# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Compound-1
_audit_block_doi                 10.5517/cc14gldl
_database_code_depnum_ccdc_archive 'CCDC 1056709'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        3-imino-2-phenethylisoindolin-1-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_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      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                   13.4616(3)
_cell_length_b                   4.95900(10)
_cell_length_c                   19.7696(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.710(2)
_cell_angle_gamma                90
_cell_volume                     1316.98(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    1907
_cell_measurement_theta_min      3.8440
_cell_measurement_theta_max      72.7480

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_T_min  0.87424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            4354
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.859
_diffrn_reflns_theta_max         73.251
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2540
_reflns_number_gt                2097
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0510P)²+0.2368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2540
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_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
O2 O 0.61674(7) 0.5269(2) 0.66913(5) 0.0265(2) Uani 1 1 d . . . . .
N1 N 0.30166(8) 0.2771(2) 0.72339(6) 0.0216(3) Uani 1 1 d . . . . .
N2 N 0.45118(7) 0.4401(2) 0.68528(5) 0.0186(2) Uani 1 1 d . . . . .
C1 C 0.33620(11) 0.8744(3) 0.47947(7) 0.0266(3) Uani 1 1 d . . . . .
H1 H 0.3995 0.8280 0.4643 0.032 Uiso 1 1 calc R U . . .
C2 C 0.28018(12) 1.0768(3) 0.44621(7) 0.0322(4) Uani 1 1 d . . . . .
H2 H 0.3055 1.1676 0.4087 0.039 Uiso 1 1 calc R U . . .
C3 C 0.18811(12) 1.1453(3) 0.46771(7) 0.0325(4) Uani 1 1 d . . . . .
H3 H 0.1500 1.2836 0.4451 0.039 Uiso 1 1 calc R U . . .
C4 C 0.15139(11) 1.0119(3) 0.52231(8) 0.0321(4) Uani 1 1 d . . . . .
H4 H 0.0878 1.0581 0.5371 0.038 Uiso 1 1 calc R U . . .
C5 C 0.20725(10) 0.8106(3) 0.55553(7) 0.0269(3) Uani 1 1 d . . . . .
H5 H 0.1814 0.7202 0.5930 0.032 Uiso 1 1 calc R U . . .
C6 C 0.30044(10) 0.7395(3) 0.53477(6) 0.0217(3) Uani 1 1 d . . . . .
C7 C 0.36135(10) 0.5276(3) 0.57325(7) 0.0241(3) Uani 1 1 d . . . . .
H7A H 0.4154 0.4645 0.5455 0.029 Uiso 1 1 calc R U . . .
H7B H 0.3186 0.3711 0.5825 0.029 Uiso 1 1 calc R U . . .
C8 C 0.40604(9) 0.6445(3) 0.64027(6) 0.0201(3) Uani 1 1 d . . . . .
H8A H 0.4571 0.7801 0.6304 0.024 Uiso 1 1 calc R U . . .
H8B H 0.3530 0.7378 0.6636 0.024 Uiso 1 1 calc R U . . .
C9 C 0.39619(9) 0.2696(3) 0.72522(6) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.47069(9) 0.1037(3) 0.76527(6) 0.0178(3) Uani 1 1 d . . . . .
C11 C 0.45850(9) -0.0984(3) 0.81258(6) 0.0209(3) Uani 1 1 d . . . . .
H11 H 0.3942 -0.1561 0.8236 0.025 Uiso 1 1 calc R U . . .
C12 C 0.54455(10) -0.2135(3) 0.84333(7) 0.0231(3) Uani 1 1 d . . . . .
H12 H 0.5387 -0.3536 0.8756 0.028 Uiso 1 1 calc R U . . .
C13 C 0.63904(10) -0.1270(3) 0.82765(7) 0.0230(3) Uani 1 1 d . . . . .
H13 H 0.6963 -0.2073 0.8499 0.028 Uiso 1 1 calc R U . . .
C14 C 0.65059(9) 0.0756(3) 0.77987(7) 0.0214(3) Uani 1 1 d . . . . .
H14 H 0.7147 0.1351 0.7689 0.026 Uiso 1 1 calc R U . . .
C15 C 0.56473(9) 0.1864(3) 0.74902(6) 0.0184(3) Uani 1 1 d . . . . .
C16 C 0.55309(9) 0.4030(3) 0.69712(6) 0.0192(3) Uani 1 1 d . . . . .
H1N H 0.2763(13) 0.148(4) 0.7522(9) 0.037(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C16 1.2162(16) . ?
N1 C9 1.2713(16) . ?
N1 H1N 0.937(19) . ?
N2 C16 1.3889(15) . ?
N2 C9 1.4007(17) . ?
N2 C8 1.4554(16) . ?
C1 C6 1.3940(19) . ?
C1 C2 1.394(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3904(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.5081(19) . ?
C7 C8 1.5331(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.4855(18) . ?
C10 C15 1.3880(17) . ?
C10 C11 1.3878(19) . ?
C11 C12 1.3950(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3961(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3852(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.4867(19) . ?

