#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/20/2222061.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_2222061
loop_
_publ_author_name
'Zhou, Jian-Cheng'
'Li, Nai-Xu'
'Zhang, Chuan-Ming'
'Zhang, Zheng-Yun'
_publ_section_title
(E)-2-[(3,5-Di-tert-butyl-2-hydroxybenzylidene)amino]benzonitrile
_journal_coeditor_code           HK2692
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1416
_journal_paper_doi               10.1107/S1600536809019527
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H26 N2 O'
_chemical_formula_moiety         'C22 H26 N2 O'
_chemical_formula_sum            'C22 H26 N2 O'
_chemical_formula_weight         334.45
_chemical_name_systematic
(E)-2-[(3,5-Di-tert-butyl-2-hydroxybenzylidene)amino]benzonitrile
_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                 104.5330(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   27.9710(4)
_cell_length_b                   7.32780(11)
_cell_length_c                   29.7840(4)
_cell_measurement_reflns_used    2369
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      3.12
_cell_volume                     5909.37(15)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.1303
_diffrn_reflns_av_sigmaI/netI    0.1083
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            30875
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.230
_refine_ls_extinction_coef       0.00170(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.812
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         11513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.812
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0611
_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)+(0.0618P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                4685
_reflns_number_total             11513
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2692.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222061
_cod_database_fobs_code          2222061
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
O O1 0.15087(5) 0.3744(2) 0.18806(5) 0.0691(5) Uani d . 1 . .
H H1A 0.1686(9) 0.398(4) 0.1684(8) 0.096(10) Uiso d . 1 . .
O O2 0.18374(5) 0.9439(2) -0.02043(5) 0.0684(5) Uani d . 1 . .
H H2A 0.1652(9) 0.925(4) 0.0006(9) 0.116(11) Uiso d . 1 . .
O O3 0.48619(5) 0.9288(2) 0.35466(5) 0.0684(5) Uani d . 1 . .
H H3A 0.5055(9) 0.923(3) 0.3328(8) 0.099(9) Uiso d . 1 . .
N N1 0.16759(6) 0.4172(2) 0.10588(6) 0.0550(5) Uani d . 1 . .
N N2 0.27218(8) 0.5702(4) 0.18410(8) 0.1010(8) Uani d . 1 . .
N N3 0.16614(6) 0.9441(2) 0.06174(6) 0.0520(5) Uani d . 1 . .
N N4 0.05724(8) 1.1104(3) -0.00802(8) 0.0945(8) Uani d . 1 . .
N N5 0.50291(6) 0.9533(2) 0.27211(6) 0.0541(5) Uani d . 1 . .
N N6 0.60959(8) 1.1213(4) 0.34472(8) 0.1030(9) Uani d . 1 . .
C C1 0.08638(7) 0.4080(3) 0.11845(7) 0.0515(6) Uani d . 1 . .
C C2 0.10180(7) 0.3837(3) 0.16714(7) 0.0549(6) Uani d . 1 . .
C C3 0.06760(7) 0.3746(3) 0.19363(7) 0.0544(6) Uani d . 1 . .
C C4 0.01780(7) 0.3800(3) 0.17000(7) 0.0594(6) Uani d . 1 . .
H H4A -0.0056 0.3731 0.1873 0.071 Uiso calc R 1 . .
C C5 0.00084(7) 0.3952(3) 0.12154(7) 0.0555(6) Uani d . 1 . .
C C6 0.03561(7) 0.4134(3) 0.09736(7) 0.0567(6) Uani d . 1 . .
H H6A 0.0254 0.4301 0.0654 0.068 Uiso calc R 1 . .
C C7 -0.05489(8) 0.3915(4) 0.09889(8) 0.0686(7) Uani d . 1 . .
C C8 -0.07643(9) 0.2160(5) 0.11300(10) 0.1213(12) Uani d . 1 . .
H H8A -0.0712 0.2130 0.1461 0.182 Uiso calc R 1 . .
H H8B -0.0605 0.1129 0.1031 0.182 Uiso calc R 1 . .
H H8C -0.1112 0.2115 0.0987 0.182 Uiso calc R 1 . .
C C9 -0.07904(9) 0.5588(5) 0.11231(11) 0.1360(15) Uani d . 1 . .
