# Electronic Supplementary Material (ESI) for ChemComm.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1547832'
_audit_update_record             
;
2017-05-04 deposited with the CCDC.
2017-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N3 O'
_chemical_formula_weight         327.38

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                   5.9781(15)
_cell_length_b                   12.919(2)
_cell_length_c                   22.346(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.713(5)
_cell_angle_gamma                90
_cell_volume                     1723.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    566(2)
_cell_measurement_reflns_used    1697
_cell_measurement_theta_min      22.9
_cell_measurement_theta_max      67.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      566(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12791
_diffrn_reflns_av_unetI/netI     0.0845
_diffrn_reflns_av_R_equivalents  0.1389
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.821
_diffrn_reflns_theta_max         25.327
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3059
_reflns_number_gt                1947
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1500P)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     SHELXL
_refine_ls_extinction_coef       0.30(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3059
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0942
_refine_ls_wR_factor_ref         0.3197
_refine_ls_wR_factor_gt          0.2566
_refine_ls_goodness_of_fit_ref   1.409
_refine_ls_restrained_S_all      1.409
_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 0.9189(4) 0.26975(17) 0.18551(10) 0.0570(8) Uani 1 1 d . . . . .
O2 O 0.7033(4) 0.12965(17) 0.20169(9) 0.0713(8) Uani 1 1 d . . . . .
N3 N 1.0051(4) 0.21867(18) 0.13611(11) 0.0603(8) Uani 1 1 d . . . . .
C4 C 0.8945(5) 0.1174(2) 0.05547(11) 0.0520(8) Uani 1 1 d . . . . .
H4A H 1.0220 0.0775 0.0634 0.062 Uiso 1 1 calc R U . . .
C5 C 0.9622(5) 0.4040(2) 0.25694(12) 0.0616(9) Uani 1 1 d . . . . .
H5A H 1.0311 0.4648 0.2703 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7699(5) 0.2141(2) 0.21922(13) 0.0596(9) Uani 1 1 d . . . . .
C7 C 0.7005(5) 0.2641(2) 0.27396(13) 0.0613(9) Uani 1 1 d . . . . .
C8 C 1.1736(5) 0.4179(2) 0.16496(13) 0.0603(9) Uani 1 1 d . . . . .
C9 C 0.7320(6) 0.4014(3) 0.34662(14) 0.0768(10) Uani 1 1 d . . . . .
H9A H 0.7959 0.4632 0.3603 0.092 Uiso 1 1 calc R U . . .
C10 C 1.0182(5) 0.3638(2) 0.20428(13) 0.0578(9) Uani 1 1 d . . . . .
C11 C 0.8477(5) 0.1962(2) 0.08940(12) 0.0587(9) Uani 1 1 d . . . . .
C12 C 1.3692(5) 0.4597(3) 0.19103(15) 0.0693(10) Uani 1 1 d . . . . .
H12A H 1.4060 0.4470 0.2313 0.083 Uiso 1 1 calc R U . . .
C13 C 0.8017(5) 0.3569(2) 0.29288(12) 0.0615(9) Uani 1 1 d . . . . .
N2 N 0.6594(6) 0.2597(3) 0.07970(14) 0.0930(11) Uani 1 1 d . . . . .
C15 C 0.5384(6) 0.2175(3) 0.30781(15) 0.0743(10) Uani 1 1 d . . . . .
H15A H 0.4741 0.1551 0.2953 0.089 Uiso 1 1 calc R U . . .
C16 C 0.7514(8) 0.0960(3) 0.00848(16) 0.0875(12) Uani 1 1 d . . . . .
H16A H 0.7830 0.0398 -0.0157 0.105 Uiso 1 1 calc R U . . .
C17 C 1.1214(6) 0.4387(3) 0.10462(14) 0.0747(10) Uani 1 1 d . . . . .
H17A H 0.9916 0.4116 0.0862 0.090 Uiso 1 1 calc R U . . .
