#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/94/2229453.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_2229453
loop_
_publ_author_name
'van Tonder, Johannes H.'
'Muller, Theunis J.'
'Bezuidenhoudt, Barend C. B.'
_publ_section_title
;
 4,5-Bis(2,4-di-tert-butylphenoxy)phthalonitrile
;
_journal_coeditor_code           LR2003
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o705
_journal_page_last               o706
_journal_paper_doi               10.1107/S1600536811006118
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C36 H44 N2 O2'
_chemical_formula_moiety         'C36 H44 N2 O2'
_chemical_formula_sum            'C36 H44 N2 O2'
_chemical_formula_weight         536.76
_chemical_name_systematic
;
4,5-Bis(2,4-di-tert-butylphenoxy)phthalonitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                99.7190(10)
_cell_angle_beta                 102.9960(10)
_cell_angle_gamma                110.9630(10)
_cell_formula_units_Z            2
_cell_length_a                   10.9468(3)
_cell_length_b                   11.0416(4)
_cell_length_c                   15.3133(5)
_cell_measurement_reflns_used    7569
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      28.57
_cell_measurement_theta_min      2.84
_cell_volume                     1619.71(9)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenberg & Putz, 2005)'
_computing_publication_material  'WingGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      175(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31007
_diffrn_reflns_theta_full        28.57
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.1
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         7785
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.5205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                5255
_reflns_number_total             7785
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lr2003.cif
_cod_data_source_block           I
_cod_database_code               2229453
_cod_database_fobs_code          2229453
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.32485(17) -0.09576(17) 0.99913(12) 0.0399(4) Uani d . 1 . .
C C2 0.2111(2) 0.0801(2) 1.06591(15) 0.0601(6) Uani d . 1 . .
C C3 0.27916(16) -0.02106(15) 0.94090(12) 0.0350(3) Uani d . 1 . .
C C4 0.22520(18) 0.06741(17) 0.97435(12) 0.0399(4) Uani d . 1 . .
C C5 0.18274(18) 0.14119(17) 0.91845(12) 0.0428(4) Uani d . 1 . .
H H5 0.1479 0.201 0.9412 0.051 Uiso calc R 1 . .
C C6 0.19232(16) 0.12561(15) 0.82952(11) 0.0344(3) Uani d . 1 . .
C C7 0.24483(15) 0.03433(15) 0.79532(11) 0.0325(3) Uani d . 1 . .
C C8 0.28764(16) -0.03739(15) 0.85123(12) 0.0356(4) Uani d . 1 . .
H H8 0.3225 -0.0972 0.8286 0.043 Uiso calc R 1 . .
C C11 0.32695(16) -0.03783(15) 0.67397(11) 0.0341(3) Uani d . 1 . .
C C12 0.46705(18) 0.02362(17) 0.71765(12) 0.0422(4) Uani d . 1 . .
H H12 0.5042 0.099 0.7687 0.051 Uiso calc R 1 . .
C C13 0.55247(17) -0.02689(18) 0.68553(12) 0.0421(4) Uani d . 1 . .
H H13 0.6467 0.0138 0.716 0.05 Uiso calc R 1 . .
C C14 0.49885(16) -0.13740(16) 0.60855(11) 0.0342(3) Uani d . 1 A .
C C15 0.35667(16) -0.19584(16) 0.56661(11) 0.0335(3) Uani d . 1 . .
H H15 0.32 -0.2701 0.5148 0.04 Uiso calc R 1 . .
C C16 0.26543(16) -0.15055(15) 0.59701(11) 0.0317(3) Uani d . 1 . .
C C17 0.10949(16) -0.22154(16) 0.54796(12) 0.0364(4) Uani d . 1 . .
C C18 0.07343(19) -0.33885(19) 0.46378(13) 0.0503(5) Uani d . 1 . .
H H18A 0.1151 -0.3052 0.419 0.075 Uiso calc R 1 . .
H H18B -0.0247 -0.3829 0.4359 0.075 Uiso calc R 1 . .
H H18C 0.1071 -0.4021 0.4836 0.075 Uiso calc R 1 . .
C C19 0.03676(18) -0.27803(18) 0.61657(13) 0.0458(4) Uani d . 1 . .
H H19A -0.0601 -0.327 0.585 0.069 Uiso calc R 1 . .
H H19B 0.0516 -0.205 0.6675 0.069 Uiso calc R 1 . .
H H19C 0.0734 -0.3373 0.64 0.069 Uiso calc R 1 . .
