##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
3,5-Dibromo-2',3',4',5',6'-pentamethyl-1,1'-biphenyl
;
_chemical_formula_moiety     'C17 H18 Br2'
_chemical_formula_sum     'C17 H18 Br2'
_chemical_formula_iupac     'C17 H18 Br2'
_chemical_formula_weight     382.13
_chemical_melting_point     ?
_chemical_melting_point_gt     451
_chemical_melting_point_lt     450
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.011(5)
_cell_length_b     14.065(8)
_cell_length_c     12.387(7)
_cell_angle_alpha     90
_cell_angle_beta     94.613(9)
_cell_angle_gamma     90
_cell_volume     1564.8(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2189
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     22.4
_cell_measurement_temperature     297(2)
_exptl_crystal_description     blocks
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.622
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     760
_exptl_absorpt_coefficient_mu     5.17
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.265
_exptl_absorpt_correction_T_max     0.316
_diffrn_ambient_temperature     297(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     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10702
_diffrn_reflns_av_R_equivalents     0.127
_diffrn_reflns_theta_min     2.19
_diffrn_reflns_theta_max     25.0
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -14
_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 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     2760
_reflns_number_gt     1588
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.115
_refine_ls_R_factor_gt     0.057
_refine_ls_wR_factor_ref     0.150
_refine_ls_goodness_of_fit_ref     0.94
_refine_ls_restrained_S_all     0.939
_refine_ls_number_reflns     2760
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0001P)²] 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
_refine_diff_density_max     0.67
_refine_diff_density_min     -0.53
_refine_ls_extinction_method     '(SHELXL97; Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0150(15)
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 0 '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, 2000)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg, 2009)'
_computing_publication_material
                               'publCIF (Westrip, 2010) 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 1.08347(7) 0.76924(6) 0.65316(7) 0.0714(4) Uani d . 1 . .
    Br Br2 0.65525(8) 1.06226(5) 0.62304(8) 0.0736(4) Uani d . 1 . .
    C C1 0.8834(7) 0.8091(5) 0.6463(5) 0.0440(16) Uani d . 1 . .
    C C2 0.8516(6) 0.9036(5) 0.6407(5) 0.0498(17) Uani d . 1 . .
    H H2 0.9275 0.9485 0.6415 0.06 Uiso calc R 1 . .
    C C3 0.7030(7) 0.9318(4) 0.6337(5) 0.0473(16) Uani d . 1 . .
    C C4 0.5917(6) 0.8654(4) 0.6332(4) 0.0376(15) Uani d . 1 . .
    H H4 0.4928 0.885 0.6279 0.045 Uiso calc R 1 . .
    C C5 0.6246(6) 0.7700(4) 0.6404(5) 0.0392(15) Uani d . 1 . .
    C C6 0.7720(6) 0.7427(4) 0.6455(5) 0.0428(15) Uani d . 1 . .
    H H6 0.7962 0.6784 0.6483 0.051 Uiso calc R 1 . .
    C C7 0.5039(6) 0.6982(4) 0.6411(5) 0.0394(15) Uani d . 1 . .
    C C8 0.4465(6) 0.6539(4) 0.5448(5) 0.0445(16) Uani d . 1 . .
    C C9 0.3389(6) 0.5839(4) 0.5454(6) 0.0468(17) Uani d . 1 . .
    C C10 0.2872(7) 0.5553(5) 0.6454(7) 0.0544(18) Uani d . 1 . .
    C C11 0.3451(7) 0.5992(5) 0.7412(6) 0.0484(17) Uani d . 1 . .
    C C12 0.4511(6) 0.6700(4) 0.7391(5) 0.0444(16) Uani d . 1 . .
    C C13 0.5038(7) 0.6859(5) 0.4388(5) 0.0609(19) Uani d . 1 . .
    H H13A 0.5304 0.6312 0.3981 0.091 Uiso calc R 1 . .
    H H13B 0.5898 0.7255 0.4535 0.091 Uiso calc R 1 . .
