#------------------------------------------------------------------------------
#$Date: 2018-03-24 08:09:01 +0200 (Sat, 24 Mar 2018) $
#$Revision: 207101 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/91/1549130.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_1549130
loop_
_publ_author_name
'Moorthy, K.'
'NizamMohideen, M.'
'Vetrivel, S.'
'Vinoth, E.'
'Arun, A.'
_publ_section_title
;
 2-Fluoro-5-nitroaniline
;
_journal_coeditor_code           HB4212
_journal_issue                   3
_journal_name_full               IUCrData
_journal_page_first              x180425
_journal_paper_doi               10.1107/S241431461800425X
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C6 H5 F N2 O2'
_chemical_formula_moiety         'C6 H5 F N2 O2'
_chemical_formula_sum            'C6 H5 F N2 O2'
_chemical_formula_weight         156.12
_chemical_name_systematic
;
2-Fluoro-5-nitroaniline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.143(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1967(9)
_cell_length_b                   3.7559(2)
_cell_length_c                   14.4539(10)
_cell_measurement_reflns_used    2057
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.45
_cell_volume                     647.31(7)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b), WinGX (Farrugia, 2012) and PLATON
(Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker KappaCCD'
_diffrn_measurement_method       'ω and φ 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  0.0404
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7982
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         2.456
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0453P)²+0.1287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                731
_reflns_number_total             1124
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4212sup1.cif
_cod_data_source_block           I
_cod_database_code               1549130
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_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_occupancy
C C1 0.24514(17) 1.0767(5) 0.94448(14) 0.0370(5) Uani d 1
C C2 0.16370(17) 0.9076(5) 0.98328(16) 0.0423(6) Uani d 1
C C3 0.17626(19) 0.8268(5) 1.07728(16) 0.0430(6) Uani d 1
H H3 0.1187 0.7157 1.0995 0.052 Uiso calc 1
C C4 0.27553(18) 0.9127(5) 1.13846(15) 0.0402(6) Uani d 1
H H4 0.2869 0.8600 1.2026 0.048 Uiso calc 1
C C5 0.35721(17) 1.0787(5) 1.10151(13) 0.0327(5) Uani d 1
C C6 0.34464(17) 1.1593(5) 1.00692(13) 0.0343(5) Uani d 1
H H6 0.4027 1.2687 0.9850 0.041 Uiso calc 1
N N1 0.46159(16) 1.1836(4) 1.16606(12) 0.0439(5) Uani d 1
N N2 0.2278(2) 1.1426(7) 0.84863(14) 0.0563(6) Uani d 1
O O1 0.47362(16) 1.1064(6) 1.24921(11) 0.0826(7) Uani d 1
O O2 0.53201(14) 1.3472(5) 1.13505(11) 0.0627(5) Uani d 1
F F1 0.06598(11) 0.8233(4) 0.92311(10) 0.0660(5) Uani d 1
H H2B 0.158(2) 1.155(7) 0.8230(19) 0.074(9) Uiso d 1
H H2A 0.271(2) 1.293(7) 0.830(2) 0.083(11) Uiso d 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'
F F 0.0171 0.0103 '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
N2 C1 C6 122.8(2)
N2 C1 C2 121.0(2)
C6 C1 C2 116.15(19)
F1 C2 C3 119.0(2)
F1 C2 C1 116.9(2)
C3 C2 C1 124.1(2)
C2 C3 C4 119.0(2)
C2 C3 H3 120.5
C4 C3 H3 120.5
C5 C4 C3 117.85(19)
C5 C4 H4 121.1
C3 C4 H4 121.1
C4 C5 C6 123.2(2)
C4 C5 N1 118.56(18)
C6 C5 N1 118.27(18)
C5 C6 C1 119.77(19)
C5 C6 H6 120.1
C1 C6 H6 120.1
O1 N1 O2 122.5(2)
O1 N1 C5 118.28(19)
O2 N1 C5 119.18(18)
C1 N2 H2B 111.9(18)
C1 N2 H2A 117(2)
H2B N2 H2A 117(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.379(3)
C1 C6 1.387(3)
C1 C2 1.392(3)
C2 F1 1.357(2)
C2 C3 1.369(3)
C3 C4 1.379(3)
C3 H3 0.9300
C4 C5 1.375(3)
C4 H4 0.9300
C5 C6 1.377(3)
C5 N1 1.465(3)
C6 H6 0.9300
N1 O1 1.215(2)
N1 O2 1.216(2)
N2 H2B 0.85(3)
N2 H2A 0.85(3)
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 H2B F1 . 0.85(3) 2.37(3) 2.718(3) 105(2)
N2 H2B O1 4_585 0.85(3) 2.45(3) 3.270(3) 162(2)
C6 H6 O2 3_687 0.93 2.51 3.348(3) 150
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
N2 C1 C2 F1 -2.2(3)
C6 C1 C2 F1 -179.70(16)
N2 C1 C2 C3 178.47(19)
C6 C1 C2 C3 1.0(3)
F1 C2 C3 C4 -179.95(17)
C1 C2 C3 C4 -0.7(3)
C2 C3 C4 C5 0.4(3)
C3 C4 C5 C6 -0.6(3)
C3 C4 C5 N1 177.80(17)
C4 C5 C6 C1 1.0(3)
N1 C5 C6 C1 -177.43(16)
N2 C1 C6 C5 -178.51(18)
C2 C1 C6 C5 -1.1(3)
C4 C5 N1 O1 3.0(3)
C6 C5 N1 O1 -178.58(19)
C4 C5 N1 O2 -176.16(18)
C6 C5 N1 O2 2.3(3)

_cod_database_fobs_code 1549130
