# Electronic Supplementary Material (ESI) for ChemComm.
# 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_jdf2_382a_cu
_database_code_depnum_ccdc_archive 'CCDC 1478957'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_audit_creation_date             2015-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl (1R*,2S*,5S*,6R*,7S*)-3-[(2,4-dimethoxyphenyl)methyl]-4-oxo-2-(prop-2-en-1-yl)-10-oxa-3-azatricyclo[5.2.1.0¹,5]dec-8-ene-6-carboxylate'
_chemical_formula_moiety         'C21 H23 N O4'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H23 N1 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   8.12275(8)
_cell_length_b                   19.6409(2)
_cell_length_c                   11.31395(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.5884(10)
_cell_angle_gamma                90
_cell_volume                     1803.16(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.2520
_cell_measurement_theta_min      6.9480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5250
_diffrn_reflns_point_group_measured_fraction_full 0.739
_diffrn_reflns_point_group_measured_fraction_max 0.722
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.353
_diffrn_reflns_theta_min         4.502
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   29.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -53.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -33.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega  135.00  161.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   50.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega  128.00  160.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega   88.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   89.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00   81.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
 14 omega  140.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 15 omega   66.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
 16 omega   72.00  130.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 17 omega   86.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   70.00  126.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 19 omega  104.00  129.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   52.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   79.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   40.9904 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0821679000
_diffrn_orient_matrix_UB_12      0.0467071000
_diffrn_orient_matrix_UB_13      -0.0949425000
_diffrn_orient_matrix_UB_21      -0.1238546000
_diffrn_orient_matrix_UB_22      -0.0569351000
_diffrn_orient_matrix_UB_23      -0.0339467000
_diffrn_orient_matrix_UB_31      -0.1178415000
_diffrn_orient_matrix_UB_32      0.0271865000
_diffrn_orient_matrix_UB_33      0.0917503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.459
_reflns_Friedel_fraction_full    0.483
_reflns_Friedel_fraction_max     0.455
_reflns_number_gt                2640
_reflns_number_total             2656
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.039
_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)+(0.0575P)²+0.5516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0799
_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:
 C4(H4), C5(H5), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C12(H12A,H12B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O1 O 0.51668(17) 0.21268(6) 0.91825(13) 0.0195(3) Uani 1 1 d . . . . .
N1 N 0.27816(18) 0.41586(8) 0.73935(13) 0.0144(3) Uani 1 1 d . . . . .
C1 C 0.7203(3) 0.12971(11) 0.87904(19) 0.0263(4) Uani 1 1 d . . . . .
H1A H 0.6585 0.1183 0.8075 0.039 Uiso 1 1 calc GR . . . .
H1B H 0.6844 0.1018 0.9426 0.039 Uiso 1 1 calc GR . . . .
H1C H 0.8354 0.1220 0.8685 0.039 Uiso 1 1 calc GR . . . .
O2 O 0.56366(18) 0.32180(7) 0.96675(14) 0.0233(3) Uani 1 1 d . . . . .
C2 C 0.6932(2) 0.20349(10) 0.90808(19) 0.0225(4) Uani 1 1 d . . . . .
H2A H 0.7515 0.2153 0.9819 0.027 Uiso 1 1 calc R . . . .
H2B H 0.7330 0.2323 0.8459 0.027 Uiso 1 1 calc R . . . .
O3 O 0.25218(16) 0.39472(6) 0.99507(11) 0.0153(3) Uani 1 1 d . . . . .
C3 C 0.4690(2) 0.27567(9) 0.94592(16) 0.0158(4) Uani 1 1 d . . . . .
O4 O 0.41487(17) 0.31683(7) 0.69627(12) 0.0201(3) Uani 1 1 d . . . . .
C4 C 0.2832(2) 0.28062(9) 0.94987(16) 0.0160(4) Uani 1 1 d . . . . .
H4 H 0.2339 0.2355 0.9591 0.019 Uiso 1 1 calc R . . . .
C5 C 0.2323(2) 0.32987(9) 1.05152(16) 0.0170(4) Uani 1 1 d . . . . .
H5 H 0.2959 0.3243 1.1266 0.020 Uiso 1 1 calc R . . . .
C6 C 0.0470(3) 0.32627(10) 1.06096(17) 0.0203(4) Uani 1 1 d . . . . .
H6 H -0.0102 0.3040 1.1189 0.024 Uiso 1 1 calc R . . . .
C7 C -0.0176(2) 0.36155(9) 0.96907(18) 0.0181(4) Uani 1 1 d . . . . .
H7 H -0.1283 0.3706 0.9511 0.022 Uiso 1 1 calc R . . . .
C8 C 0.1297(2) 0.38346(9) 0.90058(16) 0.0145(4) Uani 1 1 d . . . . .
C9 C 0.2014(2) 0.31882(9) 0.84162(16) 0.0145(4) Uani 1 1 d . . . . .
H9 H 0.1136 0.2914 0.8032 0.017 Uiso 1 1 calc R . . . .
C10 C 0.3133(2) 0.34850(9) 0.75128(16) 0.0149(3) Uani 1 1 d . . . . .
C11 C 0.1429(2) 0.44042(9) 0.81019(16) 0.0160(4) Uani 1 1 d . . . . .
H11 H 0.1768 0.4825 0.8509 0.019 Uiso 1 1 calc R . . . .
C12 C -0.0156(2) 0.45358(10) 0.73406(18) 0.0206(4) Uani 1 1 d . . . . .
H12A H -0.1009 0.4692 0.7848 0.025 Uiso 1 1 calc R . . . .
H12B H 0.0050 0.4896 0.6780 0.025 Uiso 1 1 calc R . . . .
C13 C -0.0770(3) 0.39185(11) 0.66728(17) 0.0223(4) Uani 1 1 d . . . . .
H13 H -0.0118 0.3743 0.6091 0.027 Uiso 1 1 calc R . . . .
C14 C -0.2179(3) 0.36097(11) 0.68600(19) 0.0249(4) Uani 1 1 d . . . . .
H14A H -0.2859 0.3773 0.7436 0.030 Uiso 1 1 calc R . . . .
H14B H -0.2492 0.3229 0.6416 0.030 Uiso 1 1 calc R . . . .
C15 C 0.3732(2) 0.46108(9) 0.66695(16) 0.0168(4) Uani 1 1 d . . . . .
H15A H 0.2979 0.4899 0.6205 0.020 Uiso 1 1 calc R . . . .
H15B H 0.4344 0.4340 0.6124 0.020 Uiso 1 1 calc R . . . .
C16 C 0.4929(2) 0.50589(9) 0.73858(16) 0.0152(3) Uani 1 1 d . . . . .
C17 C 0.5577(2) 0.56351(9) 0.68495(16) 0.0169(4) Uani 1 1 d . . . . .
H17 H 0.5247 0.5743 0.6074 0.020 Uiso 1 1 calc R . . . .
C18 C 0.6711(2) 0.60480(9) 0.74664(18) 0.0201(4) Uani 1 1 d . . . . .
H18 H 0.7142 0.6428 0.7101 0.024 Uiso 1 1 calc R . . . .
C19 C 0.7202(2) 0.58925(10) 0.86290(18) 0.0207(4) Uani 1 1 d . . . . .
H19 H 0.7954 0.6170 0.9045 0.025 Uiso 1 1 calc R . . . .
C20 C 0.6562(2) 0.53209(9) 0.91647(17) 0.0185(4) Uani 1 1 d . . . . .
H20 H 0.6891 0.5215 0.9941 0.022 Uiso 1 1 calc R . . . .
C21 C 0.5431(2) 0.49046(9) 0.85488(16) 0.0164(4) Uani 1 1 d . . . . .
H21 H 0.5011 0.4522 0.8915 0.020 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 C2 1.454(2) . ?
O1 C3 1.338(2) . ?
N1 C10 1.359(2) . ?
N1 C11 1.470(2) . ?
N1 C15 1.453(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.504(3) . ?
O2 C3 1.205(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O3 C5 1.437(2) . ?
O3 C8 1.444(2) . ?
C3 C4 1.515(3) . ?
O4 C10 1.225(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.572(3) . ?
C4 C9 1.559(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.516(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.337(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.517(3) . ?
C8 C9 1.559(2) . ?
C8 C11 1.523(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.515(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.538(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.502(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.321(3) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.518(2) . ?
C16 C17 1.398(2) . ?
C16 C21 1.393(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.391(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.393(3) . ?
C21 H21 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
C3 O1 C2 115.47(14) . . ?
C10 N1 C11 115.08(15) . . ?
C10 N1 C15 122.45(16) . . ?
C15 N1 C11 122.39(15) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 106.96(17) . . ?
O1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C5 O3 C8 96.08(12) . . ?
O1 C3 C4 111.44(15) . . ?
O2 C3 O1 123.54(18) . . ?
O2 C3 C4 125.01(17) . . ?
C3 C4 H4 110.9 . . ?
C3 C4 C5 110.86(15) . . ?
C3 C4 C9 113.41(15) . . ?
C5 C4 H4 110.9 . . ?
C9 C4 H4 110.9 . . ?
C9 C4 C5 99.32(14) . . ?
O3 C5 C4 100.47(14) . . ?
O3 C5 H5 114.8 . . ?
O3 C5 C6 101.80(14) . . ?
C4 C5 H5 114.8 . . ?
C6 C5 C4 108.50(15) . . ?
C6 C5 H5 114.8 . . ?
C5 C6 H6 127.0 . . ?
C7 C6 C5 106.09(17) . . ?
C7 C6 H6 127.0 . . ?
C6 C7 H7 127.7 . . ?
C6 C7 C8 104.68(17) . . ?
C8 C7 H7 127.7 . . ?
O3 C8 C7 101.43(14) . . ?
O3 C8 C9 100.55(13) . . ?
O3 C8 C11 108.51(14) . . ?
C7 C8 C9 107.82(14) . . ?
C7 C8 C11 129.25(16) . . ?
C11 C8 C9 105.78(15) . . ?
C4 C9 C8 102.12(14) . . ?
C4 C9 H9 111.1 . . ?
C8 C9 H9 111.1 . . ?
C10 C9 C4 117.90(15) . . ?
C10 C9 C8 102.86(14) . . ?
C10 C9 H9 111.1 . . ?
N1 C10 C9 108.18(16) . . ?
O4 C10 N1 125.94(18) . . ?
O4 C10 C9 125.86(16) . . ?
N1 C11 C8 101.67(14) . . ?
N1 C11 H11 109.4 . . ?
N1 C11 C12 112.16(15) . . ?
C8 C11 H11 109.4 . . ?
C8 C11 C12 114.64(16) . . ?
C12 C11 H11 109.4 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.36(15) . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C12 C13 H13 118.0 . . ?
C14 C13 C12 124.1(2) . . ?
C14 C13 H13 118.0 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
N1 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
N1 C15 C16 113.38(15) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C17 C16 C15 118.82(15) . . ?
C21 C16 C15 122.09(16) . . ?
C21 C16 C17 119.07(16) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.52(17) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.10(18) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.57(17) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.52(17) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.22(17) . . ?
C20 C21 H21 119.9 . . ?

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 C3 C4 C5 143.42(15) . . . . ?
O1 C3 C4 C9 -105.87(17) . . . . ?
N1 C11 C12 C13 58.1(2) . . . . ?
N1 C15 C16 C17 -162.69(16) . . . . ?
N1 C15 C16 C21 18.9(2) . . . . ?
O2 C3 C4 C5 -35.4(2) . . . . ?
O2 C3 C4 C9 75.3(2) . . . . ?
C2 O1 C3 O2 -3.3(3) . . . . ?
C2 O1 C3 C4 177.86(15) . . . . ?
O3 C5 C6 C7 30.10(18) . . . . ?
O3 C8 C9 C4 33.54(16) . . . . ?
O3 C8 C9 C10 -89.13(15) . . . . ?
O3 C8 C11 N1 82.74(16) . . . . ?
O3 C8 C11 C12 -156.03(15) . . . . ?
C3 O1 C2 C1 178.98(16) . . . . ?
C3 C4 C5 O3 80.43(16) . . . . ?
C3 C4 C5 C6 -173.24(15) . . . . ?
C3 C4 C9 C8 -114.60(16) . . . . ?
C3 C4 C9 C10 -2.8(2) . . . . ?
C4 C5 C6 C7 -75.31(18) . . . . ?
C4 C9 C10 N1 -124.92(16) . . . . ?
C4 C9 C10 O4 56.8(2) . . . . ?
C5 O3 C8 C7 51.52(15) . . . . ?
C5 O3 C8 C9 -59.29(15) . . . . ?
C5 O3 C8 C11 -170.02(14) . . . . ?
C5 C4 C9 C8 3.06(17) . . . . ?
C5 C4 C9 C10 114.85(17) . . . . ?
C5 C6 C7 C8 2.79(19) . . . . ?
C6 C7 C8 O3 -34.69(18) . . . . ?
C6 C7 C8 C9 70.46(18) . . . . ?
C6 C7 C8 C11 -160.39(18) . . . . ?
C7 C8 C9 C4 -72.22(17) . . . . ?
C7 C8 C9 C10 165.10(14) . . . . ?
C7 C8 C11 N1 -154.33(16) . . . . ?
C7 C8 C11 C12 -33.1(3) . . . . ?
C8 O3 C5 C4 61.94(15) . . . . ?
C8 O3 C5 C6 -49.67(15) . . . . ?
C8 C9 C10 N1 -13.54(17) . . . . ?
C8 C9 C10 O4 168.18(16) . . . . ?
C8 C11 C12 C13 -57.2(2) . . . . ?
C9 C4 C5 O3 -39.14(16) . . . . ?
C9 C4 C5 C6 67.19(17) . . . . ?
C9 C8 C11 N1 -24.43(17) . . . . ?
C9 C8 C11 C12 96.79(17) . . . . ?
C10 N1 C11 C8 17.30(19) . . . . ?
C10 N1 C11 C12 -105.63(17) . . . . ?
C10 N1 C15 C16 -102.82(18) . . . . ?
C11 N1 C10 O4 176.02(17) . . . . ?
C11 N1 C10 C9 -2.26(19) . . . . ?
C11 N1 C15 C16 73.7(2) . . . . ?
C11 C8 C9 C4 146.39(14) . . . . ?
C11 C8 C9 C10 23.71(17) . . . . ?
C11 C12 C13 C14 114.9(2) . . . . ?
C15 N1 C10 O4 -7.2(3) . . . . ?
C15 N1 C10 C9 174.51(15) . . . . ?
C15 N1 C11 C8 -159.47(14) . . . . ?
C15 N1 C11 C12 77.6(2) . . . . ?
C15 C16 C17 C18 -178.25(18) . . . . ?
C15 C16 C21 C20 178.47(17) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C16 -0.1(3) . . . . ?
C21 C16 C17 C18 0.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
5 -2 -2 0.0631 5.0000 -2.0000 -2.0000 -0.3144 -0.4375 -0.8271
1 11 3 0.0601 1.0000 11.0000 3.0000 0.1468 -0.8520 0.4565
-5 -2 1 0.0719 -5.0000 -2.0000 1.0000 0.2225 0.6992 0.6266
-1 -12 -3 0.0723 -1.0000 -12.0000 -3.0000 -0.1935 0.9089 -0.4836
2 -8 -5 0.0590 2.0000 -8.0000 -5.0000 -0.0633 0.3775 -0.9119
-2 5 -6 0.0612 -2.0000 5.0000 -6.0000 0.9675 0.1667 -0.1789
-2 9 5 0.0757 -2.0000 9.0000 5.0000 0.1100 -0.4344 0.9391
2 -7 5 0.0985 2.0000 -7.0000 5.0000 -0.9660 -0.0189 0.0328
1 -1 7 0.0840 1.0000 -1.0000 7.0000 -0.7935 -0.3045 0.4972
2 0 -7 0.0656 2.0000 0.0000 -7.0000 0.5003 -0.0101 -0.8779
4 7 -3 0.0833 4.0000 7.0000 -3.0000 0.2831 -0.7921 -0.5563
2 8 5 0.0509 2.0000 8.0000 5.0000 -0.2654 -0.8729 0.4406
0 6 6 0.0538 -0.0000 6.0000 6.0000 -0.2894 -0.5453 0.7136
-4 -7 3 0.0764 -4.0000 -7.0000 3.0000 -0.2831 0.7921 0.5563
-1 -7 -6 0.0695 -1.0000 -7.0000 -6.0000 0.3249 0.7261 -0.6230
0 7 -6 0.0643 -0.0000 7.0000 -6.0000 0.8966 -0.1949 -0.3602
3 4 6 0.0514 3.0000 4.0000 6.0000 -0.6293 -0.8030 0.3057
0 12 -2 0.0633 -0.0000 12.0000 -2.0000 0.7504 -0.6153 0.1427
-3 -10 3 0.0889 -3.0000 -10.0000 3.0000 -0.5054 0.8391 0.3569

_olex2_date_sample_data_collection 2015-09-10
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jdf3_464a_cu
_database_code_depnum_ccdc_archive 'CCDC 1478958'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl (2R*,3S*,5aS*,9aS*,9bR*)-5-benzyl-2-ethenyl-4-oxo-2H,3H,4H,5H,5aH,6H,7H,9bH-furo[3,2-d]indole-3-carboxylate'
_chemical_formula_moiety         'C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C88 H100 N4 O16'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.06181(17)
_cell_length_b                   9.47232(16)
_cell_length_c                   18.5215(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.9172(13)
_cell_angle_gamma                90
_cell_volume                     1922.20(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6665
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      74.3120
_cell_measurement_theta_min      4.0180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11845
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.451
_diffrn_reflns_theta_min         4.035
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -60.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega -106.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega   16.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7089   65.0000  152.2519 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   87.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  136.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  8 omega  123.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
  9 omega  139.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega   98.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   89.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega   73.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   84.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000  101.0955 37

#__ type_ start__ end____ width___ exp.time_
 14 omega   71.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   29.0189 35

#__ type_ start__ end____ width___ exp.time_
 15 omega   70.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  105.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega  122.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
 18 omega   75.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
 19 omega   61.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   61.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -56.0000 -165.6941 33

#__ type_ start__ end____ width___ exp.time_
 21 omega   58.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 22 omega   64.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000  -29.9824 49

#__ type_ start__ end____ width___ exp.time_
 23 omega   54.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 24 omega   60.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   60.0535 53

#__ type_ start__ end____ width___ exp.time_
 25 omega   49.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   43.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  120.0000 46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0752335000
_diffrn_orient_matrix_UB_12      -0.0009650000
_diffrn_orient_matrix_UB_13      -0.0640845000
_diffrn_orient_matrix_UB_21      -0.1181409000
_diffrn_orient_matrix_UB_22      0.0166163000
_diffrn_orient_matrix_UB_23      -0.0540029000
_diffrn_orient_matrix_UB_31      0.0127427000
_diffrn_orient_matrix_UB_32      0.1617629000
_diffrn_orient_matrix_UB_33      0.0052501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3389
_reflns_number_total             3807
_reflns_odcompleteness_completeness 98.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.042
_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)+(0.0654P)²+0.5183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1192
_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:
 C2(H2), C4(H4), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B), C13(H13A,H13B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C18(H18)
2.d X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 0.11100(8) 0.26997(10) 0.31475(5) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.04846(9) 0.12652(12) 0.21640(6) 0.0180(2) Uani 1 1 d . . . . .
C1 C 0.13049(11) 0.17888(14) 0.27089(6) 0.0170(3) Uani 1 1 d . . . . .
O2 O 0.26400(8) 0.15727(10) 0.14469(5) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.09872(11) 0.01017(14) 0.17845(6) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.0847 -0.0773 0.2043 0.021 Uiso 1 1 calc R . . . .
O3 O 0.35937(9) 0.45095(11) 0.31184(5) 0.0266(2) Uani 1 1 d . . . . .
C3 C 0.23505(11) 0.04153(13) 0.19148(6) 0.0170(3) Uani 1 1 d . . . . .
O4 O 0.40540(9) 0.26619(11) 0.38698(5) 0.0273(2) Uani 1 1 d . . . . .
C4 C 0.25445(11) 0.10681(13) 0.26745(6) 0.0164(3) Uani 1 1 d . . . . .
H4 H 0.2750 0.0367 0.3061 0.020 Uiso 1 1 calc R . . . .
C5 C -0.08189(11) 0.15539(14) 0.20934(7) 0.0200(3) Uani 1 1 d . . . . .
H5A H -0.1015 0.1903 0.2556 0.024 Uiso 1 1 calc R . . . .
H5B H -0.1262 0.0679 0.1986 0.024 Uiso 1 1 calc R . . . .
C6 C -0.12434(12) 0.26229(14) 0.15023(7) 0.0195(3) Uani 1 1 d . . . . .
C7 C -0.24285(12) 0.25467(15) 0.11324(8) 0.0236(3) Uani 1 1 d . . . . .
H7 H -0.2952 0.1836 0.1245 0.028 Uiso 1 1 calc R . . . .
C8 C -0.28286(13) 0.35311(16) 0.05964(8) 0.0286(3) Uani 1 1 d . . . . .
H8 H -0.3619 0.3472 0.0351 0.034 Uiso 1 1 calc R . . . .
C9 C -0.20657(15) 0.45964(16) 0.04244(8) 0.0296(3) Uani 1 1 d . . . . .
H9 H -0.2338 0.5251 0.0064 0.036 Uiso 1 1 calc R . . . .
C10 C -0.08887(14) 0.46812(17) 0.07937(8) 0.0300(3) Uani 1 1 d . . . . .
H10 H -0.0371 0.5399 0.0683 0.036 Uiso 1 1 calc R . . . .
C11 C -0.04826(13) 0.36991(16) 0.13268(8) 0.0253(3) Uani 1 1 d . . . . .
H11 H 0.0309 0.3762 0.1570 0.030 Uiso 1 1 calc R . . . .
C12 C 0.05802(12) -0.01396(14) 0.09801(7) 0.0205(3) Uani 1 1 d . . . . .
H12A H 0.0816 0.0650 0.0696 0.025 Uiso 1 1 calc R . . . .
H12B H -0.0299 -0.0249 0.0884 0.025 Uiso 1 1 calc R . . . .
C13 C 0.12248(13) -0.15045(15) 0.07839(7) 0.0241(3) Uani 1 1 d . . . . .
H13A H 0.0740 -0.2308 0.0897 0.029 Uiso 1 1 calc R . . . .
H13B H 0.1252 -0.1513 0.0263 0.029 Uiso 1 1 calc R . . . .
C14 C 0.25079(13) -0.16836(15) 0.11738(7) 0.0245(3) Uani 1 1 d . . . . .
H14 H 0.2968 -0.2427 0.1028 0.029 Uiso 1 1 calc R . . . .
C15 C 0.30305(12) -0.08576(15) 0.17098(7) 0.0225(3) Uani 1 1 d . . . . .
H15 H 0.3803 -0.1067 0.1952 0.027 Uiso 1 1 calc R . . . .
C16 C 0.35663(11) 0.21426(14) 0.26325(6) 0.0174(3) Uani 1 1 d . . . . .
H16 H 0.4340 0.1632 0.2648 0.021 Uiso 1 1 calc R . . . .
C17 C 0.32114(11) 0.27340(14) 0.18630(7) 0.0181(3) Uani 1 1 d . . . . .
H17 H 0.2616 0.3496 0.1878 0.022 Uiso 1 1 calc R . . . .
C18 C 0.42582(12) 0.32623(15) 0.15069(7) 0.0223(3) Uani 1 1 d . . . . .
H18 H 0.4857 0.2622 0.1416 0.027 Uiso 1 1 calc R . . . .
C19 C 0.43752(14) 0.45843(17) 0.13155(8) 0.0311(3) Uani 1 1 d . . . . .
H19A H 0.3789 0.5245 0.1400 0.037 Uiso 1 1 calc R . . . .
H19B H 0.5044 0.4860 0.1095 0.037 Uiso 1 1 calc R . . . .
C20 C 0.37137(11) 0.32599(15) 0.32203(7) 0.0195(3) Uani 1 1 d . . . . .
C21 C 0.41797(15) 0.36209(19) 0.44901(8) 0.0338(4) Uani 1 1 d . . . . .
H21A H 0.4555 0.4493 0.4360 0.041 Uiso 1 1 calc R . . . .
H21B H 0.4708 0.3198 0.4894 0.041 Uiso 1 1 calc R . . . .
C22 C 0.29589(15) 0.39382(17) 0.47210(8) 0.0319(3) Uani 1 1 d . . . . .
H22A H 0.2456 0.4418 0.4333 0.048 Uiso 1 1 calc GR . . . .
H22B H 0.3068 0.4528 0.5147 0.048 Uiso 1 1 calc GR . . . .
H22C H 0.2572 0.3072 0.4831 0.048 Uiso 1 1 calc GR . . . .


_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 1.2243(16) . ?
N1 C1 1.3549(16) . ?
N1 C2 1.4578(16) . ?
N1 C5 1.4557(16) . ?
C1 C4 1.5409(16) . ?
O2 C3 1.4601(15) . ?
O2 C17 1.4385(15) . ?
C2 H2 0.9800 . ?
C2 C3 1.5233(17) . ?
C2 C12 1.5133(17) . ?
O3 C20 1.2031(18) . ?
C3 C4 1.5248(16) . ?
C3 C15 1.4975(17) . ?
O4 C20 1.3360(16) . ?
O4 C21 1.4562(16) . ?
C4 H4 0.9800 . ?
C4 C16 1.5309(17) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5176(18) . ?
C6 C7 1.3948(18) . ?
C6 C11 1.3887(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(2) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5437(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.511(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.332(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C17 1.5312(17) . ?
C16 C20 1.5110(17) . ?
C17 H17 0.9800 . ?
C17 C18 1.4956(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.313(2) . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.502(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 N1 C2 112.04(10) . . ?
C1 N1 C5 123.48(11) . . ?
C5 N1 C2 122.51(10) . . ?
O1 C1 N1 126.24(12) . . ?
O1 C1 C4 125.36(11) . . ?
N1 C1 C4 108.39(10) . . ?
C17 O2 C3 111.86(9) . . ?
N1 C2 H2 107.9 . . ?
N1 C2 C3 102.19(10) . . ?
N1 C2 C12 120.49(11) . . ?
C3 C2 H2 107.9 . . ?
C12 C2 H2 107.9 . . ?
C12 C2 C3 109.83(10) . . ?
O2 C3 C2 110.22(10) . . ?
O2 C3 C4 103.22(10) . . ?
O2 C3 C15 107.17(10) . . ?
C2 C3 C4 103.63(9) . . ?
C15 C3 C2 108.89(11) . . ?
C15 C3 C4 123.28(11) . . ?
C20 O4 C21 115.49(11) . . ?
C1 C4 H4 112.9 . . ?
C3 C4 C1 101.83(9) . . ?
C3 C4 H4 112.9 . . ?
C3 C4 C16 103.52(9) . . ?
C16 C4 C1 112.03(10) . . ?
C16 C4 H4 112.9 . . ?
N1 C5 H5A 108.9 . . ?
N1 C5 H5B 108.9 . . ?
N1 C5 C6 113.23(10) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C7 C6 C5 119.76(12) . . ?
C11 C6 C5 121.42(12) . . ?
C11 C6 C7 118.81(13) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.11(13) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.71(13) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.38(14) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.18(14) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.81(13) . . ?
C10 C11 H11 119.6 . . ?
C2 C12 H12A 110.6 . . ?
C2 C12 H12B 110.6 . . ?
C2 C12 C13 105.89(11) . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 H12A 110.6 . . ?
C13 C12 H12B 110.6 . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C12 114.55(11) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14 117.5 . . ?
C15 C14 C13 124.97(12) . . ?
C15 C14 H14 117.5 . . ?
C3 C15 H15 120.6 . . ?
C14 C15 C3 118.71(12) . . ?
C14 C15 H15 120.6 . . ?
C4 C16 H16 108.5 . . ?
C4 C16 C17 101.19(9) . . ?
C17 C16 H16 108.5 . . ?
C20 C16 C4 115.86(10) . . ?
C20 C16 H16 108.5 . . ?
C20 C16 C17 113.75(11) . . ?
O2 C17 C16 104.85(10) . . ?
O2 C17 H17 109.3 . . ?
O2 C17 C18 109.23(10) . . ?
C16 C17 H17 109.3 . . ?
C18 C17 C16 114.71(10) . . ?
C18 C17 H17 109.3 . . ?
C17 C18 H18 118.3 . . ?
C19 C18 C17 123.33(14) . . ?
C19 C18 H18 118.3 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
O3 C20 O4 124.73(12) . . ?
O3 C20 C16 125.27(12) . . ?
O4 C20 C16 109.93(11) . . ?
O4 C21 H21A 109.4 . . ?
O4 C21 H21B 109.4 . . ?
O4 C21 C22 110.95(13) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C4 C3 -163.20(12) . . . . ?
O1 C1 C4 C16 -53.18(16) . . . . ?
N1 C1 C4 C3 15.47(13) . . . . ?
N1 C1 C4 C16 125.48(11) . . . . ?
N1 C2 C3 O2 -75.79(11) . . . . ?
N1 C2 C3 C4 34.09(12) . . . . ?
N1 C2 C3 C15 166.91(10) . . . . ?
N1 C2 C12 C13 -176.03(11) . . . . ?
N1 C5 C6 C7 150.01(12) . . . . ?
N1 C5 C6 C11 -31.10(17) . . . . ?
C1 N1 C2 C3 -25.84(13) . . . . ?
C1 N1 C2 C12 -147.85(11) . . . . ?
C1 N1 C5 C6 103.93(14) . . . . ?
C1 C4 C16 C17 -69.95(11) . . . . ?
C1 C4 C16 C20 53.57(14) . . . . ?
O2 C3 C4 C1 84.83(10) . . . . ?
O2 C3 C4 C16 -31.55(11) . . . . ?
O2 C3 C15 C14 -87.61(14) . . . . ?
O2 C17 C18 C19 125.34(14) . . . . ?
C2 N1 C1 O1 -174.77(12) . . . . ?
C2 N1 C1 C4 6.58(14) . . . . ?
C2 N1 C5 C6 -93.34(14) . . . . ?
C2 C3 C4 C1 -30.15(12) . . . . ?
C2 C3 C4 C16 -146.53(10) . . . . ?
C2 C3 C15 C14 31.60(16) . . . . ?
C2 C12 C13 C14 -36.86(15) . . . . ?
C3 O2 C17 C16 13.20(12) . . . . ?
C3 O2 C17 C18 136.61(11) . . . . ?
C3 C2 C12 C13 65.75(13) . . . . ?
C3 C4 C16 C17 39.00(11) . . . . ?
C3 C4 C16 C20 162.51(10) . . . . ?
C4 C3 C15 C14 153.11(13) . . . . ?
C4 C16 C17 O2 -32.03(11) . . . . ?
C4 C16 C17 C18 -151.84(11) . . . . ?
C4 C16 C20 O3 -117.91(14) . . . . ?
C4 C16 C20 O4 64.97(14) . . . . ?
C5 N1 C1 O1 -10.4(2) . . . . ?
C5 N1 C1 C4 170.91(11) . . . . ?
C5 N1 C2 C3 169.65(11) . . . . ?
C5 N1 C2 C12 47.65(17) . . . . ?
C5 C6 C7 C8 179.26(12) . . . . ?
C5 C6 C11 C10 -178.98(13) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C6 C11 C10 -0.1(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 C6 -0.3(2) . . . . ?
C11 C6 C7 C8 0.3(2) . . . . ?
C12 C2 C3 O2 53.24(13) . . . . ?
C12 C2 C3 C4 163.12(10) . . . . ?
C12 C2 C3 C15 -64.06(13) . . . . ?
C12 C13 C14 C15 7.9(2) . . . . ?
C13 C14 C15 C3 -4.9(2) . . . . ?
C15 C3 C4 C1 -154.04(12) . . . . ?
C15 C3 C4 C16 89.57(14) . . . . ?
C16 C17 C18 C19 -117.32(15) . . . . ?
C17 O2 C3 C2 121.70(11) . . . . ?
C17 O2 C3 C4 11.55(12) . . . . ?
C17 O2 C3 C15 -119.94(11) . . . . ?
C17 C16 C20 O3 -1.24(18) . . . . ?
C17 C16 C20 O4 -178.35(10) . . . . ?
C20 O4 C21 C22 80.76(17) . . . . ?
C20 C16 C17 O2 -156.98(10) . . . . ?
C20 C16 C17 C18 83.21(13) . . . . ?
C21 O4 C20 O3 5.30(19) . . . . ?
C21 O4 C20 C16 -177.56(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
-6 0 -6 0.0625 -6.0000 0.0000 -6.0000 -0.0669 1.0329 -0.1080
6 0 6 0.0625 6.0000 -0.0000 6.0000 0.0669 -1.0329 0.1080
-3 -5 3 0.1707 -3.0000 -5.0000 3.0000 -0.4131 0.1093 -0.8313
2 6 -4 0.1181 2.0000 6.0000 -4.0000 0.4010 0.0794 0.9751
-5 -1 10 0.0643 -5.0000 -1.0000 10.0000 -1.0160 0.0341 -0.1730
5 0 -10 0.0591 5.0000 -0.0000 -10.0000 1.0170 -0.0507 0.0112
-4 -5 -1 0.1527 -4.0000 -5.0000 -1.0000 -0.2320 0.4435 -0.8650
3 5 4 0.1279 3.0000 5.0000 4.0000 -0.0355 -0.4874 0.8680
-3 -4 -8 0.1289 -3.0000 -4.0000 -8.0000 0.2908 0.7200 -0.7273
5 -5 1 0.1730 5.0000 -5.0000 1.0000 0.3169 -0.7278 -0.7399
1 5 7 0.1107 1.0000 5.0000 7.0000 -0.3782 -0.4131 0.8583
-5 0 10 0.0623 -5.0000 0.0000 10.0000 -1.0170 0.0507 -0.0112
7 0 -3 0.0639 7.0000 -0.0000 -3.0000 0.7189 -0.6650 0.0734
-7 1 3 0.0672 -7.0000 1.0000 3.0000 -0.7199 0.6816 0.0883
-2 0 12 0.0411 -2.0000 -0.0000 12.0000 -0.9195 -0.4118 0.0375
2 0 -12 0.0558 2.0000 0.0000 -12.0000 0.9195 0.4118 -0.0375
1 0 12 0.0331 1.0000 -0.0000 12.0000 -0.6938 -0.7662 0.0757
-1 0 -12 0.0445 -1.0000 0.0000 -12.0000 0.6938 0.7662 -0.0757