    H H13C 0.4276 0.7211 0.3976 0.091 Uiso calc R 1 . .
    C C14 0.2779(8) 0.5413(5) 0.4401(6) 0.067(2) Uani d . 1 . .
    H H14A 0.2468 0.5912 0.3904 0.101 Uiso calc R 1 . .
    H H14B 0.1942 0.5016 0.4522 0.101 Uiso calc R 1 . .
    H H14C 0.3536 0.5039 0.4101 0.101 Uiso calc R 1 . .
    C C15 0.1694(8) 0.4811(6) 0.6491(8) 0.086(3) Uani d . 1 . .
    H H15A 0.1919 0.4406 0.7106 0.129 Uiso calc R 1 . .
    H H15B 0.1659 0.4437 0.584 0.129 Uiso calc R 1 . .
    H H15C 0.0747 0.5111 0.6549 0.129 Uiso calc R 1 . .
    C C16 0.2841(9) 0.5705(6) 0.8452(7) 0.084(3) Uani d . 1 . .
    H H16A 0.3278 0.6092 0.9031 0.126 Uiso calc R 1 . .
    H H16B 0.3073 0.5049 0.8599 0.126 Uiso calc R 1 . .
    H H16C 0.178 0.5789 0.8392 0.126 Uiso calc R 1 . .
    C C17 0.5056(8) 0.7204(5) 0.8418(6) 0.065(2) Uani d . 1 . .
    H H17A 0.4264 0.7581 0.8668 0.097 Uiso calc R 1 . .
    H H17B 0.5877 0.7609 0.8279 0.097 Uiso calc R 1 . .
    H H17C 0.5374 0.6744 0.896 0.097 Uiso calc 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
    Br1 0.0413(5) 0.1017(7) 0.0722(6) 0.0182(4) 0.0113(4) -0.0009(5)
    Br2 0.0704(6) 0.0468(5) 0.1041(8) 0.0015(4) 0.0105(5) -0.0050(4)
    C1 0.041(3) 0.054(4) 0.038(4) 0.012(3) 0.011(3) -0.001(3)
    C2 0.037(4) 0.073(5) 0.042(4) -0.011(3) 0.016(3) -0.005(4)
    C3 0.042(4) 0.053(4) 0.048(4) 0.001(3) 0.009(3) -0.005(3)
    C4 0.035(3) 0.046(4) 0.032(4) 0.007(3) 0.008(3) 0.000(3)
    C5 0.040(3) 0.049(4) 0.030(3) 0.001(3) 0.011(3) 0.000(3)
    C6 0.044(4) 0.045(4) 0.040(4) 0.011(3) 0.006(3) -0.002(3)
    C7 0.040(3) 0.040(3) 0.039(4) 0.003(3) 0.009(3) -0.002(3)
    C8 0.044(4) 0.048(4) 0.041(4) 0.009(3) 0.006(3) -0.002(3)
    C9 0.030(3) 0.051(4) 0.059(5) 0.006(3) 0.002(3) -0.006(3)
    C10 0.043(4) 0.050(4) 0.072(6) 0.007(3) 0.013(4) 0.012(4)
    C11 0.042(4) 0.056(4) 0.050(5) 0.015(3) 0.022(3) 0.008(4)
    C12 0.038(3) 0.054(4) 0.043(4) 0.006(3) 0.011(3) -0.004(3)
    C13 0.070(5) 0.068(5) 0.046(5) -0.005(4) 0.016(4) -0.002(4)
    C14 0.061(4) 0.071(5) 0.068(6) -0.006(4) -0.001(4) -0.020(4)
    C15 0.060(5) 0.088(6) 0.113(8) -0.023(4) 0.024(5) 0.012(5)
    C16 0.067(5) 0.110(7) 0.080(6) -0.005(5) 0.036(5) 0.016(5)
    C17 0.077(5) 0.071(5) 0.048(5) 0.006(4) 0.019(4) -0.006(4)
_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 C1 . 1.883(6) ?
    Br2 C3 . 1.887(6) ?
    C1 C2 . 1.361(8) ?
