data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. B. M. Heron
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C27 H21 Br0.50 Cl0.50 O3'
_chemical_formula_sum
 'C27 H21 Br0.50 Cl0.50 O3'
_chemical_formula_weight          451.12
 
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'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/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                    11.1956(3)
_cell_length_b                    10.5272(3)
_cell_length_c                    18.8213(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  102.6660(10)
_cell_angle_gamma                 90.00
_cell_volume                      2164.27(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     5090
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             'Light Brown'
_exptl_crystal_size_max           0.32
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.384
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              932
_exptl_absorpt_coefficient_mu     1.065
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7269
_exptl_absorpt_correction_T_max   0.9587
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             29910
_diffrn_reflns_av_R_equivalents   0.0768
_diffrn_reflns_av_sigmaI/netI     0.0570
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          2.94
_diffrn_reflns_theta_max          27.49
_reflns_number_total              4927
_reflns_number_gt                 3647
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0210P)²+2.9999P] 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      SHELXL
_refine_ls_extinction_coef        0.0084(7)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4927
_refine_ls_number_parameters      286
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0884
_refine_ls_R_factor_gt            0.0582
_refine_ls_wR_factor_ref          0.1245
_refine_ls_wR_factor_gt           0.1154
_refine_ls_goodness_of_fit_ref    1.175
_refine_ls_restrained_S_all       1.175
_refine_ls_shift/su_max           0.002
_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 -0.0186(3) 0.1335(3) 0.65079(19) 0.0417(8) Uani 1 1 d D . .
C2 C 0.0431(3) 0.2465(3) 0.65747(18) 0.0372(8) Uani 1 1 d . A .
H2 H 0.0179 0.3148 0.6837 0.045 Uiso 1 1 calc R . .
C3 C 0.1453(3) 0.2610(3) 0.62484(17) 0.0342(7) Uani 1 1 d . . .
C4 C 0.2114(3) 0.3758(3) 0.63058(18) 0.0372(8) Uani 1 1 d . A .
H4 H 0.1906 0.4429 0.6593 0.045 Uiso 1 1 calc R . .
C5 C 0.3051(3) 0.3922(3) 0.59548(17) 0.0358(7) Uani 1 1 d . . .
H5 H 0.3499 0.4696 0.6005 0.043 Uiso 1 1 calc R A .
C6 C 0.3347(3) 0.2933(3) 0.55172(17) 0.0327(7) Uani 1 1 d . A .
C7 C 0.2766(3) 0.1766(3) 0.54634(17) 0.0329(7) Uani 1 1 d . . .
C8 C 0.1798(3) 0.1584(3) 0.58371(17) 0.0356(8) Uani 1 1 d . A .
C9 C 0.1136(3) 0.0426(3) 0.58065(19) 0.0388(8) Uani 1 1 d . . .
H9 H 0.1378 -0.0280 0.5557 0.047 Uiso 1 1 calc R A .
C10 C 0.0166(4) 0.0305(3) 0.6126(2) 0.0457(9) Uani 1 1 d . A .
H10 H -0.0273 -0.0473 0.6091 0.055 Uiso 1 1 calc R . .
C11 C 0.3234(3) 0.0793(3) 0.50446(18) 0.0349(8) Uani 1 1 d . A .
H11 H 0.3026 -0.0073 0.5092 0.042 Uiso 1 1 calc R . .
C12 C 0.3946(3) 0.1115(3) 0.45996(17) 0.0344(7) Uani 1 1 d . . .
H12 H 0.4276 0.0474 0.4343 0.041 Uiso 1 1 calc R A .
C13 C 0.4240(3) 0.2487(3) 0.44954(17) 0.0334(7) Uani 1 1 d . A .
C14 C 0.3248(3) 0.3127(3) 0.39187(17) 0.0316(7) Uani 1 1 d . . .
C15 C 0.2392(3) 0.2441(3) 0.34284(18) 0.0345(7) Uani 1 1 d . A .
H15 H 0.2431 0.1539 0.3443 0.041 Uiso 1 1 calc R . .
C16 C 0.1471(3) 0.3026(3) 0.29129(18) 0.0374(8) Uani 1 1 d . . .
H16 H 0.0896 0.2533 0.2579 0.045 Uiso 1 1 calc R A .
C17 C 0.1412(3) 0.4339(3) 0.28979(18) 0.0352(8) Uani 1 1 d . A .
C18 C 0.2284(3) 0.5056(3) 0.33779(19) 0.0382(8) Uani 1 1 d . . .
H18 H 0.2254 0.5957 0.3358 0.046 Uiso 1 1 calc R A .
C19 C 0.3191(3) 0.4454(3) 0.38814(18) 0.0353(8) Uani 1 1 d . A .
H19 H 0.3782 0.4947 0.4206 0.042 Uiso 1 1 calc R . .
C20 C -0.0427(3) 0.4325(4) 0.1973(2) 0.0525(10) Uani 1 1 d . A .
H20A H -0.0084 0.3819 0.1628 0.079 Uiso 1 1 calc R . .
H20B H -0.1041 0.4913 0.1703 0.079 Uiso 1 1 calc R . .
H20C H -0.0811 0.3760 0.2271 0.079 Uiso 1 1 calc R . .
C21 C 0.5508(3) 0.2645(3) 0.43425(17) 0.0322(7) Uani 1 1 d . . .
C22 C 0.5676(3) 0.2633(3) 0.36300(18) 0.0380(8) Uani 1 1 d . A .
H22 H 0.4985 0.2548 0.3237 0.046 Uiso 1 1 calc R . .
C23 C 0.6828(3) 0.2741(3) 0.34850(19) 0.0382(8) Uani 1 1 d . . .
H23 H 0.6925 0.2712 0.2996 0.046 Uiso 1 1 calc R A .
C24 C 0.7848(3) 0.2893(3) 0.40536(18) 0.0348(8) Uani 1 1 d . A .
C25 C 0.7705(3) 0.2890(3) 0.47667(17) 0.0341(7) Uani 1 1 d . . .
H25 H 0.8398 0.2971 0.5158 0.041 Uiso 1 1 calc R A .
C26 C 0.6548(3) 0.2767(3) 0.49039(18) 0.0344(7) Uani 1 1 d . A .
H26 H 0.6458 0.2766 0.5394 0.041 Uiso 1 1 calc R . .
C27 C 0.9985(3) 0.3304(4) 0.4420(2) 0.0521(10) Uani 1 1 d . A .
H27A H 0.9825 0.4042 0.4703 0.078 Uiso 1 1 calc R . .
H27B H 1.0698 0.3474 0.4211 0.078 Uiso 1 1 calc R . .
H27C H 1.0149 0.2560 0.4740 0.078 Uiso 1 1 calc R . .
O1 O 0.4299(2) 0.3162(2) 0.51878(12) 0.0343(5) Uani 1 1 d . . .
O2 O 0.0529(2) 0.5030(2) 0.24323(13) 0.0447(6) Uani 1 1 d . . .
O3 O 0.8941(2) 0.3063(2) 0.38475(12) 0.0402(6) Uani 1 1 d . . .
Cl1 Cl -0.1496(13) 0.1157(15) 0.6823(7) 0.0334(5) Uani 0.50 1 d PD A 1
Br1 Br -0.1586(5) 0.1185(6) 0.6919(3) 0.0334(5) Uani 0.50 1 d PD A 2
 
