##############################################################################
###                                                                        ###
###        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.                                        #
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# Full details of the Crystallographic Information File format               #
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# 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 2.1.    #
#                                                                            #
# 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_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-08-07
_journal_date_accepted     2007-08-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      9
_journal_page_first     o3763
_journal_page_last     o3763
_journal_paper_category     QO
_journal_coeditor_code     BT2466
_publ_contact_author_name     'D. Velmurugan'
_publ_contact_author_address
;
Department of physics
presidency college
chennai-600005
India
;
_publ_contact_author_email     d_velu@yahoo.com
_publ_contact_author_fax     '044 091 2235 2494'
_publ_contact_author_phone     '044 091 2235 1367'
_publ_section_title
;
2-Ethyl 3,4-dimethyl 4'-bromobiphenyl-2,3,4-tricarboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'S. Thenmozhi'
;     Department of Physics
      Presidency College (Autonomous)
      Chennai 600 005
      India
;
    'A. Subbiah Pandi'
;     Department of Physics
      Presidency College (Autonomous)
      Chennai 600 005
      India
;
    'D. Velmurugan'
;     Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'C. Prakash'
;     Department of Organic Chemistry
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'K. Ravikumar'
;     Laboratory of X-ray Crystallography
      Indian Institute of Chemical Technology
      Hyderabad 500 007
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Ethyl 3,4-dimethyl 4'-bromobiphenyl-2,3,4-tricarboxylate
;
_chemical_name_common     Biphenyl
_chemical_formula_moiety     'C19 H17 Br O6'
_chemical_formula_sum     'C19 H17 Br O6'
_chemical_formula_iupac     'C19 H17 Br O6'
_chemical_formula_weight     421.24
_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     7.0122(5)
_cell_length_b     8.9766(6)
_cell_length_c     15.3539(10)
_cell_angle_alpha     75.073(10)
_cell_angle_beta     89.510(10)
_cell_angle_gamma     85.010(10)
_cell_volume     930.21(11)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2120
_cell_measurement_theta_min     2.36
_cell_measurement_theta_max     27.98
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.21
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.504
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     428
_exptl_absorpt_coefficient_mu     2.241
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2001)'
_exptl_absorpt_correction_T_min     0.631
_exptl_absorpt_correction_T_max     0.683
_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     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10647
_diffrn_reflns_av_R_equivalents     0.0215
_diffrn_reflns_av_sigmaI/netI     0.0255
_diffrn_reflns_theta_min     2.36
_diffrn_reflns_theta_max     27.98
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.943
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     19
_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 > 2sigma(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     4228
_reflns_number_gt     3380
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0475
_refine_ls_R_factor_gt     0.0373
_refine_ls_wR_factor_gt     0.1038
_refine_ls_wR_factor_ref     0.1095
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.042
_refine_ls_number_reflns     4228
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0581P)²+0.3096P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.657
_refine_diff_density_min     -0.553
_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'
    'O' 'O' 0.0106 0.0060
                         '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     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003)
;
_computing_publication_material     'SHELXL97 and PARST (Nardelli, 1995)'
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 -0.37088(4) 0.90355(3) 0.43084(2) 0.07536(14) Uani d . 1 . .
    O O1 0.3586(3) 0.90736(19) 0.18374(12) 0.0613(4) Uani d . 1 . .
    O O2 0.3180(2) 0.76398(17) 0.08639(10) 0.0477(4) Uani d . 1 . .
    O O3 0.7671(2) 0.74492(18) 0.09710(10) 0.0505(4) Uani d . 1 . .
    O O4 0.6697(2) 0.54018(19) 0.05724(10) 0.0481(4) Uani d . 1 . .
    O O5 0.9818(3) 0.4143(2) 0.18441(12) 0.0640(5) Uani d . 1 . .
    O O6 0.9334(3) 0.2182(2) 0.30234(12) 0.0640(5) Uani d . 1 . .
