 
data_marc002 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H17 Br O4' 
_chemical_formula_weight          401.24 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Br'  'Br'  -0.6763   1.2805 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            4 
_space_group_name_H-M_alt         'P 21' 
_space_group_name_Hall            'P 2yb' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
  
_cell_length_a                    6.8349(3) 
_cell_length_b                    7.3672(3) 
_cell_length_c                    18.3255(8) 
_cell_angle_alpha                 90 
_cell_angle_beta                  100.593(2) 
_cell_angle_gamma                 90 
_cell_volume                      907.04(7) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     6433 
_cell_measurement_theta_min       2.45 
_cell_measurement_theta_max       73.95 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.469 
_exptl_crystal_F_000              408 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.453 
_exptl_crystal_size_mid           0.371 
_exptl_crystal_size_min           0.086 
_exptl_absorpt_coefficient_mu     3.269 
_shelx_estimated_absorpt_T_min    0.319 
_shelx_estimated_absorpt_T_max    0.766 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.4614   
_exptl_absorpt_correction_T_max   0.7538 
_exptl_absorpt_process_details    'APEX2 (Bruker, 2007)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             19560 
_diffrn_reflns_av_unetI/netI      0.0490 
_diffrn_reflns_av_R_equivalents   0.0685 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          2.453 
_diffrn_reflns_theta_max          74.779 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.996 
_diffrn_measured_fraction_theta_full  0.998 
_diffrn_reflns_Laue_measured_fraction_max    0.996 
_diffrn_reflns_Laue_measured_fraction_full   0.998 
_diffrn_reflns_point_group_measured_fraction_max   0.990 
_diffrn_reflns_point_group_measured_fraction_full  0.996 
_reflns_number_total              3698 
_reflns_number_gt                 3523 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.839 
_reflns_Friedel_fraction_max      0.982 
_reflns_Friedel_fraction_full     0.993 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_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-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0749P)²+0.0991P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014' 
_refine_ls_extinction_coef        0.0098(15) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    -0.01(3) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          3698 
_refine_ls_number_parameters      232 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0455 
_refine_ls_R_factor_gt            0.0441 
_refine_ls_wR_factor_ref          0.1214 
_refine_ls_wR_factor_gt           0.1201 
_refine_ls_goodness_of_fit_ref    1.114 
_refine_ls_restrained_S_all       1.114 
_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_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.6532(6) 0.4414(6) 0.3727(2) 0.0272(8) Uani 1 1 d . . . . . 
C2 C 0.6327(6) 0.5490(7) 0.4422(3) 0.0307(9) Uani 1 1 d . . . . . 
C3 C 0.7719(6) 0.7007(7) 0.4489(3) 0.0323(9) Uani 1 1 d . . . . . 
C4 C 0.8755(6) 0.7012(6) 0.3940(3) 0.0297(9) Uani 1 1 d . . . . . 
C5 C 0.8057(6) 0.5548(6) 0.3372(2) 0.0267(8) Uani 1 1 d . . . . . 
H5 H 0.9214 0.4755 0.3325 0.032 Uiso 1 1 calc R U . . . 
C6 C 0.4501(6) 0.4208(5) 0.3231(2) 0.0275(9) Uani 1 1 d . . . . . 
C7 C 0.2662(8) 0.3247(8) 0.1448(3) 0.0439(12) Uani 1 1 d . . . . . 
H7 H 0.3664 0.3974 0.1297 0.053 Uiso 1 1 calc R U . . . 
C8 C 0.0970(10) 0.2723(11) 0.0937(4) 0.0590(16) Uani 1 1 d . . . . . 
H8 H 0.0813 0.3088 0.0432 0.071 Uiso 1 1 calc R U . . . 
C9 C -0.0472(10) 0.1670(9) 0.1173(4) 0.0603(17) Uani 1 1 d . . . . . 
H9 H -0.1615 0.1304 0.0827 0.072 Uiso 1 1 calc R U . . . 
C10 C -0.0262(9) 0.1152(8) 0.1898(4) 0.0529(14) Uani 1 1 d . . . . . 
