# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KP99
_database_code_depnum_ccdc_archive 'CCDC 1899786'
loop_
_audit_author_name
_audit_author_address
'Kevin Klausmeyer'
;Baylor University
United States of America
;
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 O5'
_chemical_formula_weight         354.38

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'

_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                   13.8321(7)
_cell_length_b                   8.4887(3)
_cell_length_c                   30.2097(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3547.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      26.34

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            27657
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.697
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3628
_reflns_number_gt                2840
_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-2014 (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)+(0.0434P)²+1.2761P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3628
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
O1 O 0.38978(8) 0.23743(14) 0.07568(3) 0.0373(3) Uani 1 1 d . . . . .
O2 O 0.21713(9) 0.54397(15) -0.09721(4) 0.0453(3) Uani 1 1 d . . . . .
O3 O -0.02259(7) -0.16877(12) 0.19413(3) 0.0307(3) Uani 1 1 d . . . . .
O4 O 0.04729(7) -0.13316(12) 0.27740(3) 0.0297(3) Uani 1 1 d . . . . .
O5 O 0.20055(7) 0.04329(11) 0.29365(3) 0.0277(2) Uani 1 1 d . . . . .
C1 C 0.30421(11) 0.25563(17) 0.06591(5) 0.0280(3) Uani 1 1 d . . . . .
C2 C 0.27739(11) 0.33450(16) 0.02390(5) 0.0280(3) Uani 1 1 d . . . . .
C3 C 0.35049(12) 0.37504(19) -0.00639(5) 0.0356(4) Uani 1 1 d . . . . .
H3 H 0.4160 0.3522 0.0005 0.043 Uiso 1 1 calc R U . . .
C4 C 0.32845(13) 0.4470(2) -0.04568(5) 0.0394(4) Uani 1 1 d . . . . .
H4 H 0.3787 0.4755 -0.0656 0.047 Uiso 1 1 calc R U . . .
C5 C 0.23226(12) 0.47864(19) -0.05647(5) 0.0359(4) Uani 1 1 d . . . . .
C6 C 0.15934(12) 0.44237(18) -0.02662(5) 0.0340(4) Uani 1 1 d . . . . .
H6 H 0.0940 0.4656 -0.0337 0.041 Uiso 1 1 calc R U . . .
C7 C 0.18183(11) 0.37172(17) 0.01387(5) 0.0289(3) Uani 1 1 d . . . . .
C8 C 0.10388(11) 0.34342(18) 0.04769(5) 0.0316(4) Uani 1 1 d . . . . .
H8A H 0.0413 0.3297 0.0322 0.038 Uiso 1 1 calc R U . . .
H8B H 0.0984 0.4374 0.0669 0.038 Uiso 1 1 calc R U . . .
C9 C 0.12291(11) 0.19909(17) 0.07650(5) 0.0298(3) Uani 1 1 d . . . . .
H9A H 0.0760 0.1977 0.1013 0.036 Uiso 1 1 calc R U . . .
H9B H 0.1125 0.1028 0.0586 0.036 Uiso 1 1 calc R U . . .
C10 C 0.22456(10) 0.19696(16) 0.09514(5) 0.0259(3) Uani 1 1 d . . . . .
C11 C 0.24992(11) 0.14809(16) 0.13590(5) 0.0261(3) Uani 1 1 d . . . . .
H11 H 0.3166 0.1597 0.1427 0.031 Uiso 1 1 calc R U . . .
C12 C 0.19128(10) 0.07983(16) 0.17149(5) 0.0240(3) Uani 1 1 d . . . . .
C13 C 0.10802(10) -0.00930(15) 0.16373(5) 0.0250(3) Uani 1 1 d . . . . .
H13 H 0.0853 -0.0236 0.1343 0.030 Uiso 1 1 calc R U . . .
C14 C 0.05831(10) -0.07713(16) 0.19891(5) 0.0242(3) Uani 1 1 d . . . . .
C15 C 0.09084(10) -0.05730(15) 0.24234(5) 0.0232(3) Uani 1 1 d . . . . .
