# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1456321'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16  H14  N2  O1'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.42720(10)
_cell_length_b                   11.7684(2)
_cell_length_c                   18.3674(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1389.27(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5858
_cell_measurement_theta_min      4.46
_cell_measurement_theta_max      67.74

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.604
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10018
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.462
_diffrn_reflns_theta_max         67.732
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2459
_reflns_number_gt                2382
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.965

_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       'Bruker Apex2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Superflip (Palatinus, 2007'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0416P)²+0.1109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 958 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2459
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8057(2) 0.53465(14) 0.67264(9) 0.0540(4) Uani 1 1 d . . . . .
N2 N 1.3239(2) 0.39809(16) 0.78815(9) 0.0627(4) Uani 1 1 d . . . . .
O1 O 0.5555(3) 0.42743(17) 0.97295(9) 0.0906(6) Uani 1 1 d . . . . .
C1 C 0.9182(2) 0.40860(13) 0.78273(8) 0.0368(3) Uani 1 1 d . . . . .
C2 C 0.8231(2) 0.45765(13) 0.85459(8) 0.0376(3) Uani 1 1 d . . . . .
H2 H 0.6701 0.4656 0.8461 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8510(2) 0.35942(14) 0.90801(9) 0.0429(4) Uani 1 1 d . . . . .
H3 H 0.9946 0.3641 0.9287 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8347(3) 0.24667(14) 0.86215(9) 0.0428(4) Uani 1 1 d . . . . .
H4 H 0.9637 0.2008 0.8702 0.051 Uiso 1 1 calc R U . . .
C5 C 0.8301(3) 0.28667(14) 0.78189(9) 0.0423(4) Uani 1 1 d . . . . .
H5A H 0.9170 0.2366 0.7511 0.051 Uiso 1 1 calc R U . . .
H5B H 0.6860 0.2861 0.7628 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8565(2) 0.47798(14) 0.71983(9) 0.0401(3) Uani 1 1 d . . . . .
C7 C 1.1484(2) 0.40458(14) 0.78538(8) 0.0426(4) Uani 1 1 d . . . . .
C8 C 0.9011(2) 0.57275(14) 0.87741(8) 0.0420(4) Uani 1 1 d . . . . .
C9 C 0.7752(3) 0.66708(15) 0.86653(10) 0.0535(5) Uani 1 1 d . . . . .
H9 H 0.6421 0.6574 0.8449 0.064 Uiso 1 1 calc R U . . .
C10 C 0.8390(5) 0.77435(18) 0.88643(11) 0.0717(6) Uani 1 1 d . . . . .
H10 H 0.7501 0.8378 0.8789 0.086 Uiso 1 1 calc R U . . .
C11 C 1.0318(5) 0.78934(19) 0.91728(11) 0.0772(7) Uani 1 1 d . . . . .
H11 H 1.0764 0.8632 0.9312 0.093 Uiso 1 1 calc R U . . .
C12 C 1.1604(4) 0.6971(2) 0.92803(10) 0.0703(6) Uani 1 1 d . . . . .
H12 H 1.2942 0.7078 0.9489 0.084 Uiso 1 1 calc R U . . .
C13 C 1.0961(3) 0.58884(17) 0.90859(9) 0.0526(4) Uani 1 1 d . . . . .
H13 H 1.1852 0.5256 0.9166 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6994(4) 0.36343(19) 0.96975(11) 0.0603(5) Uani 1 1 d . . . . .
H14 H 0.7189 0.3118 1.0089 0.072 Uiso 1 1 calc R U . . .
C15 C 0.6486(3) 0.17346(15) 0.87854(9) 0.0473(4) Uani 1 1 d . . . . .
H15 H 0.5156 0.2012 0.8646 0.057 Uiso 1 1 calc R U . . .
C16 C 0.6569(3) 0.07472(15) 0.91050(10) 0.0533(4) Uani 1 1 d . . . . .
H16A H 0.7872 0.0443 0.9252 0.064 Uiso 1 1 calc R U . . .
H16B H 0.5326 0.0331 0.9191 0.064 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
N1 C6 1.141(2) . ?
N2 C7 1.132(2) . ?
O1 C14 1.194(3) . ?
C1 C6 1.469(2) . ?
C1 C7 1.481(2) . ?
C1 C5 1.543(2) . ?
C1 C2 1.565(2) . ?
C2 C8 1.504(2) . ?
C2 C3 1.527(2) . ?
C2 H2 1.0000 . ?
C3 C14 1.496(3) . ?
C3 C4 1.575(2) . ?
C3 H3 1.0000 . ?
C4 C15 1.505(2) . ?
C4 C5 1.548(2) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C8 C9 1.388(2) . ?
C8 C13 1.391(2) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.303(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9500 . ?
C16 H16B 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
C6 C1 C7 108.26(13) . . ?
C6 C1 C5 114.21(13) . . ?
C7 C1 C5 109.71(13) . . ?
C6 C1 C2 110.65(12) . . ?
C7 C1 C2 111.98(13) . . ?
C5 C1 C2 102.01(12) . . ?
C8 C2 C3 117.63(13) . . ?
C8 C2 C1 115.91(13) . . ?
C3 C2 C1 102.52(12) . . ?
C8 C2 H2 106.7 . . ?
C3 C2 H2 106.7 . . ?
C1 C2 H2 106.7 . . ?
C14 C3 C2 112.76(15) . . ?
C14 C3 C4 112.89(14) . . ?
C2 C3 C4 106.65(12) . . ?
C14 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
C4 C3 H3 108.1 . . ?
C15 C4 C5 110.46(13) . . ?
C15 C4 C3 115.34(14) . . ?
C5 C4 C3 104.73(13) . . ?
C15 C4 H4 108.7 . . ?
C5 C4 H4 108.7 . . ?
C3 C4 H4 108.7 . . ?
C1 C5 C4 105.45(12) . . ?
C1 C5 H5A 110.7 . . ?
C4 C5 H5A 110.7 . . ?
C1 C5 H5B 110.7 . . ?
C4 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
N1 C6 C1 177.57(18) . . ?
N2 C7 C1 177.9(2) . . ?
C9 C8 C13 118.40(17) . . ?
C9 C8 C2 119.07(15) . . ?
C13 C8 C2 122.53(16) . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O1 C14 C3 124.16(19) . . ?
O1 C14 H14 117.9 . . ?
C3 C14 H14 117.9 . . ?
C16 C15 C4 124.64(16) . . ?
C16 C15 H15 117.7 . . ?
C4 C15 H15 117.7 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?

