# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd213396
_database_code_depnum_ccdc_archive 'CCDC 949600'
_audit_update_record             
;
2013-07-10 deposited with the CCDC.
2015-10-30 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 H13 N'
_chemical_formula_weight         219.27

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'

_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                   16.7246(15)
_cell_length_b                   7.1468(7)
_cell_length_c                   20.1020(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2402.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1549
_cell_measurement_theta_min      4.728
_cell_measurement_theta_max      39.209

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.39458
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            13564
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2372
_reflns_number_gt                1533
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0655P)²+0.1806P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2372
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
N1 N 0.73625(8) 1.00097(19) 0.66623(8) 0.0673(4) Uani 1 1 d . . .
C1 C 0.86348(9) 1.0067(2) 0.69681(8) 0.0536(4) Uani 1 1 d . . .
C2 C 0.81178(10) 1.0227(2) 0.64115(9) 0.0600(5) Uani 1 1 d . . .
C3 C 0.83984(14) 1.0492(3) 0.57721(10) 0.0821(6) Uani 1 1 d . . .
H3 H 0.8049 1.0589 0.5414 0.099 Uiso 1 1 calc R . .
C4 C 0.92094(16) 1.0609(3) 0.56847(11) 0.0959(7) Uani 1 1 d . . .
H4 H 0.9414 1.0816 0.5261 0.115 Uiso 1 1 calc R . .
C5 C 0.97300(13) 1.0424(3) 0.62170(11) 0.0899(7) Uani 1 1 d . . .
H5 H 1.0278 1.0490 0.6142 0.108 Uiso 1 1 calc R . .
C6 C 0.94541(11) 1.0145(2) 0.68498(10) 0.0678(5) Uani 1 1 d . . .
H6 H 0.9813 1.0008 0.7200 0.081 Uiso 1 1 calc R . .
C7 C 0.73861(10) 0.9790(2) 0.73293(9) 0.0598(4) Uani 1 1 d . . .
C8 C 0.81549(9) 0.9796(2) 0.75631(8) 0.0521(4) Uani 1 1 d . . .
C9 C 0.84080(9) 0.9572(2) 0.82540(8) 0.0551(4) Uani 1 1 d . . .
C10 C 0.90775(11) 1.0451(3) 0.85149(9) 0.0724(5) Uani 1 1 d . . .
H10 H 0.9398 1.1180 0.8239 0.087 Uiso 1 1 calc R . .
C11 C 0.92744(15) 1.0258(4) 0.91761(11) 0.0982(7) Uani 1 1 d . . .
H11 H 0.9722 1.0867 0.9344 0.118 Uiso 1 1 calc R . .
C12 C 0.88140(17) 0.9173(4) 0.95887(11) 0.1082(8) Uani 1 1 d . . .
H12 H 0.8951 0.9042 1.0035 0.130 Uiso 1 1 calc R . .
C13 C 0.81532(14) 0.8287(3) 0.93422(10) 0.0928(7) Uani 1 1 d . . .
H13 H 0.7840 0.7549 0.9620 0.111 Uiso 1 1 calc R . .
C14 C 0.79518(11) 0.8487(3) 0.86861(9) 0.0715(5) Uani 1 1 d . . .
H14 H 0.7499 0.7883 0.8525 0.086 Uiso 1 1 calc R . .
C15 C 0.64860(10) 1.0173(2) 0.66277(11) 0.0739(6) Uani 1 1 d . . .
H15A H 0.6227 0.9179 0.6380 0.089 Uiso 1 1 calc R . .
H15B H 0.6297 1.1395 0.6488 0.089 Uiso 1 1 calc R . .
C16 C 0.64890(9) 0.9878(2) 0.73888(10) 0.0701(5) Uani 1 1 d . . .
H16A H 0.6292 1.0937 0.7642 0.084 Uiso 1 1 calc R . .
H16B H 0.6242 0.8718 0.7533 0.084 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
N1 C7 1.350(2) . ?
N1 C2 1.369(2) . ?
N1 C15 1.472(2) . ?
C1 C6 1.392(2) . ?
C1 C2 1.419(2) . ?
C1 C8 1.453(2) . ?
C2 C3 1.381(3) . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.369(2) . ?
C7 C16 1.507(2) . ?
C8 C9 1.461(2) . ?
C9 C10 1.387(2) . ?
C9 C14 1.392(2) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.545(3) . ?
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
C7 N1 C2 110.60(13) . . ?
C7 N1 C15 94.90(14) . . ?
C2 N1 C15 153.17(16) . . ?
C6 C1 C2 117.53(16) . . ?
C6 C1 C8 133.59(16) . . ?
C2 C1 C8 108.85(14) . . ?
N1 C2 C3 132.20(17) . . ?
N1 C2 C1 105.24(15) . . ?
C3 C2 C1 122.54(17) . . ?
C4 C3 C2 117.63(19) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.79(19) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N1 C7 C8 111.59(15) . . ?
N1 C7 C16 92.57(13) . . ?
C8 C7 C16 155.24(17) . . ?
C7 C8 C1 103.68(14) . . ?
C7 C8 C9 126.74(15) . . ?
C1 C8 C9 129.57(14) . . ?
C10 C9 C14 117.30(17) . . ?
C10 C9 C8 122.96(16) . . ?
C14 C9 C8 119.69(15) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 121.63(18) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
N1 C15 C16 86.51(12) . . ?
N1 C15 H15A 114.2 . . ?
C16 C15 H15A 114.2 . . ?
N1 C15 H15B 114.2 . . ?
C16 C15 H15B 114.2 . . ?
H15A C15 H15B 111.4 . . ?
C7 C16 C15 86.00(13) . . ?
C7 C16 H16A 114.3 . . ?
C15 C16 H16A 114.3 . . ?
C7 C16 H16B 114.3 . . ?
C15 C16 H16B 114.3 . . ?
H16A C16 H16B 111.5 . . ?

