# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1866157'
_audit_update_record             
;
2018-09-06 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            CYN-UP
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H23 N5 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         325.41

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.8828(6)
_cell_length_b                   19.2484(13)
_cell_length_c                   10.8095(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.471(4)
_cell_angle_gamma                90
_cell_volume                     1695.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.3098
_cell_measurement_theta_max      21.6297
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            58559
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         28.46
_diffrn_reflns_theta_full        28.46
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             4271
_reflns_number_gt                2783
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1365
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_number_reflns         4271
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²+0.4518P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_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         0.264
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 -0.0678(3) 0.53666(13) -0.3172(2) 0.1014(9) Uani d . . . 1 . .
H H1A -0.0431 0.5048 -0.3749 0.152 Uiso calc U . R 1 . .
H H1B -0.097 0.581 -0.361 0.152 Uiso calc U . R 1 . .
H H1C -0.1579 0.519 -0.2989 0.152 Uiso calc U . R 1 . .
C C2 0.1392(2) 0.48546(9) -0.12353(19) 0.0646(5) Uani d . . . 1 . .
C C3 0.0815(2) 0.41919(9) -0.16042(19) 0.0604(5) Uani d . . . 1 . .
H H3 -0.0146 0.4119 -0.2365 0.073 Uiso calc U . R 1 . .
C C4 0.1663(2) 0.36354(9) -0.08456(18) 0.0571(4) Uani d . . . 1 . .
H H4 0.1261 0.3189 -0.1109 0.069 Uiso calc U . R 1 . .
C C5 0.3091(2) 0.37189(9) 0.02939(17) 0.0526(4) Uani d . . . 1 . .
C C6 0.3613(3) 0.43905(11) 0.0665(2) 0.0834(7) Uani d . . . 1 . .
H H6 0.4548 0.4467 0.1446 0.1 Uiso calc U . R 1 . .
C C7 0.2786(3) 0.49497(11) -0.0089(2) 0.0938(8) Uani d . . . 1 . .
H H7 0.3175 0.5397 0.0181 0.113 Uiso calc U . R 1 . .
C C8 0.4055(2) 0.31040(10) 0.10779(18) 0.0594(4) Uani d . . . 1 . .
H H8A 0.443 0.2833 0.0499 0.071 Uiso calc U . R 1 . .
H H8B 0.5017 0.3272 0.1829 0.071 Uiso calc U . R 1 . .
C C9 0.25907(19) 0.20102(8) 0.10969(15) 0.0475(4) Uani d . . . 1 . .
C C10 0.2229(2) 0.11722(9) -0.04418(17) 0.0565(4) Uani d . . . 1 . .
H H10 0.2498 0.0991 -0.1125 0.068 Uiso calc U . R 1 . .
C C11 0.1005(2) 0.10107(8) 0.10316(15) 0.0484(4) Uani d . . . 1 . .
C C12 0.18125(19) 0.15928(8) 0.17309(14) 0.0465(4) Uani d . . . 1 . .
C C13 0.1855(2) 0.18571(9) 0.30550(15) 0.0538(4) Uani d . . . 1 . .
H H13A 0.1078 0.16 0.3303 0.065 Uiso calc U . R 1 . .
H H13B 0.2942 0.1791 0.3757 0.065 Uiso calc U . R 1 . .
C C14 0.2689(3) 0.29642(10) 0.26626(19) 0.0673(5) Uani d . . . 1 . .
H H14A 0.367 0.2985 0.3491 0.081 Uiso calc U . R 1 . .
H H14B 0.2321 0.3437 0.2407 0.081 Uiso calc U . R 1 . .
C C15 -0.0215(2) 0.27072(9) 0.18705(19) 0.0613(5) Uani d . . . 1 . .
H H15A -0.0198 0.2594 0.1001 0.074 Uiso calc U . R 1 . .
H H15B -0.0489 0.3196 0.1857 0.074 Uiso calc U . R 1 . .
C C16 -0.1550(2) 0.22781(10) 0.2061(2) 0.0658(5) Uani d . . . 1 . .
