A novel coupling reaction of α-halo ketones promoted by SmI3/CuI
Liu, Yongjun; Zhao, Hengmin; Tian, Guang; Du, Feng; Qi, Yan; Wen, Yonghong; RSC Adv.  (2016) –; doi:10.1039/C5RA26604A

data_7224412
_publ_section_title
;
 A novel coupling reaction of \a-halo ketones promoted by SmI3/CuI
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA26604A
_journal_year                    2016
_chemical_formula_moiety         'C27 H24 O3'
_chemical_formula_sum            'C27 H24 O3'
_chemical_formula_weight         396.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-11-04 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.301(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4749(5)
_cell_length_b                   10.5376(4)
_cell_length_c                   17.8795(9)
_cell_measurement_reflns_used    1956
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.2700
_cell_measurement_theta_min      3.9730
_cell_volume                     2127.11(17)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -6.00   25.20   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000  -60.0000 26

  2 omega    8.00   92.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   38.0000   30.0000 70

  3 omega    1.00   85.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000  -60.0000 70

  4 omega  -50.00  -24.80   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -38.0000 -150.0000 21
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0622822000
_diffrn_orient_matrix_UB_12      -0.0077078000
_diffrn_orient_matrix_UB_13      -0.0045533000
_diffrn_orient_matrix_UB_21      -0.0030616000
_diffrn_orient_matrix_UB_22      -0.0097753000
_diffrn_orient_matrix_UB_23      -0.0395426000
_diffrn_orient_matrix_UB_31      0.0077105000
_diffrn_orient_matrix_UB_32      -0.0661648000
_diffrn_orient_matrix_UB_33      0.0063738000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8532
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.61
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84902
_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    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.8297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                2961
_reflns_number_total             4170
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra26604a2.cif
_cod_data_source_block           wyh_0125
_cod_original_cell_volume        2127.10(15)
_cod_database_code               7224412
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18),
 C23(H23), C24(H24), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C19(H19a,H19b,H19c), C28(H28a,H28b,H28c)
;
_olex2_date_sample_data_collection 2015-01-27
_olex2_submission_special_instructions 'No special instructions were received'