# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1445771'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 Cl2 N O3'
_chemical_formula_weight         312.14

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '

loop_
_symmetry_equiv_pos_as_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'
'-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                   16.880(3)
_cell_length_b                   7.9527(15)
_cell_length_c                   21.255(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2853.4(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3607
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.69

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8820
_exptl_absorpt_correction_T_max  0.9056
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14483
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2512
_reflns_number_gt                1946
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0401P)²+0.7307P] 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     SHELXL
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2512
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.74406(11) 0.0931(2) 0.48378(9) 0.0400(5) Uani 1 1 d . . .
C2 C 0.76211(13) 0.0140(3) 0.42766(9) 0.0483(5) Uani 1 1 d . . .
H2 H 0.8145 -0.0029 0.4157 0.058 Uiso 1 1 calc R . .
C3 C 0.70072(13) -0.0393(3) 0.38973(9) 0.0491(5) Uani 1 1 d . . .
C4 C 0.62318(13) -0.0140(3) 0.40579(10) 0.0533(6) Uani 1 1 d . . .
H4 H 0.5826 -0.0495 0.3794 0.064 Uiso 1 1 calc R . .
C5 C 0.60623(12) 0.0657(3) 0.46219(9) 0.0467(5) Uani 1 1 d . . .
H5 H 0.5536 0.0837 0.4733 0.056 Uiso 1 1 calc R . .
C6 C 0.66575(11) 0.1194(2) 0.50259(9) 0.0386(4) Uani 1 1 d . . .
C7 C 0.64559(11) 0.1941(2) 0.56617(9) 0.0398(5) Uani 1 1 d . . .
H7 H 0.6897 0.2627 0.5816 0.048 Uiso 1 1 calc R . .
C8 C 0.62824(12) 0.0507(3) 0.61221(9) 0.0418(5) Uani 1 1 d . . .
C9 C 0.68715(15) -0.1341(3) 0.68546(10) 0.0618(7) Uani 1 1 d . . .
H9A H 0.6534 -0.1003 0.7195 0.093 Uiso 1 1 calc R . .
H9B H 0.7385 -0.1628 0.7016 0.093 Uiso 1 1 calc R . .
H9C H 0.6646 -0.2300 0.6647 0.093 Uiso 1 1 calc R . .
C10 C 0.55346(12) 0.3844(3) 0.61018(9) 0.0437(5) Uani 1 1 d . . .
C11 C 0.49200(13) 0.4993(3) 0.60245(12) 0.0614(6) Uani 1 1 d . . .
H11 H 0.4681 0.5157 0.5635 0.074 Uiso 1 1 calc R . .
C12 C 0.46816(16) 0.5869(4) 0.65438(13) 0.0743(8) Uani 1 1 d . . .
H12 H 0.4273 0.6650 0.6513 0.089 Uiso 1 1 calc R . .
C13 C 0.50500(16) 0.5591(3) 0.71161(13) 0.0708(7) Uani 1 1 d . . .
H13 H 0.4886 0.6154 0.7477 0.085 Uiso 1 1 calc R . .
C14 C 0.56604(15) 0.4465(3) 0.71367(11) 0.0608(6) Uani 1 1 d . . .
H14 H 0.5916 0.4300 0.7519 0.073 Uiso 1 1 calc R . .
Cl1 Cl 0.82311(3) 0.15904(7) 0.53020(3) 0.05323(19) Uani 1 1 d . . .
Cl2 Cl 0.72425(5) -0.13993(9) 0.31920(3) 0.0760(2) Uani 1 1 d . . .
N1 N 0.59130(11) 0.3580(2) 0.66338(8) 0.0509(5) Uani 1 1 d . . .
O1 O 0.56501(9) -0.0136(2) 0.61886(8) 0.0608(4) Uani 1 1 d . . .
O2 O 0.69467(8) 0.00346(18) 0.64086(6) 0.0493(4) Uani 1 1 d . . .
O3 O 0.57628(8) 0.29592(17) 0.55818(6) 0.0471(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 C2 1.383(3) . ?
C1 C6 1.397(3) . ?
C1 Cl1 1.7404(19) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 Cl2 1.745(2) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(3) . ?
C7 O3 1.433(2) . ?
C7 C8 1.531(3) . ?
C7 H7 0.9800 . ?
C8 O1 1.192(2) . ?
C8 O2 1.330(2) . ?
C9 O2 1.453(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.315(3) . ?
C10 O3 1.366(2) . ?
C10 C11 1.392(3) . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(3) . ?
C13 H13 0.9300 . ?
C14 N1 1.349(3) . ?
C14 H14 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
C2 C1 C6 121.58(18) . . ?
C2 C1 Cl1 117.21(15) . . ?
C6 C1 Cl1 121.21(15) . . ?
C3 C2 C1 118.58(19) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 121.86(19) . . ?
C4 C3 Cl2 119.98(17) . . ?
C2 C3 Cl2 118.16(17) . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.74(19) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.49(18) . . ?
C5 C6 C7 120.64(17) . . ?
C1 C6 C7 121.78(17) . . ?
O3 C7 C6 107.42(15) . . ?
O3 C7 C8 109.90(15) . . ?
C6 C7 C8 108.74(16) . . ?
O3 C7 H7 110.2 . . ?
C6 C7 H7 110.2 . . ?
C8 C7 H7 110.2 . . ?
O1 C8 O2 125.41(19) . . ?
O1 C8 C7 124.52(18) . . ?
O2 C8 C7 109.98(16) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 O3 118.47(18) . . ?
N1 C10 C11 124.6(2) . . ?
O3 C10 C11 116.91(19) . . ?
C12 C11 C10 117.3(2) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 118.2(2) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
N1 C14 C13 123.7(2) . . ?
N1 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
C10 N1 C14 116.39(19) . . ?
C8 O2 C9 115.95(17) . . ?
C10 O3 C7 115.18(15) . . ?

