#------------------------------------------------------------------------------
#$Date: 2025-08-21 16:09:30 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301850 $
#$URL: svn://www.crystallography.net/cod/cif/7/04/37/7043781.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_7043781
loop_
_publ_author_name
'Geier, Stephen'
'LaFortune, James'
'Zhu, Diya'
'Kosnik, Stephanie C.'
'Macdonald, Charles L. B.'
'Stephan, Douglas W.'
'Westcott, Steve'
_publ_section_title
;
 The Phosphinoboration of Carbodiimides, Isocyanates, Isothiocyanates and
 CO2
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT02305G
_journal_year                    2017
_chemical_formula_moiety         'C25 H36 B N2 O2 P'
_chemical_formula_sum            'C25 H36 B N2 O2 P'
_chemical_formula_weight         438.34
_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   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-05-13 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                111.6550(10)
_cell_angle_beta                 98.380(2)
_cell_angle_gamma                110.8890(10)
_cell_formula_units_Z            2
_cell_length_a                   10.7605(4)
_cell_length_b                   11.2811(4)
_cell_length_c                   12.5055(4)
_cell_measurement_reflns_used    7596
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      3.11
_cell_volume                     1249.14(8)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29421
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.862
_diffrn_reflns_theta_min         3.114
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2014'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.474
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0447
_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)+(0.0421P)²+0.3982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4055
_reflns_number_total             5350
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt02305g2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7043781
_shelx_shelxl_version_number     2016/6
_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.
;
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
C1 C 0.50507(16) 0.23994(16) 0.66819(14) 0.0164(3) Uani 1 1 d . .
N1 N 0.38694(13) 0.24675(14) 0.60634(11) 0.0171(3) Uani 1 1 d . .
N2 N 0.62985(14) 0.33656(15) 0.71446(13) 0.0229(3) Uani 1 1 d . .
P1 P 0.46763(4) 0.06312(4) 0.66347(4) 0.01887(11) Uani 1 1 d . .
C20 C 0.31469(18) 0.14188(18) 0.47535(14) 0.0220(4) Uani 1 1 d . .
H20 H 0.358533 0.075191 0.455148 0.026 Uiso 1 1 calc R U
C21 C 0.3381(2) 0.2162(2) 0.39533(16) 0.0323(4) Uani 1 1 d . .
H21A H 0.295057 0.281619 0.412101 0.048 Uiso 1 1 calc R U
H21B H 0.295275 0.144978 0.309785 0.048 Uiso 1 1 calc R U
H21C H 0.439068 0.270036 0.412507 0.048 Uiso 1 1 calc R U
C22 C 0.16001(19) 0.05337(19) 0.45068(17) 0.0314(4) Uani 1 1 d . .
H22A H 0.149583 0.004241 0.501515 0.047 Uiso 1 1 calc R U
H22B H 0.116728 -0.017100 0.364909 0.047 Uiso 1 1 calc R U
H22C H 0.113773 0.115775 0.469670 0.047 Uiso 1 1 calc R U
C23 C 0.67185(18) 0.46736(18) 0.69970(16) 0.0253(4) Uani 1 1 d . .
H23 H 0.586472 0.475956 0.667501 0.030 Uiso 1 1 calc R U
C24 C 0.7518(2) 0.4532(2) 0.6086(2) 0.0433(5) Uani 1 1 d . .
H24A H 0.834078 0.442405 0.639637 0.065 Uiso 1 1 calc R U
H24B H 0.782390 0.538735 0.596334 0.065 Uiso 1 1 calc R U
H24C H 0.690554 0.369362 0.531167 0.065 Uiso 1 1 calc R U
C25 C 0.7615(2) 0.5939(2) 0.8220(2) 0.0474(6) Uani 1 1 d . .
H25A H 0.707576 0.596656 0.878870 0.071 Uiso 1 1 calc R U
H25B H 0.789916 0.681826 0.813473 0.071 Uiso 1 1 calc R U
H25C H 0.845262 0.585242 0.853021 0.071 Uiso 1 1 calc R U
C8 C 0.61176(17) 0.10256(17) 0.78957(14) 0.0187(3) Uani 1 1 d . .
