#------------------------------------------------------------------------------
#$Date: 2022-07-06 00:53:32 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276574 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/03/7130322.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_7130322
loop_
_publ_author_name
'Ataie, Saeed'
'Ovens, Jeffrey S.'
'Tom Baker, R.'
_publ_section_title
;
 Solvent-free Zn (NSNO) complex-catalysed dihydroboration of nitriles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03517K
_journal_year                    2022
_chemical_formula_moiety         'C19 H30 B2 F N O4'
_chemical_formula_sum            'C19 H30 B2 F N O4'
_chemical_formula_weight         377.06
_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   geom
_atom_sites_solution_primary     direct
_audit_update_record
;
2021-12-13 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                105.4260(10)
_cell_angle_beta                 97.8810(10)
_cell_angle_gamma                103.3220(10)
_cell_formula_units_Z            2
_cell_length_a                   6.5967(4)
_cell_length_b                   12.0859(6)
_cell_length_c                   14.3335(7)
_cell_measurement_reflns_used    8441
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      2.70
_cell_volume                     1047.70(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15994
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         1.508
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0391
_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)+(0.0547P)²+0.2357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1080
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2901
_reflns_number_total             3664
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03517k2.cif
_cod_data_source_block           K0991
_cod_database_code               7130322
_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_shelxl_version_number     2018/3
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 1.0174(2) 0.32851(13) 0.35540(8) 0.0922(4) Uani 1 1 d . . . . .
O1 O 0.42353(17) 0.20237(9) 0.77492(9) 0.0493(3) Uani 1 1 d . . . . .
O2 O 0.68988(18) 0.12352(9) 0.72809(10) 0.0583(4) Uani 1 1 d . . . . .
O3 O 0.54587(15) 0.47107(8) 0.84003(7) 0.0338(2) Uani 1 1 d . . . . .
O4 O 0.89454(15) 0.55728(8) 0.84009(7) 0.0350(2) Uani 1 1 d . . . . .
N1 N 0.76774(18) 0.33980(10) 0.77399(8) 0.0328(3) Uani 1 1 d . . . . .
C2 C 0.3393(3) 0.07285(14) 0.74721(15) 0.0577(5) Uani 1 1 d . . . . .
C6 C 0.5336(4) -0.08768(16) 0.68423(18) 0.0780(6) Uani 1 1 d . . . . .
H6A H 0.598250 -0.118822 0.629800 0.117 Uiso 1 1 calc R U . A 1
H6B H 0.397019 -0.143436 0.678083 0.117 Uiso 1 1 calc R U . A 1
H6C H 0.626392 -0.077190 0.746486 0.117 Uiso 1 1 calc R U . A 1
C7 C 0.5745(2) 0.60018(12) 0.86456(10) 0.0341(3) Uani 1 1 d . . . . .
C8 C 0.8197(2) 0.65101(12) 0.90016(10) 0.0332(3) Uani 1 1 d . . . . .
C9 C 0.8968(3) 0.66070(14) 1.00771(11) 0.0442(4) Uani 1 1 d . . . . .
H9A H 0.834882 0.585541 1.018806 0.066 Uiso 1 1 calc R U . . .
H9B H 0.853716 0.724073 1.050435 0.066 Uiso 1 1 calc R U . . .
H9C H 1.050939 0.678663 1.022511 0.066 Uiso 1 1 calc R U . . .
C10 C 0.9160(3) 0.76737(13) 0.88096(13) 0.0464(4) Uani 1 1 d . . . . .
H10A H 0.882242 0.756476 0.810505 0.070 Uiso 1 1 calc R U . . .
H10B H 1.069520 0.790987 0.904059 0.070 Uiso 1 1 calc R U . . .
H10C H 0.857958 0.829086 0.916041 0.070 Uiso 1 1 calc R U . . .
C11 C 0.4888(3) 0.62294(15) 0.76940(12) 0.0510(4) Uani 1 1 d . . . . .
H11A H 0.573237 0.600696 0.720927 0.077 Uiso 1 1 calc R U . . .
