# 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_x_a
_audit_block_doi                 10.5517/ccdc.csd.cc1lwcrl
_database_code_depnum_ccdc_archive 'CCDC 1486070'
_audit_update_record             
;
2016-06-16 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N4 O'
_chemical_formula_weight         294.35

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                   7.4064(7)
_cell_length_b                   21.498(2)
_cell_length_c                   10.1255(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.800(2)
_cell_angle_gamma                90
_cell_volume                     1535.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2965
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      22.12

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21944
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.895
_diffrn_reflns_theta_max         28.778
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3959
_reflns_number_gt                2138
_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       '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'
_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)+(0.0705P)²+0.1303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3959
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.7263(2) 0.38377(8) 0.4493(2) 0.0950(6) Uani 1 1 d . . . . .
H1N H 0.378(3) 0.4432(9) 0.256(2) 0.057(6) Uiso 1 1 d . . . . .
H1 H 0.074(3) 0.5527(10) -0.015(2) 0.075(6) Uiso 1 1 d . . . . .
C1 C 0.2110(3) 0.55973(9) 0.0189(2) 0.0564(5) Uani 1 1 d . . . . .
N1 N 0.5016(2) 0.44179(7) 0.30185(17) 0.0540(4) Uani 1 1 d . . . . .
H3 H 0.540(3) 0.6577(9) -0.016(2) 0.061(6) Uiso 1 1 d . . . . .
N3 N 0.3122(2) 0.52110(7) 0.11332(16) 0.0515(4) Uani 1 1 d . . . . .
C3 C 0.4776(3) 0.62215(9) 0.0203(2) 0.0513(5) Uani 1 1 d . . . . .
N2 N 0.8592(2) 0.66291(8) 0.02258(17) 0.0606(5) Uani 1 1 d . . . . .
H2 H 0.206(3) 0.6384(9) -0.101(2) 0.066(6) Uiso 1 1 d . . . . .
C2 C 0.2884(3) 0.61048(10) -0.0309(2) 0.0579(5) Uani 1 1 d . . . . .
C4 C 0.5937(2) 0.58173(8) 0.12075(16) 0.0426(4) Uani 1 1 d . . . . .
N4 N 0.8919(2) 0.64068(7) 0.15358(16) 0.0495(4) Uani 1 1 d . . . . .
C5 C 0.7931(2) 0.58839(8) 0.18277(17) 0.0452(4) Uani 1 1 d . . . . .
C8 C 0.6094(2) 0.48863(8) 0.26627(18) 0.0466(4) Uani 1 1 d . . . . .
C7 C 0.8009(3) 0.49639(9) 0.3215(2) 0.0531(5) Uani 1 1 d . . . . .
H7 H 0.875(3) 0.4661(10) 0.389(2) 0.067(6) Uiso 1 1 d . . . . .
C6 C 0.8917(3) 0.54624(9) 0.27867(19) 0.0505(5) Uani 1 1 d . . . . .
H6 H 1.029(3) 0.5517(8) 0.3248(19) 0.057(5) Uiso 1 1 d . . . . .
C10 C 0.5588(3) 0.39385(9) 0.3901(2) 0.0548(5) Uani 1 1 d . . . . .
C9 C 0.5029(2) 0.53138(8) 0.16373(17) 0.0433(4) Uani 1 1 d . . . . .
C11 C 0.4038(3) 0.35136(9) 0.40948(19) 0.0504(5) Uani 1 1 d . . . . .
C13 C 0.4167(4) 0.29089(11) 0.3361(3) 0.0864(8) Uani 1 1 d . . . . .
H13A H 0.4019 0.2991 0.2402 0.130 Uiso 1 1 calc R U . . .
H13B H 0.3183 0.2632 0.3430 0.130 Uiso 1 1 calc R U . . .
H13C H 0.5382 0.2720 0.3787 0.130 Uiso 1 1 calc R U . . .
C12 C 0.2041(3) 0.37715(12) 0.3479(3) 0.0858(8) Uani 1 1 d . . . . .
H12A H 0.1768 0.3818 0.2494 0.129 Uiso 1 1 calc R U . . .
