#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:28:41 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298963 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/97/7249742.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_7249742
loop_
_publ_author_name
'Xiang, Panjie'
'Sun, Kai'
'Shi, Anzai'
'An, Jiangzhen'
'Chen, Xiaolan'
'Qu, Lingbo'
'Yu, Bing'
_publ_section_title
;
 Visible-light-induced 1,3-difunctionalization of allylboronic esters
 enabled by a 1,2-boron shift
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1820
_journal_page_last               1827
_journal_paper_doi               10.1039/D4GC06330A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C19 H28 B N O4 S'
_chemical_formula_sum            'C19 H28 B N O4 S'
_chemical_formula_weight         377.33
_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_Int_Tables_number      2
_audit_creation_date             2022-06-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-07-18 deposited with the CCDC.	2025-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                84.420(3)
_cell_angle_beta                 63.871(3)
_cell_angle_gamma                87.806(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7822(7)
_cell_length_b                   10.6868(8)
_cell_length_c                   11.0049(8)
_cell_measurement_reflns_used    6241
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.33
_cell_volume                     1027.98(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9958
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            16617
_diffrn_reflns_theta_full        27.5143
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5977
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1317 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.8016.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2189
_exptl_crystal_description       needle
_exptl_crystal_F_000             404.4371
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.5365
_refine_diff_density_min         -0.8197
_refine_diff_density_rms         0.1384
_refine_ls_d_res_high            0.7692
_refine_ls_d_res_low             10.6360
_refine_ls_goodness_of_fit_ref   1.0581
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0581
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0811
_refine_ls_shift/su_max          0.0108
_refine_ls_shift/su_mean         0.0008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1344P)²+0.8366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2334
_refine_ls_wR_factor_ref         0.2616
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3533
_reflns_number_total             4702
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4gc06330a2.cif
_cod_data_source_block           a_a
_cod_depositor_comments          'Adding full bibliography for 7249742.cif.'
_cod_database_code               7249742
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C6(H6a,H6b,H6c), C5(H5a,H5b,H5c), C11(H11a,H11b,H11c),
 C4(H4a,H4b,H4c), C3(H3a,H3b,H3c), C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
S1 S 0.49998(10) 0.65122(8) 0.70819(9) 0.0520(3) Uani 1.000000 .
O4 O 0.8306(2) 0.37410(19) 0.6301(2) 0.0441(5) Uani 1.000000 .
O3 O 0.6456(3) 0.35995(19) 0.8481(2) 0.0491(6) Uani 1.000000 .
O2 O 0.4867(3) 0.5251(2) 0.6836(3) 0.0653(7) Uani 1.000000 .
O1 O 0.3636(3) 0.7221(3) 0.7790(3) 0.0771(9) Uani 1.000000 .
C8 C 0.7596(4) 0.5835(3) 0.7409(3) 0.0423(6) Uani 1.000000 .
H8 H 0.8139(4) 0.6187(3) 0.6463(3) 0.0507(8) Uiso 1.000000 R
C18 C 0.6733(4) 0.6747(3) 0.4325(4) 0.0515(8) Uani 1.000000 .
H18 H 0.6673(4) 0.5876(3) 0.4376(4) 0.0618(9) Uiso 1.000000 R
C13 C 0.6108(4) 0.7367(3) 0.5485(3) 0.0440(7) Uani 1.000000 .
C1 C 0.7732(4) 0.2447(3) 0.6577(3) 0.0440(7) Uani 1.000000 .
C7 C 0.8604(4) 0.6088(3) 0.8145(3) 0.0457(7) Uani 1.000000 .
C9 C 0.6061(4) 0.6504(3) 0.8030(3) 0.0488(7) Uani 1.000000 .
H9a H 0.6239(4) 0.7366(3) 0.8129(3) 0.0586(9) Uiso 1.000000 R
H9b H 0.5456(4) 0.6100(3) 0.8933(3) 0.0586(9) Uiso 1.000000 R
N1 N 0.8869(6) 0.8533(3) 0.8006(5) 0.0937(13) Uani 1.000000 .
C12 C 1.0188(4) 0.5531(4) 0.7392(4) 0.0568(8) Uani 1.000000 .
H12a H 1.0126(7) 0.4630(4) 0.754(2) 0.0852(13) Uiso 1.000000 GR
H12b H 1.0572(14) 0.578(2) 0.6437(5) 0.0852(13) Uiso 1.000000 GR
H12c H 1.0861(9) 0.584(2) 0.772(2) 0.0852(13) Uiso 1.000000 GR
C2 C 0.6871(4) 0.2302(3) 0.8154(3) 0.0506(8) Uani 1.000000 .
C6 C 0.9060(5) 0.1572(4) 0.5961(4) 0.0636(10) Uani 1.000000 .
