# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_cyg51
_database_code_depnum_ccdc_archive 'CCDC 870337'
#TrackingRef 'cyg51.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 Br O2'
_chemical_formula_sum            'C24 H19 Br O2'
_chemical_formula_weight         419.30

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.7877(6)
_cell_length_b                   15.8468(17)
_cell_length_c                   20.507(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1880.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    1555
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      22.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    2.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4729
_exptl_absorpt_correction_T_max  0.8099
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8357
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0989
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4012
_reflns_number_gt                3186
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0646P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(17)
_refine_ls_number_reflns         4012
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_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
Br1 Br 1.04137(10) 0.61535(4) 0.95336(3) 0.02399(18) Uani 1 1 d . . .
C1 C 0.8183(10) 0.9304(3) 0.7378(3) 0.0148(12) Uani 1 1 d . . .
C2 C 0.5900(9) 0.9430(3) 0.7724(3) 0.0152(12) Uani 1 1 d . . .
H2 H 0.4951 0.8914 0.7638 0.018 Uiso 1 1 calc R . .
C3 C 0.4599(10) 1.0178(3) 0.7417(3) 0.0146(11) Uani 1 1 d . . .
H3 H 0.2988 1.0162 0.7593 0.018 Uiso 1 1 calc R . .
C4 C 0.4435(11) 0.9983(3) 0.6697(3) 0.0162(12) Uani 1 1 d . . .
H4 H 0.3160 1.0199 0.6458 0.019 Uiso 1 1 calc R . .
C5 C 0.5998(9) 0.9521(3) 0.6386(3) 0.0153(12) Uani 1 1 d . . .
C6 C 0.6258(10) 0.9475(3) 0.8463(3) 0.0179(13) Uani 1 1 d . . .
H6A H 0.7330 0.9944 0.8564 0.021 Uiso 1 1 calc R . .
H6B H 0.4762 0.9599 0.8676 0.021 Uiso 1 1 calc R . .
C7 C 0.7234(10) 0.8658(3) 0.8742(3) 0.0141(13) Uani 1 1 d . . .
C8 C 0.6046(10) 0.7903(3) 0.8680(3) 0.0161(13) Uani 1 1 d . . .
H8 H 0.4586 0.7898 0.8469 0.019 Uiso 1 1 calc R . .
C9 C 0.6939(10) 0.7161(4) 0.8919(3) 0.0188(13) Uani 1 1 d . . .
H9 H 0.6109 0.6646 0.8876 0.023 Uiso 1 1 calc R . .
C10 C 0.9085(10) 0.7179(3) 0.9224(3) 0.0170(12) Uani 1 1 d . . .
C11 C 1.0286(11) 0.7913(4) 0.9303(3) 0.0190(12) Uani 1 1 d . . .
H11 H 1.1731 0.7917 0.9523 0.023 Uiso 1 1 calc R . .
C12 C 0.9358(10) 0.8648(3) 0.9058(3) 0.0180(12) Uani 1 1 d . . .
H12 H 1.0191 0.9161 0.9106 0.022 Uiso 1 1 calc R . .
C13 C 0.5579(9) 1.1043(3) 0.7588(3) 0.0145(11) Uani 1 1 d . . .
C14 C 0.7629(10) 1.1346(3) 0.7319(3) 0.0176(13) Uani 1 1 d . . .
H14 H 0.8427 1.1018 0.7003 0.021 Uiso 1 1 calc R . .
C15 C 0.8509(11) 1.2115(3) 0.7505(3) 0.0191(14) Uani 1 1 d . . .
H15 H 0.9898 1.2321 0.7316 0.023 Uiso 1 1 calc R . .
C16 C 0.7361(10) 1.2584(3) 0.7967(3) 0.0195(14) Uani 1 1 d . . .
H16 H 0.7984 1.3108 0.8107 0.023 Uiso 1 1 calc R . .
C17 C 0.5311(12) 1.2298(3) 0.8229(3) 0.0208(13) Uani 1 1 d . . .
