#------------------------------------------------------------------------------
#$Date: 2019-11-07 23:18:51 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223987 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/07/7700783.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_7700783
loop_
_publ_author_name
'Gazis, Theodore A.'
'Dasgupta, Ayan'
'Hill, Michael S.'
'Rawson, Jeremy M.'
'Wirth, Thomas'
'Melen, Rebecca L.'
_publ_section_title
;
 Reactions of hydrazones and hydrazides with Lewis acidic boranes.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12391
_journal_page_last               12395
_journal_paper_doi               10.1039/c9dt01359h
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C56 H30 B2 F18 N4, 2 (C H2 Cl2)'
_chemical_formula_sum            'C58 H34 B2 Cl4 F18 N4'
_chemical_formula_weight         1292.31
_chemical_properties_physical    Moisture-sensitive
_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     intrinsic
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-02-14 deposited with the CCDC.    2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                103.791(5)
_cell_angle_beta                 98.886(5)
_cell_angle_gamma                90.099(5)
_cell_formula_units_Z            1
_cell_length_a                   9.4053(6)
_cell_length_b                   11.2224(7)
_cell_length_c                   13.6936(8)
_cell_measurement_reflns_used    2576
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8390
_cell_measurement_theta_min      4.0640
_cell_volume                     1385.73(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury CCDC'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10704
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.504
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration
over a multifaceted crystal model. Empirical absorption 
correction using spherical harmonics, implemented in SCALE3 
ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       needle
_exptl_crystal_F_000             650
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6091
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0645
_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)+(0.0403P)²+1.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3327
_reflns_number_total             6091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt01359h2.cif
_cod_data_source_block           rm1848h
_cod_depositor_comments
'Adding full bibliography for 7700782--7700789.cif.'
_cod_original_cell_volume        1385.73(16)
_cod_database_code               7700783
_shelx_shelxl_version_number     2017/1
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.882
_oxdiff_exptl_absorpt_empirical_full_max 1.371
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
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
C11 C -0.1609(3) 0.9961(3) 0.2184(2) 0.0303(8) Uani 1 1 d . . . . .
C16 C -0.2159(3) 1.0933(3) 0.2835(3) 0.0345(8) Uani 1 1 d . . . . .
C12 C -0.1636(4) 1.0203(4) 0.1234(3) 0.0421(9) Uani 1 1 d . . . . .
C15 C -0.2726(4) 1.1979(4) 0.2595(3) 0.0448(9) Uani 1 1 d . . . . .
H15 H -0.309527 1.258163 0.307191 0.054 Uiso 1 1 calc R U . . .
C14 C -0.2718(4) 1.2087(4) 0.1626(3) 0.0509(10) Uani 1 1 d . . . . .
C13 C -0.2167(4) 1.1212(4) 0.0917(3) 0.0516(11) Uani 1 1 d . . . . .
H13 H -0.215340 1.129672 0.025873 0.062 Uiso 1 1 calc R U . . .
F12 F -0.1078(2) 0.9337(2) 0.05266(16) 0.0593(6) Uani 1 1 d . . . . .
F14 F -0.3279(3) 1.3098(2) 0.1350(2) 0.0768(8) Uani 1 1 d . . . . .
F16 F -0.2171(2) 1.08851(19) 0.38276(15) 0.0454(5) Uani 1 1 d . . . . .
B1 B -0.0938(4) 0.8708(4) 0.2432(3) 0.0281(8) Uani 1 1 d . . . . .
C21 C 0.0824(3) 0.8877(3) 0.2639(2) 0.0290(7) Uani 1 1 d . . . . .
C22 C 0.1717(3) 0.8450(3) 0.1916(2) 0.0335(8) Uani 1 1 d . . . . .
C26 C 0.1619(3) 0.9521(3) 0.3548(2) 0.0327(8) Uani 1 1 d . . . . .
C25 C 0.3083(3) 0.9696(3) 0.3784(3) 0.0404(9) Uani 1 1 d . . . . .
H25 H 0.353385 1.011936 0.442655 0.048 Uiso 1 1 calc R U . . .
C23 C 0.3201(3) 0.8589(3) 0.2067(3) 0.0407(9) Uani 1 1 d . . . . .
