# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_KPPC_OT20180315_Q3
_database_code_depnum_ccdc_archive 'CCDC 1833004'
_audit_update_record             
;
2018-03-27 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Q3
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         346.38

_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                   8.46(2)
_cell_length_b                   9.59(2)
_cell_length_c                   11.80(3)
_cell_angle_alpha                97.55(9)
_cell_angle_beta                 104.24(19)
_cell_angle_gamma                108.51(13)
_cell_volume                     857.(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3340
_cell_measurement_theta_min      2.2994
_cell_measurement_theta_max      25.0136
_cell_measurement_temperature    293.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364

_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      293.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            10758
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3023
_reflns_number_gt                2113
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1147
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         3023
_refine_ls_number_parameters     239
_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)+(0.0471P)²+0.2758P] 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         0.214
_refine_diff_density_min         -0.249
_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       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_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
O O1 0.0774(2) 0.81325(17) 0.36564(14) 0.0285(4) Uani d . . . 1 . .
H H1 0.0895(11) 0.763(3) 0.423(2) 0.043 Uiso calc U . R 1 . .
C C1 0.2249(3) 0.8592(2) 0.33779(18) 0.0226(5) Uani d . . . 1 . .
N N1 0.2309(2) 0.93496(19) 0.25105(15) 0.0244(4) Uani d . . . 1 . .
C C10 0.8619(3) 0.7373(2) 0.61287(19) 0.0241(5) Uani d . . . 1 . .
H H10 0.9323 0.7995 0.5763 0.029 Uiso calc U . R 1 . .
O O2 0.18267(19) 0.67919(16) 0.51949(13) 0.0247(4) Uani d . . . 1 . .
C C2 0.3878(3) 0.8464(2) 0.38224(18) 0.0197(5) Uani d . . . 1 . .
N N2 0.3923(2) 0.97588(19) 0.23393(16) 0.0254(4) Uani d . . . 1 . .
N N3 0.6175(2) 0.78951(18) 0.50187(15) 0.0213(4) Uani d . . . 1 . .
C C3 0.4867(3) 0.9237(2) 0.31270(18) 0.0211(5) Uani d . . . 1 . .
C C18 0.3216(3) 0.6479(2) 1.0286(2) 0.0327(6) Uani d . . . 1 . .
H H18 0.3229 0.6772 1.1073 0.039 Uiso calc U . R 1 . .
C C19 0.2466(3) 0.4969(3) 0.9697(2) 0.0344(6) Uani d . . . 1 . .
H H19 0.1993 0.4245 1.0096 0.041 Uiso calc U . R 1 . .
C C20 0.2418(3) 0.4532(2) 0.85275(19) 0.0275(5) Uani d . . . 1 . .
H H20 0.1917 0.3515 0.8141 0.033 Uiso calc U . R 1 . .
N N4 0.4054(2) 0.61072(18) 0.61257(14) 0.0190(4) Uani d . . . 1 . .
C C4 0.6699(3) 0.9486(2) 0.3147(2) 0.0293(6) Uani d . . . 1 . .
H H4A 0.6805 0.8531 0.2912 0.044 Uiso calc U . R 1 . .
H H4B 0.7474 0.9984 0.3944 0.044 Uiso calc U . R 1 . .
H H4C 0.7001 1.0104 0.2598 0.044 Uiso calc U . R 1 . .
C C13 0.6546(3) 0.5518(2) 0.72276(19) 0.0245(5) Uani d . . . 1 . .
H H13 0.5854 0.4893 0.7598 0.029 Uiso calc U . R 1 . .
C C12 0.8292(3) 0.5723(2) 0.74710(19) 0.0270(5) Uani d . . . 1 . .
H H12 0.8776 0.5232 0.8009 0.032 Uiso calc U . R 1 . .
C C11 0.9331(3) 0.6647(2) 0.69265(19) 0.0265(5) Uani d . . . 1 . .
H H11 1.0509 0.6779 0.7098 0.032 Uiso calc U . R 1 . .
C C5 0.0898(3) 0.9638(3) 0.1715(2) 0.0329(6) Uani d . . . 1 . .
H H5A 0.0485 0.8944 0.0948 0.049 Uiso calc U . R 1 . .
H H5B 0.1321 1.0654 0.1613 0.049 Uiso calc U . R 1 . .
