# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2014_01_27
_database_code_depnum_ccdc_archive 'CCDC 1030912'
_audit_update_record             
;
2014-10-24 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;
_audit_creation_date             
;
'Mon Jan 27 21:53:15 2014'
;
_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C43 H38 N4 O15'
_chemical_formula_sum            'C43 H38 N O15'
_chemical_formula_weight         808.74
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H20 O4'
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'
N N 0.0061 0.0033 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_symmetry_space_group_name_H-M_alt 'P 1 21 1'
_cell_length_a                   7.8734(2)
_cell_length_b                   17.4148(5)
_cell_length_c                   14.5347(4)
_cell_angle_alpha                90.0
_cell_angle_beta                 91.013(3)
_cell_angle_gamma                90.0
_cell_volume                     1992.58(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2961
_cell_measurement_temperature    125(30)
_cell_measurement_theta_max      27.1380
_cell_measurement_theta_min      2.7970
_cell_oxdiff_angle_alpha         89.985(4)
_cell_oxdiff_angle_beta          90.994(5)
_cell_oxdiff_angle_gamma         90.012(4)
_cell_oxdiff_length_a            7.8729(4)
_cell_oxdiff_length_b            17.4162(8)
_cell_oxdiff_length_c            14.5343(8)
_cell_oxdiff_measurement_reflns_used 2961
_cell_oxdiff_volume              1992.58(18)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             846
_exptl_crystal_size_max          0.2042
_exptl_crystal_size_mid          0.1076
_exptl_crystal_size_min          0.0704
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7166
_diffrn_reflns_point_group_measured_fraction_full 0.721
_diffrn_reflns_point_group_measured_fraction_max 0.697
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.352
_diffrn_reflns_theta_min         2.338
_diffrn_ambient_temperature      125(30)
_diffrn_detector_area_resol_mean 10.3590
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -65.00   31.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6864  -38.0000 -180.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   32.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6864   57.0000  -30.0000 39
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0501858000
_diffrn_orient_matrix_UB_12      -0.0114982000
_diffrn_orient_matrix_UB_13      -0.0376410000
_diffrn_orient_matrix_UB_21      0.0651838000
_diffrn_orient_matrix_UB_22      0.0255403000
_diffrn_orient_matrix_UB_23      0.0147147000
_diffrn_orient_matrix_UB_31      0.0367672000
_diffrn_orient_matrix_UB_32      -0.0295657000
_diffrn_orient_matrix_UB_33      0.0273672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.523
_reflns_Friedel_fraction_full    0.520
_reflns_Friedel_fraction_max     0.496
_reflns_number_gt                5041
_reflns_number_total             5679
_reflns_odcompleteness_completeness 88.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         5679
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0390P)²+0.4966P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1087
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C17(H17), C23(H23), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C13(H13A,H13B), C25(H25A,H25B), C29(H29A,H29B),
 C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C14(H14), C15(H15), C20(H20), C24(H24), C27(H27), C28(H28),
 C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C40(H40), C42(H42), C43(H43),
  C10(H10), C12(H12), C19(H19), C1B(H1B), C1C(H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 -0.0650(3) -0.54838(16) -0.03159(18) 0.0202(6) Uani 1 1 d . . . . .
O2 O -0.3341(3) -0.61385(16) -0.3478(2) 0.0225(7) Uani 1 1 d . . . . .
O3 O -0.0847(3) -0.44384(16) -0.1868(2) 0.0219(6) Uani 1 1 d . . . . .
O4 O 0.3197(4) -0.55985(17) -0.0487(2) 0.0250(7) Uani 1 1 d . . . . .
C1 C -0.5042(5) -0.6177(3) -0.3556(3) 0.0214(9) Uani 1 1 d . . . . .
O5 O -0.5997(3) -0.57191(16) -0.3220(2) 0.0249(7) Uani 1 1 d . . . . .
O6 O -0.0935(3) -0.49677(16) -0.39459(19) 0.0218(7) Uani 1 1 d . . . . .
O7 O -0.4376(4) -0.5790(2) 0.3381(2) 0.0380(8) Uani 1 1 d . . . . .
C7 C -0.6982(6) -0.8216(3) -0.4864(3) 0.0255(10) Uani 1 1 d . . . . .
H7 H -0.7421 -0.8666 -0.5116 0.031 Uiso 1 1 calc R . . . .
C3 C -0.0863(5) -0.5404(2) -0.3112(3) 0.0191(9) Uani 1 1 d . . . . .
H3 H -0.0325 -0.5900 -0.3236 0.023 Uiso 1 1 calc R . . . .