C16 C 0.17386(10) 0.03242(15) 0.25027(5) 0.0230(3) Uani 1 1 d . . . . .
C17 C 0.22406(10) 0.09983(16) 0.21509(5) 0.0232(3) Uani 1 1 d . . . . .
H17 H 0.2808 0.1597 0.2206 0.028 Uiso 1 1 calc R U . . .
C18 C 0.12038(13) 0.5825(2) -0.10946(5) 0.0400(4) Uani 1 1 d . . . . .
H18A H 0.0790 0.4898 -0.1057 0.060 Uiso 1 1 calc R U . . .
H18B H 0.1190 0.6160 -0.1405 0.060 Uiso 1 1 calc R U . . .
H18C H 0.0967 0.6683 -0.0906 0.060 Uiso 1 1 calc R U . . .
C19 C -0.06376(12) -0.1774(2) 0.15085(5) 0.0378(4) Uani 1 1 d . . . . .
H19A H -0.0805 -0.0712 0.1407 0.057 Uiso 1 1 calc R U . . .
H19B H -0.1222 -0.2426 0.1517 0.057 Uiso 1 1 calc R U . . .
H19C H -0.0169 -0.2243 0.1304 0.057 Uiso 1 1 calc R U . . .
C20 C -0.04558(11) -0.07200(19) 0.28976(5) 0.0338(4) Uani 1 1 d . . . . .
H20A H -0.0416 0.0428 0.2928 0.051 Uiso 1 1 calc R U . . .
H20B H -0.0655 -0.1182 0.3181 0.051 Uiso 1 1 calc R U . . .
H20C H -0.0931 -0.0988 0.2669 0.051 Uiso 1 1 calc R U . . .
C21 C 0.28322(11) 0.13789(18) 0.30360(5) 0.0302(3) Uani 1 1 d . . . . .
H21A H 0.3399 0.0952 0.2883 0.045 Uiso 1 1 calc R U . . .
H21B H 0.2947 0.1370 0.3356 0.045 Uiso 1 1 calc R U . . .
H21C H 0.2717 0.2463 0.2937 0.045 Uiso 1 1 calc R U . . .


_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 C1 1.2296(18) . ?
O2 C5 1.3658(18) . ?
O2 C18 1.427(2) . ?
O3 C14 1.3704(17) . ?
O3 C19 1.4279(18) . ?
O4 C15 1.3783(16) . ?
O4 C20 1.4349(18) . ?
O5 C16 1.3647(17) . ?
O5 C21 1.4291(17) . ?
C1 C2 1.482(2) . ?
C1 C10 1.497(2) . ?
C2 C7 1.392(2) . ?
C2 C3 1.407(2) . ?
C3 C4 1.369(2) . ?
C4 C5 1.396(2) . ?
C5 C6 1.388(2) . ?
C6 C7 1.397(2) . ?
C7 C8 1.505(2) . ?
C8 C9 1.526(2) . ?
C9 C10 1.515(2) . ?
C10 C11 1.346(2) . ?
C11 C12 1.466(2) . ?
C12 C13 1.3979(19) . ?
C12 C17 1.403(2) . ?
C13 C14 1.391(2) . ?
C14 C15 1.397(2) . ?
C15 C16 1.399(2) . ?
C16 C17 1.392(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
C5 O2 C18 118.08(12) . . ?
C14 O3 C19 116.81(11) . . ?
C15 O4 C20 114.97(11) . . ?
C16 O5 C21 117.15(11) . . ?
O1 C1 C2 120.22(13) . . ?
O1 C1 C10 121.66(13) . . ?
C2 C1 C10 118.11(13) . . ?
C7 C2 C3 119.04(14) . . ?
C7 C2 C1 121.77(13) . . ?
C3 C2 C1 119.19(14) . . ?
C4 C3 C2 120.87(16) . . ?
C3 C4 C5 120.03(15) . . ?
O2 C5 C6 124.36(15) . . ?
