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_1555046
_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 H20 O6'
_chemical_formula_sum            'C23 H20 O6'
_chemical_formula_weight         392.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-27
_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                79.033(5)
_cell_angle_beta                 76.634(7)
_cell_angle_gamma                77.369(6)
_cell_formula_units_Z            2
_cell_length_a                   7.7957(7)
_cell_length_b                   10.1827(6)
_cell_length_c                   12.7574(8)
_cell_measurement_reflns_used    2407
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4510
_cell_measurement_theta_min      3.6850
_cell_volume                     950.96(12)
_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 0.998
_diffrn_measurement_details
;
  1 omega  -25.00   24.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000   60.0000 49

  2 omega  -79.00  -30.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  143.0000  -55.0000 49

  3 omega   -6.00   23.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000 -120.0000 29

  4 omega  -65.00  -28.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  127.0000  134.0000 37

  5 omega   10.00   67.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   57.0000  -60.0000 57

  6 omega  -27.00   23.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000   60.0000 50

  7 omega  -49.00   85.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661    0.0000   90.0000 134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0774889000
_diffrn_orient_matrix_UB_12      -0.0203429000
_diffrn_orient_matrix_UB_13      -0.0070877000
_diffrn_orient_matrix_UB_21      -0.0314515000
_diffrn_orient_matrix_UB_22      -0.0089241000
_diffrn_orient_matrix_UB_23      0.0572265000
_diffrn_orient_matrix_UB_31      -0.0453300000
_diffrn_orient_matrix_UB_32      0.0686671000
_diffrn_orient_matrix_UB_33      -0.0035981000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7725
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.319
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93855
_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    1.370
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0534P)^2^+0.2099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2604
_reflns_number_total             3885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00795d2.cif
_cod_data_source_block           201709178
_cod_original_cell_volume        950.95(13)
_cod_database_code               1555046
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H41N2O2
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.77
_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 Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'