# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_TRIAL1_a
_database_code_depnum_ccdc_archive 'CCDC 1059904'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31

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           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                   7.6266(8)
_cell_length_b                   18.5193(18)
_cell_length_c                   10.0793(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.801(5)
_cell_angle_gamma                90
_cell_volume                     1347.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7665
_cell_measurement_theta_min      4.78
_cell_measurement_theta_max      68.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             594
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.625
_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      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16428
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.776
_diffrn_reflns_theta_max         68.371
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2475
_reflns_number_gt                1941
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1000P)²+0.2305P] 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         2475
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_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
C1 C 0.23862(19) 0.35688(8) 0.79562(15) 0.0450(4) Uani 1 1 d . . . . .
C2 C 0.2346(3) 0.37140(10) 1.04385(17) 0.0586(4) Uani 1 1 d . . . . .
H2A H 0.3441 0.3406 1.0876 0.070 Uiso 1 1 calc R U . . .
H2B H 0.1210 0.3431 1.0342 0.070 Uiso 1 1 calc R U . . .
C3 C 0.2404(2) 0.44008(10) 1.13111(18) 0.0617(5) Uani 1 1 d . . . . .
H3A H 0.1282 0.4437 1.1598 0.074 Uiso 1 1 calc R U . . .
H3B H 0.3511 0.4402 1.2161 0.074 Uiso 1 1 calc R U . . .
C4 C 0.2484(2) 0.50124(9) 1.03490(16) 0.0532(4) Uani 1 1 d . . . . .
C5 C 0.2582(2) 0.57493(10) 1.0493(2) 0.0651(5) Uani 1 1 d . . . . .
H5 H 0.2613 0.5967 1.1353 0.078 Uiso 1 1 calc R U . . .
C6 C 0.2636(2) 0.61781(10) 0.9362(2) 0.0654(5) Uani 1 1 d . . . . .
H6 H 0.2698 0.6688 0.9465 0.078 Uiso 1 1 calc R U . . .
C7 C 0.2602(2) 0.58771(9) 0.81038(18) 0.0559(4) Uani 1 1 d . . . . .
H7 H 0.2640 0.6181 0.7354 0.067 Uiso 1 1 calc R U . . .
C8 C 0.25111(19) 0.51228(8) 0.79195(15) 0.0449(4) Uani 1 1 d . . . . .
C9 C 0.24480(18) 0.47247(8) 0.90691(15) 0.0449(4) Uani 1 1 d . . . . .
C10 C 0.25349(18) 0.47164(8) 0.66984(15) 0.0428(3) Uani 1 1 d . . . . .
C11 C 0.2588(2) 0.51237(8) 0.54204(17) 0.0551(4) Uani 1 1 d . . . . .
H11A H 0.2467 0.4783 0.4651 0.083 Uiso 1 1 calc R U . . .
H11B H 0.3767 0.5383 0.5634 0.083 Uiso 1 1 calc R U . . .
H11C H 0.1563 0.5470 0.5143 0.083 Uiso 1 1 calc R U . . .
C12 C 0.25179(18) 0.39802(7) 0.67358(15) 0.0418(3) Uani 1 1 d . . . . .
C13 C 0.2712(2) 0.35301(7) 0.55618(15) 0.0430(4) Uani 1 1 d . . . . .
C14 C 0.1208(2) 0.31932(8) 0.46077(17) 0.0544(4) Uani 1 1 d . . . . .
H14 H 0.0013 0.3237 0.4703 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1438(3) 0.27925(9) 0.35167(18) 0.0638(5) Uani 1 1 d . . . . .
H15 H 0.0394 0.2575 0.2850 0.077 Uiso 1 1 calc R U . . .
C16 C 0.3172(3) 0.27074(8) 0.33931(18) 0.0626(5) Uani 1 1 d . . . . .
H16 H 0.3323 0.2427 0.2649 0.075 Uiso 1 1 calc R U . . .
C17 C 0.4686(3) 0.30279(9) 0.43455(18) 0.0605(5) Uani 1 1 d . . . . .
H17 H 0.5886 0.2965 0.4268 0.073 Uiso 1 1 calc R U . . .
C18 C 0.4451(2) 0.34427(8) 0.54164(16) 0.0521(4) Uani 1 1 d . . . . .
H18 H 0.5494 0.3671 0.6063 0.063 Uiso 1 1 calc R U . . .
N1 N 0.23537(17) 0.39864(7) 0.90636(13) 0.0473(3) Uani 1 1 d . . . . .
O1 O 0.23134(17) 0.29064(6) 0.79970(12) 0.0629(4) 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
C1 O1 1.2292(18) . ?
