# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_ht-dma
_database_code_depnum_ccdc_archive 'CCDC 1491905'
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_audit_creation_date             2016-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ht-dma
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H13 N5'
_chemical_formula_sum            'C13 H13 N5'
_chemical_formula_weight         239.28
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.067(3)
_cell_length_b                   7.0775(17)
_cell_length_c                   15.484(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.374(3)
_cell_angle_gamma                90
_cell_volume                     1239.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4192
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      31.5022
_cell_measurement_theta_min      2.7569
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9754
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.757
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Rigaku X-ray diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           35
_diffrn_source_power             1.75
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2082
_reflns_number_total             2398
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+0.1781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C11(H11)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.36873(8) 0.56448(13) 0.52837(7) 0.0199(2) Uani 1 1 d . . . . .
N2 N 0.16488(9) 0.40230(14) 0.40343(7) 0.0257(3) Uani 1 1 d . . . . .
H2A H 0.2140 0.3280 0.4448 0.031 Uiso 1 1 calc R . . . .
H2B H 0.1008 0.3549 0.3622 0.031 Uiso 1 1 calc R . . . .
N3 N 0.31054(11) 1.03877(15) 0.46316(9) 0.0398(3) Uani 1 1 d . . . . .
N4 N 0.02756(10) 0.78921(16) 0.28254(8) 0.0332(3) Uani 1 1 d . . . . .
N5 N 0.81269(9) 0.23389(14) 0.86359(7) 0.0251(3) Uani 1 1 d . . . . .
C1 C 0.28511(10) 0.67590(16) 0.46434(8) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.18799(10) 0.59021(16) 0.40315(8) 0.0202(3) Uani 1 1 d . . . . .
C3 C 0.29712(10) 0.87810(17) 0.46173(9) 0.0254(3) Uani 1 1 d . . . . .
C4 C 0.09974(10) 0.70328(17) 0.33614(8) 0.0232(3) Uani 1 1 d . . . . .
C5 C 0.72701(10) 0.33089(17) 0.79605(8) 0.0205(3) Uani 1 1 d . . . . .
C6 C 0.62846(10) 0.23738(16) 0.73261(8) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.6215 0.1042 0.7367 0.026 Uiso 1 1 calc R . . . .
C7 C 0.54256(10) 0.33529(17) 0.66520(8) 0.0208(3) Uani 1 1 d . . . . .
H7 H 0.4769 0.2689 0.6241 0.025 Uiso 1 1 calc R . . . .
C8 C 0.55028(10) 0.53155(16) 0.65607(8) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.64742(11) 0.62399(16) 0.71862(8) 0.0240(3) Uani 1 1 d . . . . .
H9 H 0.6543 0.7569 0.7136 0.029 Uiso 1 1 calc R . . . .
C10 C 0.73353(10) 0.52884(17) 0.78730(9) 0.0247(3) Uani 1 1 d . . . . .
H10 H 0.7978 0.5968 0.8291 0.030 Uiso 1 1 calc R . . . .
C11 C 0.46233(10) 0.63994(16) 0.58621(8) 0.0211(3) Uani 1 1 d . . . . .
H11 H 0.4740 0.7721 0.5828 0.025 Uiso 1 1 calc R . . . .
C12 C 0.91492(11) 0.33437(18) 0.92450(9) 0.0287(3) Uani 1 1 d . . . . .
H12A H 0.9590 0.3902 0.8883 0.043 Uiso 1 1 calc GR . . . .
H12B H 0.9661 0.2461 0.9697 0.043 Uiso 1 1 calc GR . . . .
H12C H 0.8887 0.4347 0.9566 0.043 Uiso 1 1 calc GR . . . .
C13 C 0.81926(11) 0.02899(17) 0.85912(9) 0.0283(3) Uani 1 1 d . . . . .
H13A H 0.7460 -0.0266 0.8615 0.042 Uiso 1 1 calc GR . . . .
H13B H 0.8864 -0.0168 0.9114 0.042 Uiso 1 1 calc GR . . . .
