# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_twin4


# start Validation Reply Form
_vrf_REFLT03_I                   
;
PROBLEM: Reflection count > 15% excess reflns - sys abs data present?
RESPONSE: 

 Indexing using Cell_Now indicated the presence of
 a twinned crystal. An extended data collection procedure
 using 10 runs, including omega and phi scans were
 initiated.

 Data was collected using Cu-source and a GADDS detector (multiwire 
 proportional counter). With the given crystal mounting, the 
 completeness looks low. However, since the crystal had two
 twin components and both of them were used for least squares
 refinement, the actual completeness is higher than indicated in the 
 CIF file.

 No efforts were made to remount the crystal and collect the
 data to increase completeness.

 APEX2 software was used to integrate the data including both the domains.
 TWINABS was used to correct the data for absorption and systematic
 errors, as well as to generate the twin4.hkl file with only one 
 component twin and twin5.hkl with both the twin components. While the 
 former file was used for structure solution, the latter was used along 
 with BASF for final least squares refinement.

;
_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.886      
RESPONSE: 

 Indexing using Cell_Now indicated the presence of
 a twinned crystal. An extended data collection procedure
 using 10 runs, including omega and phi scans were
 initiated.

 Data was collected using Cu-source and a GADDS detector (multiwire 
 proportional counter). With the given crystal mounting, the 
 completeness looks low. However, since the crystal had two
 twin components and both of them were used for least squares
 refinement, the actual completeness is higher than indicated in the 
 CIF file.

 No efforts were made to remount the crystal and collect the
 data to increase completeness.

 APEX2 software was used to integrate the data including both the domains.
 TWINABS was used to correct the data for absorption and systematic
 errors, as well as to generate the twin4.hkl file with only one 
 component twin and twin5.hkl with both the twin components. While the 
 former file was used for structure solution, the latter was used along 
 with BASF for final least squares refinement.

;
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O4'
_chemical_formula_weight         325.35

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4369(10)
_cell_length_b                   12.6589(13)
_cell_length_c                   15.5346(16)
_cell_angle_alpha                75.851(6)
_cell_angle_beta                 89.973(7)
_cell_angle_gamma                83.469(7)
_cell_volume                     1597.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    1164
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      61.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9403
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_process_details   'TWINABS; (Sheldrick, 2006)'

_exptl_special_details           
; 
 Indexing using Cell_Now indicated the presence of
 a twinned crystal. An extended data collection procedure
 using 10 runs, including omega and phi scans were
 initiated.

 Data was collected using Cu-source and a GADDS detector (multiwire 
 proportional counter). With the given crystal mounting, the 
 completeness looks low. However, since the crystal had two
 twin components and both of them were used for least squares
 refinement, the actual completeness is higher than indicated in the 
 CIF file.

 No efforts were made to remount the crystal and collect the
 data to increase completeness.

;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6568
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         60.00
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_reflns_number_total             6577
_reflns_number_gt                4704
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
; 
  CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) 
;
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Olex2
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 APEX2 software was used to integrate the data including both the domains.
 TWINABS was used to correct the data for absorption and systematic
 errors, as well as to generate the twin4.hkl file with only one 
 component twin and twin5.hkl with both the twin components. While the 
 former file was used for structure solution, the latter was used along 
 with BASF for final least squares refinement.




