#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/02/7200206.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_7200206
loop_
_publ_author_name
'Gibson, Emma K.'
'Winfield, John M.'
'Muir, Kenneth W.'
'Carr, Robert H.'
'Eaglesham, Archie'
'Gavezzotti, Angelo'
'Parker, Stewart F.'
'Lennon, David'
_publ_section_title
;
 A structural and spectroscopic investigation of the hydrochlorination
 of 4-benzylaniline: the interaction of anhydrous hydrogen chloride
 with chlorobenzene
;
_journal_issue                   2
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_page_first              288
_journal_page_last               297
_journal_paper_doi               10.1039/b810027f
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'Cl, C13 H14 N'
_chemical_formula_sum            'C13 H14 Cl N'
_chemical_formula_weight         219.7
_chemical_name_common            'Compound X'
_chemical_name_systematic
;
4-benzylaniline hydrochloride
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2005-04-19T08:08:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.4360
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5504(2)
_cell_length_b                   22.0930(8)
_cell_length_c                   9.7906(4)
_cell_measurement_reflns_used    2750
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1
_cell_volume                     1151.51(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12278
_diffrn_reflns_theta_full        27.22
_diffrn_reflns_theta_max         27.22
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS as embodied in WINGX
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.055
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;

calc w=1/[σ\^2\^(Fo\^2\^)+(0.0308P)\^2\^+0.5938P] where
P=(Fo\^2\^+2Fc\^2\^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                1964
_reflns_number_total             2504
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B810027F.txt
_cod_data_source_block           BA.HCL
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7200206
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4244(3) 0.16033(7) -0.16956(17) 0.0220(4) Uani 1 1 d . . .
H1A H 0.4633 0.1369 -0.2468 0.026 Uiso 1 1 calc R . .
H1B H 0.2418 0.1688 -0.1993 0.026 Uiso 1 1 calc R . .
C11 C 0.4850(3) 0.12144(7) -0.03591(17) 0.0165(3) Uani 1 1 d . . .
C12 C 0.3044(3) 0.08219(7) -0.01287(16) 0.0174(3) Uani 1 1 d . . .
H12 H 0.1414 0.0817 -0.0785 0.021 Uiso 1 1 calc R . .
C13 C 0.3575(3) 0.04378(7) 0.10421(16) 0.0170(3) Uani 1 1 d . . .
H13 H 0.233 0.017 0.1187 0.02 Uiso 1 1 calc R . .
C14 C 0.5946(3) 0.04523(7) 0.19911(16) 0.0147(3) Uani 1 1 d . . .
C15 C 0.7772(3) 0.08421(7) 0.18074(17) 0.0184(4) Uani 1 1 d . . .
H15 H 0.9389 0.085 0.2477 0.022 Uiso 1 1 calc R . .
C16 C 0.7218(3) 0.12229(7) 0.06321(18) 0.0198(4) Uani 1 1 d . . .
H16 H 0.8466 0.1493 0.0501 0.024 Uiso 1 1 calc R . .
C21 C 0.5641(3) 0.21974(7) -0.15330(16) 0.0177(3) Uani 1 1 d . . .
C22 C 0.5218(3) 0.26461(8) -0.06283(17) 0.0231(4) Uani 1 1 d . . .
H22 H 0.4004 0.2582 -0.0127 0.028 Uiso 1 1 calc R . .
C23 C 0.6547(4) 0.31835(8) -0.04529(18) 0.0289(4) Uani 1 1 d . . .
H23 H 0.6245 0.3486 0.0168 0.035 Uiso 1 1 calc R . .
C24 C 0.8320(4) 0.32815(8) -0.11818(19) 0.0314(4) Uani 1 1 d . . .
H24 H 0.9257 0.3647 -0.1048 0.038 Uiso 1 1 calc R . .
C25 C 0.8717(3) 0.28459(8) -0.2102(2) 0.0300(4) Uani 1 1 d . . .
H25 H 0.9908 0.2915 -0.2617 0.036 Uiso 1 1 calc R . .
C26 C 0.7384(3) 0.23066(8) -0.22787(18) 0.0226(4) Uani 1 1 d . . .
