Catalytic enantioselective bromohydroxylation of cinnamyl alcohols
Li, Jing; Shi, Yian; RSC Advances 11 (2021) 13040–13046; doi:10.1039/D1RA02297K

data_7242617
_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_moiety         'C11 H14 Br Cl O2'
_chemical_formula_sum            'C11 H14 Br Cl O2'
_chemical_formula_weight         293.58
_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   geom
_audit_creation_date             2020-08-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-04 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                   10.45924(4)
_cell_length_b                   10.51707(4)
_cell_length_c                   22.10012(8)
_cell_measurement_reflns_used    54415
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.3440
_cell_measurement_theta_min      3.9930
_cell_volume                     2431.026(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     13.00  65.00   0.50    0.05    --   42.30  77.00 -60.00  104
  2  \w     17.00  49.00   0.50    0.05    --   42.30  77.00-120.00   64
  3  \w     71.00  97.00   0.50    0.05    --   42.30  77.00 -60.00   52
  4  \w     86.00 113.00   0.50    0.05    --   42.30  77.00   0.00   54
  5  \w     14.00  72.00   0.50    0.05    --   42.30  77.00   0.00  116
  6  \w     13.00  73.00   0.50    0.05    --   42.30  77.00  90.00  120
  7  \w     83.00 116.00   0.50    0.05    --   42.30  77.00  90.00   66
  8  \w     20.00 117.00   0.50    0.05    --   42.30  57.00  60.00  194
  9  \w     50.00  76.00   0.50    0.05    --   42.30  77.00-120.00   52
 10  \w     20.00  50.00   0.50    0.05    --   42.30  37.00-180.00   60
 11  \w     21.00  73.00   0.50    0.05    --   42.30  57.00-180.00  104
 12  \w     83.00 115.00   0.50    0.05    --   42.30  57.00-180.00   64
 13  \w     13.00 117.00   0.50    0.05    --   42.30  77.00-180.00  208
 14  \w     23.00  94.00   0.50    0.05    --   42.30  37.00 -60.00  142
 15  \w     21.00  86.00   0.50    0.05    --   42.30  37.00   0.00  130
 16  \w    -83.00 -36.00   0.50    0.05    --  -42.30 125.00  90.00   94
 17  \w    -76.00 -50.00   0.50    0.05    -- -102.00 111.00  44.00   52
 18  \w   -108.00 -77.00   0.50    0.05    -- -102.00 111.00  44.00   62
 19  \w    -78.00  -4.00   0.50    0.05    --  -42.30 111.00  44.00  148
 20  \w    108.00 133.00   0.50    0.05    --  107.38 111.00  44.00   50
 21  \w     34.00 106.00   0.50    0.05    --  107.38 -77.00  90.00  144
 22  \w     48.00  77.00   0.50    0.05    --  107.38-125.00  60.00   58
 23  \w     82.00 111.00   0.50    0.05    --  107.38-125.00  60.00   58
 24  \w     42.00  73.00   0.50    0.05    --  107.38 -61.00 -60.00   62
 25  \w     37.00 108.00   0.50    0.05    --  107.38-111.00 -49.00  142
 26  \w     37.00 108.00   0.50    0.05    --  107.38-125.00 -60.00  142
 27  \w     39.00  95.00   0.50    0.05    --  107.38 -94.00   0.00  112
 28  \w     37.00  62.00   0.50    0.05    --  107.38-125.00-180.00   50
 29  \w     76.00 111.00   0.50    0.05    --  107.38-125.00-180.00   70
 30  \w     58.00  96.00   0.50    0.05    --  107.38 -94.00-180.00   76
 31  \w     36.00 102.00   0.50    0.05    --  107.38 -94.00-150.00  132
 32  \w     35.00 103.00   0.50    0.05    --  107.38 -94.00  60.00  136
 33  \w      8.00  73.00   0.50    0.05    --   42.30-111.00 -49.00  130
 34  \w     18.00  59.00   0.50    0.05    --   42.30-125.00-120.00   82
 35  \w     64.00  95.00   0.50    0.05    --   42.30-125.00-120.00   62
 36  \w   -175.00 -72.00   0.50    0.05    -- -102.00 -78.00-166.24  206
 37  \w   -108.00 -72.00   0.50    0.05    -- -102.00 -80.00 -18.44   72
 38  \w    -99.00 -73.00   0.50    0.05    -- -102.00 -80.00  30.59   52
 39  \w   -175.00-123.00   0.50    0.05    -- -102.00 -80.00  30.59  104
 40  \w   -169.00 -73.00   0.50    0.05    -- -102.00 -77.00  82.03  192
 41  \w    -98.00 -72.00   0.50    0.05    -- -102.00 -78.00  97.16   52
 42  \w   -175.00-122.00   0.50    0.05    -- -102.00 -78.00  97.16  106
 43  \w   -171.00-116.00   0.50    0.05    -- -102.00 -77.00   0.00  110
 44  \w   -172.00 -73.00   0.50    0.05    -- -102.00 -77.00 120.00  198
 45  \w   -108.00 -73.00   0.50    0.05    -- -102.00 -77.00   0.00   70
 46  \w    -99.00 -73.00   0.50    0.05    -- -102.00 -77.00  60.00   52
 47  \w   -101.00 -73.00   0.50    0.05    -- -102.00 -77.00 -60.00   56
 48  \w   -108.00 -73.00   0.50    0.05    -- -102.00 -77.00 -90.00   70
