#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:35:05 +0200 (Sat 23 de Aug de 2025) $
#$Revision: 301870 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/26/7242616.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_7242616
loop_
_publ_author_name
'Li, Jing'
'Shi, Yian'
_publ_section_title
;
 Catalytic enantioselective bromohydroxylation of cinnamyl alcohols
;
_journal_issue                   22
_journal_name_full               'RSC Advances'
_journal_page_first              13040
_journal_page_last               13046
_journal_paper_doi               10.1039/D1RA02297K
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H13 Br O2'
_chemical_formula_weight         245.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-11-04 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.30480(10)
_cell_length_b                   9.2603(2)
_cell_length_c                   27.0823(7)
_cell_measurement_reflns_used    19942
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      28.4190
_cell_measurement_theta_min      2.3190
_cell_volume                     2082.76(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            48490
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.324
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.913
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4767
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0229
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0298P)²+0.3454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0507
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4521
_reflns_number_total             4767
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra02297k2.cif
_cod_data_source_block           3_CCDC1
_cod_database_code               7242616
_shelx_shelxl_version_number     2014/7
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.06004(3) 0.14505(3) 0.45919(2) 0.02365(8) Uani 1 1 d . . . . .
O1 O 0.1555(2) 0.4480(2) 0.45241(10) 0.0307(5) Uani 1 1 d D . . . .
H1 H 0.064(3) 0.467(4) 0.4579(14) 0.046 Uiso 1 1 d D U . . .
O2 O 0.2170(3) -0.0656(2) 0.43495(8) 0.0252(5) Uani 1 1 d D . . . .
H2 H 0.269(4) -0.126(3) 0.4215(12) 0.038 Uiso 1 1 d D U . . .
C1 C 0.1735(4) 0.3347(3) 0.41733(12) 0.0277(7) Uani 1 1 d . . . . .
H1A H 0.2767 0.3448 0.4009 0.033 Uiso 1 1 calc R U . . .
H1B H 0.0899 0.3433 0.3925 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1638(3) 0.1867(3) 0.44072(11) 0.0193(6) Uani 1 1 d . . . . .
H2A H 0.2269 0.1899 0.4713 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2352(3) 0.0671(3) 0.40847(11) 0.0219(6) Uani 1 1 d . . . . .
H3A H 0.3510 0.0859 0.4058 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1700(3) 0.0586(3) 0.35662(11) 0.0215(6) Uani 1 1 d . . . . .
C5 C 0.0325(4) -0.0198(3) 0.34495(11) 0.0266(7) Uani 1 1 d . . . . .
H5 H -0.0215 -0.0705 0.3695 0.032 Uiso 1 1 calc R U . . .
C6 C -0.0250(4) -0.0230(4) 0.29674(12) 0.0328(8) Uani 1 1 d . . . . .
H6 H -0.1175 -0.0759 0.2898 0.039 Uiso 1 1 calc R U . . .
C7 C 0.0506(4) 0.0496(4) 0.25901(11) 0.0337(7) Uani 1 1 d . . . . .
C8 C 0.1884(4) 0.1274(4) 0.27071(12) 0.0350(7) Uani 1 1 d . . . . .
H8 H 0.2422 0.1772 0.2459 0.042 Uiso 1 1 calc R U . . .
C9 C 0.2474(4) 0.1326(4) 0.31843(11) 0.0298(7) Uani 1 1 d . . . . .
H9 H 0.3397 0.1859 0.3252 0.036 Uiso 1 1 calc R U . . .
C10 C -0.0108(5) 0.0426(5) 0.20645(13) 0.0494(10) Uani 1 1 d . . . . .
H10A H 0.0569 -0.0203 0.1874 0.074 Uiso 1 1 calc R U . . .
H10B H -0.0094 0.1376 0.1922 0.074 Uiso 1 1 calc R U . . .
H10C H -0.1190 0.0061 0.2063 0.074 Uiso 1 1 calc R U . . .
Br2 Br 0.61797(4) 0.88088(3) 0.39073(2) 0.03303(9) Uani 1 1 d . . . . .