H12B H 0.1953 0.4169 0.3887 0.129 Uiso 1 1 calc R U . . .
H12C H 0.1144 0.3490 0.3667 0.129 Uiso 1 1 calc R U . . .
C14 C 0.4416(4) 0.34038(17) 0.5626(2) 0.1043(10) Uani 1 1 d . . . . .
H14A H 0.3428 0.3149 0.5769 0.156 Uiso 1 1 calc R U . . .
H14B H 0.4449 0.3795 0.6089 0.156 Uiso 1 1 calc R U . . .
H14C H 0.5614 0.3197 0.5997 0.156 Uiso 1 1 calc R U . . .
C17 C 1.0851(3) 0.71935(11) 0.1747(3) 0.0679(6) Uani 1 1 d . . . . .
H17 H 1.176(4) 0.7524(11) 0.215(2) 0.086(7) Uiso 1 1 d . . . . .
C18 C 0.9777(3) 0.71061(11) 0.0384(3) 0.0673(6) Uani 1 1 d . . . . .
H18 H 0.976(4) 0.7354(12) -0.048(3) 0.096(8) Uiso 1 1 d . . . . .
C16 C 1.0281(3) 0.67395(10) 0.2469(2) 0.0587(5) Uani 1 1 d . . . . .
H16 H 1.068(3) 0.6634(10) 0.346(2) 0.069(6) Uiso 1 1 d . . . . .


_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 C10 1.220(2) . ?
C1 N3 1.314(2) . ?
C1 C2 1.396(3) . ?
C1 H1 0.98(2) . ?
N1 C10 1.345(2) . ?
N1 C8 1.399(2) . ?
N1 H1N 0.89(2) . ?
N3 C9 1.365(2) . ?
C3 C2 1.361(3) . ?
C3 C4 1.412(2) . ?
C3 H3 1.02(2) . ?
N2 C18 1.327(3) . ?
N2 N4 1.360(2) . ?
C2 H2 0.99(2) . ?
C4 C9 1.411(2) . ?
C4 C5 1.425(2) . ?
N4 C16 1.356(2) . ?
N4 C5 1.421(2) . ?
C5 C6 1.365(2) . ?
C8 C7 1.366(2) . ?
C8 C9 1.430(2) . ?
C7 C6 1.403(3) . ?
C7 H7 0.98(2) . ?
C6 H6 0.99(2) . ?
C10 C11 1.526(3) . ?
C11 C14 1.508(3) . ?
C11 C13 1.515(3) . ?
C11 C12 1.523(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C17 C16 1.362(3) . ?
C17 C18 1.379(3) . ?
C17 H17 0.98(3) . ?
C18 H18 1.03(3) . ?
C16 H16 0.98(2) . ?

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
N3 C1 C2 123.42(18) . . ?
N3 C1 H1 117.2(13) . . ?
C2 C1 H1 119.3(13) . . ?
C10 N1 C8 129.33(17) . . ?
C10 N1 H1N 116.1(12) . . ?
C8 N1 H1N 114.5(12) . . ?
C1 N3 C9 117.68(16) . . ?
C2 C3 C4 119.34(19) . . ?
C2 C3 H3 122.0(11) . . ?
C4 C3 H3 118.5(11) . . ?
C18 N2 N4 103.86(18) . . ?
C3 C2 C1 119.68(19) . . ?
C3 C2 H2 120.2(12) . . ?
C1 C2 H2 120.1(12) . . ?
C9 C4 C3 116.85(16) . . ?
C9 C4 C5 117.95(15) . . ?
C3 C4 C5 125.20(16) . . ?
C16 N4 N2 111.56(16) . . ?
C16 N4 C5 126.35(16) . . ?
N2 N4 C5 122.09(15) . . ?
C6 C5 N4 118.38(15) . . ?
C6 C5 C4 120.27(16) . . ?
N4 C5 C4 121.23(15) . . ?
C7 C8 N1 125.83(16) . . ?
C7 C8 C9 119.48(16) . . ?
N1 C8 C9 114.69(15) . . ?