H H5C -0.0043 0.9507 0.2057 0.049 Uiso calc U . R 1 . .
C C15 0.3110(3) 0.5597(2) 0.79219(18) 0.0191(5) Uani d . . . 1 . .
C C14 0.2878(3) 0.5061(2) 0.66162(18) 0.0204(5) Uani d . . . 1 . .
H H14A 0.3055 0.4107 0.6507 0.024 Uiso calc U . R 1 . .
H H14B 0.168 0.4873 0.6159 0.024 Uiso calc U . R 1 . .
C C6 0.4537(3) 0.7758(2) 0.47613(17) 0.0182(5) Uani d . . . 1 . .
C C9 0.6853(3) 0.7189(2) 0.58604(18) 0.0203(5) Uani d . . . 1 . .
C C7 0.3373(3) 0.6875(2) 0.53660(18) 0.0194(5) Uani d . . . 1 . .
C C8 0.5817(3) 0.6260(2) 0.64149(18) 0.0192(5) Uani d . . . 1 . .
C C16 0.3891(3) 0.7105(2) 0.85260(19) 0.0248(5) Uani d . . . 1 . .
H H16 0.4389 0.783 0.8137 0.03 Uiso calc U . R 1 . .
C C17 0.3935(3) 0.7539(2) 0.9705(2) 0.0294(6) Uani d . . . 1 . .
H H17 0.4455 0.8553 1.0101 0.035 Uiso calc U . R 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
O1 C1 . 1.323(4) ?
O1 H1 . 0.88(3) ?
C1 N1 . 1.332(4) ?
C1 C2 . 1.400(5) ?
N1 N2 . 1.370(4) ?
N1 C5 . 1.453(4) ?
C10 C11 . 1.376(4) ?
C10 C9 . 1.397(5) ?
C10 H10 . 0.93 ?
O2 C7 . 1.249(4) ?
C2 C3 . 1.424(4) ?
C2 C6 . 1.460(4) ?
N2 C3 . 1.328(4) ?
N3 C6 . 1.303(4) ?
N3 C9 . 1.385(4) ?
C3 C4 . 1.485(5) ?
C18 C17 . 1.368(4) ?
C18 C19 . 1.385(5) ?
C18 H18 . 0.93 ?
C19 C20 . 1.375(5) ?
C19 H19 . 0.93 ?
C20 C15 . 1.383(4) ?
C20 H20 . 0.93 ?
N4 C7 . 1.366(4) ?
N4 C8 . 1.401(5) ?
N4 C14 . 1.461(4) ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C13 C12 . 1.377(5) ?
C13 C8 . 1.405(4) ?
C13 H13 . 0.93 ?
C12 C11 . 1.380(4) ?
C12 H12 . 0.93 ?
C11 H11 . 0.93 ?
C5 H5A . 0.96 ?
C5 H5B . 0.96 ?
C5 H5C . 0.96 ?
C15 C16 . 1.388(5) ?
C15 C14 . 1.502(5) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C6 C7 . 1.473(4) ?
C9 C8 . 1.389(4) ?
C16 C17 . 1.386(4) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?

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
C1 O1 H1 . . 109.5 ?
O1 C1 N1 . . 118.2(3) ?
O1 C1 C2 . . 133.1(2) ?
N1 C1 C2 . . 108.7(2) ?
C1 N1 N2 . . 111.1(2) ?
C1 N1 C5 . . 128.7(2) ?
N2 N1 C5 . . 119.9(2) ?
C11 C10 C9 . . 120.9(2) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C1 C2 C3 . . 103.0(2) ?
C1 C2 C6 . . 132.0(2) ?
C3 C2 C6 . . 125.0(2) ?
C3 N2 N1 . . 105.7(2) ?
C6 N3 C9 . . 120.3(2) ?
N2 C3 C2 . . 111.5(3) ?
N2 C3 C4 . . 118.5(2) ?
C2 C3 C4 . . 130.0(2) ?
C17 C18 C19 . . 119.7(3) ?
C17 C18 H18 . . 120.2 ?
C19 C18 H18 . . 120.2 ?
C20 C19 C18 . . 120.4(2) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
C19 C20 C15 . . 120.4(3) ?
C19 C20 H20 . . 119.8 ?
C15 C20 H20 . . 119.8 ?
