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#$Date: 2017-05-06 00:51:59 +0300 (Sat, 06 May 2017) $
#$Revision: 196366 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/48/1544805.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_1544805
loop_
_publ_author_name
'Swarnakar, Anindya K.'
'Hering-Junghans, Christian'
'Ferguson, Michael J.'
'McDonald, Robert'
'Rivard, Eric'
_publ_section_title
;
 Reactivity of a coordinated inorganic acetylene unit, HBNH, and the
 azidoborane cation [HB(N3)]().
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              2337
_journal_page_last               2343
_journal_paper_doi               10.1039/c6sc04893e
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C12 H21 B F3 N5 O3 S'
_chemical_formula_sum            'C12 H21 B F3 N5 O3 S'
_chemical_formula_weight         383.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-01 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5787(3)
_cell_length_b                   12.2769(2)
_cell_length_c                   11.1774(2)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.19
_cell_measurement_theta_min      3.95
_cell_volume                     1863.32(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5885
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.276
_diffrn_reflns_theta_min         4.856
_exptl_absorpt_coefficient_mu    2.013
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_correction_T_min  0.4591
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       rod
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.09(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0684
_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)+(0.1687P)²+0.0029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1904
_refine_ls_wR_factor_ref         0.1940
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1733
_reflns_number_total             1850
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6sc04893e2.cif
_cod_data_source_block           riv16c6_ImMe2iPr2BHN3OTf_cmpd_8
_cod_depositor_comments
;Adding full bibliography for 1544802--1544808.cif.

 Adding full bibliography for 1544802--1544808.cif.
;
_cod_database_code               1544805
_shelx_shelxl_version_number     2014/7
_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_min   0.399
_shelx_estimated_absorpt_t_max   0.859
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, 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
S S 0.44478(16) 0.40761(16) 0.3010(2) 0.0554(6) Uani 0.5 1 d . . P A -1
F1 F 0.503(2) 0.5680(7) 0.4255(11) 0.140(5) Uani 0.5 1 d . . P A -1
F2 F 0.5325(7) 0.5775(7) 0.2343(13) 0.131(4) Uani 0.5 1 d . . P A -1
F3 F 0.6227(10) 0.4697(15) 0.3542(14) 0.113(5) Uani 0.5 1 d . . P A -1
O1 O 0.4546(6) 0.3388(6) 0.4103(6) 0.0649(16) Uani 0.5 1 d . . P A -1
O2 O 0.493(3) 0.3556(6) 0.1970(8) 0.158(8) Uani 0.5 1 d . . P A -1
O3 O 0.3552(12) 0.4667(12) 0.3072(16) 0.088(4) Uani 0.5 1 d . . P A -1
N1 N 0.5791(2) 0.1875(2) 0.6296(3) 0.0459(8) Uani 1 1 d D . . . .
N2 N 0.4569(6) 0.1405(8) 0.3477(6) 0.064(2) Uani 0.5 1 d . . P A -1
N3 N 0.494(2) 0.1202(6) 0.2469(6) 0.088(4) Uani 0.5 1 d . . P A -1
N4 N 0.5144(17) 0.0943(6) 0.1504(6) 0.053(5) Uani 0.5 1 d . . P A -1
C1 C 0.5137(16) 0.1992(5) 0.5602(5) 0.033(4) Uani 0.5 1 d . . P A -1
C2 C 0.5502(3) 0.1647(3) 0.7447(4) 0.0462(8) Uani 1 1 d . . . . .
C3 C 0.6860(9) 0.1949(15) 0.606(3) 0.079(7) Uani 0.5 1 d D . P A -1
H3 H 0.7096 0.1688 0.6860 0.095 Uiso 0.5 1 calc R U P A -1
C4 C 0.735(2) 0.3006(15) 0.6068(19) 0.109(9) Uani 0.5 1 d D . P A -1
H4A H 0.6987 0.3504 0.6595 0.131 Uiso 0.5 1 calc R U P A -1
H4B H 0.8023 0.2922 0.6358 0.131 Uiso 0.5 1 calc R U P A -1
H4C H 0.7356 0.3302 0.5254 0.131 Uiso 0.5 1 calc R U P A -1
C5 C 0.7264(14) 0.1059(13) 0.5332(16) 0.078(4) Uani 0.5 1 d D . P A -1
H5A H 0.6853 0.0408 0.5428 0.094 Uiso 0.5 1 calc R U P A -1
H5B H 0.7270 0.1277 0.4489 0.094 Uiso 0.5 1 calc R U P A -1
H5C H 0.7937 0.0897 0.5593 0.094 Uiso 0.5 1 calc R U P A -1
C6 C 0.6172(4) 0.1469(6) 0.8498(4) 0.0761(15) Uani 1 1 d . . . . .
H6A H 0.6625 0.0868 0.8323 0.091 Uiso 1 1 calc R U . . .
H6B H 0.5778 0.1288 0.9205 0.091 Uiso 1 1 calc R U . . .
H6C H 0.6550 0.2134 0.8652 0.091 Uiso 1 1 calc R U . . .
