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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      #
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# of the IUCr Commission on Journals.                                        #
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# are given in the paper "The Crystallographic Information File (CIF):       #
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#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
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#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_I
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2008-09-15
_journal_date_accepted     2008-09-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     10
_journal_page_first     o1970
_journal_page_last     o1970
_journal_paper_category     QO
_journal_coeditor_code     HK2533
_publ_contact_author_name     ' Nasim Hasan Rama'
_publ_contact_author_address
;
DEPARTMENT OF CHEMISTRY,
QUAID-I-AZAM UNIVERSITY,
ISLAMABAD 45320,
PAKISTAN
;
_publ_contact_author_email     'nasimhrama@yahoo.com'
_publ_contact_author_fax     '92-51-2873869'
_publ_contact_author_phone     '92-51-2211034'
_publ_section_title
;
Methyl 2,5-dichlorobenzoate
;
loop_
    _publ_author_name
    _publ_author_address
    'Tariq Mahmood Babar'
;
Department of Chemistry,
Quaid-i-Azam Univeristy,
Islamabad 45320,
Pakistan
;
    'Ghulam Qadeer'
;
Department of Chemistry,
Quaid-i-Azam Univeristy,
Islamabad 45320,
Pakistan
;
    'Nasim Hasan Rama'
;
Department of Chemistry,
Quaid-i-Azam Univeristy,
Islamabad 45320,
Pakistan
;
    ' Ales Ruzicka'
;  Department of General and Inorganic Chemistry,
   Faculty of Chemical Technology,
   University of Pardubice,
   Nam. Cs. Legii' 565, 53210 Pardubice,
   Czech Republic
;
    ' Zdenka Padelkova'
; Department of General and Inorganic Chemistry,
  Faculty of Chemical Technology,
  University of Pardubice,
  Nam. Cs. Legii' 565, 53210 Pardubice,
  Czech Republic
;
_chemical_name_systematic
;
methyl 2,5-dichlorobenzoate
;
_chemical_name_common     'Dichloro-ester'
_chemical_formula_moiety     'C8 H6 Cl2 O2'
_chemical_formula_sum     'C8 H6 Cl2 O2'
_chemical_formula_iupac     'C8 H6 Cl2 O2'
_chemical_formula_weight     205.03
_chemical_melting_point     '319(2)'
_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     3.8452(3)
_cell_length_b     7.0158(4)
_cell_length_c     15.8510(10)
_cell_angle_alpha     77.189(6)
_cell_angle_beta     89.130(7)
_cell_angle_gamma     83.741(5)
_cell_volume     414.46(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     6024
_cell_measurement_theta_min     1
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     150.0(10)
_exptl_crystal_description     'needle'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.680
_exptl_crystal_size_mid     0.108
_exptl_crystal_size_min     0.060
_exptl_crystal_density_diffrn     1.643
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     208
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    0 1 1 0.036
    0 -1 -1 0.046
    1 0 0 0.312
    -1 0 0 0.332
    0 0 -1 0.012
    0 0 1 0.030
_exptl_absorpt_coefficient_mu     0.732
_exptl_absorpt_correction_type     Gaussian
_exptl_absorpt_process_details
;
(Coppens, 1970)
;
_exptl_absorpt_correction_T_min     0.864
_exptl_absorpt_correction_T_max     0.971
_diffrn_ambient_temperature     150.0(10)
_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--Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     5966
_diffrn_reflns_av_R_equivalents     0.1099
_diffrn_reflns_av_sigmaI/netI     0.0720
_diffrn_reflns_theta_min     2.64
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     0.976
_diffrn_measured_fraction_theta_full     0.976
_diffrn_reflns_limit_h_min     -4
_diffrn_reflns_limit_h_max     4
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted
<i>R</i>-factor <i>wR</i> and goodness of fit <i>S</i> are based
on <i>F</i>^2^, conventional <i>R</i>-factors <i>R</i> are based
on <i>F</i>, with <i>F</i> set to zero for negative <i>F</i>^2^.
The threshold expression of <i>F</i>^2^ > \s(<i>F</i>^2^) is used
only for calculating <i>R</i>-factors(gt) <i>etc</i>. and is not
relevant to the choice of reflections for refinement. <i>R</i>-factors
based on <i>F</i>^2^ are statistically about twice as large as those
based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     1840
_reflns_number_gt     1455
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0720
_refine_ls_R_factor_gt     0.0532
_refine_ls_wR_factor_gt     0.1295
_refine_ls_wR_factor_ref     0.1456
_refine_ls_goodness_of_fit_ref     1.095
_refine_ls_restrained_S_all     1.095
_refine_ls_number_reflns     1840
_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^)+(0.0527P)^2^+0.5264P] 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     0.438
_refine_diff_density_min     -0.571
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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     'COLLECT (Hooft, 1998)'
_computing_cell_refinement
                    'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction
                    'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare <i>et al.</i>,  1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97 (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
    Cl Cl1 0.6965(2) 0.52269(12) 0.70713(5) 0.0309(2) Uani d . 1 . .
    Cl Cl2 1.3585(2) -0.28182(13) 0.92310(5) 0.0361(3) Uani d . 1 . .
