# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_n0372b-1
_audit_block_doi                 10.5517/cc1kbls8
_database_code_depnum_ccdc_archive 'CCDC 1440160'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3',5'-Diethyl-2,2':6',2''-terpyridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N3'

_chemical_formula_sum            'C19 H21 N3'
_chemical_formula_weight         291.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.0859(12)
_cell_length_b                   8.8941(5)
_cell_length_c                   8.6908(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.4477(18)
_cell_angle_gamma                90.00
_cell_volume                     1527.18(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    30990
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      34.48

_exptl_crystal_description       platy
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30990
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         34.48
_reflns_number_total             3224
_reflns_number_gt                2665
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0842P)²+0.7749P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3224
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1442
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.90265(4) 0.73510(9) 0.01041(10) 0.01655(16) Uani 1 1 d . . .
N1 N 0.83648(4) 0.75584(9) -0.01936(10) 0.02138(17) Uani 1 1 d . . .
H1A H 0.8219 0.8308 0.0256 0.026 Uiso 1 1 calc R . .
C2 C 0.92697(5) 0.61921(10) -0.06181(11) 0.02189(18) Uani 1 1 d . . .
H2A H 0.9742 0.6089 -0.0397 0.026 Uiso 1 1 calc R . .
C5 C 0.79327(5) 0.65794(11) -0.12032(12) 0.02484(19) Uani 1 1 d . . .
H5A H 0.7463 0.6714 -0.1416 0.030 Uiso 1 1 calc R . .
C3 C 0.88155(5) 0.51909(11) -0.16642(12) 0.0265(2) Uani 1 1 d . . .
H3A H 0.8970 0.4393 -0.2169 0.032 Uiso 1 1 calc R . .
C4 C 0.81300(5) 0.53849(11) -0.19540(12) 0.0262(2) Uani 1 1 d . . .
H4A H 0.7804 0.4715 -0.2650 0.031 Uiso 1 1 calc R . .
C6 C 0.95178(4) 0.83524(9) 0.13230(9) 0.01579(15) Uani 1 1 d . . .
N3 N 1.0000 0.75905(11) 0.2500 0.01695(19) Uani 1 2 d S . .
C8 C 1.0000 1.06820(13) 0.2500 0.0174(2) Uani 1 2 d S . .
H8 H 1.0000 1.1750 0.2500 0.021 Uiso 1 2 calc SR . .
C7 C 0.94953(4) 0.99267(9) 0.12553(10) 0.01636(16) Uani 1 1 d . . .
C9 C 0.89691(4) 1.08112(10) -0.00652(10) 0.01997(17) Uani 1 1 d . . .
H9A H 0.8767 1.0160 -0.1038 0.024 Uiso 1 1 calc R . .
H9B H 0.9191 1.1668 -0.0400 0.024 Uiso 1 1 calc R . .
C11 C 0.84075(5) 1.14075(12) 0.05003(12) 0.0260(2) Uani 1 1 d . . .
H11A H 0.8079 1.1970 -0.0397 0.039 Uiso 1 1 calc R . .
H11B H 0.8603 1.2073 0.1447 0.039 Uiso 1 1 calc R . .
H11C H 0.8180 1.0563 0.0814 0.039 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0178(3) 0.0157(3) 0.0152(3) 0.0006(2) 0.0047(3) 0.0004(2)
N1 0.0181(3) 0.0228(4) 0.0239(3) -0.0048(3) 0.0082(3) -0.0017(2)
C2 0.0221(4) 0.0188(4) 0.0222(4) -0.0016(3) 0.0045(3) 0.0047(3)
C5 0.0197(4) 0.0262(4) 0.0266(4) -0.0036(3) 0.0056(3) -0.0044(3)
C3 0.0319(5) 0.0189(4) 0.0251(4) -0.0048(3) 0.0052(3) 0.0032(3)
C4 0.0293(4) 0.0206(4) 0.0236(4) -0.0032(3) 0.0028(3) -0.0045(3)
C6 0.0159(3) 0.0164(3) 0.0156(3) -0.0003(2) 0.0062(3) 0.0001(2)
N3 0.0163(4) 0.0172(4) 0.0166(4) 0.000 0.0049(3) 0.000
C8 0.0198(5) 0.0148(4) 0.0186(5) 0.000 0.0077(4) 0.000
C7 0.0173(3) 0.0168(3) 0.0160(3) 0.0010(2) 0.0071(3) 0.0010(2)
C9 0.0219(4) 0.0193(4) 0.0177(3) 0.0031(3) 0.0057(3) 0.0020(3)
C11 0.0219(4) 0.0289(4) 0.0242(4) -0.0013(3) 0.0043(3) 0.0073(3)

_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 N1 1.3399(11) . ?
C1 C2 1.3944(12) . ?
C1 C6 1.4907(11) . ?
N1 C5 1.3415(12) . ?
C2 C3 1.3887(13) . ?
C5 C4 1.3846(14) . ?
C3 C4 1.3886(15) . ?
C6 N3 1.3464(9) . ?
C6 C7 1.4015(12) . ?
N3 C6 1.3463(9) 2_755 ?
C8 C7 1.3963(10) 2_755 ?
C8 C7 1.3963(10) . ?
C7 C9 1.5091(11) . ?
C9 C11 1.5269(13) . ?

