# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_chenhua-02-110
_database_code_depnum_ccdc_archive 'CCDC 1030994'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;
_audit_creation_date             2014-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H38 O3'
_chemical_formula_sum            'C27 H38 O3'
_chemical_formula_weight         410.57
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      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                   6.09236(14)
_cell_length_b                   12.7347(3)
_cell_length_c                   30.1234(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2337.10(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3785
_cell_measurement_temperature    110.01(16)
_cell_measurement_theta_max      72.5390
_cell_measurement_theta_min      4.5370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            8339
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         4.547
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.01(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00  104.00   1.0000    1.3600
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   90.00   1.0000    1.3600
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000 -180.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   63.00   1.0000    1.3600
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   90.00   1.0000    1.3600
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
  5 omega  -31.00   63.00   1.0000    1.3600
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   91.00   1.0000    5.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   91.00   1.0000    5.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   98.00   1.0000    5.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  109.00   1.0000    5.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00  109.00   1.0000    5.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00  109.00   1.0000    5.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1752151000
_diffrn_orient_matrix_UB_12      -0.0366781000
_diffrn_orient_matrix_UB_13      0.0334441000
_diffrn_orient_matrix_UB_21      0.1056624000
_diffrn_orient_matrix_UB_22      -0.0692629000
_diffrn_orient_matrix_UB_23      -0.0361224000
_diffrn_orient_matrix_UB_31      0.1487379000
_diffrn_orient_matrix_UB_32      0.0921425000
_diffrn_orient_matrix_UB_33      -0.0138266000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.618
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.864
_reflns_number_gt                3712
_reflns_number_total             3936
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1371 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.26(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.058
_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)+(0.0958P)²+0.2775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1404
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B),
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B),
  C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C30(H30)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
2.e :
 C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.1544(3) -0.39815(14) -0.41250(6) 0.0216(4) Uani 1 1 d . . . . .
O2 O 0.0620(3) -0.26047(15) -0.42865(7) 0.0283(5) Uani 1 1 d . . . . .
C3 C 0.0430(5) -0.7728(2) -0.34197(9) 0.0199(6) Uani 1 1 d . . . . .
H3 H 0.1751 -0.7808 -0.3602 0.024 Uiso 1 1 calc R . . . .
C4 C 0.1247(4) -0.5813(2) -0.33857(9) 0.0190(5) Uani 1 1 d . . . . .
H4 H 0.2510 -0.5968 -0.3576 0.023 Uiso 1 1 calc R . . . .
C5 C 0.0856(4) -0.6796(2) -0.31042(9) 0.0201(6) Uani 1 1 d . . . . .
H5 H -0.0446 -0.6686 -0.2919 0.024 Uiso 1 1 calc R . . . .
C6 C 0.1953(5) -0.47736(19) -0.42550(9) 0.0213(6) Uani 1 1 d . . . . .
C7 C 0.1939(5) -0.8953(2) -0.28406(9) 0.0260(6) Uani 1 1 d . . . . .
C8 C -0.0660(4) -0.5541(2) -0.36976(9) 0.0199(6) Uani 1 1 d . . . . .
C9 C 0.1756(4) -0.4767(2) -0.31552(9) 0.0206(5) Uani 1 1 d . . . . .
H9A H 0.3274 -0.4742 -0.3058 0.025 Uiso 1 1 calc R . . . .
H9B H 0.0808 -0.4662 -0.2900 0.025 Uiso 1 1 calc R . . . .
C10 C -0.1161(5) -0.3011(2) -0.42901(10) 0.0231(6) Uani 1 1 d . . . . .
C11 C 0.0098(5) -0.8783(2) -0.31713(9) 0.0249(6) Uani 1 1 d . . . . .
H11 H -0.1287 -0.8743 -0.3007 0.030 Uiso 1 1 calc R . . . .
C12 C -0.1472(5) -0.7494(2) -0.37399(9) 0.0236(6) Uani 1 1 d . . . . .
H12A H -0.2826 -0.7444 -0.3572 0.028 Uiso 1 1 calc R . . . .
H12B H -0.1620 -0.8074 -0.3947 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2812(5) -0.7026(2) -0.28056(9) 0.0236(6) Uani 1 1 d . . . . .
