#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:26:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029074.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_4029074
loop_
_publ_author_name
'Hao, Qingshan'
'Yu, Shuai'
'Li, Shayu'
'Chen, Jinping'
'Zeng, Yi'
'Yu, Tianjun'
'Yang, Guoqiang'
'Li, Yi'
_publ_section_title
;
 Locked planarity: a strategy for tailoring ladder-type π-conjugated
 anilido-pyridine boron difluorides.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              459
_journal_page_last               464
_journal_paper_doi               10.1021/jo402583y
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C44 H50 N4'
_chemical_formula_weight         634.88
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           22
_symmetry_space_group_name_Hall  'F 2 2'
_symmetry_space_group_name_H-M   'F 2 2 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   16.821(3)
_cell_length_b                   27.947(6)
_cell_length_c                   36.187(7)
_cell_measurement_temperature    173(2)
_cell_volume                     17011(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_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  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12239
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.13
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.9775
_exptl_crystal_density_diffrn    0.992
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5472
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         6923
_refine_ls_number_restraints     624
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1054
_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)+(0.1215P)²+14.1014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2139
_refine_ls_wR_factor_ref         0.2349
_reflns_number_gt                5028
_reflns_number_total             6923
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402583y_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        17012(6)
_cod_database_code               4029074
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x, -y, -z'
'-x, y, -z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x, -y+1/2, -z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
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
N1 N 0.2406(2) 0.20709(12) 0.15349(8) 0.0434(9) Uani 1 1 d U
N2 N 0.2320(2) 0.11063(13) 0.15577(9) 0.0413(8) Uani 1 1 d U
H2 H 0.2404 0.1337 0.1718 0.050 Uiso 1 1 calc R
N3 N 0.5112(2) 0.95765(12) 0.40327(9) 0.0472(9) Uani 1 1 d U
N4 N 0.5175(2) 0.86175(13) 0.40510(9) 0.0415(8) Uani 1 1 d U
H4 H 0.5125 0.8838 0.4223 0.050 Uiso 1 1 calc R
C1 C 0.2500 0.2500 0.16889(13) 0.0343(12) Uani 1 2 d SU
H1 H 0.2500 0.2500 0.1951 0.041 Uiso 1 2 calc SR
C2 C 0.2371(2) 0.20650(13) 0.11508(9) 0.0322(8) Uani 1 1 d U
