#------------------------------------------------------------------------------
#$Date: 2020-07-06 04:49:47 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253793 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126425.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_7126425
loop_
_publ_author_name
'Ou, Changjin'
'Zhang, Yewei'
'Ge, Wei'
'Zhong, Liping'
'Huang, Yong'
'Si, Weili'
'Wang, Wenjun'
'Zhao, Yongxiang'
'Dong, Xiaochen'
_publ_section_title
;
 A three-dimensional BODIPY-iron(iii) compound with improved
 H₂O₂-response for NIR-II photoacoustic imaging
 guided chemodynamic/photothermal therapy.
;
_journal_issue                   46
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6281
_journal_page_last               6284
_journal_paper_doi               10.1039/d0cc01164a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C33 H27 B F2 N2 O4, C6 H11 N O'
_chemical_formula_sum            'C39 H38 B F2 N3 O5'
_chemical_formula_weight         677.53
_chemical_name_common            BODIPY
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-30
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.05.22 svn.r3414 for OlexSys, GUI svn.r5347)
;
_audit_update_record
;
2019-08-30 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                113.934(4)
_cell_angle_beta                 105.531(5)
_cell_angle_gamma                98.396(5)
_cell_formula_units_Z            2
_cell_length_a                   11.152(2)
_cell_length_b                   12.967(3)
_cell_length_c                   13.780(3)
_cell_measurement_reflns_used    2704
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.26
_cell_volume                     1679.9(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.26
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7570
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.734
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5565
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.0991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0395P)²+4.4029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1891
_refine_ls_wR_factor_ref         0.2216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3184
_reflns_number_total             5565
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01164a2.cif
_cod_data_source_block           111
_cod_depositor_comments          'Adding full bibliography for 7126425.cif.'
_cod_database_code               7126425
_shelx_shelxl_version_number     2016/6
_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.
;
_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
2. Restrained distances
 O2-H2 = O1-H1 = O3-H3 = O4-H4
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C19(H19),
 C20(H20), C22(H22), C23(H23), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
F1 F 0.3342(3) 0.3897(3) 0.0956(2) 0.0515(8) Uani 1 1 d . . . . .
F2 F 0.2074(3) 0.2214(3) 0.0705(2) 0.0562(9) Uani 1 1 d . . . . .
O1 O 0.5359(4) 0.4498(4) 0.6382(3) 0.0630(12) Uani 1 1 d D . . . .
H1 H 0.455(2) 0.415(5) 0.595(4) 0.06(2) Uiso 1 1 d D . . . .
O2 O 0.7810(4) 0.4755(4) 0.7524(3) 0.0638(12) Uani 1 1 d D . . . .
H2 H 0.714(4) 0.491(6) 0.767(6) 0.09(3) Uiso 1 1 d D . . . .
O3 O -0.1560(4) 0.5185(5) 0.3033(3) 0.0734(14) Uani 1 1 d D . . . .
H3 H -0.218(6) 0.533(7) 0.329(7) 0.13(3) Uiso 1 1 d D . . . .
O4 O -0.4001(4) 0.5134(4) 0.2036(4) 0.0611(12) Uani 1 1 d D . . . .
H4 H -0.484(3) 0.478(7) 0.168(6) 0.13(3) Uiso 1 1 d D . . . .
N1 N 0.3826(4) 0.2082(4) -0.0004(3) 0.0382(10) Uani 1 1 d . . . . .
N2 N 0.1853(4) 0.2505(4) -0.0951(3) 0.0393(11) Uani 1 1 d . . . . .
C1 C 0.4800(5) 0.2022(5) 0.0779(4) 0.0429(13) Uani 1 1 d . . . . .
C2 C 0.5575(6) 0.1441(5) 0.0226(4) 0.0502(15) Uani 1 1 d . . . . .
H2A H 0.630538 0.127761 0.057628 0.060 Uiso 1 1 calc R . . . .