_olex2_date_sample_data_collection 2015-11-30
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jdf3_509b_cu_a_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1478959'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_audit_creation_date             2016-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'Methyl (1R*,2R*,5S*,8S*,9R*,10S*)-7-oxo-5-{[4-(trifluoromethyl)phenyl]methyl}-13-oxa-6-azatetracyclo[8.2.1.0¹,8.0²,6]tridecane-9-carboxylate'
_chemical_formula_moiety         'C21 H22 F3 N O4'
_chemical_formula_sum            'C21 H22 F3 N O4'
_chemical_formula_weight         409.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H22 F3 N1 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.7112(3)
_cell_length_b                   15.2229(4)
_cell_length_c                   22.2156(6)
_cell_angle_alpha                78.173(2)
_cell_angle_beta                 76.486(2)
_cell_angle_gamma                89.949(2)
_cell_volume                     3764.56(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    21806
_cell_measurement_temperature    119.99(18)
_cell_measurement_theta_max      73.3340
_cell_measurement_theta_min      4.5800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20977
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.675
_diffrn_reflns_theta_min         3.253
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -107.00  -11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -65.0000   42.7718 96

#__ type_ start__ end____ width___ exp.time_
  2 omega -107.00  -12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -62.0000 -128.7230 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -64.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega  -64.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega  -26.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589  -64.0000 -156.7581 95

#__ type_ start__ end____ width___ exp.time_
  6 omega   16.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   64.0000 -152.4784 95

#__ type_ start__ end____ width___ exp.time_
  7 omega   15.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   65.0000  136.3918 96

#__ type_ start__ end____ width___ exp.time_
  8 omega   15.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   65.0000   22.5721 96

#__ type_ start__ end____ width___ exp.time_
  9 omega  -26.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589  -64.0000    8.6219 95

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -64.0000    8.1232 96

#__ type_ start__ end____ width___ exp.time_
 11 omega   83.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242   30.0000   60.0000 94

#__ type_ start__ end____ width___ exp.time_
 12 omega   83.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242   30.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
 13 omega   31.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -30.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
 14 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000   77.5114 96

#__ type_ start__ end____ width___ exp.time_
 15 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000 -168.5889 96

#__ type_ start__ end____ width___ exp.time_
 16 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000   44.2077 96

#__ type_ start__ end____ width___ exp.time_
 17 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -64.0000  106.3265 96

#__ type_ start__ end____ width___ exp.time_
 18 omega   31.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -30.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
 19 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000  -96.7013 96

#__ type_ start__ end____ width___ exp.time_
 20 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000  -67.7277 96

#__ type_ start__ end____ width___ exp.time_
 21 omega   25.00  144.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -15.0000  120.0000 119

#__ type_ start__ end____ width___ exp.time_
 22 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000 -131.7962 96

#__ type_ start__ end____ width___ exp.time_
 23 omega   31.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -30.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
 24 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000  -25.8588 96

#__ type_ start__ end____ width___ exp.time_
 25 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000  149.0744 96

#__ type_ start__ end____ width___ exp.time_
 26 omega   17.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   57.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
 27 omega   16.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   64.0000   81.9619 95

#__ type_ start__ end____ width___ exp.time_
 28 omega   22.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   37.0000    0.0000 92

#__ type_ start__ end____ width___ exp.time_
 29 omega   22.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   37.0000  -90.0000 92

#__ type_ start__ end____ width___ exp.time_
 30 omega   15.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   65.0000  -91.5379 96

#__ type_ start__ end____ width___ exp.time_
 31 omega   22.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   37.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
 32 omega   16.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   64.0000  -54.4079 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0410824000
_diffrn_orient_matrix_UB_12      -0.0005371000
_diffrn_orient_matrix_UB_13      0.0712124000
_diffrn_orient_matrix_UB_21      -0.0879226000
_diffrn_orient_matrix_UB_22      0.0721568000
_diffrn_orient_matrix_UB_23      -0.0141505000
_diffrn_orient_matrix_UB_31      -0.0945002000
_diffrn_orient_matrix_UB_32      -0.0742283000
_diffrn_orient_matrix_UB_33      0.0071542000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.6812 17207 50576
2 0.3188 17292 50576

_diffrn_oxdiff_twin_integration_method simultaneous
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                17075
_reflns_number_total             20977
_reflns_special_details          
;
 _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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1050
_refine_ls_number_reflns         20977
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.030
_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)+(0.1090P)²+1.5254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1703
_refine_special_details          
;
 Refined as a 2-component twin with SHELX HKLF5, BASF 0.269.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7305(8) 0.2695(8)
2. 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
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C10(H10), C13(H13), C66(H66), C67(H67), C71(H71),
 C73(H73), C76(H76), C24(H24), C25(H25), C29(H29), C31(H31), C34(H34), C45(H45),
  C46(H46), C50(H50), C52(H52), C55(H55)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B),
 C68(H68A,H68B), C69(H69A,H69B), C74(H74A,H74B), C75(H75A,H75B), C77(H77A,H77B),
  C26(H26A,H26B), C27(H27A,H27B), C32(H32A,H32B), C33(H33A,H33B), C35(H35A,
 H35B), C47(H47A,H47B), C48(H48A,H48B), C53(H53A,H53B), C54(H54A,H54B),
 C56(H56A,H56B)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C20(H20), C79(H79), C80(H80), C82(H82),
 C83(H83), C37(H37), C38(H38), C40(H40), C41(H41), C58(H58), C59(H59), C61(H61),
  C62(H62)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C64(H64A,H64B,H64C), C22(H22A,H22B,H22C), C43(H43A,H43B,H43C)
;
_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
F1 F 0.5474(2) 0.87467(15) 0.52989(9) 0.0426(5) Uani 1 1 d . . . . .
O1 O 1.08130(17) 1.33761(14) 0.06826(10) 0.0224(4) Uani 1 1 d . . . . .
N1 N 0.7969(2) 1.34076(16) 0.25961(11) 0.0196(5) Uani 1 1 d . . . . .
C1 C 1.1438(3) 1.2556(2) 0.06944(18) 0.0333(7) Uani 1 1 d . . . . .
H1A H 1.1170 1.2207 0.0435 0.050 Uiso 1 1 calc GR . . . .
H1B H 1.1293 1.2216 0.1122 0.050 Uiso 1 1 calc GR . . . .
H1C H 1.2266 1.2701 0.0534 0.050 Uiso 1 1 calc GR . . . .
F2 F 0.5606(2) 0.79247(15) 0.46212(11) 0.0566(7) Uani 1 1 d . . . . .
O2 O 0.9109(2) 1.25593(15) 0.09195(11) 0.0305(5) Uani 1 1 d . . . . .
C2 C 0.9632(2) 1.32638(19) 0.08485(13) 0.0185(6) Uani 1 1 d . . . . .
F3 F 0.41223(19) 0.87669(18) 0.47954(12) 0.0559(7) Uani 1 1 d . . . . .
O3 O 0.71115(16) 1.37284(13) 0.13945(9) 0.0183(4) Uani 1 1 d . . . . .
C3 C 0.9082(2) 1.41434(19) 0.09096(13) 0.0167(5) Uani 1 1 d . . . . .
H3 H 0.9586 1.4644 0.0623 0.020 Uiso 1 1 calc R . . . .
O4 O 0.98531(17) 1.30969(15) 0.21343(10) 0.0234(4) Uani 1 1 d . . . . .
C4 C 0.8781(2) 1.42971(19) 0.16040(13) 0.0172(5) Uani 1 1 d . . . . .
H4 H 0.9158 1.4860 0.1627 0.021 Uiso 1 1 calc R . . . .
C5 C 0.7425(2) 1.43489(19) 0.17469(13) 0.0185(6) Uani 1 1 d . . . . .
C6 C 0.7065(3) 1.5245(2) 0.14121(14) 0.0243(6) Uani 1 1 d . . . . .
H6A H 0.7499 1.5747 0.1475 0.029 Uiso 1 1 calc R . . . .
H6B H 0.6228 1.5319 0.1551 0.029 Uiso 1 1 calc R . . . .
C7 C 0.7411(3) 1.5137(2) 0.07134(14) 0.0232(6) Uani 1 1 d . . . . .
H7A H 0.6741 1.5199 0.0523 0.028 Uiso 1 1 calc R . . . .
H7B H 0.8035 1.5570 0.0461 0.028 Uiso 1 1 calc R . . . .
C8 C 0.7835(2) 1.4170(2) 0.07883(13) 0.0195(6) Uani 1 1 d . . . . .
H8 H 0.7762 1.3882 0.0442 0.023 Uiso 1 1 calc R . . . .
C9 C 0.8964(2) 1.35260(19) 0.21268(13) 0.0190(6) Uani 1 1 d . . . . .
C10 C 0.7015(3) 1.3985(2) 0.24534(13) 0.0215(6) Uani 1 1 d . . . . .
H10 H 0.6967 1.4482 0.2677 0.026 Uiso 1 1 calc R . . . .
C11 C 0.5924(3) 1.3354(2) 0.27348(14) 0.0255(7) Uani 1 1 d . . . . .
H11A H 0.5808 1.2981 0.2447 0.031 Uiso 1 1 calc R . . . .
H11B H 0.5224 1.3683 0.2848 0.031 Uiso 1 1 calc R . . . .
C12 C 0.6253(3) 1.2797(2) 0.33238(14) 0.0251(6) Uani 1 1 d . . . . .
H12A H 0.6150 1.3132 0.3658 0.030 Uiso 1 1 calc R . . . .
H12B H 0.5772 1.2242 0.3481 0.030 Uiso 1 1 calc R . . . .
C13 C 0.7551(2) 1.2605(2) 0.30947(13) 0.0202(6) Uani 1 1 d . . . . .
H13 H 0.7960 1.2571 0.3436 0.024 Uiso 1 1 calc R . . . .
C14 C 0.7726(3) 1.1752(2) 0.28167(13) 0.0209(6) Uani 1 1 d . . . . .
H14A H 0.7401 1.1829 0.2447 0.025 Uiso 1 1 calc R . . . .
H14B H 0.8561 1.1664 0.2684 0.025 Uiso 1 1 calc R . . . .
C15 C 0.7136(3) 1.0932(2) 0.32965(13) 0.0202(6) Uani 1 1 d . . . . .
C16 C 0.6095(3) 1.0556(2) 0.32417(15) 0.0258(6) Uani 1 1 d . . . . .
H16 H 0.5792 1.0785 0.2893 0.031 Uiso 1 1 calc R . . . .
C17 C 0.5504(3) 0.9842(2) 0.37026(16) 0.0299(7) Uani 1 1 d . . . . .
H17 H 0.4802 0.9600 0.3663 0.036 Uiso 1 1 calc R . . . .
C18 C 0.5951(3) 0.9486(2) 0.42217(14) 0.0261(6) Uani 1 1 d . . . . .
C19 C 0.7000(3) 0.9838(2) 0.42739(15) 0.0261(6) Uani 1 1 d . . . . .
H19 H 0.7312 0.9595 0.4617 0.031 Uiso 1 1 calc R . . . .
C20 C 0.7589(3) 1.0557(2) 0.38148(14) 0.0228(6) Uani 1 1 d . . . . .
H20 H 0.8296 1.0791 0.3853 0.027 Uiso 1 1 calc R . . . .
C21 C 0.5290(3) 0.8739(2) 0.47259(17) 0.0337(7) Uani 1 1 d . . . . .
N4 N 0.2539(2) 0.03420(17) 0.25849(11) 0.0201(5) Uani 1 1 d . . . . .
F10 F 0.2947(3) 0.4490(2) 0.46174(11) 0.0699(9) Uani 1 1 d . . . . .
F11 F 0.1104(4) 0.4488(3) 0.4755(2) 0.1068(15) Uani 1 1 d . . . . .
F12 F 0.1911(3) 0.34500(19) 0.52786(10) 0.0710(9) Uani 1 1 d . . . . .
O13 O 0.57037(18) 0.12101(15) 0.07831(10) 0.0256(5) Uani 1 1 d . . . . .
O14 O 0.4036(2) 0.19406(15) 0.09166(12) 0.0320(5) Uani 1 1 d . . . . .
O15 O 0.19498(16) 0.06052(13) 0.13166(9) 0.0186(4) Uani 1 1 d . . . . .
O16 O 0.45182(18) 0.07351(16) 0.22103(10) 0.0281(5) Uani 1 1 d . . . . .
C64 C 0.6330(3) 0.2027(2) 0.07927(19) 0.0349(8) Uani 1 1 d . . . . .
H64A H 0.6184 0.2507 0.0469 0.052 Uiso 1 1 calc GR . . . .
H64B H 0.7158 0.1934 0.0716 0.052 Uiso 1 1 calc GR . . . .
H64C H 0.6063 0.2180 0.1199 0.052 Uiso 1 1 calc GR . . . .
C65 C 0.4529(3) 0.1250(2) 0.08888(14) 0.0212(6) Uani 1 1 d . . . . .
C66 C 0.3937(2) 0.0343(2) 0.09677(13) 0.0198(6) Uani 1 1 d . . . . .
H66 H 0.4462 -0.0038 0.0733 0.024 Uiso 1 1 calc R . . . .
C67 C 0.2761(2) 0.0415(2) 0.07674(13) 0.0205(6) Uani 1 1 d . . . . .
H67 H 0.2792 0.0870 0.0381 0.025 Uiso 1 1 calc R . . . .
C68 C 0.2291(3) -0.0518(2) 0.07377(15) 0.0265(7) Uani 1 1 d . . . . .
H68A H 0.2918 -0.0867 0.0552 0.032 Uiso 1 1 calc R . . . .
H68B H 0.1691 -0.0467 0.0498 0.032 Uiso 1 1 calc R . . . .
C69 C 0.1768(3) -0.0938(2) 0.14480(14) 0.0243(6) Uani 1 1 d . . . . .
H69A H 0.0922 -0.1039 0.1540 0.029 Uiso 1 1 calc R . . . .
H69B H 0.2123 -0.1498 0.1582 0.029 Uiso 1 1 calc R . . . .
C70 C 0.2112(2) -0.02004(19) 0.17488(13) 0.0184(5) Uani 1 1 d . . . . .
C71 C 0.3463(2) -0.01476(19) 0.16768(13) 0.0193(6) Uani 1 1 d . . . . .
H71 H 0.3768 -0.0749 0.1757 0.023 Uiso 1 1 calc R . . . .
C72 C 0.3603(3) 0.0363(2) 0.21780(13) 0.0208(6) Uani 1 1 d . . . . .
C73 C 0.1574(2) -0.0117(2) 0.24269(13) 0.0199(6) Uani 1 1 d . . . . .
H73 H 0.1405 -0.0717 0.2701 0.024 Uiso 1 1 calc R . . . .
C74 C 0.0550(2) 0.0474(2) 0.25977(14) 0.0212(6) Uani 1 1 d . . . . .
H74A H -0.0200 0.0144 0.2690 0.025 Uiso 1 1 calc R . . . .
H74B H 0.0571 0.0999 0.2262 0.025 Uiso 1 1 calc R . . . .
C75 C 0.0785(3) 0.0733(2) 0.31932(14) 0.0241(6) Uani 1 1 d . . . . .
H75A H 0.0375 0.1266 0.3276 0.029 Uiso 1 1 calc R . . . .
H75B H 0.0530 0.0247 0.3560 0.029 Uiso 1 1 calc R . . . .
C76 C 0.2122(3) 0.0915(2) 0.30411(14) 0.0217(6) Uani 1 1 d . . . . .
H76 H 0.2420 0.0720 0.3422 0.026 Uiso 1 1 calc R . . . .
C77 C 0.2469(3) 0.1910(2) 0.27477(14) 0.0250(6) Uani 1 1 d . . . . .
H77A H 0.3286 0.1970 0.2515 0.030 Uiso 1 1 calc R . . . .
H77B H 0.1991 0.2137 0.2452 0.030 Uiso 1 1 calc R . . . .
C78 C 0.2299(3) 0.2453(2) 0.32520(14) 0.0220(6) Uani 1 1 d . . . . .
C79 C 0.1371(3) 0.3010(2) 0.33637(15) 0.0252(6) Uani 1 1 d . . . . .
H79 H 0.0822 0.3060 0.3118 0.030 Uiso 1 1 calc R . . . .
C80 C 0.1250(3) 0.3498(2) 0.38428(16) 0.0292(7) Uani 1 1 d . . . . .
H80 H 0.0620 0.3865 0.3917 0.035 Uiso 1 1 calc R . . . .
C81 C 0.2065(3) 0.3432(2) 0.42044(15) 0.0282(7) Uani 1 1 d . . . . .
C82 C 0.2993(3) 0.2880(2) 0.41000(18) 0.0367(8) Uani 1 1 d . . . . .
H82 H 0.3543 0.2836 0.4345 0.044 Uiso 1 1 calc R . . . .
C83 C 0.3103(3) 0.2395(2) 0.36340(17) 0.0314(7) Uani 1 1 d . . . . .
H83 H 0.3727 0.2019 0.3571 0.038 Uiso 1 1 calc R . . . .
C84 C 0.1986(4) 0.3962(3) 0.47100(17) 0.0391(9) Uani 1 1 d . . . . .
N2 N 0.2146(2) 0.53487(17) 0.25656(11) 0.0190(5) Uani 1 1 d . . . . .
F4 F 0.1667(2) 0.95793(17) 0.46680(12) 0.0518(6) Uani 1 1 d . . . . .
F5 F 0.0843(3) 0.83707(19) 0.52986(11) 0.0674(8) Uani 1 1 d . . . . .
O5 O 0.05078(17) 0.61866(14) 0.07855(10) 0.0214(4) Uani 1 1 d . . . . .
F6 F -0.01494(19) 0.92335(17) 0.47544(12) 0.0499(6) Uani 1 1 d . . . . .
O6 O 0.21054(19) 0.69022(15) 0.08792(12) 0.0307(5) Uani 1 1 d . . . . .
O7 O 0.38139(16) 0.55598(13) 0.12729(9) 0.0179(4) Uani 1 1 d . . . . .
O8 O 0.04685(17) 0.57236(16) 0.22140(10) 0.0258(5) Uani 1 1 d . . . . .
C22 C -0.0086(3) 0.7023(2) 0.07802(17) 0.0306(7) Uani 1 1 d . . . . .
H22A H 0.0345 0.7479 0.0437 0.046 Uiso 1 1 calc GR . . . .
H22B H -0.0131 0.7204 0.1174 0.046 Uiso 1 1 calc GR . . . .
H22C H -0.0865 0.6939 0.0726 0.046 Uiso 1 1 calc GR . . . .
C23 C 0.1598(2) 0.6216(2) 0.08798(13) 0.0184(6) Uani 1 1 d . . . . .
C24 C 0.2094(2) 0.52905(19) 0.09681(12) 0.0171(5) Uani 1 1 d . . . . .
H24 H 0.1744 0.4904 0.0750 0.020 Uiso 1 1 calc R . . . .
C25 C 0.3450(2) 0.53390(19) 0.07471(13) 0.0185(6) Uani 1 1 d . . . . .
H25 H 0.3754 0.5771 0.0348 0.022 Uiso 1 1 calc R . . . .
C26 C 0.3905(3) 0.4387(2) 0.07404(14) 0.0237(6) Uani 1 1 d . . . . .
H26A H 0.4702 0.4412 0.0484 0.028 Uiso 1 1 calc R . . . .
H26B H 0.3401 0.4029 0.0584 0.028 Uiso 1 1 calc R . . . .
C27 C 0.3853(3) 0.4011(2) 0.14495(14) 0.0217(6) Uani 1 1 d . . . . .
H27A H 0.3382 0.3452 0.1610 0.026 Uiso 1 1 calc R . . . .
H27B H 0.4632 0.3922 0.1526 0.026 Uiso 1 1 calc R . . . .
C28 C 0.3263(2) 0.47765(19) 0.17336(13) 0.0176(5) Uani 1 1 d . . . . .
C29 C 0.1971(2) 0.48255(19) 0.16790(13) 0.0170(5) Uani 1 1 d . . . . .
H29 H 0.1591 0.4223 0.1775 0.020 Uiso 1 1 calc R . . . .
C30 C 0.1417(2) 0.5356(2) 0.21764(13) 0.0191(6) Uani 1 1 d . . . . .
C31 C 0.3241(2) 0.48892(19) 0.23961(13) 0.0196(6) Uani 1 1 d . . . . .
H31 H 0.3184 0.4297 0.2679 0.024 Uiso 1 1 calc R . . . .
C32 C 0.4136(2) 0.5496(2) 0.25362(13) 0.0201(6) Uani 1 1 d . . . . .
H32A H 0.4388 0.6015 0.2193 0.024 Uiso 1 1 calc R . . . .
H32B H 0.4819 0.5173 0.2616 0.024 Uiso 1 1 calc R . . . .
C33 C 0.3416(3) 0.5768(2) 0.31365(14) 0.0230(6) Uani 1 1 d . . . . .
H33A H 0.3759 0.6310 0.3202 0.028 Uiso 1 1 calc R . . . .
H33B H 0.3375 0.5291 0.3506 0.028 Uiso 1 1 calc R . . . .
C34 C 0.2186(3) 0.5931(2) 0.30081(13) 0.0213(6) Uani 1 1 d . . . . .
H34 H 0.1574 0.5735 0.3399 0.026 Uiso 1 1 calc R . . . .
C35 C 0.2064(3) 0.6921(2) 0.27175(14) 0.0239(6) Uani 1 1 d . . . . .
H35A H 0.2786 0.7158 0.2410 0.029 Uiso 1 1 calc R . . . .
H35B H 0.1431 0.6972 0.2500 0.029 Uiso 1 1 calc R . . . .
C36 C 0.1809(2) 0.7457(2) 0.32301(14) 0.0214(6) Uani 1 1 d . . . . .
C37 C 0.0679(3) 0.7382(2) 0.36272(16) 0.0292(7) Uani 1 1 d . . . . .
H37 H 0.0107 0.7007 0.3567 0.035 Uiso 1 1 calc R . . . .
C38 C 0.0395(3) 0.7850(2) 0.41028(16) 0.0316(7) Uani 1 1 d . . . . .
H38 H -0.0366 0.7802 0.4356 0.038 Uiso 1 1 calc R . . . .
C39 C 0.1240(3) 0.8391(2) 0.42049(15) 0.0247(6) Uani 1 1 d . . . . .
C40 C 0.2378(3) 0.8464(2) 0.38283(15) 0.0257(6) Uani 1 1 d . . . . .
H40 H 0.2953 0.8822 0.3902 0.031 Uiso 1 1 calc R . . . .
C41 C 0.2650(3) 0.7999(2) 0.33427(14) 0.0246(6) Uani 1 1 d . . . . .
H41 H 0.3411 0.8051 0.3088 0.030 Uiso 1 1 calc R . . . .
C42 C 0.0900(3) 0.8889(2) 0.47297(17) 0.0350(8) Uani 1 1 d . . . . .
N3 N 0.3291(2) 0.16488(16) 0.73645(11) 0.0198(5) Uani 1 1 d . . . . .
F7 F 0.2759(3) 0.71563(14) 0.53699(11) 0.0530(6) Uani 1 1 d . . . . .
F8 F 0.1626(2) 0.63248(17) 0.50731(14) 0.0631(8) Uani 1 1 d . . . . .
F9 F 0.3487(3) 0.64228(17) 0.46700(10) 0.0597(7) Uani 1 1 d . . . . .
O9 O 0.45404(18) 0.15968(14) 0.92467(10) 0.0232(4) Uani 1 1 d . . . . .
O10 O 0.2987(2) 0.23852(15) 0.90833(11) 0.0288(5) Uani 1 1 d . . . . .
O11 O 0.14160(17) 0.12384(13) 0.85864(9) 0.0198(4) Uani 1 1 d . . . . .
O12 O 0.47845(17) 0.19537(15) 0.78164(10) 0.0247(5) Uani 1 1 d . . . . .
C43 C 0.5148(3) 0.2430(2) 0.92412(17) 0.0317(7) Uani 1 1 d . . . . .
H43A H 0.5149 0.2854 0.8856 0.048 Uiso 1 1 calc GR . . . .
H43B H 0.5943 0.2316 0.9267 0.048 Uiso 1 1 calc GR . . . .
H43C H 0.4753 0.2671 0.9597 0.048 Uiso 1 1 calc GR . . . .
C44 C 0.3473(2) 0.16959(19) 0.91207(13) 0.0183(6) Uani 1 1 d . . . . .
C45 C 0.2992(2) 0.08178(19) 0.90342(13) 0.0168(5) Uani 1 1 d . . . . .
H45 H 0.3270 0.0308 0.9301 0.020 Uiso 1 1 calc R . . . .
C46 C 0.1641(2) 0.07670(19) 0.91756(13) 0.0191(6) Uani 1 1 d . . . . .
H46 H 0.1267 0.1025 0.9538 0.023 Uiso 1 1 calc R . . . .
C47 C 0.1178(3) -0.0199(2) 0.92241(14) 0.0244(6) Uani 1 1 d . . . . .
H47A H 0.0345 -0.0281 0.9424 0.029 Uiso 1 1 calc R . . . .
H47B H 0.1602 -0.0638 0.9458 0.029 Uiso 1 1 calc R . . . .
C48 C 0.1429(3) -0.0260(2) 0.85137(14) 0.0249(6) Uani 1 1 d . . . . .
H48A H 0.1933 -0.0747 0.8427 0.030 Uiso 1 1 calc R . . . .
H48B H 0.0708 -0.0331 0.8381 0.030 Uiso 1 1 calc R . . . .
C49 C 0.2051(3) 0.06536(19) 0.82032(13) 0.0196(6) Uani 1 1 d . . . . .
C50 C 0.3296(2) 0.07134(19) 0.83274(13) 0.0180(6) Uani 1 1 d . . . . .
H50 H 0.3714 0.0164 0.8280 0.022 Uiso 1 1 calc R . . . .
C51 C 0.3895(2) 0.1520(2) 0.78194(13) 0.0192(6) Uani 1 1 d . . . . .
C52 C 0.2224(3) 0.1060(2) 0.75037(13) 0.0216(6) Uani 1 1 d . . . . .
H52 H 0.2381 0.0583 0.7263 0.026 Uiso 1 1 calc R . . . .
C53 C 0.1358(3) 0.1688(2) 0.72484(14) 0.0257(6) Uani 1 1 d . . . . .
H53A H 0.0995 0.2049 0.7547 0.031 Uiso 1 1 calc R . . . .
H53B H 0.0751 0.1361 0.7140 0.031 Uiso 1 1 calc R . . . .
C54 C 0.2185(3) 0.2266(2) 0.66538(14) 0.0259(6) Uani 1 1 d . . . . .
H54A H 0.2378 0.1939 0.6314 0.031 Uiso 1 1 calc R . . . .
H54B H 0.1827 0.2818 0.6506 0.031 Uiso 1 1 calc R . . . .
C55 C 0.3284(3) 0.2464(2) 0.68763(13) 0.0208(6) Uani 1 1 d . . . . .
H55 H 0.3987 0.2510 0.6528 0.025 Uiso 1 1 calc R . . . .
C56 C 0.3203(3) 0.3318(2) 0.71539(13) 0.0215(6) Uani 1 1 d . . . . .
H56A H 0.2528 0.3249 0.7512 0.026 Uiso 1 1 calc R . . . .
H56B H 0.3902 0.3395 0.7304 0.026 Uiso 1 1 calc R . . . .
C57 C 0.3086(3) 0.4139(2) 0.66645(13) 0.0202(6) Uani 1 1 d . . . . .
C58 C 0.4043(3) 0.4519(2) 0.61742(14) 0.0221(6) Uani 1 1 d . . . . .
H58 H 0.4778 0.4281 0.6162 0.027 Uiso 1 1 calc R . . . .
C59 C 0.3918(3) 0.5244(2) 0.57041(14) 0.0252(6) Uani 1 1 d . . . . .
H59 H 0.4566 0.5493 0.5383 0.030 Uiso 1 1 calc R . . . .
C60 C 0.2828(3) 0.5593(2) 0.57161(15) 0.0265(6) Uani 1 1 d . . . . .
C61 C 0.1873(3) 0.5235(2) 0.62069(17) 0.0325(7) Uani 1 1 d . . . . .
H61 H 0.1141 0.5477 0.6219 0.039 Uiso 1 1 calc R . . . .
C62 C 0.2003(3) 0.4522(2) 0.66785(15) 0.0283(7) Uani 1 1 d . . . . .
H62 H 0.1360 0.4294 0.7009 0.034 Uiso 1 1 calc R . . . .
C63 C 0.2675(3) 0.6367(2) 0.52082(17) 0.0340(8) 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
F1 C21 1.342(4) . ?
O1 C1 1.445(4) . ?
O1 C2 1.347(3) . ?
N1 C9 1.354(4) . ?
N1 C10 1.474(4) . ?
N1 C13 1.467(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
F2 C21 1.343(4) . ?
O2 C2 1.199(4) . ?
C2 C3 1.503(4) . ?
F3 C21 1.341(4) . ?
O3 C5 1.442(3) . ?
O3 C8 1.442(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.566(4) . ?
C3 C8 1.545(4) . ?
O4 C9 1.231(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.550(4) . ?
C4 C9 1.526(4) . ?
C5 C6 1.524(4) . ?
C5 C10 1.514(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.553(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.542(4) . ?
C8 H8 0.9800 . ?
C10 H10 0.9800 . ?
C10 C11 1.525(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.536(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.535(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.543(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.511(4) . ?
C15 C16 1.389(4) . ?
C15 C20 1.396(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(5) . ?
C18 C19 1.380(5) . ?
C18 C21 1.491(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9300 . ?
N4 C72 1.353(4) . ?
N4 C73 1.475(4) . ?
N4 C76 1.468(4) . ?
F10 C84 1.335(5) . ?
F11 C84 1.305(5) . ?
F12 C84 1.325(4) . ?
O13 C64 1.450(4) . ?
O13 C65 1.344(3) . ?
O14 C65 1.205(4) . ?
O15 C67 1.441(3) . ?
O15 C70 1.437(3) . ?
O16 C72 1.237(4) . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?
C65 C66 1.504(4) . ?
C66 H66 0.9800 . ?
C66 C67 1.540(4) . ?
C66 C71 1.568(4) . ?
C67 H67 0.9800 . ?
C67 C68 1.543(4) . ?
C68 H68A 0.9700 . ?
C68 H68B 0.9700 . ?
C68 C69 1.552(4) . ?
C69 H69A 0.9700 . ?
C69 H69B 0.9700 . ?
C69 C70 1.518(4) . ?
C70 C71 1.553(4) . ?
C70 C73 1.522(4) . ?
C71 H71 0.9800 . ?
C71 C72 1.520(4) . ?
C73 H73 0.9800 . ?
C73 C74 1.522(4) . ?
C74 H74A 0.9700 . ?
C74 H74B 0.9700 . ?
C74 C75 1.538(4) . ?
C75 H75A 0.9700 . ?
C75 H75B 0.9700 . ?
C75 C76 1.536(4) . ?
C76 H76 0.9800 . ?
C76 C77 1.536(4) . ?
C77 H77A 0.9700 . ?
C77 H77B 0.9700 . ?
C77 C78 1.501(4) . ?
C78 C79 1.386(4) . ?
C78 C83 1.400(4) . ?
C79 H79 0.9300 . ?
C79 C80 1.399(5) . ?
C80 H80 0.9300 . ?
C80 C81 1.375(5) . ?
C81 C82 1.380(5) . ?
C81 C84 1.497(5) . ?
C82 H82 0.9300 . ?
C82 C83 1.373(5) . ?
C83 H83 0.9300 . ?
N2 C30 1.348(4) . ?
N2 C31 1.469(3) . ?
N2 C34 1.460(4) . ?
F4 C42 1.347(5) . ?
F5 C42 1.333(5) . ?
O5 C22 1.449(4) . ?
O5 C23 1.344(3) . ?
F6 C42 1.329(4) . ?
O6 C23 1.202(4) . ?
O7 C25 1.433(3) . ?
O7 C28 1.441(3) . ?
O8 C30 1.236(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.516(4) . ?
C24 H24 0.9800 . ?
C24 C25 1.546(4) . ?
C24 C29 1.566(4) . ?
C25 H25 0.9800 . ?
C25 C26 1.545(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.549(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.527(4) . ?
C28 C29 1.546(4) . ?
C28 C31 1.511(4) . ?
C29 H29 0.9800 . ?
C29 C30 1.525(4) . ?
C31 H31 0.9800 . ?
C31 C32 1.524(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.537(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.543(4) . ?
C34 H34 0.9800 . ?
C34 C35 1.534(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.507(4) . ?
C36 C37 1.399(4) . ?
C36 C41 1.384(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.370(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.375(5) . ?
C39 C40 1.389(4) . ?
C39 C42 1.496(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.386(4) . ?
C41 H41 0.9300 . ?
N3 C51 1.346(4) . ?
N3 C52 1.472(4) . ?
N3 C55 1.473(4) . ?
F7 C63 1.332(4) . ?
F8 C63 1.336(4) . ?
F9 C63 1.330(4) . ?
O9 C43 1.451(4) . ?
O9 C44 1.345(3) . ?
O10 C44 1.191(4) . ?
O11 C46 1.440(3) . ?
O11 C49 1.444(3) . ?
O12 C51 1.232(4) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 C45 1.516(4) . ?
C45 H45 0.9800 . ?
C45 C46 1.538(4) . ?
C45 C50 1.568(4) . ?
C46 H46 0.9800 . ?
C46 C47 1.541(4) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 C48 1.559(4) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C48 C49 1.521(4) . ?
C49 C50 1.552(4) . ?
C49 C52 1.516(4) . ?
C50 H50 0.9800 . ?
C50 C51 1.528(4) . ?
C52 H52 0.9800 . ?
C52 C53 1.519(4) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C53 C54 1.545(4) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C54 C55 1.533(4) . ?
C55 H55 0.9800 . ?
C55 C56 1.542(4) . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C56 C57 1.509(4) . ?
C57 C58 1.396(4) . ?
C57 C62 1.391(4) . ?
C58 H58 0.9300 . ?
C58 C59 1.389(4) . ?
C59 H59 0.9300 . ?
C59 C60 1.379(4) . ?
C60 C61 1.387(5) . ?
C60 C63 1.498(4) . ?
C61 H61 0.9300 . ?
C61 C62 1.381(5) . ?
C62 H62 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
C2 O1 C1 115.2(2) . . ?
C9 N1 C10 114.4(2) . . ?
C9 N1 C13 128.0(2) . . ?
C13 N1 C10 113.2(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 110.5(2) . . ?
O2 C2 O1 123.9(3) . . ?
O2 C2 C3 125.6(3) . . ?
C5 O3 C8 96.1(2) . . ?
C2 C3 H3 110.4 . . ?
C2 C3 C4 113.4(2) . . ?
C2 C3 C8 112.2(2) . . ?
C4 C3 H3 110.4 . . ?
C8 C3 H3 110.4 . . ?
C8 C3 C4 99.5(2) . . ?
C3 C4 H4 111.1 . . ?
C5 C4 C3 102.1(2) . . ?
C5 C4 H4 111.1 . . ?
C9 C4 C3 117.6(2) . . ?
C9 C4 H4 111.1 . . ?
C9 C4 C5 103.0(2) . . ?
O3 C5 C4 101.7(2) . . ?
O3 C5 C6 102.7(2) . . ?
O3 C5 C10 111.2(2) . . ?
C6 C5 C4 111.4(2) . . ?
C10 C5 C4 104.6(2) . . ?
C10 C5 C6 123.3(2) . . ?
C5 C6 H6A 111.7 . . ?
C5 C6 H6B 111.7 . . ?
C5 C6 C7 100.5(2) . . ?
H6A C6 H6B 109.4 . . ?
C7 C6 H6A 111.7 . . ?
C7 C6 H6B 111.7 . . ?
C6 C7 H7A 111.4 . . ?
C6 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
C8 C7 C6 101.6(2) . . ?
C8 C7 H7A 111.4 . . ?
C8 C7 H7B 111.4 . . ?
O3 C8 C3 102.7(2) . . ?
O3 C8 C7 102.7(2) . . ?
O3 C8 H8 113.3 . . ?
C3 C8 H8 113.3 . . ?
C7 C8 C3 110.4(2) . . ?
C7 C8 H8 113.3 . . ?
N1 C9 C4 107.4(2) . . ?
O4 C9 N1 125.6(3) . . ?
O4 C9 C4 127.0(2) . . ?
N1 C10 C5 103.0(2) . . ?
N1 C10 H10 109.6 . . ?
N1 C10 C11 102.6(2) . . ?
C5 C10 H10 109.6 . . ?
C5 C10 C11 121.6(3) . . ?
C11 C10 H10 109.6 . . ?
C10 C11 H11A 111.6 . . ?
C10 C11 H11B 111.6 . . ?
C10 C11 C12 100.9(2) . . ?
H11A C11 H11B 109.4 . . ?
C12 C11 H11A 111.6 . . ?
C12 C11 H11B 111.6 . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C13 C12 C11 104.6(2) . . ?
C13 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
N1 C13 C12 101.3(2) . . ?
N1 C13 H13 110.6 . . ?
N1 C13 C14 110.3(2) . . ?
C12 C13 H13 110.6 . . ?
C12 C13 C14 113.2(3) . . ?
C14 C13 H13 110.6 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.3(2) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 C20 118.4(3) . . ?
C20 C15 C14 121.4(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C21 120.2(3) . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 C21 120.2(3) . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
F1 C21 F2 104.7(3) . . ?
F1 C21 C18 112.9(3) . . ?
F2 C21 C18 112.7(3) . . ?
F3 C21 F1 105.6(3) . . ?
F3 C21 F2 107.7(3) . . ?
F3 C21 C18 112.7(3) . . ?
C72 N4 C73 115.2(2) . . ?
C72 N4 C76 129.1(3) . . ?
C76 N4 C73 113.1(2) . . ?
C65 O13 C64 115.4(2) . . ?
C70 O15 C67 96.3(2) . . ?
O13 C64 H64A 109.5 . . ?
O13 C64 H64B 109.5 . . ?
O13 C64 H64C 109.5 . . ?
H64A C64 H64B 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
O13 C65 C66 111.9(2) . . ?
O14 C65 O13 122.6(3) . . ?
O14 C65 C66 125.5(3) . . ?
C65 C66 H66 110.6 . . ?
C65 C66 C67 112.2(2) . . ?
C65 C66 C71 113.6(2) . . ?
C67 C66 H66 110.6 . . ?
C67 C66 C71 98.7(2) . . ?
C71 C66 H66 110.6 . . ?
O15 C67 C66 103.1(2) . . ?
O15 C67 H67 113.3 . . ?
O15 C67 C68 102.2(2) . . ?
C66 C67 H67 113.3 . . ?
C66 C67 C68 110.7(2) . . ?
C68 C67 H67 113.3 . . ?
C67 C68 H68A 111.4 . . ?
C67 C68 H68B 111.4 . . ?
C67 C68 C69 102.0(2) . . ?
H68A C68 H68B 109.2 . . ?
C69 C68 H68A 111.4 . . ?
C69 C68 H68B 111.4 . . ?
C68 C69 H69A 111.7 . . ?
C68 C69 H69B 111.7 . . ?
H69A C69 H69B 109.5 . . ?
C70 C69 C68 100.2(2) . . ?
C70 C69 H69A 111.7 . . ?
C70 C69 H69B 111.7 . . ?
O15 C70 C69 102.9(2) . . ?
O15 C70 C71 101.7(2) . . ?
O15 C70 C73 109.9(2) . . ?
C69 C70 C71 110.6(2) . . ?
C69 C70 C73 124.3(2) . . ?
C73 C70 C71 105.4(2) . . ?
C66 C71 H71 111.1 . . ?
C70 C71 C66 102.7(2) . . ?
C70 C71 H71 111.1 . . ?
C72 C71 C66 116.9(2) . . ?
C72 C71 C70 103.3(2) . . ?
C72 C71 H71 111.1 . . ?
N4 C72 C71 107.7(2) . . ?
O16 C72 N4 125.8(3) . . ?
O16 C72 C71 126.5(3) . . ?
N4 C73 C70 102.2(2) . . ?
N4 C73 H73 109.6 . . ?
N4 C73 C74 102.2(2) . . ?
C70 C73 H73 109.6 . . ?
C74 C73 C70 122.7(2) . . ?
C74 C73 H73 109.6 . . ?
C73 C74 H74A 111.5 . . ?
C73 C74 H74B 111.5 . . ?
C73 C74 C75 101.2(2) . . ?
H74A C74 H74B 109.3 . . ?
C75 C74 H74A 111.5 . . ?
C75 C74 H74B 111.5 . . ?
C74 C75 H75A 110.8 . . ?
C74 C75 H75B 110.8 . . ?
H75A C75 H75B 108.9 . . ?
C76 C75 C74 104.8(2) . . ?
C76 C75 H75A 110.8 . . ?
C76 C75 H75B 110.8 . . ?
N4 C76 C75 101.8(2) . . ?
N4 C76 H76 110.6 . . ?
N4 C76 C77 111.6(2) . . ?
C75 C76 H76 110.6 . . ?
C77 C76 C75 111.5(2) . . ?
C77 C76 H76 110.6 . . ?
C76 C77 H77A 109.5 . . ?
C76 C77 H77B 109.5 . . ?
H77A C77 H77B 108.1 . . ?
C78 C77 C76 110.7(2) . . ?
C78 C77 H77A 109.5 . . ?
C78 C77 H77B 109.5 . . ?
C79 C78 C77 123.1(3) . . ?
C79 C78 C83 117.8(3) . . ?
C83 C78 C77 119.1(3) . . ?
C78 C79 H79 119.6 . . ?
C78 C79 C80 120.7(3) . . ?
C80 C79 H79 119.6 . . ?
C79 C80 H80 120.1 . . ?
C81 C80 C79 119.9(3) . . ?
C81 C80 H80 120.1 . . ?
C80 C81 C82 120.1(3) . . ?
C80 C81 C84 121.6(3) . . ?
C82 C81 C84 118.3(3) . . ?
C81 C82 H82 120.1 . . ?
C83 C82 C81 119.9(3) . . ?
C83 C82 H82 120.1 . . ?
C78 C83 H83 119.2 . . ?
C82 C83 C78 121.5(3) . . ?
C82 C83 H83 119.2 . . ?
F10 C84 C81 112.5(3) . . ?
F11 C84 F10 106.0(4) . . ?
F11 C84 F12 107.5(4) . . ?
F11 C84 C81 113.5(3) . . ?
F12 C84 F10 103.4(3) . . ?
F12 C84 C81 113.1(3) . . ?
C30 N2 C31 115.0(2) . . ?
C30 N2 C34 129.0(2) . . ?
C34 N2 C31 113.3(2) . . ?
C23 O5 C22 114.8(2) . . ?
C25 O7 C28 96.4(2) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 C24 111.5(2) . . ?
O6 C23 O5 123.0(3) . . ?
O6 C23 C24 125.5(2) . . ?
C23 C24 H24 110.8 . . ?
C23 C24 C25 111.8(2) . . ?
C23 C24 C29 113.5(2) . . ?
C25 C24 H24 110.8 . . ?
C25 C24 C29 98.5(2) . . ?
C29 C24 H24 110.8 . . ?
O7 C25 C24 103.0(2) . . ?
O7 C25 H25 113.4 . . ?
O7 C25 C26 102.6(2) . . ?
C24 C25 H25 113.4 . . ?
C26 C25 C24 110.2(2) . . ?
C26 C25 H25 113.4 . . ?
C25 C26 H26A 111.3 . . ?
C25 C26 H26B 111.3 . . ?
C25 C26 C27 102.2(2) . . ?
H26A C26 H26B 109.2 . . ?
C27 C26 H26A 111.3 . . ?
C27 C26 H26B 111.3 . . ?
C26 C27 H27A 111.8 . . ?
C26 C27 H27B 111.8 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 C26 99.9(2) . . ?
C28 C27 H27A 111.8 . . ?
C28 C27 H27B 111.8 . . ?
O7 C28 C27 102.3(2) . . ?
O7 C28 C29 102.1(2) . . ?
O7 C28 C31 110.6(2) . . ?
C27 C28 C29 110.6(2) . . ?
C31 C28 C27 123.7(2) . . ?
C31 C28 C29 105.6(2) . . ?
C24 C29 H29 111.0 . . ?
C28 C29 C24 102.8(2) . . ?
C28 C29 H29 111.0 . . ?
C30 C29 C24 117.2(2) . . ?
C30 C29 C28 103.0(2) . . ?
C30 C29 H29 111.0 . . ?
N2 C30 C29 107.6(2) . . ?
O8 C30 N2 126.5(3) . . ?
O8 C30 C29 125.9(3) . . ?
N2 C31 C28 102.7(2) . . ?
N2 C31 H31 109.5 . . ?
N2 C31 C32 102.0(2) . . ?
C28 C31 H31 109.5 . . ?
C28 C31 C32 122.6(2) . . ?
C32 C31 H31 109.5 . . ?
C31 C32 H32A 111.5 . . ?
C31 C32 H32B 111.5 . . ?
C31 C32 C33 101.2(2) . . ?
H32A C32 H32B 109.3 . . ?
C33 C32 H32A 111.5 . . ?
C33 C32 H32B 111.5 . . ?
C32 C33 H33A 110.9 . . ?
C32 C33 H33B 110.9 . . ?
C32 C33 C34 104.4(2) . . ?
H33A C33 H33B 108.9 . . ?
C34 C33 H33A 110.9 . . ?
C34 C33 H33B 110.9 . . ?
N2 C34 C33 101.9(2) . . ?
N2 C34 H34 110.4 . . ?
N2 C34 C35 112.1(2) . . ?
C33 C34 H34 110.4 . . ?
C35 C34 C33 111.5(3) . . ?
C35 C34 H34 110.4 . . ?
C34 C35 H35A 109.7 . . ?
C34 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
C36 C35 C34 109.9(2) . . ?
C36 C35 H35A 109.7 . . ?
C36 C35 H35B 109.7 . . ?
C37 C36 C35 118.7(3) . . ?
C41 C36 C35 123.2(3) . . ?
C41 C36 C37 118.0(3) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 C36 121.4(3) . . ?
C38 C37 H37 119.3 . . ?
C37 C38 H38 120.1 . . ?
C37 C38 C39 119.8(3) . . ?
C39 C38 H38 120.1 . . ?
C38 C39 C40 120.3(3) . . ?
C38 C39 C42 118.3(3) . . ?
C40 C39 C42 121.4(3) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 C39 119.5(3) . . ?
C41 C40 H40 120.3 . . ?
C36 C41 C40 121.1(3) . . ?
C36 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
F4 C42 C39 112.3(3) . . ?
F5 C42 F4 106.2(3) . . ?
F5 C42 C39 112.8(3) . . ?
F6 C42 F4 106.7(3) . . ?
F6 C42 F5 106.3(3) . . ?
F6 C42 C39 112.0(3) . . ?
C51 N3 C52 115.0(2) . . ?
C51 N3 C55 128.1(3) . . ?
C52 N3 C55 112.9(2) . . ?
C44 O9 C43 114.6(2) . . ?
C46 O11 C49 96.0(2) . . ?
O9 C43 H43A 109.5 . . ?
O9 C43 H43B 109.5 . . ?
O9 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O9 C44 C45 110.7(2) . . ?
O10 C44 O9 123.8(3) . . ?
O10 C44 C45 125.5(3) . . ?
C44 C45 H45 110.3 . . ?
C44 C45 C46 112.3(2) . . ?
C44 C45 C50 113.3(2) . . ?
C46 C45 H45 110.3 . . ?
C46 C45 C50 100.1(2) . . ?
C50 C45 H45 110.3 . . ?
O11 C46 C45 102.5(2) . . ?
O11 C46 H46 113.4 . . ?
O11 C46 C47 102.6(2) . . ?
C45 C46 H46 113.4 . . ?
C45 C46 C47 110.5(2) . . ?
C47 C46 H46 113.4 . . ?
C46 C47 H47A 111.4 . . ?
C46 C47 H47B 111.4 . . ?
C46 C47 C48 101.7(2) . . ?
H47A C47 H47B 109.3 . . ?
C48 C47 H47A 111.4 . . ?
C48 C47 H47B 111.4 . . ?
C47 C48 H48A 111.7 . . ?
C47 C48 H48B 111.7 . . ?
H48A C48 H48B 109.5 . . ?
C49 C48 C47 100.2(2) . . ?
C49 C48 H48A 111.7 . . ?
C49 C48 H48B 111.7 . . ?
O11 C49 C48 102.9(2) . . ?
O11 C49 C50 101.8(2) . . ?
O11 C49 C52 111.1(2) . . ?
C48 C49 C50 111.8(2) . . ?
C52 C49 C48 122.9(3) . . ?
C52 C49 C50 104.4(2) . . ?
C45 C50 H50 111.3 . . ?
C49 C50 C45 101.3(2) . . ?
C49 C50 H50 111.3 . . ?
C51 C50 C45 117.8(2) . . ?
C51 C50 C49 103.0(2) . . ?
C51 C50 H50 111.3 . . ?
N3 C51 C50 107.1(2) . . ?
O12 C51 N3 126.3(3) . . ?
O12 C51 C50 126.5(3) . . ?
N3 C52 C49 102.8(2) . . ?
N3 C52 H52 109.3 . . ?
N3 C52 C53 102.7(2) . . ?
C49 C52 H52 109.3 . . ?
C49 C52 C53 122.3(3) . . ?
C53 C52 H52 109.3 . . ?
C52 C53 H53A 111.7 . . ?
C52 C53 H53B 111.7 . . ?
C52 C53 C54 100.6(2) . . ?
H53A C53 H53B 109.4 . . ?
C54 C53 H53A 111.7 . . ?
C54 C53 H53B 111.7 . . ?
C53 C54 H54A 110.9 . . ?
C53 C54 H54B 110.9 . . ?
H54A C54 H54B 108.9 . . ?
C55 C54 C53 104.3(2) . . ?
C55 C54 H54A 110.9 . . ?
C55 C54 H54B 110.9 . . ?
N3 C55 C54 101.2(2) . . ?
N3 C55 H55 110.3 . . ?
N3 C55 C56 111.6(2) . . ?
C54 C55 H55 110.3 . . ?
C54 C55 C56 112.9(2) . . ?
C56 C55 H55 110.3 . . ?
C55 C56 H56A 109.4 . . ?
C55 C56 H56B 109.4 . . ?
H56A C56 H56B 108.0 . . ?
C57 C56 C55 111.2(2) . . ?
C57 C56 H56A 109.4 . . ?
C57 C56 H56B 109.4 . . ?
C58 C57 C56 121.4(3) . . ?
C62 C57 C56 120.5(3) . . ?
C62 C57 C58 118.1(3) . . ?
C57 C58 H58 119.4 . . ?
C59 C58 C57 121.2(3) . . ?
C59 C58 H58 119.4 . . ?
C58 C59 H59 120.2 . . ?
C60 C59 C58 119.6(3) . . ?
C60 C59 H59 120.2 . . ?
C59 C60 C61 119.8(3) . . ?
C59 C60 C63 120.3(3) . . ?
C61 C60 C63 119.9(3) . . ?
C60 C61 H61 119.8 . . ?
C62 C61 C60 120.4(3) . . ?
C62 C61 H61 119.8 . . ?
C57 C62 H62 119.6 . . ?
C61 C62 C57 120.8(3) . . ?
C61 C62 H62 119.6 . . ?
F7 C63 F8 106.2(3) . . ?
F7 C63 C60 112.4(3) . . ?
F8 C63 C60 112.3(3) . . ?
F9 C63 F7 105.4(3) . . ?
F9 C63 F8 107.3(3) . . ?
F9 C63 C60 112.7(3) . . ?