O2 C5 C4 115.75(14) . . ?
C6 C5 C4 119.89(15) . . ?
C5 C6 C7 120.16(15) . . ?
C2 C7 C6 119.95(14) . . ?
C2 C7 C8 119.75(13) . . ?
C6 C7 C8 120.23(14) . . ?
C7 C8 C9 113.07(13) . . ?
C10 C9 C8 112.44(12) . . ?
C11 C10 C1 116.77(13) . . ?
C11 C10 C9 125.86(13) . . ?
C1 C10 C9 117.37(12) . . ?
C10 C11 C12 130.44(14) . . ?
C13 C12 C17 119.29(13) . . ?
C13 C12 C11 123.13(13) . . ?
C17 C12 C11 117.51(13) . . ?
C14 C13 C12 120.21(13) . . ?
O3 C14 C13 123.94(13) . . ?
O3 C14 C15 115.48(12) . . ?
C13 C14 C15 120.57(13) . . ?
O4 C15 C14 121.65(12) . . ?
O4 C15 C16 118.78(12) . . ?
C14 C15 C16 119.40(12) . . ?
O5 C16 C17 124.77(13) . . ?
O5 C16 C15 115.06(12) . . ?
C17 C16 C15 120.16(13) . . ?
C16 C17 C12 120.37(13) . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kp91
_database_code_depnum_ccdc_archive 'CCDC 1899788'
loop_
_audit_author_name
_audit_author_address
'Kevin Klausmeyer'
;Baylor University
United States of America
;
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 Br O4'
_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'

_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                   13.7677(8)
_cell_length_b                   10.5053(9)
_cell_length_c                   25.8983(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3745.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    2.218
_shelx_estimated_absorpt_T_min   0.649
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_T_max  0.702
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            30172
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.562
_diffrn_reflns_theta_max         26.425
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3829
_reflns_number_gt                3166
_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-2014 (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)+(0.0370P)²+2.7625P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3829
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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_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
Br1 Br 0.53776(2) 0.03221(3) 0.63643(2) 0.03073(10) Uani 1 1 d . . . . .
O3 O -0.25443(12) -0.08042(18) 0.55962(7) 0.0322(4) Uani 1 1 d . . . . .
O4 O -0.23175(12) 0.10125(19) 0.63053(6) 0.0315(4) Uani 1 1 d . . . . .
O1 O 0.51793(13) -0.10232(19) 0.73419(7) 0.0347(4) Uani 1 1 d . . . . .
O2 O -0.10145(12) -0.19173(16) 0.51433(7) 0.0290(4) Uani 1 1 d . . . . .
C1 C 0.42270(17) 0.0181(2) 0.67676(9) 0.0204(5) Uani 1 1 d . . . . .
C12 C 0.02494(16) 0.0288(2) 0.60317(9) 0.0197(5) Uani 1 1 d . . . . .
C6 C 0.33666(16) 0.0743(2) 0.66054(8) 0.0181(5) Uani 1 1 d . . . . .
C14 C -0.08141(18) -0.1020(2) 0.55146(9) 0.0217(5) Uani 1 1 d . . . . .
C10 C 0.15658(17) 0.1002(2) 0.67162(9) 0.0220(5) Uani 1 1 d . . . . .
H10 H 0.1033 0.1037 0.6978 0.026 Uiso 1 1 calc R U . . .
C16 C -0.14795(17) 0.0507(2) 0.61086(9) 0.0228(5) Uani 1 1 d . . . . .
C15 C -0.16192(17) -0.0439(2) 0.57372(9) 0.0231(5) Uani 1 1 d . . . . .
C4 C 0.25931(19) -0.0113(3) 0.73665(9) 0.0270(6) Uani 1 1 d . . . . .
H4 H 0.2030 -0.0220 0.7574 0.032 Uiso 1 1 calc R U . . .
C8 C 0.25030(18) 0.2534(2) 0.61332(10) 0.0292(6) Uani 1 1 d . . . . .
