Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones.
Essa, Ali H.; Lerrick, Reinner I.; Çiftçi, Eçe; Harrington, Ross W.; Waddell, Paul G.; Clegg, William; Hall, Michael J.; Organic & biomolecular chemistry 13 (2015) 5793–5803; doi:10.1039/c5ob00541h

data_7154446
_publ_section_title
;
 Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5793
_journal_page_last               5803
_journal_paper_doi               10.1039/c5ob00541h
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C7 H7 Cl2 N O'
_chemical_formula_sum            'C7 H7 Cl2 N O'
_chemical_formula_weight         192.04
_chemical_name_systematic
2,2-dichloro-1-(1-methyl-1H-pyrrol-2-yl)ethan-1-one
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-31
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9311(3)
_cell_length_b                   10.5722(4)
_cell_length_c                   13.4606(6)
_cell_measurement_reflns_used    4380
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.6319
_cell_measurement_theta_min      3.0206
_cell_volume                     844.04(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details
;
  1 omega  -42.00   47.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.3413   77.0000  -60.0000 89

  2 omega    6.00   78.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600   38.0000  120.0000 72

  3 omega  -50.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600    0.0000    0.0000 146
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0757184000
_diffrn_orient_matrix_UB_12      -0.0184611000
_diffrn_orient_matrix_UB_13      -0.0381066000
_diffrn_orient_matrix_UB_21      -0.0664014000
_diffrn_orient_matrix_UB_22      -0.0544991000
_diffrn_orient_matrix_UB_23      -0.0093608000
_diffrn_orient_matrix_UB_31      -0.0643878000
_diffrn_orient_matrix_UB_32      0.0345028000
_diffrn_orient_matrix_UB_33      -0.0352060000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6723
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_min         3.027
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0222
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+0.1349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0566
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                1836
_reflns_number_total             1892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00541h2.cif
_cod_data_source_block           mjh91
_cod_depositor_comments
'Adding full bibliography for 7154444--7154457.cif.'
_cod_database_code               7154446
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.765
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              44876
_olex2_submission_special_instructions 'No special instructions were received'