C7 N4 C8 . . 122.1(2) ?
C7 N4 C14 . . 118.3(2) ?
C8 N4 C14 . . 119.5(2) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C12 C13 C8 . . 119.5(2) ?
C12 C13 H13 . . 120.3 ?
C8 C13 H13 . . 120.3 ?
C13 C12 C11 . . 120.8(2) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C10 C11 C12 . . 119.8(3) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
N1 C5 H5A . . 109.5 ?
N1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
N1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C20 C15 C16 . . 118.8(3) ?
C20 C15 C14 . . 117.7(2) ?
C16 C15 C14 . . 123.4(2) ?
N4 C14 C15 . . 114.7(2) ?
N4 C14 H14A . . 108.6 ?
C15 C14 H14A . . 108.6 ?
N4 C14 H14B . . 108.6 ?
C15 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
N3 C6 C2 . . 117.7(2) ?
N3 C6 C7 . . 121.2(2) ?
C2 C6 C7 . . 121.1(3) ?
N3 C9 C8 . . 122.0(3) ?
N3 C9 C10 . . 119.0(2) ?
C8 C9 C10 . . 119.0(2) ?
O2 C7 N4 . . 120.3(2) ?
O2 C7 C6 . . 123.0(2) ?
N4 C7 C6 . . 116.7(3) ?
C9 C8 N4 . . 117.3(2) ?
C9 C8 C13 . . 120.1(3) ?
N4 C8 C13 . . 122.6(2) ?
C17 C16 C15 . . 120.6(2) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C18 C17 C16 . . 120.1(3) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 N1 N2 . . . . 179.32(17) ?
C2 C1 N1 N2 . . . . -0.3(2) ?
O1 C1 N1 C5 . . . . -6.7(3) ?
C2 C1 N1 C5 . . . . 173.8(2) ?
O1 C1 C2 C3 . . . . -179.0(2) ?
N1 C1 C2 C3 . . . . 0.5(2) ?
O1 C1 C2 C6 . . . . 0.5(4) ?
N1 C1 C2 C6 . . . . -180.0(2) ?
C1 N1 N2 C3 . . . . -0.1(2) ?
C5 N1 N2 C3 . . . . -174.76(18) ?
N1 N2 C3 C2 . . . . 0.5(2) ?
N1 N2 C3 C4 . . . . 179.02(18) ?
C1 C2 C3 N2 . . . . -0.6(2) ?
C6 C2 C3 N2 . . . . 179.83(18) ?
C1 C2 C3 C4 . . . . -178.9(2) ?
C6 C2 C3 C4 . . . . 1.5(3) ?
C17 C18 C19 C20 . . . . -1.0(4) ?
C18 C19 C20 C15 . . . . -0.3(4) ?
C8 C13 C12 C11 . . . . 0.0(3) ?
C9 C10 C11 C12 . . . . 0.0(3) ?
C13 C12 C11 C10 . . . . -0.1(3) ?
C19 C20 C15 C16 . . . . 1.6(3) ?
C19 C20 C15 C14 . . . . -174.8(2) ?
C7 N4 C14 C15 . . . . -107.3(3) ?
C8 N4 C14 C15 . . . . 74.6(3) ?
C20 C15 C14 N4 . . . . -162.3(2) ?
C16 C15 C14 N4 . . . . 21.4(3) ?
C9 N3 C6 C2 . . . . -176.92(17) ?
C9 N3 C6 C7 . . . . 1.0(3) ?
C1 C2 C6 N3 . . . . -176.4(2) ?
C3 C2 C6 N3 . . . . 3.0(3) ?
C1 C2 C6 C7 . . . . 5.6(3) ?
C3 C2 C6 C7 . . . . -174.95(19) ?
C6 N3 C9 C8 . . . . 3.1(3) ?
C6 N3 C9 C10 . . . . -179.18(19) ?
C11 C10 C9 N3 . . . . -177.60(19) ?
C11 C10 C9 C8 . . . . 0.2(3) ?
C8 N4 C7 O2 . . . . -174.97(18) ?
C14 N4 C7 O2 . . . . 7.0(3) ?
C8 N4 C7 C6 . . . . 6.2(3) ?
C14 N4 C7 C6 . . . . -171.89(17) ?
