#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:27:06 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/03/4340309.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_4340309
loop_
_publ_author_name
'Bailey, Jonathan A.'
'Ploeger, Marten'
'Pringle, Paul G.'
_publ_section_title
;
 Mono-, di-, and triborylphosphine analogues of triarylphosphines.
;
_journal_issue                   14
_journal_name_full               'Inorganic chemistry'
_journal_page_first              7763
_journal_page_last               7769
_journal_paper_doi               10.1021/ic501133n
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C10 H8 B Cl N2'
_chemical_formula_sum            'C10 H8 B Cl N2'
_chemical_formula_weight         202.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.5300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1003(2)
_cell_length_b                   3.79990(10)
_cell_length_c                   29.2151(7)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.75
_cell_volume                     893.42(4)
_computing_cell_refinement       'Apex II (Bruker, 2008)'
_computing_data_collection       'Apex II (Bruker, 2008)'
_computing_data_reduction        'SAINT V7.68A'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            26625
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.626
_diffrn_reflns_theta_min         1.403
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0473P)²+0.3957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1965
_reflns_number_total             2069
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic501133n_si_002.cif
_cod_data_source_block           jb0128_new
_cod_depositor_comments
'Adding full bibliography for 4340309--4340313.cif.'
_cod_database_code               4340309
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 0.23984(3) 1.32318(8) 1.01801(2) 0.01771(11) Uani 1 1 d . .
N1 N 0.39280(12) 1.2220(3) 0.93884(4) 0.0150(2) Uani 1 1 d . .
N2 N 0.10679(12) 1.0251(3) 0.93508(3) 0.0152(2) Uani 1 1 d . .
C9 C 0.25812(14) 0.9585(3) 0.86847(4) 0.0127(2) Uani 1 1 d . .
C5 C 0.11963(15) 0.6949(3) 0.79785(4) 0.0166(3) Uani 1 1 d . .
H5 H 0.1218 0.6190 0.7669 0.020 Uiso 1 1 calc R U
C10 C 0.26352(15) 0.8489(3) 0.82215(4) 0.0146(2) Uani 1 1 d . .
C1 C 0.40263(14) 1.1120(3) 0.89316(4) 0.0135(2) Uani 1 1 d . .
C7 C -0.02934(15) 0.7647(4) 0.86460(4) 0.0163(2) Uani 1 1 d . .
H7 H -0.1289 0.7361 0.8785 0.020 Uiso 1 1 calc R U
C3 C 0.54943(15) 1.0445(4) 0.82635(4) 0.0176(3) Uani 1 1 d . .
H3 H 0.6483 1.0751 0.8122 0.021 Uiso 1 1 calc R U
C8 C 0.10833(14) 0.9133(3) 0.88917(4) 0.0135(2) Uani 1 1 d . .
C6 C -0.02239(15) 0.6552(3) 0.81874(4) 0.0176(3) Uani 1 1 d . .
H6 H -0.1178 0.5521 0.8020 0.021 Uiso 1 1 calc R U
C2 C 0.54620(15) 1.1510(3) 0.87246(4) 0.0162(3) Uani 1 1 d . .
H2 H 0.6427 1.2493 0.8892 0.019 Uiso 1 1 calc R U
B1 B 0.24649(17) 1.1818(4) 0.95963(5) 0.0147(3) Uani 1 1 d . .
C4 C 0.41283(15) 0.8980(3) 0.80159(4) 0.0167(2) Uani 1 1 d . .
H4 H 0.4178 0.8288 0.7705 0.020 Uiso 1 1 calc R U
H1N H 0.482(2) 1.315(5) 0.9516(6) 0.027(5) Uiso 1 1 d . .
H2N H 0.015(2) 0.993(5) 0.9470(6) 0.028(4) Uiso 1 1 d . .
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'
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
B1 N1 C1 121.35(11)
B1 N2 C8 121.43(10)
C10 C9 C8 119.22(11)
C10 C9 C1 119.25(11)
C8 C9 C1 121.53(11)
C6 C5 C10 120.36(11)
C5 C10 C9 118.98(11)
C5 C10 C4 122.12(11)
C9 C10 C4 118.90(11)
C2 C1 N1 121.66(11)
C2 C1 C9 120.42(11)
N1 C1 C9 117.92(10)
C8 C7 C6 119.93(11)
C4 C3 C2 121.32(11)
C7 C8 N2 121.73(11)
C7 C8 C9 120.40(11)
N2 C8 C9 117.88(10)
C5 C6 C7 121.12(11)
C1 C2 C3 119.78(11)
N1 B1 N2 119.87(11)
N1 B1 Cl1 119.87(10)
N2 B1 Cl1 120.25(10)
C3 C4 C10 120.33(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 B1 1.7947(14)
N1 B1 1.4004(16)
N1 C1 1.4092(15)
N2 B1 1.4018(16)
N2 C8 1.4082(15)
C9 C10 1.4211(16)
C9 C8 1.4263(16)
C9 C1 1.4278(16)
C5 C6 1.3706(18)
C5 C10 1.4202(17)
C10 C4 1.4226(17)
C1 C2 1.3785(16)
C7 C8 1.3768(17)
C7 C6 1.4101(18)
C3 C4 1.3695(18)
C3 C2 1.4095(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139141936
