data_dout051
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H25 Br O2'
_chemical_formula_weight          389.32
 
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                    7.996(2)
_cell_length_b                    8.270(2)
_cell_length_c                    28.609(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1891.8(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     200(2)
_cell_measurement_reflns_used     958
_cell_measurement_theta_min       2.56
_cell_measurement_theta_max       28.30
 
_exptl_crystal_description        cube
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.43
_exptl_crystal_size_mid           0.31
_exptl_crystal_size_min           0.15
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.367
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              808
_exptl_absorpt_coefficient_mu     2.182
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.4531
_exptl_absorpt_correction_T_max   0.7341
_exptl_absorpt_process_details    'SADABS (Sheldrick, 2003)'
 
_exptl_special_details
;
Data collection is performed with four batch runs at
\f = 0.00 \% (600 frames), at \f = 90.00 \%
(600 frames), at \f = 180 \% (600 frames) and
at \f = 270 \% (600 frames).
Frame width = 0.30 \& in \w. Data is
merged, corrected for decay, and treated with
multi-scan absorption corrections.
;
 
_diffrn_ambient_temperature       200(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 AXS APEX diffractometer'
_diffrn_measurement_method        \w
_diffrn_detector_area_resol_mean  836.6
_diffrn_standards_number          0
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0
_diffrn_standards_decay_%         1
_diffrn_reflns_number             22977
_diffrn_reflns_av_R_equivalents   0.0245
_diffrn_reflns_av_sigmaI/netI     0.0175
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -38
_diffrn_reflns_limit_l_max        38
_diffrn_reflns_theta_min          2.56
_diffrn_reflns_theta_max          28.30
_reflns_number_total              4693
_reflns_number_gt                 4411
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'SMART (Bruker, 2002)'
_computing_cell_refinement        'SAINT (Bruker, 2002)'
_computing_data_reduction         SAINT
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2001)'
_computing_publication_material   'SHELXTL (Sheldrick, 2001)'
 
