#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/04/2230447.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_2230447
loop_
_publ_author_name
'Han, Jian-Rong'
'Wang, Wei'
'Zhen, Xiao-Li'
'Tian, Xia'
'Liu, Shou-Xin'
_publ_section_title
;
 (Anthracen-9-ylmethyl)benzylammonium chloride
;
_journal_coeditor_code           PV2409
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1482
_journal_paper_doi               10.1107/S1600536811016837
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H20 N +, Cl -'
_chemical_formula_moiety         'C22 H20 N +, Cl -'
_chemical_formula_sum            'C22 H20 Cl N'
_chemical_formula_weight         333.84
_chemical_name_systematic
;
(Anthracen-9-ylmethyl)benzylammonium chloride
;
_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           SHELXL-97
_cell_angle_alpha                94.45(3)
_cell_angle_beta                 104.84(3)
_cell_angle_gamma                104.48(3)
_cell_formula_units_Z            2
_cell_length_a                   6.7457(13)
_cell_length_b                   10.761(2)
_cell_length_c                   13.033(3)
_cell_measurement_reflns_used    2756
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.882
_cell_measurement_theta_min      2.368
_cell_volume                     875.3(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5882
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_correction_T_min  0.9409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.209
_refine_ls_extinction_coef       0.152(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0502P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                2342
_reflns_number_total             3048
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2409.cif
_cod_data_source_block           I
_cod_original_cell_volume        875.3(3)
_cod_database_code               2230447
_cod_database_fobs_code          2230447
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.17351(5) 0.42040(4) 0.40032(3) 0.02288(15) Uani d . 1 1 . .
N N1 0.38238(18) 0.52936(11) 0.64009(9) 0.0139(3) Uani d D 1 1 . .
C C1 0.1631(2) 0.21072(14) 0.67206(11) 0.0184(3) Uani d . 1 1 . .
C C2 -0.0472(2) 0.21057(16) 0.61273(12) 0.0242(4) Uani d . 1 1 . .
H H2 -0.0774 0.2890 0.6018 0.029 Uiso calc R 1 1 . .
C C3 -0.2034(3) 0.09727(16) 0.57217(13) 0.0305(4) Uani d . 1 1 . .
H H3 -0.3391 0.0995 0.5340 0.037 Uiso calc R 1 1 . .
C C4 -0.1629(3) -0.02440(17) 0.58713(13) 0.0341(4) Uani d . 1 1 . .
H H4 -0.2721 -0.1009 0.5597 0.041 Uiso calc R 1 1 . .
C C5 0.0344(3) -0.02903(16) 0.64127(12) 0.0305(4) Uani d . 1 1 . .
H H5 0.0595 -0.1091 0.6505 0.037 Uiso calc R 1 1 . .
C C6 0.2045(3) 0.08678(15) 0.68441(12) 0.0227(4) Uani d . 1 1 . .
C C7 0.4101(3) 0.08322(16) 0.73768(12) 0.0262(4) Uani d . 1 1 . .
H H7 0.4365 0.0029 0.7438 0.031 Uiso calc R 1 1 . .
C C8 0.5764(2) 0.19449(15) 0.78173(11) 0.0223(4) Uani d . 1 1 . .
C C9 0.7883(3) 0.18991(18) 0.83401(12) 0.0299(4) Uani d . 1 1 . .
H H9 0.8163 0.1098 0.8382 0.036 Uiso calc R 1 1 . .
C C10 0.9485(3) 0.29980(18) 0.87736(12) 0.0315(4) Uani d . 1 1 . .
H H10 1.0853 0.2948 0.9103 0.038 Uiso calc R 1 1 . .
C C11 0.9084(2) 0.42185(17) 0.87262(11) 0.0273(4) Uani d . 1 1 . .
H H11 1.0193 0.4969 0.9030 0.033 Uiso calc R 1 1 . .
C C12 0.7099(2) 0.43137(16) 0.82427(11) 0.0221(4) Uani d . 1 1 . .
H H12 0.6871 0.5130 0.8231 0.026 Uiso calc R 1 1 . .
C C13 0.5357(2) 0.31906(15) 0.77525(11) 0.0188(3) Uani d . 1 1 . .
C C14 0.3287(2) 0.32511(14) 0.72005(11) 0.0170(3) Uani d . 1 1 . .
C C15 0.2884(2) 0.45631(14) 0.71774(11) 0.0167(3) Uani d . 1 1 . .