O8 O -0.4288(5) -0.4635(2) 0.3924(2) 0.0441(9) Uani 1 1 d . . . . .
O9 O -1.0041(5) -0.8646(2) -0.4145(3) 0.0466(10) Uani 1 1 d . . . . .
O10 O -1.0650(4) -0.74666(19) -0.3795(2) 0.0346(8) Uani 1 1 d . . . . .
C11 C -0.2420(5) -0.5431(3) 0.1937(3) 0.0224(9) Uani 1 1 d . . . . .
H11 H -0.2611 -0.5949 0.2052 0.027 Uiso 1 1 calc R . . . .
C5 C -0.2410(6) -0.3268(3) -0.1854(3) 0.0244(10) Uani 1 1 d . . . . .
C6 C 0.1061(5) -0.5527(2) -0.1666(3) 0.0194(9) Uani 1 1 d . . . . .
H6 H 0.1695 -0.5896 -0.2034 0.023 Uiso 1 1 calc R . . . .
C8 C -0.1614(5) -0.6383(2) -0.1492(3) 0.0230(10) Uani 1 1 d . . . . .
H8A H -0.2141 -0.6714 -0.1043 0.028 Uiso 1 1 calc R . . . .
H8B H -0.1236 -0.6705 -0.1992 0.028 Uiso 1 1 calc R . . . .
C9 C 0.0588(5) -0.5032(3) -0.4472(3) 0.0253(10) Uani 1 1 d . . . . .
H9A H 0.1537 -0.5136 -0.4057 0.030 Uiso 1 1 calc R . . . .
H9B H 0.0801 -0.4545 -0.4772 0.030 Uiso 1 1 calc R . . . .
O11 O -0.0581(4) -0.29039(19) 0.0827(2) 0.0361(8) Uani 1 1 d . . . . .
N10 N -0.1458(5) -0.3074(2) 0.1486(3) 0.0298(9) Uani 1 1 d . . . . .
O12 O -0.2034(5) -0.2610(2) 0.2027(3) 0.0487(10) Uani 1 1 d . . . . .
C13 C 0.4485(5) -0.5240(3) 0.0067(3) 0.0271(10) Uani 1 1 d . . . . .
H13A H 0.5216 -0.4945 -0.0330 0.032 Uiso 1 1 calc R . . . .
H13B H 0.5173 -0.5636 0.0356 0.032 Uiso 1 1 calc R . . . .
C14 C -0.3336(6) -0.2296(3) -0.0800(4) 0.0342(12) Uani 1 1 d . . . . .
H14 H -0.3072 -0.1926 -0.0360 0.041 Uiso 1 1 calc R . . . .
C15 C -0.7335(5) -0.7064(2) -0.3945(3) 0.0230(10) Uani 1 1 d . . . . .
H15 H -0.8040 -0.6746 -0.3609 0.028 Uiso 1 1 calc R . . . .
C16 C -0.7949(5) -0.7732(3) -0.4334(3) 0.0239(10) Uani 1 1 d . . . . .
C17 C -0.0077(5) -0.6003(2) -0.1046(3) 0.0202(9) Uani 1 1 d . . . . .
H17 H 0.0621 -0.6405 -0.0758 0.024 Uiso 1 1 calc R . . . .
O16 O -0.4839(4) -0.90893(19) -0.5847(2) 0.0381(9) Uani 1 1 d . . . . .
N17 N -0.4243(5) -0.8485(2) -0.5559(3) 0.0297(9) Uani 1 1 d . . . . .
O18 O -0.2791(4) -0.8269(2) -0.5711(3) 0.0471(10) Uani 1 1 d . . . . .
C20 C -0.1274(5) -0.4418(3) 0.0996(3) 0.0218(9) Uani 1 1 d . . . . .
H20 H -0.0725 -0.4257 0.0469 0.026 Uiso 1 1 calc R . . . .
C21 C -0.5319(6) -0.7991(3) -0.4997(3) 0.0245(10) Uani 1 1 d . . . . .
C22 C -0.2971(5) -0.4870(3) 0.2543(3) 0.0239(10) Uani 1 1 d . . . . .
C23 C -0.2698(5) -0.5542(2) -0.2842(3) 0.0205(9) Uani 1 1 d . . . . .
H23 H -0.3350 -0.5069 -0.2940 0.025 Uiso 1 1 calc R . . . .
C24 C -0.4604(5) -0.7337(2) -0.4587(3) 0.0235(10) Uani 1 1 d . . . . .
H24 H -0.3465 -0.7217 -0.4663 0.028 Uiso 1 1 calc R . . . .
C25 C -0.1015(6) -0.3712(3) -0.2317(3) 0.0307(11) Uani 1 1 d . . . . .
