#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/58/4025844.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_4025844
loop_
_publ_author_name
'K. R. Justin Thomas'
'Payal Tyagi'
_publ_section_title
;
 Synthesis, Spectra, and Theoretical Investigations of the Triarylamines
 Based on 6H-Indolo[2,3-b]quinoxaline
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8100
_journal_page_last               8111
_journal_paper_doi               10.1021/jo1016663
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C40.75 H31.5 Cl1.5 N4 O0.25'
_chemical_formula_weight         634.37
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.588(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9993(6)
_cell_length_b                   9.6707(3)
_cell_length_c                   21.5381(7)
_cell_measurement_temperature    293(2)
_cell_volume                     3335.8(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29923
_diffrn_reflns_theta_full        24.77
_diffrn_reflns_theta_max         24.77
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.191
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1326
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0018(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         5716
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0855
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1865P)²+2.4336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2710
_refine_ls_wR_factor_ref         0.3063
_reflns_number_gt                3916
_reflns_number_total             5716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1016663_si_002.cif
_cod_data_source_block           p4
_cod_original_cell_volume        3335.85(19)
_cod_original_formula_sum        'C40.75 H31.50 Cl1.50 N4 O0.25'
_cod_database_code               4025844
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6347(2) 0.1075(4) 0.25625(18) 0.0514(9) Uani 1 1 d . . .
C2 C 0.6349(2) 0.0478(4) 0.19723(17) 0.0482(9) Uani 1 1 d . . .
C3 C 0.5631(2) -0.0149(5) 0.1507(2) 0.0597(10) Uani 1 1 d . . .
H3 H 0.5136 -0.0190 0.1601 0.072 Uiso 1 1 calc R . .
C4 C 0.5653(3) -0.0679(5) 0.0937(2) 0.0665(11) Uani 1 1 d . . .
H4 H 0.5170 -0.1072 0.0646 0.080 Uiso 1 1 calc R . .
C5 C 0.6394(3) -0.0658(5) 0.0764(2) 0.0630(11) Uani 1 1 d . . .
C6 C 0.6432(4) -0.1194(6) 0.0174(2) 0.0857(15) Uani 1 1 d . . .
H6 H 0.5955 -0.1575 -0.0130 0.103 Uiso 1 1 calc R . .
C7 C 0.7161(4) -0.1164(6) 0.0036(3) 0.0947(18) Uani 1 1 d . . .
H7 H 0.7172 -0.1519 -0.0362 0.114 Uiso 1 1 calc R . .
C8 C 0.7871(4) -0.0624(6) 0.0474(3) 0.0851(16) Uani 1 1 d . . .
H8 H 0.8360 -0.0620 0.0370 0.102 Uiso 1 1 calc R . .
C9 C 0.7877(3) -0.0076(4) 0.1074(2) 0.0647(12) Uani 1 1 d . . .
C10 C 0.8611(3) 0.0466(5) 0.1556(3) 0.0753(14) Uani 1 1 d . . .
H10 H 0.9114 0.0446 0.1474 0.090 Uiso 1 1 calc R . .
C11 C 0.8591(3) 0.0996(5) 0.2119(3) 0.0717(12) Uani 1 1 d . . .
H11 H 0.9081 0.1340 0.2422 0.086 Uiso 1 1 calc R . .
C12 C 0.7837(2) 0.1052(4) 0.2272(2) 0.0586(10) Uani 1 1 d . . .
C13 C 0.7796(3) 0.1636(5) 0.2853(2) 0.0703(12) Uani 1 1 d . . .
H13 H 0.8274 0.2024 0.3152 0.084 Uiso 1 1 calc R . .
C14 C 0.7072(3) 0.1651(5) 0.2992(2) 0.0646(11) Uani 1 1 d . . .
H14 H 0.7064 0.2054 0.3382 0.078 Uiso 1 1 calc R . .