_refine_diff_density_max         0.091
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.023

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1456333'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29

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'
O O 0.0492 0.0322 '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'

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

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

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

_cell_length_a                   9.0535(2)
_cell_length_b                   7.4148(2)
_cell_length_c                   10.4203(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.4060(10)
_cell_angle_gamma                90
_cell_volume                     677.52(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      4.38
_cell_measurement_theta_max      67.65

_exptl_crystal_description       plate-like
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.619
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12413
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.044
_diffrn_reflns_theta_max         67.659
_diffrn_reflns_theta_full        67.659
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2436
_reflns_number_gt                2418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.988

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0285P)²+0.0783P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0144(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(11)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2436
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0644
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09341(18) 0.1671(3) -0.01566(15) 0.0805(6) Uani 1 1 d . . . . .
N1 N 0.5252(2) 0.4662(3) 0.59457(17) 0.0554(5) Uani 1 1 d . . . . .
N2 N 0.1073(3) 0.7162(3) 0.3755(2) 0.0678(6) Uani 1 1 d . . . . .
C1 C 0.27105(18) 0.4225(2) 0.41315(15) 0.0312(4) Uani 1 1 d . . . . .
C2 C 0.30506(17) 0.3599(2) 0.27979(15) 0.0280(3) Uani 1 1 d . . . . .
H2 H 0.3747 0.2534 0.3008 0.034 Uiso 1 1 calc R U . . .
C3 C 0.14830(17) 0.2884(2) 0.20401(15) 0.0329(4) Uani 1 1 d . . . . .
H3 H 0.0793 0.3908 0.1660 0.039 Uiso 1 1 calc R U . . .
C4 C 0.08608(18) 0.1868(2) 0.31062(16) 0.0339(4) Uani 1 1 d . . . . .
H4 H 0.1134 0.0564 0.3081 0.041 Uiso 1 1 calc R U . . .
C5 C 0.17369(19) 0.2651(2) 0.44591(16) 0.0365(4) Uani 1 1 d . . . . .
H5A H 0.2398 0.1719 0.4993 0.044 Uiso 1 1 calc R U . . .
H5B H 0.1016 0.3096 0.4962 0.044 Uiso 1 1 calc R U . . .
C6 C 0.4132(2) 0.4498(3) 0.51651(17) 0.0377(4) Uani 1 1 d . . . . .
C7 C 0.1821(2) 0.5911(2) 0.39325(18) 0.0409(4) Uani 1 1 d . . . . .
C8 C 0.38275(18) 0.4967(2) 0.21201(14) 0.0284(3) Uani 1 1 d . . . . .
C9 C 0.54211(19) 0.4993(2) 0.24150(16) 0.0339(4) Uani 1 1 d . . . . .
H9 H 0.5988 0.4157 0.3037 0.041 Uiso 1 1 calc R U . . .
C10 C 0.61803(19) 0.6218(3) 0.18122(18) 0.0404(4) Uani 1 1 d . . . . .