H25A H -0.1298 -0.3785 -0.2963 0.037 Uiso 1 1 calc R . . . .
H25B H 0.0045 -0.3430 -0.2272 0.037 Uiso 1 1 calc R . . . .
C26 C -0.5635(6) -0.6875(2) -0.4067(3) 0.0215(9) Uani 1 1 d . . . . .
C27 C -0.5008(6) -0.2427(3) -0.1049(4) 0.0378(12) Uani 1 1 d . . . . .
H27 H -0.5869 -0.2140 -0.0788 0.045 Uiso 1 1 calc R . . . .
C28 C -0.1039(7) -0.6597(3) -0.6093(3) 0.0345(12) Uani 1 1 d . . . . .
H28 H -0.2047 -0.6852 -0.6232 0.041 Uiso 1 1 calc R . . . .
C29 C 0.2379(5) -0.5079(2) -0.1113(3) 0.0219(9) Uani 1 1 d . . . . .
H29A H 0.3205 -0.4855 -0.1520 0.026 Uiso 1 1 calc R . . . .
H29B H 0.1838 -0.4668 -0.0777 0.026 Uiso 1 1 calc R . . . .
C30 C 0.0172(5) -0.4984(2) -0.2358(3) 0.0213(9) Uani 1 1 d . . . . .
H30 H 0.1062 -0.4694 -0.2666 0.026 Uiso 1 1 calc R . . . .
C31 C -0.1001(6) -0.6032(3) -0.5421(3) 0.0288(11) Uani 1 1 d . . . . .
H31 H -0.1994 -0.5905 -0.5120 0.035 Uiso 1 1 calc R . . . .
C32 C 0.1968(6) -0.5844(3) -0.5660(3) 0.0315(11) Uani 1 1 d . . . . .
H32 H 0.2980 -0.5593 -0.5516 0.038 Uiso 1 1 calc R . . . .
C33 C 0.0494(5) -0.5655(3) -0.5192(3) 0.0236(10) Uani 1 1 d . . . . .
C34 C -0.5394(6) -0.2991(3) -0.1690(4) 0.0405(13) Uani 1 1 d . . . . .
H34 H -0.6521 -0.3091 -0.1849 0.049 Uiso 1 1 calc R . . . .
C35 C 0.1931(7) -0.6401(3) -0.6338(3) 0.0377(12) Uani 1 1 d . . . . .
H35 H 0.2919 -0.6520 -0.6648 0.045 Uiso 1 1 calc R . . . .
C36 C -0.4110(6) -0.3408(3) -0.2095(3) 0.0334(12) Uani 1 1 d . . . . .
H36 H -0.4378 -0.3783 -0.2530 0.040 Uiso 1 1 calc R . . . .
C37 C -0.1577(5) -0.5196(3) 0.1156(3) 0.0216(9) Uani 1 1 d . . . . .
C40 C -0.2686(5) -0.4097(3) 0.2415(3) 0.0252(10) Uani 1 1 d . . . . .
H40 H -0.3065 -0.3731 0.2829 0.030 Uiso 1 1 calc R . . . .
C41 C -0.2953(5) -0.5820(3) -0.1868(3) 0.0219(9) Uani 1 1 d . . . . .
H41A H -0.4055 -0.6065 -0.1840 0.026 Uiso 1 1 calc R . . . .
H41B H -0.2976 -0.5376 -0.1465 0.026 Uiso 1 1 calc R . . . .
C42 C 0.0436(7) -0.6782(3) -0.6560(4) 0.0387(13) Uani 1 1 d . . . . .
H42 H 0.0417 -0.7157 -0.7015 0.046 Uiso 1 1 calc R . . . .
C43 C -0.2050(6) -0.2711(3) -0.1201(3) 0.0272(10) Uani 1 1 d . . . . .
H43 H -0.0928 -0.2615 -0.1029 0.033 Uiso 1 1 calc R . . . .
N1 N -0.3947(5) -0.5119(3) 0.3343(3) 0.0312(9) Uani 1 1 d . . . . .
C18 C -0.1808(5) -0.3896(3) 0.1638(3) 0.0244(10) Uani 1 1 d . . . . .
N3 N -0.9688(5) -0.7959(2) -0.4089(3) 0.0309(9) Uani 1 1 d . . . . .
O13 O -0.1054(4) -0.64747(17) 0.0663(2) 0.0278(7) Uani 1 1 d . . . . .
C1A C -0.1054(5) -0.5795(2) 0.0482(3) 0.0208(9) Uani 1 1 d . . . . .
C4 C 0.3827(5) -0.4716(3) 0.0804(3) 0.0243(10) Uani 1 1 d . . . . .