C3 C 0.5098(6) 0.1154(5) -0.0895(4) 0.0459(14) Uani 1 1 d . . . . .
C4 C 0.3980(5) 0.1564(5) -0.1067(4) 0.0399(13) Uani 1 1 d . . . . .
C5 C 0.3140(5) 0.1569(4) -0.2007(4) 0.0413(13) Uani 1 1 d . . . . .
C6 C 0.2101(5) 0.2040(5) -0.1968(4) 0.0411(13) Uani 1 1 d . . . . .
C7 C 0.1091(5) 0.2079(5) -0.2817(4) 0.0447(14) Uani 1 1 d . . . . .
C8 C 0.0268(6) 0.2549(5) -0.2315(4) 0.0498(15) Uani 1 1 d . . . . .
H8 H -0.048702 0.267224 -0.267961 0.060 Uiso 1 1 calc R . . . .
C9 C 0.0735(5) 0.2817(5) -0.1170(4) 0.0408(13) Uani 1 1 d . . . . .
C10 C 0.5018(5) 0.2550(5) 0.1985(4) 0.0412(13) Uani 1 1 d . . . . .
H10 H 0.437328 0.282803 0.222768 0.049 Uiso 1 1 calc R . . . .
C11 C 0.6097(6) 0.2651(5) 0.2752(4) 0.0467(14) Uani 1 1 d . . . . .
H11 H 0.669446 0.233015 0.246202 0.056 Uiso 1 1 calc R . . . .
C12 C 0.6489(5) 0.3192(5) 0.3989(4) 0.0419(13) Uani 1 1 d . . . . .
C13 C 0.7754(6) 0.3336(5) 0.4630(4) 0.0480(14) Uani 1 1 d . . . . .
H13 H 0.831693 0.307192 0.425916 0.058 Uiso 1 1 calc R . . . .
C14 C 0.8196(5) 0.3859(5) 0.5801(4) 0.0482(14) Uani 1 1 d . . . . .
H14 H 0.905282 0.396183 0.621451 0.058 Uiso 1 1 calc R . . . .
C15 C 0.7359(5) 0.4231(5) 0.6360(4) 0.0443(13) Uani 1 1 d . . . . .
C16 C 0.6089(5) 0.4090(5) 0.5740(4) 0.0410(13) Uani 1 1 d . . . . .
C17 C 0.5660(5) 0.3574(5) 0.4571(4) 0.0428(13) Uani 1 1 d . . . . .
H17 H 0.480369 0.347826 0.416139 0.051 Uiso 1 1 calc R . . . .
C18 C 0.5713(6) 0.0570(6) -0.1747(5) 0.0628(18) Uani 1 1 d . . . . .
H18A H 0.511628 -0.017360 -0.233880 0.094 Uiso 1 1 calc GR . . . .
H18B H 0.649379 0.044449 -0.137058 0.094 Uiso 1 1 calc GR . . . .
H18C H 0.592071 0.106847 -0.207380 0.094 Uiso 1 1 calc GR . . . .
C19 C 0.0139(5) 0.3295(5) -0.0339(4) 0.0432(13) Uani 1 1 d . . . . .
H19 H 0.059262 0.351373 0.042074 0.052 Uiso 1 1 calc R . . . .
C20 C -0.1027(5) 0.3428(5) -0.0630(4) 0.0456(14) Uani 1 1 d . . . . .
H20 H -0.142614 0.320923 -0.139749 0.055 Uiso 1 1 calc R . . . .
C21 C -0.1784(5) 0.3869(5) 0.0075(4) 0.0426(13) Uani 1 1 d . . . . .
C22 C -0.3059(6) 0.3805(5) -0.0453(5) 0.0489(14) Uani 1 1 d . . . . .
H22 H -0.340108 0.349151 -0.124139 0.059 Uiso 1 1 calc R . . . .
C23 C -0.3834(6) 0.4200(5) 0.0170(5) 0.0499(15) Uani 1 1 d . . . . .
