#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:58:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180282 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/68/7116820.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_7116820
loop_
_publ_author_name
'Cong Ma'
'Jianying Zhang'
'Jianfeng Li'
'Chunming Cui'
_publ_section_title
;
 Multiple C-H borylation of phenylhydrazones to boron-nitrogen analogues
 of benzopentalene
;
_journal_name_full               Chem.Commun.
_journal_page_first              5732
_journal_paper_doi               10.1039/C5cc00471C
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C24 H18 B2 N2 S'
_chemical_formula_sum            'C24 H18 B2 N2 S'
_chemical_formula_weight         388.08
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-08-11 deposited with the CCDC.
2015-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                76.69(3)
_cell_angle_beta                 80.05(3)
_cell_angle_gamma                77.48(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4920(19)
_cell_length_b                   10.356(2)
_cell_length_c                   10.494(2)
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.0228
_cell_measurement_theta_min      2.0112
_cell_volume                     971.7(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.6
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku Saturn 724CCD camera'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Multilayer
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10239
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.9684
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0747P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1474
_reflns_number_gt                2676
_reflns_number_total             4623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00471c21.cif
_cod_data_source_block           shelxl_1
_cod_original_cell_volume        971.7(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7116820
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.10853(9) 0.22402(14) 0.65198(11) 0.0291(2) Uani 0.7474(17) 1 d PDU A 1
C22 C 0.1464(4) 0.0932(7) 0.4636(5) 0.0291(2) Uani 0.7474(17) 1 d PDU A 1
H22 H 0.1294 0.0531 0.3961 0.035 Uiso 0.7474(17) 1 calc PR A 1
C23 C 0.0403(4) 0.1678(6) 0.5367(5) 0.0291(2) Uani 0.7474(17) 1 d PDU A 1
H23 H -0.0598 0.1866 0.5254 0.035 Uiso 0.7474(17) 1 calc PR A 1
C1 C 0.2837(4) 0.0837(5) 0.5013(4) 0.0291(2) Uani 0.7474(17) 1 d PDU A 1
H1 H 0.3707 0.0372 0.4598 0.035 Uiso 0.7474(17) 1 calc PR A 1
C8 C 0.2818(2) 0.1470(2) 0.6029(2) 0.0291(2) Uani 0.7474(17) 1 d PDU A 1
C1' C 0.1367(9) 0.2120(16) 0.6283(14) 0.0291(2) Uani 0.2526(17) 1 d PDU A 2
H1' H 0.1043 0.2726 0.6874 0.035 Uiso 0.2526(17) 1 calc PR A 2
C23' C 0.1260(8) 0.0978(19) 0.4686(16) 0.0291(2) Uani 0.2526(17) 1 d PDU A 2
H23' H 0.0847 0.0674 0.4072 0.035 Uiso 0.2526(17) 1 calc PR A 2
C22' C 0.0443(8) 0.1755(17) 0.5542(13) 0.0291(2) Uani 0.2526(17) 1 d PDU A 2
H22' H -0.0587 0.2013 0.5628 0.035 Uiso 0.2526(17) 1 calc PR A 2
S1' S 0.3090(3) 0.0598(3) 0.4813(3) 0.0291(2) Uani 0.2526(17) 1 d PDU A 2
C8' C 0.2818(2) 0.1470(2) 0.6029(2) 0.0291(2) Uani 0.2526(17) 1 d PDU A 2
N1 N 0.47329(18) 0.05547(19) 0.75166(16) 0.0221(4) Uani 1 1 d . A .
N2 N 0.58992(18) 0.10061(19) 0.78662(17) 0.0233(4) Uani 1 1 d . A .
C2 C 0.6022(2) -0.1239(2) 0.8902(2) 0.0233(5) Uani 1 1 d . A .
C3 C 0.6630(2) -0.2426(2) 0.9716(2) 0.0262(5) Uani 1 1 d . . .
H3 H 0.6193 -0.3203 0.9898 0.031 Uiso 1 1 calc R . .
C4 C 0.4060(2) 0.1630(2) 0.6602(2) 0.0242(5) Uani 1 1 d . . .
C5 C 0.6671(2) -0.0106(2) 0.86789(19) 0.0218(5) Uani 1 1 d . . .
