# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_Compound9a
_database_code_depnum_ccdc_archive 'CCDC 1451682'
_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3-benzyl-3-hydroxyindolin-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N O2'
_chemical_formula_sum            'C15 H13 N O2'
_chemical_formula_weight         239.26

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.6173(5)
_cell_length_b                   9.7573(5)
_cell_length_c                   12.8363(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.175(2)
_cell_angle_gamma                90
_cell_volume                     1185.60(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3992
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.29

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.721
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            12517
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.671
_diffrn_reflns_theta_max         68.310
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2174
_reflns_number_gt                1923
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-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)+(0.1000P)²+1.0606P] 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         2174
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   0.659
_refine_ls_restrained_S_all      0.659
_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
O2 O 0.88996(9) 0.38097(8) 0.86303(7) 0.0192(2) Uani 1 1 d . . . . .
H8 H 0.9104 0.3832 0.9278 0.029 Uiso 1 1 calc R U . . .
O1 O 1.06035(9) 0.63960(9) 0.92132(7) 0.0213(2) Uani 1 1 d . . . . .
N1 N 0.99457(10) 0.66007(11) 0.74117(8) 0.0182(2) Uani 1 1 d . . . . .
H5 H 1.0554 0.7206 0.7302 0.022 Uiso 1 1 calc R U . . .
C8 C 0.98348(12) 0.61074(12) 0.83770(10) 0.0168(3) Uani 1 1 d . . . . .
C5 C 0.89400(12) 0.60012(12) 0.66046(10) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.59956(13) 0.52127(13) 0.86519(10) 0.0181(3) Uani 1 1 d . . . . .
C6 C 0.80771(12) 0.51123(12) 0.70535(10) 0.0171(3) Uani 1 1 d . . . . .
C15 C 0.57119(13) 0.39736(13) 0.91151(10) 0.0197(3) Uani 1 1 d . . . . .
H9 H 0.6439 0.3497 0.9537 0.024 Uiso 1 1 calc R U . . .
C7 C 0.85244(12) 0.51463(12) 0.82405(10) 0.0167(3) Uani 1 1 d . . . . .
C9 C 0.74524(13) 0.58361(12) 0.88383(10) 0.0182(3) Uani 1 1 d . . . . .
H7 H 0.7828 0.5802 0.9591 0.022 Uiso 1 1 calc R U . . .
H6 H 0.7369 0.6794 0.8634 0.022 Uiso 1 1 calc R U . . .
C4 C 0.88019(14) 0.61923(13) 0.55282(10) 0.0217(3) Uani 1 1 d . . . . .
H4 H 0.9393 0.6783 0.5241 0.026 Uiso 1 1 calc R U . . .
C1 C 0.70321(13) 0.43778(12) 0.64091(10) 0.0204(3) Uani 1 1 d . . . . .
H1 H 0.6454 0.3776 0.6698 0.025 Uiso 1 1 calc R U . . .
C11 C 0.48873(14) 0.59065(13) 0.80272(11) 0.0220(3) Uani 1 1 d . . . . .
H13 H 0.5064 0.6729 0.7708 0.026 Uiso 1 1 calc R U . . .
C13 C 0.32507(14) 0.41527(14) 0.83314(11) 0.0253(3) Uani 1 1 d . . . . .
H11 H 0.2338 0.3800 0.8225 0.030 Uiso 1 1 calc R U . . .
C2 C 0.68661(14) 0.45611(13) 0.53165(11) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.6168 0.4078 0.4871 0.028 Uiso 1 1 calc R U . . .
C14 C 0.43462(13) 0.34484(13) 0.89477(11) 0.0236(3) Uani 1 1 d . . . . .
H10 H 0.4168 0.2617 0.9253 0.028 Uiso 1 1 calc R U . . .
C3 C 0.77328(14) 0.54578(13) 0.48881(10) 0.0238(3) Uani 1 1 d . . . . .
H3 H 0.7598 0.5572 0.4158 0.029 Uiso 1 1 calc R U . . .
C12 C 0.35222(14) 0.53890(14) 0.78729(11) 0.0248(3) Uani 1 1 d . . . . .