H H16A -0.2514 0.2571 0.1821 0.079 Uiso calc U . R 1 . .
H H16B -0.1179 0.2175 0.3015 0.079 Uiso calc U . R 1 . .
C C17 -0.2096(2) 0.15896(10) 0.12897(18) 0.0611(4) Uani d . . . 1 . .
H H17A -0.2022 0.1649 0.0424 0.073 Uiso calc U . R 1 . .
H H17B -0.3249 0.1529 0.1107 0.073 Uiso calc U . R 1 . .
C C18 -0.1229(2) 0.09021(9) 0.18902(17) 0.0588(4) Uani d . . . 1 . .
H H18A -0.0639 0.0966 0.2854 0.071 Uiso calc U . R 1 . .
H H18B -0.2065 0.0552 0.1761 0.071 Uiso calc U . R 1 . .
N N1 0.31221(18) 0.26539(7) 0.15956(14) 0.0560(4) Uani d . . . 1 . .
N N2 0.28392(17) 0.17966(7) -0.00002(13) 0.0541(3) Uani d . . . 1 . .
N N3 0.12932(18) 0.07701(7) -0.00498(14) 0.0560(4) Uani d . . . 1 . .
N N4 0.14333(18) 0.25941(7) 0.29235(13) 0.0573(4) Uani d . . . 1 . .
N N5 -0.00821(19) 0.06305(7) 0.13487(15) 0.0618(4) Uani d . . . 1 . .
H H5 -0.0095 0.0189 0.1218 0.074 Uiso calc U . R 1 . .
O O1 0.0706(2) 0.54421(7) -0.19541(16) 0.0946(5) Uani 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 O1 . 1.406(3) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C2 O1 . 1.370(2) ?
C2 C7 . 1.371(3) ?
C2 C3 . 1.373(2) ?
C3 C4 . 1.377(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.381(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.378(2) ?
C5 C8 . 1.508(2) ?
C6 C7 . 1.373(3) ?
C6 H6 . 0.93 ?
C7 H7 . 0.93 ?
C8 N1 . 1.456(2) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 N2 . 1.354(2) ?
C9 N1 . 1.359(2) ?
C9 C12 . 1.404(2) ?
C10 N3 . 1.323(2) ?
C10 N2 . 1.327(2) ?
C10 H10 . 0.93 ?
C11 N5 . 1.360(2) ?
C11 N3 . 1.3730(19) ?
C11 C12 . 1.382(2) ?
C12 C13 . 1.505(2) ?
C13 N4 . 1.460(2) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 N4 . 1.443(2) ?
C14 N1 . 1.479(2) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 N4 . 1.469(2) ?
C15 C16 . 1.525(3) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 C17 . 1.538(3) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C18 . 1.539(2) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 N5 . 1.459(2) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
N5 H5 . 0.86 ?

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
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C7 . . 116.10(16) ?
O1 C2 C3 . . 124.88(17) ?
C7 C2 C3 . . 118.99(18) ?
C2 C3 C4 . . 119.83(16) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C3 C4 C5 . . 122.08(15) ?
C3 C4 H4 . . 119.0 ?
C5 C4 H4 . . 119.0 ?
C6 C5 C4 . . 116.87(17) ?
C6 C5 C8 . . 121.50(16) ?
C4 C5 C8 . . 121.62(15) ?
C7 C6 C5 . . 121.59(18) ?
C7 C6 H6 . . 119.2 ?
C5 C6 H6 . . 119.2 ?
C2 C7 C6 . . 120.59(18) ?
C2 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
N1 C8 C5 . . 113.59(14) ?
N1 C8 H8A . . 108.8 ?
C5 C8 H8A . . 108.8 ?
N1 C8 H8B . . 108.8 ?
C5 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
N2 C9 N1 . . 118.19(15) ?
N2 C9 C12 . . 122.53(15) ?
N1 C9 C12 . . 119.28(14) ?
N3 C10 N2 . . 129.30(15) ?
N3 C10 H10 . . 115.3 ?