H13C H 0.8298 -0.0076 0.8014 0.042 Uiso 1 1 calc GR . . . .


_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 C1 1.3879(15) . ?
N1 C11 1.2879(15) . ?
N2 C2 1.3591(15) . ?
N3 C3 1.1477(17) . ?
N4 C4 1.1463(16) . ?
N5 C5 1.3715(15) . ?
N5 C12 1.4514(15) . ?
N5 C13 1.4552(16) . ?
C1 C2 1.3660(16) . ?
C1 C3 1.4404(17) . ?
C2 C4 1.4427(16) . ?
C5 C6 1.4155(16) . ?
C5 C10 1.4124(18) . ?
C6 C7 1.3750(16) . ?
C7 C8 1.4026(17) . ?
C8 C9 1.3962(16) . ?
C8 C11 1.4442(16) . ?
C9 C10 1.3765(17) . ?

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
C11 N1 C1 120.30(10) . . ?
C5 N5 C12 119.65(10) . . ?
C5 N5 C13 120.11(10) . . ?
C12 N5 C13 118.11(10) . . ?
N1 C1 C3 121.96(10) . . ?
C2 C1 N1 118.56(10) . . ?
C2 C1 C3 119.48(11) . . ?
N2 C2 C1 124.03(11) . . ?
N2 C2 C4 116.37(10) . . ?
C1 C2 C4 119.52(11) . . ?
N3 C3 C1 177.11(14) . . ?
N4 C4 C2 178.19(13) . . ?
N5 C5 C6 121.55(11) . . ?
N5 C5 C10 121.15(10) . . ?
C10 C5 C6 117.29(10) . . ?
C7 C6 C5 121.35(11) . . ?
C6 C7 C8 121.11(10) . . ?
C7 C8 C11 122.98(10) . . ?
C9 C8 C7 117.60(10) . . ?
C9 C8 C11 119.42(10) . . ?
C10 C9 C8 122.16(11) . . ?
C9 C10 C5 120.47(11) . . ?
N1 C11 C8 122.58(10) . . ?

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
N1 C1 C2 N2 3.12(18) . . . . ?
N1 C1 C2 C4 179.83(10) . . . . ?
N5 C5 C6 C7 179.78(11) . . . . ?
N5 C5 C10 C9 179.39(11) . . . . ?
C1 N1 C11 C8 178.02(10) . . . . ?
C3 C1 C2 N2 -175.93(12) . . . . ?
C3 C1 C2 C4 0.78(17) . . . . ?
C5 C6 C7 C8 0.84(18) . . . . ?
C6 C5 C10 C9 -0.83(17) . . . . ?
C6 C7 C8 C9 -0.83(17) . . . . ?
C6 C7 C8 C11 179.86(11) . . . . ?
C7 C8 C9 C10 -0.01(18) . . . . ?
C7 C8 C11 N1 1.62(18) . . . . ?
C8 C9 C10 C5 0.85(19) . . . . ?
C9 C8 C11 N1 -177.67(11) . . . . ?
C10 C5 C6 C7 0.00(17) . . . . ?
C11 N1 C1 C2 178.93(11) . . . . ?
C11 N1 C1 C3 -2.04(17) . . . . ?
C11 C8 C9 C10 179.32(11) . . . . ?
C12 N5 C5 C6 177.22(11) . . . . ?
C12 N5 C5 C10 -3.01(17) . . . . ?
C13 N5 C5 C6 14.13(17) . . . . ?