H13A H 0.3020 -0.6447 -0.2601 0.028 Uiso 1 1 calc R . . . .
H13B H 0.4127 -0.7088 -0.2985 0.028 Uiso 1 1 calc R . . . .
C14 C 0.3356(5) -0.4971(2) -0.45154(10) 0.0260(6) Uani 1 1 d . . . . .
H14 H 0.4455 -0.5126 -0.4719 0.031 Uiso 1 1 calc R . . . .
C15 C -0.1135(4) -0.6471(2) -0.40029(9) 0.0212(6) Uani 1 1 d . . . . .
H15A H 0.0080 -0.6561 -0.4208 0.025 Uiso 1 1 calc R . . . .
H15B H -0.2442 -0.6325 -0.4176 0.025 Uiso 1 1 calc R . . . .
C16 C -0.3311(5) -0.1358(2) -0.43404(11) 0.0297(7) Uani 1 1 d . . . . .
H16A H -0.3429 -0.1311 -0.4020 0.036 Uiso 1 1 calc R . . . .
H16B H -0.1943 -0.1026 -0.4426 0.036 Uiso 1 1 calc R . . . .
C17 C 0.0273(5) -0.4533(2) -0.39182(9) 0.0203(6) Uani 1 1 d . . . . .
C18 C 0.1306(5) -0.3928(2) -0.35181(9) 0.0230(6) Uani 1 1 d . . . . .
H18A H 0.2661 -0.3587 -0.3607 0.028 Uiso 1 1 calc R . . . .
H18B H 0.0298 -0.3398 -0.3409 0.028 Uiso 1 1 calc R . . . .
C19 C -0.3223(5) -0.2519(2) -0.44725(10) 0.0266(6) Uani 1 1 d . . . . .
H19A H -0.4498 -0.2882 -0.4356 0.032 Uiso 1 1 calc R . . . .
H19B H -0.3240 -0.2582 -0.4793 0.032 Uiso 1 1 calc R . . . .
C20 C -0.6721(5) 0.1103(2) -0.46720(10) 0.0275(6) Uani 1 1 d . . . . .
H20A H -0.8160 0.0930 -0.4555 0.033 Uiso 1 1 calc R . . . .
H20B H -0.6728 0.0959 -0.4988 0.033 Uiso 1 1 calc R . . . .
C21 C -0.2758(5) -0.5243(2) -0.34439(10) 0.0234(6) Uani 1 1 d . . . . .
H21A H -0.3184 -0.5813 -0.3254 0.035 Uiso 1 1 calc GR . . . .
H21B H -0.3915 -0.5100 -0.3652 0.035 Uiso 1 1 calc GR . . . .
H21C H -0.2487 -0.4629 -0.3267 0.035 Uiso 1 1 calc GR . . . .
C22 C -0.5204(5) -0.0752(2) -0.45477(10) 0.0251(6) Uani 1 1 d . . . . .
H22A H -0.6583 -0.1015 -0.4431 0.030 Uiso 1 1 calc R . . . .
H22B H -0.5204 -0.0861 -0.4866 0.030 Uiso 1 1 calc R . . . .
C23 C 0.2462(5) -0.8044(2) -0.25432(9) 0.0262(6) Uani 1 1 d . . . . .
H23A H 0.3780 -0.8201 -0.2375 0.031 Uiso 1 1 calc R . . . .
H23B H 0.1269 -0.7945 -0.2334 0.031 Uiso 1 1 calc R . . . .
C24 C -0.6262(6) 0.2270(2) -0.45962(11) 0.0332(7) Uani 1 1 d . . . . .
H24A H -0.7406 0.2680 -0.4730 0.050 Uiso 1 1 calc GR . . . .
H24B H -0.4878 0.2451 -0.4728 0.050 Uiso 1 1 calc GR . . . .
H24C H -0.6212 0.2410 -0.4283 0.050 Uiso 1 1 calc GR . . . .
C25 C -0.0064(6) -0.9699(2) -0.35012(10) 0.0310(7) Uani 1 1 d . . . . .
H25A H -0.1490 -0.9677 -0.3644 0.037 Uiso 1 1 calc R . . . .
H25B H 0.1041 -0.9606 -0.3730 0.037 Uiso 1 1 calc R . . . .