H H9A -0.0643 0.6657 0.1028 0.204 Uiso calc R 1 . .
H H9B -0.0745 0.5608 0.1453 0.204 Uiso calc R 1 . .
H H9C -0.1137 0.5567 0.0974 0.204 Uiso calc R 1 . .
C C10 -0.06546(8) 0.3877(4) 0.04606(8) 0.0917(9) Uani d . 1 . .
H H10A -0.0528 0.4968 0.0354 0.138 Uiso calc R 1 . .
H H10B -0.1005 0.3808 0.0330 0.138 Uiso calc R 1 . .
H H10C -0.0498 0.2832 0.0366 0.138 Uiso calc R 1 . .
C C11 0.08366(8) 0.3572(3) 0.24710(7) 0.0606(6) Uani d . 1 . .
C C12 0.11144(8) 0.1771(4) 0.26034(8) 0.0839(8) Uani d . 1 . .
H H12A 0.0905 0.0771 0.2470 0.126 Uiso calc R 1 . .
H H12B 0.1207 0.1650 0.2935 0.126 Uiso calc R 1 . .
H H12C 0.1405 0.1764 0.2488 0.126 Uiso calc R 1 . .
C C13 0.11663(9) 0.5200(4) 0.26765(8) 0.0828(8) Uani d . 1 . .
H H13A 0.0988 0.6316 0.2589 0.124 Uiso calc R 1 . .
H H13B 0.1457 0.5198 0.2561 0.124 Uiso calc R 1 . .
H H13C 0.1260 0.5101 0.3008 0.124 Uiso calc R 1 . .
C C14 0.03994(8) 0.3589(3) 0.26913(7) 0.0759(7) Uani d . 1 . .
H H14A 0.0184 0.2586 0.2573 0.114 Uiso calc R 1 . .
H H14B 0.0222 0.4715 0.2618 0.114 Uiso calc R 1 . .
H H14C 0.0518 0.3475 0.3022 0.114 Uiso calc R 1 . .
C C15 0.12062(8) 0.4301(3) 0.09044(7) 0.0550(6) Uani d . 1 . .
H H15A 0.1081 0.4553 0.0591 0.066 Uiso calc R 1 . .
C C16 0.19925(8) 0.4445(3) 0.07622(8) 0.0524(6) Uani d . 1 . .
C C17 0.24714(8) 0.5059(3) 0.09644(8) 0.0567(6) Uani d . 1 . .
C C18 0.28038(9) 0.5363(3) 0.07005(10) 0.0716(7) Uani d . 1 . .
H H18A 0.3121 0.5777 0.0840 0.086 Uiso calc R 1 . .
C C19 0.26641(10) 0.5051(4) 0.02291(10) 0.0794(8) Uani d . 1 . .
H H19A 0.2886 0.5258 0.0048 0.095 Uiso calc R 1 . .
C C20 0.21944(9) 0.4430(4) 0.00270(9) 0.0761(8) Uani d . 1 . .
H H20A 0.2101 0.4226 -0.0291 0.091 Uiso calc R 1 . .
C C21 0.18616(8) 0.4108(3) 0.02871(8) 0.0632(6) Uani d . 1 . .
H H21A 0.1549 0.3664 0.0146 0.076 Uiso calc R 1 . .
C C22 0.26084(8) 0.5404(4) 0.14511(10) 0.0700(7) Uani d . 1 . .
C C23 0.24659(7) 0.9944(3) 0.04970(7) 0.0498(5) Uani d . 1 . .
C C24 0.23205(7) 0.9758(3) 0.00082(7) 0.0524(6) Uani d . 1 . .
C C25 0.26610(7) 0.9935(3) -0.02562(7) 0.0539(6) Uani d . 1 . .
C C26 0.31490(7) 1.0267(3) -0.00171(7) 0.0588(6) Uani d . 1 . .
H H26A 0.3383 1.0369 -0.0189 0.071 Uiso calc R 1 . .
C C27 0.33121(7) 1.0459(3) 0.04689(7) 0.0554(6) Uani d . 1 . .
C C28 0.29620(7) 1.0291(3) 0.07106(7) 0.0535(6) Uani d . 1 . .