N2 C10 H10 . . 115.3 ?
N5 C11 N3 . . 115.15(15) ?
N5 C11 C12 . . 124.38(14) ?
N3 C11 C12 . . 120.47(15) ?
C11 C12 C9 . . 116.51(14) ?
C11 C12 C13 . . 127.24(15) ?
C9 C12 C13 . . 116.11(14) ?
N4 C13 C12 . . 109.12(12) ?
N4 C13 H13A . . 109.9 ?
C12 C13 H13A . . 109.9 ?
N4 C13 H13B . . 109.9 ?
C12 C13 H13B . . 109.9 ?
H13A C13 H13B . . 108.3 ?
N4 C14 N1 . . 114.48(14) ?
N4 C14 H14A . . 108.6 ?
N1 C14 H14A . . 108.6 ?
N4 C14 H14B . . 108.6 ?
N1 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
N4 C15 C16 . . 113.81(15) ?
N4 C15 H15A . . 108.8 ?
C16 C15 H15A . . 108.8 ?
N4 C15 H15B . . 108.8 ?
C16 C15 H15B . . 108.8 ?
H15A C15 H15B . . 107.7 ?
C15 C16 C17 . . 119.21(15) ?
C15 C16 H16A . . 107.5 ?
C17 C16 H16A . . 107.5 ?
C15 C16 H16B . . 107.5 ?
C17 C16 H16B . . 107.5 ?
H16A C16 H16B . . 107.0 ?
C16 C17 C18 . . 121.05(15) ?
C16 C17 H17A . . 107.1 ?
C18 C17 H17A . . 107.1 ?
C16 C17 H17B . . 107.1 ?
C18 C17 H17B . . 107.1 ?
H17A C17 H17B . . 106.8 ?
N5 C18 C17 . . 116.80(14) ?
N5 C18 H18A . . 108.1 ?
C17 C18 H18A . . 108.1 ?
N5 C18 H18B . . 108.1 ?
C17 C18 H18B . . 108.1 ?
H18A C18 H18B . . 107.3 ?
C9 N1 C8 . . 123.44(14) ?
C9 N1 C14 . . 121.36(14) ?
C8 N1 C14 . . 115.08(14) ?
C10 N2 C9 . . 113.87(14) ?
C10 N3 C11 . . 115.43(14) ?
C14 N4 C13 . . 108.08(14) ?
C14 N4 C15 . . 112.63(15) ?
C13 N4 C15 . . 110.94(13) ?
C11 N5 C18 . . 125.99(14) ?
C11 N5 H5 . . 117.0 ?
C18 N5 H5 . . 117.0 ?
C2 O1 C1 . . 118.11(16) ?

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1866158'
_audit_update_record             
;
2018-09-06 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            CYN-P1
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 N5 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         312.39

_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                   9.7756(12)
_cell_length_b                   12.9665(16)
_cell_length_c                   12.9912(16)
_cell_angle_alpha                84.4412(12)
_cell_angle_beta                 86.9004(12)
_cell_angle_gamma                84.1930(12)
_cell_volume                     1628.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5821
_cell_measurement_theta_min      2.8282
_cell_measurement_theta_max      22.7733
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            50448
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_full        28.68
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             8325
_reflns_number_gt                4482
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1765
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_number_reflns         8325
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0665P)²+0.5658P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_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         0.519
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 C11 0.4823(4) -0.3897(3) 0.5736(3) 0.0954(12) Uani d . . . 1 . .
H H11A 0.3943 -0.3792 0.5427 0.143 Uiso calc U . R 1 . .
H H11B 0.5122 -0.4627 0.5814 0.143 Uiso calc U . R 1 . .
H H11C 0.5481 -0.3538 0.5299 0.143 Uiso calc U . R 1 . .
C C12 0.4407(2) -0.24452(18) 0.6738(2) 0.0490(6) Uani d . . . 1 . .
C C13 0.4462(3) -0.2078(2) 0.7689(2) 0.0580(7) Uani d . . . 1 . .