C9 C 0.58498(18) 0.04682(19) 0.87078(16) 0.0249(4) Uani 1 1 d . .
H9 H 0.490693 -0.002880 0.866432 0.030 Uiso 1 1 calc R U
C10 C 0.69367(19) 0.0626(2) 0.95794(17) 0.0304(4) Uani 1 1 d . .
H10 H 0.673414 0.023056 1.012103 0.036 Uiso 1 1 calc R U
C11 C 0.83115(19) 0.1358(2) 0.96609(17) 0.0312(4) Uani 1 1 d . .
H11 H 0.905776 0.148438 1.026823 0.037 Uiso 1 1 calc R U
C12 C 0.85963(19) 0.1905(2) 0.88542(17) 0.0297(4) Uani 1 1 d . .
H12 H 0.954181 0.240503 0.890537 0.036 Uiso 1 1 calc R U
C13 C 0.75117(18) 0.17288(18) 0.79710(16) 0.0245(4) Uani 1 1 d . .
H13 H 0.772018 0.209147 0.740988 0.029 Uiso 1 1 calc R U
C2 C 0.31803(17) 0.02923(17) 0.72083(15) 0.0202(4) Uani 1 1 d . .
C7 C 0.20954(18) -0.10879(19) 0.66435(17) 0.0285(4) Uani 1 1 d . .
H7 H 0.216311 -0.181422 0.599593 0.034 Uiso 1 1 calc R U
C6 C 0.09148(19) -0.1417(2) 0.7015(2) 0.0364(5) Uani 1 1 d . .
H6 H 0.018893 -0.236623 0.662845 0.044 Uiso 1 1 calc R U
C5 C 0.07934(19) -0.0376(2) 0.79365(19) 0.0336(5) Uani 1 1 d . .
H5 H -0.002260 -0.060019 0.817885 0.040 Uiso 1 1 calc R U
C4 C 0.18629(19) 0.1001(2) 0.85133(17) 0.0291(4) Uani 1 1 d . .
H4 H 0.178449 0.172072 0.915880 0.035 Uiso 1 1 calc R U
C3 C 0.30459(18) 0.13352(18) 0.81536(15) 0.0234(4) Uani 1 1 d . .
H3 H 0.377414 0.228407 0.855431 0.028 Uiso 1 1 calc R U
B1 B 0.34368(19) 0.34974(19) 0.66953(17) 0.0177(4) Uani 1 1 d . .
O1 O 0.24516(12) 0.37801(12) 0.61391(10) 0.0224(3) Uani 1 1 d . .
O2 O 0.39389(12) 0.42850(11) 0.79354(10) 0.0213(3) Uani 1 1 d . .
C14 C 0.20318(18) 0.45851(18) 0.71064(15) 0.0224(4) Uani 1 1 d . .
C15 C 0.33487(18) 0.53032(17) 0.82475(15) 0.0228(4) Uani 1 1 d . .
C16 C 0.07383(19) 0.3504(2) 0.71593(18) 0.0309(4) Uani 1 1 d . .
H16A H 0.001015 0.296503 0.636357 0.046 Uiso 1 1 calc R U
H16B H 0.038655 0.400026 0.777019 0.046 Uiso 1 1 calc R U
H16C H 0.098336 0.284736 0.737842 0.046 Uiso 1 1 calc R U
C17 C 0.1679(2) 0.5623(2) 0.67813(19) 0.0358(5) Uani 1 1 d . .
H17A H 0.247916 0.622113 0.662990 0.054 Uiso 1 1 calc R U
H17B H 0.147304 0.622644 0.745453 0.054 Uiso 1 1 calc R U
H17C H 0.085660 0.509080 0.604964 0.054 Uiso 1 1 calc R U
C18 C 0.3029(2) 0.5465(2) 0.94195(16) 0.0339(5) Uani 1 1 d . .
H18A H 0.238866 0.453014 0.931860 0.051 Uiso 1 1 calc R U
H18B H 0.258730 0.610735 0.962372 0.051 Uiso 1 1 calc R U
H18C H 0.390254 0.586114 1.007433 0.051 Uiso 1 1 calc R U
C19 C 0.4459(2) 0.67087(19) 0.84199(19) 0.0365(5) Uani 1 1 d . .
