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_7154457
_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         'C15 H10 Cl N O4'
_chemical_formula_sum            'C15 H10 Cl N O4'
_chemical_formula_weight         303.69
_chemical_name_systematic
'((2R*,3R*)-2-chloro-3-(4-nitrophenyl)oxiran-2-yl)(phenyl)methanone '
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-01
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Olex2 1.2
(compiled 2014.11.28 svn.r3107 for OlexSys, GUI svn.r4957)
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_audit_update_record
;
2014-12-04 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2048(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.32300(9)
_cell_length_b                   12.09364(16)
_cell_length_c                   15.09304(16)
_cell_measurement_reflns_used    12863
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.0420
_cell_measurement_theta_min      3.3630
_cell_volume                     1328.84(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_diffrn_measurement_details
;
  1 omega  -89.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440   19.0000 -120.0000 132

  2 omega  -34.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440   57.0000  -90.0000 83

  3 omega  -96.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000  150.0000 109

  4 omega  -85.00   14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000   30.0000 99

  5 omega  -58.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440   77.0000    0.0000 112

  6 omega  -96.00   15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000  -90.0000 111

  7 omega   75.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596 -178.0000  -60.0000 33

  8 omega    4.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  -99.0000   60.0000 66

  9 omega  -96.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000  -90.0000 112

 10 omega  -50.00   56.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440   38.0000   90.0000 106

 11 omega  -94.00    9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -57.0000   30.0000 103

 12 omega  -55.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  -38.0000  -90.0000 117

 13 omega   57.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  178.0000 -150.0000 51

 14 omega   -4.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  -99.0000  -90.0000 75

 15 omega  -96.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000    0.0000 112

 16 omega   -8.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596   57.0000 -150.0000 103

 17 omega   53.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596 -178.0000   90.0000 56

 18 omega   57.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  178.0000  -90.0000 51

 19 omega   57.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  178.0000 -120.0000 51

 20 omega  -15.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596   77.0000   60.0000 112

 21 omega  -96.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000 -150.0000 112

 22 omega -107.00  -35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440 -178.0000   30.0000 72

 23 omega  -59.00  -17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596    0.0000 -180.0000 42
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
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_diffrn_orient_matrix_UB_11      -0.0156100000
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_diffrn_orient_matrix_UB_21      -0.0898150000
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_diffrn_orient_matrix_UB_23      0.0091389000
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_diffrn_orient_matrix_UB_33      -0.0443869000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
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_diffrn_reflns_number            40662
_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.885
_diffrn_reflns_theta_min         3.266
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.303
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_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.300
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_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     190
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0328
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.6421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                2518
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00541h2.cif
_cod_data_source_block           mjh140034_fa
_cod_depositor_comments
'Adding full bibliography for 7154444--7154457.cif.'
_cod_original_cell_volume        1328.83(3)
_cod_database_code               7154457
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C15 H10 N1 O4 Cl1'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_shelx_res_checksum              63005
_olex2_submission_special_instructions 'No special instructions were received'