#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:35:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180188 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/84/7108443.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_7108443
loop_
_publ_author_name
'Xiaoxi Zhao'
'Liyuan Liang'
'Douglas W. Stephan'
_publ_section_title
;
 Facile synthesis of electrophilic vinyl boranes: reactions of
 alkynyl-borates and diazonium salts
;
_journal_name_full               Chem.Commun.
_journal_page_first              10189
_journal_paper_doi               10.1039/c2cc35553a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C36 H15 B Cl F18'
_chemical_formula_weight         835.74
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.803(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7455(5)
_cell_length_b                   16.6985(7)
_cell_length_c                   18.4110(9)
_cell_measurement_temperature    150(2)
_cell_volume                     3299.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28414
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7124
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1660
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.647
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.647
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1088P)²+10.7286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                5627
_reflns_number_total             7521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc35553a.txt
_cod_data_source_block           ll009_0m
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7108443
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
B1 B 0.6242(2) 0.72387(15) 0.96873(13) 0.0261(5) Uani 1 1 d .
Cl1 Cl 1.19713(7) 0.76294(5) 1.05362(5) 0.0593(2) Uani 1 1 d .
F1 F 0.74525(15) 0.85554(9) 1.04448(9) 0.0438(4) Uani 1 1 d .
F2 F 0.85570(17) 0.85006(12) 1.17746(9) 0.0589(5) Uani 1 1 d .
F3 F 0.85524(18) 0.71187(15) 1.25544(9) 0.0684(6) Uani 1 1 d .
F4 F 0.7429(2) 0.57942(12) 1.19819(9) 0.0652(5) Uani 1 1 d .
F5 F 0.63277(16) 0.58263(9) 1.06564(8) 0.0437(4) Uani 1 1 d .
F6 F 0.62228(15) 0.79340(9) 0.82376(7) 0.0394(3) Uani 1 1 d .
F7 F 0.51002(18) 0.92946(10) 0.78328(9) 0.0561(5) Uani 1 1 d .
F8 F 0.36956(19) 1.01063(11) 0.87777(13) 0.0692(6) Uani 1 1 d .
F9 F 0.35031(16) 0.95599(11) 1.01560(11) 0.0600(5) Uani 1 1 d .
F10 F 0.46842(14) 0.82208(10) 1.05868(8) 0.0420(4) Uani 1 1 d .
F11 F 0.40754(14) 0.62755(10) 0.97876(7) 0.0415(4) Uani 1 1 d .
F12 F 0.19251(15) 0.59083(12) 0.90399(9) 0.0546(5) Uani 1 1 d .
F13 F 0.18724(15) 0.57989(11) 0.75705(9) 0.0530(4) Uani 1 1 d .
F14 F 0.39959(16) 0.59897(11) 0.68554(8) 0.0503(4) Uani 1 1 d .
F15 F 0.61529(14) 0.63214(9) 0.75899(7) 0.0387(3) Uani 1 1 d .
F16 F 0.8838(2) 0.27271(14) 0.77097(15) 0.0902(8) Uani 1 1 d .
F17 F 0.8192(4) 0.33733(17) 0.67609(14) 0.1181(12) Uani 1 1 d .
F18 F 0.6927(2) 0.27818(14) 0.74047(17) 0.1007(10) Uani 1 1 d .
C1 C 0.6833(2) 0.71993(13) 1.04881(12) 0.0282(5) Uani 1 1 d .
C2 C 0.7415(2) 0.78627(15) 1.08144(13) 0.0327(5) Uani 1 1 d .
C3 C 0.7993(2) 0.78490(18) 1.14975(14) 0.0408(6) Uani 1 1 d .
C4 C 0.7990(2) 0.7150(2) 1.18901(13) 0.0455(7) Uani 1 1 d .
C5 C 0.7418(3) 0.64773(18) 1.15993(13) 0.0426(6) Uani 1 1 d .
C6 C 0.6859(2) 0.65066(15) 1.09112(12) 0.0334(5) Uani 1 1 d .
C7 C 0.5500(2) 0.80088(13) 0.94331(12) 0.0282(4) Uani 1 1 d .