H H13 0.4654 -0.2538 0.8269 0.07 Uiso calc U . R 1 . .
C C14 0.4231(3) -0.1028(2) 0.7780(2) 0.0608(7) Uani d . . . 1 . .
H H14 0.428 -0.0787 0.8427 0.073 Uiso calc U . R 1 . .
C C15 0.3928(2) -0.03161(19) 0.6939(2) 0.0546(7) Uani d . . . 1 . .
C C16 0.3844(3) -0.0710(2) 0.5999(2) 0.0618(7) Uani d . . . 1 . .
H H16 0.3621 -0.0254 0.5422 0.074 Uiso calc U . R 1 . .
C C17 0.4083(3) -0.1768(2) 0.5889(2) 0.0587(7) Uani d . . . 1 . .
H H17 0.4023 -0.2015 0.5246 0.07 Uiso calc U . R 1 . .
C C18 0.3760(3) 0.0835(2) 0.7037(3) 0.0773(10) Uani d . . . 1 . .
H H18A 0.4285 0.0982 0.761 0.093 Uiso calc U . R 1 . .
H H18B 0.4132 0.1194 0.641 0.093 Uiso calc U . R 1 . .
C C19 0.1981(2) 0.22857(17) 0.72046(18) 0.0432(5) Uani d . . . 1 . .
C C110 0.2648(3) 0.39021(19) 0.6897(2) 0.0590(7) Uani d . . . 1 . .
H H110 0.3357 0.4323 0.6723 0.071 Uiso calc U . R 1 . .
C C111 0.0408(2) 0.37857(16) 0.74127(17) 0.0395(5) Uani d . . . 1 . .
C C112 -0.2206(3) 0.40200(19) 0.7691(2) 0.0538(6) Uani d . . . 1 . .
H H11D -0.2846 0.4626 0.7799 0.065 Uiso calc U . R 1 . .
H H11E -0.2253 0.3544 0.8313 0.065 Uiso calc U . R 1 . .
C C113 -0.2689(3) 0.3490(2) 0.6796(2) 0.0602(7) Uani d . . . 1 . .
H H11F -0.2782 0.4003 0.6203 0.072 Uiso calc U . R 1 . .
H H11G -0.3598 0.3277 0.6988 0.072 Uiso calc U . R 1 . .
C C114 -0.1773(3) 0.25377(19) 0.64569(19) 0.0524(6) Uani d . . . 1 . .
H H11H -0.2262 0.2235 0.5948 0.063 Uiso calc U . R 1 . .
H H11I -0.0953 0.2787 0.6105 0.063 Uiso calc U . R 1 . .
C C115 -0.0404(2) 0.20027(16) 0.79891(17) 0.0419(5) Uani d . . . 1 . .
H H11J 0.0066 0.1376 0.8326 0.05 Uiso calc U . R 1 . .
H H11K -0.0955 0.2356 0.8517 0.05 Uiso calc U . R 1 . .
C C116 0.0654(2) 0.26971(15) 0.75264(16) 0.0367(5) Uani d . . . 1 . .
C C117 -0.2478(3) 0.1209(2) 0.7770(3) 0.0735(9) Uani d . . . 1 . .
H H11L -0.2977 0.1684 0.821 0.11 Uiso calc U . R 1 . .
H H11M -0.2131 0.0593 0.8182 0.11 Uiso calc U . R 1 . .
H H11N -0.308 0.1025 0.7272 0.11 Uiso calc U . R 1 . .
C C21 0.3167(4) 0.0728(2) 1.0190(3) 0.0862(10) Uani d . . . 1 . .
H H21A 0.2898 0.087 1.0888 0.129 Uiso calc U . R 1 . .
H H21B 0.3645 0.0043 1.0192 0.129 Uiso calc U . R 1 . .
H H21C 0.2362 0.0765 0.979 0.129 Uiso calc U . R 1 . .
C C22 0.3526(2) 0.24969(17) 0.97191(18) 0.0454(6) Uani d . . . 1 . .