C15 C 0.7102(2) 0.0483(4) 0.18226(18) 0.0476(9) Uani 1 1 d . . .
C16 C 0.7118(2) -0.0089(4) 0.12184(19) 0.0538(10) Uani 1 1 d . . .
C17 C 0.4883(2) 0.1764(4) 0.23840(17) 0.0524(9) Uani 1 1 d . . .
C18 C 0.4886(3) 0.2751(5) 0.1920(2) 0.0712(12) Uani 1 1 d . . .
H18 H 0.5382 0.2981 0.1852 0.085 Uiso 1 1 calc R . .
C19 C 0.4149(4) 0.3394(6) 0.1558(2) 0.0869(15) Uani 1 1 d . . .
H19 H 0.4154 0.4049 0.1243 0.104 Uiso 1 1 calc R . .
C20 C 0.3417(3) 0.3089(6) 0.1653(3) 0.0903(17) Uani 1 1 d . . .
H20 H 0.2925 0.3525 0.1404 0.108 Uiso 1 1 calc R . .
C21 C 0.3415(3) 0.2125(6) 0.2121(3) 0.0825(15) Uani 1 1 d . . .
H21 H 0.2919 0.1919 0.2195 0.099 Uiso 1 1 calc R . .
C22 C 0.4137(3) 0.1468(5) 0.2480(2) 0.0658(11) Uani 1 1 d . . .
H22 H 0.4126 0.0813 0.2793 0.079 Uiso 1 1 calc R . .
C23 C 0.5723(2) 0.0613(4) 0.33996(18) 0.0520(9) Uani 1 1 d . . .
C24 C 0.5668(2) 0.1528(4) 0.38713(17) 0.0498(9) Uani 1 1 d . . .
H24 H 0.5537 0.2451 0.3767 0.060 Uiso 1 1 calc R . .
C25 C 0.5813(2) 0.1045(4) 0.45047(17) 0.0462(8) Uani 1 1 d . . .
C26 C 0.5839(2) 0.1711(4) 0.51100(16) 0.0440(8) Uani 1 1 d . . .
C27 C 0.5802(2) 0.3253(4) 0.58833(18) 0.0487(9) Uani 1 1 d . . .
C28 C 0.5676(3) 0.4600(4) 0.6068(2) 0.0593(10) Uani 1 1 d . . .
H28 H 0.5508 0.5287 0.5748 0.071 Uiso 1 1 calc R . .
C29 C 0.5796(3) 0.4919(5) 0.6709(2) 0.0676(12) Uani 1 1 d . . .
H29 H 0.5723 0.5823 0.6827 0.081 Uiso 1 1 calc R . .
C30 C 0.6026(3) 0.3896(5) 0.7186(2) 0.0717(13) Uani 1 1 d . . .
H30 H 0.6100 0.4119 0.7621 0.086 Uiso 1 1 calc R . .
C31 C 0.6147(3) 0.2569(5) 0.70278(19) 0.0647(11) Uani 1 1 d . . .
H31 H 0.6303 0.1898 0.7356 0.078 Uiso 1 1 calc R . .
C32 C 0.6037(2) 0.2206(4) 0.63744(18) 0.0503(9) Uani 1 1 d . . .
C33 C 0.6061(2) 0.0655(4) 0.56124(17) 0.0458(8) Uani 1 1 d . . .
C34 C 0.6015(2) -0.0347(4) 0.46632(18) 0.0485(9) Uani 1 1 d . . .
C35 C 0.6066(2) -0.1268(4) 0.4186(2) 0.0570(10) Uani 1 1 d . . .
H35 H 0.6198 -0.2194 0.4286 0.068 Uiso 1 1 calc R . .
C36 C 0.5916(2) -0.0769(4) 0.3560(2) 0.0579(10) Uani 1 1 d . . .
H36 H 0.5945 -0.1373 0.3233 0.069 Uiso 1 1 calc R . .
