#------------------------------------------------------------------------------
#$Date: 2020-05-05 15:46:55 +0300 (Tue, 05 May 2020) $
#$Revision: 251573 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/61/7126187.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_7126187
loop_
_publ_author_name
'Zeng, Yao-Fu'
'Liu, Xu-Ge'
'Tan, Dong-Hang'
'Fan, Wen-Xin'
'Li, Yi-Na'
'Guo, Yu'
'Wang, Honggen'
_publ_section_title
;
 Halohydroxylation of alkenyl MIDA boronates: switchable stereoselectivity
 induced by B(MIDA) substituent.
;
_journal_issue                   31
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4332
_journal_page_last               4335
_journal_paper_doi               10.1039/d0cc00722f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C14 H17 B Br N O5'
_chemical_formula_sum            'C14 H17 B Br N O5'
_chemical_formula_weight         370.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-09-26 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.374(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.4754(5)
_cell_length_b                   6.47129(11)
_cell_length_c                   24.0236(6)
_cell_measurement_reflns_used    4211
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.2560
_cell_measurement_theta_min      4.0300
_cell_volume                     3041.07(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  78.00   1.00    5.00    --   44.52  57.00-120.00   57
  2  ω     79.00 111.00   1.00    5.00    --   44.52  57.00-120.00   32
  3  ω     86.00 168.00   1.00   12.00    --  100.00  30.00 -30.00   82
  4  ω     77.00 106.00   1.00    5.00    --   44.52 125.00  90.00   29
  5  ω     28.00 126.00   1.00   12.00    --  100.00 -30.00 -30.00   98
  6  ω     82.00  96.00   1.00   12.00    --  100.00 -94.00   0.00   14
  7  ω     81.00 121.00   1.00   12.00    --  100.00 -77.00   0.00   40
  8  ω     60.00 120.00   1.00   12.00    --  100.00-125.00   0.00   60
  9  ω     26.00  52.00   1.00   12.00    --  100.00 -94.00   0.00   26
 10  ω     27.00  73.00   1.00   12.00    --  100.00 -77.00   0.00   46
 11  ω    -69.00  19.00   1.00    5.00    --  -44.52  57.00-180.00   88
 12  ω   -151.00 -96.00   1.00   12.00    --  -90.00-125.00 150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0126162000
_diffrn_orient_matrix_UB_12      -0.2344901000
_diffrn_orient_matrix_UB_13      -0.0087173000
_diffrn_orient_matrix_UB_21      0.0656365000
_diffrn_orient_matrix_UB_22      -0.0404716000
_diffrn_orient_matrix_UB_23      0.0579296000
_diffrn_orient_matrix_UB_31      -0.0416781000
_diffrn_orient_matrix_UB_32      0.0074981000
_diffrn_orient_matrix_UB_33      0.0390074000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6092
_diffrn_reflns_theta_full        67.0742
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.04
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6162
_exptl_crystal_description       needle
_exptl_crystal_F_000             1503.0215
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.4472
_refine_diff_density_min         -0.5750
_refine_diff_density_rms         0.0778
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             10.9412
_refine_ls_goodness_of_fit_ref   1.0609
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0609
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0459P)²+2.3241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0753
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -25
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2563
_reflns_number_total             2719
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc00722f2.cif
_cod_data_source_block           zyf_170608_2
_cod_depositor_comments
'Adding full bibliography for 7126186--7126187.cif.'
_cod_original_cell_volume        3041.05(13)
_cod_database_code               7126187
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C21(H21a,H21b)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C15(H15), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C20(H20c,H20b,H20a)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.616
_oxdiff_exptl_absorpt_empirical_full_min 0.501
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-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_refinement_flags_posn
Br1 Br 0.052897(10) 0.73508(3) 0.038188(9) 0.01641(10) Uani 1.000000 .
O1 O 0.21356(8) 0.7175(2) 0.12100(6) 0.0172(3) Uani 1.000000 .
O2 O 0.24271(7) 0.4623(2) 0.06110(6) 0.0206(3) Uani 1.000000 .
O3 O 0.20863(8) 0.8248(3) 0.20763(7) 0.0247(3) Uani 1.000000 .
O5 O 0.16834(8) 0.9163(3) -0.00028(7) 0.0279(4) Uani 1.000000 .
O6 O 0.32442(9) 0.2210(3) 0.09396(9) 0.0345(4) Uani 1.000000 .
