# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1484546'
_audit_update_record             
;
2016-06-10 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_I                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The specimen used was an extremely thin plate (0.01 mm) of
not-so-good quality (very fragile and difficult to handle). Even with 
very long exposure time for each frame no diffraction was observed below 
1 A. Disorder in the structure also contributed to the low resolution,
high Rint-value and unusually high s.u.'s for the geometric parameters
(checkCIF Alert level B messages).
;
_vrf_PLAT023_I                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      20.86 Degree
RESPONSE: Same as above.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(1S,6S,7S,8R)-8-Butyl-7-((3,5-dinitrobenzoyl)oxymethyl)bicyclo[4.3.0]non-3-ene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N2 O6'
_chemical_formula_sum            'C21 H26 N2 O6'
_chemical_formula_weight         402.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   10.866(5)
_cell_length_b                   5.196(2)
_cell_length_c                   18.617(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.703(11)
_cell_angle_gamma                90
_cell_volume                     1006.8(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2295
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      20.86

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'InCoatec ImuS Microfocus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 Venture with Photon 100 CMOS detector'
_diffrn_measurement_method       
'Sets of exposures each taken over 0.5° ω rotation'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            5899
_diffrn_reflns_av_unetI/netI     0.1400
_diffrn_reflns_av_R_equivalents  0.2140
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         20.864
_diffrn_reflns_theta_full        20.864
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2089
_reflns_number_gt                1718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.553

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'APEX2 (Bruker, 2014)'
_computing_structure_solution    'APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXT (Sheldrick, 2015a)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015b)'

_refine_special_details          
;
Two disorder positions refined for n-butyl group attached to C10.
Occupancies 0.74(3) and 0.26(3).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0936P)²+2.6032P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2089
_refine_ls_number_parameters     278
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0854
_refine_ls_wR_factor_ref         0.2246
_refine_ls_wR_factor_gt          0.2150
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.035
_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 0.4965(7) 0.0115(19) 0.3931(4) 0.034(2) Uani 1 1 d . . . . .
N1 N 0.7700(10) 0.288(2) 0.6525(7) 0.034(3) Uani 1 1 d . . . . .
C1 C 0.5467(10) 0.212(3) 0.3832(7) 0.023(3) Uani 1 1 d . U . . .
O2 O 0.5244(7) 0.3323(19) 0.3180(5) 0.032(2) Uani 1 1 d . . . . .
N2 N 0.8755(9) 0.896(2) 0.4771(7) 0.025(2) Uani 1 1 d . U . . .
C2 C 0.6411(11) 0.353(3) 0.4451(7) 0.028(3) Uani 1 1 d . U . . .
O3 O 0.7262(8) 0.077(2) 0.6594(5) 0.040(2) Uani 1 1 d . . . . .
C3 C 0.6602(11) 0.265(2) 0.5163(7) 0.028(3) Uani 1 1 d . U . . .
H31 H 0.6121 0.1220 0.5254 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7491(10) 0.382(3) 0.5752(6) 0.025(3) Uani 1 1 d . U . . .
O4 O 0.8317(8) 0.420(2) 0.7046(5) 0.044(2) Uani 1 1 d . . . . .
C5 C 0.8206(10) 0.596(2) 0.5648(7) 0.024(3) Uani 1 1 d . U . . .
H51 H 0.8798 0.6815 0.6053 0.029 Uiso 1 1 calc R U . . .
O5 O 0.9445(7) 1.0018(19) 0.5311(5) 0.039(2) Uani 1 1 d . . . . .
C6 C 0.7990(10) 0.672(2) 0.4921(7) 0.021(3) Uani 1 1 d . U . . .
O6 O 0.8619(7) 0.9540(18) 0.4128(5) 0.036(2) Uani 1 1 d . . . . .
C7 C 0.7120(10) 0.562(2) 0.4316(6) 0.023(3) Uani 1 1 d . U . . .