H12 H 0.2789 0.5871 0.7462 0.030 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
O2 C7 1.4204(14) . ?
O2 H8 0.8200 . ?
O1 C8 1.2238(15) . ?
N1 C8 1.3509(16) . ?
N1 C5 1.4131(16) . ?
N1 H5 0.8600 . ?
C8 C7 1.5558(16) . ?
C5 C4 1.3772(18) . ?
C5 C6 1.3936(17) . ?
C10 C11 1.3912(18) . ?
C10 C15 1.3953(18) . ?
C10 C9 1.5072(17) . ?
C6 C1 1.3834(17) . ?
C6 C7 1.5088(17) . ?
C15 C14 1.3908(18) . ?
C15 H9 0.9300 . ?
C7 C9 1.5441(16) . ?
C9 H7 0.9700 . ?
C9 H6 0.9700 . ?
C4 C3 1.3955(19) . ?
C4 H4 0.9300 . ?
C1 C2 1.3948(19) . ?
C1 H1 0.9300 . ?
C11 C12 1.3878(18) . ?
C11 H13 0.9300 . ?
C13 C14 1.383(2) . ?
C13 C12 1.387(2) . ?
C13 H11 0.9300 . ?
C2 C3 1.3873(19) . ?
C2 H2 0.9300 . ?
C14 H10 0.9300 . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H8 109.5 . . ?
C8 N1 C5 111.73(10) . . ?
C8 N1 H5 124.1 . . ?
C5 N1 H5 124.1 . . ?
O1 C8 N1 126.10(11) . . ?
O1 C8 C7 126.10(11) . . ?
N1 C8 C7 107.77(10) . . ?
C4 C5 C6 122.69(12) . . ?
C4 C5 N1 127.71(11) . . ?
C6 C5 N1 109.57(11) . . ?
C11 C10 C15 118.67(12) . . ?
C11 C10 C9 119.41(11) . . ?
C15 C10 C9 121.89(11) . . ?
C1 C6 C5 119.87(12) . . ?
C1 C6 C7 131.50(11) . . ?
C5 C6 C7 108.63(10) . . ?
C14 C15 C10 120.26(12) . . ?
C14 C15 H9 119.9 . . ?
C10 C15 H9 119.9 . . ?
O2 C7 C6 110.17(9) . . ?
O2 C7 C9 112.06(10) . . ?
C6 C7 C9 114.53(10) . . ?
O2 C7 C8 111.31(9) . . ?
C6 C7 C8 101.99(9) . . ?
C9 C7 C8 106.26(9) . . ?
C10 C9 C7 115.39(10) . . ?
C10 C9 H7 108.4 . . ?
C7 C9 H7 108.4 . . ?
C10 C9 H6 108.4 . . ?
C7 C9 H6 108.4 . . ?
H7 C9 H6 107.5 . . ?
C5 C4 C3 116.85(12) . . ?
C5 C4 H4 121.6 . . ?
C3 C4 H4 121.6 . . ?
C6 C1 C2 118.48(12) . . ?
C6 C1 H1 120.8 . . ?
C2 C1 H1 120.8 . . ?
C12 C11 C10 120.95(12) . . ?
C12 C11 H13 119.5 . . ?
C10 C11 H13 119.5 . . ?
C14 C13 C12 119.56(12) . . ?
C14 C13 H11 120.2 . . ?
C12 C13 H11 120.2 . . ?
C3 C2 C1 120.62(12) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C13 C14 C15 120.55(12) . . ?
C13 C14 H10 119.7 . . ?
C15 C14 H10 119.7 . . ?
C2 C3 C4 121.49(12) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C13 C12 C11 120.01(12) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_Compound9c
_database_code_depnum_ccdc_archive 'CCDC 1451683'
_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3-hydroxy-3-(3-methylbenzyl)indolin-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N O2'
_chemical_formula_sum            'C16 H15 N O2'
_chemical_formula_weight         253.29

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.952(3)
_cell_length_b                   11.340(4)
_cell_length_c                   10.721(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.771(7)
_cell_angle_gamma                90
_cell_volume                     1312.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3992
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.29

_exptl_crystal_description       'Needle shaped'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            20234
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.887
_diffrn_reflns_theta_max         28.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3311
_reflns_number_gt                2302
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-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)+(0.1000P)²] 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         3311
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_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
O2 O 0.01654(9) 0.38529(9) 0.84246(10) 0.0191(3) Uani 1 1 d . . . . .