H10 H -0.1267 0.0438 0.2053 0.063 Uiso 1 1 calc R U . . . 
C11 C 0.1402(8) 0.1658(7) 0.2409(3) 0.0427(11) Uani 1 1 d . . . . . 
H11 H 0.1554 0.1306 0.2915 0.051 Uiso 1 1 calc R U . . . 
C12 C 0.2838(6) 0.2695(6) 0.2160(3) 0.0325(9) Uani 1 1 d . . . . . 
C13 C 0.7362(7) 0.2524(7) 0.3963(3) 0.0363(10) Uani 1 1 d . . . . . 
H13A H 0.6446 0.1894 0.4231 0.054 Uiso 1 1 calc R U . . . 
H13B H 0.8665 0.2648 0.4288 0.054 Uiso 1 1 calc R U . . . 
H13C H 0.7504 0.1822 0.3522 0.054 Uiso 1 1 calc R U . . . 
C14 C 1.0427(7) 0.8248(7) 0.3861(3) 0.0396(11) Uani 1 1 d . . . . . 
H14A H 1.0351 0.9348 0.4156 0.059 Uiso 1 1 calc R U . . . 
H14B H 1.0334 0.8578 0.3338 0.059 Uiso 1 1 calc R U . . . 
H14C H 1.1696 0.7633 0.4039 0.059 Uiso 1 1 calc R U . . . 
C15 C 0.8098(7) 0.5961(7) 0.2007(3) 0.0323(9) Uani 1 1 d . . . . . 
H15 H 0.9211 0.5166 0.2067 0.039 Uiso 1 1 calc R U . . . 
C16 C 0.7352(7) 0.6672(7) 0.1312(3) 0.0366(10) Uani 1 1 d . . . . . 
H16 H 0.7945 0.6372 0.0897 0.044 Uiso 1 1 calc R U . . . 
C17 C 0.5735(8) 0.7821(7) 0.1230(3) 0.0373(10) Uani 1 1 d . . . . . 
C18 C 0.4866(8) 0.8301(7) 0.1825(3) 0.0386(11) Uani 1 1 d . . . . . 
H18 H 0.3745 0.9086 0.1759 0.046 Uiso 1 1 calc R U . . . 
C19 C 0.5658(7) 0.7619(7) 0.2520(3) 0.0350(10) Uani 1 1 d . . . . . 
H19 H 0.5114 0.7990 0.2937 0.042 Uiso 1 1 calc R U . . . 
C20 C 0.7246(6) 0.6391(6) 0.2618(3) 0.0287(9) Uani 1 1 d . . . . . 
O1 O 0.2980(5) 0.4896(6) 0.3333(2) 0.0438(9) Uani 1 1 d . . . . . 
O2 O 0.4621(4) 0.3107(5) 0.26562(18) 0.0336(7) Uani 1 1 d . . . . . 
O3 O 0.5286(5) 0.5081(6) 0.4871(2) 0.0436(9) Uani 1 1 d . . . . . 
O4 O 0.8048(5) 0.8140(6) 0.5088(2) 0.0435(9) Uani 1 1 d . . . . . 
H4 H 0.707(12) 0.853(12) 0.517(4) 0.065 Uiso 1 1 d . U . . . 
Br1 Br 0.46638(10) 0.88088(9) 0.02817(3) 0.0548(3) 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 C6 1.520(6) . ? 
C1 C2 1.527(6) . ? 
C1 C13 1.536(6) . ? 
C1 C5 1.568(5) . ? 
C2 O3 1.222(5) . ? 
C2 C3 1.458(7) . ? 
C3 C4 1.332(6) . ? 
C3 O4 1.365(6) . ? 
C4 C14 1.489(6) . ? 
C4 C5 1.514(6) . ? 
C5 C20 1.523(6) . ? 
C5 H5 1.0000 . ? 
C6 O1 1.202(5) . ? 
C6 O2 1.344(5) . ? 
C7 C12 1.351(7) . ? 
C7 C8 1.402(8) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.385(11) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.364(10) . ? 
C9 H9 0.9500 . ? 
