 
data_d8v19681 
  
_audit_creation_method            SHELXL-2013 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C38 H36 B2 O2' 
_chemical_formula_weight          546.29 
  
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' 
 'B'  'B'   0.0013   0.0007 
 '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' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            61 
_space_group_name_H-M_alt         'P b c a' 
_space_group_name_Hall            '-P 2ac 2ab' 
  
_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+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-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                    18.752(2) 
_cell_length_b                    7.4170(10) 
_cell_length_c                    21.713(2) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      3019.9(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     192(2) 
_cell_measurement_reflns_used     4177 
_cell_measurement_theta_min       6.999 
_cell_measurement_theta_max       54.513 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.202 
_exptl_crystal_F_000              1160 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.180 
_exptl_crystal_size_mid           0.150 
_exptl_crystal_size_min           0.120 
_exptl_absorpt_coefficient_mu     0.071 
_shelx_estimated_absorpt_T_min    0.987 
_shelx_estimated_absorpt_T_max    0.992 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.4877 
_exptl_absorpt_correction_T_max   0.7456 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       192(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             13983 
_diffrn_reflns_av_unetI/netI      0.0483 
_diffrn_reflns_av_R_equivalents   0.0628 
_diffrn_reflns_limit_h_min        -23 
_diffrn_reflns_limit_h_max        18 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -26 
_diffrn_reflns_limit_l_max        25 
_diffrn_reflns_theta_min          2.871 
_diffrn_reflns_theta_max          26.000 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.997 
_diffrn_measured_fraction_theta_full  0.997 
_diffrn_reflns_Laue_measured_fraction_max    0.997 
_diffrn_reflns_Laue_measured_fraction_full   0.997 
_diffrn_reflns_point_group_measured_fraction_max   0.997 
_diffrn_reflns_point_group_measured_fraction_full  0.997 
_reflns_number_total              2956 
_reflns_number_gt                 2169 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_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-2013 (Sheldrick, 2013)' 
_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)+(0.0645P)²+1.4640P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0058(18) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2956 
_refine_ls_number_parameters      195 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0760 
_refine_ls_R_factor_gt            0.0537 
_refine_ls_wR_factor_ref          0.1487 
_refine_ls_wR_factor_gt           0.1312 
_refine_ls_goodness_of_fit_ref    1.027 
_refine_ls_restrained_S_all       1.027 
_refine_ls_shift/su_max           0.010 
_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 
O1 O 0.54329(7) 0.62455(19) 0.61339(5) 0.0358(4) Uani 1 1 d . . . . . 
C1 C 0.52227(10) 0.5672(3) 0.55549(8) 0.0307(4) Uani 1 1 d . . . . . 
C2 C 0.48657(10) 0.4056(3) 0.55346(8) 0.0319(5) Uani 1 1 d . . . . . 
H2 H 0.4777 0.3424 0.5907 0.038 Uiso 1 1 calc R U . . . 
C3 C 0.46289(9) 0.3319(3) 0.49764(8) 0.0298(4) Uani 1 1 d . . . . . 
C4 C 0.42369(10) 0.1619(3) 0.49313(8) 0.0299(4) Uani 1 1 d . . . . . 
C5 C 0.40716(10) 0.0557(3) 0.54456(8) 0.0341(5) Uani 1 1 d . . . . . 
H5 H 0.4229 0.0926 0.5842 0.041 Uiso 1 1 calc R U . . . 
C6 C 0.36883(11) -0.0997(3) 0.53856(9) 0.0356(5) Uani 1 1 d . . . . . 
H6 H 0.3585 -0.1690 0.5743 0.043 Uiso 1 1 calc R U . . . 
C7 C 0.34422(10) -0.1601(3) 0.48112(8) 0.0329(5) Uani 1 1 d . . . . . 
C8 C 0.36127(10) -0.0573(3) 0.43013(9) 0.0327(5) Uani 1 1 d . . . . . 
H8 H 0.3456 -0.0967 0.3907 0.039 Uiso 1 1 calc R U . . . 
C9 C 0.40092(10) 0.1035(3) 0.43426(8) 0.0306(4) Uani 1 1 d . . . . . 
C10 C 0.29959(12) -0.3272(3) 0.47589(10) 0.0440(6) Uani 1 1 d . . . . . 
H10A H 0.2782 -0.3329 0.4348 0.066 Uiso 1 1 calc R U . . . 
H10B H 0.2618 -0.3243 0.5070 0.066 Uiso 1 1 calc R U . . . 
H10C H 0.3296 -0.4336 0.4825 0.066 Uiso 1 1 calc R U . . . 
C11 C 0.60751(10) 0.8174(3) 0.69019(8) 0.0300(4) Uani 1 1 d . . . . . 
C12 C 0.58048(11) 0.9592(3) 0.72578(9) 0.0374(5) Uani 1 1 d . . . . . 
C13 C 0.60660(12) 0.9891(3) 0.78513(9) 0.0401(5) Uani 1 1 d . . . . . 
H13 H 0.5875 1.0854 0.8088 0.048 Uiso 1 1 calc R U . . . 
C14 C 0.65920(11) 0.8826(3) 0.81023(8) 0.0370(5) Uani 1 1 d . . . . . 
C15 C 0.68538(11) 0.7412(3) 0.77536(9) 0.0390(5) Uani 1 1 d . . . . . 
H15 H 0.7212 0.6656 0.7923 0.047 Uiso 1 1 calc R U . . . 
C16 C 0.66054(11) 0.7069(3) 0.71606(9) 0.0358(5) Uani 1 1 d . . . . . 
C17 C 0.69170(15) 0.5516(4) 0.68002(11) 0.0605(7) Uani 1 1 d . . . . . 
H17A H 0.6571 0.4526 0.6785 0.091 Uiso 1 1 calc R U . . . 
H17B H 0.7355 0.5101 0.7001 0.091 Uiso 1 1 calc R U . . . 
H17C H 0.7027 0.5915 0.6380 0.091 Uiso 1 1 calc R U . . . 
C18 C 0.52170(15) 1.0783(4) 0.70154(11) 0.0627(8) Uani 1 1 d . . . . . 
H18A H 0.5409 1.1584 0.6697 0.094 Uiso 1 1 calc R U . . . 
H18B H 0.5021 1.1505 0.7353 0.094 Uiso 1 1 calc R U . . . 
H18C H 0.4839 1.0032 0.6838 0.094 Uiso 1 1 calc R U . . . 
C19 C 0.68841(13) 0.9193(4) 0.87382(9) 0.0505(6) Uani 1 1 d . . . . . 
H19A H 0.7333 0.9860 0.8704 0.076 Uiso 1 1 calc R U . . . 
H19B H 0.6969 0.8047 0.8951 0.076 Uiso 1 1 calc R U . . . 
H19C H 0.6539 0.9909 0.8973 0.076 Uiso 1 1 calc R U . . . 
B1 B 0.58197(12) 0.7802(3) 0.62236(9) 0.0320(5) 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 
O1 B1 1.377(3) . ? 
O1 C1 1.385(2) . ? 
C1 C2 1.373(3) . ? 
C1 C3 1.403(3) 5_666 ? 
C2 C3 1.402(3) . ? 
C2 H2 0.9500 . ? 
C3 C1 1.403(3) 5_666 ? 
C3 C4 1.463(3) . ? 
C4 C5 1.401(3) . ? 
C4 C9 1.415(2) . ? 
C5 C6 1.365(3) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.403(3) . ? 
C6 H6 0.9500 . ? 
C7 C8 1.382(3) . ? 
C7 C10 1.500(3) . ? 
C8 C9 1.408(3) . ? 
C8 H8 0.9500 . ? 
C9 B1 1.536(3) 5_666 ? 
C10 H10A 0.9800 . ? 
C10 H10B 0.9800 . ? 
C10 H10C 0.9800 . ? 
C11 C12 1.400(3) . ? 
C11 C16 1.406(3) . ? 
C11 B1 1.573(3) . ? 
C12 C13 1.396(3) . ? 
C12 C18 1.507(3) . ? 
C13 C14 1.376(3) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.383(3) . ? 
C14 C19 1.510(3) . ? 
C15 C16 1.393(3) . ? 
C15 H15 0.9500 . ? 
C16 C17 1.510(3) . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C17 H17C 0.9800 . ? 
C18 H18A 0.9800 . ? 
C18 H18B 0.9800 . ? 
C18 H18C 0.9800 . ? 
C19 H19A 0.9800 . ? 
C19 H19B 0.9800 . ? 
C19 H19C 0.9800 . ? 
B1 C9 1.536(3) 5_666 ? 
  
