data_5000375
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C18 H19 Br O4'
_chemical_formula_weight          379.24
_chemical_melting_point           ?
_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        ?
_diffrn_measurement_method        ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             7247
_diffrn_reflns_av_R_equivalents   0.3263
_diffrn_reflns_av_sigmaI/netI     0.4990
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        4
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        28
_diffrn_reflns_theta_min          1.36
_diffrn_reflns_theta_max          19.99
_reflns_number_total              3013
_reflns_number_observed           938
_reflns_observed_criterion        >2sigma(I)
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme
 'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^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     ?
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0014(6)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          3013
_refine_ls_number_parameters      198
_refine_ls_number_restraints      71
_refine_ls_R_factor_all           0.3458
_refine_ls_R_factor_obs           0.1512
_refine_ls_wR_factor_all          0.2858
_refine_ls_wR_factor_obs          0.2110
_refine_ls_goodness_of_fit_all    0.988
_refine_ls_goodness_of_fit_obs    1.380
_refine_ls_restrained_S_all       0.979
_refine_ls_restrained_S_obs       1.326
_refine_ls_shift/esd_max          0.405
_refine_ls_shift/esd_mean         0.061
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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
Br1 Br 0.3251(6) 1.6577(2) -0.48891(14) 0.058(2) Uani 1 d D .
C1A C 0.3684(33) 1.6447(11) -0.3347(9) 0.033(9) Uiso 1 d D .
H1AA H 0.2891(33) 1.6328(11) -0.3093(9) 0.039 Uiso 1 calc R .
C2A C 0.2904(33) 1.6418(11) -0.3859(9) 0.026(9) Uiso 1 d D .
H2AA H 0.1646(33) 1.6265(11) -0.3969(9) 0.031 Uiso 1 calc R .
C3A C 0.4232(35) 1.6643(16) -0.4165(9) 0.023(9) Uiso 1 d D .
C4A C 0.6162(32) 1.6848(13) -0.4103(8) 0.013(8) Uiso 1 d D .
H4AA H 0.6928(32) 1.6966(13) -0.4363(8) 0.015 Uiso 1 calc R .
C5A C 0.6788(36) 1.6849(15) -0.3577(9) 0.039(10) Uiso 1 d D .
H5AA H 0.8060(36) 1.6993(15) -0.3475(9) 0.047 Uiso 1 calc R .
C6A C 0.5613(36) 1.6648(16) -0.3214(9) 0.030 Uiso 1 d D .
C7A C 0.6351(36) 1.6664(16) -0.2662(9) 0.029(9) Uiso 1 d D .
O1A O 0.5221(23) 1.6509(10) -0.2346(7) 0.029(6) Uiso 1 d D .
O2A O 0.8245(22) 1.6770(9) -0.2565(6) 0.014(5) Uiso 1 d D .
C8A C 0.8933(31) 1.6683(14) -0.2026(8) 0.025(9) Uiso 1 d D .
H8AA H 0.8149(31) 1.6316(14) -0.1865(8) 0.030 Uiso 1 calc R .
C9A C 1.1000(29) 1.6417(12) -0.2045(8) 0.009(8) Uiso 1 d D .
H9AA H 1.1642(29) 1.6746(12) -0.2270(8) 0.010 Uiso 1 calc R .
C10A C 1.0979(35) 1.5652(13) -0.2276(10) 0.035(10) Uiso 1 d D .
H10A H 1.2285(47) 1.5461(38) -0.2254(58) 0.052 Uiso 1 calc R .
H10B H 1.0467(223) 1.5677(18) -0.2626(18) 0.052 Uiso 1 calc R .
H10C H 1.0173(193) 1.5336(25) -0.2095(38) 0.052 Uiso 1 calc R .
C11A C 1.2224(32) 1.6403(13) -0.1538(8) 0.024(9) Uiso 1 d D .
H11A H 1.3413(32) 1.6123(13) -0.1583(8) 0.029 Uiso 1 calc R .
C12A C 1.2844(30) 1.7141(12) -0.1307(9) 0.021(9) Uiso 1 d D .
H12A H 1.3152(30) 1.7448(12) -0.1592(9) 0.025 Uiso 1 calc R .
C13A C 1.4754(29) 1.7073(13) -0.0963(9) 0.019(9) Uiso 1 d D .
