# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_15a
_database_code_depnum_ccdc_archive 'CCDC 1439395'
_audit_update_record             
;
2015-11-28 deposited with the CCDC.
2016-01-15 downloaded from the CCDC.
;
_audit_creation_date             2015-03-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.03 svn.r3071 for OlexSys, GUI svn.r4932)
;
_chemical_name_common            ?
_chemical_name_systematic        
(4bS,4b1S,6R,7S,7aR,12bS)-7-(benzyloxy)-6-((benzyloxy)methyl)-4b1,6,7,7a,12b,13-hexahydro-4bH-benzo[h]chromeno[2,3,4-de]chromene
_chemical_formula_moiety         '0.5(C33 H31 N O4)'
_chemical_formula_sum            'C16.50 H15.50 N0.50 O2'
_chemical_formula_weight         252.79
_chemical_absolute_configuration ?
_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 0.0033 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'

_cell_length_a                   9.1243(3)
_cell_length_b                   11.1741(3)
_cell_length_c                   13.3627(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.9468(13)
_cell_angle_gamma                90
_cell_volume                     1322.24(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.276
_cell_measurement_theta_min      2.935
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plates
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.626
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23644
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         2.935
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5480
_reflns_number_total             6519
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 2214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.087(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         6519
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.097
_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)+(0.0516P)²+0.1540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1), C2(H2), C3(H3), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C30(H30), C31(H31),
  C32(H32), C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O -0.72722(18) -1.03986(16) -0.16965(14) 0.0369(4) Uani 1 1 d . . . . .
O2 O -0.39114(19) -0.80101(14) -0.03817(13) 0.0314(4) Uani 1 1 d . . . . .
O3 O -0.2981(2) -0.76221(16) -0.22218(14) 0.0377(4) Uani 1 1 d . . . . .
O4 O -0.43671(19) -1.05376(15) -0.21547(12) 0.0330(4) Uani 1 1 d . . . . .
N1 N -0.6194(2) -1.03368(18) 0.11615(16) 0.0337(5) Uani 1 1 d . . . . .
H1A H -0.6603 -1.0926 0.1407 0.040 Uiso 1 1 calc R . . . .
C1 C -0.2282(3) -1.0772(3) 0.2626(2) 0.0404(6) Uani 1 1 d . . . . .
H1 H -0.1729 -1.1298 0.3112 0.049 Uiso 1 1 calc R . . . .
C2 C -0.1563(3) -0.9813(3) 0.2281(2) 0.0429(7) Uani 1 1 d . . . . .
H2 H -0.0535 -0.9684 0.2546 0.051 Uiso 1 1 calc R . . . .
C3 C -0.2388(3) -0.9058(3) 0.15447(18) 0.0381(6) Uani 1 1 d . . . . .
H3 H -0.1903 -0.8422 0.1311 0.046 Uiso 1 1 calc R . . . .
C4 C -0.3928(3) -0.9220(2) 0.11405(17) 0.0292(5) Uani 1 1 d . . . . .
C5 C -0.4669(3) -1.0163(2) 0.15072(18) 0.0286(5) Uani 1 1 d . . . . .
C6 C -0.3810(3) -1.0944(2) 0.22499(19) 0.0347(5) Uani 1 1 d . . . . .
H6 H -0.4282 -1.1583 0.2489 0.042 Uiso 1 1 calc R . . . .
C7 C -0.4808(3) -0.84051(19) 0.03038(18) 0.0291(5) Uani 1 1 d . . . . .
H7 H -0.5099 -0.7695 0.0640 0.035 Uiso 1 1 calc R . . . .
C8 C -0.6255(3) -0.89961(19) -0.03114(18) 0.0278(5) Uani 1 1 d . . . . .
H8 H -0.6883 -0.8384 -0.0736 0.033 Uiso 1 1 calc R . . . .
C9 C -0.7158(3) -0.9564(2) 0.03932(19) 0.0318(5) Uani 1 1 d . . . . .
H9 H -0.7575 -0.8928 0.0748 0.038 Uiso 1 1 calc R . . . .
