# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1502480'
_audit_update_record             
;
2016-09-04 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 N3 O3'
_chemical_formula_weight         303.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.3562(19)
_cell_length_b                   14.494(3)
_cell_length_c                   10.9559(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.598(3)
_cell_angle_gamma                90.00
_cell_volume                     1626.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2182
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      23.74

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10300
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         28.38
_reflns_number_total             3999
_reflns_number_gt                2400
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.4762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3999
_refine_ls_number_parameters     201
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      1.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48745(16) 0.25802(11) 0.47443(16) 0.0438(4) Uani 1 1 d . . .
C2 C 0.55098(19) 0.32246(13) 0.5554(2) 0.0587(5) Uani 1 1 d . . .
H2 H 0.5531 0.3147 0.6399 0.070 Uiso 1 1 calc R . .
C3 C 0.6117(2) 0.39885(14) 0.5117(2) 0.0747(6) Uani 1 1 d . . .
H3 H 0.6555 0.4412 0.5668 0.090 Uiso 1 1 calc R . .
C4 C 0.6068(2) 0.41117(16) 0.3878(3) 0.0769(7) Uani 1 1 d . . .
H4 H 0.6460 0.4625 0.3580 0.092 Uiso 1 1 calc R . .
C5 C 0.5443(2) 0.34818(15) 0.3076(2) 0.0674(6) Uani 1 1 d . . .
H5 H 0.5418 0.3575 0.2233 0.081 Uiso 1 1 calc R . .
C6 C 0.48407(17) 0.27050(13) 0.34722(17) 0.0515(4) Uani 1 1 d . . .
C7 C 0.41632(16) 0.17678(11) 0.52387(16) 0.0436(4) Uani 1 1 d . . .
H7 H 0.4236 0.1238 0.4697 0.052 Uiso 1 1 calc R . .
C8 C 0.40172(19) 0.08320(13) 0.70831(19) 0.0585(5) Uani 1 1 d . . .
H8A H 0.3917 0.0270 0.6598 0.070 Uiso 1 1 calc R . .
H8B H 0.3154 0.1075 0.7133 0.070 Uiso 1 1 calc R . .
C9 C 0.4715(2) 0.06235(16) 0.8362(2) 0.0698(6) Uani 1 1 d . . .
H9A H 0.4785 0.1185 0.8849 0.084 Uiso 1 1 calc R . .
H9B H 0.4205 0.0183 0.8757 0.084 Uiso 1 1 calc R . .
C10 C 0.6726(2) 0.08897(15) 0.7734(2) 0.0667(6) Uani 1 1 d . . .
H10A H 0.7577 0.0623 0.7690 0.080 Uiso 1 1 calc R . .
H10B H 0.6858 0.1453 0.8214 0.080 Uiso 1 1 calc R . .
C11 C 0.60714(17) 0.11152(14) 0.64592(18) 0.0557(5) Uani 1 1 d . . .
H11A H 0.6600 0.1553 0.6083 0.067 Uiso 1 1 calc R . .
H11B H 0.5992 0.0560 0.5960 0.067 Uiso 1 1 calc R . .
C12 C 0.27299(16) 0.19937(12) 0.51714(16) 0.0459(4) Uani 1 1 d . . .
N2 N 0.24165(14) 0.28044(11) 0.55797(14) 0.0518(4) Uani 1 1 d . . .
C14 C 0.16799(17) 0.13957(13) 0.46355(19) 0.0544(5) Uani 1 1 d . . .
C16 C 0.4164(2) 0.20376(17) 0.25405(19) 0.0739(6) Uani 1 1 d . . .
H16A H 0.4260 0.2240 0.1725 0.111 Uiso 1 1 calc R . .
H16B H 0.3254 0.2009 0.2617 0.111 Uiso 1 1 calc R . .
H16C H 0.4547 0.1437 0.2685 0.111 Uiso 1 1 calc R . .
N1 N 0.47710(13) 0.15081(9) 0.64887(13) 0.0446(3) Uani 1 1 d . . .
O1 O 0.59778(14) 0.02599(10) 0.83396(14) 0.0737(4) Uani 1 1 d . . .
O2 O 0.05051(12) 0.17846(9) 0.46304(13) 0.0624(4) Uani 1 1 d D . .
O3 O 0.18487(14) 0.06349(10) 0.42482(18) 0.0851(5) Uani 1 1 d . . .
C17 C -0.0624(2) 0.12395(17) 0.4088(3) 0.0878(8) Uani 1 1 d D . .
H17A H -0.0496 0.1019 0.3279 0.105 Uiso 1 1 calc R . .
H17B H -0.0723 0.0709 0.4605 0.105 Uiso 1 1 calc R . .
C18 C -0.1772(2) 0.1804(2) 0.3983(3) 0.1006(9) Uani 1 1 d D . .