C3 C 0.2500 0.2500 0.09592(13) 0.0306(11) Uani 1 2 d SU
H3 H 0.2500 0.2500 0.0697 0.037 Uiso 1 2 calc SR
C4 C 0.2250(2) 0.16091(13) 0.09700(10) 0.0339(8) Uani 1 1 d U
C5 C 0.2137(2) 0.15733(14) 0.05970(9) 0.0319(8) Uani 1 1 d U
H5 H 0.2125 0.1857 0.0453 0.038 Uiso 1 1 calc R
C6 C 0.2037(2) 0.11257(14) 0.04175(10) 0.0328(8) Uani 1 1 d U
C7 C 0.2041(2) 0.07145(14) 0.06258(10) 0.0368(9) Uani 1 1 d U
H7 H 0.1990 0.0413 0.0507 0.044 Uiso 1 1 calc R
C8 C 0.2118(2) 0.07341(13) 0.10036(10) 0.0340(8) Uani 1 1 d U
C9 C 0.2213(2) 0.11647(13) 0.11737(9) 0.0287(8) Uani 1 1 d U
C10 C 0.1946(3) 0.10909(16) -0.00059(13) 0.0480(10) Uani 1 1 d U
C11 C 0.1109(3) 0.0862(2) -0.00866(14) 0.0737(16) Uani 1 1 d U
H11C H 0.0714 0.0997 0.0083 0.111 Uiso 1 1 calc R
H11A H 0.1138 0.0515 -0.0052 0.111 Uiso 1 1 calc R
H11B H 0.0953 0.0932 -0.0342 0.111 Uiso 1 1 calc R
C12 C 0.2024(4) 0.15863(18) -0.01955(12) 0.0681(14) Uani 1 1 d U
H12C H 0.2548 0.1722 -0.0140 0.102 Uiso 1 1 calc R
H12B H 0.1609 0.1801 -0.0103 0.102 Uiso 1 1 calc R
H12A H 0.1966 0.1549 -0.0463 0.102 Uiso 1 1 calc R
C13 C 0.2602(4) 0.0789(2) -0.01638(14) 0.0786(16) Uani 1 1 d U
H13A H 0.2722 0.0526 0.0007 0.118 Uiso 1 1 calc R
H13C H 0.3078 0.0986 -0.0199 0.118 Uiso 1 1 calc R
H13B H 0.2434 0.0658 -0.0402 0.118 Uiso 1 1 calc R
C14 C 0.2188(2) 0.03877(13) 0.12972(9) 0.0326(8) Uani 1 1 d U
C15 C 0.2271(3) 0.06288(13) 0.16366(10) 0.0351(9) Uani 1 1 d U
C16 C 0.2314(3) 0.03753(15) 0.19665(10) 0.0441(10) Uani 1 1 d U
H16 H 0.2326 0.0536 0.2198 0.053 Uiso 1 1 calc R
C17 C 0.2337(3) -0.01014(16) 0.19478(11) 0.0535(12) Uani 1 1 d U
H17 H 0.2416 -0.0271 0.2172 0.064 Uiso 1 1 calc R
C18 C 0.2254(2) -0.03772(14) 0.16186(10) 0.0369(9) Uani 1 1 d U
C19 C 0.2169(2) -0.01323(12) 0.12917(10) 0.0377(9) Uani 1 1 d U
H19 H 0.2099 -0.0300 0.1066 0.045 Uiso 1 1 calc R
C20 C 0.2313(3) -0.09324(16) 0.16437(13) 0.0481(11) Uani 1 1 d U
C21 C 0.1789(3) -0.11385(19) 0.19379(14) 0.0631(13) Uani 1 1 d U
H21C H 0.1970 -0.1028 0.2181 0.095 Uiso 1 1 calc R
H21A H 0.1814 -0.1489 0.1928 0.095 Uiso 1 1 calc R
H21B H 0.1240 -0.1034 0.1897 0.095 Uiso 1 1 calc R
C22 C 0.3160(3) -0.1058(2) 0.17097(17) 0.0713(15) Uani 1 1 d U
H22A H 0.3214 -0.1407 0.1725 0.107 Uiso 1 1 calc R
H22C H 0.3338 -0.0913 0.1942 0.107 Uiso 1 1 calc R
H22B H 0.3486 -0.0937 0.1506 0.107 Uiso 1 1 calc R
C23 C 0.2074(4) -0.11788(17) 0.12800(13) 0.0658(14) Uani 1 1 d U
H23A H 0.2139 -0.1526 0.1305 0.099 Uiso 1 1 calc R
H23C H 0.2414 -0.1063 0.1079 0.099 Uiso 1 1 calc R
H23B H 0.1518 -0.1105 0.1224 0.099 Uiso 1 1 calc R
C24 C 0.5000 1.0000 0.4208(2) 0.076(2) Uani 1 2 d SU
H24 H 0.5000 1.0000 0.4465 0.091 Uiso 1 2 d SR
C25 C 0.5120(3) 0.95845(15) 0.36631(11) 0.0420(10) Uani 1 1 d U
C26 C 0.5000 1.0000 0.34711(18) 0.0459(15) Uani 1 2 d SU