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 0.1(3) . . . . ?
Cl1 C1 C2 C3 -179.83(16) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C2 C3 Cl2 -179.69(15) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
Cl2 C3 C4 C5 179.76(16) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 -175.29(19) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
Cl1 C1 C6 C5 178.83(15) . . . . ?
C2 C1 C6 C7 175.31(17) . . . . ?
Cl1 C1 C6 C7 -4.8(3) . . . . ?
C5 C6 C7 O3 -38.5(2) . . . . ?
C1 C6 C7 O3 145.18(18) . . . . ?
C5 C6 C7 C8 80.4(2) . . . . ?
C1 C6 C7 C8 -95.9(2) . . . . ?
O3 C7 C8 O1 30.5(3) . . . . ?
C6 C7 C8 O1 -86.8(2) . . . . ?
O3 C7 C8 O2 -152.78(16) . . . . ?
C6 C7 C8 O2 89.91(19) . . . . ?
N1 C10 C11 C12 -1.9(4) . . . . ?
O3 C10 C11 C12 179.3(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 1.7(4) . . . . ?
C12 C13 C14 N1 -1.6(4) . . . . ?
O3 C10 N1 C14 -179.15(19) . . . . ?
C11 C10 N1 C14 2.0(3) . . . . ?
C13 C14 N1 C10 -0.2(3) . . . . ?
O1 C8 O2 C9 -2.5(3) . . . . ?
C7 C8 O2 C9 -179.15(17) . . . . ?
N1 C10 O3 C7 -6.0(3) . . . . ?
C11 C10 O3 C7 172.87(18) . . . . ?
C6 C7 O3 C10 -174.86(16) . . . . ?
C8 C7 O3 C10 67.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_S
_database_code_depnum_ccdc_archive 'CCDC 1523822'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39

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      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                   5.6319(14)
_cell_length_b                   11.918(3)
_cell_length_c                   14.202(4)
_cell_angle_alpha                80.529(6)
_cell_angle_beta                 81.438(6)
_cell_angle_gamma                78.190(6)
_cell_volume                     913.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1516
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      24.80

