#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/74/2007485.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_2007485
loop_
_publ_author_name
'Kandasamy Chinnakali'
'Hoong-Kun Fun'
'Kamaraj Sriraghavan'
'Vaylakkavoor T.Ramakrishnan'
_publ_section_title
;
 2-(4-Nitroanilino)-2-phenylethanol
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              955
_journal_page_last               957
_journal_paper_doi               10.1107/S0108270198001826
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C14 H14 N2 O3'
_chemical_formula_sum            'C14 H14 N2 O3'
_chemical_formula_weight         258.27
_chemical_name_systematic
;
2-(4-nitroanilino)-phenethylalcohol
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-P 3*'
_symmetry_space_group_name_H-M   'R -3 :R'
_cell_angle_alpha                118.340(10)
_cell_angle_beta                 118.340(10)
_cell_angle_gamma                118.340(10)
_cell_formula_units_Z            6
_cell_length_a                   18.618(2)
_cell_length_b                   18.618(2)
_cell_length_c                   18.618(2)
_cell_measurement_reflns_used    42
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.386
_cell_measurement_theta_min      5.373
_cell_volume                     2141(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material
; SHELXL93;
  PLATON (Spek, 1990)
;
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4 diffractometer'
_diffrn_measurement_method       'θ/2θ 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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4190
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.798
_refine_ls_goodness_of_fit_obs   1.069
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.798
_refine_ls_restrained_S_obs      1.069
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_obs          .0446
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0625P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1246
_refine_ls_wR_factor_obs         .1092
_reflns_number_observed          1487
_reflns_number_total             3220
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sk1162.cif
_cod_data_source_block           sk1162
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0625P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0625P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2007485
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'z, x, y'
'y, z, x'
'-x, -y, -z'
'-z, -x, -y'
'-y, -z, -x'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 .0660(2) -.4360(2) -.3447(2) .0889(5) Uani d . 1 . O
O2 .2627(2) -.2309(2) -.0694(2) .0756(5) Uani d . 1 . O
O3 .8785(2) .5669(2) .2560(2) .0571(4) Uani d . 1 . O
N1 .2039(2) -.2738(2) -.1793(2) .0590(4) Uani d . 1 . N
N2 .5682(2) .2765(2) .0742(2) .0543(5) Uani d . 1 . N
C1 .2975(2) -.1312(2) -.1134(3) .0464(4) Uani d . 1 . C
C2 .4594(3) .0545(3) .0753(3) .0509(5) Uani d . 1 . C
C3 .5501(3) .1908(3) .1392(3) .0512(5) Uani d . 1 . C
C4 .4805(2) .1445(2) .0153(2) .0435(4) Uani d . 1 . C
C5 .3141(3) -.0466(3) -.1764(3) .0518(5) Uani d . 1 . C
C6 .2247(3) -.1820(3) -.2397(3) .0529(5) Uani d . 1 . C
C7 .7446(3) .4777(3) .2688(3) .0493(5) Uani d . 1 . C
C8 .8288(3) .5853(3) .2902(3) .0530(5) Uani d . 1 . C
C9 .7242(3) .5300(3) .3363(3) .0605(5) Uani d . 1 . C
C10 .5557(5) .4200(5) .2105(5) .0897(8) Uani d . 1 . C
C11 .5443(6) .4774(7) .2774(7) .1318(12) Uani d . 1 . C
H11 .4299(6) .4022(7) .1916(7) .158 Uiso calc R 1 . H
C12 .7000(8) .6433(7) .4680(8) .1410(13) Uani d . 1 . C
H12 .6927(8) .6826(7) .5125(8) .169 Uiso calc R 1 . H
C13 .8656(6) .7505(5) .5922(6) .1192(11) Uani d . 1 . C
H13 .9711(6) .8621(5) .7218(6) .143 Uiso calc R 1 . H
C14 .8796(5) .6958(4) .5282(4) .0831(7) Uani d . 1 . C
H1N2 .520(3) .242(3) .001(3) .050(6) Uiso d . 1 . H
H1O3 .780(4) .459(4) .134(4) .100(9) Uiso d . 1 . H
H2 .506(3) .082(3) .155(3) .060(6) Uiso d . 1 . H
H3 .669(3) .323(3) .276(3) .062(5) Uiso d . 1 . H
H5 .275(3) -.073(3) -.252(3) .057(5) Uiso d . 1 . H
H6 .116(3) -.311(3) -.371(3) .056(5) Uiso d . 1 . H
H7 .837(2) .522(2) .354(2) .039(4) Uiso d . 1 . H
H8A .951(3) .726(3) .425(3) .060(5) Uiso d . 1 . H
H8B .742(2) .547(2) .208(2) .047(5) Uiso d . 1 . H
H10 .432(3) .288(3) .064(3) .092(8) Uiso d . 1 . H
H14 .994(3) .768(3) .616(3) .099(9) Uiso d . 1 . H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 N1 O2 121.5(4) yes
O1 N1 C1 118.9(4) yes
O2 N1 C1 119.6(2) yes
C4 N2 C7 124.6(4) yes
C2 C1 C6 120.9(5) ?