H18A H -0.1861 0.2054 0.4778 0.151 Uiso 1 1 calc R . .
H18B H -0.2526 0.1436 0.3687 0.151 Uiso 1 1 calc R . .
H18C H -0.1699 0.2299 0.3415 0.151 Uiso 1 1 calc R . .
N3 N 0.21901(19) 0.35039(14) 0.59306(19) 0.0809(6) 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 C2 1.385(2) . ?
C1 C6 1.401(2) . ?
C1 C7 1.530(2) . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C16 1.502(3) . ?
C7 N1 1.468(2) . ?
C7 C12 1.511(2) . ?
C7 H7 0.9800 . ?
C8 N1 1.465(2) . ?
C8 C9 1.508(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O1 1.414(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O1 1.424(2) . ?
C10 C11 1.495(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N1 1.467(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.315(2) . ?
C12 C14 1.445(3) . ?
N2 N3 1.121(2) . ?
C14 O3 1.204(2) . ?
C14 O2 1.340(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O2 C17 1.462(2) . ?
C17 C18 1.434(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C2 C1 C6 119.29(17) . . ?
C2 C1 C7 119.99(16) . . ?
C6 C1 C7 120.65(15) . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 122.3(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 118.05(18) . . ?
C5 C6 C16 119.73(18) . . ?
C1 C6 C16 122.21(17) . . ?
N1 C7 C12 112.46(13) . . ?
N1 C7 C1 111.44(14) . . ?
C12 C7 C1 109.72(13) . . ?
N1 C7 H7 107.7 . . ?
C12 C7 H7 107.7 . . ?
C1 C7 H7 107.7 . . ?
N1 C8 C9 109.51(16) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O1 C9 C8 111.99(18) . . ?
O1 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
O1 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O1 C10 C11 111.89(17) . . ?
O1 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
O1 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N1 C11 C10 110.75(16) . . ?
N1 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 C14 117.72(16) . . ?
N2 C12 C7 117.88(15) . . ?
C14 C12 C7 124.34(15) . . ?
N3 N2 C12 177.77(19) . . ?
O3 C14 O2 124.29(18) . . ?
O3 C14 C12 123.55(17) . . ?
O2 C14 C12 112.15(16) . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N1 C11 107.58(14) . . ?
C8 N1 C7 113.80(14) . . ?
C11 N1 C7 110.24(13) . . ?
C9 O1 C10 109.80(15) . . ?
C14 O2 C17 116.42(16) . . ?
C18 C17 O2 109.1(2) . . ?
C18 C17 H17A 109.9 . . ?
O2 C17 H17A 109.9 . . ?
C18 C17 H17B 109.9 . . ?
O2 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(3) . . . . ?
C7 C1 C2 C3 -177.40(17) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C16 179.8(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C7 C1 C6 C5 176.50(16) . . . . ?
C2 C1 C6 C16 -179.66(18) . . . . ?
C7 C1 C6 C16 -2.6(3) . . . . ?
C2 C1 C7 N1 -29.2(2) . . . . ?
C6 C1 C7 N1 153.78(15) . . . . ?
C2 C1 C7 C12 96.02(19) . . . . ?
C6 C1 C7 C12 -80.99(19) . . . . ?
N1 C8 C9 O1 -59.8(2) . . . . ?
O1 C10 C11 N1 58.1(2) . . . . ?
N1 C7 C12 N2 77.73(19) . . . . ?
C1 C7 C12 N2 -46.9(2) . . . . ?
N1 C7 C12 C14 -105.31(19) . . . . ?
C1 C7 C12 C14 130.06(18) . . . . ?
C14 C12 N2 N3 -167(5) . . . . ?
C7 C12 N2 N3 10(5) . . . . ?
N2 C12 C14 O3 -178.92(19) . . . . ?
C7 C12 C14 O3 4.1(3) . . . . ?
N2 C12 C14 O2 0.6(2) . . . . ?
C7 C12 C14 O2 -176.36(15) . . . . ?
C9 C8 N1 C11 58.3(2) . . . . ?
C9 C8 N1 C7 -179.26(16) . . . . ?
C10 C11 N1 C8 -58.1(2) . . . . ?
C10 C11 N1 C7 177.29(15) . . . . ?
C12 C7 N1 C8 47.39(19) . . . . ?
C1 C7 N1 C8 171.07(14) . . . . ?
C12 C7 N1 C11 168.35(14) . . . . ?
C1 C7 N1 C11 -67.97(17) . . . . ?
C8 C9 O1 C10 57.4(2) . . . . ?
C11 C10 O1 C9 -56.4(2) . . . . ?
O3 C14 O2 C17 -1.4(3) . . . . ?
C12 C14 O2 C17 179.07(19) . . . . ?