H8A H 0.2690 0.3232 0.6370 0.035 Uiso 1 1 calc R U . . .
H8B H 0.2429 0.2904 0.5784 0.035 Uiso 1 1 calc R U . . .
C9 C 0.15384(18) 0.2005(2) 0.63030(9) 0.0240(5) Uani 1 1 d . . . . .
H9 H 0.0993 0.2630 0.6326 0.029 Uiso 1 1 calc R U . . .
C5 C 0.25218(16) 0.0552(2) 0.69044(8) 0.0192(5) Uani 1 1 d . . . . .
C17 C -0.05506(17) 0.0880(2) 0.62578(9) 0.0224(5) Uani 1 1 d . . . . .
H17 H -0.0463 0.1527 0.6510 0.027 Uiso 1 1 calc R U . . .
C2 C 0.42945(18) -0.0513(2) 0.72246(9) 0.0238(5) Uani 1 1 d . . . . .
C3 C 0.34713(18) -0.0625(2) 0.75309(10) 0.0289(6) Uani 1 1 d . . . . .
H3 H 0.3508 -0.1052 0.7854 0.035 Uiso 1 1 calc R U . . .
C7 C 0.33200(17) 0.1554(2) 0.61207(9) 0.0226(5) Uani 1 1 d . . . . .
H7A H 0.3227 0.0991 0.5818 0.027 Uiso 1 1 calc R U . . .
H7B H 0.3947 0.2002 0.6077 0.027 Uiso 1 1 calc R U . . .
C11 C 0.12585(17) 0.0663(2) 0.61622(9) 0.0201(5) Uani 1 1 d . . . . .
H11 H 0.1766 0.0196 0.5962 0.024 Uiso 1 1 calc R U . . .
C13 C 0.01147(17) -0.0663(2) 0.56654(9) 0.0189(5) Uani 1 1 d . . . . .
H13 H 0.0663 -0.1071 0.5517 0.023 Uiso 1 1 calc R U . . .
C19 C -0.02115(19) -0.2596(3) 0.49318(10) 0.0292(6) Uani 1 1 d . . . . .
H19A H 0.0245 -0.1993 0.4775 0.044 Uiso 1 1 calc R U . . .
H19B H -0.0444 -0.3191 0.4668 0.044 Uiso 1 1 calc R U . . .
H19C H 0.0117 -0.3071 0.5207 0.044 Uiso 1 1 calc R U . . .
C20 C -0.2977(2) 0.0065(3) 0.52410(11) 0.0405(7) Uani 1 1 d . . . . .
H20A H -0.2996 0.0917 0.5395 0.061 Uiso 1 1 calc R U . . .
H20B H -0.3639 -0.0214 0.5161 0.061 Uiso 1 1 calc R U . . .
H20C H -0.2592 0.0088 0.4923 0.061 Uiso 1 1 calc R U . . .
C21 C -0.2239(2) 0.2153(3) 0.65990(12) 0.0391(7) Uani 1 1 d . . . . .
H21A H -0.1897 0.1975 0.6923 0.059 Uiso 1 1 calc R U . . .
H21B H -0.2889 0.2481 0.6675 0.059 Uiso 1 1 calc R U . . .
H21C H -0.1875 0.2789 0.6401 0.059 Uiso 1 1 calc R U . . .
C18 C 0.5225(2) -0.1872(3) 0.77761(11) 0.0377(7) Uani 1 1 d . . . . .
H18A H 0.5058 -0.1407 0.8092 0.056 Uiso 1 1 calc R U . . .
H18B H 0.5885 -0.2216 0.7807 0.056 Uiso 1 1 calc R U . . .
H18C H 0.4765 -0.2573 0.7726 0.056 Uiso 1 1 calc R U . . .


_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 C1 1.903(2) . ?
O3 C15 1.379(3) . ?
O3 C20 1.426(3) . ?
O4 C16 1.368(3) . ?
O4 C21 1.424(3) . ?
O1 C2 1.365(3) . ?
O1 C18 1.437(3) . ?