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
C9 N1 H1N 111.5(11) . . ?
C16 N2 C9 112.16(11) . . ?
C16 N2 C8 124.34(11) . . ?
C9 N2 C8 123.37(10) . . ?
C6 C1 C2 120.79(14) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.10(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.74(14) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.17(14) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.93(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.27(13) . . ?
C5 C6 C7 119.96(12) . . ?
C1 C6 C7 121.74(13) . . ?
C6 C7 C8 110.03(11) . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N2 C8 C7 112.95(11) . . ?
N2 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 N2 122.07(12) . . ?
N1 C9 C10 132.16(12) . . ?
N2 C9 C10 105.77(10) . . ?
C15 C10 C11 121.25(12) . . ?
C15 C10 C9 107.89(11) . . ?
C11 C10 C9 130.85(11) . . ?
C10 C11 C12 117.26(12) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C11 C12 C13 121.35(13) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 121.00(12) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 117.23(12) . . ?
C15 C14 H14 121.4 . . ?
C13 C14 H14 121.4 . . ?
C14 C15 C10 121.90(13) . . ?
C14 C15 C16 129.66(12) . . ?
C10 C15 C16 108.44(11) . . ?
O2 C16 N2 125.01(12) . . ?
O2 C16 C15 129.27(12) . . ?
N2 C16 C15 105.72(10) . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate/Petroleum Ether'
####################################################################### 
# 
# 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_compound-1
_database_code_depnum_ccdc_archive 'CCDC 1406595'
_audit_update_record             
;
2015-06-14 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(E)-3-(3-(2-(2-cyano-N-methylbenzamido)ethyl)phenyl)acrylic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   33.970(16)
_cell_length_b                   6.299(3)
_cell_length_c                   16.431(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.257(8)
_cell_angle_gamma                90
_cell_volume                     3513(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3201
_cell_measurement_theta_min      2.4002
_cell_measurement_theta_max      27.6218