H10 H 0.7263 0.6222 0.2021 0.048 Uiso 1 1 calc R U . . .
C11 C 0.5364(2) 0.7442(3) 0.09034(17) 0.0413(4) Uani 1 1 d . . . . .
H11 H 0.5884 0.8284 0.0487 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3791(2) 0.7431(2) 0.06054(16) 0.0384(4) Uani 1 1 d . . . . .
H12 H 0.3230 0.8267 -0.0020 0.046 Uiso 1 1 calc R U . . .
C13 C 0.30246(19) 0.6210(2) 0.12120(15) 0.0336(4) Uani 1 1 d . . . . .
H13 H 0.1942 0.6222 0.1005 0.040 Uiso 1 1 calc R U . . .
C14 C 0.1630(2) 0.1605(3) 0.09669(19) 0.0504(5) Uani 1 1 d . . . . .
H14 H 0.2347 0.0653 0.1209 0.060 Uiso 1 1 calc R U . . .
C16 C -0.08315(19) 0.2010(3) 0.28524(17) 0.0404(4) Uani 1 1 d . . . . .
H16 H -0.1246 0.3159 0.2964 0.048 Uiso 1 1 calc R U . . .
C17 C -0.1783(2) 0.0681(3) 0.2490(2) 0.0527(5) Uani 1 1 d . . . . .
H17A H -0.1413 -0.0489 0.2367 0.063 Uiso 1 1 calc R U . . .
H17B H -0.2848 0.0881 0.2347 0.063 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 C14 1.184(2) . ?
N1 C6 1.138(2) . ?
N2 C7 1.136(3) . ?
C1 C6 1.473(2) . ?
C1 C7 1.474(2) . ?
C1 C5 1.551(2) . ?
C1 C2 1.567(2) . ?
C2 C8 1.507(2) . ?
C2 C3 1.536(2) . ?
C2 H2 1.0000 . ?
C3 C14 1.497(2) . ?
C3 C4 1.559(2) . ?
C3 H3 1.0000 . ?
C4 C16 1.492(2) . ?
C4 C5 1.548(2) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C8 C13 1.389(2) . ?
C8 C9 1.398(2) . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 C17 1.301(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9500 . ?
C17 H17B 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
C6 C1 C7 109.51(15) . . ?
C6 C1 C5 112.57(13) . . ?
C7 C1 C5 110.40(13) . . ?
C6 C1 C2 111.13(13) . . ?
C7 C1 C2 110.35(13) . . ?
C5 C1 C2 102.72(13) . . ?
C8 C2 C3 118.06(13) . . ?
C8 C2 C1 115.71(13) . . ?
C3 C2 C1 101.41(12) . . ?
C8 C2 H2 107.0 . . ?
C3 C2 H2 107.0 . . ?
C1 C2 H2 107.0 . . ?
C14 C3 C2 111.09(13) . . ?
C14 C3 C4 109.94(15) . . ?
C2 C3 C4 104.58(12) . . ?
C14 C3 H3 110.4 . . ?
C2 C3 H3 110.4 . . ?
C4 C3 H3 110.4 . . ?
C16 C4 C5 113.94(14) . . ?
C16 C4 C3 112.12(13) . . ?
C5 C4 C3 105.87(12) . . ?
C16 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
C4 C5 C1 105.80(12) . . ?
C4 C5 H5A 110.6 . . ?
C1 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C1 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
N1 C6 C1 177.7(2) . . ?
N2 C7 C1 176.7(2) . . ?
C13 C8 C9 118.50(15) . . ?
C13 C8 C2 122.66(14) . . ?
C9 C8 C2 118.84(14) . . ?
C10 C9 C8 120.79(16) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.04(16) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.71(16) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.48(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.49(15) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O1 C14 C3 126.0(2) . . ?
O1 C14 H14 117.0 . . ?
C3 C14 H14 117.0 . . ?
C17 C16 C4 125.06(19) . . ?
C17 C16 H16 117.5 . . ?
C4 C16 H16 117.5 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.023