O2 C14 1.374(3) . ?
O2 C19 1.425(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.393(3) . ?
C12 C13 1.390(3) . ?
C12 C17 1.394(3) . ?
C12 C11 1.483(3) . ?
C6 C5 1.412(3) . ?
C6 C7 1.518(3) . ?
C14 C13 1.389(3) . ?
C14 C15 1.390(3) . ?
C10 C5 1.481(3) . ?
C10 C9 1.502(3) . ?
C10 C11 1.538(3) . ?
C16 C17 1.392(3) . ?
C16 C15 1.397(3) . ?
C4 C5 1.389(3) . ?
C4 C3 1.390(4) . ?
C8 C9 1.505(3) . ?
C8 C7 1.525(3) . ?
C9 C11 1.506(3) . ?
C2 C3 1.388(4) . ?

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
C15 O3 C20 112.2(2) . . ?
C16 O4 C21 117.5(2) . . ?
C2 O1 C18 117.2(2) . . ?
C14 O2 C19 117.14(18) . . ?
C6 C1 C2 122.4(2) . . ?
C6 C1 Br1 120.72(17) . . ?
C2 C1 Br1 116.84(18) . . ?
C13 C12 C17 120.1(2) . . ?
C13 C12 C11 118.1(2) . . ?
C17 C12 C11 121.7(2) . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 121.6(2) . . ?
C5 C6 C7 119.9(2) . . ?
O2 C14 C13 124.5(2) . . ?
O2 C14 C15 115.5(2) . . ?
C13 C14 C15 119.9(2) . . ?
C5 C10 C9 118.7(2) . . ?
C5 C10 C11 118.53(19) . . ?
C9 C10 C11 59.39(15) . . ?
O4 C16 C17 124.2(2) . . ?
O4 C16 C15 114.6(2) . . ?
C17 C16 C15 121.2(2) . . ?
O3 C15 C14 120.3(2) . . ?
O3 C15 C16 120.5(2) . . ?
C14 C15 C16 119.2(2) . . ?
C5 C4 C3 121.3(2) . . ?
C9 C8 C7 114.0(2) . . ?
C10 C9 C8 116.4(2) . . ?
C10 C9 C11 61.49(15) . . ?
C8 C9 C11 120.0(2) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 C10 120.5(2) . . ?
C6 C5 C10 120.4(2) . . ?
C16 C17 C12 119.0(2) . . ?
O1 C2 C3 124.6(2) . . ?
O1 C2 C1 117.0(2) . . ?
C3 C2 C1 118.4(2) . . ?
C2 C3 C4 120.2(2) . . ?
C6 C7 C8 113.1(2) . . ?
C12 C11 C9 122.9(2) . . ?
C12 C11 C10 122.1(2) . . ?
C9 C11 C10 59.12(15) . . ?
C14 C13 C12 120.6(2) . . ?

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.067

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kp94
_database_code_depnum_ccdc_archive 'CCDC 1899787'
loop_
_audit_author_name
_audit_author_address
'Kevin Klausmeyer'
;Baylor University
United States of America
;
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 O4'
_chemical_formula_weight         340.40

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.0800(2)
_cell_length_b                   8.7733(3)
_cell_length_c                   28.3213(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1759.18(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.322
_exptl_crystal_size_min          0.147
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            14446
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.731
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4355
_reflns_number_gt                3868
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.999

_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 (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)+(0.0387P)²+0.2776P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1463 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.2(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4355
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_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
O4 O 1.34241(19) 0.97754(14) 0.87996(5) 0.0298(3) Uani 1 1 d . . . . .
O3 O 1.21468(19) 1.12861(14) 0.95542(5) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.9310(2) 1.01951(16) 1.00701(5) 0.0364(4) Uani 1 1 d . . . . .
O1 O 0.11145(19) 0.33512(17) 0.77199(5) 0.0346(3) Uani 1 1 d . . . . .
C4 C 0.6220(3) 0.50577(19) 0.82197(6) 0.0218(4) Uani 1 1 d . . . . .
