 
data_ocakmak4
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H14 Br4 O2'
_chemical_formula_weight          557.91
 
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'
 

_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                    12.8322(6)
_cell_length_b                    13.2320(7)
_cell_length_c                    11.1619(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  115.092(3)
_cell_angle_gamma                 90.00
_cell_volume                      1716.38(15)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.22
_exptl_crystal_size_mid           0.17
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.159
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1064
_exptl_absorpt_coefficient_mu     9.382

_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_max   0.324
_exptl_absorpt_correction_T_min   0.161
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             18137
_diffrn_reflns_av_R_equivalents   0.0902
_diffrn_reflns_av_sigmaI/netI     0.0518
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          1.75
_diffrn_reflns_theta_max          26.00
_reflns_number_total              3374
_reflns_number_gt                 2440
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0316P)²+1.6141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3374
_refine_ls_number_parameters      199
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0776
_refine_ls_R_factor_gt            0.0484
_refine_ls_wR_factor_ref          0.0931
_refine_ls_wR_factor_gt           0.0843
_refine_ls_goodness_of_fit_ref    1.069
_refine_ls_restrained_S_all       1.069
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.4490(5) 0.5750(4) 0.6436(6) 0.0403(13) Uani 1 1 d . . .
C2 C 0.3638(5) 0.5192(5) 0.6654(6) 0.0489(15) Uani 1 1 d . . .
H2 H 0.3827 0.4574 0.7090 0.059 Uiso 1 1 calc R . .
C3 C 0.2563(6) 0.5553(6) 0.6232(8) 0.0631(19) Uani 1 1 d . . .
H3 H 0.2019 0.5183 0.6392 0.076 Uiso 1 1 calc R . .
C4 C 0.2243(6) 0.6472(6) 0.5559(8) 0.0639(19) Uani 1 1 d . . .
H4 H 0.1490 0.6702 0.5260 0.077 Uiso 1 1 calc R . .
C5 C 0.3038(6) 0.7030(5) 0.5342(7) 0.0549(16) Uani 1 1 d . . .
H5 H 0.2823 0.7644 0.4901 0.066 Uiso 1 1 calc R . .
C6 C 0.4182(5) 0.6692(4) 0.5775(5) 0.0422(13) Uani 1 1 d . . .
C7 C 0.5053(5) 0.7253(4) 0.5606(5) 0.0397(13) Uani 1 1 d . . .
C8 C 0.6186(5) 0.6943(4) 0.6113(5) 0.0377(12) Uani 1 1 d . . .
C9 C 0.6483(5) 0.5953(4) 0.6669(5) 0.0377(12) Uani 1 1 d . . .
C10 C 0.5619(5) 0.5392(4) 0.6788(6) 0.0417(13) Uani 1 1 d . . .
C11 C 0.7086(5) 0.7628(4) 0.5973(6) 0.0416(13) Uani 1 1 d . . .
H11 H 0.6920 0.7655 0.5032 0.050 Uiso 1 1 calc R . .
C12 C 0.8319(5) 0.7239(5) 0.6720(6) 0.0467(14) Uani 1 1 d . . .
H12 H 0.8801 0.7580 0.6358 0.056 Uiso 1 1 calc R . .
C13 C 0.8319(5) 0.6132(4) 0.6439(6) 0.0471(14) Uani 1 1 d . . .
H13 H 0.7921 0.6070 0.5475 0.057 Uiso 1 1 calc R . .
C14 C 0.7642(5) 0.5473(4) 0.6977(5) 0.0422(13) Uani 1 1 d . . .
H14 H 0.7503 0.4821 0.6519 0.051 Uiso 1 1 calc R . .
C15 C 0.7376(7) 0.9365(5) 0.5733(8) 0.0664(19) Uani 1 1 d . . .
H15A H 0.7295 1.0025 0.6041 0.100 Uiso 1 1 calc R . .
H15B H 0.6926 0.9326 0.4794 0.100 Uiso 1 1 calc R . .
H15C H 0.8171 0.9245 0.5933 0.100 Uiso 1 1 calc R . .
C16 C 0.8809(7) 0.4317(6) 0.8727(8) 0.078(2) Uani 1 1 d . . .
H16A H 0.9190 0.4266 0.9673 0.117 Uiso 1 1 calc R . .
H16B H 0.9365 0.4253 0.8367 0.117 Uiso 1 1 calc R . .
H16C H 0.8249 0.3787 0.8384 0.117 Uiso 1 1 calc R . .
O1 O 0.6985(4) 0.8620(3) 0.6375(4) 0.0478(10) Uani 1 1 d . . .
O2 O 0.8244(4) 0.5284(3) 0.8361(4) 0.0526(10) Uani 1 1 d . . .
Br1 Br 0.45782(6) 0.83913(5) 0.44673(7) 0.05663(19) Uani 1 1 d . . .
Br2 Br 0.59379(6) 0.40425(5) 0.74250(7) 0.05523(19) Uani 1 1 d . . .
Br3 Br 0.89231(6) 0.75739(6) 0.86092(7) 0.0635(2) Uani 1 1 d . . .
Br4 Br 0.98757(7) 0.56455(7) 0.69106(10) 0.0799(3) Uani 1 1 d . . .
 