H23 H -0.469045 0.414195 -0.019830 0.060 Uiso 1 1 calc R . . . .
C24 C -0.3331(5) 0.4678(5) 0.1338(5) 0.0455(14) Uani 1 1 d . . . . .
C25 C -0.2063(6) 0.4734(5) 0.1874(5) 0.0487(14) Uani 1 1 d . . . . .
C26 C -0.1299(5) 0.4342(5) 0.1247(5) 0.0464(14) Uani 1 1 d . . . . .
H26 H -0.044451 0.439694 0.161821 0.056 Uiso 1 1 calc R . . . .
C27 C 0.0911(7) 0.1715(6) -0.4050(5) 0.0643(18) Uani 1 1 d . . . . .
H27A H 0.159072 0.222903 -0.408715 0.096 Uiso 1 1 calc GR . . . .
H27B H 0.008330 0.176806 -0.443181 0.096 Uiso 1 1 calc GR . . . .
H27C H 0.094552 0.091866 -0.441285 0.096 Uiso 1 1 calc GR . . . .
C28 C 0.3328(6) 0.1066(5) -0.3131(4) 0.0498(15) Uani 1 1 d . . . . .
C29 C 0.3954(6) 0.1788(6) -0.3467(5) 0.0586(17) Uani 1 1 d . . . . .
H29 H 0.429393 0.259496 -0.298421 0.070 Uiso 1 1 calc R . . . .
C30 C 0.4071(8) 0.1312(7) -0.4515(6) 0.076(2) Uani 1 1 d . . . . .
H30 H 0.448954 0.179971 -0.473998 0.091 Uiso 1 1 calc R . . . .
C31 C 0.3577(8) 0.0124(7) -0.5232(6) 0.085(2) Uani 1 1 d . . . . .
H31 H 0.365563 -0.018659 -0.594257 0.102 Uiso 1 1 calc R . . . .
C32 C 0.2965(8) -0.0612(7) -0.4909(6) 0.080(2) Uani 1 1 d . . . . .
H32 H 0.263339 -0.141811 -0.539620 0.096 Uiso 1 1 calc R . . . .
C33 C 0.2849(7) -0.0140(6) -0.3853(5) 0.0678(19) Uani 1 1 d . . . . .
H33 H 0.244776 -0.063379 -0.362372 0.081 Uiso 1 1 calc R . . . .
B1 B 0.2756(6) 0.2674(5) 0.0190(5) 0.0400(15) Uani 1 1 d . . . . .
O5 O -0.2718(5) 0.6277(5) 0.4698(4) 0.0845(16) Uani 1 1 d . . . . .
N3 N -0.1344(6) 0.7298(5) 0.6539(5) 0.0734(16) Uani 1 1 d . . . . .
C34 C -0.1804(8) 0.6420(6) 0.5485(6) 0.072(2) Uani 1 1 d . . . . .
H34 H -0.136661 0.584787 0.533950 0.087 Uiso 1 1 calc R . . . .
C35 C -0.0259(9) 0.7355(9) 0.7449(7) 0.108(3) Uani 1 1 d . . . . .
H35A H -0.057916 0.721465 0.798650 0.129 Uiso 1 1 calc R . . . .
H35B H 0.013540 0.674241 0.712983 0.129 Uiso 1 1 calc R . . . .
C36 C 0.0717(10) 0.8498(13) 0.8044(10) 0.156(5) Uani 1 1 d . . . . .
H36A H 0.115281 0.857924 0.754557 0.187 Uiso 1 1 calc R . . . .
H36B H 0.136342 0.855138 0.870693 0.187 Uiso 1 1 calc R . . . .
C37 C 0.0093(14) 0.9492(10) 0.8416(9) 0.157(5) Uani 1 1 d . . . . .
H37A H -0.025390 0.946684 0.898345 0.188 Uiso 1 1 calc R . . . .