C C20 0.05301(19) -0.1242(2) 0.51307(14) 0.0495(5) Uani d . 1 . .
H H20A 0.0705 -0.0513 0.5649 0.074 Uiso calc R 1 . .
H H20B -0.0443 -0.1713 0.4826 0.074 Uiso calc R 1 . .
H H20C 0.0974 -0.0891 0.4698 0.074 Uiso calc R 1 . .
C C21 0.58891(17) -0.19560(18) 0.56883(12) 0.0414(4) Uani d . 1 . .
C C25 0.09512(16) 0.28072(16) 0.79279(11) 0.0334(3) Uani d . 1 . .
C C26 -0.03540(17) 0.22322(16) 0.80045(12) 0.0406(4) Uani d . 1 . .
H H26 -0.0763 0.1312 0.7942 0.049 Uiso calc R 1 . .
C C27 -0.10495(16) 0.30261(16) 0.81741(12) 0.0385(4) Uani d . 1 . .
H H27 -0.1921 0.2638 0.8236 0.046 Uiso calc R 1 . .
C C28 -0.04634(15) 0.43969(15) 0.82533(11) 0.0310(3) Uani d . 1 . .
C C29 0.08501(15) 0.49289(15) 0.81665(10) 0.0300(3) Uani d . 1 . .
H H29 0.1251 0.5846 0.8218 0.036 Uiso calc R 1 . .
C C30 0.16077(15) 0.41736(15) 0.80073(10) 0.0294(3) Uani d . 1 . .
C C31 -0.12629(16) 0.52644(17) 0.84061(12) 0.0371(4) Uani d . 1 . .
C C32 -0.1880(2) 0.5004(2) 0.91925(15) 0.0562(5) Uani d . 1 . .
H H32A -0.2375 0.5556 0.9278 0.084 Uiso calc R 1 . .
H H32B -0.1156 0.5223 0.9759 0.084 Uiso calc R 1 . .
H H32C -0.2498 0.4071 0.9035 0.084 Uiso calc R 1 . .
C C33 -0.0344(2) 0.6768(2) 0.8677(2) 0.0792(8) Uani d . 1 . .
H H33A 0.0028 0.698 0.8184 0.119 Uiso calc R 1 . .
H H33B 0.0394 0.6995 0.9237 0.119 Uiso calc R 1 . .
H H33C -0.0876 0.7274 0.8781 0.119 Uiso calc R 1 . .
C C34 -0.2414(3) 0.4900(3) 0.75103(16) 0.0823(8) Uani d . 1 . .
H H34A -0.203 0.5063 0.7014 0.124 Uiso calc R 1 . .
H H34B -0.2919 0.5442 0.7592 0.124 Uiso calc R 1 . .
H H34C -0.3022 0.3964 0.7358 0.124 Uiso calc R 1 . .
C C35 0.30789(15) 0.48317(16) 0.79499(11) 0.0352(4) Uani d . 1 . .
C C36 0.40825(18) 0.4698(2) 0.87618(14) 0.0540(5) Uani d . 1 . .
H H36A 0.5008 0.517 0.876 0.081 Uiso calc R 1 . .
H H36B 0.389 0.3762 0.8696 0.081 Uiso calc R 1 . .
H H36C 0.398 0.5077 0.9339 0.081 Uiso calc R 1 . .
C C37 0.31886(19) 0.4175(2) 0.70201(13) 0.0485(4) Uani d . 1 . .
H H37A 0.2603 0.4318 0.6517 0.073 Uiso calc R 1 . .
H H37B 0.2908 0.3224 0.6945 0.073 Uiso calc R 1 . .
H H37C 0.4124 0.4571 0.7017 0.073 Uiso calc R 1 . .
C C38 0.35244(18) 0.63396(18) 0.80263(15) 0.0504(5) Uani d . 1 . .
H H38A 0.29 0.6458 0.7532 0.076 Uiso calc R 1 . .
H H38B 0.4437 0.6712 0.7979 0.076 Uiso calc R 1 . .
H H38C 0.3515 0.6793 0.8616 0.076 Uiso calc R 1 . .
N N1 0.36199(18) -0.15552(17) 1.04487(12) 0.0546(4) Uani d . 1 . .
N N2 0.1971(3) 0.0875(3) 1.13809(15) 0.0937(8) Uani d . 1 . .
O O1 0.24505(12) 0.02227(11) 0.70557(8) 0.0384(3) Uani d . 1 . .