H11B H 0.497015 0.707060 0.783002 0.077 Uiso 1 1 calc R U . . .
H11C H 0.341536 0.575565 0.743613 0.077 Uiso 1 1 calc R U . . .
C12 C 0.4489(3) 0.63746(14) 0.94248(13) 0.0477(4) Uani 1 1 d . . . . .
H12A H 0.478615 0.723827 0.964052 0.072 Uiso 1 1 calc R U . . .
H12B H 0.489817 0.610922 0.998620 0.072 Uiso 1 1 calc R U . . .
H12C H 0.297748 0.601503 0.914660 0.072 Uiso 1 1 calc R U . . .
C13 C 0.9771(2) 0.34193(13) 0.74755(10) 0.0354(3) Uani 1 1 d . . . . .
H13A H 1.019602 0.273392 0.759197 0.042 Uiso 1 1 calc R U . . .
H13B H 1.082855 0.414654 0.791728 0.042 Uiso 1 1 calc R U . . .
C14 C 0.9818(2) 0.33819(12) 0.64170(10) 0.0346(3) Uani 1 1 d . . . . .
C15 C 0.8232(3) 0.36029(14) 0.58138(11) 0.0428(4) Uani 1 1 d . . . . .
H15 H 0.705209 0.377145 0.606135 0.051 Uiso 1 1 calc R U . . .
C16 C 0.8353(3) 0.35800(16) 0.48504(12) 0.0542(5) Uani 1 1 d . . . . .
H16 H 0.727553 0.373551 0.444584 0.065 Uiso 1 1 calc R U . . .
C17 C 1.0061(3) 0.33283(16) 0.45062(12) 0.0580(5) Uani 1 1 d . . . . .
C18 C 1.1678(3) 0.31189(18) 0.50736(14) 0.0627(5) Uani 1 1 d . . . . .
H18 H 1.285309 0.295628 0.481793 0.075 Uiso 1 1 calc R U . . .
C19 C 1.1545(3) 0.31520(16) 0.60363(12) 0.0504(4) Uani 1 1 d . . . . .
H19 H 1.265142 0.301525 0.643857 0.061 Uiso 1 1 calc R U . . .
B1 B 0.6270(3) 0.22500(15) 0.75873(13) 0.0364(4) Uani 1 1 d . . . . .
B2 B 0.7333(2) 0.45311(14) 0.81719(11) 0.0299(3) Uani 1 1 d . . . . .
C1A C 0.5037(6) 0.0229(3) 0.6818(4) 0.0427(11) Uani 0.407(4) 1 d . . P B 1
C3A C 0.1288(9) 0.0235(5) 0.7163(8) 0.096(3) Uani 0.407(4) 1 d . . P B 1
H3A1 H 0.056418 0.060104 0.765268 0.144 Uiso 0.407(4) 1 calc R U P B 1
H3A2 H 0.096110 -0.061627 0.707393 0.144 Uiso 0.407(4) 1 calc R U P B 1
H3A3 H 0.081349 0.036128 0.653855 0.144 Uiso 0.407(4) 1 calc R U P B 1
C4A C 0.4159(13) 0.0499(5) 0.8537(4) 0.098(3) Uani 0.407(4) 1 d . . P B 1
H4AA H 0.376815 -0.035272 0.844784 0.146 Uiso 0.407(4) 1 calc R U P B 1
H4AB H 0.346455 0.089042 0.902831 0.146 Uiso 0.407(4) 1 calc R U P B 1
H4AC H 0.569222 0.082439 0.875842 0.146 Uiso 0.407(4) 1 calc R U P B 1
C5A C 0.4098(11) 0.0029(5) 0.5752(4) 0.091(2) Uani 0.407(4) 1 d . . P B 1
H5AA H 0.517139 -0.006920 0.536144 0.136 Uiso 0.407(4) 1 calc R U P B 1
H5AB H 0.361698 0.071216 0.569190 0.136 Uiso 0.407(4) 1 calc R U P B 1
H5AC H 0.289995 -0.068479 0.551392 0.136 Uiso 0.407(4) 1 calc R U P B 1
C1B C 0.5271(4) 0.0296(2) 0.7543(3) 0.0459(8) Uani 0.593(4) 1 d . . P B 2