C18 C 0.4739(8) 0.2630(3) 0.35922(18) 0.0913(12) Uani 1 1 d . . . . .
H18A H 0.3638 0.2327 0.3815 0.110 Uiso 1 1 calc R U . . .
C19 C 1.1760(6) 0.1420(3) 0.15340(16) 0.0774(11) Uani 1 1 d . . . . .
H19A H 1.2278 0.1089 0.1182 0.116 Uiso 1 1 calc R U . . .
H19B H 1.1131 0.0910 0.1790 0.116 Uiso 1 1 calc R U . . .
H19C H 1.2994 0.1757 0.1744 0.116 Uiso 1 1 calc R U . . .
C20 C 0.5748(8) 0.3556(3) 0.37817(16) 0.0901(13) Uani 1 1 d . . . . .
H20A H 0.5318 0.3862 0.4135 0.108 Uiso 1 1 calc R U . . .
C21 C 1.5089(6) 0.5196(3) 0.1583(2) 0.0872(12) Uani 1 1 d . . . . .
H21A H 1.6402 0.5462 0.1763 0.105 Uiso 1 1 calc R U . . .
C22 C 0.5165(7) 0.2347(3) 0.03040(17) 0.0912(12) Uani 1 1 d . . . . .
H22A H 0.3888 0.2739 0.0216 0.109 Uiso 1 1 calc R U . . .
C23 C 1.2613(6) 0.4990(3) 0.07259(16) 0.0854(12) Uani 1 1 d . . . . .
H23A H 1.2246 0.5123 0.0324 0.102 Uiso 1 1 calc R U . . .
C24 C 1.4535(7) 0.5402(3) 0.0982(2) 0.0942(13) Uani 1 1 d . . . . .
H24A H 1.5459 0.5814 0.0758 0.113 Uiso 1 1 calc R U . . .
C25 C 0.5676(8) 0.1509(4) -0.00501(16) 0.0963(13) Uani 1 1 d . . . . .
H25A H 0.4745 0.1332 -0.0379 0.116 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 C6 1.393(4) . ?
N1 N3 1.405(3) . ?
N1 C10 1.408(4) . ?
O2 C6 1.219(3) . ?
N3 C11 1.402(4) . ?
N3 C19 1.462(4) . ?
C4 C11 1.307(4) . ?
C4 C16 1.352(5) . ?
C5 C10 1.343(4) . ?
C5 C13 1.417(4) . ?
C6 C7 1.461(4) . ?
C7 C15 1.394(5) . ?
C7 C13 1.399(4) . ?
C8 C12 1.391(4) . ?
C8 C17 1.396(4) . ?
C8 C10 1.483(4) . ?
C9 C20 1.339(5) . ?
C9 C13 1.412(4) . ?
C11 N2 1.401(4) . ?
C12 C21 1.373(5) . ?
N2 C22 1.400(5) . ?
C15 C18 1.362(5) . ?
C16 C25 1.330(6) . ?
C17 C23 1.369(5) . ?
C18 C20 1.396(6) . ?
C21 C24 1.395(6) . ?
C22 C25 1.384(6) . ?
C23 C24 1.367(5) . ?

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 N1 N3 116.8(2) . . ?
C6 N1 C10 123.8(2) . . ?
N3 N1 C10 118.3(2) . . ?
C11 N3 N1 115.1(2) . . ?
C11 N3 C19 119.5(2) . . ?
N1 N3 C19 112.9(2) . . ?
C11 C4 C16 117.7(3) . . ?
C10 C5 C13 122.3(3) . . ?
O2 C6 N1 119.7(3) . . ?
O2 C6 C7 124.3(3) . . ?
N1 C6 C7 116.0(3) . . ?
C15 C7 C13 120.5(3) . . ?
C15 C7 C6 119.7(3) . . ?
C13 C7 C6 119.8(3) . . ?
C12 C8 C17 118.3(3) . . ?
C12 C8 C10 118.2(3) . . ?
C17 C8 C10 123.0(3) . . ?
