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_7154444
_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_formula_moiety         'C10 H6 Cl3 N O'
_chemical_formula_sum            'C10 H6 Cl3 N O'
_chemical_formula_weight         262.51
_chemical_name_systematic        2,2,2-trichloro-1-(1H-indol-3-yl)ethan-1-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-30
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Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
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_audit_update_record
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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                   20.5153(14)
_cell_length_b                   6.7406(4)
_cell_length_c                   7.4148(5)
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.5101
_cell_measurement_theta_min      2.9152
_cell_volume                     1025.36(12)
_computing_cell_refinement
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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)
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_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)
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_computing_data_reduction
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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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details
;
  1 omega   16.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.1850   77.0000   60.0000 31

  2 omega   -1.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000 -120.0000 90

  3 omega  -23.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000 -180.0000 86
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_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_21      0.0223930000
_diffrn_orient_matrix_UB_22      0.0076181000
_diffrn_orient_matrix_UB_23      -0.0698909000
_diffrn_orient_matrix_UB_31      0.0045961000
_diffrn_orient_matrix_UB_32      -0.0342371000
_diffrn_orient_matrix_UB_33      -0.0165331000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5188
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_min         2.921
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79138
_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.
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_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    1.700
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0268P)^2^+0.4527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1121
_reflns_number_total             1240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00541h2.cif
_cod_data_source_block           mjh85
_cod_depositor_comments
'Adding full bibliography for 7154444--7154457.cif.'
_cod_database_code               7154444
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C10 H7 Cl2 N O'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8)
;
_shelx_res_checksum              55329
_olex2_submission_special_instructions 'No special instructions were received'