H26 H 0.5000 1.0000 0.3209 0.055 Uiso 1 2 calc SR
C27 C 0.5285(2) 0.91141(14) 0.34839(11) 0.0371(9) Uani 1 1 d U
C28 C 0.5386(3) 0.90627(16) 0.30963(12) 0.0456(10) Uani 1 1 d U
H28 H 0.5410 0.9347 0.2953 0.055 Uiso 1 1 calc R
C29 C 0.5454(3) 0.86296(16) 0.29083(11) 0.0446(10) Uani 1 1 d U
C30 C 0.5459(2) 0.82019(14) 0.31241(10) 0.0401(10) Uani 1 1 d U
H30 H 0.5545 0.7901 0.3008 0.048 Uiso 1 1 calc R
C31 C 0.5336(2) 0.82248(13) 0.35119(10) 0.0333(9) Uani 1 1 d U
C32 C 0.5264(2) 0.87136(14) 0.36837(10) 0.0365(9) Uani 1 1 d U
C33 C 0.5536(3) 0.85805(17) 0.24886(15) 0.0564(11) Uani 1 1 d U
C34 C 0.4799(3) 0.82907(17) 0.23460(12) 0.0617(14) Uani 1 1 d U
H34C H 0.4315 0.8416 0.2461 0.093 Uiso 1 1 calc R
H34A H 0.4863 0.7952 0.2411 0.093 Uiso 1 1 calc R
H34B H 0.4760 0.8323 0.2077 0.093 Uiso 1 1 calc R
C35 C 0.6265(3) 0.8355(2) 0.23801(13) 0.0727(15) Uani 1 1 d U
H35B H 0.6276 0.8026 0.2473 0.109 Uiso 1 1 calc R
H35C H 0.6715 0.8534 0.2483 0.109 Uiso 1 1 calc R
H35A H 0.6303 0.8352 0.2110 0.109 Uiso 1 1 calc R
C36 C 0.5516(4) 0.90759(18) 0.22923(13) 0.0780(17) Uani 1 1 d U
H36C H 0.5920 0.9286 0.2401 0.117 Uiso 1 1 calc R
H36B H 0.4989 0.9220 0.2324 0.117 Uiso 1 1 calc R
H36A H 0.5626 0.9034 0.2028 0.117 Uiso 1 1 calc R
C37 C 0.5172(3) 0.81156(15) 0.41196(11) 0.0412(10) Uani 1 1 d U
C38 C 0.5320(2) 0.78564(13) 0.37900(10) 0.0346(8) Uani 1 1 d U
C39 C 0.5349(2) 0.73809(13) 0.38043(10) 0.0368(9) Uani 1 1 d U
H39 H 0.5445 0.7210 0.3582 0.044 Uiso 1 1 calc R
C40 C 0.5243(3) 0.71146(15) 0.41400(11) 0.0437(10) Uani 1 1 d U
C41 C 0.5119(3) 0.73762(16) 0.44580(11) 0.0532(12) Uani 1 1 d U
H41 H 0.5080 0.7211 0.4687 0.064 Uiso 1 1 calc R
C42 C 0.5048(3) 0.78884(17) 0.44579(12) 0.0528(11) Uani 1 1 d U
H42 H 0.4923 0.8062 0.4676 0.063 Uiso 1 1 calc R
C43 C 0.5188(3) 0.65790(16) 0.41383(12) 0.0449(10) Uani 1 1 d U
C44 C 0.4313(3) 0.64287(17) 0.42473(13) 0.0486(11) Uani 1 1 d U
H44C H 0.4207 0.6523 0.4504 0.073 Uiso 1 1 calc R
H44A H 0.4255 0.6081 0.4223 0.073 Uiso 1 1 calc R
H44B H 0.3934 0.6589 0.4083 0.073 Uiso 1 1 calc R
C45 C 0.5421(3) 0.63557(16) 0.37715(11) 0.0537(12) Uani 1 1 d U
H45A H 0.5479 0.6009 0.3802 0.080 Uiso 1 1 calc R
H45C H 0.5926 0.6492 0.3688 0.080 Uiso 1 1 calc R
H45B H 0.5007 0.6421 0.3588 0.080 Uiso 1 1 calc R
C46 C 0.5766(3) 0.6385(2) 0.44556(13) 0.0590(13) Uani 1 1 d U
H46C H 0.5569 0.6490 0.4697 0.089 Uiso 1 1 calc R
H46B H 0.6303 0.6510 0.4416 0.089 Uiso 1 1 calc R
H46A H 0.5779 0.6034 0.4448 0.089 Uiso 1 1 calc R
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'
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
C1 N1 C2 115.7(3) . .
C15 N2 C9 108.1(3) . .
C15 N2 H2 125.9 . .
C9 N2 H2 125.9 . .
C25 N3 C24 117.0(5) . .
C32 N4 C37 111.3(4) . .
C32 N4 H4 124.3 . .
C37 N4 H4 124.3 . .
N1 C1 N1 130.5(4) 14 .
N1 C1 H1 114.7 14 .