C37 C 0.6374(2) -0.1874(4) 0.5677(2) 0.0634(11) Uani 1 1 d D . .
H37A H 0.6050 -0.2623 0.5415 0.076 Uiso 1 1 calc R A 1
H37B H 0.6269 -0.1838 0.6092 0.076 Uiso 1 1 calc R A 1
C38 C 0.7307(3) -0.2097(8) 0.5799(5) 0.088(2) Uani 0.673(6) 1 d PD B 1
H38A H 0.7404 -0.2073 0.5380 0.106 Uiso 0.673(6) 1 calc PR B 1
H38B H 0.7620 -0.1343 0.6067 0.106 Uiso 0.673(6) 1 calc PR B 1
C39 C 0.7629(4) -0.3451(8) 0.6140(4) 0.100(2) Uani 0.673(6) 1 d PD B 1
H39A H 0.7312 -0.4213 0.5882 0.120 Uiso 0.673(6) 1 calc PR B 1
H39B H 0.7561 -0.3468 0.6569 0.120 Uiso 0.673(6) 1 calc PR B 1
C40 C 0.8549(4) -0.3612(13) 0.6219(5) 0.104(3) Uani 0.673(6) 1 d PD B 1
H40A H 0.8756 -0.4465 0.6442 0.155 Uiso 0.673(6) 1 calc PR B 1
H40B H 0.8860 -0.2853 0.6472 0.155 Uiso 0.673(6) 1 calc PR B 1
H40C H 0.8612 -0.3620 0.5792 0.155 Uiso 0.673(6) 1 calc PR B 1
C38' C 0.7247(6) -0.221(2) 0.6148(6) 0.088(2) Uani 0.327(6) 1 d PD B 2
H38C H 0.7460 -0.1461 0.6459 0.106 Uiso 0.327(6) 1 calc PR B 2
H38D H 0.7240 -0.3051 0.6392 0.106 Uiso 0.327(6) 1 calc PR B 2
C39' C 0.7780(9) -0.240(2) 0.5710(7) 0.100(2) Uani 0.327(6) 1 d PD B 2
H39C H 0.7734 -0.1581 0.5439 0.120 Uiso 0.327(6) 1 calc PR B 2
H39D H 0.7575 -0.3182 0.5420 0.120 Uiso 0.327(6) 1 calc PR B 2
C40' C 0.8697(9) -0.263(3) 0.6122(11) 0.104(3) Uani 0.327(6) 1 d PD B 2
H40D H 0.9040 -0.2464 0.5855 0.155 Uiso 0.327(6) 1 calc PR B 2
H40E H 0.8772 -0.3573 0.6276 0.155 Uiso 0.327(6) 1 calc PR B 2
H40F H 0.8854 -0.2017 0.6492 0.155 Uiso 0.327(6) 1 calc PR B 2
N1 N 0.56115(19) 0.1059(4) 0.27429(15) 0.0556(8) Uani 1 1 d . . .
N2 N 0.61497(19) -0.0571(3) 0.53290(15) 0.0507(8) Uani 1 1 d . B .
N3 N 0.61656(18) 0.0869(3) 0.62335(14) 0.0511(8) Uani 1 1 d . . .
N4 N 0.56999(19) 0.2990(3) 0.52360(15) 0.0497(8) Uani 1 1 d . . .
O1 O 0.9414(12) 0.019(2) 0.4137(11) 0.142(7) Uani 0.25 1 d P C 1
Cl1 Cl 0.8172(2) 0.0304(3) 0.46445(16) 0.1573(12) Uani 0.75 1 d PD D 2
Cl2 Cl 0.9143(3) -0.1896(5) 0.4411(2) 0.220(2) Uani 0.75 1 d PD D 2
C41 C 0.8226(6) -0.1122(11) 0.4191(6) 0.150(4) Uani 0.75 1 d PD D 2
H41A H 0.7812 -0.1786 0.4222 0.180 Uiso 0.75 1 calc PR D 2
H41B H 0.8076 -0.0850 0.3733 0.180 Uiso 0.75 1 calc PR D 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 120.0(3) . . ?