H71 H 0.7003 0.6265 0.3823 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4292(12) 0.208(3) 0.2553(7) 0.036(3) Uani 1 1 d . . . . .
H81 H 0.3491 0.1772 0.2692 0.044 Uiso 1 1 calc R U . A 1
H82 H 0.4626 0.0397 0.2445 0.044 Uiso 1 1 calc R U . A 1
C12 C 0.3164(15) 0.342(3) 0.0499(8) 0.055(4) Uani 1 1 d . . . . .
H121 H 0.3329 0.1800 0.0253 0.066 Uiso 1 1 calc R U . B 1
C13 C 0.2879(13) 0.270(3) 0.1245(7) 0.041(4) Uani 1 1 d . . . . .
H131 H 0.2890 0.0776 0.1285 0.049 Uiso 1 1 calc R U . C 1
C14 C 0.1617(12) 0.364(3) 0.1326(8) 0.046(4) Uani 1 1 d . . . . .
H141 H 0.0929 0.2417 0.1076 0.055 Uiso 1 1 calc R U . . .
H142 H 0.1663 0.3703 0.1865 0.055 Uiso 1 1 calc R U . . .
C15 C 0.1292(13) 0.625(3) 0.0990(9) 0.050(4) Uani 1 1 d . . . . .
H151 H 0.0928 0.7505 0.1241 0.059 Uiso 1 1 calc R U . . .
C16 C 0.1501(12) 0.682(3) 0.0365(10) 0.049(4) Uani 1 1 d . . . . .
H161 H 0.1334 0.8508 0.0167 0.059 Uiso 1 1 calc R U . . .
C17 C 0.2006(14) 0.483(3) -0.0052(8) 0.053(4) Uani 1 1 d . . . . .
H171 H 0.2286 0.5653 -0.0458 0.063 Uiso 1 1 calc R U . . .
H172 H 0.1321 0.3573 -0.0281 0.063 Uiso 1 1 calc R U . . .
C9 C 0.4010(11) 0.375(3) 0.1869(7) 0.032(3) Uani 0.74(3) 1 d D . P D 1
H91 H 0.3797 0.5522 0.2003 0.038 Uiso 0.74(3) 1 calc R U P D 1
C11 C 0.4409(12) 0.494(3) 0.0739(8) 0.048(4) Uani 0.74(3) 1 d D . P D 1
H111 H 0.4230 0.6802 0.0769 0.058 Uiso 0.74(3) 1 calc R U P D 1
H112 H 0.4911 0.4696 0.0377 0.058 Uiso 0.74(3) 1 calc R U P D 1
C10 C 0.5144(12) 0.391(4) 0.1509(8) 0.044(4) Uani 0.74(3) 1 d D . P D 1
H10 H 0.5419 0.2108 0.1440 0.053 Uiso 0.74(3) 1 calc R U P D 1
C18 C 0.6307(14) 0.537(6) 0.1938(9) 0.060(6) Uani 0.74(3) 1 d D . P D 1
H181 H 0.6668 0.4529 0.2431 0.072 Uiso 0.74(3) 1 calc R U P D 1
H182 H 0.6039 0.7130 0.2033 0.072 Uiso 0.74(3) 1 calc R U P D 1
C19 C 0.7354(15) 0.558(7) 0.1554(11) 0.084(7) Uani 0.74(3) 1 d D . P D 1
H191 H 0.7465 0.3889 0.1335 0.101 Uiso 0.74(3) 1 calc R U P D 1
H192 H 0.7092 0.6839 0.1139 0.101 Uiso 0.74(3) 1 calc R U P D 1
C20 C 0.8620(16) 0.641(4) 0.2089(12) 0.067(8) Uani 0.74(3) 1 d D . P D 1
H201 H 0.8470 0.8021 0.2333 0.081 Uiso 0.74(3) 1 calc R U P D 1