O3 O 0.8608(3) 0.5726(2) 0.47234(8) 0.0284(5) Uani 1 1 d D . . . .
H3 H 0.831(5) 0.586(4) 0.4998(9) 0.043 Uiso 1 1 d D U . . .
O4 O 0.3708(2) 0.6716(2) 0.43867(8) 0.0270(5) Uani 1 1 d D . . . .
H4 H 0.308(4) 0.606(3) 0.4451(13) 0.041 Uiso 1 1 d D U . . .
C11 C 0.8247(3) 0.6911(3) 0.44053(12) 0.0242(6) Uani 1 1 d . . . . .
H11A H 0.8524 0.6653 0.4069 0.029 Uiso 1 1 calc R U . . .
H11B H 0.8902 0.7734 0.4499 0.029 Uiso 1 1 calc R U . . .
C12 C 0.6479(3) 0.7335(3) 0.44269(11) 0.0223(6) Uani 1 1 d . . . . .
H12 H 0.6277 0.7792 0.4747 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5285(3) 0.6104(3) 0.43645(10) 0.0210(6) Uani 1 1 d . . . . .
H13 H 0.5402 0.5474 0.4653 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5546(3) 0.5176(3) 0.39114(11) 0.0199(5) Uani 1 1 d . . . . .
C15 C 0.6551(4) 0.3975(3) 0.39390(12) 0.0268(7) Uani 1 1 d . . . . .
H15 H 0.7015 0.3728 0.4240 0.032 Uiso 1 1 calc R U . . .
C16 C 0.6871(4) 0.3142(3) 0.35253(13) 0.0311(7) Uani 1 1 d . . . . .
H16 H 0.7555 0.2350 0.3551 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6183(4) 0.3478(3) 0.30735(11) 0.0290(6) Uani 1 1 d . . . . .
C18 C 0.5144(4) 0.4644(3) 0.30518(12) 0.0305(7) Uani 1 1 d . . . . .
H18 H 0.4646 0.4865 0.2754 0.037 Uiso 1 1 calc R U . . .
C19 C 0.4826(4) 0.5491(3) 0.34614(12) 0.0276(7) Uani 1 1 d . . . . .
H19 H 0.4128 0.6273 0.3435 0.033 Uiso 1 1 calc R U . . .
C20 C 0.6562(5) 0.2614(4) 0.26147(14) 0.0434(9) Uani 1 1 d . . . . .
H20A H 0.7460 0.3043 0.2446 0.065 Uiso 1 1 calc R U . . .
H20B H 0.5641 0.2609 0.2400 0.065 Uiso 1 1 calc R U . . .
H20C H 0.6826 0.1640 0.2706 0.065 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C1 O1 H1 113(3) . . ?
C3 O2 H2 109(3) . . ?
O1 C1 C2 112.5(3) . . ?
O1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 113.3(2) . . ?
C1 C2 Br1 109.58(19) . . ?
C3 C2 Br1 111.75(19) . . ?
C1 C2 H2A 107.3 . . ?
C3 C2 H2A 107.3 . . ?
Br1 C2 H2A 107.3 . . ?
O2 C3 C4 112.6(2) . . ?
O2 C3 C2 107.1(2) . . ?
C4 C3 C2 115.5(2) . . ?
O2 C3 H3A 107.1 . . ?
C4 C3 H3A 107.1 . . ?
C2 C3 H3A 107.1 . . ?
C5 C4 C9 117.8(3) . . ?
C5 C4 C3 122.3(3) . . ?
C9 C4 C3 119.9(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 117.4(3) . . ?
C6 C7 C10 121.6(3) . . ?
C8 C7 C10 121.0(3) . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C4 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 O3 H3 112(3) . . ?
C13 O4 H4 107(3) . . ?
O3 C11 C12 112.2(2) . . ?
O3 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
O3 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 115.6(2) . . ?
C13 C12 Br2 110.9(2) . . ?
C11 C12 Br2 105.8(2) . . ?
C13 C12 H12 108.1 . . ?
C11 C12 H12 108.1 . . ?
Br2 C12 H12 108.1 . . ?
