#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:27:06 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/03/4340310.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_4340310
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         'C22 H18 B N2 P'
_chemical_formula_sum            'C22 H18 B N2 P'
_chemical_formula_weight         352.16
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                113.860(5)
_cell_angle_beta                 102.299(6)
_cell_angle_gamma                105.052(6)
_cell_formula_units_Z            2
_cell_length_a                   9.1263(8)
_cell_length_b                   10.6800(10)
_cell_length_c                   11.0452(10)
_cell_measurement_reflns_used    6143
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.24
_cell_volume                     886.98(16)
_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 0.997
_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  0.0600
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30860
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.642
_diffrn_reflns_theta_min         2.161
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0339P)²+0.3782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3288
_reflns_number_total             4118
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic501133n_si_002.cif
_cod_data_source_block           mp32_1_new
_cod_depositor_comments
'Adding full bibliography for 4340309--4340313.cif.'
_cod_original_cell_volume        886.98(15)
_cod_database_code               4340310
#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, -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
P1 P 0.39593(5) 0.28941(4) 0.50267(4) 0.02558(11) Uani 1 1 d . .
N2 N 0.51027(15) 0.10069(14) 0.29241(13) 0.0242(3) Uani 1 1 d . .
H2N H 0.429(2) 0.0220(19) 0.2757(17) 0.029 Uiso 1 1 d . U
N1 N 0.66323(16) 0.36414(15) 0.40851(14) 0.0288(3) Uani 1 1 d . .
H1N H 0.683(2) 0.458(2) 0.4655(19) 0.035 Uiso 1 1 d . U
C17 C 0.24962(17) 0.10372(16) 0.44397(15) 0.0238(3) Uani 1 1 d . .
C1 C 0.76356(18) 0.34454(17) 0.32875(16) 0.0274(3) Uani 1 1 d . .
C9 C 0.73376(17) 0.19704(17) 0.22771(15) 0.0255(3) Uani 1 1 d . .
C11 C 0.53401(18) 0.34824(16) 0.68032(16) 0.0253(3) Uani 1 1 d . .
C18 C 0.12581(19) 0.03405(18) 0.31092(16) 0.0289(3) Uani 1 1 d . .
H18 H 0.1242 0.0826 0.2554 0.035 Uiso 1 1 calc R U
C8 C 0.60494(17) 0.07261(16) 0.20761(15) 0.0234(3) Uani 1 1 d . .
C16 C 0.63750(19) 0.27799(18) 0.70557(17) 0.0293(3) Uani 1 1 d . .
H16 H 0.6360 0.1939 0.6285 0.035 Uiso 1 1 calc R U
C22 C 0.24616(18) 0.03106(17) 0.52430(16) 0.0263(3) Uani 1 1 d . .
H22 H 0.3279 0.0764 0.6154 0.032 Uiso 1 1 calc R U
C2 C 0.8891(2) 0.46327(19) 0.34636(18) 0.0361(4) Uani 1 1 d . .
H2 H 0.9081 0.5616 0.4133 0.043 Uiso 1 1 calc R U
C10 C 0.83270(19) 0.1735(2) 0.14353(17) 0.0312(4) Uani 1 1 d . .
C7 C 0.5758(2) -0.06904(18) 0.10695(16) 0.0292(3) Uani 1 1 d . .
H7 H 0.4913 -0.1520 0.0948 0.035 Uiso 1 1 calc R U
C20 C 0.00449(19) -0.17498(18) 0.33981(17) 0.0308(3) Uani 1 1 d . .
H20 H -0.0781 -0.2697 0.3044 0.037 Uiso 1 1 calc R U
C12 C 0.5398(2) 0.47172(18) 0.79546(17) 0.0339(4) Uani 1 1 d . .
H12 H 0.4708 0.5213 0.7809 0.041 Uiso 1 1 calc R U
C21 C 0.12409(19) -0.10709(17) 0.47222(17) 0.0293(3) Uani 1 1 d . .
H21 H 0.1230 -0.1551 0.5282 0.035 Uiso 1 1 calc R U
C6 C 0.6719(2) -0.0899(2) 0.02233(17) 0.0346(4) Uani 1 1 d . .
H6 H 0.6492 -0.1875 -0.0488 0.042 Uiso 1 1 calc R U
C5 C 0.7971(2) 0.0265(2) 0.03990(17) 0.0365(4) Uani 1 1 d . .