    C C1 0.3577(3) 0.5793(2) 0.31186(13) 0.0411(4) Uani d . 1 . .
    C C2 0.4405(3) 0.4438(3) 0.36956(14) 0.0503(5) Uani d . 1 . .
    H H2 0.3833 0.4037 0.4245 0.060 Uiso calc R 1 . .
    C C3 0.6051(3) 0.3678(3) 0.34720(14) 0.0482(5) Uani d . 1 . .
    H H3 0.6581 0.2779 0.3874 0.058 Uiso calc R 1 . .
    C C4 0.6932(3) 0.4239(2) 0.26515(13) 0.0398(4) Uani d . 1 . .
    C C5 0.6081(3) 0.5563(2) 0.20462(12) 0.0370(4) Uani d . 1 . .
    C C6 0.4436(3) 0.6351(2) 0.22834(13) 0.0382(4) Uani d . 1 . .
    C C1' 0.1801(3) 0.6579(2) 0.33965(13) 0.0427(4) Uani d . 1 . .
    C C2' 0.1654(4) 0.6749(3) 0.42695(15) 0.0567(6) Uani d . 1 . .
    H H2' 0.2670 0.6372 0.4674 0.068 Uiso calc R 1 . .
    C C3' 0.0018(4) 0.7471(3) 0.45488(16) 0.0609(6) Uani d . 1 . .
    H H3' -0.0064 0.7586 0.5133 0.073 Uiso calc R 1 . .
    C C4' -0.1480(3) 0.8014(3) 0.39456(16) 0.0500(5) Uani d . 1 . .
    C C5' -0.1396(3) 0.7849(3) 0.30811(16) 0.0491(5) Uani d . 1 . .
    H H5' -0.2424 0.8214 0.2683 0.059 Uiso calc R 1 . .
    C C6' 0.0253(3) 0.7125(3) 0.28117(15) 0.0456(5) Uani d . 1 . .
    H H6' 0.0320 0.7005 0.2228 0.055 Uiso calc R 1 . .
    C C7 0.3685(3) 0.7860(2) 0.16512(14) 0.0420(4) Uani d . 1 . .
    C C8 0.2483(5) 0.9014(3) 0.01784(19) 0.0765(9) Uani d . 1 . .
    H H8A 0.3369 0.9804 0.0122 0.092 Uiso calc R 1 . .
    H H8B 0.1250 0.9418 0.0351 0.092 Uiso calc R 1 . .
    C C9 0.2297(6) 0.8634(4) -0.0678(2) 0.0856(10) Uani d . 1 . .
    H H9A 0.3530 0.8280 -0.0860 0.128 Uiso calc R 1 . .
    H H9B 0.1792 0.9537 -0.1125 0.128 Uiso calc R 1 . .
    H H9C 0.1445 0.7833 -0.0615 0.128 Uiso calc R 1 . .
    C C10 0.6951(3) 0.6246(2) 0.11437(13) 0.0384(4) Uani d . 1 . .
    C C11 0.7451(4) 0.5970(4) -0.03205(16) 0.0622(7) Uani d . 1 . .
    H H11A 0.6755 0.6935 -0.0616 0.093 Uiso calc R 1 . .
    H H11B 0.7318 0.5229 -0.0664 0.093 Uiso calc R 1 . .
    H H11C 0.8780 0.6125 -0.0274 0.093 Uiso calc R 1 . .
    C C12 0.8826(3) 0.3531(2) 0.24429(14) 0.0434(5) Uani d . 1 . .
    C C13 1.1191(4) 0.1446(4) 0.2883(2) 0.0771(9) Uani d . 1 . .
    H H13A 1.1171 0.1152 0.2325 0.116 Uiso calc R 1 . .
    H H13B 1.1483 0.0542 0.3370 0.116 Uiso calc R 1 . .
    H H13C 1.2148 0.2156 0.2860 0.116 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 C4' . 1.895(2) ?
