#------------------------------------------------------------------------------
#$Date: 2024-08-05 22:45:03 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293893 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/32/7063282.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_7063282
loop_
_publ_author_name
'Li, Jun-Fei'
'Guan, Xiao-Hui'
'Feng, Hui-Jun'
'Zhou, Dai-Mei'
'Liu, Qiao-Yun'
'Zhang, Wen-Yao'
'Guo, Cai-Hong'
'Bai, Jun-Hua'
'Wang, Jun-Wen'
_publ_section_title
;
 A novel pyrazolium ionic liquid used for CO2 cycloaddition
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12706
_journal_page_last               12712
_journal_paper_doi               10.1039/D4NJ01776E
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C19 H21 N2, Br, H2 O'
_chemical_formula_sum            'C19 H23 Br N2 O'
_chemical_formula_weight         375.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-12-25
_audit_creation_method
; 
Olex2 1.5 
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) 
;
_audit_update_record
;
2024-02-20 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.492(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.9502(13)
_cell_length_b                   10.2847(9)
_cell_length_c                   24.072(2)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      65.12
_cell_measurement_theta_min      3.72
_cell_volume                     3650.6(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            32836
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        65.384
_diffrn_reflns_theta_max         65.384
_diffrn_reflns_theta_min         2.997
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.106
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1197 before and 0.0608 after correction. 
The Ratio of minimum to maximum transmission is 0.8394. 
The λ/2 correction factor is Not present. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0595P)²+3.5083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5219
_reflns_number_total             6184
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj01776e2.cif
_cod_data_source_block           cu_230826a_0m_a
_cod_depositor_comments          'Adding full bibliography for 7063282.cif.'
_cod_original_cell_volume        3650.6(6)
_cod_database_code               7063282
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_max   0.746
_shelx_estimated_absorpt_t_min   0.707
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H,H) groups 
2.a Riding coordinates: 
 O1(H1A,H1B), O2(H2A,H2B) 
2.b Secondary CH2 refined with riding coordinates: 
 C26(H26A,H26B), C33(H33A,H33B), C7(H7A,H7B), C13(H13A,H13B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), 
 C30(H30), C31(H31), C32(H32), C35(H35), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), 
  C9(H9), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19) 
2.d Idealised Me refined as rotating group: 
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C11(H11A,H11B,H11C), C12(H12A,H12B, 
 H12C) 
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.72739(16) 0.1835(2) 0.48366(10) 0.0299(5) Uani 1 1 d . . . . .
N4 N 0.80834(16) 0.2194(2) 0.51453(10) 0.0312(5) Uani 1 1 d . . . . .
C20 C 0.6890(2) -0.1109(3) 0.55743(14) 0.0403(7) Uani 1 1 d . . . . .
H20 H 0.734328 -0.158767 0.544708 0.048 Uiso 1 1 calc R U . . .
C21 C 0.6531(3) -0.1529(4) 0.60438(16) 0.0513(9) Uani 1 1 d . . . . .
H21 H 0.674446 -0.228960 0.622861 0.062 Uiso 1 1 calc R U . . .
C22 C 0.5861(2) -0.0818(4) 0.62327(14) 0.0482(9) Uani 1 1 d . . . . .
H22 H 0.562678 -0.109726 0.654691 0.058 Uiso 1 1 calc R U . . .
C23 C 0.5541(2) 0.0292(3) 0.59622(15) 0.0444(8) Uani 1 1 d . . . . .
H23 H 0.508648 0.076721 0.609066 0.053 Uiso 1 1 calc R U . . .
C24 C 0.5891(2) 0.0710(3) 0.54966(14) 0.0398(7) Uani 1 1 d . . . . .
H24 H 0.566775 0.146642 0.531227 0.048 Uiso 1 1 calc R U . . .
C25 C 0.6571(2) 0.0014(3) 0.53003(13) 0.0313(6) Uani 1 1 d . . . . .
C26 C 0.6952(2) 0.0476(3) 0.47903(13) 0.0329(7) Uani 1 1 d . . . . .
H26A H 0.745284 -0.008491 0.473676 0.039 Uiso 1 1 calc R U . . .
H26B H 0.648708 0.039446 0.445980 0.039 Uiso 1 1 calc R U . . .
C27 C 0.8693(2) 0.1650(3) 0.61313(14) 0.0365(7) Uani 1 1 d . . . . .