C8 C 0.5551(2) 0.83137(14) 0.87331(13) 0.0314(5) Uani 1 1 d .
C9 C 0.4982(3) 0.90197(15) 0.85105(15) 0.0409(6) Uani 1 1 d .
C10 C 0.4273(3) 0.94322(16) 0.89874(18) 0.0459(7) Uani 1 1 d .
C11 C 0.4177(2) 0.91505(16) 0.96820(17) 0.0420(6) Uani 1 1 d .
C12 C 0.4794(2) 0.84605(15) 0.98976(14) 0.0335(5) Uani 1 1 d .
C13 C 0.5196(2) 0.62932(12) 0.87201(11) 0.0251(4) Uani 1 1 d .
C14 C 0.4080(2) 0.61977(14) 0.90598(12) 0.0293(5) Uani 1 1 d .
C15 C 0.2973(2) 0.60185(16) 0.86881(14) 0.0351(5) Uani 1 1 d .
C16 C 0.2945(2) 0.59517(15) 0.79409(14) 0.0362(5) Uani 1 1 d .
C17 C 0.4026(2) 0.60466(15) 0.75804(12) 0.0338(5) Uani 1 1 d .
C18 C 0.5129(2) 0.62147(13) 0.79655(12) 0.0284(4) Uani 1 1 d .
C19 C 0.8597(2) 0.64693(13) 0.94373(11) 0.0256(4) Uani 1 1 d .
C20 C 0.8922(2) 0.72508(14) 0.92709(12) 0.0311(5) Uani 1 1 d .
H20A H 0.8426 0.7544 0.8923 0.037 Uiso 1 1 calc R
C21 C 0.9962(2) 0.76079(15) 0.96067(14) 0.0358(5) Uani 1 1 d .
H21A H 1.0189 0.8139 0.9485 0.043 Uiso 1 1 calc R
C22 C 1.0664(2) 0.71816(15) 1.01204(14) 0.0349(5) Uani 1 1 d .
C23 C 1.0366(2) 0.64021(15) 1.02993(14) 0.0346(5) Uani 1 1 d .
H23A H 1.0854 0.6118 1.0658 0.042 Uiso 1 1 calc R
C24 C 0.9338(2) 0.60426(13) 0.99449(13) 0.0297(5) Uani 1 1 d .
H24A H 0.9139 0.5502 1.0050 0.036 Uiso 1 1 calc R
C25 C 0.7588(2) 0.53540(13) 0.86885(12) 0.0272(4) Uani 1 1 d .
C26 C 0.8582(2) 0.52595(15) 0.82337(13) 0.0341(5) Uani 1 1 d .
H26A H 0.9182 0.5674 0.8200 0.041 Uiso 1 1 calc R
C27 C 0.8695(3) 0.45656(17) 0.78334(15) 0.0421(6) Uani 1 1 d .
H27A H 0.9365 0.4506 0.7519 0.051 Uiso 1 1 calc R
C28 C 0.7832(3) 0.39574(16) 0.78905(15) 0.0403(6) Uani 1 1 d .
C29 C 0.6868(2) 0.40265(15) 0.83611(14) 0.0372(5) Uani 1 1 d .
H29A H 0.6297 0.3598 0.8413 0.045 Uiso 1 1 calc R
C30 C 0.6748(2) 0.47284(14) 0.87555(12) 0.0300(5) Uani 1 1 d .
H30A H 0.6084 0.4782 0.9074 0.036 Uiso 1 1 calc R
C31 C 0.6354(2) 0.65135(13) 0.91566(11) 0.0251(4) Uani 1 1 d .
C32 C 0.7444(2) 0.61139(13) 0.90971(11) 0.0253(4) Uani 1 1 d .
C33 C 0.7953(3) 0.31997(19) 0.7436(2) 0.0563(8) Uani 1 1 d .
C34 C 0.8616(8) -0.0479(4) 0.8824(4) 0.139(3) Uani 1 1 d .
H34A H 0.8186 -0.0345 0.8358 0.209 Uiso 1 1 calc R
H34B H 0.8002 -0.0545 0.9196 0.209 Uiso 1 1 calc R
H34C H 0.9080 -0.0980 0.8774 0.209 Uiso 1 1 calc R
C35 C 0.9373(6) 0.0085(4) 0.9012(3) 0.111(2) Uani 1 1 d .