N3 C6 C7 O2 . . . . 175.63(19) ?
C2 C6 C7 O2 . . . . -6.5(3) ?
N3 C6 C7 N4 . . . . -5.5(3) ?
C2 C6 C7 N4 . . . . 172.31(18) ?
N3 C9 C8 N4 . . . . -2.5(3) ?
C10 C9 C8 N4 . . . . 179.81(18) ?
N3 C9 C8 C13 . . . . 177.41(19) ?
C10 C9 C8 C13 . . . . -0.3(3) ?
C7 N4 C8 C9 . . . . -2.4(3) ?
C14 N4 C8 C9 . . . . 175.63(17) ?
C7 N4 C8 C13 . . . . 177.69(19) ?
C14 N4 C8 C13 . . . . -4.3(3) ?
C12 C13 C8 C9 . . . . 0.2(3) ?
C12 C13 C8 N4 . . . . -179.90(19) ?
C20 C15 C16 C17 . . . . -1.7(3) ?
C14 C15 C16 C17 . . . . 174.6(2) ?
C19 C18 C17 C16 . . . . 1.0(4) ?
C15 C16 C17 C18 . . . . 0.4(3) ?



####################################################################### 
# 
# 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_KPPC_OT20180316_Q5
_database_code_depnum_ccdc_archive 'CCDC 1833005'
_audit_update_record             
;
2018-03-27 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Q5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         284.32

_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                   9.998(5)
_cell_length_b                   9.281(4)
_cell_length_c                   14.416(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.77(2)
_cell_angle_gamma                90
_cell_volume                     1330.9(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.3698
_cell_measurement_theta_max      26.4157
_cell_measurement_temperature    293.(2)

_exptl_crystal_description       rectangle
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.031
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600

_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      293.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            53577
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             2742
_reflns_number_gt                2461
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0993
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_number_reflns         2742
_refine_ls_number_parameters     195
_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)+(0.0498P)²+0.6374P] 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         0.232
_refine_diff_density_min         -0.271
_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       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_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
O O1 0.20110(9) 0.50227(10) 0.41724(6) 0.0216(2) Uani d . . . 1 . .
H H1 0.2413(13) 0.5642(18) 0.3781(8) 0.032 Uiso calc U . R 1 . .
C C1 0.26114(12) 0.51452(13) 0.50317(9) 0.0167(3) Uani d . . . 1 . .
N N1 0.21784(10) 0.43331(11) 0.57078(7) 0.0182(2) Uani d . . . 1 . .
O O2 0.33753(9) 0.68950(10) 0.34712(6) 0.0219(2) Uani d . . . 1 . .
C C2 0.36853(12) 0.59897(13) 0.54312(8) 0.0157(3) Uani d . . . 1 . .
N N2 0.28952(11) 0.45843(12) 0.65562(7) 0.0202(2) Uani d . . . 1 . .
N N3 0.55072(10) 0.76227(11) 0.55659(7) 0.0167(2) Uani d . . . 1 . .
C C3 0.37965(12) 0.55722(13) 0.63917(9) 0.0181(3) Uani d . . . 1 . .
N N4 0.50670(10) 0.84930(11) 0.37174(7) 0.0163(2) Uani d . . . 1 . .
C C4 0.47335(15) 0.60999(15) 0.71910(9) 0.0252(3) Uani d . . . 1 . .
H H4A 0.5641 0.5863 0.7086 0.038 Uiso calc U . R 1 . .
H H4B 0.4515 0.565 0.7756 0.038 Uiso calc U . R 1 . .
H H4C 0.4647 0.7126 0.7245 0.038 Uiso calc U . R 1 . .
C C5 0.10617(13) 0.33282(14) 0.56319(9) 0.0219(3) Uani d . . . 1 . .
H H5A 0.0925 0.2963 0.5006 0.033 Uiso calc U . R 1 . .
H H5B 0.0263 0.3813 0.5782 0.033 Uiso calc U . R 1 . .
H H5C 0.1258 0.2543 0.6058 0.033 Uiso calc U . R 1 . .
C C9 0.63355(12) 0.86217(13) 0.52126(8) 0.0169(3) Uani d . . . 1 . .
C C8 0.61542(12) 0.90795(13) 0.42789(8) 0.0162(3) Uani d . . . 1 . .
