# 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_h7u1
_database_code_depnum_ccdc_archive 'CCDC 1572025'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         390.47
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   6.5160(8)
_cell_length_b                   14.1444(19)
_cell_length_c                   20.123(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1854.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    199
_cell_measurement_theta_min      0.2372
_cell_measurement_theta_max      20.3127
_cell_measurement_temperature    103.0(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.036
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_T_max  0.989

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.0(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            21312
_diffrn_reflns_av_R_equivalents  0.1066
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             3387
_reflns_number_gt                2634
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1271
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_number_reflns         3387
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.024(3)
_refine_ls_abs_structure_details 
;

Flack x determined using 873 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 853)'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N001 0.3772(5) 0.6149(3) 0.65481(16) 0.0240(9) Uani d . . . 1 . .
N N002 0.1518(5) 0.6054(3) 0.82974(16) 0.0249(9) Uani d . . . 1 . .
N N003 0.5003(6) 0.5295(3) 0.76237(15) 0.0251(8) Uani d . . D 1 . .
N N004 0.0291(6) 0.6903(3) 0.72212(15) 0.0243(9) Uani d . . D 1 . .
C C005 -0.1540(7) 0.7300(3) 0.74001(19) 0.0238(10) Uani d . . . 1 . .
C C006 0.2391(7) 0.6703(3) 0.62356(19) 0.0232(10) Uani d . . . 1 . .
C C007 -0.2348(7) 0.7757(3) 0.68237(19) 0.0265(10) Uani d . . . 1 . .
H H007 -0.359801 0.810042 0.679844 0.032 Uiso calc U . R 1 . .
C C008 0.2900(7) 0.5501(3) 0.8607(2) 0.0281(11) Uani d . . . 1 . .
C C009 0.6810(7) 0.4884(3) 0.7443(2) 0.0267(10) Uani d . . . 1 . .
C C00A 0.0661(6) 0.7069(3) 0.65683(18) 0.0226(10) Uani d . . . 1 . .
C C00B 0.6939(7) 0.5311(3) 0.62112(19) 0.0256(10) Uani d . . . 1 . .
C C00C 0.7608(7) 0.4419(3) 0.8018(2) 0.0301(11) Uani d . . . 1 . .
H H00C 0.884529 0.406506 0.804021 0.036 Uiso calc U . R 1 . .
C C00D 0.2930(7) 0.6811(3) 0.55491(19) 0.0270(11) Uani d . . . 1 . .
H H00D 0.221455 0.716927 0.522386 0.032 Uiso calc U . R 1 . .
C C00E 0.5188(7) 0.5879(3) 0.60833(19) 0.0261(10) Uani d . . . 1 . .
C C00F 0.4632(7) 0.5130(3) 0.82767(18) 0.0249(10) Uani d . . . 1 . .
C C00G 0.0103(7) 0.6332(3) 0.87576(19) 0.0267(11) Uani d . . . 1 . .
C C00H -0.2388(7) 0.7285(3) 0.8048(2) 0.0248(10) Uani d . . . 1 . .
C C00I -0.1646(7) 0.6889(3) 0.86347(19) 0.0270(11) Uani d . . . 1 . .
C C00J 0.4676(7) 0.6296(3) 0.54566(19) 0.0277(11) Uani d . . . 1 . .
H H00J 0.541328 0.622664 0.505229 0.033 Uiso calc U . R 1 . .
C C00K 0.7648(7) 0.4897(3) 0.6797(2) 0.0258(10) Uani d . . . 1 . .
C C00L -0.1010(7) 0.7612(3) 0.63209(19) 0.0258(10) Uani d . . . 1 . .
H H00L -0.116032 0.78339 0.587809 0.031 Uiso calc U . R 1 . .
C C00M 0.2381(7) 0.5407(3) 0.9298(2) 0.0312(11) Uani d . . . 1 . .
H H00M 0.310741 0.505476 0.962379 0.037 Uiso calc U . R 1 . .
C C00N 0.0652(7) 0.5920(4) 0.9392(2) 0.0315(12) Uani d . . . 1 . .
H H00N -0.006793 0.599626 0.979882 0.038 Uiso calc U . R 1 . .
C C00O -0.3123(7) 0.7104(4) 0.9204(2) 0.0336(12) Uani d . . . 1 . .
