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#$Date: 2025-08-18 17:02:58 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301777 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/02/1520283.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_1520283
loop_
_publ_author_name
'Tizzard, Graham J.'
'Hursthouse, Michael B.'
'Spencer, John'
_publ_section_title
;
 C31H33O2BBrP
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1047
_journal_year                    2009
_chemical_formula_moiety         'C25 H23 B O2 P, Br'
_chemical_formula_sum            'C25 H23 B Br O2 P'
_chemical_formula_weight         477.12
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.740(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8278(4)
_cell_length_b                   9.4884(5)
_cell_length_c                   12.0388(5)
_cell_measurement_reflns_used    44453
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1118.78(9)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CrystalMaker (CrystalMaker Software Ltd, 2009'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0786
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15595
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    1.928
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.5127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shard
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.040(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4905
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0428
_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)+(0.0235P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                4183
_reflns_number_total             4905
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-1047.cif
_cod_data_source_block           2009src0712r
_cod_depositor_comments
;
Citation :
Tizzard, Graham J. and Hursthouse, Michael B. and Spencer, John (2009)
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/1047)

More at:
http://ecrystals.chem.soton.ac.uk/1047/
;
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               1520283
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.88938(5) 0.51480(4) 0.67793(4) 0.03051(11) Uani 1 1 d . . .
C1 C 0.2774(3) 0.7812(4) 0.4889(3) 0.0212(8) Uani 1 1 d . . .
C2 C 0.3588(4) 0.6649(4) 0.4690(3) 0.0259(8) Uani 1 1 d . . .
H2 H 0.3595 0.6277 0.3958 0.031 Uiso 1 1 calc R . .
C3 C 0.4380(4) 0.6041(4) 0.5558(3) 0.0295(9) Uani 1 1 d . . .
H3 H 0.4948 0.5260 0.5419 0.035 Uiso 1 1 calc R . .
C4 C 0.4355(4) 0.6565(4) 0.6642(3) 0.0290(9) Uani 1 1 d . . .
H4 H 0.4901 0.6147 0.7241 0.035 Uiso 1 1 calc R . .
C5 C 0.3519(4) 0.7706(4) 0.6829(3) 0.0308(9) Uani 1 1 d . . .
H5 H 0.3489 0.8062 0.7565 0.037 Uiso 1 1 calc R . .
C6 C 0.2734(4) 0.8328(4) 0.5967(3) 0.0277(9) Uani 1 1 d . . .
H6 H 0.2167 0.9109 0.6106 0.033 Uiso 1 1 calc R . .
C7 C 0.0207(3) 0.7873(4) 0.3384(3) 0.0220(8) Uani 1 1 d . . .
C8 C -0.0238(4) 0.6732(4) 0.3993(3) 0.0246(8) Uani 1 1 d . . .
H8 H 0.0323 0.6375 0.4610 0.029 Uiso 1 1 calc R . .
C9 C -0.1500(4) 0.6118(4) 0.3696(3) 0.0287(9) Uani 1 1 d . . .
H9 H -0.1795 0.5332 0.4102 0.034 Uiso 1 1 calc R . .
C10 C -0.2326(4) 0.6651(4) 0.2810(3) 0.0294(9) Uani 1 1 d . . .
H10 H -0.3177 0.6215 0.2595 0.035 Uiso 1 1 calc R . .
C11 C -0.1914(4) 0.7824(4) 0.2232(3) 0.0278(8) Uani 1 1 d . . .
H11 H -0.2504 0.8209 0.1644 0.033 Uiso 1 1 calc R . .
C12 C -0.0642(4) 0.8440(4) 0.2508(3) 0.0241(8) Uani 1 1 d . . .
H12 H -0.0357 0.9234 0.2106 0.029 Uiso 1 1 calc R . .
C13 C 0.1506(4) 1.0474(3) 0.4153(3) 0.0202(7) Uani 1 1 d . . .
C14 C 0.0300(4) 1.0885(4) 0.4571(3) 0.0254(8) Uani 1 1 d . . .