;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1079P)²+0.0000P] 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
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6577
_refine_ls_number_parameters     438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1867
_refine_ls_wR_factor_gt          0.1642
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6805(4) 0.0727(2) -0.11074(18) 0.0229(8) Uani 1 1 d . . .
H1 H 0.6708 0.0781 -0.1655 0.034 Uiso 1 1 calc R . .
O2 O 0.8806(4) 0.0331(2) 0.22937(17) 0.0197(7) Uani 1 1 d . . .
O3 O 0.4459(4) 0.2578(2) 0.03037(19) 0.0265(8) Uani 1 1 d . . .
O4 O 0.6651(4) 0.24922(19) 0.11531(17) 0.0192(7) Uani 1 1 d . . .
N1 N 1.0057(4) 0.1275(2) 0.1082(2) 0.0155(8) Uani 1 1 d . . .
C1 C 0.8048(6) 0.1240(3) -0.0952(3) 0.0179(10) Uani 1 1 d . . .
C2 C 0.8503(5) 0.1112(3) -0.0065(3) 0.0156(10) Uani 1 1 d . . .
C3 C 0.9814(5) 0.1579(3) 0.0144(2) 0.0125(10) Uani 1 1 d . . .
C4 C 1.0706(6) 0.2203(3) -0.0495(3) 0.0182(10) Uani 1 1 d . . .
H4 H 1.1605 0.2517 -0.0345 0.022 Uiso 1 1 calc R . .
C5 C 1.0189(6) 0.2336(3) -0.1375(3) 0.0201(11) Uani 1 1 d . . .
H5 H 1.0752 0.2768 -0.1835 0.024 Uiso 1 1 calc R . .
C6 C 0.8910(6) 0.1874(3) -0.1606(2) 0.0189(11) Uani 1 1 d . . .
H6 H 0.8612 0.1987 -0.2215 0.023 Uiso 1 1 calc R . .
C7 C 0.7816(6) 0.0494(3) 0.0770(3) 0.0177(10) Uani 1 1 d . . .
H7 H 0.7963 -0.0304 0.0780 0.021 Uiso 1 1 calc R . .
C8 C 0.8909(6) 0.0679(3) 0.1484(3) 0.0173(10) Uani 1 1 d . . .
C9 C 0.6035(5) 0.0836(3) 0.0891(3) 0.0164(10) Uani 1 1 d . . .
H9A H 0.5391 0.0565 0.0476 0.020 Uiso 1 1 calc R . .
H9B H 0.5747 0.0480 0.1503 0.020 Uiso 1 1 calc R . .
C10 C 0.5613(6) 0.2049(3) 0.0734(3) 0.0179(10) Uani 1 1 d . . .
C11 C 0.6353(6) 0.3670(3) 0.1079(3) 0.0233(11) Uani 1 1 d . . .
H11C H 0.6872 0.3848 0.1589 0.028 Uiso 1 1 calc R . .
H11D H 0.5190 0.3888 0.1095 0.028 Uiso 1 1 calc R . .
C12 C 0.6989(6) 0.4299(3) 0.0229(3) 0.0296(12) Uani 1 1 d . . .
H12D H 0.8134 0.4069 0.0206 0.044 Uiso 1 1 calc R . .
H12E H 0.6818 0.5086 0.0201 0.044 Uiso 1 1 calc R . .
H12F H 0.6432 0.4155 -0.0276 0.044 Uiso 1 1 calc R . .
C13 C 1.1320(6) 0.1611(3) 0.1576(3) 0.0174(10) Uani 1 1 d . . .
H13C H 1.2256 0.1737 0.1196 0.021 Uiso 1 1 calc R . .
H13D H 1.1659 0.1013 0.2106 0.021 Uiso 1 1 calc R . .
C14 C 1.0755(5) 0.2645(3) 0.1864(2) 0.0164(10) Uani 1 1 d . . .
C15 C 1.0007(6) 0.2571(3) 0.2678(3) 0.0202(11) Uani 1 1 d . . .
H15 H 0.9913 0.1873 0.3062 0.024 Uiso 1 1 calc R . .