C3 C 0.5368(3) 0.37656(19) 0.84235(6) 0.0215(4) Uani 1 1 d . . . . .
C2 C 0.3669(3) 0.3242(2) 0.82419(6) 0.0249(4) Uani 1 1 d . . . . .
H2 H 0.3094 0.2365 0.8376 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3631(3) 0.5243(2) 0.76607(6) 0.0278(4) Uani 1 1 d . . . . .
H6 H 0.3043 0.5750 0.7403 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5348(3) 0.5752(2) 0.78373(6) 0.0262(4) Uani 1 1 d . . . . .
H5 H 0.5943 0.6602 0.7692 0.031 Uiso 1 1 calc R U . . .
C1 C 0.2793(3) 0.3981(2) 0.78666(7) 0.0259(4) Uani 1 1 d . . . . .
C10 C 0.8023(3) 0.5663(2) 0.84090(6) 0.0231(4) Uani 1 1 d . . . . .
H10 H 0.8747 0.6347 0.8192 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8727(3) 0.8130(2) 0.95082(6) 0.0226(4) Uani 1 1 d . . . . .
H13 H 0.7665 0.7769 0.9680 0.027 Uiso 1 1 calc R U . . .
C17 C 1.0881(2) 0.7901(2) 0.88527(6) 0.0219(4) Uani 1 1 d . . . . .
H17 H 1.1301 0.7379 0.8578 0.026 Uiso 1 1 calc R U . . .
C12 C 0.9300(3) 0.7379(2) 0.90976(6) 0.0209(4) Uani 1 1 d . . . . .
C16 C 1.1845(3) 0.9186(2) 0.90106(6) 0.0219(4) Uani 1 1 d . . . . .
C15 C 1.1245(3) 0.99695(19) 0.94132(6) 0.0225(4) Uani 1 1 d . . . . .
C11 C 0.8214(3) 0.60185(19) 0.89385(6) 0.0209(4) Uani 1 1 d . . . . .
H11 H 0.7075 0.5773 0.9133 0.025 Uiso 1 1 calc R U . . .
C14 C 0.9712(3) 0.9410(2) 0.96669(6) 0.0239(4) Uani 1 1 d . . . . .
C7 C 0.6321(3) 0.29694(19) 0.88333(7) 0.0247(4) Uani 1 1 d . . . . .
H7A H 0.5927 0.1887 0.8838 0.030 Uiso 1 1 calc R U . . .
H7B H 0.5898 0.3444 0.9132 0.030 Uiso 1 1 calc R U . . .
C9 C 0.9195(3) 0.4654(2) 0.87223(6) 0.0240(4) Uani 1 1 d . . . . .
H9 H 1.0594 0.4754 0.8683 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8478(3) 0.3052(2) 0.88044(7) 0.0272(4) Uani 1 1 d . . . . .
H8A H 0.9022 0.2656 0.9102 0.033 Uiso 1 1 calc R U . . .
H8B H 0.8918 0.2389 0.8544 0.033 Uiso 1 1 calc R U . . .
C21 C 1.4425(3) 0.8820(2) 0.84811(7) 0.0334(5) Uani 1 1 d . . . . .
H21A H 1.4633 0.7822 0.8628 0.050 Uiso 1 1 calc R U . . .
H21B H 1.5647 0.9286 0.8405 0.050 Uiso 1 1 calc R U . . .
H21C H 1.3688 0.8693 0.8191 0.050 Uiso 1 1 calc R U . . .
C20 C 1.3798(3) 1.0989(2) 0.98334(7) 0.0320(5) Uani 1 1 d . . . . .
H20A H 1.3437 1.0430 1.0119 0.048 Uiso 1 1 calc R U . . .
H20B H 1.4391 1.1957 0.9922 0.048 Uiso 1 1 calc R U . . .
H20C H 1.4693 1.0378 0.9649 0.048 Uiso 1 1 calc R U . . .
C19 C 0.8015(3) 0.9524(3) 1.03934(7) 0.0370(5) Uani 1 1 d . . . . .
