#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/56/2235604.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_2235604
loop_
_publ_author_name
'Sun, Feng'
'Shen, Xuan'
'Zhao, Rui'
'Wang, Xin'
'Zhu, Dun-Ru'
_publ_section_title
;
 2-(2,4-Difluorophenyl)-5-nitropyridine
;
_journal_coeditor_code           RZ2765
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2001
_journal_paper_doi               10.1107/S1600536812024713
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H6 F2 N2 O2'
_chemical_formula_moiety         'C11 H6 F2 N2 O2'
_chemical_formula_sum            'C11 H6 F2 N2 O2'
_chemical_formula_weight         236.18
_chemical_name_systematic
;
2-(2,4-Difluorophenyl)-5-nitropyridine
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.185(4)
_cell_length_b                   3.7457(6)
_cell_length_c                   11.894(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      1.88
_cell_volume                     988.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6331
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.115
_refine_ls_abs_structure_details 'Flack (1983), 823 Friedel pairs'
_refine_ls_abs_structure_Flack   1.3(9)
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0338
_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)+(0.0417P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                1450
_reflns_number_total             1750
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2765.cif
_cod_data_source_block           I
_cod_database_code               2235604
_cod_database_fobs_code          2235604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
_atom_site_symmetry_multiplicity
F F1 0.43717(7) 0.8814(4) 0.19399(11) 0.0706(5) Uani d . 1 1
F F2 0.64096(6) 0.8761(5) 0.29027(14) 0.0783(5) Uani d . 1 1
N N1 0.39001(8) 0.6832(5) 0.52314(14) 0.0468(5) Uani d . 1 1
N N2 0.23174(9) 0.3925(7) 0.5480(2) 0.0604(6) Uani d . 1 1
C C1 0.33559(10) 0.6124(6) 0.56308(18) 0.0487(6) Uani d . 1 1
H H1A 0.3278 0.6546 0.6388 0.058 Uiso calc R 1 1
C C2 0.29008(9) 0.4788(6) 0.4966(2) 0.0461(5) Uani d . 1 1
C C3 0.29993(10) 0.4202(6) 0.38367(19) 0.0499(6) Uani d . 1 1
H H3A 0.2696 0.3316 0.3376 0.060 Uiso calc R 1 1
C C4 0.35623(9) 0.4973(6) 0.34139(19) 0.0480(6) Uani d . 1 1
H H4A 0.3644 0.4647 0.2654 0.058 Uiso calc R 1 1
C C5 0.40050(9) 0.6236(5) 0.41293(17) 0.0392(5) Uani d . 1 1
C C6 0.46353(9) 0.6929(5) 0.37757(17) 0.0406(5) Uani d . 1 1
C C7 0.48022(10) 0.8139(6) 0.27144(19) 0.0457(6) Uani d . 1 1
C C8 0.53882(12) 0.8781(6) 0.2407(2) 0.0529(6) Uani d . 1 1
H H8A 0.5485 0.9618 0.1693 0.064 Uiso calc R 1 1
C C9 0.58240(10) 0.8137(6) 0.3194(2) 0.0524(6) Uani d . 1 1
C C10 0.57000(11) 0.6967(7) 0.4255(2) 0.0552(7) Uani d . 1 1
H H10A 0.6007 0.6581 0.4773 0.066 Uiso calc R 1 1