C26 C 0.2330(9) -1.0839(3) -0.30334(13) 0.0560(13) Uani 1 1 d . . . . .
C27 C -0.5007(5) 0.0422(2) -0.44481(10) 0.0263(6) Uani 1 1 d . . . . .
H27A H -0.5111 0.0524 -0.4130 0.032 Uiso 1 1 calc R . . . .
H27B H -0.3564 0.0659 -0.4541 0.032 Uiso 1 1 calc R . . . .
C28 C 0.0245(8) -1.0776(2) -0.32882(12) 0.0427(9) Uani 1 1 d . . . . .
H28A H -0.0978 -1.0918 -0.3091 0.051 Uiso 1 1 calc R . . . .
H28B H 0.0247 -1.1310 -0.3518 0.051 Uiso 1 1 calc R . . . .
C30 C 0.3014(6) -0.9864(3) -0.28077(11) 0.0374(8) Uani 1 1 d . . . . .
H30 H 0.4268 -0.9886 -0.2632 0.045 Uiso 1 1 calc R . . . .
O3 O 0.3315(9) -1.1651(3) -0.29881(15) 0.118(2) 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 C10 1.352(3) . ?
O1 C17 1.451(3) . ?
O2 C10 1.202(4) . ?
C3 H3 0.9800 . ?
C3 C5 1.542(4) . ?
C3 C11 1.551(4) . ?
C3 C12 1.537(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.531(4) . ?
C4 C8 1.534(4) . ?
C4 C9 1.533(3) . ?
C5 H5 0.9800 . ?
C5 C13 1.521(4) . ?
C6 C14 1.187(4) . ?
C6 C17 1.473(4) . ?
C7 C11 1.516(4) . ?
C7 C23 1.498(4) . ?
C7 C30 1.337(4) . ?
C8 C15 1.527(4) . ?
C8 C17 1.553(3) . ?
C8 C21 1.537(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C18 1.553(4) . ?
C10 C19 1.507(4) . ?
C11 H11 0.9800 . ?
C11 C25 1.536(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C15 1.539(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C23 1.534(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C19 1.533(4) . ?
C16 C22 1.522(4) . ?
C17 C18 1.563(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C24 1.529(4) . ?
C20 C27 1.516(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C27 1.530(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C28 1.526(4) . ?
C26 C28 1.486(6) . ?
C26 C30 1.475(5) . ?
C26 O3 1.204(5) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C30 H30 0.9300 . ?

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
C10 O1 C17 117.9(2) . . ?
C5 C3 H3 106.7 . . ?
C5 C3 C11 113.0(2) . . ?
C11 C3 H3 106.7 . . ?
C12 C3 H3 106.7 . . ?
C12 C3 C5 111.4(2) . . ?
C12 C3 C11 111.8(2) . . ?
C5 C4 H4 106.3 . . ?
C5 C4 C8 114.0(2) . . ?
C5 C4 C9 119.4(2) . . ?
C8 C4 H4 106.3 . . ?
C9 C4 H4 106.3 . . ?
C9 C4 C8 103.6(2) . . ?
C3 C5 H5 108.9 . . ?
C4 C5 C3 108.3(2) . . ?
C4 C5 H5 108.9 . . ?
C13 C5 C3 110.4(2) . . ?
C13 C5 C4 111.3(2) . . ?
C13 C5 H5 108.9 . . ?
C14 C6 C17 177.8(3) . . ?
C23 C7 C11 116.1(2) . . ?
C30 C7 C11 122.4(3) . . ?
C30 C7 C23 121.5(3) . . ?
C4 C8 C17 99.9(2) . . ?
C4 C8 C21 112.4(2) . . ?
C15 C8 C4 109.7(2) . . ?
C15 C8 C17 116.9(2) . . ?
C15 C8 C21 109.5(2) . . ?
C21 C8 C17 108.2(2) . . ?
C4 C9 H9A 110.9 . . ?
C4 C9 H9B 110.9 . . ?
C4 C9 C18 104.1(2) . . ?
H9A C9 H9B 109.0 . . ?
C18 C9 H9A 110.9 . . ?
C18 C9 H9B 110.9 . . ?
O1 C10 C19 111.7(2) . . ?
O2 C10 O1 123.1(3) . . ?
