# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ic18036
_database_code_depnum_ccdc_archive 'CCDC 1523958'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-03-29 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         ?
_chemical_formula_sum            'C16 H20 N2 O'
_chemical_formula_weight         256.34

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                   8.1090(2)
_cell_length_b                   9.1450(2)
_cell_length_c                   9.2939(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.4248(6)
_cell_angle_gamma                90
_cell_volume                     684.88(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8704
_cell_measurement_theta_min      4.79
_cell_measurement_theta_max      70.18

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.614
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5807
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_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  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4672
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.788
_diffrn_reflns_theta_max         69.997
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2573
_reflns_number_gt                2546
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.993

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0358P)²+0.1043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0119(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1166 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2573
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.34831(15) 0.65005(14) 0.43409(12) 0.0280(3) Uani 1 1 d . . . . .
H1 H 0.4268 0.6803 0.3903 0.042 Uiso 1 1 calc R U . . .
N1 N 0.48424(16) 0.63480(16) 0.67270(14) 0.0230(3) Uani 1 1 d . . . . .
N2 N 0.39377(17) 0.23970(16) 0.71586(15) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.62609(19) 0.69679(18) 0.74522(16) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.6871(2) 0.83928(19) 0.74229(19) 0.0283(4) Uani 1 1 d . . . . .
H2 H 0.6302 0.9123 0.6833 0.034 Uiso 1 1 calc R U . . .
C3 C 0.8337(2) 0.8708(2) 0.8286(2) 0.0332(4) Uani 1 1 d . . . . .
H3 H 0.8784 0.9668 0.8278 0.040 Uiso 1 1 calc R U . . .
C4 C 0.9170(2) 0.7639(2) 0.9167(2) 0.0332(4) Uani 1 1 d . . . . .
H4 H 1.0169 0.7885 0.9750 0.040 Uiso 1 1 calc R U . . .
C5 C 0.85620(19) 0.6234(2) 0.92023(18) 0.0276(4) Uani 1 1 d . . . . .
H5 H 0.9137 0.5514 0.9802 0.033 Uiso 1 1 calc R U . . .
C6 C 0.70813(18) 0.58790(18) 0.83406(16) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.60970(19) 0.45818(18) 0.81510(17) 0.0224(3) Uani 1 1 d . . . . .
C8 C 0.6287(2) 0.31304(19) 0.88956(19) 0.0271(4) Uani 1 1 d . . . . .
H8A H 0.6649 0.3271 0.9939 0.033 Uiso 1 1 calc R U . . .
H8B H 0.7137 0.2540 0.8475 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4625(2) 0.23461(19) 0.86970(18) 0.0294(4) Uani 1 1 d . . . . .
H9A H 0.4771 0.1316 0.9014 0.035 Uiso 1 1 calc R U . . .
H9B H 0.3845 0.2821 0.9299 0.035 Uiso 1 1 calc R U . . .
C10 C 0.47704(19) 0.49060(18) 0.71633(16) 0.0217(3) Uani 1 1 d . . . . .
C11 C 0.33770(19) 0.38811(18) 0.66679(17) 0.0232(3) Uani 1 1 d . . . . .
H11 H 0.3257 0.3876 0.5585 0.028 Uiso 1 1 calc R U . . .
C12 C 0.1718(2) 0.4430(2) 0.71394(19) 0.0308(4) Uani 1 1 d . . . . .