C13 N5 C5 C10 -166.09(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ht-ding
_database_code_depnum_ccdc_archive 'CCDC 1491906'
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_audit_creation_date             2016-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H25 N5'
_chemical_formula_sum            'C19 H25 N5'
_chemical_formula_weight         323.44
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.594(3)
_cell_length_b                   13.655(3)
_cell_length_c                   20.363(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.363(2)
_cell_angle_gamma                90
_cell_volume                     3739.5(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    153.1500
_cell_measurement_reflns_used    13635
_cell_measurement_theta_min      1.8017
_cell_measurement_theta_max      31.4970

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30554
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.343
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6355
_reflns_number_total             7273
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         7273
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0860P)²+1.0690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18B-C17B = C18A-C17A = C17B-C16B = C17A-C16A = C19B-C18B = C19A-C18A
 1.52 with sigma of 0.02
3. Others
 Fixed Sof: C16A(0.66667) H16A(0.66667) H16B(0.66667) C16B(0.33333)
 H16C(0.33333) H16D(0.33333) C17A(0.66667) H17A(0.66667) H17B(0.66667)
 C17B(0.33333) H17C(0.33333) H17D(0.33333) C18A(0.66667) H18A(0.66667)
 H18B(0.66667) C18B(0.33333) H18C(0.33333) H18D(0.33333) C19A(0.66667)
 H19A(0.66667) H19B(0.66667) H19C(0.66667) C19B(0.33333) H19D(0.33333)
 H19E(0.33333) H19F(0.33333)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12C,H12D), C13(H13C,H13D), C14(H14C,H14D), C16(H16E,H16F), C17(H17E,
 H17F), C18(H18E,H18F), C12A(H12A,H12B), C13A(H13A,H13B), C14A(H14A,H14B),
 C16A(H16A,H16B), C16B(H16C,H16D), C17A(H17A,H17B), C17B(H17C,H17D), C18A(H18A,
 H18B), C18B(H18C,H18D)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C6A(H6A), C7A(H7A), C9A(H9A),
 C10A(H10A), C11A(H11A)
4.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N2A(H2AA,H2AB)
4.d Idealised Me refined as rotating group:
 C15(H15D,H15E,H15F), C19(H19G,H19H,H19I), C15A(H15A,H15B,H15C), C19A(H19A,
 H19B,H19C), C19B(H19D,H19E,H19F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.17056(10) 0.37782(9) 0.20371(6) 0.0261(3) Uani 1 1 d . . . . .
N2 N 0.13406(11) 0.20352(10) 0.26955(8) 0.0341(3) Uani 1 1 d . . . . .
H2A H 0.1938 0.2120 0.2587 0.041 Uiso 1 1 calc R . . . .
H2B H 0.1196 0.1489 0.2890 0.041 Uiso 1 1 calc R . . . .
N3 N -0.05125(11) 0.50073(11) 0.21336(8) 0.0396(4) Uani 1 1 d . . . . .
N4 N -0.10512(12) 0.24223(12) 0.29660(9) 0.0468(4) Uani 1 1 d . . . . .
N5 N 0.55338(10) 0.56512(10) 0.09386(7) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.08000(12) 0.36183(11) 0.22628(8) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.06433(12) 0.27454(11) 0.25634(8) 0.0275(3) Uani 1 1 d . . . . .
C3 C 0.00453(12) 0.43661(12) 0.22042(8) 0.0284(3) Uani 1 1 d . . . . .
C4 C -0.03040(13) 0.25705(12) 0.27871(9) 0.0325(4) Uani 1 1 d . . . . .
C5 C 0.46508(12) 0.53965(11) 0.11401(8) 0.0262(3) Uani 1 1 d . . . . .
C6 C 0.44425(12) 0.44099(11) 0.12989(8) 0.0274(3) Uani 1 1 d . . . . .
H6 H 0.4922 0.3916 0.1258 0.033 Uiso 1 1 calc R . . . .
C7 C 0.35599(12) 0.41591(11) 0.15099(8) 0.0275(3) Uani 1 1 d . . . . .
H7 H 0.3445 0.3495 0.1615 0.033 Uiso 1 1 calc R . . . .
C8 C 0.28232(12) 0.48611(11) 0.15731(8) 0.0263(3) Uani 1 1 d . . . . .
C9 C 0.30209(12) 0.58321(12) 0.14056(8) 0.0297(4) Uani 1 1 d . . . . .
H9 H 0.2532 0.6321 0.1437 0.036 Uiso 1 1 calc R . . . .
C10 C 0.39017(12) 0.60955(11) 0.11971(8) 0.0291(4) Uani 1 1 d . . . . .
