#------------------------------------------------------------------------------
#$Date: 2008-03-30 12:21:05 +0200 (Sun, 30 Mar 2008) $
#$Revision: 321 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100384.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_2100384
_journal_coeditor_code           NS0011
_journal_date_accepted           2005-10-21
_journal_date_recd_electronic    2005-07-22
_journal_issue                   1
_journal_name_full               'Acta Crystallographica, Section B'
_journal_page_first              143
_journal_page_last               152
_journal_paper_category          FA
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C6 H5 N O3'
_chemical_formula_sum            'C6 H5 N O3'
_chemical_formula_weight         139.11
_chemical_name_common            para-nitrophenol
_chemical_name_systematic
;
 4-nitrophenol
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                 103.09(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1460(10)
_cell_length_b                   8.903(2)
_cell_length_c                   11.763(5)
_cell_measurement_reflns_used    665
_cell_measurement_temperature    333(2)
_cell_measurement_theta_max      21.73
_cell_measurement_theta_min      3.97
_cell_volume                     626.9(3)
_computing_cell_refinement       'KUMA KM4CCD software, 1999'
_computing_data_collection       'KUMA KM4CCD software, 1999'
_computing_data_reduction        'KUMA KM4CCD software, 1999'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      333(2)
_diffrn_measured_fraction_theta_full 0.827
_diffrn_measured_fraction_theta_max 0.751
_diffrn_measurement_device_type  'KUMA Diffraction KM4CCD'
_diffrn_measurement_method       'omega scan'
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2046
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         4.33
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.124
_refine_ls_extinction_coef       0.095(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1667
_reflns_number_gt                725
_reflns_number_total             1067
_reflns_threshold_expression     >2sigma(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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_occupancy
_atom_site_type_symbol
O1 0.1247(4) -0.0116(2) 0.1843(2) 0.0991(8) Uani d 1 O
O2 0.9450(3) 0.2033(2) 0.55718(18) 0.0987(8) Uani d 1 O
O3 0.7074(3) 0.3670(2) 0.58425(18) 0.1006(8) Uani d 1 O
N 0.7574(3) 0.2557(2) 0.53377(19) 0.0717(7) Uani d 1 N
C1 0.2719(4) 0.0572(3) 0.2714(2) 0.0675(7) Uani d 1 C
C2 0.2171(4) 0.1807(2) 0.3299(2) 0.0669(7) Uani d 1 C
C3 0.3745(4) 0.2451(2) 0.4162(2) 0.0637(7) Uani d 1 C
C4 0.5873(3) 0.1869(2) 0.44417(18) 0.0558(6) Uani d 1 C
C5 0.6432(4) 0.0621(2) 0.3872(2) 0.0653(7) Uani d 1 C
C6 0.4844(5) -0.0023(3) 0.3018(3) 0.0733(7) Uani d 1 C
H5 0.341(3) 0.327(3) 0.455(2) 0.069(6) Uiso d 1 H
H3 0.803(4) 0.020(2) 0.414(2) 0.081(7) Uiso d 1 H
H6 0.076(4) 0.225(3) 0.311(2) 0.085(7) Uiso d 1 H
H2 0.512(5) -0.086(3) 0.261(3) 0.096(8) Uiso d 1 H
H1 0.004(7) 0.041(5) 0.171(4) 0.151(17) Uiso d 1 H
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
O1 0.1001(14) 0.0811(12) 0.0971(19) -0.0032(10) -0.0172(13) -0.0069(11)
O2 0.0667(11) 0.1140(15) 0.1029(19) 0.0164(9) -0.0071(11) -0.0170(12)
O3 0.0972(13) 0.0949(13) 0.1001(17) 0.0141(10) 0.0019(12) -0.0347(12)
N 0.0721(12) 0.0752(12) 0.0650(15) 0.0064(10) 0.0094(11) -0.0031(11)
C1 0.0726(13) 0.0597(11) 0.0635(18) -0.0038(10) 0.0014(12) 0.0068(11)
C2 0.0587(12) 0.0631(12) 0.076(2) 0.0070(10) 0.0095(13) 0.0137(12)
C3 0.0680(13) 0.0556(11) 0.0689(18) 0.0085(9) 0.0185(12) 0.0015(11)
C4 0.0597(11) 0.0577(10) 0.0492(16) 0.0019(9) 0.0104(11) 0.0040(10)
C5 0.0655(13) 0.0658(12) 0.0648(17) 0.0110(10) 0.0148(12) 0.0022(12)
C6 0.0867(16) 0.0647(12) 0.0668(19) 0.0087(12) 0.0143(14) -0.0066(13)
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
O2 N O3 121.8(2)
O2 N C4 119.7(2)
O3 N C4 118.4(2)
O1 C1 C2 122.9(2)
O1 C1 C6 117.0(2)
C2 C1 C6 120.0(2)
C3 C2 C1 119.7(2)
C2 C3 C4 119.8(2)
C3 C4 C5 121.0(2)
C3 C4 N 120.5(2)
C5 C4 N 118.53(19)
C6 C5 C4 118.9(2)
C5 C6 C1 120.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.350(3)
O2 N 1.216(2)
O3 N 1.230(2)
N C4 1.442(3)
C1 C2 1.379(3)
C1 C6 1.380(3)
C2 C3 1.360(3)
C3 C4 1.375(3)
C4 C5 1.380(3)
C5 C6 1.359(4)