C20 C9 C13 120.7(3) . . ?
C5 C10 N1 118.4(3) . . ?
C5 C10 C8 121.7(3) . . ?
N1 C10 C8 119.8(2) . . ?
C4 C11 N2 123.9(3) . . ?
C4 C11 N3 116.0(3) . . ?
N2 C11 N3 120.0(3) . . ?
C21 C12 C8 121.1(3) . . ?
C7 C13 C9 117.7(3) . . ?
C7 C13 C5 119.4(3) . . ?
C9 C13 C5 122.8(3) . . ?
C22 N2 C11 116.3(3) . . ?
C18 C15 C7 120.2(3) . . ?
C25 C16 C4 123.5(4) . . ?
C23 C17 C8 120.0(3) . . ?
C15 C18 C20 119.4(4) . . ?
C9 C20 C18 121.5(3) . . ?
C12 C21 C24 119.8(4) . . ?
C25 C22 N2 119.2(4) . . ?
C24 C23 C17 121.7(3) . . ?
C23 C24 C21 119.0(4) . . ?
C16 C25 C22 119.3(4) . . ?

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_H
_database_code_depnum_ccdc_archive 'CCDC 1548078'
_audit_update_record             
;
2017-05-05 deposited with the CCDC.
2017-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H21 N3 O'
_chemical_formula_weight         403.47

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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.047(6)
_cell_length_b                   20.569(9)
_cell_length_c                   10.343(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.101(17)
_cell_angle_gamma                90
_cell_volume                     2145.3(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    566(2)
_cell_measurement_reflns_used    2302
_cell_measurement_theta_min      23.2
_cell_measurement_theta_max      67.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      566(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28605
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_av_R_equivalents  0.1700
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.980
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3834
_reflns_number_gt                3367
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1781P)²+0.2335P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.23(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3834
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0859
_refine_ls_wR_factor_ref         0.2917
_refine_ls_wR_factor_gt          0.2497
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38814(16) 0.74756(10) 0.05671(18) 0.0790(6) Uani 1 1 d . . . . .
N1 N 0.53619(17) 0.67809(9) 0.21364(18) 0.0592(6) Uani 1 1 d . . . . .
N2 N 0.45344(18) 0.62564(9) 0.14863(19) 0.0629(6) Uani 1 1 d . . . . .
N3 N 0.2505(2) 0.57804(11) 0.0909(2) 0.0814(7) Uani 1 1 d . . . . .
C21 C 0.6945(2) 0.59506(10) 0.3548(2) 0.0588(6) Uani 1 1 d . . . . .
C14 C 0.3395(2) 0.62035(10) 0.1735(2) 0.0589(6) Uani 1 1 d . . . . .
C9 C 0.6584(2) 0.66461(10) 0.3264(2) 0.0555(6) Uani 1 1 d . . . . .
C10 C 0.3229(2) 0.65563(11) 0.2796(2) 0.0657(6) Uani 1 1 d . . . . .
H10 H 0.3879 0.6845 0.3357 0.079 Uiso 1 1 calc R U . . .
C5 C 0.6968(2) 0.78040(10) 0.3616(2) 0.0592(6) Uani 1 1 d . . . . .
C22 C 0.8695(2) 0.69984(10) 0.5167(2) 0.0583(6) Uani 1 1 d . . . . .
C23 C 0.8781(2) 0.67134(12) 0.6418(2) 0.0693(7) Uani 1 1 d . . . . .
H23 H 0.8013 0.6598 0.6523 0.083 Uiso 1 1 calc R U . . .
C4 C 0.5772(2) 0.79320(11) 0.2438(2) 0.0610(6) Uani 1 1 d . . . . .
C7 C 0.7382(2) 0.71397(10) 0.3993(2) 0.0568(6) Uani 1 1 d . . . . .
C16 C 0.6487(3) 0.55766(11) 0.4368(2) 0.0702(7) Uani 1 1 d . . . . .