C C7 0.42768(12) 0.74413(13) 0.40243(8) 0.0162(3) Uani d . . . 1 . .
C C6 0.45326(12) 0.70362(13) 0.50231(8) 0.0153(3) Uani d . . . 1 . .
C C10 0.73924(12) 0.92088(14) 0.58119(9) 0.0201(3) Uani d . . . 1 . .
H H10 0.7516 0.8916 0.6432 0.024 Uiso calc U . R 1 . .
C C14 0.47509(13) 0.89808(14) 0.27436(8) 0.0193(3) Uani d . . . 1 . .
H H14A 0.5009 0.9983 0.2694 0.023 Uiso calc U . R 1 . .
H H14B 0.3789 0.8913 0.2575 0.023 Uiso calc U . R 1 . .
C C13 0.70459(12) 1.00742(13) 0.39479(9) 0.0196(3) Uani d . . . 1 . .
H H13 0.6948 1.0356 0.3326 0.024 Uiso calc U . R 1 . .
C C12 0.80729(13) 1.06322(14) 0.45549(9) 0.0211(3) Uani d . . . 1 . .
H H12 0.8661 1.13 0.4337 0.025 Uiso calc U . R 1 . .
C C11 0.82448(13) 1.02119(15) 0.54897(9) 0.0224(3) Uani d . . . 1 . .
H H11 0.8933 1.0609 0.5892 0.027 Uiso calc U . R 1 . .
C C15 0.54749(14) 0.80875(15) 0.20724(9) 0.0222(3) Uani d . . . 1 . .
H H15A 0.5301 0.8476 0.1455 0.033 Uiso calc U . R 1 . .
H H15B 0.5159 0.7111 0.2078 0.033 Uiso calc U . R 1 . .
H H15C 0.6424 0.8108 0.2259 0.033 Uiso calc U . R 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
O1 C1 . 1.3260(16) ?
O1 H1 . 0.925(18) ?
C1 N1 . 1.3380(17) ?
C1 C2 . 1.4052(18) ?
N1 N2 . 1.3739(16) ?
N1 C5 . 1.4505(17) ?
O2 C7 . 1.2493(15) ?
C2 C3 . 1.4315(18) ?
C2 C6 . 1.4516(18) ?
N2 C3 . 1.3236(18) ?
N3 C6 . 1.3057(16) ?
N3 C9 . 1.3747(17) ?
C3 C4 . 1.4927(18) ?
N4 C7 . 1.3576(17) ?
N4 C8 . 1.3987(16) ?
N4 C14 . 1.4786(16) ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C5 H5A . 0.96 ?
C5 H5B . 0.96 ?
C5 H5C . 0.96 ?
C9 C8 . 1.4057(18) ?
C9 C10 . 1.4059(18) ?
C8 C13 . 1.4002(18) ?
C7 C6 . 1.4853(17) ?
C10 C11 . 1.374(2) ?
C10 H10 . 0.93 ?
C14 C15 . 1.5127(19) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C13 C12 . 1.3812(19) ?
C13 H13 . 0.93 ?
C12 C11 . 1.397(2) ?
C12 H12 . 0.93 ?
C11 H11 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?

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
C1 O1 H1 . . 109.5 ?
O1 C1 N1 . . 118.87(11) ?
O1 C1 C2 . . 133.34(12) ?
N1 C1 C2 . . 107.79(11) ?
C1 N1 N2 . . 112.02(11) ?
C1 N1 C5 . . 127.61(11) ?
N2 N1 C5 . . 120.33(10) ?
C1 C2 C3 . . 103.14(11) ?
C1 C2 C6 . . 131.31(11) ?
C3 C2 C6 . . 125.55(11) ?
C3 N2 N1 . . 105.17(10) ?
C6 N3 C9 . . 120.02(11) ?
N2 C3 C2 . . 111.89(11) ?
N2 C3 C4 . . 118.35(11) ?
C2 C3 C4 . . 129.75(12) ?
C7 N4 C8 . . 122.35(11) ?
C7 N4 C14 . . 116.98(10) ?
C8 N4 C14 . . 120.65(11) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N1 C5 H5A . . 109.5 ?
N1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
N1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N3 C9 C8 . . 122.28(11) ?
N3 C9 C10 . . 118.52(11) ?
C8 C9 C10 . . 119.20(12) ?
