#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/97/2219726.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_2219726
loop_
_publ_author_name
'Cui, Li-Jing'
'Dai, Jing'
_publ_section_title
;
 4-Methyl-3-nitrobenzonitrile
;
_journal_coeditor_code           WK2090
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1898
_journal_paper_doi               10.1107/S1600536808027414
_journal_volume                  64
_journal_year                    2008
_chemical_formula_moiety         'C8 H6 N2 O2'
_chemical_formula_sum            'C8 H6 N2 O2'
_chemical_formula_weight         162.15
_chemical_name_systematic        ?
_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(3)
_cell_angle_beta                 99.13(3)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            4
_cell_length_a                   3.9088(8)
_cell_length_b                   13.576(3)
_cell_length_c                   14.819(4)
_cell_measurement_reflns_used    1764
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      3.07
_cell_volume                     776.4(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      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7589
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0676
_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)+(0.1036P)²+0.2336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2077
_reflns_number_gt                1336
_reflns_number_total             1761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            wk2090.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219726
_cod_database_fobs_code          2219726
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 1.0921(7) 0.79875(18) 0.59741(14) 0.1001(9) Uani d . 1
O O2 1.3658(7) 0.89476(18) 0.52048(17) 0.0932(8) Uani d . 1
N N1 1.1627(5) 0.82762(16) 0.52533(14) 0.0584(6) Uani d . 1
N N2 0.5214(8) 0.45178(18) 0.38967(18) 0.0803(8) Uani d . 1
C C1 1.0021(5) 0.77768(15) 0.44045(14) 0.0444(5) Uani d . 1
C C8 0.6195(7) 0.53049(18) 0.38358(16) 0.0568(6) Uani d . 1
C C2 0.9631(5) 0.82620(16) 0.35611(15) 0.0462(5) Uani d . 1
C C6 0.8914(6) 0.68242(16) 0.45126(14) 0.0470(5) Uani d . 1
H H6 0.9185 0.6535 0.5088 0.056 Uiso calc R 1
C C4 0.6963(6) 0.67560(17) 0.28898(15) 0.0530(6) Uani d . 1
H H4 0.5942 0.6412 0.2374 0.064 Uiso calc R 1
C C5 0.7388(6) 0.63055(16) 0.37444(15) 0.0463(5) Uani d . 1
C C3 0.8057(7) 0.77130(18) 0.28090(16) 0.0559(6) Uani d . 1
H H3 0.7738 0.8004 0.2234 0.067 Uiso calc R 1
C C7 1.0660(8) 0.93151(18) 0.3406(2) 0.0672(7) Uani d . 1
H H7A 1.1700 0.9601 0.3976 0.101 Uiso calc R 1
H H7B 0.8641 0.9687 0.3157 0.101 Uiso calc R 1
H H7C 1.2293 0.9326 0.2985 0.101 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 0.145(2) 0.1075(18) 0.0430(11) -0.0405(15) 0.0006(12) -0.0087(11)
O2 0.0966(17) 0.0881(15) 0.0906(16) -0.0397(13) 0.0017(12) -0.0237(12)
N1 0.0605(12) 0.0593(12) 0.0523(12) -0.0039(10) -0.0011(9) -0.0117(9)
N2 0.106(2) 0.0562(14) 0.0755(16) -0.0203(13) 0.0039(14) -0.0061(11)
C1 0.0410(10) 0.0476(12) 0.0436(11) 0.0013(9) 0.0041(8) -0.0064(9)
C8 0.0662(15) 0.0501(13) 0.0521(14) -0.0036(11) 0.0029(11) -0.0063(10)
C2 0.0447(11) 0.0456(11) 0.0496(12) 0.0061(9) 0.0119(9) 0.0026(9)
C6 0.0517(12) 0.0478(12) 0.0402(11) 0.0010(9) 0.0034(9) 0.0011(9)
C4 0.0619(14) 0.0521(13) 0.0417(12) 0.0062(10) -0.0014(10) -0.0048(9)
C5 0.0483(12) 0.0446(11) 0.0452(12) 0.0015(9) 0.0049(8) -0.0036(9)
C3 0.0708(16) 0.0543(13) 0.0415(12) 0.0083(11) 0.0058(10) 0.0059(9)
C7 0.0707(17) 0.0504(14) 0.0807(19) -0.0005(12) 0.0125(14) 0.0096(12)
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'
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'
H H 0.0000 0.0000 '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 122.4(2)
O1 N1 C1 118.5(2)
O2 N1 C1 119.1(2)
C6 C1 C2 123.55(19)
C6 C1 N1 115.43(19)
C2 C1 N1 121.0(2)
N2 C8 C5 178.9(3)
C3 C2 C1 115.6(2)
C3 C2 C7 118.4(2)
C1 C2 C7 125.9(2)
C1 C6 C5 118.75(19)
C1 C6 H6 120.6
C5 C6 H6 120.6
C3 C4 C5 119.9(2)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 119.7(2)
C6 C5 C8 120.1(2)
C4 C5 C8 120.2(2)
C4 C3 C2 122.4(2)
C4 C3 H3 118.8
C2 C3 H3 118.8
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.210(3)
O2 N1 1.218(3)
N1 C1 1.478(3)
N2 C8 1.144(3)
C1 C6 1.381(3)
C1 C2 1.400(3)
C8 C5 1.450(3)
C2 C3 1.400(3)
C2 C7 1.513(3)
C6 C5 1.390(3)
C6 H6 0.9300
C4 C3 1.379(3)
C4 C5 1.392(3)
C4 H4 0.9300
C3 H3 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 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
O1 N1 C1 C6 -23.2(3)
O2 N1 C1 C6 155.4(2)
O1 N1 C1 C2 155.8(2)
O2 N1 C1 C2 -25.6(3)
C6 C1 C2 C3 -0.8(3)
N1 C1 C2 C3 -179.68(19)
C6 C1 C2 C7 177.4(2)
N1 C1 C2 C7 -1.4(3)
C2 C1 C6 C5 1.3(3)
N1 C1 C6 C5 -179.76(19)
C1 C6 C5 C4 -0.9(3)
C1 C6 C5 C8 -179.9(2)
C3 C4 C5 C6 0.0(3)
C3 C4 C5 C8 179.1(2)
C5 C4 C3 C2 0.5(4)
C1 C2 C3 C4 -0.1(3)
C7 C2 C3 C4 -178.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 512297