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 C2 C3 C4 -94.9(3) . . . . ?
O1 C2 C3 C8 153.3(2) . . . . ?
N1 C10 C11 C12 35.7(3) . . . . ?
N1 C13 C14 C15 -171.2(2) . . . . ?
C1 O1 C2 O2 -9.9(4) . . . . ?
C1 O1 C2 C3 171.9(2) . . . . ?
O2 C2 C3 C4 86.8(4) . . . . ?
O2 C2 C3 C8 -24.9(4) . . . . ?
C2 C3 C4 C5 -117.6(2) . . . . ?
C2 C3 C4 C9 -5.7(3) . . . . ?
C2 C3 C8 O3 83.2(3) . . . . ?
C2 C3 C8 C7 -167.9(2) . . . . ?
O3 C5 C6 C7 -37.7(3) . . . . ?
O3 C5 C10 N1 84.3(3) . . . . ?
O3 C5 C10 C11 -29.6(4) . . . . ?
C3 C4 C5 O3 33.7(2) . . . . ?
C3 C4 C5 C6 -75.1(3) . . . . ?
C3 C4 C5 C10 149.5(2) . . . . ?
C3 C4 C9 N1 -130.7(3) . . . . ?
C3 C4 C9 O4 50.7(4) . . . . ?
C4 C3 C8 O3 -37.0(3) . . . . ?
C4 C3 C8 C7 71.9(3) . . . . ?
C4 C5 C6 C7 70.4(3) . . . . ?
C4 C5 C10 N1 -24.7(3) . . . . ?
C4 C5 C10 C11 -138.5(3) . . . . ?
C5 O3 C8 C3 59.4(2) . . . . ?
C5 O3 C8 C7 -55.3(2) . . . . ?
C5 C4 C9 N1 -19.4(3) . . . . ?
C5 C4 C9 O4 162.0(3) . . . . ?
C5 C6 C7 C8 3.4(3) . . . . ?
C5 C10 C11 C12 149.8(3) . . . . ?
C6 C5 C10 N1 -153.1(3) . . . . ?
C6 C5 C10 C11 93.0(4) . . . . ?
C6 C7 C8 O3 31.8(3) . . . . ?
C6 C7 C8 C3 -77.2(3) . . . . ?
C8 O3 C5 C4 -57.1(2) . . . . ?
C8 O3 C5 C6 58.3(2) . . . . ?
C8 O3 C5 C10 -167.9(2) . . . . ?
C8 C3 C4 C5 1.8(3) . . . . ?
C8 C3 C4 C9 113.6(3) . . . . ?
C9 N1 C10 C5 13.6(3) . . . . ?
C9 N1 C10 C11 140.6(3) . . . . ?
C9 N1 C13 C12 -163.0(3) . . . . ?
C9 N1 C13 C14 -42.9(4) . . . . ?
C9 C4 C5 O3 -88.7(2) . . . . ?
C9 C4 C5 C6 162.4(2) . . . . ?
C9 C4 C5 C10 27.1(3) . . . . ?
C10 N1 C9 O4 -177.4(3) . . . . ?
C10 N1 C9 C4 4.0(3) . . . . ?
C10 N1 C13 C12 -7.8(3) . . . . ?
C10 N1 C13 C14 112.3(3) . . . . ?
C10 C5 C6 C7 -164.1(3) . . . . ?
C10 C11 C12 C13 -41.9(3) . . . . ?
C11 C12 C13 N1 30.7(3) . . . . ?
C11 C12 C13 C14 -87.4(3) . . . . ?
C12 C13 C14 C15 -58.6(3) . . . . ?
C13 N1 C9 O4 -22.5(5) . . . . ?
C13 N1 C9 C4 158.9(3) . . . . ?
C13 N1 C10 C5 -145.1(2) . . . . ?
C13 N1 C10 C11 -18.1(3) . . . . ?
C13 C14 C15 C16 105.3(3) . . . . ?
C13 C14 C15 C20 -72.2(4) . . . . ?
C14 C15 C16 C17 -175.6(3) . . . . ?
C14 C15 C20 C19 175.9(3) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C15 C20 C19 -1.6(5) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
C16 C17 C18 C21 178.0(3) . . . . ?
C17 C18 C19 C20 1.3(5) . . . . ?
C17 C18 C21 F1 -150.1(3) . . . . ?
C17 C18 C21 F2 91.5(4) . . . . ?
C17 C18 C21 F3 -30.6(5) . . . . ?
C18 C19 C20 C15 0.0(5) . . . . ?
C19 C18 C21 F1 28.8(5) . . . . ?
C19 C18 C21 F2 -89.6(4) . . . . ?
C19 C18 C21 F3 148.3(3) . . . . ?
C20 C15 C16 C17 2.0(5) . . . . ?
C21 C18 C19 C20 -177.6(3) . . . . ?
N4 C73 C74 C75 -37.2(3) . . . . ?
N4 C76 C77 C78 -166.3(2) . . . . ?
O13 C65 C66 C67 -152.1(2) . . . . ?
O13 C65 C66 C71 97.1(3) . . . . ?
O14 C65 C66 C67 28.2(4) . . . . ?
O14 C65 C66 C71 -82.7(4) . . . . ?
O15 C67 C68 C69 -31.3(3) . . . . ?
O15 C70 C71 C66 -31.9(3) . . . . ?
O15 C70 C71 C72 90.1(2) . . . . ?
O15 C70 C73 N4 -85.9(3) . . . . ?
O15 C70 C73 C74 27.4(4) . . . . ?
C64 O13 C65 O14 8.3(4) . . . . ?
C64 O13 C65 C66 -171.5(3) . . . . ?
C65 C66 C67 O15 -81.7(3) . . . . ?
C65 C66 C67 C68 169.7(2) . . . . ?
C65 C66 C71 C70 115.3(3) . . . . ?
C65 C66 C71 C72 3.0(3) . . . . ?
C66 C67 C68 C69 78.0(3) . . . . ?
C66 C71 C72 N4 128.6(3) . . . . ?
C66 C71 C72 O16 -51.2(4) . . . . ?
C67 O15 C70 C69 -58.8(2) . . . . ?
C67 O15 C70 C71 55.7(2) . . . . ?
C67 O15 C70 C73 167.0(2) . . . . ?
C67 C66 C71 C70 -3.5(3) . . . . ?
C67 C66 C71 C72 -115.8(3) . . . . ?
C67 C68 C69 C70 -3.8(3) . . . . ?
C68 C69 C70 O15 38.2(3) . . . . ?
C68 C69 C70 C71 -69.7(3) . . . . ?
C68 C69 C70 C73 163.5(3) . . . . ?
C69 C70 C71 C66 76.8(3) . . . . ?
C69 C70 C71 C72 -161.2(2) . . . . ?
C69 C70 C73 N4 151.9(3) . . . . ?
C69 C70 C73 C74 -94.8(4) . . . . ?
C70 O15 C67 C66 -60.0(2) . . . . ?
C70 O15 C67 C68 55.0(2) . . . . ?
C70 C71 C72 N4 16.6(3) . . . . ?
C70 C71 C72 O16 -163.1(3) . . . . ?
C70 C73 C74 C75 -150.5(3) . . . . ?
C71 C66 C67 O15 38.2(3) . . . . ?
C71 C66 C67 C68 -70.4(3) . . . . ?
C71 C70 C73 N4 22.9(3) . . . . ?
C71 C70 C73 C74 136.2(3) . . . . ?
C72 N4 C73 C70 -13.6(3) . . . . ?
C72 N4 C73 C74 -141.3(3) . . . . ?
C72 N4 C76 C75 163.7(3) . . . . ?
C72 N4 C76 C77 44.7(4) . . . . ?
C73 N4 C72 O16 177.6(3) . . . . ?
C73 N4 C72 C71 -2.1(3) . . . . ?
C73 N4 C76 C75 3.3(3) . . . . ?
C73 N4 C76 C77 -115.7(3) . . . . ?
C73 C70 C71 C66 -146.5(2) . . . . ?
C73 C70 C71 C72 -24.5(3) . . . . ?
C73 C74 C75 C76 40.7(3) . . . . ?
C74 C75 C76 N4 -27.2(3) . . . . ?
C74 C75 C76 C77 91.9(3) . . . . ?
C75 C76 C77 C78 80.6(3) . . . . ?
C76 N4 C72 O16 17.6(5) . . . . ?
C76 N4 C72 C71 -162.1(3) . . . . ?
C76 N4 C73 C70 149.6(2) . . . . ?
C76 N4 C73 C74 21.9(3) . . . . ?
C76 C77 C78 C79 -104.7(3) . . . . ?
C76 C77 C78 C83 74.8(4) . . . . ?
C77 C78 C79 C80 179.6(3) . . . . ?
C77 C78 C83 C82 179.7(3) . . . . ?
C78 C79 C80 C81 0.6(5) . . . . ?
C79 C78 C83 C82 -0.8(5) . . . . ?
C79 C80 C81 C82 -0.7(5) . . . . ?
C79 C80 C81 C84 178.3(3) . . . . ?
C80 C81 C82 C83 0.0(5) . . . . ?
C80 C81 C84 F10 -121.9(4) . . . . ?
C80 C81 C84 F11 -1.5(5) . . . . ?
C80 C81 C84 F12 121.4(4) . . . . ?
C81 C82 C83 C78 0.7(6) . . . . ?
C82 C81 C84 F10 57.2(5) . . . . ?
C82 C81 C84 F11 177.5(4) . . . . ?
C82 C81 C84 F12 -59.5(5) . . . . ?
C83 C78 C79 C80 0.1(5) . . . . ?
C84 C81 C82 C83 -179.0(3) . . . . ?
N2 C31 C32 C33 37.7(3) . . . . ?
N2 C34 C35 C36 166.0(2) . . . . ?
O5 C23 C24 C25 151.4(2) . . . . ?
O5 C23 C24 C29 -98.2(3) . . . . ?
O6 C23 C24 C25 -27.2(4) . . . . ?
O6 C23 C24 C29 83.2(3) . . . . ?
O7 C25 C26 C27 29.9(3) . . . . ?
O7 C28 C29 C24 30.6(3) . . . . ?
O7 C28 C29 C30 -91.6(2) . . . . ?
O7 C28 C31 N2 87.3(3) . . . . ?
O7 C28 C31 C32 -26.2(4) . . . . ?
C22 O5 C23 O6 -9.1(4) . . . . ?
C22 O5 C23 C24 172.3(2) . . . . ?
C23 C24 C25 O7 80.5(3) . . . . ?
C23 C24 C25 C26 -170.7(2) . . . . ?
C23 C24 C29 C28 -113.8(2) . . . . ?
C23 C24 C29 C30 -1.6(3) . . . . ?
C24 C25 C26 C27 -79.2(3) . . . . ?
C24 C29 C30 N2 -128.5(3) . . . . ?
C24 C29 C30 O8 51.6(4) . . . . ?
C25 O7 C28 C27 59.3(2) . . . . ?
C25 O7 C28 C29 -55.2(2) . . . . ?
C25 O7 C28 C31 -167.2(2) . . . . ?
C25 C24 C29 C28 4.6(3) . . . . ?
C25 C24 C29 C30 116.7(2) . . . . ?
C25 C26 C27 C28 5.6(3) . . . . ?
C26 C27 C28 O7 -39.5(3) . . . . ?
C26 C27 C28 C29 68.7(3) . . . . ?
C26 C27 C28 C31 -164.7(3) . . . . ?
C27 C28 C29 C24 -77.6(3) . . . . ?
C27 C28 C29 C30 160.1(2) . . . . ?
C27 C28 C31 N2 -151.2(3) . . . . ?
C27 C28 C31 C32 95.4(3) . . . . ?
C28 O7 C25 C24 59.9(2) . . . . ?
C28 O7 C25 C26 -54.6(2) . . . . ?
C28 C29 C30 N2 -16.5(3) . . . . ?
C28 C29 C30 O8 163.7(3) . . . . ?
C28 C31 C32 C33 151.4(3) . . . . ?
C29 C24 C25 O7 -39.1(2) . . . . ?
C29 C24 C25 C26 69.7(3) . . . . ?
C29 C28 C31 N2 -22.4(3) . . . . ?
C29 C28 C31 C32 -135.9(3) . . . . ?
C30 N2 C31 C28 13.0(3) . . . . ?
C30 N2 C31 C32 140.8(2) . . . . ?
C30 N2 C34 C33 -163.1(3) . . . . ?
C30 N2 C34 C35 -43.8(4) . . . . ?
C31 N2 C30 O8 -177.7(3) . . . . ?
C31 N2 C30 C29 2.5(3) . . . . ?
C31 N2 C34 C33 -2.6(3) . . . . ?
C31 N2 C34 C35 116.7(3) . . . . ?
C31 C28 C29 C24 146.3(2) . . . . ?
C31 C28 C29 C30 24.0(3) . . . . ?
C31 C32 C33 C34 -40.6(3) . . . . ?
C32 C33 C34 N2 26.8(3) . . . . ?
C32 C33 C34 C35 -92.9(3) . . . . ?
C33 C34 C35 C36 -80.5(3) . . . . ?
C34 N2 C30 O8 -17.5(5) . . . . ?
C34 N2 C30 C29 162.7(3) . . . . ?
C34 N2 C31 C28 -150.4(2) . . . . ?
C34 N2 C31 C32 -22.6(3) . . . . ?
C34 C35 C36 C37 -75.4(3) . . . . ?
C34 C35 C36 C41 102.4(3) . . . . ?
C35 C36 C37 C38 179.8(3) . . . . ?
C35 C36 C41 C40 -178.7(3) . . . . ?
C36 C37 C38 C39 -1.5(5) . . . . ?
C37 C36 C41 C40 -0.9(5) . . . . ?
C37 C38 C39 C40 0.0(5) . . . . ?
C37 C38 C39 C42 -179.8(3) . . . . ?
C38 C39 C40 C41 1.0(5) . . . . ?
C38 C39 C42 F4 -161.7(3) . . . . ?
C38 C39 C42 F5 78.3(4) . . . . ?
C38 C39 C42 F6 -41.6(4) . . . . ?
C39 C40 C41 C36 -0.5(5) . . . . ?
C40 C39 C42 F4 18.6(5) . . . . ?
C40 C39 C42 F5 -101.4(4) . . . . ?
C40 C39 C42 F6 138.6(3) . . . . ?
C41 C36 C37 C38 1.9(5) . . . . ?
C42 C39 C40 C41 -179.2(3) . . . . ?
N3 C52 C53 C54 36.7(3) . . . . ?
N3 C55 C56 C57 -174.9(2) . . . . ?
O9 C44 C45 C46 155.2(2) . . . . ?
O9 C44 C45 C50 -92.2(3) . . . . ?
O10 C44 C45 C46 -24.8(4) . . . . ?
O10 C44 C45 C50 87.7(3) . . . . ?
O11 C46 C47 C48 31.9(3) . . . . ?
O11 C49 C50 C45 33.8(2) . . . . ?
O11 C49 C50 C51 -88.5(2) . . . . ?
O11 C49 C52 N3 84.7(3) . . . . ?
O11 C49 C52 C53 -29.6(4) . . . . ?
C43 O9 C44 O10 -8.9(4) . . . . ?
C43 O9 C44 C45 171.0(2) . . . . ?
C44 C45 C46 O11 83.5(3) . . . . ?
C44 C45 C46 C47 -167.8(2) . . . . ?
C44 C45 C50 C49 -118.0(2) . . . . ?
C44 C45 C50 C51 -6.7(3) . . . . ?
C45 C46 C47 C48 -76.9(3) . . . . ?
C45 C50 C51 N3 -130.5(3) . . . . ?
C45 C50 C51 O12 51.6(4) . . . . ?
C46 O11 C49 C48 58.6(2) . . . . ?
C46 O11 C49 C50 -57.3(2) . . . . ?
C46 O11 C49 C52 -168.1(2) . . . . ?
C46 C45 C50 C49 1.7(3) . . . . ?
C46 C45 C50 C51 113.1(3) . . . . ?
C46 C47 C48 C49 3.4(3) . . . . ?
C47 C48 C49 O11 -37.8(3) . . . . ?
C47 C48 C49 C50 70.7(3) . . . . ?
C47 C48 C49 C52 -163.9(3) . . . . ?
C48 C49 C50 C45 -75.4(3) . . . . ?
C48 C49 C50 C51 162.3(2) . . . . ?
C48 C49 C52 N3 -152.9(3) . . . . ?
C48 C49 C52 C53 92.7(4) . . . . ?
C49 O11 C46 C45 59.3(2) . . . . ?
C49 O11 C46 C47 -55.4(2) . . . . ?
C49 C50 C51 N3 -20.0(3) . . . . ?
C49 C50 C51 O12 162.1(3) . . . . ?
C49 C52 C53 C54 151.1(3) . . . . ?
C50 C45 C46 O11 -37.0(3) . . . . ?
C50 C45 C46 C47 71.8(3) . . . . ?
C50 C49 C52 N3 -24.3(3) . . . . ?
C50 C49 C52 C53 -138.6(3) . . . . ?
C51 N3 C52 C49 12.8(3) . . . . ?
C51 N3 C52 C53 140.7(3) . . . . ?
C51 N3 C55 C54 -164.0(3) . . . . ?
C51 N3 C55 C56 -43.7(4) . . . . ?
C52 N3 C51 O12 -177.2(3) . . . . ?
C52 N3 C51 C50 4.9(3) . . . . ?
C52 N3 C55 C54 -7.7(3) . . . . ?
C52 N3 C55 C56 112.6(3) . . . . ?
C52 C49 C50 C45 149.5(2) . . . . ?
C52 C49 C50 C51 27.2(3) . . . . ?
C52 C53 C54 C55 -42.8(3) . . . . ?
C53 C54 C55 N3 31.1(3) . . . . ?
C53 C54 C55 C56 -88.3(3) . . . . ?
C54 C55 C56 C57 -61.6(3) . . . . ?
C55 N3 C51 O12 -21.3(5) . . . . ?
C55 N3 C51 C50 160.8(3) . . . . ?
C55 N3 C52 C49 -146.8(2) . . . . ?
C55 N3 C52 C53 -18.9(3) . . . . ?
C55 C56 C57 C58 -74.4(4) . . . . ?
C55 C56 C57 C62 103.4(3) . . . . ?
C56 C57 C58 C59 176.4(3) . . . . ?
C56 C57 C62 C61 -175.5(3) . . . . ?
C57 C58 C59 C60 -0.7(5) . . . . ?
C58 C57 C62 C61 2.4(5) . . . . ?
C58 C59 C60 C61 1.9(5) . . . . ?
C58 C59 C60 C63 -179.2(3) . . . . ?
C59 C60 C61 C62 -1.1(5) . . . . ?
C59 C60 C63 F7 -94.2(4) . . . . ?
C59 C60 C63 F8 146.1(3) . . . . ?
C59 C60 C63 F9 24.8(5) . . . . ?
C60 C61 C62 C57 -1.1(5) . . . . ?
C61 C60 C63 F7 84.7(4) . . . . ?
C61 C60 C63 F8 -35.0(5) . . . . ?
C61 C60 C63 F9 -156.4(3) . . . . ?
C62 C57 C58 C59 -1.5(5) . . . . ?
C63 C60 C61 C62 -179.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
-5 -6 3 0.0525 -4.9984 -5.9973 2.9903 0.4215 -0.0356 0.9389
5 6 -3 0.0525 4.9984 5.9973 -2.9903 -0.4215 0.0356 -0.9389
-6 5 -2 0.0669 -5.9934 4.9987 -1.9951 0.1015 0.9159 0.1811
6 -5 2 0.0669 5.9934 -4.9987 1.9951 -0.1015 -0.9159 -0.1811
-1 -1 13 0.0223 -1.0028 -1.0042 12.9841 0.9664 -0.1680 0.2622
1 1 -13 0.0223 1.0028 1.0042 -12.9841 -0.9664 0.1680 -0.2622
5 6 9 0.0649 4.9954 5.9928 8.9961 0.4322 -0.1341 -0.8525
1 -2 -13 0.0263 1.0020 -1.9942 -12.9866 -0.9649 -0.0482 -0.0396
-1 -1 -14 0.0148 -0.9959 -0.9941 -13.9852 -0.9545 0.2137 0.0679

