#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/01/2230136.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230136
loop_
_publ_author_name
'Saraswathi, B. S.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 N-(3-Chlorophenyl)-N'-(2-methylphenyl)succinamide
 monohydrate
;
_journal_coeditor_code           RZ2582
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1223
_journal_paper_doi               10.1107/S1600536811014942
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H17 Cl N2 O2, H2 O'
_chemical_formula_moiety         'C17 H17 Cl N2 O2, H2 O'
_chemical_formula_sum            'C17 H19 Cl N2 O3'
_chemical_formula_weight         334.79
_chemical_name_common
;
N-(3-Chlorophenyl)-N'-(2-methylphenyl)succinamide monohydrate
;
_chemical_name_systematic
;
N-(3-Chlorophenyl)-N'-(2-methylphenyl)butanediamide 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                 90.11(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.875(4)
_cell_length_b                   13.908(3)
_cell_length_c                   8.088(2)
_cell_measurement_reflns_used    1620
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.73
_cell_volume                     1673.3(7)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω
;
_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  0.0737
_diffrn_reflns_av_sigmaI/netI    0.1066
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6273
_diffrn_reflns_theta_full        25.51
_diffrn_reflns_theta_max         25.51
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.9001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3080
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.2231
_refine_ls_R_factor_gt           0.1154
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1040P)²+1.4616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2385
_refine_ls_wR_factor_ref         0.2853
_reflns_number_gt                1436
_reflns_number_total             3080
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2582.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230136
_cod_database_fobs_code          2230136
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.24505(16) 0.43031(14) 0.5534(3) 0.0888(8) Uani d . 1 1 . .
O O1 0.4988(3) 0.2577(3) 0.2806(6) 0.0588(13) Uani d . 1 1 . .
O O2 0.6939(3) 0.1531(3) 0.3675(5) 0.0509(12) Uani d . 1 1 . .
N N1 0.4157(4) 0.1301(4) 0.3620(7) 0.0526(14) Uani d D 1 1 . .
H H1N 0.414(4) 0.0680(15) 0.367(8) 0.063 Uiso d D 1 1 . .
N N2 0.7588(4) 0.2301(4) 0.1544(6) 0.0511(15) Uani d D 1 1 . .
H H2N 0.757(4) 0.246(4) 0.052(3) 0.061 Uiso d D 1 1 . .
C C1 0.3450(4) 0.1731(5) 0.4498(8) 0.0480(17) Uani d . 1 1 . .
C C2 0.3334(4) 0.2716(4) 0.4599(8) 0.0497(17) Uani d . 1 1 . .
H H2 0.3746 0.3134 0.4120 0.060 Uiso calc R 1 1 . .
C C3 0.2595(5) 0.3062(5) 0.5426(9) 0.0571(19) Uani d . 1 1 . .
C C4 0.1978(5) 0.2489(6) 0.6174(9) 0.0622(19) Uani d . 1 1 . .
H H4 0.1488 0.2749 0.6729 0.075 Uiso calc R 1 1 . .
C C5 0.2105(5) 0.1503(5) 0.6079(10) 0.072(2) Uani d . 1 1 . .
H H5 0.1695 0.1093 0.6582 0.087 Uiso calc R 1 1 . .
C C6 0.2826(5) 0.1127(5) 0.5254(9) 0.062(2) Uani d . 1 1 . .
H H6 0.2900 0.0464 0.5198 0.074 Uiso calc R 1 1 . .
C C7 0.4836(4) 0.1708(5) 0.2793(8) 0.0446(16) Uani d . 1 1 . .
C C8 0.5394(4) 0.1008(5) 0.1842(8) 0.0542(18) Uani d . 1 1 . .
H H8A 0.5022 0.0715 0.0994 0.065 Uiso calc R 1 1 . .
H H8B 0.5591 0.0502 0.2585 0.065 Uiso calc R 1 1 . .
C C9 0.6221(5) 0.1455(5) 0.1022(8) 0.0540(18) Uani d . 1 1 . .
H H9A 0.6479 0.0991 0.0263 0.065 Uiso calc R 1 1 . .
