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### Electronic paper (Acta Crystallographica Section E) ###
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# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section E. It conforms to the requirements of Notes #
# for Authors for Section E, and has been peer reviewed under the auspices #
# of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
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data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
2-Methyl-5-nitrobenzonitrile
;
_chemical_name_common ?
_chemical_formula_moiety 'C8 H6 N2 O2'
_chemical_formula_sum 'C8 H6 N2 O2'
_chemical_formula_iupac 'C8 H6 N2 O2'
_chemical_formula_weight 162.15
_chemical_melting_point ?
_chemical_melting_point_gt 349
_chemical_melting_point_lt 350
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
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'
_cell_length_a 3.8946(8)
_cell_length_b 7.6350(15)
_cell_length_c 26.180(5)
_cell_angle_alpha 90.00
_cell_angle_beta 91.65(3)
_cell_angle_gamma 90.00
_cell_volume 778.1(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 1763
_cell_measurement_theta_min 3.09
_cell_measurement_theta_max 27.66
_cell_measurement_temperature 293(2)
_exptl_crystal_description 'block'
_exptl_crystal_colour 'Colourless'
_exptl_crystal_size_max 0.4
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.2
_exptl_crystal_density_diffrn 1.384
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 336
_exptl_absorpt_coefficient_mu 0.103
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_absorpt_correction_T_min 0.93
_exptl_absorpt_correction_T_max 0.98
_exptl_special_details
;
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Rigaku Mercury2'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number 7390
_diffrn_reflns_av_R_equivalents 0.0385
_diffrn_reflns_av_sigmaI/netI 0.0307
_diffrn_reflns_theta_min 3.09
_diffrn_reflns_theta_max 27.47
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -33
_diffrn_reflns_limit_l_max 33
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 1761
_reflns_number_gt 1273
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0707
_refine_ls_R_factor_gt 0.0495
_refine_ls_wR_factor_gt 0.1269
_refine_ls_wR_factor_ref 0.1408
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_restrained_S_all 1.040
_refine_ls_number_reflns 1761
_refine_ls_number_parameters 109
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+0.1332P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.144
_refine_diff_density_min -0.176
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
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'
_computing_data_collection 'CrystalClear (Rigaku/MSC, 2005)'
_computing_cell_refinement 'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction 'CrystalClear (Rigaku/MSC, 2005)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
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_disorder_assembly
_atom_site_disorder_group
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)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
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_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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
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) ?
data_global
_journal_date_recd_electronic 2008-03-31
_journal_date_accepted 2008-04-19
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2008
_journal_volume 64
_journal_issue 6
_journal_page_first o972
_journal_page_last o972
_journal_paper_category QO
_journal_coeditor_code BX2137
_publ_contact_author_name 'Dr Guo-Xi Wang'
_publ_contact_author_address
;
Ordered Matter Science Research Center, College of Chemistry and Chemical
Engineering, Southeast UniVersity,
Nanjing 210096, P. R. China
;
_publ_contact_author_email fudavid88@yahoo.com.cn
_publ_contact_author_fax '862552090626'
_publ_contact_author_phone '862552090626'
_publ_section_title
;
2-Methyl-5-nitrobenzonitrile
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Liang, Wen-Xian' .
;
Ordered Matter Science Research Center,
College of Chemistry and Chemical Engineering, Southeast University,
Nanjing 210096, People's Republic of China
;
'Wang, Guo-Xi' .
;
Ordered Matter Science Research Center,
College of Chemistry and Chemical Engineering, Southeast University,
Nanjing 210096, People's Republic of China
;