#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/09/2230952.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_2230952
loop_
_publ_author_name
'Liu, Peng'
'Wu, Jian-Feng'
'Wang, Ping-An'
'He, Wei'
'Wang, Hai-Bo'
_publ_section_title
;
 1-(4-Amino-3,5-dichlorophenyl)ethanol
;
_journal_coeditor_code           ZK2012
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1839
_journal_paper_doi               10.1107/S1600536811024196
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H9 Cl2 N O'
_chemical_formula_moiety         'C8 H9 Cl2 N O'
_chemical_formula_sum            'C8 H9 Cl2 N O'
_chemical_formula_weight         206.06
_chemical_name_systematic
;
1-(4-Amino-3,5-dichlorophenyl)ethanol
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.049(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   16.472(2)
_cell_length_b                   16.110(2)
_cell_length_c                   14.6756(19)
_cell_measurement_reflns_used    5355
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.55
_cell_volume                     3723.2(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9273
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.9501
_exptl_absorpt_correction_T_min  0.9092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.456
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3279
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0323
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                2855
_reflns_number_total             3279
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zk2012.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2230952
_cod_database_fobs_code          2230952
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.10844(4) 0.04952(4) 0.86690(4) 0.0620(2) Uani d . 1 1 . .
Cl Cl2 1.09417(4) 0.16958(4) 1.20328(4) 0.0598(2) Uani d . 1 1 . .
Cl Cl3 0.70719(3) -0.07065(4) 0.67509(4) 0.0557(2) Uani d . 1 1 . .
Cl Cl4 0.44673(4) 0.14455(3) 0.61899(4) 0.0527(2) Uani d . 1 1 . .
O O1 0.78216(11) 0.06516(11) 0.85101(13) 0.0617(5) Uani d . 1 1 . .
O O2 0.31701(9) -0.14705(11) 0.48677(12) 0.0519(4) Uani d D 1 1 . .
N N1 1.18071(11) 0.10254(12) 1.06839(15) 0.0468(4) Uani d . 1 1 . .
N N2 0.63069(12) 0.09603(13) 0.67790(13) 0.0440(4) Uani d . 1 1 . .
C C1 1.04879(13) 0.08619(12) 0.93915(14) 0.0416(5) Uani d . 1 1 . .
C C2 0.96140(14) 0.08983(14) 0.90409(15) 0.0458(5) Uani d . 1 1 . .
C C3 0.91343(12) 0.11733(12) 0.96181(14) 0.0414(5) Uani d . 1 1 . .
C C4 0.95554(13) 0.14186(12) 1.05372(15) 0.0408(5) Uani d . 1 1 . .
C C5 1.04275(12) 0.13832(12) 1.08668(13) 0.0389(4) Uani d . 1 1 . .
C C6 1.09322(12) 0.11026(11) 1.03173(13) 0.0375(4) Uani d . 1 1 . .
C C7 0.81676(14) 0.12321(15) 0.92535(18) 0.0517(5) Uani d . 1 1 . .
C C8 0.78811(16) 0.20783(16) 0.8855(2) 0.0712(8) Uani d . 1 1 . .
H H8A 0.7272 0.2094 0.8632 0.107 Uiso calc R 1 1 . .
H H8B 0.8106 0.2193 0.8334 0.107 Uiso calc R 1 1 . .
H H8C 0.8082 0.2489 0.9344 0.107 Uiso calc R 1 1 . .
C C9 0.59864(12) -0.05077(12) 0.64539(13) 0.0377(4) Uani d . 1 1 . .
C C10 0.54210(12) -0.11507(13) 0.61455(14) 0.0388(4) Uani d . 1 1 . .
C C11 0.45556(12) -0.10121(12) 0.58610(13) 0.0380(4) Uani d . 1 1 . .
C C12 0.42693(12) -0.02043(13) 0.58929(14) 0.0406(5) Uani d . 1 1 . .
C C13 0.48443(12) 0.04327(12) 0.62044(13) 0.0366(4) Uani d . 1 1 . .
C C14 0.57235(11) 0.03095(12) 0.65081(12) 0.0354(4) Uani d . 1 1 . .
C C15 0.39451(13) -0.17286(14) 0.55311(16) 0.0458(5) Uani d . 1 1 . .
C C16 0.37270(17) -0.21407(17) 0.6356(2) 0.0578(6) Uani d . 1 1 . .
H H1 0.3668(13) -0.0092(11) 0.5668(14) 0.035(5) Uiso d . 1 1 . .
H H2 0.5640(15) -0.1665(14) 0.6168(17) 0.048(6) Uiso d . 1 1 . .
H H3 0.9238(15) 0.1595(14) 1.0923(18) 0.048(6) Uiso d . 1 1 . .
H H4 0.4188(13) -0.2126(14) 0.5260(15) 0.045(6) Uiso d . 1 1 . .
H H5 0.9332(14) 0.0707(13) 0.8489(16) 0.045(6) Uiso d . 1 1 . .
H H6 0.3307(18) -0.2551(16) 0.612(2) 0.069(7) Uiso d . 1 1 . .
H H8 0.6703(16) 0.0815(14) 0.7248(17) 0.045(6) Uiso d . 1 1 . .
H H9 0.3513(16) -0.1676(16) 0.6741(18) 0.058(7) Uiso d . 1 1 . .
H H10 0.4207(17) -0.2342(17) 0.6731(19) 0.062(7) Uiso d . 1 1 . .
H H11 0.6117(18) 0.1357(18) 0.6943(19) 0.061(9) Uiso d . 1 1 . .
H H12 0.7895(15) 0.1125(15) 0.9809(17) 0.051(6) Uiso d . 1 1 . .