H19A H 0.6775 0.9425 1.0243 0.056 Uiso 1 1 calc R U . . .
H19B H 0.7905 1.0171 1.0674 0.056 Uiso 1 1 calc R U . . .
H19C H 0.8474 0.8513 1.0486 0.056 Uiso 1 1 calc R U . . .
C18 C 0.0080(3) 0.4156(3) 0.73683(8) 0.0412(5) Uani 1 1 d . . . . .
H18A H -0.0098 0.5215 0.7469 0.062 Uiso 1 1 calc R U . . .
H18B H -0.1155 0.3672 0.7324 0.062 Uiso 1 1 calc R U . . .
H18C H 0.0781 0.4135 0.7070 0.062 Uiso 1 1 calc R U . . .


_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
O4 C16 1.369(2) . ?
O4 C21 1.421(2) . ?
O3 C15 1.379(2) . ?
O3 C20 1.435(2) . ?
O2 C14 1.364(2) . ?
O2 C19 1.423(2) . ?
O1 C1 1.375(2) . ?
O1 C18 1.424(3) . ?
C4 C5 1.388(3) . ?
C4 C3 1.408(2) . ?
C4 C10 1.483(3) . ?
C3 C2 1.387(3) . ?
C3 C7 1.513(3) . ?
C2 C1 1.391(3) . ?
C6 C1 1.385(3) . ?
C6 C5 1.388(3) . ?
C10 C9 1.503(3) . ?
C10 C11 1.538(2) . ?
C13 C14 1.396(3) . ?
C13 C12 1.397(2) . ?
C17 C16 1.391(2) . ?
C17 C12 1.395(3) . ?
C12 C11 1.490(2) . ?
C16 C15 1.398(2) . ?
C15 C14 1.391(3) . ?
C11 C9 1.513(2) . ?
C7 C8 1.531(3) . ?
C9 C8 1.513(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
C16 O4 C21 117.50(14) . . ?
C15 O3 C20 112.62(14) . . ?
C14 O2 C19 117.66(15) . . ?
C1 O1 C18 117.16(17) . . ?
C5 C4 C3 118.89(17) . . ?
C5 C4 C10 120.51(16) . . ?
C3 C4 C10 120.60(16) . . ?
C2 C3 C4 119.10(17) . . ?
C2 C3 C7 121.22(16) . . ?
C4 C3 C7 119.69(16) . . ?
C3 C2 C1 121.05(17) . . ?
C1 C6 C5 118.74(18) . . ?
C4 C5 C6 121.96(18) . . ?
O1 C1 C6 124.37(18) . . ?
O1 C1 C2 115.39(17) . . ?
C6 C1 C2 120.22(17) . . ?
C4 C10 C9 118.53(15) . . ?
C4 C10 C11 120.04(15) . . ?
C9 C10 C11 59.67(12) . . ?
C14 C13 C12 120.15(17) . . ?
C16 C17 C12 119.98(16) . . ?
C17 C12 C13 119.51(16) . . ?
C17 C12 C11 121.80(16) . . ?
C13 C12 C11 118.68(16) . . ?
O4 C16 C17 124.47(16) . . ?
O4 C16 C15 114.74(15) . . ?
C17 C16 C15 120.79(16) . . ?
O3 C15 C14 120.49(16) . . ?
O3 C15 C16 120.50(16) . . ?
C14 C15 C16 119.01(16) . . ?
C12 C11 C9 121.28(16) . . ?
C12 C11 C10 120.18(15) . . ?
C9 C11 C10 59.03(11) . . ?
O2 C14 C15 114.67(16) . . ?
O2 C14 C13 124.85(17) . . ?
C15 C14 C13 120.48(17) . . ?
C3 C7 C8 112.44(16) . . ?
C10 C9 C8 116.91(16) . . ?
C10 C9 C11 61.30(11) . . ?
C8 C9 C11 121.25(16) . . ?
C9 C8 C7 112.77(15) . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-3