H H28A 0.3057 1.0411 0.1032 0.064 Uiso calc R 1 . .
C C29 0.25076(8) 0.9747(3) -0.07914(7) 0.0609(6) Uani d . 1 . .
C C30 0.29447(8) 1.0043(4) -0.10075(8) 0.0781(8) Uani d . 1 . .
H H30A 0.3198 0.9165 -0.0884 0.117 Uiso calc R 1 . .
H H30B 0.3074 1.1252 -0.0936 0.117 Uiso calc R 1 . .
H H30C 0.2836 0.9898 -0.1338 0.117 Uiso calc R 1 . .
C C31 0.23030(8) 0.7842(4) -0.09238(8) 0.0809(8) Uani d . 1 . .
H H31A 0.2549 0.6950 -0.0790 0.121 Uiso calc R 1 . .
H H31B 0.2216 0.7721 -0.1255 0.121 Uiso calc R 1 . .
H H31C 0.2015 0.7655 -0.0809 0.121 Uiso calc R 1 . .
C C32 0.21179(8) 1.1207(4) -0.10026(7) 0.0864(8) Uani d . 1 . .
H H32A 0.1837 1.1074 -0.0875 0.130 Uiso calc R 1 . .
H H32B 0.2017 1.1055 -0.1333 0.130 Uiso calc R 1 . .
H H32C 0.2258 1.2400 -0.0931 0.130 Uiso calc R 1 . .
C C33 0.38584(7) 1.0851(3) 0.06904(8) 0.0656(7) Uani d . 1 . .
C C34 0.40101(8) 1.2618(4) 0.04893(9) 0.1017(10) Uani d . 1 . .
H H34A 0.3957 1.2494 0.0160 0.153 Uiso calc R 1 . .
H H34B 0.4353 1.2857 0.0626 0.153 Uiso calc R 1 . .
H H34C 0.3815 1.3612 0.0556 0.153 Uiso calc R 1 . .
C C35 0.39540(8) 1.1110(4) 0.12172(8) 0.0823(8) Uani d . 1 . .
H H35A 0.3764 1.2125 0.1280 0.124 Uiso calc R 1 . .
H H35B 0.4299 1.1342 0.1347 0.124 Uiso calc R 1 . .
H H35C 0.3859 1.0025 0.1353 0.124 Uiso calc R 1 . .
C C36 0.41687(8) 0.9228(4) 0.06066(9) 0.0991(10) Uani d . 1 . .
H H36A 0.4118 0.9037 0.0279 0.149 Uiso calc R 1 . .
H H36B 0.4072 0.8154 0.0746 0.149 Uiso calc R 1 . .
H H36C 0.4512 0.9474 0.0742 0.149 Uiso calc R 1 . .
C C37 0.21240(7) 0.9782(3) 0.07787(7) 0.0528(6) Uani d . 1 . .
H H37A 0.2242 0.9931 0.1097 0.063 Uiso calc R 1 . .
C C38 0.13442(7) 0.9239(3) 0.09128(7) 0.0498(5) Uani d . 1 . .
C C39 0.14876(8) 0.8607(3) 0.13675(8) 0.0606(6) Uani d . 1 . .
H H39A 0.1817 0.8311 0.1496 0.073 Uiso calc R 1 . .
C C40 0.08411(8) 0.9640(3) 0.07310(8) 0.0543(6) Uani d . 1 . .
C C41 0.05055(8) 0.9410(3) 0.09933(9) 0.0678(7) Uani d . 1 . .
H H41A 0.0174 0.9668 0.0866 0.081 Uiso calc R 1 . .
C C42 0.06576(9) 0.8799(3) 0.14438(9) 0.0725(7) Uani d . 1 . .
H H42A 0.0431 0.8648 0.1622 0.087 Uiso calc R 1 . .
C C43 0.11512(9) 0.8414(3) 0.16280(8) 0.0701(7) Uani d . 1 . .
H H43A 0.1257 0.8017 0.1934 0.084 Uiso calc R 1 . .
C C44 0.06939(8) 1.0420(4) 0.02734(9) 0.0669(7) Uani d . 1 . .
C C45 0.42247(7) 0.9779(3) 0.28519(7) 0.0497(6) Uani d . 1 . .
