Divergent C-H activation synthesis of chalcones, quinolones and indoles.
Shi, Yuesen; Xing, Huimin; Huang, Tianle; Liu, Xuexin; Chen, Jian; Guo, Xiaoyu; Li, Guo-Bo; Wu, Yong; Chemical communications (Cambridge, England) 56 (2020) 1585–1588; doi:10.1039/c9cc08926h

data_7125729
_publ_section_title
;
 Divergent C-H activation synthesis of chalcones, quinolones and indoles.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1585
_journal_page_last               1588
_journal_paper_doi               10.1039/c9cc08926h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C24 H20 N2 O4'
_chemical_formula_sum            'C24 H20 N2 O4'
_chemical_formula_weight         400.42
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-09
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-06 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.108(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2065(14)
_cell_length_b                   8.0264(5)
_cell_length_c                   17.9481(17)
_cell_measurement_reflns_used    2347
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8010
_cell_measurement_theta_min      3.3870
_cell_volume                     2096.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
  1 omega   -6.00   22.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -150.0000 28

  2 omega   18.00   76.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       17.0762   38.0000  -90.0000 58

  3 omega  -49.00   27.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       17.0762  -57.0000  -30.0000 76

  4 omega  -12.00   13.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.6544  -99.0000  -30.0000 25

  5 omega  -50.00  -24.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.6544  -57.0000  150.0000 26

  6 omega  -59.00  -33.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.6544  -57.0000   30.0000 26

  7 omega   18.00   76.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       16.7637   38.0000  150.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0076951000
_diffrn_orient_matrix_UB_12      -0.0088800000
_diffrn_orient_matrix_UB_13      0.0418662000
_diffrn_orient_matrix_UB_21      -0.0480900000
_diffrn_orient_matrix_UB_22      -0.0041244000
_diffrn_orient_matrix_UB_23      -0.0129841000
_diffrn_orient_matrix_UB_31      0.0014648000
_diffrn_orient_matrix_UB_32      -0.0878650000
_diffrn_orient_matrix_UB_33      -0.0036444000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13664
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.494
_diffrn_reflns_theta_min         3.386
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM / Hexane'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0559P)^2^+0.2968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2979
_reflns_number_total             4974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08926h2.cif
_cod_data_source_block           190508_s3_sys
_cod_depositor_comments
'Adding full bibliography for 7125729--7125730.cif.'
_cod_original_cell_volume        2096.5(3)
_cod_database_code               7125729
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.72
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              11138
_olex2_submission_special_instructions 'No special instructions were received'