_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^)+(0.0500P)^2^+0.0390P] 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: 1986 Friedel pairs'
_refine_ls_abs_structure_Flack    -0.008(6)
_refine_ls_number_reflns          4693
_refine_ls_number_parameters      217
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0265
_refine_ls_R_factor_gt            0.0241
_refine_ls_wR_factor_ref          0.0684
_refine_ls_wR_factor_gt           0.0670
_refine_ls_goodness_of_fit_ref    1.025
_refine_ls_restrained_S_all       1.025
_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
Br Br 0.30319(2) -0.78110(2) 0.023301(7) 0.04849(7) Uani 1 1 d . . .
O1 O 0.76089(15) -0.31791(18) 0.06198(5) 0.0516(3) Uani 1 1 d . . .
O2 O 0.61677(14) -0.10087(15) 0.08766(4) 0.0398(2) Uani 1 1 d . . .
C1 C 0.31531(19) -0.23334(19) 0.06205(5) 0.0368(3) Uani 1 1 d . . .
H1A H 0.3178 -0.1230 0.0712 0.044 Uiso 1 1 calc R . .
C2 C 0.16370(19) -0.3090(2) 0.05301(7) 0.0413(4) Uani 1 1 d . . .
H2A H 0.0626 -0.2492 0.0554 0.050 Uiso 1 1 calc R . .
C3 C 0.15828(19) -0.4718(2) 0.04039(6) 0.0385(3) Uani 1 1 d . . .
H3A H 0.0544 -0.5236 0.0344 0.046 Uiso 1 1 calc R . .
C4 C 0.3068(2) -0.55624(18) 0.03676(5) 0.0358(3) Uani 1 1 d . . .
C5 C 0.4602(2) -0.4823(2) 0.04445(6) 0.0356(3) Uani 1 1 d . . .
H5A H 0.5613 -0.5413 0.0408 0.043 Uiso 1 1 calc R . .
C6 C 0.46320(18) -0.3199(2) 0.05759(5) 0.0326(3) Uani 1 1 d . . .
C7 C 0.62988(19) -0.24883(19) 0.06874(6) 0.0374(3) Uani 1 1 d . . .
C8 C 0.77305(19) -0.0233(2) 0.10162(6) 0.0370(3) Uani 1 1 d . . .
H8A H 0.8596 -0.0416 0.0770 0.044 Uiso 1 1 calc R . .
C9 C 0.8344(2) -0.0925(2) 0.14787(6) 0.0414(4) Uani 1 1 d . . .
H9A H 0.7469 -0.0788 0.1720 0.050 Uiso 1 1 calc R . .
H9B H 0.8567 -0.2096 0.1443 0.050 Uiso 1 1 calc R . .
C10 C 0.9927(2) -0.00701(19) 0.16313(5) 0.0350(3) Uani 1 1 d . . .
C11 C 0.9849(2) 0.17866(18) 0.16553(5) 0.0346(3) Uani 1 1 d . . .
C12 C 0.9033(2) 0.24104(19) 0.11957(6) 0.0381(3) Uani 1 1 d . . .
H12A H 0.8806 0.3582 0.1229 0.046 Uiso 1 1 calc R . .
H12B H 0.9843 0.2275 0.0937 0.046 Uiso 1 1 calc R . .
C13 C 0.7400(2) 0.1553(2) 0.10634(6) 0.0402(4) Uani 1 1 d . . .
H13A H 0.6546 0.1743 0.1308 0.048 Uiso 1 1 calc R . .
H13B H 0.6972 0.1989 0.0764 0.048 Uiso 1 1 calc R . .
C14 C 1.1299(2) -0.0920(2) 0.17267(6) 0.0417(4) Uani 1 1 d . . .
H14A H 1.1244 -0.2059 0.1686 0.050 Uiso 1 1 calc R . .
C15 C 1.2922(2) -0.0225(2) 0.18937(7) 0.0469(4) Uani 1 1 d . . .
H15A H 1.3758 -0.0276 0.1639 0.056 Uiso 1 1 calc R . .
H15B H 1.3346 -0.0873 0.2159 0.056 Uiso 1 1 calc R . .
C16 C 1.2695(2) 0.1527(2) 0.20477(6) 0.0438(4) Uani 1 1 d . . .
H16A H 1.3803 0.2048 0.2080 0.053 Uiso 1 1 calc R . .
H16B H 1.2135 0.1556 0.2356 0.053 Uiso 1 1 calc R . .
C17 C 1.1644(2) 0.24579(19) 0.16903(5) 0.0366(3) Uani 1 1 d . . .
H17A H 1.2179 0.2285 0.1378 0.044 Uiso 1 1 calc R . .
C18 C 0.8762(3) 0.2314(3) 0.20739(6) 0.0526(4) Uani 1 1 d . . .
H18A H 0.8714 0.3497 0.2087 0.079 Uiso 1 1 calc R . .
H18B H 0.9252 0.1899 0.2364 0.079 Uiso 1 1 calc R . .
H18C H 0.7629 0.1880 0.2037 0.079 Uiso 1 1 calc R . .
C19 C 1.1751(3) 0.4295(2) 0.17947(8) 0.0516(5) Uani 1 1 d . . .
H19A H 1.0901 0.4872 0.1606 0.062 Uiso 1 1 calc R . .
H19B H 1.1496 0.4484 0.2129 0.062 Uiso 1 1 calc R . .
C20 C 1.3426(3) 0.4956(2) 0.16869(8) 0.0608(6) Uani 1 1 d . . .
H20A H 1.3759 0.4925 0.1368 0.073 Uiso 1 1 calc R . .
C21 C 1.4496(3) 0.5576(3) 0.19795(10) 0.0643(6) Uani 1 1 d . . .
H21A H 1.4230 0.5638 0.2303 0.077 Uiso 1 1 calc R . .
H21B H 1.5542 0.5966 0.1870 0.077 Uiso 1 1 calc R . .
 