    C1 C6 . 1.370(8) ?
    C2 C3 . 1.392(8) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.370(8) ?
    C4 C5 . 1.376(8) ?
    C4 H4 . 0.93 ?
    C5 C6 . 1.379(7) ?
    C5 C7 . 1.484(8) ?
    C6 H6 . 0.93 ?
    C7 C12 . 1.397(8) ?
    C7 C8 . 1.408(8) ?
    C8 C9 . 1.382(8) ?
    C8 C13 . 1.517(9) ?
    C9 C10 . 1.417(10) ?
    C9 C14 . 1.499(9) ?
    C10 C11 . 1.401(10) ?
    C10 C15 . 1.491(9) ?
    C11 C12 . 1.381(8) ?
    C11 C16 . 1.496(10) ?
    C12 C17 . 1.504(9) ?
    C13 H13A . 0.96 ?
    C13 H13B . 0.96 ?
    C13 H13C . 0.96 ?
    C14 H14A . 0.96 ?
    C14 H14B . 0.96 ?
    C14 H14C . 0.96 ?
    C15 H15A . 0.96 ?
    C15 H15B . 0.96 ?
    C15 H15C . 0.96 ?
    C16 H16A . 0.96 ?
    C16 H16B . 0.96 ?
    C16 H16C . 0.96 ?
    C17 H17A . 0.96 ?
    C17 H17B . 0.96 ?
    C17 H17C . 0.96 ?
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 . . 121.0(6) ?
    C2 C1 Br1 . . 119.3(5) ?
    C6 C1 Br1 . . 119.7(5) ?
    C1 C2 C3 . . 118.6(6) ?
    C1 C2 H2 . . 120.7 ?
    C3 C2 H2 . . 120.7 ?
    C4 C3 C2 . . 120.4(6) ?
    C4 C3 Br2 . . 120.0(5) ?
    C2 C3 Br2 . . 119.6(5) ?
    C3 C4 C5 . . 120.7(6) ?
    C3 C4 H4 . . 119.6 ?
    C5 C4 H4 . . 119.6 ?
    C4 C5 C6 . . 118.4(6) ?
    C4 C5 C7 . . 120.6(5) ?
    C6 C5 C7 . . 121.0(5) ?
    C1 C6 C5 . . 120.9(6) ?
    C1 C6 H6 . . 119.6 ?
    C5 C6 H6 . . 119.6 ?
    C12 C7 C8 . . 118.9(6) ?
    C12 C7 C5 . . 120.0(6) ?
    C8 C7 C5 . . 121.0(6) ?
    C9 C8 C7 . . 121.4(6) ?
    C9 C8 C13 . . 120.2(6) ?
    C7 C8 C13 . . 118.4(6) ?
    C8 C9 C10 . . 119.2(6) ?
    C8 C9 C14 . . 119.2(7) ?
    C10 C9 C14 . . 121.6(6) ?
    C11 C10 C9 . . 119.3(6) ?
    C11 C10 C15 . . 120.1(7) ?
    C9 C10 C15 . . 120.7(7) ?
    C12 C11 C10 . . 120.9(6) ?
    C12 C11 C16 . . 120.9(7) ?
    C10 C11 C16 . . 118.2(7) ?
    C11 C12 C7 . . 120.4(6) ?
    C11 C12 C17 . . 120.2(6) ?
    C7 C12 C17 . . 119.3(6) ?
    C8 C13 H13A . . 109.5 ?
    C8 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C8 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C9 C14 H14A . . 109.5 ?
    C9 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C9 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C10 C15 H15A . . 109.5 ?
    C10 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C10 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C11 C16 H16A . . 109.5 ?
    C11 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C11 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C12 C17 H17A . . 109.5 ?
    C12 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C12 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 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 . . . . -0.2(9) ?
    Br1 C1 C2 C3 . . . . 178.9(5) ?
    C1 C2 C3 C4 . . . . 0.4(9) ?
    C1 C2 C3 Br2 . . . . -178.8(5) ?