C6 C 0.7939(2) -0.0135(2) 0.9189(2) 0.0255(5) Uani 1 1 d . . .
H6 H 0.8385 0.0637 0.9002 0.031 Uiso 1 1 calc R . .
C7 C 0.2223(2) -0.1438(2) 0.7841(2) 0.0253(5) Uani 1 1 d . . .
H7 H 0.1710 -0.0583 0.8002 0.030 Uiso 1 1 calc R . .
C9 C 0.4704(2) 0.2718(2) 0.6366(2) 0.0266(5) Uani 1 1 d . A .
H9 H 0.4436 0.3549 0.5777 0.032 Uiso 1 1 calc R . .
C10 C 0.1467(2) -0.2344(2) 0.7602(2) 0.0261(5) Uani 1 1 d . . .
H10 H 0.0441 -0.2110 0.7614 0.031 Uiso 1 1 calc R . .
C11 C 0.3741(2) -0.1766(2) 0.78468(19) 0.0228(5) Uani 1 1 d . A .
C12 C 0.6951(2) 0.3289(2) 0.7419(2) 0.0244(5) Uani 1 1 d . A .
C13 C 0.7875(2) -0.2464(2) 1.0258(2) 0.0274(5) Uani 1 1 d . . .
H13 H 0.8286 -0.3265 1.0820 0.033 Uiso 1 1 calc R . .
C14 C 0.4442(2) -0.3048(2) 0.7624(2) 0.0287(5) Uani 1 1 d . . .
H14 H 0.5460 -0.3311 0.7654 0.034 Uiso 1 1 calc R . .
C15 C 0.2195(2) -0.3591(3) 0.7347(2) 0.0316(6) Uani 1 1 d . . .
H15 H 0.1675 -0.4199 0.7163 0.038 Uiso 1 1 calc R . .
C16 C 0.8525(2) -0.1330(2) 0.9979(2) 0.0283(5) Uani 1 1 d . . .
H16 H 0.9391 -0.1378 1.0340 0.034 Uiso 1 1 calc R . .
C17 C 0.8550(2) 0.5137(3) 0.7786(3) 0.0357(6) Uani 1 1 d . . .
H17 H 0.9086 0.5766 0.7908 0.043 Uiso 1 1 calc R . .
C18 C 0.7464(2) 0.4235(2) 0.6362(2) 0.0283(5) Uani 1 1 d . . .
H18 H 0.7261 0.4258 0.5501 0.034 Uiso 1 1 calc R . .
B1 B 0.4711(3) -0.0838(3) 0.8092(2) 0.0233(5) Uani 1 1 d . . .
C19 C 0.3685(3) -0.3940(3) 0.7362(2) 0.0340(6) Uani 1 1 d . . .
H19 H 0.4190 -0.4794 0.7192 0.041 Uiso 1 1 calc R . .
C20 C 0.8056(2) 0.4218(3) 0.8854(2) 0.0327(6) Uani 1 1 d . A .
H20 H 0.8257 0.4206 0.9713 0.039 Uiso 1 1 calc R . .
B2 B 0.5942(3) 0.2374(3) 0.7218(2) 0.0250(6) Uani 1 1 d . . .
C21 C 0.7268(2) 0.3315(2) 0.8669(2) 0.0295(5) Uani 1 1 d . . .
H21 H 0.6930 0.2690 0.9414 0.035 Uiso 1 1 calc R A .
C24 C 0.8262(2) 0.5140(3) 0.6533(3) 0.0356(6) Uani 1 1 d . . .