N4 C8 C13 . . 122.95(11) ?
N4 C8 C9 . . 117.03(11) ?
C13 C8 C9 . . 120.02(11) ?
O2 C7 N4 . . 119.35(11) ?
O2 C7 C6 . . 123.97(11) ?
N4 C7 C6 . . 116.67(11) ?
N3 C6 C2 . . 117.84(11) ?
N3 C6 C7 . . 121.39(11) ?
C2 C6 C7 . . 120.77(11) ?
C11 C10 C9 . . 120.56(12) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
N4 C14 C15 . . 111.65(11) ?
N4 C14 H14A . . 109.3 ?
C15 C14 H14A . . 109.3 ?
N4 C14 H14B . . 109.3 ?
C15 C14 H14B . . 109.3 ?
H14A C14 H14B . . 108.0 ?
C12 C13 C8 . . 119.32(12) ?
C12 C13 H13 . . 120.3 ?
C8 C13 H13 . . 120.3 ?
C13 C12 C11 . . 121.20(12) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C10 C11 C12 . . 119.66(12) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 N1 N2 . . . . -179.82(10) ?
C2 C1 N1 N2 . . . . 0.46(14) ?
O1 C1 N1 C5 . . . . -2.43(19) ?
C2 C1 N1 C5 . . . . 177.84(11) ?
O1 C1 C2 C3 . . . . 179.98(13) ?
N1 C1 C2 C3 . . . . -0.35(13) ?
O1 C1 C2 C6 . . . . -0.6(2) ?
N1 C1 C2 C6 . . . . 179.04(12) ?
C1 N1 N2 C3 . . . . -0.36(13) ?
C5 N1 N2 C3 . . . . -177.96(11) ?
N1 N2 C3 C2 . . . . 0.12(13) ?
N1 N2 C3 C4 . . . . 179.12(11) ?
C1 C2 C3 N2 . . . . 0.14(14) ?
C6 C2 C3 N2 . . . . -179.30(11) ?
C1 C2 C3 C4 . . . . -178.71(13) ?
C6 C2 C3 C4 . . . . 1.9(2) ?
C6 N3 C9 C8 . . . . 1.82(17) ?
C6 N3 C9 C10 . . . . -178.66(11) ?
C7 N4 C8 C13 . . . . 174.38(11) ?
C14 N4 C8 C13 . . . . -4.16(18) ?
C7 N4 C8 C9 . . . . -5.29(17) ?
C14 N4 C8 C9 . . . . 176.17(10) ?
N3 C9 C8 N4 . . . . 1.21(17) ?
C10 C9 C8 N4 . . . . -178.31(10) ?
N3 C9 C8 C13 . . . . -178.47(11) ?
C10 C9 C8 C13 . . . . 2.01(18) ?
C8 N4 C7 O2 . . . . -175.36(11) ?
C14 N4 C7 O2 . . . . 3.22(16) ?
C8 N4 C7 C6 . . . . 5.99(16) ?
C14 N4 C7 C6 . . . . -175.42(10) ?
C9 N3 C6 C2 . . . . -179.88(10) ?
C9 N3 C6 C7 . . . . -1.02(17) ?
C1 C2 C6 N3 . . . . -177.15(12) ?
C3 C2 C6 N3 . . . . 2.12(18) ?
C1 C2 C6 C7 . . . . 3.99(19) ?
C3 C2 C6 C7 . . . . -176.74(11) ?
O2 C7 C6 N3 . . . . 178.63(11) ?
N4 C7 C6 N3 . . . . -2.80(17) ?
O2 C7 C6 C2 . . . . -2.55(18) ?
N4 C7 C6 C2 . . . . 176.03(10) ?
N3 C9 C10 C11 . . . . -179.93(11) ?
C8 C9 C10 C11 . . . . -0.39(18) ?
C7 N4 C14 C15 . . . . -88.52(13) ?
C8 N4 C14 C15 . . . . 90.09(14) ?
N4 C8 C13 C12 . . . . 178.22(11) ?
C9 C8 C13 C12 . . . . -2.11(18) ?
C8 C13 C12 C11 . . . . 0.60(19) ?
C9 C10 C11 C12 . . . . -1.12(19) ?
C13 C12 C11 C10 . . . . 1.02(19) ?



