450(10)
  -0.0169(7) -0.0020(8) -0.0180(7) C
  C3 0.0450(10)
  0.0433(9) 0.0386(9) -0.0163(7) -0.0041(8) -0.0127(7) C
  C3' 0.0410(10)
  0.0670(10)
  0.0530(10)
  -0.0212(8) 0.0029(9) -0.0218(9) C
  C4' 0.0440(10)
  0.0570(10)
  0.0420(10)
  -0.0157(8) 0.0036(9) -0.0148(8) C
  C4 0.0383(9) 0.0447(9) 0.0365(9) -0.0156(7) 0.0030(8) -0.0127(7) C
  C5 0.0411(9) 0.0461(9) 0.0384(9) -0.0161(7) -0.0040(8) -0.0109(7) C
  C5' 0.0480(10)
  0.0477(9) 0.0331(9) -0.0151(8) 0.0045(8) -0.0156(7) C
  C6 0.0460(10)
  0.0492(9) 0.0381(9) -0.0193(7) -0.0040(8) -0.0110(7) C
  C6' 0.0440(10)
  0.0347(8) 0.0329(9) -0.0127(7) -0.0003(8) -0.0071(7) C
  C7' 0.0420(10)
  0.0496(9) 0.0380(10)
  -0.0177(7) 0.0048(8) -0.0145(8) C
  C8' 0.0500(10)
  0.0540(10)
  0.0345(9) -0.0209(8) 0.0090(8) -0.0195(7) C
  C9' 0.0440(10)
  0.0381(8) 0.0317(9) -0.0139(7) -0.0015(8) -0.0081(7) C
  C10' 0.0410(10)
  0.0410(9) 0.0339(9) -0.0114(7) 0.0005(8) -0.0099(7) C
  C20 0.0430(10)
  0.0440(10)
  0.0480(10)
  -0.0082(8) -0.0123(8) -0.0091(8) C
  C21 0.071(2) 0.0600(10)
  0.0610(10)
  -0.0150(10)
  0.0100(10)
  -0.0280(10)
  C
  C30 0.0550(10)
  0.0900(10)
  0.0720(10)
  -0.0260(10)
  -0.0040(10)
  -0.0360(10)
  C
  C31 0.0570(10)
  0.0490(10)
  0.0410(10)
  -0.0193(8) -0.0089(9) -0.0120(8) C
  C34 0.097(2) 0.0480(10)
  0.069(2) -0.0160(10)
  -0.007(2) 0.0030(10)
  C
  C35 0.122(2) 0.0710(10)
  0.096(2) -0.0500(10)
  0.006(2) -0.0150(10)
  C
  C40 0.0650(10)
  0.111(2) 0.097(2) -0.0370(10)
  -0.0110(10)
  -0.0460(10)
  C
  C50 0.0780(10)
  0.0930(10)
  0.0800(10)
  -0.0280(10)
  -0.0250(10)
  -0.0350(10)
  C
  C51 0.0480(10)
  0.0490(10)
  0.0480(10)
  -0.0162(8) -0.0080(9) -0.0119(8) C
  C54 0.078(2) 0.0510(10)
  0.085(2) -0.0030(10)
  -0.0130(10)
  -0.0160(10)
  C
  C55 0.092(2) 0.056(2) 0.106(2) -0.0100(10)
  -0.019(2) 0.003(2) C
  C60 0.082(2) 0.0940(10)
  0.0580(10)
  -0.0350(10)
  -0.0090(10)
  -0.0290(10)
  C
  C61 0.0670(10)
  0.0660(10)
  0.0400(10)
  -0.0250(10)
  -0.0020(10)
  -0.0080(10)
  C
  C70 0.0650(10)
  0.0690(10)
  0.0490(10)
  -0.0263(9) -0.0070(10)
  -0.0167(9) C
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C2' . . 1.360(3) yes
  O1 C9' . . 1.375(3) yes
  O2 C4' . . 1.240(3) yes
  O32 C31 . . 1.207(3) yes
  O33 C31 . . 1.346(3) yes
  O33 C34 . . 1.443(3) yes
  O52 C51 . . 1.210(3) yes
  O53 C51 . . 1.341(2) yes
  O53 C54 . . 1.447(3) yes
  N1 C2 . . 1.375(2) yes
  N1 C6 . . 1.378(2) yes
  N1 H1 . . 0.950 no
  C2' C3' . . 1.346(3) yes
  C2' C20 . . 1.471(4) yes
  C2 C3 . . 1.358(3) yes
  C2 C21 . . 1.501(3) yes
  C3 C4 . . 1.519(3) yes
  C3 C31 . . 1.465(3) yes
  C3' C4' . . 1.438(4) yes
  C3' H3' . . 0.950 no
  C4' C10' . . 1.457(3) yes
  C4 C5 . . 1.523(2) yes
  C34 H341 . . 0.950 no
  C34 H342 . . 0.950 no
  C35 H351 . . 0.950 no
  C35 H352 . . 0.950 no
  C35 H353 . . 0.950 no
  C40 C50 . . 1.372(3) no
  C40 H40 . . 0.950 no
  C50 C60 . . 1.367(5) no
  C50 H50 . . 0.950 no
  C54 C55 . . 1.486(4) yes
  C54 H541 . . 0.950 no
  C4 C6' . . 1.521(4) yes
  C4 H4 . . 0.962 no
  C5 C6 . . 1.352(3) yes
  C5 C51 . . 1.467(3) yes
  C5' C6' . . 1.378(3) no
  C5' C10' . . 1.396(4) no
  C5' H5' . . 0.950 no
  C6 C61 . . 1.502(3) yes
  C6' C7' . . 1.401(3) no
  C7' C8' . . 1.376(4) no
  C7' H7' . . 0.950 no
  C8' C9' . . 1.380(3) no
  C8' H8' . . 0.950 no
  C9' C10' . . 1.389(3) no
  C20 C30 . . 1.388(4) no
  C20 C70 . . 1.386(3) no
  C21 H211 . . 0.950 no
  C21 H212 . . 0.950 no
  C21 H213 . . 0.950 no
  C30 C40 . . 1.378(5) no
  C30 H30 . . 0.950 no
  C34 C35 . . 1.468(6) yes
  C54 H542 . . 0.950 no
  C55 H551 . . 0.950 no
  C55 H552 . . 0.950 no
  C55 H553 . . 0.950 no
  C60 C70 . . 1.376(5) no
  C60 H60 . . 0.950 no
  C61 H611 . . 0.950 no
  C61 H612 . . 0.950 no
  C61 H613 . . 0.950 no
  C70 H70 . . 0.950 no