H37B H 0.074597 1.024542 0.875947 0.188 Uiso 1 1 calc R . . . .
C38 C -0.0977(13) 0.9378(8) 0.7419(10) 0.143(4) Uani 1 1 d . . . . .
H38A H -0.139519 0.999011 0.767447 0.172 Uiso 1 1 calc R . . . .
H38B H -0.061849 0.947681 0.688311 0.172 Uiso 1 1 calc R . . . .
C39 C -0.1940(9) 0.8215(8) 0.6853(7) 0.104(3) Uani 1 1 d . . . . .
H39A H -0.236824 0.815428 0.736207 0.125 Uiso 1 1 calc R . . . .
H39B H -0.259537 0.813119 0.617801 0.125 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
C16 O1 H1 108(4) . . ?
C15 O2 H2 102(5) . . ?
C25 O3 H3 108(6) . . ?
C24 O4 H4 111(6) . . ?
C1 N1 C4 108.7(4) . . ?
C1 N1 B1 127.6(4) . . ?
C4 N1 B1 123.6(4) . . ?
C6 N2 B1 124.2(4) . . ?
C9 N2 C6 107.7(4) . . ?
C9 N2 B1 128.1(4) . . ?
N1 C1 C2 107.9(4) . . ?
N1 C1 C10 124.2(5) . . ?
C2 C1 C10 127.7(5) . . ?
C1 C2 H2A 125.1 . . ?
C3 C2 C1 109.9(5) . . ?
C3 C2 H2A 125.1 . . ?
C2 C3 C4 106.6(5) . . ?
C2 C3 C18 124.9(5) . . ?
C4 C3 C18 128.4(5) . . ?
N1 C4 C3 106.9(4) . . ?
C5 C4 N1 120.2(5) . . ?
C5 C4 C3 132.9(5) . . ?
C4 C5 C6 122.7(4) . . ?
C4 C5 C28 120.6(5) . . ?
C6 C5 C28 116.7(5) . . ?
N2 C6 C7 107.7(4) . . ?
C5 C6 N2 119.7(5) . . ?
C5 C6 C7 132.4(5) . . ?
C6 C7 C27 129.1(5) . . ?
C8 C7 C6 106.9(4) . . ?
C8 C7 C27 124.0(5) . . ?
C7 C8 H8 125.3 . . ?
C7 C8 C9 109.3(5) . . ?
C9 C8 H8 125.3 . . ?
N2 C9 C8 108.4(4) . . ?
N2 C9 C19 124.1(4) . . ?
C8 C9 C19 127.5(5) . . ?
C1 C10 H10 118.8 . . ?
C11 C10 C1 122.5(5) . . ?
C11 C10 H10 118.8 . . ?
C10 C11 H11 115.3 . . ?
C10 C11 C12 129.4(5) . . ?
C12 C11 H11 115.3 . . ?
C13 C12 C11 118.5(5) . . ?
C13 C12 C17 117.8(5) . . ?
C17 C12 C11 123.7(5) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.6(5) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
O2 C15 C14 119.1(5) . . ?
O2 C15 C16 121.0(5) . . ?
C14 C15 C16 119.9(5) . . ?
O1 C16 C15 114.6(5) . . ?
O1 C16 C17 125.4(5) . . ?
C17 C16 C15 120.1(5) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.0(5) . . ?
C16 C17 H17 119.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C19 H19 119.2 . . ?
C20 C19 C9 121.6(5) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 115.3 . . ?
C19 C20 C21 129.3(5) . . ?
C21 C20 H20 115.3 . . ?
C22 C21 C20 118.5(5) . . ?
C26 C21 C20 123.3(5) . . ?
C26 C21 C22 118.1(5) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.3(5) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.7(5) . . ?
C24 C23 H23 120.1 . . ?
O4 C24 C23 124.3(5) . . ?
O4 C24 C25 116.2(5) . . ?
