#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/23/2222373.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_2222373
loop_
_publ_author_name
'Tang, Zhan'
'Xu, Min'
'Zheng, Gui-Ru'
'Feng, Hai'
_publ_section_title
;
 1-(2-Chlorophenyl)-2-(isopropylamino)ethanol
;
_journal_coeditor_code           IS2416
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1501
_journal_paper_doi               10.1107/S1600536809019953
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H16 Cl N O'
_chemical_formula_moiety         'C11 H16 Cl N O'
_chemical_formula_sum            'C11 H16 Cl N O'
_chemical_formula_weight         213.70
_chemical_name_systematic
;
1-(2-Chlorophenyl)-2-(isopropylamino)ethanol
;
_space_group_IT_number           114
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.0195(5)
_cell_length_b                   14.0195(5)
_cell_length_c                   12.1243(4)
_cell_measurement_reflns_used    13301
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.3
_cell_volume                     2382.99(14)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         RT
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22063
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.9388
_exptl_absorpt_correction_T_min  0.8710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.328
_refine_ls_abs_structure_details 'Flack (1983), 1181 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0010(10)
_refine_ls_extinction_coef       0.0308(10)
_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   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0434
_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/[σ²(Fo²)+(0.002P)²+1.96P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                1796
_reflns_number_total             2711
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2416.cif
_cod_data_source_block           I
_cod_database_code               2222373
_cod_database_fobs_code          2222373
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'
'-y+1/2, -x+1/2, z+1/2'
'-y, x, -z'
'y, -x, -z'
'y+1/2, x+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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.89802(8) 0.90968(7) 0.76779(8) 0.0866(3) Uani d . 1 . .
O O1 0.82940(16) 1.14673(15) 0.54268(18) 0.0616(6) Uani d . 1 . .
H H201 0.8801 1.1727 0.5581 0.074 Uiso calc R 1 . .
C C2 0.81036(19) 1.07851(19) 0.7258(2) 0.0484(6) Uani d . 1 . .
C C1 0.8209(2) 1.06095(19) 0.6030(2) 0.0492(7) Uani d . 1 . .
H H1 0.8769 1.0208 0.5896 0.059 Uiso calc R 1 . .
N N1 0.74199(17) 0.99152(18) 0.4402(2) 0.0527(6) Uani d . 1 . .
H H301 0.7679 1.0439 0.4192 0.063 Uiso d . 1 . .
C C4 0.8307(3) 1.0339(3) 0.9173(3) 0.0717(10) Uani d . 1 . .
H H4 0.8532 0.9910 0.9697 0.086 Uiso calc R 1 . .
C C3 0.8417(2) 1.0153(2) 0.8060(2) 0.0557(7) Uani d . 1 . .
C C8 0.7325(2) 1.0115(2) 0.5591(2) 0.0538(7) Uani d . 1 . .
H H8A 0.7227 0.9521 0.5987 0.065 Uiso calc R 1 . .
H H8B 0.6772 1.0517 0.5714 0.065 Uiso calc R 1 . .
C C9 0.6502(2) 0.9762(2) 0.3839(3) 0.0658(9) Uani d . 1 . .
H H9 0.6062 1.0272 0.4054 0.079 Uiso calc R 1 . .
C C7 0.7657(2) 1.1617(2) 0.7621(3) 0.0649(8) Uani d . 1 . .
H H7 0.7436 1.2054 0.7104 0.078 Uiso calc R 1 . .
C C11 0.6655(3) 0.9809(3) 0.2604(3) 0.0907(12) Uani d . 1 . .
H H11A 0.7094 0.9319 0.2385 0.109 Uiso calc R 1 . .
H H11B 0.6911 1.0422 0.2411 0.109 Uiso calc R 1 . .
H H11C 0.6057 0.9717 0.2233 0.109 Uiso calc R 1 . .
C C6 0.7534(2) 1.1809(3) 0.8735(3) 0.0753(10) Uani d . 1 . .
H H6 0.7233 1.2367 0.8959 0.090 Uiso calc R 1 . .
C C10 0.6073(3) 0.8813(3) 0.4176(3) 0.0885(12) Uani d . 1 . .
H H10A 0.5965 0.8810 0.4958 0.106 Uiso calc R 1 . .
H H10B 0.6505 0.8307 0.3986 0.106 Uiso calc R 1 . .