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7305(8)
2 0.2695(8)

####################################################################### 
# 
# 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_jdf2_382b_cu
_database_code_depnum_ccdc_archive 'CCDC 1478960'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_audit_creation_date             2015-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl (1R*,2R*,5S*,6R*,7S*)-3-[(2,4-dimethoxyphenyl)methyl]-4-oxo-2-(prop-2-en-1-yl)-10-oxa-3-azatricyclo[5.2.1.0¹,5]dec-8-ene-6-carboxylate'
_chemical_formula_moiety         'C21 H23 N O4'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H23 N1 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   22.8332(4)
_cell_length_b                   9.84289(14)
_cell_length_c                   16.7747(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3770.04(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11151
_cell_measurement_temperature    120.00(12)
_cell_measurement_theta_max      74.2960
_cell_measurement_theta_min      4.8800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30290
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.395
_diffrn_reflns_theta_min         4.893
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   25.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00   31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega  -64.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega   40.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   60.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  112.00  162.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
  8 omega   71.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  107.00  133.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  146.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 11 omega   47.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   52.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
 13 omega  118.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
 14 omega   43.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
 15 omega  102.00  146.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   74.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   67.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 18 omega   48.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
 19 omega  111.00  152.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
 20 omega   51.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   93.00  142.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
 22 omega   64.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   45.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   32.00   81.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
 25 omega  119.00  145.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   85.00  160.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
 27 omega  102.00  147.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 28 omega   35.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 29 omega   91.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   38.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -51.0000  146.2998 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0530062000
_diffrn_orient_matrix_UB_12      0.0010454000
_diffrn_orient_matrix_UB_13      0.0569025000
_diffrn_orient_matrix_UB_21      0.0198165000
_diffrn_orient_matrix_UB_22      -0.1372350000
_diffrn_orient_matrix_UB_23      0.0350158000
_diffrn_orient_matrix_UB_31      0.0368058000
_diffrn_orient_matrix_UB_32      0.0753547000
_diffrn_orient_matrix_UB_33      0.0629011000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3356
_reflns_number_total             3855
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.019
_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)+(0.0640P)²+0.9356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          
;
The N-benzyl group exhibited positional disorder and was modelled across two positions, each of 50% occupancy.
Thermal parameters were restrained through use of RIGU command.
;
_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. Rigid body (RIGU) restrains
 C15A, C15B, C16A, C16B, C17A, C21A, C21B, C17B, C18A, C20A, C20B, C19A, C19A,
 C21A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: C16A(0.5) C15A(0.5) H15A(0.5) H15B(0.5) C17A(0.5) H17A(0.5)
 C18A(0.5) H18A(0.5) C21A(0.5) H21A(0.5) C20A(0.5) H20A(0.5) C19A(0.5)
 H19A(0.5) C20B(0.5) H20B(0.5) C21B(0.5) H21B(0.5) C19B(0.5) H19B(0.5)
 C18B(0.5) H18B(0.5) C16B(0.5) C17B(0.5) H17B(0.5) C15B(0.5) H15C(0.5) H15D(0.5)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C9(H9), C11(H11), C5(H5)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15A(H15A,H15B), C2(H2A,H2B), C15B(H15C,H15D)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C13(H13), C17A(H17A), C18A(H18A), C21A(H21A), C20A(H20A),
 C19A(H19A), C20B(H20B), C21B(H21B), C19B(H19B), C18B(H18B), C17B(H17B)
4.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
4.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O3 O 0.28354(4) 0.02643(7) 0.17161(5) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.11041(4) 0.16704(8) 0.11374(6) 0.0270(2) Uani 1 1 d . . . . .
O2 O 0.15703(4) -0.03250(8) 0.12481(6) 0.0325(2) Uani 1 1 d . . . . .
O4 O 0.20564(4) 0.19182(12) -0.01526(6) 0.0384(2) Uani 1 1 d . . . . .
N1 N 0.30140(5) 0.13748(11) 0.01021(7) 0.0280(2) Uani 1 1 d . . . . .
C6 C 0.28284(5) 0.17258(12) 0.27801(7) 0.0258(3) Uani 1 1 d . . . . .
H6 H 0.2799 0.1930 0.3320 0.031 Uiso 1 1 calc R . . . .
C12 C 0.38715(6) 0.02419(13) 0.07470(8) 0.0301(3) Uani 1 1 d . . . . .
H12A H 0.3648 -0.0593 0.0788 0.036 Uiso 1 1 calc R . . . .
H12B H 0.4088 0.0219 0.0250 0.036 Uiso 1 1 calc R . . . .
C4 C 0.20284(5) 0.17027(11) 0.17659(7) 0.0229(3) Uani 1 1 d . . . . .
H4 H 0.1858 0.2444 0.2080 0.027 Uiso 1 1 calc R . . . .
C7 C 0.32258(5) 0.21921(11) 0.22687(7) 0.0235(2) Uani 1 1 d . . . . .
H7 H 0.3537 0.2773 0.2377 0.028 Uiso 1 1 calc R . . . .
C8 C 0.30617(5) 0.15723(10) 0.14727(7) 0.0207(2) Uani 1 1 d . . . . .
C3 C 0.15533(5) 0.08857(12) 0.13608(7) 0.0241(2) Uani 1 1 d . . . . .
C9 C 0.24911(5) 0.22564(10) 0.11716(7) 0.0212(2) Uani 1 1 d . . . . .
H9 H 0.2521 0.3247 0.1214 0.025 Uiso 1 1 calc R . . . .
C11 C 0.34524(5) 0.14563(12) 0.07436(7) 0.0239(3) Uani 1 1 d . . . . .
H11 H 0.3679 0.2296 0.0684 0.029 Uiso 1 1 calc R . . . .
C5 C 0.24322(5) 0.07894(11) 0.22996(7) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.2226 0.0098 0.2613 0.029 Uiso 1 1 calc R . . . .
C10 C 0.24718(6) 0.18242(12) 0.03057(8) 0.0262(3) Uani 1 1 d . . . . .
C13 C 0.42910(7) 0.03326(15) 0.14295(9) 0.0370(3) Uani 1 1 d . . . . .
H13 H 0.4141 0.0236 0.1942 0.044 Uiso 1 1 calc R . . . .
C16A C 0.3503(5) 0.2085(8) -0.1079(7) 0.0257(15) Uani 0.5 1 d . U P A 1
C15A C 0.3131(6) 0.1014(13) -0.0679(8) 0.0315(17) Uani 0.5 1 d . U P A 1
H15A H 0.2766 0.0909 -0.0969 0.038 Uiso 0.5 1 calc R . P A 1
H15B H 0.3335 0.0149 -0.0689 0.038 Uiso 0.5 1 calc R . P A 1
C17A C 0.3444(7) 0.3453(11) -0.0904(9) 0.033(2) Uani 0.5 1 d . U P A 1
H17A H 0.3180 0.3720 -0.0513 0.039 Uiso 0.5 1 calc R . P A 1
C18A C 0.3771(4) 0.4436(6) -0.1301(5) 0.0383(13) Uani 0.5 1 d . U P A 1
H18A H 0.3722 0.5351 -0.1180 0.046 Uiso 0.5 1 calc R . P A 1
C14 C 0.48568(7) 0.05393(19) 0.13560(11) 0.0473(4) Uani 1 1 d . . . . .
H14A H 0.5022 0.0641 0.0853 0.057 Uiso 1 1 calc R . . . .
H14B H 0.5092 0.0585 0.1807 0.057 Uiso 1 1 calc R . . . .
C2 C 0.06445(6) 0.09837(13) 0.06972(9) 0.0311(3) Uani 1 1 d . . . . .
H2A H 0.0386 0.0508 0.1061 0.037 Uiso 1 1 calc R . . . .
H2B H 0.0813 0.0327 0.0332 0.037 Uiso 1 1 calc R . . . .
C1 C 0.03113(7) 0.20439(17) 0.02454(11) 0.0473(4) Uani 1 1 d . . . . .
H1A H 0.0569 0.2491 -0.0123 0.071 Uiso 1 1 calc GR . . . .
H1B H 0.0154 0.2698 0.0612 0.071 Uiso 1 1 calc GR . . . .
H1C H -0.0003 0.1622 -0.0043 0.071 Uiso 1 1 calc GR . . . .
C21A C 0.3907(3) 0.1723(5) -0.1655(4) 0.0334(11) Uani 0.5 1 d . U P A 1
H21A H 0.3960 0.0808 -0.1773 0.040 Uiso 0.5 1 calc R . P A 1
C20A C 0.4236(2) 0.2681(6) -0.2060(4) 0.0400(11) Uani 0.5 1 d . U P A 1
H20A H 0.4498 0.2409 -0.2453 0.048 Uiso 0.5 1 calc R . P A 1
C19A C 0.4173(3) 0.4035(7) -0.1880(3) 0.0401(14) Uani 0.5 1 d . U P A 1
H19A H 0.4398 0.4682 -0.2144 0.048 Uiso 0.5 1 calc R . P A 1
C20B C 0.4267(2) 0.3335(8) -0.2007(3) 0.0419(14) Uani 0.5 1 d . U P A 2
H20B H 0.4553 0.3184 -0.2392 0.050 Uiso 0.5 1 calc R . P A 2
C21B C 0.3981(3) 0.2246(6) -0.1674(4) 0.0376(12) Uani 0.5 1 d . U P A 2
H21B H 0.4072 0.1367 -0.1836 0.045 Uiso 0.5 1 calc R . P A 2
C19B C 0.4138(2) 0.4641(6) -0.1780(3) 0.0394(12) Uani 0.5 1 d . . P A 2
H19B H 0.4332 0.5368 -0.2016 0.047 Uiso 0.5 1 calc R . P A 2
C18B C 0.3717(3) 0.4873(6) -0.1199(5) 0.0345(12) Uani 0.5 1 d . . P A 2
H18B H 0.3632 0.5755 -0.1038 0.041 Uiso 0.5 1 calc R . P A 2
C16B C 0.3549(5) 0.2465(9) -0.1088(7) 0.0270(16) Uani 0.5 1 d . U P A 2
C17B C 0.3420(6) 0.3775(11) -0.0858(9) 0.0275(16) Uani 0.5 1 d . U P A 2
H17B H 0.3135 0.3930 -0.0473 0.033 Uiso 0.5 1 calc R . P A 2
C15B C 0.3216(5) 0.1254(11) -0.0764(7) 0.0287(17) Uani 0.5 1 d . U P A 2
H15C H 0.3463 0.0456 -0.0811 0.034 Uiso 0.5 1 calc R . P A 2
H15D H 0.2874 0.1106 -0.1096 0.034 Uiso 0.5 1 calc R . P A 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
O3 C8 1.4461(13) . ?
O3 C5 1.4398(15) . ?
O1 C3 1.3377(15) . ?
O1 C2 1.4502(15) . ?
O2 C3 1.2072(15) . ?
O4 C10 1.2244(16) . ?
N1 C11 1.4718(16) . ?
N1 C10 1.3582(17) . ?
N1 C15A 1.384(14) . ?
N1 C15B 1.529(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.3304(18) . ?
C6 C5 1.5225(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.5313(17) . ?
C12 C13 1.496(2) . ?
C4 H4 0.9800 . ?
C4 C3 1.5118(16) . ?
C4 C9 1.5514(16) . ?
C4 C5 1.5682(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.5151(16) . ?
C8 C9 1.5512(15) . ?
C8 C11 1.5180(17) . ?
C9 H9 0.9800 . ?
C9 C10 1.5142(17) . ?
C11 H11 0.9800 . ?
C5 H5 0.9800 . ?
C13 H13 0.9300 . ?
C13 C14 1.314(2) . ?
C16A C15A 1.511(9) . ?
C16A C17A 1.385(9) . ?
C16A C21A 1.383(12) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C17A H17A 0.9300 . ?
C17A C18A 1.391(15) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.394(10) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.497(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C21A H21A 0.9300 . ?
C21A C20A 1.383(6) . ?
C20A H20A 0.9300 . ?
C20A C19A 1.374(8) . ?
C19A H19A 0.9300 . ?
C20B H20B 0.9300 . ?
C20B C21B 1.373(8) . ?
C20B C19B 1.373(7) . ?
C21B H21B 0.9300 . ?
C21B C16B 1.410(12) . ?
C19B H19B 0.9300 . ?
C19B C18B 1.388(9) . ?
C18B H18B 0.9300 . ?
C18B C17B 1.398(14) . ?
C16B C17B 1.377(9) . ?
C16B C15B 1.515(9) . ?
C17B H17B 0.9300 . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?

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
C5 O3 C8 95.78(8) . . ?
C3 O1 C2 115.37(9) . . ?
C11 N1 C15B 119.6(4) . . ?
C10 N1 C11 114.72(10) . . ?
C10 N1 C15A 119.9(6) . . ?
C10 N1 C15B 122.6(4) . . ?
C15A N1 C11 125.1(6) . . ?
C7 C6 H6 127.1 . . ?
C7 C6 C5 105.83(10) . . ?
C5 C6 H6 127.1 . . ?
H12A C12 H12B 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 C11 110.88(11) . . ?
C3 C4 H4 110.7 . . ?
C3 C4 C9 112.74(10) . . ?
C3 C4 C5 111.93(9) . . ?
C9 C4 H4 110.7 . . ?
C9 C4 C5 99.67(9) . . ?
C5 C4 H4 110.7 . . ?
C6 C7 H7 127.4 . . ?
C6 C7 C8 105.12(10) . . ?
C8 C7 H7 127.4 . . ?
O3 C8 C7 101.42(9) . . ?
O3 C8 C9 100.27(8) . . ?
O3 C8 C11 111.74(9) . . ?
C7 C8 C9 108.66(9) . . ?
C7 C8 C11 126.51(10) . . ?
C11 C8 C9 105.30(9) . . ?
O1 C3 C4 111.66(10) . . ?
O2 C3 O1 123.42(11) . . ?
O2 C3 C4 124.92(11) . . ?
C4 C9 H9 110.5 . . ?
C8 C9 C4 102.13(9) . . ?
C8 C9 H9 110.5 . . ?
C10 C9 C4 119.87(10) . . ?
C10 C9 C8 102.41(9) . . ?
C10 C9 H9 110.5 . . ?
N1 C11 C12 112.65(10) . . ?
N1 C11 C8 101.16(9) . . ?
N1 C11 H11 109.2 . . ?
C12 C11 H11 109.2 . . ?
C8 C11 C12 115.03(10) . . ?
C8 C11 H11 109.2 . . ?
O3 C5 C6 101.38(9) . . ?
O3 C5 C4 101.16(9) . . ?
O3 C5 H5 115.0 . . ?
C6 C5 C4 107.73(9) . . ?
C6 C5 H5 115.0 . . ?
C4 C5 H5 115.0 . . ?
O4 C10 N1 124.95(12) . . ?
O4 C10 C9 127.12(12) . . ?
N1 C10 C9 107.83(10) . . ?
C12 C13 H13 117.7 . . ?
C14 C13 C12 124.56(14) . . ?
C14 C13 H13 117.7 . . ?
C17A C16A C15A 122.0(10) . . ?
C21A C16A C15A 120.4(7) . . ?
C21A C16A C17A 117.6(8) . . ?
N1 C15A C16A 110.5(9) . . ?
N1 C15A H15A 109.6 . . ?
N1 C15A H15B 109.6 . . ?
C16A C15A H15A 109.6 . . ?
C16A C15A H15B 109.6 . . ?
H15A C15A H15B 108.1 . . ?
C16A C17A H17A 119.2 . . ?
C16A C17A C18A 121.6(9) . . ?
C18A C17A H17A 119.2 . . ?
C17A C18A H18A 120.3 . . ?
C17A C18A C19A 119.3(7) . . ?
C19A C18A H18A 120.3 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
O1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
O1 C2 C1 107.49(11) . . ?
H2A C2 H2B 108.5 . . ?
C1 C2 H2A 110.2 . . ?
C1 C2 H2B 110.2 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C16A C21A H21A 119.0 . . ?
C16A C21A C20A 122.0(5) . . ?
C20A C21A H21A 119.0 . . ?
C21A C20A H20A 120.1 . . ?
C19A C20A C21A 119.8(5) . . ?
C19A C20A H20A 120.1 . . ?
C18A C19A H19A 120.1 . . ?
C20A C19A C18A 119.7(5) . . ?
C20A C19A H19A 120.1 . . ?
C21B C20B H20B 119.5 . . ?
C19B C20B H20B 119.5 . . ?
C19B C20B C21B 121.1(5) . . ?
C20B C21B H21B 120.1 . . ?
C20B C21B C16B 119.8(5) . . ?
C16B C21B H21B 120.1 . . ?
C20B C19B H19B 120.1 . . ?
C20B C19B C18B 119.8(5) . . ?
C18B C19B H19B 120.1 . . ?
C19B C18B H18B 120.1 . . ?
C19B C18B C17B 119.7(7) . . ?
C17B C18B H18B 120.1 . . ?
C21B C16B C15B 118.7(7) . . ?
C17B C16B C21B 119.2(8) . . ?
C17B C16B C15B 122.0(9) . . ?
C18B C17B H17B 119.8 . . ?
C16B C17B C18B 120.4(10) . . ?
C16B C17B H17B 119.8 . . ?
N1 C15B H15C 108.4 . . ?
N1 C15B H15D 108.4 . . ?
C16B C15B N1 115.5(8) . . ?
C16B C15B H15C 108.4 . . ?
C16B C15B H15D 108.4 . . ?
H15C C15B H15D 107.5 . . ?

