# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_NV1433
_database_code_depnum_ccdc_archive 'CCDC 1439720'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_CHEMW03_NV1433              
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: SQUEEZE used to treat a disordered dichloromethane solvent 
molecule, but the actual contents of the crystal, rather than just the 
model contents, have been used in the reported formulae and in the 
calculation of the molecular weight, density, F(000), and linear 
absorption coefficient.  See_refine_sepcial_details.
;
_vrf_PLAT051_NV1433              
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      73.06 %     
RESPONSE: SQUEEZE used to treat a disordered dichloromethane solvent 
molecule, but the actual contents of the crystal, rather than just the 
model contents, have been used in the reported formulae and in the 
calculation of the molecular weight, density, F(000), and linear 
absorption coefficient.  See_refine_sepcial_details.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(E)-3-Benzyl-5-benzylideneoxazolidin-2-one '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N O2, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C17.50 H16 Cl N O2'
_chemical_formula_weight         307.78

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.98282(12)
_cell_length_b                   11.5033(3)
_cell_length_c                   22.3942(4)
_cell_angle_alpha                83.2783(17)
_cell_angle_beta                 89.5639(15)
_cell_angle_gamma                85.3431(17)
_cell_volume                     1525.57(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    15527
_cell_measurement_theta_min      1.9480
_cell_measurement_theta_max      74.1420

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    2.257
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.30441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)
;

_exptl_special_details           
;
Data collection and full structure determination
done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch

Solvent used: dichloromethane
Cooling Device: Oxford Instruments Cryojet XL
Crystal mount: on a glass fibre
Frames collected: 3221
Seconds exposure per frame: 1.0-4.0
Degrees rotation per frame: 1.0
Crystal-detector distance (mm): 55.0
Client: Lorenz Fehr
Sample code: FEH-FC-32  (NV1433)
;

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector                 'Atlas CCD camera on \k goniostat'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            28793
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.986
_diffrn_reflns_theta_max         74.285
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6131
_reflns_number_gt                5742
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_cell_refinement       
'CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_data_reduction        
'CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2014 and PLATON (Spek, 2009)'

# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.018 0.272 0.248 120 42 ' '
2 -0.087 0.728 0.752 120 42 ' '
# Missing Reflections Below sin(th)/lambda= 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 3 1 11.655
1 -1 2 9.745
1 2 2 10.762
1 3 3 14.137
0 0 6 12.004
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
; See _refine_special_details for a description.

TITL z         P -1         R = 0.34
CELL    5.9828   11.5033   22.3942     83.28     89.56     85.34
SPGR P-1
# Solvent Accessible Volume =     248.5
# Electrons Found in S.A.V. =      84.6
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.289 0.176 0.224 !      18.87 eA-3
C102 0.653 0.279 0.281 !      12.97 eA-3
C103 0.439 0.375 0.263 !       4.99 eA-3
C104 0.434 0.290 0.231 !       3.80 eA-3
C105 0.239 0.258 0.233 !       3.32 eA-3
C106 0.558 0.233 0.251 !       0.89 eA-3
Q107 0.754 0.153 0.087 !       0.72 eA-3
C108 0.982 0.238 0.256 !       0.65 eA-3
Q109 0.137 0.644 0.106 !       0.64 eA-3
Q110 0.640 0.646 0.252 !       0.64 eA-3
Q111 0.710 0.410 0.072 !       0.63 eA-3
Q112 0.991 0.353 0.420 !       0.63 eA-3
C113 0.438 0.174 0.258 !       0.62 eA-3
C114 0.166 0.195 0.189 !       0.60 eA-3
Q115 0.464 0.342 0.037 !       0.59 eA-3
Q116 0.978 0.802 0.373 !       0.57 eA-3
Q117 0.687 0.538 0.367 !       0.57 eA-3
C118 0.712 0.375 0.262 !       0.57 eA-3
Q119 0.372 0.623 0.404 !       0.56 eA-3
Q120 0.827 0.716 0.103 !       0.56 eA-3
Q121 0.721 0.660 0.205 !       0.56 eA-3
Q122 0.429 0.091 0.251 !       0.55 eA-3
Q123 0.573 0.890 0.395 !       0.52 eA-3
Q124 0.779 0.236 0.435 !       0.52 eA-3
Q125 0.548 0.642 0.306 !       0.50 eA-3
;
_refine_special_details          
; The asymmetric unit contains two molecules of the lactone plus one 
highly disordered molecule of CH2Cl2.  The conformations of the two 
lactone molecules differ only in the orientation of the benzyl ring.  
The disordered solvent molecule could not be modelled adequately, so the 
SQUEEZE routine of the program PLATON was employed.  When the solvent 
molecule is omitted from the model, each unit cell contains two cavities of 
125 Å³. The electron count in each void was calculated to be 
approximately 42 e.  One CH2Cl2 molecule has 42 e, so it has been assumed 
that one CH2Cl2 molecule lies in each void.  This approximation has been 
used in the subsequent calculation of the empirical formula, formula 
weight, density, linear absorption coefficient and F(000).  Based on 
the assumption, the ratio of lactone to CH2Cl2 molecules in the structure 
is 2:1.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.7012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6131
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.040

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 1.21537(15) 0.90683(9) 0.17704(4) 0.0294(2) Uani 1 1 d . . . . .
O2 O 1.27424(16) 0.95513(9) 0.07765(5) 0.0335(2) Uani 1 1 d . . . . .
N1 N 0.93520(19) 1.00054(10) 0.12269(5) 0.0263(2) Uani 1 1 d . . . . .
C1 C 1.1486(2) 0.95577(12) 0.12003(6) 0.0256(3) Uani 1 1 d . . . . .
C2 C 1.0370(2) 0.91875(12) 0.21718(6) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.8422(2) 0.98402(12) 0.18268(6) 0.0251(3) Uani 1 1 d . . . . .
H31 H 0.7106 0.9369 0.1841 0.030 Uiso 1 1 calc R U . . .
H32 H 0.7989 1.0601 0.1979 0.030 Uiso 1 1 calc R U . . .
C4 C 1.0638(2) 0.87439(12) 0.27439(6) 0.0275(3) Uani 1 1 d . . . . .
H4 H 1.2073 0.8364 0.2851 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8988(2) 0.87694(12) 0.32299(6) 0.0261(3) Uani 1 1 d . . . . .
C6 C 0.9603(3) 0.81733(12) 0.37947(6) 0.0310(3) Uani 1 1 d . . . . .
H6 H 1.1063 0.7786 0.3851 0.037 Uiso 1 1 calc R U . . .
C7 C 0.8117(3) 0.81411(13) 0.42715(7) 0.0380(3) Uani 1 1 d . . . . .
H7 H 0.8562 0.7728 0.4650 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5987(3) 0.87051(14) 0.42018(7) 0.0375(3) Uani 1 1 d . . . . .
H8 H 0.4967 0.8679 0.4530 0.045 Uiso 1 1 calc R U . . .
C9 C 0.5356(3) 0.93089(14) 0.36480(7) 0.0344(3) Uani 1 1 d . . . . .
H9 H 0.3899 0.9702 0.3598 0.041 Uiso 1 1 calc R U . . .
C10 C 0.6828(2) 0.93425(13) 0.31696(6) 0.0308(3) Uani 1 1 d . . . . .
H10 H 0.6370 0.9760 0.2794 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8030(2) 1.05284(12) 0.07081(6) 0.0274(3) Uani 1 1 d . . . . .
H111 H 0.6659 1.0107 0.0688 0.033 Uiso 1 1 calc R U . . .
H112 H 0.8908 1.0432 0.0338 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7365(2) 1.18193(12) 0.07303(5) 0.0240(3) Uani 1 1 d . . . . .
C13 C 0.5237(2) 1.22808(13) 0.05443(6) 0.0306(3) Uani 1 1 d . . . . .
H13 H 0.4184 1.1777 0.0424 0.037 Uiso 1 1 calc R U . . .
C14 C 0.4635(3) 1.34757(14) 0.05321(7) 0.0375(3) Uani 1 1 d . . . . .
H14 H 0.3176 1.3785 0.0402 0.045 Uiso 1 1 calc R U . . .
C15 C 0.6145(3) 1.42141(13) 0.07073(7) 0.0365(3) Uani 1 1 d . . . . .
H15 H 0.5736 1.5032 0.0694 0.044 Uiso 1 1 calc R U . . .
C16 C 0.8260(3) 1.37570(14) 0.09022(7) 0.0389(3) Uani 1 1 d . . . . .
H16 H 0.9298 1.4261 0.1029 0.047 Uiso 1 1 calc R U . . .
C17 C 0.8868(2) 1.25660(13) 0.09135(7) 0.0331(3) Uani 1 1 d . . . . .
H17 H 1.0324 1.2258 0.1047 0.040 Uiso 1 1 calc R U . . .
O21 O 0.54238(15) 0.36121(9) 0.67870(4) 0.0300(2) Uani 1 1 d . . . . .
O22 O 0.62366(16) 0.40942(9) 0.58053(5) 0.0330(2) Uani 1 1 d . . . . .
N2 N 0.27286(18) 0.45230(10) 0.61969(5) 0.0251(2) Uani 1 1 d . . . . .
C21 C 0.4874(2) 0.40944(11) 0.62050(6) 0.0247(3) Uani 1 1 d . . . . .
C22 C 0.3553(2) 0.37242(12) 0.71572(6) 0.0243(3) Uani 1 1 d . . . . .
C23 C 0.1669(2) 0.43593(11) 0.67806(5) 0.0232(3) Uani 1 1 d . . . . .
H231 H 0.0372 0.3878 0.6774 0.028 Uiso 1 1 calc R U . . .
H232 H 0.1173 0.5120 0.6924 0.028 Uiso 1 1 calc R U . . .
C24 C 0.3720(2) 0.32814(12) 0.77328(6) 0.0275(3) Uani 1 1 d . . . . .
H24 H 0.5132 0.2890 0.7854 0.033 Uiso 1 1 calc R U . . .
C25 C 0.2014(2) 0.33189(12) 0.82032(6) 0.0252(3) Uani 1 1 d . . . . .
C26 C 0.2567(2) 0.27499(13) 0.87783(6) 0.0296(3) Uani 1 1 d . . . . .
H26 H 0.4019 0.2361 0.8849 0.036 Uiso 1 1 calc R U . . .
C27 C 0.1034(3) 0.27452(14) 0.92454(6) 0.0339(3) Uani 1 1 d . . . . .
H27 H 0.1443 0.2348 0.9630 0.041 Uiso 1 1 calc R U . . .
C28 C -0.1089(3) 0.33143(13) 0.91574(6) 0.0327(3) Uani 1 1 d . . . . .
H28 H -0.2134 0.3315 0.9479 0.039 Uiso 1 1 calc R U . . .
C29 C -0.1663(2) 0.38838(13) 0.85916(6) 0.0305(3) Uani 1 1 d . . . . .
H29 H -0.3113 0.4278 0.8527 0.037 Uiso 1 1 calc R U . . .
C30 C -0.0151(2) 0.38852(12) 0.81208(6) 0.0286(3) Uani 1 1 d . . . . .
H30 H -0.0582 0.4275 0.7736 0.034 Uiso 1 1 calc R U . . .
C31 C 0.1551(2) 0.50743(12) 0.56546(6) 0.0260(3) Uani 1 1 d . . . . .
H311 H 0.0179 0.4671 0.5601 0.031 Uiso 1 1 calc R U . . .
H312 H 0.2524 0.4990 0.5300 0.031 Uiso 1 1 calc R U . . .
C32 C 0.0919(2) 0.63600(12) 0.56940(5) 0.0249(3) Uani 1 1 d . . . . .
C33 C -0.1159(2) 0.67317(13) 0.59145(7) 0.0328(3) Uani 1 1 d . . . . .
H33 H -0.2222 0.6175 0.6024 0.039 Uiso 1 1 calc R U . . .
C34 C -0.1702(3) 0.79072(14) 0.59764(8) 0.0406(4) Uani 1 1 d . . . . .
H34 H -0.3123 0.8150 0.6132 0.049 Uiso 1 1 calc R U . . .
C35 C -0.0174(3) 0.87254(14) 0.58114(7) 0.0402(4) Uani 1 1 d . . . . .
H35 H -0.0545 0.9532 0.5850 0.048 Uiso 1 1 calc R U . . .
C36 C 0.1897(3) 0.83635(14) 0.55898(8) 0.0407(4) Uani 1 1 d . . . . .
H36 H 0.2953 0.8924 0.5478 0.049 Uiso 1 1 calc R U . . .
C37 C 0.2446(2) 0.71932(13) 0.55289(7) 0.0336(3) Uani 1 1 d . . . . .
H37 H 0.3870 0.6955 0.5374 0.040 Uiso 1 1 calc R U . . .