C C46 0.37210(7) 1.0054(3) 0.26459(7) 0.0524(6) Uani d . 1 . .
H H46A 0.3621 1.0202 0.2326 0.063 Uiso calc R 1 . .
C C47 0.33720(7) 1.0114(3) 0.28913(7) 0.0528(6) Uani d . 1 . .
C C48 0.35431(7) 0.9892(3) 0.33760(7) 0.0575(6) Uani d . 1 . .
H H48A 0.3311 0.9926 0.3551 0.069 Uiso calc R 1 . .
C C49 0.40353(7) 0.9625(3) 0.36098(7) 0.0535(6) Uani d . 1 . .
C C50 0.43758(7) 0.9546(3) 0.33395(7) 0.0524(6) Uani d . 1 . .
C C51 0.28202(7) 1.0428(3) 0.26768(8) 0.0640(7) Uani d . 1 . .
C C52 0.27148(8) 1.0677(4) 0.21492(7) 0.0810(8) Uani d . 1 . .
H H52A 0.2810 0.9593 0.2013 0.121 Uiso calc R 1 . .
H H52B 0.2900 1.1698 0.2081 0.121 Uiso calc R 1 . .
H H52C 0.2369 1.0895 0.2024 0.121 Uiso calc R 1 . .
C C53 0.26556(8) 1.2169(4) 0.28790(9) 0.0998(10) Uani d . 1 . .
H H53A 0.2715 1.2047 0.3209 0.150 Uiso calc R 1 . .
H H53B 0.2309 1.2363 0.2746 0.150 Uiso calc R 1 . .
H H53C 0.2839 1.3191 0.2808 0.150 Uiso calc R 1 . .
C C54 0.25289(8) 0.8771(4) 0.27695(9) 0.0947(9) Uani d . 1 . .
H H54A 0.2591 0.8579 0.3098 0.142 Uiso calc R 1 . .
H H54B 0.2630 0.7712 0.2627 0.142 Uiso calc R 1 . .
H H54C 0.2183 0.8979 0.2641 0.142 Uiso calc R 1 . .
C C55 0.41951(8) 0.9427(3) 0.41447(7) 0.0596(6) Uani d . 1 . .
C C56 0.37603(8) 0.9617(4) 0.43647(7) 0.0748(7) Uani d . 1 . .
H H56A 0.3520 0.8692 0.4243 0.112 Uiso calc R 1 . .
H H56B 0.3613 1.0800 0.4294 0.112 Uiso calc R 1 . .
H H56C 0.3875 0.9478 0.4695 0.112 Uiso calc R 1 . .
C C57 0.45652(8) 1.0928(4) 0.43532(7) 0.0792(8) Uani d . 1 . .
H H57A 0.4663 1.0794 0.4684 0.119 Uiso calc R 1 . .
H H57B 0.4414 1.2101 0.4276 0.119 Uiso calc R 1 . .
H H57C 0.4850 1.0830 0.4230 0.119 Uiso calc R 1 . .
C C58 0.44251(8) 0.7541(4) 0.42697(8) 0.0768(7) Uani d . 1 . .
H H58A 0.4189 0.6616 0.4136 0.115 Uiso calc R 1 . .
H H58B 0.4518 0.7405 0.4601 0.115 Uiso calc R 1 . .
H H58C 0.4712 0.7419 0.4150 0.115 Uiso calc R 1 . .
C C59 0.45650(7) 0.9795(3) 0.25691(7) 0.0524(6) Uani d . 1 . .
H H59A 0.4442 1.0009 0.2253 0.063 Uiso calc R 1 . .
C C60 0.53436(7) 0.9589(3) 0.24184(7) 0.0502(6) Uani d . 1 . .
C C61 0.58307(8) 1.0150(3) 0.25981(8) 0.0542(6) Uani d . 1 . .
C C62 0.61611(8) 1.0212(3) 0.23255(9) 0.0667(7) Uani d . 1 . .
H H62A 0.6485 1.0578 0.2453 0.080 Uiso calc R 1 . .
C C63 0.60124(9) 0.9730(3) 0.18625(9) 0.0738(7) Uani d . 1 . .