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1456334'
_audit_update_record             
;
2016-02-26 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(1S,5R,6R,8S)-2-imino-8-phenyl-6-vinyl-3-oxabicyclo[3.2.1]octane-1-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 N2 O'
_chemical_formula_weight         252.31

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

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

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

_cell_length_a                   6.9841(7)
_cell_length_b                   12.5978(13)
_cell_length_c                   15.7350(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.885(6)
_cell_angle_gamma                90
_cell_volume                     1371.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.612
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13907
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.835
_diffrn_reflns_theta_max         68.161
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4790
_reflns_number_gt                3486
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.988

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1632P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.6(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4790
_refine_ls_number_parameters     344
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2498
_refine_ls_wR_factor_gt          0.2313
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5786(6) 0.0578(3) 0.0425(3) 0.0487(11) Uani 1 1 d . . . . .
N1 N 0.9083(8) 0.3556(4) -0.0593(4) 0.0524(14) Uani 1 1 d . . . . .
N2 N 0.8891(7) 0.1021(4) 0.0300(4) 0.0553(14) Uani 1 1 d . . . . .
H2 H 0.9180 0.0424 0.0677 0.083 Uiso 1 1 d R U . . .
C1 C 0.6379(8) 0.2179(5) -0.0384(4) 0.0422(13) Uani 1 1 d . . . . .
C2 C 0.4629(8) 0.2710(4) -0.0059(4) 0.0397(13) Uani 1 1 d . . . . .
H2A H 0.4158 0.3286 -0.0473 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3213(8) 0.1774(5) -0.0216(4) 0.0419(13) Uani 1 1 d . . . . .
H3 H 0.1864 0.2016 -0.0177 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3383(9) 0.1396(5) -0.1132(4) 0.0478(15) Uani 1 1 d . . . . .
H4A H 0.3308 0.0603 -0.1153 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5427(9) 0.1751(5) -0.1269(4) 0.0444(14) Uani 1 1 d . . . . .
H5A H 0.6173 0.1145 -0.1454 0.053 Uiso 1 1 calc R U . . .
H5B H 0.5361 0.2315 -0.1710 0.053 Uiso 1 1 calc R U . . .
C6 C 0.3799(8) 0.0932(5) 0.0431(4) 0.0491(15) Uani 1 1 d . . . . .
H6A H 0.3659 0.1207 0.1009 0.059 Uiso 1 1 calc R U . . .
H6B H 0.2919 0.0317 0.0315 0.059 Uiso 1 1 calc R U . . .
C7 C 0.7111(8) 0.1225(5) 0.0160(4) 0.0449(14) Uani 1 1 d . . . . .