C1 N1 1.3647(18) . ?
C1 C12 1.4775(18) . ?
C2 N1 1.4766(18) . ?
C2 C3 1.539(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.505(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.372(2) . ?
C4 C9 1.388(2) . ?
C5 C6 1.400(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.408(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(2) . ?
C8 C10 1.4477(19) . ?
C9 N1 1.369(2) . ?
C10 C12 1.364(2) . ?
C10 C11 1.5044(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.4932(19) . ?
C13 C14 1.385(2) . ?
C13 C18 1.390(2) . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 H18 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
O1 C1 N1 121.68(13) . . ?
O1 C1 C12 123.94(13) . . ?
N1 C1 C12 114.37(13) . . ?
N1 C2 C3 104.24(13) . . ?
N1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C4 C3 C2 104.67(13) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C9 117.66(16) . . ?
C5 C4 C3 133.84(16) . . ?
C9 C4 C3 108.50(14) . . ?
C4 C5 C6 119.54(16) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 121.53(16) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 120.55(16) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 115.50(14) . . ?
C9 C8 C10 116.56(14) . . ?
C7 C8 C10 127.90(14) . . ?
N1 C9 C8 122.91(13) . . ?
N1 C9 C4 111.86(14) . . ?
C8 C9 C4 125.23(15) . . ?
C12 C10 C8 119.55(13) . . ?
C12 C10 C11 121.86(13) . . ?
C8 C10 C11 118.59(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 C1 122.83(13) . . ?
C10 C12 C13 122.13(12) . . ?
C1 C12 C13 114.99(12) . . ?
C14 C13 C18 118.62(14) . . ?
C14 C13 C12 122.02(13) . . ?
C18 C13 C12 119.36(13) . . ?
C15 C14 C13 120.30(16) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.31(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.15(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.55(16) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 121.02(15) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C1 N1 C9 123.67(12) . . ?
C1 N1 C2 125.49(13) . . ?
C9 N1 C2 110.70(12) . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.032

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dcm-ethylacetate'
####################################################################### 
# 
# 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_TRIAL1_a
_database_code_depnum_ccdc_archive 'CCDC 1059951'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31

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      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                   8.1792(3)
_cell_length_b                   8.2361(3)
_cell_length_c                   11.9209(4)
_cell_angle_alpha                91.062(2)
_cell_angle_beta                 95.422(2)
_cell_angle_gamma                119.402(2)
_cell_volume                     694.53(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4135
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      68.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.730
_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      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7560
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.735
_diffrn_reflns_theta_max         68.392
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2525
_reflns_number_gt                2032
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1000P)²+0.5849P] 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         2525
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   0.639
_refine_ls_restrained_S_all      0.639
_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
C1 C 0.6273(4) 0.8610(4) -0.02437(17) 0.0890(8) Uani 1 1 d . . . . .
H1A H 0.7624 0.9053 -0.0248 0.134 Uiso 1 1 calc R U . . .
H1B H 0.5946 0.9473 -0.0627 0.134 Uiso 1 1 calc R U . . .
H1C H 0.5538 0.7362 -0.0638 0.134 Uiso 1 1 calc R U . . .
C2 C 0.6401(3) 0.7574(3) 0.15672(17) 0.0604(5) Uani 1 1 d . . . . .
C3 C 0.5905(2) 0.7585(2) 0.27444(14) 0.0491(4) Uani 1 1 d . . . . .
C4 C 0.7340(2) 0.9184(2) 0.34964(15) 0.0495(4) Uani 1 1 d . . . . .
C5 C 0.8042(2) 1.0617(2) 0.54976(16) 0.0534(4) Uani 1 1 d . . . . .
H5A H 0.8108 1.1817 0.5323 0.064 Uiso 1 1 calc R U . . .
H5B H 0.9342 1.0813 0.5626 0.064 Uiso 1 1 calc R U . . .
C6 C 0.6993(3) 0.9853(2) 0.65366(16) 0.0560(4) Uani 1 1 d . . . . .
H6A H 0.7780 0.9617 0.7120 0.067 Uiso 1 1 calc R U . . .
H6B H 0.6653 1.0743 0.6869 0.067 Uiso 1 1 calc R U . . .
C7 C 0.5238(2) 0.8047(2) 0.60814(14) 0.0466(4) Uani 1 1 d . . . . .
C8 C 0.5313(2) 0.7753(2) 0.49427(13) 0.0417(4) Uani 1 1 d . . . . .
C9 C 0.3952(2) 0.6226(2) 0.42368(13) 0.0420(4) Uani 1 1 d . . . . .
C10 C 0.2414(2) 0.4891(2) 0.47563(14) 0.0480(4) Uani 1 1 d . . . . .
