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_1555050
_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         'C22 H17 Cl O6'
_chemical_formula_sum            'C22 H17 Cl O6'
_chemical_formula_weight         412.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-29 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.817(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6483(3)
_cell_length_b                   17.4042(4)
_cell_length_c                   15.2455(4)
_cell_measurement_reflns_used    5696
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8740
_cell_measurement_theta_min      3.8980
_cell_volume                     3872.99(16)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -104.00  -43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  120.0000 61

  2 omega  -72.00  -46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 26

  3 omega   26.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 38

  4 omega  -23.00    2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 25

  5 omega  -31.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 53

  6 omega  -32.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 65

  7 omega    6.00   52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 46

  8 omega   18.00   44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 26

  9 omega   21.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 34

 10 omega   -1.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 76

 11 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 26

 12 omega   96.00  126.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 30

 13 omega   69.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 46

 14 omega   60.00  124.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -120.0000 64

 15 omega   90.00  170.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 80

 16 omega   40.00   65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 25

 17 omega   54.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 44

 18 omega   48.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 40

 19 omega   38.00   66.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 28

 20 omega   46.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 45

 21 omega   42.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 64

 22 omega   37.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 35

 23 omega   45.00   73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 28

 24 omega   97.00  122.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0237160000
_diffrn_orient_matrix_UB_12      0.0657889000
_diffrn_orient_matrix_UB_13      0.0655185000
_diffrn_orient_matrix_UB_21      -0.0168599000
_diffrn_orient_matrix_UB_22      0.0588827000
_diffrn_orient_matrix_UB_23      -0.0750763000
_diffrn_orient_matrix_UB_31      -0.1014805000
_diffrn_orient_matrix_UB_32      0.0056466000
_diffrn_orient_matrix_UB_33      0.0189693000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16152
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.862
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96597
_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    1.416
_exptl_crystal_description       prism
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     548
_refine_ls_number_reflns         6898
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0613
_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^)+(0.1094P)^2^+1.6638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5474
_reflns_number_total             6898
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00795d2.cif
_cod_data_source_block           201806307
_cod_original_cell_volume        3872.98(15)
_cod_database_code               1555050
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N1
_shelx_estimated_absorpt_t_max   0.789
_shelx_estimated_absorpt_t_min   0.719
_reflns_odcompleteness_completeness 99.61
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21-O6A
 1.43 with sigma of 0.02
 C1A-O6'A
 1.43 with sigma of 0.02
 O6'-C21'
 1.43 with sigma of 0.02
 C1A-C1B
 1.55 with sigma of 0.02
 C18'-O5'A
 1.1 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5'A) \\sim Ueq, Uanis(O5') \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O5A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O5') = Uanis(O5'A)
Uanis(O6') = Uanis(O6'A)
Uanis(C21') = Uanis(C1A)
Uanis(C22') = Uanis(C1B)
Uanis(O5) = Uanis(O5A)
Uanis(O6) = Uanis(O6A)
4. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(O5'A)=
 Sof(O6'A)=1-FVAR(1)
 Sof(C21')=Sof(H21A)=Sof(H21B)=Sof(C22')=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(O5')=Sof(O6')=FVAR(1)
 Sof(H21E)=Sof(H21F)=Sof(O5A)=Sof(O6A)=1-FVAR(2)
 Sof(H21C)=Sof(H21D)=Sof(O5)=Sof(O6)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C19(H19C,H19D), C21(H21C,H21D), C21(H21E,H21F), C1A(H1AA,H1AB), C19'(H19A,
 H19B), C21'(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C6'(H6'),
 C7'(H7'), C8'(H8'), C9'(H9'), C10'(H10'), C12'(H12'), C13'(H13')
5.c Idealised Me refined as rotating group:
 C20(H20D,H20E,H20F), C22(H22D,H22E,H22F), C1B(H1BA,H1BB,H1BC), C20'(H20A,H20B,
 H20C), C22'(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'