H H00A -0.238224 0.738907 0.958409 0.04 Uiso calc U . R 1 . .
H H00B -0.381395 0.651954 0.9357 0.04 Uiso calc U . R 1 . .
C C00P 0.6288(7) 0.4572(3) 0.8527(2) 0.0295(11) Uani d . . . 1 . .
H H00P 0.643619 0.434937 0.896967 0.035 Uiso calc U . R 1 . .
C C00Q 0.9668(7) 0.4405(3) 0.6674(2) 0.0322(11) Uani d . . . 1 . .
H H00E 0.967442 0.376846 0.687778 0.039 Uiso calc U . R 1 . .
H H00F 1.082102 0.477669 0.685939 0.039 Uiso calc U . R 1 . .
C C00R 0.8447(7) 0.5113(3) 0.56500(19) 0.0302(11) Uani d . . . 1 . .
H H00G 0.924968 0.568611 0.553993 0.036 Uiso calc U . R 1 . .
H H00H 0.771701 0.48963 0.524624 0.036 Uiso calc U . R 1 . .
C C00S -0.4686(7) 0.7802(4) 0.8916(2) 0.0366(12) Uani d . . . 1 . .
H H00I -0.609748 0.761685 0.904313 0.044 Uiso calc U . R 1 . .
H H00K -0.441849 0.844839 0.908401 0.044 Uiso calc U . R 1 . .
C C00T 0.9840(8) 0.4336(4) 0.5920(2) 0.0404(13) Uani d . . . 1 . .
H H00O 0.937936 0.370752 0.576309 0.048 Uiso calc U . R 1 . .
H H00Q 1.127489 0.443721 0.577519 0.048 Uiso calc U . R 1 . .
C C00U -0.4429(7) 0.7767(4) 0.8165(2) 0.0333(12) Uani d . . . 1 . .
H H00R -0.555763 0.74019 0.795844 0.04 Uiso calc U . R 1 . .
H H00S -0.44241 0.841273 0.797563 0.04 Uiso calc U . R 1 . .
H H1AB 0.110(6) 0.655(3) 0.7549(16) 0.057(16) Uiso d . . D 1 . .
H H2AB 0.421(6) 0.565(3) 0.7294(17) 0.071(18) Uiso d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N001 C006 . 1.349(5) ?
N001 C00E . 1.369(5) ?
N002 C008 . 1.346(6) ?
N002 C00G . 1.364(5) ?
N003 C00F . 1.356(5) ?
N003 C009 . 1.362(6) ?
N003 H2AB . 0.9800(14) ?
N004 C00A . 1.356(5) ?
N004 C005 . 1.367(6) ?
N004 H1AB . 0.9801(14) ?
C005 C00H . 1.415(5) ?
C005 C007 . 1.428(6) ?
C006 C00A . 1.409(6) ?
C006 C00D . 1.433(6) ?
C007 C00L . 1.351(6) ?
C007 H007 . 0.95 ?
C008 C00F . 1.410(6) ?
C008 C00M . 1.438(6) ?
C009 C00K . 1.410(6) ?
C009 C00C . 1.430(6) ?
C00A C00L . 1.422(6) ?
C00B C00K . 1.395(6) ?
C00B C00E . 1.418(6) ?
C00B C00R . 1.523(6) ?
C00C C00P . 1.354(6) ?
C00C H00C . 0.95 ?
C00D C00J . 1.364(6) ?
C00D H00D . 0.95 ?
C00E C00J . 1.432(6) ?
C00F C00P . 1.429(6) ?
C00G C00I . 1.407(6) ?
C00G C00N . 1.448(6) ?
C00H C00I . 1.394(6) ?
C00H C00U . 1.513(6) ?
C00I C00O . 1.527(6) ?
C00J H00J . 0.95 ?
C00K C00Q . 1.510(6) ?
C00L H00L . 0.95 ?
C00M C00N . 1.354(7) ?
C00M H00M . 0.95 ?
C00N H00N . 0.95 ?
C00O C00S . 1.532(7) ?
C00O H00A . 0.99 ?
C00O H00B . 0.99 ?
C00P H00P . 0.95 ?
C00Q C00T . 1.523(6) ?
C00Q H00E . 0.99 ?