C14 C1 N1 119.1(3) . . ?
C2 C1 N1 120.8(3) . . ?
C1 C2 C15 118.8(3) . . ?
C1 C2 C3 123.5(3) . . ?
C15 C2 C3 117.7(3) . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 122.0(4) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C16 119.0(4) . . ?
C6 C5 C4 123.1(4) . . ?
C16 C5 C4 117.8(3) . . ?
C7 C6 C5 120.8(5) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 120.9(5) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C16 118.3(5) . . ?
C8 C9 C10 123.1(4) . . ?
C16 C9 C10 118.6(4) . . ?
C11 C10 C9 121.5(4) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 121.6(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C15 118.2(3) . . ?
C13 C12 C11 122.7(4) . . ?
C15 C12 C11 119.1(4) . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C1 121.1(4) . . ?
C13 C14 H14 119.5 . . ?
C1 C14 H14 119.5 . . ?
C12 C15 C2 120.3(3) . . ?
C12 C15 C16 119.6(3) . . ?
C2 C15 C16 120.1(3) . . ?
C5 C16 C15 120.6(3) . . ?
C5 C16 C9 119.8(4) . . ?
C15 C16 C9 119.6(4) . . ?
C22 C17 C18 118.5(4) . . ?
C22 C17 N1 120.2(4) . . ?
C18 C17 N1 121.3(4) . . ?
C19 C18 C17 119.8(5) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 121.3(5) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 119.1(5) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 120.4(5) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 121.0(5) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C24 C23 C36 120.2(4) . . ?
C24 C23 N1 121.2(4) . . ?
C36 C23 N1 118.5(3) . . ?
C23 C24 C25 118.6(4) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C24 C25 C34 120.7(3) . . ?
C24 C25 C26 133.1(3) . . ?
C34 C25 C26 106.1(3) . . ?
N4 C26 C25 131.2(3) . . ?
N4 C26 C33 122.3(3) . . ?
C25 C26 C33 106.5(3) . . ?
N4 C27 C28 118.8(3) . . ?
N4 C27 C32 122.2(3) . . ?
C28 C27 C32 119.0(3) . . ?
C29 C28 C27 120.9(4) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 119.9(4) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 121.2(4) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 120.5(4) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
N3 C32 C31 119.0(4) . . ?
N3 C32 C27 122.5(3) . . ?
C31 C32 C27 118.6(4) . . ?
N3 C33 N2 126.8(3) . . ?
N3 C33 C26 124.6(3) . . ?
N2 C33 C26 108.6(3) . . ?
C35 C34 N2 129.4(3) . . ?
C35 C34 C25 120.5(3) . . ?
N2 C34 C25 110.0(3) . . ?
C36 C35 C34 117.7(4) . . ?
C36 C35 H35 121.1 . . ?
C34 C35 H35 121.1 . . ?
C35 C36 C23 122.2(4) . . ?
C35 C36 H36 118.9 . . ?
C23 C36 H36 118.9 . . ?
N2 C37 C38' 124.0(9) . . ?
N2 C37 C38 106.8(4) . . ?
C38' C37 C38 30.3(5) . . ?
N2 C37 H37A 110.4 . . ?
C38' C37 H37A 117.7 . . ?
C38 C37 H37A 110.4 . . ?
N2 C37 H37B 110.4 . . ?
C38' C37 H37B 80.4 . . ?
C38 C37 H37B 110.4 . . ?
H37A C37 H37B 108.6 . . ?
C39 C38 C37 113.0(5) . . ?
C39 C38 H38A 109.0 . . ?
C37 C38 H38A 109.0 . . ?
C39 C38 H38B 109.0 . . ?
C37 C38 H38B 109.0 . . ?
H38A C38 H38B 107.8 . . ?