C14 O2 C17 C18 -171.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1502481'
_audit_update_record             
;
2016-09-04 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Cl N3 O3'
_chemical_formula_weight         323.77

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.309(5)
_cell_length_b                   14.264(7)
_cell_length_c                   10.935(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.732(8)
_cell_angle_gamma                90.00
_cell_volume                     1589.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2544
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.60

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9271
_exptl_absorpt_correction_T_max  0.9626
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7833
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2784
_reflns_number_gt                2081
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     200
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1435
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      1.020
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.41377(9) 0.18858(6) 0.25101(6) 0.0786(3) Uani 1 1 d . . .
O1 O 0.6112(2) 0.02845(14) 0.84387(18) 0.0677(6) Uani 1 1 d . . .
O2 O 0.1898(2) 0.06202(14) 0.4326(2) 0.0807(7) Uani 1 1 d . . .
O3 O 0.05829(16) 0.17977(13) 0.46933(19) 0.0591(5) Uani 1 1 d . . .
N1 N 0.48552(18) 0.15087(14) 0.65630(18) 0.0425(5) Uani 1 1 d . . .
N2 N 0.2500(2) 0.27991(16) 0.56719(18) 0.0483(5) Uani 1 1 d . . .
N3 N 0.2290(3) 0.3509(2) 0.6032(3) 0.0762(8) Uani 1 1 d . . .
C2 C 0.4931(2) 0.25688(15) 0.4805(2) 0.0417(5) Uani 1 1 d . . .
C3 C 0.5576(3) 0.32394(18) 0.5580(3) 0.0564(7) Uani 1 1 d . . .
H3 H 0.5610 0.3179 0.6431 0.068 Uiso 1 1 calc R . .
C4 C 0.6175(3) 0.4004(2) 0.5108(3) 0.0707(6) Uani 1 1 d U . .
H4 H 0.6619 0.4445 0.5641 0.085 Uiso 1 1 calc R . .
C5 C 0.6110(3) 0.4103(2) 0.3859(3) 0.0701(6) Uani 1 1 d U . .
H5 H 0.6498 0.4620 0.3545 0.084 Uiso 1 1 calc R . .
C6 C 0.5489(3) 0.3461(2) 0.3075(3) 0.0680(6) Uani 1 1 d U . .
H6 H 0.5447 0.3533 0.2225 0.082 Uiso 1 1 calc R . .
C7 C 0.4914(2) 0.26932(19) 0.3550(2) 0.0495(6) Uani 1 1 d . . .
C8 C 0.4238(2) 0.17541(15) 0.5310(2) 0.0403(5) Uani 1 1 d . . .
H8 H 0.4307 0.1211 0.4776 0.048 Uiso 1 1 calc R . .
C9 C 0.1751(2) 0.13910(18) 0.4710(2) 0.0510(6) Uani 1 1 d . . .
C10 C -0.0562(3) 0.1262(2) 0.4152(4) 0.0812(10) Uani 1 1 d . . .
H10A H -0.0460 0.1057 0.3326 0.097 Uiso 1 1 calc R . .
H10B H -0.0655 0.0710 0.4651 0.097 Uiso 1 1 calc R . .
C11 C -0.1701(3) 0.1839(3) 0.4099(4) 0.0904(11) Uani 1 1 d . . .
H11A H -0.1715 0.2126 0.4891 0.136 Uiso 1 1 calc R . .
H11B H -0.2474 0.1463 0.3885 0.136 Uiso 1 1 calc R . .
H11C H -0.1680 0.2318 0.3484 0.136 Uiso 1 1 calc R . .
C12 C 0.2806(2) 0.19867(16) 0.5252(2) 0.0429(6) Uani 1 1 d . . .
C13 C 0.4132(3) 0.08071(19) 0.7157(3) 0.0555(7) Uani 1 1 d . . .
H13A H 0.4068 0.0232 0.6678 0.067 Uiso 1 1 calc R . .
H13B H 0.3250 0.1031 0.7192 0.067 Uiso 1 1 calc R . .
C14 C 0.4821(3) 0.0618(2) 0.8437(3) 0.0659(8) Uani 1 1 d . . .
H14A H 0.4852 0.1190 0.8919 0.079 Uiso 1 1 calc R . .
H14B H 0.4327 0.0157 0.8828 0.079 Uiso 1 1 calc R . .
C15 C 0.6830(3) 0.0933(2) 0.7830(3) 0.0653(8) Uani 1 1 d . . .
H15A H 0.7699 0.0684 0.7800 0.078 Uiso 1 1 calc R . .
H15B H 0.6929 0.1512 0.8300 0.078 Uiso 1 1 calc R . .
C16 C 0.6175(3) 0.1139(2) 0.6544(2) 0.0535(6) Uani 1 1 d . . .
H16A H 0.6690 0.1593 0.6165 0.064 Uiso 1 1 calc R . .