H10 H 0.1441 0.3807 0.4325 0.058 Uiso 1 1 calc R U . . .
C11 C 0.2319(2) 0.5156(2) 0.58837(15) 0.0538(4) Uani 1 1 d . . . . .
H11 H 0.1272 0.4241 0.6218 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3718(2) 0.6732(2) 0.65591(15) 0.0535(4) Uani 1 1 d . . . . .
H12 H 0.3611 0.6885 0.7336 0.064 Uiso 1 1 calc R U . . .
C13 C 0.4283(2) 0.6181(2) 0.30686(14) 0.0458(4) Uani 1 1 d . . . . .
C14 C 0.2794(3) 0.4642(2) 0.22412(15) 0.0556(4) Uani 1 1 d . . . . .
H14A H 0.2289 0.3441 0.2600 0.067 Uiso 1 1 calc R U . . .
H14B H 0.3381 0.4536 0.1575 0.067 Uiso 1 1 calc R U . . .
C15 C 0.1171(3) 0.4987(3) 0.18530(16) 0.0643(5) Uani 1 1 d . . . . .
H15A H 0.0606 0.5130 0.2520 0.077 Uiso 1 1 calc R U . . .
H15B H 0.1668 0.6168 0.1472 0.077 Uiso 1 1 calc R U . . .
C16 C -0.0342(3) 0.3407(3) 0.10508(19) 0.0873(8) Uani 1 1 d . . . . .
H16A H 0.0208 0.3274 0.0383 0.131 Uiso 1 1 calc R U . . .
H16B H -0.1357 0.3681 0.0819 0.131 Uiso 1 1 calc R U . . .
H16C H -0.0856 0.2240 0.1431 0.131 Uiso 1 1 calc R U . . .
N1 N 0.69094(18) 0.91663(17) 0.45749(12) 0.0461(3) Uani 1 1 d . . . . .
O1 O 0.5845(2) 0.85231(19) 0.09106(10) 0.0659(4) Uani 1 1 d . . . . .
O2 O 0.7165(3) 0.6770(3) 0.12441(16) 0.1191(8) Uani 1 1 d . . . . .
O3 O 0.88113(17) 1.04478(19) 0.32047(12) 0.0670(4) 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
C1 O1 1.446(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.191(2) . ?
C2 O1 1.317(2) . ?
C2 C3 1.498(2) . ?
C3 C13 1.361(2) . ?
C3 C4 1.468(2) . ?
C4 O3 1.231(2) . ?
C4 N1 1.363(2) . ?
C5 N1 1.472(2) . ?
C5 C6 1.538(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.515(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.370(2) . ?
C7 C8 1.387(2) . ?
C8 N1 1.373(2) . ?
C8 C9 1.392(2) . ?
C9 C10 1.411(2) . ?
C9 C13 1.447(2) . ?
C10 C11 1.373(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.508(2) . ?
C14 C15 1.522(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.513(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.34(19) . . ?
O2 C2 C3 124.64(18) . . ?
O1 C2 C3 111.99(15) . . ?
C13 C3 C4 124.43(16) . . ?
C13 C3 C2 121.54(16) . . ?
C4 C3 C2 114.00(15) . . ?
O3 C4 N1 121.64(17) . . ?
O3 C4 C3 124.43(17) . . ?
N1 C4 C3 113.93(14) . . ?
N1 C5 C6 104.61(13) . . ?
N1 C5 H5A 110.8 . . ?
C6 C5 H5A 110.8 . . ?
N1 C5 H5B 110.8 . . ?
C6 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C7 C6 C5 104.35(14) . . ?
C7 C6 H6A 110.9 . . ?
C5 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
C12 C7 C8 117.92(15) . . ?
C12 C7 C6 133.70(16) . . ?
C8 C7 C6 108.36(15) . . ?
N1 C8 C7 111.93(14) . . ?
N1 C8 C9 122.96(15) . . ?
C7 C8 C9 125.11(15) . . ?
C8 C9 C10 115.55(15) . . ?
C8 C9 C13 116.72(14) . . ?
C10 C9 C13 127.72(15) . . ?
C11 C10 C9 120.13(15) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 122.24(16) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C7 C12 C11 119.04(16) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C3 C13 C9 118.48(15) . . ?
C3 C13 C14 122.14(16) . . ?
C9 C13 C14 119.32(15) . . ?
C13 C14 C15 112.40(14) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 111.91(19) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 N1 C8 123.42(14) . . ?
C4 N1 C5 125.99(14) . . ?
C8 N1 C5 110.59(14) . . ?
C2 O1 C1 116.25(16) . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.034

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dcm ethylacetate'
