Synthesis of Spiro- and Fused Heterocycles via (4+4) Annulation of Sulfonylphthalide with o-Hydroxystyrenyl Derivatives.
Suresh, Alati; Baiju, Thekke V.; Kumar, Tarun; Namboothiri, Irishi N. N.; The Journal of organic chemistry 84 (2019) 3158–3168; doi:10.1021/acs.joc.8b03039

data_4033943
_publ_section_title
;
 Synthesis of Spiro- and Fused Heterocycles via (4+4) Annulation of
 Sulfonylphthalide with o-Hydroxystyrenyl Derivatives.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3158
_journal_page_last               3168
_journal_paper_doi               10.1021/acs.joc.8b03039
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C20 H13 Br N2 O6'
_chemical_formula_sum            'C20 H13 Br N2 O6'
_chemical_formula_weight         457.23
_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   mixed
_audit_creation_date             2018-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                82.7874(18)
_cell_angle_beta                 85.8772(17)
_cell_angle_gamma                79.2104(17)
_cell_formula_units_Z            2
_cell_length_a                   6.90037(13)
_cell_length_b                   7.83220(17)
_cell_length_c                   16.9797(4)
_cell_measurement_reflns_used    13376
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0440
_cell_measurement_theta_min      2.4120
_cell_volume                     893.21(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -110.00  70.00   0.50    8.00    --  -20.00   0.00 108.00  360
  2  \w    -69.00  19.00   0.50    8.00    --  -20.00 -72.00-180.00  176
  3  \w    -71.00  10.00   0.50    8.00    --  -20.00 -72.00  36.00  162
  4  \w    -35.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  108
  5  \w    -59.00 -28.50   0.50    8.00    --  -20.00  72.00-180.00   61
  6  \w   -110.00  70.00   0.50    8.00    --  -20.00   0.00-180.00  360
  7  \w    -60.00  19.00   0.50    8.00    --  -20.00 -72.00 -36.00  158
  8  \w    -59.00   0.50   0.50    8.00    --  -20.00  72.00-108.00  119
  9  \w    -61.00   1.00   0.50    8.00    --  -20.00 -72.00 108.00  124
 10  \w     -9.00  21.50   0.50    8.00    --  -20.00  72.00  36.00   61
 11  \w    -59.00 -28.50   0.50    8.00    --  -20.00  72.00 -36.00   61
 12  \w    -59.00   1.00   0.50    8.00    --  -20.00  72.00 108.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0015772000
_diffrn_orient_matrix_UB_12      0.0915250000
_diffrn_orient_matrix_UB_13      -0.0053511000
_diffrn_orient_matrix_UB_21      0.0124283000
_diffrn_orient_matrix_UB_22      -0.0020289000
_diffrn_orient_matrix_UB_23      -0.0417240000
_diffrn_orient_matrix_UB_31      -0.1040190000
_diffrn_orient_matrix_UB_32      0.0152008000
_diffrn_orient_matrix_UB_33      -0.0027955000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15857
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.421
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.700
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0428P)^2^+0.4420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2937
_reflns_number_total             3148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03039_si_002.cif
_cod_data_source_block           inn-as-302b_mo
_cod_database_code               4033943
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 91.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.10
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.339
_oxdiff_exptl_absorpt_empirical_full_min 0.710