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
N1 C1 C2 122.47(8) . . ?
N1 C1 C6 118.24(7) . . ?
C2 C1 C6 119.20(7) . . ?
C1 N1 C5 117.41(8) . . ?
C3 C2 C1 119.38(8) . . ?
N1 C5 C4 123.99(9) . . ?
C4 C3 C2 118.37(9) . . ?
C5 C4 C3 118.35(8) . . ?
N3 C6 C7 122.70(8) . . ?
N3 C6 C1 113.08(7) . . ?
C7 C6 C1 124.21(7) . . ?
C6 N3 C6 119.56(10) 2_755 . ?
C7 C8 C7 122.48(11) 2_755 . ?
C8 C7 C6 116.27(8) . . ?
C8 C7 C9 119.82(8) . . ?
C6 C7 C9 123.90(7) . . ?
C7 C9 C11 112.53(7) . . ?

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
C2 C1 N1 C5 1.37(13) . . . . ?
C6 C1 N1 C5 -175.29(8) . . . . ?
N1 C1 C2 C3 -1.21(14) . . . . ?
C6 C1 C2 C3 175.42(8) . . . . ?
C1 N1 C5 C4 -0.39(15) . . . . ?
C1 C2 C3 C4 0.03(14) . . . . ?
N1 C5 C4 C3 -0.73(16) . . . . ?
C2 C3 C4 C5 0.87(15) . . . . ?
N1 C1 C6 N3 127.16(7) . . . . ?
C2 C1 C6 N3 -49.61(10) . . . . ?
N1 C1 C6 C7 -53.88(11) . . . . ?
C2 C1 C6 C7 129.34(9) . . . . ?
C7 C6 N3 C6 0.44(6) . . . 2_755 ?
C1 C6 N3 C6 179.42(7) . . . 2_755 ?
C7 C8 C7 C6 0.39(5) 2_755 . . . ?
C7 C8 C7 C9 -179.29(8) 2_755 . . . ?
N3 C6 C7 C8 -0.84(10) . . . . ?
C1 C6 C7 C8 -179.70(6) . . . . ?
N3 C6 C7 C9 178.83(6) . . . . ?
C1 C6 C7 C9 -0.03(12) . . . . ?
C8 C7 C9 C11 -79.93(9) . . . . ?
C6 C7 C9 C11 100.41(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        34.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_n0373b-1
_audit_block_doi                 10.5517/cc1kblt9
_database_code_depnum_ccdc_archive 'CCDC 1440161'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3',5'-Bis(2-cyclohexylethyl)-2,2':6',2''-terpyridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H39 N3'
_chemical_formula_sum            'C31 H39 N3'
_chemical_formula_weight         453.65

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   30.5673(18)
_cell_length_b                   9.9939(5)
_cell_length_c                   8.7408(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.271(2)
_cell_angle_gamma                90.00
_cell_volume                     2563.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    17425
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      30.41

