Synthesis, crystal structure, DFT calculations and Hirshfeld surface analysis of 2-(1-decyl-2-oxoindolin-3-ylidene)propanedinitrile
Rayni, Ibtissam; El Bakri, Youness; Lai, Chin-Hung; El Ghayati, L'houssaine; Essassi, El Mokhtar; Mague, Joel T.; Acta Crystallographica Section E 75 (2019) 21–25; doi:10.1107/S2056989018017267

data_2242782
_publ_section_title
;
 Synthesis, crystal structure, DFT calculations and Hirshfeld surface
 analysis of 2-(1-decyl-2-oxoindolin-3-ylidene)propanedinitrile
;
_journal_coeditor_code           VM2214
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              21
_journal_page_last               25
_journal_paper_doi               10.1107/S2056989018017267
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C21 H25 N3 O'
_chemical_formula_moiety         'C21 H25 N3 O'
_chemical_formula_sum            'C21 H25 N3 O'
_chemical_formula_weight         335.44
_chemical_name_systematic
;
2-(1-decyl-2-oxoindolin-3-ylidene)propanedinitrile
;
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.965(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   44.4837(12)
_cell_length_b                   4.72930(10)
_cell_length_c                   18.3432(5)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.3174
_cell_measurement_theta_min      4.1562
_cell_volume                     3691.05(17)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL 2014/7</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25556
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         72.309
_diffrn_reflns_theta_min         2.077
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>TWINABS</i>; Sheldrick, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0647P)^2^+0.6236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                2656
_reflns_number_total             3592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vm2214sup1.cif
_cod_data_source_block           I
_cod_database_code               2242782
_cod_database_fobs_code          2242782
_shelx_estimated_absorpt_t_min   0.847
_shelx_estimated_absorpt_t_max   0.982
_shelx_hkl_checksum              90168
_shelx_res_checksum              28370