C28 C 0.9494(2) 0.1510(4) 0.65091(17) 0.0526(9) Uani 1 1 d . . . . .
H28 H 1.001100 0.120317 0.638360 0.063 Uiso 1 1 calc R U . . .
C29 C 0.9530(3) 0.1823(5) 0.70716(17) 0.0642(12) Uani 1 1 d . . . . .
H29 H 1.006904 0.171103 0.732163 0.077 Uiso 1 1 calc R U . . .
C30 C 0.8777(3) 0.2298(4) 0.72652(16) 0.0594(11) Uani 1 1 d . . . . .
H30 H 0.881161 0.253500 0.764091 0.071 Uiso 1 1 calc R U . . .
C31 C 0.7975(3) 0.2419(4) 0.68973(16) 0.0512(9) Uani 1 1 d . . . . .
H31 H 0.745856 0.271919 0.702556 0.061 Uiso 1 1 calc R U . . .
C32 C 0.7934(2) 0.2092(3) 0.63350(15) 0.0426(8) Uani 1 1 d . . . . .
H32 H 0.738720 0.217121 0.608983 0.051 Uiso 1 1 calc R U . . .
C33 C 0.8681(2) 0.1321(3) 0.55187(14) 0.0390(7) Uani 1 1 d . . . . .
H33A H 0.929207 0.138318 0.543405 0.047 Uiso 1 1 calc R U . . .
H33B H 0.847667 0.043113 0.545005 0.047 Uiso 1 1 calc R U . . .
C34 C 0.6880(2) 0.2896(3) 0.45740(12) 0.0316(6) Uani 1 1 d . . . . .
C35 C 0.7452(2) 0.3936(3) 0.47224(13) 0.0354(7) Uani 1 1 d . . . . .
H35 H 0.735143 0.479174 0.460357 0.042 Uiso 1 1 calc R U . . .
C36 C 0.8201(2) 0.3474(3) 0.50794(13) 0.0337(7) Uani 1 1 d . . . . .
C37 C 0.5993(2) 0.2849(3) 0.41947(13) 0.0389(7) Uani 1 1 d . . . . .
H37A H 0.603721 0.228997 0.388116 0.058 Uiso 1 1 calc R U . . .
H37B H 0.582709 0.370874 0.405993 0.058 Uiso 1 1 calc R U . . .
H37C H 0.553971 0.251869 0.439739 0.058 Uiso 1 1 calc R U . . .
C38 C 0.9026(2) 0.4166(3) 0.53585(16) 0.0442(8) Uani 1 1 d . . . . .
H38A H 0.902035 0.421413 0.575626 0.066 Uiso 1 1 calc R U . . .
H38B H 0.903355 0.502922 0.520736 0.066 Uiso 1 1 calc R U . . .
H38C H 0.955563 0.370345 0.529243 0.066 Uiso 1 1 calc R U . . .
N1 N 0.66849(15) 0.5625(2) 0.29027(10) 0.0256(5) Uani 1 1 d . . . . .
N2 N 0.75259(15) 0.6009(2) 0.31674(10) 0.0275(5) Uani 1 1 d . . . . .
C1 C 0.54793(19) 0.6370(3) 0.34082(12) 0.0289(6) Uani 1 1 d . . . . .
C2 C 0.5964(2) 0.6717(3) 0.39315(13) 0.0362(7) Uani 1 1 d . . . . .
H2 H 0.654079 0.707365 0.395815 0.043 Uiso 1 1 calc R U . . .
C3 C 0.5581(3) 0.6528(3) 0.44145(14) 0.0460(8) Uani 1 1 d . . . . .
H3 H 0.590842 0.675197 0.476416 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4728(3) 0.6015(3) 0.43807(15) 0.0467(9) Uani 1 1 d . . . . .
H4 H 0.448088 0.588252 0.470644 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4237(2) 0.5697(3) 0.38644(15) 0.0430(8) Uani 1 1 d . . . . .
H5 H 0.365168 0.537041 0.384003 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4615(2) 0.5862(3) 0.33780(13) 0.0341(7) Uani 1 1 d . . . . .
H6 H 0.428479 0.562859 0.303041 0.041 Uiso 1 1 calc R U . . .
C7 C 0.58899(19) 0.6492(3) 0.28769(12) 0.0288(6) Uani 1 1 d . . . . .
