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#$Date: 2025-08-21 14:21:36 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/05/7010509.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_7010509
loop_
_publ_author_name
'Coapes, R. Benjamin'
'Souza, Fabio E. S.'
'Fox, Mark A.'
'Batsanov, Andrei S.'
'Goeta, Andrés E.'
'Yufit, Dimitrii S.'
'Leech, Michael A.'
'Howard, Judith A. K.'
'Scott, Andrew J.'
'Clegg, William'
'Marder, Todd B.'
_publ_section_title
;
 Phosphine promoted substituent redistribution reactions of
 B-chlorocatechol borane: molecular structures of ClBcat, BrBcat and
 L·ClBcat (cat = 1,2-O2C6H4;
 L = PMe3, PEt3, PBut3, PCy3, NEt3)†
;
_journal_issue                   8
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              1201
_journal_paper_doi               10.1039/b010025k
_journal_year                    2001
_chemical_formula_sum            'C9 H13 B Cl O2 P'
_chemical_formula_weight         230.42
_chemical_name_systematic
;
2-chloro-2-(trimethylphosphino)-1,3,2-benzodioxaborole
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 117.195(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.2244(10)
_cell_length_b                   16.3667(14)
_cell_length_c                   12.7944(11)
_cell_measurement_reflns_used    10821
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      1.87
_cell_volume                     2276.8(3)
_computing_cell_refinement       'local programs'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS-96 (Sheldrick, 1990)'
_diffrn_ambient_temperature      160(2)
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14114
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       Block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.110
_refine_ls_goodness_of_fit_obs   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         5258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_restrained_S_obs      1.109
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_obs          0.0317
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0341P)²+1.1991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0842
_refine_ls_wR_factor_obs         0.0799
_reflns_number_observed          4754
_reflns_number_total             5258
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            b010025k.txt
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+1.1991P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+1.1991P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7010509
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O 0.41862(9) 0.12158(6) 0.05064(9) 0.0210(2) Uani 1 d . .
B1 B 0.34434(15) 0.18522(10) 0.06666(14) 0.0193(3) Uani 1 d . .
O2 O 0.34126(9) 0.16941(6) 0.17741(9) 0.0207(2) Uani 1 d . .
C1 C 0.47208(12) 0.08036(8) 0.15542(12) 0.0189(3) Uani 1 d . .
C2 C 0.42633(12) 0.10876(9) 0.23041(12) 0.0189(3) Uani 1 d . .
C3 C 0.46623(14) 0.07780(9) 0.34181(13) 0.0240(3) Uani 1 d . .
H3 H 0.4354 0.0976 0.3931 0.029 Uiso 1 calc R .
C4 C 0.55491(15) 0.01545(10) 0.37601(14) 0.0299(3) Uani 1 d . .
H4 H 0.5844 -0.0079 0.4521 0.036 Uiso 1 calc R .
C5 C 0.60007(14) -0.01257(10) 0.30153(15) 0.0305(4) Uani 1 d . .
H5 H 0.6601 -0.0547 0.3276 0.037 Uiso 1 calc R .
C6 C 0.55951(14) 0.01965(9) 0.18828(14) 0.0255(3) Uani 1 d . .
H6 H 0.5907 0.0006 0.1370 0.031 Uiso 1 calc R .
Cl1 Cl 0.40795(4) 0.29181(2) 0.06642(3) 0.02616(10) Uani 1 d . .
P1 P 0.17894(3) 0.18554(2) -0.06737(3) 0.01914(9) Uani 1 d . .
C7 C 0.10143(16) 0.09128(10) -0.07133(14) 0.0304(3) Uani 1 d . .
H7A H 0.1542 0.0451 -0.0676 0.046 Uiso 1 calc R .
H7B H 0.0243 0.0884 -0.1444 0.046 Uiso 1 calc R .
H7C H 0.0836 0.0890 -0.0041 0.046 Uiso 1 calc R .
C8 C 0.08546(15) 0.26713(10) -0.05914(14) 0.0287(3) Uani 1 d . .
H8A H 0.0753 0.2610 0.0121 0.043 Uiso 1 calc R .
H8B H 0.0047 0.2655 -0.1283 0.043 Uiso 1 calc R .
H8C H 0.1253 0.3196 -0.0567 0.043 Uiso 1 calc R .
C9 C 0.18995(16) 0.19344(11) -0.20263(14) 0.0301(4) Uani 1 d . .
H9A H 0.2335 0.2438 -0.2021 0.045 Uiso 1 calc R .
H9B H 0.1072 0.1945 -0.2690 0.045 Uiso 1 calc R .
H9C H 0.2351 0.1463 -0.2103 0.045 Uiso 1 calc R .
B2 B 0.16877(15) 0.69282(10) 0.42532(14) 0.0193(3) Uani 1 d . .
O3 O 0.04670(9) 0.66813(7) 0.40832(9) 0.0220(2) Uani 1 d . .
O4 O 0.20499(9) 0.63581(6) 0.35939(9) 0.0208(2) Uani 1 d . .
C11 C 0.00580(13) 0.61324(9) 0.31719(12) 0.0193(3) Uani 1 d . .
C12 C 0.09955(13) 0.59474(8) 0.28738(12) 0.0186(3) Uani 1 d . .
C13 C 0.08136(14) 0.54184(9) 0.19720(13) 0.0237(3) Uani 1 d . .
H13 H 0.1451 0.5300 0.1765 0.028 Uiso 1 calc R .
C14 C -0.03556(16) 0.50616(10) 0.13722(14) 0.0285(3) Uani 1 d . .