H H9B 0.6033 0.2009 0.0380 0.065 Uiso calc R 1 1 . .
C C10 0.6931(4) 0.1764(4) 0.2227(8) 0.0404(15) Uani d . 1 1 . .
C C11 0.8362(5) 0.2665(5) 0.2395(7) 0.0478(17) Uani d . 1 1 . .
C C12 0.9000(5) 0.2044(5) 0.3062(8) 0.059(2) Uani d . 1 1 . .
C C13 0.9760(5) 0.2453(7) 0.3794(9) 0.073(2) Uani d . 1 1 . .
H H13 1.0195 0.2058 0.4264 0.087 Uiso calc R 1 1 . .
C C14 0.9870(6) 0.3428(8) 0.3827(10) 0.083(3) Uani d . 1 1 . .
H H14 1.0384 0.3685 0.4312 0.100 Uiso calc R 1 1 . .
C C15 0.9247(6) 0.4031(6) 0.3169(11) 0.081(3) Uani d . 1 1 . .
H H15 0.9335 0.4693 0.3196 0.097 Uiso calc R 1 1 . .
C C16 0.8483(6) 0.3649(5) 0.2460(9) 0.066(2) Uani d . 1 1 . .
H H16 0.8047 0.4056 0.2024 0.079 Uiso calc R 1 1 . .
C C17 0.8932(6) 0.0992(6) 0.2956(10) 0.087(3) Uani d . 1 1 . .
H H17A 0.8438 0.0775 0.3621 0.131 Uiso calc R 1 1 . .
H H17B 0.9479 0.0708 0.3352 0.131 Uiso calc R 1 1 . .
H H17C 0.8834 0.0807 0.1827 0.131 Uiso calc R 1 1 . .
O O3 0.5938(4) 0.0811(3) 0.6426(6) 0.0690(15) Uani d D 1 1 . .
H H31O 0.614(5) 0.098(5) 0.549(5) 0.104 Uiso d D 1 1 . .
H H32O 0.561(5) 0.125(4) 0.679(8) 0.104 Uiso d D 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 129.7(6) ?
C7 N1 H1N . . 118(4) ?
C1 N1 H1N . . 113(4) ?
C10 N2 C11 . . 125.5(5) ?
C10 N2 H2N . . 121(5) ?
C11 N2 H2N . . 113(5) ?
C2 C1 C6 . . 119.2(6) ?
C2 C1 N1 . . 123.0(6) ?
C6 C1 N1 . . 117.8(6) ?
C3 C2 C1 . . 118.3(6) ?
C3 C2 H2 . . 120.8 ?
C1 C2 H2 . . 120.8 ?
C4 C3 C2 . . 123.6(7) ?
C4 C3 Cl1 . . 118.4(6) ?
C2 C3 Cl1 . . 118.0(6) ?
C3 C4 C5 . . 117.6(7) ?
C3 C4 H4 . . 121.2 ?
C5 C4 H4 . . 121.2 ?
C6 C5 C4 . . 120.8(7) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 120.5(7) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
O1 C7 N1 . . 123.5(6) ?
O1 C7 C8 . . 122.8(6) ?
N1 C7 C8 . . 113.7(6) ?
C7 C8 C9 . . 114.0(5) ?
C7 C8 H8A . . 108.8 ?
C9 C8 H8A . . 108.8 ?
C7 C8 H8B . . 108.8 ?
C9 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
C10 C9 C8 . . 113.6(5) ?
C10 C9 H9A . . 108.9 ?
C8 C9 H9A . . 108.8 ?
C10 C9 H9B . . 108.8 ?
C8 C9 H9B . . 108.8 ?
H9A C9 H9B . . 107.7 ?
O2 C10 N2 . . 122.4(6) ?
O2 C10 C9 . . 123.8(6) ?
N2 C10 C9 . . 113.7(5) ?
C16 C11 C12 . . 120.8(7) ?
C16 C11 N2 . . 118.2(6) ?
C12 C11 N2 . . 120.9(6) ?
C11 C12 C13 . . 117.6(7) ?
