#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/44/2214478.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_2214478
loop_
_publ_author_name
'Liu, Y.-F.'
'Xia, H.-T.'
'Yang, S.-P.'
'Wang, D.-Q.'
_publ_section_title
;
 2-[(4-Chlorophenyl)aminomethyl]-6-methoxyphenol
;
_journal_coeditor_code           AT2320
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3561
_journal_page_last               o3561
_journal_paper_doi               10.1107/S1600536807027766
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H14 Cl N O2'
_chemical_formula_moiety         'C14 H14 Cl N O2'
_chemical_formula_sum            'C14 H14 Cl N O2'
_chemical_formula_weight         263.71
_chemical_name_systematic
;
2-[(4-Chlorophenyl)aminomethyl]-6-methoxyphenol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.496(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.346(2)
_cell_length_b                   5.4437(12)
_cell_length_c                   20.478(2)
_cell_measurement_reflns_used    1485
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.463
_cell_measurement_theta_min      3.165
_cell_volume                     2558.4(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6143
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.9176
_exptl_absorpt_correction_T_min  0.8468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.358
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0527
_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/[\s^2^(Fo^2^)+(0.058P)^2^+2.5185P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1583
_reflns_number_gt                1305
_reflns_number_total             2264
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            at2320.cif
_cod_data_source_block           I
_cod_original_cell_volume        2558.5(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2214478
_cod_database_fobs_code          2214478
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'
'-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_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 Cl1 0.04664(4) 0.6829(2) 0.07190(5) 0.0730(4) Uani d . 1
N N1 0.30405(13) 0.7025(6) 0.17647(17) 0.0618(9) Uani d . 1
H H1 0.3194 0.8409 0.1719 0.074 Uiso calc R 1
O O1 0.43176(9) 0.1644(5) 0.25625(10) 0.0528(7) Uani d . 1
H H1A 0.4576 0.0604 0.2658 0.079 Uiso calc R 1
O O2 0.46516(10) -0.1488(4) 0.17665(11) 0.0522(7) Uani d . 1
C C1 0.34326(15) 0.5057(7) 0.20886(18) 0.0559(10) Uani d . 1
H H1B 0.3266 0.4155 0.2386 0.067 Uiso calc R 1
H H1C 0.3796 0.5772 0.2382 0.067 Uiso calc R 1
C C2 0.35693(13) 0.3247(6) 0.15996(16) 0.0410(8) Uani d . 1
C C3 0.40223(13) 0.1606(6) 0.18656(15) 0.0371(8) Uani d . 1
C C4 0.41828(13) -0.0012(6) 0.14358(16) 0.0401(8) Uani d . 1
C C5 0.38754(15) -0.0042(7) 0.07349(16) 0.0492(9) Uani d . 1
H H5 0.3976 -0.1139 0.0445 0.059 Uiso calc R 1
C C6 0.34193(15) 0.1566(7) 0.04686(17) 0.0530(10) Uani d . 1
H H6 0.3210 0.1543 -0.0003 0.064 Uiso calc R 1
C C7 0.32685(15) 0.3204(7) 0.08898(17) 0.0492(9) Uani d . 1
H H7 0.2963 0.4294 0.0699 0.059 Uiso calc R 1
C C8 0.48033(15) -0.3420(7) 0.13784(19) 0.0556(10) Uani d . 1
H H8A 0.4469 -0.4441 0.1170 0.083 Uiso calc R 1
H H8B 0.5112 -0.4393 0.1683 0.083 Uiso calc R 1
H H8C 0.4930 -0.2716 0.1023 0.083 Uiso calc R 1
C C9 0.24382(14) 0.6881(7) 0.15203(18) 0.0457(9) Uani d . 1
C C10 0.21322(16) 0.5003(7) 0.17032(18) 0.0528(9) Uani d . 1
H H10 0.2333 0.3736 0.1989 0.063 Uiso calc R 1
C C11 0.15244(16) 0.5013(7) 0.14589(19) 0.0538(10) Uani d . 1
H H11 0.1322 0.3748 0.1582 0.065 Uiso calc R 1
C C12 0.12270(14) 0.6849(7) 0.10439(16) 0.0457(9) Uani d . 1
C C13 0.15200(16) 0.8713(7) 0.08636(19) 0.0572(10) Uani d . 1
H H13 0.1316 0.9980 0.0582 0.069 Uiso calc R 1
C C14 0.21174(17) 0.8717(7) 0.1099(2) 0.0567(10) Uani d . 1
