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_4035212
_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_formula_moiety         'C17 H12 N4 O2 S'
_chemical_formula_sum            'C17 H12 N4 O2 S'
_chemical_formula_weight         336.37
_chemical_melting_point          623
_chemical_name_systematic
1,9-(N,N'-2,2-diaminoisopropyl)-3,7-dicyanodibenzothiophene-5,5-dioxide
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-25
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.9424(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.8345(10)
_cell_length_b                   9.7054(5)
_cell_length_c                   17.1644(8)
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.04
_cell_measurement_theta_min      2.37
_cell_volume                     3106.0(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37838
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         32.088
_diffrn_reflns_theta_min         2.366
_diffrn_source                   'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Krause et al., 2015) was used for absorption correction.
wR2(int) was 0.1330 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.9423.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       'triangular plate'
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0540P)^2^+3.3470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4545
_reflns_number_total             5434
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02029_si_002.cif
_cod_data_source_block           6_16srv076
_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_database_code               4035212
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.912
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H16A)=Uiso(H16B)=Uiso(H16C)=FVAR(1)
 Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C2(H2A), C4(H4)
3.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              112
_shelx_hkl_checksum              79942
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'