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
O3 C8 C9 C4 36.34(10) . . . . ?
O3 C8 C9 C10 -88.33(10) . . . . ?
O3 C8 C11 N1 80.09(11) . . . . ?
O3 C8 C11 C12 -41.60(14) . . . . ?
C6 C7 C8 O3 -34.00(11) . . . . ?
C6 C7 C8 C9 71.09(11) . . . . ?
C6 C7 C8 C11 -162.30(11) . . . . ?
C4 C9 C10 O4 54.86(17) . . . . ?
C4 C9 C10 N1 -128.62(11) . . . . ?
C7 C6 C5 O3 31.47(12) . . . . ?
C7 C6 C5 C4 -74.30(12) . . . . ?
C7 C8 C9 C4 -69.54(10) . . . . ?
C7 C8 C9 C10 165.79(9) . . . . ?
C7 C8 C11 N1 -155.82(10) . . . . ?
C7 C8 C11 C12 82.49(14) . . . . ?
C8 O3 C5 C6 -50.40(10) . . . . ?
C8 O3 C5 C4 60.48(9) . . . . ?
C8 C9 C10 O4 166.85(13) . . . . ?
C8 C9 C10 N1 -16.63(12) . . . . ?
C3 O1 C2 C1 -159.10(13) . . . . ?
C3 C4 C9 C8 -118.99(10) . . . . ?
C3 C4 C9 C10 -6.85(14) . . . . ?
C3 C4 C5 O3 83.06(11) . . . . ?
C3 C4 C5 C6 -171.03(10) . . . . ?
C9 C4 C3 O1 -89.77(12) . . . . ?
C9 C4 C3 O2 90.23(15) . . . . ?
C9 C4 C5 O3 -36.37(10) . . . . ?
C9 C4 C5 C6 69.54(11) . . . . ?
C9 C8 C11 N1 -27.85(11) . . . . ?
C9 C8 C11 C12 -149.54(10) . . . . ?
C11 N1 C10 O4 175.40(12) . . . . ?
C11 N1 C10 C9 -1.21(14) . . . . ?
C11 N1 C15A C16A -67.2(10) . . . . ?
C11 N1 C15B C16B -64.7(8) . . . . ?
C11 C12 C13 C14 -112.23(17) . . . . ?
C11 C8 C9 C4 152.43(9) . . . . ?
C11 C8 C9 C10 27.76(11) . . . . ?
C5 O3 C8 C7 51.62(10) . . . . ?
C5 O3 C8 C9 -60.00(9) . . . . ?
C5 O3 C8 C11 -171.15(9) . . . . ?
C5 C6 C7 C8 1.55(12) . . . . ?
C5 C4 C3 O1 158.81(10) . . . . ?
C5 C4 C3 O2 -21.19(17) . . . . ?
C5 C4 C9 C8 -0.16(10) . . . . ?
C5 C4 C9 C10 111.98(11) . . . . ?
C10 N1 C11 C12 142.14(11) . . . . ?
C10 N1 C11 C8 18.80(13) . . . . ?
C10 N1 C15A C16A 105.9(7) . . . . ?
C10 N1 C15B C16B 94.5(7) . . . . ?
C13 C12 C11 N1 -177.37(11) . . . . ?
C13 C12 C11 C8 -62.13(14) . . . . ?
C16A C17A C18A C19A -0.9(17) . . . . ?
C16A C21A C20A C19A 1.5(10) . . . . ?
C15A N1 C11 C12 -44.4(6) . . . . ?
C15A N1 C11 C8 -167.8(6) . . . . ?
C15A N1 C10 O4 1.6(6) . . . . ?
C15A N1 C10 C9 -175.0(5) . . . . ?
C15A C16A C17A C18A -177.2(12) . . . . ?
C15A C16A C21A C20A 176.9(8) . . . . ?
C17A C16A C15A N1 -34.5(14) . . . . ?
C17A C16A C21A C20A -1.4(13) . . . . ?
C17A C18A C19A C20A 0.9(13) . . . . ?
C2 O1 C3 O2 -3.83(18) . . . . ?
C2 O1 C3 C4 176.17(10) . . . . ?
C21A C16A C15A N1 147.2(11) . . . . ?
C21A C16A C17A C18A 1.1(17) . . . . ?
C21A C20A C19A C18A -1.1(9) . . . . ?
C20B C21B C16B C17B 0.1(13) . . . . ?
C20B C21B C16B C15B 176.6(7) . . . . ?
C20B C19B C18B C17B -1.0(12) . . . . ?
C21B C20B C19B C18B 0.8(9) . . . . ?
C21B C16B C17B C18B -0.3(16) . . . . ?
C21B C16B C15B N1 149.1(9) . . . . ?
C19B C20B C21B C16B -0.3(10) . . . . ?
C19B C18B C17B C16B 0.8(16) . . . . ?
C17B C16B C15B N1 -34.5(13) . . . . ?
C15B N1 C11 C12 -57.1(5) . . . . ?
C15B N1 C11 C8 179.6(5) . . . . ?
C15B N1 C10 O4 15.3(5) . . . . ?
C15B N1 C10 C9 -161.3(5) . . . . ?
C15B C16B C17B C18B -176.7(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
4 0 10 0.0301 4.0001 0.0001 9.9997 0.3570 0.4294 0.7762
-4 0 -10 0.0301 -4.0001 -0.0001 -9.9997 -0.3570 -0.4294 -0.7762
-3 6 1 0.1021 -3.0008 6.0000 0.9995 0.2222 -0.8479 0.4045
3 -6 -1 0.1021 3.0008 -6.0000 -0.9995 -0.2222 0.8479 -0.4045
12 0 -7 0.0311 11.9996 0.0001 -7.0004 -1.0344 -0.0073 0.0013
-12 0 7 0.0311 -11.9996 -0.0001 7.0004 1.0344 0.0073 -0.0013
-6 -5 -5 0.0852 -5.9992 -5.0001 -4.9992 0.0283 0.3923 -0.9120
10 5 1 0.0792 9.9990 5.0001 0.9991 -0.4679 -0.4531 0.8076
-13 0 -5 0.0242 -12.9998 -0.0001 -4.9994 0.4046 -0.4327 -0.7929
13 0 5 0.0390 12.9998 0.0001 4.9994 -0.4046 0.4327 0.7929
-15 1 2 0.0235 -14.9998 0.9999 2.0004 0.9100 -0.3644 -0.3509
15 0 -1 0.0382 14.9996 0.0001 -1.0006 -0.8520 0.2622 0.4891
2 -1 -11 0.0255 1.9998 -1.0000 -10.9998 -0.7330 -0.2083 -0.6937
-3 0 11 0.0279 -2.9997 0.0000 11.0000 0.7849 0.3257 0.5815
-6 -6 1 0.0941 -5.9989 -6.0000 1.0009 0.3687 0.7396 -0.6100

_olex2_date_sample_data_collection 2015-09-10
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jdf2_400b_cu
_database_code_depnum_ccdc_archive 'CCDC 1478961'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_audit_creation_date             2015-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl (1R*,2R*,10S*,11R*,12S*)-5-benzyl-9-oxo-15-oxa-5,8-diazatetracyclo[10.2.1.0¹,¹°.0²,8]pentadecane-11-carboxylate'
_chemical_formula_moiety         'C22 H28 N2 O4'
_chemical_formula_sum            'C22 H28 N2 O4'
_chemical_formula_weight         384.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H28 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.1612(2)
_cell_length_b                   9.24516(11)
_cell_length_c                   10.76938(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.7643(12)
_cell_angle_gamma                90
_cell_volume                     1993.37(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7665
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      74.2510
_cell_measurement_theta_min      5.2580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12732
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.397
_diffrn_reflns_theta_min         4.417
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  120.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega  -43.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -69.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -37.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7089  -57.0000  150.0000 65

#__ type_ start__ end____ width___ exp.time_
  6 omega   92.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000  164.4845 39

#__ type_ start__ end____ width___ exp.time_
  7 omega   84.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   93.6186 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   79.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000  139.9270 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   55.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
 10 omega  104.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
 11 omega  113.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  152.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega  149.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega  149.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega  125.00  152.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega  109.00  138.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   93.00  142.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
 18 omega   68.00  114.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
 19 omega   89.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   46.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 21 omega   54.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 22 omega   38.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   93.6186 37

#__ type_ start__ end____ width___ exp.time_
 23 omega   43.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000  139.9270 29

#__ type_ start__ end____ width___ exp.time_
 24 omega   35.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 25 omega   33.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 26 omega   35.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 27 omega   47.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000 -180.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0163103000
_diffrn_orient_matrix_UB_12      -0.1466576000
_diffrn_orient_matrix_UB_13      0.0643621000
_diffrn_orient_matrix_UB_21      -0.0730296000
_diffrn_orient_matrix_UB_22      -0.0480524000
_diffrn_orient_matrix_UB_23      -0.0339913000
_diffrn_orient_matrix_UB_31      0.0179229000
_diffrn_orient_matrix_UB_32      -0.0627443000
_diffrn_orient_matrix_UB_33      -0.1243521000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3657
_reflns_number_total             4055
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.048
_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)+(0.0783P)²+0.4675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1280
_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:
 C4(H4), C5(H5), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,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 0.12832(5) 0.55524(10) 0.26785(9) 0.0200(2) Uani 1 1 d . . . . .
N1 N 0.25256(5) 0.29831(11) 0.14990(10) 0.0167(2) Uani 1 1 d . . . . .
C1 C 0.21191(10) 0.67251(18) 0.40555(18) 0.0412(4) Uani 1 1 d . . . . .
H1A H 0.2455 0.6246 0.3645 0.062 Uiso 1 1 calc GR . . . .
H1B H 0.2006 0.6137 0.4735 0.062 Uiso 1 1 calc GR . . . .
H1C H 0.2287 0.7642 0.4373 0.062 Uiso 1 1 calc GR . . . .
O2 O 0.06793(5) 0.66336(11) 0.10538(11) 0.0311(3) Uani 1 1 d . . . . .
N2 N 0.36877(5) 0.11446(12) 0.30628(11) 0.0195(2) Uani 1 1 d . . . . .
C2 C 0.15162(8) 0.69572(15) 0.31515(16) 0.0296(3) Uani 1 1 d . . . . .
H2A H 0.1172 0.7432 0.3560 0.036 Uiso 1 1 calc R . . . .
H2B H 0.1623 0.7565 0.2469 0.036 Uiso 1 1 calc R . . . .
O3 O 0.12326(4) 0.23877(9) 0.25705(8) 0.0157(2) Uani 1 1 d . . . . .
C3 C 0.09034(6) 0.55539(14) 0.15732(12) 0.0188(3) Uani 1 1 d . . . . .
O4 O 0.22561(4) 0.52753(10) 0.08169(9) 0.0202(2) Uani 1 1 d . . . . .
C4 C 0.07863(6) 0.40437(13) 0.10498(11) 0.0170(3) Uani 1 1 d . . . . .
H4 H 0.0440 0.4078 0.0331 0.020 Uiso 1 1 calc R . . . .
C5 C 0.05946(6) 0.28884(14) 0.19940(12) 0.0180(3) Uani 1 1 d . . . . .
H5 H 0.0304 0.3259 0.2591 0.022 Uiso 1 1 calc R . . . .
C6 C 0.03129(6) 0.15404(14) 0.12671(13) 0.0218(3) Uani 1 1 d . . . . .
H6A H 0.0016 0.1809 0.0529 0.026 Uiso 1 1 calc R . . . .
H6B H 0.0077 0.0914 0.1789 0.026 Uiso 1 1 calc R . . . .
C7 C 0.09585(6) 0.08063(14) 0.09120(12) 0.0193(3) Uani 1 1 d . . . . .
H7A H 0.1034 -0.0127 0.1315 0.023 Uiso 1 1 calc R . . . .
H7B H 0.0947 0.0693 0.0014 0.023 Uiso 1 1 calc R . . . .
C8 C 0.14797(6) 0.19190(13) 0.14290(11) 0.0145(2) Uani 1 1 d . . . . .
C9 C 0.14227(6) 0.33138(13) 0.06489(11) 0.0151(2) Uani 1 1 d . . . . .
H9 H 0.1358 0.3084 -0.0246 0.018 Uiso 1 1 calc R . . . .
C10 C 0.21011(6) 0.40200(13) 0.10003(11) 0.0156(2) Uani 1 1 d . . . . .
C11 C 0.22212(6) 0.15641(13) 0.16610(11) 0.0152(3) Uani 1 1 d . . . . .
H11 H 0.2337 0.0910 0.1003 0.018 Uiso 1 1 calc R . . . .
C12 C 0.24423(6) 0.08869(14) 0.29334(12) 0.0180(3) Uani 1 1 d . . . . .
H12A H 0.2110 0.0183 0.3113 0.022 Uiso 1 1 calc R . . . .
H12B H 0.2455 0.1636 0.3566 0.022 Uiso 1 1 calc R . . . .
C13 C 0.31227(6) 0.01437(14) 0.30401(13) 0.0209(3) Uani 1 1 d . . . . .
H13A H 0.3177 -0.0431 0.3799 0.025 Uiso 1 1 calc R . . . .
H13B H 0.3132 -0.0511 0.2339 0.025 Uiso 1 1 calc R . . . .
C14 C 0.36848(6) 0.19750(15) 0.19039(12) 0.0203(3) Uani 1 1 d . . . . .
H14A H 0.3545 0.1343 0.1203 0.024 Uiso 1 1 calc R . . . .
H14B H 0.4137 0.2287 0.1827 0.024 Uiso 1 1 calc R . . . .
C15 C 0.32338(6) 0.32912(14) 0.18181(13) 0.0209(3) Uani 1 1 d . . . . .
H15A H 0.3293 0.3791 0.2615 0.025 Uiso 1 1 calc R . . . .
H15B H 0.3375 0.3943 0.1194 0.025 Uiso 1 1 calc R . . . .
C16 C 0.43185(6) 0.03382(14) 0.33076(13) 0.0215(3) Uani 1 1 d . . . . .
H16A H 0.4400 -0.0175 0.2554 0.026 Uiso 1 1 calc R . . . .
H16B H 0.4276 -0.0375 0.3954 0.026 Uiso 1 1 calc R . . . .
C17 C 0.49105(6) 0.13016(14) 0.37152(12) 0.0187(3) Uani 1 1 d . . . . .
C18 C 0.48526(7) 0.24694(15) 0.45098(13) 0.0242(3) Uani 1 1 d . . . . .
H18 H 0.4436 0.2714 0.4737 0.029 Uiso 1 1 calc R . . . .
C19 C 0.54097(8) 0.32734(16) 0.49667(14) 0.0291(3) Uani 1 1 d . . . . .
H19 H 0.5365 0.4042 0.5508 0.035 Uiso 1 1 calc R . . . .
C20 C 0.60331(7) 0.29377(16) 0.46207(15) 0.0282(3) Uani 1 1 d . . . . .
H20 H 0.6406 0.3475 0.4932 0.034 Uiso 1 1 calc R . . . .
C21 C 0.60972(7) 0.17987(16) 0.38091(14) 0.0258(3) Uani 1 1 d . . . . .
H21 H 0.6512 0.1576 0.3564 0.031 Uiso 1 1 calc R . . . .
C22 C 0.55372(6) 0.09861(14) 0.33605(13) 0.0212(3) Uani 1 1 d . . . . .
H22 H 0.5583 0.0221 0.2816 0.025 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 C2 1.4527(16) . ?
O1 C3 1.3374(16) . ?
N1 C10 1.3534(16) . ?
N1 C11 1.4674(15) . ?
N1 C15 1.4568(15) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.481(2) . ?
O2 C3 1.2058(17) . ?
N2 C13 1.4657(16) . ?
N2 C14 1.4647(16) . ?
N2 C16 1.4708(15) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O3 C5 1.4374(14) . ?
O3 C8 1.4461(14) . ?
C3 C4 1.5138(17) . ?
O4 C10 1.2240(16) . ?
C4 H4 0.9800 . ?
C4 C5 1.5546(17) . ?
C4 C9 1.5551(16) . ?
C5 H5 0.9800 . ?
C5 C6 1.5439(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.5552(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5278(16) . ?
C8 C9 1.5360(16) . ?
C8 C11 1.5223(16) . ?
C9 H9 0.9800 . ?
C9 C10 1.5226(16) . ?
C11 H11 0.9800 . ?
C11 C12 1.5246(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5265(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5153(18) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5124(18) . ?
C17 C18 1.3911(19) . ?
C17 C22 1.3932(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.394(2) . ?
C22 H22 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
C3 O1 C2 116.03(10) . . ?
C10 N1 C11 115.26(10) . . ?
C10 N1 C15 120.77(10) . . ?
C15 N1 C11 123.97(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C13 N2 C16 109.68(10) . . ?
C14 N2 C13 113.05(10) . . ?
C14 N2 C16 109.57(10) . . ?
O1 C2 C1 107.91(12) . . ?
O1 C2 H2A 110.1 . . ?
O1 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C5 O3 C8 96.30(8) . . ?
O1 C3 C4 112.23(10) . . ?
O2 C3 O1 123.90(12) . . ?
O2 C3 C4 123.87(12) . . ?
C3 C4 H4 109.2 . . ?
C3 C4 C5 115.47(10) . . ?
C3 C4 C9 113.96(10) . . ?
C5 C4 H4 109.2 . . ?
C5 C4 C9 99.23(9) . . ?
C9 C4 H4 109.2 . . ?
O3 C5 C4 103.00(9) . . ?
O3 C5 H5 113.7 . . ?
O3 C5 C6 102.48(10) . . ?
C4 C5 H5 113.7 . . ?
C6 C5 C4 109.14(10) . . ?
C6 C5 H5 113.7 . . ?
C5 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
C5 C6 C7 102.03(9) . . ?
H6A C6 H6B 109.2 . . ?
C7 C6 H6A 111.4 . . ?
C7 C6 H6B 111.4 . . ?
C6 C7 H7A 111.7 . . ?
C6 C7 H7B 111.7 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 C6 100.14(10) . . ?
C8 C7 H7A 111.7 . . ?
C8 C7 H7B 111.7 . . ?
O3 C8 C7 102.75(9) . . ?
O3 C8 C9 101.67(9) . . ?
O3 C8 C11 110.80(9) . . ?
C7 C8 C9 111.22(10) . . ?
C11 C8 C7 122.32(10) . . ?
C11 C8 C9 106.23(9) . . ?
C4 C9 H9 110.4 . . ?
C8 C9 C4 102.91(9) . . ?
C8 C9 H9 110.4 . . ?
C10 C9 C4 119.43(10) . . ?
C10 C9 C8 102.53(9) . . ?
C10 C9 H9 110.4 . . ?
N1 C10 C9 107.61(10) . . ?
O4 C10 N1 125.04(11) . . ?
O4 C10 C9 127.26(11) . . ?
N1 C11 C8 101.78(9) . . ?
N1 C11 H11 109.1 . . ?
N1 C11 C12 113.08(10) . . ?
C8 C11 H11 109.1 . . ?
C8 C11 C12 114.42(10) . . ?
C12 C11 H11 109.1 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C11 C12 C13 114.67(10) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
N2 C13 C12 114.01(10) . . ?
N2 C13 H13A 108.8 . . ?
N2 C13 H13B 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.6 . . ?
N2 C14 H14A 108.6 . . ?
N2 C14 H14B 108.6 . . ?
N2 C14 C15 114.52(11) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
N1 C15 C14 114.95(11) . . ?
N1 C15 H15A 108.5 . . ?
N1 C15 H15B 108.5 . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
N2 C16 H16A 109.0 . . ?
N2 C16 H16B 109.0 . . ?
N2 C16 C17 112.93(11) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C18 C17 C16 121.00(11) . . ?
C18 C17 C22 118.41(12) . . ?
C22 C17 C16 120.49(12) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.70(13) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.40(14) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.64(14) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.79(13) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 121.04(13) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 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 C3 C4 C5 45.57(14) . . . . ?
O1 C3 C4 C9 -68.38(13) . . . . ?
N1 C11 C12 C13 -80.57(13) . . . . ?
O2 C3 C4 C5 -134.37(13) . . . . ?
O2 C3 C4 C9 111.68(14) . . . . ?
N2 C14 C15 N1 -78.04(15) . . . . ?
N2 C16 C17 C18 38.56(17) . . . . ?
N2 C16 C17 C22 -145.26(12) . . . . ?
C2 O1 C3 O2 -10.17(18) . . . . ?
C2 O1 C3 C4 169.90(11) . . . . ?
O3 C5 C6 C7 -31.78(12) . . . . ?
O3 C8 C9 C4 -34.22(11) . . . . ?
O3 C8 C9 C10 90.34(10) . . . . ?
O3 C8 C11 N1 -86.96(11) . . . . ?
O3 C8 C11 C12 35.35(14) . . . . ?
C3 O1 C2 C1 -157.52(14) . . . . ?
C3 C4 C5 O3 -86.56(12) . . . . ?
C3 C4 C5 C6 165.10(10) . . . . ?
C3 C4 C9 C8 122.73(11) . . . . ?
C3 C4 C9 C10 10.10(15) . . . . ?
C4 C5 C6 C7 76.91(12) . . . . ?
C4 C9 C10 N1 131.71(11) . . . . ?
C4 C9 C10 O4 -51.73(17) . . . . ?
C5 O3 C8 C7 -58.48(10) . . . . ?
C5 O3 C8 C9 56.71(10) . . . . ?
C5 O3 C8 C11 169.27(10) . . . . ?
C5 C4 C9 C8 -0.56(11) . . . . ?
C5 C4 C9 C10 -113.19(11) . . . . ?
C5 C6 C7 C8 -3.41(12) . . . . ?
C6 C7 C8 O3 37.59(11) . . . . ?
C6 C7 C8 C9 -70.49(12) . . . . ?
C6 C7 C8 C11 162.61(11) . . . . ?
C7 C8 C9 C4 74.56(11) . . . . ?
C7 C8 C9 C10 -160.88(10) . . . . ?
C7 C8 C11 N1 151.74(11) . . . . ?
C7 C8 C11 C12 -85.95(14) . . . . ?
C8 O3 C5 C4 -58.09(10) . . . . ?
C8 O3 C5 C6 55.21(10) . . . . ?
C8 C9 C10 N1 18.88(12) . . . . ?
C8 C9 C10 O4 -164.57(12) . . . . ?
C8 C11 C12 C13 163.50(10) . . . . ?
C9 C4 C5 O3 35.65(11) . . . . ?
C9 C4 C5 C6 -72.69(11) . . . . ?
C9 C8 C11 N1 22.67(12) . . . . ?
C9 C8 C11 C12 144.98(10) . . . . ?
C10 N1 C11 C8 -11.40(13) . . . . ?
C10 N1 C11 C12 -134.63(11) . . . . ?
C10 N1 C15 C14 -158.35(11) . . . . ?
C11 N1 C10 O4 178.42(11) . . . . ?
C11 N1 C10 C9 -4.93(14) . . . . ?
C11 N1 C15 C14 20.47(18) . . . . ?
C11 C8 C9 C4 -150.18(10) . . . . ?
C11 C8 C9 C10 -25.62(12) . . . . ?
C11 C12 C13 N2 71.03(15) . . . . ?
C13 N2 C14 C15 82.03(14) . . . . ?
C13 N2 C16 C17 -163.34(11) . . . . ?
C14 N2 C13 C12 -63.67(14) . . . . ?
C14 N2 C16 C17 72.01(14) . . . . ?
C15 N1 C10 O4 -2.66(19) . . . . ?
C15 N1 C10 C9 173.99(11) . . . . ?
C15 N1 C11 C8 169.72(11) . . . . ?
C15 N1 C11 C12 46.49(15) . . . . ?
C16 N2 C13 C12 173.72(11) . . . . ?
C16 N2 C14 C15 -155.31(11) . . . . ?
C16 C17 C18 C19 174.39(13) . . . . ?
C16 C17 C22 C21 -174.95(12) . . . . ?
C17 C18 C19 C20 1.0(2) . . . . ?
C18 C17 C22 C21 1.33(19) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C19 C20 C21 C22 -0.9(2) . . . . ?
C20 C21 C22 C17 0.1(2) . . . . ?
C22 C17 C18 C19 -1.9(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
-13 -1 0 0.0331 -13.0002 -0.9999 0.0001 -0.0654 0.9974 -0.1703
13 1 0 0.0331 13.0002 0.9999 -0.0001 0.0654 -0.9974 0.1703
3 -5 -5 0.1218 2.9999 -4.9999 -4.9999 0.4604 0.1911 0.9892
-11 2 3 0.0983 -11.0001 2.0000 3.0000 -0.2796 0.6053 -0.6957
-7 5 1 0.0541 -7.0001 5.0000 1.0000 -0.7831 0.2370 -0.5635
6 2 -6 0.1246 5.9999 2.0000 -6.0000 -0.5816 -0.3303 0.7282
-9 1 6 0.1397 -9.0000 1.0000 6.0000 0.0927 0.4053 -0.9702
-1 0 7 0.1765 -0.9998 -0.0001 6.9999 0.4342 -0.1649 -0.8884
-1 0 -7 0.1525 -1.0003 0.0001 -6.9999 -0.4669 0.3110 0.8525
-1 6 0 0.0579 -1.0001 5.9999 -0.0001 -0.8963 -0.2153 -0.3944
5 -6 -1 0.0482 5.0001 -5.9999 -1.0000 0.8971 -0.0429 0.5904
-3 -6 0 0.0586 -3.0000 -5.9999 0.0001 0.8310 0.5074 0.3227
-13 1 -1 0.0390 -13.0003 1.0000 -0.9999 -0.4231 0.9353 -0.1714
13 -1 0 0.0358 13.0002 -1.0000 -0.0001 0.3587 -0.9013 0.2958