O2 C10 C19 125.2(3) . . ?
C3 C11 H11 108.2 . . ?
C7 C11 C3 110.1(2) . . ?
C7 C11 H11 108.2 . . ?
C7 C11 C25 111.3(2) . . ?
C25 C11 C3 110.8(2) . . ?
C25 C11 H11 108.2 . . ?
C3 C12 H12A 109.0 . . ?
C3 C12 H12B 109.0 . . ?
C3 C12 C15 112.7(2) . . ?
H12A C12 H12B 107.8 . . ?
C15 C12 H12A 109.0 . . ?
C15 C12 H12B 109.0 . . ?
C5 C13 H13A 109.4 . . ?
C5 C13 H13B 109.4 . . ?
C5 C13 C23 111.0(2) . . ?
H13A C13 H13B 108.0 . . ?
C23 C13 H13A 109.4 . . ?
C23 C13 H13B 109.4 . . ?
C6 C14 H14 180.0 . . ?
C8 C15 C12 111.8(2) . . ?
C8 C15 H15A 109.2 . . ?
C8 C15 H15B 109.2 . . ?
C12 C15 H15A 109.2 . . ?
C12 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
H16A C16 H16B 107.6 . . ?
C19 C16 H16A 108.7 . . ?
C19 C16 H16B 108.7 . . ?
C22 C16 H16A 108.7 . . ?
C22 C16 H16B 108.7 . . ?
C22 C16 C19 114.1(2) . . ?
O1 C17 C6 109.6(2) . . ?
O1 C17 C8 107.7(2) . . ?
O1 C17 C18 113.5(2) . . ?
C6 C17 C8 112.2(2) . . ?
C6 C17 C18 110.7(2) . . ?
C8 C17 C18 103.0(2) . . ?
C9 C18 C17 105.9(2) . . ?
C9 C18 H18A 110.6 . . ?
C9 C18 H18B 110.6 . . ?
C17 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
H18A C18 H18B 108.7 . . ?
C10 C19 C16 109.6(2) . . ?
C10 C19 H19A 109.7 . . ?
C10 C19 H19B 109.7 . . ?
C16 C19 H19A 109.7 . . ?
C16 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
H20A C20 H20B 108.0 . . ?
C24 C20 H20A 109.4 . . ?
C24 C20 H20B 109.4 . . ?
C27 C20 H20A 109.4 . . ?
C27 C20 H20B 109.4 . . ?
C27 C20 C24 111.3(3) . . ?
C8 C21 H21A 109.5 . . ?
C8 C21 H21B 109.5 . . ?
C8 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 C27 110.8(2) . . ?
H22A C22 H22B 108.1 . . ?
C27 C22 H22A 109.5 . . ?
C27 C22 H22B 109.5 . . ?
C7 C23 C13 112.0(2) . . ?
C7 C23 H23A 109.2 . . ?
C7 C23 H23B 109.2 . . ?
C13 C23 H23A 109.2 . . ?
C13 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C25 H25A 108.8 . . ?
C11 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C28 C25 C11 113.8(2) . . ?
C28 C25 H25A 108.8 . . ?
C28 C25 H25B 108.8 . . ?
C30 C26 C28 115.8(3) . . ?
O3 C26 C28 122.1(4) . . ?
O3 C26 C30 122.0(4) . . ?
C20 C27 C22 114.7(2) . . ?
C20 C27 H27A 108.6 . . ?
C20 C27 H27B 108.6 . . ?
C22 C27 H27A 108.6 . . ?
C22 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C25 C28 H28A 109.3 . . ?
C25 C28 H28B 109.3 . . ?
C26 C28 C25 111.8(3) . . ?
C26 C28 H28A 109.3 . . ?
C26 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
C7 C30 C26 123.9(3) . . ?
C7 C30 H30 118.0 . . ?
C26 C30 H30 118.0 . . ?

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
O1 C10 C19 C16 138.6(2) . . . . ?
O1 C17 C18 C9 138.5(2) . . . . ?
O2 C10 C19 C16 -41.1(4) . . . . ?
C3 C5 C13 C23 -56.6(3) . . . . ?
C3 C11 C25 C28 164.0(3) . . . . ?
C3 C12 C15 C8 -53.1(3) . . . . ?