 
_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_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C10 1.413(8) . ?
C1 C6 1.417(8) . ?
C1 C2 1.423(8) . ?
C2 C3 1.342(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.420(8) . ?
C7 C8 1.380(8) . ?
C7 Br1 1.897(5) . ?
C8 C9 1.431(7) . ?
C8 C11 1.527(8) . ?
C9 C10 1.386(8) . ?
C9 C14 1.516(8) . ?
C10 Br2 1.901(6) . ?
C11 O1 1.411(6) . ?
C11 C12 1.531(8) . ?
C11 H11 0.9800 . ?
C12 C13 1.498(8) . ?
C12 Br3 1.964(6) . ?
C12 H12 0.9800 . ?
C13 C14 1.523(8) . ?
C13 Br4 1.946(6) . ?
C13 H13 0.9800 . ?
C14 O2 1.426(7) . ?
C14 H14 0.9800 . ?
C15 O1 1.428(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O2 1.442(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C10 C1 C6 117.8(5) . . ?
C10 C1 C2 123.4(5) . . ?
C6 C1 C2 118.7(5) . . ?
C3 C2 C1 120.3(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.5(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 119.8(6) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.1(7) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.5(6) . . ?
C5 C6 C7 123.6(6) . . ?
C1 C6 C7 117.9(5) . . ?
C8 C7 C6 122.8(5) . . ?
C8 C7 Br1 119.6(4) . . ?
C6 C7 Br1 117.2(4) . . ?
C7 C8 C9 119.4(5) . . ?
C7 C8 C11 119.5(5) . . ?
C9 C8 C11 120.9(5) . . ?
C10 C9 C8 117.1(5) . . ?
C10 C9 C14 120.1(5) . . ?
C8 C9 C14 122.5(5) . . ?
C9 C10 C1 124.2(5) . . ?
C9 C10 Br2 119.0(4) . . ?
C1 C10 Br2 116.8(4) . . ?
O1 C11 C8 110.2(4) . . ?
O1 C11 C12 110.7(5) . . ?
C8 C11 C12 113.4(5) . . ?
O1 C11 H11 107.5 . . ?
C8 C11 H11 107.5 . . ?
C12 C11 H11 107.5 . . ?
C13 C12 C11 107.9(5) . . ?
C13 C12 Br3 114.2(4) . . ?
C11 C12 Br3 110.8(4) . . ?
C13 C12 H12 107.9 . . ?
C11 C12 H12 107.9 . . ?
Br3 C12 H12 107.9 . . ?
C12 C13 C14 115.3(5) . . ?
C12 C13 Br4 111.0(4) . . ?
C14 C13 Br4 113.3(4) . . ?
C12 C13 H13 105.4 . . ?
C14 C13 H13 105.4 . . ?
Br4 C13 H13 105.4 . . ?
O2 C14 C9 110.3(4) . . ?
O2 C14 C13 113.0(5) . . ?
C9 C14 C13 109.9(5) . . ?
O2 C14 H14 107.8 . . ?
C9 C14 H14 107.8 . . ?
C13 C14 H14 107.8 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 O1 C15 112.6(5) . . ?