C23 C24 C25 119.6(5) . . ?
O3 C25 C24 120.1(5) . . ?
O3 C25 C26 119.6(5) . . ?
C26 C25 C24 120.3(5) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 C21 121.0(5) . . ?
C25 C26 H26 119.5 . . ?
C7 C27 H27A 109.5 . . ?
C7 C27 H27B 109.5 . . ?
C7 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C5 121.0(5) . . ?
C29 C28 C33 119.4(5) . . ?
C33 C28 C5 119.7(5) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.8(6) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.7 . . ?
C31 C30 C29 120.6(7) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 119.8 . . ?
C30 C31 C32 120.5(6) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 120.4 . . ?
C31 C32 C33 119.3(7) . . ?
C33 C32 H32 120.4 . . ?
C28 C33 H33 119.8 . . ?
C32 C33 C28 120.4(6) . . ?
C32 C33 H33 119.8 . . ?
F1 B1 N1 109.0(4) . . ?
F1 B1 N2 110.1(5) . . ?
F2 B1 F1 106.8(4) . . ?
F2 B1 N1 110.4(5) . . ?
F2 B1 N2 111.4(5) . . ?
N2 B1 N1 109.1(4) . . ?
C34 N3 C35 123.0(7) . . ?
C34 N3 C39 120.8(7) . . ?
C39 N3 C35 116.2(7) . . ?
O5 C34 N3 127.5(8) . . ?
O5 C34 H34 116.2 . . ?
N3 C34 H34 116.2 . . ?
N3 C35 H35A 109.4 . . ?
N3 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C36 C35 N3 111.3(9) . . ?
C36 C35 H35A 109.4 . . ?
C36 C35 H35B 109.4 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 C37 110.7(9) . . ?
H36A C36 H36B 108.1 . . ?
C37 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 108.1 . . ?
C38 C37 C36 110.6(9) . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
C37 C38 H38A 109.6 . . ?
C37 C38 H38B 109.6 . . ?
H38A C38 H38B 108.1 . . ?
C39 C38 C37 110.2(9) . . ?
C39 C38 H38A 109.6 . . ?
C39 C38 H38B 109.6 . . ?
N3 C39 C38 111.1(8) . . ?
N3 C39 H39A 109.4 . . ?
N3 C39 H39B 109.4 . . ?
C38 C39 H39A 109.4 . . ?
C38 C39 H39B 109.4 . . ?
H39A C39 H39B 108.0 . . ?
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
F1 B1 1.423(7) . ?
F2 B1 1.391(6) . ?
O1 H1 0.87(2) . ?
O1 C16 1.362(6) . ?
O2 H2 0.86(2) . ?
O2 C15 1.367(6) . ?
O3 H3 0.87(2) . ?
O3 C25 1.368(7) . ?
O4 H4 0.88(2) . ?
O4 C24 1.374(6) . ?
N1 C1 1.347(6) . ?
N1 C4 1.413(6) . ?
N1 B1 1.536(7) . ?
N2 C6 1.406(6) . ?
N2 C9 1.362(6) . ?
N2 B1 1.530(7) . ?
C1 C2 1.404(7) . ?
C1 C10 1.450(7) . ?
C2 H2A 0.9300 . ?
C2 C3 1.358(7) . ?
C3 C4 1.425(7) . ?
C3 C18 1.512(7) . ?
C4 C5 1.383(7) . ?
C5 C6 1.389(7) . ?
C5 C28 1.505(7) . ?
C6 C7 1.413(7) . ?
C7 C8 1.361(7) . ?
C7 C27 1.513(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.395(7) . ?
C9 C19 1.445(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.321(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.459(7) . ?
C12 C13 1.389(7) . ?
C12 C17 1.397(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(7) . ?
C15 C16 1.385(7) . ?
C16 C17 1.374(7) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.314(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.452(7) . ?
C21 C22 1.387(7) . ?