H35A H 0.8870 0.0582 0.9003 0.134 Uiso 1 1 calc R
H35C H 0.9949 0.0134 0.8611 0.134 Uiso 1 1 calc R
C36 C 1.0138(6) 0.0121(4) 0.9667(3) 0.113(2) Uani 1 1 d .
H36A H 1.0911 -0.0169 0.9558 0.135 Uiso 1 1 calc R
H36C H 1.0377 0.0691 0.9722 0.135 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'
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
C31 B1 C7 120.05(19) .
C31 B1 C1 120.8(2) .
C7 B1 C1 119.16(19) .
C2 C1 C6 115.0(2) .
C2 C1 B1 121.4(2) .
C6 C1 B1 123.6(2) .
F1 C2 C3 117.0(2) .
F1 C2 C1 119.3(2) .
C3 C2 C1 123.6(2) .
F2 C3 C4 120.3(2) .
F2 C3 C2 120.8(3) .
C4 C3 C2 118.9(2) .
F3 C4 C3 120.2(3) .
F3 C4 C5 119.8(3) .
C3 C4 C5 120.1(2) .
F4 C5 C6 120.4(3) .
F4 C5 C4 119.9(2) .
C6 C5 C4 119.7(3) .
F5 C6 C5 116.7(2) .
F5 C6 C1 120.6(2) .
C5 C6 C1 122.7(2) .
C8 C7 C12 114.7(2) .
C8 C7 B1 122.3(2) .
C12 C7 B1 122.9(2) .
F6 C8 C9 116.4(2) .
F6 C8 C7 120.1(2) .
C9 C8 C7 123.4(2) .
F7 C9 C10 120.2(2) .
F7 C9 C8 120.5(2) .
C10 C9 C8 119.3(3) .
F8 C10 C11 120.3(3) .
F8 C10 C9 120.1(3) .
C11 C10 C9 119.5(2) .
F9 C11 C10 119.8(2) .
F9 C11 C12 120.3(3) .
C10 C11 C12 119.9(2) .
F10 C12 C11 117.3(2) .
F10 C12 C7 119.7(2) .
C11 C12 C7 123.0(2) .
C14 C13 C18 115.7(2) .
C14 C13 C31 120.08(19) .
C18 C13 C31 124.1(2) .
F11 C14 C15 118.1(2) .
F11 C14 C13 118.8(2) .
C15 C14 C13 123.1(2) .
F12 C15 C14 121.1(2) .
F12 C15 C16 119.6(2) .
C14 C15 C16 119.3(2) .
F13 C16 C17 120.3(2) .
F13 C16 C15 120.1(2) .
C17 C16 C15 119.7(2) .
F14 C17 C16 119.6(2) .
F14 C17 C18 120.4(2) .
C16 C17 C18 120.0(2) .
F15 C18 C17 117.92(19) .
F15 C18 C13 119.9(2) .
C17 C18 C13 122.2(2) .
C20 C19 C24 119.1(2) .
C20 C19 C32 119.8(2) .
C24 C19 C32 121.08(19) .
C21 C20 C19 120.8(2) .
C21 C20 H20A 119.6 .
C19 C20 H20A 119.6 .
C22 C21 C20 119.1(2) .
C22 C21 H21A 120.5 .
C20 C21 H21A 120.5 .
C21 C22 C23 121.6(2) .
C21 C22 Cl1 118.92(19) .
C23 C22 Cl1 119.5(2) .
C22 C23 C24 118.8(2) .
C22 C23 H23A 120.6 .
C24 C23 H23A 120.6 .
C23 C24 C19 120.6(2) .
C23 C24 H24A 119.7 .
C19 C24 H24A 119.7 .
C30 C25 C26 119.1(2) .
C30 C25 C32 120.8(2) .
C26 C25 C32 120.0(2) .
C27 C26 C25 120.2(2) .
C27 C26 H26A 119.9 .
C25 C26 H26A 119.9 .
C26 C27 C28 119.9(2) .
C26 C27 H27A 120.0 .
C28 C27 H27A 120.0 .