_exptl_crystal_description       platy
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17425
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         30.41
_reflns_number_total             3858
_reflns_number_gt                2429
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1170P)²+4.4347P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3858
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.2414
_refine_ls_wR_factor_gt          0.2059
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C5 C 0.44284(7) 0.7651(2) 1.0031(2) 0.0212(4) Uani 1 1 d . . .
C6 C 0.39750(6) 0.7548(2) 0.9640(2) 0.0226(4) Uani 1 1 d . . .
H6A H 0.3829 0.6921 1.0150 0.027 Uiso 1 1 calc R . .
C3 C 0.43962(11) 0.9386(3) 0.8108(3) 0.0420(7) Uani 1 1 d . . .
H3A H 0.4540 1.0007 0.7582 0.050 Uiso 1 1 calc R . .
N2 N 0.46533(9) 0.8560(2) 0.9305(3) 0.0458(6) Uani 1 1 d . . .
C1 C 0.37334(9) 0.8372(3) 0.8492(3) 0.0420(7) Uani 1 1 d . . .
H1A H 0.3410 0.8320 0.8212 0.050 Uiso 1 1 calc R . .
C2 C 0.39277(11) 0.9284(3) 0.7702(3) 0.0446(7) Uani 1 1 d . . .
H2B H 0.3742 0.9834 0.6889 0.054 Uiso 1 1 calc R . .
C7 C 0.34822(7) 0.3972(2) 0.9109(2) 0.0206(4) Uani 1 1 d . . .
H7A H 0.3444 0.4674 0.8268 0.025 Uiso 1 1 calc R . .
C9 C 0.30478(7) 0.3953(2) 0.9650(3) 0.0264(5) Uani 1 1 d . . .
H9A H 0.2999 0.4851 1.0053 0.032 Uiso 1 1 calc R . .
H9B H 0.3086 0.3308 1.0538 0.032 Uiso 1 1 calc R . .
C8 C 0.35462(8) 0.2632(2) 0.8363(3) 0.0293(5) Uani 1 1 d . . .
H8A H 0.3609 0.1929 0.9195 0.035 Uiso 1 1 calc R . .
H8B H 0.3812 0.2688 0.7931 0.035 Uiso 1 1 calc R . .
C10 C 0.31224(8) 0.2239(3) 0.7018(3) 0.0351(6) Uani 1 1 d . . .
H10A H 0.3081 0.2883 0.6128 0.042 Uiso 1 1 calc R . .
H10B H 0.3169 0.1341 0.6613 0.042 Uiso 1 1 calc R . .
C12 C 0.26966(8) 0.2225(3) 0.7588(3) 0.0367(6) Uani 1 1 d . . .
H12A H 0.2428 0.2019 0.6680 0.044 Uiso 1 1 calc R . .
H12B H 0.2724 0.1514 0.8399 0.044 Uiso 1 1 calc R . .
C11 C 0.26284(7) 0.3564(2) 0.8298(3) 0.0316(5) Uani 1 1 d . . .
H11A H 0.2359 0.3516 0.8713 0.038 Uiso 1 1 calc R . .
H11B H 0.2570 0.4258 0.7458 0.038 Uiso 1 1 calc R . .
N1 N 0.5000 0.7451(2) 1.2500 0.0199(5) Uani 1 2 d S . .
C15 C 0.5000 0.4697(3) 1.2500 0.0174(5) Uani 1 2 d S . .
H15 H 0.5000 0.3747 1.2500 0.021 Uiso 1 2 calc SR . .
C14 C 0.46806(6) 0.5372(2) 1.1288(2) 0.0174(4) Uani 1 1 d . . .
C13 C 0.47067(6) 0.6770(2) 1.1325(2) 0.0177(4) Uani 1 1 d . . .
C17 C 0.43315(6) 0.4615(2) 1.0023(2) 0.0197(4) Uani 1 1 d . . .
H17A H 0.4461 0.3744 0.9833 0.024 Uiso 1 1 calc R . .
H17B H 0.4258 0.5128 0.9014 0.024 Uiso 1 1 calc R . .
C18 C 0.38907(7) 0.4371(2) 1.0506(2) 0.0215(4) Uani 1 1 d . . .
H18A H 0.3947 0.3654 1.1320 0.026 Uiso 1 1 calc R . .
H18B H 0.3813 0.5196 1.1000 0.026 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C5 0.0217(10) 0.0216(10) 0.0168(9) -0.0026(7) -0.0005(7) 0.0036(8)
C6 0.0131(9) 0.0283(11) 0.0218(10) 0.0015(8) -0.0027(7) 0.0042(8)
C3 0.0605(18) 0.0277(12) 0.0328(13) 0.0088(10) 0.0046(12) 0.0060(12)
N2 0.0550(15) 0.0363(13) 0.0415(13) 0.0076(10) 0.0058(11) 0.0027(11)
C1 0.0293(12) 0.0466(15) 0.0373(14) -0.0042(12) -0.0115(10) 0.0159(11)
C2 0.0596(18) 0.0338(14) 0.0290(13) 0.0019(11) -0.0063(12) 0.0231(13)
C7 0.0187(9) 0.0233(10) 0.0188(9) -0.0022(8) 0.0036(7) -0.0046(8)
C9 0.0184(9) 0.0310(12) 0.0285(11) -0.0033(9) 0.0044(8) -0.0063(8)
C8 0.0253(11) 0.0281(12) 0.0291(12) -0.0070(9) -0.0012(9) 0.0007(9)
C10 0.0359(13) 0.0308(12) 0.0304(12) -0.0103(10) -0.0043(10) 0.0002(10)
C12 0.0311(12) 0.0293(12) 0.0391(14) -0.0028(10) -0.0076(10) -0.0101(10)
C11 0.0185(10) 0.0352(13) 0.0371(13) -0.0022(10) 0.0011(9) -0.0065(9)
N1 0.0170(11) 0.0206(12) 0.0199(12) 0.000 0.0012(9) 0.000
C15 0.0161(12) 0.0173(13) 0.0199(13) 0.000 0.0069(10) 0.000
C14 0.0131(8) 0.0235(10) 0.0160(9) -0.0007(7) 0.0046(7) -0.0003(7)
C13 0.0133(8) 0.0226(10) 0.0162(8) 0.0001(7) 0.0028(7) 0.0013(7)
C17 0.0164(9) 0.0244(10) 0.0176(9) -0.0037(7) 0.0037(7) -0.0027(7)
C18 0.0179(9) 0.0289(11) 0.0170(9) -0.0024(8) 0.0039(7) -0.0061(8)