N1 C1 H1 114.7 . .
N1 C2 C3 118.2(4) . .
N1 C2 C4 117.9(3) . .
C3 C2 C4 123.8(3) . .
C2 C3 C2 121.4(4) . 14
C2 C3 H3 119.3 . .
C2 C3 H3 119.3 14 .
C5 C4 C9 115.8(3) . .
C5 C4 C2 122.1(4) . .
C9 C4 C2 122.1(3) . .
C4 C5 C6 122.2(4) . .
C4 C5 H5 118.9 . .
C6 C5 H5 118.9 . .
C7 C6 C5 119.0(3) . .
C7 C6 C10 119.5(3) . .
C5 C6 C10 121.5(3) . .
C6 C7 C8 120.8(4) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C9 C8 C7 119.7(3) . .
C9 C8 C14 104.5(3) . .
C7 C8 C14 135.5(4) . .
C8 C9 N2 111.0(3) . .
C8 C9 C4 122.3(3) . .
N2 C9 C4 126.6(3) . .
C13 C10 C6 109.9(4) . .
C13 C10 C12 105.7(4) . .
C6 C10 C12 112.0(4) . .
C13 C10 C11 111.0(4) . .
C6 C10 C11 107.4(4) . .
C12 C10 C11 110.9(4) . .
C10 C11 H11C 109.5 . .
C10 C11 H11A 109.5 . .
H11C C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11C C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C12 H12C 109.5 . .
C10 C12 H12B 109.5 . .
H12C C12 H12B 109.5 . .
C10 C12 H12A 109.5 . .
H12C C12 H12A 109.5 . .
H12B C12 H12A 109.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
H13C C13 H13B 109.5 . .
C15 C14 C8 109.2(3) . .
C15 C14 C19 119.5(3) . .
C8 C14 C19 131.2(3) . .
N2 C15 C16 132.4(4) . .
N2 C15 C14 106.9(3) . .
C16 C15 C14 120.7(3) . .
C17 C16 C15 117.8(4) . .
C17 C16 H16 121.1 . .
C15 C16 H16 121.1 . .
C16 C17 C18 125.4(4) . .
C16 C17 H17 117.3 . .
C18 C17 H17 117.3 . .
C19 C18 C17 117.4(4) . .
C19 C18 C20 123.6(3) . .
C17 C18 C20 118.9(3) . .
C18 C19 C14 118.9(3) . .
C18 C19 H19 120.5 . .
C14 C19 H19 120.5 . .
C22 C20 C21 111.0(4) . .
C22 C20 C23 106.4(5) . .
C21 C20 C23 106.4(4) . .
C22 C20 C18 107.8(4) . .
C21 C20 C18 112.8(4) . .
C23 C20 C18 112.3(4) . .
C20 C21 H21C 109.5 . .
C20 C21 H21A 109.5 . .
H21C C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21C C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C22 H22A 109.5 . .
C20 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
C20 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
H22C C22 H22B 109.5 . .
C20 C23 H23A 109.5 . .
C20 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
C20 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
H23C C23 H23B 109.5 . .
N3 C24 N3 124.3(7) 2_675 .
N3 C24 H24 117.8 2_675 .
N3 C24 H24 117.8 . .
N3 C25 C26 121.4(4) . .
N3 C25 C27 114.9(4) . .
C26 C25 C27 123.7(4) . .
C25 C26 C25 118.9(5) 2_675 .
C25 C26 H26 120.5 2_675 .
C25 C26 H26 120.5 . .
C32 C27 C28 117.0(4) . .
C32 C27 C25 120.0(4) . .
C28 C27 C25 122.7(4) . .
C29 C28 C27 125.4(4) . .
C29 C28 H28 117.3 . .
C27 C28 H28 117.3 . .
C28 C29 C30 117.4(3) . .
C28 C29 C33 124.7(4) . .
C30 C29 C33 117.8(4) . .
C31 C30 C29 120.1(4) . .
C31 C30 H30 119.9 . .
C29 C30 H30 119.9 . .
C30 C31 C38 131.4(4) . .
C30 C31 C32 117.4(3) . .
C38 C31 C32 111.0(3) . .
C27 C32 N4 134.1(4) . .
