#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/80/2228086.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_2228086
loop_
_publ_author_name
'Arumugam, Natarajan'
'Abdul Rahim, Aisyah Saad'
'Osman, Hasnah'
'Quah, Ching Kheng'
'Fun, Hoong-Kun'
_publ_section_title
;
 Ethyl
 1-sec-butyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate
;
_journal_coeditor_code           WN2406
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2412
_journal_page_last               o2413
_journal_paper_doi               10.1107/S1600536810033945
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H21 Cl N2 O2'
_chemical_formula_moiety         'C20 H21 Cl N2 O2'
_chemical_formula_sum            'C20 H21 Cl N2 O2'
_chemical_formula_weight         356.84
_chemical_name_systematic
;
Ethyl
1-sec-butyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.043(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4321(9)
_cell_length_b                   12.6218(12)
_cell_length_c                   13.6896(12)
_cell_measurement_reflns_used    5929
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.07
_cell_measurement_theta_min      2.83
_cell_volume                     1788.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21234
_diffrn_reflns_theta_full        36.17
_diffrn_reflns_theta_max         36.17
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.337
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.389
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         8437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0914P)²+0.4364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1745
_reflns_number_gt                6651
_reflns_number_total             8437
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2406.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228086
_cod_database_fobs_code          2228086
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
Cl Cl1 1.44482(3) -0.12780(3) 0.05943(3) 0.02804(10) Uani d . 1 . .
O O1 0.66151(9) 0.53169(7) 0.09366(8) 0.02287(19) Uani d . 1 . .
O O2 0.49447(10) 0.47833(8) 0.17101(8) 0.0244(2) Uani d . 1 . .
N N1 0.97430(9) 0.22053(7) 0.11935(8) 0.01566(17) Uani d . 1 A .
N N2 0.88205(10) 0.08363(8) 0.19214(8) 0.01724(18) Uani d . 1 . .
C C1 1.08637(12) -0.04972(9) 0.10289(9) 0.0184(2) Uani d . 1 A .
H H1A 1.0056 -0.0819 0.0969 0.022 Uiso calc R 1 . .
C C2 1.19323(13) -0.10669(10) 0.08102(9) 0.0198(2) Uani d . 1 . .
H H2A 1.1846 -0.1769 0.0607 0.024 Uiso calc R 1 . .
C C3 1.31246(12) -0.05767(10) 0.08982(9) 0.0193(2) Uani d . 1 . .
C C4 1.32851(12) 0.04663(10) 0.12105(10) 0.0204(2) Uani d . 1 . .
H H4A 1.4096 0.0782 0.1271 0.025 Uiso calc R 1 . .
C C5 1.22138(12) 0.10309(9) 0.14312(9) 0.0186(2) Uani d . 1 A .
H H5A 1.2310 0.1730 0.1643 0.022 Uiso calc R 1 . .
C C6 1.09949(11) 0.05585(9) 0.13384(8) 0.01582(18) Uani d . 1 . .
C C7 0.98702(11) 0.12116(9) 0.14997(8) 0.01543(18) Uani d . 1 A .
C C8 0.85402(10) 0.25092(8) 0.14249(8) 0.01417(17) Uani d . 1 . .
C C9 0.79079(11) 0.34784(9) 0.12560(8) 0.01504(18) Uani d . 1 A .
H H9A 0.8286 0.4032 0.0947 0.018 Uiso calc R 1 . .
C C10 0.66963(11) 0.35881(8) 0.15650(8) 0.01520(18) Uani d . 1 . .
C C11 0.61175(11) 0.27463(9) 0.20282(9) 0.0176(2) Uani d . 1 A .
H H11A 0.5306 0.2846 0.2229 0.021 Uiso calc R 1 . .
C C12 0.67240(12) 0.17741(9) 0.21918(9) 0.0187(2) Uani d . 1 . .
H H12A 0.6338 0.1219 0.2493 0.022 Uiso calc R 1 A .
C C13 0.79468(11) 0.16691(9) 0.18806(8) 0.01594(19) Uani d . 1 A .
C C14 0.59808(11) 0.46053(9) 0.14271(9) 0.01683(19) Uani d . 1 A .
C C15 0.60047(14) 0.63413(10) 0.07588(11) 0.0256(3) Uani d . 1 . .
H H15A 0.6041 0.6740 0.1367 0.031 Uiso calc R 1 . .
H H15B 0.5107 0.6256 0.0489 0.031 Uiso calc R 1 . .
C C16 0.67404(16) 0.69051(12) 0.00368(13) 0.0320(3) Uani d . 1 . .
H H16A 0.6341 0.7577 -0.0131 0.048 Uiso calc R 1 . .