O O2 0.15855(12) 0.19450(11) 0.76953(8) 0.0400(3) Uani d . 1 . .
C C22A 0.7447(3) -0.1104(4) 0.6219(2) 0.0569(8) Uani d PD 0.814(6) A 1
H H22A 0.7633 -0.1136 0.6856 0.085 Uiso calc PR 0.814(6) A 1
H H22B 0.7686 -0.0186 0.6198 0.085 Uiso calc PR 0.814(6) A 1
H H22C 0.7982 -0.1465 0.593 0.085 Uiso calc PR 0.814(6) A 1
C C23A 0.5683(3) -0.1892(5) 0.46811(18) 0.0696(12) Uani d PD 0.814(6) A 1
H H23A 0.6292 -0.2192 0.4438 0.104 Uiso calc PR 0.814(6) A 1
H H23B 0.5879 -0.0981 0.4658 0.104 Uiso calc PR 0.814(6) A 1
H H23C 0.4748 -0.2464 0.4314 0.104 Uiso calc PR 0.814(6) A 1
C C24A 0.5532(5) -0.3364(4) 0.5778(5) 0.0921(16) Uani d PD 0.814(6) A 1
H H24A 0.6091 -0.3733 0.5526 0.138 Uiso calc PR 0.814(6) A 1
H H24B 0.4579 -0.3913 0.5441 0.138 Uiso calc PR 0.814(6) A 1
H H24C 0.5696 -0.3348 0.6423 0.138 Uiso calc PR 0.814(6) A 1
C C22B 0.5042(14) -0.2940(15) 0.4618(7) 0.050(3) Uani d PD 0.186(6) A 2
H H22D 0.5663 -0.3179 0.4347 0.075 Uiso calc PR 0.186(6) A 2
H H22E 0.4646 -0.2471 0.425 0.075 Uiso calc PR 0.186(6) A 2
H H22F 0.4323 -0.3743 0.4633 0.075 Uiso calc PR 0.186(6) A 2
C C23B 0.6083(13) -0.2968(14) 0.6183(9) 0.0414(4) Uani d PD 0.186(6) A 2
H H23D 0.664 -0.3346 0.5936 0.062 Uiso calc PR 0.186(6) A 2
H H23E 0.5203 -0.3674 0.6093 0.062 Uiso calc PR 0.186(6) A 2
H H23F 0.653 -0.2532 0.6837 0.062 Uiso calc PR 0.186(6) A 2
C C24B 0.7055(16) -0.0922(14) 0.5672(16) 0.075(5) Uani d PD 0.186(6) A 2
H H24D 0.7568 -0.0353 0.6294 0.112 Uiso calc PR 0.186(6) A 2
H H24E 0.6791 -0.04 0.5286 0.112 Uiso calc PR 0.186(6) A 2
H H24F 0.7615 -0.1295 0.5424 0.112 Uiso calc PR 0.186(6) 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 0 '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 0.006 '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
N1 C1 C3 . . 179.26(18) ?
N2 C2 C4 . . 178.4(3) ?
C8 C3 C4 . . 119.70(15) ?
C8 C3 C1 . . 120.12(14) ?
C4 C3 C1 . . 120.18(15) ?
C5 C4 C3 . . 120.20(15) ?
C5 C4 C2 . . 120.12(15) ?
C3 C4 C2 . . 119.67(15) ?
C6 C5 C4 . . 119.99(14) ?
C6 C5 H5 . . 120 ?
C4 C5 H5 . . 120 ?
O2 C6 C5 . . 125.57(13) ?
O2 C6 C7 . . 114.72(14) ?
C5 C6 C7 . . 119.68(14) ?
O1 C7 C8 . . 124.80(13) ?
O1 C7 C6 . . 115.18(13) ?
C8 C7 C6 . . 120.00(14) ?
C7 C8 C3 . . 120.42(14) ?
C7 C8 H8 . . 119.8 ?
C3 C8 H8 . . 119.8 ?
C12 C11 C16 . . 122.65(13) ?
C12 C11 O1 . . 117.89(14) ?
C16 C11 O1 . . 119.32(14) ?
C11 C12 C13 . . 120.01(16) ?
C11 C12 H12 . . 120 ?
C13 C12 H12 . . 120 ?
C14 C13 C12 . . 120.56(16) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 117.32(14) ?
C13 C14 C21 . . 122.73(15) ?
C15 C14 C21 . . 119.95(14) ?
C14 C15 C16 . . 124.54(15) ?