C C11 0.51028(9) 0.6372(6) 0.45341(19) 0.0468(6) Uani d . 1 1
H H11A 0.5011 0.5571 0.5254 0.056 Uiso calc R 1 1
O O1 0.19644(9) 0.2185(6) 0.49287(19) 0.0910(7) Uani d . 1 1
O O2 0.22205(9) 0.4973(7) 0.6427(2) 0.1016(8) Uani d . 1 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
F1 0.0672(10) 0.0979(13) 0.0468(8) 0.0059(9) -0.0017(7) 0.0135(8)
F2 0.0529(8) 0.1004(11) 0.0818(11) -0.0123(8) 0.0206(8) -0.0020(9)
N1 0.0453(11) 0.0560(12) 0.0390(11) -0.0035(9) 0.0008(8) -0.0029(9)
N2 0.0466(13) 0.0676(13) 0.0671(16) -0.0070(11) 0.0044(12) 0.0016(11)
C1 0.0491(13) 0.0584(14) 0.0387(13) -0.0033(12) 0.0016(10) -0.0016(10)
C2 0.0423(12) 0.0445(12) 0.0514(15) 0.0006(10) 0.0018(11) 0.0024(11)
C3 0.0468(13) 0.0535(13) 0.0494(14) -0.0034(11) -0.0103(11) -0.0086(12)
C4 0.0531(14) 0.0548(14) 0.0360(12) 0.0004(11) -0.0040(11) -0.0040(11)
C5 0.0446(12) 0.0343(11) 0.0386(11) 0.0014(10) -0.0010(9) 0.0006(9)
C6 0.0492(14) 0.0339(11) 0.0387(12) 0.0036(9) 0.0022(11) -0.0021(10)
C7 0.0543(15) 0.0437(13) 0.0392(12) 0.0042(11) 0.0012(11) 0.0027(11)
C8 0.0614(16) 0.0494(16) 0.0480(13) -0.0010(12) 0.0133(12) 0.0017(11)
C9 0.0449(14) 0.0506(14) 0.0617(16) -0.0035(11) 0.0146(13) -0.0053(12)
C10 0.0486(15) 0.0605(16) 0.0564(16) 0.0036(11) 0.0012(12) 0.0028(13)
C11 0.0443(13) 0.0487(14) 0.0474(13) 0.0022(10) 0.0016(11) 0.0038(11)
O1 0.0561(11) 0.1191(18) 0.0978(18) -0.0343(12) -0.0064(12) -0.0072(13)
O2 0.0777(15) 0.151(2) 0.0764(15) -0.0335(14) 0.0293(12) -0.0233(16)
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
C1 N1 C5 118.19(19)
O1 N2 O2 124.2(2)
O1 N2 C2 117.6(2)
O2 N2 C2 118.2(2)
N1 C1 C2 122.4(2)
N1 C1 H1A 118.8
C2 C1 H1A 118.8
C1 C2 C3 120.1(2)
C1 C2 N2 119.2(2)
C3 C2 N2 120.7(2)
C4 C3 C2 117.8(2)
C4 C3 H3A 121.1
C2 C3 H3A 121.1
C3 C4 C5 119.4(2)
C3 C4 H4A 120.3
C5 C4 H4A 120.3
N1 C5 C4 122.1(2)
N1 C5 C6 114.14(19)
C4 C5 C6 123.72(19)
C11 C6 C7 116.04(19)
C11 C6 C5 119.54(19)
C7 C6 C5 124.4(2)
F1 C7 C8 117.1(2)
F1 C7 C6 119.44(19)
C8 C7 C6 123.5(2)
C9 C8 C7 117.1(2)
C9 C8 H8A 121.4
C7 C8 H8A 121.4
C10 C9 F2 118.8(2)
C10 C9 C8 123.2(2)
F2 C9 C8 118.0(2)
C9 C10 C11 117.8(2)
C9 C10 H10A 121.1
C11 C10 H10A 121.1
C10 C11 C6 122.3(2)
C10 C11 H11A 118.9
C6 C11 H11A 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C7 1.351(3)
F2 C9 1.365(2)
N1 C1 1.324(3)
N1 C5 1.350(3)
N2 O1 1.212(3)
N2 O2 1.213(3)
N2 C2 1.467(3)
C1 C2 1.377(3)
C1 H1A 0.9300
C2 C3 1.378(3)
C3 C4 1.377(3)
C3 H3A 0.9300
C4 C5 1.383(3)
C4 H4A 0.9300
C5 C6 1.483(3)
C6 C11 1.390(3)
C6 C7 1.391(3)
C7 C8 1.372(3)
C8 C9 1.367(4)
C8 H8A 0.9300
C9 C10 1.364(4)
C10 C11 1.384(3)
C10 H10A 0.9300
C11 H11A 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
_geom_hbond_publ_flag
C10 H10A O1 3_555 0.93 2.56 3.306(3) 138 yes
C8 H8A N1 2_674 0.93 2.58 3.448(3) 156 yes
C4 H4A F1 ? 0.93 2.40 2.893(3) 113 yes