_olex2_date_sample_data_collection 2015-10-19
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jdf3_432b_cu
_database_code_depnum_ccdc_archive 'CCDC 1478962'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl (1R*,2R*,5S*,6R*,7S*)-3-benzyl-2-(but-3-en-1-yl)-4-oxo-10-oxa-3-azatricyclo[5.2.1.0¹,5]dec-8-ene-6-carboxylate'
_chemical_formula_moiety         'C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C352 H432 N16 O64'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8686(9)
_cell_length_b                   23.9445(18)
_cell_length_c                   33.107(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.065(8)
_cell_angle_gamma                90
_cell_volume                     7823.1(11)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2778
_cell_measurement_temperature    119.98(14)
_cell_measurement_theta_max      54.1130
_cell_measurement_theta_min      5.3660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.1087
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            25119
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        54.239
_diffrn_reflns_theta_max         54.239
_diffrn_reflns_theta_min         3.246
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.98(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -115.00  -29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   60.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   33.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega   38.00   64.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   96.00  123.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   40.00   74.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00   66.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   72.00   98.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   33.00   90.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
 10 omega   67.00   94.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega  112.00  144.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega   45.00   77.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 13 omega   92.00  119.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   34.00   87.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   84.00  121.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
 16 omega  104.00  131.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   73.00  128.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
 18 omega  150.00  178.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 19 omega   34.00   76.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -90.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0083600000
_diffrn_orient_matrix_UB_12      -0.0320143000
_diffrn_orient_matrix_UB_13      -0.0403125000
_diffrn_orient_matrix_UB_21      0.1000214000
_diffrn_orient_matrix_UB_22      -0.0439019000
_diffrn_orient_matrix_UB_23      0.0164114000
_diffrn_orient_matrix_UB_31      -0.1194923000
_diffrn_orient_matrix_UB_32      -0.0344712000
_diffrn_orient_matrix_UB_33      0.0164886000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6725
_reflns_number_total             8978
_reflns_odcompleteness_completeness 93.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     54.18
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     974
_refine_ls_number_reflns         8978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0730
_refine_ls_restrained_S_all      1.039
_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)+(0.0731P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1761
_refine_special_details          
;
 Refined with Twin Law (-1 0 0, 0 -1 0, 0 0 1). BASF 0.4371
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5629(16) 0.4371(16)
2. 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
3.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C18(H18), C19(H19), C68(H68), C70(H70), C84(H84), C85(H85),
 C24(H24), C26(H26), C40(H40), C41(H41), C46(H46), C48(H48), C62(H62), C63(H63)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B), C13(H13A,H13B), C21(H21A,H21B), C71(H71A,H71B),
 C78(H78A,H78B), C79(H79A,H79B), C87(H87A,H87B), C27(H27A,H27B), C34(H34A,H34B),
  C35(H35A,H35B), C43(H43A,H43B), C49(H49A,H49B), C56(H56A,H56B), C57(H57A,
 H57B), C65(H65A,H65B)
3.c Me refined with riding coordinates:
 C22(H22A,H22B,H22C), C88(H88A,H88B,H88C), C44(H44A,H44B,H44C), C66(H66A,H66B,
 H66C)
3.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C16(H16), C17(H17),
 C73(H73), C74(H74), C75(H75), C76(H76), C77(H77), C80(H80), C82(H82), C83(H83),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C36(H36), C38(H38),
 C39(H39), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55), C58(H58), C60(H60),
  C61(H61)
3.e X=CH2 refined with riding coordinates:
 C15(H15A,H15B), C81(H81A,H81B), C37(H37A,H37B), C59(H59A,H59B)
;
_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 0.7507(5) 0.78479(17) 0.26545(12) 0.0349(11) Uani 1 1 d . . . . .
N1 N 0.7025(5) 0.6924(2) 0.25447(14) 0.0281(12) Uani 1 1 d . . . . .
C1 C 0.7459(6) 0.7440(3) 0.24299(18) 0.0284(15) Uani 1 1 d . . . . .
O2 O 0.5964(4) 0.70473(16) 0.17211(11) 0.0286(9) Uani 1 1 d . . . . .
C2 C 0.7174(6) 0.6490(2) 0.22268(17) 0.0263(13) Uani 1 1 d . . . . .
H2 H 0.8036 0.6294 0.2267 0.032 Uiso 1 1 calc R . . . .
O3 O 0.5321(5) 0.82437(17) 0.19695(13) 0.0352(10) Uani 1 1 d . . . . .
C3 C 0.7274(6) 0.6852(2) 0.18524(18) 0.0253(13) Uani 1 1 d . . . . .
O4 O 0.7213(4) 0.87600(15) 0.19316(12) 0.0304(10) Uani 1 1 d . . . . .
C4 C 0.7906(6) 0.7411(2) 0.19916(16) 0.0230(13) Uani 1 1 d . . . . .
H4 H 0.8896 0.7393 0.1975 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6754(7) 0.6788(3) 0.29629(18) 0.0321(15) Uani 1 1 d . . . . .
H5A H 0.5928 0.6569 0.2976 0.039 Uiso 1 1 calc R . . . .
H5B H 0.6599 0.7132 0.3111 0.039 Uiso 1 1 calc R . . . .
C6 C 0.7875(7) 0.6467(2) 0.31684(17) 0.0305(15) Uani 1 1 d . . . . .
C7 C 0.9225(7) 0.6570(2) 0.30743(17) 0.0336(16) Uani 1 1 d . . . . .
H7 H 0.9442 0.6823 0.2871 0.040 Uiso 1 1 calc R . . . .
C8 C 1.0254(8) 0.6295(3) 0.32831(18) 0.0376(16) Uani 1 1 d . . . . .
H8 H 1.1154 0.6365 0.3217 0.045 Uiso 1 1 calc R . . . .
C9 C 0.9956(8) 0.5925(3) 0.3584(2) 0.0428(18) Uani 1 1 d . . . . .
H9 H 1.0650 0.5750 0.3726 0.051 Uiso 1 1 calc R . . . .
C10 C 0.8611(8) 0.5811(3) 0.3678(2) 0.0446(19) Uani 1 1 d . . . . .
H10 H 0.8404 0.5555 0.3880 0.054 Uiso 1 1 calc R . . . .
C11 C 0.7572(8) 0.6082(3) 0.34677(18) 0.0382(17) Uani 1 1 d . . . . .
H11 H 0.6672 0.6003 0.3529 0.046 Uiso 1 1 calc R . . . .
C12 C 0.6023(7) 0.6065(2) 0.22280(18) 0.0330(14) Uani 1 1 d . . . . .
H12A H 0.5165 0.6255 0.2188 0.040 Uiso 1 1 calc R . . . .
H12B H 0.5992 0.5877 0.2487 0.040 Uiso 1 1 calc R . . . .
C13 C 0.6239(7) 0.5630(3) 0.18883(19) 0.0391(16) Uani 1 1 d . . . . .
H13A H 0.6180 0.5815 0.1628 0.047 Uiso 1 1 calc R . . . .
H13B H 0.7138 0.5470 0.1913 0.047 Uiso 1 1 calc R . . . .
C14 C 0.5210(9) 0.5174(3) 0.1907(2) 0.0485(19) Uani 1 1 d . . . . .
H14 H 0.4300 0.5275 0.1895 0.058 Uiso 1 1 calc R . . . .
C15 C 0.5501(12) 0.4636(3) 0.1940(2) 0.071(3) Uani 1 1 d . . . . .
H15A H 0.6399 0.4520 0.1953 0.085 Uiso 1 1 calc R . . . .
H15B H 0.4806 0.4374 0.1950 0.085 Uiso 1 1 calc R . . . .
C16 C 0.7927(6) 0.6690(2) 0.14513(17) 0.0283(14) Uani 1 1 d . . . . .
H16 H 0.8537 0.6401 0.1404 0.034 Uiso 1 1 calc R . . . .
C17 C 0.7437(7) 0.7048(2) 0.11871(17) 0.0300(15) Uani 1 1 d . . . . .
H17 H 0.7644 0.7068 0.0913 0.036 Uiso 1 1 calc R . . . .
C18 C 0.6454(7) 0.7426(3) 0.14218(18) 0.0328(16) Uani 1 1 d . . . . .
H18 H 0.5753 0.7607 0.1258 0.039 Uiso 1 1 calc R . . . .
C19 C 0.7348(6) 0.7833(2) 0.16813(18) 0.0269(14) Uani 1 1 d . . . . .
H19 H 0.8080 0.7996 0.1520 0.032 Uiso 1 1 calc R . . . .
C20 C 0.6496(7) 0.8284(2) 0.18780(18) 0.0304(16) Uani 1 1 d . . . . .
C21 C 0.6473(7) 0.9203(3) 0.2135(2) 0.0427(17) Uani 1 1 d . . . . .
H21A H 0.6265 0.9094 0.2410 0.051 Uiso 1 1 calc R . . . .
H21B H 0.5628 0.9277 0.1994 0.051 Uiso 1 1 calc R . . . .
C22 C 0.7339(9) 0.9715(3) 0.2135(2) 0.052(2) Uani 1 1 d . . . . .
H22A H 0.6869 1.0013 0.2268 0.078 Uiso 1 1 calc R . . . .
H22B H 0.8171 0.9638 0.2275 0.078 Uiso 1 1 calc R . . . .
H22C H 0.7536 0.9821 0.1861 0.078 Uiso 1 1 calc R . . . .
N4 N 1.0769(6) 0.20312(19) -0.00731(14) 0.0288(12) Uani 1 1 d . . . . .
O13 O 1.1278(5) 0.29577(16) -0.01811(12) 0.0318(10) Uani 1 1 d . . . . .
O14 O 0.9679(4) 0.21838(16) 0.07522(12) 0.0275(9) Uani 1 1 d . . . . .
O15 O 0.9190(5) 0.34350(16) 0.05524(12) 0.0296(10) Uani 1 1 d . . . . .
O16 O 1.1234(4) 0.38348(15) 0.05053(11) 0.0239(9) Uani 1 1 d . . . . .
C67 C 1.1206(6) 0.2559(2) 0.00401(17) 0.0239(14) Uani 1 1 d . . . . .
C68 C 1.0842(7) 0.1612(2) 0.02413(17) 0.0274(14) Uani 1 1 d . . . . .
H68 H 1.1666 0.1389 0.0205 0.033 Uiso 1 1 calc R . . . .
C69 C 1.0976(7) 0.1963(2) 0.06201(17) 0.0257(13) Uani 1 1 d . . . . .
C70 C 1.1668(6) 0.2515(2) 0.04782(17) 0.0215(13) Uani 1 1 d . . . . .
H70 H 1.2656 0.2479 0.0492 0.026 Uiso 1 1 calc R . . . .
C71 C 1.0532(7) 0.1898(3) -0.04927(18) 0.0352(16) Uani 1 1 d . . . . .
H71A H 1.0526 0.2240 -0.0650 0.042 Uiso 1 1 calc R . . . .
H71B H 0.9649 0.1724 -0.0520 0.042 Uiso 1 1 calc R . . . .
C72 C 1.1613(7) 0.1505(3) -0.06601(17) 0.0326(16) Uani 1 1 d . . . . .
C73 C 1.1249(8) 0.1006(3) -0.08445(18) 0.0390(17) Uani 1 1 d . . . . .
H73 H 1.0338 0.0911 -0.0864 0.047 Uiso 1 1 calc R . . . .
C74 C 1.2220(11) 0.0649(3) -0.1000(2) 0.060(2) Uani 1 1 d . . . . .
H74 H 1.1967 0.0314 -0.1121 0.072 Uiso 1 1 calc R . . . .
C75 C 1.3577(10) 0.0796(3) -0.0972(2) 0.057(2) Uani 1 1 d . . . . .
H75 H 1.4238 0.0564 -0.1081 0.068 Uiso 1 1 calc R . . . .
C76 C 1.3945(10) 0.1286(3) -0.0784(2) 0.054(2) Uani 1 1 d . . . . .
H76 H 1.4856 0.1380 -0.0761 0.064 Uiso 1 1 calc R . . . .
C77 C 1.2957(8) 0.1640(3) -0.06277(19) 0.0401(17) Uani 1 1 d . . . . .
H77 H 1.3212 0.1970 -0.0501 0.048 Uiso 1 1 calc R . . . .
C78 C 0.9602(7) 0.1223(3) 0.02388(19) 0.0342(15) Uani 1 1 d . . . . .
H78A H 0.8788 0.1448 0.0264 0.041 Uiso 1 1 calc R . . . .
H78B H 0.9562 0.1031 -0.0019 0.041 Uiso 1 1 calc R . . . .
C79 C 0.9627(8) 0.0793(3) 0.0576(2) 0.0414(17) Uani 1 1 d . . . . .
H79A H 0.9699 0.0985 0.0833 0.050 Uiso 1 1 calc R . . . .
H79B H 0.8775 0.0590 0.0575 0.050 Uiso 1 1 calc R . . . .
C80 C 1.0776(9) 0.0379(3) 0.0542(2) 0.048(2) Uani 1 1 d . . . . .
H80 H 1.0925 0.0213 0.0292 0.058 Uiso 1 1 calc R . . . .
C81 C 1.1564(10) 0.0240(3) 0.0836(2) 0.060(2) Uani 1 1 d . . . . .
H81A H 1.1444 0.0398 0.1090 0.072 Uiso 1 1 calc R . . . .
H81B H 1.2254 -0.0018 0.0794 0.072 Uiso 1 1 calc R . . . .
C82 C 1.1598(6) 0.1795(2) 0.10201(18) 0.0270(14) Uani 1 1 d . . . . .
H82 H 1.2184 0.1498 0.1067 0.032 Uiso 1 1 calc R . . . .
C83 C 1.1143(6) 0.2153(2) 0.12879(17) 0.0252(13) Uani 1 1 d . . . . .
H83 H 1.1342 0.2163 0.1562 0.030 Uiso 1 1 calc R . . . .
C84 C 1.0218(6) 0.2550(2) 0.10528(17) 0.0250(13) Uani 1 1 d . . . . .
H84 H 0.9540 0.2746 0.1216 0.030 Uiso 1 1 calc R . . . .
C85 C 1.1163(6) 0.2938(2) 0.07954(16) 0.0218(13) Uani 1 1 d . . . . .
H85 H 1.1919 0.3077 0.0959 0.026 Uiso 1 1 calc R . . . .
C86 C 1.0386(6) 0.3419(2) 0.06096(16) 0.0218(13) Uani 1 1 d . . . . .
C87 C 1.0586(7) 0.4308(2) 0.03030(18) 0.0322(15) Uani 1 1 d . . . . .
H87A H 1.0123 0.4543 0.0498 0.039 Uiso 1 1 calc R . . . .
H87B H 0.9933 0.4178 0.0105 0.039 Uiso 1 1 calc R . . . .
C88 C 1.1716(7) 0.4627(3) 0.0100(2) 0.0452(18) Uani 1 1 d . . . . .
H88A H 1.1347 0.4945 -0.0039 0.068 Uiso 1 1 calc R . . . .
H88B H 1.2355 0.4751 0.0299 0.068 Uiso 1 1 calc R . . . .
H88C H 1.2166 0.4388 -0.0091 0.068 Uiso 1 1 calc R . . . .
N2 N 1.1989(5) 0.78745(19) 0.25295(14) 0.0262(12) Uani 1 1 d . . . . .
O5 O 1.2581(5) 0.69766(16) 0.26894(12) 0.0352(11) Uani 1 1 d . . . . .
O6 O 1.0936(4) 0.76455(16) 0.17025(11) 0.0279(9) Uani 1 1 d . . . . .
O7 O 1.0402(5) 0.64704(18) 0.20041(13) 0.0364(10) Uani 1 1 d . . . . .
O8 O 1.2392(5) 0.60312(16) 0.20713(13) 0.0344(10) Uani 1 1 d . . . . .
C23 C 1.2463(7) 0.7354(3) 0.24413(17) 0.0279(15) Uani 1 1 d . . . . .
C24 C 1.2017(6) 0.8269(2) 0.21891(17) 0.0256(13) Uani 1 1 d . . . . .
H24 H 1.2810 0.8513 0.2216 0.031 Uiso 1 1 calc R . . . .
C25 C 1.2218(6) 0.7883(2) 0.18324(17) 0.0256(14) Uani 1 1 d . . . . .
C26 C 1.2917(6) 0.7353(2) 0.20064(17) 0.0247(13) Uani 1 1 d . . . . .
H26 H 1.3905 0.7387 0.1989 0.030 Uiso 1 1 calc R . . . .
C27 C 1.1756(7) 0.8048(3) 0.29443(18) 0.0320(15) Uani 1 1 d . . . . .
H27A H 1.1652 0.7718 0.3111 0.038 Uiso 1 1 calc R . . . .
H27B H 1.0913 0.8256 0.2956 0.038 Uiso 1 1 calc R . . . .
C28 C 1.2874(7) 0.8405(2) 0.31180(18) 0.0313(15) Uani 1 1 d . . . . .
C29 C 1.2608(8) 0.8803(2) 0.34098(17) 0.0362(17) Uani 1 1 d . . . . .
H29 H 1.1719 0.8859 0.3493 0.043 Uiso 1 1 calc R . . . .
C30 C 1.3624(8) 0.9116(3) 0.35809(19) 0.0418(19) Uani 1 1 d . . . . .
H30 H 1.3424 0.9383 0.3776 0.050 Uiso 1 1 calc R . . . .
C31 C 1.4965(8) 0.9029(3) 0.34574(18) 0.0408(18) Uani 1 1 d . . . . .
H31 H 1.5663 0.9237 0.3572 0.049 Uiso 1 1 calc R . . . .
C32 C 1.5247(8) 0.8640(3) 0.31694(18) 0.0372(16) Uani 1 1 d . . . . .
H32 H 1.6140 0.8584 0.3089 0.045 Uiso 1 1 calc R . . . .
C33 C 1.4226(7) 0.8326(2) 0.29949(16) 0.0303(15) Uani 1 1 d . . . . .
H33 H 1.4431 0.8065 0.2797 0.036 Uiso 1 1 calc R . . . .
C34 C 1.0736(6) 0.8629(3) 0.21637(18) 0.0327(15) Uani 1 1 d . . . . .
H34A H 1.0610 0.8825 0.2417 0.039 Uiso 1 1 calc R . . . .
H34B H 0.9955 0.8390 0.2121 0.039 Uiso 1 1 calc R . . . .
C35 C 1.0826(7) 0.9057(3) 0.18162(19) 0.0385(16) Uani 1 1 d . . . . .
H35A H 1.1142 0.8871 0.1574 0.046 Uiso 1 1 calc R . . . .
H35B H 0.9930 0.9206 0.1761 0.046 Uiso 1 1 calc R . . . .
C36 C 1.1747(9) 0.9516(3) 0.1916(2) 0.055(2) Uani 1 1 d . . . . .
H36 H 1.1529 0.9741 0.2135 0.066 Uiso 1 1 calc R . . . .
C37 C 1.2879(10) 0.9633(3) 0.1714(3) 0.068(3) Uani 1 1 d . . . . .
H37A H 1.3127 0.9416 0.1493 0.081 Uiso 1 1 calc R . . . .
H37B H 1.3420 0.9931 0.1793 0.081 Uiso 1 1 calc R . . . .
C38 C 1.2874(7) 0.8017(2) 0.14303(17) 0.0285(14) Uani 1 1 d . . . . .
H38 H 1.3447 0.8315 0.1372 0.034 Uiso 1 1 calc R . . . .
C39 C 1.2459(7) 0.7623(3) 0.11809(17) 0.0307(15) Uani 1 1 d . . . . .
H39 H 1.2701 0.7580 0.0911 0.037 Uiso 1 1 calc R . . . .
C40 C 1.1506(7) 0.7251(3) 0.14221(17) 0.0303(15) Uani 1 1 d . . . . .
H40 H 1.0843 0.7043 0.1261 0.036 Uiso 1 1 calc R . . . .
C41 C 1.2393(6) 0.6888(2) 0.17116(17) 0.0258(13) Uani 1 1 d . . . . .
H41 H 1.3148 0.6716 0.1565 0.031 Uiso 1 1 calc R . . . .
C42 C 1.1592(7) 0.6453(2) 0.19369(17) 0.0282(15) Uani 1 1 d . . . . .
C43 C 1.1797(8) 0.5665(3) 0.2366(2) 0.0417(18) Uani 1 1 d . . . . .
H43A H 1.1140 0.5871 0.2525 0.050 Uiso 1 1 calc R . . . .
H43B H 1.2497 0.5531 0.2548 0.050 Uiso 1 1 calc R . . . .
C44 C 1.1110(9) 0.5174(3) 0.2169(2) 0.059(2) Uani 1 1 d . . . . .
H44A H 1.0724 0.4938 0.2373 0.088 Uiso 1 1 calc R . . . .
H44B H 1.0406 0.5306 0.1993 0.088 Uiso 1 1 calc R . . . .
H44C H 1.1762 0.4966 0.2016 0.088 Uiso 1 1 calc R . . . .
N3 N 0.5804(5) 0.31602(19) -0.00207(13) 0.0244(11) Uani 1 1 d . . . . .
O9 O 0.6168(5) 0.22434(16) -0.01993(12) 0.0365(11) Uani 1 1 d . . . . .
O10 O 0.4728(4) 0.29007(15) 0.07912(11) 0.0238(9) Uani 1 1 d . . . . .
O11 O 0.4119(5) 0.16833(16) 0.05075(13) 0.0343(10) Uani 1 1 d . . . . .
O12 O 0.6116(5) 0.12654(16) 0.04119(12) 0.0323(10) Uani 1 1 d . . . . .
C45 C 0.6183(6) 0.2616(2) 0.00552(17) 0.0254(14) Uani 1 1 d . . . . .
C46 C 0.5939(6) 0.3530(2) 0.03295(16) 0.0232(13) Uani 1 1 d . . . . .
H46 H 0.6791 0.3739 0.0307 0.028 Uiso 1 1 calc R . . . .
C47 C 0.6052(6) 0.3117(2) 0.06753(17) 0.0261(13) Uani 1 1 d . . . . .
C48 C 0.6672(6) 0.2581(2) 0.04854(17) 0.0212(13) Uani 1 1 d . . . . .
H48 H 0.7664 0.2594 0.0496 0.025 Uiso 1 1 calc R . . . .
C49 C 0.5549(7) 0.3359(3) -0.04261(17) 0.0319(15) Uani 1 1 d . . . . .
H49A H 0.4750 0.3595 -0.0422 0.038 Uiso 1 1 calc R . . . .
H49B H 0.5354 0.3041 -0.0598 0.038 Uiso 1 1 calc R . . . .
C50 C 0.6709(6) 0.3686(2) -0.06089(15) 0.0258(14) Uani 1 1 d . . . . .
C51 C 0.8043(7) 0.3574(2) -0.05134(17) 0.0277(14) Uani 1 1 d . . . . .
H51 H 0.8239 0.3301 -0.0322 0.033 Uiso 1 1 calc R . . . .
C52 C 0.9111(7) 0.3863(2) -0.06997(18) 0.0336(15) Uani 1 1 d . . . . .
H52 H 1.0005 0.3783 -0.0632 0.040 Uiso 1 1 calc R . . . .
C53 C 0.8823(8) 0.4267(3) -0.09825(17) 0.0352(16) Uani 1 1 d . . . . .
H53 H 0.9527 0.4456 -0.1110 0.042 Uiso 1 1 calc R . . . .
C54 C 0.7508(8) 0.4393(2) -0.10769(17) 0.0380(17) Uani 1 1 d . . . . .
H54 H 0.7317 0.4669 -0.1266 0.046 Uiso 1 1 calc R . . . .
C55 C 0.6453(7) 0.4105(2) -0.08892(16) 0.0292(15) Uani 1 1 d . . . . .
H55 H 0.5562 0.4195 -0.0953 0.035 Uiso 1 1 calc R . . . .
C56 C 0.4775(6) 0.3942(2) 0.03677(17) 0.0267(13) Uani 1 1 d . . . . .
H56A H 0.3939 0.3736 0.0407 0.032 Uiso 1 1 calc R . . . .
H56B H 0.4692 0.4150 0.0118 0.032 Uiso 1 1 calc R . . . .
C57 C 0.4961(7) 0.4352(2) 0.07181(17) 0.0305(14) Uani 1 1 d . . . . .
H57A H 0.4119 0.4553 0.0759 0.037 Uiso 1 1 calc R . . . .
H57B H 0.5152 0.4143 0.0962 0.037 Uiso 1 1 calc R . . . .
C58 C 0.6071(8) 0.4765(2) 0.06523(18) 0.0375(16) Uani 1 1 d . . . . .
H58 H 0.6075 0.4951 0.0406 0.045 Uiso 1 1 calc R . . . .
C59 C 0.7035(7) 0.4890(3) 0.0905(2) 0.0428(17) Uani 1 1 d . . . . .
H59A H 0.7075 0.4715 0.1155 0.051 Uiso 1 1 calc R . . . .
H59B H 0.7683 0.5155 0.0835 0.051 Uiso 1 1 calc R . . . .
C60 C 0.6687(6) 0.3218(2) 0.10851(16) 0.0204(13) Uani 1 1 d . . . . .
H60 H 0.7290 0.3501 0.1155 0.025 Uiso 1 1 calc R . . . .
C61 C 0.6208(6) 0.2822(2) 0.13221(17) 0.0249(14) Uani 1 1 d . . . . .
H61 H 0.6422 0.2762 0.1592 0.030 Uiso 1 1 calc R . . . .
C62 C 0.5244(7) 0.2487(2) 0.10656(17) 0.0262(14) Uani 1 1 d . . . . .
H62 H 0.4550 0.2282 0.1216 0.031 Uiso 1 1 calc R . . . .
C63 C 0.6119(6) 0.2122(2) 0.07743(17) 0.0229(13) Uani 1 1 d . . . . .
H63 H 0.6870 0.1951 0.0924 0.028 Uiso 1 1 calc R . . . .
C64 C 0.5325(7) 0.1678(2) 0.05550(17) 0.0253(14) Uani 1 1 d . . . . .
C65 C 0.5424(8) 0.0854(3) 0.0173(2) 0.0476(18) Uani 1 1 d . . . . .
H65A H 0.4769 0.1034 -0.0003 0.057 Uiso 1 1 calc R . . . .
H65B H 0.4944 0.0596 0.0347 0.057 Uiso 1 1 calc R . . . .
C66 C 0.6434(10) 0.0549(4) -0.0072(3) 0.096(4) Uani 1 1 d . . . . .
H66A H 0.5983 0.0272 -0.0233 0.144 Uiso 1 1 calc R . . . .
H66B H 0.6900 0.0806 -0.0245 0.144 Uiso 1 1 calc R . . . .
H66C H 0.7074 0.0369 0.0104 0.144 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 1.228(8) . ?
N1 C1 1.362(8) . ?
N1 C2 1.486(8) . ?
N1 C5 1.448(8) . ?
C1 C4 1.519(8) . ?
O2 C3 1.442(8) . ?
O2 C18 1.429(8) . ?
C2 H2 0.9800 . ?
C2 C3 1.515(9) . ?
C2 C12 1.526(9) . ?
O3 C20 1.202(8) . ?
C3 C4 1.547(8) . ?
C3 C16 1.526(9) . ?
O4 C20 1.353(8) . ?
O4 C21 1.454(8) . ?
C4 H4 0.9800 . ?
C4 C19 1.543(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.508(10) . ?
C6 C7 1.391(10) . ?
C6 C11 1.387(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.393(10) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.398(10) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.547(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.492(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.325(11) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.316(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.539(10) . ?
C18 H18 0.9800 . ?
C18 C19 1.570(9) . ?
C19 H19 0.9800 . ?
C19 C20 1.516(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.493(10) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N4 C67 1.386(8) . ?
N4 C68 1.448(8) . ?
N4 C71 1.444(8) . ?
O13 C67 1.206(7) . ?
O14 C69 1.453(8) . ?
O14 C84 1.429(7) . ?
O15 C86 1.196(7) . ?
O16 C86 1.346(7) . ?
O16 C87 1.463(7) . ?
C67 C70 1.524(8) . ?
C68 H68 0.9800 . ?
C68 C69 1.516(8) . ?
C68 C78 1.536(9) . ?
C69 C70 1.561(8) . ?
C69 C82 1.513(9) . ?
C70 H70 0.9800 . ?
C70 C85 1.542(8) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C71 C72 1.527(10) . ?
C72 C73 1.389(9) . ?
C72 C77 1.369(10) . ?
C73 H73 0.9300 . ?
C73 C74 1.384(12) . ?
C74 H74 0.9300 . ?
C74 C75 1.388(13) . ?
C75 H75 0.9300 . ?
C75 C76 1.376(12) . ?
C76 H76 0.9300 . ?
C76 C77 1.392(11) . ?
C77 H77 0.9300 . ?
C78 H78A 0.9700 . ?
C78 H78B 0.9700 . ?
C78 C79 1.520(9) . ?
C79 H79A 0.9700 . ?
C79 H79B 0.9700 . ?
C79 C80 1.510(11) . ?
C80 H80 0.9300 . ?
C80 C81 1.289(11) . ?
C81 H81A 0.9300 . ?
C81 H81B 0.9300 . ?
C82 H82 0.9300 . ?
C82 C83 1.312(9) . ?
C83 H83 0.9300 . ?
C83 C84 1.530(9) . ?
C84 H84 0.9800 . ?
C84 C85 1.569(8) . ?
C85 H85 0.9800 . ?
C85 C86 1.513(8) . ?
C87 H87A 0.9700 . ?
C87 H87B 0.9700 . ?
C87 C88 1.511(9) . ?
C88 H88A 0.9600 . ?
C88 H88B 0.9600 . ?
C88 H88C 0.9600 . ?
N2 C23 1.363(8) . ?
N2 C24 1.471(8) . ?
N2 C27 1.453(8) . ?
O5 C23 1.226(8) . ?
O6 C25 1.453(7) . ?
O6 C40 1.439(8) . ?
O7 C42 1.196(8) . ?
O8 C42 1.356(8) . ?
O8 C43 1.439(8) . ?
C23 C26 1.508(8) . ?
C24 H24 0.9800 . ?
C24 C25 1.513(9) . ?
C24 C34 1.533(9) . ?
C25 C26 1.555(9) . ?
C25 C38 1.515(9) . ?
C26 H26 0.9800 . ?
C26 C41 1.568(8) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.509(9) . ?
C28 C29 1.381(9) . ?
C28 C33 1.408(10) . ?
C29 H29 0.9300 . ?
C29 C30 1.374(10) . ?
C30 H30 0.9300 . ?
C30 C31 1.401(12) . ?
C31 H31 0.9300 . ?
C31 C32 1.362(10) . ?
C32 H32 0.9300 . ?
C32 C33 1.382(9) . ?
C33 H33 0.9300 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.543(9) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.464(11) . ?
C36 H36 0.9300 . ?
C36 C37 1.333(13) . ?
C37 H37A 0.9300 . ?
C37 H37B 0.9300 . ?
C38 H38 0.9300 . ?
C38 C39 1.320(9) . ?
C39 H39 0.9300 . ?
C39 C40 1.521(9) . ?
C40 H40 0.9800 . ?
C40 C41 1.562(9) . ?
C41 H41 0.9800 . ?
C41 C42 1.506(9) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 C44 1.504(10) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
N3 C45 1.380(8) . ?
N3 C46 1.465(7) . ?
N3 C49 1.446(8) . ?
O9 C45 1.226(7) . ?
O10 C47 1.458(8) . ?
O10 C62 1.437(7) . ?
O11 C64 1.201(8) . ?
O12 C64 1.345(8) . ?
O12 C65 1.436(8) . ?
C45 C48 1.506(8) . ?
C46 H46 0.9800 . ?
C46 C47 1.517(8) . ?
C46 C56 1.518(8) . ?
C47 C48 1.555(8) . ?
C47 C60 1.513(8) . ?
C48 H48 0.9800 . ?
C48 C63 1.556(8) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C49 C50 1.513(9) . ?
C50 C51 1.380(9) . ?
C50 C55 1.390(8) . ?
C51 H51 0.9300 . ?
C51 C52 1.404(9) . ?
C52 H52 0.9300 . ?
C52 C53 1.375(9) . ?
C53 H53 0.9300 . ?
C53 C54 1.369(11) . ?
C54 H54 0.9300 . ?
C54 C55 1.394(10) . ?
C55 H55 0.9300 . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C56 C57 1.532(9) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C57 C58 1.491(10) . ?
C58 H58 0.9300 . ?
C58 C59 1.300(10) . ?
C59 H59A 0.9300 . ?
C59 H59B 0.9300 . ?
C60 H60 0.9300 . ?
C60 C61 1.319(9) . ?
C61 H61 0.9300 . ?
C61 C62 1.506(9) . ?
C62 H62 0.9800 . ?
C62 C63 1.562(8) . ?
C63 H63 0.9800 . ?
C63 C64 1.508(9) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C65 C66 1.478(12) . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?