H6a H 0.947(2) 0.169(2) 0.4988(4) 0.0954(15) Uiso 1.000000 GR
H6b H 0.9833(16) 0.176(2) 0.623(3) 0.0954(15) Uiso 1.000000 GR
H6c H 0.8723(9) 0.0718(4) 0.627(3) 0.0954(15) Uiso 1.000000 GR
C17 C 0.7449(4) 0.7437(4) 0.3087(4) 0.0580(9) Uani 1.000000 .
H17 H 0.7868(4) 0.7019(4) 0.2301(4) 0.0696(10) Uiso 1.000000 R
C10 C 0.8777(5) 0.7477(3) 0.8051(4) 0.0597(9) Uani 1.000000 .
C16 C 0.7564(4) 0.8737(4) 0.2975(4) 0.0566(8) Uani 1.000000 .
C5 C 0.6680(5) 0.2419(4) 0.5887(4) 0.0622(10) Uani 1.000000 .
H5a H 0.587(2) 0.301(2) 0.626(2) 0.0933(14) Uiso 1.000000 GR
H5b H 0.7249(9) 0.264(3) 0.4929(6) 0.0933(14) Uiso 1.000000 GR
H5c H 0.626(3) 0.1591(8) 0.604(3) 0.0933(14) Uiso 1.000000 GR
C14 C 0.6221(5) 0.8660(3) 0.5409(4) 0.0606(9) Uani 1.000000 .
H14 H 0.5801(5) 0.9076(3) 0.6197(4) 0.0727(11) Uiso 1.000000 R
C11 C 0.7888(5) 0.5623(4) 0.9648(4) 0.0613(9) Uani 1.000000 .
H11a H 0.6922(16) 0.602(2) 1.0104(7) 0.0919(14) Uiso 1.000000 GR
H11b H 0.774(3) 0.4729(5) 0.9748(4) 0.0919(14) Uiso 1.000000 GR
H11c H 0.8548(17) 0.582(3) 1.0040(8) 0.0919(14) Uiso 1.000000 GR
B1 B 0.7431(4) 0.4353(3) 0.7390(4) 0.0408(7) Uani 1.000000 .
C15 C 0.6961(5) 0.9328(4) 0.4159(4) 0.0652(10) Uani 1.000000 .
H15 H 0.7057(5) 1.0196(4) 0.4113(4) 0.0782(12) Uiso 1.000000 R
C4 C 0.7905(7) 0.1860(4) 0.8820(4) 0.0783(14) Uani 1.000000 .
H4a H 0.8843(18) 0.233(2) 0.839(2) 0.118(2) Uiso 1.000000 GR
H4b H 0.7408(18) 0.199(3) 0.9767(9) 0.118(2) Uiso 1.000000 GR
H4c H 0.812(4) 0.0981(9) 0.872(3) 0.118(2) Uiso 1.000000 GR
C3 C 0.5413(6) 0.1517(4) 0.8716(5) 0.0843(15) Uani 1.000000 .
H3a H 0.496(3) 0.145(3) 0.9691(5) 0.126(2) Uiso 1.000000 GR
H3b H 0.4711(19) 0.192(2) 0.841(3) 0.126(2) Uiso 1.000000 GR
H3c H 0.5651(9) 0.0693(13) 0.840(3) 0.126(2) Uiso 1.000000 GR
C19 C 0.8303(6) 0.9490(5) 0.1613(5) 0.0842(14) Uani 1.000000 .
H19a H 0.921(2) 0.988(3) 0.1521(17) 0.126(2) Uiso 1.000000 GR
H19b H 0.855(4) 0.8943(8) 0.0903(5) 0.126(2) Uiso 1.000000 GR
H19c H 0.7612(17) 1.013(2) 0.1547(16) 0.126(2) Uiso 1.000000 GR
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 0.00347 0.00161 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 0.00141 0.00067 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 0.01158 0.00611 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 0.00653 0.00323 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'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'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
O1 S1 O2 119.19(19) . . ?
C13 S1 O2 107.90(16) . . ?
C13 S1 O1 107.98(16) . . ?
C9 S1 O2 108.05(16) . . ?
C9 S1 O1 106.61(17) . . ?
C9 S1 C13 106.45(15) . . ?
B1 O4 C1 107.2(2) . . ?
B1 O3 C2 106.5(2) . . ?
C7 C8 H8 107.30(16) . . ?
C9 C8 H8 107.30(16) . . ?
C9 C8 C7 111.6(2) . . ?
B1 C8 H8 107.30(16) . . ?
B1 C8 C7 110.0(2) . . ?
B1 C8 C9 113.1(3) . . ?
C13 C18 H18 120.5(2) . . ?
C17 C18 H18 120.5(2) . . ?
C17 C18 C13 118.9(3) . . ?
C18 C13 S1 119.6(3) . . ?
C14 C13 S1 119.7(3) . . ?
C14 C13 C18 120.5(3) . . ?
C2 C1 O4 102.3(2) . . ?
