data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. A. K. Croft
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety           'C17 H15 Br'
_chemical_formula_sum
 'C17 H15 Br'
_chemical_formula_weight          299.20
 
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'
 '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    P2(1)/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                    8.4575(6)
_cell_length_b                    25.0260(15)
_cell_length_c                    6.5393(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  106.485(5)
_cell_angle_gamma                 90.00
_cell_volume                      1327.20(16)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2588
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        'Cut Shard'
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.22
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.497
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              608
_exptl_absorpt_coefficient_mu     3.076
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5510
_exptl_absorpt_correction_T_max   0.9134
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)' 

_diffrn_ambient_temperature           120(2) 
_diffrn_radiation_wavelength           0.71073 
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on κ-goniostat' 
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             14309
_diffrn_reflns_av_R_equivalents   0.0468
_diffrn_reflns_av_sigmaI/netI     0.0489
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -32
_diffrn_reflns_limit_k_max        32
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_theta_min          2.99
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3033
_reflns_number_gt                 1987
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_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)+(0.0269P)²+1.2800P] 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        0.0033(7)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3033
_refine_ls_number_parameters      164
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0883
_refine_ls_R_factor_gt            0.0464
_refine_ls_wR_factor_ref          0.1032
_refine_ls_wR_factor_gt           0.0873
_refine_ls_goodness_of_fit_ref    1.015
_refine_ls_restrained_S_all       1.015
_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 0.2201(4) 0.40859(12) 0.6564(5) 0.0476(8) Uani 1 1 d . . .
H1A H 0.3228 0.3911 0.6471 0.057 Uiso 1 1 calc R . .
H1B H 0.1944 0.3947 0.7851 0.057 Uiso 1 1 calc R . .
C2 C 0.0815(4) 0.39388(11) 0.4618(4) 0.0386(7) Uani 1 1 d . . .
H2 H -0.0220 0.4117 0.4715 0.046 Uiso 1 1 calc R . .
C3 C 0.0567(4) 0.33234(11) 0.4607(5) 0.0443(7) Uani 1 1 d . . .
H3A H 0.1390 0.3163 0.5843 0.053 Uiso 1 1 calc R . .
H3B H -0.0546 0.3241 0.4734 0.053 Uiso 1 1 calc R . .
C4 C 0.0765(3) 0.30805(11) 0.2510(5) 0.0395(7) Uani 1 1 d . . .
H4 H 0.0625 0.2683 0.2467 0.047 Uiso 1 1 calc R . .
C5 C 0.2444(3) 0.32449(12) 0.2333(4) 0.0385(7) Uani 1 1 d . . .
C6 C 0.3689(4) 0.29104(13) 0.2137(5) 0.0484(8) Uani 1 1 d . . .
H6 H 0.3558 0.2534 0.2166 0.058 Uiso 1 1 calc R . .
C7 C 0.5134(4) 0.31294(15) 0.1899(5) 0.0545(9) Uani 1 1 d . . .
H7 H 0.5987 0.2901 0.1737 0.065 Uiso 1 1 calc R . .
C8 C 0.5339(4) 0.36737(15) 0.1895(5) 0.0524(8) Uani 1 1 d . . .
H8 H 0.6333 0.3819 0.1731 0.063 Uiso 1 1 calc R . .
C9 C 0.4102(4) 0.40128(13) 0.2130(4) 0.0440(7) Uani 1 1 d . . .
H9 H 0.4259 0.4389 0.2164 0.053 Uiso 1 1 calc R . .
C10 C 0.2641(3) 0.37992(12) 0.2313(4) 0.0358(6) Uani 1 1 d . . .
C11 C 0.1147(3) 0.41048(11) 0.2475(4) 0.0370(6) Uani 1 1 d . . .
H11 H 0.1301 0.4500 0.2389 0.044 Uiso 1 1 calc R . .
C12 C -0.0304(3) 0.39052(12) 0.0702(4) 0.0382(7) Uani 1 1 d . . .
C13 C -0.1368(4) 0.42129(14) -0.0849(5) 0.0488(8) Uani 1 1 d . . .
H13 H -0.1243 0.4590 -0.0854 0.059 Uiso 1 1 calc R . .
C14 C -0.2622(4) 0.39644(17) -0.2397(5) 0.0579(9) Uani 1 1 d . . .
H14 H -0.3353 0.4173 -0.3470 0.070 Uiso 1 1 calc R . .
C15 C -0.2816(4) 0.34209(17) -0.2394(5) 0.0598(10) Uani 1 1 d . . .
H15 H -0.3679 0.3256 -0.3463 0.072 Uiso 1 1 calc R . .
C16 C -0.1759(4) 0.31100(14) -0.0837(5) 0.0505(8) Uani 1 1 d . . .
H16 H -0.1899 0.2733 -0.0834 0.061 Uiso 1 1 calc R . .
C17 C -0.0501(3) 0.33520(12) 0.0707(5) 0.0395(7) Uani 1 1 d . . .
Br1 Br 0.25718(6) 0.485279(16) 0.68740(7) 0.0809(2) 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 C2 1.511(4) . ?
C1 Br1 1.946(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.554(4) . ?
C2 C11 1.562(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.551(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C17 1.510(4) . ?
C4 C5 1.515(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.379(4) . ?
C5 C10 1.398(4) . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.506(4) . ?
C11 C12 1.514(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.383(4) . ?
C12 C17 1.395(4) . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
 
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 Br1 113.1(2) . . ?
C2 C1 H1A 109.0 . . ?
Br1 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
Br1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 108.5(2) . . ?
C1 C2 C11 113.4(2) . . ?
C3 C2 C11 108.5(2) . . ?
C1 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C11 C2 H2 108.8 . . ?
C4 C3 C2 110.2(2) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C17 C4 C5 106.9(2) . . ?
C17 C4 C3 106.5(2) . . ?
C5 C4 C3 107.4(2) . . ?
C17 C4 H4 111.9 . . ?
C5 C4 H4 111.9 . . ?
C3 C4 H4 111.9 . . ?
C6 C5 C10 120.4(3) . . ?
C6 C5 C4 126.8(3) . . ?
C10 C5 C4 112.8(2) . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C5 119.8(3) . . ?
C9 C10 C11 126.7(3) . . ?
C5 C10 C11 113.5(2) . . ?
C10 C11 C12 107.0(2) . . ?
C10 C11 C2 107.2(2) . . ?
C12 C11 C2 106.6(2) . . ?
C10 C11 H11 111.9 . . ?
C12 C11 H11 111.9 . . ?
C2 C11 H11 111.9 . . ?
C13 C12 C17 120.1(3) . . ?
C13 C12 C11 126.5(3) . . ?
C17 C12 C11 113.4(2) . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 120.1(3) . . ?
C16 C17 C4 127.0(3) . . ?
C12 C17 C4 112.9(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.376
_refine_diff_density_min   -0.570
_refine_diff_density_rms    0.055