H10 H 0.4008 0.6760 0.1089 0.035 Uiso 1 1 calc R . . . .
C11 C 0.19056(12) 0.46319(11) 0.18178(8) 0.0276(3) Uani 1 1 d . . . . .
H11 H 0.1423 0.5136 0.1818 0.033 Uiso 1 1 calc R . . . .
C12 C 0.58611(12) 0.66703(12) 0.09152(8) 0.0287(3) Uani 1 1 d . . . . .
H12C H 0.6588 0.6699 0.1060 0.034 Uiso 1 1 calc R . . . .
H12D H 0.5537 0.7060 0.1233 0.034 Uiso 1 1 calc R . . . .
C13 C 0.56262(12) 0.71303(12) 0.02300(8) 0.0301(4) Uani 1 1 d . . . . .
H13C H 0.4901 0.7088 0.0079 0.036 Uiso 1 1 calc R . . . .
H13D H 0.5967 0.6754 -0.0086 0.036 Uiso 1 1 calc R . . . .
C14 C 0.59485(14) 0.82006(13) 0.02206(9) 0.0373(4) Uani 1 1 d . . . . .
H14C H 0.5624 0.8575 0.0546 0.045 Uiso 1 1 calc R . . . .
H14D H 0.6677 0.8243 0.0356 0.045 Uiso 1 1 calc R . . . .
C15 C 0.56787(18) 0.86576(17) -0.04643(11) 0.0547(6) Uani 1 1 d . . . . .
H15D H 0.5993 0.8284 -0.0789 0.082 Uiso 1 1 calc GR . . . .
H15E H 0.5914 0.9336 -0.0454 0.082 Uiso 1 1 calc GR . . . .
H15F H 0.4955 0.8646 -0.0591 0.082 Uiso 1 1 calc GR . . . .
C16 C 0.62298(12) 0.49083(12) 0.07727(9) 0.0316(4) Uani 1 1 d . . . . .
H16E H 0.6619 0.5184 0.0442 0.038 Uiso 1 1 calc R . . . .
H16F H 0.5847 0.4344 0.0564 0.038 Uiso 1 1 calc R . . . .
C17 C 0.69495(13) 0.45415(13) 0.13700(9) 0.0355(4) Uani 1 1 d . . . . .
H17E H 0.7447 0.5057 0.1512 0.043 Uiso 1 1 calc R . . . .
H17F H 0.6576 0.4413 0.1744 0.043 Uiso 1 1 calc R . . . .
C18 C 0.74857(15) 0.36074(13) 0.12106(10) 0.0420(5) Uani 1 1 d . . . . .
H18E H 0.7923 0.3390 0.1616 0.050 Uiso 1 1 calc R . . . .
H18F H 0.6985 0.3087 0.1088 0.050 Uiso 1 1 calc R . . . .
C19 C 0.81060(17) 0.37178(16) 0.06547(12) 0.0552(6) Uani 1 1 d . . . . .
H19G H 0.7680 0.3929 0.0250 0.083 Uiso 1 1 calc GR . . . .
H19H H 0.8414 0.3088 0.0575 0.083 Uiso 1 1 calc GR . . . .
H19I H 0.8626 0.4208 0.0779 0.083 Uiso 1 1 calc GR . . . .
N1A N 0.33017(10) 0.57545(10) 0.32019(7) 0.0288(3) Uani 1 1 d . . . . .
N2A N 0.42668(12) 0.73271(10) 0.27762(8) 0.0396(4) Uani 1 1 d . . . . .
H2AA H 0.3666 0.7402 0.2882 0.048 Uiso 1 1 calc R . . . .
H2AB H 0.4583 0.7833 0.2639 0.048 Uiso 1 1 calc R . . . .
N3A N 0.50762(12) 0.39119(11) 0.31342(8) 0.0389(4) Uani 1 1 d . . . . .
N4A N 0.65239(12) 0.63968(13) 0.25906(8) 0.0434(4) Uani 1 1 d . . . . .