H12A H 0.0922 0.3606 0.7106 0.037 Uiso 1 1 calc R U . . .
H12B H 0.1906 0.4781 0.8152 0.037 Uiso 1 1 calc R U . . .
C13 C 0.0964(2) 0.5669(2) 0.6171(2) 0.0330(4) Uani 1 1 d . . . . .
H13A H 0.0872 0.5330 0.5154 0.040 Uiso 1 1 calc R U . . .
H13B H -0.0177 0.5850 0.6414 0.040 Uiso 1 1 calc R U . . .
C14 C 0.1897(2) 0.7114(2) 0.6267(2) 0.0325(4) Uani 1 1 d . . . . .
H14A H 0.2028 0.7433 0.7292 0.039 Uiso 1 1 calc R U . . .
H14B H 0.1201 0.7853 0.5708 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3606(2) 0.71163(19) 0.57279(17) 0.0245(3) Uani 1 1 d . . . . .
H15 H 0.3972 0.8155 0.5655 0.029 Uiso 1 1 calc R U . . .
C16 C 0.2670(2) 0.1278(2) 0.6799(2) 0.0397(4) Uani 1 1 d . . . . .
H16A H 0.1763 0.1415 0.7400 0.059 Uiso 1 1 calc R U . . .
H16B H 0.3160 0.0307 0.6981 0.059 Uiso 1 1 calc R U . . .
H16C H 0.2237 0.1362 0.5775 0.059 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 C15 1.4000(19) . ?
O1 H1 0.8400 . ?
N1 C10 1.383(2) . ?
N1 C1 1.388(2) . ?
N1 C15 1.467(2) . ?
N2 C16 1.463(2) . ?
N2 C9 1.476(2) . ?
N2 C11 1.487(2) . ?
C1 C2 1.395(2) . ?
C1 C6 1.412(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.430(2) . ?
C7 C10 1.366(2) . ?
C7 C8 1.497(2) . ?
C8 C9 1.520(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.500(2) . ?
C11 C12 1.545(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.531(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.520(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.526(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15 1.0000 . ?
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
C15 O1 H1 109.5 . . ?
C10 N1 C1 107.88(13) . . ?
C10 N1 C15 126.45(14) . . ?
C1 N1 C15 125.61(14) . . ?
C16 N2 C9 112.25(14) . . ?
C16 N2 C11 112.69(14) . . ?
C9 N2 C11 113.28(13) . . ?
N1 C1 C2 130.43(15) . . ?
N1 C1 C6 107.86(14) . . ?
C2 C1 C6 121.70(15) . . ?
C3 C2 C1 117.72(16) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.29(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.95(16) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.17(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 119.16(15) . . ?
C5 C6 C7 133.77(15) . . ?
C1 C6 C7 107.05(13) . . ?
C10 C7 C6 106.83(14) . . ?
C10 C7 C8 122.39(15) . . ?
C6 C7 C8 130.66(14) . . ?
C7 C8 C9 108.55(13) . . ?
C7 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N2 C9 C8 109.64(14) . . ?
N2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C7 C10 N1 110.37(14) . . ?
C7 C10 C11 125.44(15) . . ?
N1 C10 C11 124.11(14) . . ?
N2 C11 C10 106.39(12) . . ?
N2 C11 C12 117.13(14) . . ?
C10 C11 C12 111.09(14) . . ?
N2 C11 H11 107.3 . . ?
C10 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C13 C12 C11 112.16(14) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 116.42(15) . . ?
C14 C13 H13A 108.2 . . ?
C12 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
C12 C13 H13B 108.2 . . ?
H13A C13 H13B 107.3 . . ?
C13 C14 C15 116.50(15) . . ?
C13 C14 H14A 108.2 . . ?
C15 C14 H14A 108.2 . . ?
C13 C14 H14B 108.2 . . ?
C15 C14 H14B 108.2 . . ?
H14A C14 H14B 107.3 . . ?
O1 C15 N1 111.31(13) . . ?
O1 C15 C14 109.15(13) . . ?
N1 C15 C14 111.89(14) . . ?
O1 C15 H15 108.1 . . ?
N1 C15 H15 108.1 . . ?
C14 C15 H15 108.1 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
O1 H1 N2 0.84 1.93 2.7642(18) 176.8 2_656
C2 H2 O1 0.95 2.45 3.277(2) 145.8 2_656