H H63A 0.6233 0.9785 0.1675 0.089 Uiso calc R 1 . .
C C64 0.55325(9) 0.9169(3) 0.16834(8) 0.0709(7) Uani d . 1 . .
H H64A 0.5430 0.8843 0.1372 0.085 Uiso calc R 1 . .
C C65 0.52018(8) 0.9078(3) 0.19529(7) 0.0606(6) Uani d . 1 . .
H H65A 0.4881 0.8674 0.1825 0.073 Uiso calc R 1 . .
C C66 0.59803(8) 1.0731(4) 0.30739(9) 0.0685(7) Uani d . 1 . .
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'
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
C6 C1 C2 . . 118.4(2) ?
C6 C1 C15 . . 119.16(19) ?
C2 C1 C15 . . 122.39(18) ?
C15 N1 C16 . . 120.80(19) ?
C2 O1 H1A . . 111.2(16) ?
O1 C2 C3 . . 119.90(19) ?
O1 C2 C1 . . 119.2(2) ?
C3 C2 C1 . . 120.84(18) ?
C24 O2 H2A . . 112.0(16) ?
C2 C3 C4 . . 117.13(19) ?
C2 C3 C11 . . 121.75(18) ?
C4 C3 C11 . . 121.1(2) ?
C50 O3 H3A . . 112.0(14) ?
C37 N3 C38 . . 121.36(18) ?
C3 C4 C5 . . 123.9(2) ?
C3 C4 H4A . . 118.1 ?
C5 C4 H4A . . 118.1 ?
C6 C5 C4 . . 116.83(18) ?
C6 C5 C7 . . 123.6(2) ?
C4 C5 C7 . . 119.6(2) ?
C59 N5 C60 . . 120.71(18) ?
C5 C6 C1 . . 122.7(2) ?
C5 C6 H6A . . 118.6 ?
C1 C6 H6A . . 118.6 ?
C9 C7 C8 . . 112.4(2) ?
C9 C7 C10 . . 107.8(2) ?
C8 C7 C10 . . 106.3(2) ?
C9 C7 C5 . . 110.1(2) ?
C8 C7 C5 . . 108.8(2) ?
C10 C7 C5 . . 111.5(2) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C14 C11 C12 . . 107.80(19) ?
C14 C11 C13 . . 106.72(19) ?
C12 C11 C13 . . 110.55(18) ?
C14 C11 C3 . . 112.63(17) ?
C12 C11 C3 . . 109.47(19) ?
C13 C11 C3 . . 109.63(18) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N1 C15 C1 . . 124.0(2) ?
N1 C15 H15A . . 118.0 ?
C1 C15 H15A . . 118.0 ?
C21 C16 C17 . . 118.3(2) ?
C21 C16 N1 . . 124.3(2) ?
C17 C16 N1 . . 117.3(2) ?
C18 C17 C16 . . 121.1(2) ?
C18 C17 C22 . . 120.3(2) ?
C16 C17 C22 . . 118.6(2) ?
C17 C18 C19 . . 119.7(2) ?
C17 C18 H18A . . 120.2 ?
C19 C18 H18A . . 120.2 ?
C20 C19 C18 . . 119.7(2) ?
C20 C19 H19A . . 120.2 ?
C18 C19 H19A . . 120.2 ?
C21 C20 C19 . . 121.2(2) ?
C21 C20 H20A . . 119.4 ?
C19 C20 H20A . . 119.4 ?
C20 C21 C16 . . 120.0(2) ?
C20 C21 H21A . . 120.0 ?
C16 C21 H21A . . 120.0 ?
N2 C22 C17 . . 179.1(3) ?
C28 C23 C24 . . 118.8(2) ?
C28 C23 C37 . . 118.89(19) ?
C24 C23 C37 . . 122.30(18) ?
O2 C24 C25 . . 119.71(19) ?
O2 C24 C23 . . 119.35(19) ?
C25 C24 C23 . . 120.92(18) ?
C24 C25 C26 . . 116.80(19) ?
C24 C25 C29 . . 121.59(18) ?
C26 C25 C29 . . 121.6(2) ?
C25 C26 C27 . . 124.4(2) ?
C25 C26 H26A . . 117.8 ?
C27 C26 H26A . . 117.8 ?
