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_7154455
_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         'C14 H11 Cl N2 O4'
_chemical_formula_sum            'C14 H11 Cl N2 O4'
_chemical_formula_weight         306.70
_chemical_name_systematic
'((2R*,3R*)-2-chloro-3-(4-nitrophenyl)oxiran-2-yl)(1-methyl-1H-pyrrol-2-yl)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             2014-07-30
_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                 116.111(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4142(4)
_cell_length_b                   21.2032(8)
_cell_length_c                   8.5672(4)
_cell_measurement_reflns_used    5809
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.5389
_cell_measurement_theta_min      2.8563
_cell_volume                     1372.47(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details
;
  1 omega  -39.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  102.0000 -137.0000 27

  2 omega  -82.00  -50.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  -57.0000  120.0000 32

  3 omega  -18.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000 -180.0000 106

  4 omega   -3.00   23.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -99.0000  150.0000 26

  5 omega   20.00   48.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   57.0000  120.0000 28

  6 omega   -8.00   49.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   38.0000   90.0000 57

  7 omega   17.00   46.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -99.0000   90.0000 29

  8 omega  -16.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   38.0000    0.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0184157000
_diffrn_orient_matrix_UB_12      -0.0315988000
_diffrn_orient_matrix_UB_13      0.0137360000
_diffrn_orient_matrix_UB_21      0.0912128000
_diffrn_orient_matrix_UB_22      -0.0050279000
_diffrn_orient_matrix_UB_23      0.0546594000
_diffrn_orient_matrix_UB_31      -0.0126800000
_diffrn_orient_matrix_UB_32      0.0097336000
_diffrn_orient_matrix_UB_33      0.0729432000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14096
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.602
_diffrn_reflns_theta_min         2.862
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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    1.484
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0322P)^2^+0.8344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2729
_reflns_number_total             3057
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00541h2.cif
_cod_data_source_block           mjh130005
_cod_depositor_comments
'Adding full bibliography for 7154444--7154457.cif.'
_cod_original_cell_volume        1372.47(12)
_cod_database_code               7154455
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.906
_reflns_odcompleteness_completeness 99.72
_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. Restrained distances
 C7-C6A \\sim C7-C6
 with sigma of 0.02
 O2A-C8 \\sim O2-C8
 with sigma of 0.02
 O2-C7 \\sim O2A-C7
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2A)
Uanis(O1) = Uanis(O1A)
Uanis(C6) = Uanis(C6A)
Uanis(C5) = Uanis(C5A)
Uanis(C4) = Uanis(C4A)
Uanis(C3) = Uanis(C3A)
Uanis(C2) = Uanis(C2A)
Uanis(N1) = Uanis(N1A)
Uanis(C1) = Uanis(C1A)
4. Same fragment restrains
{O1, C6, C5, C4, C3, C2, N1, C1}
as
{O1A, C6A, C5A, C4A, C3A, C2A, N1A, C1A}
5. Others
 Sof(H8B)=Sof(O1A)=Sof(C6A)=Sof(C5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=
 Sof(C2A)=Sof(H2A)=Sof(N1A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(O2A)=1-
 FVAR(1)
 Sof(O1)=Sof(C6)=Sof(C5)=Sof(C4)=Sof(H4)=Sof(C3)=Sof(H3)=Sof(C2)=Sof(H2)=
 Sof(N1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(O2)=Sof(H8A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C8(H8A), C8(H8B)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C10(H10), C11(H11), C13(H13), C14(H14), C4A(H4A),
 C3A(H3A), C2A(H2A)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              82195
_olex2_submission_special_instructions 'No special instructions were received'