C16 C 0.9403(6) 0.3518(3) 0.2923(3) 0.0246(11) Uani 1 1 d . . .
H16 H 0.8868 0.3465 0.3468 0.030 Uiso 1 1 calc R . .
C17 C 0.9574(6) 0.4539(3) 0.2381(3) 0.0283(12) Uani 1 1 d . . .
H17 H 0.9141 0.5185 0.2546 0.034 Uiso 1 1 calc R . .
C18 C 1.0378(6) 0.4614(3) 0.1598(3) 0.0304(13) Uani 1 1 d . . .
H18 H 1.0538 0.5313 0.1236 0.037 Uiso 1 1 calc R . .
C19 C 1.0952(6) 0.3673(3) 0.1341(3) 0.0256(12) Uani 1 1 d . . .
H19 H 1.1490 0.3734 0.0797 0.031 Uiso 1 1 calc R . .
O1B O 0.7781(4) 0.0503(2) 0.39118(18) 0.0239(8) Uani 1 1 d . . .
H1B H 0.7888 0.0549 0.3367 0.036 Uiso 1 1 calc R . .
O2B O 0.5927(4) 0.05635(19) 0.72576(17) 0.0177(7) Uani 1 1 d . . .
O3B O 0.9928(4) 0.2157(2) 0.5091(2) 0.0328(8) Uani 1 1 d . . .
O4B O 0.7804(4) 0.2510(2) 0.59011(18) 0.0231(7) Uani 1 1 d . . .
N1B N 0.4459(4) 0.1520(2) 0.6009(2) 0.0146(8) Uani 1 1 d . . .
C1B C 0.6435(5) 0.1151(3) 0.4035(3) 0.0156(10) Uani 1 1 d . . .
C2B C 0.6019(5) 0.1111(3) 0.4906(2) 0.0122(9) Uani 1 1 d . . .
C3B C 0.4627(6) 0.1726(3) 0.5073(3) 0.0186(11) Uani 1 1 d . . .
C4B C 0.3628(6) 0.2388(3) 0.4398(3) 0.0164(10) Uani 1 1 d . . .
H4B H 0.2673 0.2793 0.4521 0.020 Uiso 1 1 calc R . .
C5B C 0.4090(6) 0.2428(3) 0.3537(3) 0.0190(10) Uani 1 1 d . . .
H5B H 0.3443 0.2885 0.3060 0.023 Uiso 1 1 calc R . .
C6B C 0.5461(6) 0.1826(3) 0.3347(3) 0.0189(11) Uani 1 1 d . . .
H6B H 0.5738 0.1872 0.2747 0.023 Uiso 1 1 calc R . .
C7B C 0.6852(5) 0.0481(3) 0.5776(3) 0.0156(10) Uani 1 1 d . . .
H7B H 0.6812 -0.0320 0.5838 0.019 Uiso 1 1 calc R . .
C8B C 0.5737(6) 0.0853(3) 0.6444(3) 0.0157(10) Uani 1 1 d . . .
C9B C 0.8576(6) 0.0670(3) 0.5896(3) 0.0205(11) Uani 1 1 d . . .
H9BA H 0.8885 0.0415 0.6535 0.025 Uiso 1 1 calc R . .
H9BB H 0.9267 0.0219 0.5574 0.025 Uiso 1 1 calc R . .
C10B C 0.8875(6) 0.1838(3) 0.5574(3) 0.0204(10) Uani 1 1 d . . .
C11B C 0.7867(6) 0.3676(3) 0.5574(3) 0.0269(11) Uani 1 1 d . . .
H11A H 0.6771 0.4064 0.5519 0.032 Uiso 1 1 calc R . .
H11B H 0.8331 0.3823 0.4977 0.032 Uiso 1 1 calc R . .
C12B C 0.8859(7) 0.4109(3) 0.6189(3) 0.0335(13) Uani 1 1 d . . .
H12A H 0.8438 0.3925 0.6789 0.050 Uiso 1 1 calc R . .
H12B H 0.8814 0.4907 0.5977 0.050 Uiso 1 1 calc R . .
H12C H 0.9968 0.3775 0.6202 0.050 Uiso 1 1 calc R . .
C13B C 0.3179(6) 0.2007(3) 0.6467(3) 0.0189(10) Uani 1 1 d . . .
H13A H 0.2867 0.1441 0.6979 0.023 Uiso 1 1 calc R . .
H13B H 0.2238 0.2266 0.6059 0.023 Uiso 1 1 calc R . .
C14B C 0.3663(6) 0.2956(3) 0.6792(3) 0.0194(10) Uani 1 1 d . . .