_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 1.3819(16) . ?
O1 C2 1.3987(15) . ?
O2 C1 1.2065(16) . ?
N1 C1 1.3411(17) . ?
N1 C3 1.4480(16) . ?
N1 C11 1.4527(16) . ?
C2 C4 1.3282(19) . ?
C2 C3 1.5015(18) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 C5 1.4650(19) . ?
C4 H4 0.9500 . ?
C5 C10 1.402(2) . ?
C5 C6 1.4030(18) . ?
C6 C7 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.5123(18) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C13 1.3865(19) . ?
C12 C17 1.3888(19) . ?
C13 C14 1.390(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O21 C21 1.3864(16) . ?
O21 C22 1.3943(15) . ?
O22 C21 1.2060(16) . ?
N2 C21 1.3366(17) . ?
N2 C23 1.4476(15) . ?
N2 C31 1.4607(16) . ?
C22 C24 1.3309(19) . ?
C22 C23 1.5006(17) . ?
C23 H231 0.9900 . ?
C23 H232 0.9900 . ?
C24 C25 1.4632(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.4039(18) . ?
C25 C30 1.4048(19) . ?
C26 C27 1.386(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.385(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.3840(19) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.5092(18) . ?
C31 H311 0.9900 . ?
C31 H312 0.9900 . ?
C32 C33 1.3874(19) . ?
C32 C37 1.3943(19) . ?
C33 C34 1.388(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.382(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.382(2) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 109.68(10) . . ?
C1 N1 C3 112.90(11) . . ?
C1 N1 C11 124.38(11) . . ?
C3 N1 C11 122.58(11) . . ?
O2 C1 N1 129.79(13) . . ?
O2 C1 O1 121.71(12) . . ?
N1 C1 O1 108.49(11) . . ?
C4 C2 O1 119.46(12) . . ?
C4 C2 C3 132.81(12) . . ?
O1 C2 C3 107.72(10) . . ?
N1 C3 C2 101.17(10) . . ?
N1 C3 H31 111.5 . . ?
C2 C3 H31 111.5 . . ?
N1 C3 H32 111.5 . . ?
C2 C3 H32 111.5 . . ?
H31 C3 H32 109.4 . . ?
C2 C4 C5 127.83(13) . . ?
C2 C4 H4 116.1 . . ?
C5 C4 H4 116.1 . . ?
C10 C5 C6 117.57(13) . . ?
C10 C5 C4 124.58(12) . . ?
C6 C5 C4 117.84(13) . . ?
C7 C6 C5 121.03(14) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.52(14) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.28(14) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.53(15) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 121.06(13) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
N1 C11 C12 112.49(11) . . ?
N1 C11 H111 109.1 . . ?
C12 C11 H111 109.1 . . ?
N1 C11 H112 109.1 . . ?
C12 C11 H112 109.1 . . ?
H111 C11 H112 107.8 . . ?
C13 C12 C17 118.99(13) . . ?
C13 C12 C11 119.58(12) . . ?
C17 C12 C11 121.39(12) . . ?
C12 C13 C14 120.39(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.33(14) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.61(14) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.22(14) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.45(14) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C21 O21 C22 109.70(10) . . ?
C21 N2 C23 112.95(10) . . ?
C21 N2 C31 123.78(11) . . ?
C23 N2 C31 123.25(10) . . ?
O22 C21 N2 130.20(13) . . ?
O22 C21 O21 121.40(12) . . ?
N2 C21 O21 108.40(11) . . ?
C24 C22 O21 118.94(12) . . ?
C24 C22 C23 133.34(12) . . ?
O21 C22 C23 107.71(10) . . ?
N2 C23 C22 101.22(10) . . ?
N2 C23 H231 111.5 . . ?
C22 C23 H231 111.5 . . ?
N2 C23 H232 111.5 . . ?
C22 C23 H232 111.5 . . ?
H231 C23 H232 109.3 . . ?
C22 C24 C25 128.44(12) . . ?
C22 C24 H24 115.8 . . ?
C25 C24 H24 115.8 . . ?
C26 C25 C30 117.38(12) . . ?
C26 C25 C24 118.00(12) . . ?
C30 C25 C24 124.62(12) . . ?
C27 C26 C25 121.23(13) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C28 C27 C26 120.64(13) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 118.90(13) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C30 C29 C28 120.91(14) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C25 120.94(13) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
N2 C31 C32 111.07(11) . . ?
N2 C31 H311 109.4 . . ?
C32 C31 H311 109.4 . . ?
N2 C31 H312 109.4 . . ?
C32 C31 H312 109.4 . . ?
H311 C31 H312 108.0 . . ?
C33 C32 C37 118.72(13) . . ?
C33 C32 C31 120.77(12) . . ?
C37 C32 C31 120.48(12) . . ?
C32 C33 C34 120.79(14) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C35 C34 C33 119.98(14) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C36 C35 C34 119.63(15) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C37 C36 C35 120.54(14) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C32 120.35(14) . . ?
C36 C37 H37 119.8 . . ?
C32 C37 H37 119.8 . . ?

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
C3 N1 C1 O2 -179.53(14) . . . . ?
C11 N1 C1 O2 4.7(2) . . . . ?
C3 N1 C1 O1 -0.22(15) . . . . ?
C11 N1 C1 O1 -176.02(12) . . . . ?
C2 O1 C1 O2 -179.42(12) . . . . ?
C2 O1 C1 N1 1.21(15) . . . . ?
C1 O1 C2 C4 178.12(12) . . . . ?
C1 O1 C2 C3 -1.67(14) . . . . ?
C1 N1 C3 C2 -0.75(14) . . . . ?
C11 N1 C3 C2 175.13(12) . . . . ?
C4 C2 C3 N1 -178.33(15) . . . . ?
O1 C2 C3 N1 1.43(13) . . . . ?
O1 C2 C4 C5 -179.61(12) . . . . ?
C3 C2 C4 C5 0.1(3) . . . . ?
C2 C4 C5 C10 -3.7(2) . . . . ?
C2 C4 C5 C6 175.90(14) . . . . ?
C10 C5 C6 C7 0.8(2) . . . . ?
C4 C5 C6 C7 -178.77(13) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C8 C9 C10 C5 0.1(2) . . . . ?
C6 C5 C10 C9 -0.7(2) . . . . ?
C4 C5 C10 C9 178.91(13) . . . . ?
C1 N1 C11 C12 -116.08(14) . . . . ?
C3 N1 C11 C12 68.52(16) . . . . ?
N1 C11 C12 C13 -140.33(12) . . . . ?
N1 C11 C12 C17 41.98(17) . . . . ?
C17 C12 C13 C14 1.1(2) . . . . ?
C11 C12 C13 C14 -176.67(13) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C15 C16 C17 0.9(2) . . . . ?
C15 C16 C17 C12 -0.1(2) . . . . ?
C13 C12 C17 C16 -0.9(2) . . . . ?
C11 C12 C17 C16 176.79(13) . . . . ?
C23 N2 C21 O22 -179.09(14) . . . . ?
C31 N2 C21 O22 2.3(2) . . . . ?
C23 N2 C21 O21 0.10(15) . . . . ?
C31 N2 C21 O21 -178.50(11) . . . . ?
C22 O21 C21 O22 -179.81(12) . . . . ?
C22 O21 C21 N2 0.91(14) . . . . ?
C21 O21 C22 C24 178.04(12) . . . . ?
C21 O21 C22 C23 -1.51(14) . . . . ?
C21 N2 C23 C22 -0.96(14) . . . . ?
C31 N2 C23 C22 177.65(11) . . . . ?
C24 C22 C23 N2 -178.00(15) . . . . ?
O21 C22 C23 N2 1.45(13) . . . . ?
O21 C22 C24 C25 178.42(12) . . . . ?
C23 C22 C24 C25 -2.2(3) . . . . ?
C22 C24 C25 C26 177.89(14) . . . . ?
C22 C24 C25 C30 -2.1(2) . . . . ?
C30 C25 C26 C27 0.2(2) . . . . ?
C24 C25 C26 C27 -179.78(13) . . . . ?
C25 C26 C27 C28 -0.6(2) . . . . ?
C26 C27 C28 C29 0.4(2) . . . . ?
C27 C28 C29 C30 0.1(2) . . . . ?
C28 C29 C30 C25 -0.5(2) . . . . ?
C26 C25 C30 C29 0.4(2) . . . . ?
C24 C25 C30 C29 -179.66(13) . . . . ?
C21 N2 C31 C32 -114.21(14) . . . . ?
C23 N2 C31 C32 67.33(16) . . . . ?
N2 C31 C32 C33 -92.50(15) . . . . ?
N2 C31 C32 C37 85.23(15) . . . . ?
C37 C32 C33 C34 -0.7(2) . . . . ?
C31 C32 C33 C34 177.05(14) . . . . ?
C32 C33 C34 C35 0.7(2) . . . . ?
C33 C34 C35 C36 -0.5(3) . . . . ?
C34 C35 C36 C37 0.4(3) . . . . ?
C35 C36 C37 C32 -0.4(2) . . . . ?
C33 C32 C37 C36 0.6(2) . . . . ?
C31 C32 C37 C36 -177.21(13) . . . . ?




