data_2100387
_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               93.45(3)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 3.8310(10)
_cell_length_b                 11.093(2)
_cell_length_c                 14.835(3)
_cell_measurement_reflns_used  1153
_cell_measurement_temperature  375(2)
_cell_measurement_theta_max    22.87
_cell_measurement_theta_min    3.56
_cell_volume                   629.3(2)
_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    375(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.940
_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 0.0614
_diffrn_reflns_av_sigmaI/netI  0.0357
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_h_min     -2
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_l_max     21
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_number          4985
_diffrn_reflns_theta_full      25.00
_diffrn_reflns_theta_max       31.37
_diffrn_reflns_theta_min       5.43
_diffrn_standards_decay_%      ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       ?
_exptl_absorpt_coefficient_mu  0.120
_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  1.468
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     needle
_exptl_crystal_F_000           288
_exptl_crystal_size_max        0.98
_exptl_crystal_size_mid        0.53
_exptl_crystal_size_min        0.45
_refine_diff_density_max       0.255
_refine_diff_density_min       -0.215
_refine_ls_extinction_coef     0.05(3)
_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 1.158
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   112
_refine_ls_number_reflns       1955
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.158
_refine_ls_R_factor_all        0.1070
_refine_ls_R_factor_gt         0.0776
_refine_ls_shift/su_max        0.022
_refine_ls_shift/su_mean       0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1467P)^2^+0.0501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.2549
_refine_ls_wR_factor_ref       0.2937
_reflns_number_gt              1165
_reflns_number_total           1955
_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 -0.2067(6) 0.2435(2) 0.99594(14) 0.0797(7) Uani d . 1 . . N
O1 0.0736(6) 0.04282(18) 0.66656(13) 0.0886(6) Uani d . 1 . . O
O2 -0.3598(7) 0.1803(2) 1.04908(14) 0.1116(9) Uani d . 1 . . O
O3 -0.1235(9) 0.3468(2) 1.01367(19) 0.1251(10) Uani d . 1 . . O
C1 0.0112(5) 0.0971(2) 0.74600(14) 0.0616(6) Uani d . 1 . . C
C2 0.0792(6) 0.2171(2) 0.76264(15) 0.0649(6) Uani d . 1 . . C
C3 0.0117(6) 0.2663(2) 0.84548(15) 0.0667(6) Uani d . 1 . . C
C4 -0.1259(5) 0.19319(19) 0.90950(14) 0.0599(5) Uani d . 1 . . C
C5 -0.1928(5) 0.0730(2) 0.89397(15) 0.0632(6) Uani d . 1 . . C
C6 -0.1233(6) 0.0251(2) 0.81166(17) 0.0666(6) Uani d . 1 . . C
H5 -0.281(7) 0.026(3) 0.944(2) 0.083(8) Uiso d . 1 . . H
H6 -0.175(8) -0.065(3) 0.802(2) 0.094(8) Uiso d . 1 . . H
H3 0.070(7) 0.350(3) 0.866(2) 0.088(8) Uiso d . 1 . . H
H2 0.168(8) 0.264(3) 0.719(2) 0.089(8) Uiso d . 1 . . H
H1 0.169(11) 0.104(5) 0.625(3) 0.144(14) 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 0.0944(14) 0.0850(15) 0.0603(11) 0.0058(11) 0.0089(9) -0.0033(10)
O1 0.1260(15) 0.0761(12) 0.0660(11) 0.0092(10) 0.0234(10) -0.0051(8)
O2 0.154(2) 0.1214(18) 0.0629(11) -0.0072(14) 0.0372(12) 0.0049(11)
O3 0.184(3) 0.0986(17) 0.0956(17) -0.0173(16) 0.0327(16) -0.0314(13)
C1 0.0640(11) 0.0642(11) 0.0570(11) 0.0077(8) 0.0066(8) 0.0024(9)
C2 0.0740(12) 0.0618(12) 0.0603(12) -0.0023(9) 0.0141(9) 0.0131(9)
C3 0.0770(13) 0.0547(11) 0.0684(13) -0.0026(9) 0.0056(10) 0.0066(9)
C4 0.0617(10) 0.0678(12) 0.0507(10) 0.0039(9) 0.0058(8) 0.0030(8)
C5 0.0663(11) 0.0657(12) 0.0577(11) -0.0056(8) 0.0043(8) 0.0130(9)
C6 0.0745(12) 0.0578(11) 0.0675(13) -0.0043(9) 0.0057(9) 0.0034(9)
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 . . 121.9(2) ?
O3 N C4 . . 119.2(2) ?
O2 N C4 . . 118.9(2) ?
O1 C1 C2 . . 122.92(19) ?
O1 C1 C6 . . 116.6(2) ?
C2 C1 C6 . . 120.5(2) ?
C1 C2 C3 . . 119.87(18) ?
C4 C3 C2 . . 118.7(2) ?
C5 C4 C3 . . 122.1(2) ?
C5 C4 N . . 118.31(19) ?
C3 C4 N . . 119.6(2) ?
C6 C5 C4 . . 118.74(18) ?
C5 C6 C1 . . 120.2(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
N O3 . 1.215(3) ?
N O2 . 1.230(3) ?
N C4 . 1.449(3) ?
O1 C1 . 1.357(3) ?
C1 C2 . 1.376(3) ?
C1 C6 . 1.383(3) ?
C2 C3 . 1.383(3) ?
C3 C4 . 1.378(3) ?
C4 C5 . 1.374(3) ?
C5 C6 . 1.373(3) ?