#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/65/2216554.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_2216554
loop_
_publ_author_name
'Shui-Ping Deng'
'Shan Liu'
'Guang-Liang Song'
'Hong-Jun Zhu'
_publ_section_title
;
 2-Benzoylanilinium chloride monohydrate
;
_journal_coeditor_code           HK2364
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4603
_journal_page_last               o4603
_journal_paper_doi               10.1107/S1600536807055195
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H12 N O +, Cl -, H2 O'
_chemical_formula_moiety         'C13 H12 N O +, Cl -, H2 O'
_chemical_formula_sum            'C13 H14 Cl N O2'
_chemical_formula_weight         251.70
_chemical_name_systematic
;
2-Benzoylanilinium chloride 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                 90.50(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7710(10)
_cell_length_b                   17.450(4)
_cell_length_c                   15.277(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1271.8(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'ω/2θ 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  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0741
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2786
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.9181
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.07P)²+0.6P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1744
_reflns_number_gt                1522
_reflns_number_total             2479
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2364.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216554
_cod_database_fobs_code          2216554
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
Cl Cl 1.0018(2) 0.34988(6) 1.01031(6) 0.0466(3) Uani d . 1
O OW 0.4922(7) 0.56862(19) 0.8837(2) 0.0602(9) Uani d D 1
H HWA 0.366(8) 0.591(3) 0.914(3) 0.10(2) Uiso d D 1
H HWB 0.632(7) 0.596(3) 0.903(4) 0.11(2) Uiso d D 1
O O -0.0034(6) 0.47495(18) 0.81909(19) 0.0541(8) Uani d . 1
N N 0.4887(6) 0.41120(18) 0.88813(19) 0.0394(8) Uani d . 1
H H0A 0.6493 0.3993 0.9149 0.059 Uiso calc R 1
H H0B 0.3457 0.3968 0.9213 0.059 Uiso calc R 1
H H0C 0.4809 0.4616 0.8794 0.059 Uiso calc R 1
C C1 0.6114(11) 0.2658(3) 0.7154(3) 0.0650(13) Uani d . 1
H H1A 0.7167 0.2215 0.7081 0.078 Uiso calc R 1
C C2 0.4379(11) 0.2909(3) 0.6492(3) 0.0651(14) Uani d . 1
H H2A 0.4250 0.2633 0.5973 0.078 Uiso calc R 1
C C3 0.2834(10) 0.3566(3) 0.6594(3) 0.0585(12) Uani d . 1
H H3A 0.1667 0.3732 0.6141 0.070 Uiso calc R 1
C C4 0.2994(8) 0.3992(2) 0.7374(2) 0.0408(9) Uani d . 1
C C5 0.4727(8) 0.3716(2) 0.8040(2) 0.0384(9) Uani d . 1
C C6 0.6292(9) 0.3067(2) 0.7928(3) 0.0516(11) Uani d . 1
H H6A 0.7479 0.2899 0.8375 0.062 Uiso calc R 1
C C7 0.1231(8) 0.4689(2) 0.7509(3) 0.0432(10) Uani d . 1
C C8 0.1051(8) 0.5295(3) 0.6834(3) 0.0457(10) Uani d . 1
C C9 -0.0827(10) 0.5888(3) 0.6937(3) 0.0626(13) Uani d . 1
H H9A -0.2023 0.5887 0.7415 0.075 Uiso calc R 1
C C10 -0.0957(12) 0.6478(3) 0.6347(4) 0.0761(15) Uani d . 1
H H10A -0.2215 0.6877 0.6437 0.091 Uiso calc R 1
C C11 0.0721(12) 0.6489(3) 0.5634(3) 0.0679(14) Uani d . 1
H H11A 0.0594 0.6887 0.5231 0.082 Uiso calc R 1
C C12 0.2563(13) 0.5918(3) 0.5519(3) 0.0771(16) Uani d . 1
H H12A 0.3717 0.5923 0.5032 0.093 Uiso calc R 1
C C13 0.2776(11) 0.5322(3) 0.6115(3) 0.0638(13) Uani d . 1
H H13A 0.4093 0.4937 0.6029 0.077 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl 0.0380(5) 0.0552(6) 0.0465(6) 0.0004(5) 0.0016(4) 0.0006(5)