#   End of CIF   ============================================================
####################################################################### 
# 
# 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_NV1430
_database_code_depnum_ccdc_archive 'CCDC 1439788'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(E)-5-benzylideneoxazolidin-2-one '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4980(2)
_cell_length_b                   5.69208(16)
_cell_length_c                   19.4188(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.668(3)
_cell_angle_gamma                90
_cell_volume                     828.73(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    4412
_cell_measurement_theta_min      3.7160
_cell_measurement_theta_max      27.9770

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.0989
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.74838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)
;

_exptl_special_details           
;
Data collection and full structure determination
done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch

Solvent used: dichloromethane
Cooling Device: Oxford Instruments Cryojet XL
Crystal mount: on a glass fibre
Frames collected: 417
Seconds exposure per frame: 25.0
Degrees rotation per frame: 1.0
Crystal-detector distance (mm): 55.0
Client: Lorenz Fehr
Sample code: FEH-FB-43  (NV1430)
;

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector                 'Atlas CCD camera on \k goniostat'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            8396
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.901
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1878
_reflns_number_gt                1587
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_cell_refinement       
'CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_data_reduction        
'CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2014 and PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²+0.3124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   'geom & difmap'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0090(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1878
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.038

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 0.61968(11) 0.11941(14) 0.09130(4) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.61909(12) -0.00793(16) 0.20088(4) 0.0307(2) Uani 1 1 d . . . . .
N1 N 0.70924(14) 0.36743(18) 0.17186(5) 0.0243(2) Uani 1 1 d . . . . .
H1 H 0.7543(19) 0.412(3) 0.2125(8) 0.034(4) Uiso 1 1 d . . . . .
C1 C 0.64883(15) 0.1513(2) 0.16079(6) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.68031(14) 0.31727(19) 0.05574(6) 0.0192(2) Uani 1 1 d . . . . .
C3 C 0.74198(15) 0.4943(2) 0.10848(5) 0.0214(2) Uani 1 1 d . . . . .
H31 H 0.8700 0.5322 0.1034 0.026 Uiso 1 1 calc R U . . .
H32 H 0.6711 0.6408 0.1058 0.026 Uiso 1 1 calc R U . . .
C4 C 0.67482(14) 0.31544(19) -0.01268(5) 0.0201(2) Uani 1 1 d . . . . .
H4 H 0.6203 0.1819 -0.0334 0.024 Uiso 1 1 calc R U . . .
C5 C 0.74231(14) 0.4937(2) -0.06005(5) 0.0200(2) Uani 1 1 d . . . . .
C6 C 0.73256(15) 0.4464(2) -0.13105(6) 0.0244(3) Uani 1 1 d . . . . .
H6 H 0.6778 0.3053 -0.1466 0.029 Uiso 1 1 calc R U . . .
C7 C 0.80131(16) 0.6019(2) -0.17865(6) 0.0295(3) Uani 1 1 d . . . . .
H7 H 0.7944 0.5656 -0.2264 0.035 Uiso 1 1 calc R U . . .
C8 C 0.88007(16) 0.8099(2) -0.15736(6) 0.0284(3) Uani 1 1 d . . . . .
H8 H 0.9277 0.9161 -0.1901 0.034 Uiso 1 1 calc R U . . .
C9 C 0.88853(15) 0.8612(2) -0.08775(6) 0.0259(3) Uani 1 1 d . . . . .
H9 H 0.9417 1.0040 -0.0727 0.031 Uiso 1 1 calc R U . . .
C10 C 0.82024(15) 0.7062(2) -0.03973(6) 0.0234(3) Uani 1 1 d . . . . .
H10 H 0.8265 0.7451 0.0078 0.028 Uiso 1 1 calc R U . . .



_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 1.3764(13) . ?
O1 C2 1.3998(13) . ?
O2 C1 1.2169(14) . ?
N1 C1 1.3278(16) . ?
N1 C3 1.4504(14) . ?
N1 H1 0.892(15) . ?
C2 C4 1.3287(15) . ?
C2 C3 1.5058(15) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 C5 1.4638(15) . ?
C4 H4 0.9500 . ?
C5 C10 1.3985(16) . ?
C5 C6 1.4057(15) . ?
C6 C7 1.3838(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3843(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3836(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3859(16) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 109.20(8) . . ?
C1 N1 C3 112.64(9) . . ?
C1 N1 H1 122.0(9) . . ?
C3 N1 H1 123.0(9) . . ?
O2 C1 N1 130.63(11) . . ?
O2 C1 O1 120.06(10) . . ?
N1 C1 O1 109.31(10) . . ?
C4 C2 O1 118.72(10) . . ?
C4 C2 C3 133.71(10) . . ?
O1 C2 C3 107.57(9) . . ?
N1 C3 C2 100.96(9) . . ?
N1 C3 H31 111.6 . . ?
C2 C3 H31 111.6 . . ?
N1 C3 H32 111.6 . . ?
C2 C3 H32 111.6 . . ?
H31 C3 H32 109.4 . . ?
C2 C4 C5 128.03(10) . . ?
C2 C4 H4 116.0 . . ?
C5 C4 H4 116.0 . . ?
C10 C5 C6 117.33(10) . . ?
C10 C5 C4 124.65(10) . . ?
C6 C5 C4 118.00(10) . . ?
C7 C6 C5 121.15(11) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.57(11) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.11(11) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.68(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 121.13(11) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 O2 174.37(12) . . . . ?
C3 N1 C1 O1 -5.48(13) . . . . ?
C2 O1 C1 O2 -174.06(10) . . . . ?
C2 O1 C1 N1 5.81(12) . . . . ?
C1 O1 C2 C4 175.73(10) . . . . ?
C1 O1 C2 C3 -3.90(11) . . . . ?
C1 N1 C3 C2 2.86(12) . . . . ?
C4 C2 C3 N1 -178.83(12) . . . . ?
O1 C2 C3 N1 0.72(11) . . . . ?
O1 C2 C4 C5 -175.19(10) . . . . ?
C3 C2 C4 C5 4.3(2) . . . . ?
C2 C4 C5 C10 -2.62(18) . . . . ?
C2 C4 C5 C6 175.71(11) . . . . ?
C10 C5 C6 C7 1.50(17) . . . . ?
C4 C5 C6 C7 -176.96(10) . . . . ?
C5 C6 C7 C8 -0.68(18) . . . . ?
C6 C7 C8 C9 -0.29(18) . . . . ?
C7 C8 C9 C10 0.39(18) . . . . ?
C8 C9 C10 C5 0.49(17) . . . . ?
C6 C5 C10 C9 -1.40(16) . . . . ?
C4 C5 C10 C9 176.94(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.892(15) 1.975(15) 2.8624(13) 173.2(13) 2_655 yes

####################################################################### 
# 
# 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_NV1431
_database_code_depnum_ccdc_archive 'CCDC 1439789'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Methyl (E)-4-[1-(3-benzyl-2-oxooxazolidin-5-ylidene)ethyl]benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.37

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.43088(18)
_cell_length_b                   15.8294(2)
_cell_length_c                   18.0723(3)
_cell_angle_alpha                92.4918(12)
_cell_angle_beta                 101.8823(12)
_cell_angle_gamma                100.5457(12)
_cell_volume                     3408.98(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    31641
_cell_measurement_theta_min      2.4730
_cell_measurement_theta_max      74.2680

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.752
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.00908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)
;

_exptl_special_details           
;
Data collection and full structure determination
done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch

Solvent used: dichloromethane
Cooling Device: Oxford Instruments Cryojet XL
Crystal mount: on a glass fibre
Frames collected: 3151
Seconds exposure per frame: 1.0-7.5
Degrees rotation per frame: 1.0
Crystal-detector distance (mm): 55.0
Client: Lorenz Fehr
Sample code: FEH-FC-3  (NV1431)
;

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector                 'Atlas CCD camera on \k goniostat'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            64083
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.507
_diffrn_reflns_theta_max         74.282
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13734
_reflns_number_gt                12322
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_cell_refinement       
'CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_data_reduction        
'CrysAlisPro, Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2014 and PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.8725P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00065(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         13734
_refine_ls_number_parameters     910
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.033