C2 C1 N1 119.6(4) ?
C6 C1 N1 119.6(3) ?
C3 C2 C1 119.9(5) ?
C2 C3 C4 120.8(3) ?
N2 C4 C3 122.5(2) ?
N2 C4 C5 119.9(4) ?
C3 C4 C5 117.7(4) ?
C6 C5 C4 121.5(4) ?
C5 C6 C1 119.2(3) ?
N2 C7 C8 109.1(4) ?
N2 C7 C9 114.1(4) ?
C8 C7 C9 109.0(5) ?
O3 C8 C7 113.3(5) ?
C10 C9 C14 118.8(7) ?
C10 C9 C7 121.3(4) ?
C14 C9 C7 119.8(6) ?
C9 C10 C11 120.2(4) ?
C12 C11 C10 120.4(11) ?
C13 C12 C11 119.5(14) ?
C12 C13 C14 120.8(7) ?
C9 C14 C13 120.3(7) ?
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
O1 N1 . 1.224(3) yes
O2 N1 . 1.231(5) yes
O3 C8 . 1.426(8) yes
N1 C1 . 1.441(7) yes
N2 C4 . 1.356(6) yes
N2 C7 . 1.443(4) yes
C1 C2 . 1.379(4) ?
C1 C6 . 1.381(7) ?
C2 C3 . 1.365(9) ?
C3 C4 . 1.399(6) ?
C4 C5 . 1.406(3) ?
C5 C6 . 1.359(9) ?
C7 C8 . 1.516(9) ?
C7 C9 . 1.521(9) ?
C9 C10 . 1.375(10) ?
C9 C14 . 1.379(4) ?
C10 C11 . 1.393(17) ?
C11 C12 . 1.365(9) ?
C12 C13 . 1.358(17) ?
C13 C14 . 1.386(16) ?
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
_geom_hbond_publ_flag
O3 H1O3 O3 3_554 0.88(3) 1.85(4) 2.710(5) 164(3) yes
C2 H2 O2 1_555 0.92(5) 2.40(5) 2.733(7) 101(2) yes
C6 H6 O1 4_544 0.98(3) 2.42(4) 3.346(5) 159(5) yes
C8 H8A O2 6_666 1.01(3) 2.48(4) 3.481(4) 172(5) yes
C8 H8B O1 6_555 0.99(4) 2.54(3) 3.490(6) 160(3) yes
N2 H1N2 O2 6_555 0.74(5) 2.62(4) 3.209(5) 138(2) yes
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_publ_flag
O1 N1 C1 C2 -176.4(5) yes
O2 N1 C1 C2 4.3(7) yes
O1 N1 C1 C6 3.2(7) ?
O2 N1 C1 C6 -176.2(5) ?
C6 C1 C2 C3 -0.3(9) ?
N1 C1 C2 C3 179.2(5) ?
C1 C2 C3 C4 0.2(9) ?
C7 N2 C4 C3 2.9(8) ?
C7 N2 C4 C5 -176.6(5) ?
C2 C3 C4 N2 -179.1(5) ?
C2 C3 C4 C5 0.4(9) ?
N2 C4 C5 C6 178.5(6) ?
C3 C4 C5 C6 -1.0(9) ?
C4 C5 C6 C1 0.9(10) ?
C2 C1 C6 C5 -0.3(9) ?
N1 C1 C6 C5 -179.8(5) ?
C4 N2 C7 C8 162.4(5) ?
C4 N2 C7 C9 -75.5(7) yes
N2 C7 C8 O3 -63.2(5) yes
C9 C7 C8 O3 171.7(2) ?
N2 C7 C9 C10 -27.3(10) ?
C8 C7 C9 C10 94.9(7) ?
N2 C7 C9 C14 156.1(6) ?
C8 C7 C9 C14 -81.8(7) ?
C14 C9 C10 C11 0.7(15) ?
C7 C9 C10 C11 -176.0(10) ?
C9 C10 C11 C12 0(2) ?
C10 C11 C12 C13 -1(2) ?
C11 C12 C13 C14 2(2) ?
C10 C9 C14 C13 -0.6(13) ?
C7 C9 C14 C13 176.2(8) ?
C12 C13 C14 C9 -0.6(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21185875