H16 H 0.5890 0.5753 0.4696 0.084 Uiso 1 1 calc R U . . .
C6 C 0.7710(3) 0.83397(11) 0.4378(3) 0.0688(6) Uani 1 1 d . . . . .
H6 H 0.8500 0.8271 0.5166 0.083 Uiso 1 1 calc R U . . .
C8 C 0.4928(2) 0.74036(11) 0.1618(2) 0.0628(6) Uani 1 1 d . . . . .
C3 C 0.5353(3) 0.85706(12) 0.2042(3) 0.0717(7) Uani 1 1 d . . . . .
H3 H 0.4561 0.8649 0.1263 0.086 Uiso 1 1 calc R U . . .
C27 C 0.9859(2) 0.71633(12) 0.5036(3) 0.0718(7) Uani 1 1 d . . . . .
H27 H 0.9820 0.7348 0.4199 0.086 Uiso 1 1 calc R U . . .
C20 C 0.7799(3) 0.56771(14) 0.3039(3) 0.0833(8) Uani 1 1 d . . . . .
H20 H 0.8112 0.5922 0.2485 0.100 Uiso 1 1 calc R U . . .
C24 C 1.0010(3) 0.66007(15) 0.7512(3) 0.0854(8) Uani 1 1 d . . . . .
H24 H 1.0058 0.6407 0.8345 0.102 Uiso 1 1 calc R U . . .
C11 C 0.2093(3) 0.64724(14) 0.3002(3) 0.0786(7) Uani 1 1 d . . . . .
H11 H 0.1959 0.6704 0.3705 0.094 Uiso 1 1 calc R U . . .
C15 C 0.4609(3) 0.60229(16) 0.0195(3) 0.0865(9) Uani 1 1 d . . . . .
H15A H 0.4347 0.6364 -0.0499 0.130 Uiso 1 1 calc R U . . .
H15B H 0.4026 0.5658 -0.0164 0.130 Uiso 1 1 calc R U . . .
H15C H 0.5502 0.5893 0.0395 0.130 Uiso 1 1 calc R U . . .
C25 C 1.1148(3) 0.67699(15) 0.7382(3) 0.0889(9) Uani 1 1 d . . . . .
H25 H 1.1967 0.6694 0.8125 0.107 Uiso 1 1 calc R U . . .
C17 C 0.6915(3) 0.49413(13) 0.4703(3) 0.0845(8) Uani 1 1 d . . . . .
H17 H 0.6626 0.4698 0.5280 0.101 Uiso 1 1 calc R U . . .
C2 C 0.6106(3) 0.90836(12) 0.2799(3) 0.0773(7) Uani 1 1 d . . . . .
H2 H 0.5831 0.9508 0.2527 0.093 Uiso 1 1 calc R U . . .
C1 C 0.7279(3) 0.89643(11) 0.3970(3) 0.0759(7) Uani 1 1 d . . . . .
H1 H 0.7782 0.9312 0.4488 0.091 Uiso 1 1 calc R U . . .
C26 C 1.1084(3) 0.70526(14) 0.6151(3) 0.0828(8) Uani 1 1 d . . . . .
H26 H 1.1859 0.7170 0.6063 0.099 Uiso 1 1 calc R U . . .
C12 C 0.1147(3) 0.60400(17) 0.2157(4) 0.0929(9) Uani 1 1 d . . . . .
H12 H 0.0363 0.5975 0.2269 0.111 Uiso 1 1 calc R U . . .
C18 C 0.7756(4) 0.46707(14) 0.4192(4) 0.0960(10) Uani 1 1 d . . . . .
H18 H 0.8032 0.4242 0.4410 0.115 Uiso 1 1 calc R U . . .
C13 C 0.1403(3) 0.57108(16) 0.1150(4) 0.0976(10) Uani 1 1 d . . . . .
H13 H 0.0768 0.5416 0.0587 0.117 Uiso 1 1 calc R U . . .
C19 C 0.8196(4) 0.50317(15) 0.3356(4) 0.1026(11) Uani 1 1 d . . . . .