H H15A 0.1356 0.4454 0.6977 0.020 Uiso calc R 1 1 . .
H H15B 0.3499 0.5065 0.7891 0.020 Uiso calc R 1 1 . .
C C16 0.3787(2) 0.66897(14) 0.64641(11) 0.0159(3) Uani d . 1 1 . .
H H16A 0.2322 0.6725 0.6209 0.019 Uiso calc R 1 1 . .
H H16B 0.4571 0.7116 0.6000 0.019 Uiso calc R 1 1 . .
C C17 0.4765(2) 0.74042(14) 0.75999(11) 0.0160(3) Uani d . 1 1 . .
C C18 0.3455(2) 0.75556(14) 0.82421(12) 0.0214(4) Uani d . 1 1 . .
H H18 0.1978 0.7247 0.7963 0.026 Uiso calc R 1 1 . .
C C19 0.4352(3) 0.81680(15) 0.93001(12) 0.0277(4) Uani d . 1 1 . .
H H19 0.3472 0.8261 0.9729 0.033 Uiso calc R 1 1 . .
C C20 0.6531(3) 0.86365(16) 0.97157(13) 0.0300(4) Uani d . 1 1 . .
H H20 0.7122 0.9046 1.0424 0.036 Uiso calc R 1 1 . .
C C21 0.7851(3) 0.84988(15) 0.90801(12) 0.0254(4) Uani d . 1 1 . .
H H21 0.9326 0.8817 0.9360 0.030 Uiso calc R 1 1 . .
C C22 0.6962(2) 0.78841(14) 0.80265(11) 0.0194(3) Uani d . 1 1 . .
H H22 0.7848 0.7793 0.7601 0.023 Uiso calc R 1 1 . .
H H1A 0.5219(14) 0.5298(15) 0.6487(11) 0.027(4) Uiso d D 1 1 . .
H H1B 0.3065(17) 0.4908(14) 0.5707(8) 0.018(4) 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 N1 C16 . . 114.67(10) ?
C15 N1 H1A . . 112.3(10) ?
C16 N1 H1A . . 106.5(10) ?
C15 N1 H1B . . 109.8(9) ?
C16 N1 H1B . . 106.0(9) ?
H1A N1 H1B . . 107.2(9) ?
C14 C1 C2 . . 123.40(14) ?
C14 C1 C6 . . 118.93(14) ?
C2 C1 C6 . . 117.67(14) ?
C3 C2 C1 . . 120.89(16) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 121.11(16) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C3 . . 120.06(16) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 121.12(16) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C7 C6 C5 . . 121.68(15) ?
C7 C6 C1 . . 119.21(15) ?
C5 C6 C1 . . 119.11(15) ?
C8 C7 C6 . . 122.54(15) ?
C8 C7 H7 . . 118.7 ?
C6 C7 H7 . . 118.7 ?
C7 C8 C9 . . 122.15(15) ?
C7 C8 C13 . . 119.11(14) ?
C9 C8 C13 . . 118.74(15) ?
C10 C9 C8 . . 121.28(16) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C9 C10 C11 . . 120.10(15) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C12 C11 C10 . . 120.87(16) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C11 C12 C13 . . 121.55(16) ?
C11 C12 H12 . . 119.2 ?
C13 C12 H12 . . 119.2 ?
C14 C13 C12 . . 123.26(14) ?
C14 C13 C8 . . 119.31(14) ?
C12 C13 C8 . . 117.42(14) ?
C1 C14 C13 . . 120.77(14) ?
C1 C14 C15 . . 120.96(13) ?
C13 C14 C15 . . 118.23(13) ?
N1 C15 C14 . . 112.01(10) ?
N1 C15 H15A . . 109.2 ?
C14 C15 H15A . . 109.2 ?
N1 C15 H15B . . 109.2 ?
C14 C15 H15B . . 109.2 ?
H15A C15 H15B . . 107.9 ?
N1 C16 C17 . . 111.53(12) ?
N1 C16 H16A . . 109.3 ?
C17 C16 H16A . . 109.3 ?
N1 C16 H16B . . 109.3 ?
C17 C16 H16B . . 109.3 ?
H16A C16 H16B . . 108.0 ?
C22 C17 C18 . . 119.11(13) ?
C22 C17 C16 . . 120.99(12) ?
C18 C17 C16 . . 119.88(13) ?
C19 C18 C17 . . 120.05(14) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C20 C19 C18 . . 120.37(14) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
C19 C20 C21 . . 120.05(14) ?