H14 H -0.0517 0.4693 0.0744 0.034 Uiso 1 calc R .
C15 C -0.12795(15) 0.52377(10) 0.16813(14) 0.0288(3) Uani 1 d . .
H15 H -0.2058 0.4981 0.1267 0.035 Uiso 1 calc R .
C16 C -0.10931(14) 0.57854(10) 0.25903(13) 0.0247(3) Uani 1 d . .
H16 H -0.1729 0.5911 0.2795 0.030 Uiso 1 calc R .
Cl2 Cl 0.16405(4) 0.80243(2) 0.37044(3) 0.02915(10) Uani 1 d . .
P2 P 0.29380(3) 0.69546(2) 0.59120(3) 0.01798(9) Uani 1 d . .
C17 C 0.28369(15) 0.60551(10) 0.66714(15) 0.0293(3) Uani 1 d . .
H17A H 0.3450 0.6086 0.7499 0.044 Uiso 1 calc R .
H17B H 0.2993 0.5570 0.6311 0.044 Uiso 1 calc R .
H17C H 0.2013 0.6019 0.6618 0.044 Uiso 1 calc R .
C18 C 0.28049(15) 0.78312(10) 0.66868(14) 0.0266(3) Uani 1 d . .
H18A H 0.3390 0.7783 0.7522 0.040 Uiso 1 calc R .
H18B H 0.1967 0.7863 0.6599 0.040 Uiso 1 calc R .
H18C H 0.2985 0.8326 0.6363 0.040 Uiso 1 calc R .
C19 C 0.44347(14) 0.69771(10) 0.59783(15) 0.0276(3) Uani 1 d . .
H19A H 0.4516 0.7471 0.5586 0.041 Uiso 1 calc R .
H19B H 0.4542 0.6493 0.5584 0.041 Uiso 1 calc R .
H19C H 0.5064 0.6980 0.6802 0.041 Uiso 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'
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'
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 B1 105.28(11) . . ?
O1 B1 O2 107.74(11) . . ?
O1 B1 Cl1 111.86(10) . . ?
O2 B1 Cl1 110.79(10) . . ?
O1 B1 P1 109.77(10) . . ?
O2 B1 P1 112.05(10) . . ?
Cl1 B1 P1 104.68(8) . . ?
C2 O2 B1 104.97(11) . . ?
O1 C1 C6 127.62(14) . . ?
O1 C1 C2 110.33(12) . . ?
C6 C1 C2 122.04(14) . . ?
O2 C2 C3 127.49(13) . . ?
O2 C2 C1 110.69(12) . . ?
C3 C2 C1 121.82(14) . . ?
C2 C3 C4 116.62(14) . . ?
C5 C4 C3 121.43(14) . . ?
C4 C5 C6 121.64(15) . . ?
C1 C6 C5 116.45(15) . . ?
C8 P1 C7 107.40(8) . . ?
C8 P1 C9 109.44(8) . . ?
C7 P1 C9 107.71(8) . . ?
C8 P1 B1 112.35(7) . . ?
C7 P1 B1 109.93(8) . . ?
C9 P1 B1 109.87(7) . . ?
O4 B2 O3 107.25(12) . . ?
O4 B2 Cl2 110.71(10) . . ?
O3 B2 Cl2 110.24(10) . . ?
O4 B2 P2 110.29(10) . . ?
O3 B2 P2 113.75(10) . . ?
Cl2 B2 P2 104.64(8) . . ?
C11 O3 B2 104.94(11) . . ?
C12 O4 B2 105.21(11) . . ?
O3 C11 C16 127.88(13) . . ?
O3 C11 C12 110.37(12) . . ?
C16 C11 C12 121.74(14) . . ?
O4 C12 C13 127.88(13) . . ?
O4 C12 C11 110.33(12) . . ?
C13 C12 C11 121.79(14) . . ?
C12 C13 C14 116.99(14) . . ?
C15 C14 C13 121.08(14) . . ?
C14 C15 C16 121.64(15) . . ?
C11 C16 C15 116.75(14) . . ?
C19 P2 C18 107.81(8) . . ?
C19 P2 C17 108.17(8) . . ?
C18 P2 C17 108.07(8) . . ?
C19 P2 B2 108.91(7) . . ?
C18 P2 B2 113.05(7) . . ?
C17 P2 B2 110.68(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3706(17) . ?
O1 B1 1.4565(18) . ?
B1 O2 1.4578(18) . ?
B1 Cl1 1.9105(17) . ?
B1 P1 1.9646(17) . ?
O2 C2 1.3719(17) . ?
C1 C6 1.3768(20) . ?
C1 C2 1.3928(20) . ?
C2 C3 1.3751(20) . ?
C3 C4 1.4051(23) . ?
C4 C5 1.3799(25) . ?
C5 C6 1.4024(23) . ?
P1 C8 1.7917(16) . ?
P1 C7 1.7991(16) . ?
P1 C9 1.8007(16) . ?
B2 O4 1.4559(18) . ?
B2 O3 1.4631(19) . ?
B2 Cl2 1.9178(17) . ?
B2 P2 1.9691(17) . ?
O3 C11 1.3725(17) . ?
O4 C12 1.3699(17) . ?
C11 C16 1.3782(20) . ?
C11 C12 1.3964(20) . ?
C12 C13 1.3770(20) . ?
C13 C14 1.4037(22) . ?
C14 C15 1.3867(24) . ?
C15 C16 1.4020(23) . ?
P2 C19 1.7928(16) . ?
P2 C18 1.7931(15) . ?
P2 C17 1.7990(16) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139154182