H7A H 0.543994 0.626494 0.255337 0.035 Uiso 1 1 calc R U . . .
H7B H 0.607400 0.738519 0.283212 0.035 Uiso 1 1 calc R U . . .
C8 C 0.66490(19) 0.4315(3) 0.29248(11) 0.0269(6) Uani 1 1 d . . . . .
C9 C 0.7475(2) 0.3872(3) 0.31925(12) 0.0311(6) Uani 1 1 d . . . . .
H9 H 0.763739 0.300866 0.326653 0.037 Uiso 1 1 calc R U . . .
C10 C 0.8020(2) 0.4946(3) 0.33314(12) 0.0305(6) Uani 1 1 d . . . . .
C11 C 0.5817(2) 0.3588(3) 0.26817(14) 0.0382(7) Uani 1 1 d . . . . .
H11A H 0.594438 0.267226 0.269370 0.057 Uiso 1 1 calc R U . . .
H11B H 0.562607 0.385266 0.229812 0.057 Uiso 1 1 calc R U . . .
H11C H 0.534450 0.376860 0.289624 0.057 Uiso 1 1 calc R U . . .
C12 C 0.8990(2) 0.5029(3) 0.36002(16) 0.0436(8) Uani 1 1 d . . . . .
H12A H 0.919481 0.418928 0.374184 0.065 Uiso 1 1 calc R U . . .
H12B H 0.905107 0.564078 0.390538 0.065 Uiso 1 1 calc R U . . .
H12C H 0.934866 0.531081 0.332675 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7862(2) 0.7326(3) 0.30900(13) 0.0318(6) Uani 1 1 d . . . . .
H13A H 0.839510 0.748300 0.337134 0.038 Uiso 1 1 calc R U . . .
H13B H 0.740205 0.794974 0.315207 0.038 Uiso 1 1 calc R U . . .
C14 C 0.81046(19) 0.7552(3) 0.25109(13) 0.0321(6) Uani 1 1 d . . . . .
C15 C 0.8048(2) 0.8799(3) 0.22934(15) 0.0438(8) Uani 1 1 d . . . . .
H15 H 0.780638 0.946223 0.248566 0.053 Uiso 1 1 calc R U . . .
C16 C 0.8348(3) 0.9067(3) 0.17923(17) 0.0538(10) Uani 1 1 d . . . . .
H16 H 0.830165 0.990931 0.164958 0.065 Uiso 1 1 calc R U . . .
C17 C 0.8714(2) 0.8106(3) 0.15022(15) 0.0467(8) Uani 1 1 d . . . . .
H17 H 0.892758 0.829671 0.116995 0.056 Uiso 1 1 calc R U . . .
C18 C 0.8758(2) 0.6858(4) 0.17109(15) 0.0480(9) Uani 1 1 d . . . . .
H18 H 0.899761 0.619705 0.151634 0.058 Uiso 1 1 calc R U . . .
C19 C 0.8449(2) 0.6581(3) 0.22078(14) 0.0412(8) Uani 1 1 d . . . . .
H19 H 0.847219 0.573091 0.234078 0.049 Uiso 1 1 calc R U . . .
Br1 Br 0.63453(2) 0.01642(3) 0.31713(2) 0.04061(13) Uani 1 1 d . . . . .
Br2 Br 0.86561(3) -0.22633(4) 0.46748(2) 0.06326(16) Uani 1 1 d . . . . .
O1 O 0.8502(2) 0.0242(4) 0.38264(16) 0.0900(11) Uani 1 1 d . . . . .
H1A H 0.800613 0.028493 0.359641 0.135 Uiso 1 1 d R U . . .
H1B H 0.832553 -0.003447 0.412311 0.135 Uiso 1 1 d R U . . .
O2 O 0.9568(3) 0.2301(4) 0.42662(17) 0.0951(11) Uani 1 1 d . . . . .
H2A H 0.933298 0.157634 0.415202 0.143 Uiso 1 1 d R U . . .
H2B H 0.998468 0.217504 0.454702 0.143 Uiso 1 1 d R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N4 N3 C26 123.1(2) . . ?
C34 N3 N4 108.5(2) . . ?
C34 N3 C26 128.3(3) . . ?
N3 N4 C33 124.4(2) . . ?
C36 N4 N3 108.9(2) . . ?