 49  \w   -106.00 -73.00   0.50    0.05    -- -102.00 -77.00-113.57   66
 50  \w   -173.00 -73.00   0.50    0.05    -- -102.00 -77.00-180.00  200
 51  \w   -174.00 -74.00   0.50    0.05    -- -102.00 -77.00 -30.00  200
 52  \w   -145.00 -74.00   0.50    0.05    -- -102.00 -75.00-135.71  142
 53  \w   -140.00 -74.00   0.50    0.05    -- -102.00 -75.00-158.42  132
 54  \w    -99.00 -74.00   0.50    0.05    -- -102.00 -74.00 -51.81   50
 55  \w   -152.00-126.00   0.50    0.05    -- -102.00 -74.00 -51.81   52
 56  \w   -168.00-127.00   0.50    0.05    -- -102.00 -73.00-129.19   82
 57  \w   -157.00 -74.00   0.50    0.05    -- -102.00 -74.00-147.76  166
 58  \w   -105.00 -75.00   0.50    0.05    -- -102.00 -73.00-129.19   60
 59  \w   -175.00 -75.00   0.50    0.05    -- -102.00 -73.00-104.20  200
 60  \w   -127.00 -75.00   0.50    0.05    -- -102.00 -71.00  26.51  104
 61  \w   -169.00 -73.00   0.50    0.05    -- -102.00 -76.00  42.22  192
 62  \w   -139.00-113.00   0.50    0.05    -- -102.00 -71.00   2.51   52
 63  \w   -166.00-140.00   0.50    0.05    -- -102.00 -71.00  26.51   52
 64  \w   -153.00-117.00   0.50    0.05    -- -102.00 -77.00  60.00   72
 65  \w   -100.00 -75.00   0.50    0.05    -- -102.00 -71.00   2.51   50
 66  \w   -101.00 -76.00   0.50    0.05    -- -102.00 -70.00   9.45   50
 67  \w   -126.00 -77.00   0.50    0.05    -- -102.00 -68.00  95.36   98
 68  \w   -101.00 -76.00   0.50    0.05    -- -102.00 -69.00 125.41   50
 69  \w   -100.00 -75.00   0.50    0.05    -- -102.00 -72.00 146.95   50
 70  \w   -158.00 -73.00   0.50    0.05    -- -102.00 -76.00 164.10  170
 71  \w   -108.00 -79.00   0.50    0.05    -- -102.00 -63.00  57.60   58
 72  \w   -167.00 -77.00   0.50    0.05    -- -102.00 -66.00 -23.53  180
 73  \w   -108.00 -77.00   0.50    0.05    -- -102.00 -66.00 -94.18   62
 74  \w   -175.00 -78.00   0.50    0.05    -- -102.00 -61.00 -60.00  194
 75  \w   -175.00-117.00   0.50    0.05    -- -102.00 -66.00 -94.18  116
 76  \w   -156.00-131.00   0.50    0.05    -- -102.00 -61.00 -90.00   50
 77  \w   -103.00 -78.00   0.50    0.05    -- -102.00 -61.00 120.00   50
 78  \w   -138.00-111.00   0.50    0.05    -- -102.00 -61.00 120.00   54
 79  \w   -103.00 -78.00   0.50    0.05    -- -102.00 -61.00 -90.00   50
 80  \w   -149.00-124.00   0.50    0.05    -- -102.00-111.00 -49.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0171154000
_diffrn_orient_matrix_UB_12      -0.0249465000
_diffrn_orient_matrix_UB_13      0.0682126000
_diffrn_orient_matrix_UB_21      -0.1374414000
_diffrn_orient_matrix_UB_22      0.0521096000
_diffrn_orient_matrix_UB_23      -0.0033950000
_diffrn_orient_matrix_UB_31      -0.0500872000
_diffrn_orient_matrix_UB_32      -0.1346194000
_diffrn_orient_matrix_UB_33      -0.0139550000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            58808
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.528
_diffrn_reflns_theta_min         4.001
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.465
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.015(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0174
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0191P)^2^+1.2153P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0432
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4919
_reflns_number_total             4930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra02297k2.cif
_cod_data_source_block           00
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2431.027(16)
_cod_original_formula_moiety     '2(C11 H14 Br Cl O2)'
_cod_original_formula_sum        'C22 H28 Br2 Cl2 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     587.16
_cod_database_code               7242617
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C O H Cl Br'
_diffrn_oxdiff_digest_frames
;
01f71722cfc85792020b0e6fd2bef88742000847760
;
_diffrn_oxdiff_digest_hkl
;
01a3b6ceda650ae42a978efd001ee6840f5c82
;
_reflns_odcompleteness_completeness 99.96
_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:
 C24(H24), C8(H8), C23(H23), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C17(H17), C2(H2), C18(H18), C3(H3), C6(H6)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C29(H29A,H29B,H29C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O27(H27), O12(H12)
;
_shelx_res_checksum              21758
_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 2.359
_oxdiff_exptl_absorpt_empirical_full_min 0.843