N5A N -0.09852(10) 0.57556(10) 0.41673(7) 0.0306(3) Uani 1 1 d . . . . .
C1A C 0.42471(12) 0.56201(11) 0.30358(8) 0.0267(3) Uani 1 1 d . . . . .
C2A C 0.47067(12) 0.64302(12) 0.28247(8) 0.0294(4) Uani 1 1 d . . . . .
C3A C 0.47366(12) 0.46857(12) 0.30846(8) 0.0297(4) Uani 1 1 d . . . . .
C4A C 0.57146(13) 0.63826(12) 0.26858(8) 0.0323(4) Uani 1 1 d . . . . .
C5A C -0.00895(12) 0.55685(12) 0.39625(8) 0.0267(3) Uani 1 1 d . . . . .
C6A C 0.04930(12) 0.63344(12) 0.37473(8) 0.0290(4) Uani 1 1 d . . . . .
H6A H 0.0243 0.6985 0.3730 0.035 Uiso 1 1 calc R . . . .
C7A C 0.14068(12) 0.61572(12) 0.35641(8) 0.0289(4) Uani 1 1 d . . . . .
H7A H 0.1774 0.6689 0.3421 0.035 Uiso 1 1 calc R . . . .
C8A C 0.18169(12) 0.52088(11) 0.35818(8) 0.0266(3) Uani 1 1 d . . . . .
C9A C 0.12446(12) 0.44488(11) 0.37892(8) 0.0276(3) Uani 1 1 d . . . . .
H9A H 0.1501 0.3801 0.3806 0.033 Uiso 1 1 calc R . . . .
C10A C 0.03183(12) 0.46127(12) 0.39706(8) 0.0278(3) Uani 1 1 d . . . . .
H10A H -0.0052 0.4076 0.4103 0.033 Uiso 1 1 calc R . . . .
C11A C 0.27905(12) 0.50393(12) 0.33965(8) 0.0273(3) Uani 1 1 d . . . . .
H11A H 0.3058 0.4395 0.3418 0.033 Uiso 1 1 calc R . . . .
C12A C -0.15483(12) 0.49675(12) 0.44246(8) 0.0304(4) Uani 1 1 d . . . . .
H12A H -0.1995 0.5254 0.4716 0.036 Uiso 1 1 calc R . . . .
H12B H -0.1079 0.4525 0.4699 0.036 Uiso 1 1 calc R . . . .
C13A C -0.21687(13) 0.43671(13) 0.38823(8) 0.0324(4) Uani 1 1 d . . . . .
H13A H -0.2757 0.4754 0.3690 0.039 Uiso 1 1 calc R . . . .
H13B H -0.1768 0.4231 0.3524 0.039 Uiso 1 1 calc R . . . .
C14A C -0.25133(14) 0.34028(13) 0.41467(10) 0.0394(4) Uani 1 1 d . . . . .
H14A H -0.2907 0.3042 0.3776 0.047 Uiso 1 1 calc R . . . .
H14B H -0.1922 0.3001 0.4310 0.047 Uiso 1 1 calc R . . . .
C15A C -0.31364(15) 0.35174(14) 0.47032(10) 0.0445(5) Uani 1 1 d . . . . .
H15A H -0.2752 0.3869 0.5074 0.067 Uiso 1 1 calc GR . . . .
H15B H -0.3319 0.2869 0.4853 0.067 Uiso 1 1 calc GR . . . .
H15C H -0.3741 0.3888 0.4541 0.067 Uiso 1 1 calc GR . . . .