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 0.70265(6) 0.75802(5) 0.13698(5) 0.03087(17) Uani 1 1 d . . . . .
O2 O 0.79831(7) 0.65090(6) 0.16436(6) 0.0449(2) Uani 1 1 d . . . . .
O3 O 0.12105(7) 0.99381(6) 0.16045(6) 0.0470(2) Uani 1 1 d . . . . .
O4 O 0.05449(6) 0.85518(6) 0.11684(5) 0.03677(19) Uani 1 1 d . . . . .
N1 N 0.62786(8) 0.65067(6) 0.19662(6) 0.0314(2) Uani 1 1 d . . . . .
C1 C 0.71658(9) 0.68099(7) 0.16665(7) 0.0321(2) Uani 1 1 d . . . . .
C2 C 0.59901(8) 0.77558(7) 0.14534(6) 0.0249(2) Uani 1 1 d . . . . .
C3 C 0.53760(9) 0.69715(7) 0.17378(7) 0.0281(2) Uani 1 1 d . . . . .
H31 H 0.5058 0.7126 0.2173 0.034 Uiso 1 1 calc R U . . .
H32 H 0.4770 0.6636 0.1332 0.034 Uiso 1 1 calc R U . . .
C4 C 0.57367(8) 0.85252(7) 0.13278(6) 0.0246(2) Uani 1 1 d . . . . .
C5 C 0.46179(8) 0.86930(6) 0.13801(6) 0.0236(2) Uani 1 1 d . . . . .
C6 C 0.44953(9) 0.95062(7) 0.16438(6) 0.0283(2) Uani 1 1 d . . . . .
H6 H 0.5139 0.9952 0.1804 0.034 Uiso 1 1 calc R U . . .
C7 C 0.34460(9) 0.96719(7) 0.16747(7) 0.0293(2) Uani 1 1 d . . . . .
H7 H 0.3379 1.0224 0.1865 0.035 Uiso 1 1 calc R U . . .
C8 C 0.24910(9) 0.90307(7) 0.14268(6) 0.0265(2) Uani 1 1 d . . . . .
C9 C 0.25987(9) 0.82196(7) 0.11567(6) 0.0277(2) Uani 1 1 d . . . . .
H9 H 0.1951 0.7780 0.0984 0.033 Uiso 1 1 calc R U . . .
C10 C 0.36480(9) 0.80556(7) 0.11397(6) 0.0264(2) Uani 1 1 d . . . . .
H10 H 0.3713 0.7498 0.0961 0.032 Uiso 1 1 calc R U . . .
C11 C 0.60696(11) 0.56325(8) 0.22069(7) 0.0375(3) Uani 1 1 d . . . . .
H111 H 0.5663 0.5626 0.2624 0.045 Uiso 1 1 calc R U . . .
H112 H 0.6796 0.5462 0.2405 0.045 Uiso 1 1 calc R U . . .
C12 C 0.53941(10) 0.49879(7) 0.15673(7) 0.0318(2) Uani 1 1 d . . . . .
C13 C 0.42311(10) 0.48406(7) 0.14110(8) 0.0382(3) Uani 1 1 d . . . . .
H13 H 0.3855 0.5121 0.1726 0.046 Uiso 1 1 calc R U . . .
C14 C 0.36197(13) 0.42812(9) 0.07929(10) 0.0523(4) Uani 1 1 d . . . . .
H14 H 0.2824 0.4184 0.0679 0.063 Uiso 1 1 calc R U . . .
C15 C 0.41755(17) 0.38649(9) 0.03415(9) 0.0595(4) Uani 1 1 d . . . . .
H15 H 0.3758 0.3482 -0.0082 0.071 Uiso 1 1 calc R U . . .
C16 C 0.53252(16) 0.40044(9) 0.05051(10) 0.0571(4) Uani 1 1 d . . . . .
H16 H 0.5701 0.3711 0.0200 0.069 Uiso 1 1 calc R U . . .
C17 C 0.59341(12) 0.45673(8) 0.11091(9) 0.0452(3) Uani 1 1 d . . . . .
H17 H 0.6730 0.4669 0.1214 0.054 Uiso 1 1 calc R U . . .
C18 C 0.65793(9) 0.92551(7) 0.11427(7) 0.0323(2) Uani 1 1 d . . . . .
H181 H 0.6872 0.9672 0.1588 0.048 Uiso 1 1 calc R U . . .
H182 H 0.6215 0.9541 0.0718 0.048 Uiso 1 1 calc R U . . .
H183 H 0.7197 0.9026 0.1002 0.048 Uiso 1 1 calc R U . . .
C19 C 0.13707(9) 0.92392(7) 0.14203(7) 0.0307(2) Uani 1 1 d . . . . .
C20 C -0.05864(10) 0.86872(10) 0.10881(8) 0.0433(3) Uani 1 1 d . . . . .
H201 H -0.0764 0.9035 0.0660 0.065 Uiso 1 1 calc R U . . .
H202 H -0.0659 0.8990 0.1555 0.065 Uiso 1 1 calc R U . . .
H203 H -0.1107 0.8129 0.0995 0.065 Uiso 1 1 calc R U . . .
O21 O 0.24625(6) 0.73820(5) 0.28954(5) 0.03048(17) Uani 1 1 d . . . . .
O22 O 0.32135(7) 0.63600(6) 0.23896(6) 0.0406(2) Uani 1 1 d . . . . .
O23 O -0.32324(8) 0.98540(6) 0.31988(6) 0.0474(2) Uani 1 1 d . . . . .
O24 O -0.38183(7) 0.84475(6) 0.33125(5) 0.03732(19) Uani 1 1 d . . . . .
N2 N 0.13268(8) 0.63881(6) 0.20511(6) 0.0303(2) Uani 1 1 d . . . . .
C21 C 0.23926(9) 0.66582(7) 0.24223(7) 0.0301(2) Uani 1 1 d . . . . .
C22 C 0.13947(8) 0.75783(7) 0.28288(6) 0.0265(2) Uani 1 1 d . . . . .
C23 C 0.05730(9) 0.68840(7) 0.22979(7) 0.0301(2) Uani 1 1 d . . . . .
H231 H 0.0053 0.6533 0.2565 0.036 Uiso 1 1 calc R U . . .
H232 H 0.0136 0.7128 0.1867 0.036 Uiso 1 1 calc R U . . .
C24 C 0.12735(9) 0.83104(7) 0.31627(6) 0.0272(2) Uani 1 1 d . . . . .
C25 C 0.01447(9) 0.85045(7) 0.31453(6) 0.0260(2) Uani 1 1 d . . . . .
C26 C -0.00423(9) 0.93455(7) 0.30792(7) 0.0312(2) Uani 1 1 d . . . . .
H26 H 0.0556 0.9793 0.3029 0.037 Uiso 1 1 calc R U . . .
C27 C -0.10866(9) 0.95375(7) 0.30850(7) 0.0312(2) Uani 1 1 d . . . . .
H27 H -0.1201 1.0111 0.3030 0.037 Uiso 1 1 calc R U . . .
C28 C -0.19672(9) 0.88912(7) 0.31715(6) 0.0273(2) Uani 1 1 d . . . . .
C29 C -0.17898(9) 0.80542(7) 0.32444(6) 0.0285(2) Uani 1 1 d . . . . .
H29 H -0.2385 0.7610 0.3304 0.034 Uiso 1 1 calc R U . . .
C30 C -0.07486(9) 0.78629(7) 0.32308(6) 0.0282(2) Uani 1 1 d . . . . .
H30 H -0.0640 0.7288 0.3280 0.034 Uiso 1 1 calc R U . . .
C31 C 0.09507(10) 0.56608(7) 0.14734(7) 0.0353(3) Uani 1 1 d . . . . .
H311 H 0.0229 0.5322 0.1540 0.042 Uiso 1 1 calc R U . . .
H312 H 0.1507 0.5280 0.1541 0.042 Uiso 1 1 calc R U . . .
C32 C 0.08031(10) 0.59554(7) 0.06822(7) 0.0315(2) Uani 1 1 d . . . . .
C33 C -0.01814(10) 0.62120(8) 0.03403(8) 0.0374(3) Uani 1 1 d . . . . .
H33 H -0.0779 0.6179 0.0598 0.045 Uiso 1 1 calc R U . . .
C34 C -0.02960(11) 0.65157(9) -0.03748(8) 0.0440(3) Uani 1 1 d . . . . .
H34 H -0.0969 0.6694 -0.0602 0.053 Uiso 1 1 calc R U . . .
C35 C 0.05654(13) 0.65603(9) -0.07583(8) 0.0459(3) Uani 1 1 d . . . . .
H35 H 0.0483 0.6764 -0.1250 0.055 Uiso 1 1 calc R U . . .
C36 C 0.15456(12) 0.63071(9) -0.04237(8) 0.0449(3) Uani 1 1 d . . . . .
H36 H 0.2141 0.6340 -0.0684 0.054 Uiso 1 1 calc R U . . .
C37 C 0.16632(10) 0.60044(8) 0.02919(8) 0.0375(3) Uani 1 1 d . . . . .
H37 H 0.2339 0.5829 0.0517 0.045 Uiso 1 1 calc R U . . .
C38 C 0.22838(9) 0.89773(8) 0.35524(7) 0.0374(3) Uani 1 1 d . . . . .
H381 H 0.2924 0.8696 0.3713 0.056 Uiso 1 1 calc R U . . .
H382 H 0.2120 0.9261 0.3998 0.056 Uiso 1 1 calc R U . . .
H383 H 0.2464 0.9408 0.3200 0.056 Uiso 1 1 calc R U . . .
C39 C -0.30552(9) 0.91326(8) 0.32216(6) 0.0313(2) Uani 1 1 d . . . . .
C40 C -0.48818(10) 0.86201(10) 0.34205(8) 0.0428(3) Uani 1 1 d . . . . .
H401 H -0.5104 0.9062 0.3091 0.064 Uiso 1 1 calc R U . . .
H402 H -0.4808 0.8825 0.3951 0.064 Uiso 1 1 calc R U . . .
H403 H -0.5453 0.8090 0.3292 0.064 Uiso 1 1 calc R U . . .
