Oxidative NHCs catalysis: direct activation of β sp3 carbons of saturated acid chlorides
Zhu, Shi-Ya; Zhang, Hua; Ma, Qing-Wei; Liu, Dou; Hui, Xin-Ping; Chemical Communications  (2018) –; doi:10.1039/C8CC08578A

data_7122640
_publ_section_title
;
 Oxidative NHCs catalysis: direct activation of \b sp3 carbons of
 saturated acid chlorides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08578A
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H14 Cl N O3'
_chemical_formula_sum            'C18 H14 Cl N O3'
_chemical_formula_weight         327.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2018-10-06 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.292(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8920(7)
_cell_length_b                   6.7802(4)
_cell_length_c                   11.6465(8)
_cell_measurement_reflns_used    993
_cell_measurement_temperature    295.26(10)
_cell_measurement_theta_max      21.4950
_cell_measurement_theta_min      4.0200
_cell_volume                     781.12(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.26(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.8134
_diffrn_measurement_details
;
  1 omega  -10.00   88.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  -90.0000 49

  2 omega   56.00  100.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000  120.0000 22

  3 omega   51.00   95.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  -90.0000 22

  4 omega  -33.00   17.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000  120.0000 25

  5 omega  -12.00   20.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   90.0000 16

  6 omega  -19.00   19.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -90.0000 19

  7 omega  -35.00   53.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000    0.0000 44

  8 omega   -8.00   18.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000  -30.0000 13
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0520029000
_diffrn_orient_matrix_UB_12      -0.0063300000
_diffrn_orient_matrix_UB_13      0.0415566000
_diffrn_orient_matrix_UB_21      -0.0418068000
_diffrn_orient_matrix_UB_22      -0.0497224000
_diffrn_orient_matrix_UB_23      -0.0402942000
_diffrn_orient_matrix_UB_31      0.0262311000
_diffrn_orient_matrix_UB_32      -0.0918287000
_diffrn_orient_matrix_UB_33      0.0189675000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5099
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2008
_reflns_number_total             2865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc08578a2.cif
_cod_data_source_block           zhushiy_1207_1
_cod_database_code               7122640
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 2016-12-07
_olex2_submission_special_instructions 'No special instructions were received'