C27 C32 C31 122.4(3) . .
N4 C32 C31 103.4(3) . .
C35 C33 C29 112.8(5) . .
C35 C33 C36 106.5(5) . .
C29 C33 C36 111.8(4) . .
C35 C33 C34 111.0(4) . .
C29 C33 C34 107.6(4) . .
C36 C33 C34 107.0(5) . .
C33 C34 H34C 109.5 . .
C33 C34 H34A 109.5 . .
H34C C34 H34A 109.5 . .
C33 C34 H34B 109.5 . .
H34C C34 H34B 109.5 . .
H34A C34 H34B 109.5 . .
C33 C35 H35B 109.5 . .
C33 C35 H35C 109.5 . .
H35B C35 H35C 109.5 . .
C33 C35 H35A 109.5 . .
H35B C35 H35A 109.5 . .
H35C C35 H35A 109.5 . .
C33 C36 H36C 109.5 . .
C33 C36 H36B 109.5 . .
H36C C36 H36B 109.5 . .
C33 C36 H36A 109.5 . .
H36C C36 H36A 109.5 . .
H36B C36 H36A 109.5 . .
C42 C37 C38 122.2(4) . .
C42 C37 N4 127.0(4) . .
C38 C37 N4 110.8(3) . .
C39 C38 C37 118.9(4) . .
C39 C38 C31 137.8(4) . .
C37 C38 C31 103.1(3) . .
C38 C39 C40 123.1(4) . .
C38 C39 H39 118.5 . .
C40 C39 H39 118.5 . .
C41 C40 C39 116.7(4) . .
C41 C40 C43 121.5(4) . .
C39 C40 C43 121.4(4) . .
C40 C41 C42 122.7(4) . .
C40 C41 H41 118.6 . .
C42 C41 H41 118.6 . .
C37 C42 C41 116.2(4) . .
C37 C42 H42 121.9 . .
C41 C42 H42 121.9 . .
C40 C43 C45 113.5(4) . .
C40 C43 C44 108.8(4) . .
C45 C43 C44 110.4(4) . .
C40 C43 C46 107.4(4) . .
C45 C43 C46 109.3(4) . .
C44 C43 C46 107.2(3) . .
C43 C44 H44C 109.5 . .
C43 C44 H44A 109.5 . .
H44C C44 H44A 109.5 . .
C43 C44 H44B 109.5 . .
H44C C44 H44B 109.5 . .
H44A C44 H44B 109.5 . .
C43 C45 H45A 109.5 . .
C43 C45 H45C 109.5 . .
H45A C45 H45C 109.5 . .
C43 C45 H45B 109.5 . .
H45A C45 H45B 109.5 . .
H45C C45 H45B 109.5 . .
C43 C46 H46C 109.5 . .
C43 C46 H46B 109.5 . .
H46C C46 H46B 109.5 . .
C43 C46 H46A 109.5 . .
H46C C46 H46A 109.5 . .
H46B C46 H46A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.332(4) .
N1 C2 1.391(4) .
N2 C15 1.367(5) .
N2 C9 1.411(5) .
N2 H2 0.8800 .
N3 C25 1.337(5) .
N3 C24 1.355(5) .
N4 C32 1.364(5) .
N4 C37 1.425(5) .
N4 H4 0.8800 .
C1 N1 1.332(4) 14
C1 H1 0.9500 .
C2 C3 1.416(4) .
C2 C4 1.447(5) .
C3 C2 1.416(4) 14
C3 H3 0.9500 .
C4 C5 1.367(5) .
C4 C9 1.446(5) .
C5 C6 1.419(5) .
C5 H5 0.9500 .
C6 C7 1.374(5) .
C6 C10 1.543(6) .
C7 C8 1.374(5) .
C7 H7 0.9500 .
C8 C9 1.361(5) .
C8 C14 1.442(5) .
C10 C13 1.502(8) .
C10 C12 1.551(6) .
C10 C11 1.574(7) .
C11 H11C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C12 H12C 0.9800 .
C12 H12B 0.9800 .
C12 H12A 0.9800 .
C13 H13A 0.9800 .
C13 H13C 0.9800 .
C13 H13B 0.9800 .
C14 C15 1.408(5) .