H14 H -0.0419 1.0223 0.4612 0.031 Uiso 1 1 calc R . .
C15 C 0.0133(3) 1.2252(4) 0.4927(3) 0.0282(9) Uani 1 1 d . . .
H15 H -0.0688 1.2517 0.5237 0.034 Uiso 1 1 calc R . .
C16 C 0.1151(4) 1.3237(4) 0.4835(3) 0.0285(8) Uani 1 1 d . . .
H16 H 0.1024 1.4178 0.5075 0.034 Uiso 1 1 calc R . .
C17 C 0.2353(4) 1.2861(4) 0.4395(3) 0.0327(10) Uani 1 1 d . . .
H17 H 0.3042 1.3547 0.4314 0.039 Uiso 1 1 calc R . .
C18 C 0.2554(4) 1.1472(4) 0.4071(3) 0.0303(9) Uani 1 1 d . . .
H18 H 0.3393 1.1199 0.3795 0.036 Uiso 1 1 calc R . .
C19 C 0.2885(4) 0.8650(4) 0.2575(3) 0.0230(8) Uani 1 1 d . . .
H19A H 0.3730 0.9185 0.2791 0.028 Uiso 1 1 calc R . .
H19B H 0.3154 0.7658 0.2461 0.028 Uiso 1 1 calc R . .
C20 C 0.2284(3) 0.9219(4) 0.1469(3) 0.0211(7) Uani 1 1 d . . .
C21 C 0.2280(4) 1.0666(4) 0.1232(3) 0.0249(8) Uani 1 1 d . . .
H21 H 0.2602 1.1317 0.1793 0.030 Uiso 1 1 calc R . .
C22 C 0.1816(4) 1.1148(4) 0.0194(3) 0.0286(9) Uani 1 1 d . . .
H22 H 0.1794 1.2131 0.0047 0.034 Uiso 1 1 calc R . .
C23 C 0.1379(6) 1.0204(4) -0.0639(5) 0.0244(9) Uani 1 1 d . . .
H23 H 0.1095 1.0550 -0.1361 0.029 Uiso 1 1 calc R . .
C24 C 0.1347(3) 0.8753(4) -0.0439(3) 0.0225(8) Uani 1 1 d . . .
C25 C 0.1804(3) 0.8286(4) 0.0642(3) 0.0209(7) Uani 1 1 d . . .
H25 H 0.1781 0.7307 0.0806 0.025 Uiso 1 1 calc R . .
B1 B 0.0811(4) 0.7678(5) -0.1380(3) 0.0236(9) Uani 1 1 d . . .
O2 O 0.0278(2) 0.8215(3) -0.23696(19) 0.0271(6) Uani 1 1 d . . .
H2A H -0.0107 0.7569 -0.2755 0.041 Uiso 1 1 calc R . .
O3 O 0.0867(3) 0.6282(3) -0.1125(2) 0.0292(6) Uani 1 1 d . . .
H3A H 0.0410 0.5825 -0.1623 0.044 Uiso 1 1 calc R . .
P1 P 0.18209(9) 0.86970(10) 0.37418(7) 0.0202(2) Uani 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'
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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 120.0(3) . .
C6 C1 P1 119.7(3) . .
C2 C1 P1 120.3(3) . .
C3 C2 C1 119.9(3) . .
C3 C2 H2 120.1 . .
C1 C2 H2 120.1 . .
C2 C3 C4 120.4(4) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C5 C4 C3 119.0(4) . .
C5 C4 H4 120.5 . .
C3 C4 H4 120.5 . .
C6 C5 C4 121.0(4) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C5 C6 C1 119.8(3) . .
C5 C6 H6 120.1 . .
C1 C6 H6 120.1 . .
C12 C7 C8 120.0(3) . .
C12 C7 P1 118.4(3) . .
C8 C7 P1 121.5(3) . .
C9 C8 C7 120.1(4) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C10 C9 C8 120.0(4) . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C9 C10 C11 120.2(4) . .
C9 C10 H10 119.9 . .
