#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/36/2233601.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_2233601
loop_
_publ_author_name
'Dong, Su-Lan'
'Cheng, Xiaochun'
_publ_section_title
;
 3-Methyl-4-nitrophenol
;
_journal_coeditor_code           PV2508
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o518
_journal_paper_doi               10.1107/S160053681200253X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C7 H7 N O3'
_chemical_formula_moiety         'C7 H7 N O3'
_chemical_formula_sum            'C7 H7 N O3'
_chemical_formula_weight         153.14
_chemical_name_common            3-methyl-4-nitrophenol
_chemical_name_systematic
;
3-Methyl-4-nitrophenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 91.217(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2993(14)
_cell_length_b                   13.023(3)
_cell_length_c                   7.4445(16)
_cell_measurement_reflns_used    2201
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.82
_cell_measurement_theta_min      2.79
_cell_volume                     707.5(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3860
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0433
_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)+(0.0847P)²+0.2660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                1071
_reflns_number_total             1293
_reflns_threshold_expression     I>2σ
_cod_data_source_file            pv2508.cif
_cod_data_source_block           I
_cod_original_cell_volume        707.5(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233601
_cod_database_fobs_code          2233601
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
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_symmetry_multiplicity
O O3 1.09340(18) 0.37232(10) 0.0133(2) 0.0532(4) Uani d . 1 1
H H3 1.1635 0.3301 -0.0293 0.080 Uiso calc R 1 1
C C7 0.9309(2) 0.21737(13) 0.0839(2) 0.0388(5) Uani d . 1 1
H H7 1.0295 0.1779 0.0476 0.047 Uiso calc R 1 1
C C3 0.6322(2) 0.23242(13) 0.1996(2) 0.0370(4) Uani d . 1 1
C C5 0.8008(3) 0.38512(14) 0.1339(2) 0.0417(5) Uani d . 1 1
H H5 0.8101 0.4563 0.1303 0.050 Uiso calc R 1 1
C C4 0.6461(2) 0.33913(14) 0.1958(2) 0.0402(5) Uani d . 1 1
H H4 0.5497 0.3792 0.2356 0.048 Uiso calc R 1 1
C C1 0.7737(3) 0.05198(14) 0.1483(3) 0.0542(6) Uani d . 1 1
H H1A 0.7391 0.0288 0.2652 0.081 Uiso calc R 1 1
H H1B 0.8940 0.0268 0.1226 0.081 Uiso calc R 1 1
H H1C 0.6877 0.0266 0.0597 0.081 Uiso calc R 1 1
C C2 0.7745(2) 0.16801(13) 0.1442(2) 0.0366(4) Uani d . 1 1
C C6 0.9445(2) 0.32372(14) 0.0763(2) 0.0378(4) Uani d . 1 1
N N1 0.4618(2) 0.19093(13) 0.2651(2) 0.0467(4) Uani d . 1 1
O O2 0.3574(2) 0.24929(12) 0.3445(2) 0.0635(5) Uani d . 1 1
O O1 0.4233(2) 0.10112(12) 0.2411(3) 0.0868(7) Uani d . 1 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'
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
C6 O3 H3 109.5
C6 C7 C2 122.19(15)
C6 C7 H7 118.9
C2 C7 H7 118.9
C4 C3 C2 122.34(15)
C4 C3 N1 116.23(15)
C2 C3 N1 121.42(16)
C4 C5 C6 118.99(16)
C4 C5 H5 120.5
C6 C5 H5 120.5
C5 C4 C3 120.33(16)
C5 C4 H4 119.8
C3 C4 H4 119.8
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C2 C3 115.82(15)
C7 C2 C1 118.12(16)
C3 C2 C1 126.04(16)
O3 C6 C7 122.66(15)
O3 C6 C5 117.02(16)
C7 C6 C5 120.31(15)
O1 N1 O2 121.27(16)
O1 N1 C3 120.45(16)
O2 N1 C3 118.28(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C6 1.351(2)
O3 H3 0.8200
C7 C6 1.390(3)
C7 C2 1.393(2)
C7 H7 0.9300
C3 C4 1.394(3)
C3 C2 1.404(2)
C3 N1 1.450(2)
C5 C4 1.367(2)
C5 C6 1.393(3)
C5 H5 0.9300
C4 H4 0.9300
C1 C2 1.511(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
N1 O1 1.215(2)
N1 O2 1.236(2)
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 H3 O2 4_654 0.82 2.00 2.811(2) 169 yes
C4 H4 O2 . 0.93 2.35 2.671(2) 100 no
C5 H5 O3 3_765 0.93 2.58 3.437(2) 154 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
C6 C5 C4 C3 -0.6(3)
C2 C3 C4 C5 1.1(3)
N1 C3 C4 C5 -179.15(15)
C6 C7 C2 C3 -1.0(2)
C6 C7 C2 C1 -179.66(16)
C4 C3 C2 C7 -0.4(2)
N1 C3 C2 C7 179.95(15)
C4 C3 C2 C1 178.20(17)
N1 C3 C2 C1 -1.5(3)
C2 C7 C6 O3 -178.06(16)
C2 C7 C6 C5 1.6(3)
C4 C5 C6 O3 178.90(16)
C4 C5 C6 C7 -0.8(3)
C4 C3 N1 O1 165.72(19)
C2 C3 N1 O1 -14.6(3)
C4 C3 N1 O2 -13.9(2)
C2 C3 N1 O2 165.86(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16475