C14 C19 1.454(5) .
C15 C16 1.390(5) .
C16 C17 1.334(6) .
C16 H16 0.9500 .
C17 C18 1.426(6) .
C17 H17 0.9500 .
C18 C19 1.374(5) .
C18 C20 1.557(6) .
C19 H19 0.9500 .
C20 C22 1.486(7) .
C20 C21 1.498(7) .
C20 C23 1.539(7) .
C21 H21C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C22 H22A 0.9800 .
C22 H22C 0.9800 .
C22 H22B 0.9800 .
C23 H23A 0.9800 .
C23 H23C 0.9800 .
C23 H23B 0.9800 .
C24 N3 1.355(5) 2_675
C24 H24 0.9304 .
C25 C26 1.368(5) .
C25 C27 1.492(5) .
C26 C25 1.368(5) 2_675
C26 H26 0.9500 .
C27 C32 1.333(5) .
C27 C28 1.420(6) .
C28 C29 1.393(6) .
C28 H28 0.9500 .
C29 C30 1.428(6) .
C29 C33 1.531(6) .
C30 C31 1.420(5) .
C30 H30 0.9500 .
C31 C38 1.440(5) .
C31 C32 1.506(5) .
C33 C35 1.434(7) .
C33 C36 1.557(6) .
C33 C34 1.567(7) .
C34 H34C 0.9800 .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C35 H35B 0.9800 .
C35 H35C 0.9800 .
C35 H35A 0.9800 .
C36 H36C 0.9800 .
C36 H36B 0.9800 .
C36 H36A 0.9800 .
C37 C42 1.395(6) .
C37 C38 1.418(6) .
C38 C39 1.331(5) .
C39 C40 1.436(5) .
C39 H39 0.9500 .
C40 C41 1.379(6) .
C40 C43 1.500(6) .
C41 C42 1.437(6) .
C41 H41 0.9500 .
C42 H42 0.9500 .
C43 C45 1.518(6) .
C43 C44 1.581(6) .
C43 C46 1.599(6) .
C44 H44C 0.9800 .
C44 H44A 0.9800 .
C44 H44B 0.9800 .
C45 H45A 0.9800 .
C45 H45C 0.9800 .
C45 H45B 0.9800 .
C46 H46C 0.9800 .
C46 H46B 0.9800 .
C46 H46A 0.9800 .
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_4
C2 N1 C1 N1 -2.6(3) 14
C1 N1 C2 C3 5.0(5) .
C1 N1 C2 C4 -178.5(3) .
N1 C2 C3 C2 -2.6(3) 14
C4 C2 C3 C2 -178.9(4) 14
N1 C2 C4 C5 174.1(4) .
C3 C2 C4 C5 -9.6(6) .
N1 C2 C4 C9 -3.7(5) .
C3 C2 C4 C9 172.5(3) .
C9 C4 C5 C6 -3.6(6) .
C2 C4 C5 C6 178.4(3) .
C4 C5 C6 C7 1.0(6) .
C4 C5 C6 C10 -177.4(4) .
C5 C6 C7 C8 1.8(6) .
C10 C6 C7 C8 -179.7(4) .
C6 C7 C8 C9 -1.8(6) .
C6 C7 C8 C14 -176.0(4) .
C7 C8 C9 N2 -177.1(4) .
C14 C8 C9 N2 -1.3(5) .
C7 C8 C9 C4 -1.0(6) .
C14 C8 C9 C4 174.8(4) .
C15 N2 C9 C8 -1.7(5) .
C15 N2 C9 C4 -177.5(4) .
C5 C4 C9 C8 3.6(6) .
C2 C4 C9 C8 -178.4(4) .
C5 C4 C9 N2 179.0(4) .
C2 C4 C9 N2 -3.0(6) .
C7 C6 C10 C13 -58.2(5) .
C5 C6 C10 C13 120.3(5) .
C7 C6 C10 C12 -175.3(4) .
C5 C6 C10 C12 3.2(6) .
C7 C6 C10 C11 62.7(5) .
C5 C6 C10 C11 -118.8(4) .
C9 C8 C14 C15 3.7(4) .
C7 C8 C14 C15 178.5(5) .