H19A H 0.532318 0.700923 0.904620 0.055 Uiso 1 1 calc R U
H19B H 0.411970 0.743540 0.867153 0.055 Uiso 1 1 calc R U
H19C H 0.464910 0.658803 0.765333 0.055 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'
O O 0.0106 0.0060 '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
N2 C1 N1 125.99(14)
N2 C1 P1 119.06(12)
N1 C1 P1 114.64(11)
B1 N1 C1 119.97(13)
B1 N1 C20 123.11(13)
C1 N1 C20 116.92(12)
C1 N2 C23 122.00(14)
C2 P1 C8 103.01(7)
C2 P1 C1 102.12(7)
C8 P1 C1 104.17(7)
N1 C20 C22 111.53(14)
N1 C20 C21 110.82(14)
C22 C20 C21 112.04(14)
N1 C20 H20 107.4
C22 C20 H20 107.4
C21 C20 H20 107.4
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C20 C22 H22A 109.5
C20 C22 H22B 109.5
H22A C22 H22B 109.5
C20 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
N2 C23 C25 108.67(15)
N2 C23 C24 106.72(15)
C25 C23 C24 112.08(17)
N2 C23 H23 109.8
C25 C23 H23 109.8
C24 C23 H23 109.8
C23 C24 H24A 109.5
C23 C24 H24B 109.5
H24A C24 H24B 109.5
C23 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C23 C25 H25A 109.5
C23 C25 H25B 109.5
H25A C25 H25B 109.5
C23 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
C9 C8 C13 118.01(15)
C9 C8 P1 120.70(13)
C13 C8 P1 120.75(12)
C10 C9 C8 121.09(16)
C10 C9 H9 119.5
C8 C9 H9 119.5
C11 C10 C9 120.09(16)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C12 119.60(16)
C10 C11 H11 120.2
C12 C11 H11 120.2
C11 C12 C13 120.39(17)
C11 C12 H12 119.8
C13 C12 H12 119.8
C12 C13 C8 120.79(16)
C12 C13 H13 119.6
C8 C13 H13 119.6
C7 C2 C3 118.15(16)
C7 C2 P1 117.67(14)
C3 C2 P1 124.15(13)
C6 C7 C2 120.83(18)
C6 C7 H7 119.6
C2 C7 H7 119.6
C5 C6 C7 120.26(18)
C5 C6 H6 119.9
C7 C6 H6 119.9
C6 C5 C4 119.81(18)
C6 C5 H5 120.1
C4 C5 H5 120.1
C3 C4 C5 120.27(18)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C3 C2 120.68(16)
C4 C3 H3 119.7
C2 C3 H3 119.7
O2 B1 O1 113.49(15)
O2 B1 N1 122.66(15)
O1 B1 N1 123.83(15)
B1 O1 C14 105.96(12)
B1 O2 C15 107.11(12)
O1 C14 C17 108.63(14)
O1 C14 C16 106.43(13)
C17 C14 C16 110.35(15)
O1 C14 C15 102.61(12)
C17 C14 C15 114.52(15)
C16 C14 C15 113.60(14)
O2 C15 C18 108.16(14)
O2 C15 C19 106.99(14)
C18 C15 C19 110.49(15)
O2 C15 C14 102.12(12)
C18 C15 C14 114.82(15)
C19 C15 C14 113.50(15)
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C15 C19 H19A 109.5
C15 C19 H19B 109.5
H19A C19 H19B 109.5
C15 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.261(2)
C1 N1 1.4306(19)
C1 P1 1.8649(16)
N1 B1 1.416(2)
N1 C20 1.493(2)
