Rh(iii)-Catalyzed acylation of heteroarenes with cyclobutenones via C-H/C-C bond activation.
Cui, Yixin; Bai, Dachang; Liu, Bingxian; Chang, Junbiao; Li, Xingwei; Chemical communications (Cambridge, England) 56 (2020) 15631–15634; doi:10.1039/d0cc05965j

data_7127488
_publ_section_title
;
 Rh(iii)-Catalyzed acylation of heteroarenes with cyclobutenones via
 C-H/C-C bond activation.
;
_journal_issue                   100
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              15631
_journal_page_last               15634
_journal_paper_doi               10.1039/d0cc05965j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C23 H18 Cl N3 O'
_chemical_formula_sum            'C23 H18 Cl N3 O'
_chemical_formula_weight         387.87
_chemical_name_systematic        cyx
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-13 deposited with the CCDC.	2020-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.3148(3)
_cell_length_b                   7.58000(10)
_cell_length_c                   27.7096(5)
_cell_measurement_reflns_used    5183
_cell_measurement_temperature    292.90(10)
_cell_measurement_theta_max      71.3770
_cell_measurement_theta_min      4.8250
_cell_volume                     3846.82(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.90(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9802
_diffrn_measured_fraction_theta_max 0.9802
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -63.00 -35.00   1.00    1.21    --  -35.62  96.00 -57.00   28
  2  \w    -26.00  23.00   1.00    1.21    --  -35.62  96.00 -57.00   49
  3  \w     26.00  74.00   1.00    1.21    --   35.62  46.00  85.00   48
  4  \w    103.00 176.00   1.00    4.83    --  107.12  96.00 -57.00   73
  5  \w     78.00 130.00   1.00    4.83    --  107.12 -86.00  88.00   52
  6  \w     98.00 175.00   1.00    4.83    --  107.12  46.00  85.00   77
  7  \w    -26.00   0.00   1.00    1.21    --  -35.62  86.00-154.00   26
  8  \w     56.00 108.00   1.00    1.21    --   35.62-178.00  90.00   52
  9  \w     59.00 107.00   1.00    1.21    --   35.62 178.00-120.00   48
 10  \w     37.00  64.00   1.00    4.83    --  107.12 -30.00 -90.00   27
 11  \w     91.00 165.00   1.00    4.83    --  107.12  45.00-150.00   74
 12  \w     94.00 120.00   1.00    4.83    --  107.12 -30.00 -90.00   26
 13  \w     45.00  98.00   1.00    4.83    --  107.12 -95.00   0.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0290987000
_diffrn_orient_matrix_UB_12      0.1145478000
_diffrn_orient_matrix_UB_13      -0.0417160000
_diffrn_orient_matrix_UB_21      0.0731656000
_diffrn_orient_matrix_UB_22      0.0219399000
_diffrn_orient_matrix_UB_23      0.0267703000
_diffrn_orient_matrix_UB_31      0.0296602000
_diffrn_orient_matrix_UB_32      -0.1663944000
_diffrn_orient_matrix_UB_33      -0.0251721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            9900
_diffrn_reflns_theta_full        71.4331
_diffrn_reflns_theta_max         71.43
_diffrn_reflns_theta_min         4.83
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.3393
_exptl_crystal_description       block
_exptl_crystal_F_000             1623.4173
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.5398
_refine_diff_density_min         -0.5542
_refine_diff_density_rms         0.1231
_refine_ls_d_res_high            0.8132
_refine_ls_d_res_low             9.1574
_refine_ls_goodness_of_fit_ref   1.0363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0363
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0869
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1110P)^2^+10.5025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2393
_refine_ls_wR_factor_ref         0.2446
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              0
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                3241
_reflns_number_total             3667
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc05965j2.cif
_cod_data_source_block           CYX-20191021
_cod_depositor_comments          'Adding full bibliography for 7127488.cif.'
_cod_database_code               7127488
_chemical_oxdiff_formula         'C1 H1 O1 N1 Cl1'
_diffrn_oxdiff_digest_frames
;
01d9b6eb0d7e725771fb673b17180ac141006613c56
;
_diffrn_oxdiff_digest_hkl
;
011ac830ae5ce99300cba60a470b5311150035
;
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C17(H17), C5(H5), C8(H8), C7(H7), C28(H28), C27(H27), C24(H24), C14(H14),
 C25(H25), C26(H26), C13(H13), C12(H12)
2.b Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c), C19(H19a,H19b,H19c)
;
_olex2_date_sample_data_collection 2019-10-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.394
_oxdiff_exptl_absorpt_empirical_full_min 0.236