Crystal structure of 4-(3,4-dicyanophenoxy)-<i>N</i>-[3-(dimethylamino)propyl]benzamide monohydrate: a phenoxyphthalonitrile derivative
Çolak, Senem; Yıldız, Salih Zeki; Çaylak Delibaş, Nagihan; Pişkin, Hasan; Hökelek, Tuncer; Acta Crystallographica Section E 71 (2015) 1042–1044; doi:10.1107/S2056989015014991

data_2241012
_publ_section_title
;
 Crystal structure of
 4-(3,4-dicyanophenoxy)-<i>N</i>-[3-(dimethylamino)propyl]benzamide
 monohydrate: a phenoxyphthalonitrile derivative
;
_journal_coeditor_code           SU5187
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1042
_journal_page_last               1044
_journal_paper_doi               10.1107/S2056989015014991
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C20 H20 N4 O2, H2 O'
_chemical_formula_moiety         'C20 H20 N4 O2, H2 O'
_chemical_formula_sum            'C20 H22 N4 O3'
_chemical_formula_weight         366.42
_chemical_name_systematic
;
4-(3,4-Dicyanophenoxy)-<i>N</i>-[3-(dimethylamino)propyl]benzamide
monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.819(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9004(4)
_cell_length_b                   10.5012(3)
_cell_length_c                   14.1343(4)
_cell_measurement_reflns_used    3102
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.43
_cell_volume                     1886.72(10)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11419
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0573P)^2^+0.8262P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                3181
_reflns_number_total             4167
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su5187sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2241012
_cod_database_fobs_code          2241012