#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/95/2219524.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_2219524
loop_
_publ_author_name
'Dai, Jing'
_publ_section_title
;
 4-Cyanoanilinium perchlorate
;
_journal_coeditor_code           BX2181
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2025
_journal_paper_doi               10.1107/S1600536808030687
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H7 N2 + , Cl O4 -'
_chemical_formula_moiety         'C7 H7 N2 + , Cl O4 -'
_chemical_formula_sum            'C7 H7 Cl N2 O4'
_chemical_formula_weight         218.60
_chemical_name_systematic
;
4-Cyanoanilinium perchlorate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                94.87(3)
_cell_angle_beta                 95.68(3)
_cell_angle_gamma                103.99(3)
_cell_formula_units_Z            2
_cell_length_a                   4.9905(10)
_cell_length_b                   6.9465(14)
_cell_length_c                   13.998(3)
_cell_measurement_reflns_used    1806
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.041
_cell_volume                     465.57(18)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4861
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.338
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0359
_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)+(0.0483P)²+0.1253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                1851
_reflns_number_total             2126
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2181.cif
_cod_data_source_block           I
_cod_original_cell_volume        465.57(17)
_cod_database_code               2219524
_cod_database_fobs_code          2219524
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N N1 0.6157(3) 0.2508(2) 0.12597(11) 0.0399(4) Uani d . 1
H H1A 0.4771 0.2405 0.0791 0.048 Uiso calc R 1
H H1B 0.6876 0.1460 0.1180 0.048 Uiso calc R 1
H H1C 0.7468 0.3623 0.1238 0.048 Uiso calc R 1
N N2 0.0727(7) 0.2647(4) 0.5503(2) 0.1058(10) Uani d . 1
C C1 0.1672(6) 0.2642(4) 0.47983(19) 0.0743(8) Uani d . 1
C C2 0.2877(5) 0.2620(3) 0.38998(16) 0.0549(5) Uani d . 1
C C3 0.2722(5) 0.4100(3) 0.33016(17) 0.0557(5) Uani d . 1
H H3 0.1860 0.5101 0.3478 0.067 Uiso calc R 1
C C4 0.3859(4) 0.4064(3) 0.24466(15) 0.0458(4) Uani d . 1
H H4 0.3789 0.5049 0.2041 0.055 Uiso calc R 1
C C5 0.5097(3) 0.2566(3) 0.21961(13) 0.0362(4) Uani d . 1
C C6 0.5293(4) 0.1094(3) 0.27829(14) 0.0464(5) Uani d . 1
H H6 0.6169 0.0104 0.2604 0.056 Uiso calc R 1
C C7 0.4158(5) 0.1127(4) 0.36408(16) 0.0574(6) Uani d . 1
H H7 0.4252 0.0145 0.4046 0.069 Uiso calc R 1
Cl Cl1 -0.00044(8) 0.22266(6) 0.91125(3) 0.03315(14) Uani d . 1
O O1 -0.2849(3) 0.1812(2) 0.92711(11) 0.0552(4) Uani d . 1
O O2 0.1712(3) 0.3237(2) 0.99794(12) 0.0598(4) Uani d . 1
O O3 0.0665(3) 0.0398(2) 0.88369(13) 0.0593(4) Uani d . 1
O O4 0.0420(4) 0.3478(2) 0.83610(12) 0.0668(5) Uani d . 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
N1 0.0442(8) 0.0392(8) 0.0403(9) 0.0162(7) 0.0100(6) 0.0048(6)
N2 0.141(3) 0.0996(19) 0.0746(17) 0.0122(17) 0.0625(17) -0.0038(14)
C1 0.0839(18) 0.0741(17) 0.0597(16) 0.0059(14) 0.0296(13) -0.0047(13)
C2 0.0545(12) 0.0599(13) 0.0450(12) 0.0039(10) 0.0167(9) -0.0053(10)
C3 0.0560(13) 0.0514(12) 0.0617(14) 0.0159(10) 0.0210(10) -0.0056(10)
C4 0.0485(11) 0.0424(10) 0.0506(12) 0.0168(8) 0.0126(9) 0.0046(8)
C5 0.0328(8) 0.0375(9) 0.0366(9) 0.0068(7) 0.0046(7) 0.0004(7)
C6 0.0547(11) 0.0455(10) 0.0441(11) 0.0205(9) 0.0097(9) 0.0072(8)
C7 0.0714(15) 0.0609(13) 0.0425(12) 0.0163(11) 0.0126(10) 0.0140(10)
Cl1 0.0306(2) 0.0284(2) 0.0426(3) 0.00948(15) 0.00733(15) 0.00697(15)
O1 0.0333(7) 0.0667(9) 0.0627(10) 0.0079(6) 0.0146(6) -0.0046(7)
O2 0.0531(9) 0.0534(9) 0.0661(10) 0.0147(7) -0.0150(7) -0.0090(7)
O3 0.0595(9) 0.0396(7) 0.0839(12) 0.0271(7) 0.0058(8) -0.0036(7)
O4 0.0880(12) 0.0539(9) 0.0623(11) 0.0127(8) 0.0217(9) 0.0293(8)
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
C5 N1 H1A 109.5
C5 N1 H1B 109.5
H1A N1 H1B 109.5
C5 N1 H1C 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
N2 C1 C2 179.6(3)
C7 C2 C3 120.66(19)
C7 C2 C1 119.9(2)
C3 C2 C1 119.4(2)
C4 C3 C2 119.1(2)
C4 C3 H3 120.4
C2 C3 H3 120.4
C5 C4 C3 119.54(19)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 122.22(18)
C4 C5 N1 118.25(16)
C6 C5 N1 119.50(16)
C7 C6 C5 118.39(19)
C7 C6 H6 120.8
C5 C6 H6 120.8
C6 C7 C2 120.1(2)
C6 C7 H7 120.0
C2 C7 H7 120.0
O4 Cl1 O3 109.51(11)
O4 Cl1 O1 109.25(11)
O3 Cl1 O1 108.89(10)
O4 Cl1 O2 109.01(11)
O3 Cl1 O2 110.69(10)
O1 Cl1 O2 109.47(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.462(2)
N1 H1A 0.8900
N1 H1B 0.8900
N1 H1C 0.8900
N2 C1 1.135(3)
C1 C2 1.447(3)
C2 C7 1.385(3)
C2 C3 1.392(3)
C3 C4 1.375(3)
C3 H3 0.9300
C4 C5 1.371(3)
C4 H4 0.9300
C5 C6 1.380(3)
C6 C7 1.378(3)
C6 H6 0.9300
C7 H7 0.9300
Cl1 O4 1.4202(15)
Cl1 O3 1.4215(14)
Cl1 O1 1.4222(14)
Cl1 O2 1.4346(16)
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 H1A O2 1_554 0.89 2.04 2.881(2) 157.8
N1 H1B O3 2_656 0.89 1.98 2.855(2) 165.7
N1 H1C O4 2_666 0.89 2.04 2.871(2) 155.8
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
C7 C2 C3 C4 0.0(3)
C1 C2 C3 C4 -179.7(2)
C2 C3 C4 C5 0.6(3)
C3 C4 C5 C6 -1.2(3)
C3 C4 C5 N1 176.83(18)
C4 C5 C6 C7 1.1(3)
N1 C5 C6 C7 -176.89(19)
C5 C6 C7 C2 -0.4(3)
C3 C2 C7 C6 -0.1(4)
C1 C2 C7 C6 179.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655613