O31 O 0.75599(7) 0.72046(6) 0.80954(5) 0.03654(19) Uani 1 1 d . . . . .
O32 O 0.83122(9) 0.62254(7) 0.75341(6) 0.0551(3) Uani 1 1 d . . . . .
O33 O 0.12038(8) 0.85816(8) 0.80179(6) 0.0587(3) Uani 1 1 d . . . . .
O34 O 0.17508(8) 0.87984(8) 0.92714(6) 0.0514(3) Uani 1 1 d . . . . .
N3 N 0.64450(10) 0.63134(7) 0.71582(6) 0.0400(2) Uani 1 1 d . . . . .
C41 C 0.74964(11) 0.65324(8) 0.75684(7) 0.0397(3) Uani 1 1 d . . . . .
C42 C 0.64934(9) 0.74002(7) 0.80398(7) 0.0302(2) Uani 1 1 d . . . . .
C43 C 0.57280(10) 0.68745(7) 0.73564(7) 0.0340(2) Uani 1 1 d . . . . .
H431 H 0.5045 0.6542 0.7485 0.041 Uiso 1 1 calc R U . . .
H432 H 0.5510 0.7240 0.6942 0.041 Uiso 1 1 calc R U . . .
C44 C 0.63174(9) 0.79328(7) 0.85734(6) 0.0297(2) Uani 1 1 d . . . . .
C45 C 0.51873(9) 0.81125(7) 0.85650(6) 0.0269(2) Uani 1 1 d . . . . .
C46 C 0.44233(9) 0.81774(7) 0.78947(6) 0.0300(2) Uani 1 1 d . . . . .
H46 H 0.4628 0.8107 0.7421 0.036 Uiso 1 1 calc R U . . .
C47 C 0.33718(9) 0.83426(7) 0.79105(6) 0.0308(2) Uani 1 1 d . . . . .
H47 H 0.2865 0.8386 0.7449 0.037 Uiso 1 1 calc R U . . .
C48 C 0.30517(9) 0.84455(7) 0.85963(6) 0.0282(2) Uani 1 1 d . . . . .
C49 C 0.38105(10) 0.84034(8) 0.92678(7) 0.0352(2) Uani 1 1 d . . . . .
H49 H 0.3607 0.8486 0.9741 0.042 Uiso 1 1 calc R U . . .
C50 C 0.48631(10) 0.82415(8) 0.92505(7) 0.0344(2) Uani 1 1 d . . . . .
H50 H 0.5376 0.8218 0.9715 0.041 Uiso 1 1 calc R U . . .
C51 C 0.60832(14) 0.56472(8) 0.65274(8) 0.0465(3) Uani 1 1 d . . . . .
H511 H 0.5343 0.5306 0.6555 0.056 Uiso 1 1 calc R U . . .
H512 H 0.6622 0.5252 0.6580 0.056 Uiso 1 1 calc R U . . .
C52 C 0.59951(11) 0.60026(7) 0.57602(7) 0.0365(3) Uani 1 1 d . . . . .
C53 C 0.50032(11) 0.62053(10) 0.53807(9) 0.0480(3) Uani 1 1 d . . . . .
H53 H 0.4367 0.6119 0.5603 0.058 Uiso 1 1 calc R U . . .
C54 C 0.49312(13) 0.65352(11) 0.46740(9) 0.0553(4) Uani 1 1 d . . . . .
H54 H 0.4249 0.6679 0.4419 0.066 Uiso 1 1 calc R U . . .
C55 C 0.58460(14) 0.66532(10) 0.43435(9) 0.0527(4) Uani 1 1 d . . . . .
H55 H 0.5793 0.6866 0.3857 0.063 Uiso 1 1 calc R U . . .
C56 C 0.68358(14) 0.64601(10) 0.47234(10) 0.0569(4) Uani 1 1 d . . . . .
H56 H 0.7472 0.6550 0.4501 0.068 Uiso 1 1 calc R U . . .
C57 C 0.69136(12) 0.61362(9) 0.54258(9) 0.0476(3) Uani 1 1 d . . . . .
H57 H 0.7603 0.6004 0.5682 0.057 Uiso 1 1 calc R U . . .
C58 C 0.72645(10) 0.83228(9) 0.92311(7) 0.0386(3) Uani 1 1 d . . . . .
H581 H 0.7226 0.7979 0.9666 0.058 Uiso 1 1 calc R U . . .
H582 H 0.7201 0.8914 0.9369 0.058 Uiso 1 1 calc R U . . .
H583 H 0.7983 0.8329 0.9085 0.058 Uiso 1 1 calc R U . . .
C59 C 0.19106(10) 0.86093(7) 0.85846(7) 0.0322(2) Uani 1 1 d . . . . .
C60 C 0.06376(14) 0.89279(13) 0.92987(11) 0.0668(5) Uani 1 1 d . . . . .
H601 H 0.0652 0.9214 0.9793 0.100 Uiso 1 1 calc R U . . .
H602 H 0.0121 0.8369 0.9224 0.100 Uiso 1 1 calc R U . . .
H603 H 0.0386 0.9289 0.8897 0.100 Uiso 1 1 calc R U . . .
O41 O 1.20229(7) 0.75684(6) 0.61180(5) 0.03793(19) Uani 1 1 d . . . . .
O42 O 1.30583(8) 0.65449(7) 0.64035(7) 0.0557(3) Uani 1 1 d . . . . .
O43 O 0.58313(8) 0.88266(8) 0.66669(6) 0.0540(3) Uani 1 1 d . . . . .
O44 O 0.54526(8) 0.89376(8) 0.54277(6) 0.0545(3) Uani 1 1 d . . . . .
N4 N 1.13652(9) 0.64977(7) 0.67489(7) 0.0422(3) Uani 1 1 d . . . . .
C61 C 1.22212(10) 0.68187(9) 0.64337(8) 0.0412(3) Uani 1 1 d . . . . .
C62 C 1.09649(9) 0.76998(7) 0.61959(7) 0.0308(2) Uani 1 1 d . . . . .
C63 C 1.05091(10) 0.70165(7) 0.66659(8) 0.0357(3) Uani 1 1 d . . . . .
H631 H 1.0447 0.7267 0.7163 0.043 Uiso 1 1 calc R U . . .
H632 H 0.9769 0.6680 0.6397 0.043 Uiso 1 1 calc R U . . .
C64 C 1.05197(9) 0.83128(7) 0.58384(6) 0.0301(2) Uani 1 1 d . . . . .
C65 C 0.93883(9) 0.84422(7) 0.59003(6) 0.0274(2) Uani 1 1 d . . . . .
C66 C 0.86538(10) 0.86360(8) 0.52671(7) 0.0364(3) Uani 1 1 d . . . . .
H66 H 0.8888 0.8690 0.4800 0.044 Uiso 1 1 calc R U . . .
C67 C 0.75864(10) 0.87518(8) 0.53053(7) 0.0366(3) Uani 1 1 d . . . . .
H67 H 0.7091 0.8870 0.4864 0.044 Uiso 1 1 calc R U . . .
C68 C 0.72408(9) 0.86945(7) 0.59883(6) 0.0280(2) Uani 1 1 d . . . . .
C69 C 0.79777(9) 0.85272(7) 0.66294(6) 0.0302(2) Uani 1 1 d . . . . .
H69 H 0.7754 0.8501 0.7101 0.036 Uiso 1 1 calc R U . . .
C70 C 0.90357(9) 0.83979(7) 0.65869(6) 0.0294(2) Uani 1 1 d . . . . .
H70 H 0.9528 0.8278 0.7029 0.035 Uiso 1 1 calc R U . . .
C71 C 1.12513(12) 0.56729(9) 0.70793(9) 0.0469(3) Uani 1 1 d . . . . .
H711 H 1.0988 0.5732 0.7557 0.056 Uiso 1 1 calc R U . . .
H712 H 1.1993 0.5505 0.7204 0.056 Uiso 1 1 calc R U . . .
C72 C 1.04363(11) 0.49775(8) 0.65447(7) 0.0373(3) Uani 1 1 d . . . . .
C73 C 0.93066(12) 0.48287(8) 0.65547(8) 0.0416(3) Uani 1 1 d . . . . .
H73 H 0.9048 0.5154 0.6912 0.050 Uiso 1 1 calc R U . . .
C74 C 0.85515(14) 0.42084(10) 0.60473(9) 0.0527(4) Uani 1 1 d . . . . .
H74 H 0.7776 0.4113 0.6053 0.063 Uiso 1 1 calc R U . . .
C75 C 0.89255(17) 0.37281(10) 0.55325(9) 0.0621(4) Uani 1 1 d . . . . .
H75 H 0.8410 0.3295 0.5190 0.075 Uiso 1 1 calc R U . . .
C76 C 1.00490(18) 0.38786(10) 0.55163(10) 0.0630(5) Uani 1 1 d . . . . .
H76 H 1.0305 0.3550 0.5160 0.076 Uiso 1 1 calc R U . . .
C77 C 1.08034(14) 0.45030(9) 0.60148(9) 0.0500(3) Uani 1 1 d . . . . .
H77 H 1.1574 0.4609 0.5996 0.060 Uiso 1 1 calc R U . . .
C78 C 1.11323(11) 0.88676(9) 0.53387(8) 0.0422(3) Uani 1 1 d . . . . .
H781 H 1.0970 0.9449 0.5372 0.063 Uiso 1 1 calc R U . . .
H782 H 1.0884 0.8616 0.4812 0.063 Uiso 1 1 calc R U . . .
H783 H 1.1941 0.8898 0.5508 0.063 Uiso 1 1 calc R U . . .
C79 C 0.61187(9) 0.88210(7) 0.60736(7) 0.0316(2) Uani 1 1 d . . . . .
C80 C 0.43164(13) 0.89907(15) 0.54792(10) 0.0685(5) Uani 1 1 d . . . . .
H801 H 0.4336 0.9360 0.5933 0.103 Uiso 1 1 calc R U . . .
H802 H 0.3893 0.8412 0.5512 0.103 Uiso 1 1 calc R U . . .
H803 H 0.3953 0.9235 0.5027 0.103 Uiso 1 1 calc R U . . .