H16B H 0.6122 0.0569 0.6054 0.064 Uiso 1 1 calc R . .


_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
Cl1 C7 1.727(3) . ?
O1 C14 1.413(3) . ?
O1 C15 1.413(3) . ?
O2 C9 1.195(3) . ?
O3 C9 1.334(3) . ?
O3 C10 1.455(3) . ?
N1 C13 1.458(3) . ?
N1 C16 1.462(3) . ?
N1 C8 1.463(3) . ?
N2 N3 1.120(3) . ?
N2 C12 1.303(3) . ?
C2 C3 1.380(4) . ?
C2 C7 1.382(3) . ?
C2 C8 1.512(3) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.348(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9300 . ?
C8 C12 1.505(3) . ?
C8 H8 0.9800 . ?
C9 C12 1.435(4) . ?
C10 C11 1.429(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.495(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.494(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C14 O1 C15 109.9(2) . . ?
C9 O3 C10 116.9(2) . . ?
C13 N1 C16 107.3(2) . . ?
C13 N1 C8 113.73(19) . . ?
C16 N1 C8 110.27(18) . . ?
N3 N2 C12 177.2(3) . . ?
C3 C2 C7 117.0(2) . . ?
C3 C2 C8 121.2(2) . . ?
C7 C2 C8 121.8(2) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 122.2(3) . . ?
C2 C7 Cl1 120.2(2) . . ?
C6 C7 Cl1 117.6(2) . . ?
N1 C8 C12 112.13(18) . . ?
N1 C8 C2 111.32(18) . . ?
C12 C8 C2 109.28(18) . . ?
N1 C8 H8 108.0 . . ?
C12 C8 H8 108.0 . . ?
C2 C8 H8 108.0 . . ?
O2 C9 O3 123.9(2) . . ?
O2 C9 C12 124.1(2) . . ?
O3 C9 C12 112.0(2) . . ?
C11 C10 O3 108.9(3) . . ?
C11 C10 H10A 109.9 . . ?
O3 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
O3 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
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 . . ?
N2 C12 C9 117.6(2) . . ?
N2 C12 C8 118.0(2) . . ?
C9 C12 C8 124.3(2) . . ?
N1 C13 C14 109.8(2) . . ?
N1 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N1 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
O1 C14 C13 112.0(2) . . ?
O1 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
O1 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
O1 C15 C16 112.2(2) . . ?
O1 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
O1 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N1 C16 C15 110.2(2) . . ?
N1 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 0.1(4) . . . . ?
C8 C2 C3 C4 -177.9(2) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C3 C2 C7 C6 -1.3(4) . . . . ?
C8 C2 C7 C6 176.7(2) . . . . ?
C3 C2 C7 Cl1 179.66(19) . . . . ?
C8 C2 C7 Cl1 -2.4(3) . . . . ?
C5 C6 C7 C2 1.3(4) . . . . ?
C5 C6 C7 Cl1 -179.7(2) . . . . ?
C13 N1 C8 C12 49.9(3) . . . . ?
C16 N1 C8 C12 170.6(2) . . . . ?
C13 N1 C8 C2 172.7(2) . . . . ?
C16 N1 C8 C2 -66.7(2) . . . . ?
C3 C2 C8 N1 -28.7(3) . . . . ?
C7 C2 C8 N1 153.4(2) . . . . ?
C3 C2 C8 C12 95.7(3) . . . . ?
C7 C2 C8 C12 -82.2(3) . . . . ?
C10 O3 C9 O2 -1.0(4) . . . . ?
C10 O3 C9 C12 179.4(3) . . . . ?
C9 O3 C10 C11 -174.1(3) . . . . ?
N3 N2 C12 C9 -163(5) . . . . ?
N3 N2 C12 C8 14(5) . . . . ?
O2 C9 C12 N2 -177.7(3) . . . . ?
O3 C9 C12 N2 1.9(3) . . . . ?
O2 C9 C12 C8 5.4(4) . . . . ?
O3 C9 C12 C8 -175.0(2) . . . . ?
N1 C8 C12 N2 75.9(3) . . . . ?
C2 C8 C12 N2 -48.1(3) . . . . ?
N1 C8 C12 C9 -107.3(3) . . . . ?
C2 C8 C12 C9 128.8(2) . . . . ?
C16 N1 C13 C14 58.9(3) . . . . ?
C8 N1 C13 C14 -178.8(2) . . . . ?
C15 O1 C14 C13 56.7(3) . . . . ?
N1 C13 C14 O1 -59.7(3) . . . . ?
C14 O1 C15 C16 -56.1(3) . . . . ?
C13 N1 C16 C15 -58.4(3) . . . . ?
C8 N1 C16 C15 177.2(2) . . . . ?
O1 C15 C16 N1 58.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.045