C14 C15 H15 . . 117.7 ?
C16 C15 H15 . . 117.7 ?
C11 C16 C15 . . 114.91(14) ?
C11 C16 C17 . . 123.53(13) ?
C15 C16 C17 . . 121.56(14) ?
C18 C17 C20 . . 107.50(15) ?
C18 C17 C16 . . 111.47(13) ?
C20 C17 C16 . . 111.28(14) ?
C18 C17 C19 . . 108.14(15) ?
C20 C17 C19 . . 109.01(14) ?
C16 C17 C19 . . 109.35(14) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C24B C21 C24A . . 135.6(7) ?
C24B C21 C23B . . 117.8(9) ?
C24A C21 C23B . . 27.0(4) ?
C24B C21 C23A . . 72.6(9) ?
C24A C21 C23A . . 112.7(3) ?
C23B C21 C23A . . 133.6(5) ?
C24B C21 C14 . . 110.0(5) ?
C24A C21 C14 . . 109.31(17) ?
C23B C21 C14 . . 108.7(5) ?
C23A C21 C14 . . 108.60(16) ?
C24B C21 C22A . . 36.7(9) ?
C24A C21 C22A . . 108.2(2) ?
C23B C21 C22A . . 84.1(5) ?
C23A C21 C22A . . 106.40(19) ?
C14 C21 C22A . . 111.68(16) ?
C24B C21 C22B . . 108.7(8) ?
C24A C21 C22B . . 75.0(5) ?
C23B C21 C22B . . 100.4(6) ?
C23A C21 C22B . . 40.0(5) ?
C14 C21 C22B . . 110.8(4) ?
C22A C21 C22B . . 133.0(4) ?
C26 C25 C30 . . 122.53(13) ?
C26 C25 O2 . . 117.88(14) ?
C30 C25 O2 . . 119.43(13) ?
C27 C26 C25 . . 119.90(15) ?
C27 C26 H26 . . 120 ?
C25 C26 H26 . . 120 ?
C26 C27 C28 . . 120.78(15) ?
C26 C27 H27 . . 119.6 ?
C28 C27 H27 . . 119.6 ?
C27 C28 C29 . . 117.23(13) ?
C27 C28 C31 . . 120.53(13) ?
C29 C28 C31 . . 122.23(14) ?
C28 C29 C30 . . 124.32(14) ?
C28 C29 H29 . . 117.8 ?
C30 C29 H29 . . 117.8 ?
C25 C30 C29 . . 115.24(13) ?
C25 C30 C35 . . 122.92(13) ?
C29 C30 C35 . . 121.83(14) ?
C34 C31 C33 . . 109.46(19) ?
C34 C31 C32 . . 109.21(17) ?
C33 C31 C32 . . 106.95(16) ?
C34 C31 C28 . . 108.44(14) ?
C33 C31 C28 . . 112.04(14) ?
C32 C31 C28 . . 110.70(13) ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C31 C33 H33A . . 109.5 ?
C31 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C31 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C31 C34 H34A . . 109.5 ?
C31 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C31 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C36 C35 C38 . . 107.50(15) ?
C36 C35 C37 . . 110.04(14) ?
C38 C35 C37 . . 107.12(14) ?
C36 C35 C30 . . 109.04(14) ?
C38 C35 C30 . . 111.76(12) ?
C37 C35 C30 . . 111.30(14) ?
C35 C36 H36A . . 109.5 ?
C35 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C35 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C35 C37 H37A . . 109.5 ?
C35 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C35 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C35 C38 H38A . . 109.5 ?
C35 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C35 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C7 O1 C11 . . 118.38(12) ?
C6 O2 C25 . . 120.00(12) ?
C21 C22A H22A . . 109.5 ?
C21 C22A H22B . . 109.5 ?
C21 C22A H22C . . 109.5 ?
C21 C23A H23A . . 109.5 ?
C21 C23A H23B . . 109.5 ?
C21 C23A H23C . . 109.5 ?
C21 C24A H24A . . 109.5 ?
C21 C24A H24B . . 109.5 ?
C21 C24A H24C . . 109.5 ?
C21 C22B H22D . . 109.5 ?
C21 C22B H22E . . 109.5 ?
H22D C22B H22E . . 109.5 ?
C21 C22B H22F . . 109.5 ?
H22D C22B H22F . . 109.5 ?
H22E C22B H22F . . 109.5 ?
C21 C23B H23D . . 109.5 ?