C11 C12 C17 . . 123.3(7) ?
C13 C12 C17 . . 119.1(8) ?
C14 C13 C12 . . 120.6(8) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C15 C14 C13 . . 121.6(9) ?
C15 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
C14 C15 C16 . . 119.1(8) ?
C14 C15 H15 . . 120.4 ?
C16 C15 H15 . . 120.4 ?
C15 C16 C11 . . 120.3(8) ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
C12 C17 H17A . . 109.5 ?
C12 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C12 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
H31O O3 H32O . . 108(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 . 1.742(7) ?
O1 C7 . 1.230(7) ?
O2 C10 . 1.215(7) ?
N1 C7 . 1.338(8) ?
N1 C1 . 1.404(8) ?
N1 H1N . 0.86(2) ?
N2 C10 . 1.350(8) ?
N2 C11 . 1.432(8) ?
N2 H2N . 0.86(2) ?
C1 C2 . 1.384(9) ?
C1 C6 . 1.393(9) ?
C2 C3 . 1.375(9) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.358(9) ?
C4 C5 . 1.386(9) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.368(10) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.494(9) ?
C8 C9 . 1.531(9) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.499(9) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11 C16 . 1.381(9) ?
C11 C12 . 1.391(9) ?
C12 C13 . 1.396(10) ?
C12 C17 . 1.469(10) ?
C13 C14 . 1.366(11) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.357(11) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.378(11) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
O3 H31O . 0.85(2) ?
O3 H32O . 0.84(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O3 3_656 0.86(2) 2.08(2) 2.940(7) 175(6)
N2 H2N O2 4_565 0.86(2) 2.25(4) 2.991(7) 145(6)
O3 H31O O2 . 0.85(2) 2.04(3) 2.861(6) 163(8)
O3 H32O O1 4_566 0.84(2) 2.05(3) 2.877(6) 171(9)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . 2.1(11) ?
C7 N1 C1 C6 . . . . -180.0(7) ?
C6 C1 C2 C3 . . . . -1.0(10) ?
N1 C1 C2 C3 . . . . 177.0(6) ?
C1 C2 C3 C4 . . . . 1.1(10) ?
C1 C2 C3 Cl1 . . . . -179.5(5) ?
C2 C3 C4 C5 . . . . -0.4(11) ?
Cl1 C3 C4 C5 . . . . -179.9(6) ?
C3 C4 C5 C6 . . . . -0.2(12) ?
C4 C5 C6 C1 . . . . 0.3(12) ?
C2 C1 C6 C5 . . . . 0.3(11) ?
N1 C1 C6 C5 . . . . -177.7(7) ?
C1 N1 C7 O1 . . . . 6.9(11) ?
C1 N1 C7 C8 . . . . -173.0(6) ?
O1 C7 C8 C9 . . . . 5.4(9) ?
N1 C7 C8 C9 . . . . -174.7(6) ?
C7 C8 C9 C10 . . . . 69.5(7) ?
C11 N2 C10 O2 . . . . -0.2(10) ?
C11 N2 C10 C9 . . . . -177.8(6) ?
C8 C9 C10 O2 . . . . 13.0(9) ?
C8 C9 C10 N2 . . . . -169.4(5) ?
C10 N2 C11 C16 . . . . -119.5(7) ?
C10 N2 C11 C12 . . . . 63.9(8) ?
C16 C11 C12 C13 . . . . 0.1(9) ?
N2 C11 C12 C13 . . . . 176.6(6) ?
C16 C11 C12 C17 . . . . -176.8(7) ?
N2 C11 C12 C17 . . . . -0.2(9) ?
C11 C12 C13 C14 . . . . -0.8(10) ?
C17 C12 C13 C14 . . . . 176.2(7) ?
C12 C13 C14 C15 . . . . 0.6(13) ?
C13 C14 C15 C16 . . . . 0.4(13) ?
C14 C15 C16 C11 . . . . -1.2(12) ?
C12 C11 C16 C15 . . . . 0.9(10) ?
N2 C11 C16 C15 . . . . -175.7(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656667