H202 H 0.9211 0.6827 0.1787 0.081 Uiso 0.74(3) 1 calc R U P D 1
C21 C 0.932(4) 0.453(7) 0.271(2) 0.096(13) Uani 0.74(3) 1 d D . P D 1
H211 H 1.0170 0.5212 0.2964 0.145 Uiso 0.74(3) 1 calc R U P D 1
H212 H 0.9403 0.2862 0.2482 0.145 Uiso 0.74(3) 1 calc R U P D 1
H213 H 0.8819 0.4328 0.3066 0.145 Uiso 0.74(3) 1 calc R U P D 1
C9B C 0.4010(11) 0.375(3) 0.1869(7) 0.032(3) Uani 0.26(3) 1 d D . P D 2
H91B H 0.3750 0.5474 0.2013 0.038 Uiso 0.26(3) 1 calc R U P D 2
C11B C 0.4409(12) 0.494(3) 0.0739(8) 0.048(4) Uani 0.26(3) 1 d D . P D 2
H11B H 0.4217 0.6809 0.0720 0.058 Uiso 0.26(3) 1 calc R U P D 2
H12B H 0.4929 0.4588 0.0392 0.058 Uiso 0.26(3) 1 calc R U P D 2
C10B C 0.5162(13) 0.418(5) 0.1535(9) 0.044(4) Uani 0.26(3) 1 d D . P D 2
H10B H 0.5570 0.2473 0.1510 0.053 Uiso 0.26(3) 1 calc R U P D 2
C18B C 0.619(2) 0.598(8) 0.1954(11) 0.060(6) Uani 0.26(3) 1 d D U P D 2
H18B H 0.6533 0.5355 0.2476 0.072 Uiso 0.26(3) 1 calc R U P D 2
H19B H 0.5803 0.7695 0.1975 0.072 Uiso 0.26(3) 1 calc R U P D 2
C19B C 0.730(3) 0.630(9) 0.162(3) 0.084(7) Uani 0.26(3) 1 d D U P D 2
H20B H 0.6960 0.6514 0.1073 0.101 Uiso 0.26(3) 1 calc R U P D 2
H21B H 0.7786 0.7876 0.1829 0.101 Uiso 0.26(3) 1 calc R U P D 2
C20B C 0.820(3) 0.402(9) 0.179(3) 0.050 Uiso 0.26(3) 1 d D U P D 2
H22B H 0.8733 0.4081 0.1438 0.060 Uiso 0.26(3) 1 calc R U P D 2
H23B H 0.7673 0.2438 0.1673 0.060 Uiso 0.26(3) 1 calc R U P D 2
C21B C 0.911(13) 0.37(3) 0.258(5) 0.096(13) Uani 0.26(3) 1 d D . P D 2
H24B H 0.9659 0.2227 0.2605 0.145 Uiso 0.26(3) 1 calc R U P D 2
H25B H 0.8605 0.3521 0.2939 0.145 Uiso 0.26(3) 1 calc R U P D 2
H26B H 0.9645 0.5281 0.2714 0.145 Uiso 0.26(3) 1 calc R U P D 2


_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 1.213(14) . ?
N1 O3 1.218(13) . ?
N1 O4 1.219(12) . ?
N1 C4 1.474(15) . ?
C1 O2 1.326(14) . ?
C1 C2 1.498(16) . ?
O2 C8 1.467(14) . ?
N2 O5 1.202(11) . ?
N2 O6 1.202(11) . ?
N2 C6 1.502(15) . ?
C2 C3 1.361(16) . ?
C2 C7 1.397(16) . ?
C3 C4 1.377(16) . ?
C3 H31 0.9500 . ?
C4 C5 1.403(15) . ?
C5 C6 1.364(16) . ?
C5 H51 0.9500 . ?
C6 C7 1.368(15) . ?
C7 H71 0.9500 . ?
C8 C9 1.497(17) . ?
C8 H81 0.9900 . ?
C8 H82 0.9900 . ?
C12 C11 1.52(2) . ?