C10 C11 1.385(8) . ? 
C10 H10 0.9500 . ? 
C11 C12 1.386(7) . ? 
C11 H11 0.9500 . ? 
C12 O2 1.413(5) . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
C14 H14A 0.9800 . ? 
C14 H14B 0.9800 . ? 
C14 H14C 0.9800 . ? 
C15 C16 1.385(7) . ? 
C15 C20 1.391(6) . ? 
C15 H15 0.9500 . ? 
C16 C17 1.378(7) . ? 
C16 H16 0.9500 . ? 
C17 C18 1.381(7) . ? 
C17 Br1 1.902(5) . ? 
C18 C19 1.382(7) . ? 
C18 H18 0.9500 . ? 
C19 C20 1.399(6) . ? 
C19 H19 0.9500 . ? 
O4 H4 0.77(8) . ? 
  
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 
C6 C1 C2 109.7(3) . . ? 
C6 C1 C13 109.1(4) . . ? 
C2 C1 C13 108.8(4) . . ? 
C6 C1 C5 114.1(4) . . ? 
C2 C1 C5 103.9(3) . . ? 
C13 C1 C5 111.1(3) . . ? 
O3 C2 C3 125.7(5) . . ? 
O3 C2 C1 126.0(5) . . ? 
C3 C2 C1 108.0(3) . . ? 
C4 C3 O4 125.1(4) . . ? 
C4 C3 C2 111.6(4) . . ? 
O4 C3 C2 123.0(4) . . ? 
C3 C4 C14 126.8(4) . . ? 
C3 C4 C5 111.9(4) . . ? 
C14 C4 C5 121.3(4) . . ? 
C4 C5 C20 110.5(4) . . ? 
C4 C5 C1 104.1(3) . . ? 
C20 C5 C1 115.8(3) . . ? 
C4 C5 H5 108.8 . . ? 
C20 C5 H5 108.8 . . ? 
C1 C5 H5 108.8 . . ? 
O1 C6 O2 123.8(4) . . ? 
O1 C6 C1 125.8(4) . . ? 
O2 C6 C1 110.4(3) . . ? 
C12 C7 C8 118.6(5) . . ? 
C12 C7 H7 120.7 . . ? 
C8 C7 H7 120.7 . . ? 
C9 C8 C7 119.5(6) . . ? 
C9 C8 H8 120.3 . . ? 
C7 C8 H8 120.3 . . ? 
C10 C9 C8 120.5(6) . . ? 
C10 C9 H9 119.7 . . ? 
C8 C9 H9 119.7 . . ? 
C9 C10 C11 120.7(6) . . ? 
C9 C10 H10 119.7 . . ? 
C11 C10 H10 119.7 . . ? 
C10 C11 C12 117.9(6) . . ? 
C10 C11 H11 121.0 . . ? 
C12 C11 H11 121.0 . . ? 
C7 C12 C11 122.8(5) . . ? 
C7 C12 O2 118.0(4) . . ? 
C11 C12 O2 119.0(5) . . ? 
C1 C13 H13A 109.5 . . ? 
C1 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C1 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C4 C14 H14A 109.5 . . ? 
C4 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C4 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C16 C15 C20 121.1(4) . . ? 
C16 C15 H15 119.5 . . ? 
C20 C15 H15 119.5 . . ? 
C17 C16 C15 119.0(4) . . ? 
C17 C16 H16 120.5 . . ? 
C15 C16 H16 120.5 . . ? 
C16 C17 C18 121.6(5) . . ? 
C16 C17 Br1 120.0(4) . . ? 
C18 C17 Br1 118.3(4) . . ? 
C17 C18 C19 118.8(5) . . ? 
C17 C18 H18 120.6 . . ? 
C19 C18 H18 120.6 . . ? 
C18 C19 C20 121.1(4) . . ? 
C18 C19 H19 119.4 . . ? 
C20 C19 H19 119.4 . . ? 
C15 C20 C19 118.3(4) . . ? 
C15 C20 C5 120.1(4) . . ? 
C19 C20 C5 121.7(4) . . ? 