C21 C26 1.382(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.375(7) . ?
C24 C25 1.385(8) . ?
C25 C26 1.376(7) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.383(8) . ?
C28 C33 1.389(8) . ?
C29 H29 0.9300 . ?
C29 C30 1.373(8) . ?
C30 H30 0.9300 . ?
C30 C31 1.371(10) . ?
C31 H31 0.9300 . ?
C31 C32 1.375(10) . ?
C32 H32 0.9300 . ?
C32 C33 1.383(8) . ?
C33 H33 0.9300 . ?
O5 C34 1.200(8) . ?
N3 C34 1.326(8) . ?
N3 C35 1.459(9) . ?
N3 C39 1.418(9) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.456(13) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.525(15) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.497(15) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.469(12) . ?
C39 H39A 0.9700 . ?
C39 H39B 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
O1 C16 C17 C12 179.5(5) . . . . ?
O2 C15 C16 O1 -0.7(8) . . . . ?
O2 C15 C16 C17 179.2(5) . . . . ?
O3 C25 C26 C21 179.2(5) . . . . ?
O4 C24 C25 O3 2.2(8) . . . . ?
O4 C24 C25 C26 -177.4(5) . . . . ?
N1 C1 C2 C3 0.9(7) . . . . ?
N1 C1 C10 C11 -168.1(5) . . . . ?
N1 C4 C5 C6 -2.0(8) . . . . ?
N1 C4 C5 C28 177.4(5) . . . . ?
N2 C6 C7 C8 -0.3(6) . . . . ?
N2 C6 C7 C27 178.3(6) . . . . ?
N2 C9 C19 C20 -170.4(5) . . . . ?
C1 N1 C4 C3 1.4(6) . . . . ?
C1 N1 C4 C5 -176.6(5) . . . . ?
C1 N1 B1 F1 60.5(7) . . . . ?
C1 N1 B1 F2 -56.5(7) . . . . ?
C1 N1 B1 N2 -179.3(5) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C1 C2 C3 C18 177.0(6) . . . . ?
C1 C10 C11 C12 177.5(5) . . . . ?
C2 C1 C10 C11 7.4(9) . . . . ?
C2 C3 C4 N1 -0.8(6) . . . . ?
C2 C3 C4 C5 176.7(6) . . . . ?
C3 C4 C5 C6 -179.3(6) . . . . ?
C3 C4 C5 C28 0.1(9) . . . . ?
C4 N1 C1 C2 -1.4(6) . . . . ?
C4 N1 C1 C10 174.9(5) . . . . ?
C4 N1 B1 F1 -115.2(5) . . . . ?
C4 N1 B1 F2 127.8(5) . . . . ?
C4 N1 B1 N2 5.0(7) . . . . ?
C4 C5 C6 N2 -1.8(8) . . . . ?
C4 C5 C6 C7 -175.7(6) . . . . ?
C4 C5 C28 C29 -98.0(7) . . . . ?
C4 C5 C28 C33 83.0(7) . . . . ?
C5 C6 C7 C8 174.2(6) . . . . ?
C5 C6 C7 C27 -7.3(10) . . . . ?
C5 C28 C29 C30 -177.6(6) . . . . ?
C5 C28 C33 C32 177.3(6) . . . . ?
C6 N2 C9 C8 0.3(6) . . . . ?
C6 N2 C9 C19 177.9(5) . . . . ?
C6 N2 B1 F1 110.7(5) . . . . ?
C6 N2 B1 F2 -131.0(5) . . . . ?
C6 N2 B1 N1 -8.9(7) . . . . ?
C6 C5 C28 C29 81.4(7) . . . . ?
C6 C5 C28 C33 -97.5(7) . . . . ?
C6 C7 C8 C9 0.5(7) . . . . ?
C7 C8 C9 N2 -0.5(7) . . . . ?
C7 C8 C9 C19 -177.9(5) . . . . ?
