Tandem Diels-Alder/oxidation-aromatization reactions involving 2-styrylchromones and arynes.
Addepalli, Yesu; Yu, Zhimei; Ji, Jie; Zou, Cheng; Wang, Zhen; He, Yun; Organic & biomolecular chemistry 16 (2018) 6077–6085; doi:10.1039/c8ob01199k

data_7156359
_publ_section_title
;
 Tandem Diels-Alder/oxidation-aromatization reactions involving
 2-styrylchromones and arynes.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6077
_journal_page_last               6085
_journal_paper_doi               10.1039/c8ob01199k
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C23 H14 O2'
_chemical_formula_sum            'C23 H14 O2'
_chemical_formula_weight         322.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-06-23
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-03-26 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1068(5)
_cell_length_b                   13.5461(9)
_cell_length_c                   26.1677(13)
_cell_measurement_reflns_used    3424
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5690
_cell_measurement_theta_min      3.3860
_cell_volume                     3228.1(3)
_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
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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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.998
_diffrn_measurement_details
;
  1 omega  -16.00   24.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000    0.0000 80

  2 omega  -25.00   24.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000   90.0000 98

  3 omega   -6.00   19.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419 -103.0000  161.0000 50

  4 omega  -21.00    4.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -103.0000  161.0000 50

  5 omega  -75.00  -36.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  -30.0000 78

  6 omega  -83.00  -55.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -38.0000   30.0000 56

  7 omega  -42.00  -16.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  103.0000  -96.0000 52

  8 omega   36.00   89.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  178.0000 -120.0000 106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0431460000
_diffrn_orient_matrix_UB_12      -0.0100736000
_diffrn_orient_matrix_UB_13      0.0220032000
_diffrn_orient_matrix_UB_21      0.0644729000
_diffrn_orient_matrix_UB_22      -0.0118501000
_diffrn_orient_matrix_UB_23      0.0138734000
_diffrn_orient_matrix_UB_31      0.0066946000
_diffrn_orient_matrix_UB_32      0.0499616000
_diffrn_orient_matrix_UB_33      0.0077146000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18344
_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         26.371
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90883
_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    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0507P)^2^+0.8242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2171
_reflns_number_total             3312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01199k2.cif
_cod_data_source_block           170623_s3_wz
_cod_depositor_comments          'Adding full bibliography for 7156359.cif.'
_cod_database_code               7156359
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3cl1
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'