C10 C 0.4088(6) -0.3931(3) 0.0753(3) 0.0318(11) Uani 1 1 d . . . . .
H10 H 0.4623 -0.3723 0.0246 0.038 Uiso 1 1 calc R . . . .
C12 C 0.2996(5) -0.5013(3) 0.1566(3) 0.0319(11) Uani 1 1 d . . . . .
H12 H 0.2802 -0.5538 0.1606 0.038 Uiso 1 1 calc R . . . .
C19 C 0.2463(6) -0.4536(4) 0.2257(3) 0.0391(14) Uani 1 1 d . . . . .
H19 H 0.1913 -0.4743 0.2760 0.047 Uiso 1 1 calc R . . . .
C1B C 0.2736(7) -0.3757(4) 0.2212(4) 0.0451(15) Uani 1 1 d . . . . .
H1B H 0.2376 -0.3438 0.2682 0.054 Uiso 1 1 calc R . . . .
C1C C 0.3553(7) -0.3452(3) 0.1458(4) 0.0436(14) Uani 1 1 d . . . . .
H1C H 0.3743 -0.2926 0.1423 0.052 Uiso 1 1 calc R . . . .


_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 C17 1.472(5) . ?
O1 C1A 1.326(5) . ?
O2 C1 1.345(5) . ?
O2 C23 1.475(5) . ?
O3 C25 1.430(5) . ?
O3 C30 1.442(5) . ?
O4 C13 1.429(5) . ?
O4 C29 1.430(5) . ?
C1 O5 1.207(5) . ?
C1 C26 1.495(6) . ?
O6 C3 1.432(5) . ?
O6 C9 1.439(5) . ?
O7 N1 1.218(5) . ?
C7 C16 1.381(6) . ?
C7 C21 1.385(6) . ?
C3 C23 1.525(5) . ?
C3 C30 1.540(6) . ?
O8 N1 1.227(5) . ?
O9 N3 1.231(5) . ?
O10 N3 1.227(5) . ?
C11 C22 1.391(6) . ?
C11 C37 1.389(6) . ?
C5 C25 1.512(6) . ?
C5 C36 1.401(7) . ?
C5 C43 1.383(6) . ?
C6 C17 1.529(6) . ?
C6 C29 1.518(6) . ?
C6 C30 1.541(6) . ?
C8 C17 1.516(6) . ?
C8 C41 1.535(6) . ?
C9 C33 1.510(6) . ?
O11 N10 1.227(5) . ?
N10 O12 1.222(5) . ?
N10 C18 1.475(6) . ?
C13 C4 1.507(6) . ?
C14 C27 1.380(7) . ?
C14 C43 1.382(6) . ?
C15 C16 1.378(6) . ?
C15 C26 1.394(6) . ?
C16 N3 1.476(6) . ?
O16 N17 1.224(5) . ?
N17 O18 1.229(5) . ?
N17 C21 1.468(6) . ?
C20 C37 1.397(6) . ?
C20 C18 1.376(6) . ?
C21 C24 1.400(6) . ?
C22 C40 1.378(6) . ?
C22 N1 1.472(6) . ?
C23 C41 1.515(6) . ?
C24 C26 1.379(6) . ?
C27 C34 1.384(8) . ?
C28 C31 1.388(6) . ?
C28 C42 1.395(7) . ?
C31 C33 1.385(6) . ?
C32 C33 1.396(6) . ?
C32 C35 1.384(7) . ?
C34 C36 1.386(7) . ?
C35 C42 1.386(7) . ?
C37 C1A 1.496(6) . ?
C40 C18 1.381(6) . ?
O13 C1A 1.213(5) . ?
C4 C10 1.385(7) . ?
C4 C12 1.397(6) . ?
C10 C1C 1.394(7) . ?
C12 C19 1.376(7) . ?
C19 C1B 1.376(8) . ?
C1B C1C 1.388(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
C1A O1 C17 117.5(3) . . ?
C1 O2 C23 114.8(3) . . ?
C25 O3 C30 113.9(3) . . ?
C13 O4 C29 113.0(3) . . ?
O2 C1 C26 112.6(4) . . ?
O5 C1 O2 124.1(4) . . ?
O5 C1 C26 123.2(4) . . ?
C3 O6 C9 112.9(3) . . ?
C16 C7 C21 116.0(4) . . ?
O6 C3 C23 106.2(3) . . ?
O6 C3 C30 111.3(3) . . ?
C23 C3 C30 112.6(3) . . ?
C37 C11 C22 118.1(4) . . ?
C36 C5 C25 119.9(4) . . ?