C C23 0.4411(3) 0.3211(2) 0.9311(2) 0.0619(7) Uani d . . . 1 . .
H H23 0.5294 0.2982 0.9073 0.074 Uiso calc U . R 1 . .
C C24 0.3995(3) 0.4260(2) 0.9254(2) 0.0608(7) Uani d . . . 1 . .
H H24 0.4599 0.4731 0.897 0.073 Uiso calc U . R 1 . .
C C25 0.2696(3) 0.46287(18) 0.96117(18) 0.0459(6) Uani d . . . 1 . .
C C26 0.1841(3) 0.3901(2) 1.0027(2) 0.0581(7) Uani d . . . 1 . .
H H26 0.0967 0.4129 1.0284 0.07 Uiso calc U . R 1 . .
C C27 0.2233(3) 0.2844(2) 1.0077(2) 0.0567(7) Uani d . . . 1 . .
H H27 0.1624 0.2371 1.0352 0.068 Uiso calc U . R 1 . .
C C28 0.2253(3) 0.57730(18) 0.9593(2) 0.0557(7) Uani d . . . 1 . .
H H28A 0.1579 0.5892 1.0155 0.067 Uiso calc U . R 1 . .
H H28B 0.3042 0.6139 0.9704 0.067 Uiso calc U . R 1 . .
C C29 0.1262(2) 0.72353(15) 0.84561(16) 0.0344(5) Uani d . . . 1 . .
C C210 0.1052(3) 0.88027(17) 0.9104(2) 0.0484(6) Uani d . . . 1 . .
H H210 0.1184 0.9191 0.9649 0.058 Uiso calc U . R 1 . .
C C211 0.0337(2) 0.87712(16) 0.74693(17) 0.0390(5) Uani d . . . 1 . .
C C212 -0.0942(3) 0.90628(18) 0.5790(2) 0.0530(6) Uani d . . . 1 . .
H H21D -0.0255 0.8672 0.5377 0.064 Uiso calc U . R 1 . .
H H21E -0.1263 0.9688 0.5365 0.064 Uiso calc U . R 1 . .
C C213 -0.2152(3) 0.84106(19) 0.6042(2) 0.0576(7) Uani d . . . 1 . .
H H21F -0.2441 0.8199 0.5398 0.069 Uiso calc U . R 1 . .
H H21G -0.2911 0.8854 0.6324 0.069 Uiso calc U . R 1 . .
C C214 -0.1910(2) 0.74317(17) 0.67985(19) 0.0451(6) Uani d . . . 1 . .
H H21H -0.1807 0.7656 0.7479 0.054 Uiso calc U . R 1 . .
H H21I -0.2737 0.7072 0.6839 0.054 Uiso calc U . R 1 . .
C C215 0.0626(2) 0.70652(16) 0.66215(16) 0.0365(5) Uani d . . . 1 . .
H H21J 0.0811 0.7486 0.598 0.044 Uiso calc U . R 1 . .
H H21K 0.1324 0.6477 0.667 0.044 Uiso calc U . R 1 . .
C C216 0.0736(2) 0.77028(15) 0.75125(16) 0.0330(4) Uani d . . . 1 . .
C C217 -0.0853(3) 0.6213(2) 0.56087(19) 0.0572(7) Uani d . . . 1 . .
H H21L -0.1686 0.5875 0.5635 0.086 Uiso calc U . R 1 . .
H H21M -0.0077 0.5713 0.5506 0.086 Uiso calc U . R 1 . .
H H21N -0.0872 0.6751 0.5046 0.086 Uiso calc U . R 1 . .
N N11 0.2320(2) 0.12331(14) 0.72103(18) 0.0545(6) Uani d . . . 1 . .
N N12 0.2998(2) 0.28929(15) 0.68792(18) 0.0562(6) Uani d . . . 1 . .
N N13 0.1440(2) 0.44037(14) 0.71250(17) 0.0514(5) Uani d . . . 1 . .
N N14 -0.0823(2) 0.43509(14) 0.75661(16) 0.0494(5) Uani d . . . 1 . .