N7 N 0.17856(8) 0.3648(3) 0.11999(7) 0.0143(3) Uani 1.000000 .
C8 C 0.27625(11) 0.3055(4) 0.09711(10) 0.0216(4) Uani 1.000000 .
C9 C 0.12155(10) 0.5983(3) 0.01517(9) 0.0164(4) Uani 1.000000 .
C10 C 0.19937(10) 0.6926(3) 0.16910(9) 0.0170(4) Uani 1.000000 .
C11 C 0.04397(12) 0.9676(4) -0.10492(10) 0.0241(5) Uani 1.000000 .
C12 C 0.12199(11) 0.2142(3) 0.09006(10) 0.0190(4) Uani 1.000000 .
C13 C 0.13608(12) 0.7315(3) -0.03080(10) 0.0200(5) Uani 1.000000 .
C14 C -0.04301(11) 0.8384(4) -0.20032(9) 0.0239(5) Uani 1.000000 .
C15 C -0.01302(12) 0.9988(4) -0.15963(10) 0.0267(5) Uani 1.000000 .
C16 C 0.04346(10) 0.6100(3) -0.13005(9) 0.0188(4) Uani 1.000000 .
C17 C -0.01344(11) 0.6426(4) -0.18424(9) 0.0214(5) Uani 1.000000 .
C18 C 0.16983(10) 0.4818(3) 0.16973(9) 0.0171(4) Uani 1.000000 .
C19 C 0.07276(12) 0.7722(3) -0.08962(10) 0.0188(5) Uani 1.000000 .
C20 C -0.10468(12) 0.8738(5) -0.25966(10) 0.0336(6) Uani 1.000000 .
C21 C 0.24626(12) 0.2538(3) 0.14214(11) 0.0204(5) Uani 1.000000 .
B22 B 0.18797(11) 0.5461(4) 0.07614(10) 0.0156(4) Uani 1.000000 .
H16 H 0.06269(10) 0.4755(3) -0.12039(9) 0.0225(5) Uiso 1.000000 R
H17 H -0.03280(11) 0.5294(4) -0.21104(9) 0.0257(6) Uiso 1.000000 R
H15 H -0.03192(12) 1.1336(4) -0.16939(10) 0.0320(6) Uiso 1.000000 R
H11 H 0.06324(12) 1.0804(4) -0.07796(10) 0.0290(6) Uiso 1.000000 R
H5 H 0.1882(13) 0.973(2) -0.0198(7) 0.0419(6) Uiso 1.000000 GR
H9 H 0.10160(10) 0.4646(3) -0.00529(9) 0.0197(5) Uiso 1.000000 R
H12a H 0.1221(5) 0.1116(14) 0.12012(19) 0.0284(7) Uiso 1.000000 GR
H12b H 0.07816(13) 0.2876(5) 0.0737(6) 0.0284(7) Uiso 1.000000 GR
H12c H 0.1285(4) 0.1444(17) 0.0566(5) 0.0284(7) Uiso 1.000000 GR
H13 H 0.16972(12) 0.6552(3) -0.04206(10) 0.0241(6) Uiso 1.000000 R
H18a H 0.12088(10) 0.4921(3) 0.16175(9) 0.0205(5) Uiso 1.000000 R
H18b H 0.19469(10) 0.4133(3) 0.20969(9) 0.0205(5) Uiso 1.000000 R
H20c H -0.1416(4) 0.935(3) -0.25111(12) 0.0505(9) Uiso 1.000000 GR
H20b H -0.0925(3) 0.968(2) -0.2856(4) 0.0505(9) Uiso 1.000000 GR
H20a H -0.1200(6) 0.7416(6) -0.2808(4) 0.0505(9) Uiso 1.000000 GR
H21a H 0.27690(12) 0.3014(3) 0.18364(11) 0.0244(6) Uiso 1.000000 R
H21b H 0.23961(12) 0.1028(3) 0.14339(11) 0.0244(6) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00963 0.00408 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
B22 O1 C10 113.21(16) . . ?
B22 O2 C8 113.19(16) . . ?
H5 O5 C13 109.5 . . ?
C18 N7 C12 111.81(15) . . ?
C21 N7 C12 109.52(16) . . ?
C21 N7 C18 112.39(15) . . ?
B22 N7 C12 116.66(15) . . ?