H17 H 0.4501 1.2631 0.8539 0.025 Uiso 1 1 calc R . .
C18 C 0.4448(11) 1.1531(3) 0.8040(3) 0.0172(12) Uani 1 1 d . . .
H18 H 0.3044 1.1333 0.8225 0.021 Uiso 1 1 calc R . .
C19 C 0.5937(9) 0.9207(3) 0.5699(3) 0.0158(12) Uani 1 1 d . . .
C20 C 0.4062(11) 0.9360(4) 0.5301(3) 0.0357(18) Uani 1 1 d . . .
H20 H 0.2811 0.9689 0.5461 0.043 Uiso 1 1 calc R . .
C21 C 0.3977(13) 0.9041(4) 0.4673(3) 0.0356(18) Uani 1 1 d . . .
H21 H 0.2656 0.9147 0.4410 0.043 Uiso 1 1 calc R . .
C22 C 0.5758(11) 0.8575(4) 0.4423(3) 0.0272(15) Uani 1 1 d . . .
H22 H 0.5710 0.8374 0.3986 0.033 Uiso 1 1 calc R . .
C23 C 0.7607(12) 0.8405(5) 0.4815(3) 0.0360(18) Uani 1 1 d . . .
H23 H 0.8835 0.8067 0.4653 0.043 Uiso 1 1 calc R . .
C24 C 0.7727(10) 0.8713(4) 0.5439(4) 0.0326(15) Uani 1 1 d . . .
H24 H 0.9042 0.8590 0.5699 0.039 Uiso 1 1 calc R . .
O1 O 1.0033(6) 0.9220(2) 0.76192(19) 0.0191(9) Uani 1 1 d . . .
O2 O 0.8059(6) 0.9280(2) 0.67014(19) 0.0169(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0263(3) 0.0275(3) 0.0181(3) 0.0035(3) -0.0034(3) 0.0042(3)
C1 0.023(3) 0.007(3) 0.014(3) 0.000(2) -0.002(3) -0.001(2)
C2 0.016(3) 0.017(3) 0.013(3) 0.000(2) 0.001(2) -0.005(2)
C3 0.013(2) 0.019(3) 0.012(3) -0.001(2) 0.000(3) 0.001(2)
C4 0.015(3) 0.015(3) 0.018(3) 0.001(2) -0.003(3) -0.005(3)
C5 0.017(3) 0.013(3) 0.015(3) 0.002(2) 0.002(2) -0.007(2)
C6 0.020(3) 0.017(3) 0.016(3) -0.004(2) 0.002(3) -0.007(2)
C7 0.019(3) 0.021(3) 0.003(3) 0.000(2) 0.002(2) -0.003(2)
C8 0.016(3) 0.022(3) 0.010(3) -0.002(2) 0.002(2) -0.003(2)
C9 0.023(3) 0.015(3) 0.018(3) -0.002(2) 0.001(3) -0.005(2)
C10 0.022(3) 0.021(3) 0.008(3) 0.004(2) 0.001(2) 0.005(2)
C11 0.018(3) 0.031(3) 0.008(3) 0.001(2) -0.003(3) -0.003(3)
C12 0.020(3) 0.023(3) 0.011(3) 0.000(2) 0.001(3) -0.006(2)
C13 0.015(2) 0.014(3) 0.014(3) 0.002(2) -0.004(2) 0.006(3)
C14 0.021(3) 0.016(3) 0.016(3) 0.001(2) 0.004(3) 0.001(2)
C15 0.023(3) 0.012(3) 0.022(4) 0.009(2) -0.003(3) -0.002(2)
C16 0.029(3) 0.008(3) 0.021(4) 0.001(2) -0.014(3) 0.000(2)
C17 0.035(4) 0.014(3) 0.013(3) 0.002(2) 0.002(3) 0.009(3)
C18 0.018(3) 0.018(3) 0.016(3) 0.005(2) 0.003(3) 0.004(3)
C19 0.023(3) 0.011(2) 0.013(3) 0.001(2) 0.002(2) -0.006(2)
C20 0.033(4) 0.041(4) 0.034(4) -0.016(3) -0.006(3) 0.018(3)
C21 0.049(4) 0.042(4) 0.016(4) -0.013(3) -0.014(3) 0.011(3)
C22 0.034(4) 0.033(3) 0.014(3) 0.001(2) 0.005(3) -0.001(3)
C23 0.037(4) 0.058(5) 0.013(4) -0.011(3) 0.010(3) 0.008(4)
C24 0.022(3) 0.050(4) 0.026(4) -0.004(4) -0.001(3) 0.007(3)
O1 0.016(2) 0.022(2) 0.019(2) 0.0032(16) -0.0019(18) -0.0004(16)
O2 0.0132(19) 0.025(2) 0.013(2) -0.0004(17) -0.0023(17) -0.0004(17)

_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
Br1 C10 1.907(5) . ?