H23 H 0.373300 0.827794 0.155026 0.049 Uiso 1 1 calc R U . . .
C24 C 0.3845(3) 0.9209(4) 0.3018(3) 0.0424(9) Uani 1 1 d . . . . .
F22 F 0.11024(19) 0.7837(2) 0.09651(14) 0.0439(5) Uani 1 1 d . . . . .
F24 F 0.53105(19) 0.9342(2) 0.32157(18) 0.0603(7) Uani 1 1 d . . . . .
F26 F 0.08701(19) 1.00700(19) 0.43138(14) 0.0428(5) Uani 1 1 d . . . . .
C31 C -0.1563(3) 0.7430(3) 0.1610(2) 0.0299(8) Uani 1 1 d . . . . .
C36 C -0.2885(3) 0.7301(3) 0.0966(3) 0.0349(8) Uani 1 1 d . . . . .
C33 C -0.1355(4) 0.5217(3) 0.0822(3) 0.0399(9) Uani 1 1 d . . . . .
H33 H -0.083385 0.450891 0.078482 0.048 Uiso 1 1 calc R U . . .
C32 C -0.0871(3) 0.6311(3) 0.1499(2) 0.0354(8) Uani 1 1 d . . . . .
C35 C -0.3448(4) 0.6246(4) 0.0254(3) 0.0401(9) Uani 1 1 d . . . . .
H35 H -0.432568 0.623289 -0.016824 0.048 Uiso 1 1 calc R U . . .
C34 C -0.2648(4) 0.5231(4) 0.0204(3) 0.0421(9) Uani 1 1 d . . . . .
F32 F 0.04012(19) 0.62709(19) 0.21114(15) 0.0454(5) Uani 1 1 d . . . . .
F34 F -0.3160(2) 0.4169(2) -0.04792(16) 0.0589(7) Uani 1 1 d . . . . .
F36 F -0.37311(19) 0.8292(2) 0.10199(16) 0.0470(5) Uani 1 1 d . . . . .
N1 N -0.0741(3) 0.7631(3) 0.39145(19) 0.0295(6) Uani 1 1 d . . . . .
N2 N -0.1482(3) 0.8551(2) 0.34826(19) 0.0291(6) Uani 1 1 d . . . . .
H2A H -0.135304 0.926791 0.394130 0.035 Uiso 1 1 calc R U . . .
H2B H -0.242070 0.835507 0.334765 0.035 Uiso 1 1 calc R U . . .
C41 C -0.3143(3) 0.6687(3) 0.3907(2) 0.0298(7) Uani 1 1 d . . . . .
C46 C -0.3891(4) 0.7141(4) 0.4703(3) 0.0454(10) Uani 1 1 d . . . . .
H46 H -0.339350 0.754562 0.533767 0.054 Uiso 1 1 calc R U . . .
C45 C -0.5370(4) 0.6996(4) 0.4559(3) 0.0570(12) Uani 1 1 d . . . . .
H45 H -0.586994 0.732250 0.509031 0.068 Uiso 1 1 calc R U . . .
C44 C -0.6108(4) 0.6369(4) 0.3631(4) 0.0614(13) Uani 1 1 d . . . . .
H44 H -0.710528 0.626243 0.353736 0.074 Uiso 1 1 calc R U . . .
C42 C -0.3885(4) 0.6058(4) 0.2974(3) 0.0446(10) Uani 1 1 d . . . . .
H42 H -0.339048 0.574247 0.243740 0.054 Uiso 1 1 calc R U . . .
C43 C -0.5371(4) 0.5901(4) 0.2843(3) 0.0612(13) Uani 1 1 d . . . . .
H43 H -0.587161 0.547476 0.221642 0.073 Uiso 1 1 calc R U . . .
C47 C -0.1531(3) 0.6788(3) 0.4095(2) 0.0271(7) Uani 1 1 d . . . . .
C48 C -0.0740(3) 0.5871(3) 0.4560(2) 0.0291(7) Uani 1 1 d . . . . .
C49 C 0.0727(3) 0.6039(3) 0.4921(3) 0.0385(9) Uani 1 1 d . . . . .
H49 H 0.121971 0.673744 0.487348 0.046 Uiso 1 1 calc R U . . .
C50 C -0.1457(3) 0.4824(3) 0.4650(3) 0.0388(9) Uani 1 1 d . . . . .