C28 C27 C26 . . 116.37(18) ?
C28 C27 C33 . . 124.2(2) ?
C26 C27 C33 . . 119.4(2) ?
C27 C28 C23 . . 122.7(2) ?
C27 C28 H28A . . 118.6 ?
C23 C28 H28A . . 118.6 ?
C31 C29 C30 . . 107.98(19) ?
C31 C29 C32 . . 110.41(19) ?
C30 C29 C32 . . 106.64(19) ?
C31 C29 C25 . . 109.70(19) ?
C30 C29 C25 . . 112.03(17) ?
C32 C29 C25 . . 110.02(19) ?
C29 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C29 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
C29 C31 H31A . . 109.5 ?
C29 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C29 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C29 C32 H32A . . 109.5 ?
C29 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C29 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C36 C33 C34 . . 111.7(2) ?
C36 C33 C27 . . 109.3(2) ?
C34 C33 C27 . . 109.54(18) ?
C36 C33 C35 . . 107.60(19) ?
C34 C33 C35 . . 107.5(2) ?
C27 C33 C35 . . 111.24(19) ?
C33 C34 H34A . . 109.5 ?
C33 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C33 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C33 C35 H35A . . 109.5 ?
C33 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C33 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C33 C36 H36A . . 109.5 ?
C33 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C33 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
N3 C37 C23 . . 123.80(19) ?
N3 C37 H37A . . 118.1 ?
C23 C37 H37A . . 118.1 ?
C39 C38 N3 . . 124.82(19) ?
C39 C38 C40 . . 117.4(2) ?
N3 C38 C40 . . 117.72(19) ?
C43 C39 C38 . . 121.0(2) ?
C43 C39 H39A . . 119.5 ?
C38 C39 H39A . . 119.5 ?
C41 C40 C38 . . 121.1(2) ?
C41 C40 C44 . . 120.9(2) ?
C38 C40 C44 . . 117.9(2) ?
C40 C41 C42 . . 120.4(2) ?
C40 C41 H41A . . 119.8 ?
C42 C41 H41A . . 119.8 ?
C41 C42 C43 . . 119.2(2) ?
C41 C42 H42A . . 120.4 ?
C43 C42 H42A . . 120.4 ?
C39 C43 C42 . . 121.0(2) ?
C39 C43 H43A . . 119.5 ?
C42 C43 H43A . . 119.5 ?
N4 C44 C40 . . 177.1(3) ?
C46 C45 C50 . . 118.3(2) ?
C46 C45 C59 . . 119.23(19) ?
C50 C45 C59 . . 122.45(18) ?
C47 C46 C45 . . 123.19(19) ?
C47 C46 H46A . . 118.4 ?
C45 C46 H46A . . 118.4 ?
C46 C47 C48 . . 116.18(18) ?
C46 C47 C51 . . 124.39(19) ?
C48 C47 C51 . . 119.4(2) ?
C49 C48 C47 . . 124.5(2) ?
C49 C48 H48A . . 117.7 ?
C47 C48 H48A . . 117.7 ?
C48 C49 C50 . . 116.76(19) ?
C48 C49 C55 . . 121.43(19) ?
C50 C49 C55 . . 121.82(18) ?
O3 C50 C49 . . 119.65(19) ?
O3 C50 C45 . . 119.30(19) ?
C49 C50 C45 . . 121.03(19) ?
C54 C51 C53 . . 111.4(2) ?
C54 C51 C47 . . 109.5(2) ?
C53 C51 C47 . . 109.39(18) ?
C54 C51 C52 . . 107.80(19) ?
C53 C51 C52 . . 107.7(2) ?
C47 C51 C52 . . 111.05(19) ?
C51 C52 H52A . . 109.5 ?
C51 C52 H52B . . 109.5 ?
H52A C52 H52B . . 109.5 ?
C51 C52 H52C . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
C51 C53 H53A . . 109.5 ?
C51 C53 H53B . . 109.5 ?
H53A C53 H53B . . 109.5 ?
C51 C53 H53C . . 109.5 ?
H53A C53 H53C . . 109.5 ?
H53B C53 H53C . . 109.5 ?
C51 C54 H54A . . 109.5 ?