B22 N7 C18 103.93(14) . . ?
B22 N7 C21 102.15(14) . . ?
O6 C8 O2 123.7(2) . . ?
C21 C8 O2 110.95(17) . . ?
C21 C8 O6 125.4(2) . . ?
C13 C9 Br1 110.23(14) . . ?
B22 C9 Br1 108.82(12) . . ?
B22 C9 C13 114.09(17) . . ?
H9 C9 Br1 107.83(6) . . ?
H9 C9 C13 107.83(11) . . ?
H9 C9 B22 107.83(11) . . ?
O3 C10 O1 123.8(2) . . ?
C18 C10 O1 111.65(17) . . ?
C18 C10 O3 124.54(19) . . ?
C19 C11 C15 120.2(2) . . ?
H11 C11 C15 119.88(14) . . ?
H11 C11 C19 119.88(14) . . ?
H12a C12 N7 109.5 . . ?
H12b C12 N7 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 N7 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C9 C13 O5 107.57(16) . . ?
C19 C13 O5 112.96(18) . . ?
C19 C13 C9 113.33(18) . . ?
H13 C13 O5 107.57(12) . . ?
H13 C13 C9 107.57(11) . . ?
H13 C13 C19 107.57(11) . . ?
C17 C14 C15 117.2(2) . . ?
C20 C14 C15 121.5(2) . . ?
C20 C14 C17 121.3(2) . . ?
C14 C15 C11 121.9(2) . . ?
H15 C15 C11 119.06(14) . . ?
H15 C15 C14 119.06(13) . . ?
C19 C16 C17 120.7(2) . . ?
H16 C16 C17 119.65(13) . . ?
H16 C16 C19 119.65(13) . . ?
C16 C17 C14 121.4(2) . . ?
H17 C17 C14 119.29(14) . . ?
H17 C17 C16 119.29(13) . . ?
C10 C18 N7 105.01(15) . . ?
H18a C18 N7 110.74(10) . . ?
H18a C18 C10 110.74(11) . . ?
H18b C18 N7 110.74(10) . . ?
H18b C18 C10 110.74(11) . . ?
H18b C18 H18a 108.8 . . ?
C13 C19 C11 122.1(2) . . ?
C16 C19 C11 118.6(2) . . ?
C16 C19 C13 119.31(19) . . ?
H20c C20 C14 109.5 . . ?
H20b C20 C14 109.5 . . ?
H20b C20 H20c 109.5 . . ?
H20a C20 C14 109.5 . . ?
H20a C20 H20c 109.5 . . ?
H20a C20 H20b 109.5 . . ?
C8 C21 N7 106.05(17) . . ?
H21a C21 N7 110.52(11) . . ?
H21a C21 C8 110.52(12) . . ?
H21b C21 N7 110.52(10) . . ?
H21b C21 C8 110.52(12) . . ?
H21b C21 H21a 108.7 . . ?
O2 B22 O1 111.11(16) . . ?
N7 B22 O1 100.05(14) . . ?
N7 B22 O2 102.51(16) . . ?
C9 B22 O1 115.42(17) . . ?
C9 B22 O2 110.71(15) . . ?
C9 B22 N7 115.94(16) . . ?
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
Br1 C9 1.9841(19) . ?
O1 C10 1.321(3) . ?
O1 B22 1.485(3) . ?
O2 C8 1.335(3) . ?
O2 B22 1.469(2) . ?
O3 C10 1.215(3) . ?
O5 C13 1.424(3) . ?
O5 H5 0.8400 . ?
O6 C8 1.200(3) . ?
N7 C12 1.490(3) . ?
N7 C18 1.490(2) . ?
N7 C21 1.508(3) . ?
N7 B22 1.644(3) . ?
C8 C21 1.507(3) . ?
C9 C13 1.531(3) . ?
C9 B22 1.603(3) . ?
C9 H9 1.0000 . ?
C10 C18 1.508(3) . ?
C11 C15 1.392(3) . ?
C11 C19 1.389(3) . ?
C11 H11 0.9500 . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?
C13 C19 1.526(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.389(4) . ?
C14 C17 1.398(4) . ?
C14 C20 1.510(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 C19 1.391(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18a 0.9900 . ?
C18 H18b 0.9900 . ?
C20 H20c 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20a 0.9800 . ?
C21 H21a 0.9900 . ?
C21 H21b 0.9900 . ?
