##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# 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_global
_audit_creation_method     ?
_journal_date_recd_electronic     2008-07-05
_journal_date_accepted     2008-07-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1542
_journal_page_last     o1542
_journal_paper_category     QO
_journal_coeditor_code     BQ2090
_publ_contact_author
;Muhammad Nawaz Tahir
University of Sargodha
Department of Physics
Sargodha
Pakistan
;
_publ_contact_author_email     'dmntahir_uos@yahoo.com'
_publ_contact_author_fax     '0092 48 32 22 121'
_publ_contact_author_phone     '0092 48 92 30 170'
_publ_section_title
;
3-(4-Chlorophenyl)-2-methylacrylic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Muhammad, Niaz'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
    'Tahir, M. Nawaz'
;
University of Sargodha
Department of Physics
Sargodha
Pakistan
;
    'Zia-ur-Rehman'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
    'Ali, Saqib'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
    'Shaheen, Farkhanda'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-(4-Chlorophenyl)-2-methylacrylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H9 Cl O2'
_chemical_formula_sum     'C10 H9 Cl O2'
_chemical_formula_iupac     'C10 H9 Cl O2'
_chemical_formula_weight     196.62
_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     7.2164(6)
_cell_length_b     8.2746(7)
_cell_length_c     9.1762(8)
_cell_angle_alpha     115.182(4)
_cell_angle_beta     108.022(4)
_cell_angle_gamma     90.052(5)
_cell_volume     465.91(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2692
_cell_measurement_theta_min     2.61
_cell_measurement_theta_max     30.25
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.402
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     204
_exptl_absorpt_coefficient_mu     0.371
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.910
_exptl_absorpt_correction_T_max     0.930
_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     ω
_diffrn_detector_area_resol_mean     7.2
_diffrn_reflns_number     7513
_diffrn_reflns_av_R_equivalents     0.0291
_diffrn_reflns_av_sigmaI/netI     0.0387
_diffrn_reflns_theta_min     2.61
_diffrn_reflns_theta_max     30.25
_diffrn_reflns_theta_full     30.25
_diffrn_measured_fraction_theta_max     0.965
_diffrn_measured_fraction_theta_full     0.965
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_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 >
σ(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     2692
_reflns_number_gt     1782
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0886
_refine_ls_R_factor_gt     0.0593
_refine_ls_wR_factor_gt     0.1976
_refine_ls_wR_factor_ref     0.2173
_refine_ls_goodness_of_fit_ref     1.099
_refine_ls_restrained_S_all     1.099
_refine_ls_number_reflns     2692
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1083P)²+0.1931P] 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     0.530
_refine_diff_density_min     -0.265
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'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'APEX2 (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 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2003)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    Cl Cl1 0.80795(12) 0.09608(15) 0.42599(12) 0.0771(4) Uani . . 1.000
    O O1 -0.2602(3) 0.5461(3) 0.1669(2) 0.0510(6) Uani . . 1.000
    O O2 -0.3959(3) 0.3388(3) -0.1034(2) 0.0543(6) Uani . . 1.000
    C C1 -0.2554(3) 0.4027(3) 0.0322(3) 0.0390(7) Uani . . 1.000
    C C2 -0.0735(3) 0.3196(3) 0.0525(3) 0.0371(7) Uani . . 1.000
    C C3 -0.0680(4) 0.1670(4) -0.1102(3) 0.0484(8) Uani . . 1.000
    C C4 0.0606(3) 0.3764(3) 0.2098(3) 0.0403(7) Uani . . 1.000
    C C5 0.2464(3) 0.3096(3) 0.2602(3) 0.0364(6) Uani . . 1.000
    C C6 0.3638(4) 0.2508(4) 0.1573(3) 0.0432(8) Uani . . 1.000
    C C7 0.5363(4) 0.1864(4) 0.2086(3) 0.0461(8) Uani . . 1.000
    C C8 0.5923(4) 0.1793(4) 0.3641(3) 0.0438(7) Uani . . 1.000
    C C9 0.4803(4) 0.2379(4) 0.4686(3) 0.0493(8) Uani . . 1.000
    C C10 0.3099(4) 0.3051(4) 0.4171(3) 0.0451(7) Uani . . 1.000