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9844
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   sadabs
_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            5331
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.464
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3372
_reflns_number_gt                2222
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1690P)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         3372
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.2489
_refine_ls_wR_factor_gt          0.1936
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.5341(5) 1.1298(2) 0.1651(2) 0.0538(7) Uani 1 1 d . . . . .
H1 H 0.6388 1.1287 0.2102 0.065 Uiso 1 1 calc R U . . .
C2 C 0.5451(6) 1.2048(3) 0.0806(2) 0.0646(8) Uani 1 1 d . . . . .
H2 H 0.6550 1.2555 0.0697 0.077 Uiso 1 1 calc R U . . .
C3 C 0.3957(7) 1.2058(3) 0.0120(2) 0.0736(10) Uani 1 1 d . . . . .
H3 H 0.4059 1.2560 -0.0454 0.088 Uiso 1 1 calc R U . . .
C4 C 0.2347(6) 1.1336(3) 0.0288(2) 0.0755(10) Uani 1 1 d . . . . .
H4 H 0.1338 1.1339 -0.0175 0.091 Uiso 1 1 calc R U . . .
C5 C 0.2173(6) 1.0584(3) 0.1145(2) 0.0628(8) Uani 1 1 d . . . . .
H5 H 0.1038 1.0096 0.1256 0.075 Uiso 1 1 calc R U . . .
C6 C 0.3682(5) 1.0563(2) 0.18286(19) 0.0473(7) Uani 1 1 d . . . . .
C7 C 0.3659(5) 0.9675(2) 0.27250(18) 0.0474(7) Uani 1 1 d . . . . .
H7 H 0.2236 0.9301 0.2787 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5951(5) 0.8792(2) 0.26615(18) 0.0482(7) Uani 1 1 d . . . . .
H8 H 0.7381 0.9014 0.2753 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6124(5) 0.7728(2) 0.24870(18) 0.0483(7) Uani 1 1 d . . . . .
H9 H 0.4715 0.7465 0.2427 0.058 Uiso 1 1 calc R U . . .
C10 C 0.8503(5) 0.6942(2) 0.23845(18) 0.0488(7) Uani 1 1 d . . . . .
C11 C 1.0348(5) 0.4993(2) 0.1998(2) 0.0507(7) Uani 1 1 d . . . . .
C12 C 1.1578(7) 0.4572(3) 0.2901(3) 0.0863(11) Uani 1 1 d . . . . .
H12A H 1.2437 0.5147 0.3013 0.129 Uiso 1 1 calc R U . . .
H12B H 1.2712 0.3864 0.2825 0.129 Uiso 1 1 calc R U . . .
H12C H 1.0366 0.4440 0.3438 0.129 Uiso 1 1 calc R U . . .
C13 C 1.2055(6) 0.5400(3) 0.1149(3) 0.0762(10) Uani 1 1 d . . . . .
H13A H 1.1142 0.5743 0.0621 0.114 Uiso 1 1 calc R U . . .
H13B H 1.3257 0.4753 0.0964 0.114 Uiso 1 1 calc R U . . .
H13C H 1.2854 0.5963 0.1320 0.114 Uiso 1 1 calc R U . . .
C14 C 0.9116(7) 0.4054(3) 0.1775(3) 0.0812(11) Uani 1 1 d . . . . .
H14A H 0.7936 0.3861 0.2307 0.122 Uiso 1 1 calc R U . . .
H14B H 1.0326 0.3378 0.1668 0.122 Uiso 1 1 calc R U . . .
H14C H 0.8312 0.4334 0.1208 0.122 Uiso 1 1 calc R U . . .
C15 C 0.1697(4) 1.0875(2) 0.39452(16) 0.0410(6) Uani 1 1 d . . . . .
C16 C 0.1863(5) 1.1280(2) 0.47925(19) 0.0525(7) Uani 1 1 d . . . . .
H16 H 0.3248 1.1030 0.5109 0.063 Uiso 1 1 calc R U . . .
C17 C -0.2111(5) 1.1916(2) 0.38583(19) 0.0501(7) Uani 1 1 d . . . . .
H17 H -0.3489 1.2136 0.3535 0.060 Uiso 1 1 calc R U . . .
C18 C -0.2133(5) 1.2417(2) 0.46726(18) 0.0490(7) Uani 1 1 d . . . . .
C19 C -0.0047(5) 1.2049(2) 0.51447(19) 0.0532(7) Uani 1 1 d . . . . .
H19 H 0.0032 1.2336 0.5708 0.064 Uiso 1 1 calc R U . . .
C20 C -0.4203(6) 1.3337(3) 0.4989(2) 0.0685(9) Uani 1 1 d . . . . .
H20A H -0.4012 1.4070 0.4618 0.103 Uiso 1 1 calc R U . . .
H20B H -0.4200 1.3380 0.5658 0.103 Uiso 1 1 calc R U . . .
H20C H -0.5722 1.3151 0.4893 0.103 Uiso 1 1 calc R U . . .
N1 N -0.0270(4) 1.11380(19) 0.34942(15) 0.0474(6) Uani 1 1 d . . . . .
O1 O 0.3704(3) 1.01455(16) 0.35987(12) 0.0518(5) Uani 1 1 d . . . . .
O2 O 1.0433(4) 0.71801(19) 0.24819(17) 0.0703(7) Uani 1 1 d . . . . .
O3 O 0.8238(3) 0.59280(15) 0.21778(13) 0.0508(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(4) . ?
C1 C6 1.376(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.344(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(4) . ?
C7 O1 1.449(3) . ?
C7 C8 1.491(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.314(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.472(4) . ?
C9 H9 0.9300 . ?
C10 O2 1.210(3) . ?
C10 O3 1.331(3) . ?
C11 O3 1.477(3) . ?
C11 C13 1.506(4) . ?
C11 C12 1.512(4) . ?
C11 C14 1.527(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N1 1.319(3) . ?
C15 O1 1.359(3) . ?
C15 C16 1.391(4) . ?
C16 C19 1.354(4) . ?
C16 H16 0.9300 . ?
C17 N1 1.344(3) . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.396(4) . ?
C18 C20 1.498(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 120.0(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 120.5(2) . . ?
O1 C7 C8 103.70(19) . . ?
O1 C7 C6 113.7(2) . . ?
C8 C7 C6 109.3(2) . . ?
O1 C7 H7 110.0 . . ?
C8 C7 H7 110.0 . . ?
C6 C7 H7 110.0 . . ?
C9 C8 C7 125.6(2) . . ?
C9 C8 H8 117.2 . . ?
C7 C8 H8 117.2 . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
O2 C10 O3 124.6(2) . . ?
O2 C10 C9 124.8(2) . . ?
O3 C10 C9 110.6(2) . . ?
O3 C11 C13 109.9(2) . . ?
O3 C11 C12 109.9(2) . . ?
C13 C11 C12 113.1(3) . . ?
O3 C11 C14 101.9(2) . . ?
C13 C11 C14 111.4(3) . . ?
C12 C11 C14 110.0(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 O1 120.2(2) . . ?
N1 C15 C16 123.9(2) . . ?
O1 C15 C16 115.9(2) . . ?
C19 C16 C15 118.2(2) . . ?
C19 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
N1 C17 C18 125.6(2) . . ?
N1 C17 H17 117.2 . . ?
C18 C17 H17 117.2 . . ?
C17 C18 C19 115.3(2) . . ?
C17 C18 C20 121.9(2) . . ?
C19 C18 C20 122.7(2) . . ?
C16 C19 C18 120.8(2) . . ?
C16 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 N1 C17 115.9(2) . . ?
C15 O1 C7 119.17(18) . . ?
C10 O3 C11 122.0(2) . . ?