H5 H 0.8609 0.0088 -0.0180 0.044 Uiso 1 1 calc R U
C15 C 0.74192(19) 0.32953(19) 0.84148(18) 0.0342(4) Uani 1 1 d . .
H15 H 0.8109 0.2803 0.8571 0.041 Uiso 1 1 calc R U
B1 B 0.5341(2) 0.24525(19) 0.39286(17) 0.0247(3) Uani 1 1 d . .
C19 C 0.00577(19) -0.10406(19) 0.25890(17) 0.0332(4) Uani 1 1 d . .
H19 H -0.0759 -0.1504 0.1676 0.040 Uiso 1 1 calc R U
C14 C 0.7463(2) 0.4524(2) 0.95450(18) 0.0381(4) Uani 1 1 d . .
H14 H 0.8185 0.4879 1.0477 0.046 Uiso 1 1 calc R U
C4 C 0.9621(2) 0.2989(2) 0.1669(2) 0.0409(4) Uani 1 1 d . .
H4 H 1.0310 0.2851 0.1134 0.049 Uiso 1 1 calc R U
C3 C 0.9883(2) 0.4388(2) 0.2655(2) 0.0432(5) Uani 1 1 d . .
H3 H 1.0755 0.5211 0.2796 0.052 Uiso 1 1 calc R U
C13 C 0.6455(2) 0.5231(2) 0.93157(18) 0.0411(4) Uani 1 1 d . .
H13 H 0.6484 0.6076 1.0092 0.049 Uiso 1 1 calc R U
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'
P P 0.1023 0.0942 '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
C17 P1 C11 104.87(7)
C17 P1 B1 102.06(7)
C11 P1 B1 100.60(7)
C8 N2 B1 123.17(13)
C1 N1 B1 123.14(14)
C22 C17 C18 117.93(14)
C22 C17 P1 125.32(11)
C18 C17 P1 116.63(11)
C2 C1 N1 121.83(15)
C2 C1 C9 120.15(15)
N1 C1 C9 118.02(13)
C1 C9 C10 119.38(14)
C1 C9 C8 121.20(13)
C10 C9 C8 119.41(14)
C12 C11 C16 118.18(14)
C12 C11 P1 118.44(12)
C16 C11 P1 123.36(12)
C19 C18 C17 121.23(14)
C7 C8 N2 122.11(14)
C7 C8 C9 120.29(14)
N2 C8 C9 117.60(13)
C15 C16 C11 120.80(15)
C21 C22 C17 120.62(14)
C1 C2 C3 120.07(17)
C5 C10 C4 123.04(15)
C5 C10 C9 118.49(15)
C4 C10 C9 118.47(16)
C8 C7 C6 119.51(15)
C21 C20 C19 119.55(15)
C13 C12 C11 120.64(16)
C20 C21 C22 120.56(14)
C5 C6 C7 121.62(16)
C6 C5 C10 120.64(15)
C14 C15 C16 120.26(16)
N1 B1 N2 116.85(14)
N1 B1 P1 118.76(12)
N2 B1 P1 124.33(12)
C18 C19 C20 120.09(14)
C13 C14 C15 119.73(16)
C3 C4 C10 120.69(16)
C4 C3 C2 121.21(16)
C14 C13 C12 120.38(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C17 1.8309(15)
P1 C11 1.8360(15)
P1 B1 1.9448(18)
N2 C8 1.4021(19)
N2 B1 1.414(2)
N1 C1 1.397(2)
N1 B1 1.410(2)
C17 C22 1.395(2)
C17 C18 1.400(2)
C1 C2 1.382(2)
C1 C9 1.424(2)
C9 C10 1.425(2)
C9 C8 1.427(2)
C11 C12 1.392(2)
C11 C16 1.399(2)
C18 C19 1.383(2)
C8 C7 1.378(2)
C16 C15 1.383(2)
C22 C21 1.391(2)
C2 C3 1.402(3)
C10 C5 1.415(2)
C10 C4 1.423(2)
C7 C6 1.406(2)
C20 C21 1.381(2)
C20 C19 1.386(2)
C12 C13 1.390(2)
C6 C5 1.364(2)
C15 C14 1.381(2)
C14 C13 1.377(3)
C4 C3 1.365(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101876248