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9560
_exptl_absorpt_process_details   
;
RIGAKU/MSC(2004), CrystalClear Version 1.3.6,  
  Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX77381-5209, USA
;
_exptl_special_details           
;
?
;
_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  
;
Mercury70 (2x2 bin mode)
;
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 14.6306
_diffrn_reflns_number            12961
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.400
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4016
_reflns_number_gt                2811
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0661P)²+1.3959P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4016
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.090
_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 0.63739(6) 0.0358(3) 0.48696(11) 0.1003(6) Uani 1 1 d . . . . .
O2 O 0.53382(5) 0.0548(3) 0.93108(10) 0.0906(5) Uani 1 1 d . . . . .
H2O H 0.5263(7) -0.096(4) 0.9787(16) 0.109 Uiso 1 1 d . U . . .
O3 O 0.48308(5) 0.2477(3) 0.96749(10) 0.0924(6) Uani 1 1 d . . . . .
N1 N 0.73743(8) 0.0036(4) 0.54632(12) 0.0973(7) Uani 1 1 d . . . . .
N2 N 0.64072(4) 0.3734(2) 0.44260(8) 0.0511(4) Uani 1 1 d . . . . .
C1 C 0.72703(7) 0.0070(3) 0.47957(12) 0.0651(5) Uani 1 1 d . . . . .
C2 C 0.71355(6) 0.0118(3) 0.39490(10) 0.0509(4) Uani 1 1 d . . . . .
C3 C 0.73723(6) -0.0688(3) 0.33550(11) 0.0622(5) Uani 1 1 d . . . . .
H3 H 0.7624 -0.1263 0.3500 0.075 Uiso 1 1 calc R U . . .
C4 C 0.72389(7) -0.0648(3) 0.25506(12) 0.0680(6) Uani 1 1 d . . . . .
H4 H 0.7401 -0.1184 0.2139 0.082 Uiso 1 1 calc R U . . .
C5 C 0.68760(7) 0.0156(3) 0.23441(11) 0.0661(6) Uani 1 1 d . . . . .
H5 H 0.6785 0.0156 0.1790 0.079 Uiso 1 1 calc R U . . .
C6 C 0.66397(6) 0.0968(3) 0.29316(11) 0.0600(5) Uani 1 1 d . . . . .
H6 H 0.6388 0.1536 0.2780 0.072 Uiso 1 1 calc R U . . .
C7 C 0.67676(5) 0.0960(3) 0.37427(10) 0.0488(4) Uani 1 1 d . . . . .
C8 C 0.64991(6) 0.1682(3) 0.43976(11) 0.0579(5) Uani 1 1 d . . . . .
C9 C 0.66032(6) 0.5366(3) 0.39652(12) 0.0623(5) Uani 1 1 d . . . . .
H9A H 0.6868 0.4881 0.3839 0.094 Uiso 1 1 calc R U . . .
H9B H 0.6623 0.6671 0.4289 0.094 Uiso 1 1 calc R U . . .
H9C H 0.6451 0.5646 0.3457 0.094 Uiso 1 1 calc R U . . .
C10 C 0.61342(5) 0.4463(3) 0.50326(11) 0.0568(5) Uani 1 1 d . . . . .
H10A H 0.5952 0.3291 0.5159 0.068 Uiso 1 1 calc R U . . .
H10B H 0.5975 0.5648 0.4801 0.068 Uiso 1 1 calc R U . . .
C11 C 0.63440(6) 0.5200(3) 0.58142(10) 0.0583(5) Uani 1 1 d . . . . .
H11A H 0.6502 0.4018 0.6052 0.070 Uiso 1 1 calc R U . . .
H11B H 0.6526 0.6378 0.5692 0.070 Uiso 1 1 calc R U . . .
C12 C 0.60515(5) 0.5940(3) 0.64191(10) 0.0521(5) Uani 1 1 d . . . . .
C13 C 0.58845(6) 0.7952(3) 0.63569(11) 0.0580(5) Uani 1 1 d . . . . .
H13 H 0.5954 0.8869 0.5926 0.070 Uiso 1 1 calc R U . . .
C14 C 0.56175(6) 0.8629(3) 0.69187(12) 0.0616(5) Uani 1 1 d . . . . .
H14 H 0.5508 1.0014 0.6875 0.074 Uiso 1 1 calc R U . . .
C15 C 0.55098(5) 0.7305(3) 0.75408(11) 0.0578(5) Uani 1 1 d . . . . .
H15 H 0.5333 0.7798 0.7932 0.069 Uiso 1 1 calc R U . . .
C16 C 0.56595(5) 0.5249(3) 0.75992(10) 0.0523(4) Uani 1 1 d . . . . .
C17 C 0.59339(5) 0.4611(3) 0.70375(10) 0.0529(5) Uani 1 1 d . . . . .
H17 H 0.6043 0.3225 0.7080 0.063 Uiso 1 1 calc R U . . .
C18 C 0.55347(6) 0.3720(3) 0.82109(10) 0.0579(5) Uani 1 1 d . . . . .
H18 H 0.5690 0.2471 0.8270 0.070 Uiso 1 1 calc R U . . .
C19 C 0.52342(6) 0.3871(4) 0.86869(11) 0.0653(5) Uani 1 1 d . . . . .
H19 H 0.5076 0.5115 0.8658 0.078 Uiso 1 1 calc R U . . .
C20 C 0.51334(6) 0.2203(4) 0.92588(11) 0.0626(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.226(2) . ?
O2 C20 1.254(3) . ?
O2 H2O 1.26(3) . ?
O3 C20 1.268(2) . ?
N1 C1 1.139(3) . ?
N2 C8 1.331(2) . ?
N2 C9 1.454(2) . ?
N2 C10 1.462(2) . ?
C1 C2 1.448(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.387(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.508(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.506(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.387(2) . ?
C12 C13 1.390(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(2) . ?
C16 C18 1.467(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.314(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.459(3) . ?
C19 H19 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
C20 O2 H2O 122.8(11) . . ?
C8 N2 C9 123.76(16) . . ?
C8 N2 C10 119.01(15) . . ?
C9 N2 C10 116.66(15) . . ?
N1 C1 C2 179.6(3) . . ?
C3 C2 C7 120.70(16) . . ?
C3 C2 C1 119.92(18) . . ?
C7 C2 C1 119.38(17) . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.31(18) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.64(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 120.21(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 118.80(16) . . ?
C6 C7 C8 120.65(18) . . ?
C2 C7 C8 120.35(16) . . ?
O1 C8 N2 123.41(18) . . ?
O1 C8 C7 118.74(18) . . ?
N2 C8 C7 117.85(15) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 112.59(15) . . ?
N2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 110.68(15) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C17 C12 C13 118.38(17) . . ?
C17 C12 C11 120.85(18) . . ?
C13 C12 C11 120.74(17) . . ?
C14 C13 C12 120.49(18) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.43(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.43(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 118.25(17) . . ?
C15 C16 C18 122.90(17) . . ?
C17 C16 C18 118.84(18) . . ?
C12 C17 C16 121.95(18) . . ?
C12 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C19 C18 C16 127.8(2) . . ?
C19 C18 H18 116.1 . . ?
C16 C18 H18 116.1 . . ?
C18 C19 C20 122.6(2) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
O2 C20 O3 122.4(2) . . ?
O2 C20 C19 119.91(19) . . ?
O3 C20 C19 117.7(2) . . ?

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
O2 H2O O2 1.26(3) 2.58(3) 3.361(3) 117.7(15) 5_657
O2 H2O O3 1.26(3) 1.35(3) 2.610(2) 176(2) 5_657

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.032



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