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 -1.5(5) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 C7 -174.6(3) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C2 C1 C6 C7 175.8(2) . . . . ?
C5 C6 C7 O1 -136.9(3) . . . . ?
C1 C6 C7 O1 48.3(3) . . . . ?
C5 C6 C7 C8 107.8(3) . . . . ?
C1 C6 C7 C8 -67.0(3) . . . . ?
O1 C7 C8 C9 132.4(3) . . . . ?
C6 C7 C8 C9 -106.0(3) . . . . ?
C7 C8 C9 C10 176.5(2) . . . . ?
C8 C9 C10 O2 2.7(4) . . . . ?
C8 C9 C10 O3 -177.8(2) . . . . ?
N1 C15 C16 C19 -4.4(4) . . . . ?
O1 C15 C16 C19 177.1(2) . . . . ?
N1 C17 C18 C19 -1.0(4) . . . . ?
N1 C17 C18 C20 175.8(3) . . . . ?
C15 C16 C19 C18 0.5(4) . . . . ?
C17 C18 C19 C16 2.0(4) . . . . ?
C20 C18 C19 C16 -174.8(3) . . . . ?
O1 C15 N1 C17 -176.3(2) . . . . ?
C16 C15 N1 C17 5.2(4) . . . . ?
C18 C17 N1 C15 -2.5(4) . . . . ?
N1 C15 O1 C7 0.7(3) . . . . ?
C16 C15 O1 C7 179.2(2) . . . . ?
C8 C7 O1 C15 -171.3(2) . . . . ?
C6 C7 O1 C15 70.2(3) . . . . ?
O2 C10 O3 C11 -3.0(4) . . . . ?
C9 C10 O3 C11 177.5(2) . . . . ?
C13 C11 O3 C10 -60.4(3) . . . . ?
C12 C11 O3 C10 64.7(3) . . . . ?
C14 C11 O3 C10 -178.6(2) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.065

_shelxl_version_number           2014/6

