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_7154452
_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         'C18 H19 Cl2 N O6'
_chemical_formula_sum            'C18 H19 Cl2 N O6'
_chemical_formula_weight         416.24
_chemical_name_systematic
'diethyl 2-(1,1-dichloro-2-(1-methyl-1H-indol-3-yl)-2-oxoethyl)-2-hydroxymalonate '
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-31
_audit_creation_method
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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                87.574(5)
_cell_angle_beta                 70.982(6)
_cell_angle_gamma                75.760(5)
_cell_formula_units_Z            2
_cell_length_a                   8.6111(5)
_cell_length_b                   10.1757(6)
_cell_length_c                   11.1365(7)
_cell_measurement_reflns_used    2555
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.5310
_cell_measurement_theta_min      2.8773
_cell_volume                     893.45(10)
_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      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_details
;
  1 omega  -79.00   15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  -77.0000  -90.0000 94

  2 omega  -87.00    0.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  -77.0000  150.0000 87

  3 omega  -41.00   55.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   77.0000   30.0000 96

  4 omega   13.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -94.0000  169.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0126476000
_diffrn_orient_matrix_UB_12      -0.0530388000
_diffrn_orient_matrix_UB_13      -0.0441091000
_diffrn_orient_matrix_UB_21      0.0183211000
_diffrn_orient_matrix_UB_22      -0.0486549000
_diffrn_orient_matrix_UB_23      0.0441348000
_diffrn_orient_matrix_UB_31      -0.0870833000
_diffrn_orient_matrix_UB_32      0.0003218000
_diffrn_orient_matrix_UB_33      0.0255490000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7004
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.594
_diffrn_reflns_theta_min         2.883
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85236
_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    1.547
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0304P)^2^+0.3719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3089
_reflns_number_total             3683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00541h2.cif
_cod_data_source_block           mjh95
_cod_depositor_comments
'Adding full bibliography for 7154444--7154457.cif.'
_cod_database_code               7154452
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C30 H30 N Cl2 O6'
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.856
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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
2.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C17(H17a,H17b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C15(H15a,H15b,H15c), C18(H18a,H18b,H18c)
;
_shelx_res_checksum              76088
_olex2_submission_special_instructions 'No special instructions were received'