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
Br 0.04588(10) 0.03866(9) 0.06092(11) -0.01333(7) -0.00254(8) -0.00265(7)
O1 0.0259(5) 0.0515(8) 0.0775(9) -0.0165(7) 0.0005(5) 0.0004(5)
O2 0.0274(5) 0.0387(6) 0.0533(6) -0.0077(5) -0.0025(5) -0.0033(5)
C1 0.0301(7) 0.0349(7) 0.0455(7) 0.0003(6) -0.0015(6) 0.0000(7)
C2 0.0245(7) 0.0430(9) 0.0563(9) 0.0000(7) -0.0023(6) 0.0032(6)
C3 0.0264(7) 0.0430(8) 0.0462(8) -0.0017(7) -0.0045(6) -0.0044(6)
C4 0.0352(7) 0.0346(7) 0.0375(7) -0.0032(5) -0.0010(6) -0.0013(7)
C5 0.0268(7) 0.0401(8) 0.0399(7) -0.0050(7) 0.0001(6) 0.0011(6)
C6 0.0249(7) 0.0378(8) 0.0352(7) -0.0017(6) -0.0006(5) -0.0011(5)
C7 0.0273(7) 0.0388(9) 0.0462(8) -0.0037(6) -0.0013(6) -0.0014(6)
C8 0.0264(7) 0.0379(8) 0.0465(8) -0.0018(6) -0.0019(6) -0.0057(6)
C9 0.0401(9) 0.0340(7) 0.0500(9) 0.0061(6) -0.0058(7) -0.0081(6)
C10 0.0396(8) 0.0298(7) 0.0356(7) 0.0028(6) -0.0024(6) -0.0051(6)
C11 0.0372(8) 0.0315(7) 0.0349(7) 0.0001(5) -0.0015(6) -0.0005(6)
C12 0.0387(8) 0.0312(8) 0.0443(8) 0.0050(6) -0.0088(6) -0.0036(6)
C13 0.0349(8) 0.0369(8) 0.0488(8) 0.0027(7) -0.0068(6) -0.0010(6)
C14 0.0481(9) 0.0296(7) 0.0473(8) 0.0017(6) -0.0095(7) -0.0011(7)
C15 0.0458(9) 0.0364(8) 0.0584(10) 0.0024(7) -0.0165(9) 0.0015(8)
C16 0.0504(10) 0.0352(7) 0.0457(8) 0.0014(6) -0.0150(7) -0.0032(7)
C17 0.0409(8) 0.0312(7) 0.0376(7) 0.0004(5) -0.0070(6) -0.0048(6)
C18 0.0579(11) 0.0519(10) 0.0479(9) -0.0080(8) 0.0101(8) 0.0002(9)
C19 0.0600(12) 0.0314(8) 0.0634(11) -0.0020(7) -0.0224(10) -0.0040(8)
C20 0.0848(16) 0.0449(10) 0.0528(10) 0.0090(8) -0.0177(10) -0.0235(11)
C21 0.0566(13) 0.0552(12) 0.0813(15) -0.0116(11) -0.0198(11) -0.0050(10)
 
_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
Br C4 1.8993(16) . ?
O1 C7 1.209(2) . ?
O2 C7 1.342(2) . ?
O2 C8 1.4605(18) . ?
C1 C2 1.388(2) . ?
C1 C6 1.388(2) . ?
C2 C3 1.395(3) . ?
C3 C4 1.382(2) . ?
C4 C5 1.388(2) . ?
C5 C6 1.395(2) . ?
C6 C7 1.491(2) . ?
C8 C13 1.506(2) . ?
C8 C9 1.523(2) . ?
C9 C10 1.514(2) . ?
C10 C14 1.331(2) . ?
C10 C11 1.538(2) . ?
C11 C17 1.542(2) . ?
C11 C18 1.542(2) . ?
C11 C12 1.556(2) . ?
C12 C13 1.533(2) . ?
C14 C15 1.498(2) . ?
C15 C16 1.525(3) . ?
C16 C17 1.531(2) . ?
C17 C19 1.550(2) . ?
C19 C20 1.479(3) . ?
C20 C21 1.302(3) . ?
 
