##############################################################################
### ###
### 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. #
# #
##############################################################################
data_global
_audit_creation_method ?
_journal_date_recd_electronic 2008-06-22
_journal_date_accepted 2008-06-27
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2008
_journal_volume 64
_journal_issue 8
_journal_page_first o1373
_journal_page_last o1373
_journal_paper_category QO
_journal_coeditor_code AT2580
_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
;
2-Methyl-3-(3-methylphenyl)acrylic acid
;
loop_
_publ_author_name
_publ_author_address
'Muhammad, Niaz'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
'Saqib Ali'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
'Tahir, M. Nawaz'
;
University of Sargodha
Department of Physics
Sagrodha
Pakistan
;
'Zia-ur-Rehman'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
2-Methyl-3-(3-methylphenyl)acrylic acid
;
_chemical_name_common ?
_chemical_formula_moiety 'C11 H12 O2'
_chemical_formula_sum 'C11 H12 O2'
_chemical_formula_iupac 'C11 H12 O2'
_chemical_formula_weight 176.21
_chemical_melting_point ?
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
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'
_cell_length_a 7.4430(9)
_cell_length_b 13.4094(16)
_cell_length_c 10.2746(12)
_cell_angle_alpha 90.00
_cell_angle_beta 110.745(4)
_cell_angle_gamma 90.00
_cell_volume 959.0(2)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2820
_cell_measurement_theta_min 2.61
_cell_measurement_theta_max 30.15
_cell_measurement_temperature 296(2)
_exptl_crystal_description prismatic
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.26
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.15
_exptl_crystal_density_diffrn 1.220
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 376
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min 0.980
_exptl_absorpt_correction_T_max 0.986
_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 \w
_diffrn_detector_area_resol_mean 7.2
_diffrn_reflns_number 11342
_diffrn_reflns_av_R_equivalents 0.0471
_diffrn_reflns_av_sigmaI/netI 0.0649
_diffrn_reflns_theta_min 2.61
_diffrn_reflns_theta_max 30.15
_diffrn_reflns_theta_full 30.15
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 14
_diffrn_standards_number 0
_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 2820
_reflns_number_gt 1075
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1689
_refine_ls_R_factor_gt 0.0558
_refine_ls_wR_factor_gt 0.1379
_refine_ls_wR_factor_ref 0.1848
_refine_ls_goodness_of_fit_ref 1.017
_refine_ls_restrained_S_all 1.017
_refine_ls_number_reflns 2820
_refine_ls_number_parameters 120
_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^)+(0.0657P)^2^+0.1910P] 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 0.235
_refine_diff_density_min -0.196
_refine_ls_extinction_method 'empirical'
_refine_ls_extinction_coef 0.006(2)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
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'
_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
'Ortep3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
;
WinGx publication routines (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
O O1 0.1630(3) -0.00578(12) 0.4174(2) 0.0795(8) Uani . . 1.000
O O2 0.0675(2) 0.12222(11) 0.51106(18) 0.0699(7) Uani . . 1.000
C C1 0.1639(3) 0.08682(17) 0.4441(2) 0.0515(8) Uani . . 1.000
C C2 0.2797(3) 0.15393(16) 0.3911(2) 0.0484(7) Uani . . 1.000
C C3 0.4010(3) 0.11136(17) 0.3377(2) 0.0533(8) Uani . . 1.000
C C4 0.5340(3) 0.15354(16) 0.2764(2) 0.0497(8) Uani . . 1.000
C C5 0.6214(3) 0.08770(17) 0.2126(2) 0.0534(8) Uani . . 1.000
C C6 0.7448(3) 0.11877(18) 0.1461(2) 0.0553(8) Uani . . 1.000
C C7 0.7829(4) 0.21882(19) 0.1470(3) 0.0637(9) Uani . . 1.000
C C8 0.7031(4) 0.2856(2) 0.2118(3) 0.0699(10) Uani . . 1.000
C C9 0.5794(4) 0.25412(17) 0.2757(3) 0.0646(9) Uani . . 1.000
C C10 0.2492(3) 0.26372(17) 0.4024(3) 0.0658(10) Uani . . 1.000
C C11 0.8342(4) 0.0464(2) 0.0760(3) 0.0788(11) Uani . . 1.000
H H1 0.10360 -0.03595 0.45872 0.0954 Uiso . . 1.000