H26 H 0.7667 0.2009 -0.2917 0.027 Uiso 1 1 calc R . .
Cl1 Cl 0.82139(7) 0.060695(17) 0.62976(4) 0.01799(12) Uani 1 1 d . . .
N1 N 0.6554(3) 0.00457(7) 0.32301(15) 0.0173(3) Uani 1 1 d . . .
H111 H 0.701(3) 0.0263(9) 0.410(2) 0.031(5) Uiso 1 1 d . . .
H112 H 0.786(4) -0.0196(9) 0.323(2) 0.030(5) Uiso 1 1 d . . .
H113 H 0.521(4) -0.0191(9) 0.330(2) 0.031(5) Uiso 1 1 d . . .
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 0 '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'
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
C21 C1 C11 114.72(13) . . ?
C21 C1 H1A 108.6 . . ?
C11 C1 H1A 108.6 . . ?
C21 C1 H1B 108.6 . . ?
C11 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C12 C11 C16 118.40(14) . . ?
C12 C11 C1 119.82(14) . . ?
C16 C11 C1 121.74(14) . . ?
C13 C12 C11 121.32(14) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 118.75(14) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 121.49(14) . . ?
C13 C14 N1 119.60(14) . . ?
C15 C14 N1 118.92(13) . . ?
C14 C15 C16 119.18(14) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C11 120.85(15) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C26 C21 C22 118.61(15) . . ?
C26 C21 C1 120.62(15) . . ?
C22 C21 C1 120.77(15) . . ?
C23 C22 C21 120.66(16) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.12(16) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.71(16) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.19(17) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.69(16) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C14 N1 H111 111.8(12) . . ?
C14 N1 H112 111.0(12) . . ?
H111 N1 H112 106.9(16) . . ?
C14 N1 H113 113.6(12) . . ?
H111 N1 H113 103.9(16) . . ?
H112 N1 H113 109.2(16) . . ?
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
C1 C21 1.510(2) . ?
C1 C11 1.521(2) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C11 C12 1.391(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.95 . ?
C13 C14 1.380(2) . ?
C13 H13 0.95 . ?
C14 C15 1.380(2) . ?
C14 N1 1.470(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C21 C26 1.388(2) . ?
C21 C22 1.393(2) . ?
C22 C23 1.383(3) . ?
C22 H22 0.95 . ?
C23 C24 1.386(3) . ?
C23 H23 0.95 . ?
C24 C25 1.378(3) . ?
C24 H24 0.95 . ?
C25 C26 1.387(2) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
N1 H111 0.94(2) . ?
N1 H112 0.90(2) . ?
N1 H113 0.93(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
N1 H111 Cl1 0.94(2) 2.20(2) 3.1369(15) 169.7(17) .
N1 H113 Cl1 0.93(2) 2.24(2) 3.1603(15) 168.6(16) 3_656
N1 H112 Cl1 0.90(2) 2.29(2) 3.1571(15) 163.1(16) 3_756
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C1 C11 C12 150.95(15) . . . . ?
C21 C1 C11 C16 -31.3(2) . . . . ?
C16 C11 C12 C13 -1.1(2) . . . . ?
C1 C11 C12 C13 176.63(15) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C12 C13 C14 N1 -179.47(14) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
N1 C14 C15 C16 179.38(14) . . . . ?
C14 C15 C16 C11 -0.1(2) . . . . ?
C12 C11 C16 C15 1.0(2) . . . . ?
C1 C11 C16 C15 -176.69(14) . . . . ?
C11 C1 C21 C26 114.17(17) . . . . ?
C11 C1 C21 C22 -65.6(2) . . . . ?
C26 C21 C22 C23 -1.4(2) . . . . ?
C1 C21 C22 C23 178.31(14) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 C25 1.2(2) . . . . ?
C23 C24 C25 C26 -1.2(3) . . . . ?
C24 C25 C26 C21 -0.1(3) . . . . ?
C22 C21 C26 C25 1.4(2) . . . . ?
C1 C21 C26 C25 -178.30(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 174552