    O O1 0.6439(7) -0.0150(4) 0.62680(14) 0.0347(6) Uani d . 1 . .
    O O2 0.8542(6) 0.2744(4) 0.57949(13) 0.0288(5) Uani d . 1 . .
    C C1 0.9066(8) 0.1286(5) 0.72871(18) 0.0220(6) Uani d . 1 . .
    C C2 0.8841(8) 0.2952(5) 0.76262(19) 0.0235(6) Uani d . 1 . .
    C C3 1.0100(9) 0.2857(5) 0.8458(2) 0.0278(7) Uani d . 1 . .
    H H3 0.9954 0.3983 0.8680 0.033 Uiso d R 1 . .
    C C4 1.1574(9) 0.1080(5) 0.89485(19) 0.0286(7) Uani d . 1 . .
    H H4 1.2435 0.1006 0.9501 0.034 Uiso d R 1 . .
    C C5 1.1755(8) -0.0580(5) 0.8613(2) 0.0257(7) Uani d . 1 . .
    C C6 1.0489(8) -0.0510(5) 0.77933(19) 0.0245(6) Uani d . 1 . .
    H H6 1.0581 -0.1648 0.7581 0.029 Uiso d R 1 . .
    C C7 0.7825(8) 0.1206(5) 0.64006(18) 0.0229(6) Uani d . 1 . .
    C C8 0.7421(9) 0.2749(5) 0.49289(19) 0.0294(7) Uani d . 1 . .
    H H8A 0.8509 0.1593 0.4761 0.035 Uiso d R 1 . .
    H H8B 0.8089 0.3898 0.4536 0.035 Uiso d R 1 . .
    H H8C 0.4924 0.2757 0.4914 0.035 Uiso d 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
    Cl1 0.0411(5) 0.0249(4) 0.0250(4) 0.0029(3) -0.0044(3) -0.0047(3)
    Cl2 0.0429(5) 0.0328(5) 0.0276(4) 0.0027(4) -0.0115(3) 0.0014(3)
    O1 0.0496(16) 0.0344(14) 0.0231(11) -0.0124(11) -0.0066(10) -0.0089(10)
    O2 0.0368(13) 0.0354(13) 0.0137(10) -0.0082(10) -0.0056(8) -0.0017(9)
    C1 0.0214(15) 0.0287(16) 0.0156(13) -0.0036(12) -0.0005(10) -0.0039(11)
    C2 0.0233(15) 0.0256(16) 0.0205(14) -0.0043(12) -0.0010(11) -0.0021(12)
    C3 0.0331(18) 0.0295(18) 0.0230(15) -0.0050(13) -0.0007(12) -0.0096(13)
    C4 0.0336(18) 0.0348(18) 0.0172(14) -0.0055(14) -0.0045(12) -0.0042(12)
    C5 0.0233(16) 0.0303(17) 0.0206(14) -0.0028(12) -0.0014(11) 0.0003(12)
    C6 0.0302(17) 0.0236(16) 0.0205(14) -0.0008(12) -0.0026(11) -0.0073(12)
    C7 0.0257(15) 0.0265(16) 0.0166(13) 0.0004(12) -0.0013(11) -0.0062(11)
    C8 0.0367(19) 0.0368(19) 0.0141(13) 0.0003(14) -0.0047(12) -0.0061(12)
_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
    Cl1 C2 . 1.728(3) ?
    Cl2 C5 . 1.737(3) ?
    O1 C7 . 1.199(4) ?
    O2 C7 . 1.326(4) ?
    O2 C8 . 1.444(3) ?
    C1 C2 . 1.385(5) ?
    C1 C6 . 1.395(4) ?
    C1 C7 . 1.505(4) ?
    C2 C3 . 1.396(4) ?
    C3 H3 . 0.9300 ?
    C4 C3 . 1.382(5) ?
    C4 C5 . 1.378(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.384(4) ?
    C6 H6 . 0.9301 ?
    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
    C7 O2 C8 . . 115.5(3) ?
    C2 C1 C6 . . 119.3(3) ?
    C2 C1 C7 . . 125.6(3) ?
    C6 C1 C7 . . 115.1(3) ?
    C1 C2 Cl1 . . 123.1(2) ?
    C1 C2 C3 . . 120.7(3) ?
    C3 C2 Cl1 . . 116.3(3) ?
    C4 C3 C2 . . 119.7(3) ?
    C4 C3 H3 . . 120.1 ?
    C2 C3 H3 . . 120.3 ?
    C5 C4 C3 . . 119.5(3) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.2 ?
    C4 C5 C6 . . 121.4(3) ?
    C4 C5 Cl2 . . 119.7(2) ?
    C6 C5 Cl2 . . 118.9(3) ?
    C5 C6 C1 . . 119.3(3) ?
    C5 C6 H6 . . 120.4 ?
    C1 C6 H6 . . 120.2 ?
    O1 C7 O2 . . 124.7(3) ?
    O1 C7 C1 . . 122.4(3) ?
    O2 C7 C1 . . 112.9(3) ?
    O2 C8 H8A . . 109.4 ?
    O2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    O2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?