_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 1.3784(14) . ?
O1 C2 1.4027(12) . ?
O2 C1 1.2057(14) . ?
O3 C19 1.2043(15) . ?
O4 C19 1.3418(14) . ?
O4 C20 1.4400(13) . ?
N1 C1 1.3471(16) . ?
N1 C3 1.4520(13) . ?
N1 C11 1.4626(15) . ?
C2 C4 1.3302(15) . ?
C2 C3 1.5027(14) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 C5 1.4836(14) . ?
C4 C18 1.5096(14) . ?
C5 C6 1.3985(14) . ?
C5 C10 1.4004(14) . ?
C6 C7 1.3883(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3930(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.3928(15) . ?
C8 C19 1.4868(14) . ?
C9 C10 1.3818(14) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.5055(17) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C17 1.3872(18) . ?
C12 C13 1.3881(17) . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H181 0.9800 . ?
C18 H182 0.9800 . ?
C18 H183 0.9800 . ?
C20 H201 0.9800 . ?
C20 H202 0.9800 . ?
C20 H203 0.9800 . ?
O21 C21 1.3780(14) . ?
O21 C22 1.4005(12) . ?
O22 C21 1.2109(14) . ?
O23 C39 1.2028(15) . ?
O24 C39 1.3438(15) . ?
O24 C40 1.4472(13) . ?
N2 C21 1.3378(15) . ?
N2 C23 1.4505(13) . ?
N2 C31 1.4600(15) . ?
C22 C24 1.3305(15) . ?
C22 C23 1.5051(15) . ?
C23 H231 0.9900 . ?
C23 H232 0.9900 . ?
C24 C25 1.4849(14) . ?
C24 C38 1.5078(15) . ?
C25 C26 1.3987(15) . ?
C25 C30 1.4000(15) . ?
C26 C27 1.3883(15) . ?
C26 H26 0.9500 . ?
C27 C28 1.3942(16) . ?
C27 H27 0.9500 . ?
C28 C29 1.3898(16) . ?
C28 C39 1.4901(14) . ?
C29 C30 1.3869(15) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.5089(17) . ?
C31 H311 0.9900 . ?
C31 H312 0.9900 . ?
C32 C37 1.3899(17) . ?
C32 C33 1.3917(17) . ?
C33 C34 1.387(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.381(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.388(2) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H381 0.9800 . ?
C38 H382 0.9800 . ?
C38 H383 0.9800 . ?
C40 H401 0.9800 . ?
C40 H402 0.9800 . ?
C40 H403 0.9800 . ?
O31 C41 1.3769(16) . ?
O31 C42 1.4007(13) . ?
O32 C41 1.2133(16) . ?
O33 C59 1.1976(16) . ?
O34 C59 1.3268(16) . ?
O34 C60 1.4459(16) . ?
N3 C41 1.3382(18) . ?
N3 C43 1.4509(15) . ?
N3 C51 1.4577(17) . ?
C42 C44 1.3313(16) . ?
C42 C43 1.5033(17) . ?
C43 H431 0.9900 . ?
C43 H432 0.9900 . ?
C44 C45 1.4807(15) . ?
C44 C58 1.5079(16) . ?
C45 C46 1.3974(15) . ?
C45 C50 1.3975(16) . ?
C46 C47 1.3847(16) . ?
C46 H46 0.9500 . ?
C47 C48 1.3893(16) . ?
C47 H47 0.9500 . ?
C48 C49 1.3876(16) . ?
C48 C59 1.4841(15) . ?
C49 C50 1.3848(16) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.5094(19) . ?
C51 H511 0.9900 . ?
C51 H512 0.9900 . ?
C52 C53 1.382(2) . ?
C52 C57 1.3859(18) . ?
C53 C54 1.393(2) . ?
C53 H53 0.9500 . ?
C54 C55 1.377(2) . ?
C54 H54 0.9500 . ?
C55 C56 1.374(2) . ?
C55 H55 0.9500 . ?
C56 C57 1.381(2) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?
C58 H581 0.9800 . ?
C58 H582 0.9800 . ?
C58 H583 0.9800 . ?
C60 H601 0.9800 . ?
C60 H602 0.9800 . ?
C60 H603 0.9800 . ?
O41 C61 1.3794(17) . ?
O41 C62 1.4024(13) . ?
O42 C61 1.2083(15) . ?
O43 C79 1.1982(16) . ?
O44 C79 1.3261(15) . ?
O44 C80 1.4518(16) . ?
N4 C61 1.3387(18) . ?
N4 C63 1.4472(14) . ?
N4 C71 1.4546(18) . ?
C62 C64 1.3300(17) . ?
C62 C63 1.5055(17) . ?
C63 H631 0.9900 . ?
C63 H632 0.9900 . ?
C64 C65 1.4835(15) . ?
C64 C78 1.5080(16) . ?
C65 C66 1.3930(16) . ?
C65 C70 1.3990(16) . ?
C66 C67 1.3872(17) . ?
C66 H66 0.9500 . ?
C67 C68 1.3894(16) . ?
C67 H67 0.9500 . ?
C68 C69 1.3892(16) . ?
C68 C79 1.4825(15) . ?
C69 C70 1.3843(15) . ?
C69 H69 0.9500 . ?
C70 H70 0.9500 . ?
C71 C72 1.5059(19) . ?
C71 H711 0.9900 . ?
C71 H712 0.9900 . ?
C72 C73 1.3848(19) . ?
C72 C77 1.3900(18) . ?
C73 C74 1.384(2) . ?
C73 H73 0.9500 . ?
C74 C75 1.380(2) . ?
C74 H74 0.9500 . ?
C75 C76 1.380(3) . ?
C75 H75 0.9500 . ?
C76 C77 1.380(2) . ?
C76 H76 0.9500 . ?
C77 H77 0.9500 . ?
C78 H781 0.9800 . ?
C78 H782 0.9800 . ?
C78 H783 0.9800 . ?
C80 H801 0.9800 . ?
C80 H802 0.9800 . ?
C80 H803 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
C1 O1 C2 109.29(8) . . ?
C19 O4 C20 116.81(10) . . ?
C1 N1 C3 111.48(9) . . ?
C1 N1 C11 122.33(10) . . ?
C3 N1 C11 121.70(9) . . ?
O2 C1 N1 129.52(12) . . ?
O2 C1 O1 121.75(11) . . ?
N1 C1 O1 108.73(9) . . ?
C4 C2 O1 120.88(9) . . ?
C4 C2 C3 131.77(9) . . ?
O1 C2 C3 107.22(8) . . ?
N1 C3 C2 100.73(8) . . ?
N1 C3 H31 111.6 . . ?
C2 C3 H31 111.6 . . ?
N1 C3 H32 111.6 . . ?
C2 C3 H32 111.6 . . ?
H31 C3 H32 109.4 . . ?
C2 C4 C5 120.59(9) . . ?
C2 C4 C18 121.29(9) . . ?
C5 C4 C18 118.11(9) . . ?
C6 C5 C10 117.90(9) . . ?
C6 C5 C4 120.80(9) . . ?
C10 C5 C4 121.25(9) . . ?
C7 C6 C5 120.96(10) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.20(10) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 119.50(10) . . ?
C9 C8 C19 121.20(10) . . ?
C7 C8 C19 119.23(10) . . ?
C10 C9 C8 119.93(10) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 121.50(10) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
N1 C11 C12 112.12(10) . . ?
N1 C11 H111 109.2 . . ?
C12 C11 H111 109.2 . . ?
N1 C11 H112 109.2 . . ?
C12 C11 H112 109.2 . . ?
H111 C11 H112 107.9 . . ?
C17 C12 C13 119.66(12) . . ?
C17 C12 C11 119.94(12) . . ?
C13 C12 C11 120.33(11) . . ?
C12 C13 C14 119.71(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 119.78(14) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.22(14) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.20(14) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.41(14) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C4 C18 H181 109.5 . . ?
C4 C18 H182 109.5 . . ?
H181 C18 H182 109.5 . . ?
C4 C18 H183 109.5 . . ?
H181 C18 H183 109.5 . . ?
H182 C18 H183 109.5 . . ?
O3 C19 O4 123.57(10) . . ?
O3 C19 C8 124.85(11) . . ?
O4 C19 C8 111.57(9) . . ?
O4 C20 H201 109.5 . . ?
O4 C20 H202 109.5 . . ?
H201 C20 H202 109.5 . . ?
O4 C20 H203 109.5 . . ?
H201 C20 H203 109.5 . . ?
H202 C20 H203 109.5 . . ?
C21 O21 C22 109.41(8) . . ?
C39 O24 C40 116.41(10) . . ?
C21 N2 C23 112.64(9) . . ?
C21 N2 C31 124.06(10) . . ?
C23 N2 C31 123.28(9) . . ?
O22 C21 N2 129.71(11) . . ?
O22 C21 O21 121.31(11) . . ?
N2 C21 O21 108.98(9) . . ?
C24 C22 O21 120.18(9) . . ?
C24 C22 C23 131.92(9) . . ?
O21 C22 C23 107.69(9) . . ?
N2 C23 C22 100.89(8) . . ?
N2 C23 H231 111.6 . . ?
C22 C23 H231 111.6 . . ?
N2 C23 H232 111.6 . . ?
C22 C23 H232 111.6 . . ?
H231 C23 H232 109.4 . . ?