H H16B 0.6735 0.6483 -0.0547 0.048 Uiso calc R 1 . .
H H16C 0.7615 0.7016 0.0327 0.048 Uiso calc R 1 . .
C C17A 0.87973(15) -0.01159(11) 0.25461(12) 0.0170(3) Uani d P 0.855(4) A 1
H H17A 0.9624 -0.0480 0.2532 0.020 Uiso calc PR 0.855(4) A 1
C C18A 0.87305(16) 0.02241(14) 0.36090(11) 0.0228(3) Uani d P 0.855(4) A 1
H H18A 0.7882 0.0516 0.3663 0.027 Uiso calc PR 0.855(4) A 1
H H18B 0.8847 -0.0393 0.4034 0.027 Uiso calc PR 0.855(4) A 1
C C19A 0.97501(17) 0.10445(16) 0.39550(12) 0.0268(4) Uani d P 0.855(4) A 1
H H19A 0.9705 0.1207 0.4635 0.040 Uiso calc PR 0.855(4) A 1
H H19B 0.9599 0.1676 0.3568 0.040 Uiso calc PR 0.855(4) A 1
H H19C 1.0590 0.0768 0.3881 0.040 Uiso calc PR 0.855(4) A 1
C C20A 0.77336(17) -0.08965(12) 0.21576(16) 0.0277(4) Uani d P 0.855(4) A 1
H H20A 0.7817 -0.1070 0.1486 0.042 Uiso calc PR 0.855(4) A 1
H H20B 0.6904 -0.0579 0.2194 0.042 Uiso calc PR 0.855(4) A 1
H H20C 0.7812 -0.1529 0.2549 0.042 Uiso calc PR 0.855(4) A 1
C C17B 0.9122(10) 0.0082(8) 0.2857(7) 0.0179(16) Uiso d P 0.145(4) A 2
H H17B 0.9924 -0.0301 0.2791 0.021 Uiso calc PR 0.145(4) A 2
C C18B 0.8027(10) -0.0706(8) 0.2733(8) 0.027(2) Uiso d P 0.145(4) A 2
H H18C 0.7234 -0.0335 0.2817 0.032 Uiso calc PR 0.145(4) A 2
H H18D 0.8175 -0.1225 0.3257 0.032 Uiso calc PR 0.145(4) A 2
C C19B 0.7823(14) -0.1313(11) 0.1720(11) 0.039(3) Uiso d P 0.145(4) A 2
H H19D 0.7234 -0.1891 0.1764 0.059 Uiso calc PR 0.145(4) A 2
H H19E 0.8636 -0.1582 0.1569 0.059 Uiso calc PR 0.145(4) A 2
H H19F 0.7472 -0.0836 0.1210 0.059 Uiso calc PR 0.145(4) A 2
C C20B 0.9247(12) 0.0562(10) 0.3823(8) 0.027(2) Uiso d P 0.145(4) A 2
H H20D 0.9400 0.0021 0.4316 0.040 Uiso calc PR 0.145(4) A 2
H H20E 0.8466 0.0934 0.3909 0.040 Uiso calc PR 0.145(4) A 2
H H20F 0.9959 0.1050 0.3886 0.040 Uiso calc PR 0.145(4) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O1 C15 . . 116.59(10) ?
C7 N1 C8 . . 104.38(9) ?
C7 N2 C13 . . 105.87(9) ?
C7 N2 C17A . . 126.20(10) ?
C13 N2 C17A . . 125.61(10) ?
C7 N2 C17B . . 116.8(4) ?
C13 N2 C17B . . 123.2(3) ?
C2 C1 C6 . . 120.43(12) ?
C2 C1 H1A . . 119.8 ?
C6 C1 H1A . . 119.8 ?
C3 C2 C1 . . 119.14(11) ?
C3 C2 H2A . . 120.4 ?
C1 C2 H2A . . 120.4 ?
C2 C3 C4 . . 121.67(11) ?
C2 C3 Cl1 . . 119.06(10) ?
C4 C3 Cl1 . . 119.26(10) ?
C3 C4 C5 . . 118.92(12) ?
C3 C4 H4A . . 120.5 ?
C5 C4 H4A . . 120.5 ?
C4 C5 C6 . . 120.60(11) ?
C4 C5 H5A . . 119.7 ?
C6 C5 H5A . . 119.7 ?
C5 C6 C1 . . 119.22(10) ?
C5 C6 C7 . . 118.75(10) ?
C1 C6 C7 . . 121.88(11) ?
N1 C7 N2 . . 113.76(9) ?
N1 C7 C6 . . 122.25(10) ?
