#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/83/2218340.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_2218340
loop_
_publ_author_name
'Liang, Wen-Xian'
'Wang, Guo-Xi'
_publ_section_title
;
 2-Methyl-5-nitrobenzonitrile
;
_journal_coeditor_code           BX2137
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o972
_journal_paper_doi               10.1107/S1600536808010982
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C8 H6 N2 O2'
_chemical_formula_moiety         'C8 H6 N2 O2'
_chemical_formula_sum            'C8 H6 N2 O2'
_chemical_formula_weight         162.15
_chemical_melting_point_gt       349
_chemical_melting_point_lt       350
_chemical_name_systematic
;
2-Methyl-5-nitrobenzonitrile
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8946(8)
_cell_length_b                   7.6350(15)
_cell_length_c                   26.180(5)
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      3.09
_cell_volume                     778.1(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 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      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       ω
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            7390
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0495
_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)+(0.0668P)²+0.1332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                1273
_reflns_number_total             1761
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2137.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218340
_cod_database_fobs_code          2218340
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
N N1 0.8171(4) 0.3298(2) 0.18614(5) 0.0590(4) Uani d . 1
C C3 0.8617(4) 0.6612(2) 0.08273(6) 0.0450(4) Uani d . 1
C C2 0.7935(4) 0.5051(2) 0.10776(5) 0.0451(4) Uani d . 1
H H2A 0.6877 0.4120 0.0907 0.054 Uiso calc R 1
C C7 0.7618(5) 0.6787(2) 0.02938(6) 0.0534(4) Uani d . 1
C C4 1.0183(4) 0.8045(2) 0.10793(6) 0.0489(4) Uani d . 1
C C1 0.8882(4) 0.4929(2) 0.15883(6) 0.0469(4) Uani d . 1
N N2 0.6808(5) 0.6958(2) -0.01239(6) 0.0745(5) Uani d . 1
C C5 1.1068(4) 0.7835(2) 0.15941(7) 0.0569(5) Uani d . 1
H H5A 1.2101 0.8762 0.1770 0.068 Uiso calc R 1
O O1 0.9413(5) 0.3114(2) 0.22899(6) 0.0954(6) Uani d . 1
O O2 0.6345(4) 0.2205(2) 0.16517(6) 0.0838(5) Uani d . 1
C C6 1.0461(4) 0.6299(2) 0.18501(6) 0.0550(5) Uani d . 1
H H6A 1.1100 0.6182 0.2193 0.066 Uiso calc R 1
C C8 1.0878(5) 0.9721(2) 0.08010(7) 0.0636(5) Uani d . 1
H H8A 1.1998 1.0535 0.1030 0.095 Uiso calc R 1
H H8B 0.8748 1.0213 0.0676 0.095 Uiso calc R 1
H H8C 1.2333 0.9487 0.0519 0.095 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
N1 0.0639(9) 0.0679(10) 0.0450(8) 0.0035(8) -0.0017(7) 0.0075(7)
C3 0.0453(8) 0.0507(9) 0.0387(8) -0.0026(7) -0.0039(6) -0.0050(6)
C2 0.0460(8) 0.0481(9) 0.0407(8) -0.0017(7) -0.0045(6) -0.0051(6)
C7 0.0660(11) 0.0465(9) 0.0473(9) -0.0131(8) -0.0079(8) -0.0006(7)
C4 0.0438(8) 0.0519(9) 0.0509(9) -0.0024(7) -0.0011(7) -0.0091(7)
C1 0.0445(8) 0.0559(10) 0.0401(8) 0.0037(7) -0.0011(6) -0.0006(7)
N2 0.1069(14) 0.0667(10) 0.0486(9) -0.0268(9) -0.0196(9) 0.0072(7)
C5 0.0547(10) 0.0629(11) 0.0525(10) -0.0062(8) -0.0072(8) -0.0186(8)
O1 0.1169(13) 0.1119(13) 0.0559(8) -0.0133(10) -0.0234(8) 0.0294(8)
O2 0.1135(13) 0.0681(9) 0.0688(9) -0.0226(9) -0.0121(9) 0.0108(7)
C6 0.0540(10) 0.0721(12) 0.0385(8) 0.0022(8) -0.0078(7) -0.0093(7)
C8 0.0640(11) 0.0545(10) 0.0721(12) -0.0136(9) -0.0039(9) -0.0046(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
O2 N1 O1 123.27(16)
O2 N1 C1 118.58(14)
O1 N1 C1 118.15(15)
C4 C3 C2 122.14(14)
C4 C3 C7 118.83(14)
C2 C3 C7 119.02(13)
C1 C2 C3 117.73(14)
C1 C2 H2A 121.1
C3 C2 H2A 121.1
N2 C7 C3 178.63(19)
C5 C4 C3 117.16(15)
C5 C4 C8 121.71(15)
C3 C4 C8 121.12(15)
C2 C1 C6 122.09(15)
C2 C1 N1 118.73(14)
C6 C1 N1 119.18(14)
C6 C5 C4 121.98(15)
C6 C5 H5A 119.0
C4 C5 H5A 119.0
C5 C6 C1 118.89(15)
C5 C6 H6A 120.6
C1 C6 H6A 120.6
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O2 1.217(2)
N1 O1 1.2168(19)
N1 C1 1.467(2)
C3 C4 1.407(2)
C3 C2 1.390(2)
C3 C7 1.445(2)
C2 C1 1.380(2)
C2 H2A 0.9300
C7 N2 1.137(2)
C4 C5 1.391(2)
C4 C8 1.501(2)
C1 C6 1.385(2)
C5 C6 1.375(3)
C5 H5A 0.9300
C6 H6A 0.9300
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
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
C4 C3 C2 C1 -0.7(2)
C7 C3 C2 C1 -179.26(14)
C2 C3 C4 C5 0.6(2)
C7 C3 C4 C5 179.19(15)
C2 C3 C4 C8 -179.73(15)
C7 C3 C4 C8 -1.1(2)
C3 C2 C1 C6 0.0(2)
C3 C2 C1 N1 179.64(13)
O2 N1 C1 C2 -10.4(2)
O1 N1 C1 C2 170.40(16)
O2 N1 C1 C6 169.28(16)
O1 N1 C1 C6 -9.9(2)
C3 C4 C5 C6 0.2(2)
C8 C4 C5 C6 -179.50(16)
C4 C5 C6 C1 -0.8(3)
C2 C1 C6 C5 0.7(3)
N1 C1 C6 C5 -178.91(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 310867