C22 C24 C25 121.13(10) . . ?
C22 C24 C38 120.71(10) . . ?
C25 C24 C38 118.14(9) . . ?
C26 C25 C30 118.00(10) . . ?
C26 C25 C24 120.73(9) . . ?
C30 C25 C24 121.20(10) . . ?
C27 C26 C25 121.13(10) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 120.14(10) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 C27 119.29(10) . . ?
C29 C28 C39 122.10(10) . . ?
C27 C28 C39 118.54(10) . . ?
C30 C29 C28 120.42(10) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C25 121.00(10) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
N2 C31 C32 111.72(9) . . ?
N2 C31 H311 109.3 . . ?
C32 C31 H311 109.3 . . ?
N2 C31 H312 109.3 . . ?
C32 C31 H312 109.3 . . ?
H311 C31 H312 107.9 . . ?
C37 C32 C33 118.75(12) . . ?
C37 C32 C31 120.58(11) . . ?
C33 C32 C31 120.63(11) . . ?
C34 C33 C32 120.45(12) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 120.27(13) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C36 C35 C34 119.71(14) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C37 120.14(13) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C36 C37 C32 120.68(12) . . ?
C36 C37 H37 119.7 . . ?
C32 C37 H37 119.7 . . ?
C24 C38 H381 109.5 . . ?
C24 C38 H382 109.5 . . ?
H381 C38 H382 109.5 . . ?
C24 C38 H383 109.5 . . ?
H381 C38 H383 109.5 . . ?
H382 C38 H383 109.5 . . ?
O23 C39 O24 123.51(10) . . ?
O23 C39 C28 124.59(11) . . ?
O24 C39 C28 111.88(10) . . ?
O24 C40 H401 109.5 . . ?
O24 C40 H402 109.5 . . ?
H401 C40 H402 109.5 . . ?
O24 C40 H403 109.5 . . ?
H401 C40 H403 109.5 . . ?
H402 C40 H403 109.5 . . ?
C41 O31 C42 109.26(10) . . ?
C59 O34 C60 115.46(12) . . ?
C41 N3 C43 112.46(11) . . ?
C41 N3 C51 124.01(11) . . ?
C43 N3 C51 123.22(11) . . ?
O32 C41 N3 129.90(13) . . ?
O32 C41 O31 121.04(13) . . ?
N3 C41 O31 109.06(10) . . ?
C44 C42 O31 119.58(10) . . ?
C44 C42 C43 132.72(11) . . ?
O31 C42 C43 107.58(9) . . ?
N3 C43 C42 100.85(10) . . ?
N3 C43 H431 111.6 . . ?
C42 C43 H431 111.6 . . ?
N3 C43 H432 111.6 . . ?
C42 C43 H432 111.6 . . ?
H431 C43 H432 109.4 . . ?
C42 C44 C45 121.41(10) . . ?
C42 C44 C58 119.96(10) . . ?
C45 C44 C58 118.51(10) . . ?
C46 C45 C50 117.68(10) . . ?
C46 C45 C44 122.76(10) . . ?
C50 C45 C44 119.55(10) . . ?
C47 C46 C45 121.01(10) . . ?
C47 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C46 C47 C48 120.54(10) . . ?
C46 C47 H47 119.7 . . ?
C48 C47 H47 119.7 . . ?
C49 C48 C47 119.14(10) . . ?
C49 C48 C59 122.22(10) . . ?
C47 C48 C59 118.64(10) . . ?
C50 C49 C48 120.19(11) . . ?
C50 C49 H49 119.9 . . ?
C48 C49 H49 119.9 . . ?
C49 C50 C45 121.40(11) . . ?
C49 C50 H50 119.3 . . ?
C45 C50 H50 119.3 . . ?
N3 C51 C52 113.34(11) . . ?
N3 C51 H511 108.9 . . ?
C52 C51 H511 108.9 . . ?
N3 C51 H512 108.9 . . ?
C52 C51 H512 108.9 . . ?
H511 C51 H512 107.7 . . ?
C53 C52 C57 118.79(13) . . ?
C53 C52 C51 120.82(12) . . ?
C57 C52 C51 120.39(13) . . ?
C52 C53 C54 120.39(13) . . ?
C52 C53 H53 119.8 . . ?
C54 C53 H53 119.8 . . ?
C55 C54 C53 120.20(15) . . ?
C55 C54 H54 119.9 . . ?
C53 C54 H54 119.9 . . ?
C56 C55 C54 119.48(15) . . ?
C56 C55 H55 120.3 . . ?
C54 C55 H55 120.3 . . ?
C55 C56 C57 120.57(14) . . ?
C55 C56 H56 119.7 . . ?
C57 C56 H56 119.7 . . ?
C56 C57 C52 120.57(14) . . ?
C56 C57 H57 119.7 . . ?
C52 C57 H57 119.7 . . ?
C44 C58 H581 109.5 . . ?
C44 C58 H582 109.5 . . ?
H581 C58 H582 109.5 . . ?
C44 C58 H583 109.5 . . ?
H581 C58 H583 109.5 . . ?
H582 C58 H583 109.5 . . ?
O33 C59 O34 122.97(11) . . ?
O33 C59 C48 124.06(11) . . ?
O34 C59 C48 112.96(10) . . ?
O34 C60 H601 109.5 . . ?
O34 C60 H602 109.5 . . ?
H601 C60 H602 109.5 . . ?
O34 C60 H603 109.5 . . ?
H601 C60 H603 109.5 . . ?
H602 C60 H603 109.5 . . ?
C61 O41 C62 109.21(10) . . ?
C79 O44 C80 115.10(11) . . ?
C61 N4 C63 113.06(11) . . ?
C61 N4 C71 123.68(11) . . ?
C63 N4 C71 123.03(11) . . ?
O42 C61 N4 129.57(14) . . ?
O42 C61 O41 121.62(13) . . ?
N4 C61 O41 108.82(10) . . ?
C64 C62 O41 120.06(10) . . ?
C64 C62 C63 131.95(10) . . ?
O41 C62 C63 107.83(9) . . ?
N4 C63 C62 100.77(10) . . ?
N4 C63 H631 111.6 . . ?
C62 C63 H631 111.6 . . ?
N4 C63 H632 111.6 . . ?
C62 C63 H632 111.6 . . ?
H631 C63 H632 109.4 . . ?
C62 C64 C65 120.52(10) . . ?
C62 C64 C78 120.86(11) . . ?
C65 C64 C78 118.57(10) . . ?
C66 C65 C70 118.11(10) . . ?
C66 C65 C64 119.92(10) . . ?
C70 C65 C64 121.95(10) . . ?
C67 C66 C65 121.25(11) . . ?
C67 C66 H66 119.4 . . ?
C65 C66 H66 119.4 . . ?
C66 C67 C68 120.03(11) . . ?
C66 C67 H67 120.0 . . ?
C68 C67 H67 120.0 . . ?
C69 C68 C67 119.27(10) . . ?
C69 C68 C79 117.72(10) . . ?
C67 C68 C79 123.00(10) . . ?
C70 C69 C68 120.57(10) . . ?
C70 C69 H69 119.7 . . ?
C68 C69 H69 119.7 . . ?
C69 C70 C65 120.72(10) . . ?
C69 C70 H70 119.6 . . ?
C65 C70 H70 119.6 . . ?
N4 C71 C72 111.51(11) . . ?
N4 C71 H711 109.3 . . ?
C72 C71 H711 109.3 . . ?
N4 C71 H712 109.3 . . ?
C72 C71 H712 109.3 . . ?
H711 C71 H712 108.0 . . ?
C73 C72 C77 119.31(13) . . ?
C73 C72 C71 120.34(12) . . ?
C77 C72 C71 120.30(13) . . ?
C74 C73 C72 120.40(13) . . ?
C74 C73 H73 119.8 . . ?
C72 C73 H73 119.8 . . ?
C75 C74 C73 119.95(16) . . ?
C75 C74 H74 120.0 . . ?
C73 C74 H74 120.0 . . ?
C76 C75 C74 119.87(15) . . ?
C76 C75 H75 120.1 . . ?
C74 C75 H75 120.1 . . ?
C77 C76 C75 120.42(15) . . ?
C77 C76 H76 119.8 . . ?
C75 C76 H76 119.8 . . ?
C76 C77 C72 120.04(15) . . ?
C76 C77 H77 120.0 . . ?
C72 C77 H77 120.0 . . ?
C64 C78 H781 109.5 . . ?
C64 C78 H782 109.5 . . ?
H781 C78 H782 109.5 . . ?
C64 C78 H783 109.5 . . ?
H781 C78 H783 109.5 . . ?
H782 C78 H783 109.5 . . ?
O43 C79 O44 122.43(11) . . ?
O43 C79 C68 123.89(11) . . ?
O44 C79 C68 113.68(10) . . ?
O44 C80 H801 109.5 . . ?
O44 C80 H802 109.5 . . ?
H801 C80 H802 109.5 . . ?
O44 C80 H803 109.5 . . ?
H801 C80 H803 109.5 . . ?
H802 C80 H803 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
C3 N1 C1 O2 -168.29(12) . . . . ?
C11 N1 C1 O2 -11.8(2) . . . . ?
C3 N1 C1 O1 12.51(13) . . . . ?
C11 N1 C1 O1 169.03(10) . . . . ?
C2 O1 C1 O2 178.06(11) . . . . ?
C2 O1 C1 N1 -2.67(12) . . . . ?
C1 O1 C2 C4 168.78(10) . . . . ?
C1 O1 C2 C3 -7.61(11) . . . . ?
C1 N1 C3 C2 -16.12(12) . . . . ?
C11 N1 C3 C2 -172.81(10) . . . . ?
C4 C2 C3 N1 -162.02(12) . . . . ?
O1 C2 C3 N1 13.82(11) . . . . ?
O1 C2 C4 C5 176.95(9) . . . . ?
C3 C2 C4 C5 -7.67(18) . . . . ?
O1 C2 C4 C18 -4.14(16) . . . . ?
C3 C2 C4 C18 171.23(11) . . . . ?
C2 C4 C5 C6 146.16(11) . . . . ?