C8 C 0.7953(8) 0.2924(5) -0.0481(4) 0.0422(13) Uani 1 1 d . . . . .
C9 C 0.4870(9) 0.3182(5) 0.0829(4) 0.0440(14) Uani 1 1 d . . . . .
C10 C 0.6574(11) 0.3137(6) 0.1402(4) 0.0534(16) Uani 1 1 d . . . . .
H10 H 0.7685 0.2813 0.1229 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6676(13) 0.3551(6) 0.2208(5) 0.0623(19) Uani 1 1 d . . . . .
H11 H 0.7855 0.3509 0.2588 0.075 Uiso 1 1 calc R U . . .
C12 C 0.5097(14) 0.4028(6) 0.2476(4) 0.065(2) Uani 1 1 d . . . . .
H12 H 0.5177 0.4316 0.3038 0.078 Uiso 1 1 calc R U . . .
C13 C 0.3398(13) 0.4084(6) 0.1923(5) 0.0637(19) Uani 1 1 d . . . . .
H13 H 0.2298 0.4415 0.2103 0.076 Uiso 1 1 calc R U . . .
C14 C 0.3280(10) 0.3662(5) 0.1106(5) 0.0517(16) Uani 1 1 d . . . . .
H14 H 0.2095 0.3702 0.0730 0.062 Uiso 1 1 calc R U . . .
C15 C 0.1856(11) 0.1850(6) -0.1784(5) 0.0564(17) Uani 1 1 d . . . . .
H15 H 0.1755 0.2602 -0.1800 0.068 Uiso 1 1 calc R U . . .
C16 C 0.0658(12) 0.1335(9) -0.2328(5) 0.080(2) Uani 1 1 d . . . . .
H16A H 0.0695 0.0581 -0.2341 0.096 Uiso 1 1 calc R U . . .
H16B H -0.0262 0.1709 -0.2718 0.096 Uiso 1 1 calc R U . . .
O2 O 0.4645(7) 0.5706(4) 0.4262(4) 0.0631(14) Uani 1 1 d . . . . .
N3 N 0.1427(9) 0.8513(5) 0.5514(4) 0.0580(15) Uani 1 1 d . . . . .
N4 N 0.1599(8) 0.6091(5) 0.4496(4) 0.0657(17) Uani 1 1 d . . . . .
H4 H 0.1122 0.5569 0.4121 0.099 Uiso 1 1 d R U . . .
C17 C 0.4138(9) 0.7207(5) 0.5208(4) 0.0431(14) Uani 1 1 d . . . . .
C18 C 0.5897(9) 0.7779(5) 0.4915(4) 0.0446(14) Uani 1 1 d . . . . .
H18 H 0.6409 0.8297 0.5372 0.054 Uiso 1 1 calc R U . . .
C19 C 0.7286(9) 0.6823(5) 0.4969(4) 0.0485(15) Uani 1 1 d . . . . .
H19 H 0.8646 0.7061 0.4950 0.058 Uiso 1 1 calc R U . . .
C20 C 0.7086(10) 0.6295(6) 0.5843(5) 0.0574(17) Uani 1 1 d . . . . .
H20 H 0.7026 0.5509 0.5754 0.069 Uiso 1 1 calc R U . . .
C21 C 0.5109(10) 0.6661(6) 0.6050(4) 0.0561(17) Uani 1 1 d . . . . .
H21A H 0.5257 0.7169 0.6534 0.067 Uiso 1 1 calc R U . . .
H21B H 0.4331 0.6049 0.6199 0.067 Uiso 1 1 calc R U . . .
C22 C 0.3360(9) 0.6303(6) 0.4607(4) 0.0487(15) Uani 1 1 d . . . . .
C23 C 0.6629(10) 0.6087(6) 0.4243(5) 0.0596(18) Uani 1 1 d . . . . .
H23A H 0.6694 0.6459 0.3694 0.072 Uiso 1 1 calc R U . . .
H23B H 0.7515 0.5471 0.4271 0.072 Uiso 1 1 calc R U . . .
C24 C 0.2557(10) 0.7912(5) 0.5368(4) 0.0500(16) Uani 1 1 d . . . . .
C25 C 0.5631(10) 0.8355(5) 0.4071(4) 0.0482(15) Uani 1 1 d . . . . .
C26 C 0.3903(12) 0.8439(6) 0.3531(4) 0.0579(18) Uani 1 1 d . . . . .
H26 H 0.2772 0.8124 0.3694 0.069 Uiso 1 1 calc R U . . .
C27 C 0.3787(16) 0.8969(7) 0.2762(5) 0.079(3) Uani 1 1 d . . . . .
H27 H 0.2578 0.9033 0.2406 0.094 Uiso 1 1 calc R U . . .