C51 C54 H54B . . 109.5 ?
H54A C54 H54B . . 109.5 ?
C51 C54 H54C . . 109.5 ?
H54A C54 H54C . . 109.5 ?
H54B C54 H54C . . 109.5 ?
C56 C55 C58 . . 108.01(19) ?
C56 C55 C57 . . 106.92(19) ?
C58 C55 C57 . . 110.48(19) ?
C56 C55 C49 . . 112.19(17) ?
C58 C55 C49 . . 109.25(18) ?
C57 C55 C49 . . 109.96(18) ?
C55 C56 H56A . . 109.5 ?
C55 C56 H56B . . 109.5 ?
H56A C56 H56B . . 109.5 ?
C55 C56 H56C . . 109.5 ?
H56A C56 H56C . . 109.5 ?
H56B C56 H56C . . 109.5 ?
C55 C57 H57A . . 109.5 ?
C55 C57 H57B . . 109.5 ?
H57A C57 H57B . . 109.5 ?
C55 C57 H57C . . 109.5 ?
H57A C57 H57C . . 109.5 ?
H57B C57 H57C . . 109.5 ?
C55 C58 H58A . . 109.5 ?
C55 C58 H58B . . 109.5 ?
H58A C58 H58B . . 109.5 ?
C55 C58 H58C . . 109.5 ?
H58A C58 H58C . . 109.5 ?
H58B C58 H58C . . 109.5 ?
N5 C59 C45 . . 124.14(19) ?
N5 C59 H59A . . 117.9 ?
C45 C59 H59A . . 117.9 ?
C65 C60 C61 . . 117.9(2) ?
C65 C60 N5 . . 124.12(19) ?
C61 C60 N5 . . 118.0(2) ?
C62 C61 C60 . . 121.3(2) ?
C62 C61 C66 . . 120.0(2) ?
C60 C61 C66 . . 118.7(2) ?
C61 C62 C63 . . 120.1(2) ?
C61 C62 H62A . . 119.9 ?
C63 C62 H62A . . 119.9 ?
C64 C63 C62 . . 118.9(2) ?
C64 C63 H63A . . 120.6 ?
C62 C63 H63A . . 120.6 ?
C65 C64 C63 . . 121.5(2) ?
C65 C64 H64A . . 119.2 ?
C63 C64 H64A . . 119.2 ?
C64 C65 C60 . . 120.3(2) ?
C64 C65 H65A . . 119.9 ?
C60 C65 H65A . . 119.9 ?
N6 C66 C61 . . 179.0(3) ?
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
C1 C6 . 1.402(3) ?
C1 C2 . 1.417(3) ?
C1 C15 . 1.429(3) ?
N1 C15 . 1.282(2) ?
N1 C16 . 1.413(2) ?
O1 C2 . 1.359(2) ?
O1 H1A . 0.87(2) ?
C2 C3 . 1.386(3) ?
N2 C22 . 1.145(3) ?
O2 C24 . 1.361(2) ?
O2 H2A . 0.92(3) ?
C3 C4 . 1.395(2) ?
C3 C11 . 1.548(3) ?
O3 C50 . 1.358(2) ?
O3 H3A . 0.95(2) ?
N3 C37 . 1.287(2) ?
N3 C38 . 1.405(2) ?
C4 C5 . 1.406(3) ?
C4 H4A . 0.9300 ?
N4 C44 . 1.138(3) ?
C5 C6 . 1.354(3) ?
C5 C7 . 1.536(3) ?
N5 C59 . 1.277(2) ?
N5 C60 . 1.409(2) ?
C6 H6A . 0.9300 ?
N6 C66 . 1.134(3) ?
C7 C9 . 1.501(3) ?
C7 C8 . 1.523(4) ?
C7 C10 . 1.527(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C14 . 1.526(3) ?
C11 C12 . 1.532(3) ?
C11 C13 . 1.538(3) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9300 ?
C16 C21 . 1.392(3) ?
C16 C17 . 1.398(3) ?
C17 C18 . 1.378(3) ?
C17 C22 . 1.426(3) ?
C18 C19 . 1.379(3) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.378(3) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.373(3) ?
C20 H20A . 0.9300 ?
C21 H21A . 0.9300 ?