C4 C5 C13 C23 -176.9(2) . . . . ?
C4 C8 C15 C12 52.6(3) . . . . ?
C4 C8 C17 O1 -163.0(2) . . . . ?
C4 C8 C17 C6 76.3(3) . . . . ?
C4 C8 C17 C18 -42.8(2) . . . . ?
C4 C9 C18 C17 7.1(3) . . . . ?
C5 C3 C11 C7 -50.1(3) . . . . ?
C5 C3 C11 C25 -173.7(2) . . . . ?
C5 C3 C12 C15 54.6(3) . . . . ?
C5 C4 C8 C15 -57.1(3) . . . . ?
C5 C4 C8 C17 179.5(2) . . . . ?
C5 C4 C8 C21 65.0(3) . . . . ?
C5 C4 C9 C18 -162.5(2) . . . . ?
C5 C13 C23 C7 54.2(3) . . . . ?
C6 C17 C18 C9 -97.8(2) . . . . ?
C7 C11 C25 C28 41.1(4) . . . . ?
C8 C4 C5 C3 58.1(3) . . . . ?
C8 C4 C5 C13 179.6(2) . . . . ?
C8 C4 C9 C18 -34.5(3) . . . . ?
C8 C17 C18 C9 22.3(3) . . . . ?
C9 C4 C5 C3 -178.9(2) . . . . ?
C9 C4 C5 C13 -57.4(3) . . . . ?
C9 C4 C8 C15 171.6(2) . . . . ?
C9 C4 C8 C17 48.2(2) . . . . ?
C9 C4 C8 C21 -66.3(3) . . . . ?
C10 O1 C17 C6 -65.9(3) . . . . ?
C10 O1 C17 C8 171.8(2) . . . . ?
C10 O1 C17 C18 58.5(3) . . . . ?
C11 C3 C5 C4 177.8(2) . . . . ?
C11 C3 C5 C13 55.7(3) . . . . ?
C11 C3 C12 C15 -177.9(2) . . . . ?
C11 C7 C23 C13 -51.2(3) . . . . ?
C11 C7 C30 C26 -9.8(6) . . . . ?
C11 C25 C28 C26 -54.2(4) . . . . ?
C12 C3 C5 C4 -55.3(3) . . . . ?
C12 C3 C5 C13 -177.4(2) . . . . ?
C12 C3 C11 C7 -176.8(2) . . . . ?
C12 C3 C11 C25 59.6(3) . . . . ?
C15 C8 C17 O1 78.8(3) . . . . ?
C15 C8 C17 C6 -41.9(3) . . . . ?
C15 C8 C17 C18 -161.0(2) . . . . ?
C16 C22 C27 C20 175.3(3) . . . . ?
C17 O1 C10 O2 2.6(4) . . . . ?
C17 O1 C10 C19 -177.1(2) . . . . ?
C17 C8 C15 C12 165.3(2) . . . . ?
C19 C16 C22 C27 -172.7(3) . . . . ?
C21 C8 C15 C12 -71.2(3) . . . . ?
C21 C8 C17 O1 -45.4(3) . . . . ?
C21 C8 C17 C6 -166.0(2) . . . . ?
C21 C8 C17 C18 74.9(2) . . . . ?
C22 C16 C19 C10 173.9(3) . . . . ?
C23 C7 C11 C3 48.4(3) . . . . ?
C23 C7 C11 C25 171.6(2) . . . . ?
C23 C7 C30 C26 168.9(4) . . . . ?
C24 C20 C27 C22 -173.9(3) . . . . ?
C28 C26 C30 C7 -3.4(6) . . . . ?
C30 C7 C11 C3 -132.9(3) . . . . ?
C30 C7 C11 C25 -9.6(4) . . . . ?
C30 C7 C23 C13 130.1(3) . . . . ?
C30 C26 C28 C25 34.6(5) . . . . ?
O3 C26 C28 C25 -150.5(5) . . . . ?
O3 C26 C30 C7 -178.4(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.154 0.274 0.157 11.0 0.3 ?
2 0.154 0.774 0.343 11.0 0.4 ?
3 0.346 0.226 0.843 11.0 0.3 ?
4 0.654 0.726 0.657 11.0 0.4 ?

_olex2_submission_special_instructions 'No special instructions were received'