C11 C -0.8442(3) -1.0293(2) -0.0248(2) 0.0354(6) Uani 1 1 d . . . . .
C12 C -0.9664(3) -1.0625(3) 0.0151(3) 0.0472(7) Uani 1 1 d . . . . .
H12 H -0.9702 -1.0366 0.0805 0.057 Uiso 1 1 calc R . . . .
C13 C -1.0817(3) -1.1330(3) -0.0409(3) 0.0562(9) Uani 1 1 d . . . . .
H13 H -1.1604 -1.1568 -0.0123 0.067 Uiso 1 1 calc R . . . .
C14 C -1.0794(3) -1.1681(3) -0.1402(3) 0.0560(9) Uani 1 1 d . . . . .
H14 H -1.1580 -1.2139 -0.1789 0.067 Uiso 1 1 calc R . . . .
C15 C -0.9609(3) -1.1350(2) -0.1813(3) 0.0463(7) Uani 1 1 d . . . . .
H15 H -0.9601 -1.1575 -0.2482 0.056 Uiso 1 1 calc R . . . .
C16 C -0.8422(3) -1.0680(2) -0.1230(2) 0.0364(6) Uani 1 1 d . . . . .
C17 C -0.5907(3) -0.9965(2) -0.10175(18) 0.0273(5) Uani 1 1 d . . . . .
H17 H -0.5418 -1.0634 -0.0590 0.033 Uiso 1 1 calc R . . . .
C18 C -0.4865(3) -0.9537(2) -0.16654(17) 0.0279(5) Uani 1 1 d . . . . .
H18 H -0.5382 -0.8956 -0.2180 0.034 Uiso 1 1 calc R . . . .
C19 C -0.3476(3) -0.89724(19) -0.09534(17) 0.0268(5) Uani 1 1 d . . . . .
H19 H -0.2988 -0.9585 -0.0460 0.032 Uiso 1 1 calc R . . . .
C20 C -0.2317(3) -0.8510(2) -0.14978(18) 0.0305(5) Uani 1 1 d . . . . .
H20A H -0.1466 -0.8173 -0.0998 0.037 Uiso 1 1 calc R . . . .
H20B H -0.1950 -0.9164 -0.1849 0.037 Uiso 1 1 calc R . . . .
C21 C -0.1904(4) -0.7071(2) -0.2702(2) 0.0424(6) Uani 1 1 d . . . . .
H21A H -0.1023 -0.6839 -0.2172 0.051 Uiso 1 1 calc R . . . .
H21B H -0.2344 -0.6348 -0.3052 0.051 Uiso 1 1 calc R . . . .
C22 C -0.1408(3) -0.7869(2) -0.34685(19) 0.0332(5) Uani 1 1 d . . . . .
C23 C -0.0086(3) -0.8533(2) -0.31764(19) 0.0367(6) Uani 1 1 d . . . . .
H23 H 0.0499 -0.8481 -0.2504 0.044 Uiso 1 1 calc R . . . .
C24 C 0.0367(3) -0.9270(3) -0.3878(2) 0.0410(6) Uani 1 1 d . . . . .
H24 H 0.1252 -0.9714 -0.3673 0.049 Uiso 1 1 calc R . . . .
C25 C -0.0484(3) -0.9351(3) -0.4875(2) 0.0453(7) Uani 1 1 d . . . . .
H25 H -0.0173 -0.9843 -0.5346 0.054 Uiso 1 1 calc R . . . .
C26 C -0.1788(3) -0.8703(3) -0.5173(2) 0.0512(8) Uani 1 1 d . . . . .
H26 H -0.2366 -0.8759 -0.5848 0.061 Uiso 1 1 calc R . . . .
C27 C -0.2255(3) -0.7963(3) -0.4476(2) 0.0458(7) Uani 1 1 d . . . . .
H27 H -0.3143 -0.7526 -0.4686 0.055 Uiso 1 1 calc R . . . .
C28 C -0.4868(4) -1.0553(3) -0.3240(2) 0.0475(7) Uani 1 1 d . . . . .