C12 C13 1.55(2) . ?
C12 C17 1.558(19) . ?
C12 H121 1.0000 . ?
C13 C14 1.504(19) . ?
C13 C9 1.530(17) . ?
C13 H131 1.0000 . ?
C14 C15 1.49(2) . ?
C14 H141 0.9900 . ?
C14 H142 0.9900 . ?
C15 C16 1.28(2) . ?
C15 H151 0.9500 . ?
C16 C17 1.49(2) . ?
C16 H161 0.9500 . ?
C17 H171 0.9900 . ?
C17 H172 0.9900 . ?
C9 C10 1.565(17) . ?
C9 H91 1.0000 . ?
C11 C10 1.524(18) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C10 C18 1.495(19) . ?
C10 H10 1.0000 . ?
C18 C19 1.512(17) . ?
C18 H181 0.9900 . ?
C18 H182 0.9900 . ?
C19 C20 1.51(2) . ?
C19 H191 0.9900 . ?
C19 H192 0.9900 . ?
C20 C21 1.53(2) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 H211 0.9800 . ?
C21 H212 0.9800 . ?
C21 H213 0.9800 . ?
C10B C18B 1.50(2) . ?
C10B H10B 1.0000 . ?
C18B C19B 1.512(18) . ?
C18B H18B 0.9900 . ?
C18B H19B 0.9900 . ?
C19B C20B 1.51(2) . ?
C19B H20B 0.9900 . ?
C19B H21B 0.9900 . ?
C20B C21B 1.53(2) . ?
C20B H22B 0.9900 . ?
C20B H23B 0.9900 . ?
C21B H24B 0.9800 . ?
C21B H25B 0.9800 . ?
C21B H26B 0.9800 . ?

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
O3 N1 O4 124.5(11) . . ?
O3 N1 C4 116.4(11) . . ?
O4 N1 C4 119.0(10) . . ?
O1 C1 O2 125.0(11) . . ?
O1 C1 C2 122.8(11) . . ?
O2 C1 C2 112.2(10) . . ?
C1 O2 C8 114.9(9) . . ?
O5 N2 O6 125.9(10) . . ?
O5 N2 C6 116.5(10) . . ?
O6 N2 C6 117.7(10) . . ?
C3 C2 C7 120.0(11) . . ?
C3 C2 C1 117.6(11) . . ?
C7 C2 C1 122.3(11) . . ?
C2 C3 C4 120.2(11) . . ?
C2 C3 H31 119.9 . . ?
C4 C3 H31 119.9 . . ?
C3 C4 C5 122.0(11) . . ?
C3 C4 N1 120.6(11) . . ?
C5 C4 N1 117.5(10) . . ?
C6 C5 C4 115.0(10) . . ?
C6 C5 H51 122.5 . . ?
C4 C5 H51 122.5 . . ?
C5 C6 C7 125.3(10) . . ?
C5 C6 N2 117.5(10) . . ?
C7 C6 N2 117.2(10) . . ?
C6 C7 C2 117.5(11) . . ?
C6 C7 H71 121.2 . . ?
C2 C7 H71 121.2 . . ?
O2 C8 C9 110.3(10) . . ?
O2 C8 H81 109.6 . . ?
C9 C8 H81 109.6 . . ?
O2 C8 H82 109.6 . . ?
C9 C8 H82 109.6 . . ?
H81 C8 H82 108.1 . . ?
C11 C12 C13 104.7(10) . . ?
C11 C12 C17 115.6(12) . . ?
C13 C12 C17 111.8(12) . . ?
C11 C12 H121 108.2 . . ?
C13 C12 H121 108.2 . . ?
C17 C12 H121 108.2 . . ?
C14 C13 C9 111.3(10) . . ?
C14 C13 C12 115.6(11) . . ?
C9 C13 C12 105.6(11) . . ?
C14 C13 H131 108.0 . . ?
C9 C13 H131 108.0 . . ?