C43 C5 C25 121.5(4) . . ?
C43 C5 C36 118.6(4) . . ?
C17 C6 C30 117.0(3) . . ?
C29 C6 C17 111.7(4) . . ?
C29 C6 C30 109.3(3) . . ?
C17 C8 C41 114.4(4) . . ?
O6 C9 C33 113.2(3) . . ?
O11 N10 C18 117.5(4) . . ?
O12 N10 O11 124.3(4) . . ?
O12 N10 C18 118.2(4) . . ?
O4 C13 C4 114.6(3) . . ?
C27 C14 C43 120.5(5) . . ?
C16 C15 C26 118.6(4) . . ?
C7 C16 N3 119.7(4) . . ?
C15 C16 C7 123.4(4) . . ?
C15 C16 N3 116.6(4) . . ?
O1 C17 C6 106.4(3) . . ?
O1 C17 C8 108.9(3) . . ?
C8 C17 C6 117.2(4) . . ?
O16 N17 O18 123.7(4) . . ?
O16 N17 C21 118.3(4) . . ?
O18 N17 C21 118.0(4) . . ?
C18 C20 C37 118.2(4) . . ?
C7 C21 N17 118.0(4) . . ?
C7 C21 C24 123.1(4) . . ?
C24 C21 N17 118.9(4) . . ?
C11 C22 N1 117.8(4) . . ?
C40 C22 C11 123.2(4) . . ?
C40 C22 N1 119.0(4) . . ?
O2 C23 C3 105.4(3) . . ?
O2 C23 C41 108.2(3) . . ?
C41 C23 C3 115.7(3) . . ?
C26 C24 C21 118.2(4) . . ?
O3 C25 C5 108.1(4) . . ?
C15 C26 C1 114.9(4) . . ?
C24 C26 C1 124.4(4) . . ?
C24 C26 C15 120.5(4) . . ?
C14 C27 C34 119.4(5) . . ?
C31 C28 C42 120.0(5) . . ?
O4 C29 C6 108.0(3) . . ?
O3 C30 C3 111.9(3) . . ?
O3 C30 C6 109.4(3) . . ?
C3 C30 C6 113.8(3) . . ?
C33 C31 C28 120.9(4) . . ?
C35 C32 C33 120.4(5) . . ?
C31 C33 C9 122.6(4) . . ?
C31 C33 C32 118.9(4) . . ?
C32 C33 C9 118.5(4) . . ?
C27 C34 C36 120.4(5) . . ?
C32 C35 C42 120.7(5) . . ?
C34 C36 C5 120.3(5) . . ?
C11 C37 C20 120.6(4) . . ?
C11 C37 C1A 118.2(4) . . ?
C20 C37 C1A 121.2(4) . . ?
C22 C40 C18 116.4(4) . . ?
C23 C41 C8 115.9(3) . . ?
C35 C42 C28 119.2(5) . . ?
C14 C43 C5 120.9(4) . . ?
O7 N1 O8 124.4(4) . . ?
O7 N1 C22 117.9(4) . . ?
O8 N1 C22 117.7(4) . . ?
C20 C18 N10 118.6(4) . . ?
C20 C18 C40 123.5(4) . . ?
C40 C18 N10 117.9(4) . . ?
O9 N3 C16 117.0(4) . . ?
O10 N3 O9 124.2(4) . . ?
O10 N3 C16 118.6(4) . . ?
O1 C1A C37 111.2(4) . . ?
O13 C1A O1 126.2(4) . . ?
O13 C1A C37 122.6(4) . . ?
C10 C4 C13 120.4(4) . . ?
C10 C4 C12 118.7(4) . . ?
C12 C4 C13 120.8(4) . . ?
C4 C10 C1C 120.3(5) . . ?
C19 C12 C4 120.7(5) . . ?
C12 C19 C1B 120.7(5) . . ?
C19 C1B C1C 119.4(5) . . ?