    H H1 -0.377(5) 0.580(5) 0.142(5) 0.0612 Uiso . . 1.000
    H H3A -0.19861 0.10124 -0.17914 0.0725 Uiso . . 1.000
    H H3B 0.01747 0.08750 -0.08293 0.0725 Uiso . . 1.000
    H H3C -0.01950 0.21487 -0.17241 0.0725 Uiso . . 1.000
    H H4 0.03229 0.46997 0.29797 0.0484 Uiso . . 1.000
    H H6 0.32524 0.25512 0.05263 0.0518 Uiso . . 1.000
    H H7 0.61382 0.14812 0.13947 0.0554 Uiso . . 1.000
    H H9 0.51873 0.23233 0.57269 0.0592 Uiso . . 1.000
    H H10 0.23624 0.34816 0.48924 0.0541 Uiso . . 1.000
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 0.0555(5) 0.1129(8) 0.0698(6) 0.0449(5) 0.0181(4) 0.0492(5)
    O1 0.0415(10) 0.0576(12) 0.0430(10) 0.0207(8) 0.0116(8) 0.0147(9)
    O2 0.0436(10) 0.0686(13) 0.0391(10) 0.0217(9) 0.0075(8) 0.0183(9)
    C1 0.0377(11) 0.0459(13) 0.0373(12) 0.0117(10) 0.0140(9) 0.0213(10)
    C2 0.0357(11) 0.0379(12) 0.0411(12) 0.0091(9) 0.0141(9) 0.0202(10)
    C3 0.0444(13) 0.0477(14) 0.0430(13) 0.0116(11) 0.0115(11) 0.0138(11)
    C4 0.0365(11) 0.0418(12) 0.0395(12) 0.0109(9) 0.0122(9) 0.0160(10)
    C5 0.0335(10) 0.0351(11) 0.0363(11) 0.0060(9) 0.0105(9) 0.0131(9)
    C6 0.0397(12) 0.0562(15) 0.0408(12) 0.0112(10) 0.0143(10) 0.0276(12)
    C7 0.0359(11) 0.0604(16) 0.0443(13) 0.0130(11) 0.0152(10) 0.0245(12)
    C8 0.0349(11) 0.0487(14) 0.0413(12) 0.0103(10) 0.0060(10) 0.0192(11)
    C9 0.0461(13) 0.0627(17) 0.0323(12) 0.0133(12) 0.0063(10) 0.0200(12)
    C10 0.0412(12) 0.0563(15) 0.0310(11) 0.0105(11) 0.0116(10) 0.0141(11)
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C8 . . 1.734(3) no
    O1 C1 . . 1.310(3) no
    O2 C1 . . 1.231(3) no
    O1 H1 . . 0.88(4) no
    C1 C2 . . 1.480(3) no
    C2 C3 . . 1.503(4) no
    C2 C4 . . 1.341(3) no
    C4 C5 . . 1.467(3) no
    C5 C10 . . 1.386(4) no
    C5 C6 . . 1.397(4) no
    C6 C7 . . 1.381(4) no
    C7 C8 . . 1.385(4) no
    C8 C9 . . 1.376(4) no
    C9 C10 . . 1.382(4) no
    C3 H3A . . 0.9600 no
    C3 H3B . . 0.9600 no
    C3 H3C . . 0.9600 no
    C4 H4 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C7 H7 . . 0.9300 no
    C9 H9 . . 0.9300 no
    C10 H10 . . 0.9300 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 O1 H1 . . . 109(3) no
    O1 C1 O2 . . . 121.8(2) no
    O1 C1 C2 . . . 116.5(2) no
    O2 C1 C2 . . . 121.7(2) no
    C1 C2 C4 . . . 118.9(2) no
    C3 C2 C4 . . . 126.8(2) no
    C1 C2 C3 . . . 114.2(2) no
    C2 C4 C5 . . . 128.1(2) no
    C4 C5 C10 . . . 118.9(2) no
    C6 C5 C10 . . . 118.1(2) no
    C4 C5 C6 . . . 122.9(2) no
    C5 C6 C7 . . . 121.0(2) no
    C6 C7 C8 . . . 119.2(3) no
    Cl1 C8 C7 . . . 118.7(2) no
    Cl1 C8 C9 . . . 120.3(2) no
    C7 C8 C9 . . . 120.9(3) no
    C8 C9 C10 . . . 119.2(3) no
    C5 C10 C9 . . . 121.4(2) no
    C2 C3 H3A . . . 109.00 no
    C2 C3 H3B . . . 109.00 no
    C2 C3 H3C . . . 109.00 no
    H3A C3 H3B . . . 109.00 no
    H3A C3 H3C . . . 109.00 no
    H3B C3 H3C . . . 110.00 no
    C2 C4 H4 . . . 116.00 no
    C5 C4 H4 . . . 116.00 no
    C5 C6 H6 . . . 119.00 no
    C7 C6 H6 . . . 119.00 no
    C6 C7 H7 . . . 120.00 no
    C8 C7 H7 . . . 120.00 no
    C8 C9 H9 . . . 120.00 no
    C10 C9 H9 . . . 120.00 no
    C5 C10 H10 . . . 119.00 no
    C9 C10 H10 . . . 119.00 no
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
    O1 C1 C2 C3 . . . . -174.4(2) no
    O1 C1 C2 C4 . . . . 9.9(4) no
    O2 C1 C2 C3 . . . . 6.7(4) no
    O2 C1 C2 C4 . . . . -169.1(3) no
    C1 C2 C4 C5 . . . . 177.8(3) no
    C3 C2 C4 C5 . . . . 2.6(5) no
    C2 C4 C5 C6 . . . . 35.4(4) no
    C2 C4 C5 C10 . . . . -145.0(3) no
    C4 C5 C6 C7 . . . . -179.0(3) no
    C10 C5 C6 C7 . . . . 1.3(5) no
    C4 C5 C10 C9 . . . . 177.8(3) no
    C6 C5 C10 C9 . . . . -2.5(5) no
    C5 C6 C7 C8 . . . . 0.4(5) no
    C6 C7 C8 Cl1 . . . . 179.4(3) no
    C6 C7 C8 C9 . . . . -1.0(5) no
    Cl1 C8 C9 C10 . . . . 179.5(3) no
    C7 C8 C9 C10 . . . . -0.2(5) no
    C8 C9 C10 C5 . . . . 2.0(5) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O1 H1 O2 2_465 0.88(4) 1.76(4) 2.643(3) 176.4(14) yes
    C3 H3A O2 . 0.96 2.41 2.765(4) 101 yes
    C4 H4 O1 . 0.93 2.32 2.720(3) 106 yes
    C9 H9 O2 1_656 0.93 2.57 3.458(3) 159 yes
    C3 H3a Cg 2_555 0.96 2.84 3.638(3) 141 yes