N2 C7 C6 . . 123.86(10) ?
N1 C8 C9 . . 128.88(10) ?
N1 C8 C13 . . 110.60(9) ?
C9 C8 C13 . . 120.52(10) ?
C10 C9 C8 . . 117.80(10) ?
C10 C9 H9A . . 121.1 ?
C8 C9 H9A . . 121.1 ?
C9 C10 C11 . . 121.19(10) ?
C9 C10 C14 . . 120.64(10) ?
C11 C10 C14 . . 118.17(10) ?
C12 C11 C10 . . 121.83(10) ?
C12 C11 H11A . . 119.1 ?
C10 C11 H11A . . 119.1 ?
C11 C12 C13 . . 116.72(10) ?
C11 C12 H12A . . 121.6 ?
C13 C12 H12A . . 121.6 ?
N2 C13 C12 . . 132.68(10) ?
N2 C13 C8 . . 105.39(9) ?
C12 C13 C8 . . 121.93(10) ?
O2 C14 O1 . . 123.27(11) ?
O2 C14 C10 . . 124.96(11) ?
O1 C14 C10 . . 111.77(10) ?
O1 C15 C16 . . 106.49(11) ?
O1 C15 H15A . . 110.4 ?
C16 C15 H15A . . 110.4 ?
O1 C15 H15B . . 110.4 ?
C16 C15 H15B . . 110.4 ?
H15A C15 H15B . . 108.6 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N2 C17A C18A . . 109.21(12) ?
N2 C17A C20A . . 112.67(14) ?
C18A C17A C20A . . 113.35(13) ?
N2 C17A H17A . . 107.1 ?
C18A C17A H17A . . 107.1 ?
C20A C17A H17A . . 107.1 ?
C19A C18A C17A . . 112.15(12) ?
C19A C18A H18A . . 109.2 ?
C17A C18A H18A . . 109.2 ?
C19A C18A H18B . . 109.2 ?
C17A C18A H18B . . 109.2 ?
H18A C18A H18B . . 107.9 ?
C20B C17B C18B . . 111.2(9) ?
C20B C17B N2 . . 118.1(8) ?
C18B C17B N2 . . 103.4(8) ?
C20B C17B H17B . . 107.9 ?
C18B C17B H17B . . 107.9 ?
N2 C17B H17B . . 107.9 ?
C17B C18B C19B . . 116.0(9) ?
C17B C18B H18C . . 108.3 ?
C19B C18B H18C . . 108.3 ?
C17B C18B H18D . . 108.3 ?
C19B C18B H18D . . 108.3 ?
H18C C18B H18D . . 107.4 ?
C18B C19B H19D . . 109.5 ?
C18B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
C18B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
C17B C20B H20D . . 109.5 ?
C17B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
C17B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 109.5 ?
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
Cl1 C3 . 1.7332(12) ?
O1 C14 . 1.3433(15) ?
O1 C15 . 1.4486(15) ?
O2 C14 . 1.2131(15) ?
N1 C7 . 1.3240(14) ?
N1 C8 . 1.3854(14) ?
N2 C7 . 1.3828(15) ?
N2 C13 . 1.3879(14) ?
N2 C17A . 1.4769(16) ?
N2 C17B . 1.595(9) ?
C1 C2 . 1.3897(17) ?
C1 C6 . 1.3998(16) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.3812(19) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3879(18) ?
C4 C5 . 1.3895(17) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3960(17) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.4725(15) ?
C8 C9 . 1.3956(15) ?
C8 C13 . 1.4112(15) ?
C9 C10 . 1.3881(16) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.4104(16) ?
C10 C14 . 1.4854(15) ?
C11 C12 . 1.3863(16) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.3998(16) ?
C12 H12A . 0.9300 ?
C15 C16 . 1.503(2) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17A C18A . 1.527(2) ?
C17A C20A . 1.530(2) ?
C17A H17A . 0.9800 ?
C18A C19A . 1.518(3) ?
C18A H18A . 0.9700 ?
C18A H18B . 0.9700 ?
C19A H19A . 0.9600 ?
C19A H19B . 0.9600 ?
C19A H19C . 0.9600 ?
C20A H20A . 0.9600 ?
C20A H20B . 0.9600 ?
C20A H20C . 0.9600 ?
C17B C20B . 1.447(15) ?
C17B C18B . 1.508(15) ?
C17B H17B . 0.9800 ?
C18B C19B . 1.576(18) ?
C18B H18C . 0.9700 ?
C18B H18D . 0.9700 ?
C19B H19D . 0.9600 ?
C19B H19E . 0.9600 ?
C19B H19F . 0.9600 ?