C3B C 0.1999(6) 0.0410(3) 0.6396(3) 0.0712(12) Uani 0.593(4) 1 d . . P B 2
H3BA H 0.291298 0.061968 0.595777 0.107 Uiso 0.593(4) 1 calc R U P B 2
H3BB H 0.094759 0.085618 0.642086 0.107 Uiso 0.593(4) 1 calc R U P B 2
H3BC H 0.128061 -0.043933 0.615073 0.107 Uiso 0.593(4) 1 calc R U P B 2
C4B C 0.1757(6) 0.0436(3) 0.8122(4) 0.0675(11) Uani 0.593(4) 1 d . . P B 2
H4BA H 0.057075 0.075556 0.797824 0.101 Uiso 0.593(4) 1 calc R U P B 2
H4BB H 0.244526 0.079488 0.881615 0.101 Uiso 0.593(4) 1 calc R U P B 2
H4BC H 0.123758 -0.042337 0.797439 0.101 Uiso 0.593(4) 1 calc R U P B 2
C5B C 0.6055(5) 0.0267(3) 0.8582(2) 0.0577(9) Uani 0.593(4) 1 d . . P B 2
H5BA H 0.507958 -0.038088 0.871271 0.087 Uiso 0.593(4) 1 calc R U P B 2
H5BB H 0.612219 0.102017 0.906010 0.087 Uiso 0.593(4) 1 calc R U P B 2
H5BC H 0.746248 0.014361 0.863677 0.087 Uiso 0.593(4) 1 calc R U P B 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 0.0000 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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C2 106.70(12) . . ?
B1 O2 C1A 109.16(18) . . ?
B1 O2 C1B 103.54(15) . . ?
B2 O3 C7 105.88(10) . . ?
B2 O4 C8 106.19(10) . . ?
B1 N1 B2 127.04(13) . . ?
B1 N1 C13 116.34(12) . . ?
B2 N1 C13 116.52(11) . . ?
C3A C2 O1 119.1(3) . . ?
C1B C2 O1 104.56(16) . . ?
C1B C2 C4B 118.8(2) . . ?
O1 C2 C4B 108.21(18) . . ?
C1B C2 C3B 116.5(2) . . ?
O1 C2 C3B 102.36(18) . . ?
C4B C2 C3B 105.0(3) . . ?
C3A C2 C1A 120.2(4) . . ?
O1 C2 C1A 103.59(18) . . ?
C3A C2 C4A 108.4(5) . . ?
O1 C2 C4A 100.6(2) . . ?
C1A C2 C4A 101.9(4) . . ?
C1A C6 H6A 109.5 . . ?
C1A C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1A C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 C12 108.99(11) . . ?
O3 C7 C11 106.60(11) . . ?
C12 C7 C11 110.46(13) . . ?
O3 C7 C8 102.08(10) . . ?
C12 C7 C8 114.60(12) . . ?
C11 C7 C8 113.39(12) . . ?
O4 C8 C10 108.57(11) . . ?
O4 C8 C9 106.86(11) . . ?
C10 C8 C9 110.35(12) . . ?
O4 C8 C7 101.91(10) . . ?
C10 C8 C7 115.40(12) . . ?
C9 C8 C7 112.99(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 114.48(11) . . ?
N1 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
N1 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C19 C14 C15 118.05(14) . . ?
C19 C14 C13 118.94(13) . . ?
C15 C14 C13 122.98(13) . . ?
C14 C15 C16 121.18(16) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 118.47(17) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C16 C17 C18 122.67(16) . . ?
C16 C17 F1 118.81(18) . . ?
C18 C17 F1 118.52(18) . . ?
