Crystal structure of <i>N</i>,<i>N</i>'-bis[3-(methylsulfanyl)propyl]-1,8:4,5-naphthalenetetracarboxylic diimide
Park, Juhyeon; Lee, Seung Heon; Choi, Myong Yong; Moon, Cheol Joo; Kim, Tae Ho; Acta Crystallographica Section E 75 (2019) 934–938; doi:10.1107/S2056989019007771

data_2242963
_publ_section_title
;
 Crystal structure of
 <i>N</i>,<i>N</i>'-bis[3-(methylsulfanyl)propyl]-1,8:4,5-naphthalenetetracarboxylic
 diimide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              934
_journal_page_last               938
_journal_paper_doi               10.1107/S2056989019007771
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C22 H22 N2 O4 S2'
_chemical_formula_moiety         'C22 H22 N2 O4 S2'
_chemical_formula_sum            'C22 H22 N2 O4 S2'
_chemical_formula_weight         442.53
_chemical_name_systematic
'<i>N</i>,<i>N</i>'-Bis[3-(methylsulfanyl)propyl]-1,8:4,5-naphthalenetetracarboxylic diimide'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.333(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0500(2)
_cell_length_b                   4.94070(10)
_cell_length_c                   24.9626(7)
_cell_measurement_reflns_used    1676
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      3.12
_cell_volume                     989.99(4)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2010)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5641
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.636
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       rod
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0403P)^2^+0.3426P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                1360
_reflns_number_total             1732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sj5571sup1.cif
_cod_data_source_block           I
_cod_database_code               2242963
_cod_database_fobs_code          2242963
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.988
_shelx_hkl_checksum              25425
_shelx_res_checksum              94515