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 
B1 O1 C1 122.42(15) . . ? 
C2 C1 O1 115.86(16) . . ? 
C2 C1 C3 122.41(17) . 5_666 ? 
O1 C1 C3 121.73(18) . 5_666 ? 
C1 C2 C3 121.51(18) . . ? 
C1 C2 H2 119.2 . . ? 
C3 C2 H2 119.2 . . ? 
C2 C3 C1 116.09(18) . 5_666 ? 
C2 C3 C4 123.60(17) . . ? 
C1 C3 C4 120.30(16) 5_666 . ? 
C5 C4 C9 118.77(18) . . ? 
C5 C4 C3 122.82(16) . . ? 
C9 C4 C3 118.40(17) . . ? 
C6 C5 C4 121.00(17) . . ? 
C6 C5 H5 119.5 . . ? 
C4 C5 H5 119.5 . . ? 
C5 C6 C7 121.84(18) . . ? 
C5 C6 H6 119.1 . . ? 
C7 C6 H6 119.1 . . ? 
C8 C7 C6 117.38(19) . . ? 
C8 C7 C10 121.64(17) . . ? 
C6 C7 C10 120.97(18) . . ? 
C7 C8 C9 122.58(17) . . ? 
C7 C8 H8 118.7 . . ? 
C9 C8 H8 118.7 . . ? 
C8 C9 C4 118.41(17) . . ? 
C8 C9 B1 122.35(16) . 5_666 ? 
C4 C9 B1 119.22(18) . 5_666 ? 
C7 C10 H10A 109.5 . . ? 
C7 C10 H10B 109.5 . . ? 
H10A C10 H10B 109.5 . . ? 
C7 C10 H10C 109.5 . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
C12 C11 C16 118.27(17) . . ? 
C12 C11 B1 122.56(17) . . ? 
C16 C11 B1 119.16(17) . . ? 
C13 C12 C11 120.09(19) . . ? 
C13 C12 C18 119.08(19) . . ? 
C11 C12 C18 120.80(18) . . ? 
C14 C13 C12 121.74(19) . . ? 
C14 C13 H13 119.1 . . ? 
C12 C13 H13 119.1 . . ? 
C13 C14 C15 118.20(18) . . ? 
C13 C14 C19 121.2(2) . . ? 
C15 C14 C19 120.5(2) . . ? 
C14 C15 C16 121.73(19) . . ? 
C14 C15 H15 119.1 . . ? 
C16 C15 H15 119.1 . . ? 
C15 C16 C11 119.96(19) . . ? 
C15 C16 C17 119.29(19) . . ? 
C11 C16 C17 120.75(18) . . ? 
C16 C17 H17A 109.5 . . ? 
C16 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
C16 C17 H17C 109.5 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
C12 C18 H18A 109.5 . . ? 
C12 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
C12 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C14 C19 H19A 109.5 . . ? 
C14 C19 H19B 109.5 . . ? 
H19A C19 H19B 109.5 . . ? 
C14 C19 H19C 109.5 . . ? 
H19A C19 H19C 109.5 . . ? 
H19B C19 H19C 109.5 . . ? 
O1 B1 C9 117.88(16) . 5_666 ? 
O1 B1 C11 116.10(17) . . ? 
C9 B1 C11 125.97(18) 5_666 . ? 
  