C38 C39 C40 109.5(6) . . ?
C38 C39 H39A 109.8 . . ?
C40 C39 H39A 109.8 . . ?
C38 C39 H39B 109.8 . . ?
C40 C39 H39B 109.8 . . ?
H39A C39 H39B 108.2 . . ?
C39' C38' C37 105.1(8) . . ?
C39' C38' H38C 110.7 . . ?
C37 C38' H38C 110.7 . . ?
C39' C38' H38D 110.7 . . ?
C37 C38' H38D 110.7 . . ?
H38C C38' H38D 108.8 . . ?
C38' C39' C40' 111.2(12) . . ?
C38' C39' H39C 109.4 . . ?
C40' C39' H39C 109.4 . . ?
C38' C39' H39D 109.4 . . ?
C40' C39' H39D 109.4 . . ?
H39C C39' H39D 108.0 . . ?
C39' C40' H40D 109.5 . . ?
C39' C40' H40E 109.5 . . ?
H40D C40' H40E 109.5 . . ?
C39' C40' H40F 109.5 . . ?
H40D C40' H40F 109.5 . . ?
H40E C40' H40F 109.5 . . ?
C17 N1 C1 122.5(3) . . ?
C17 N1 C23 119.6(3) . . ?
C1 N1 C23 115.8(3) . . ?
C33 N2 C34 108.7(3) . . ?
C33 N2 C37 124.9(3) . . ?
C34 N2 C37 126.3(3) . . ?
C33 N3 C32 113.7(3) . . ?
C26 N4 C27 114.7(3) . . ?
Cl2 C41 Cl1 115.4(7) . . ?
Cl2 C41 H41A 108.4 . . ?
Cl1 C41 H41A 108.4 . . ?
Cl2 C41 H41B 108.4 . . ?
Cl1 C41 H41B 108.4 . . ?
H41A C41 H41B 107.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C14 1.387(6) . ?
C1 C2 1.397(5) . ?
C1 N1 1.428(4) . ?
C2 C15 1.420(5) . ?
C2 C3 1.429(5) . ?
C3 C4 1.342(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.430(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(6) . ?
C5 C16 1.403(6) . ?
C6 C7 1.369(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.362(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(7) . ?
C8 H8 0.9300 . ?
C9 C16 1.424(5) . ?
C9 C10 1.429(7) . ?
C10 C11 1.327(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.426(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(6) . ?
C12 C15 1.411(5) . ?
C13 C14 1.360(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.423(5) . ?
C17 C22 1.382(6) . ?
C17 C18 1.383(6) . ?
C17 N1 1.398(5) . ?
C18 C19 1.382(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.358(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.374(5) . ?
C23 C36 1.391(6) . ?
C23 N1 1.429(5) . ?
C24 C25 1.384(5) . ?
C24 H24 0.9300 . ?
C25 C34 1.403(5) . ?
C25 C26 1.441(5) . ?
C26 N4 1.305(5) . ?
C26 C33 1.443(5) . ?
C27 N4 1.370(5) . ?
C27 C28 1.400(5) . ?
C27 C32 1.421(5) . ?
C28 C29 1.363(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.385(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.360(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.401(5) . ?
C31 H31 0.9300 . ?
C32 N3 1.362(5) . ?
C33 N3 1.306(4) . ?
C33 N2 1.365(5) . ?
C34 C35 1.385(5) . ?
C34 N2 1.391(5) . ?
C35 C36 1.373(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 N2 1.450(5) . ?
C37 C38' 1.525(5) . ?
C37 C38 1.533(5) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.512(5) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.524(5) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C38' C39' 1.523(5) . ?
C38' H38C 0.9700 . ?
C38' H38D 0.9700 . ?
C39' C40' 1.530(5) . ?
C39' H39C 0.9700 . ?
C39' H39D 0.9700 . ?
C40' H40D 0.9600 . ?
C40' H40E 0.9600 . ?