H H14 0.2313 0.9998 0.0970 0.068 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
Cl1 0.0505(6) 0.1044(9) 0.0590(6) -0.0045(6) 0.0117(5) -0.0064(6)
N1 0.0519(19) 0.0502(19) 0.083(2) -0.0038(17) 0.0220(17) -0.0036(18)
O1 0.0489(13) 0.0746(17) 0.0284(12) 0.0063(14) 0.0040(10) -0.0055(13)
O2 0.0528(14) 0.0581(16) 0.0402(13) 0.0090(13) 0.0081(11) -0.0035(13)
C1 0.045(2) 0.067(3) 0.050(2) 0.005(2) 0.0076(17) -0.009(2)
C2 0.0374(17) 0.046(2) 0.0382(18) -0.0056(17) 0.0108(15) -0.0015(17)
C3 0.0385(17) 0.0428(19) 0.0282(16) -0.0087(16) 0.0087(14) -0.0015(16)
C4 0.0407(18) 0.044(2) 0.0340(18) -0.0035(17) 0.0110(15) 0.0001(17)
C5 0.058(2) 0.055(2) 0.0333(18) 0.000(2) 0.0135(17) -0.0085(18)
C6 0.058(2) 0.065(3) 0.0287(17) -0.002(2) 0.0048(16) 0.0006(19)
C7 0.0440(19) 0.055(2) 0.044(2) -0.0001(19) 0.0085(16) 0.0052(19)
C8 0.060(2) 0.046(2) 0.062(2) 0.002(2) 0.0216(19) -0.004(2)
C9 0.046(2) 0.046(2) 0.047(2) -0.0067(19) 0.0193(16) -0.0142(19)
C10 0.061(2) 0.046(2) 0.050(2) 0.005(2) 0.0163(18) 0.0047(19)
C11 0.060(2) 0.054(2) 0.055(2) -0.013(2) 0.0289(19) 0.000(2)
C12 0.048(2) 0.053(2) 0.0360(18) -0.0043(19) 0.0146(16) -0.0067(18)
C13 0.060(2) 0.051(2) 0.054(2) 0.000(2) 0.0097(19) 0.003(2)
C14 0.061(2) 0.040(2) 0.071(3) -0.011(2) 0.025(2) 0.003(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
C9 N1 C1 125.7(3)
C9 N1 H1 117.1
C1 N1 H1 117.1
C3 O1 H1A 109.5
C4 O2 C8 118.6(3)
N1 C1 C2 115.9(3)
N1 C1 H1B 108.3
C2 C1 H1B 108.3
N1 C1 H1C 108.3
C2 C1 H1C 108.3
H1B C1 H1C 107.4
C3 C2 C7 118.3(3)
C3 C2 C1 118.8(3)
C7 C2 C1 123.0(3)
O1 C3 C2 118.3(3)
O1 C3 C4 120.6(3)
C2 C3 C4 121.1(3)
O2 C4 C5 125.3(3)
O2 C4 C3 114.9(3)
C5 C4 C3 119.8(3)
C6 C5 C4 119.4(3)
C6 C5 H5 120.3
C4 C5 H5 120.3
C7 C6 C5 120.9(3)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C2 120.6(3)
C6 C7 H7 119.7
C2 C7 H7 119.7
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C14 C9 N1 119.7(3)
C14 C9 C10 117.4(3)
N1 C9 C10 122.9(3)
C9 C10 C11 120.1(3)
C9 C10 H10 120.0
C11 C10 H10 120.0
C12 C11 C10 120.6(3)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 120.1(3)
C11 C12 Cl1 120.7(3)
C13 C12 Cl1 119.1(3)
C12 C13 C14 119.8(4)
C12 C13 H13 120.1
C14 C13 H13 120.1
C13 C14 C9 122.1(3)
C13 C14 H14 119.0
C9 C14 H14 119.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C12 1.746(3)
N1 C9 1.384(4)
N1 C1 1.441(4)
N1 H1 0.8600
O1 C3 1.367(3)
O1 H1A 0.8200
O2 C4 1.375(4)
O2 C8 1.439(4)
C1 C2 1.519(5)
C1 H1B 0.9700
C1 H1C 0.9700
C2 C3 1.382(4)
C2 C7 1.393(4)
C3 C4 1.390(4)
C4 C5 1.380(4)
C5 C6 1.376(5)
C5 H5 0.9300
C6 C7 1.373(5)
C6 H6 0.9300
C7 H7 0.9300
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C14 1.380(5)
C9 C10 1.388(5)
C10 C11 1.395(5)
C10 H10 0.9300
C11 C12 1.355(5)
C11 H11 0.9300
C12 C13 1.360(5)
C13 C14 1.371(5)
C13 H13 0.9300
C14 H14 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
O1 H1A O2 . 0.82 2.21 2.667(3) 115.3
O1 H1A O2 2_655 0.82 2.18 2.965(3) 161.0
C7 H7 N1 . 0.93 2.59 2.917(5) 100.9
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
C9 N1 C1 C2 82.9(4)
N1 C1 C2 C3 167.8(3)
N1 C1 C2 C7 -10.4(5)
C7 C2 C3 O1 -179.9(3)
C1 C2 C3 O1 1.8(4)
C7 C2 C3 C4 1.3(5)
C1 C2 C3 C4 -177.0(3)
C8 O2 C4 C5 -7.4(5)
C8 O2 C4 C3 172.5(3)
O1 C3 C4 O2 -0.6(4)
C2 C3 C4 O2 178.1(3)
O1 C3 C4 C5 179.3(3)
C2 C3 C4 C5 -2.0(5)
O2 C4 C5 C6 -179.0(3)
C3 C4 C5 C6 1.1(5)
C4 C5 C6 C7 0.3(5)
C5 C6 C7 C2 -1.0(5)
C3 C2 C7 C6 0.2(5)
C1 C2 C7 C6 178.4(3)
C1 N1 C9 C14 -166.9(3)
C1 N1 C9 C10 15.9(5)
C14 C9 C10 C11 0.4(5)
N1 C9 C10 C11 177.7(3)
C9 C10 C11 C12 -0.2(5)
C10 C11 C12 C13 -0.3(5)
C10 C11 C12 Cl1 178.4(3)
C11 C12 C13 C14 0.5(5)
Cl1 C12 C13 C14 -178.1(3)
C12 C13 C14 C9 -0.3(6)
N1 C9 C14 C13 -177.5(3)
C10 C9 C14 C13 -0.1(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 240009
2 PubChem 272786