C12 C13 H131 108.0 . . ?
C15 C14 C13 111.5(12) . . ?
C15 C14 H141 109.3 . . ?
C13 C14 H141 109.3 . . ?
C15 C14 H142 109.3 . . ?
C13 C14 H142 109.3 . . ?
H141 C14 H142 108.0 . . ?
C16 C15 C14 120.3(14) . . ?
C16 C15 H151 119.9 . . ?
C14 C15 H151 119.9 . . ?
C15 C16 C17 120.2(13) . . ?
C15 C16 H161 119.9 . . ?
C17 C16 H161 119.9 . . ?
C16 C17 C12 109.4(11) . . ?
C16 C17 H171 109.8 . . ?
C12 C17 H171 109.8 . . ?
C16 C17 H172 109.8 . . ?
C12 C17 H172 109.8 . . ?
H171 C17 H172 108.3 . . ?
C8 C9 C13 111.3(10) . . ?
C8 C9 C10 113.6(10) . . ?
C13 C9 C10 104.6(10) . . ?
C8 C9 H91 109.0 . . ?
C13 C9 H91 109.0 . . ?
C10 C9 H91 109.0 . . ?
C12 C11 C10 105.9(11) . . ?
C12 C11 H111 110.5 . . ?
C10 C11 H111 110.5 . . ?
C12 C11 H112 110.5 . . ?
C10 C11 H112 110.5 . . ?
H111 C11 H112 108.7 . . ?
C18 C10 C11 117.2(12) . . ?
C18 C10 C9 116.5(11) . . ?
C11 C10 C9 99.0(10) . . ?
C18 C10 H10 107.8 . . ?
C11 C10 H10 107.8 . . ?
C9 C10 H10 107.8 . . ?
C10 C18 C19 114.7(13) . . ?
C10 C18 H181 108.6 . . ?
C19 C18 H181 108.6 . . ?
C10 C18 H182 108.6 . . ?
C19 C18 H182 108.6 . . ?
H181 C18 H182 107.6 . . ?
C20 C19 C18 112.0(14) . . ?
C20 C19 H191 109.2 . . ?
C18 C19 H191 109.2 . . ?
C20 C19 H192 109.2 . . ?
C18 C19 H192 109.2 . . ?
H191 C19 H192 107.9 . . ?
C19 C20 C21 118(2) . . ?
C19 C20 H201 107.8 . . ?
C21 C20 H201 107.8 . . ?
C19 C20 H202 107.8 . . ?
C21 C20 H202 107.8 . . ?
H201 C20 H202 107.1 . . ?
C20 C21 H211 109.5 . . ?
C20 C21 H212 109.5 . . ?
H211 C21 H212 109.5 . . ?
C20 C21 H213 109.5 . . ?
H211 C21 H213 109.5 . . ?
H212 C21 H213 109.5 . . ?
C18B C10B H10B 107.8 . . ?
C10B C18B C19B 114.8(15) . . ?
C10B C18B H18B 108.6 . . ?
C19B C18B H18B 108.6 . . ?
C10B C18B H19B 108.6 . . ?
C19B C18B H19B 108.6 . . ?
H18B C18B H19B 107.5 . . ?
C20B C19B C18B 112.1(16) . . ?
C20B C19B H20B 109.2 . . ?
C18B C19B H20B 109.2 . . ?
C20B C19B H21B 109.2 . . ?
C18B C19B H21B 109.2 . . ?
H20B C19B H21B 107.9 . . ?
C19B C20B C21B 118(2) . . ?
C19B C20B H22B 107.8 . . ?
C21B C20B H22B 107.8 . . ?
C19B C20B H23B 107.8 . . ?
C21B C20B H23B 107.8 . . ?
H22B C20B H23B 107.1 . . ?
C20B C21B H24B 109.5 . . ?
C20B C21B H25B 109.5 . . ?
H24B C21B H25B 109.5 . . ?
