#------------------------------------------------------------------------------
#$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100385.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_2100385
_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_melting_point        384K
_chemical_name_common          para-nitrophenol
_chemical_name_systematic
;
 4-nitrophenol
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_H-M P21/n
_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               92.60(2)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 3.7740(10)
_cell_length_b                 11.147(4)
_cell_length_c                 14.695(3)
_cell_measurement_reflns_used  805
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    22.54
_cell_measurement_theta_min    3.96
_cell_volume                   617.6(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    302(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.897
_diffrn_measured_fraction_theta_max 0.828
_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 0.0411
_diffrn_reflns_av_sigmaI/netI  0.0345
_diffrn_reflns_limit_h_max     3
_diffrn_reflns_limit_h_min     -4
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_l_max     18
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_number          1991
_diffrn_reflns_theta_full      25.00
_diffrn_reflns_theta_max       27.20
_diffrn_reflns_theta_min       5.52
_diffrn_standards_decay_%      ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       ?
_exptl_absorpt_coefficient_mu  0.123
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_crystal_colour          'pale yellow'
_exptl_crystal_density_diffrn  1.496
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     needle
_exptl_crystal_F_000           288
_exptl_crystal_size_max        0.82
_exptl_crystal_size_mid        0.36
_exptl_crystal_size_min        0.25
_refine_diff_density_max       0.180
_refine_diff_density_min       -0.178
_refine_ls_extinction_coef     0.019(9)
_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 1.188
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   112
_refine_ls_number_reflns       1140
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.188
_refine_ls_R_factor_all        0.0976
_refine_ls_R_factor_gt         0.0734
_refine_ls_shift/su_max        0.005
_refine_ls_shift/su_mean       0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.6259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1865
_refine_ls_wR_factor_ref       0.2012
_reflns_number_gt              830
_reflns_number_total           1140
_reflns_threshold_expression   >2sigma(I)
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'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N -0.2005(9) 0.7396(3) 0.4939(2) 0.0596(10) Uani d . 1 . . N
O1 0.0815(9) 0.5394(3) 0.16181(19) 0.0673(9) Uani d . 1 . . O
O2 -0.3609(9) 0.6775(3) 0.5476(2) 0.0825(12) Uani d . 1 . . O
O3 -0.1121(11) 0.8431(3) 0.5113(2) 0.0904(13) Uani d . 1 . . O
C1 0.0170(9) 0.5939(3) 0.2415(2) 0.0457(9) Uani d . 1 . . C
C2 0.0906(10) 0.7138(4) 0.2589(3) 0.0484(10) Uani d . 1 . . C
C3 0.0213(10) 0.7617(4) 0.3423(3) 0.0506(10) Uani d . 1 . . C
C4 -0.1185(9) 0.6892(3) 0.4068(2) 0.0442(9) Uani d . 1 . . C
C5 -0.1907(9) 0.5698(4) 0.3903(2) 0.0471(9) Uani d . 1 . . C
C6 -0.1206(10) 0.5218(4) 0.3078(3) 0.0497(10) Uani d . 1 . . C
H1 0.137(13) 0.597(5) 0.125(4) 0.083(17) Uiso d . 1 . . H
H2 0.182(11) 0.761(4) 0.212(3) 0.066(12) Uiso d . 1 . . H
H3 0.051(11) 0.841(4) 0.358(3) 0.068(13) Uiso d . 1 . . H
H5 -0.288(11) 0.523(4) 0.438(3) 0.068(12) Uiso d . 1 . . H
H6 -0.171(9) 0.440(4) 0.294(2) 0.050(10) 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
N 0.066(2) 0.062(2) 0.0507(18) -0.0028(17) 0.0054(15) -0.0015(18)
O1 0.092(2) 0.063(2) 0.0484(16) 0.0086(17) 0.0151(15) -0.0021(16)
O2 0.109(3) 0.089(3) 0.0517(17) -0.016(2) 0.0277(17) 0.0048(17)
O3 0.130(3) 0.070(2) 0.073(2) -0.018(2) 0.028(2) -0.0190(19)
C1 0.051(2) 0.046(2) 0.0411(18) 0.0051(15) 0.0032(14) 0.0031(17)
C2 0.053(2) 0.046(2) 0.0465(19) -0.0006(17) 0.0102(15) 0.0088(18)
C3 0.056(2) 0.045(2) 0.050(2) -0.0040(17) 0.0036(16) 0.0026(19)
C4 0.0436(18) 0.051(2) 0.0379(17) 0.0010(15) 0.0036(13) 0.0014(17)
C5 0.0454(19) 0.052(2) 0.0438(18) -0.0031(16) 0.0068(14) 0.0099(18)
C6 0.053(2) 0.041(2) 0.055(2) -0.0034(16) 0.0016(16) -0.0001(19)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 N O2 . . 122.3(4) ?
O3 N C4 . . 119.0(3) ?
O2 N C4 . . 118.7(3) ?
O1 C1 C6 . . 116.0(3) ?
O1 C1 C2 . . 123.5(3) ?
C6 C1 C2 . . 120.5(3) ?
C3 C2 C1 . . 119.8(4) ?
C4 C3 C2 . . 118.8(4) ?
C3 C4 C5 . . 121.9(3) ?
C3 C4 N . . 119.2(3) ?
C5 C4 N . . 118.9(3) ?
C6 C5 C4 . . 119.4(3) ?
C5 C6 C1 . . 119.6(4) ?
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
N O3 . 1.224(4) ?
N O2 . 1.230(4) ?
N C4 . 1.445(5) ?
O1 C1 . 1.351(4) ?
C1 C6 . 1.383(5) ?
C1 C2 . 1.386(5) ?
C2 C3 . 1.373(5) ?
C3 C4 . 1.370(5) ?
C4 C5 . 1.377(5) ?
C5 C6 . 1.362(5) ?