#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/09/2210967.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_2210967
loop_
_publ_author_name
'Qian, Heng-Yu'
'Yin, Zhi-Gang'
'Jia Jia'
'Zhou Na'
'Feng Ling-Qin'
_publ_section_title
;
 4-Nitroaniline: a redetermination
;
_journal_coeditor_code           DN2073
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5048
_journal_page_last               o5049
_journal_paper_doi               10.1107/S1600536806040608
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C6 H6 N2 O2'
_chemical_formula_moiety         'C6 H6 N2 O2'
_chemical_formula_sum            'C6 H6 N2 O2'
_chemical_formula_weight         138.13
_chemical_name_systematic
;
4-nitroaniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.43(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6010(10)
_cell_length_b                   6.0430(10)
_cell_length_c                   12.352(2)
_cell_measurement_reflns_used    1869
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.7
_cell_volume                     641.81(17)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω 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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4953
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.0481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                1010
_reflns_number_total             1334
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            dn2073.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210967
_cod_database_fobs_code          2210967
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_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
O O1 0.13518(12) 0.12030(18) 1.07067(8) 0.0798(3) Uani d . 1
O O2 0.27899(12) 0.40842(16) 1.05394(8) 0.0771(4) Uani d . 1
N N1 0.24026(11) 0.21968(18) 1.02619(8) 0.0546(3) Uani d . 1
N N2 0.54929(14) -0.1791(2) 0.68754(9) 0.0763(4) Uani d . 1
H H2A 0.5222 -0.3085 0.6650 0.092 Uiso calc R 1
H H2B 0.6239 -0.1100 0.6571 0.092 Uiso calc R 1
C C1 0.32067(12) 0.11439(18) 0.93955(9) 0.0442(3) Uani d . 1
C C2 0.27604(14) -0.09554(18) 0.90513(10) 0.0497(3) Uani d . 1
H H2 0.1950 -0.1690 0.9383 0.060 Uiso calc R 1
C C3 0.35252(13) -0.19298(19) 0.82193(10) 0.0524(3) Uani d . 1
H H3 0.3231 -0.3337 0.7989 0.063 Uiso calc R 1
C C4 0.47456(13) -0.0844(2) 0.77078(10) 0.0512(3) Uani d . 1
C C5 0.51814(14) 0.1269(2) 0.80791(10) 0.0521(3) Uani d . 1
H H5 0.5995 0.2011 0.7754 0.062 Uiso calc R 1
C C6 0.44237(13) 0.22455(19) 0.89115(9) 0.0477(3) Uani d . 1
H H6 0.4722 0.3644 0.9154 0.057 Uiso calc R 1
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 0.0764(6) 0.0864(7) 0.0780(7) -0.0224(5) 0.0336(5) -0.0069(5)
O2 0.0841(7) 0.0619(6) 0.0864(7) -0.0141(5) 0.0241(5) -0.0223(5)
N1 0.0529(6) 0.0585(7) 0.0527(6) -0.0050(5) 0.0062(5) 0.0015(5)
N2 0.0780(8) 0.0774(8) 0.0744(8) -0.0006(6) 0.0196(6) -0.0184(6)
C1 0.0439(6) 0.0453(6) 0.0434(6) -0.0013(5) 0.0004(5) 0.0035(5)
C2 0.0491(6) 0.0469(6) 0.0530(7) -0.0087(5) 0.0001(5) 0.0083(5)
C3 0.0586(7) 0.0411(6) 0.0573(7) -0.0031(5) -0.0049(6) -0.0003(5)
C4 0.0490(7) 0.0543(7) 0.0501(7) 0.0059(5) -0.0020(5) -0.0003(5)
C5 0.0455(6) 0.0576(7) 0.0533(7) -0.0073(5) 0.0052(5) 0.0044(5)
C6 0.0489(6) 0.0438(6) 0.0502(7) -0.0075(5) -0.0016(5) 0.0025(5)
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
O1 N1 O2 121.65(11)
O1 N1 C1 119.37(11)
O2 N1 C1 118.97(10)
C4 N2 H2A 120.0
C4 N2 H2B 120.0
H2A N2 H2B 120.0
C6 C1 C2 120.78(11)
C6 C1 N1 119.36(10)
C2 C1 N1 119.86(10)
C3 C2 C1 119.27(11)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 121.13(11)
C2 C3 H3 119.4
C4 C3 H3 119.4
N2 C4 C3 121.32(12)
N2 C4 C5 120.31(12)
C3 C4 C5 118.37(11)
C6 C5 C4 120.69(11)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 119.76(11)
C5 C6 H6 120.1
C1 C6 H6 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2265(13)
O2 N1 1.2343(13)
N1 C1 1.4371(15)
N2 C4 1.3531(16)
N2 H2A 0.8600
N2 H2B 0.8600
C1 C6 1.3884(16)
C1 C2 1.3890(16)
C2 C3 1.3672(17)
C2 H2 0.9300
C3 C4 1.4017(17)
C3 H3 0.9300
C4 C5 1.4047(17)
C5 C6 1.3651(17)
C5 H5 0.9300
C6 H6 0.9300
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
N2 H2A O1 4_655 0.86 2.43 3.1290(17) 138.7
N2 H2B O2 4_665 0.86 2.23 3.0765(17) 168.1
C6 H6 O2 3_667 0.93 2.56 3.3229(17) 139.2
C3 H3 Cg1 2_546 0.93 2.81 3.5103(15) 132.7
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13846959