H13A H 1.5614(83) 1.6739(59) -0.1112(27) 0.029 Uiso 1 calc R .
H13B H 1.4481(36) 1.6892(72) -0.0637(19) 0.029 Uiso 1 calc R .
H13C H 1.5364(105) 1.7546(19) -0.0925(43) 0.029 Uiso 1 calc R .
C14A C 1.1332(32) 1.7503(13) -0.1090(9) 0.027(9) Uiso 1 d D .
H14A H 1.1932(32) 1.7931(13) -0.0913(9) 0.033 Uiso 1 calc R .
C15A C 0.9590(33) 1.7786(14) -0.1411(9) 0.023(9) Uiso 1 d D .
H15A H 0.9129(33) 1.8245(14) -0.1326(9) 0.028 Uiso 1 calc R .
C16A C 0.8660(34) 1.7462(14) -0.1792(10) 0.027(9) Uiso 1 d D .
H16A H 0.7655(34) 1.7737(14) -0.1957(10) 0.033 Uiso 1 calc R .
C17A C 1.0511(35) 1.7003(12) -0.0660(9) 0.028(9) Uiso 1 d D .
H17A H 1.1455(35) 1.6996(12) -0.0365(9) 0.033 Uiso 1 calc R .
H17B H 0.9316(35) 1.7218(12) -0.0561(9) 0.033 Uiso 1 calc R .
C18A C 1.0132(36) 1.6280(14) -0.0821(10) 0.017(9) Uiso 1 d D .
O3A O 1.1112(23) 1.5992(9) -0.1193(6) 0.023(6) Uiso 1 d D .
O4A O 0.8960(23) 1.5858(9) -0.0645(7) 0.025(6) Uiso 1 d D .
Br2 Br 1.0912(7) 1.4900(2) 0.44233(15) 0.078(2) Uani 1 d D .
C1B C 1.0454(33) 1.5917(12) 0.3037(9) 0.030(10) Uiso 1 d D .
H1BA H 0.9566(33) 1.6205(12) 0.2840(9) 0.036 Uiso 1 calc R .
C2B C 0.9964(35) 1.5680(12) 0.3531(9) 0.046(11) Uiso 1 d D .
H2BA H 0.8834(35) 1.5803(12) 0.3678(9) 0.055 Uiso 1 calc R .
C3B C 1.1417(38) 1.5253(15) 0.3741(9) 0.038(10) Uiso 1 d D .
C4B C 1.3198(32) 1.5034(14) 0.3612(8) 0.015(8) Uiso 1 d D .
H4BA H 1.4098(32) 1.4765(14) 0.3820(8) 0.018 Uiso 1 calc R .
C5B C 1.3489(32) 1.5271(13) 0.3119(9) 0.017(9) Uiso 1 d D .
H5BA H 1.4588(32) 1.5115(13) 0.2970(9) 0.020 Uiso 1 calc R .
C6B C 1.2167(35) 1.5734(14) 0.2852(9) 0.019(9) Uiso 1 d D .
C7B C 1.2586(37) 1.5952(15) 0.2323(9) 0.024(9) Uiso 1 d D .
O1B O 1.1408(23) 1.6378(10) 0.2101(7) 0.030(6) Uiso 1 d D .
O2B O 1.4203(23) 1.5704(9) 0.2167(6) 0.025(6) Uiso 1 d D .
C8B C 1.4681(30) 1.5962(13) 0.1670(8) 0.007(8) Uiso 1 d D .
H8BA H 1.3752(30) 1.6345(13) 0.1550(8) 0.008 Uiso 1 calc R .
C9B C 1.6694(30) 1.6294(12) 0.1764(8) 0.016(9) Uiso 1 d D .
H9BA H 1.7546(30) 1.5929(12) 0.1943(8) 0.019 Uiso 1 calc R .
C10B C 1.6611(35) 1.6955(13) 0.2107(9) 0.029(10) Uiso 1 d D .
H10D H 1.7789(100) 1.7236(47) 0.2100(45) 0.044 Uiso 1 calc R .
H10E H 1.6483(224) 1.6794(13) 0.2448(14) 0.044 Uiso 1 calc R .
H10F H 1.5510(131) 1.7254(44) 0.1992(35) 0.044 Uiso 1 calc R .
