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_4033942
_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_absolute_configuration unk
_chemical_formula_moiety         'C20 H13 Br N2 O6'
_chemical_formula_sum            'C20 H13 Br N2 O6'
_chemical_formula_weight         457.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1343(4)
_cell_length_b                   11.9258(6)
_cell_length_c                   18.2918(10)
_cell_measurement_reflns_used    5579
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0290
_cell_measurement_theta_min      2.0780
_cell_volume                     1774.45(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9875
_diffrn_measured_fraction_theta_max 0.9875
_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    -87.00  15.00   0.50    8.00    --  -20.00   0.00 108.00  204
  2  \w    -73.00   7.00   0.50    8.00    --  -20.00 -72.00  36.00  160
  3  \w    -80.00 -54.50   0.50    8.00    --  -20.00 -72.00-180.00   51
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0509175000
_diffrn_orient_matrix_UB_12      -0.0160211000
_diffrn_orient_matrix_UB_13      0.0297519000
_diffrn_orient_matrix_UB_21      -0.0693567000
_diffrn_orient_matrix_UB_22      -0.0005890000
_diffrn_orient_matrix_UB_23      -0.0235597000
_diffrn_orient_matrix_UB_31      0.0148147000
_diffrn_orient_matrix_UB_32      -0.0571991000
_diffrn_orient_matrix_UB_33      -0.0079678000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9696
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.04
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.7114
_exptl_crystal_description       block
_exptl_crystal_F_000             919.3829
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.3498
_refine_diff_density_min         -0.3537
_refine_diff_density_rms         0.0823
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.022(8)
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             9.9901
_refine_ls_goodness_of_fit_ref   1.0493
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0493
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0368P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.972
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                2893
_reflns_number_total             3079
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b03039_si_001.cif
_cod_data_source_block           INN-AS-302-A_Mo
_cod_original_cell_volume        1774.46(17)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4033942
_chemical_oxdiff_formula         C20H13N2Br1O6
_reflns_odcompleteness_completeness 93.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.22
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C20(H20), C12(H12), C18(H18), C10(H10), C9(H9), C17(H17)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.762