Substrate-oriented selectivity in the Mg-mediated conjugate addition of bromoform to electron-deficient alkenes.
Satam, Nishikant; Nemu, Saumyadip; Gururaja, Guddeangadi N.; Namboothiri, Irishi N. N.; Organic & biomolecular chemistry 18 (2020) 5697–5707; doi:10.1039/d0ob00599a

data_7157572
_publ_section_title
;
 Substrate-oriented selectivity in the Mg-mediated conjugate addition of
 bromoform to electron-deficient alkenes.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5697
_journal_page_last               5707
_journal_paper_doi               10.1039/d0ob00599a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C22 H20 Br2 O'
_chemical_formula_sum            'C22 H20 Br2 O'
_chemical_formula_weight         460.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-06-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_audit_update_record
;
2020-03-21 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.177(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3505(4)
_cell_length_b                   14.6227(6)
_cell_length_c                   13.7913(6)
_cell_measurement_reflns_used    4827
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.1920
_cell_measurement_theta_min      2.0600
_cell_volume                     1880.67(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -110.00  16.00   0.50    8.00    --  -20.00   0.00-108.00  252
  2  \w    -70.00  17.00   0.50    8.00    --  -20.00 -72.00-180.00  174
  3  \w    -22.00 -19.50   0.50    8.00    --  -20.00 -72.00  36.00    5
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0056808000
_diffrn_orient_matrix_UB_12      0.0473639000
_diffrn_orient_matrix_UB_13      -0.0101390000
_diffrn_orient_matrix_UB_21      -0.0752464000
_diffrn_orient_matrix_UB_22      0.0047424000
_diffrn_orient_matrix_UB_23      0.0018387000
_diffrn_orient_matrix_UB_31      0.0095138000
_diffrn_orient_matrix_UB_32      0.0093277000
_diffrn_orient_matrix_UB_33      0.0505285000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7482
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.033
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56146
_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    1.625
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0318
_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/[\s^2^(Fo^2^)+(0.0331P)^2^+0.2036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2774
_reflns_number_total             3305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00599a2.cif
_cod_data_source_block           inn-nss-db-7_mo
_cod_depositor_comments
'Adding full bibliography for 7157571--7157573.cif.'
_cod_original_cell_volume        1880.67(15)
_cod_database_code               7157572
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C22H20Br2O1
_reflns_odcompleteness_completeness 88.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00F), C00G(H00G,H00H), C00I(H00I,H00J), C00J(H00K,H00L)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00K(H00M),
 C00L(H00N), C00M(H00O), C00N(H00P), C00O(H00Q), C00P(H00R)
;
_shelx_res_checksum              23736
_shelx_hkl_checksum              24100
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.856
_oxdiff_exptl_absorpt_empirical_full_min 0.801