H19 H 0.8761 0.4845 0.2997 0.123 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.230(3) . ?
N1 C8 1.396(3) . ?
N1 N2 1.396(3) . ?
N1 C9 1.405(3) . ?
N2 C14 1.389(3) . ?
N2 C15 1.453(3) . ?
N3 C14 1.329(3) . ?
N3 C13 1.345(4) . ?
C21 C20 1.375(3) . ?
C21 C16 1.384(3) . ?
C21 C9 1.482(3) . ?
C14 C10 1.389(3) . ?
C9 C7 1.354(3) . ?
C10 C11 1.367(4) . ?
C10 H10 0.9300 . ?
C5 C6 1.407(3) . ?
C5 C4 1.409(3) . ?
C5 C7 1.443(3) . ?
C22 C23 1.388(3) . ?
C22 C27 1.389(3) . ?
C22 C7 1.492(3) . ?
C23 C24 1.387(4) . ?
C23 H23 0.9300 . ?
C4 C3 1.397(3) . ?
C4 C8 1.458(3) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C6 C1 1.375(3) . ?
C6 H6 0.9300 . ?
C3 C2 1.373(4) . ?
C3 H3 0.9300 . ?
C27 C26 1.392(4) . ?
C27 H27 0.9300 . ?
C20 C19 1.394(4) . ?
C20 H20 0.9300 . ?
C24 C25 1.363(5) . ?
C24 H24 0.9300 . ?
C11 C12 1.379(5) . ?
C11 H11 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C25 C26 1.375(5) . ?
C25 H25 0.9300 . ?
C17 C18 1.362(4) . ?
C17 H17 0.9300 . ?
C2 C1 1.388(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C26 H26 0.9300 . ?
C12 C13 1.366(5) . ?
C12 H12 0.9300 . ?
C18 C19 1.370(5) . ?
C18 H18 0.9300 . ?
C13 H13 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 N2 118.00(18) . . ?
C8 N1 C9 124.26(18) . . ?
N2 N1 C9 117.74(17) . . ?
C14 N2 N1 115.86(17) . . ?
C14 N2 C15 122.72(19) . . ?
N1 N2 C15 115.2(2) . . ?
C14 N3 C13 116.0(2) . . ?
C20 C21 C16 119.1(2) . . ?
C20 C21 C9 119.3(2) . . ?
C16 C21 C9 121.5(2) . . ?
N3 C14 C10 123.2(2) . . ?
N3 C14 N2 114.9(2) . . ?
C10 C14 N2 121.85(19) . . ?
C7 C9 N1 120.04(19) . . ?
C7 C9 C21 123.51(19) . . ?
N1 C9 C21 116.41(18) . . ?
C11 C10 C14 118.9(2) . . ?
C11 C10 H10 120.6 . . ?
C14 C10 H10 120.6 . . ?
C6 C5 C4 117.6(2) . . ?
C6 C5 C7 122.9(2) . . ?
C4 C5 C7 119.5(2) . . ?
C23 C22 C27 118.7(2) . . ?
C23 C22 C7 121.0(2) . . ?
C27 C22 C7 120.3(2) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 C8 118.3(2) . . ?
C5 C4 C8 121.01(19) . . ?
C9 C7 C5 119.8(2) . . ?
C9 C7 C22 120.18(19) . . ?
C5 C7 C22 119.98(19) . . ?
C21 C16 C17 120.3(2) . . ?
C21 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O1 C8 N1 120.1(2) . . ?
O1 C8 C4 124.9(2) . . ?
N1 C8 C4 115.02(19) . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C22 C27 C26 120.3(3) . . ?
C22 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C24 C25 C26 119.9(2) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C6 C1 C2 121.1(2) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C25 C26 C27 120.1(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C13 C12 C11 117.7(3) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
N3 C13 C12 125.0(3) . . ?
N3 C13 H13 117.5 . . ?
C12 C13 H13 117.5 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-2

