#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/17/8101790.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101790
loop_
_publ_author_name
'Oueslati, A.'
'Kefi, R.'
'Akriche, S.'
'Ben Nasr, C.'
_publ_section_title
;
Crystal structure of o-cyanoaniline hydrochloride, (NCC₆H₄NH₃)Cl
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              365
_journal_page_last               366
_journal_volume                  220
_journal_year                    2005
_chemical_formula_moiety         'C7 H7 Cl1 N2'
_chemical_formula_structural     (NCC6H4NH3)Cl
_chemical_formula_sum            'C7 H7 Cl N2'
_chemical_formula_weight         154.60
_chemical_name_systematic
;
 o-cyanoaniline hydrochloride
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 93.18(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.658(5)
_cell_length_b                   15.406(9)
_cell_length_c                   8.234(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      8
_cell_volume                     716.6(10)
_computing_molecular_graphics    DIAMOND
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf-Nonius Mach3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2471
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.64
_diffrn_standards_interval_count 400
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       0.055(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1263
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0204
_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/[σ²(Fo²)+(0.0393P)²+0.0979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0524
_reflns_number_gt                1260
_reflns_number_total             1263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1546.cff
_cod_data_source_block           cad4
_cod_original_sg_symbol_H-M      C1c1
_cod_database_code               8101790
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.12742(5) -0.208513(19) -0.63907(4) 0.03297(14) Uani 1 4 a d . . .
N1 N -0.3798(2) -0.18422(8) -0.82051(16) 0.0275(3) Uani 1 4 a d . . .
H1 H -0.257(4) -0.2039(11) -0.761(2) 0.029(5) Uiso 1 4 a d . . .
H2 H -0.384(4) -0.2177(12) -0.916(3) 0.040(5) Uiso 1 4 a d . . .
H3 H -0.505(4) -0.2001(12) -0.774(3) 0.038(5) Uiso 1 4 a d . . .
N2 N 0.1280(3) -0.16284(10) -1.0680(2) 0.0460(4) Uani 1 4 a d . . .
C1 C -0.3558(2) -0.09146(9) -0.85013(16) 0.0246(3) Uani 1 4 a d . . .
C2 C -0.1656(3) -0.06116(10) -0.93531(18) 0.0275(3) Uani 1 4 a d . . .
C3 C -0.1358(3) 0.02782(11) -0.9552(2) 0.0353(4) Uani 1 4 a d . . .
H7 H -0.006(4) 0.0443(13) -1.026(2) 0.042(5) Uiso 1 4 a d . . .
C4 C -0.2957(3) 0.08494(11) -0.8940(2) 0.0390(4) Uani 1 4 a d . . .
H6 H -0.276(4) 0.1407(16) -0.907(3) 0.049(6) Uiso 1 4 a d . . .
C5 C -0.4863(3) 0.05461(10) -0.8130(2) 0.0386(4) Uani 1 4 a d . . .
H5 H -0.599(4) 0.0959(13) -0.773(2) 0.037(5) Uiso 1 4 a d . . .
C6 C -0.5155(3) -0.03411(10) -0.79008(18) 0.0314(3) Uani 1 4 a d . . .
H4 H -0.630(4) -0.0575(12) -0.732(3) 0.039(5) Uiso 1 4 a d . . .
C7 C -0.0021(3) -0.11925(10) -1.00621(17) 0.0314(3) Uani 1 4 a d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.02484(19) 0.03657(19) 0.0381(2) 0.00847(15) 0.00715(12) 0.00242(14)
N1 0.0243(6) 0.0285(6) 0.0301(6) -0.0006(5) 0.0063(5) -0.0014(5)
N2 0.0336(7) 0.0521(9) 0.0541(8) -0.0057(7) 0.0169(6) 0.0016(7)
C1 0.0208(7) 0.0287(7) 0.0242(6) -0.0018(5) 0.0005(5) 0.0005(5)
C2 0.0217(7) 0.0339(8) 0.0272(6) 0.0000(6) 0.0024(5) -0.0005(6)
C3 0.0321(8) 0.0381(9) 0.0359(9) 0.0018(6) 0.0037(6) -0.0053(7)
C4 0.0442(10) 0.0270(7) 0.0455(9) 0.0014(6) -0.0002(7) -0.0013(6)
C5 0.0372(9) 0.0364(8) 0.0424(9) -0.0072(7) 0.0040(7) 0.0093(7)
C6 0.0242(7) 0.0375(8) 0.0330(7) -0.0025(6) 0.0064(6) 0.0003(6)
C7 0.0242(8) 0.0373(8) 0.0331(8) 0.0004(6) 0.0057(6) -0.0042(6)
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 110.6(11) . . ?
C1 N1 H2 113.2(12) . . ?
H1 N1 H2 105.2(17) . . ?
C1 N1 H3 116.1(12) . . ?
H1 N1 H3 107.3(18) . . ?
H2 N1 H3 103.6(19) . . ?
C6 C1 C2 120.38(14) . . ?
C6 C1 N1 120.04(14) . . ?
C2 C1 N1 119.56(12) . . ?
C3 C2 C1 119.34(15) . . ?
C3 C2 C7 118.79(15) . . ?
C1 C2 C7 121.86(14) . . ?
C4 C3 C2 119.99(17) . . ?
C4 C3 H7 124.9(12) . . ?
C2 C3 H7 114.7(12) . . ?
C3 C4 C5 120.46(16) . . ?
C3 C4 H6 119.4(15) . . ?
C5 C4 H6 120.1(15) . . ?
C4 C5 C6 120.03(15) . . ?
C4 C5 H5 119.2(12) . . ?
C6 C5 H5 120.8(12) . . ?
C1 C6 C5 119.79(15) . . ?
C1 C6 H4 116.0(13) . . ?
C5 C6 H4 124.1(13) . . ?
N2 C7 C2 176.98(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.457(2) . ?
N1 H1 0.88(2) . ?
N1 H2 0.94(2) . ?
N1 H3 0.86(3) . ?
N2 C7 1.138(2) . ?
C1 C6 1.375(2) . ?
C1 C2 1.397(2) . ?
C2 C3 1.392(2) . ?
C2 C7 1.434(2) . ?
C3 C4 1.377(3) . ?
C3 H7 1.00(2) . ?
C4 C5 1.380(3) . ?
C4 H6 0.87(2) . ?
C5 C6 1.391(2) . ?
C5 H5 0.97(2) . ?
C6 H4 0.90(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Cl1 0.89(2) 2.34(2) 3.183(4) 159.0(16) 4_555 yes
N1 H2 Cl1 0.94(2) 2.16(2) 3.102(3) 176.5(19) . yes
N1 H3 Cl1 0.86(2) 2.42(2) 3.257(4) 166.5(17) 4_455 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13371882