_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
C5 C6 1.335(3) . ?
C5 N2 1.395(3) . ?
C5 C13 1.496(3) . ?
C6 C1 1.347(3) . ?
C3 C2 1.379(4) . ?
C3 N2 1.390(3) . ?
C1 C2 1.375(4) . ?
C7 C8 1.526(3) . ?
C7 C9 1.529(3) . ?
C7 C18 1.534(3) . ?
C9 C11 1.530(3) . ?
C8 C10 1.536(3) . ?
C10 C12 1.518(4) . ?
C12 C11 1.514(4) . ?
N1 C13 1.344(2) 2_657 ?
N1 C13 1.344(2) . ?
C15 C14 1.397(2) . ?
C15 C14 1.397(2) 2_657 ?
C14 C13 1.399(3) . ?
C14 C17 1.508(3) . ?
C17 C18 1.540(3) . ?

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
C6 C5 N2 122.9(2) . . ?
C6 C5 C13 118.51(19) . . ?
N2 C5 C13 118.61(19) . . ?
C5 C6 C1 117.1(2) . . ?
C2 C3 N2 118.5(3) . . ?
C3 N2 C5 118.8(2) . . ?
C6 C1 C2 123.8(2) . . ?
C1 C2 C3 118.9(2) . . ?
C8 C7 C9 110.37(18) . . ?
C8 C7 C18 113.26(17) . . ?
C9 C7 C18 109.92(16) . . ?
C7 C9 C11 112.11(19) . . ?
C7 C8 C10 111.68(18) . . ?
C12 C10 C8 111.6(2) . . ?
C11 C12 C10 110.8(2) . . ?
C12 C11 C9 111.08(19) . . ?
C13 N1 C13 119.1(2) 2_657 . ?
C14 C15 C14 122.3(3) . 2_657 ?
C15 C14 C13 116.19(18) . . ?
C15 C14 C17 120.97(18) . . ?
C13 C14 C17 122.84(17) . . ?
N1 C13 C14 123.01(18) . . ?
N1 C13 C5 113.31(18) . . ?
C14 C13 C5 123.62(17) . . ?
C14 C17 C18 111.85(16) . . ?
C7 C18 C17 113.74(16) . . ?

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
N2 C5 C6 C1 -0.1(3) . . . . ?
C13 C5 C6 C1 178.8(2) . . . . ?
C2 C3 N2 C5 0.8(4) . . . . ?
C6 C5 N2 C3 -0.8(4) . . . . ?
C13 C5 N2 C3 -179.7(2) . . . . ?
C5 C6 C1 C2 1.0(4) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
N2 C3 C2 C1 0.0(4) . . . . ?
C8 C7 C9 C11 -54.5(2) . . . . ?
C18 C7 C9 C11 179.85(19) . . . . ?
C9 C7 C8 C10 53.8(3) . . . . ?
C18 C7 C8 C10 177.55(19) . . . . ?
C7 C8 C10 C12 -55.3(3) . . . . ?
C8 C10 C12 C11 55.9(3) . . . . ?
C10 C12 C11 C9 -56.1(3) . . . . ?
C7 C9 C11 C12 56.0(3) . . . . ?
C14 C15 C14 C13 1.89(12) 2_657 . . . ?
C14 C15 C14 C17 -178.23(19) 2_657 . . . ?
C13 N1 C13 C14 2.14(14) 2_657 . . . ?
C13 N1 C13 C5 -175.16(18) 2_657 . . . ?
C15 C14 C13 N1 -4.1(3) . . . . ?
C17 C14 C13 N1 176.07(15) . . . . ?
C15 C14 C13 C5 172.97(16) . . . . ?
C17 C14 C13 C5 -6.9(3) . . . . ?
C6 C5 C13 N1 -125.46(19) . . . . ?
N2 C5 C13 N1 53.5(2) . . . . ?
C6 C5 C13 C14 57.3(3) . . . . ?
N2 C5 C13 C14 -123.8(2) . . . . ?
C15 C14 C17 C18 90.2(2) . . . . ?
C13 C14 C17 C18 -89.9(2) . . . . ?
C8 C7 C18 C17 64.3(2) . . . . ?
C9 C7 C18 C17 -171.68(18) . . . . ?
C14 C17 C18 C7 163.62(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        30.41
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.079