C11B C 1.7604(33) 1.6506(14) 0.1281(8) 0.025(9) Uiso 1 d D .
H11B H 1.8721(33) 1.6827(14) 0.1374(8) 0.030 Uiso 1 calc R .
C12B C 1.8319(30) 1.5857(12) 0.0983(9) 0.019(8) Uiso 1 d D .
H12B H 1.8921(30) 1.5503(12) 0.1229(9) 0.022 Uiso 1 calc R .
C13B C 1.9946(30) 1.6139(14) 0.0655(9) 0.030(10) Uiso 1 d D .
H13D H 2.0410(154) 1.5738(22) 0.0464(43) 0.046 Uiso 1 calc R .
H13E H 2.1008(100) 1.6339(75) 0.0872(10) 0.046 Uiso 1 calc R .
H13F H 1.9415(65) 1.6512(59) 0.0426(41) 0.046 Uiso 1 calc R .
C14B C 1.6808(31) 1.5491(12) 0.0684(9) 0.017(9) Uiso 1 d D .
H14B H 1.7445(31) 1.5125(12) 0.0485(9) 0.021 Uiso 1 calc R .
C15B C 1.5231(35) 1.5102(15) 0.0919(10) 0.048(11) Uiso 1 d D .
H15B H 1.4788(35) 1.4670(15) 0.0761(10) 0.057 Uiso 1 calc R .
C16B C 1.4407(36) 1.5287(14) 0.1310(10) 0.037(10) Uiso 1 d D .
H16B H 1.3464(36) 1.4957(14) 0.1397(10) 0.044 Uiso 1 calc R .
C17B C 1.5792(35) 1.6071(13) 0.0285(9) 0.030 Uiso 1 d D .
H17C H 1.6698(35) 1.6194(13) 0.0039(9) 0.036 Uiso 1 calc R .
H17D H 1.4653(35) 1.5846(13) 0.0105(9) 0.036 Uiso 1 calc R .
C18B C 1.5221(41) 1.6722(16) 0.0523(10) 0.046(11) Uiso 1 d D .
O3B O 1.6143(27) 1.6926(10) 0.0974(7) 0.045(7) Uiso 1 d D .
O4B O 1.3983(24) 1.7156(9) 0.0326(6) 0.020(6) Uiso 1 d 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 0.108(4) 0.048(3) 0.016(2) 0.010(2) -0.013(2) -0.037(3)
Br2 0.155(4) 0.061(4) 0.023(3) -0.010(3) 0.039(3) -0.048(3)
_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 C3A 1.98(2) . ?
C1A C6A 1.39(2) . ?
C1A C2A 1.41(3) . ?
C2A C3A 1.34(3) . ?
C3A C4A 1.37(2) . ?
C4A C5A 1.42(3) . ?
C5A C6A 1.36(3) . ?
C6A C7A 1.50(3) . ?
C7A O1A 1.23(2) . ?
C7A O2A 1.32(2) . ?
O2A C8A 1.47(2) . ?
C8A C9A 1.51(2) . ?
C8A C16A 1.57(3) . ?
C9A C11A 1.52(2) . ?
C9A C10A 1.52(2) . ?
C11A O3A 1.45(2) . ?
C11A C12A 1.52(3) . ?
C12A C14A 1.40(3) . ?
C12A C13A 1.53(2) . ?
C14A C15A 1.50(3) . ?
C14A C17A 1.60(3) . ?
C15A C16A 1.29(3) . ?
C17A C18A 1.40(3) . ?
C18A O4A 1.24(2) . ?
C18A O3A 1.35(2) . ?
Br2 C3B 1.98(2) . ?
C1B C6B 1.36(3) . ?
C1B C2B 1.45(3) . ?
C2B C3B 1.35(3) . ?
C3B C4B 1.36(2) . ?
C4B C5B 1.41(3) . ?
C5B C6B 1.39(3) . ?
C6B C7B 1.51(3) . ?
C7B O1B 1.23(2) . ?
C7B O2B 1.30(2) . ?
O2B C8B 1.47(2) . ?
C8B C9B 1.51(2) . ?
C8B C16B 1.56(3) . ?
C9B C10B 1.52(2) . ?
C9B C11B 1.53(3) . ?
C11B O3B 1.45(2) . ?
C11B C12B 1.53(3) . ?