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
C7 N1 C2 C3 -179.93(17) . . . . ?
C15 N1 C2 C3 -19.0(4) . . . . ?
C7 N1 C2 C1 1.90(17) . . . . ?
C15 N1 C2 C1 162.8(3) . . . . ?
C6 C1 C2 N1 176.96(13) . . . . ?
C8 C1 C2 N1 -1.48(16) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
C8 C1 C2 C3 -179.88(15) . . . . ?
N1 C2 C3 C4 -178.16(19) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
C8 C1 C6 C5 179.90(17) . . . . ?
C2 N1 C7 C8 -1.65(18) . . . . ?
C15 N1 C7 C8 -173.15(13) . . . . ?
C2 N1 C7 C16 172.83(13) . . . . ?
C15 N1 C7 C16 1.33(13) . . . . ?
N1 C7 C8 C1 0.64(16) . . . . ?
C16 C7 C8 C1 -166.1(3) . . . . ?
N1 C7 C8 C9 -179.28(13) . . . . ?
C16 C7 C8 C9 14.0(4) . . . . ?
C6 C1 C8 C7 -177.54(17) . . . . ?
C2 C1 C8 C7 0.55(16) . . . . ?
C6 C1 C8 C9 2.4(3) . . . . ?
C2 C1 C8 C9 -179.54(14) . . . . ?
C7 C8 C9 C10 -147.01(17) . . . . ?
C1 C8 C9 C10 33.1(2) . . . . ?
C7 C8 C9 C14 30.7(2) . . . . ?
C1 C8 C9 C14 -149.18(16) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C8 C9 C10 C11 177.35(17) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C9 0.4(3) . . . . ?
C10 C9 C14 C13 -0.1(3) . . . . ?
C8 C9 C14 C13 -177.96(16) . . . . ?
C7 N1 C15 C16 -1.30(12) . . . . ?
C2 N1 C15 C16 -163.4(3) . . . . ?
N1 C7 C16 C15 -1.27(12) . . . . ?
C8 C7 C16 C15 166.4(3) . . . . ?
N1 C15 C16 C7 1.17(11) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_cd214275
_database_code_depnum_ccdc_archive 'CCDC 1003610'
_audit_update_record             
;
2014-05-16 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.33

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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.2535(19)
_cell_length_b                   14.994(3)
_cell_length_c                   10.714(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.697(4)
_cell_angle_gamma                90
_cell_volume                     1455.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2506
_cell_measurement_theta_min      4.738
_cell_measurement_theta_max      50.578