C00Q H00F . 0.99 ?
C00R C00T . 1.525(6) ?
C00R H00G . 0.99 ?
C00R H00H . 0.99 ?
C00S C00U . 1.522(6) ?
C00S H00I . 0.99 ?
C00S H00K . 0.99 ?
C00T H00O . 0.99 ?
C00T H00Q . 0.99 ?
C00U H00R . 0.99 ?
C00U H00S . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C006 N001 C00E . . 107.1(3) ?
C008 N002 C00G . . 107.8(3) ?
C00F N003 C009 . . 109.8(4) ?
C00F N003 H2AB . . 130.(3) ?
C009 N003 H2AB . . 120.(3) ?
C00A N004 C005 . . 109.8(4) ?
C00A N004 H1AB . . 130.(3) ?
C005 N004 H1AB . . 120.(3) ?
N004 C005 C00H . . 125.2(4) ?
N004 C005 C007 . . 107.1(3) ?
C00H C005 C007 . . 127.6(4) ?
N001 C006 C00A . . 121.7(3) ?
N001 C006 C00D . . 110.3(4) ?
C00A C006 C00D . . 127.9(4) ?
C00L C007 C005 . . 107.6(4) ?
C00L C007 H007 . . 126.2 ?
C005 C007 H007 . . 126.2 ?
N002 C008 C00F . . 122.3(4) ?
N002 C008 C00M . . 110.1(4) ?
C00F C008 C00M . . 127.5(4) ?
N003 C009 C00K . . 125.1(4) ?
N003 C009 C00C . . 107.1(4) ?
C00K C009 C00C . . 127.7(4) ?
N004 C00A C006 . . 122.6(4) ?
N004 C00A C00L . . 107.2(4) ?
C006 C00A C00L . . 130.1(3) ?
C00K C00B C00E . . 131.1(4) ?
C00K C00B C00R . . 109.6(4) ?
C00E C00B C00R . . 119.3(4) ?
C00P C00C C009 . . 107.9(4) ?
C00P C00C H00C . . 126.1 ?
C009 C00C H00C . . 126.1 ?
C00J C00D C006 . . 106.2(4) ?
C00J C00D H00D . . 126.9 ?
C006 C00D H00D . . 126.9 ?
N001 C00E C00B . . 125.2(4) ?
N001 C00E C00J . . 109.2(4) ?
C00B C00E C00J . . 125.5(4) ?
N003 C00F C008 . . 122.3(4) ?
N003 C00F C00P . . 107.6(4) ?
C008 C00F C00P . . 130.1(4) ?
N002 C00G C00I . . 126.1(4) ?
N002 C00G C00N . . 108.4(4) ?
C00I C00G C00N . . 125.5(4) ?
C00I C00H C005 . . 130.6(4) ?
C00I C00H C00U . . 110.7(4) ?
C005 C00H C00U . . 118.7(4) ?
C00H C00I C00G . . 130.9(4) ?
C00H C00I C00O . . 109.7(4) ?
C00G C00I C00O . . 119.3(4) ?
C00D C00J C00E . . 107.1(4) ?
C00D C00J H00J . . 126.4 ?
C00E C00J H00J . . 126.4 ?
C00B C00K C009 . . 131.0(4) ?
C00B C00K C00Q . . 110.0(4) ?
C009 C00K C00Q . . 118.9(4) ?
C007 C00L C00A . . 108.3(4) ?
C007 C00L H00L . . 125.9 ?
C00A C00L H00L . . 125.9 ?
C00N C00M C008 . . 106.4(4) ?
C00N C00M H00M . . 126.8 ?
C008 C00M H00M . . 126.8 ?
C00M C00N C00G . . 107.4(4) ?
C00M C00N H00N . . 126.3 ?
C00G C00N H00N . . 126.3 ?
C00I C00O C00S . . 105.3(3) ?
C00I C00O H00A . . 110.7 ?
C00S C00O H00A . . 110.7 ?
C00I C00O H00B . . 110.7 ?
C00S C00O H00B . . 110.7 ?
H00A C00O H00B . . 108.8 ?
C00C C00P C00F . . 107.6(4) ?
C00C C00P H00P . . 126.2 ?
C00F C00P H00P . . 126.2 ?