C28 C 0.5440(18) 0.9411(7) 0.2504(6) 0.082(3) Uani 1 1 d . . . . .
H28 H 0.5372 0.9761 0.1966 0.099 Uiso 1 1 calc R U . . .
C29 C 0.7148(16) 0.9340(6) 0.3025(5) 0.074(2) Uani 1 1 d . . . . .
H29 H 0.8272 0.9651 0.2853 0.089 Uiso 1 1 calc R U . . .
C30 C 0.7276(12) 0.8820(6) 0.3806(5) 0.0599(18) Uani 1 1 d . . . . .
H30 H 0.8485 0.8779 0.4164 0.072 Uiso 1 1 calc R U . . .
C31 C 0.8763(12) 0.6528(9) 0.6531(6) 0.089(3) Uani 1 1 d . . . . .
H31 H 0.9977 0.6609 0.6330 0.107 Uiso 1 1 calc R U . . .
C32 C 0.8799(15) 0.6630(9) 0.7315(6) 0.088(3) Uani 1 1 d . . . . .
H32A H 0.7642 0.6560 0.7564 0.106 Uiso 1 1 calc R U . . .
H32B H 0.9985 0.6778 0.7667 0.106 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 C7 1.342(7) . ?
O1 C6 1.459(7) . ?
N1 C8 1.151(8) . ?
N2 C7 1.259(8) . ?
N2 H2 0.9622 . ?
C1 C8 1.469(9) . ?
C1 C7 1.522(8) . ?
C1 C5 1.555(9) . ?
C1 C2 1.541(9) . ?
C2 C9 1.506(9) . ?
C2 C3 1.538(8) . ?
C2 H2A 1.0000 . ?
C3 C6 1.489(9) . ?
C3 C4 1.537(9) . ?
C3 H3 1.0000 . ?
C4 C15 1.489(10) . ?
C4 C5 1.539(9) . ?
C4 H4A 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 C14 1.387(10) . ?
C9 C10 1.392(9) . ?
C10 C11 1.364(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(11) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.288(11) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?
O2 C22 1.342(8) . ?
O2 C23 1.471(8) . ?
N3 C24 1.140(9) . ?
N4 C22 1.247(9) . ?
N4 H4 0.9148 . ?
C17 C24 1.465(9) . ?
C17 C22 1.531(9) . ?
C17 C18 1.548(9) . ?
C17 C21 1.562(9) . ?
C18 C25 1.503(9) . ?
C18 C19 1.542(9) . ?
C18 H18 1.0000 . ?
C19 C23 1.494(10) . ?
C19 C20 1.551(10) . ?
C19 H19 1.0000 . ?
C20 C31 1.510(11) . ?
C20 C21 1.532(11) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C25 C26 1.382(10) . ?
C25 C30 1.404(11) . ?
C26 C27 1.375(12) . ?
C26 H26 0.9500 . ?
C27 C28 1.392(15) . ?
C27 H27 0.9500 . ?
C28 C29 1.354(15) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(11) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.237(14) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9500 . ?
C32 H32B 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
C7 O1 C6 120.9(5) . . ?
C7 N2 H2 112.7 . . ?
C8 C1 C7 111.4(5) . . ?
C8 C1 C5 111.3(5) . . ?
C7 C1 C5 107.4(5) . . ?
C8 C1 C2 113.3(5) . . ?
C7 C1 C2 112.2(5) . . ?
C5 C1 C2 100.7(5) . . ?
C9 C2 C3 116.0(5) . . ?
C9 C2 C1 119.1(5) . . ?
C3 C2 C1 97.8(5) . . ?
C9 C2 H2A 107.7 . . ?
C3 C2 H2A 107.7 . . ?
C1 C2 H2A 107.7 . . ?
C6 C3 C2 109.0(5) . . ?
C6 C3 C4 111.7(6) . . ?
C2 C3 C4 105.0(5) . . ?
C6 C3 H3 110.3 . . ?
C2 C3 H3 110.3 . . ?
C4 C3 H3 110.3 . . ?
C15 C4 C3 112.7(6) . . ?
C15 C4 C5 112.5(6) . . ?
C3 C4 C5 103.5(5) . . ?