C36 N4 C33 126.6(3) . . ?
C21 C20 H20 120.0 . . ?
C25 C20 H20 120.0 . . ?
C25 C20 C21 119.9(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C25 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 C24 119.0(3) . . ?
C20 C25 C26 120.4(3) . . ?
C24 C25 C26 120.7(3) . . ?
N3 C26 C25 113.4(2) . . ?
N3 C26 H26A 108.9 . . ?
N3 C26 H26B 108.9 . . ?
C25 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C28 C27 C33 119.1(3) . . ?
C32 C27 C28 118.1(3) . . ?
C32 C27 C33 122.8(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.5(4) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.8(4) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 120.3 . . ?
C31 C30 C29 119.3(4) . . ?
C31 C30 H30 120.3 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0(4) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 121.3(3) . . ?
C27 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
N4 C33 C27 111.6(2) . . ?
N4 C33 H33A 109.3 . . ?
N4 C33 H33B 109.3 . . ?
C27 C33 H33A 109.3 . . ?
C27 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?
N3 C34 C35 107.6(3) . . ?
N3 C34 C37 122.7(3) . . ?
C35 C34 C37 129.7(3) . . ?
C34 C35 H35 126.3 . . ?
C36 C35 C34 107.4(3) . . ?
C36 C35 H35 126.3 . . ?
N4 C36 C35 107.7(3) . . ?
N4 C36 C38 122.2(3) . . ?
C35 C36 C38 130.1(3) . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N2 N1 C7 121.0(2) . . ?
C8 N1 N2 108.0(2) . . ?
C8 N1 C7 124.5(2) . . ?
N1 N2 C13 120.9(2) . . ?
C10 N2 N1 108.7(2) . . ?
C10 N2 C13 127.3(2) . . ?
C2 C1 C7 121.4(3) . . ?
C6 C1 C2 119.1(3) . . ?
C6 C1 C7 119.5(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C1 110.5(2) . . ?
N1 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C1 C7 H7A 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C9 108.1(2) . . ?
N1 C8 C11 121.5(3) . . ?
C9 C8 C11 130.4(3) . . ?
C8 C9 H9 126.3 . . ?
C8 C9 C10 107.3(2) . . ?
C10 C9 H9 126.3 . . ?
N2 C10 C9 107.8(3) . . ?
N2 C10 C12 122.0(3) . . ?
C9 C10 C12 130.1(3) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 108.9 . . ?
N2 C13 H13B 108.9 . . ?
N2 C13 C14 113.4(2) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C15 C14 C13 118.8(3) . . ?
C15 C14 C19 118.3(3) . . ?
C19 C14 C13 122.7(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 120.9(3) . . ?
C18 C19 H19 119.5 . . ?
H1A O1 H1B 101.9 . . ?
H2A O2 H2B 109.5 . . ?
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
N3 N4 1.363(3) . ?
N3 C26 1.477(4) . ?
N3 C34 1.347(4) . ?
N4 C33 1.466(4) . ?
N4 C36 1.340(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.397(5) . ?
C20 C25 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.376(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.361(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.388(4) . ?
C25 C26 1.512(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.387(5) . ?
C27 C32 1.384(5) . ?
C27 C33 1.510(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.384(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.377(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.374(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.386(5) . ?
C32 H32 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.379(4) . ?
C34 C37 1.481(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.379(4) . ?
C36 C38 1.485(4) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
N1 N2 1.370(3) . ?
N1 C7 1.479(3) . ?
N1 C8 1.350(4) . ?
N2 C10 1.342(4) . ?
N2 C13 1.468(3) . ?
C1 C2 1.392(4) . ?
C1 C6 1.385(4) . ?
C1 C7 1.512(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.373(4) . ?
C8 C11 1.486(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(4) . ?
C10 C12 1.490(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.515(4) . ?
C14 C15 1.382(4) . ?
C14 C19 1.385(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(5) . ?
C19 H19 0.9300 . ?
O1 H1A 0.8499 . ?
O1 H1B 0.8499 . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8501 . ?
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
N3 N4 C33 C27 -109.1(3) . . . . ?
N3 N4 C36 C35 0.0(3) . . . . ?
N3 N4 C36 C38 -179.5(3) . . . . ?
N3 C34 C35 C36 0.2(3) . . . . ?
N4 N3 C26 C25 78.3(3) . . . . ?