C40' H40F 0.9600 . ?
Cl1 C41 1.710(8) . ?
Cl2 C41 1.650(8) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C15 -0.4(6) . . . . ?
N1 C1 C2 C15 -178.2(3) . . . . ?
C14 C1 C2 C3 179.3(4) . . . . ?
N1 C1 C2 C3 1.6(6) . . . . ?
C1 C2 C3 C4 178.2(4) . . . . ?
C15 C2 C3 C4 -2.0(6) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 -179.6(5) . . . . ?
C3 C4 C5 C16 1.5(7) . . . . ?
C16 C5 C6 C7 -0.1(8) . . . . ?
C4 C5 C6 C7 -179.1(5) . . . . ?
C5 C6 C7 C8 0.6(9) . . . . ?
C6 C7 C8 C9 -0.3(8) . . . . ?
C7 C8 C9 C16 -0.4(7) . . . . ?
C7 C8 C9 C10 178.2(5) . . . . ?
C8 C9 C10 C11 179.1(4) . . . . ?
C16 C9 C10 C11 -2.4(6) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?
C10 C11 C12 C13 -178.3(4) . . . . ?
C10 C11 C12 C15 2.3(7) . . . . ?
C15 C12 C13 C14 0.7(7) . . . . ?
C11 C12 C13 C14 -178.7(4) . . . . ?
C12 C13 C14 C1 0.5(7) . . . . ?
C2 C1 C14 C13 -0.6(7) . . . . ?
N1 C1 C14 C13 177.2(4) . . . . ?
C13 C12 C15 C2 -1.7(6) . . . . ?
C11 C12 C15 C2 177.7(4) . . . . ?
C13 C12 C15 C16 178.4(4) . . . . ?
C11 C12 C15 C16 -2.2(6) . . . . ?
C1 C2 C15 C12 1.6(5) . . . . ?
C3 C2 C15 C12 -178.2(4) . . . . ?
C1 C2 C15 C16 -178.5(3) . . . . ?
C3 C2 C15 C16 1.7(5) . . . . ?
C6 C5 C16 C15 179.2(4) . . . . ?
C4 C5 C16 C15 -1.8(6) . . . . ?
C6 C5 C16 C9 -0.5(6) . . . . ?
C4 C5 C16 C9 178.5(4) . . . . ?
C12 C15 C16 C5 -179.9(4) . . . . ?
C2 C15 C16 C5 0.2(6) . . . . ?
C12 C15 C16 C9 -0.2(5) . . . . ?
C2 C15 C16 C9 180.0(3) . . . . ?
C8 C9 C16 C5 0.8(6) . . . . ?
C10 C9 C16 C5 -177.8(4) . . . . ?
C8 C9 C16 C15 -179.0(4) . . . . ?
C10 C9 C16 C15 2.4(6) . . . . ?
C22 C17 C18 C19 -1.2(6) . . . . ?
N1 C17 C18 C19 177.8(4) . . . . ?
C17 C18 C19 C20 0.8(8) . . . . ?
C18 C19 C20 C21 0.3(8) . . . . ?
C19 C20 C21 C22 -1.0(8) . . . . ?
C20 C21 C22 C17 0.5(7) . . . . ?
C18 C17 C22 C21 0.6(6) . . . . ?
N1 C17 C22 C21 -178.4(4) . . . . ?
C36 C23 C24 C25 0.3(5) . . . . ?
N1 C23 C24 C25 -177.7(3) . . . . ?
C23 C24 C25 C34 0.4(5) . . . . ?
C23 C24 C25 C26 177.2(4) . . . . ?
C24 C25 C26 N4 3.1(7) . . . . ?
C34 C25 C26 N4 -179.8(4) . . . . ?
C24 C25 C26 C33 -177.2(4) . . . . ?
C34 C25 C26 C33 -0.1(4) . . . . ?
N4 C27 C28 C29 -177.9(4) . . . . ?