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_ic17656
_database_code_depnum_ccdc_archive 'CCDC 1523959'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-03-29 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         ?
_chemical_formula_sum            'C17 H20 N2 O3'
_chemical_formula_weight         300.35

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

_cell_length_a                   5.86390(10)
_cell_length_b                   8.5853(2)
_cell_length_c                   29.2551(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1472.80(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9116
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      70.21

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.760
_shelx_estimated_absorpt_T_min   0.821
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5897
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_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  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9796
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.021
_diffrn_reflns_theta_max         69.983
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2801
_reflns_number_gt                2743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0432P)²+0.3043P] 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_abs_structure_details 
; 
 Flack x determined using 1106 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2801
_refine_ls_number_parameters     207
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_restrained_S_all      1.427
_refine_ls_shift/su_max          0.003
_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 0.4936(3) 0.1511(2) 0.81682(6) 0.0384(4) Uani 1 1 d . . . . .
O2 O 0.1864(3) 0.2655(2) 0.78309(6) 0.0396(4) Uani 1 1 d . . . . .
O3 O 0.3075(3) -0.26105(19) 0.82827(5) 0.0337(4) Uani 1 1 d . . . . .
N1 N 0.2613(3) 0.09349(19) 0.96024(6) 0.0238(4) Uani 1 1 d . . . . .
H1 H 0.3805 0.1484 0.9516 0.029 Uiso 1 1 calc R U . . .
N2 N 0.0194(3) -0.1437(2) 0.86576(6) 0.0242(4) Uani 1 1 d . . . . .
C1 C 0.1761(4) 0.0844(2) 1.00417(7) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.2505(4) 0.1567(2) 1.04431(7) 0.0277(5) Uani 1 1 d . . . . .
H2 H 0.3793 0.2238 1.0445 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1282(4) 0.1263(3) 1.08372(7) 0.0304(5) Uani 1 1 d . . . . .
H3 H 0.1739 0.1741 1.1115 0.036 Uiso 1 1 calc R U . . .
C4 C -0.0611(4) 0.0268(3) 1.08375(7) 0.0305(5) Uani 1 1 d . . . . .
H4 H -0.1404 0.0081 1.1115 0.037 Uiso 1 1 calc R U . . .
C5 C -0.1342(4) -0.0444(2) 1.04413(7) 0.0276(4) Uani 1 1 d . . . . .
H5 H -0.2632 -0.1114 1.0444 0.033 Uiso 1 1 calc R U . . .
C6 C -0.0141(3) -0.0161(2) 1.00331(7) 0.0226(4) Uani 1 1 d . . . . .
C7 C -0.0410(3) -0.0669(2) 0.95692(7) 0.0224(4) Uani 1 1 d . . . . .
C8 C 0.1279(3) 0.0018(2) 0.93210(7) 0.0213(4) Uani 1 1 d . . . . .
C9 C 0.1694(3) -0.0177(2) 0.88177(7) 0.0217(4) Uani 1 1 d . . . . .
H9 H 0.3312 -0.0514 0.8773 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1315(4) 0.1333(2) 0.85461(7) 0.0262(4) Uani 1 1 d . . . . .
H10A H -0.0338 0.1466 0.8489 0.031 Uiso 1 1 calc R U . . .
H10B H 0.1836 0.2228 0.8732 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2564(4) 0.1348(3) 0.80930(7) 0.0271(5) Uani 1 1 d . . . . .
H11 H 0.2249 0.0364 0.7921 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5821(7) 0.2415(6) 0.78094(15) 0.0439(10) Uani 0.803(7) 1 d . . P A 1
H12A H 0.6296 0.1749 0.7550 0.053 Uiso 0.803(7) 1 calc R U P A 1
H12B H 0.7147 0.3034 0.7913 0.053 Uiso 0.803(7) 1 calc R U P A 1
C13 C 0.3878(7) 0.3455(5) 0.76754(16) 0.0567(12) Uani 0.803(7) 1 d . . P A 1
H13A H 0.4017 0.4486 0.7824 0.068 Uiso 0.803(7) 1 calc R U P A 1
H13B H 0.3837 0.3604 0.7340 0.068 Uiso 0.803(7) 1 calc R U P A 1
C12' C 0.542(4) 0.298(2) 0.7883(7) 0.0439(10) Uani 0.197(7) 1 d . . P A 2