C8 C9 C19 C20 6.7(9) . . . . ?
C9 N2 C6 C5 -175.3(5) . . . . ?
C9 N2 C6 C7 0.0(6) . . . . ?
C9 N2 B1 F1 -65.5(7) . . . . ?
C9 N2 B1 F2 52.7(7) . . . . ?
C9 N2 B1 N1 174.9(5) . . . . ?
C9 C19 C20 C21 178.8(5) . . . . ?
C10 C1 C2 C3 -175.2(6) . . . . ?
C10 C11 C12 C13 -171.1(6) . . . . ?
C10 C11 C12 C17 9.1(10) . . . . ?
C11 C12 C13 C14 178.8(5) . . . . ?
C11 C12 C17 C16 -179.3(5) . . . . ?
C12 C13 C14 C15 1.4(9) . . . . ?
C13 C12 C17 C16 0.9(8) . . . . ?
C13 C14 C15 O2 -179.7(5) . . . . ?
C13 C14 C15 C16 -0.9(9) . . . . ?
C14 C15 C16 O1 -179.5(5) . . . . ?
C14 C15 C16 C17 0.4(8) . . . . ?
C15 C16 C17 C12 -0.5(8) . . . . ?
C17 C12 C13 C14 -1.4(8) . . . . ?
C18 C3 C4 N1 -177.7(6) . . . . ?
C18 C3 C4 C5 -0.2(10) . . . . ?
C19 C20 C21 C22 -172.9(6) . . . . ?
C19 C20 C21 C26 6.6(10) . . . . ?
C20 C21 C22 C23 179.4(5) . . . . ?
C20 C21 C26 C25 -179.2(5) . . . . ?
C21 C22 C23 C24 0.8(9) . . . . ?
C22 C21 C26 C25 0.4(8) . . . . ?
C22 C23 C24 O4 177.5(5) . . . . ?
C22 C23 C24 C25 -1.6(8) . . . . ?
C23 C24 C25 O3 -178.6(5) . . . . ?
C23 C24 C25 C26 1.8(9) . . . . ?
C24 C25 C26 C21 -1.2(9) . . . . ?
C26 C21 C22 C23 -0.2(8) . . . . ?
C27 C7 C8 C9 -178.2(6) . . . . ?
C28 C5 C6 N2 178.8(5) . . . . ?
C28 C5 C6 C7 4.9(9) . . . . ?
C28 C29 C30 C31 -0.2(11) . . . . ?
C29 C28 C33 C32 -1.7(10) . . . . ?
C29 C30 C31 C32 -0.6(12) . . . . ?
C30 C31 C32 C33 0.2(12) . . . . ?
C31 C32 C33 C28 0.9(11) . . . . ?
C33 C28 C29 C30 1.3(10) . . . . ?
B1 N1 C1 C2 -177.6(5) . . . . ?
B1 N1 C1 C10 -1.3(9) . . . . ?
B1 N1 C4 C3 177.8(5) . . . . ?
B1 N1 C4 C5 -0.1(8) . . . . ?
B1 N2 C6 C5 7.8(8) . . . . ?
B1 N2 C6 C7 -176.9(5) . . . . ?
B1 N2 C9 C8 177.0(5) . . . . ?
B1 N2 C9 C19 -5.4(9) . . . . ?
N3 C35 C36 C37 51.3(12) . . . . ?
C34 N3 C35 C36 130.3(9) . . . . ?
C34 N3 C39 C38 -128.7(8) . . . . ?
C35 N3 C34 O5 176.9(8) . . . . ?
C35 N3 C39 C38 54.3(11) . . . . ?
C35 C36 C37 C38 -55.0(14) . . . . ?
C36 C37 C38 C39 56.2(13) . . . . ?
C37 C38 C39 N3 -55.1(12) . . . . ?
C39 N3 C34 O5 0.1(12) . . . . ?
C39 N3 C35 C36 -52.8(11) . . . . ?