C1B C1C C10 120.2(5) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 0 0 0.1012 1.0000 0.0000 0.0000 0.0502 0.0652 0.0368
-1 0 0 0.1012 -1.0000 -0.0000 -0.0000 -0.0502 -0.0652 -0.0368
0 -1 -1 0.0466 -0.0000 -1.0000 -1.0000 0.0491 -0.0403 0.0022
0 1 1 0.0466 0.0000 1.0000 1.0000 -0.0491 0.0403 -0.0022
0 1 -1 0.0161 0.0000 1.0000 -1.0000 0.0261 0.0108 -0.0569
0 -1 1 0.0543 -0.0000 -1.0000 1.0000 -0.0261 -0.0108 0.0569
####################################################################### 
# 
# 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_mikkel17072014_100k
_database_code_depnum_ccdc_archive 'CCDC 1030934'
_audit_update_record             
;
2014-10-24 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;
_audit_creation_date             2014-08-21
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H34 O5'
_chemical_formula_sum            'C29 H34 O5'
_chemical_formula_weight         462.56
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         O5C29H34
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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.3233(6)
_cell_length_b                   10.2871(8)
_cell_length_c                   26.846(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2574.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28015
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.0240
_cell_measurement_theta_min      2.5330
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             992
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            114218
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.074
_diffrn_reflns_theta_min         2.312
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9470
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -94.00    5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  -38.0000  -30.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   55.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633   38.0000  150.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega  -57.00   29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633   91.0000   16.3376 86

#__ type_ start__ end____ width___ exp.time_
  4 omega  -61.00   60.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633   19.0000  -30.0000 121

#__ type_ start__ end____ width___ exp.time_
  5 omega  -86.00  -11.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  141.0000 -121.0000 75

#__ type_ start__ end____ width___ exp.time_
  6 omega  -76.00   -2.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  125.0000  133.7571 74

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133  178.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
  8 omega  -10.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133   57.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
  9 omega  -91.00  -14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  148.0000    2.9240 77

#__ type_ start__ end____ width___ exp.time_
 10 omega  -91.00  -14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  148.0000  -79.0724 77

#__ type_ start__ end____ width___ exp.time_
 11 omega  -87.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  143.0000 -168.0459 75

#__ type_ start__ end____ width___ exp.time_
 12 omega -108.00  -35.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633 -178.0000 -120.0000 73

#__ type_ start__ end____ width___ exp.time_
 13 omega   11.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133 -141.0000 -178.0000 73

#__ type_ start__ end____ width___ exp.time_
 14 omega  -70.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133    0.0000 -180.0000 177

#__ type_ start__ end____ width___ exp.time_
 15 omega   -6.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133   38.0000  -60.0000 99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0108851000
_diffrn_orient_matrix_UB_12      -0.0335793000
_diffrn_orient_matrix_UB_13      -0.0226460000
_diffrn_orient_matrix_UB_21      0.0295539000
_diffrn_orient_matrix_UB_22      0.0533631000
_diffrn_orient_matrix_UB_23      -0.0131623000
_diffrn_orient_matrix_UB_31      0.0697178000
_diffrn_orient_matrix_UB_32      -0.0279215000
_diffrn_orient_matrix_UB_33      0.0020489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                6450
_reflns_number_total             9266
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 2409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         9266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.7593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1273
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C10(H10), C15(H15), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C20(H20A,H20B),
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.6573(3) 0.3127(3) 0.24982(9) 0.0415(6) Uani 1 1 d . . . . .
H1 H 0.6943 0.3287 0.2174 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4704(2) 0.5830(2) 0.46689(8) 0.0257(4) Uani 1 1 d . . . . .
H5 H 0.4395 0.6530 0.4904 0.031 Uiso 1 1 calc R U . . .
C6 C -0.0037(2) 0.7398(2) 0.34240(8) 0.0303(5) Uani 1 1 d . . . . .
C7 C 0.6387(2) 0.5911(2) 0.46176(8) 0.0283(4) Uani 1 1 d . . . . .
H7 H 0.6765 0.6054 0.4962 0.034 Uiso 1 1 calc R U . . .
C9 C 0.4845(2) 0.8267(2) 0.38934(9) 0.0314(5) Uani 1 1 d . . . . .
H9A H 0.4524 0.9168 0.3829 0.038 Uiso 1 1 calc R U . . .
H9B H 0.5188 0.7904 0.3573 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3536(2) 0.7466(2) 0.40653(8) 0.0270(4) Uani 1 1 d . . . . .
H10 H 0.3143 0.7875 0.4375 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7000(2) 0.7035(2) 0.42935(8) 0.0306(5) Uani 1 1 d . . . . .
H11A H 0.7963 0.7254 0.4424 0.037 Uiso 1 1 calc R U . . .
H11B H 0.7132 0.6699 0.3951 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4310(2) 0.4511(2) 0.49062(9) 0.0290(4) Uani 1 1 d . . . . .
H12A H 0.4448 0.3804 0.4661 0.035 Uiso 1 1 calc R U . . .
H12B H 0.4939 0.4339 0.5196 0.035 Uiso 1 1 calc R U . . .
C13 C 0.4967(2) 0.3741(2) 0.31750(8) 0.0286(4) Uani 1 1 d . . . . .
C14 C 0.2153(3) 0.3270(2) 0.50908(9) 0.0320(5) Uani 1 1 d . . . . .