C1 O1 1.187(7) . ?
C1 O2 1.389(7) . ?
C1 C2 1.514(8) . ?
C2 C6 1.530(8) . ?
C2 C3 1.540(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.511(7) . ?
C3 C13 1.524(7) . ?
C3 H3 1.0000 . ?
C4 C5 1.328(8) . ?
C4 H4 0.9500 . ?
C5 O2 1.410(7) . ?
C5 C19 1.495(8) . ?
C6 C7 1.524(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.386(7) . ?
C7 C12 1.390(8) . ?
C8 C9 1.374(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.365(8) . ?
C11 C12 1.377(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.374(8) . ?
C13 C14 1.394(8) . ?
C14 C15 1.376(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.369(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.379(8) . ?
C19 C24 1.403(8) . ?
C20 C21 1.386(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.367(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.366(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.371(10) . ?
C23 H23 0.9500 . ?
C24 H24 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
O1 C1 O2 117.4(5) . . ?
O1 C1 C2 127.3(5) . . ?
O2 C1 C2 115.3(5) . . ?
C1 C2 C6 110.6(5) . . ?
C1 C2 C3 109.6(4) . . ?
C6 C2 C3 115.8(5) . . ?
C1 C2 H2 106.8 . . ?
C6 C2 H2 106.8 . . ?
C3 C2 H2 106.8 . . ?
C4 C3 C13 115.6(4) . . ?
C4 C3 C2 105.8(4) . . ?
C13 C3 C2 114.6(4) . . ?
C4 C3 H3 106.7 . . ?
C13 C3 H3 106.7 . . ?
C2 C3 H3 106.7 . . ?
C5 C4 C3 122.7(5) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 O2 120.3(5) . . ?
C4 C5 C19 128.4(5) . . ?
O2 C5 C19 111.3(5) . . ?
C7 C6 C2 112.4(5) . . ?
C7 C6 H6A 109.1 . . ?
C2 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C2 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C12 118.1(5) . . ?
C8 C7 C6 121.1(5) . . ?
C12 C7 C6 120.8(5) . . ?
C9 C8 C7 121.3(5) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 118.5(5) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C10 C9 121.8(5) . . ?
C11 C10 Br1 118.8(4) . . ?
C9 C10 Br1 119.5(4) . . ?
C10 C11 C12 118.6(5) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C7 121.7(5) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
C18 C13 C14 118.6(5) . . ?
C18 C13 C3 119.0(5) . . ?
C14 C13 C3 122.4(5) . . ?
C15 C14 C13 120.7(6) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.4(6) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.5(5) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.7(5) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C13 121.1(6) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C20 C19 C24 117.1(5) . . ?
C20 C19 C5 121.1(5) . . ?
C24 C19 C5 121.7(5) . . ?
C19 C20 C21 120.9(6) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 121.3(6) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 118.4(6) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C22 C23 C24 121.3(6) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 121.0(6) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C1 O2 C5 119.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.137