H50 H -0.244198 0.470564 0.441834 0.047 Uiso 1 1 calc R U . . .
Cl1 Cl 0.35604(17) 0.20051(19) 0.19610(16) 0.1244(7) Uani 1 1 d D . . . .
C1SA C 0.1744(6) 0.2135(7) 0.1802(5) 0.120(3) Uani 0.654(18) 1 d D . P A 1
H1S1 H 0.130624 0.138350 0.187265 0.144 Uiso 0.654(18) 1 calc R U P A 1
H1S2 H 0.141697 0.221030 0.111295 0.144 Uiso 0.654(18) 1 calc R U P A 1
Cl2A Cl 0.1116(8) 0.3394(11) 0.2662(6) 0.121(2) Uani 0.654(18) 1 d D . P A 1
C1SB C 0.1744(6) 0.2135(7) 0.1802(5) 0.120(3) Uani 0.346(18) 1 d D . P A 2
H1S3 H 0.146571 0.254386 0.125636 0.144 Uiso 0.346(18) 1 calc R U P A 2
H1S4 H 0.129344 0.131710 0.158794 0.144 Uiso 0.346(18) 1 calc R U P A 2
Cl2B Cl 0.1134(16) 0.2861(14) 0.2777(12) 0.121(2) Uani 0.346(18) 1 d D . P 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 0.0000 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'
Cl Cl 0.1484 0.1585 '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
C12 C11 C16 110.3(3) .
C12 C11 B1 121.2(3) .
C16 C11 B1 128.4(3) .
F16 C16 C15 114.2(3) .
F16 C16 C11 119.0(3) .
C15 C16 C11 126.8(3) .
F12 C12 C13 116.0(3) .
F12 C12 C11 116.5(3) .
C13 C12 C11 127.5(4) .
C14 C15 C16 116.8(4) .
C14 C15 H15 121.6 .
C16 C15 H15 121.6 .
F14 C14 C15 118.9(4) .
F14 C14 C13 118.7(4) .
C15 C14 C13 122.4(4) .
C14 C13 C12 116.1(4) .
C14 C13 H13 121.9 .
C12 C13 H13 121.9 .
C11 B1 C21 108.5(3) .
C11 B1 C31 115.3(3) .
C21 B1 C31 114.1(3) .
C11 B1 N2 107.3(2) .
C21 B1 N2 108.8(2) .
C31 B1 N2 102.4(2) .
C26 C21 C22 110.8(3) .
C26 C21 B1 124.1(3) .
C22 C21 B1 125.1(3) .
F22 C22 C23 115.2(3) .
F22 C22 C21 118.5(3) .
C23 C22 C21 126.3(3) .
C25 C26 F26 115.0(3) .
C25 C26 C21 127.7(3) .
F26 C26 C21 117.3(3) .
C24 C25 C26 116.0(3) .
C24 C25 H25 122.0 .
C26 C25 H25 122.0 .
C24 C23 C22 116.3(3) .
C24 C23 H23 121.8 .
C22 C23 H23 121.8 .
F24 C24 C25 118.5(3) .
F24 C24 C23 118.7(3) .
C25 C24 C23 122.8(3) .
C36 C31 C32 111.2(3) .
C36 C31 B1 124.4(3) .
C32 C31 B1 124.4(3) .
F36 C36 C35 115.1(3) .
F36 C36 C31 118.6(3) .
C35 C36 C31 126.3(3) .
C34 C33 C32 116.3(4) .
C34 C33 H33 121.8 .
C32 C33 H33 121.8 .
F32 C32 C33 115.3(3) .
F32 C32 C31 118.4(3) .
C33 C32 C31 126.4(3) .
C34 C35 C36 116.5(3) .
C34 C35 H35 121.7 .
C36 C35 H35 121.7 .
C35 C34 F34 118.7(3) .
C35 C34 C33 123.2(3) .
F34 C34 C33 118.1(4) .
C47 N1 N2 116.9(2) .
N1 N2 B1 113.6(2) .
N1 N2 H2A 108.8 .
B1 N2 H2A 108.8 .
N1 N2 H2B 108.8 .
B1 N2 H2B 108.8 .
H2A N2 H2B 107.7 .