C20B H20D . 0.9600 ?
C20B H20E . 0.9600 ?
C20B H20F . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C12 H12A O2 2_645 0.93 2.57 3.4994(16) 174 yes
C16 H16A Cl1 1_465 0.96 2.73 3.4651(17) 134 yes
C19A H19B Cg1 1_555 0.96 2.71 3.3457(18) 124 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.27(18) ?
C1 C2 C3 C4 . . . . 0.76(19) ?
C1 C2 C3 Cl1 . . . . -178.33(9) ?
C2 C3 C4 C5 . . . . -0.55(19) ?
Cl1 C3 C4 C5 . . . . 178.54(10) ?
C3 C4 C5 C6 . . . . -0.15(19) ?
C4 C5 C6 C1 . . . . 0.63(18) ?
C4 C5 C6 C7 . . . . -174.93(11) ?
C2 C1 C6 C5 . . . . -0.42(17) ?
C2 C1 C6 C7 . . . . 175.00(11) ?
C8 N1 C7 N2 . . . . 0.02(14) ?
C8 N1 C7 C6 . . . . 176.15(11) ?
C13 N2 C7 N1 . . . . -0.09(14) ?
C17A N2 C7 N1 . . . . -163.48(13) ?
C17B N2 C7 N1 . . . . -141.6(4) ?
C13 N2 C7 C6 . . . . -176.15(11) ?
C17A N2 C7 C6 . . . . 20.5(2) ?
C17B N2 C7 C6 . . . . 42.4(5) ?
C5 C6 C7 N1 . . . . 38.83(17) ?
C1 C6 C7 N1 . . . . -136.61(12) ?
C5 C6 C7 N2 . . . . -145.43(12) ?
C1 C6 C7 N2 . . . . 39.13(17) ?
C7 N1 C8 C9 . . . . -179.25(12) ?
C7 N1 C8 C13 . . . . 0.06(13) ?
N1 C8 C9 C10 . . . . -179.71(11) ?
C13 C8 C9 C10 . . . . 1.04(17) ?
C8 C9 C10 C11 . . . . -0.44(17) ?
C8 C9 C10 C14 . . . . 178.73(10) ?
C9 C10 C11 C12 . . . . -0.32(18) ?
C14 C10 C11 C12 . . . . -179.51(11) ?
C10 C11 C12 C13 . . . . 0.44(18) ?
C7 N2 C13 C12 . . . . -179.65(13) ?
C17A N2 C13 C12 . . . . -16.1(2) ?
C17B N2 C13 C12 . . . . -41.3(5) ?
C7 N2 C13 C8 . . . . 0.12(13) ?
C17A N2 C13 C8 . . . . 163.64(13) ?
C17B N2 C13 C8 . . . . 138.5(5) ?
C11 C12 C13 N2 . . . . 179.91(13) ?
C11 C12 C13 C8 . . . . 0.17(18) ?
N1 C8 C13 N2 . . . . -0.11(13) ?
C9 C8 C13 N2 . . . . 179.26(10) ?
N1 C8 C13 C12 . . . . 179.69(11) ?
C9 C8 C13 C12 . . . . -0.94(18) ?
C15 O1 C14 O2 . . . . 0.54(19) ?
C15 O1 C14 C10 . . . . 179.96(11) ?
C9 C10 C14 O2 . . . . -176.84(12) ?
C11 C10 C14 O2 . . . . 2.36(19) ?
C9 C10 C14 O1 . . . . 3.75(16) ?
C11 C10 C14 O1 . . . . -177.05(11) ?
C14 O1 C15 C16 . . . . -168.74(13) ?
C7 N2 C17A C18A . . . . 108.23(14) ?
C13 N2 C17A C18A . . . . -52.01(18) ?
C17B N2 C17A C18A . . . . 38.7(9) ?
C7 N2 C17A C20A . . . . -124.87(14) ?
C13 N2 C17A C20A . . . . 74.90(18) ?
C17B N2 C17A C20A . . . . 165.6(10) ?
N2 C17A C18A C19A . . . . -50.27(16) ?
C20A C17A C18A C19A . . . . -176.79(13) ?
C7 N2 C17B C20B . . . . 92.8(8) ?
C13 N2 C17B C20B . . . . -41.5(10) ?
C17A N2 C17B C20B . . . . -145.1(15) ?
C7 N2 C17B C18B . . . . -144.0(5) ?
C13 N2 C17B C18B . . . . 81.8(7) ?
C17A N2 C17B C18B . . . . -21.9(7) ?
C20B C17B C18B C19B . . . . -178.0(9) ?
N2 C17B C18B C19B . . . . 54.3(10) ?