C29 C -0.4261(3) -1.1667(2) -0.36241(18) 0.0346(5) Uani 1 1 d . . . . .
C30 C -0.3410(4) -1.1601(3) -0.4346(3) 0.0592(9) Uani 1 1 d . . . . .
H30 H -0.3214 -1.0859 -0.4601 0.071 Uiso 1 1 calc R . . . .
C31 C -0.2847(5) -1.2626(4) -0.4695(3) 0.0785(13) Uani 1 1 d . . . . .
H31 H -0.2270 -1.2570 -0.5179 0.094 Uiso 1 1 calc R . . . .
C32 C -0.3136(4) -1.3729(3) -0.4328(3) 0.0581(9) Uani 1 1 d . . . . .
H32 H -0.2757 -1.4418 -0.4565 0.070 Uiso 1 1 calc R . . . .
C33 C -0.3982(3) -1.3808(3) -0.3613(2) 0.0433(6) Uani 1 1 d . . . . .
H33 H -0.4180 -1.4552 -0.3362 0.052 Uiso 1 1 calc R . . . .
C34 C -0.4541(3) -1.2782(3) -0.3266(2) 0.0380(6) Uani 1 1 d . . . . .
H34 H -0.5118 -1.2843 -0.2781 0.046 Uiso 1 1 calc R . . . .
H28A H -0.603(4) -1.061(4) -0.341(3) 0.069(11) Uiso 1 1 d . . . . .
H28B H -0.459(5) -0.980(4) -0.359(3) 0.080(13) Uiso 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 C16 1.380(3) . ?
O1 C17 1.437(3) . ?
O2 C7 1.437(3) . ?
O2 C19 1.430(3) . ?
O3 C20 1.416(3) . ?
O3 C21 1.436(3) . ?
O4 C18 1.424(3) . ?
O4 C28 1.412(3) . ?
N1 H1A 0.8600 . ?
N1 C5 1.371(3) . ?
N1 C9 1.462(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.392(4) . ?
C1 C6 1.377(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(3) . ?
C4 C5 1.402(3) . ?
C4 C7 1.514(3) . ?
C5 C6 1.409(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.527(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.530(3) . ?
C8 C17 1.519(3) . ?
C9 H9 0.9800 . ?
C9 C11 1.512(4) . ?
C11 C12 1.397(4) . ?
C11 C16 1.386(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(4) . ?
C17 H17 0.9800 . ?
C17 C18 1.510(3) . ?
C18 H18 0.9800 . ?
C18 C19 1.526(3) . ?
C19 H19 0.9800 . ?
C19 C20 1.512(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.507(4) . ?
C22 C23 1.389(4) . ?
C22 C27 1.385(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.374(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.368(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.387(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.502(4) . ?
C28 H28A 1.03(4) . ?
C28 H28B 1.03(5) . ?
C29 C30 1.378(4) . ?
C29 C34 1.381(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.381(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.375(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.369(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.380(4) . ?
C34 H34 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
C16 O1 C17 115.42(19) . . ?
C19 O2 C7 112.57(16) . . ?
C20 O3 C21 112.32(19) . . ?
C28 O4 C18 114.90(18) . . ?
C5 N1 H1A 118.6 . . ?
C5 N1 C9 122.87(19) . . ?
C9 N1 H1A 118.6 . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C6 C1 C2 120.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.7(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 C7 121.0(2) . . ?
C5 C4 C7 119.7(2) . . ?
N1 C5 C4 121.6(2) . . ?
N1 C5 C6 119.8(2) . . ?
C4 C5 C6 118.6(2) . . ?
C1 C6 C5 120.8(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O2 C7 C4 111.9(2) . . ?
O2 C7 H7 107.6 . . ?
O2 C7 C8 109.93(18) . . ?
C4 C7 H7 107.6 . . ?
C4 C7 C8 111.91(18) . . ?
C8 C7 H7 107.6 . . ?
C7 C8 H8 108.6 . . ?
C7 C8 C9 111.84(19) . . ?
C9 C8 H8 108.6 . . ?
