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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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# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-bromo-4-methylbenzonitrile
;
_chemical_name_common
;
2-bromo-4-methylbenzonitrile
;
_chemical_formula_moiety     'C8 H6 Br N'
_chemical_formula_sum     'C8 H6 Br N'
_chemical_formula_iupac     'C8 H6 Br N'
_chemical_formula_weight     196.05
_chemical_melting_point     ?
_symmetry_cell_setting     'Triclinic'
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.5168(11)
_cell_length_b     7.8383(11)
_cell_length_c     7.9428(11)
_cell_angle_alpha     69.243(7)
_cell_angle_beta     64.375(8)
_cell_angle_gamma     87.567(8)
_cell_volume     391.14(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3073
_cell_measurement_theta_min     2.18
_cell_measurement_theta_max     21.15
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.41
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.665
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     192
_exptl_absorpt_coefficient_mu     5.172
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min     0.226
_exptl_absorpt_correction_T_max     0.440
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(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     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8084
_diffrn_reflns_av_R_equivalents     0.0247
_diffrn_reflns_av_sigmaI/netI     0.0294
_diffrn_reflns_theta_min     2.80
_diffrn_reflns_theta_max     28.32
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² 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     1921
_reflns_number_gt     1244
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0672
_refine_ls_R_factor_gt     0.0332
_refine_ls_wR_factor_gt     0.0731
_refine_ls_wR_factor_ref     0.0839
_refine_ls_goodness_of_fit_ref     1.007
_refine_ls_restrained_S_all     1.007
_refine_ls_number_reflns     1921
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0326P)²+0.2649P] where P=(Fo²+2Fc²)/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     0.444
_refine_diff_density_min     -0.491
_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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                              'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
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
    Br Br1 0.32613(7) 0.89370(4) 0.35907(6) 0.07874(19) Uani d . 1 . .
    C C1 0.2019(4) 0.3498(4) 0.7427(4) 0.0525(7) Uani d . 1 . .
    C C2 0.2395(4) 0.5395(4) 0.6606(4) 0.0512(7) Uani d . 1 . .
    H H2 0.2419 0.6033 0.7387 0.061 Uiso calc R 1 . .
    C C3 0.2732(4) 0.6352(4) 0.4660(4) 0.0457(6) Uani d . 1 . .
    C C4 0.2711(4) 0.5439(4) 0.3461(4) 0.0445(6) Uani d . 1 . .
    C C5 0.2349(5) 0.3537(4) 0.4270(5) 0.0532(7) Uani d . 1 . .
    H H5 0.2337 0.2899 0.3485 0.064 Uiso calc R 1 . .
    C C6 0.2008(5) 0.2588(4) 0.6222(5) 0.0582(8) Uani d . 1 . .
    H H6 0.1765 0.1310 0.6747 0.070 Uiso calc R 1 . .
    C C7 0.1639(6) 0.2446(5) 0.9569(5) 0.0764(10) Uani d . 1 . .
    H H7A 0.2191 0.3191 1.0006 0.115 Uiso calc R 1 . .
    H H7B 0.2253 0.1339 0.9654 0.115 Uiso calc R 1 . .
    H H7C 0.0231 0.2136 1.0415 0.115 Uiso calc R 1 . .
    C C8 0.3088(5) 0.6413(4) 0.1400(5) 0.0540(7) Uani d . 1 . .
    N N1 0.3389(5) 0.7126(4) -0.0230(5) 0.0771(9) Uani d . 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
    Br1 0.1226(4) 0.0413(2) 0.0893(3) 0.01752(18) -0.0609(3) -0.02676(18)
    C1 0.0514(18) 0.0578(18) 0.0451(17) 0.0061(14) -0.0231(14) -0.0136(14)
    C2 0.0571(18) 0.0587(18) 0.0515(18) 0.0159(14) -0.0288(15) -0.0308(15)
    C3 0.0525(17) 0.0403(14) 0.0491(17) 0.0096(12) -0.0251(14) -0.0193(13)
    C4 0.0449(16) 0.0480(16) 0.0410(16) 0.0047(12) -0.0188(13) -0.0174(13)
    C5 0.0641(19) 0.0478(16) 0.0525(18) 0.0029(14) -0.0249(15) -0.0249(14)
    C6 0.069(2) 0.0437(16) 0.056(2) 0.0005(14) -0.0258(16) -0.0151(15)
    C7 0.086(3) 0.085(3) 0.050(2) 0.007(2) -0.0321(19) -0.0132(18)
    C8 0.0586(19) 0.0560(18) 0.0478(19) -0.0003(14) -0.0225(15) -0.0205(15)
    N1 0.098(2) 0.077(2) 0.0512(18) -0.0056(17) -0.0332(17) -0.0171(16)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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
    Br1 C3 . 1.882(3) ?
    C1 C2 . 1.380(4) ?
    C1 C6 . 1.384(4) ?
    C1 C7 . 1.503(4) ?
    C2 C3 . 1.368(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.384(4) ?
    C4 C5 . 1.383(4) ?
    C4 C8 . 1.440(4) ?
    C5 C6 . 1.371(4) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 N1 . 1.133(4) ?
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
    C2 C1 C6 . . 118.2(3) ?
    C2 C1 C7 . . 121.0(3) ?
    C6 C1 C7 . . 120.8(3) ?
    C3 C2 C1 . . 121.0(3) ?
    C3 C2 H2 . . 119.5 ?
    C1 C2 H2 . . 119.5 ?
    C2 C3 C4 . . 120.8(3) ?
    C2 C3 Br1 . . 119.6(2) ?
    C4 C3 Br1 . . 119.6(2) ?
    C5 C4 C3 . . 118.6(3) ?
    C5 C4 C8 . . 119.6(3) ?
    C3 C4 C8 . . 121.8(3) ?
    C6 C5 C4 . . 120.3(3) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C5 C6 C1 . . 121.2(3) ?
    C5 C6 H6 . . 119.4 ?
    C1 C6 H6 . . 119.4 ?
    C1 C7 H7A . . 109.5 ?
    C1 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C1 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    N1 C8 C4 . . 177.7(3) ?
data_global
_journal_date_recd_electronic     2009-11-16
_journal_date_accepted     2009-11-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     12
_journal_page_first     o3166
_journal_page_last     o3166
_journal_paper_category     QO
_journal_coeditor_code     HB5232
_publ_contact_author_name     'Munawar, Ali Munawar'
_publ_contact_author_address
;
Institute of Chemistry, University of the Punjab,
New Campus, Lahore,
Pakistan
;
_publ_contact_author_email     munawaralimunawar@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '+92429230463'
_publ_section_title
;
2-Bromo-4-methylbenzonitrile
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Shahid, Muhammad' .
;
Institute of Chemistry, University of the Punjab,
New Campus, Lahore,
Pakistan
;
    'Munawar, Munawar Ali' .
;
Institute of Chemistry, University of the Punjab,
New Campus, Lahore,
Pakistan
;
    'Nadeem, Sohail' .
;
Institute of Chemistry, University of the Punjab,
New Campus, Lahore,
Pakistan
;
    'Nasir, Waqar' .
;
Institute of Chemistry, University of the Punjab,
New Campus, Lahore,
Pakistan
;
    'Salim, Muhammad' .
;
Institute of Chemistry, University of the Punjab,
New Campus, Lahore,
Pakistan
;
