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_4035211
_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         'C14 H4 N4 O6 S, 0.5(C4 H8 O)'
_chemical_formula_sum            'C16 H8 N4 O6.5 S'
_chemical_formula_weight         392.32
_chemical_name_systematic
'3,7-dicyano-1,9-dinitrodibenzothiophene-S,S-dioxide : tetrahydrofuran'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-07
_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                 114.786(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3642(9)
_cell_length_b                   9.6436(6)
_cell_length_c                   13.6194(9)
_cell_measurement_reflns_used    6644
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.88
_cell_measurement_theta_min      2.68
_cell_volume                     1593.56(18)
_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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       \w-scan
_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  0.0641
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14526
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.061
_diffrn_reflns_theta_min         2.679
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 14526 reflections, Rint = 0.0641
 (8050 with I > 3sig(I), Rint = 0.0544)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.0040(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5431
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+1.8134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4437
_reflns_number_total             5431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02029_si_002.cif
_cod_data_source_block           5-thf_15srv108
_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               4035211
_ccdc_comments                   'solvent-free see CCDC-1850071, 1850072'
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5217(13)
 0.4783(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 O7-C17 \\sim O7-C19
 with sigma of 0.02
 C18-C17 \\sim C18-C17_$1 \\sim C19-C17_$1
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 O7, C17, C18, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O7(0.5) C18(0.5) H18A(0.5) H18B(0.5) C19(0.5) H19A(0.5) H19B(0.5)
6.a Riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C9(H9), C11(H11)
;
_shelx_res_checksum              79324
_shelx_hkl_checksum              93417
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'