C17 C8 C7 111.09(18) . . ?
C17 C8 H8 108.6 . . ?
C17 C8 C9 108.09(18) . . ?
N1 C9 C8 110.79(18) . . ?
N1 C9 H9 109.0 . . ?
N1 C9 C11 109.39(19) . . ?
C8 C9 H9 109.0 . . ?
C11 C9 C8 109.5(2) . . ?
C11 C9 H9 109.0 . . ?
C12 C11 C9 120.5(3) . . ?
C16 C11 C9 121.3(2) . . ?
C16 C11 C12 118.1(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
O1 C16 C11 122.8(2) . . ?
O1 C16 C15 116.3(3) . . ?
C11 C16 C15 120.9(3) . . ?
O1 C17 C8 110.69(18) . . ?
O1 C17 H17 108.4 . . ?
O1 C17 C18 108.33(18) . . ?
C8 C17 H17 108.4 . . ?
C18 C17 C8 112.61(18) . . ?
C18 C17 H17 108.4 . . ?
O4 C18 C17 109.20(18) . . ?
O4 C18 H18 110.5 . . ?
O4 C18 C19 107.56(17) . . ?
C17 C18 H18 110.5 . . ?
C17 C18 C19 108.47(17) . . ?
C19 C18 H18 110.5 . . ?
O2 C19 C18 110.36(17) . . ?
O2 C19 H19 107.8 . . ?
O2 C19 C20 108.47(18) . . ?
C18 C19 H19 107.8 . . ?
C20 C19 C18 114.43(18) . . ?
C20 C19 H19 107.8 . . ?
O3 C20 C19 109.54(19) . . ?
O3 C20 H20A 109.8 . . ?
O3 C20 H20B 109.8 . . ?
C19 C20 H20A 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
O3 C21 H21A 108.9 . . ?
O3 C21 H21B 108.9 . . ?
O3 C21 C22 113.6(2) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C23 C22 C21 120.5(2) . . ?
C27 C22 C21 121.1(2) . . ?
C27 C22 C23 118.4(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 120.6(3) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
O4 C28 C29 107.8(2) . . ?
O4 C28 H28A 107(2) . . ?
O4 C28 H28B 114(2) . . ?
C29 C28 H28A 108(2) . . ?
C29 C28 H28B 112(2) . . ?
H28A C28 H28B 108(3) . . ?
C30 C29 C28 120.7(3) . . ?
C30 C29 C34 118.3(3) . . ?
C34 C29 C28 121.0(2) . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.6(3) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 120.2 . . ?
C33 C32 C31 119.7(3) . . ?
C33 C32 H32 120.2 . . ?
C32 C33 H33 120.1 . . ?
C32 C33 C34 119.9(3) . . ?
C34 C33 H33 120.1 . . ?
C29 C34 H34 119.4 . . ?
C33 C34 C29 121.2(2) . . ?
C33 C34 H34 119.4 . . ?

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 C17 C18 O4 -68.1(2) . . . . ?
O1 C17 C18 C19 174.92(17) . . . . ?
O2 C7 C8 C9 173.22(17) . . . . ?
O2 C7 C8 C17 52.3(2) . . . . ?
O2 C19 C20 O3 -63.7(2) . . . . ?
O3 C21 C22 C23 -96.1(3) . . . . ?
O3 C21 C22 C27 83.7(3) . . . . ?
O4 C18 C19 O2 -175.90(16) . . . . ?
O4 C18 C19 C20 61.4(2) . . . . ?
O4 C28 C29 C30 -124.6(3) . . . . ?
O4 C28 C29 C34 55.5(4) . . . . ?
N1 C5 C6 C1 -178.5(2) . . . . ?
N1 C9 C11 C12 76.3(3) . . . . ?
N1 C9 C11 C16 -101.8(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C2 C3 C4 C7 -177.9(2) . . . . ?
C3 C4 C5 N1 177.7(2) . . . . ?
C3 C4 C5 C6 -2.3(3) . . . . ?
C3 C4 C7 O2 33.6(3) . . . . ?
