Interaction of 4-oxoalkane-1,1,2,2-tetracarbonitriles with Lawesson's reagent – a new approach to the synthesis of 2,2'-disulfanediylbis(1H-pyrroles). The synthesis of photochromic diarylethene with disulfide bridge
Belikov, Mikhail Yu; Fedoseev, Sergey V.; Ievlev, Mikhail Yu; Ershov, Oleg V.; Tafeenko, Viktor; RSC Adv.  (2015) –; doi:10.1039/C5RA11304K

data_7221635
_publ_section_title
;
 Interaction of 4-oxoalkane-1,1,2,2-tetracarbonitriles with Lawesson's
 reagent -- a new approach to the synthesis of
 2,2'-disulfanediylbis(1H-pyrroles). The synthesis of photochromic
 diarylethene with disulfide bridge
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA11304K
_journal_year                    2015
_chemical_formula_moiety         'C22 H26 N4 S2'
_chemical_formula_sum            'C22 H26 N4 S2'
_chemical_formula_weight         410.59
_chemical_melting_point          499.5(5)
_chemical_name_common
2,2'-disulfanediylbis(4,5,6,7,8,9-hexahydro-1H-cycloocta[b]pyrrole-3-carbonitrile)
_chemical_name_systematic
2,2'-disulfanediylbis(4,5,6,7,8,9-hexahydro-1H-cycloocta[b]pyrrole-3-carbonitrile)
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2b'
_symmetry_space_group_name_H-M   'P b n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-11 deposited with the CCDC.
2015-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6655(3)
_cell_length_b                   13.8908(6)
_cell_length_c                   16.1834(7)
_cell_measurement_temperature    295(2)
_cell_volume                     2172.81(15)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      ' 2361 frames, detector distance = 42 mm'
_diffrn_measurement_device_type  STOE
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.1183
_diffrn_reflns_av_sigmaI/netI    0.1424
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8748
_diffrn_reflns_theta_full        72.73
_diffrn_reflns_theta_max         72.73
_diffrn_reflns_theta_min         5.33
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.325
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .08
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00052(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                1692
_reflns_number_total             2154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra11304k2.cif
_cod_data_source_block           fs774
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '499-500' was changed to '499.5(5)' -
the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'ORTHORHOMBIC' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      'p bna'
_cod_database_code               7221635