H H13 1.2082(18) 0.1076(17) 1.030(2) 0.062(8) Uiso d . 1 1 . .
H H15 1.2046(18) 0.1337(17) 1.118(2) 0.062(8) Uiso d . 1 1 . .
H H16 0.794(2) 0.016(2) 0.867(2) 0.084(10) Uiso d . 1 1 . .
H H18 0.3276(19) -0.1363(17) 0.4388(16) 0.070(9) 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 H16 . . 113(2) ?
C15 O2 H18 . . 106(2) ?
C6 N1 H13 . . 116(2) ?
C6 N1 H15 . . 115.7(18) ?
H13 N1 H15 . . 108(3) ?
C14 N2 H8 . . 109.3(16) ?
C14 N2 H11 . . 113(2) ?
H8 N2 H11 . . 105(3) ?
C2 C1 C6 . . 122.87(18) ?
C2 C1 Cl1 . . 119.93(16) ?
C6 C1 Cl1 . . 117.20(15) ?
C1 C2 C3 . . 120.23(19) ?
C1 C2 H5 . . 123.4(15) ?
C3 C2 H5 . . 116.1(15) ?
C4 C3 C2 . . 118.29(18) ?
C4 C3 C7 . . 119.86(19) ?
C2 C3 C7 . . 121.82(18) ?
C5 C4 C3 . . 120.33(19) ?
C5 C4 H3 . . 121.3(15) ?
C3 C4 H3 . . 118.4(15) ?
C4 C5 C6 . . 123.30(18) ?
C4 C5 Cl2 . . 119.27(15) ?
C6 C5 Cl2 . . 117.44(15) ?
N1 C6 C5 . . 122.21(18) ?
N1 C6 C1 . . 122.73(18) ?
C5 C6 C1 . . 114.97(17) ?
O1 C7 C8 . . 106.7(2) ?
O1 C7 C3 . . 111.71(19) ?
C8 C7 C3 . . 111.63(19) ?
O1 C7 H12 . . 108.6(13) ?
C8 C7 H12 . . 107.1(13) ?
C3 C7 H12 . . 110.9(13) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C14 . . 122.46(17) ?
C10 C9 Cl3 . . 119.32(15) ?
C14 C9 Cl3 . . 118.18(14) ?
C9 C10 C11 . . 121.09(19) ?
C9 C10 H2 . . 117.1(15) ?
C11 C10 H2 . . 121.8(15) ?
C10 C11 C12 . . 118.14(18) ?
C10 C11 C15 . . 120.22(18) ?
C12 C11 C15 . . 121.64(17) ?
C13 C12 C11 . . 120.04(17) ?
C13 C12 H1 . . 120.7(11) ?
C11 C12 H1 . . 119.2(11) ?
C12 C13 C14 . . 123.08(17) ?
C12 C13 Cl4 . . 118.96(15) ?
C14 C13 Cl4 . . 117.93(15) ?
C9 C14 C13 . . 115.17(16) ?
C9 C14 N2 . . 121.63(17) ?
C13 C14 N2 . . 123.02(18) ?
O2 C15 C16 . . 107.45(18) ?
O2 C15 C11 . . 112.01(18) ?
C16 C15 C11 . . 111.70(19) ?
O2 C15 H4 . . 109.2(14) ?
C16 C15 H4 . . 106.3(13) ?
C11 C15 H4 . . 109.9(14) ?
C15 C16 H6 . . 109.3(17) ?
C15 C16 H9 . . 108.2(13) ?
H6 C16 H9 . . 112(2) ?
C15 C16 H10 . . 106.3(16) ?
H6 C16 H10 . . 113(2) ?
H9 C16 H10 . . 108(2) ?
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
Cl1 C1 . 1.7463(19) ?
Cl2 C5 . 1.7462(19) ?
Cl3 C9 . 1.7415(19) ?
Cl4 C13 . 1.7437(19) ?
O1 C7 . 1.423(3) ?
O1 H16 . 0.84(3) ?
O2 C15 . 1.422(3) ?
O2 H18 . 0.792(17) ?
N1 C6 . 1.388(3) ?
N1 H13 . 0.82(3) ?
N1 H15 . 0.87(3) ?
N2 C14 . 1.399(3) ?
N2 H8 . 0.83(3) ?
N2 H11 . 0.78(3) ?
C1 C2 . 1.381(3) ?
C1 C6 . 1.396(3) ?
C2 C3 . 1.389(3) ?
C2 H5 . 0.86(2) ?
C3 C4 . 1.381(3) ?
C3 C7 . 1.527(3) ?
C4 C5 . 1.376(3) ?
C4 H3 . 0.92(2) ?
C5 C6 . 1.392(3) ?
C7 C8 . 1.504(3) ?
C7 H12 . 1.05(2) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.378(3) ?
C9 C14 . 1.395(3) ?
C10 C11 . 1.381(3) ?
C10 H2 . 0.90(2) ?
C11 C12 . 1.390(3) ?
C11 C15 . 1.514(3) ?
C12 C13 . 1.380(3) ?
C12 H1 . 0.96(2) ?
C13 C14 . 1.399(3) ?
C15 C16 . 1.513(3) ?
C15 H4 . 0.91(2) ?
C16 H6 . 0.95(3) ?
C16 H9 . 1.06(3) ?
C16 H10 . 0.88(3) ?
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 H13 O2 6_656 0.82(3) 2.17(3) 2.927(3) 154(3)
O1 H16 N1 5_757 0.83(3) 2.12(3) 2.941(3) 169(3)
O2 H18 N2 5_656 0.79(3) 2.13(3) 2.912(3) 172(2)