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
C7 O2 C8 116.37(12) . . ?
C2 C1 C6 119.63(14) . . ?
C1 C2 C3 120.68(14) . . ?
C4 C3 C2 118.73(14) . . ?
C3 C4 C5 121.67(14) . . ?
C3 C4 Br 119.80(12) . . ?
C5 C4 Br 118.48(12) . . ?
C4 C5 C6 118.83(14) . . ?
C1 C6 C5 120.44(14) . . ?
C1 C6 C7 122.57(14) . . ?
C5 C6 C7 116.92(13) . . ?
O1 C7 O2 124.26(14) . . ?
O1 C7 C6 123.65(14) . . ?
O2 C7 C6 112.08(13) . . ?
O2 C8 C13 107.78(13) . . ?
O2 C8 C9 110.36(14) . . ?
C13 C8 C9 110.32(14) . . ?
C10 C9 C8 110.12(13) . . ?
C14 C10 C9 120.09(14) . . ?
C14 C10 C11 123.47(15) . . ?
C9 C10 C11 116.42(14) . . ?
C10 C11 C17 108.92(13) . . ?
C10 C11 C18 109.86(14) . . ?
C17 C11 C18 111.86(14) . . ?
C10 C11 C12 108.07(12) . . ?
C17 C11 C12 109.02(13) . . ?
C18 C11 C12 109.03(14) . . ?
C13 C12 C11 114.37(13) . . ?
C8 C13 C12 109.03(13) . . ?
C10 C14 C15 125.22(15) . . ?
C14 C15 C16 110.73(16) . . ?
C15 C16 C17 110.49(14) . . ?
C16 C17 C11 111.91(13) . . ?
C16 C17 C19 109.49(13) . . ?
C11 C17 C19 114.62(14) . . ?
C20 C19 C17 111.84(18) . . ?
C21 C20 C19 127.3(2) . . ?
 
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
C6 C1 C2 C3 1.3(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C2 C3 C4 Br 176.28(13) . . . . ?
C3 C4 C5 C6 2.0(2) . . . . ?
Br C4 C5 C6 -175.53(12) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C1 C6 C7 -177.24(16) . . . . ?
C4 C5 C6 C1 -1.2(2) . . . . ?
C4 C5 C6 C7 175.80(15) . . . . ?
C8 O2 C7 O1 -1.5(2) . . . . ?
C8 O2 C7 C6 177.60(14) . . . . ?
C1 C6 C7 O1 -174.55(17) . . . . ?
C5 C6 C7 O1 8.6(2) . . . . ?
C1 C6 C7 O2 6.4(2) . . . . ?
C5 C6 C7 O2 -170.53(14) . . . . ?
C7 O2 C8 C13 161.28(14) . . . . ?
C7 O2 C8 C9 -78.18(18) . . . . ?
O2 C8 C9 C10 -177.76(13) . . . . ?
C13 C8 C9 C10 -58.76(18) . . . . ?
C8 C9 C10 C14 -125.33(17) . . . . ?
C8 C9 C10 C11 53.28(19) . . . . ?
C14 C10 C11 C17 13.0(2) . . . . ?
C9 C10 C11 C17 -165.61(13) . . . . ?
C14 C10 C11 C18 -109.89(19) . . . . ?
C9 C10 C11 C18 71.55(18) . . . . ?
C14 C10 C11 C12 131.26(17) . . . . ?
C9 C10 C11 C12 -47.30(19) . . . . ?
C10 C11 C12 C13 49.20(19) . . . . ?
C17 C11 C12 C13 167.45(14) . . . . ?
C18 C11 C12 C13 -70.17(17) . . . . ?
O2 C8 C13 C12 -178.33(13) . . . . ?
C9 C8 C13 C12 61.11(18) . . . . ?
C11 C12 C13 C8 -57.92(19) . . . . ?
C9 C10 C14 C15 -178.10(17) . . . . ?
C11 C10 C14 C15 3.4(3) . . . . ?
C10 C14 C15 C16 13.0(3) . . . . ?
C14 C15 C16 C17 -45.0(2) . . . . ?
C15 C16 C17 C11 64.0(2) . . . . ?
C15 C16 C17 C19 -167.77(17) . . . . ?
C10 C11 C17 C16 -45.47(17) . . . . ?
C18 C11 C17 C16 76.17(17) . . . . ?
C12 C11 C17 C16 -163.18(14) . . . . ?
C10 C11 C17 C19 -170.92(14) . . . . ?
C18 C11 C17 C19 -49.28(19) . . . . ?
C12 C11 C17 C19 71.37(18) . . . . ?
C16 C17 C19 C20 70.2(2) . . . . ?
C11 C17 C19 C20 -163.07(15) . . . . ?
C17 C19 C20 C21 -115.7(3) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.474
_refine_diff_density_min   -0.164
_refine_diff_density_rms    0.043