C15B C 0.3715(6) 0.3984(3) 0.6212(3) 0.0248(11) Uani 1 1 d . . .
H15B H 0.3360 0.4106 0.5612 0.030 Uiso 1 1 calc R . .
C16B C 0.4275(6) 0.4829(3) 0.6498(3) 0.0308(13) Uani 1 1 d . . .
H16B H 0.4296 0.5526 0.6097 0.037 Uiso 1 1 calc R . .
C17B C 0.4807(6) 0.4659(3) 0.7370(3) 0.0300(12) Uani 1 1 d . . .
H17B H 0.5225 0.5231 0.7563 0.036 Uiso 1 1 calc R . .
C18B C 0.4727(7) 0.3651(4) 0.7959(3) 0.0348(13) Uani 1 1 d . . .
H18B H 0.5068 0.3537 0.8561 0.042 Uiso 1 1 calc R . .
C19B C 0.4154(6) 0.2813(3) 0.7674(3) 0.0241(11) Uani 1 1 d . . .
H19B H 0.4093 0.2128 0.8085 0.029 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 C1 1.346(5) . ?
O1 H1 0.8400 . ?
O2 C8 1.234(5) . ?
O3 C10 1.215(5) . ?
O4 C10 1.340(5) . ?
O4 C11 1.460(4) . ?
N1 C8 1.354(5) . ?
N1 C3 1.422(5) . ?
N1 C13 1.472(5) . ?
C1 C6 1.393(6) . ?
C1 C2 1.395(5) . ?
C2 C3 1.387(6) . ?
C2 C7 1.496(5) . ?
C3 C4 1.388(6) . ?
C4 C5 1.399(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.520(6) . ?
C7 C9 1.541(6) . ?
C7 H7 1.0000 . ?
C9 C10 1.496(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C12 1.500(6) . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C12 H12D 0.9800 . ?
C12 H12E 0.9800 . ?
C12 H12F 0.9800 . ?
C13 C14 1.512(5) . ?
C13 H13C 0.9900 . ?
C13 H13D 0.9900 . ?
C14 C19 1.383(5) . ?
C14 C15 1.400(6) . ?
C15 C16 1.388(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O1B C1B 1.366(5) . ?
O1B H1B 0.8400 . ?
O2B C8B 1.232(4) . ?
O3B C10B 1.204(5) . ?
O4B C10B 1.355(5) . ?
O4B C11B 1.446(5) . ?
N1B C8B 1.359(5) . ?
N1B C3B 1.422(5) . ?
N1B C13B 1.455(5) . ?
C1B C2B 1.387(5) . ?
C1B C6B 1.394(6) . ?
C2B C3B 1.394(6) . ?
C2B C7B 1.518(5) . ?
C3B C4B 1.387(6) . ?
C4B C5B 1.383(6) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.384(6) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C9B 1.519(6) . ?
C7B C8B 1.523(6) . ?
C7B H7B 1.0000 . ?
C9B C10B 1.491(6) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C11B C12B 1.508(6) . ?
C11B H11A 0.9900 . ?
C11B H11B 0.9900 . ?
C12B H12A 0.9800 . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
C13B C14B 1.507(5) . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C14B C19B 1.393(6) . ?
C14B C15B 1.396(6) . ?
C15B C16B 1.383(6) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.385(6) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.385(6) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.380(6) . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?

