#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/23/8102374.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_8102374
loop_
_publ_author_name
'Hui-Duo Xian'
'Hua-Qiong Li'
'Jian-Feng Liu'
'Guo-Liang Zhao'
_publ_section_title
;
 Crystal structure of 2-(4-methylanilinomethyl)-6-methoxyphenol
 perchlorate monohydrate, [C15H16NO2]ClO4 · H2O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              189
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C15 H16 N O2, Cl O4, H2 O'
_chemical_formula_sum            'C15 H18 Cl N O7'
_chemical_formula_weight         359.75
_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                90.286(3)
_cell_angle_beta                 92.226(3)
_cell_angle_gamma                101.786(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7572(3)
_cell_length_b                   9.5138(4)
_cell_length_c                   11.5187(5)
_cell_measurement_reflns_used    2639
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      1.77
_cell_volume                     831.46(6)
_computing_cell_refinement       'SAINT (Bruker,2004)'
_computing_data_collection       'SMART (Bruker,2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker,2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick,1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick,1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'ω scans'
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12672
_diffrn_reflns_theta_full        27.63
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.463
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1554P)²+0.3106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2439
_refine_ls_wR_factor_ref         0.2788
_reflns_number_gt                2236
_reflns_number_total             3775
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2462.cff
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_formula_sum        'C15 H18 Cl N O7 '
_cod_database_code               8102374
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.27031(13) 0.85432(10) 0.27965(8) 0.0707(4) Uani 1 1 d . . .
N1 N -0.1779(4) 0.6148(3) -0.4822(2) 0.0561(7) Uani 1 1 d . . .
H1D H -0.1227 0.7009 -0.4950 0.067 Uiso 1 1 calc R . .
O1 O 0.2341(13) 0.9006(13) 0.1806(5) 0.302(6) Uani 1 1 d . . .
O1W O 0.2651(4) 1.0820(3) -0.4470(2) 0.0764(8) Uani 1 1 d D . .
H1WA H 0.291(6) 1.080(6) -0.5157(18) 0.115 Uiso 1 1 d D . .
H1WB H 0.340(6) 1.044(6) -0.413(3) 0.115 Uiso 1 1 d D . .
O2 O 0.3770(9) 0.7593(6) 0.2701(8) 0.235(4) Uani 1 1 d . . .
O3 O 0.3748(8) 0.9648(6) 0.3441(5) 0.193(3) Uani 1 1 d . . .
O4 O 0.1287(6) 0.7919(6) 0.3461(5) 0.164(2) Uani 1 1 d . . .
O5 O 0.0282(4) 0.8524(3) -0.3899(2) 0.0685(7) Uani 1 1 d D . .
H5A H 0.103(5) 0.927(3) -0.395(4) 0.103 Uiso 1 1 d D . .
O6 O 0.1962(4) 0.9931(3) -0.2048(2) 0.0747(8) Uani 1 1 d . . .
C1 C -0.4868(6) 0.2959(5) -0.8874(4) 0.0865(14) Uani 1 1 d . . .
H1A H -0.4767 0.3585 -0.9530 0.130 Uiso 1 1 calc R . .
H1B H -0.6089 0.2555 -0.8765 0.130 Uiso 1 1 calc R . .
H1C H -0.4249 0.2202 -0.9011 0.130 Uiso 1 1 calc R . .
C2 C -0.4080(5) 0.3804(4) -0.7797(3) 0.0619(9) Uani 1 1 d . . .
C3 C -0.3299(6) 0.5232(5) -0.7837(3) 0.0749(11) Uani 1 1 d . . .
H3A H -0.3269 0.5698 -0.8546 0.090 Uiso 1 1 calc R . .
C4 C -0.2553(5) 0.6003(4) -0.6855(3) 0.0690(10) Uani 1 1 d . . .
H4A H -0.2037 0.6971 -0.6907 0.083 Uiso 1 1 calc R . .
C5 C -0.2581(4) 0.5332(3) -0.5810(3) 0.0547(8) Uani 1 1 d . . .
C6 C -0.3341(6) 0.3893(4) -0.5745(4) 0.0774(12) Uani 1 1 d . . .
H6A H -0.3363 0.3427 -0.5036 0.093 Uiso 1 1 calc R . .
C7 C -0.4069(6) 0.3149(4) -0.6738(4) 0.0803(12) Uani 1 1 d . . .
H7A H -0.4566 0.2177 -0.6688 0.096 Uiso 1 1 calc R . .
C8 C -0.1789(5) 0.5745(4) -0.3772(3) 0.0580(8) Uani 1 1 d . . .
H8A H -0.2412 0.4822 -0.3634 0.070 Uiso 1 1 calc R . .
C9 C -0.0951(5) 0.6547(4) -0.2777(3) 0.0558(8) Uani 1 1 d . . .
C10 C -0.1166(5) 0.5896(4) -0.1684(3) 0.0691(10) Uani 1 1 d . . .
H10A H -0.1845 0.4975 -0.1624 0.083 Uiso 1 1 calc R . .
C11 C -0.0376(6) 0.6615(5) -0.0708(3) 0.0712(10) Uani 1 1 d . . .
H11A H -0.0540 0.6187 0.0014 0.085 Uiso 1 1 calc R . .
C12 C 0.0668(5) 0.7980(4) -0.0791(3) 0.0636(9) Uani 1 1 d . . .