H H10C 0.5479 0.8721 0.3798 0.106 Uiso calc R 1 . .
C C5 0.7860(3) 1.1172(3) 0.9497(3) 0.0779(11) Uani d . 1 . .
H H5 0.7781 1.1300 1.0244 0.093 Uiso calc R 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'
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'
O O 0.0106 0.0060 '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
C1 O1 H201 . . 109.5 ?
C3 C2 C7 . . 117.1(3) ?
C3 C2 C1 . . 123.6(3) ?
C7 C2 C1 . . 119.3(3) ?
O1 C1 C8 . . 106.1(2) ?
O1 C1 C2 . . 112.2(2) ?
C8 C1 C2 . . 109.8(2) ?
O1 C1 H1 . . 109.6 ?
C8 C1 H1 . . 109.6 ?
C2 C1 H1 . . 109.6 ?
C9 N1 C8 . . 113.7(2) ?
C9 N1 H301 . . 110.9 ?
C8 N1 H301 . . 99.5 ?
C5 C4 C3 . . 119.2(3) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C3 C2 . . 121.9(3) ?
C4 C3 Cl1 . . 118.1(3) ?
C2 C3 Cl1 . . 120.0(2) ?
N1 C8 C1 . . 110.9(2) ?
N1 C8 H8A . . 109.5 ?
C1 C8 H8A . . 109.5 ?
N1 C8 H8B . . 109.5 ?
C1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
N1 C9 C10 . . 110.5(3) ?
N1 C9 C11 . . 109.2(3) ?
C10 C9 C11 . . 111.2(3) ?
N1 C9 H9 . . 108.7 ?
C10 C9 H9 . . 108.7 ?
C11 C9 H9 . . 108.7 ?
C6 C7 C2 . . 121.7(3) ?
C6 C7 H7 . . 119.2 ?
C2 C7 H7 . . 119.2 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C5 C6 C7 . . 119.4(3) ?
C5 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C6 C5 C4 . . 120.8(3) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 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
Cl1 C3 . 1.741(3) ?
O1 C1 . 1.413(3) ?
O1 H201 . 0.8200 ?
C2 C3 . 1.387(4) ?
C2 C7 . 1.395(4) ?
C2 C1 . 1.516(4) ?
C1 C8 . 1.517(4) ?
C1 H1 . 0.9800 ?
N1 C9 . 1.473(4) ?
N1 C8 . 1.475(4) ?
N1 H301 . 0.8580 ?
C4 C5 . 1.382(5) ?
C4 C3 . 1.383(4) ?
C4 H4 . 0.9300 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.516(5) ?
C9 C11 . 1.514(5) ?
C9 H9 . 0.9800 ?
C7 C6 . 1.387(5) ?
C7 H7 . 0.9300 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C6 C5 . 1.364(5) ?
C6 H6 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C5 H5 . 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 H201 N1 7_576 0.82 1.97 2.765(3) 164
N1 H301 O1 . 0.86 2.25 2.789(3) 121
C6 H6 O1 8_455 0.93 2.45 3.283(4) 149
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
C3 C2 C1 O1 . . . . -150.5(3) ?
C7 C2 C1 O1 . . . . 30.5(4) ?
C3 C2 C1 C8 . . . . 91.8(3) ?
C7 C2 C1 C8 . . . . -87.2(3) ?
C5 C4 C3 C2 . . . . 1.0(5) ?
C5 C4 C3 Cl1 . . . . -179.8(3) ?
C7 C2 C3 C4 . . . . -0.9(5) ?
C1 C2 C3 C4 . . . . -180.0(3) ?
C7 C2 C3 Cl1 . . . . 179.9(2) ?
C1 C2 C3 Cl1 . . . . 0.9(4) ?
C9 N1 C8 C1 . . . . -159.3(3) ?
O1 C1 C8 N1 . . . . 59.9(3) ?
C2 C1 C8 N1 . . . . -178.6(2) ?
C8 N1 C9 C10 . . . . -71.4(4) ?
C8 N1 C9 C11 . . . . 166.0(3) ?
C3 C2 C7 C6 . . . . 0.3(5) ?
C1 C2 C7 C6 . . . . 179.4(3) ?
C2 C7 C6 C5 . . . . 0.2(5) ?
C7 C6 C5 C4 . . . . -0.2(6) ?
C3 C4 C5 C6 . . . . -0.4(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2708