OW 0.0421(18) 0.062(2) 0.076(2) -0.0039(17) 0.0082(17) -0.0183(17)
O 0.0365(15) 0.074(2) 0.0516(18) 0.0013(14) 0.0056(14) 0.0060(15)
N 0.0293(16) 0.052(2) 0.0368(17) -0.0025(15) 0.0005(14) 0.0011(15)
C1 0.075(3) 0.044(3) 0.076(3) 0.005(2) 0.001(3) -0.004(2)
C2 0.089(4) 0.050(3) 0.057(3) -0.008(3) 0.006(3) -0.014(2)
C3 0.062(3) 0.063(3) 0.049(2) -0.009(3) -0.008(2) -0.002(2)
C4 0.036(2) 0.043(2) 0.044(2) -0.0054(18) 0.0012(17) 0.0018(18)
C5 0.035(2) 0.041(2) 0.039(2) -0.0065(18) 0.0046(16) 0.0012(17)
C6 0.053(3) 0.046(3) 0.056(3) 0.001(2) -0.003(2) 0.000(2)
C7 0.031(2) 0.059(3) 0.040(2) -0.0082(19) -0.0008(17) 0.000(2)
C8 0.038(2) 0.056(3) 0.043(2) -0.005(2) -0.0028(18) 0.002(2)
C9 0.054(3) 0.069(3) 0.065(3) 0.016(3) 0.006(2) 0.006(3)
C10 0.076(4) 0.060(3) 0.092(4) 0.021(3) -0.010(3) 0.003(3)
C11 0.093(4) 0.050(3) 0.060(3) -0.006(3) -0.017(3) 0.006(3)
C12 0.109(5) 0.066(3) 0.056(3) 0.001(3) 0.017(3) 0.008(3)
C13 0.075(3) 0.056(3) 0.060(3) 0.010(3) 0.014(3) 0.008(2)
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'
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'
Cl Cl 0.1484 0.1585 '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
HWB OW HWA 96(3)
C5 N H0A 109.5
C5 N H0B 109.5
H0A N H0B 109.5
C5 N H0C 109.5
H0A N H0C 109.5
H0B N H0C 109.5
C2 C1 C6 119.8(5)
C2 C1 H1A 120.1
C6 C1 H1A 120.1
C3 C2 C1 120.3(4)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C2 C3 C4 120.8(4)
C2 C3 H3A 119.6
C4 C3 H3A 119.6
C5 C4 C3 117.7(4)
C5 C4 C7 120.8(3)
C3 C4 C7 121.4(4)
C6 C5 C4 121.1(4)
C6 C5 N 118.4(3)
C4 C5 N 120.4(3)
C5 C6 C1 120.2(4)
C5 C6 H6A 119.9
C1 C6 H6A 119.9
O C7 C8 120.6(4)
O C7 C4 118.4(4)
C8 C7 C4 121.0(3)
C13 C8 C9 117.3(4)
C13 C8 C7 123.3(4)
C9 C8 C7 119.4(4)
C10 C9 C8 120.9(5)
C10 C9 H9A 119.5
C8 C9 H9A 119.5
C11 C10 C9 121.1(5)
C11 C10 H10A 119.5
C9 C10 H10A 119.5
C12 C11 C10 119.0(5)
C12 C11 H11A 120.5
C10 C11 H11A 120.5
C11 C12 C13 121.1(5)
C11 C12 H12A 119.5
C13 C12 H12A 119.5
C8 C13 C12 120.6(5)
C8 C13 H13A 119.7
C12 C13 H13A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
OW HWA 0.86(4)
OW HWB 0.87(5)
O C7 1.213(4)
N C5 1.461(5)
N H0A 0.8900
N H0B 0.8900
N H0C 0.8900
C1 C2 1.372(7)
C1 C6 1.383(6)
C1 H1A 0.9300
C2 C3 1.372(6)
C2 H2A 0.9300
C3 C4 1.406(6)
C3 H3A 0.9300
C4 C5 1.391(5)
C4 C7 1.493(6)
C5 C6 1.369(5)
C6 H6A 0.9300
C7 C8 1.480(6)
C8 C13 1.379(6)
C8 C9 1.379(6)
C9 C10 1.369(7)
C9 H9A 0.9300
C10 C11 1.358(7)
C10 H10A 0.9300
C11 C12 1.341(7)
C11 H11A 0.9300
C12 C13 1.385(7)
C12 H12A 0.9300
C13 H13A 0.9300
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
_geom_hbond_publ_flag
N H0A Cl . 0.89 2.38 3.247(3) 165.4 yes
N H0B Cl 1_455 0.89 2.29 3.178(3) 174.7 yes
N H0C OW . 0.89 1.87 2.748(5) 168.7 yes
OW HWB Cl 3_767 0.87(5) 2.38(3) 3.226(4) 165(5) yes
OW HWA Cl 3_667 0.86(4) 2.35(4) 3.204(4) 176(5) yes
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
C6 C1 C2 C3 0.4(8)
C1 C2 C3 C4 -0.1(7)
C2 C3 C4 C5 -1.1(6)
C2 C3 C4 C7 -177.2(4)
C3 C4 C5 C6 2.1(6)
C7 C4 C5 C6 178.2(4)
C3 C4 C5 N -177.1(4)
C7 C4 C5 N -1.0(5)
C4 C5 C6 C1 -1.8(6)
N C5 C6 C1 177.4(4)
C2 C1 C6 C5 0.5(7)
C5 C4 C7 O -43.9(5)
C3 C4 C7 O 132.0(4)
C5 C4 C7 C8 135.4(4)
C3 C4 C7 C8 -48.7(5)
O C7 C8 C13 169.0(4)
C4 C7 C8 C13 -10.3(6)
O C7 C8 C9 -7.7(6)
C4 C7 C8 C9 173.0(4)
C13 C8 C9 C10 -0.1(7)
C7 C8 C9 C10 176.9(5)
C8 C9 C10 C11 1.3(8)
C9 C10 C11 C12 -1.2(9)
C10 C11 C12 C13 -0.1(8)
C9 C8 C13 C12 -1.2(7)
C7 C8 C13 C12 -178.0(4)
C11 C12 C13 C8 1.3(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21120360