N2 C23 1.472(2)
P1 C2 1.8309(17)
P1 C8 1.8351(16)
C20 C22 1.517(2)
C20 C21 1.520(2)
C20 H20 1.0000
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 C25 1.511(3)
C23 C24 1.521(3)
C23 H23 1.0000
C24 H24A 0.9800
C24 H24B 0.9800
C24 H24C 0.9800
C25 H25A 0.9800
C25 H25B 0.9800
C25 H25C 0.9800
C8 C9 1.392(2)
C8 C13 1.394(2)
C9 C10 1.387(2)
C9 H9 0.9500
C10 C11 1.380(3)
C10 H10 0.9500
C11 C12 1.381(3)
C11 H11 0.9500
C12 C13 1.385(2)
C12 H12 0.9500
C13 H13 0.9500
C2 C7 1.392(2)
C2 C3 1.395(2)
C7 C6 1.389(3)
C7 H7 0.9500
C6 C5 1.370(3)
C6 H6 0.9500
C5 C4 1.384(3)
C5 H5 0.9500
C4 C3 1.384(2)
C4 H4 0.9500
C3 H3 0.9500
B1 O2 1.372(2)
B1 O1 1.378(2)
O1 C14 1.461(2)
O2 C15 1.4617(19)
C14 C17 1.518(2)
C14 C16 1.518(2)
C14 C15 1.562(2)
C15 C18 1.515(2)
C15 C19 1.520(2)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
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
N2 C1 N1 B1 -63.1(2)
P1 C1 N1 B1 123.28(14)
N2 C1 N1 C20 116.87(18)
P1 C1 N1 C20 -56.73(16)
N1 C1 N2 C23 -5.9(3)
P1 C1 N2 C23 167.43(12)
N2 C1 P1 C2 132.40(14)
N1 C1 P1 C2 -53.52(13)
N2 C1 P1 C8 25.44(15)
N1 C1 P1 C8 -160.47(11)
B1 N1 C20 C22 -56.7(2)
C1 N1 C20 C22 123.34(15)
B1 N1 C20 C21 68.9(2)
C1 N1 C20 C21 -111.09(16)
C1 N2 C23 C25 133.51(18)
C1 N2 C23 C24 -105.44(19)
C2 P1 C8 C9 26.92(15)
C1 P1 C8 C9 133.21(14)
C2 P1 C8 C13 -161.63(13)
C1 P1 C8 C13 -55.34(15)
C13 C8 C9 C10 1.0(3)
P1 C8 C9 C10 172.70(14)
C8 C9 C10 C11 0.6(3)
C9 C10 C11 C12 -1.3(3)
C10 C11 C12 C13 0.3(3)
C11 C12 C13 C8 1.4(3)
C9 C8 C13 C12 -2.0(3)
P1 C8 C13 C12 -173.71(14)
C8 P1 C2 C7 -112.79(13)
C1 P1 C2 C7 139.35(13)
C8 P1 C2 C3 68.80(14)
C1 P1 C2 C3 -39.06(15)
C3 C2 C7 C6 -0.2(2)
P1 C2 C7 C6 -178.72(13)
C2 C7 C6 C5 0.9(3)
C7 C6 C5 C4 -1.2(3)
C6 C5 C4 C3 0.7(3)
C5 C4 C3 C2 -0.1(2)
C7 C2 C3 C4 -0.2(2)
P1 C2 C3 C4 178.22(12)
C1 N1 B1 O2 -11.8(2)
C20 N1 B1 O2 168.21(15)
C1 N1 B1 O1 170.08(15)
C20 N1 B1 O1 -9.9(3)
O2 B1 O1 C14 -13.66(18)
N1 B1 O1 C14 164.61(16)
O1 B1 O2 C15 -6.14(18)
N1 B1 O2 C15 175.57(15)
B1 O1 C14 C17 147.54(15)
B1 O1 C14 C16 -93.65(15)
B1 O1 C14 C15 25.93(15)
B1 O2 C15 C18 143.11(15)
B1 O2 C15 C19 -97.86(16)
B1 O2 C15 C14 21.62(16)
O1 C14 C15 O2 -28.82(15)
C17 C14 C15 O2 -146.32(14)
C16 C14 C15 O2 85.63(16)
O1 C14 C15 C18 -145.60(14)
C17 C14 C15 C18 96.89(18)
C16 C14 C15 C18 -31.1(2)
O1 C14 C15 C19 85.96(16)
C17 C14 C15 C19 -31.5(2)
C16 C14 C15 C19 -159.58(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139171271