C20B C21B H26B 109.5 . . ?
H24B C21B H26B 109.5 . . ?
H25B C21B H26B 109.5 . . ?

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 C1 O2 C8 1.1(15) . . . . ?
C2 C1 O2 C8 -178.0(8) . . . . ?
O1 C1 C2 C3 -6.8(16) . . . . ?
O2 C1 C2 C3 172.3(10) . . . . ?
O1 C1 C2 C7 170.7(10) . . . . ?
O2 C1 C2 C7 -10.2(14) . . . . ?
C7 C2 C3 C4 0.2(16) . . . . ?
C1 C2 C3 C4 177.7(10) . . . . ?
C2 C3 C4 C5 1.2(16) . . . . ?
C2 C3 C4 N1 179.8(10) . . . . ?
O3 N1 C4 C3 14.6(14) . . . . ?
O4 N1 C4 C3 -167.3(10) . . . . ?
O3 N1 C4 C5 -166.7(9) . . . . ?
O4 N1 C4 C5 11.4(14) . . . . ?
C3 C4 C5 C6 -2.4(14) . . . . ?
N1 C4 C5 C6 179.0(9) . . . . ?
C4 C5 C6 C7 2.5(15) . . . . ?
C4 C5 C6 N2 -178.4(8) . . . . ?
O5 N2 C6 C5 -4.6(13) . . . . ?
O6 N2 C6 C5 175.9(9) . . . . ?
O5 N2 C6 C7 174.6(9) . . . . ?
O6 N2 C6 C7 -4.8(13) . . . . ?
C5 C6 C7 C2 -1.2(15) . . . . ?
N2 C6 C7 C2 179.6(8) . . . . ?
C3 C2 C7 C6 -0.2(15) . . . . ?
C1 C2 C7 C6 -177.7(10) . . . . ?
C1 O2 C8 C9 173.8(9) . . . . ?
C11 C12 C13 C14 121.2(13) . . . . ?
C17 C12 C13 C14 -4.7(16) . . . . ?
C11 C12 C13 C9 -2.3(14) . . . . ?
C17 C12 C13 C9 -128.2(11) . . . . ?
C9 C13 C14 C15 83.5(14) . . . . ?
C12 C13 C14 C15 -37.0(16) . . . . ?
C13 C14 C15 C16 40.9(18) . . . . ?
C14 C15 C16 C17 3(2) . . . . ?
C15 C16 C17 C12 -47.5(18) . . . . ?
C11 C12 C17 C16 -74.5(15) . . . . ?
C13 C12 C17 C16 45.1(15) . . . . ?
O2 C8 C9 C13 -171.4(9) . . . . ?
O2 C8 C9 C10 70.8(13) . . . . ?
C14 C13 C9 C8 86.1(13) . . . . ?
C12 C13 C9 C8 -147.7(10) . . . . ?
C14 C13 C9 C10 -150.8(11) . . . . ?
C12 C13 C9 C10 -24.6(13) . . . . ?
C13 C12 C11 C10 29.4(14) . . . . ?
C17 C12 C11 C10 152.9(12) . . . . ?
C12 C11 C10 C18 -169.6(13) . . . . ?
C12 C11 C10 C9 -43.5(14) . . . . ?
C8 C9 C10 C18 -70.5(16) . . . . ?
C13 C9 C10 C18 167.9(14) . . . . ?
C8 C9 C10 C11 163.0(11) . . . . ?
C13 C9 C10 C11 41.4(13) . . . . ?
C11 C10 C18 C19 -60(2) . . . . ?
C9 C10 C18 C19 -177.4(19) . . . . ?
C10 C18 C19 C20 -164(2) . . . . ?
C18 C19 C20 C21 68(4) . . . . ?
C9B C10B C18B C19B 178(2) . . . . ?
C10B C18B C19B C20B -76(4) . . . . ?
C18B C19B C20B C21B -75(10) . . . . ?

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'slow evaporation'