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 
B1 O1 C1 C2 177.38(18) . . . . ? 
B1 O1 C1 C3 -2.2(3) . . . 5_666 ? 
O1 C1 C2 C3 -179.52(17) . . . . ? 
C3 C1 C2 C3 0.1(3) 5_666 . . . ? 
C1 C2 C3 C1 -0.1(3) . . . 5_666 ? 
C1 C2 C3 C4 -178.99(18) . . . . ? 
C2 C3 C4 C5 -1.0(3) . . . . ? 
C1 C3 C4 C5 -179.79(18) 5_666 . . . ? 
C2 C3 C4 C9 178.36(18) . . . . ? 
C1 C3 C4 C9 -0.5(3) 5_666 . . . ? 
C9 C4 C5 C6 -1.1(3) . . . . ? 
C3 C4 C5 C6 178.26(18) . . . . ? 
C4 C5 C6 C7 -0.1(3) . . . . ? 
C5 C6 C7 C8 1.1(3) . . . . ? 
C5 C6 C7 C10 -177.41(19) . . . . ? 
C6 C7 C8 C9 -0.8(3) . . . . ? 
C10 C7 C8 C9 177.65(18) . . . . ? 
C7 C8 C9 C4 -0.3(3) . . . . ? 
C7 C8 C9 B1 -178.36(18) . . . 5_666 ? 
C5 C4 C9 C8 1.3(3) . . . . ? 
C3 C4 C9 C8 -178.07(16) . . . . ? 
C5 C4 C9 B1 179.35(17) . . . 5_666 ? 
C3 C4 C9 B1 0.0(3) . . . 5_666 ? 
C16 C11 C12 C13 0.5(3) . . . . ? 
B1 C11 C12 C13 -178.17(19) . . . . ? 
C16 C11 C12 C18 -177.8(2) . . . . ? 
B1 C11 C12 C18 3.5(3) . . . . ? 
C11 C12 C13 C14 0.4(3) . . . . ? 
C18 C12 C13 C14 178.7(2) . . . . ? 
C12 C13 C14 C15 -1.0(3) . . . . ? 
C12 C13 C14 C19 178.3(2) . . . . ? 
C13 C14 C15 C16 0.9(3) . . . . ? 
C19 C14 C15 C16 -178.5(2) . . . . ? 
C14 C15 C16 C11 0.0(3) . . . . ? 
C14 C15 C16 C17 179.4(2) . . . . ? 
C12 C11 C16 C15 -0.7(3) . . . . ? 
B1 C11 C16 C15 178.03(19) . . . . ? 
C12 C11 C16 C17 179.9(2) . . . . ? 
B1 C11 C16 C17 -1.4(3) . . . . ? 
C1 O1 B1 C9 2.6(3) . . . 5_666 ? 
C1 O1 B1 C11 -174.72(16) . . . . ? 
C12 C11 B1 O1 -111.8(2) . . . . ? 
C16 C11 B1 O1 69.6(2) . . . . ? 
C12 C11 B1 C9 71.1(3) . . . 5_666 ? 
C16 C11 B1 C9 -107.6(2) . . . 5_666 ? 
  
_refine_diff_density_max    0.266 
_refine_diff_density_min   -0.184 
_refine_diff_density_rms    0.042 
  
_shelxl_version_number 2013-4 
  
  
  