C8 C7 C6 120.17(17) . . ?
C8 C7 H7 119.7(12) . . ?
C6 C7 H7 120.1(12) . . ?
C5 C6 C7 121.61(17) . . ?
C5 C6 H6 120.5(11) . . ?
C7 C6 H6 117.7(11) . . ?
O1 C10 N1 121.94(18) . . ?
O1 C10 C11 121.46(17) . . ?
N1 C10 C11 116.58(16) . . ?
N3 C9 C4 123.01(15) . . ?
N3 C9 C8 116.48(15) . . ?
C4 C9 C8 120.50(15) . . ?
C14 C11 C13 110.5(2) . . ?
C14 C11 C12 109.3(2) . . ?
C13 C11 C12 108.10(19) . . ?
C14 C11 C10 108.40(17) . . ?
C13 C11 C10 106.72(17) . . ?
C12 C11 C10 113.83(16) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C17 C18 105.1(2) . . ?
C16 C17 H17 126.0(15) . . ?
C18 C17 H17 128.7(15) . . ?
N2 C18 C17 112.6(2) . . ?
N2 C18 H18 117.6(14) . . ?
C17 C18 H18 129.8(14) . . ?
N4 C16 C17 106.9(2) . . ?
N4 C16 H16 121.3(13) . . ?
C17 C16 H16 131.8(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N3 C9 -0.5(3) . . . . ?
C4 C3 C2 C1 1.5(3) . . . . ?
N3 C1 C2 C3 -0.8(3) . . . . ?
C2 C3 C4 C9 -1.0(3) . . . . ?
C2 C3 C4 C5 179.96(18) . . . . ?
C18 N2 N4 C16 -0.3(2) . . . . ?
C18 N2 N4 C5 -179.61(16) . . . . ?
C16 N4 C5 C6 -39.1(3) . . . . ?
N2 N4 C5 C6 140.05(18) . . . . ?
C16 N4 C5 C4 136.88(19) . . . . ?
N2 N4 C5 C4 -43.9(2) . . . . ?
C9 C4 C5 C6 1.3(2) . . . . ?
C3 C4 C5 C6 -179.67(17) . . . . ?
C9 C4 C5 N4 -174.69(15) . . . . ?
C3 C4 C5 N4 4.4(3) . . . . ?
C10 N1 C8 C7 -3.2(3) . . . . ?
C10 N1 C8 C9 177.54(19) . . . . ?
N1 C8 C7 C6 -178.68(18) . . . . ?
C9 C8 C7 C6 0.5(3) . . . . ?
N4 C5 C6 C7 174.51(17) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C8 C7 C6 C5 0.6(3) . . . . ?
C8 N1 C10 O1 -3.4(4) . . . . ?
C8 N1 C10 C11 178.33(18) . . . . ?
C1 N3 C9 C4 1.1(3) . . . . ?
C1 N3 C9 C8 -179.98(16) . . . . ?
C3 C4 C9 N3 -0.4(2) . . . . ?
C5 C4 C9 N3 178.77(15) . . . . ?
C3 C4 C9 C8 -179.26(16) . . . . ?
C5 C4 C9 C8 -0.1(2) . . . . ?
C7 C8 C9 N3 -179.73(16) . . . . ?
N1 C8 C9 N3 -0.4(2) . . . . ?
C7 C8 C9 C4 -0.8(3) . . . . ?
N1 C8 C9 C4 178.52(15) . . . . ?
O1 C10 C11 C14 48.2(3) . . . . ?
N1 C10 C11 C14 -133.5(2) . . . . ?
O1 C10 C11 C13 -70.8(3) . . . . ?
N1 C10 C11 C13 107.5(2) . . . . ?
O1 C10 C11 C12 170.0(2) . . . . ?
N1 C10 C11 C12 -11.7(3) . . . . ?
N4 N2 C18 C17 0.3(2) . . . . ?
C16 C17 C18 N2 -0.1(3) . . . . ?
N2 N4 C16 C17 0.3(2) . . . . ?
C5 N4 C16 C17 179.52(17) . . . . ?
C18 C17 C16 N4 -0.1(2) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.037