H1 H 0.0061 0.3876 0.9164 0.029 Uiso 1 1 calc R U . . .
O1 O 0.00945(9) 0.63532(9) 0.91513(10) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.06623(11) 0.64872(11) 0.72039(11) 0.0171(3) Uani 1 1 d . . . . .
H003 H 0.0468 0.7213 0.7045 0.021 Uiso 1 1 calc R U . . .
C10 C 0.05525(12) 0.59367(13) 0.82803(13) 0.0156(3) Uani 1 1 d . . . . .
C12 C 0.13630(12) 0.46331(13) 0.69239(13) 0.0163(3) Uani 1 1 d . . . . .
C13 C 0.18006(13) 0.37342(14) 0.62612(14) 0.0191(3) Uani 1 1 d . . . . .
H2 H 0.1951 0.2992 0.6623 0.023 Uiso 1 1 calc R U . . .
C9 C 0.10836(13) 0.46832(13) 0.82394(13) 0.0162(3) Uani 1 1 d . . . . .
C16 C 0.13340(13) 0.59685(14) 0.51567(14) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.1170 0.6708 0.4792 0.023 Uiso 1 1 calc R U . . .
C11 C 0.11355(12) 0.57327(13) 0.63639(13) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.32271(13) 0.54529(14) 0.91891(14) 0.0204(3) Uani 1 1 d . . . . .
C14 C 0.20144(14) 0.39538(14) 0.50425(14) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.2312 0.3354 0.4584 0.025 Uiso 1 1 calc R U . . .
C15 C 0.17884(13) 0.50572(14) 0.45045(15) 0.0206(3) Uani 1 1 d . . . . .
H4 H 0.1944 0.5191 0.3690 0.025 Uiso 1 1 calc R U . . .
C8 C 0.22403(13) 0.45527(14) 0.92727(14) 0.0196(3) Uani 1 1 d . . . . .
H11 H 0.1990 0.4615 1.0096 0.024 Uiso 1 1 calc R U . . .
H10 H 0.2587 0.3772 0.9211 0.024 Uiso 1 1 calc R U . . .
C6 C 0.41044(14) 0.52788(16) 0.84168(15) 0.0255(4) Uani 1 1 d . . . . .
H9 H 0.4101 0.4573 0.7975 0.031 Uiso 1 1 calc R U . . .
C4 C 0.32568(14) 0.64971(16) 0.98612(18) 0.0296(4) Uani 1 1 d . . . . .
H12 H 0.2691 0.6625 1.0403 0.036 Uiso 1 1 calc R U . . .
C1 C 0.49864(15) 0.61221(18) 0.82822(16) 0.0335(5) Uani 1 1 d . . . . .
C2 C 0.49755(16) 0.71614(18) 0.8945(2) 0.0411(5) Uani 1 1 d . . . . .
H14 H 0.5553 0.7745 0.8860 0.049 Uiso 1 1 calc R U . . .
C3 C 0.41236(16) 0.73486(17) 0.9728(2) 0.0426(5) Uani 1 1 d . . . . .
H13 H 0.4132 0.8054 1.0172 0.051 Uiso 1 1 calc R U . . .
C7 C 0.59324(17) 0.5889(3) 0.74510(19) 0.0547(7) Uani 1 1 d . . . . .
H7 H 0.6114 0.6610 0.7049 0.082 Uiso 1 1 calc R U . . .
H6 H 0.5613 0.5320 0.6817 0.082 Uiso 1 1 calc R U . . .
H8 H 0.6676 0.5590 0.7955 0.082 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
O2 C9 1.4160(18) . ?
O2 H1 0.8200 . ?
O1 C10 1.2271(18) . ?
N1 C10 1.3354(19) . ?
N1 C11 1.4036(19) . ?