H12A H 0.1204 0.8457 -0.0124 0.076 Uiso 1 1 calc R . .
C13 C 0.0915(5) 0.8634(4) -0.1851(3) 0.0585(9) Uani 1 1 d . . .
C14 C 0.0096(4) 0.7929(4) -0.2857(3) 0.0548(8) Uani 1 1 d . . .
C15 C 0.2804(6) 1.0748(5) -0.1057(3) 0.0824(12) Uani 1 1 d . . .
H15A H 0.3497 1.1639 -0.1310 0.124 Uiso 1 1 calc R . .
H15B H 0.3554 1.0212 -0.0649 0.124 Uiso 1 1 calc R . .
H15C H 0.1924 1.0938 -0.0549 0.124 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cl1 O2 110.5(6) . . ?
O1 Cl1 O3 109.2(6) . . ?
O2 Cl1 O3 102.5(5) . . ?
O1 Cl1 O4 117.2(5) . . ?
O2 Cl1 O4 108.1(4) . . ?
O3 Cl1 O4 108.3(3) . . ?
C8 N1 C5 127.2(3) . . ?
C8 N1 H1D 116.4 . . ?
C5 N1 H1D 116.4 . . ?
H1WA O1W H1WB 104(3) . . ?
C14 O5 H5A 117(4) . . ?
C13 O6 C15 117.5(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.2(3) . . ?
C3 C2 C1 122.0(4) . . ?
C7 C2 C1 120.8(4) . . ?
C2 C3 C4 122.1(4) . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 H3A 118.9 . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 N1 118.2(3) . . ?
C6 C5 N1 122.2(3) . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C2 C7 C6 121.9(4) . . ?
C2 C7 H7A 119.0 . . ?
C6 C7 H7A 119.0 . . ?
N1 C8 C9 127.6(3) . . ?
N1 C8 H8A 116.2 . . ?
C9 C8 H8A 116.2 . . ?
C14 C9 C10 119.4(3) . . ?
C14 C9 C8 122.6(3) . . ?
C10 C9 C8 118.0(3) . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
O6 C13 C12 126.0(3) . . ?
O6 C13 C14 114.0(3) . . ?
C12 C13 C14 119.9(3) . . ?
O5 C14 C13 122.1(3) . . ?
O5 C14 C9 118.4(3) . . ?
C13 C14 C9 119.5(3) . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
Cl1 O1 1.266(6) . ?
Cl1 O2 1.351(5) . ?
Cl1 O3 1.382(4) . ?
Cl1 O4 1.396(4) . ?
N1 C8 1.270(4) . ?
N1 C5 1.422(4) . ?
N1 H1D 0.8600 . ?
O1W H1WA 0.823(19) . ?
O1W H1WB 0.832(19) . ?
O5 C14 1.330(4) . ?
O5 H5A 0.818(19) . ?
O6 C13 1.357(5) . ?
O6 C15 1.435(4) . ?
C1 C2 1.513(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.371(6) . ?
C2 C7 1.374(6) . ?
C3 C4 1.386(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.364(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(5) . ?
C6 C7 1.381(5) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.432(5) . ?
C8 H8A 0.9300 . ?
C9 C14 1.402(5) . ?
C9 C10 1.406(5) . ?
C10 C11 1.369(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.375(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.400(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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 H1D O5 0.86 2.02 2.677(3) 132.0 .
N1 H1D O1W 0.86 2.61 3.197(4) 126.3 2_574
O1W H1WA O3 0.823(19) 2.14(3) 2.877(6) 148(5) 1_554
O1W H1WB O3 0.832(19) 2.34(3) 3.109(8) 154(5) 2_675
O5 H5A O1W 0.818(19) 1.86(2) 2.656(4) 165(5) .
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
C7 C2 C3 C4 -1.1(6) . . . . ?
C1 C2 C3 C4 -179.1(4) . . . . ?
C2 C3 C4 C5 0.3(7) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C3 C4 C5 N1 179.0(3) . . . . ?
C8 N1 C5 C4 174.3(3) . . . . ?
C8 N1 C5 C6 -7.1(6) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
N1 C5 C6 C7 -178.7(4) . . . . ?
C3 C2 C7 C6 1.4(6) . . . . ?
C1 C2 C7 C6 179.3(4) . . . . ?
C5 C6 C7 C2 -0.8(7) . . . . ?
C5 N1 C8 C9 178.4(3) . . . . ?
N1 C8 C9 C14 -2.8(6) . . . . ?
N1 C8 C9 C10 178.7(4) . . . . ?
C14 C9 C10 C11 0.8(6) . . . . ?
C8 C9 C10 C11 179.4(3) . . . . ?
C9 C10 C11 C12 -1.2(6) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C15 O6 C13 C12 -4.4(6) . . . . ?
C15 O6 C13 C14 177.9(3) . . . . ?
C11 C12 C13 O6 -176.9(4) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
O6 C13 C14 O5 -2.8(5) . . . . ?
C12 C13 C14 O5 179.3(3) . . . . ?
O6 C13 C14 C9 176.9(3) . . . . ?
C12 C13 C14 C9 -1.0(5) . . . . ?
C10 C9 C14 O5 179.9(3) . . . . ?
C8 C9 C14 O5 1.5(5) . . . . ?
C10 C9 C14 C13 0.3(5) . . . . ?
C8 C9 C14 C13 -178.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653955