C11 C10 H10 119.9 . .
C10 C11 C12 120.5(4) . .
C10 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
C11 C12 C7 119.1(3) . .
C11 C12 H12 120.5 . .
C7 C12 H12 120.5 . .
C14 C13 C18 119.3(3) . .
C14 C13 P1 122.6(3) . .
C18 C13 P1 118.0(3) . .
C15 C14 C13 120.4(3) . .
C15 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
C14 C15 C16 120.4(3) . .
C14 C15 H15 119.8 . .
C16 C15 H15 119.8 . .
C15 C16 C17 120.3(4) . .
C15 C16 H16 119.8 . .
C17 C16 H16 119.8 . .
C16 C17 C18 119.8(4) . .
C16 C17 H17 120.1 . .
C18 C17 H17 120.1 . .
C17 C18 C13 119.7(3) . .
C17 C18 H18 120.2 . .
C13 C18 H18 120.2 . .
C20 C19 P1 117.6(2) . .
C20 C19 H19A 107.9 . .
P1 C19 H19A 107.9 . .
C20 C19 H19B 107.9 . .
P1 C19 H19B 107.9 . .
H19A C19 H19B 107.2 . .
C25 C20 C21 118.9(3) . .
C25 C20 C19 119.3(3) . .
C21 C20 C19 121.6(3) . .
C22 C21 C20 120.5(4) . .
C22 C21 H21 119.8 . .
C20 C21 H21 119.8 . .
C21 C22 C23 120.2(4) . .
C21 C22 H22 119.9 . .
C23 C22 H22 119.9 . .
C22 C23 C24 121.4(5) . .
C22 C23 H23 119.3 . .
C24 C23 H23 119.3 . .
C23 C24 C25 117.2(4) . .
C23 C24 B1 121.5(4) . .
C25 C24 B1 121.2(3) . .
C20 C25 C24 121.7(3) . .
C20 C25 H25 119.2 . .
C24 C25 H25 119.2 . .
O3 B1 O2 124.6(4) . .
O3 B1 C24 117.5(3) . .
O2 B1 C24 117.8(3) . .
B1 O2 H2A 109.5 . .
B1 O3 H3A 109.5 . .
C7 P1 C13 107.95(17) . .
C7 P1 C1 111.95(16) . .
C13 P1 C1 108.42(17) . .
C7 P1 C19 110.97(17) . .
C13 P1 C19 111.09(16) . .
C1 P1 C19 106.47(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.391(5) .
C1 C2 1.395(5) .
C1 P1 1.810(4) .
C2 C3 1.377(5) .
C2 H2 0.9500 .
C3 C4 1.399(5) .
C3 H3 0.9500 .
C4 C5 1.388(5) .
C4 H4 0.9500 .
C5 C6 1.375(5) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C12 1.397(5) .
C7 C8 1.398(5) .
C7 P1 1.788(4) .
C8 C9 1.390(5) .
C8 H8 0.9500 .
C9 C10 1.382(6) .
C9 H9 0.9500 .
C10 C11 1.390(5) .
C10 H10 0.9500 .
C11 C12 1.396(5) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C14 1.382(5) .
C13 C18 1.408(5) .
C13 P1 1.791(3) .
C14 C15 1.380(5) .
C14 H14 0.9500 .
C15 C16 1.380(5) .
C15 H15 0.9500 .
C16 C17 1.381(5) .
C16 H16 0.9500 .
C17 C18 1.393(6) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C19 C20 1.510(5) .
C19 P1 1.820(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C25 1.387(5) .
C20 C21 1.403(5) .
C21 C22 1.372(5) .
C21 H21 0.9500 .
C22 C23 1.386(6) .
C22 H22 0.9500 .
C23 C24 1.398(5) .
C23 H23 0.9500 .
C24 C25 1.412(5) .
C24 B1 1.582(6) .
C25 H25 0.9500 .
B1 O3 1.359(5) .
B1 O2 1.361(5) .
O2 H2A 0.8400 .
O3 H3A 0.8400 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 91885451
