Synthesis of Tetracyclic 2,3-Dihydro-1,3-diazepines from a Dinitrodibenzothiophene Derivative.
Montanaro, Stephanie; Wright, Iain A.; Batsanov, Andrei S.; Bryce, Martin R.; The Journal of organic chemistry 83 (2018) 12320–12326; doi:10.1021/acs.joc.8b02029

data_4035210
_publ_section_title
;
 Synthesis of Tetracyclic 2,3-Dihydro-1,3-diazepines from a
 Dinitrodibenzothiophene Derivative.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12320
_journal_page_last               12326
_journal_paper_doi               10.1021/acs.joc.8b02029
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H4 N4 O6 S'
_chemical_formula_sum            'C14 H4 N4 O6 S'
_chemical_formula_weight         356.27
_chemical_name_systematic
1,9-dinitro-3,7-dicyanodibenzothiophene-5,5-dioxide
_space_group_crystal_system      tetragonal
_space_group_IT_number           106
_space_group_name_Hall           'P 4c -2ab'
_space_group_name_H-M_alt        'P 42 b c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-06-18
_audit_creation_method
;
Olex2 1.2-beta
(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            8
_cell_length_a                   10.4555(9)
_cell_length_b                   10.4555(9)
_cell_length_c                   26.750(2)
_cell_measurement_reflns_used    9338
_cell_measurement_temperature    120
_cell_measurement_theta_max      34.56
_cell_measurement_theta_min      3.05
_cell_volume                     2924.2(4)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 multi-CPU (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            47341
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.755
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2016/2 (Krause et al., 2015) was used for absorption correction. 
 wR2(int) was 0.1804 before and 0.0795 after correction. 
 The Ratio of minimum to maximum transmission is 0.9172. 
 The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       'square plate'
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.384
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     175
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0632P)^2^+6.2854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1535
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3264
_reflns_number_total             3349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02029_si_002.cif
_cod_data_source_block           t-5_16srv083
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2924.2(6)
_cod_database_code               4035210
_ccdc_comments                   'orthorhombic form see CCDC-1850071'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.905
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6(3)
 0.4(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 S1B-O2B \\sim S1B-O1B \\sim S1A-O1A \\sim S1A-O2A
 with sigma of 0.02
 S1A-C6A \\sim S1A-C6A_$1 \\sim S1B-C6B \\sim S1B-C6B_$2
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(O2B) = Uiso(O1B)
Uiso(O1A) = Uiso(O2A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Fixed Sof: S1A(0.5) O2A(0.5) O2B(0.5) O1B(0.5) S1B(0.5) O1A(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C3A(H3A), C1B(H1B), C3B(H3B)
;
_shelx_res_checksum              47332
_shelx_hkl_checksum              89358
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'