C6 C1 O4 108.8(3) . . ?
C6 C1 C2 115.5(3) . . ?
C5 C1 O4 105.4(2) . . ?
C5 C1 C2 113.3(3) . . ?
C5 C1 C6 110.7(3) . . ?
C12 C7 C8 109.8(3) . . ?
C10 C7 C8 106.7(3) . . ?
C10 C7 C12 107.8(3) . . ?
C11 C7 C8 113.7(3) . . ?
C11 C7 C12 111.3(3) . . ?
C11 C7 C10 107.2(3) . . ?
C8 C9 S1 114.7(2) . . ?
H9a C9 S1 108.59(11) . . ?
H9a C9 C8 108.59(17) . . ?
H9b C9 S1 108.59(12) . . ?
H9b C9 C8 108.59(16) . . ?
H9b C9 H9a 107.6 . . ?
H12a C12 C7 109.5 . . ?
H12b C12 C7 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C7 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C1 C2 O3 102.5(2) . . ?
C4 C2 O3 106.3(3) . . ?
C4 C2 C1 112.6(3) . . ?
C3 C2 O3 108.4(3) . . ?
C3 C2 C1 114.1(3) . . ?
C3 C2 C4 112.0(4) . . ?
H6a C6 C1 109.5 . . ?
H6b C6 C1 109.5 . . ?
H6b C6 H6a 109.5 . . ?
H6c C6 C1 109.5 . . ?
H6c C6 H6a 109.5 . . ?
H6c C6 H6b 109.5 . . ?
H17 C17 C18 119.0(2) . . ?
C16 C17 C18 122.0(3) . . ?
C16 C17 H17 119.0(2) . . ?
N1 C10 C7 178.1(5) . . ?
C15 C16 C17 117.7(3) . . ?
C19 C16 C17 121.7(4) . . ?
C19 C16 C15 120.6(4) . . ?
H5a C5 C1 109.5 . . ?
H5b C5 C1 109.5 . . ?
H5b C5 H5a 109.5 . . ?
H5c C5 C1 109.5 . . ?
H5c C5 H5a 109.5 . . ?
H5c C5 H5b 109.5 . . ?
H14 C14 C13 120.2(2) . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.2(2) . . ?
H11a C11 C7 109.5 . . ?
H11b C11 C7 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C7 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
O3 B1 O4 114.4(3) . . ?
C8 B1 O4 122.0(3) . . ?
C8 B1 O3 123.6(3) . . ?
C14 C15 C16 121.4(3) . . ?
H15 C15 C16 119.3(2) . . ?
H15 C15 C14 119.3(2) . . ?
H4a C4 C2 109.5 . . ?
H4b C4 C2 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 C2 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
H3a C3 C2 109.5 . . ?
H3b C3 C2 109.5 . . ?
H3b C3 H3a 109.5 . . ?
H3c C3 C2 109.5 . . ?
H3c C3 H3a 109.5 . . ?
H3c C3 H3b 109.5 . . ?
H19a C19 C16 109.5 . . ?
H19b C19 C16 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C16 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
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
S1 O2 1.422(3) . ?
S1 O1 1.443(3) . ?
S1 C13 1.785(3) . ?
S1 C9 1.766(3) . ?
O4 C1 1.466(3) . ?
O4 B1 1.343(4) . ?
O3 C2 1.464(3) . ?
O3 B1 1.364(4) . ?
C8 H8 0.9800 . ?
C8 C7 1.571(4) . ?
C8 C9 1.530(4) . ?
C8 B1 1.601(4) . ?
C18 H18 0.9300 . ?
C18 C13 1.374(4) . ?
C18 C17 1.376(5) . ?
C13 C14 1.381(5) . ?
C1 C2 1.553(4) . ?
C1 C6 1.509(5) . ?
C1 C5 1.527(5) . ?
C7 C12 1.529(5) . ?
C7 C10 1.489(4) . ?
C7 C11 1.523(5) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
N1 C10 1.130(5) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C2 C4 1.527(6) . ?
C2 C3 1.528(6) . ?
C6 H6a 0.9600 . ?
C6 H6b 0.9600 . ?
C6 H6c 0.9600 . ?
C17 H17 0.9300 . ?
C17 C16 1.387(5) . ?
C16 C15 1.378(6) . ?
C16 C19 1.508(6) . ?
C5 H5a 0.9600 . ?
C5 H5b 0.9600 . ?
C5 H5c 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.378(6) . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C15 H15 0.9300 . ?
C4 H4a 0.9600 . ?
C4 H4b 0.9600 . ?
C4 H4c 0.9600 . ?
C3 H3a 0.9600 . ?
C3 H3b 0.9600 . ?
C3 H3c 0.9600 . ?
C19 H19a 0.9600 . ?
C19 H19b 0.9600 . ?
C19 H19c 0.9600 . ?