C15 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C1 C5 C4 105.5(5) . . ?
C1 C5 H5A 110.6 . . ?
C4 C5 H5A 110.6 . . ?
C1 C5 H5B 110.6 . . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.8 . . ?
O1 C6 C3 112.7(5) . . ?
O1 C6 H6A 109.0 . . ?
C3 C6 H6A 109.0 . . ?
O1 C6 H6B 109.0 . . ?
C3 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 O1 121.9(6) . . ?
N2 C7 C1 120.5(6) . . ?
O1 C7 C1 117.5(5) . . ?
N1 C8 C1 174.8(6) . . ?
C14 C9 C10 117.7(6) . . ?
C14 C9 C2 118.1(6) . . ?
C10 C9 C2 124.2(6) . . ?
C11 C10 C9 121.2(7) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.8(7) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 119.2(7) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.3(8) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.8(7) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C16 C15 C4 127.1(8) . . ?
C16 C15 H15 116.4 . . ?
C4 C15 H15 116.4 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C22 O2 C23 120.6(5) . . ?
C22 N4 H4 120.7 . . ?
C24 C17 C22 110.2(5) . . ?
C24 C17 C18 114.6(5) . . ?
C22 C17 C18 113.0(5) . . ?
C24 C17 C21 111.8(6) . . ?
C22 C17 C21 105.7(5) . . ?
C18 C17 C21 100.8(5) . . ?
C25 C18 C19 115.2(6) . . ?
C25 C18 C17 118.7(5) . . ?
C19 C18 C17 98.0(5) . . ?
C25 C18 H18 108.1 . . ?
C19 C18 H18 108.1 . . ?
C17 C18 H18 108.1 . . ?
C23 C19 C18 108.5(5) . . ?
C23 C19 C20 110.9(6) . . ?
C18 C19 C20 104.5(5) . . ?
C23 C19 H19 110.9 . . ?
C18 C19 H19 110.9 . . ?
C20 C19 H19 110.9 . . ?
C31 C20 C21 115.0(8) . . ?
C31 C20 C19 113.3(6) . . ?
C21 C20 C19 104.6(5) . . ?
C31 C20 H20 107.8 . . ?
C21 C20 H20 107.8 . . ?
C19 C20 H20 107.8 . . ?
C20 C21 C17 104.6(6) . . ?
C20 C21 H21A 110.8 . . ?
C17 C21 H21A 110.8 . . ?
C20 C21 H21B 110.8 . . ?
C17 C21 H21B 110.8 . . ?
H21A C21 H21B 108.9 . . ?
N4 C22 O2 121.6(6) . . ?
N4 C22 C17 120.4(6) . . ?
O2 C22 C17 117.9(5) . . ?
O2 C23 C19 112.3(6) . . ?
O2 C23 H23A 109.2 . . ?
C19 C23 H23A 109.2 . . ?
O2 C23 H23B 109.2 . . ?
C19 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
N3 C24 C17 175.0(7) . . ?
C26 C25 C30 117.8(7) . . ?
C26 C25 C18 124.9(7) . . ?
C30 C25 C18 117.2(6) . . ?
C27 C26 C25 121.3(9) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C28 C27 C26 120.0(8) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C27 119.6(8) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C30 C29 C28 120.9(10) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C25 120.4(8) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C32 C31 C20 129.9(10) . . ?
C32 C31 H31 115.0 . . ?
C20 C31 H31 115.0 . . ?
C31 C32 H32A 120.0 . . ?
C31 C32 H32B 120.0 . . ?
H32A C32 H32B 120.0 . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.079