 
_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 C2 1.368(5) . ?
C1 C10 1.405(5) . ?
C1 Cl1 1.708(12) . ?
C1 Br1 1.900(6) . ?
C2 C3 1.420(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(5) . ?
C3 C8 1.431(4) . ?
C4 C5 1.368(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(4) . ?
C5 H5 0.9500 . ?
C6 O1 1.367(4) . ?
C6 C7 1.383(4) . ?
C7 C8 1.429(5) . ?
C7 C11 1.458(4) . ?
C8 C9 1.421(5) . ?
C9 C10 1.357(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.321(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.504(4) . ?
C12 H12 0.9500 . ?
C13 O1 1.473(4) . ?
C13 C21 1.518(5) . ?
C13 C14 1.529(4) . ?
C14 C15 1.380(4) . ?
C14 C19 1.400(4) . ?
C15 C16 1.395(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(5) . ?
C16 H16 0.9500 . ?
C17 O2 1.377(4) . ?
C17 C18 1.397(4) . ?
C18 C19 1.381(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O2 1.427(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.394(5) . ?
C21 C26 1.396(4) . ?
C22 C23 1.381(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(4) . ?
C23 H23 0.9500 . ?
C24 O3 1.374(4) . ?
C24 C25 1.386(5) . ?
C25 C26 1.381(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 O3 1.429(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
 
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
C2 C1 C10 121.7(3) . . ?
C2 C1 Cl1 121.2(6) . . ?
C10 C1 Cl1 116.9(6) . . ?
C2 C1 Br1 118.7(3) . . ?
C10 C1 Br1 119.6(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 C8 119.3(3) . . ?
C2 C3 C8 119.4(3) . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
O1 C6 C7 121.7(3) . . ?
O1 C6 C5 116.1(3) . . ?
C7 C6 C5 122.1(3) . . ?
C6 C7 C8 118.6(3) . . ?
C6 C7 C11 116.4(3) . . ?
C8 C7 C11 124.9(3) . . ?
C9 C8 C7 122.7(3) . . ?
C9 C8 C3 118.0(3) . . ?
C7 C8 C3 119.2(3) . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C1 119.7(3) . . ?
C9 C10 H10 120.1 . . ?
C1 C10 H10 120.1 . . ?
C12 C11 C7 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C7 C11 H11 120.0 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
O1 C13 C12 108.5(3) . . ?
O1 C13 C21 104.6(2) . . ?
C12 C13 C21 111.7(3) . . ?
O1 C13 C14 107.5(2) . . ?
C12 C13 C14 111.7(3) . . ?
C21 C13 C14 112.4(3) . . ?
C15 C14 C19 118.2(3) . . ?
C15 C14 C13 122.3(3) . . ?
C19 C14 C13 119.6(3) . . ?
C14 C15 C16 122.2(3) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
O2 C17 C16 124.4(3) . . ?
O2 C17 C18 115.4(3) . . ?
C16 C17 C18 120.2(3) . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.7(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 117.6(3) . . ?
C22 C21 C13 120.7(3) . . ?
C26 C21 C13 121.7(3) . . ?
C23 C22 C21 121.2(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 120.1(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
O3 C24 C25 124.9(3) . . ?
O3 C24 C23 115.4(3) . . ?
C25 C24 C23 119.7(3) . . ?
C26 C25 C24 119.6(3) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C21 121.9(3) . . ?
C25 C26 H26 119.1 . . ?
C21 C26 H26 119.1 . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C6 O1 C13 115.3(2) . . ?
C17 O2 C20 116.7(3) . . ?
C24 O3 C27 116.3(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.539
_refine_diff_density_min   -0.481
_refine_diff_density_rms    0.066