    O1 C7 . 1.192(3) ?
    O2 C7 . 1.330(3) ?
    O2 C8 . 1.450(3) ?
    O3 C10 . 1.199(3) ?
    O4 C10 . 1.320(3) ?
    O4 C11 . 1.447(3) ?
    O5 C12 . 1.194(3) ?
    O6 C12 . 1.327(3) ?
    O6 C13 . 1.448(3) ?
    C1 C2 . 1.390(3) ?
    C1 C6 . 1.402(3) ?
    C1 C1' . 1.491(3) ?
    C2 C3 . 1.376(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.391(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.396(3) ?
    C4 C12 . 1.491(3) ?
    C5 C6 . 1.395(3) ?
    C5 C10 . 1.510(3) ?
    C6 C7 . 1.503(3) ?
    C1' C6' . 1.386(3) ?
    C1' C2' . 1.390(3) ?
    C2' C3' . 1.388(3) ?
    C2' H2' . 0.9300 ?
    C3' C4' . 1.376(4) ?
    C3' H3' . 0.9300 ?
    C4' C5' . 1.373(3) ?
    C5' C6' . 1.389(3) ?
    C5' H5' . 0.9300 ?
    C6' H6' . 0.9300 ?
    C8 C9 . 1.450(4) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 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 . . 116.2(2) .
    C10 O4 C11 . . 115.7(2) .
    C12 O6 C13 . . 115.8(2) .
    C2 C1 C6 . . 118.17(19) ?
    C2 C1 C1' . . 119.34(18) ?
    C6 C1 C1' . . 122.48(18) ?
    C3 C2 C1 . . 121.47(19) ?
    C3 C2 H2 . . 119.3 ?
    C1 C2 H2 . . 119.3 ?
    C2 C3 C4 . . 120.70(19) ?
    C2 C3 H3 . . 119.7 ?
    C4 C3 H3 . . 119.7 ?
    C3 C4 C5 . . 118.76(19) ?
    C3 C4 C12 . . 121.23(18) ?
    C5 C4 C12 . . 119.83(17) ?
    C4 C5 C6 . . 120.33(17) ?
    C4 C5 C10 . . 121.90(17) ?
    C6 C5 C10 . . 117.67(17) ?
    C5 C6 C1 . . 120.48(18) ?
    C5 C6 C7 . . 118.51(17) ?
    C1 C6 C7 . . 120.89(18) ?
    C6' C1' C2' . . 118.3(2) ?
    C6' C1' C1 . . 121.85(18) ?
    C2' C1' C1 . . 119.83(19) ?
    C1' C2' C3' . . 121.2(2) ?
    C1' C2' H2' . . 119.4 ?
    C3' C2' H2' . . 119.4 ?
    C4' C3' C2' . . 118.8(2) ?
    C4' C3' H3' . . 120.6 ?
    C2' C3' H3' . . 120.6 ?
    C3' C4' C5' . . 121.6(2) ?
    C3' C4' Br1 . . 119.43(17) ?
    C5' C4' Br1 . . 118.95(18) ?
    C4' C5' C6' . . 118.8(2) ?
    C4' C5' H5' . . 120.6 ?
    C6' C5' H5' . . 120.6 ?
    C5' C6' C1' . . 121.2(2) ?
    C5' C6' H6' . . 119.4 ?
    C1' C6' H6' . . 119.4 ?
    O1 C7 O2 . . 125.6(2) ?
    O1 C7 C6 . . 124.0(2) ?
    O2 C7 C6 . . 110.38(17) ?
    O2 C8 C9 . . 109.7(3) ?
    O2 C8 H8A . . 109.7 ?
    C9 C8 H8A . . 109.7 ?
    O2 C8 H8B . . 109.7 ?
    C9 C8 H8B . . 109.7 ?
    H8A C8 H8B . . 108.2 ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    O3 C10 O4 . . 125.60(18) ?