O4 C13 C14 113.0(2) . . ?
O4 C13 C12 107.2(2) . . ?
C14 C13 C12 115.0(2) . . ?
O4 C13 H13 107.1 . . ?
C14 C13 H13 107.1 . . ?
C12 C13 H13 107.1 . . ?
C19 C14 C15 118.2(3) . . ?
C19 C14 C13 122.0(2) . . ?
C15 C14 C13 119.7(3) . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C20 120.6(3) . . ?
C16 C17 C20 121.4(3) . . ?
C17 C18 C19 121.8(3) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C14 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Br1 C2 1.963(3) . ?
O1 C1 1.424(4) . ?
O1 H1 0.80(2) . ?
O2 C3 1.431(3) . ?
O2 H2 0.79(2) . ?
C1 C2 1.512(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.530(4) . ?
C2 H2A 0.9800 . ?
C3 C4 1.507(4) . ?
C3 H3A 0.9800 . ?
C4 C5 1.390(4) . ?
C4 C9 1.397(4) . ?
C5 C6 1.391(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(5) . ?
C7 C10 1.514(5) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Br2 C12 1.976(3) . ?
O3 C11 1.427(4) . ?
O3 H3 0.79(2) . ?
O4 C13 1.429(3) . ?
O4 H4 0.82(2) . ?
C11 C12 1.521(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.520(4) . ?
C12 H12 0.9800 . ?
C13 C14 1.514(4) . ?
C13 H13 0.9800 . ?
C14 C19 1.389(4) . ?
C14 C15 1.392(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(4) . ?
C17 C20 1.511(4) . ?
C18 C19 1.384(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.80(2) 1.99(2) 2.759(3) 163(4) 1_455
O2 H2 O4 0.79(2) 2.11(3) 2.750(3) 138(3) 1_545
O3 H3 O2 0.79(2) 2.01(2) 2.781(3) 163(4) 4_556
O4 H4 O1 0.82(2) 1.94(2) 2.760(3) 174(4) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -161.3(2) . . . . ?
O1 C1 C2 Br1 73.1(3) . . . . ?
C1 C2 C3 O2 -179.7(2) . . . . ?
Br1 C2 C3 O2 -55.3(3) . . . . ?
C1 C2 C3 C4 -53.4(3) . . . . ?
Br1 C2 C3 C4 71.0(3) . . . . ?
O2 C3 C4 C5 36.5(4) . . . . ?
C2 C3 C4 C5 -87.0(3) . . . . ?
O2 C3 C4 C9 -144.2(3) . . . . ?
C2 C3 C4 C9 92.4(3) . . . . ?
C9 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C5 C6 C7 C10 178.6(3) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C10 C7 C8 C9 -178.8(3) . . . . ?
C7 C8 C9 C4 0.2(5) . . . . ?
C5 C4 C9 C8 0.0(5) . . . . ?
C3 C4 C9 C8 -179.3(3) . . . . ?
O3 C11 C12 C13 -50.1(4) . . . . ?
O3 C11 C12 Br2 -173.2(2) . . . . ?
C11 C12 C13 O4 -179.0(2) . . . . ?
Br2 C12 C13 O4 -58.6(2) . . . . ?
C11 C12 C13 C14 -52.4(4) . . . . ?
Br2 C12 C13 C14 68.0(3) . . . . ?
O4 C13 C14 C19 33.7(4) . . . . ?
C12 C13 C14 C19 -89.8(3) . . . . ?
O4 C13 C14 C15 -147.0(3) . . . . ?
C12 C13 C14 C15 89.4(3) . . . . ?
C19 C14 C15 C16 2.2(4) . . . . ?
C13 C14 C15 C16 -177.1(3) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 C18 -1.4(5) . . . . ?
C15 C16 C17 C20 177.9(3) . . . . ?
C16 C17 C18 C19 2.0(5) . . . . ?
C20 C17 C18 C19 -177.3(3) . . . . ?
C17 C18 C19 C14 -0.5(5) . . . . ?
C15 C14 C19 C18 -1.6(4) . . . . ?
C13 C14 C19 C18 177.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168342122