C18 C4 C5 C6 -32.78(14) . . . . ?
C2 C4 C5 C10 -36.41(15) . . . . ?
C18 C4 C5 C10 144.65(10) . . . . ?
C10 C5 C6 C7 0.78(16) . . . . ?
C4 C5 C6 C7 178.29(10) . . . . ?
C5 C6 C7 C8 -1.33(17) . . . . ?
C6 C7 C8 C9 0.78(17) . . . . ?
C6 C7 C8 C19 -176.22(10) . . . . ?
C7 C8 C9 C10 0.31(16) . . . . ?
C19 C8 C9 C10 177.25(10) . . . . ?
C8 C9 C10 C5 -0.87(16) . . . . ?
C6 C5 C10 C9 0.32(16) . . . . ?
C4 C5 C10 C9 -177.18(10) . . . . ?
C1 N1 C11 C12 -87.58(13) . . . . ?
C3 N1 C11 C12 66.58(14) . . . . ?
N1 C11 C12 C17 90.07(13) . . . . ?
N1 C11 C12 C13 -86.96(14) . . . . ?
C17 C12 C13 C14 -0.70(18) . . . . ?
C11 C12 C13 C14 176.34(11) . . . . ?
C12 C13 C14 C15 0.82(19) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C17 -1.1(2) . . . . ?
C15 C16 C17 C12 1.2(2) . . . . ?
C13 C12 C17 C16 -0.29(19) . . . . ?
C11 C12 C17 C16 -177.34(12) . . . . ?
C20 O4 C19 O3 2.86(17) . . . . ?
C20 O4 C19 C8 -176.01(10) . . . . ?
C9 C8 C19 O3 -175.66(12) . . . . ?
C7 C8 C19 O3 1.29(18) . . . . ?
C9 C8 C19 O4 3.19(15) . . . . ?
C7 C8 C19 O4 -179.86(10) . . . . ?
C23 N2 C21 O22 175.13(12) . . . . ?
C31 N2 C21 O22 -3.4(2) . . . . ?
C23 N2 C21 O21 -4.60(13) . . . . ?
C31 N2 C21 O21 176.86(10) . . . . ?
C22 O21 C21 O22 -179.20(10) . . . . ?
C22 O21 C21 N2 0.56(12) . . . . ?
C21 O21 C22 C24 -171.89(10) . . . . ?
C21 O21 C22 C23 3.42(11) . . . . ?
C21 N2 C23 C22 6.27(12) . . . . ?
C31 N2 C23 C22 -175.18(10) . . . . ?
C24 C22 C23 N2 168.93(12) . . . . ?
O21 C22 C23 N2 -5.62(11) . . . . ?
O21 C22 C24 C25 -175.70(9) . . . . ?
C23 C22 C24 C25 10.31(19) . . . . ?
O21 C22 C24 C38 5.92(16) . . . . ?
C23 C22 C24 C38 -168.07(12) . . . . ?
C22 C24 C25 C26 -143.19(11) . . . . ?
C38 C24 C25 C26 35.23(15) . . . . ?
C22 C24 C25 C30 39.90(16) . . . . ?
C38 C24 C25 C30 -141.68(11) . . . . ?
C30 C25 C26 C27 -1.08(17) . . . . ?
C24 C25 C26 C27 -178.08(10) . . . . ?
C25 C26 C27 C28 1.18(17) . . . . ?
C26 C27 C28 C29 -0.60(17) . . . . ?
C26 C27 C28 C39 176.36(10) . . . . ?
C27 C28 C29 C30 -0.05(16) . . . . ?
C39 C28 C29 C30 -176.90(10) . . . . ?
C28 C29 C30 C25 0.13(17) . . . . ?
C26 C25 C30 C29 0.42(16) . . . . ?
C24 C25 C30 C29 177.41(10) . . . . ?
C21 N2 C31 C32 -99.45(13) . . . . ?
C23 N2 C31 C32 82.16(13) . . . . ?
N2 C31 C32 C37 94.50(12) . . . . ?
N2 C31 C32 C33 -83.23(13) . . . . ?
C37 C32 C33 C34 -0.40(17) . . . . ?
C31 C32 C33 C34 177.36(11) . . . . ?
C32 C33 C34 C35 0.51(19) . . . . ?
C33 C34 C35 C36 -0.5(2) . . . . ?
C34 C35 C36 C37 0.4(2) . . . . ?
C35 C36 C37 C32 -0.29(19) . . . . ?
C33 C32 C37 C36 0.30(17) . . . . ?
C31 C32 C37 C36 -177.47(11) . . . . ?
C40 O24 C39 O23 -2.82(17) . . . . ?
C40 O24 C39 C28 175.86(9) . . . . ?
C29 C28 C39 O23 176.25(12) . . . . ?
C27 C28 C39 O23 -0.62(17) . . . . ?
C29 C28 C39 O24 -2.41(15) . . . . ?
C27 C28 C39 O24 -179.28(10) . . . . ?
C43 N3 C41 O32 -177.23(14) . . . . ?
C51 N3 C41 O32 -3.4(2) . . . . ?
C43 N3 C41 O31 3.67(14) . . . . ?
C51 N3 C41 O31 177.47(11) . . . . ?
C42 O31 C41 O32 -176.71(12) . . . . ?
C42 O31 C41 N3 2.47(13) . . . . ?
C41 O31 C42 C44 169.14(11) . . . . ?
C41 O31 C42 C43 -7.29(12) . . . . ?
C41 N3 C43 C42 -7.63(13) . . . . ?
C51 N3 C43 C42 178.52(11) . . . . ?
C44 C42 C43 N3 -167.05(12) . . . . ?
O31 C42 C43 N3 8.72(11) . . . . ?
O31 C42 C44 C45 -175.91(9) . . . . ?
C43 C42 C44 C45 -0.54(19) . . . . ?
O31 C42 C44 C58 0.17(16) . . . . ?
C43 C42 C44 C58 175.54(12) . . . . ?
C42 C44 C45 C46 -36.46(16) . . . . ?
C58 C44 C45 C46 147.40(11) . . . . ?
C42 C44 C45 C50 144.84(12) . . . . ?
C58 C44 C45 C50 -31.29(15) . . . . ?
C50 C45 C46 C47 -1.57(16) . . . . ?
C44 C45 C46 C47 179.71(10) . . . . ?
C45 C46 C47 C48 -0.17(17) . . . . ?
C46 C47 C48 C49 1.69(17) . . . . ?
C46 C47 C48 C59 -179.14(10) . . . . ?
C47 C48 C49 C50 -1.43(18) . . . . ?
C59 C48 C49 C50 179.44(11) . . . . ?
C48 C49 C50 C45 -0.36(19) . . . . ?
C46 C45 C50 C49 1.84(17) . . . . ?
C44 C45 C50 C49 -179.40(11) . . . . ?
C41 N3 C51 C52 -99.87(15) . . . . ?
C43 N3 C51 C52 73.28(16) . . . . ?
N3 C51 C52 C53 -90.33(16) . . . . ?
N3 C51 C52 C57 89.29(15) . . . . ?
C57 C52 C53 C54 0.2(2) . . . . ?
C51 C52 C53 C54 179.82(13) . . . . ?
C52 C53 C54 C55 0.7(2) . . . . ?
C53 C54 C55 C56 -1.4(2) . . . . ?
C54 C55 C56 C57 1.1(2) . . . . ?
C55 C56 C57 C52 -0.2(2) . . . . ?
C53 C52 C57 C56 -0.5(2) . . . . ?
C51 C52 C57 C56 179.90(14) . . . . ?
C60 O34 C59 O33 3.1(2) . . . . ?
C60 O34 C59 C48 -177.43(12) . . . . ?
C49 C48 C59 O33 -173.75(13) . . . . ?
C47 C48 C59 O33 7.11(18) . . . . ?
C49 C48 C59 O34 6.74(16) . . . . ?
C47 C48 C59 O34 -172.40(11) . . . . ?
C63 N4 C61 O42 -179.95(13) . . . . ?
C71 N4 C61 O42 -5.3(2) . . . . ?
C63 N4 C61 O41 0.13(15) . . . . ?
C71 N4 C61 O41 174.76(11) . . . . ?
C62 O41 C61 O42 176.34(12) . . . . ?
C62 O41 C61 N4 -3.73(13) . . . . ?
C61 O41 C62 C64 -170.24(11) . . . . ?
C61 O41 C62 C63 5.70(12) . . . . ?
C61 N4 C63 C62 3.15(14) . . . . ?
C71 N4 C63 C62 -171.52(12) . . . . ?
C64 C62 C63 N4 170.06(12) . . . . ?
O41 C62 C63 N4 -5.21(12) . . . . ?
O41 C62 C64 C65 178.37(9) . . . . ?
C63 C62 C64 C65 3.57(19) . . . . ?
O41 C62 C64 C78 0.72(17) . . . . ?
C63 C62 C64 C78 -174.08(12) . . . . ?
C62 C64 C65 C66 -140.76(12) . . . . ?
C78 C64 C65 C66 36.94(16) . . . . ?
C62 C64 C65 C70 40.93(16) . . . . ?
C78 C64 C65 C70 -141.37(11) . . . . ?
C70 C65 C66 C67 -2.30(18) . . . . ?
C64 C65 C66 C67 179.33(11) . . . . ?
C65 C66 C67 C68 1.47(19) . . . . ?
C66 C67 C68 C69 0.48(18) . . . . ?
C66 C67 C68 C79 179.25(11) . . . . ?
C67 C68 C69 C70 -1.55(17) . . . . ?
C79 C68 C69 C70 179.62(10) . . . . ?
C68 C69 C70 C65 0.69(17) . . . . ?
C66 C65 C70 C69 1.22(16) . . . . ?
C64 C65 C70 C69 179.55(10) . . . . ?
C61 N4 C71 C72 -100.39(15) . . . . ?
C63 N4 C71 C72 73.71(17) . . . . ?
N4 C71 C72 C73 -89.39(15) . . . . ?
N4 C71 C72 C77 87.91(15) . . . . ?
C77 C72 C73 C74 0.61(19) . . . . ?
C71 C72 C73 C74 177.94(12) . . . . ?
C72 C73 C74 C75 0.7(2) . . . . ?
C73 C74 C75 C76 -1.2(2) . . . . ?
C74 C75 C76 C77 0.4(3) . . . . ?
C75 C76 C77 C72 0.9(2) . . . . ?
C73 C72 C77 C76 -1.4(2) . . . . ?
C71 C72 C77 C76 -178.69(14) . . . . ?
C80 O44 C79 O43 -5.6(2) . . . . ?
C80 O44 C79 C68 175.02(13) . . . . ?
C69 C68 C79 O43 3.56(18) . . . . ?
C67 C68 C79 O43 -175.22(13) . . . . ?
C69 C68 C79 O44 -177.06(11) . . . . ?
C67 C68 C79 O44 4.16(17) . . . . ?