C27 C28 C29 120.7(2) .
C27 C28 C33 119.4(3) .
C29 C28 C33 119.9(3) .
C28 C29 C30 119.3(2) .
C28 C29 H29A 120.4 .
C30 C29 H29A 120.4 .
C29 C30 C25 120.7(2) .
C29 C30 H30A 119.7 .
C25 C30 H30A 119.7 .
C32 C31 C13 122.34(19) .
C32 C31 B1 121.6(2) .
C13 C31 B1 116.02(18) .
C31 C32 C19 118.35(19) .
C31 C32 C25 124.9(2) .
C19 C32 C25 116.73(19) .
F18 C33 F17 106.3(3) .
F18 C33 F16 106.8(3) .
F17 C33 F16 108.9(3) .
F18 C33 C28 111.9(3) .
F17 C33 C28 111.2(3) .
F16 C33 C28 111.5(3) .
C35 C34 H34A 109.5 .
C35 C34 H34B 109.5 .
H34A C34 H34B 109.5 .
C35 C34 H34C 109.5 .
H34A C34 H34C 109.5 .
H34B C34 H34C 109.5 .
C34 C35 C36 126.2(6) .
C34 C35 H35A 105.8 .
C36 C35 H35A 105.8 .
C34 C35 H35C 105.8 .
C36 C35 H35C 105.8 .
H35A C35 H35C 106.2 .
C36 C36 C35 128.1(7) 3_757
C36 C36 H36A 105.3 3_757
C35 C36 H36A 105.3 .
C36 C36 H36C 105.3 3_757
C35 C36 H36C 105.3 .
H36A C36 H36C 106.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 C31 1.564(3) .
B1 C7 1.572(3) .
B1 C1 1.578(3) .
Cl1 C22 1.736(2) .
F1 C2 1.344(3) .
F2 C3 1.335(3) .
F3 C4 1.338(3) .
F4 C5 1.340(3) .
F5 C6 1.345(3) .
F6 C8 1.349(3) .
F7 C9 1.341(3) .
F8 C10 1.333(3) .
F9 C11 1.347(3) .
F10 C12 1.341(3) .
F11 C14 1.346(2) .
F12 C15 1.339(3) .
F13 C16 1.335(3) .
F14 C17 1.337(3) .
F15 C18 1.340(3) .
F16 C33 1.317(4) .
F17 C33 1.313(4) .
F18 C33 1.304(4) .
C1 C2 1.394(3) .
C1 C6 1.394(3) .
C2 C3 1.375(4) .
C3 C4 1.373(4) .
C4 C5 1.377(4) .
C5 C6 1.376(3) .
C7 C8 1.389(3) .
C7 C12 1.393(3) .
C8 C9 1.381(3) .
C9 C10 1.375(4) .
C10 C11 1.371(4) .
C11 C12 1.378(4) .
C13 C14 1.389(3) .
C13 C18 1.394(3) .
C13 C31 1.494(3) .
C14 C15 1.376(3) .
C15 C16 1.379(3) .
C16 C17 1.375(4) .
C17 C18 1.379(3) .
C19 C20 1.389(3) .
C19 C24 1.394(3) .
C19 C32 1.484(3) .
C20 C21 1.385(3) .
C20 H20A 0.9500 .
C21 C22 1.378(4) .
C21 H21A 0.9500 .
C22 C23 1.384(3) .
C23 C24 1.391(3) .
C23 H23A 0.9500 .
C24 H24A 0.9500 .
C25 C30 1.390(3) .
C25 C26 1.398(3) .
C25 C32 1.487(3) .
C26 C27 1.382(4) .
C26 H26A 0.9500 .
C27 C28 1.383(4) .
C27 H27A 0.9500 .
C28 C29 1.387(4) .
C28 C33 1.526(4) .
C29 C30 1.388(3) .
C29 H29A 0.9500 .
C30 H30A 0.9500 .
C31 C32 1.357(3) .
C34 C35 1.282(9) .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
C35 C36 1.427(7) .
C35 H35A 0.9900 .
C35 H35C 0.9900 .
C36 C36 1.339(9) 3_757
C36 H36A 0.9900 .
C36 H36C 0.9900 .