C42 C41 C46 119.6(3) .
C42 C41 C47 120.9(3) .
C46 C41 C47 119.3(3) .
C45 C46 C41 120.2(3) .
C45 C46 H46 119.9 .
C41 C46 H46 119.9 .
C44 C45 C46 120.2(4) .
C44 C45 H45 119.9 .
C46 C45 H45 119.9 .
C43 C44 C45 119.8(4) .
C43 C44 H44 120.1 .
C45 C44 H44 120.1 .
C41 C42 C43 119.7(3) .
C41 C42 H42 120.1 .
C43 C42 H42 120.1 .
C44 C43 C42 120.5(4) .
C44 C43 H43 119.8 .
C42 C43 H43 119.8 .
N1 C47 C48 115.6(3) .
N1 C47 C41 126.2(3) .
C48 C47 C41 118.1(3) .
C49 C48 C50 118.8(3) .
C49 C48 C47 120.7(3) .
C50 C48 C47 120.5(3) .
C50 C49 C48 120.3(3) 2_566
C50 C49 H49 119.9 2_566
C48 C49 H49 119.9 .
C49 C50 C48 120.9(3) 2_566
C49 C50 H50 119.5 2_566
C48 C50 H50 119.5 .
Cl1 C1SA Cl2A 115.3(4) .
Cl1 C1SA H1S1 108.5 .
Cl2A C1SA H1S1 108.5 .
Cl1 C1SA H1S2 108.5 .
Cl2A C1SA H1S2 108.5 .
H1S1 C1SA H1S2 107.5 .
Cl2B C1SB Cl1 115.1(7) .
Cl2B C1SB H1S3 108.5 .
Cl1 C1SB H1S3 108.5 .
Cl2B C1SB H1S4 108.5 .
Cl1 C1SB H1S4 108.5 .
H1S3 C1SB H1S4 107.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 C12 1.387(5) .
C11 C16 1.391(5) .
C11 B1 1.630(5) .
C16 F16 1.375(4) .
C16 C15 1.379(5) .
C12 F12 1.367(4) .
C12 C13 1.375(5) .
C15 C14 1.362(5) .
C15 H15 0.9300 .
C14 F14 1.361(4) .
C14 C13 1.370(6) .
C13 H13 0.9300 .
B1 C21 1.640(4) .
B1 C31 1.641(5) .
B1 N2 1.647(4) .
C21 C26 1.382(4) .
C21 C22 1.395(4) .
C22 F22 1.357(4) .
C22 C23 1.382(4) .
C26 C25 1.368(4) .
C26 F26 1.378(4) .
C25 C24 1.368(5) .
C25 H25 0.9300 .
C23 C24 1.367(5) .
C23 H23 0.9300 .
C24 F24 1.364(4) .
C31 C36 1.394(4) .
C31 C32 1.402(5) .
C36 F36 1.362(4) .
C36 C35 1.386(5) .
C33 C34 1.372(5) .
C33 C32 1.378(5) .
C33 H33 0.9300 .
C32 F32 1.358(4) .
C35 C34 1.360(5) .
C35 H35 0.9300 .
C34 F34 1.362(4) .
N1 C47 1.294(4) .
N1 N2 1.437(4) .
N2 H2A 0.8900 .
N2 H2B 0.8900 .
C41 C42 1.381(5) .
C41 C46 1.385(5) .
C41 C47 1.497(4) .
C46 C45 1.378(5) .
C46 H46 0.9300 .
C45 C44 1.375(6) .
C45 H45 0.9300 .
C44 C43 1.372(6) .
C44 H44 0.9300 .
C42 C43 1.387(5) .
C42 H42 0.9300 .
C43 H43 0.9300 .
C47 C48 1.479(4) .
C48 C49 1.389(4) .
C48 C50 1.394(4) .
C49 C50 1.380(5) 2_566
C49 H49 0.9300 .
C50 H50 0.9300 .
Cl1 C1SB 1.699(5) .
Cl1 C1SA 1.699(5) .
C1SA Cl2A 1.776(10) .
C1SA H1S1 0.9700 .
C1SA H1S2 0.9700 .
C1SB Cl2B 1.580(15) .
C1SB H1S3 0.9700 .
C1SB H1S4 0.9700 .