H14A H 0.1321 0.3302 0.5320 0.038 Uiso 1 1 calc R U . . .
H14B H 0.2853 0.2640 0.5228 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3866(2) 0.6015(2) 0.41785(8) 0.0249(4) Uani 1 1 d . . . . .
H15 H 0.2933 0.5543 0.4209 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0905(3) 0.8436(2) 0.32654(9) 0.0344(5) Uani 1 1 d . . . . .
H16 H -0.0823 0.9259 0.3423 0.041 Uiso 1 1 calc R U . . .
C17 C 0.5455(3) 0.2648(2) 0.34428(9) 0.0345(5) Uani 1 1 d . . . . .
H17 H 0.5070 0.2472 0.3764 0.041 Uiso 1 1 calc R U . . .
C18 C -0.0021(3) 0.3017(3) 0.38873(10) 0.0385(5) Uani 1 1 d . . . . .
H18 H -0.0814 0.3437 0.3734 0.046 Uiso 1 1 calc R U . . .
C19 C 0.2331(3) 0.1752(2) 0.43406(9) 0.0356(5) Uani 1 1 d . . . . .
H19 H 0.3119 0.1325 0.4494 0.043 Uiso 1 1 calc R U . . .
C20 C 0.3901(2) 0.4689(2) 0.34145(8) 0.0299(5) Uani 1 1 d . . . . .
H20A H 0.3514 0.5297 0.3162 0.036 Uiso 1 1 calc R U . . .
H20B H 0.3092 0.4211 0.3568 0.036 Uiso 1 1 calc R U . . .
C21 C 0.6125(2) 0.8317(2) 0.42577(9) 0.0316(5) Uani 1 1 d . . . . .
H21 H 0.6793 0.9006 0.4134 0.038 Uiso 1 1 calc R U . . .
C22 C 0.1656(2) 0.2809(2) 0.45815(9) 0.0311(5) Uani 1 1 d . . . . .
C23 C 0.6504(3) 0.1812(3) 0.32422(10) 0.0411(6) Uani 1 1 d . . . . .
H23 H 0.6828 0.1085 0.3429 0.049 Uiso 1 1 calc R U . . .
C24 C 0.5531(3) 0.3975(3) 0.26998(8) 0.0338(5) Uani 1 1 d . . . . .
H24 H 0.5213 0.4704 0.2513 0.041 Uiso 1 1 calc R U . . .
C25 C 0.0993(2) 0.7545(3) 0.38591(9) 0.0344(5) Uani 1 1 d . . . . .
H25A H 0.0785 0.8361 0.4041 0.041 Uiso 1 1 calc R U . . .
H25B H 0.0871 0.6810 0.4093 0.041 Uiso 1 1 calc R U . . .
C26 C -0.0154(3) 0.6189(3) 0.31780(10) 0.0374(5) Uani 1 1 d . . . . .
H26 H 0.0437 0.5483 0.3278 0.045 Uiso 1 1 calc R U . . .
C27 C 0.0481(2) 0.3439(2) 0.43494(9) 0.0329(5) Uani 1 1 d . . . . .
H27 H 0.0031 0.4154 0.4510 0.040 Uiso 1 1 calc R U . . .
C28 C 0.7067(3) 0.2055(3) 0.27686(10) 0.0429(6) Uani 1 1 d . . . . .
H28 H 0.7778 0.1497 0.2632 0.051 Uiso 1 1 calc R U . . .
C29 C -0.1895(3) 0.8268(3) 0.28748(10) 0.0408(6) Uani 1 1 d . . . . .
H29 H -0.2480 0.8974 0.2771 0.049 Uiso 1 1 calc R U . . .
C30 C -0.2015(3) 0.7056(3) 0.26391(10) 0.0437(6) Uani 1 1 d . . . . .
H30 H -0.2693 0.6937 0.2379 0.052 Uiso 1 1 calc R U . . .
C31 C -0.1139(3) 0.6022(3) 0.27870(11) 0.0432(6) Uani 1 1 d . . . . .
H31 H -0.1210 0.5207 0.2623 0.052 Uiso 1 1 calc R U . . .
C32 C 0.1832(3) 0.1333(3) 0.38739(10) 0.0417(6) Uani 1 1 d . . . . .
H32 H 0.2287 0.0627 0.3710 0.050 Uiso 1 1 calc R U . . .
C33 C 0.0658(3) 0.1961(3) 0.36495(10) 0.0421(6) Uani 1 1 d . . . . .
H33 H 0.0320 0.1671 0.3335 0.051 Uiso 1 1 calc R U . . .