_exptl_crystal_description       prismatic
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7634
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.369
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2687
_reflns_number_gt                2064
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1121P)²+0.0146P] 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         2687
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1820
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
N1 N 0.41351(16) 0.11241(9) 0.44326(14) 0.0379(4) Uani 1 1 d . . . . .
O1 O 0.62525(17) 0.02848(10) 0.33746(13) 0.0576(5) Uani 1 1 d . . . . .
C1 C 0.33722(19) 0.17789(12) 0.50020(16) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.1850(2) 0.18653(14) 0.48423(19) 0.0475(5) Uani 1 1 d . . . . .
H2 H 0.1216 0.1456 0.4361 0.057 Uiso 1 1 calc R U . . .
C3 C 0.1316(2) 0.25745(14) 0.5418(2) 0.0550(6) Uani 1 1 d . . . . .
H3 H 0.0302 0.2650 0.5323 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2261(3) 0.31778(15) 0.6134(2) 0.0579(6) Uani 1 1 d . . . . .
H4 H 0.1871 0.3658 0.6505 0.069 Uiso 1 1 calc R U . . .
C5 C 0.3785(3) 0.30840(13) 0.6315(2) 0.0509(5) Uani 1 1 d . . . . .
H5 H 0.4417 0.3490 0.6807 0.061 Uiso 1 1 calc R U . . .
C6 C 0.4334(2) 0.23695(12) 0.57400(17) 0.0383(5) Uani 1 1 d . . . . .
C7 C 0.58871(19) 0.20627(11) 0.57429(16) 0.0352(4) Uani 1 1 d . . . . .
C8 C 0.55215(19) 0.12908(11) 0.48094(16) 0.0343(4) Uani 1 1 d . . . . .
C9 C 0.6633(2) 0.07146(11) 0.43395(18) 0.0388(5) Uani 1 1 d . . . . .
C10 C 0.8190(2) 0.07106(15) 0.5073(2) 0.0558(6) Uani 1 1 d . . . . .
H10A H 0.8634 0.1280 0.4943 0.067 Uiso 1 1 calc R U . . .
H10B H 0.8728 0.0254 0.4716 0.067 Uiso 1 1 calc R U . . .
C11 C 0.8405(2) 0.05488(14) 0.6502(2) 0.0605(6) Uani 1 1 d . . . . .
H11A H 0.7738 0.0078 0.6644 0.073 Uiso 1 1 calc R U . . .
H11B H 0.9404 0.0337 0.6811 0.073 Uiso 1 1 calc R U . . .
C12 C 0.8148(2) 0.13538(15) 0.7288(2) 0.0564(6) Uani 1 1 d . . . . .
H12A H 0.8477 0.1208 0.8182 0.068 Uiso 1 1 calc R U . . .
H12B H 0.8760 0.1840 0.7096 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6565(2) 0.16795(14) 0.70835(17) 0.0461(5) Uani 1 1 d . . . . .
H13A H 0.6512 0.2138 0.7712 0.055 Uiso 1 1 calc R U . . .
H13B H 0.5952 0.1187 0.7251 0.055 Uiso 1 1 calc R U . . .
C14 C 0.67905(19) 0.28122(11) 0.53051(17) 0.0364(4) Uani 1 1 d . . . . .
C15 C 0.7526(2) 0.34420(13) 0.6159(2) 0.0476(5) Uani 1 1 d . . . . .
H15 H 0.7531 0.3382 0.7024 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8242(3) 0.41494(14) 0.5745(2) 0.0556(6) Uani 1 1 d . . . . .
H16 H 0.8725 0.4564 0.6329 0.067 Uiso 1 1 calc R U . . .
C17 C 0.8249(2) 0.42491(13) 0.4466(2) 0.0562(6) Uani 1 1 d . . . . .
H17 H 0.8735 0.4730 0.4187 0.067 Uiso 1 1 calc R U . . .
C18 C 0.7537(2) 0.36353(14) 0.3609(2) 0.0515(6) Uani 1 1 d . . . . .
H18 H 0.7541 0.3699 0.2747 0.062 Uiso 1 1 calc R U . . .
C19 C 0.6812(2) 0.29211(12) 0.40237(17) 0.0412(5) Uani 1 1 d . . . . .
H19 H 0.6333 0.2508 0.3435 0.049 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
N1 C8 1.289(2) . ?
N1 C1 1.418(2) . ?
O1 C9 1.208(2) . ?
C1 C6 1.384(3) . ?
C1 C2 1.390(3) . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(3) . ?
C7 C8 1.522(2) . ?
C7 C14 1.530(2) . ?
C7 C13 1.556(2) . ?
C8 C9 1.506(2) . ?
C9 C10 1.495(3) . ?
C10 C11 1.522(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.517(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.387(2) . ?
C14 C15 1.392(2) . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 H19 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
C8 N1 C1 106.36(14) . . ?
C6 C1 C2 121.91(18) . . ?
C6 C1 N1 111.75(15) . . ?
C2 C1 N1 126.32(17) . . ?
C3 C2 C1 117.76(19) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 121.43(19) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.0(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 119.93(18) . . ?
C5 C6 C7 132.14(18) . . ?
C1 C6 C7 107.94(15) . . ?
C6 C7 C8 98.38(13) . . ?
C6 C7 C14 110.79(14) . . ?
C8 C7 C14 114.80(14) . . ?
C6 C7 C13 108.66(14) . . ?
C8 C7 C13 108.66(14) . . ?
C14 C7 C13 114.29(14) . . ?
N1 C8 C9 119.20(16) . . ?
N1 C8 C7 115.33(15) . . ?
C9 C8 C7 125.46(15) . . ?
O1 C9 C10 122.03(17) . . ?
O1 C9 C8 119.46(17) . . ?
C10 C9 C8 118.50(16) . . ?
C9 C10 C11 116.42(17) . . ?
C9 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
C9 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C12 C11 C10 115.34(18) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 115.52(17) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C7 116.66(17) . . ?
C12 C13 H13A 108.1 . . ?
C7 C13 H13A 108.1 . . ?
C12 C13 H13B 108.1 . . ?
C7 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
C19 C14 C15 117.86(17) . . ?
C19 C14 C7 120.56(15) . . ?
C15 C14 C7 121.42(16) . . ?
C16 C15 C14 121.05(19) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.35(19) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.59(19) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.22(19) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.93(18) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?