C17 C18 C19 118.30(17) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C14 C19 C18 121.32(17) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
O2 B1 O1 112.82(13) . . ?
O2 B1 N1 121.18(14) . . ?
O1 B1 N1 125.98(14) . . ?
O3 B2 O4 113.42(12) . . ?
O3 B2 N1 125.67(13) . . ?
O4 B2 N1 120.91(13) . . ?
C6 C1A O2 114.3(3) . . ?
C6 C1A C5A 104.5(4) . . ?
O2 C1A C5A 116.7(4) . . ?
C6 C1A C2 116.9(3) . . ?
O2 C1A C2 97.6(2) . . ?
C5A C1A C2 107.1(4) . . ?
C2 C3A H3A1 109.5 . . ?
C2 C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C2 C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
C2 C4A H4AA 109.5 . . ?
C2 C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
C2 C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C1A C5A H5AA 109.5 . . ?
C1A C5A H5AB 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
C1A C5A H5AC 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C2 C1B C6 122.1(3) . . ?
C2 C1B C5B 112.1(3) . . ?
C6 C1B C5B 106.1(2) . . ?
C2 C1B O2 102.14(19) . . ?
C6 C1B O2 103.2(2) . . ?
C5B C1B O2 110.5(2) . . ?
C2 C3B H3BA 109.5 . . ?
C2 C3B H3BB 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
C2 C3B H3BC 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
C2 C4B H4BA 109.5 . . ?
C2 C4B H4BB 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
C2 C4B H4BC 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
C1B C5B H5BA 109.5 . . ?
C1B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
C1B C5B H5BC 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 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
F1 C17 1.3649(19) . ?
O1 B1 1.371(2) . ?
O1 C2 1.4576(18) . ?
O2 B1 1.366(2) . ?
O2 C1A 1.445(4) . ?
O2 C1B 1.536(3) . ?
O3 B2 1.3713(18) . ?
O3 C7 1.4656(16) . ?
O4 B2 1.3751(18) . ?
O4 C8 1.4574(16) . ?
N1 B1 1.423(2) . ?
N1 B2 1.4287(19) . ?
N1 C13 1.4778(18) . ?
C2 C3A 1.338(6) . ?
C2 C1B 1.453(3) . ?
C2 C4B 1.559(4) . ?
C2 C3B 1.583(4) . ?
C2 C1A 1.642(5) . ?
C2 C4A 1.655(7) . ?
C6 C1A 1.404(4) . ?
C6 C1B 1.517(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 C12 1.515(2) . ?
C7 C11 1.522(2) . ?
C7 C8 1.550(2) . ?
C8 C10 1.516(2) . ?
C8 C9 1.520(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 C14 1.511(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C19 1.382(2) . ?
C14 C15 1.384(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.354(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.364(3) . ?
C18 C19 1.385(2) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C1A C5A 1.501(8) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C3A H3A3 0.9700 . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A H4AC 0.9700 . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A H5AC 0.9700 . ?
C1B C5B 1.520(5) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C3B H3BC 0.9700 . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B H4BC 0.9700 . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C5B H5BC 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10A F1 0.97 2.57 3.401(2) 144.0 2_766 yes
C12 H12C O4 0.97 2.60 3.5502(19) 166.1 1_455 yes
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
B1 O1 C2 C3A -152.6(5) . . . . ?
B1 O1 C2 C1B 22.6(2) . . . . ?
B1 O1 C2 C4B 150.2(2) . . . . ?
B1 O1 C2 C3B -99.3(2) . . . . ?
B1 O1 C2 C1A -15.9(2) . . . . ?
B1 O1 C2 C4A 89.2(3) . . . . ?
B2 O3 C7 C12 -147.64(12) . . . . ?
B2 O3 C7 C11 93.13(13) . . . . ?
B2 O3 C7 C8 -26.05(13) . . . . ?
B2 O4 C8 C10 -148.75(12) . . . . ?
B2 O4 C8 C9 92.23(13) . . . . ?
B2 O4 C8 C7 -26.52(13) . . . . ?