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 N1 C2 113.9(5) . . ?
C1 N1 C5 122.0(5) . . ?
C5 N1 C2 122.6(5) . . ?
O1 C1 N1 124.3(5) . . ?
O1 C1 C4 127.2(6) . . ?
N1 C1 C4 108.4(5) . . ?
C18 O2 C3 96.4(5) . . ?
N1 C2 H2 109.0 . . ?
N1 C2 C3 100.8(4) . . ?
N1 C2 C12 113.0(5) . . ?
C3 C2 H2 109.0 . . ?
C3 C2 C12 115.7(5) . . ?
C12 C2 H2 109.0 . . ?
O2 C3 C2 111.9(5) . . ?
O2 C3 C4 99.8(4) . . ?
O2 C3 C16 101.5(4) . . ?
C2 C3 C4 106.1(5) . . ?
C2 C3 C16 126.5(5) . . ?
C16 C3 C4 108.0(5) . . ?
C20 O4 C21 114.4(5) . . ?
C1 C4 C3 102.0(5) . . ?
C1 C4 H4 110.3 . . ?
C1 C4 C19 120.1(5) . . ?
C3 C4 H4 110.3 . . ?
C19 C4 C3 103.1(5) . . ?
C19 C4 H4 110.3 . . ?
N1 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
N1 C5 C6 114.2(5) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C7 C6 C5 120.7(5) . . ?
C11 C6 C5 120.2(6) . . ?
C11 C6 C7 119.0(6) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(6) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(7) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.7(7) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.9(6) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 120.3(7) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C2 C12 H12A 109.6 . . ?
C2 C12 H12B 109.6 . . ?
C2 C12 C13 110.1(5) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 C12 111.6(6) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14 117.7 . . ?
C15 C14 C13 124.6(9) . . ?
C15 C14 H14 117.7 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C3 C16 H16 127.5 . . ?
C17 C16 C3 105.0(5) . . ?
C17 C16 H16 127.5 . . ?
C16 C17 H17 126.9 . . ?
C16 C17 C18 106.2(5) . . ?
C18 C17 H17 126.9 . . ?
O2 C18 C17 101.0(5) . . ?
O2 C18 H18 115.2 . . ?
O2 C18 C19 101.9(4) . . ?
C17 C18 H18 115.2 . . ?
C17 C18 C19 106.7(5) . . ?
C19 C18 H18 115.2 . . ?
C4 C19 C18 99.1(5) . . ?
C4 C19 H19 111.2 . . ?
C18 C19 H19 111.2 . . ?
C20 C19 C4 112.2(5) . . ?
C20 C19 C18 111.4(5) . . ?
C20 C19 H19 111.2 . . ?
O3 C20 O4 122.6(6) . . ?
O3 C20 C19 125.9(6) . . ?
O4 C20 C19 111.5(6) . . ?
O4 C21 H21A 110.1 . . ?
O4 C21 H21B 110.1 . . ?
O4 C21 C22 108.1(6) . . ?
H21A C21 H21B 108.4 . . ?
C22 C21 H21A 110.1 . . ?
C22 C21 H21B 110.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C67 N4 C68 115.0(5) . . ?
C67 N4 C71 120.8(5) . . ?
C71 N4 C68 123.1(5) . . ?
C84 O14 C69 96.1(4) . . ?
C86 O16 C87 114.8(5) . . ?
N4 C67 C70 106.7(5) . . ?
O13 C67 N4 125.2(5) . . ?
O13 C67 C70 127.9(5) . . ?
N4 C68 H68 109.3 . . ?
N4 C68 C69 102.3(4) . . ?
N4 C68 C78 112.2(5) . . ?
C69 C68 H68 109.3 . . ?
C69 C68 C78 114.1(5) . . ?
C78 C68 H68 109.3 . . ?
O14 C69 C68 112.0(5) . . ?
O14 C69 C70 99.7(4) . . ?
O14 C69 C82 100.9(4) . . ?
C68 C69 C70 105.0(5) . . ?
C82 C69 C68 127.7(5) . . ?
C82 C69 C70 108.1(5) . . ?
C67 C70 C69 102.4(5) . . ?
C67 C70 H70 110.3 . . ?
C67 C70 C85 120.4(5) . . ?
C69 C70 H70 110.3 . . ?
C85 C70 C69 102.1(5) . . ?
C85 C70 H70 110.3 . . ?
N4 C71 H71A 109.2 . . ?
N4 C71 H71B 109.2 . . ?
N4 C71 C72 111.9(5) . . ?
H71A C71 H71B 107.9 . . ?
C72 C71 H71A 109.2 . . ?
C72 C71 H71B 109.2 . . ?
C73 C72 C71 120.6(6) . . ?
C77 C72 C71 120.2(6) . . ?
C77 C72 C73 119.2(6) . . ?
C72 C73 H73 119.5 . . ?
C74 C73 C72 121.1(8) . . ?
C74 C73 H73 119.5 . . ?
C73 C74 H74 120.4 . . ?
C73 C74 C75 119.2(7) . . ?
C75 C74 H74 120.4 . . ?
C74 C75 H75 120.0 . . ?
C76 C75 C74 120.0(8) . . ?
C76 C75 H75 120.0 . . ?
C75 C76 H76 119.9 . . ?
C75 C76 C77 120.2(9) . . ?
C77 C76 H76 119.9 . . ?
C72 C77 C76 120.4(7) . . ?
C72 C77 H77 119.8 . . ?
C76 C77 H77 119.8 . . ?
C68 C78 H78A 108.9 . . ?
C68 C78 H78B 108.9 . . ?
H78A C78 H78B 107.7 . . ?
C79 C78 C68 113.2(5) . . ?
C79 C78 H78A 108.9 . . ?
C79 C78 H78B 108.9 . . ?
C78 C79 H79A 108.8 . . ?
C78 C79 H79B 108.8 . . ?
H79A C79 H79B 107.7 . . ?
C80 C79 C78 113.7(6) . . ?
C80 C79 H79A 108.8 . . ?
C80 C79 H79B 108.8 . . ?
C79 C80 H80 117.8 . . ?
C81 C80 C79 124.5(7) . . ?
C81 C80 H80 117.8 . . ?
C80 C81 H81A 120.0 . . ?
C80 C81 H81B 120.0 . . ?
H81A C81 H81B 120.0 . . ?
C69 C82 H82 126.9 . . ?
C83 C82 C69 106.2(5) . . ?
C83 C82 H82 126.9 . . ?
C82 C83 H83 127.3 . . ?
C82 C83 C84 105.4(5) . . ?
C84 C83 H83 127.3 . . ?
O14 C84 C83 101.2(4) . . ?
O14 C84 H84 115.1 . . ?
O14 C84 C85 101.9(4) . . ?
C83 C84 H84 115.1 . . ?
C83 C84 C85 106.8(5) . . ?
C85 C84 H84 115.1 . . ?
C70 C85 C84 100.0(4) . . ?
C70 C85 H85 110.6 . . ?
C84 C85 H85 110.6 . . ?
C86 C85 C70 112.8(4) . . ?
C86 C85 C84 111.7(5) . . ?
C86 C85 H85 110.6 . . ?
O15 C86 O16 123.3(5) . . ?
O15 C86 C85 126.1(5) . . ?
O16 C86 C85 110.7(5) . . ?
O16 C87 H87A 110.6 . . ?
O16 C87 H87B 110.6 . . ?
O16 C87 C88 105.9(5) . . ?
H87A C87 H87B 108.7 . . ?
C88 C87 H87A 110.6 . . ?
C88 C87 H87B 110.6 . . ?
C87 C88 H88A 109.5 . . ?
C87 C88 H88B 109.5 . . ?
C87 C88 H88C 109.5 . . ?
H88A C88 H88B 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?
C23 N2 C24 114.6(5) . . ?
C23 N2 C27 121.3(5) . . ?
C27 N2 C24 122.9(5) . . ?
C40 O6 C25 96.1(4) . . ?
C42 O8 C43 116.0(5) . . ?
N2 C23 C26 107.9(5) . . ?
O5 C23 N2 124.2(5) . . ?
O5 C23 C26 127.6(5) . . ?
N2 C24 H24 109.2 . . ?
N2 C24 C25 102.0(4) . . ?
N2 C24 C34 112.8(5) . . ?
C25 C24 H24 109.2 . . ?
C25 C24 C34 114.2(5) . . ?
C34 C24 H24 109.2 . . ?
O6 C25 C24 110.8(5) . . ?
O6 C25 C26 100.1(4) . . ?
O6 C25 C38 101.3(4) . . ?
C24 C25 C26 105.5(4) . . ?
C24 C25 C38 127.8(5) . . ?
C38 C25 C26 108.0(5) . . ?
C23 C26 C25 102.7(5) . . ?
C23 C26 H26 110.5 . . ?
C23 C26 C41 119.8(5) . . ?
C25 C26 H26 110.5 . . ?
C25 C26 C41 101.8(5) . . ?
C41 C26 H26 110.5 . . ?
N2 C27 H27A 108.8 . . ?
N2 C27 H27B 108.8 . . ?
N2 C27 C28 113.9(6) . . ?
H27A C27 H27B 107.7 . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
C29 C28 C27 121.1(6) . . ?
C29 C28 C33 118.4(6) . . ?
C33 C28 C27 120.5(5) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 C28 121.7(7) . . ?
C30 C29 H29 119.1 . . ?
C29 C30 H30 120.4 . . ?
C29 C30 C31 119.2(6) . . ?
C31 C30 H30 120.4 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0(6) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C33 120.9(7) . . ?
C33 C32 H32 119.5 . . ?
C28 C33 H33 120.1 . . ?
C32 C33 C28 119.8(6) . . ?
C32 C33 H33 120.1 . . ?
C24 C34 H34A 109.3 . . ?
C24 C34 H34B 109.3 . . ?
C24 C34 C35 111.5(5) . . ?
H34A C34 H34B 108.0 . . ?
C35 C34 H34A 109.3 . . ?
C35 C34 H34B 109.3 . . ?
C34 C35 H35A 109.3 . . ?
C34 C35 H35B 109.3 . . ?
H35A C35 H35B 108.0 . . ?
C36 C35 C34 111.5(5) . . ?
C36 C35 H35A 109.3 . . ?
C36 C35 H35B 109.3 . . ?
C35 C36 H36 117.8 . . ?
C37 C36 C35 124.4(8) . . ?
C37 C36 H36 117.8 . . ?
C36 C37 H37A 120.0 . . ?
C36 C37 H37B 120.0 . . ?
H37A C37 H37B 120.0 . . ?
C25 C38 H38 127.3 . . ?
C39 C38 C25 105.4(5) . . ?
C39 C38 H38 127.3 . . ?
C38 C39 H39 126.8 . . ?
C38 C39 C40 106.4(5) . . ?
C40 C39 H39 126.8 . . ?
O6 C40 C39 101.4(5) . . ?
O6 C40 H40 115.1 . . ?
O6 C40 C41 100.9(4) . . ?
C39 C40 H40 115.1 . . ?
C39 C40 C41 107.5(5) . . ?
C41 C40 H40 115.1 . . ?
C26 C41 H41 110.8 . . ?
C40 C41 C26 99.8(5) . . ?
C40 C41 H41 110.8 . . ?
C42 C41 C26 110.9(5) . . ?
C42 C41 C40 113.3(5) . . ?
C42 C41 H41 110.8 . . ?
O7 C42 O8 122.5(6) . . ?
O7 C42 C41 125.7(6) . . ?
O8 C42 C41 111.8(6) . . ?
O8 C43 H43A 109.3 . . ?
O8 C43 H43B 109.3 . . ?
O8 C43 C44 111.4(6) . . ?
H43A C43 H43B 108.0 . . ?
C44 C43 H43A 109.3 . . ?
C44 C43 H43B 109.3 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C45 N3 C46 113.8(4) . . ?
C45 N3 C49 121.8(5) . . ?
C49 N3 C46 123.4(5) . . ?
C62 O10 C47 95.4(4) . . ?
C64 O12 C65 115.0(5) . . ?
N3 C45 C48 108.1(5) . . ?
O9 C45 N3 124.0(5) . . ?
O9 C45 C48 127.9(5) . . ?
N3 C46 H46 109.0 . . ?
N3 C46 C47 102.1(4) . . ?
N3 C46 C56 113.0(5) . . ?
C47 C46 H46 109.0 . . ?
C47 C46 C56 114.5(5) . . ?
C56 C46 H46 109.0 . . ?
O10 C47 C46 111.4(5) . . ?
O10 C47 C48 99.6(4) . . ?
O10 C47 C60 101.0(4) . . ?
C46 C47 C48 105.2(5) . . ?
C60 C47 C46 127.1(5) . . ?
C60 C47 C48 109.4(5) . . ?
C45 C48 C47 102.2(5) . . ?
C45 C48 H48 110.6 . . ?
C45 C48 C63 120.5(5) . . ?
C47 C48 H48 110.6 . . ?
C47 C48 C63 101.3(5) . . ?
C63 C48 H48 110.6 . . ?
N3 C49 H49A 108.7 . . ?
N3 C49 H49B 108.7 . . ?
N3 C49 C50 114.3(5) . . ?
H49A C49 H49B 107.6 . . ?
C50 C49 H49A 108.7 . . ?
C50 C49 H49B 108.7 . . ?
C51 C50 C49 122.0(5) . . ?
C51 C50 C55 117.8(6) . . ?
C55 C50 C49 120.2(6) . . ?
C50 C51 H51 119.4 . . ?
C50 C51 C52 121.3(5) . . ?
C52 C51 H51 119.4 . . ?
C51 C52 H52 120.3 . . ?
C53 C52 C51 119.5(6) . . ?
C53 C52 H52 120.3 . . ?
C52 C53 H53 119.8 . . ?
C54 C53 C52 120.3(6) . . ?
C54 C53 H53 119.8 . . ?
C53 C54 H54 120.1 . . ?
C53 C54 C55 119.9(6) . . ?
C55 C54 H54 120.1 . . ?
C50 C55 C54 121.3(6) . . ?
C50 C55 H55 119.4 . . ?
C54 C55 H55 119.4 . . ?
C46 C56 H56A 109.0 . . ?
C46 C56 H56B 109.0 . . ?
C46 C56 C57 112.9(5) . . ?
H56A C56 H56B 107.8 . . ?
C57 C56 H56A 109.0 . . ?
C57 C56 H56B 109.0 . . ?
C56 C57 H57A 108.8 . . ?
C56 C57 H57B 108.8 . . ?
H57A C57 H57B 107.7 . . ?
C58 C57 C56 113.7(5) . . ?
C58 C57 H57A 108.8 . . ?
C58 C57 H57B 108.8 . . ?
C57 C58 H58 116.7 . . ?
C59 C58 C57 126.6(6) . . ?
C59 C58 H58 116.7 . . ?
C58 C59 H59A 120.0 . . ?
C58 C59 H59B 120.0 . . ?
H59A C59 H59B 120.0 . . ?
C47 C60 H60 127.2 . . ?
C61 C60 C47 105.7(5) . . ?
C61 C60 H60 127.2 . . ?
C60 C61 H61 127.0 . . ?
C60 C61 C62 105.9(5) . . ?
C62 C61 H61 127.0 . . ?
O10 C62 C61 102.3(4) . . ?
O10 C62 H62 114.9 . . ?
O10 C62 C63 101.0(4) . . ?
C61 C62 H62 114.9 . . ?
C61 C62 C63 107.2(5) . . ?
C63 C62 H62 114.9 . . ?
C48 C63 C62 100.3(4) . . ?
C48 C63 H63 109.9 . . ?
C62 C63 H63 109.9 . . ?
C64 C63 C48 112.6(5) . . ?
C64 C63 C62 113.8(5) . . ?
C64 C63 H63 109.9 . . ?
O11 C64 O12 122.6(5) . . ?
O11 C64 C63 124.7(5) . . ?
O12 C64 C63 112.7(5) . . ?
O12 C65 H65A 109.9 . . ?
O12 C65 H65B 109.9 . . ?
O12 C65 C66 108.7(6) . . ?
H65A C65 H65B 108.3 . . ?
C66 C65 H65A 109.9 . . ?
C66 C65 H65B 109.9 . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
C65 C66 H66C 109.5 . . ?
H66A C66 H66B 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 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 C4 C3 -166.6(6) . . . . ?
O1 C1 C4 C19 -53.6(9) . . . . ?
N1 C1 C4 C3 15.5(6) . . . . ?
N1 C1 C4 C19 128.4(6) . . . . ?
N1 C2 C3 O2 -79.1(5) . . . . ?
N1 C2 C3 C4 28.7(6) . . . . ?
N1 C2 C3 C16 156.6(6) . . . . ?
N1 C2 C12 C13 179.6(5) . . . . ?
N1 C5 C6 C7 35.1(8) . . . . ?
N1 C5 C6 C11 -147.8(5) . . . . ?
C1 N1 C2 C3 -20.2(7) . . . . ?
C1 N1 C2 C12 -144.2(6) . . . . ?
C1 N1 C5 C6 -100.5(7) . . . . ?
C1 C4 C19 C18 -111.2(6) . . . . ?
C1 C4 C19 C20 6.5(8) . . . . ?
O2 C3 C4 C1 88.6(5) . . . . ?
O2 C3 C4 C19 -36.6(5) . . . . ?
O2 C3 C16 C17 33.3(6) . . . . ?
O2 C18 C19 C4 35.2(6) . . . . ?
O2 C18 C19 C20 -83.1(6) . . . . ?
C2 N1 C1 O1 -175.1(6) . . . . ?
C2 N1 C1 C4 2.9(7) . . . . ?
C2 N1 C5 C6 64.6(7) . . . . ?
C2 C3 C4 C1 -27.7(6) . . . . ?
C2 C3 C4 C19 -152.9(5) . . . . ?
C2 C3 C16 C17 161.8(6) . . . . ?
C2 C12 C13 C14 174.2(6) . . . . ?
C3 O2 C18 C17 50.1(5) . . . . ?
C3 O2 C18 C19 -59.8(5) . . . . ?
C3 C2 C12 C13 64.2(7) . . . . ?
C3 C4 C19 C18 1.2(6) . . . . ?
C3 C4 C19 C20 118.9(5) . . . . ?
C3 C16 C17 C18 -1.2(6) . . . . ?
C4 C3 C16 C17 -71.1(6) . . . . ?
C4 C19 C20 O3 -82.4(8) . . . . ?
C4 C19 C20 O4 99.4(6) . . . . ?
C5 N1 C1 O1 -8.9(10) . . . . ?
C5 N1 C1 C4 169.1(6) . . . . ?
C5 N1 C2 C3 173.7(6) . . . . ?
C5 N1 C2 C12 49.7(8) . . . . ?
C5 C6 C7 C8 176.1(5) . . . . ?
C5 C6 C11 C10 -175.7(5) . . . . ?
C6 C7 C8 C9 -0.4(9) . . . . ?
C7 C6 C11 C10 1.5(9) . . . . ?
C7 C8 C9 C10 1.4(10) . . . . ?
C8 C9 C10 C11 -1.0(10) . . . . ?
C9 C10 C11 C6 -0.5(9) . . . . ?
C11 C6 C7 C8 -1.1(8) . . . . ?
C12 C2 C3 O2 43.1(7) . . . . ?
C12 C2 C3 C4 150.9(5) . . . . ?
C12 C2 C3 C16 -81.2(8) . . . . ?
C12 C13 C14 C15 -122.9(8) . . . . ?
C16 C3 C4 C1 -165.8(5) . . . . ?
C16 C3 C4 C19 69.0(6) . . . . ?
C16 C17 C18 O2 -31.5(6) . . . . ?
C16 C17 C18 C19 74.5(6) . . . . ?
C17 C18 C19 C4 -70.2(6) . . . . ?
C17 C18 C19 C20 171.5(5) . . . . ?
C18 O2 C3 C2 171.2(5) . . . . ?
C18 O2 C3 C4 59.4(5) . . . . ?
C18 O2 C3 C16 -51.4(5) . . . . ?
C18 C19 C20 O3 27.7(9) . . . . ?
C18 C19 C20 O4 -150.6(5) . . . . ?
C20 O4 C21 C22 -174.4(5) . . . . ?
C21 O4 C20 O3 4.2(8) . . . . ?
C21 O4 C20 C19 -177.6(5) . . . . ?
N4 C67 C70 C69 -18.3(6) . . . . ?
N4 C67 C70 C85 -130.5(5) . . . . ?
N4 C68 C69 O14 79.9(5) . . . . ?
N4 C68 C69 C70 -27.4(6) . . . . ?
N4 C68 C69 C82 -155.3(6) . . . . ?
N4 C68 C78 C79 -177.8(5) . . . . ?
N4 C71 C72 C73 125.6(6) . . . . ?
N4 C71 C72 C77 -54.0(8) . . . . ?
O13 C67 C70 C69 166.3(6) . . . . ?
O13 C67 C70 C85 54.1(9) . . . . ?
O14 C69 C70 C67 -87.8(5) . . . . ?
O14 C69 C70 C85 37.5(5) . . . . ?
O14 C69 C82 C83 -32.4(6) . . . . ?
O14 C84 C85 C70 -34.6(5) . . . . ?
O14 C84 C85 C86 84.9(5) . . . . ?
C67 N4 C68 C69 17.0(7) . . . . ?
C67 N4 C68 C78 139.7(5) . . . . ?
C67 N4 C71 C72 108.4(7) . . . . ?
C67 C70 C85 C84 110.1(6) . . . . ?
C67 C70 C85 C86 -8.7(8) . . . . ?
C68 N4 C67 O13 176.8(6) . . . . ?
C68 N4 C67 C70 1.2(7) . . . . ?
C68 N4 C71 C72 -58.7(8) . . . . ?
C68 C69 C70 C67 28.3(6) . . . . ?
C68 C69 C70 C85 153.5(5) . . . . ?
C68 C69 C82 C83 -161.6(6) . . . . ?
C68 C78 C79 C80 -64.7(7) . . . . ?
C69 O14 C84 C83 -50.6(5) . . . . ?
C69 O14 C84 C85 59.5(5) . . . . ?
C69 C68 C78 C79 -62.0(7) . . . . ?
C69 C70 C85 C84 -2.2(5) . . . . ?
C69 C70 C85 C86 -121.0(5) . . . . ?
C69 C82 C83 C84 0.2(6) . . . . ?
C70 C69 C82 C83 71.7(6) . . . . ?
C70 C85 C86 O15 90.4(7) . . . . ?
C70 C85 C86 O16 -88.2(6) . . . . ?
C71 N4 C67 O13 8.7(10) . . . . ?
C71 N4 C67 C70 -166.9(5) . . . . ?
C71 N4 C68 C69 -175.2(6) . . . . ?
C71 N4 C68 C78 -52.5(8) . . . . ?
C71 C72 C73 C74 179.6(6) . . . . ?
C71 C72 C77 C76 -179.3(6) . . . . ?
C72 C73 C74 C75 -0.4(10) . . . . ?
C73 C72 C77 C76 1.1(10) . . . . ?
C73 C74 C75 C76 1.5(11) . . . . ?
C74 C75 C76 C77 -1.3(11) . . . . ?
C75 C76 C77 C72 0.0(10) . . . . ?
C77 C72 C73 C74 -0.8(10) . . . . ?
C78 C68 C69 O14 -41.5(7) . . . . ?
C78 C68 C69 C70 -148.8(5) . . . . ?
C78 C68 C69 C82 83.3(8) . . . . ?
C78 C79 C80 C81 132.7(8) . . . . ?
C82 C69 C70 C67 167.3(5) . . . . ?
C82 C69 C70 C85 -67.5(6) . . . . ?
C82 C83 C84 O14 32.7(6) . . . . ?
C82 C83 C84 C85 -73.6(6) . . . . ?
C83 C84 C85 C70 71.1(5) . . . . ?
C83 C84 C85 C86 -169.3(4) . . . . ?
C84 O14 C69 C68 -170.6(5) . . . . ?
C84 O14 C69 C70 -60.0(5) . . . . ?
C84 O14 C69 C82 50.8(5) . . . . ?
C84 C85 C86 O15 -21.3(8) . . . . ?
C84 C85 C86 O16 160.0(4) . . . . ?
C86 O16 C87 C88 -162.6(5) . . . . ?
C87 O16 C86 O15 -1.8(8) . . . . ?
C87 O16 C86 C85 176.9(4) . . . . ?
N2 C23 C26 C25 -17.0(6) . . . . ?
N2 C23 C26 C41 -128.8(6) . . . . ?
N2 C24 C25 O6 82.7(5) . . . . ?
N2 C24 C25 C26 -24.8(6) . . . . ?
N2 C24 C25 C38 -153.2(6) . . . . ?
N2 C24 C34 C35 177.3(5) . . . . ?
N2 C27 C28 C29 150.2(6) . . . . ?
N2 C27 C28 C33 -32.0(8) . . . . ?
O5 C23 C26 C25 168.3(6) . . . . ?
O5 C23 C26 C41 56.6(9) . . . . ?
O6 C25 C26 C23 -89.1(5) . . . . ?
O6 C25 C26 C41 35.5(5) . . . . ?
O6 C25 C38 C39 -33.6(6) . . . . ?
O6 C40 C41 C26 -37.2(5) . . . . ?
O6 C40 C41 C42 80.7(5) . . . . ?
C23 N2 C24 C25 15.2(7) . . . . ?
C23 N2 C24 C34 138.1(5) . . . . ?
C23 N2 C27 C28 100.2(7) . . . . ?
C23 C26 C41 C40 113.0(6) . . . . ?
C23 C26 C41 C42 -6.7(8) . . . . ?
C24 N2 C23 O5 176.3(6) . . . . ?
C24 N2 C23 C26 1.4(7) . . . . ?
C24 N2 C27 C28 -66.5(8) . . . . ?
C24 C25 C26 C23 26.0(6) . . . . ?
C24 C25 C26 C41 150.6(5) . . . . ?
C24 C25 C38 C39 -161.4(6) . . . . ?
C24 C34 C35 C36 -74.1(7) . . . . ?
C25 O6 C40 C39 -49.4(5) . . . . ?
C25 O6 C40 C41 61.2(5) . . . . ?
C25 C24 C34 C35 -66.8(7) . . . . ?
C25 C26 C41 C40 0.7(6) . . . . ?
C25 C26 C41 C42 -119.0(5) . . . . ?
C25 C38 C39 C40 1.8(7) . . . . ?
C26 C25 C38 C39 71.0(6) . . . . ?
C26 C41 C42 O7 88.0(7) . . . . ?
C26 C41 C42 O8 -90.0(6) . . . . ?
C27 N2 C23 O5 8.6(10) . . . . ?
C27 N2 C23 C26 -166.2(5) . . . . ?
C27 N2 C24 C25 -177.3(6) . . . . ?
C27 N2 C24 C34 -54.4(8) . . . . ?
C27 C28 C29 C30 177.6(6) . . . . ?
C27 C28 C33 C32 -177.2(5) . . . . ?
C28 C29 C30 C31 -0.3(9) . . . . ?
C29 C28 C33 C32 0.7(9) . . . . ?
C29 C30 C31 C32 0.4(9) . . . . ?
C30 C31 C32 C33 0.0(9) . . . . ?
C31 C32 C33 C28 -0.6(9) . . . . ?
C33 C28 C29 C30 -0.3(9) . . . . ?
C34 C24 C25 O6 -39.3(7) . . . . ?
C34 C24 C25 C26 -146.7(5) . . . . ?
C34 C24 C25 C38 84.8(7) . . . . ?
C34 C35 C36 C37 117.7(8) . . . . ?
C38 C25 C26 C23 165.4(5) . . . . ?
C38 C25 C26 C41 -70.0(6) . . . . ?
C38 C39 C40 O6 30.8(6) . . . . ?
C38 C39 C40 C41 -74.6(6) . . . . ?
C39 C40 C41 C26 68.6(5) . . . . ?
C39 C40 C41 C42 -173.5(5) . . . . ?
C40 O6 C25 C24 -171.1(5) . . . . ?
C40 O6 C25 C26 -60.1(5) . . . . ?
C40 O6 C25 C38 50.8(5) . . . . ?
C40 C41 C42 O7 -23.2(8) . . . . ?
C40 C41 C42 O8 158.7(5) . . . . ?
C42 O8 C43 C44 91.1(7) . . . . ?
C43 O8 C42 O7 -12.0(8) . . . . ?
C43 O8 C42 C41 166.1(5) . . . . ?
N3 C45 C48 C47 18.9(6) . . . . ?
N3 C45 C48 C63 130.0(5) . . . . ?
N3 C46 C47 O10 -79.6(5) . . . . ?
N3 C46 C47 C48 27.3(6) . . . . ?
N3 C46 C47 C60 156.8(6) . . . . ?
N3 C46 C56 C57 -176.4(5) . . . . ?
N3 C49 C50 C51 31.5(8) . . . . ?
N3 C49 C50 C55 -150.0(5) . . . . ?
O9 C45 C48 C47 -164.5(6) . . . . ?
O9 C45 C48 C63 -53.4(9) . . . . ?
O10 C47 C48 C45 86.8(5) . . . . ?
O10 C47 C48 C63 -38.1(5) . . . . ?
O10 C47 C60 C61 33.7(6) . . . . ?
O10 C62 C63 C48 35.6(5) . . . . ?
O10 C62 C63 C64 -85.0(5) . . . . ?
C45 N3 C46 C47 -16.5(7) . . . . ?
C45 N3 C46 C56 -140.0(5) . . . . ?
C45 N3 C49 C50 -100.4(7) . . . . ?
C45 C48 C63 C62 -109.6(6) . . . . ?
C45 C48 C63 C64 11.8(8) . . . . ?
C46 N3 C45 O9 -178.6(6) . . . . ?
C46 N3 C45 C48 -1.9(7) . . . . ?
C46 N3 C49 C50 67.6(7) . . . . ?
C46 C47 C48 C45 -28.6(6) . . . . ?
C46 C47 C48 C63 -153.6(5) . . . . ?
C46 C47 C60 C61 161.5(6) . . . . ?
C46 C56 C57 C58 69.5(7) . . . . ?
C47 O10 C62 C61 49.9(5) . . . . ?
C47 O10 C62 C63 -60.7(5) . . . . ?
C47 C46 C56 C57 67.3(7) . . . . ?
C47 C48 C63 C62 1.9(5) . . . . ?
C47 C48 C63 C64 123.4(5) . . . . ?
C47 C60 C61 C62 -1.8(6) . . . . ?
C48 C47 C60 C61 -70.6(6) . . . . ?
C48 C63 C64 O11 -93.1(7) . . . . ?
C48 C63 C64 O12 86.6(6) . . . . ?
C49 N3 C45 O9 -9.6(10) . . . . ?
C49 N3 C45 C48 167.2(5) . . . . ?
C49 N3 C46 C47 174.6(5) . . . . ?
C49 N3 C46 C56 51.2(8) . . . . ?
C49 C50 C51 C52 177.0(5) . . . . ?
C49 C50 C55 C54 -176.8(5) . . . . ?
C50 C51 C52 C53 0.1(8) . . . . ?
C51 C50 C55 C54 1.8(8) . . . . ?
C51 C52 C53 C54 1.1(9) . . . . ?
C52 C53 C54 C55 -0.8(9) . . . . ?
C53 C54 C55 C50 -0.7(8) . . . . ?
C55 C50 C51 C52 -1.5(8) . . . . ?
C56 C46 C47 O10 42.8(6) . . . . ?
C56 C46 C47 C48 149.7(5) . . . . ?
C56 C46 C47 C60 -80.8(8) . . . . ?
C56 C57 C58 C59 -131.0(7) . . . . ?
C60 C47 C48 C45 -167.8(5) . . . . ?
C60 C47 C48 C63 67.2(6) . . . . ?
C60 C61 C62 O10 -31.3(6) . . . . ?
C60 C61 C62 C63 74.5(6) . . . . ?
C61 C62 C63 C48 -71.1(5) . . . . ?
C61 C62 C63 C64 168.3(5) . . . . ?
C62 O10 C47 C46 172.1(4) . . . . ?
C62 O10 C47 C48 61.5(5) . . . . ?
C62 O10 C47 C60 -50.5(4) . . . . ?
C62 C63 C64 O11 20.3(8) . . . . ?
C62 C63 C64 O12 -160.0(4) . . . . ?
C64 O12 C65 C66 161.1(7) . . . . ?
C65 O12 C64 O11 4.4(8) . . . . ?
C65 O12 C64 C63 -175.3(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
0 -15 5 0.0093 -0.0040 -15.0176 4.9888 0.2797 0.7408 0.6004
0 15 -5 0.0093 0.0040 15.0176 -4.9888 -0.2797 -0.7408 -0.6004
6 -1 6 0.1406 6.0039 -1.0090 6.0187 -0.2605 0.7436 -0.5834
-6 1 -6 0.1406 -6.0039 1.0090 -6.0187 0.2605 -0.7436 0.5834
0 8 19 0.0066 -0.0153 8.0072 19.0244 -1.0231 -0.0408 0.0395
0 -8 -19 0.0066 0.0153 -8.0072 -19.0244 1.0231 0.0408 -0.0395

_olex2_date_sample_data_collection 2015-11-18
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5629(16)
2 0.4371(16)

# start Validation Reply Form
_vrf_THETM01_jdf3_432b_cu        
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Small, poor quality, poorly diffracting crystal, with no diffraction at high resolution.
;
_vrf_PLAT023_jdf3_432b_cu        
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      54.24 Degree
RESPONSE: Small, poor quality, poorly diffracting crystal, with no diffraction at high resolution.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_jdf2_400a_cu
_database_code_depnum_ccdc_archive 'CCDC 1478963'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_audit_creation_date             2015-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl (1R*,2S*,10S*,11R*,12S*)-5-benzyl-9-oxo-15-oxa-5,8-diazatetracyclo[10.2.1.0¹,¹°.0²,8]pentadecane-11-carboxylate'
_chemical_formula_moiety         'C22 H28 N2 O4'
_chemical_formula_sum            'C22 H28 N2 O4'
_chemical_formula_weight         384.46
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H28 N2 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'

_cell_length_a                   9.67334(14)
_cell_length_b                   11.20885(18)
_cell_length_c                   18.6086(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.3265(14)
_cell_angle_gamma                90
_cell_volume                     2011.93(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8503
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      74.3810
_cell_measurement_theta_min      4.5850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14342
_diffrn_reflns_point_group_measured_fraction_full 0.822
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.354
_diffrn_reflns_theta_min         2.111
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega   22.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   57.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega   50.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega   42.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
  6 omega   42.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   88.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000  -58.5319 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   92.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   67.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000  -73.9609 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   60.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000  -94.7755 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   81.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega  125.00  151.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  133.00  160.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega  136.00  166.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega  124.00  153.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   98.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   86.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   87.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
 21 omega   45.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   -7.5474 73

#__ type_ start__ end____ width___ exp.time_
 22 omega   49.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
 23 omega   43.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000 -150.0000 63