C3 C4 C7 C8 157.5(2) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C4 C7 C8 C9 48.2(2) . . . . ?
C4 C7 C8 C17 -72.7(2) . . . . ?
C5 N1 C9 C8 27.3(3) . . . . ?
C5 N1 C9 C11 148.1(2) . . . . ?
C5 C4 C7 O2 -145.62(19) . . . . ?
C5 C4 C7 C8 -21.7(3) . . . . ?
C6 C1 C2 C3 -1.5(4) . . . . ?
C7 O2 C19 C18 64.1(2) . . . . ?
C7 O2 C19 C20 -169.82(19) . . . . ?
C7 C4 C5 N1 -3.1(3) . . . . ?
C7 C4 C5 C6 177.0(2) . . . . ?
C7 C8 C9 N1 -50.7(2) . . . . ?
C7 C8 C9 C11 -171.40(18) . . . . ?
C7 C8 C17 O1 -171.83(18) . . . . ?
C7 C8 C17 C18 -50.4(2) . . . . ?
C8 C9 C11 C12 -162.2(2) . . . . ?
C8 C9 C11 C16 19.8(3) . . . . ?
C8 C17 C18 O4 169.09(18) . . . . ?
C8 C17 C18 C19 52.2(2) . . . . ?
C9 N1 C5 C4 0.0(3) . . . . ?
C9 N1 C5 C6 180.0(2) . . . . ?
C9 C8 C17 O1 65.1(2) . . . . ?
C9 C8 C17 C18 -173.46(18) . . . . ?
C9 C11 C12 C13 -177.5(2) . . . . ?
C9 C11 C16 O1 -2.2(4) . . . . ?
C9 C11 C16 C15 -180.0(2) . . . . ?
C11 C12 C13 C14 -2.4(4) . . . . ?
C12 C11 C16 O1 179.7(2) . . . . ?
C12 C11 C16 C15 1.9(4) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C14 C15 C16 O1 179.3(2) . . . . ?
C14 C15 C16 C11 -2.7(4) . . . . ?
C16 O1 C17 C8 -48.0(3) . . . . ?
C16 O1 C17 C18 -171.96(19) . . . . ?
C16 C11 C12 C13 0.7(4) . . . . ?
C17 O1 C16 C11 16.4(3) . . . . ?
C17 O1 C16 C15 -165.7(2) . . . . ?
C17 C8 C9 N1 71.9(2) . . . . ?
C17 C8 C9 C11 -48.8(2) . . . . ?
C17 C18 C19 O2 -57.9(2) . . . . ?
C17 C18 C19 C20 179.43(18) . . . . ?
C18 O4 C28 C29 -179.3(2) . . . . ?
C18 C19 C20 O3 60.0(3) . . . . ?
C19 O2 C7 C4 64.6(2) . . . . ?
C19 O2 C7 C8 -60.4(2) . . . . ?
C20 O3 C21 C22 72.7(3) . . . . ?
C21 O3 C20 C19 174.9(2) . . . . ?
C21 C22 C23 C24 179.7(2) . . . . ?
C21 C22 C27 C26 -179.8(3) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C23 C22 C27 C26 -0.1(4) . . . . ?
C23 C24 C25 C26 -0.4(5) . . . . ?
C24 C25 C26 C27 0.2(5) . . . . ?
C25 C26 C27 C22 0.0(5) . . . . ?
C27 C22 C23 C24 -0.1(4) . . . . ?
C28 O4 C18 C17 114.4(3) . . . . ?
C28 O4 C18 C19 -128.1(2) . . . . ?
C28 C29 C30 C31 179.7(4) . . . . ?
C28 C29 C34 C33 -179.8(3) . . . . ?
C29 C30 C31 C32 0.3(7) . . . . ?
C30 C29 C34 C33 0.3(4) . . . . ?
C30 C31 C32 C33 -0.2(7) . . . . ?
C31 C32 C33 C34 0.1(5) . . . . ?
C32 C33 C34 C29 -0.2(4) . . . . ?
C34 C29 C30 C31 -0.4(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