C12B C14B 1.41(2) . ?
C12B C13B 1.57(2) . ?
C14B C15B 1.48(3) . ?
C14B C17B 1.61(3) . ?
C15B C16B 1.27(3) . ?
C17B C18B 1.42(3) . ?
C18B O4B 1.24(2) . ?
C18B O3B 1.35(2) . ?
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
C6A C1A C2A 121.4(23) . . ?
C3A C2A C1A 110.5(22) . . ?
C2A C3A C4A 135.8(23) . . ?
C2A C3A Br1 112.2(18) . . ?
C4A C3A Br1 111.7(17) . . ?
C3A C4A C5A 108.5(21) . . ?
C6A C5A C4A 123.2(23) . . ?
C5A C6A C1A 120.5(22) . . ?
C5A C6A C7A 120.9(22) . . ?
C1A C6A C7A 118.6(22) . . ?
O1A C7A O2A 125.5(21) . . ?
O1A C7A C6A 118.7(23) . . ?
O2A C7A C6A 115.4(21) . . ?
C7A O2A C8A 113.2(17) . . ?
O2A C8A C9A 102.7(17) . . ?
O2A C8A C16A 104.2(18) . . ?
C9A C8A C16A 116.9(18) . . ?
C8A C9A C11A 115.0(18) . . ?
C8A C9A C10A 109.6(18) . . ?
C11A C9A C10A 108.9(19) . . ?
O3A C11A C9A 106.6(17) . . ?
O3A C11A C12A 110.2(18) . . ?
C9A C11A C12A 116.9(20) . . ?
C14A C12A C11A 113.1(19) . . ?
C14A C12A C13A 115.0(20) . . ?
C11A C12A C13A 111.1(18) . . ?
C12A C14A C15A 121.0(21) . . ?
C12A C14A C17A 110.3(19) . . ?
C15A C14A C17A 106.5(18) . . ?
C16A C15A C14A 127.0(24) . . ?
C15A C16A C8A 131.0(23) . . ?
C18A C17A C14A 112.8(20) . . ?
O4A C18A O3A 114.7(22) . . ?
O4A C18A C17A 125.5(23) . . ?
O3A C18A C17A 119.8(22) . . ?
C18A O3A C11A 125.8(20) . . ?
C6B C1B C2B 122.4(23) . . ?
C3B C2B C1B 108.6(22) . . ?
C2B C3B C4B 135.7(24) . . ?
C2B C3B Br2 112.3(19) . . ?
C4B C3B Br2 111.9(18) . . ?
C3B C4B C5B 110.6(21) . . ?
C6B C5B C4B 121.2(22) . . ?
C1B C6B C5B 121.0(22) . . ?
C1B C6B C7B 121.2(22) . . ?
C5B C6B C7B 117.5(21) . . ?
O1B C7B O2B 127.7(22) . . ?
O1B C7B C6B 115.8(22) . . ?
O2B C7B C6B 116.4(21) . . ?
C7B O2B C8B 116.3(18) . . ?
O2B C8B C9B 105.1(16) . . ?
O2B C8B C16B 105.9(18) . . ?
C9B C8B C16B 118.3(18) . . ?
C8B C9B C10B 109.4(18) . . ?
C8B C9B C11B 113.9(18) . . ?
C10B C9B C11B 110.1(19) . . ?
O3B C11B C12B 111.1(18) . . ?
O3B C11B C9B 106.6(17) . . ?
C12B C11B C9B 114.4(20) . . ?
C14B C12B C11B 113.5(19) . . ?
C14B C12B C13B 111.6(19) . . ?
C11B C12B C13B 108.3(18) . . ?
C12B C14B C15B 121.3(21) . . ?
C12B C14B C17B 108.1(18) . . ?
C15B C14B C17B 107.5(18) . . ?
C16B C15B C14B 127.9(26) . . ?
C15B C16B C8B 132.1(24) . . ?
C18B C17B C14B 112.3(20) . . ?
O4B C18B O3B 116.2(24) . . ?
O4B C18B C17B 123.8(23) . . ?
O3B C18B C17B 119.8(22) . . ?
C18B O3B C11B 126.3(20) . . ?
_refine_diff_density_max    0.680
_refine_diff_density_min   -0.575
_refine_diff_density_rms    0.140