H H14A -0.0777 0.5006 0.7594 0.059 Uiso calc U . R 1 . .
N N15 -0.13299(19) 0.17037(14) 0.72315(15) 0.0454(5) Uani d . . . 1 . .
N N21 0.16566(19) 0.61962(13) 0.86095(14) 0.0413(4) Uani d . . . 1 . .
N N22 0.1410(2) 0.77899(14) 0.92746(14) 0.0427(5) Uani d . . . 1 . .
N N23 0.0537(2) 0.93434(13) 0.82782(16) 0.0473(5) Uani d . . . 1 . .
N N24 -0.0280(2) 0.93695(14) 0.66709(16) 0.0499(5) Uani d . . . 1 . .
H H24A -0.0277 1.003 0.6693 0.06 Uiso calc U . R 1 . .
N N25 -0.07402(18) 0.66735(13) 0.65852(13) 0.0376(4) Uani d . . . 1 . .
O O11 0.4711(2) -0.35085(14) 0.67059(17) 0.0725(6) Uani d . . . 1 . .
O O21 0.4040(2) 0.14683(13) 0.97493(15) 0.0660(5) Uani 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
C11 O11 . 1.397(4) ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
C12 C17 . 1.372(4) ?
C12 C13 . 1.372(4) ?
C12 O11 . 1.385(3) ?
C13 C14 . 1.373(4) ?
C13 H13 . 0.93 ?
C14 C15 . 1.385(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.377(4) ?
C15 C18 . 1.502(3) ?
C16 C17 . 1.388(4) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C18 N11 . 1.463(3) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 N12 . 1.355(3) ?
C19 N11 . 1.371(3) ?
C19 C116 . 1.409(3) ?
C110 N12 . 1.321(3) ?
C110 N13 . 1.323(3) ?
C110 H110 . 0.93 ?
C111 N14 . 1.359(3) ?
C111 N13 . 1.365(3) ?
C111 C116 . 1.403(3) ?
C112 N14 . 1.455(3) ?
C112 C113 . 1.525(4) ?
C112 H11D . 0.97 ?
C112 H11E . 0.97 ?
C113 C114 . 1.536(4) ?
C113 H11F . 0.97 ?
C113 H11G . 0.97 ?
C114 N15 . 1.453(3) ?
C114 H11H . 0.97 ?
C114 H11I . 0.97 ?
C115 N15 . 1.476(3) ?
C115 C116 . 1.502(3) ?
C115 H11J . 0.97 ?
C115 H11K . 0.97 ?
C117 N15 . 1.461(3) ?
C117 H11L . 0.96 ?
C117 H11M . 0.96 ?
C117 H11N . 0.96 ?
C21 O21 . 1.409(3) ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
C22 C27 . 1.371(3) ?
C22 O21 . 1.374(3) ?
C22 C23 . 1.380(3) ?
C23 C24 . 1.376(3) ?
C23 H23 . 0.93 ?
C24 C25 . 1.383(3) ?
C24 H24 . 0.93 ?
C25 C26 . 1.376(3) ?
C25 C28 . 1.501(3) ?
C26 C27 . 1.382(3) ?
C26 H26 . 0.93 ?
C27 H27 . 0.93 ?
C28 N21 . 1.468(3) ?
C28 H28A . 0.97 ?
C28 H28B . 0.97 ?
C29 N22 . 1.362(3) ?
C29 N21 . 1.362(2) ?
C29 C216 . 1.413(3) ?
C210 N23 . 1.318(3) ?
C210 N22 . 1.325(3) ?
C210 H210 . 0.93 ?
C211 N24 . 1.363(3) ?
C211 N23 . 1.377(3) ?
C211 C216 . 1.397(3) ?
C212 N24 . 1.452(3) ?
C212 C213 . 1.526(3) ?
C212 H21D . 0.97 ?
C212 H21E . 0.97 ?
C213 C214 . 1.535(3) ?
C213 H21F . 0.97 ?
C213 H21G . 0.97 ?