C14 O2 C16 116.0(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
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C10 C1 C2 C3 -176.5(6) . . . . ?
C6 C1 C2 C3 0.4(8) . . . . ?
C1 C2 C3 C4 0.8(10) . . . . ?
C2 C3 C4 C5 -1.3(10) . . . . ?
C3 C4 C5 C6 0.6(10) . . . . ?
C4 C5 C6 C1 0.6(9) . . . . ?
C4 C5 C6 C7 -178.4(6) . . . . ?
C10 C1 C6 C5 176.0(5) . . . . ?
C2 C1 C6 C5 -1.0(8) . . . . ?
C10 C1 C6 C7 -5.0(8) . . . . ?
C2 C1 C6 C7 178.0(5) . . . . ?
C5 C6 C7 C8 175.6(5) . . . . ?
C1 C6 C7 C8 -3.4(8) . . . . ?
C5 C6 C7 Br1 -11.5(7) . . . . ?
C1 C6 C7 Br1 169.5(4) . . . . ?
C6 C7 C8 C9 9.3(8) . . . . ?
Br1 C7 C8 C9 -163.5(4) . . . . ?
C6 C7 C8 C11 -175.5(5) . . . . ?
Br1 C7 C8 C11 11.7(7) . . . . ?
C7 C8 C9 C10 -6.4(7) . . . . ?
C11 C8 C9 C10 178.5(5) . . . . ?
C7 C8 C9 C14 166.7(5) . . . . ?
C11 C8 C9 C14 -8.4(8) . . . . ?
C8 C9 C10 C1 -2.1(8) . . . . ?
C14 C9 C10 C1 -175.4(5) . . . . ?
C8 C9 C10 Br2 176.4(4) . . . . ?
C14 C9 C10 Br2 3.1(7) . . . . ?
C6 C1 C10 C9 7.8(8) . . . . ?
C2 C1 C10 C9 -175.3(5) . . . . ?
C6 C1 C10 Br2 -170.7(4) . . . . ?
C2 C1 C10 Br2 6.2(7) . . . . ?
C7 C8 C11 O1 48.8(7) . . . . ?
C9 C8 C11 O1 -136.2(5) . . . . ?
C7 C8 C11 C12 173.4(5) . . . . ?
C9 C8 C11 C12 -11.5(7) . . . . ?
O1 C11 C12 C13 169.7(4) . . . . ?
C8 C11 C12 C13 45.4(6) . . . . ?
O1 C11 C12 Br3 44.1(5) . . . . ?
C8 C11 C12 Br3 -80.3(5) . . . . ?
C11 C12 C13 C14 -65.7(6) . . . . ?
Br3 C12 C13 C14 57.9(6) . . . . ?
C11 C12 C13 Br4 163.8(4) . . . . ?
Br3 C12 C13 Br4 -72.6(5) . . . . ?
C10 C9 C14 O2 -69.5(6) . . . . ?
C8 C9 C14 O2 117.6(5) . . . . ?
C10 C9 C14 C13 165.3(5) . . . . ?
C8 C9 C14 C13 -7.6(7) . . . . ?
C12 C13 C14 O2 -78.0(6) . . . . ?
Br4 C13 C14 O2 51.4(6) . . . . ?
C12 C13 C14 C9 45.7(7) . . . . ?
Br4 C13 C14 C9 175.1(4) . . . . ?
C8 C11 O1 C15 -152.7(5) . . . . ?
C12 C11 O1 C15 81.2(6) . . . . ?
C9 C14 O2 C16 136.4(6) . . . . ?
C13 C14 O2 C16 -100.2(6) . . . . ?
 
_diffrn_measured_fraction_theta_max    1.000
_diffrn_reflns_theta_full              26.00
_diffrn_measured_fraction_theta_full   1.000
_refine_diff_density_max    0.399
_refine_diff_density_min   -0.510
_refine_diff_density_rms    0.090