C32 C27 C28 C29 1.6(6) . . . . ?
C27 C28 C29 C30 -1.6(6) . . . . ?
C28 C29 C30 C31 0.8(7) . . . . ?
C29 C30 C31 C32 -0.2(7) . . . . ?
C30 C31 C32 N3 179.8(4) . . . . ?
C30 C31 C32 C27 0.3(6) . . . . ?
N4 C27 C32 N3 -0.9(5) . . . . ?
C28 C27 C32 N3 179.5(3) . . . . ?
N4 C27 C32 C31 178.6(3) . . . . ?
C28 C27 C32 C31 -1.0(5) . . . . ?
N4 C26 C33 N3 -1.9(5) . . . . ?
C25 C26 C33 N3 178.3(3) . . . . ?
N4 C26 C33 N2 178.8(3) . . . . ?
C25 C26 C33 N2 -0.9(4) . . . . ?
C24 C25 C34 C35 -0.7(5) . . . . ?
C26 C25 C34 C35 -178.2(3) . . . . ?
C24 C25 C34 N2 178.6(3) . . . . ?
C26 C25 C34 N2 1.0(4) . . . . ?
N2 C34 C35 C36 -178.8(4) . . . . ?
C25 C34 C35 C36 0.3(5) . . . . ?
C34 C35 C36 C23 0.3(6) . . . . ?
C24 C23 C36 C35 -0.6(6) . . . . ?
N1 C23 C36 C35 177.3(4) . . . . ?
N2 C37 C38 C39 -177.9(7) . . . . ?
C38' C37 C38 C39 52.3(18) . . . . ?
C37 C38 C39 C40 177.9(8) . . . . ?
N2 C37 C38' C39' -71.4(16) . . . . ?
C38 C37 C38' C39' -8.9(12) . . . . ?
C37 C38' C39' C40' 175.6(17) . . . . ?
C22 C17 N1 C1 164.9(4) . . . . ?
C18 C17 N1 C1 -14.0(6) . . . . ?
C22 C17 N1 C23 -32.3(5) . . . . ?
C18 C17 N1 C23 148.8(4) . . . . ?
C14 C1 N1 C17 117.2(4) . . . . ?
C2 C1 N1 C17 -65.1(5) . . . . ?
C14 C1 N1 C23 -46.2(5) . . . . ?
C2 C1 N1 C23 131.5(4) . . . . ?
C24 C23 N1 C17 -54.9(5) . . . . ?
C36 C23 N1 C17 127.2(4) . . . . ?
C24 C23 N1 C1 109.0(4) . . . . ?
C36 C23 N1 C1 -68.9(5) . . . . ?
N3 C33 N2 C34 -177.7(3) . . . . ?
C26 C33 N2 C34 1.5(4) . . . . ?
N3 C33 N2 C37 0.5(6) . . . . ?
C26 C33 N2 C37 179.7(3) . . . . ?
C35 C34 N2 C33 177.6(4) . . . . ?
C25 C34 N2 C33 -1.6(4) . . . . ?
C35 C34 N2 C37 -0.6(6) . . . . ?
C25 C34 N2 C37 -179.7(3) . . . . ?
C38' C37 N2 C33 -72.6(8) . . . . ?
C38 C37 N2 C33 -100.5(5) . . . . ?
C38' C37 N2 C34 105.2(8) . . . . ?
C38 C37 N2 C34 77.3(6) . . . . ?
N2 C33 N3 C32 179.7(3) . . . . ?
C26 C33 N3 C32 0.6(5) . . . . ?
C31 C32 N3 C33 -178.8(3) . . . . ?
C27 C32 N3 C33 0.7(5) . . . . ?
C25 C26 N4 C27 -178.7(3) . . . . ?
C33 C26 N4 C27 1.6(5) . . . . ?
C28 C27 N4 C26 179.3(3) . . . . ?
C32 C27 N4 C26 -0.3(5) . . . . ?