C16A C -0.1546(2) 0.6669(2) 0.40219(16) 0.0306(7) Uiso 0.6667 1 d D . P A 1
H16A H -0.2240 0.6502 0.3836 0.037 Uiso 0.6667 1 calc R . P A 1
H16B H -0.1255 0.7031 0.3675 0.037 Uiso 0.6667 1 calc R . P A 1
C16B C -0.1344(5) 0.6768(4) 0.4197(3) 0.0327(15) Uiso 0.3333 1 d D . P A 2
H16C H -0.2075 0.6762 0.4183 0.039 Uiso 0.3333 1 calc R . P A 2
H16D H -0.1192 0.7131 0.3803 0.039 Uiso 0.3333 1 calc R . P A 2
C17A C -0.1564(2) 0.7348(2) 0.46191(14) 0.0391(6) Uiso 0.6667 1 d D . P A 1
H17A H -0.2070 0.7863 0.4497 0.047 Uiso 0.6667 1 calc R . P A 1
H17B H -0.1772 0.6964 0.4988 0.047 Uiso 0.6667 1 calc R . P A 1
C17B C -0.0886(4) 0.7279(4) 0.4804(3) 0.0328(11) Uiso 0.3333 1 d D . P A 2
H17C H -0.0159 0.7166 0.4866 0.039 Uiso 0.3333 1 calc R . P A 2
H17D H -0.1148 0.6995 0.5191 0.039 Uiso 0.3333 1 calc R . P A 2
C18A C -0.0578(2) 0.7835(3) 0.48631(16) 0.0477(7) Uiso 0.6667 1 d D . P A 1
H18A H -0.0369 0.8235 0.4502 0.057 Uiso 0.6667 1 calc R . P A 1
H18B H -0.0065 0.7327 0.4988 0.057 Uiso 0.6667 1 calc R . P A 1
C18B C -0.1082(6) 0.8374(5) 0.4783(4) 0.0650(19) Uiso 0.3333 1 d D . P A 2
H18C H -0.0897 0.8650 0.4369 0.078 Uiso 0.3333 1 calc R . P A 2
H18D H -0.1799 0.8496 0.4785 0.078 Uiso 0.3333 1 calc R . P A 2
C19A C -0.0664(4) 0.8506(4) 0.5481(3) 0.0833(15) Uiso 0.6667 1 d D . P A 1
H19A H -0.0776 0.8097 0.5858 0.125 Uiso 0.6667 1 calc GR . P A 1
H19B H -0.1223 0.8959 0.5372 0.125 Uiso 0.6667 1 calc GR . P A 1
H19C H -0.0048 0.8879 0.5596 0.125 Uiso 0.6667 1 calc GR . P A 1
C19B C -0.0488(10) 0.8876(10) 0.5374(6) 0.103(4) Uiso 0.3333 1 d D . P A 2
H19D H -0.0328 0.9545 0.5251 0.154 Uiso 0.3333 1 calc GR . P A 2
H19E H 0.0128 0.8512 0.5512 0.154 Uiso 0.3333 1 calc GR . P A 2
H19F H -0.0881 0.8897 0.5741 0.154 Uiso 0.3333 1 calc GR . P A 2


_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 C1 1.392(2) . ?
N1 C11 1.291(2) . ?
N2 C2 1.355(2) . ?
N3 C3 1.153(2) . ?
N4 C4 1.146(2) . ?
N5 C5 1.369(2) . ?
N5 C12 1.464(2) . ?
N5 C16 1.460(2) . ?
C1 C2 1.371(2) . ?
C1 C3 1.440(2) . ?
C2 C4 1.447(2) . ?
C5 C6 1.424(2) . ?
C5 C10 1.413(2) . ?
C6 C7 1.375(2) . ?
C7 C8 1.406(2) . ?
C8 C9 1.405(2) . ?
C8 C11 1.443(2) . ?
C9 C10 1.375(2) . ?
C12 C13 1.521(2) . ?
C13 C14 1.527(2) . ?
C14 C15 1.523(3) . ?
C16 C17 1.530(2) . ?
C17 C18 1.527(2) . ?
C18 C19 1.514(3) . ?
N1A C1A 1.388(2) . ?
N1A C11A 1.294(2) . ?
N2A C2A 1.360(2) . ?
N3A C3A 1.152(2) . ?
N4A C4A 1.145(2) . ?
N5A C5A 1.367(2) . ?
N5A C12A 1.461(2) . ?
N5A C16A 1.470(3) . ?
N5A C16B 1.470(6) . ?
C1A C2A 1.370(2) . ?