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
C1 O1 H1 109.5 . . ?
C10 O4 C11 117.2(3) . . ?
C8 N1 C3 111.2(3) . . ?
C8 N1 C13 123.1(3) . . ?
C3 N1 C13 125.5(3) . . ?
O1 C1 C6 124.9(4) . . ?
O1 C1 C2 116.9(4) . . ?
C6 C1 C2 118.2(4) . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 C7 109.5(3) . . ?
C1 C2 C7 130.4(4) . . ?
C2 C3 C4 122.9(3) . . ?
C2 C3 N1 108.3(3) . . ?
C4 C3 N1 128.8(4) . . ?
C3 C4 C5 115.4(4) . . ?
C3 C4 H4 122.3 . . ?
C5 C4 H4 122.3 . . ?
C6 C5 C4 123.3(4) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C2 C7 C8 102.4(3) . . ?
C2 C7 C9 115.2(3) . . ?
C8 C7 C9 113.7(3) . . ?
C2 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C9 C7 H7 108.4 . . ?
O2 C8 N1 125.0(4) . . ?
O2 C8 C7 126.6(4) . . ?
N1 C8 C7 108.5(3) . . ?
C10 C9 C7 113.5(3) . . ?
C10 C9 H9A 108.9 . . ?
C7 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C7 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O3 C10 O4 123.3(4) . . ?
O3 C10 C9 125.3(4) . . ?
O4 C10 C9 111.4(4) . . ?
O4 C11 C12 110.6(3) . . ?
O4 C11 H11C 109.5 . . ?
C12 C11 H11C 109.5 . . ?
O4 C11 H11D 109.5 . . ?
C12 C11 H11D 109.5 . . ?
H11C C11 H11D 108.1 . . ?
C11 C12 H12D 109.5 . . ?
C11 C12 H12E 109.5 . . ?
H12D C12 H12E 109.5 . . ?
C11 C12 H12F 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?
N1 C13 C14 111.6(3) . . ?
N1 C13 H13C 109.3 . . ?
C14 C13 H13C 109.3 . . ?
N1 C13 H13D 109.3 . . ?
C14 C13 H13D 109.3 . . ?
H13C C13 H13D 108.0 . . ?
C19 C14 C15 118.6(4) . . ?
C19 C14 C13 121.6(4) . . ?
C15 C14 C13 119.7(3) . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C1B O1B H1B 109.5 . . ?
C10B O4B C11B 116.7(3) . . ?
C8B N1B C3B 110.9(4) . . ?
C8B N1B C13B 122.7(3) . . ?
C3B N1B C13B 126.2(3) . . ?
O1B C1B C2B 116.9(4) . . ?
O1B C1B C6B 124.1(4) . . ?
C2B C1B C6B 118.9(4) . . ?
C1B C2B C3B 119.6(4) . . ?
C1B C2B C7B 130.6(4) . . ?
C3B C2B C7B 109.8(3) . . ?
C4B C3B C2B 122.4(4) . . ?
C4B C3B N1B 129.2(4) . . ?
C2B C3B N1B 108.3(4) . . ?
C5B C4B C3B 116.7(4) . . ?
C5B C4B H4B 121.6 . . ?
C3B C4B H4B 121.6 . . ?
C4B C5B C6B 122.4(4) . . ?
C4B C5B H5B 118.8 . . ?
C6B C5B H5B 118.8 . . ?
C5B C6B C1B 120.0(4) . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
C2B C7B C9B 116.1(3) . . ?
C2B C7B C8B 101.0(3) . . ?
C9B C7B C8B 113.7(3) . . ?
C2B C7B H7B 108.5 . . ?
C9B C7B H7B 108.5 . . ?
C8B C7B H7B 108.5 . . ?
O2B C8B N1B 124.8(4) . . ?
O2B C8B C7B 125.4(4) . . ?
N1B C8B C7B 109.7(3) . . ?
C10B C9B C7B 113.9(4) . . ?
C10B C9B H9BA 108.8 . . ?
C7B C9B H9BA 108.8 . . ?
C10B C9B H9BB 108.8 . . ?
C7B C9B H9BB 108.8 . . ?
H9BA C9B H9BB 107.7 . . ?
O3B C10B O4B 123.6(4) . . ?
O3B C10B C9B 125.3(4) . . ?
O4B C10B C9B 111.1(4) . . ?
O4B C11B C12B 111.2(3) . . ?
O4B C11B H11A 109.4 . . ?
C12B C11B H11A 109.4 . . ?
O4B C11B H11B 109.4 . . ?
C12B C11B H11B 109.4 . . ?
H11A C11B H11B 108.0 . . ?
C11B C12B H12A 109.5 . . ?
C11B C12B H12B 109.5 . . ?
H12A C12B H12B 109.5 . . ?
C11B C12B H12C 109.5 . . ?
H12A C12B H12C 109.5 . . ?
H12B C12B H12C 109.5 . . ?
N1B C13B C14B 112.2(4) . . ?
N1B C13B H13A 109.2 . . ?
C14B C13B H13A 109.2 . . ?
N1B C13B H13B 109.2 . . ?
C14B C13B H13B 109.2 . . ?
H13A C13B H13B 107.9 . . ?
C19B C14B C15B 118.1(4) . . ?
C19B C14B C13B 120.7(3) . . ?
C15B C14B C13B 121.1(4) . . ?
C16B C15B C14B 121.0(4) . . ?
C16B C15B H15B 119.5 . . ?
C14B C15B H15B 119.5 . . ?
C15B C16B C17B 120.0(4) . . ?
C15B C16B H16B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C16B C17B C18B 119.7(4) . . ?
C16B C17B H17B 120.2 . . ?
C18B C17B H17B 120.2 . . ?
C19B C18B C17B 120.1(4) . . ?
C19B C18B H18B 119.9 . . ?
C17B C18B H18B 119.9 . . ?
C18B C19B C14B 121.1(4) . . ?
C18B C19B H19B 119.5 . . ?
C14B C19B H19B 119.5 . . ?