C6 O2 C12 117.7(3) . . ? 
C3 O4 H4 111(6) . . ? 
  
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 O3 58.3(6) . . . . ? 
C13 C1 C2 O3 -60.9(6) . . . . ? 
C5 C1 C2 O3 -179.4(5) . . . . ? 
C6 C1 C2 C3 -126.5(4) . . . . ? 
C13 C1 C2 C3 114.3(4) . . . . ? 
C5 C1 C2 C3 -4.2(5) . . . . ? 
O3 C2 C3 C4 174.9(5) . . . . ? 
C1 C2 C3 C4 -0.3(5) . . . . ? 
O3 C2 C3 O4 1.6(8) . . . . ? 
C1 C2 C3 O4 -173.7(4) . . . . ? 
O4 C3 C4 C14 -1.1(8) . . . . ? 
C2 C3 C4 C14 -174.2(4) . . . . ? 
O4 C3 C4 C5 178.2(4) . . . . ? 
C2 C3 C4 C5 5.1(6) . . . . ? 
C3 C4 C5 C20 117.4(4) . . . . ? 
C14 C4 C5 C20 -63.2(5) . . . . ? 
C3 C4 C5 C1 -7.5(5) . . . . ? 
C14 C4 C5 C1 171.9(4) . . . . ? 
C6 C1 C5 C4 126.0(4) . . . . ? 
C2 C1 C5 C4 6.7(4) . . . . ? 
C13 C1 C5 C4 -110.1(4) . . . . ? 
C6 C1 C5 C20 4.6(5) . . . . ? 
C2 C1 C5 C20 -114.8(4) . . . . ? 
C13 C1 C5 C20 128.4(4) . . . . ? 
C2 C1 C6 O1 5.3(6) . . . . ? 
C13 C1 C6 O1 124.4(5) . . . . ? 
C5 C1 C6 O1 -110.7(5) . . . . ? 
C2 C1 C6 O2 -173.6(4) . . . . ? 
C13 C1 C6 O2 -54.6(4) . . . . ? 
C5 C1 C6 O2 70.4(4) . . . . ? 
C12 C7 C8 C9 0.3(9) . . . . ? 
C7 C8 C9 C10 0.5(10) . . . . ? 
C8 C9 C10 C11 -0.5(10) . . . . ? 
C9 C10 C11 C12 -0.2(9) . . . . ? 
C8 C7 C12 C11 -1.1(8) . . . . ? 
C8 C7 C12 O2 175.0(5) . . . . ? 
C10 C11 C12 C7 1.0(8) . . . . ? 
C10 C11 C12 O2 -175.0(5) . . . . ? 
C20 C15 C16 C17 -0.1(7) . . . . ? 
C15 C16 C17 C18 1.1(7) . . . . ? 
C15 C16 C17 Br1 -179.6(4) . . . . ? 
C16 C17 C18 C19 0.6(8) . . . . ? 
Br1 C17 C18 C19 -178.8(4) . . . . ? 
C17 C18 C19 C20 -3.2(8) . . . . ? 
C16 C15 C20 C19 -2.4(7) . . . . ? 
C16 C15 C20 C5 178.2(4) . . . . ? 
C18 C19 C20 C15 4.1(7) . . . . ? 
C18 C19 C20 C5 -176.6(4) . . . . ? 
C4 C5 C20 C15 120.8(4) . . . . ? 
C1 C5 C20 C15 -121.3(4) . . . . ? 
C4 C5 C20 C19 -58.5(5) . . . . ? 
C1 C5 C20 C19 59.4(5) . . . . ? 
O1 C6 O2 C12 -2.1(7) . . . . ? 
C1 C6 O2 C12 176.8(4) . . . . ? 
C7 C12 O2 C6 116.6(5) . . . . ? 
C11 C12 O2 C6 -67.2(6) . . . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O4 H4 O3  0.77(8) 1.96(8) 2.703(5) 162(8) 2_656 
  
_refine_diff_density_max    0.634 
_refine_diff_density_min   -0.412 
_refine_diff_density_rms    0.060 
  
  
  