H12C H 0.5028 0.3951 0.8047 0.053 Uiso 0.197(7) 1 calc R U P A 2
H12D H 0.7011 0.3024 0.7771 0.053 Uiso 0.197(7) 1 calc R U P A 2
C13' C 0.388(3) 0.2619(18) 0.7541(5) 0.0567(12) Uani 0.197(7) 1 d . . P A 2
H13C H 0.4149 0.1579 0.7406 0.068 Uiso 0.197(7) 1 calc R U P A 2
H13D H 0.3830 0.3419 0.7298 0.068 Uiso 0.197(7) 1 calc R U P A 2
C14 C -0.2174(4) -0.1697(2) 0.93530(7) 0.0263(5) Uani 1 1 d . . . . .
H14A H -0.3699 -0.1461 0.9481 0.032 Uiso 1 1 calc R U . . .
H14B H -0.1821 -0.2805 0.9415 0.032 Uiso 1 1 calc R U . . .
C15 C -0.2152(4) -0.1391(3) 0.88380(7) 0.0271(5) Uani 1 1 d . . . . .
H15A H -0.3089 -0.2187 0.8681 0.033 Uiso 1 1 calc R U . . .
H15B H -0.2831 -0.0357 0.8775 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1077(4) -0.2611(2) 0.84062(7) 0.0261(4) Uani 1 1 d . . . . .
C17 C -0.0477(5) -0.3935(3) 0.82779(10) 0.0458(7) Uani 1 1 d . . . . .
H17A H -0.1877 -0.3519 0.8142 0.069 Uiso 1 1 calc DR U . . .
H17B H -0.0858 -0.4538 0.8552 0.069 Uiso 1 1 calc R U . . .
H17C H 0.0293 -0.4611 0.8056 0.069 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 C12 1.405(4) . ?
O1 C11 1.415(3) . ?
O1 C12' 1.54(2) . ?
O2 C11 1.420(3) . ?
O2 C13 1.440(4) . ?
O2 C13' 1.453(17) . ?
O3 C16 1.226(3) . ?
N1 C1 1.381(3) . ?
N1 C8 1.382(3) . ?
N1 H1 0.8800 . ?
N2 C16 1.351(3) . ?
N2 C9 1.471(3) . ?
N2 C15 1.474(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.434(3) . ?
C7 C8 1.363(3) . ?
C7 C14 1.499(3) . ?
C8 C9 1.502(3) . ?
C9 C10 1.537(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.515(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 1.0000 . ?
C12 C13 1.499(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12' C13' 1.38(3) . ?
C12' H12C 0.9900 . ?
C12' H12D 0.9900 . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C14 C15 1.529(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.505(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C12 O1 C11 107.5(2) . . ?
C11 O1 C12' 100.2(9) . . ?
C11 O2 C13 108.1(2) . . ?
C11 O2 C13' 93.6(6) . . ?
C1 N1 C8 108.50(17) . . ?
C1 N1 H1 125.7 . . ?
C8 N1 H1 125.7 . . ?
C16 N2 C9 119.50(18) . . ?
C16 N2 C15 124.97(18) . . ?
C9 N2 C15 115.11(16) . . ?
N1 C1 C2 130.05(19) . . ?
N1 C1 C6 107.71(18) . . ?
C2 C1 C6 122.23(19) . . ?
C3 C2 C1 117.0(2) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.11(19) . . ?
C5 C6 C7 134.0(2) . . ?
C1 C6 C7 106.86(18) . . ?
C8 C7 C6 107.00(18) . . ?
C8 C7 C14 122.10(19) . . ?
C6 C7 C14 130.86(18) . . ?
C7 C8 N1 109.92(18) . . ?
C7 C8 C9 126.30(19) . . ?
N1 C8 C9 123.78(18) . . ?
N2 C9 C8 107.31(16) . . ?
N2 C9 C10 111.66(16) . . ?
C8 C9 C10 112.90(16) . . ?
N2 C9 H9 108.3 . . ?
C8 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C11 C10 C9 112.93(17) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
O1 C11 O2 106.89(18) . . ?
O1 C11 C10 109.89(18) . . ?
O2 C11 C10 109.84(17) . . ?
O1 C11 H11 110.1 . . ?
O2 C11 H11 110.1 . . ?
C10 C11 H11 110.1 . . ?
O1 C12 C13 104.1(3) . . ?
O1 C12 H12A 110.9 . . ?
C13 C12 H12A 110.9 . . ?
O1 C12 H12B 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 109.0 . . ?
O2 C13 C12 104.9(3) . . ?
O2 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
O2 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C13' C12' O1 95.1(14) . . ?
C13' C12' H12C 112.7 . . ?
O1 C12' H12C 112.7 . . ?
C13' C12' H12D 112.7 . . ?
O1 C12' H12D 112.7 . . ?
H12C C12' H12D 110.2 . . ?
C12' C13' O2 96.0(13) . . ?
C12' C13' H13C 112.5 . . ?
O2 C13' H13C 112.5 . . ?
C12' C13' H13D 112.6 . . ?
O2 C13' H13D 112.6 . . ?
H13C C13' H13D 110.1 . . ?
C7 C14 C15 107.98(17) . . ?
C7 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
C7 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
N2 C15 C14 110.85(17) . . ?
N2 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O3 C16 N2 121.8(2) . . ?
O3 C16 C17 120.4(2) . . ?
N2 C16 C17 117.8(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.045