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 C2 C3 177.3(3) . . . . ?
C6 C1 C2 C3 -2.1(6) . . . . ?
O1 C1 C2 C7 -0.8(6) . . . . ?
C6 C1 C2 C7 179.8(4) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
C7 C2 C3 C4 179.9(4) . . . . ?
C1 C2 C3 N1 -177.0(3) . . . . ?
C7 C2 C3 N1 1.5(4) . . . . ?
C8 N1 C3 C2 -3.0(4) . . . . ?
C13 N1 C3 C2 -179.4(3) . . . . ?
C8 N1 C3 C4 178.8(4) . . . . ?
C13 N1 C3 C4 2.4(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
N1 C3 C4 C5 178.2(4) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
O1 C1 C6 C5 -178.1(4) . . . . ?
C2 C1 C6 C5 1.3(6) . . . . ?
C3 C2 C7 C8 0.3(4) . . . . ?
C1 C2 C7 C8 178.6(4) . . . . ?
C3 C2 C7 C9 124.3(4) . . . . ?
C1 C2 C7 C9 -57.4(5) . . . . ?
C3 N1 C8 O2 -178.1(3) . . . . ?
C13 N1 C8 O2 -1.7(6) . . . . ?
C3 N1 C8 C7 3.2(4) . . . . ?
C13 N1 C8 C7 179.7(3) . . . . ?
C2 C7 C8 O2 179.2(4) . . . . ?
C9 C7 C8 O2 54.2(5) . . . . ?
C2 C7 C8 N1 -2.1(4) . . . . ?
C9 C7 C8 N1 -127.1(4) . . . . ?
C2 C7 C9 C10 -48.6(5) . . . . ?
C8 C7 C9 C10 69.2(4) . . . . ?
C11 O4 C10 O3 0.1(6) . . . . ?
C11 O4 C10 C9 -178.1(3) . . . . ?
C7 C9 C10 O3 135.2(4) . . . . ?
C7 C9 C10 O4 -46.7(5) . . . . ?
C10 O4 C11 C12 -82.9(5) . . . . ?
C8 N1 C13 C14 -83.6(4) . . . . ?
C3 N1 C13 C14 92.3(5) . . . . ?
N1 C13 C14 C19 -91.4(5) . . . . ?
N1 C13 C14 C15 88.4(5) . . . . ?
C19 C14 C15 C16 3.5(7) . . . . ?
C13 C14 C15 C16 -176.3(4) . . . . ?
C14 C15 C16 C17 -1.9(7) . . . . ?
C15 C16 C17 C18 -1.2(7) . . . . ?
C16 C17 C18 C19 2.6(8) . . . . ?
C17 C18 C19 C14 -0.9(8) . . . . ?
C15 C14 C19 C18 -2.1(7) . . . . ?
C13 C14 C19 C18 177.6(4) . . . . ?
O1B C1B C2B C3B -177.8(3) . . . . ?
C6B C1B C2B C3B 1.2(6) . . . . ?
O1B C1B C2B C7B 2.4(6) . . . . ?
C6B C1B C2B C7B -178.6(4) . . . . ?
C1B C2B C3B C4B -0.2(6) . . . . ?