H24 H 0.8612 0.5763 0.5793 0.043 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'
S S 0.1246 0.1234 '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
C8 S1 C23 91.33(13)
C23 C22 C1 111.0(3)
C23 C22 H22 124.5
C1 C22 H22 124.5
C22 C23 S1 112.4(2)
C22 C23 H23 123.8
S1 C23 H23 123.8
C8 C1 C22 114.4(3)
C8 C1 H1 122.8
C22 C1 H1 122.8
C1 C8 C4 128.1(2)
C1 C8 S1 110.8(2)
C4 C8 S1 120.82(16)
C22' C1' H1' 124.3
C22' C23' S1' 114.6(5)
C22' C23' H23' 122.7
S1' C23' H23' 122.7
C23' C22' C1' 109.9(5)
C23' C22' H22' 125.0
C1' C22' H22' 125.0
C4 N1 N2 106.53(17)
C4 N1 B1 141.01(19)
N2 N1 B1 112.11(17)
C5 N2 N1 107.04(17)
C5 N2 B2 142.01(19)
N1 N2 B2 110.78(17)
C5 C2 C3 118.79(19)
C5 C2 B1 106.99(19)
C3 C2 B1 134.2(2)
C13 C3 C2 119.6(2)
C13 C3 H3 120.2
C2 C3 H3 120.2
C9 C4 N1 111.86(18)
C9 C4 C8 128.3(2)
N1 C4 C8 119.9(2)
C6 C5 C2 122.3(2)
C6 C5 N2 126.4(2)
C2 C5 N2 111.23(18)
C16 C6 C5 117.5(2)
C16 C6 H6 121.3
C5 C6 H6 121.3
C10 C7 C11 120.9(2)
C10 C7 H7 119.6
C11 C7 H7 119.6
C4 C9 B2 107.8(2)
C4 C9 H9 126.1
B2 C9 H9 126.1
C7 C10 C15 120.6(2)
C7 C10 H10 119.7
C15 C10 H10 119.7
C14 C11 C7 117.2(2)
C14 C11 B1 116.97(19)
C7 C11 B1 125.8(2)
C18 C12 C21 116.5(2)
C18 C12 B2 120.56(19)
C21 C12 B2 122.6(2)
C3 C13 C16 120.2(2)
C3 C13 H13 119.9
C16 C13 H13 119.9
C19 C14 C11 121.6(2)
C19 C14 H14 119.2
C11 C14 H14 119.2
C19 C15 C10 119.5(2)
C19 C15 H15 120.3
C10 C15 H15 120.3
C6 C16 C13 121.5(2)
C6 C16 H16 119.2
C13 C16 H16 119.2
C20 C17 C24 119.7(2)
C20 C17 H17 120.1
C24 C17 H17 120.1
C24 C18 C12 121.8(2)
C24 C18 H18 119.1
C12 C18 H18 119.1
N1 B1 C11 128.9(2)
N1 B1 C2 102.57(19)
C11 B1 C2 128.2(2)
C15 C19 C14 120.1(2)
C15 C19 H19 119.9
C14 C19 H19 119.9
C17 C20 C21 119.8(2)
C17 C20 H20 120.1
C21 C20 H20 120.1
N2 B2 C9 102.98(19)
N2 B2 C12 127.4(2)
C9 B2 C12 129.5(2)
C20 C21 C12 122.2(2)
C20 C21 H21 118.9
C12 C21 H21 118.9
C18 C24 C17 120.0(2)
C18 C24 H24 120.0
C17 C24 H24 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.713(2)
S1 C23 1.726(3)
C22 C23 1.367(4)
C22 C1 1.403(4)
C22 H22 0.9500
C23 H23 0.9500
C1 C8 1.370(4)
C1 H1 0.9500
C8 C4 1.468(3)
C1' C22' 1.425(8)
C1' H1' 0.9500
C23' C22' 1.370(8)
C23' S1' 1.717(7)
C23' H23' 0.9500
C22' H22' 0.9500
N1 C4 1.407(3)
N1 N2 1.422(2)
N1 B1 1.433(3)
N2 C5 1.410(3)
N2 B2 1.429(3)
C2 C5 1.396(3)