    O3 C10 C5 . . 123.02(18) ?
    O4 C10 C5 . . 111.24(17) ?
    O4 C11 H11A . . 109.5 ?
    O4 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    O4 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    O5 C12 O6 . . 123.6(2) ?
    O5 C12 C4 . . 123.66(19) ?
    O6 C12 C4 . . 112.61(18) ?
    O6 C13 H13A . . 109.5 ?
    O6 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    O6 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 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
    C6 C1 C2 C3 . . . . 1.7(3) ?
    C1' C1 C2 C3 . . . . -179.5(2) ?
    C1 C2 C3 C4 . . . . -0.6(4) ?
    C2 C3 C4 C5 . . . . -2.0(3) ?
    C2 C3 C4 C12 . . . . 173.1(2) ?
    C3 C4 C5 C6 . . . . 3.4(3) ?
    C12 C4 C5 C6 . . . . -171.74(19) ?
    C3 C4 C5 C10 . . . . 179.8(2) ?
    C12 C4 C5 C10 . . . . 4.7(3) ?
    C4 C5 C6 C1 . . . . -2.4(3) ?
    C10 C5 C6 C1 . . . . -178.90(19) ?
    C4 C5 C6 C7 . . . . 173.77(19) ?
    C10 C5 C6 C7 . . . . -2.8(3) ?
    C2 C1 C6 C5 . . . . -0.3(3) ?
    C1' C1 C6 C5 . . . . -178.98(19) ?
    C2 C1 C6 C7 . . . . -176.3(2) ?
    C1' C1 C6 C7 . . . . 5.0(3) ?
    C2 C1 C1' C6' . . . . -134.7(2) ?
    C6 C1 C1' C6' . . . . 44.0(3) ?
    C2 C1 C1' C2' . . . . 43.9(3) ?
    C6 C1 C1' C2' . . . . -137.4(2) ?
    C6' C1' C2' C3' . . . . -1.2(4) ?
    C1 C1' C2' C3' . . . . -179.8(2) ?
    C1' C2' C3' C4' . . . . 0.4(4) ?
    C2' C3' C4' C5' . . . . 0.4(4) ?
    C2' C3' C4' Br1 . . . . -178.9(2) ?
    C3' C4' C5' C6' . . . . -0.5(4) ?
    Br1 C4' C5' C6' . . . . 178.81(17) ?
    C4' C5' C6' C1' . . . . -0.2(3) ?
    C2' C1' C6' C5' . . . . 1.1(3) ?
    C1 C1' C6' C5' . . . . 179.7(2) ?
    C8 O2 C7 O1 . . . . 1.1(3) ?
    C8 O2 C7 C6 . . . . -178.1(2) ?
    C5 C6 C7 O1 . . . . -116.9(2) ?
    C1 C6 C7 O1 . . . . 59.2(3) ?
    C5 C6 C7 O2 . . . . 62.3(2) ?
    C1 C6 C7 O2 . . . . -121.6(2) ?
    C7 O2 C8 C9 . . . . 170.5(3) ?
    C11 O4 C10 O3 . . . . 3.2(3) ?
    C11 O4 C10 C5 . . . . 179.0(2) ?
    C4 C5 C10 O3 . . . . -109.6(2) ?
    C6 C5 C10 O3 . . . . 66.9(3) ?
    C4 C5 C10 O4 . . . . 74.4(2) ?
    C6 C5 C10 O4 . . . . -109.1(2) ?
    C13 O6 C12 O5 . . . . -1.2(4) ?
    C13 O6 C12 C4 . . . . -178.0(2) ?
    C3 C4 C12 O5 . . . . -164.0(2) ?
    C5 C4 C12 O5 . . . . 11.0(3) ?
    C3 C4 C12 O6 . . . . 12.7(3) ?
    C5 C4 C12 O6 . . . . -172.2(2) ?