C7B C2B C3B C4B 179.7(4) . . . . ?
C1B C2B C3B N1B 178.6(3) . . . . ?
C7B C2B C3B N1B -1.5(4) . . . . ?
C8B N1B C3B C4B -177.5(4) . . . . ?
C13B N1B C3B C4B -2.2(6) . . . . ?
C8B N1B C3B C2B 3.8(4) . . . . ?
C13B N1B C3B C2B 179.2(4) . . . . ?
C2B C3B C4B C5B -1.1(6) . . . . ?
N1B C3B C4B C5B -179.5(4) . . . . ?
C3B C4B C5B C6B 1.3(6) . . . . ?
C4B C5B C6B C1B -0.2(6) . . . . ?
O1B C1B C6B C5B 177.9(4) . . . . ?
C2B C1B C6B C5B -1.0(6) . . . . ?
C1B C2B C7B C9B 55.5(5) . . . . ?
C3B C2B C7B C9B -124.4(4) . . . . ?
C1B C2B C7B C8B 178.9(4) . . . . ?
C3B C2B C7B C8B -0.9(4) . . . . ?
C3B N1B C8B O2B 178.0(3) . . . . ?
C13B N1B C8B O2B 2.4(6) . . . . ?
C3B N1B C8B C7B -4.5(4) . . . . ?
C13B N1B C8B C7B 180.0(3) . . . . ?
C2B C7B C8B O2B -179.2(4) . . . . ?
C9B C7B C8B O2B -54.1(5) . . . . ?
C2B C7B C8B N1B 3.2(4) . . . . ?
C9B C7B C8B N1B 128.3(4) . . . . ?
C2B C7B C9B C10B 41.2(5) . . . . ?
C8B C7B C9B C10B -75.4(4) . . . . ?
C11B O4B C10B O3B 5.9(6) . . . . ?
C11B O4B C10B C9B -174.4(3) . . . . ?
C7B C9B C10B O3B -130.5(5) . . . . ?
C7B C9B C10B O4B 49.8(5) . . . . ?
C10B O4B C11B C12B -95.2(5) . . . . ?
C8B N1B C13B C14B 75.9(4) . . . . ?
C3B N1B C13B C14B -98.9(4) . . . . ?
N1B C13B C14B C19B -99.0(5) . . . . ?
N1B C13B C14B C15B 77.5(5) . . . . ?
C19B C14B C15B C16B 1.6(7) . . . . ?
C13B C14B C15B C16B -175.0(4) . . . . ?
C14B C15B C16B C17B 0.5(7) . . . . ?
C15B C16B C17B C18B -2.1(8) . . . . ?
C16B C17B C18B C19B 1.5(8) . . . . ?
C17B C18B C19B C14B 0.7(8) . . . . ?
C15B C14B C19B C18B -2.2(7) . . . . ?
C13B C14B C19B C18B 174.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.886
_diffrn_reflns_theta_full        60.00
_diffrn_measured_fraction_theta_full 0.886
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.088
_database_code_depnum_ccdc_archive 'CCDC 976050'