N1 H003 0.8600 . ?
C10 C9 1.539(2) . ?
C12 C13 1.374(2) . ?
C12 C11 1.388(2) . ?
C12 C9 1.494(2) . ?
C13 C14 1.389(2) . ?
C13 H2 0.9300 . ?
C9 C8 1.5421(19) . ?
C16 C11 1.375(2) . ?
C16 C15 1.387(2) . ?
C16 H5 0.9300 . ?
C5 C4 1.384(2) . ?
C5 C6 1.385(2) . ?
C5 C8 1.500(2) . ?
C14 C15 1.382(2) . ?
C14 H3 0.9300 . ?
C15 H4 0.9300 . ?
C8 H11 0.9700 . ?
C8 H10 0.9700 . ?
C6 C1 1.384(2) . ?
C6 H9 0.9300 . ?
C4 C3 1.378(3) . ?
C4 H12 0.9300 . ?
C1 C2 1.377(3) . ?
C1 C7 1.500(3) . ?
C2 C3 1.374(3) . ?
C2 H14 0.9300 . ?
C3 H13 0.9300 . ?
C7 H7 0.9600 . ?
C7 H6 0.9600 . ?
C7 H8 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H1 109.5 . . ?
C10 N1 C11 111.52(13) . . ?
C10 N1 H003 124.2 . . ?
C11 N1 H003 124.2 . . ?
O1 C10 N1 125.89(14) . . ?
O1 C10 C9 125.62(13) . . ?
N1 C10 C9 108.49(12) . . ?
C13 C12 C11 119.69(14) . . ?
C13 C12 C9 131.41(14) . . ?
C11 C12 C9 108.88(13) . . ?
C12 C13 C14 118.87(15) . . ?
C12 C13 H2 120.6 . . ?
C14 C13 H2 120.6 . . ?
O2 C9 C12 111.79(12) . . ?
O2 C9 C10 109.23(12) . . ?
C12 C9 C10 101.59(11) . . ?
O2 C9 C8 110.60(12) . . ?
C12 C9 C8 113.55(12) . . ?
C10 C9 C8 109.66(12) . . ?
C11 C16 C15 117.22(14) . . ?
C11 C16 H5 121.4 . . ?
C15 C16 H5 121.4 . . ?
C16 C11 C12 122.45(14) . . ?
C16 C11 N1 128.33(14) . . ?
C12 C11 N1 109.20(13) . . ?
C4 C5 C6 118.42(16) . . ?
C4 C5 C8 120.31(15) . . ?
C6 C5 C8 121.24(15) . . ?
C15 C14 C13 120.53(15) . . ?
C15 C14 H3 119.7 . . ?
C13 C14 H3 119.7 . . ?
C14 C15 C16 121.23(15) . . ?
C14 C15 H4 119.4 . . ?
C16 C15 H4 119.4 . . ?
C5 C8 C9 113.83(12) . . ?
C5 C8 H11 108.8 . . ?
C9 C8 H11 108.8 . . ?
C5 C8 H10 108.8 . . ?
C9 C8 H10 108.8 . . ?
H11 C8 H10 107.7 . . ?
C1 C6 C5 122.08(17) . . ?
C1 C6 H9 119.0 . . ?
C5 C6 H9 119.0 . . ?
C3 C4 C5 120.10(18) . . ?
C3 C4 H12 120.0 . . ?
C5 C4 H12 120.0 . . ?
C2 C1 C6 118.05(18) . . ?
C2 C1 C7 121.61(19) . . ?
C6 C1 C7 120.3(2) . . ?
C3 C2 C1 120.92(17) . . ?
C3 C2 H14 119.5 . . ?
C1 C2 H14 119.5 . . ?
C2 C3 C4 120.40(19) . . ?
C2 C3 H13 119.8 . . ?
C4 C3 H13 119.8 . . ?
C1 C7 H7 109.5 . . ?
C1 C7 H6 109.5 . . ?
H7 C7 H6 109.5 . . ?
C1 C7 H8 109.5 . . ?
H7 C7 H8 109.5 . . ?
H6 C7 H8 109.5 . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.057