C21 C23B H23E . . 109.5 ?
H23D C23B H23E . . 109.5 ?
C21 C23B H23F . . 109.5 ?
H23D C23B H23F . . 109.5 ?
H23E C23B H23F . . 109.5 ?
C21 C24B H24D . . 109.5 ?
C21 C24B H24E . . 109.5 ?
H24D C24B H24E . . 109.5 ?
C21 C24B H24F . . 109.5 ?
H24D C24B H24F . . 109.5 ?
H24E C24B H24F . . 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
C1 N1 . 1.145(2) ?
C1 C3 . 1.438(2) ?
C2 N2 . 1.143(3) ?
C2 C4 . 1.434(3) ?
C3 C8 . 1.383(2) ?
C3 C4 . 1.395(2) ?
C4 C5 . 1.393(2) ?
C5 C6 . 1.376(2) ?
C5 H5 . 0.93 ?
C6 O2 . 1.3578(19) ?
C6 C7 . 1.412(2) ?
C7 O1 . 1.3588(19) ?
C7 C8 . 1.376(2) ?
C8 H8 . 0.93 ?
C11 C12 . 1.379(2) ?
C11 C16 . 1.393(2) ?
C11 O1 . 1.4110(17) ?
C12 C13 . 1.384(2) ?
C12 H12 . 0.93 ?
C13 C14 . 1.383(2) ?
C13 H13 . 0.93 ?
C14 C15 . 1.394(2) ?
C14 C21 . 1.532(2) ?
C15 C16 . 1.397(2) ?
C15 H15 . 0.93 ?
C16 C17 . 1.536(2) ?
C17 C18 . 1.529(2) ?
C17 C20 . 1.531(2) ?
C17 C19 . 1.539(2) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 C24B . 1.384(13) ?
C21 C24A . 1.500(4) ?
C21 C23B . 1.501(12) ?
C21 C23A . 1.525(3) ?
C21 C22A . 1.557(3) ?
C21 C22B . 1.650(11) ?
C25 C26 . 1.382(2) ?
C25 C30 . 1.390(2) ?
C25 O2 . 1.4089(17) ?
C26 C27 . 1.380(2) ?
C26 H26 . 0.93 ?
C27 C28 . 1.388(2) ?
C27 H27 . 0.93 ?
C28 C29 . 1.392(2) ?
C28 C31 . 1.534(2) ?
C29 C30 . 1.3999(19) ?
C29 H29 . 0.93 ?
C30 C35 . 1.542(2) ?
C31 C34 . 1.518(3) ?
C31 C33 . 1.525(3) ?
C31 C32 . 1.528(2) ?
C32 H32A . 0.96 ?
C32 H32B . 0.96 ?
C32 H32C . 0.96 ?
C33 H33A . 0.96 ?
C33 H33B . 0.96 ?
C33 H33C . 0.96 ?
C34 H34A . 0.96 ?
C34 H34B . 0.96 ?
C34 H34C . 0.96 ?
C35 C36 . 1.529(2) ?
C35 C38 . 1.533(2) ?
C35 C37 . 1.536(2) ?
C36 H36A . 0.96 ?
C36 H36B . 0.96 ?
C36 H36C . 0.96 ?
C37 H37A . 0.96 ?
C37 H37B . 0.96 ?
C37 H37C . 0.96 ?
C38 H38A . 0.96 ?
C38 H38B . 0.96 ?
C38 H38C . 0.96 ?
C22A H22A . 0.96 ?
C22A H22B . 0.96 ?
C22A H22C . 0.96 ?
C23A H23A . 0.96 ?
C23A H23B . 0.96 ?
C23A H23C . 0.96 ?
C24A H24A . 0.96 ?
C24A H24B . 0.96 ?
C24A H24C . 0.96 ?
C22B H22D . 0.96 ?
C22B H22E . 0.96 ?
C22B H22F . 0.96 ?
C23B H23D . 0.96 ?
C23B H23E . 0.96 ?
C23B H23F . 0.96 ?
C24B H24D . 0.96 ?
C24B H24E . 0.96 ?
C24B H24F . 0.96 ?
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
C19 H19B O1 . 0.96 2.5 3.117(2) 122
C20 H20A O1 . 0.96 2.32 2.982(3) 125
C36 H36B O2 . 0.96 2.52 3.122(3) 121
C37 H37B O2 . 0.96 2.29 2.966(2) 127
C22A H22A N2 2_657 0.96 2.59 3.535(4) 170