O1 O 0.69969(17) 0.46848(17) 0.44486(6) 0.0342(4) Uani 1 1 d . . . . .
H1A H 0.6708 0.4525 0.4159 0.051 Uiso 1 1 calc R U . . .
O2 O 0.28146(16) 0.45534(16) 0.50654(6) 0.0300(3) Uani 1 1 d . . . . .
O3 O 0.47033(15) 0.53880(16) 0.37901(6) 0.0281(3) Uani 1 1 d . . . . .
O4 O 0.24541(16) 0.75685(17) 0.36743(5) 0.0302(3) Uani 1 1 d . . . . .
O8 O 0.55960(19) 0.87406(18) 0.47381(7) 0.0392(4) Uani 1 1 d . . . . .
H8 H 0.6243 0.9154 0.4888 0.059 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
C1 C24 1.413(4) . ?
C1 C28 1.398(4) . ?
C5 C7 1.577(3) . ?
C5 C12 1.543(3) . ?
C5 C15 1.543(3) . ?
C6 C16 1.406(3) . ?
C6 C25 1.520(3) . ?
C6 C26 1.413(3) . ?
C7 C11 1.556(3) . ?
C7 O1 1.456(3) . ?
C9 C10 1.543(3) . ?
C9 C21 1.544(3) . ?
C10 C15 1.554(3) . ?
C10 O4 1.459(3) . ?
C11 C21 1.554(3) . ?
C12 O2 1.459(3) . ?
C13 C17 1.410(3) . ?
C13 C20 1.534(3) . ?
C13 C24 1.401(3) . ?
C14 C22 1.519(3) . ?
C14 O2 1.459(3) . ?
C15 O3 1.453(2) . ?
C16 C29 1.407(4) . ?
C17 C23 1.409(3) . ?
C18 C27 1.395(4) . ?
C18 C33 1.410(4) . ?
C19 C22 1.413(3) . ?
C19 C32 1.404(4) . ?
C20 O3 1.447(3) . ?
C21 O8 1.448(3) . ?
C22 C27 1.417(3) . ?
C23 C28 1.398(4) . ?
C25 O4 1.450(3) . ?
C26 C31 1.405(4) . ?
C29 C30 1.403(4) . ?
C30 C31 1.398(4) . ?
C32 C33 1.406(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
C28 C1 C24 121.0(2) . . ?
C12 C5 C7 108.61(18) . . ?
C15 C5 C7 115.01(17) . . ?
C15 C5 C12 109.90(17) . . ?
C16 C6 C25 121.4(2) . . ?
C16 C6 C26 118.9(2) . . ?
C26 C6 C25 119.7(2) . . ?
C11 C7 C5 116.95(18) . . ?
O1 C7 C5 111.72(18) . . ?
O1 C7 C11 109.04(17) . . ?
C10 C9 C21 116.11(18) . . ?
C9 C10 C15 114.46(18) . . ?
O4 C10 C9 107.05(17) . . ?
O4 C10 C15 110.30(17) . . ?
C21 C11 C7 118.23(18) . . ?
O2 C12 C5 108.80(17) . . ?
C17 C13 C20 120.2(2) . . ?
C24 C13 C17 118.7(2) . . ?
C24 C13 C20 121.0(2) . . ?
O2 C14 C22 111.67(18) . . ?
C5 C15 C10 112.70(17) . . ?
O3 C15 C5 106.58(16) . . ?
O3 C15 C10 113.11(17) . . ?
C6 C16 C29 120.6(2) . . ?
C23 C17 C13 121.0(2) . . ?
C27 C18 C33 119.4(2) . . ?
C32 C19 C22 119.8(2) . . ?
O3 C20 C13 105.84(17) . . ?
C9 C21 C11 114.59(19) . . ?
O8 C21 C9 108.14(18) . . ?
O8 C21 C11 112.27(19) . . ?
C19 C22 C14 121.1(2) . . ?
C19 C22 C27 119.7(2) . . ?
C27 C22 C14 119.2(2) . . ?
C28 C23 C17 120.0(2) . . ?
C13 C24 C1 120.0(2) . . ?
O4 C25 C6 109.43(18) . . ?
C31 C26 C6 120.4(2) . . ?
C18 C27 C22 120.5(2) . . ?
C23 C28 C1 119.3(2) . . ?
C30 C29 C16 119.9(2) . . ?
C31 C30 C29 120.1(2) . . ?
C30 C31 C26 120.1(3) . . ?
C19 C32 C33 120.0(2) . . ?
C32 C33 C18 120.6(2) . . ?
C14 O2 C12 113.02(17) . . ?
C20 O3 C15 116.28(15) . . ?
C25 O4 C10 113.69(16) . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