C23 C28 . 1.397(2) ?
C23 C24 . 1.416(3) ?
C23 C37 . 1.427(3) ?
C24 C25 . 1.386(3) ?
C25 C26 . 1.393(3) ?
C25 C29 . 1.550(3) ?
C26 C27 . 1.411(3) ?
C26 H26A . 0.9300 ?
C27 C28 . 1.359(3) ?
C27 C33 . 1.532(3) ?
C28 H28A . 0.9300 ?
C29 C31 . 1.522(3) ?
C29 C30 . 1.533(3) ?
C29 C32 . 1.544(3) ?
C30 H30A . 0.9600 ?
C30 H30B . 0.9600 ?
C30 H30C . 0.9600 ?
C31 H31A . 0.9600 ?
C31 H31B . 0.9600 ?
C31 H31C . 0.9600 ?
C32 H32A . 0.9600 ?
C32 H32B . 0.9600 ?
C32 H32C . 0.9600 ?
C33 C36 . 1.529(3) ?
C33 C34 . 1.531(3) ?
C33 C35 . 1.536(3) ?
C34 H34A . 0.9600 ?
C34 H34B . 0.9600 ?
C34 H34C . 0.9600 ?
C35 H35A . 0.9600 ?
C35 H35B . 0.9600 ?
C35 H35C . 0.9600 ?
C36 H36A . 0.9600 ?
C36 H36B . 0.9600 ?
C36 H36C . 0.9600 ?
C37 H37A . 0.9300 ?
C38 C39 . 1.392(3) ?
C38 C40 . 1.406(3) ?
C39 C43 . 1.369(3) ?
C39 H39A . 0.9300 ?
C40 C41 . 1.374(3) ?
C40 C44 . 1.440(3) ?
C41 C42 . 1.377(3) ?
C41 H41A . 0.9300 ?
C42 C43 . 1.381(3) ?
C42 H42A . 0.9300 ?
C43 H43A . 0.9300 ?
C45 C46 . 1.403(2) ?
C45 C50 . 1.417(3) ?
C45 C59 . 1.421(3) ?
C46 C47 . 1.359(3) ?
C46 H46A . 0.9300 ?
C47 C48 . 1.412(3) ?
C47 C51 . 1.532(3) ?
C48 C49 . 1.392(2) ?
C48 H48A . 0.9300 ?
C49 C50 . 1.394(3) ?
C49 C55 . 1.550(3) ?
C51 C54 . 1.526(3) ?
C51 C53 . 1.531(3) ?
C51 C52 . 1.535(3) ?
C52 H52A . 0.9600 ?
C52 H52B . 0.9600 ?
C52 H52C . 0.9600 ?
C53 H53A . 0.9600 ?
C53 H53B . 0.9600 ?
C53 H53C . 0.9600 ?
C54 H54A . 0.9600 ?
C54 H54B . 0.9600 ?
C54 H54C . 0.9600 ?
C55 C56 . 1.526(3) ?
C55 C58 . 1.531(3) ?
C55 C57 . 1.531(3) ?
C56 H56A . 0.9600 ?
C56 H56B . 0.9600 ?
C56 H56C . 0.9600 ?
C57 H57A . 0.9600 ?
C57 H57B . 0.9600 ?
C57 H57C . 0.9600 ?
C58 H58A . 0.9600 ?
C58 H58B . 0.9600 ?
C58 H58C . 0.9600 ?
C59 H59A . 0.9300 ?
C60 C65 . 1.394(3) ?
C60 C61 . 1.395(3) ?
C61 C62 . 1.376(3) ?
C61 C66 . 1.437(3) ?
C62 C63 . 1.383(3) ?
C62 H62A . 0.9300 ?
C63 C64 . 1.377(3) ?
C63 H63A . 0.9300 ?
C64 C65 . 1.370(3) ?
C64 H64A . 0.9300 ?
C65 H65A . 0.9300 ?
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
O3 H3A N5 . 0.95(2) 1.81(2) 2.622(2) 143(2)
O2 H2A N3 . 0.92(3) 1.82(3) 2.615(2) 143(2)
O1 H1A N1 . 0.87(2) 1.86(2) 2.623(2) 145(2)