#__ type_ start__ end____ width___ exp.time_
 24 omega   29.00   54.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   81.00  163.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
 26 omega  -24.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.4589  -57.0000  -60.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0432678000
_diffrn_orient_matrix_UB_12      0.1322992000
_diffrn_orient_matrix_UB_13      0.0003144000
_diffrn_orient_matrix_UB_21      0.0939143000
_diffrn_orient_matrix_UB_22      0.0254356000
_diffrn_orient_matrix_UB_23      -0.0614843000
_diffrn_orient_matrix_UB_31      -0.1217173000
_diffrn_orient_matrix_UB_32      -0.0273231000
_diffrn_orient_matrix_UB_33      -0.0557731000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.552
_reflns_Friedel_fraction_full    0.637
_reflns_Friedel_fraction_max     0.600
_reflns_number_gt                6178
_reflns_number_total             6546
_reflns_odcompleteness_completeness 98.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2040 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6546
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.022
_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)+(0.0693P)²+0.2017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1152
_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:
 C26(H26), C27(H27), C31(H31), C33(H33), C11(H11), C4(H4), C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C28(H28A,H28B), C29(H29A,H29B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C2(H2A,H2B), C12(H12A,
 H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C6(H6A,H6B), C16(H16A,
 H16B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C40(H40), C41(H41), C42(H42), C43(H43), C44(H44), C22(H22), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C1(H1A,H1B,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
N3 N -0.9386(2) -0.4557(2) -0.24951(11) 0.0227(4) Uani 1 1 d . . . . .
N4 N -0.9191(3) -0.2752(2) -0.36373(13) 0.0292(5) Uani 1 1 d . . . . .
O5 O -0.73300(19) -0.77677(18) -0.11998(10) 0.0267(4) Uani 1 1 d . . . . .
O6 O -0.9563(2) -0.7426(2) -0.10022(12) 0.0340(5) Uani 1 1 d . . . . .
O7 O -0.98008(17) -0.45729(18) -0.09385(9) 0.0213(4) Uani 1 1 d . . . . .
O8 O -0.8425(2) -0.64234(18) -0.25058(10) 0.0283(4) Uani 1 1 d . . . . .
C23 C -0.6389(3) -0.9513(3) -0.16916(17) 0.0359(7) Uani 1 1 d . . . . .
H23A H -0.5865 -0.9010 -0.1988 0.054 Uiso 1 1 calc GR . . . .
H23B H -0.6597 -1.0251 -0.1938 0.054 Uiso 1 1 calc GR . . . .
H23C H -0.5857 -0.9670 -0.1245 0.054 Uiso 1 1 calc GR . . . .
C24 C -0.7720(3) -0.8896(3) -0.15410(16) 0.0307(6) Uani 1 1 d . . . . .
H24A H -0.8287 -0.8761 -0.1986 0.037 Uiso 1 1 calc R . . . .
H24B H -0.8242 -0.9378 -0.1224 0.037 Uiso 1 1 calc R . . . .
C25 C -0.8392(3) -0.7079(3) -0.10185(14) 0.0243(5) Uani 1 1 d . . . . .
C26 C -0.7876(2) -0.5834(2) -0.08386(14) 0.0218(5) Uani 1 1 d . . . . .
H26 H -0.6949 -0.5873 -0.0588 0.026 Uiso 1 1 calc R . . . .
C27 C -0.8843(3) -0.5099(3) -0.03926(13) 0.0242(5) Uani 1 1 d . . . . .
H27 H -0.9296 -0.5568 -0.0033 0.029 Uiso 1 1 calc R . . . .
C28 C -0.8062(3) -0.3994(3) -0.00775(15) 0.0298(6) Uani 1 1 d . . . . .
H28A H -0.7129 -0.4197 0.0110 0.036 Uiso 1 1 calc R . . . .
H28B H -0.8552 -0.3628 0.0302 0.036 Uiso 1 1 calc R . . . .
C29 C -0.8048(3) -0.3169(3) -0.07449(14) 0.0275(6) Uani 1 1 d . . . . .
H29A H -0.8566 -0.2441 -0.0681 0.033 Uiso 1 1 calc R . . . .
H29B H -0.7110 -0.2970 -0.0852 0.033 Uiso 1 1 calc R . . . .
C30 C -0.8760(3) -0.3961(2) -0.13263(14) 0.0212(5) Uani 1 1 d . . . . .
C31 C -0.7849(2) -0.5023(2) -0.15157(13) 0.0201(5) Uani 1 1 d . . . . .
H31 H -0.6902 -0.4762 -0.1586 0.024 Uiso 1 1 calc R . . . .
C32 C -0.8574(3) -0.5454(3) -0.22198(13) 0.0215(5) Uani 1 1 d . . . . .
C33 C -0.9368(3) -0.3489(2) -0.20425(14) 0.0232(5) Uani 1 1 d . . . . .
H33 H -1.0314 -0.3198 -0.2000 0.028 Uiso 1 1 calc R . . . .
C34 C -0.8460(3) -0.2496(3) -0.23264(15) 0.0293(6) Uani 1 1 d . . . . .
H34A H -0.8354 -0.1876 -0.1963 0.035 Uiso 1 1 calc R . . . .
H34B H -0.7547 -0.2824 -0.2384 0.035 Uiso 1 1 calc R . . . .
C35 C -0.8988(4) -0.1923(3) -0.30356(17) 0.0367(7) Uani 1 1 d . . . . .
H35A H -0.9862 -0.1529 -0.2969 0.044 Uiso 1 1 calc R . . . .
H35B H -0.8332 -0.1314 -0.3159 0.044 Uiso 1 1 calc R . . . .
C36 C -1.0431(3) -0.3490(3) -0.35771(16) 0.0349(7) Uani 1 1 d . . . . .
H36A H -1.0863 -0.3640 -0.4056 0.042 Uiso 1 1 calc R . . . .
H36B H -1.1089 -0.3052 -0.3310 0.042 Uiso 1 1 calc R . . . .
C37 C -1.0117(3) -0.4672(3) -0.32056(14) 0.0324(6) Uani 1 1 d . . . . .
H37A H -1.0981 -0.5093 -0.3158 0.039 Uiso 1 1 calc R . . . .
H37B H -0.9560 -0.5153 -0.3507 0.039 Uiso 1 1 calc R . . . .
C38 C -0.9287(4) -0.2084(3) -0.43194(17) 0.0383(7) Uani 1 1 d . . . . .
H38A H -0.8559 -0.1486 -0.4304 0.046 Uiso 1 1 calc R . . . .
H38B H -1.0171 -0.1672 -0.4373 0.046 Uiso 1 1 calc R . . . .
C39 C -0.9154(3) -0.2882(3) -0.49658(15) 0.0328(6) Uani 1 1 d . . . . .
C40 C -0.8135(3) -0.3757(3) -0.49421(15) 0.0321(6) Uani 1 1 d . . . . .
H40 H -0.7587 -0.3886 -0.4517 0.039 Uiso 1 1 calc R . . . .
C41 C -0.7923(4) -0.4441(3) -0.55443(18) 0.0462(8) Uani 1 1 d . . . . .
H41 H -0.7238 -0.5024 -0.5521 0.055 Uiso 1 1 calc R . . . .
C42 C -0.8727(5) -0.4255(4) -0.61763(19) 0.0602(13) Uani 1 1 d . . . . .
H42 H -0.8576 -0.4710 -0.6581 0.072 Uiso 1 1 calc R . . . .
C43 C -0.9753(5) -0.3400(6) -0.6213(2) 0.0688(16) Uani 1 1 d . . . . .
H43 H -1.0303 -0.3282 -0.6639 0.083 Uiso 1 1 calc R . . . .
C44 C -0.9961(4) -0.2708(4) -0.5602(2) 0.0516(10) Uani 1 1 d . . . . .
H44 H -1.0649 -0.2127 -0.5625 0.062 Uiso 1 1 calc R . . . .
O1 O -0.23324(19) -0.16877(18) -0.13281(11) 0.0271(4) Uani 1 1 d . . . . .
C22 C -0.4621(3) -0.6771(3) -0.52772(15) 0.0291(6) Uani 1 1 d . . . . .
H22 H -0.4921 -0.7494 -0.5099 0.035 Uiso 1 1 calc R . . . .
N1 N -0.4573(2) -0.49181(19) -0.25459(10) 0.0185(4) Uani 1 1 d . . . . .
C1 C -0.1392(3) 0.0088(3) -0.17816(16) 0.0335(6) Uani 1 1 d . . . . .
H1A H -0.0876 -0.0362 -0.2110 0.050 Uiso 1 1 calc GR . . . .
H1B H -0.0849 0.0178 -0.1332 0.050 Uiso 1 1 calc GR . . . .
H1C H -0.1607 0.0860 -0.1983 0.050 Uiso 1 1 calc GR . . . .
O2 O -0.4551(2) -0.2026(2) -0.10965(13) 0.0359(5) Uani 1 1 d . . . . .
C2 C -0.2718(3) -0.0561(3) -0.16572(17) 0.0327(6) Uani 1 1 d . . . . .
H2A H -0.3268 -0.0100 -0.1343 0.039 Uiso 1 1 calc R . . . .
H2B H -0.3260 -0.0688 -0.2111 0.039 Uiso 1 1 calc R . . . .
O3 O -0.47861(16) -0.48652(17) -0.09795(9) 0.0195(4) Uani 1 1 d . . . . .
N2 N -0.4711(2) -0.6797(2) -0.36939(11) 0.0233(4) Uani 1 1 d . . . . .
C3 C -0.3380(3) -0.2377(3) -0.11282(14) 0.0245(5) Uani 1 1 d . . . . .
C10 C -0.3681(3) -0.4042(2) -0.23160(13) 0.0210(5) Uani 1 1 d . . . . .
O4 O -0.3517(2) -0.30918(18) -0.26212(10) 0.0296(4) Uani 1 1 d . . . . .
C11 C -0.4501(2) -0.5989(2) -0.20843(12) 0.0194(5) Uani 1 1 d . . . . .
H11 H -0.5434 -0.6277 -0.2006 0.023 Uiso 1 1 calc R . . . .
C4 C -0.2855(2) -0.3616(2) -0.09478(14) 0.0217(5) Uani 1 1 d . . . . .
H4 H -0.1909 -0.3574 -0.0720 0.026 Uiso 1 1 calc R . . . .
C12 C -0.3644(3) -0.6980(2) -0.24012(14) 0.0230(5) Uani 1 1 d . . . . .
H12A H -0.2761 -0.6651 -0.2518 0.028 Uiso 1 1 calc R . . . .
H12B H -0.3456 -0.7590 -0.2037 0.028 Uiso 1 1 calc R . . . .
C13 C -0.4344(3) -0.7562(2) -0.30760(13) 0.0258(5) Uani 1 1 d . . . . .
H13A H -0.3734 -0.8183 -0.3230 0.031 Uiso 1 1 calc R . . . .
H13B H -0.5184 -0.7948 -0.2942 0.031 Uiso 1 1 calc R . . . .
C5 C -0.3785(3) -0.4335(2) -0.04673(13) 0.0221(5) Uani 1 1 d . . . . .
H5 H -0.4198 -0.3852 -0.0100 0.027 Uiso 1 1 calc R . . . .
C14 C -0.5838(3) -0.5970(3) -0.35924(13) 0.0246(5) Uani 1 1 d . . . . .
H14A H -0.6508 -0.6372 -0.3315 0.029 Uiso 1 1 calc R . . . .
H14B H -0.6295 -0.5791 -0.4062 0.029 Uiso 1 1 calc R . . . .
C15 C -0.5451(3) -0.4788(3) -0.32176(13) 0.0244(5) Uani 1 1 d . . . . .
H15A H -0.4971 -0.4292 -0.3546 0.029 Uiso 1 1 calc R . . . .
H15B H -0.6296 -0.4377 -0.3114 0.029 Uiso 1 1 calc R . . . .
C6 C -0.2984(3) -0.5434(3) -0.01590(13) 0.0253(5) Uani 1 1 d . . . . .
H6A H -0.3434 -0.5783 0.0239 0.030 Uiso 1 1 calc R . . . .
H6B H -0.2035 -0.5231 0.0001 0.030 Uiso 1 1 calc R . . . .
C16 C -0.3548(3) -0.6289(3) -0.40358(13) 0.0254(5) Uani 1 1 d . . . . .
H16A H -0.2789 -0.6857 -0.4008 0.030 Uiso 1 1 calc R . . . .
H16B H -0.3234 -0.5577 -0.3775 0.030 Uiso 1 1 calc R . . . .
C17 C -0.3914(3) -0.5969(3) -0.48167(14) 0.0245(5) Uani 1 1 d . . . . .
C7 C -0.3045(3) -0.6284(3) -0.08202(13) 0.0236(5) Uani 1 1 d . . . . .
H7A H -0.2125 -0.6497 -0.0951 0.028 Uiso 1 1 calc R . . . .
H7B H -0.3565 -0.7003 -0.0735 0.028 Uiso 1 1 calc R . . . .
C18 C -0.3492(3) -0.4884(3) -0.50905(16) 0.0305(6) Uani 1 1 d . . . . .
H18 H -0.3032 -0.4334 -0.4784 0.037 Uiso 1 1 calc R . . . .
C19 C -0.3752(3) -0.4613(3) -0.58172(16) 0.0369(6) Uani 1 1 d . . . . .
H19 H -0.3464 -0.3887 -0.5996 0.044 Uiso 1 1 calc R . . . .
C8 C -0.3800(2) -0.5493(2) -0.13890(12) 0.0187(5) Uani 1 1 d . . . . .
C20 C -0.4444(3) -0.5429(3) -0.62737(15) 0.0352(6) Uani 1 1 d . . . . .
H20 H -0.4610 -0.5255 -0.6761 0.042 Uiso 1 1 calc R . . . .
C21 C -0.4886(3) -0.6502(3) -0.60051(15) 0.0333(6) Uani 1 1 d . . . . .
H21 H -0.5360 -0.7045 -0.6311 0.040 Uiso 1 1 calc R . . . .
C9 C -0.2896(2) -0.4458(2) -0.16179(12) 0.0183(5) Uani 1 1 d . . . . .
H9 H -0.1964 -0.4736 -0.1707 0.022 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
N3 C32 1.353(4) . ?
N3 C33 1.463(4) . ?
N3 C37 1.457(3) . ?
N4 C35 1.457(4) . ?
N4 C36 1.468(4) . ?
N4 C38 1.471(4) . ?
O5 C24 1.452(4) . ?
O5 C25 1.349(3) . ?
O6 C25 1.200(3) . ?
O7 C27 1.448(3) . ?
O7 C30 1.454(3) . ?
O8 C32 1.223(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 C24 1.506(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.510(4) . ?
C26 H26 0.9800 . ?
C26 C27 1.536(3) . ?
C26 C31 1.556(4) . ?
C27 H27 0.9800 . ?
C27 C28 1.543(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.550(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.523(4) . ?
C30 C31 1.538(3) . ?
C30 C33 1.512(4) . ?
C31 H31 0.9800 . ?
C31 C32 1.517(3) . ?
C33 H33 0.9800 . ?
C33 C34 1.536(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.521(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.515(4) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.512(5) . ?
C39 C40 1.389(5) . ?
C39 C44 1.382(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.385(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.376(6) . ?
C42 H42 0.9300 . ?
C42 C43 1.378(8) . ?
C43 H43 0.9300 . ?
C43 C44 1.403(8) . ?
C44 H44 0.9300 . ?
O1 C2 1.440(4) . ?
O1 C3 1.349(3) . ?
C22 H22 0.9300 . ?
C22 C17 1.386(4) . ?
C22 C21 1.392(4) . ?
N1 C10 1.355(3) . ?
N1 C11 1.475(3) . ?
N1 C15 1.465(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.507(4) . ?
O2 C3 1.205(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O3 C5 1.435(3) . ?
O3 C8 1.448(3) . ?
N2 C13 1.456(3) . ?
N2 C14 1.454(3) . ?
N2 C16 1.450(3) . ?
C3 C4 1.508(4) . ?
C10 O4 1.223(3) . ?
C10 C9 1.527(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.530(3) . ?
C11 C8 1.520(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.543(4) . ?
C4 C9 1.562(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.527(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C5 H5 0.9800 . ?
C5 C6 1.542(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.531(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.554(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.512(3) . ?
C17 C18 1.392(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.524(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(5) . ?
C8 C9 1.533(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(5) . ?
C21 H21 0.9300 . ?
C9 H9 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
C32 N3 C33 114.1(2) . . ?
C32 N3 C37 120.3(2) . . ?
C37 N3 C33 125.4(2) . . ?
C35 N4 C36 111.4(2) . . ?
C35 N4 C38 109.5(2) . . ?
C36 N4 C38 110.8(3) . . ?
C25 O5 C24 115.5(2) . . ?
C27 O7 C30 96.30(17) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
O5 C24 C23 106.5(2) . . ?
O5 C24 H24A 110.4 . . ?
O5 C24 H24B 110.4 . . ?
C23 C24 H24A 110.4 . . ?
C23 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
O5 C25 C26 109.8(2) . . ?
O6 C25 O5 123.9(3) . . ?
O6 C25 C26 126.2(3) . . ?
C25 C26 H26 109.9 . . ?
C25 C26 C27 114.3(2) . . ?
C25 C26 C31 112.7(2) . . ?
C27 C26 H26 109.9 . . ?
C27 C26 C31 99.9(2) . . ?
C31 C26 H26 109.9 . . ?
O7 C27 C26 102.87(19) . . ?
O7 C27 H27 113.7 . . ?
O7 C27 C28 102.1(2) . . ?
C26 C27 H27 113.7 . . ?
C26 C27 C28 109.6(2) . . ?
C28 C27 H27 113.7 . . ?
C27 C28 H28A 111.4 . . ?
C27 C28 H28B 111.4 . . ?
C27 C28 C29 102.0(2) . . ?
H28A C28 H28B 109.2 . . ?
C29 C28 H28A 111.4 . . ?
C29 C28 H28B 111.4 . . ?
C28 C29 H29A 111.6 . . ?
C28 C29 H29B 111.6 . . ?
H29A C29 H29B 109.4 . . ?
C30 C29 C28 101.0(2) . . ?
C30 C29 H29A 111.6 . . ?
C30 C29 H29B 111.6 . . ?
O7 C30 C29 102.43(19) . . ?
O7 C30 C31 100.3(2) . . ?
O7 C30 C33 111.4(2) . . ?
C29 C30 C31 112.2(2) . . ?
C33 C30 C29 123.2(2) . . ?
C33 C30 C31 105.1(2) . . ?
C26 C31 H31 110.9 . . ?
C30 C31 C26 102.82(19) . . ?
C30 C31 H31 110.9 . . ?
C32 C31 C26 118.6(2) . . ?
C32 C31 C30 102.1(2) . . ?
C32 C31 H31 110.9 . . ?
N3 C32 C31 107.9(2) . . ?
O8 C32 N3 125.4(2) . . ?
O8 C32 C31 126.6(2) . . ?
N3 C33 C30 102.0(2) . . ?
N3 C33 H33 110.4 . . ?
N3 C33 C34 112.1(2) . . ?
C30 C33 H33 110.4 . . ?
C30 C33 C34 111.2(2) . . ?
C34 C33 H33 110.4 . . ?
C33 C34 H34A 108.2 . . ?
C33 C34 H34B 108.2 . . ?
H34A C34 H34B 107.4 . . ?
C35 C34 C33 116.2(3) . . ?
C35 C34 H34A 108.2 . . ?
C35 C34 H34B 108.2 . . ?
N4 C35 C34 114.5(2) . . ?
N4 C35 H35A 108.6 . . ?
N4 C35 H35B 108.6 . . ?
C34 C35 H35A 108.6 . . ?
C34 C35 H35B 108.6 . . ?
H35A C35 H35B 107.6 . . ?
N4 C36 H36A 109.0 . . ?
N4 C36 H36B 109.0 . . ?
N4 C36 C37 113.0(2) . . ?
H36A C36 H36B 107.8 . . ?
C37 C36 H36A 109.0 . . ?
C37 C36 H36B 109.0 . . ?
N3 C37 C36 113.8(3) . . ?
N3 C37 H37A 108.8 . . ?
N3 C37 H37B 108.8 . . ?
C36 C37 H37A 108.8 . . ?
C36 C37 H37B 108.8 . . ?
H37A C37 H37B 107.7 . . ?
N4 C38 H38A 109.1 . . ?
N4 C38 H38B 109.1 . . ?
N4 C38 C39 112.4(2) . . ?
H38A C38 H38B 107.9 . . ?
C39 C38 H38A 109.1 . . ?
C39 C38 H38B 109.1 . . ?
C40 C39 C38 119.7(3) . . ?
C44 C39 C38 121.4(3) . . ?
C44 C39 C40 118.7(3) . . ?
C39 C40 H40 119.6 . . ?
C41 C40 C39 120.8(3) . . ?
C41 C40 H40 119.6 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.0(4) . . ?
C42 C41 H41 120.0 . . ?
C41 C42 H42 119.8 . . ?
C41 C42 C43 120.4(4) . . ?
C43 C42 H42 119.8 . . ?
C42 C43 H43 120.3 . . ?
C42 C43 C44 119.4(4) . . ?
C44 C43 H43 120.3 . . ?
C39 C44 C43 120.6(4) . . ?
C39 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C3 O1 C2 116.3(2) . . ?
C17 C22 H22 119.8 . . ?
C17 C22 C21 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C10 N1 C11 113.89(19) . . ?
C10 N1 C15 120.8(2) . . ?
C15 N1 C11 125.3(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 107.0(2) . . ?
O1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C5 O3 C8 96.46(17) . . ?
C14 N2 C13 114.4(2) . . ?
C16 N2 C13 115.3(2) . . ?
C16 N2 C14 114.8(2) . . ?
O1 C3 C4 109.9(2) . . ?
O2 C3 O1 123.7(3) . . ?
O2 C3 C4 126.3(3) . . ?
N1 C10 C9 108.1(2) . . ?
O4 C10 N1 125.9(2) . . ?
O4 C10 C9 126.0(2) . . ?
N1 C11 H11 110.5 . . ?
N1 C11 C12 111.71(18) . . ?
N1 C11 C8 101.3(2) . . ?
C12 C11 H11 110.5 . . ?
C8 C11 H11 110.5 . . ?
C8 C11 C12 112.0(2) . . ?
C3 C4 H4 109.9 . . ?
C3 C4 C5 114.1(2) . . ?
C3 C4 C9 113.0(2) . . ?
C5 C4 H4 109.9 . . ?
C5 C4 C9 99.54(19) . . ?
C9 C4 H4 109.9 . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.0(2) . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
N2 C13 C12 117.7(2) . . ?
N2 C13 H13A 107.9 . . ?
N2 C13 H13B 107.9 . . ?
C12 C13 H13A 107.9 . . ?
C12 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
O3 C5 C4 103.02(18) . . ?
O3 C5 H5 113.7 . . ?
O3 C5 C6 102.2(2) . . ?
C4 C5 H5 113.7 . . ?
C6 C5 C4 109.5(2) . . ?
C6 C5 H5 113.7 . . ?
N2 C14 H14A 108.1 . . ?
N2 C14 H14B 108.1 . . ?
N2 C14 C15 116.8(2) . . ?
H14A C14 H14B 107.3 . . ?
C15 C14 H14A 108.1 . . ?
C15 C14 H14B 108.1 . . ?
N1 C15 C14 114.1(2) . . ?
N1 C15 H15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C5 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
C5 C6 C7 101.94(19) . . ?
H6A C6 H6B 109.2 . . ?
C7 C6 H6A 111.4 . . ?
C7 C6 H6B 111.4 . . ?
N2 C16 H16A 109.1 . . ?
N2 C16 H16B 109.1 . . ?
N2 C16 C17 112.4(2) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C22 C17 C16 120.6(3) . . ?
C22 C17 C18 119.0(2) . . ?
C18 C17 C16 120.3(3) . . ?
C6 C7 H7A 111.7 . . ?
C6 C7 H7B 111.7 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 C6 100.4(2) . . ?
C8 C7 H7A 111.7 . . ?
C8 C7 H7B 111.7 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
O3 C8 C11 110.91(19) . . ?
O3 C8 C7 102.57(18) . . ?
O3 C8 C9 101.0(2) . . ?
C11 C8 C7 122.6(2) . . ?
C11 C8 C9 105.51(19) . . ?
C7 C8 C9 112.3(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C10 C9 C4 118.4(2) . . ?
C10 C9 C8 102.13(19) . . ?
C10 C9 H9 111.0 . . ?
C4 C9 H9 111.0 . . ?
C8 C9 C4 102.51(18) . . ?
C8 C9 H9 111.0 . . ?

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
N3 C33 C34 C35 68.2(3) . . . . ?
N4 C36 C37 N3 55.1(3) . . . . ?
N4 C38 C39 C40 -44.4(4) . . . . ?
N4 C38 C39 C44 140.3(3) . . . . ?
O5 C25 C26 C27 -160.7(2) . . . . ?
O5 C25 C26 C31 86.1(3) . . . . ?
O6 C25 C26 C27 18.8(4) . . . . ?
O6 C25 C26 C31 -94.3(3) . . . . ?
O7 C27 C28 C29 -32.7(2) . . . . ?
O7 C30 C31 C26 -36.4(2) . . . . ?
O7 C30 C31 C32 87.0(2) . . . . ?
O7 C30 C33 N3 -80.2(2) . . . . ?
O7 C30 C33 C34 160.0(2) . . . . ?
C24 O5 C25 O6 13.9(4) . . . . ?
C24 O5 C25 C26 -166.5(2) . . . . ?
C25 O5 C24 C23 -179.7(2) . . . . ?
C25 C26 C27 O7 -86.5(2) . . . . ?
C25 C26 C27 C28 165.5(2) . . . . ?
C25 C26 C31 C30 123.4(2) . . . . ?
C25 C26 C31 C32 11.8(3) . . . . ?
C26 C27 C28 C29 75.9(3) . . . . ?
C26 C31 C32 N3 131.1(2) . . . . ?
C26 C31 C32 O8 -51.1(3) . . . . ?
C27 O7 C30 C29 -57.9(2) . . . . ?
C27 O7 C30 C31 57.8(2) . . . . ?
C27 O7 C30 C33 168.6(2) . . . . ?
C27 C26 C31 C30 1.7(2) . . . . ?
C27 C26 C31 C32 -109.9(2) . . . . ?
C27 C28 C29 C30 -2.4(3) . . . . ?
C28 C29 C30 O7 36.7(3) . . . . ?
C28 C29 C30 C31 -70.0(3) . . . . ?
C28 C29 C30 C33 162.9(2) . . . . ?
C29 C30 C31 C26 71.6(2) . . . . ?
C29 C30 C31 C32 -165.0(2) . . . . ?
C29 C30 C33 N3 157.6(2) . . . . ?
C29 C30 C33 C34 37.9(3) . . . . ?
C30 O7 C27 C26 -58.1(2) . . . . ?
C30 O7 C27 C28 55.5(2) . . . . ?
C30 C31 C32 N3 19.1(2) . . . . ?
C30 C31 C32 O8 -163.1(2) . . . . ?
C30 C33 C34 C35 -178.3(2) . . . . ?
C31 C26 C27 O7 34.1(2) . . . . ?
C31 C26 C27 C28 -74.0(2) . . . . ?
C31 C30 C33 N3 27.5(2) . . . . ?
C31 C30 C33 C34 -92.2(2) . . . . ?
C32 N3 C33 C30 -16.5(3) . . . . ?
C32 N3 C33 C34 102.6(3) . . . . ?
C32 N3 C37 C36 -154.1(2) . . . . ?
C33 N3 C32 O8 -179.7(2) . . . . ?
C33 N3 C32 C31 -1.8(3) . . . . ?
C33 N3 C37 C36 21.7(4) . . . . ?
C33 C30 C31 C26 -152.1(2) . . . . ?
C33 C30 C31 C32 -28.7(2) . . . . ?
C33 C34 C35 N4 -58.4(3) . . . . ?
C35 N4 C36 C37 -93.6(3) . . . . ?
C35 N4 C38 C39 166.3(3) . . . . ?
C36 N4 C35 C34 74.0(3) . . . . ?
C36 N4 C38 C39 -70.5(3) . . . . ?
C37 N3 C32 O8 -3.4(4) . . . . ?
C37 N3 C32 C31 174.4(2) . . . . ?
C37 N3 C33 C30 167.4(2) . . . . ?
C37 N3 C33 C34 -73.5(3) . . . . ?
C38 N4 C35 C34 -163.1(3) . . . . ?
C38 N4 C36 C37 144.2(3) . . . . ?
C38 C39 C40 C41 -175.1(3) . . . . ?
C38 C39 C44 C43 175.2(3) . . . . ?
C39 C40 C41 C42 0.1(5) . . . . ?
C40 C39 C44 C43 -0.2(5) . . . . ?
C40 C41 C42 C43 -0.6(5) . . . . ?
C41 C42 C43 C44 0.8(6) . . . . ?
C42 C43 C44 C39 -0.4(6) . . . . ?
C44 C39 C40 C41 0.3(4) . . . . ?
O1 C3 C4 C5 159.4(2) . . . . ?
O1 C3 C4 C9 -87.8(3) . . . . ?
C22 C17 C18 C19 -1.1(4) . . . . ?
N1 C10 C9 C4 -128.4(2) . . . . ?
N1 C10 C9 C8 -16.8(2) . . . . ?
N1 C11 C12 C13 -70.7(3) . . . . ?
N1 C11 C8 O3 79.7(2) . . . . ?
N1 C11 C8 C7 -158.9(2) . . . . ?
N1 C11 C8 C9 -28.8(2) . . . . ?
O2 C3 C4 C5 -19.9(4) . . . . ?
O2 C3 C4 C9 92.9(3) . . . . ?
C2 O1 C3 O2 -13.1(4) . . . . ?
C2 O1 C3 C4 167.6(2) . . . . ?
O3 C5 C6 C7 32.4(2) . . . . ?
O3 C8 C9 C10 -87.3(2) . . . . ?
O3 C8 C9 C4 35.8(2) . . . . ?
N2 C14 C15 N1 -49.5(3) . . . . ?
N2 C16 C17 C22 -47.2(3) . . . . ?
N2 C16 C17 C18 135.6(3) . . . . ?
C3 O1 C2 C1 175.8(2) . . . . ?
C3 C4 C5 O3 86.3(2) . . . . ?
C3 C4 C5 C6 -165.5(2) . . . . ?
C3 C4 C9 C10 -11.2(3) . . . . ?
C3 C4 C9 C8 -122.6(2) . . . . ?
C10 N1 C11 C12 -100.0(2) . . . . ?
C10 N1 C11 C8 19.4(2) . . . . ?
C10 N1 C15 C14 151.6(2) . . . . ?
O4 C10 C9 C4 52.7(3) . . . . ?
O4 C10 C9 C8 164.3(2) . . . . ?
C11 N1 C10 O4 177.3(2) . . . . ?
C11 N1 C10 C9 -1.6(3) . . . . ?
C11 N1 C15 C14 -24.9(3) . . . . ?
C11 C12 C13 N2 58.8(3) . . . . ?
C11 C8 C9 C10 28.3(2) . . . . ?
C11 C8 C9 C4 151.36(19) . . . . ?
C4 C5 C6 C7 -76.3(2) . . . . ?
C12 C11 C8 O3 -161.1(2) . . . . ?
C12 C11 C8 C7 -39.8(3) . . . . ?
C12 C11 C8 C9 90.4(2) . . . . ?
C13 N2 C14 C15 84.8(3) . . . . ?
C13 N2 C16 C17 155.5(2) . . . . ?
C5 O3 C8 C11 -169.2(2) . . . . ?
C5 O3 C8 C7 58.3(2) . . . . ?
C5 O3 C8 C9 -57.7(2) . . . . ?
C5 C4 C9 C10 110.2(2) . . . . ?
C5 C4 C9 C8 -1.2(2) . . . . ?
C5 C6 C7 C8 2.7(2) . . . . ?
C14 N2 C13 C12 -69.7(3) . . . . ?
C14 N2 C16 C17 -68.3(3) . . . . ?
C15 N1 C10 O4 0.4(4) . . . . ?
C15 N1 C10 C9 -178.5(2) . . . . ?
C15 N1 C11 C12 76.7(3) . . . . ?
C15 N1 C11 C8 -163.9(2) . . . . ?
C6 C7 C8 O3 -36.9(2) . . . . ?
C6 C7 C8 C11 -162.1(2) . . . . ?
C6 C7 C8 C9 70.7(2) . . . . ?
C16 N2 C13 C12 66.8(3) . . . . ?
C16 N2 C14 C15 -51.8(3) . . . . ?
C16 C17 C18 C19 176.2(3) . . . . ?
C17 C22 C21 C20 -0.1(4) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
C7 C8 C9 C10 164.1(2) . . . . ?
C7 C8 C9 C4 -72.8(2) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C19 C20 C21 C22 -0.8(5) . . . . ?
C8 O3 C5 C4 58.0(2) . . . . ?
C8 O3 C5 C6 -55.6(2) . . . . ?
C8 C11 C12 C13 176.5(2) . . . . ?
C21 C22 C17 C16 -176.2(3) . . . . ?
C21 C22 C17 C18 1.0(4) . . . . ?
C9 C4 C5 O3 -34.4(2) . . . . ?
C9 C4 C5 C6 73.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
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 -2 11 0.0498 0.9875 -1.9909 11.0083 -0.3027 -0.6347 -0.6798
0 2 -11 0.0383 0.0115 1.9901 -11.0082 0.2593 0.7285 0.5582
-6 0 2 0.1658 -5.9956 0.0069 1.9999 0.2610 -0.6859 0.6180
6 0 -2 0.1403 5.9956 -0.0069 -1.9999 -0.2610 0.6859 -0.6180
0 7 1 0.0473 0.0128 7.0081 0.9711 0.9269 0.1197 -0.2472
1 -7 -1 0.0350 0.9862 -7.0089 -0.9711 -0.9703 -0.0259 0.1256
6 0 3 0.1380 5.9922 -0.0015 3.0001 -0.2585 0.3783 -0.8966
0 2 11 0.0523 -0.0038 2.0139 10.9917 0.2701 -0.6250 -0.6676
0 -2 -11 0.0361 0.0038 -2.0139 -10.9917 -0.2701 0.6250 0.6676
0 -6 -6 0.0318 -0.0074 -6.0125 -5.9752 -0.7970 0.2138 0.4984
0 5 8 0.0487 0.0041 5.0137 7.9794 0.6656 -0.3627 -0.5825
0 -7 0 0.0318 -0.0135 -7.0071 0.0289 -0.9264 -0.1813 0.1915
0 -6 6 0.0283 -0.0157 -5.9996 6.0248 -0.7912 -0.5245 -0.1702
-1 7 -5 0.0402 -0.9821 7.0024 -5.0289 0.9673 0.3951 0.2087

_olex2_date_sample_data_collection 2015-10-19
_olex2_submission_special_instructions 'No special instructions were received'