C2 C3 1.398(3)
C2 B1 1.556(3)
C3 C13 1.387(3)
C3 H3 0.9500
C4 C9 1.350(3)
C5 C6 1.391(3)
C6 C16 1.385(3)
C6 H6 0.9500
C7 C10 1.386(3)
C7 C11 1.407(3)
C7 H7 0.9500
C9 B2 1.531(3)
C9 H9 0.9500
C10 C15 1.387(3)
C10 H10 0.9500
C11 C14 1.402(3)
C11 B1 1.555(3)
C12 C18 1.396(3)
C12 C21 1.403(3)
C12 B2 1.554(3)
C13 C16 1.392(3)
C13 H13 0.9500
C14 C19 1.385(3)
C14 H14 0.9500
C15 C19 1.384(3)
C15 H15 0.9500
C16 H16 0.9500
C17 C20 1.379(3)
C17 C24 1.388(3)
C17 H17 0.9500
C18 C24 1.384(3)
C18 H18 0.9500
C19 H19 0.9500
C20 C21 1.381(3)
C20 H20 0.9500
C21 H21 0.9500
C24 H24 0.9500
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
C1 C22 C23 S1 -0.7(7)
C8 S1 C23 C22 -0.1(5)
C23 C22 C1 C8 1.4(8)
C22 C1 C8 C4 -176.1(4)
C22 C1 C8 S1 -1.4(6)
C23 S1 C8 C1 0.9(4)
C23 S1 C8 C4 175.9(3)
S1' C23' C22' C1' 3(2)
C4 N1 N2 C5 -174.24(17)
B1 N1 N2 C5 0.4(2)
C4 N1 N2 B2 2.0(2)
B1 N1 N2 B2 176.70(18)
C5 C2 C3 C13 -1.4(3)
B1 C2 C3 C13 177.0(2)
N2 N1 C4 C9 -0.7(2)
B1 N1 C4 C9 -172.8(3)
N2 N1 C4 C8 178.95(18)
B1 N1 C4 C8 6.8(4)
C1 C8 C4 C9 99.7(4)
S1 C8 C4 C9 -74.5(3)
C1 C8 C4 N1 -79.9(4)
S1 C8 C4 N1 105.9(2)
C3 C2 C5 C6 3.0(3)
B1 C2 C5 C6 -175.83(19)
C3 C2 C5 N2 -178.53(19)
B1 C2 C5 N2 2.7(2)
N1 N2 C5 C6 176.41(19)
B2 N2 C5 C6 2.1(4)
N1 N2 C5 C2 -2.0(2)
B2 N2 C5 C2 -176.3(3)
C2 C5 C6 C16 -2.2(3)
N2 C5 C6 C16 179.5(2)
N1 C4 C9 B2 -0.8(3)
C8 C4 C9 B2 179.6(2)
C11 C7 C10 C15 -0.9(3)
C10 C7 C11 C14 -1.0(3)
C10 C7 C11 B1 179.6(2)
C2 C3 C13 C16 -0.7(3)
C7 C11 C14 C19 2.2(3)
B1 C11 C14 C19 -178.3(2)
C7 C10 C15 C19 1.5(3)
C5 C6 C16 C13 -0.1(3)
C3 C13 C16 C6 1.5(3)
C21 C12 C18 C24 0.8(3)
B2 C12 C18 C24 174.5(2)
C4 N1 B1 C11 -0.7(4)
N2 N1 B1 C11 -172.6(2)
C4 N1 B1 C2 173.0(2)
N2 N1 B1 C2 1.1(2)
C14 C11 B1 N1 132.9(2)
C7 C11 B1 N1 -47.7(3)
C14 C11 B1 C2 -39.2(3)
C7 C11 B1 C2 140.1(2)
C5 C2 B1 N1 -2.2(2)
C3 C2 B1 N1 179.2(2)
C5 C2 B1 C11 171.5(2)
C3 C2 B1 C11 -7.0(4)
C10 C15 C19 C14 -0.3(4)
C11 C14 C19 C15 -1.6(4)
C24 C17 C20 C21 -0.5(4)
C5 N2 B2 C9 171.8(3)
N1 N2 B2 C9 -2.4(2)
C5 N2 B2 C12 -11.7(5)
N1 N2 B2 C12 174.1(2)
C4 C9 B2 N2 1.9(2)
C4 C9 B2 C12 -174.5(2)
C18 C12 B2 N2 145.5(2)
C21 C12 B2 N2 -41.3(4)
C18 C12 B2 C9 -38.9(3)
C21 C12 B2 C9 134.3(3)
C17 C20 C21 C12 0.3(4)
C18 C12 C21 C20 -0.5(3)
B2 C12 C21 C20 -174.0(2)
C12 C18 C24 C17 -1.1(4)
C20 C17 C24 C18 0.9(4)
