A simple approach to indeno-coumarins via visible-light-induced cyclization of aryl alkynoates with diethyl bromomalonate
Li, Qingrui; Yin, Yunnian; Li, Yabo; Zhang, Jianye; Huang, Mengmeng; Kim, Jung Keun; Wu, Yangjie; Organic Chemistry Frontiers 6 (2019) 3238–; doi:10.1039/C9QO00795D

data_1555049
_publ_section_title
;
 A simple approach to indeno-coumarins via visible-light-induced
 cyclization of aryl alkynoates with diethyl bromomalonate
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3238
_journal_paper_doi               10.1039/C9QO00795D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C23 H22 O6'
_chemical_formula_sum            'C23 H22 O6'
_chemical_formula_weight         394.40
_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             2018-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-29 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.242(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7414(4)
_cell_length_b                   8.7416(3)
_cell_length_c                   16.4090(5)
_cell_measurement_reflns_used    2377
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6740
_cell_measurement_theta_min      5.0740
_cell_volume                     2049.53(11)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega  -40.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   60.0000 26

  2 omega -108.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   30.0000 51

  3 omega   66.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 35

  4 omega    8.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 33

  5 omega    9.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 91

  6 omega   49.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 55

  7 omega   45.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 49

  8 omega  -30.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000    0.0000 38

  9 omega   26.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000    0.0000 33

 10 omega   16.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 61

 11 omega   90.00  175.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 12 omega   54.00   93.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 39

 13 omega   38.00  114.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 76

 14 omega   40.00  108.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 68

 15 omega   61.00   87.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 26

 16 omega  100.00  175.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 75

 17 omega   70.00   95.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 25

 18 omega   60.00   86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 26

 19 omega   88.00  169.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0096887000
_diffrn_orient_matrix_UB_12      0.0648257000
_diffrn_orient_matrix_UB_13      0.0889665000
_diffrn_orient_matrix_UB_21      -0.0049004000
_diffrn_orient_matrix_UB_22      0.1638313000
_diffrn_orient_matrix_UB_23      -0.0355036000
_diffrn_orient_matrix_UB_31      -0.1073045000
_diffrn_orient_matrix_UB_32      -0.0016038000
_diffrn_orient_matrix_UB_33      -0.0142665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8150
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.895
_diffrn_reflns_theta_min         5.563
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83965
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1037P)^2^+0.5816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2901
_reflns_number_total             3871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00795d2.cif
_cod_data_source_block           201803161
_cod_database_code               1555049
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H30N3O5
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.844
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'