C214 N25 . 1.464(3) ?
C214 H21H . 0.97 ?
C214 H21I . 0.97 ?
C215 N25 . 1.480(3) ?
C215 C216 . 1.501(3) ?
C215 H21J . 0.97 ?
C215 H21K . 0.97 ?
C217 N25 . 1.467(3) ?
C217 H21L . 0.96 ?
C217 H21M . 0.96 ?
C217 H21N . 0.96 ?
N14 H14A . 0.86 ?
N24 H24A . 0.86 ?

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
O11 C11 H11A . . 109.5 ?
O11 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O11 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C17 C12 C13 . . 120.0(2) ?
C17 C12 O11 . . 124.0(2) ?
C13 C12 O11 . . 116.0(2) ?
C12 C13 C14 . . 119.7(3) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C13 C14 C15 . . 122.1(3) ?
C13 C14 H14 . . 118.9 ?
C15 C14 H14 . . 118.9 ?
C16 C15 C14 . . 116.9(2) ?
C16 C15 C18 . . 121.5(3) ?
C14 C15 C18 . . 121.5(3) ?
C15 C16 C17 . . 121.9(3) ?
C15 C16 H16 . . 119.0 ?
C17 C16 H16 . . 119.0 ?
C12 C17 C16 . . 119.3(3) ?
C12 C17 H17 . . 120.3 ?
C16 C17 H17 . . 120.3 ?
N11 C18 C15 . . 112.4(2) ?
N11 C18 H18A . . 109.1 ?
C15 C18 H18A . . 109.1 ?
N11 C18 H18B . . 109.1 ?
C15 C18 H18B . . 109.1 ?
H18A C18 H18B . . 107.9 ?
N12 C19 N11 . . 115.8(2) ?
N12 C19 C116 . . 122.8(2) ?
N11 C19 C116 . . 121.4(2) ?
N12 C110 N13 . . 129.6(2) ?
N12 C110 H110 . . 115.2 ?
N13 C110 H110 . . 115.2 ?
N14 C111 N13 . . 112.14(19) ?
N14 C111 C116 . . 126.3(2) ?
N13 C111 C116 . . 121.6(2) ?
N14 C112 C113 . . 116.1(2) ?
N14 C112 H11D . . 108.3 ?
C113 C112 H11D . . 108.3 ?
N14 C112 H11E . . 108.3 ?
C113 C112 H11E . . 108.3 ?
H11D C112 H11E . . 107.4 ?
C112 C113 C114 . . 116.9(2) ?
C112 C113 H11F . . 108.1 ?
C114 C113 H11F . . 108.1 ?
C112 C113 H11G . . 108.1 ?
C114 C113 H11G . . 108.1 ?
H11F C113 H11G . . 107.3 ?
N15 C114 C113 . . 119.3(2) ?
N15 C114 H11H . . 107.5 ?
C113 C114 H11H . . 107.5 ?
N15 C114 H11I . . 107.5 ?
C113 C114 H11I . . 107.5 ?
H11H C114 H11I . . 107.0 ?
N15 C115 C116 . . 114.08(18) ?
N15 C115 H11J . . 108.7 ?
C116 C115 H11J . . 108.7 ?
N15 C115 H11K . . 108.7 ?
C116 C115 H11K . . 108.7 ?
H11J C115 H11K . . 107.6 ?
C111 C116 C19 . . 115.8(2) ?
C111 C116 C115 . . 122.80(19) ?
C19 C116 C115 . . 121.41(19) ?
N15 C117 H11L . . 109.5 ?
N15 C117 H11M . . 109.5 ?
H11L C117 H11M . . 109.5 ?
N15 C117 H11N . . 109.5 ?
H11L C117 H11N . . 109.5 ?
H11M C117 H11N . . 109.5 ?
O21 C21 H21A . . 109.5 ?
O21 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O21 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C27 C22 O21 . . 124.7(2) ?
C27 C22 C23 . . 119.4(2) ?
O21 C22 C23 . . 116.0(2) ?