    C2 C3 C4 C5 . . . . 0.5(9) ?
    Br2 C3 C4 C5 . . . . 179.7(4) ?
    C3 C4 C5 C6 . . . . -1.6(8) ?
    C3 C4 C5 C7 . . . . 179.3(6) ?
    C2 C1 C6 C5 . . . . -0.9(9) ?
    Br1 C1 C6 C5 . . . . -180.0(4) ?
    C4 C5 C6 C1 . . . . 1.8(9) ?
    C7 C5 C6 C1 . . . . -179.1(6) ?
    C4 C5 C7 C12 . . . . -89.5(7) ?
    C6 C5 C7 C12 . . . . 91.4(7) ?
    C4 C5 C7 C8 . . . . 94.0(7) ?
    C6 C5 C7 C8 . . . . -85.0(7) ?
    C12 C7 C8 C9 . . . . 0.5(9) ?
    C5 C7 C8 C9 . . . . 177.0(5) ?
    C12 C7 C8 C13 . . . . 179.5(5) ?
    C5 C7 C8 C13 . . . . -4.0(8) ?
    C7 C8 C9 C10 . . . . -1.0(9) ?
    C13 C8 C9 C10 . . . . -180.0(6) ?
    C7 C8 C9 C14 . . . . 177.9(5) ?
    C13 C8 C9 C14 . . . . -1.0(9) ?
    C8 C9 C10 C11 . . . . 0.6(9) ?
    C14 C9 C10 C11 . . . . -178.3(6) ?
    C8 C9 C10 C15 . . . . 179.0(6) ?
    C14 C9 C10 C15 . . . . 0.1(9) ?
    C9 C10 C11 C12 . . . . 0.2(9) ?
    C15 C10 C11 C12 . . . . -178.2(6) ?
    C9 C10 C11 C16 . . . . 177.5(6) ?
    C15 C10 C11 C16 . . . . -0.9(9) ?
    C10 C11 C12 C7 . . . . -0.8(9) ?
    C16 C11 C12 C7 . . . . -178.0(6) ?
    C10 C11 C12 C17 . . . . 176.4(6) ?
    C16 C11 C12 C17 . . . . -0.8(9) ?
    C8 C7 C12 C11 . . . . 0.4(9) ?
    C5 C7 C12 C11 . . . . -176.1(5) ?
    C8 C7 C12 C17 . . . . -176.8(5) ?
    C5 C7 C12 C17 . . . . 6.7(8) ?
data_global
_journal_date_recd_electronic     2010-04-12
_journal_date_accepted     2010-04-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1248
_journal_page_last     o1248
_journal_paper_category     QO
_journal_coeditor_code     PK2243
_publ_contact_author_name     'Raţ, Ciprian I.'
_publ_contact_author_address
;
11 Arany Janos
40028 Cluj-Napoca
România
;
_publ_contact_author_email     'crat@chem.ubbcluj.ro'
_publ_contact_author_fax     '+40 264 590818'
_publ_contact_author_phone     '+40 264 593833'
_publ_section_title
;
3,5-Dibromo-2',3',4',5',6'-pentamethyl-1,1'-biphenyl
;
loop_
    _publ_author_name
    _publ_author_address
    'Roşca, Sorin'
;
Universitatea Babeş-Bolyai, Facultatea de Chimie şi Inginerie Chimicã
11 Arany Janos
400028 Cluj-Napoca
Romania
;
    'Olaru, Marian'
;
Universitatea Babeş-Bolyai, Facultatea de Chimie şi Inginerie Chimicã
11 Arany Janos
400028 Cluj-Napoca
Romania
;
    'Raţ, Ciprian I.'
;
Universitatea Babeş-Bolyai, Facultatea de Chimie şi Inginerie Chimicã
11 Arany Janos
400028 Cluj-Napoca
Romania
;
    'Silvestru, Cristian'
;
Universitatea Babeş-Bolyai, Facultatea de Chimie şi Inginerie Chimicã
11 Arany Janos
400028 Cluj-Napoca
Romania
;