C00K C00Q C00T . . 104.9(4) ?
C00K C00Q H00E . . 110.8 ?
C00T C00Q H00E . . 110.8 ?
C00K C00Q H00F . . 110.8 ?
C00T C00Q H00F . . 110.8 ?
H00E C00Q H00F . . 108.8 ?
C00B C00R C00T . . 104.6(3) ?
C00B C00R H00G . . 110.8 ?
C00T C00R H00G . . 110.8 ?
C00B C00R H00H . . 110.8 ?
C00T C00R H00H . . 110.8 ?
H00G C00R H00H . . 108.9 ?
C00U C00S C00O . . 106.4(4) ?
C00U C00S H00I . . 110.5 ?
C00O C00S H00I . . 110.5 ?
C00U C00S H00K . . 110.5 ?
C00O C00S H00K . . 110.5 ?
H00I C00S H00K . . 108.6 ?
C00Q C00T C00R . . 105.4(4) ?
C00Q C00T H00O . . 110.7 ?
C00R C00T H00O . . 110.7 ?
C00Q C00T H00Q . . 110.7 ?
C00R C00T H00Q . . 110.7 ?
H00O C00T H00Q . . 108.8 ?
C00H C00U C00S . . 105.5(4) ?
C00H C00U H00R . . 110.7 ?
C00S C00U H00R . . 110.7 ?
C00H C00U H00S . . 110.7 ?
C00S C00U H00S . . 110.7 ?
H00R C00U H00S . . 108.8 ?

####################################################################### 
# 
# 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_koga10_1
_database_code_depnum_ccdc_archive 'CCDC 1572026'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         418.53

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8312(12)
_cell_length_b                   9.604(2)
_cell_length_c                   11.229(3)
_cell_angle_alpha                82.626(4)
_cell_angle_beta                 81.110(4)
_cell_angle_gamma                80.418(4)
_cell_volume                     504.7(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2177
_cell_measurement_theta_min      2.6918
_cell_measurement_theta_max      30.1523
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             222

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              'fine focus sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7072
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_full        28.69
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             2597
_reflns_number_gt                2041
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1514
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_refine_ls_number_reflns         2597
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.529
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.142(19)

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'

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.0283(3) 0.73816(14) 0.44294(12) 0.0145(3) Uani d . . . 1 . .
C C2 -0.1640(3) 0.83843(15) 0.52654(13) 0.0180(3) Uani d . . . 1 . .
H H2 -0.3198 0.9108 0.5139 0.022 Uiso calc U . R 1 . .
C C3 -0.0295(3) 0.81132(15) 0.62727(13) 0.0178(3) Uani d . . . 1 . .
H H3 -0.0743 0.8612 0.6972 0.021 Uiso calc U . R 1 . .
C C4 0.1898(3) 0.69480(14) 0.60824(12) 0.0143(3) Uani d . . . 1 . .
C C5 0.3843(3) 0.62816(14) 0.68646(12) 0.0138(3) Uani d . . . 1 . .
C C6 0.4039(3) 0.66466(15) 0.80472(13) 0.0166(3) Uani d . . . 1 . .
H H6 0.2876 0.7388 0.8454 0.02 Uiso calc U . R 1 . .
C C7 0.6207(3) 0.57271(15) 0.84692(13) 0.0159(3) Uani d . . . 1 . .
H H7 0.6852 0.5705 0.923 0.019 Uiso calc U . R 1 . .
C C8 0.7364(3) 0.47804(14) 0.75425(12) 0.0138(3) Uani d . . . 1 . .
C C9 0.9631(3) 0.36416(15) 0.76139(12) 0.0141(3) Uani d . . . 1 . .
C C10 1.0954(3) 0.27106(15) 0.67400(12) 0.0144(3) Uani d . . . 1 . .
C C11 1.0853(3) 0.33327(15) 0.88069(13) 0.0169(3) Uani d . . . 1 . .
H H11A 0.9679 0.393 0.9409 0.02 Uiso calc U . R 1 . .
H H11B 1.2795 0.3579 0.8683 0.02 Uiso calc U . R 1 . .
C C12 1.0940(4) 0.17619(16) 0.92962(13) 0.0224(4) Uani d . . . 1 . .
H H12A 1.1859 0.1575 1.0042 0.027 Uiso calc U . R 1 . .