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
C8 N1 C1 C6 0.67(19) . . . . ?
C8 N1 C1 C2 178.84(17) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
N1 C1 C2 C3 -176.39(16) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -179.20(18) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
N1 C1 C6 C5 176.48(16) . . . . ?
C2 C1 C6 C7 178.05(16) . . . . ?
N1 C1 C6 C7 -3.68(19) . . . . ?
C5 C6 C7 C8 -175.57(19) . . . . ?
C1 C6 C7 C8 4.62(17) . . . . ?
C5 C6 C7 C14 -54.9(3) . . . . ?
C1 C6 C7 C14 125.25(15) . . . . ?
C5 C6 C7 C13 71.4(2) . . . . ?
C1 C6 C7 C13 -108.40(16) . . . . ?
C1 N1 C8 C9 -178.75(14) . . . . ?
C1 N1 C8 C7 2.75(19) . . . . ?
C6 C7 C8 N1 -4.66(18) . . . . ?
C14 C7 C8 N1 -122.26(16) . . . . ?
C13 C7 C8 N1 108.37(17) . . . . ?
C6 C7 C8 C9 176.95(15) . . . . ?
C14 C7 C8 C9 59.3(2) . . . . ?
C13 C7 C8 C9 -70.0(2) . . . . ?
N1 C8 C9 O1 20.9(2) . . . . ?
C7 C8 C9 O1 -160.76(16) . . . . ?
N1 C8 C9 C10 -160.49(17) . . . . ?
C7 C8 C9 C10 17.8(2) . . . . ?
O1 C9 C10 C11 -130.7(2) . . . . ?
C8 C9 C10 C11 50.7(2) . . . . ?
C9 C10 C11 C12 -79.7(2) . . . . ?
C10 C11 C12 C13 67.9(3) . . . . ?
C11 C12 C13 C7 -65.6(2) . . . . ?
C6 C7 C13 C12 -178.59(16) . . . . ?
C8 C7 C13 C12 75.36(19) . . . . ?
C14 C7 C13 C12 -54.3(2) . . . . ?
C6 C7 C14 C19 -89.0(2) . . . . ?
C8 C7 C14 C19 21.3(2) . . . . ?
C13 C7 C14 C19 147.81(17) . . . . ?
C6 C7 C14 C15 86.3(2) . . . . ?
C8 C7 C14 C15 -163.43(17) . . . . ?
C13 C7 C14 C15 -36.9(2) . . . . ?
C19 C14 C15 C16 0.3(3) . . . . ?
C7 C14 C15 C16 -175.11(19) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C15 C14 C19 C18 -0.2(3) . . . . ?
C7 C14 C19 C18 175.22(17) . . . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.085

_shelxl_version_number           2013-4