O3 C7 C8 O4 31.88(12) . . . . ?
C12 C7 C8 O4 149.52(12) . . . . ?
C11 C7 C8 O4 -82.38(13) . . . . ?
O3 C7 C8 C10 149.29(12) . . . . ?
C12 C7 C8 C10 -93.07(15) . . . . ?
C11 C7 C8 C10 35.03(17) . . . . ?
O3 C7 C8 C9 -82.42(13) . . . . ?
C12 C7 C8 C9 35.22(17) . . . . ?
C11 C7 C8 C9 163.32(13) . . . . ?
B1 N1 C13 C14 89.79(15) . . . . ?
B2 N1 C13 C14 -93.61(15) . . . . ?
N1 C13 C14 C19 -166.87(13) . . . . ?
N1 C13 C14 C15 15.1(2) . . . . ?
C19 C14 C15 C16 0.8(2) . . . . ?
C13 C14 C15 C16 178.87(14) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C15 C16 C17 F1 178.95(15) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
F1 C17 C18 C19 -179.36(16) . . . . ?
C15 C14 C19 C18 -1.2(2) . . . . ?
C13 C14 C19 C18 -179.38(15) . . . . ?
C17 C18 C19 C14 0.5(3) . . . . ?
C1A O2 B1 O1 24.5(3) . . . . ?
C1B O2 B1 O1 -16.2(2) . . . . ?
C1A O2 B1 N1 -157.4(3) . . . . ?
C1B O2 B1 N1 161.85(19) . . . . ?
C2 O1 B1 O2 -3.31(19) . . . . ?
C2 O1 B1 N1 178.71(16) . . . . ?
B2 N1 B1 O2 -171.62(14) . . . . ?
C13 N1 B1 O2 4.6(2) . . . . ?
B2 N1 B1 O1 6.2(2) . . . . ?
C13 N1 B1 O1 -177.61(14) . . . . ?
C7 O3 B2 O4 10.48(15) . . . . ?
C7 O3 B2 N1 -169.61(13) . . . . ?
C8 O4 B2 O3 11.28(15) . . . . ?
C8 O4 B2 N1 -168.65(12) . . . . ?
B1 N1 B2 O3 -9.0(2) . . . . ?
C13 N1 B2 O3 174.82(12) . . . . ?
B1 N1 B2 O4 170.92(13) . . . . ?
C13 N1 B2 O4 -5.27(19) . . . . ?
B1 O2 C1A C6 -154.9(3) . . . . ?
B1 O2 C1A C5A 82.7(4) . . . . ?
B1 O2 C1A C2 -30.8(3) . . . . ?
C3A C2 C1A C6 -73.9(6) . . . . ?
O1 C2 C1A C6 150.1(3) . . . . ?
C4A C2 C1A C6 45.9(4) . . . . ?
C3A C2 C1A O2 163.9(5) . . . . ?
O1 C2 C1A O2 27.9(3) . . . . ?
C4A C2 C1A O2 -76.3(3) . . . . ?
C3A C2 C1A C5A 42.9(6) . . . . ?
O1 C2 C1A C5A -93.2(3) . . . . ?
C4A C2 C1A C5A 162.7(4) . . . . ?
O1 C2 C1B C6 -145.3(2) . . . . ?
C4B C2 C1B C6 94.0(4) . . . . ?
C3B C2 C1B C6 -33.1(4) . . . . ?
O1 C2 C1B C5B 87.3(2) . . . . ?
C4B C2 C1B C5B -33.4(3) . . . . ?
C3B C2 C1B C5B -160.6(2) . . . . ?
O1 C2 C1B O2 -31.0(3) . . . . ?
C4B C2 C1B O2 -151.7(2) . . . . ?
C3B C2 C1B O2 81.2(3) . . . . ?
B1 O2 C1B C2 29.1(3) . . . . ?
B1 O2 C1B C6 156.57(19) . . . . ?
B1 O2 C1B C5B -90.3(2) . . . . ?