H H12B 0.8981 0.1543 0.9509 0.027 Uiso calc U . R 1 . .
C C13 1.2574(4) 0.07999(17) 0.83563(14) 0.0243(4) Uani d . . . 1 . .
H H13A 1.138 0.0106 0.8223 0.029 Uiso calc U . R 1 . .
H H13B 1.4297 0.0265 0.8667 0.029 Uiso calc U . R 1 . .
C C14 1.3426(3) 0.16683(16) 0.71475(13) 0.0193(3) Uani d . . . 1 . .
H H14A 1.4966 0.2194 0.7238 0.023 Uiso calc U . R 1 . .
H H14B 1.4161 0.1015 0.6519 0.023 Uiso calc U . R 1 . .
N N1 0.1844(3) 0.65409(13) 0.49716(11) 0.0144(3) Uani d . . . 1 . .
N N2 0.5852(2) 0.51708(12) 0.65833(10) 0.0135(3) Uani d . . . 1 . .
H H1H 0.317(5) 0.573(2) 0.451(2) 0.058(7) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.3673(18) ?
C1 C10 2_666 1.417(2) ?
C1 C2 . 1.439(2) ?
C2 C3 . 1.366(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.420(2) ?
C3 H3 . 0.95 ?
C4 N1 . 1.3594(18) ?
C4 C5 . 1.405(2) ?
C5 N2 . 1.3515(18) ?
C5 C6 . 1.4367(19) ?
C6 C7 . 1.356(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.455(2) ?
C7 H7 . 0.95 ?
C8 N2 . 1.3720(18) ?
C8 C9 . 1.417(2) ?
C9 C10 . 1.418(2) ?
C9 C11 . 1.5217(19) ?
C10 C1 2_666 1.4170(19) ?
C10 C14 . 1.514(2) ?
C11 C12 . 1.534(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.530(2) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.536(2) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
N1 H1H . 1.06(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C10 . 2_666 126.12(13) ?
N1 C1 C2 . . 106.58(12) ?
C10 C1 C2 2_666 . 127.28(13) ?
C3 C2 C1 . . 107.96(13) ?
C3 C2 H2 . . 126.0 ?
C1 C2 H2 . . 126.0 ?
C2 C3 C4 . . 107.38(13) ?
C2 C3 H3 . . 126.3 ?
C4 C3 H3 . . 126.3 ?
N1 C4 C5 . . 123.51(13) ?
N1 C4 C3 . . 108.07(13) ?
C5 C4 C3 . . 128.42(13) ?
N2 C5 C4 . . 123.15(13) ?
N2 C5 C6 . . 109.97(12) ?
C4 C5 C6 . . 126.88(13) ?
C7 C6 C5 . . 106.66(13) ?
C7 C6 H6 . . 126.7 ?
C5 C6 H6 . . 126.7 ?
C6 C7 C8 . . 107.38(13) ?
C6 C7 H7 . . 126.3 ?
C8 C7 H7 . . 126.3 ?
N2 C8 C9 . . 125.59(13) ?
N2 C8 C7 . . 108.02(12) ?
C9 C8 C7 . . 126.39(13) ?
C8 C9 C10 . . 129.94(13) ?
C8 C9 C11 . . 116.45(13) ?
C10 C9 C11 . . 113.61(12) ?
C1 C10 C9 2_666 . 129.58(13) ?
C1 C10 C14 2_666 . 116.72(12) ?
C9 C10 C14 . . 113.70(12) ?
C9 C11 C12 . . 111.00(12) ?
C9 C11 H11A . . 109.4 ?
C12 C11 H11A . . 109.4 ?
C9 C11 H11B . . 109.4 ?
C12 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
C13 C12 C11 . . 111.02(12) ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12B . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 111.17(12) ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13B . . 109.4 ?
C14 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C10 C14 C13 . . 111.85(12) ?
C10 C14 H14A . . 109.2 ?
C13 C14 H14A . . 109.2 ?
C10 C14 H14B . . 109.2 ?
C13 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C4 N1 C1 . . 110.00(12) ?
C4 N1 H1H . . 130.2(12) ?
C1 N1 H1H . . 119.8(12) ?
C5 N2 C8 . . 107.96(11) ?