C9 C8 C14 C19 -177.6(4) .
C7 C8 C14 C19 -2.8(8) .
C9 N2 C15 C16 -178.3(5) .
C9 N2 C15 C14 4.0(5) .
C8 C14 C15 N2 -4.8(5) .
C19 C14 C15 N2 176.3(4) .
C8 C14 C15 C16 177.1(4) .
C19 C14 C15 C16 -1.7(6) .
N2 C15 C16 C17 -172.2(5) .
C14 C15 C16 C17 5.2(7) .
C15 C16 C17 C18 -5.6(8) .
C16 C17 C18 C19 2.3(7) .
C16 C17 C18 C20 178.8(5) .
C17 C18 C19 C14 1.5(6) .
C20 C18 C19 C14 -174.8(4) .
C15 C14 C19 C18 -1.7(6) .
C8 C14 C19 C18 179.7(4) .
C19 C18 C20 C22 103.6(5) .
C17 C18 C20 C22 -72.6(6) .
C19 C18 C20 C21 -133.4(5) .
C17 C18 C20 C21 50.3(6) .
C19 C18 C20 C23 -13.2(7) .
C17 C18 C20 C23 170.5(4) .
C25 N3 C24 N3 0.8(3) 2_675
C24 N3 C25 C26 -1.6(6) .
C24 N3 C25 C27 177.2(3) .
N3 C25 C26 C25 0.8(3) 2_675
C27 C25 C26 C25 -177.8(5) 2_675
N3 C25 C27 C32 12.4(6) .
C26 C25 C27 C32 -168.9(4) .
N3 C25 C27 C28 -174.2(4) .
C26 C25 C27 C28 4.5(7) .
C32 C27 C28 C29 1.0(7) .
C25 C27 C28 C29 -172.6(4) .
C27 C28 C29 C30 -3.1(7) .
C27 C28 C29 C33 177.9(4) .
C28 C29 C30 C31 4.8(6) .
C33 C29 C30 C31 -176.1(4) .
C29 C30 C31 C38 -179.3(4) .
C29 C30 C31 C32 -4.5(6) .
C28 C27 C32 N4 -179.6(4) .
C25 C27 C32 N4 -5.9(7) .
C28 C27 C32 C31 -0.6(6) .
C25 C27 C32 C31 173.1(4) .
C37 N4 C32 C27 178.2(4) .
C37 N4 C32 C31 -1.0(5) .
C30 C31 C32 C27 2.4(6) .
C38 C31 C32 C27 178.2(4) .
C30 C31 C32 N4 -178.3(3) .
C38 C31 C32 N4 -2.5(4) .
C28 C29 C33 C35 118.8(5) .
C30 C29 C33 C35 -60.3(6) .
C28 C29 C33 C36 -1.3(7) .
C30 C29 C33 C36 179.7(5) .
C28 C29 C33 C34 -118.4(5) .
C30 C29 C33 C34 62.5(5) .
C32 N4 C37 C42 -176.0(5) .
C32 N4 C37 C38 4.2(5) .
C42 C37 C38 C39 -0.7(7) .
N4 C37 C38 C39 179.1(4) .
C42 C37 C38 C31 174.8(4) .
N4 C37 C38 C31 -5.4(5) .
C30 C31 C38 C39 -6.0(9) .
C32 C31 C38 C39 179.0(5) .
C30 C31 C38 C37 179.8(4) .
C32 C31 C38 C37 4.8(4) .
C37 C38 C39 C40 -0.4(6) .
C31 C38 C39 C40 -173.9(4) .
C38 C39 C40 C41 -1.1(7) .
C38 C39 C40 C43 173.0(4) .
C39 C40 C41 C42 3.9(7) .
C43 C40 C41 C42 -170.3(5) .
C38 C37 C42 C41 3.2(7) .
N4 C37 C42 C41 -176.6(4) .
C40 C41 C42 C37 -4.8(8) .
C41 C40 C43 C45 -174.5(4) .
C39 C40 C43 C45 11.7(6) .
C41 C40 C43 C44 62.2(6) .
C39 C40 C43 C44 -111.6(5) .
C41 C40 C43 C46 -53.5(6) .
C39 C40 C43 C46 132.7(4) .