H H3 0.40046 0.04203 0.33992 0.0639 Uiso . . 1.000
H H5 0.59610 0.01991 0.21458 0.0640 Uiso . . 1.000
H H7 0.86445 0.24181 0.10285 0.0764 Uiso . . 1.000
H H8 0.73305 0.35299 0.21244 0.0838 Uiso . . 1.000
H H9 0.52556 0.30031 0.31872 0.0774 Uiso . . 1.000
H H10A 0.15463 0.27413 0.44482 0.0988 Uiso . . 1.000
H H10B 0.20537 0.29296 0.31123 0.0988 Uiso . . 1.000
H H10C 0.36802 0.29433 0.45849 0.0988 Uiso . . 1.000
H H11A 0.79146 -0.01992 0.08522 0.1182 Uiso . . 1.000
H H11B 0.97157 0.04960 0.11877 0.1182 Uiso . . 1.000
H H11C 0.79701 0.06301 -0.02083 0.1182 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
O1 0.1052(15) 0.0487(10) 0.1240(17) -0.0062(9) 0.0893(13) -0.0004(10)
O2 0.0786(12) 0.0602(11) 0.0958(13) -0.0042(8) 0.0617(11) -0.0100(9)
C1 0.0537(13) 0.0479(13) 0.0629(15) 0.0003(10) 0.0330(12) -0.0028(11)
C2 0.0460(12) 0.0467(12) 0.0570(14) -0.0032(10) 0.0239(11) 0.0020(11)
C3 0.0583(14) 0.0481(12) 0.0634(15) -0.0046(11) 0.0339(12) 0.0003(12)
C4 0.0510(13) 0.0508(12) 0.0549(14) -0.0052(10) 0.0282(12) 0.0009(11)
C5 0.0525(14) 0.0513(13) 0.0611(15) -0.0035(10) 0.0261(12) 0.0021(11)
C6 0.0490(13) 0.0649(16) 0.0589(15) -0.0034(11) 0.0278(12) 0.0047(12)
C7 0.0631(15) 0.0742(17) 0.0646(16) -0.0139(13) 0.0358(14) 0.0053(13)
C8 0.0812(19) 0.0581(15) 0.0849(19) -0.0194(13) 0.0475(17) -0.0021(13)
C9 0.0767(17) 0.0525(14) 0.0804(18) -0.0098(12) 0.0475(15) -0.0045(13)
C10 0.0574(15) 0.0538(15) 0.097(2) -0.0010(11) 0.0408(15) -0.0017(14)
C11 0.0757(18) 0.088(2) 0.091(2) 0.0014(15) 0.0521(17) -0.0051(16)
_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
O1 C1 . . 1.271(3) no
O2 C1 . . 1.250(3) no
O1 H1 . . 0.8200 no
C1 C2 . . 1.477(3) no
C2 C10 . . 1.500(3) no
C2 C3 . . 1.339(3) no
C3 C4 . . 1.462(3) no
C4 C9 . . 1.391(3) no
C4 C5 . . 1.391(3) no
C5 C6 . . 1.389(3) no
C6 C7 . . 1.371(4) no
C6 C11 . . 1.498(4) no
C7 C8 . . 1.370(4) no
C8 C9 . . 1.373(4) no
C3 H3 . . 0.9300 no
C5 H5 . . 0.9300 no
C7 H7 . . 0.9300 no
C8 H8 . . 0.9300 no
C9 H9 . . 0.9300 no
C10 H10A . . 0.9600 no
C10 H10B . . 0.9600 no
C10 H10C . . 0.9600 no
C11 H11A . . 0.9600 no
C11 H11B . . 0.9600 no
C11 H11C . . 0.9600 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 . . . 109.00 no
O1 C1 O2 . . . 122.0(2) no
O1 C1 C2 . . . 118.3(2) no
O2 C1 C2 . . . 119.7(2) no
C1 C2 C10 . . . 116.4(2) no
C3 C2 C10 . . . 126.3(2) no
C1 C2 C3 . . . 117.2(2) no
C2 C3 C4 . . . 132.0(2) no
C3 C4 C9 . . . 125.5(2) no
C5 C4 C9 . . . 117.3(2) no
C3 C4 C5 . . . 117.3(2) no
C4 C5 C6 . . . 122.9(2) no
C5 C6 C11 . . . 121.8(2) no
C7 C6 C11 . . . 120.8(2) no
C5 C6 C7 . . . 117.5(2) no
C6 C7 C8 . . . 121.2(3) no
C7 C8 C9 . . . 120.7(2) no
C4 C9 C8 . . . 120.4(2) no
C2 C3 H3 . . . 114.00 no
C4 C3 H3 . . . 114.00 no
C4 C5 H5 . . . 119.00 no
C6 C5 H5 . . . 119.00 no
C6 C7 H7 . . . 119.00 no
C8 C7 H7 . . . 119.00 no
C7 C8 H8 . . . 120.00 no
C9 C8 H8 . . . 120.00 no
C4 C9 H9 . . . 120.00 no
C8 C9 H9 . . . 120.00 no
C2 C10 H10A . . . 109.00 no
C2 C10 H10B . . . 109.00 no
C2 C10 H10C . . . 109.00 no
H10A C10 H10B . . . 109.00 no
H10A C10 H10C . . . 109.00 no
H10B C10 H10C . . . 109.00 no
C6 C11 H11A . . . 109.00 no
C6 C11 H11B . . . 109.00 no
C6 C11 H11C . . . 110.00 no
H11A C11 H11B . . . 109.00 no
H11A C11 H11C . . . 109.00 no
H11B C11 H11C . . . 109.00 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 . . . . -10.6(3) no
O1 C1 C2 C10 . . . . 169.3(2) no
O2 C1 C2 C3 . . . . 170.7(2) no
O2 C1 C2 C10 . . . . -9.4(3) no
C1 C2 C3 C4 . . . . 179.6(2) no
C10 C2 C3 C4 . . . . -0.3(4) no
C2 C3 C4 C5 . . . . -171.3(2) no
C2 C3 C4 C9 . . . . 8.3(4) no
C3 C4 C5 C6 . . . . 177.54(19) no
C9 C4 C5 C6 . . . . -2.0(3) no
C3 C4 C9 C8 . . . . -178.4(2) no
C5 C4 C9 C8 . . . . 1.2(4) no
C4 C5 C6 C7 . . . . 1.3(3) no
C4 C5 C6 C11 . . . . -178.9(2) no
C5 C6 C7 C8 . . . . 0.4(4) no
C11 C6 C7 C8 . . . . -179.5(3) no
C6 C7 C8 C9 . . . . -1.2(4) no
C7 C8 C9 C4 . . . . 0.4(4) 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 3_556 0.82 1.83 2.611(3) 160 yes
C3 H3 O1 . 0.93 2.27 2.703(3) 108 yes
C8 H8 O1 2_655 0.93 2.59 3.394(3) 145 yes
C10 H10A O2 . 0.96 2.31 2.783(3) 109 yes
C10 H10C Cg 4_555 0.9600 2.75 3.610(3) 149.00 yes
C1 O2 Cg 1_455 1.250(3) 3.574(2) 3.895(3) 95.38(13) yes