N4 N3 C34 C35 -0.1(3) . . . . ?
N4 N3 C34 C37 179.1(3) . . . . ?
C20 C21 C22 C23 0.4(6) . . . . ?
C20 C25 C26 N3 -126.9(3) . . . . ?
C21 C20 C25 C24 -0.3(5) . . . . ?
C21 C20 C25 C26 -179.8(3) . . . . ?
C21 C22 C23 C24 -0.2(6) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C23 C24 C25 C20 0.5(5) . . . . ?
C23 C24 C25 C26 180.0(3) . . . . ?
C24 C25 C26 N3 53.6(4) . . . . ?
C25 C20 C21 C22 -0.2(6) . . . . ?
C26 N3 N4 C33 -7.5(4) . . . . ?
C26 N3 N4 C36 176.7(2) . . . . ?
C26 N3 C34 C35 -176.6(3) . . . . ?
C26 N3 C34 C37 2.6(4) . . . . ?
C27 C28 C29 C30 -1.0(6) . . . . ?
C28 C27 C32 C31 1.6(5) . . . . ?
C28 C27 C33 N4 -144.3(3) . . . . ?
C28 C29 C30 C31 2.2(6) . . . . ?
C29 C30 C31 C32 -1.5(6) . . . . ?
C30 C31 C32 C27 -0.4(5) . . . . ?
C32 C27 C28 C29 -0.9(5) . . . . ?
C32 C27 C33 N4 35.6(4) . . . . ?
C33 N4 C36 C35 -175.6(3) . . . . ?
C33 N4 C36 C38 4.9(4) . . . . ?
C33 C27 C28 C29 179.0(3) . . . . ?
C33 C27 C32 C31 -178.3(3) . . . . ?
C34 N3 N4 C33 175.8(3) . . . . ?
C34 N3 N4 C36 0.1(3) . . . . ?
C34 N3 C26 C25 -105.7(3) . . . . ?
C34 C35 C36 N4 -0.1(3) . . . . ?
C34 C35 C36 C38 179.3(3) . . . . ?
C36 N4 C33 C27 65.9(4) . . . . ?
C37 C34 C35 C36 -179.0(3) . . . . ?
N1 N2 C10 C9 -2.7(3) . . . . ?
N1 N2 C10 C12 176.0(3) . . . . ?
N1 N2 C13 C14 -71.7(3) . . . . ?
N1 C8 C9 C10 -0.3(3) . . . . ?
N2 N1 C7 C1 -84.2(3) . . . . ?
N2 N1 C8 C9 -1.3(3) . . . . ?
N2 N1 C8 C11 179.0(2) . . . . ?
N2 C13 C14 C15 152.3(3) . . . . ?
N2 C13 C14 C19 -32.9(4) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 C7 N1 63.2(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 C4 C5 C6 1.7(5) . . . . ?
C4 C5 C6 C1 -1.3(5) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C6 C1 C7 N1 -114.5(3) . . . . ?
C7 N1 N2 C10 155.4(2) . . . . ?
C7 N1 N2 C13 -43.1(3) . . . . ?
C7 N1 C8 C9 -153.0(3) . . . . ?
C7 N1 C8 C11 27.3(4) . . . . ?
C7 C1 C2 C3 -176.6(3) . . . . ?
C7 C1 C6 C5 177.6(3) . . . . ?
C8 N1 N2 C10 2.5(3) . . . . ?
C8 N1 N2 C13 164.1(2) . . . . ?
C8 N1 C7 C1 64.0(3) . . . . ?
C8 C9 C10 N2 1.9(3) . . . . ?
C8 C9 C10 C12 -176.7(3) . . . . ?
C10 N2 C13 C14 86.2(4) . . . . ?
C11 C8 C9 C10 179.3(3) . . . . ?
C13 N2 C10 C9 -162.7(3) . . . . ?
C13 N2 C10 C12 16.0(4) . . . . ?
C13 C14 C15 C16 173.6(3) . . . . ?
C13 C14 C19 C18 -172.5(3) . . . . ?
C14 C15 C16 C17 -0.5(6) . . . . ?
C15 C14 C19 C18 2.3(5) . . . . ?
C15 C16 C17 C18 1.6(6) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
C17 C18 C19 C14 -1.2(6) . . . . ?
C19 C14 C15 C16 -1.4(5) . . . . ?