C1A C3A 1.436(2) . ?
C2A C4A 1.440(2) . ?
C5A C6A 1.419(2) . ?
C5A C10A 1.417(2) . ?
C6A C7A 1.369(2) . ?
C7A C8A 1.408(2) . ?
C8A C9A 1.399(2) . ?
C8A C11A 1.447(2) . ?
C9A C10A 1.381(2) . ?
C12A C13A 1.527(2) . ?
C13A C14A 1.522(2) . ?
C14A C15A 1.518(3) . ?
C16A C17A 1.532(4) . ?
C16B C17B 1.477(8) . ?
C17A C18A 1.515(4) . ?
C17B C18B 1.519(9) . ?
C18A C19A 1.574(6) . ?
C18B C19B 1.511(12) . ?

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
C11 N1 C1 119.76(13) . . ?
C5 N5 C12 122.37(13) . . ?
C5 N5 C16 121.26(13) . . ?
C16 N5 C12 116.27(13) . . ?
N1 C1 C3 120.99(14) . . ?
C2 C1 N1 119.09(14) . . ?
C2 C1 C3 119.89(15) . . ?
N2 C2 C1 124.14(15) . . ?
N2 C2 C4 116.62(14) . . ?
C1 C2 C4 119.17(15) . . ?
N3 C3 C1 174.89(18) . . ?
N4 C4 C2 179.3(2) . . ?
N5 C5 C6 121.38(14) . . ?
N5 C5 C10 121.80(14) . . ?
C10 C5 C6 116.81(14) . . ?
C7 C6 C5 121.20(14) . . ?
C6 C7 C8 121.63(14) . . ?
C7 C8 C11 123.15(14) . . ?
C9 C8 C7 117.22(14) . . ?
C9 C8 C11 119.60(14) . . ?
C10 C9 C8 121.85(15) . . ?
C9 C10 C5 121.27(15) . . ?
N1 C11 C8 123.45(14) . . ?
N5 C12 C13 113.46(13) . . ?
C12 C13 C14 112.61(14) . . ?
C15 C14 C13 111.85(16) . . ?
N5 C16 C17 113.85(14) . . ?
C18 C17 C16 111.97(15) . . ?
C19 C18 C17 114.25(16) . . ?
C11A N1A C1A 122.18(14) . . ?
C5A N5A C12A 120.53(14) . . ?
C5A N5A C16A 123.78(16) . . ?
C5A N5A C16B 120.3(3) . . ?
C12A N5A C16A 114.46(17) . . ?
C12A N5A C16B 118.9(3) . . ?
N1A C1A C3A 122.47(14) . . ?
C2A C1A N1A 116.77(14) . . ?
C2A C1A C3A 120.76(15) . . ?
N2A C2A C1A 122.28(15) . . ?
N2A C2A C4A 116.57(14) . . ?
C1A C2A C4A 121.03(15) . . ?
N3A C3A C1A 175.78(18) . . ?
N4A C4A C2A 176.11(19) . . ?
N5A C5A C6A 121.21(15) . . ?
N5A C5A C10A 122.19(14) . . ?
C10A C5A C6A 116.58(14) . . ?
C7A C6A C5A 121.53(15) . . ?
C6A C7A C8A 121.80(15) . . ?
C7A C8A C11A 120.95(14) . . ?
C9A C8A C7A 117.03(15) . . ?
C9A C8A C11A 122.02(15) . . ?
C10A C9A C8A 121.97(15) . . ?
C9A C10A C5A 121.09(14) . . ?
N1A C11A C8A 120.77(15) . . ?
N5A C12A C13A 113.51(14) . . ?
C14A C13A C12A 112.00(15) . . ?
C15A C14A C13A 114.12(15) . . ?
N5A C16A C17A 114.9(2) . . ?
N5A C16B C17B 112.1(5) . . ?
C18A C17A C16A 114.2(3) . . ?
C16B C17B C18B 113.0(5) . . ?
C17A C18A C19A 110.6(3) . . ?
C19B C18B C17B 110.7(8) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