C19 C20 H20 . . 120.0 ?
C21 C20 H20 . . 120.0 ?
C22 C21 C20 . . 119.72(15) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C17 C22 C21 . . 120.71(13) ?
C17 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
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
N1 C15 . 1.4990(17) ?
N1 C16 . 1.5051(18) ?
N1 H1A . 0.917(8) ?
N1 H1B . 0.922(8) ?
C1 C14 . 1.410(2) ?
C1 C2 . 1.431(2) ?
C1 C6 . 1.442(2) ?
C2 C3 . 1.360(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.421(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.352(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.425(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.394(2) ?
C7 C8 . 1.383(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.432(2) ?
C8 C13 . 1.438(2) ?
C9 C10 . 1.353(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.408(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.359(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.426(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.418(2) ?
C14 C15 . 1.504(2) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.512(2) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C22 . 1.386(2) ?
C17 C18 . 1.3922(19) ?
C18 C19 . 1.391(2) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.374(2) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.388(2) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.386(2) ?
C21 H21 . 0.9300 ?
C22 H22 . 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
N1 H1A Cl1 2_666 0.917(8) 2.257(11) 3.0963(13) 151.9(13)
N1 H1B Cl1 . 0.922(8) 2.165(9) 3.0781(16) 170.3(12)
C16 H16A Cl1 2_566 0.970 2.600 3.4824(16) 151
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
C14 C1 C2 C3 . . . . -177.07(13) ?
C6 C1 C2 C3 . . . . 1.8(2) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
C2 C3 C4 C5 . . . . -0.9(2) ?
C3 C4 C5 C6 . . . . 0.2(2) ?
C4 C5 C6 C7 . . . . -178.11(14) ?
C4 C5 C6 C1 . . . . 1.5(2) ?
C14 C1 C6 C7 . . . . -3.89(19) ?
C2 C1 C6 C7 . . . . 177.20(12) ?
C14 C1 C6 C5 . . . . 176.47(12) ?
C2 C1 C6 C5 . . . . -2.44(19) ?
C5 C6 C7 C8 . . . . -178.83(13) ?
C1 C6 C7 C8 . . . . 1.5(2) ?
C6 C7 C8 C9 . . . . -178.44(13) ?
C6 C7 C8 C13 . . . . 1.7(2) ?
C7 C8 C9 C10 . . . . -179.48(14) ?
C13 C8 C9 C10 . . . . 0.4(2) ?
C8 C9 C10 C11 . . . . 0.6(2) ?
C9 C10 C11 C12 . . . . -0.4(2) ?
C10 C11 C12 C13 . . . . -0.9(2) ?
C11 C12 C13 C14 . . . . -177.20(13) ?
C11 C12 C13 C8 . . . . 1.9(2) ?
C7 C8 C13 C14 . . . . -2.6(2) ?
C9 C8 C13 C14 . . . . 177.55(11) ?
C7 C8 C13 C12 . . . . 178.28(12) ?
C9 C8 C13 C12 . . . . -1.57(19) ?
C2 C1 C14 C13 . . . . -178.15(12) ?
C6 C1 C14 C13 . . . . 3.01(19) ?
C2 C1 C14 C15 . . . . 4.2(2) ?
C6 C1 C14 C15 . . . . -174.63(12) ?
C12 C13 C14 C1 . . . . 179.28(12) ?
C8 C13 C14 C1 . . . . 0.21(19) ?
C12 C13 C14 C15 . . . . -3.02(19) ?
C8 C13 C14 C15 . . . . 177.92(12) ?
C16 N1 C15 C14 . . . . -170.73(11) ?
C1 C14 C15 N1 . . . . -106.13(14) ?
C13 C14 C15 N1 . . . . 76.17(15) ?
C15 N1 C16 C17 . . . . 52.24(15) ?
N1 C16 C17 C22 . . . . 81.05(17) ?
N1 C16 C17 C18 . . . . -97.18(15) ?
C22 C17 C18 C19 . . . . -0.7(2) ?
C16 C17 C18 C19 . . . . 177.52(14) ?
C17 C18 C19 C20 . . . . 0.6(2) ?
C18 C19 C20 C21 . . . . -0.1(2) ?
C19 C20 C21 C22 . . . . -0.2(2) ?
C18 C17 C22 C21 . . . . 0.5(2) ?
C16 C17 C22 C21 . . . . -177.76(13) ?
C20 C21 C22 C17 . . . . 0.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656729