C24 C23 C22 . . 120.3(2) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C25 . . 121.4(2) ?
C23 C24 H24 . . 119.3 ?
C25 C24 H24 . . 119.3 ?
C26 C25 C24 . . 117.1(2) ?
C26 C25 C28 . . 121.1(2) ?
C24 C25 C28 . . 121.7(2) ?
C25 C26 C27 . . 122.4(2) ?
C25 C26 H26 . . 118.8 ?
C27 C26 H26 . . 118.8 ?
C22 C27 C26 . . 119.5(2) ?
C22 C27 H27 . . 120.3 ?
C26 C27 H27 . . 120.3 ?
N21 C28 C25 . . 112.18(19) ?
N21 C28 H28A . . 109.2 ?
C25 C28 H28A . . 109.2 ?
N21 C28 H28B . . 109.2 ?
C25 C28 H28B . . 109.2 ?
H28A C28 H28B . . 107.9 ?
N22 C29 N21 . . 115.35(19) ?
N22 C29 C216 . . 122.46(18) ?
N21 C29 C216 . . 122.19(18) ?
N23 C210 N22 . . 129.8(2) ?
N23 C210 H210 . . 115.1 ?
N22 C210 H210 . . 115.1 ?
N24 C211 N23 . . 112.00(19) ?
N24 C211 C216 . . 126.5(2) ?
N23 C211 C216 . . 121.5(2) ?
N24 C212 C213 . . 116.0(2) ?
N24 C212 H21D . . 108.3 ?
C213 C212 H21D . . 108.3 ?
N24 C212 H21E . . 108.3 ?
C213 C212 H21E . . 108.3 ?
H21D C212 H21E . . 107.4 ?
C212 C213 C214 . . 117.1(2) ?
C212 C213 H21F . . 108.0 ?
C214 C213 H21F . . 108.0 ?
C212 C213 H21G . . 108.0 ?
C214 C213 H21G . . 108.0 ?
H21F C213 H21G . . 107.3 ?
N25 C214 C213 . . 118.5(2) ?
N25 C214 H21H . . 107.7 ?
C213 C214 H21H . . 107.7 ?
N25 C214 H21I . . 107.7 ?
C213 C214 H21I . . 107.7 ?
H21H C214 H21I . . 107.1 ?
N25 C215 C216 . . 113.34(17) ?
N25 C215 H21J . . 108.9 ?
C216 C215 H21J . . 108.9 ?
N25 C215 H21K . . 108.9 ?
C216 C215 H21K . . 108.9 ?
H21J C215 H21K . . 107.7 ?
C211 C216 C29 . . 116.24(18) ?
C211 C216 C215 . . 123.16(19) ?
C29 C216 C215 . . 120.60(18) ?
N25 C217 H21L . . 109.5 ?
N25 C217 H21M . . 109.5 ?
H21L C217 H21M . . 109.5 ?
N25 C217 H21N . . 109.5 ?
H21L C217 H21N . . 109.5 ?
H21M C217 H21N . . 109.5 ?
C19 N11 C18 . . 119.4(2) ?
C110 N12 C19 . . 114.5(2) ?
C110 N13 C111 . . 115.28(19) ?
C111 N14 C112 . . 130.09(19) ?
C111 N14 H14A . . 115.0 ?
C112 N14 H14A . . 115.0 ?
C114 N15 C117 . . 112.9(2) ?
C114 N15 C115 . . 114.47(17) ?
C117 N15 C115 . . 110.0(2) ?
C29 N21 C28 . . 119.15(18) ?
C210 N22 C29 . . 114.53(19) ?
C210 N23 C211 . . 115.28(18) ?
C211 N24 C212 . . 129.92(19) ?
C211 N24 H24A . . 115.0 ?
C212 N24 H24A . . 115.0 ?
C214 N25 C217 . . 112.27(18) ?
C214 N25 C215 . . 114.70(16) ?
C217 N25 C215 . . 110.31(17) ?
C12 O11 C11 . . 117.7(2) ?
C22 O21 C21 . . 116.9(2) ?