C7 C 0.3215(8) 0.1932(14) 0.5728(15) 0.061(5) Uani 0.5 1 d D . P B -1
H7 H 0.3272 0.2167 0.4874 0.074 Uiso 0.5 1 calc R U P B -1
C8 C 0.2654(15) 0.2764(13) 0.6443(18) 0.087(5) Uani 0.5 1 d D . P B -1
H8A H 0.1988 0.2841 0.6113 0.105 Uiso 0.5 1 calc R U P B -1
H8B H 0.2611 0.2525 0.7278 0.105 Uiso 0.5 1 calc R U P B -1
H8C H 0.2995 0.3466 0.6403 0.105 Uiso 0.5 1 calc R U P B -1
C9 C 0.2747(12) 0.0809(12) 0.5810(12) 0.069(3) Uani 0.5 1 d D . P B -1
H9A H 0.2093 0.0826 0.5441 0.083 Uiso 0.5 1 calc R U P B -1
H9B H 0.3161 0.0279 0.5389 0.083 Uiso 0.5 1 calc R U P B -1
H9C H 0.2687 0.0597 0.6652 0.083 Uiso 0.5 1 calc R U P B -1
C10 C 0.5337(8) 0.5128(11) 0.3316(13) 0.079(3) Uani 0.5 1 d . . P A -1
B B 0.515(2) 0.2259(7) 0.4168(7) 0.049(6) Uani 0.5 1 d . . P A -1
H1B H 0.5831 0.2340 0.3854 0.059 Uiso 0.5 1 calc R U P A -1
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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O3 S O2 129.8(13) . .
O3 S O1 109.1(8) . .
O2 S O1 111.0(5) . .
O3 S C10 101.5(7) . .
O2 S C10 99.2(13) . .
O1 S C10 101.0(6) . .
S O1 B 124.8(6) . .
C1 N1 C2 115.0(8) . .
C1 N1 C3 127.6(14) . .
C2 N1 C3 117.3(12) . .
N3 N2 B 112.5(14) . .
N4 N3 N2 169(3) . .
N1 C1 N1 106.3(6) . 4_655
N1 C1 B 131.3(18) . .
N1 C1 B 122.4(15) 4_655 .
C2 C2 N1 106.6(2) 4_655 .
C2 C2 C6 127.3(3) 4_655 .
N1 C2 C6 126.1(4) . .
C4 C3 C5 119.7(11) . .
C4 C3 N1 120.0(16) . .
C5 C3 N1 114.7(13) . .
N1 C7 C8 105.3(11) 4_655 .
N1 C7 C9 108.0(11) 4_655 .
C8 C7 C9 111.8(11) . .
F1 C10 F3 109.7(15) . .
F1 C10 F2 109.7(12) . .
F3 C10 F2 113.3(12) . .
F1 C10 S 107.9(13) . .
F3 C10 S 110.9(10) . .
F2 C10 S 105.2(9) . .
N2 B O1 108.1(15) . .
N2 B C1 110.9(11) . .
O1 B C1 102.4(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S O3 1.419(17) .
S O2 1.48(3) .
S O1 1.491(7) .
S C10 1.801(12) .
F1 C10 1.32(2) .
F2 C10 1.346(18) .
F3 C10 1.34(2) .
O1 B 1.609(16) .
N1 C1 1.188(17) .
N1 C2 1.373(5) .
N1 C3 1.478(9) .
N2 N3 1.261(19) .
N2 B 1.519(19) .
N3 N4 1.157(15) .
C1 N1 1.487(18) 4_655
C1 B 1.636(9) .
C2 C2 1.364(8) 4_655
C2 C6 1.502(6) .
C3 C4 1.455(12) .
C3 C5 1.470(13) .
C7 N1 1.494(10) 4_655
C7 C8 1.504(13) .
C7 C9 1.521(13) .
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
O3 S O1 B 152.1(13) . . . .
O2 S O1 B 2.9(19) . . . .
C10 S O1 B -101.5(12) . . . .
B N2 N3 N4 -163(6) . . . .
C2 N1 C1 N1 1.9(6) . . . 4_655
C3 N1 C1 N1 -177.9(9) . . . 4_655
C2 N1 C1 B -179.6(6) . . . .
C3 N1 C1 B 0.6(12) . . . .
C1 N1 C2 C2 -1.3(4) . . . 4_655
C3 N1 C2 C2 178.5(8) . . . 4_655
C1 N1 C2 C6 -179.6(5) . . . .
C3 N1 C2 C6 0.2(10) . . . .
C1 N1 C3 C4 84(2) . . . .
C2 N1 C3 C4 -96(2) . . . .
C1 N1 C3 C5 -70(2) . . . .
C2 N1 C3 C5 110.5(19) . . . .
O3 S C10 F1 47.1(13) . . . .
O2 S C10 F1 -178.8(12) . . . .
O1 S C10 F1 -65.1(10) . . . .
O3 S C10 F3 167.3(13) . . . .
O2 S C10 F3 -58.7(13) . . . .
O1 S C10 F3 55.0(11) . . . .
O3 S C10 F2 -69.9(11) . . . .
O2 S C10 F2 64.1(12) . . . .
O1 S C10 F2 177.8(8) . . . .
N3 N2 B O1 104.1(15) . . . .
N3 N2 B C1 -144.4(15) . . . .
S O1 B N2 -71.4(15) . . . .
S O1 B C1 171.5(10) . . . .
N1 C1 B N2 124.6(15) . . . .
N1 C1 B N2 -57.1(14) 4_655 . . .
N1 C1 B O1 -120.3(12) . . . .
N1 C1 B O1 58.0(13) 4_655 . . .
C1 N1 C2 C2 1.0(3) . 4_655 4_655 .
C1 N1 C2 C6 179.3(5) . 4_655 4_655 4_655
C7 N1 C2 C2 176.6(9) . 4_655 4_655 .
C7 N1 C2 C6 -5.1(12) . 4_655 4_655 4_655
C1 N1 C7 C8 -127.9(10) . 4_655 . .
C1 N1 C7 C9 112.5(10) . 4_655 . .
C2 N1 C7 C8 57.1(16) 4_655 4_655 . .
C2 N1 C7 C9 -62.5(14) 4_655 4_655 . .
