# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_171130_sc171128
_database_code_depnum_ccdc_archive 'CCDC 1967873'
loop_
_audit_author_name
_audit_author_address
sc
; Zhejiang University of Technology
China
;
_audit_update_record             
;
2019-11-25 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N5 O2'
_chemical_formula_sum            'C16 H17 N5 O2'
_chemical_formula_weight         311.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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'

_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      triclinic
_space_group_IT_number           2
_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                   7.1753(5)
_cell_length_b                   10.1901(9)
_cell_length_c                   11.0558(9)
_cell_angle_alpha                109.818(7)
_cell_angle_beta                 97.305(6)
_cell_angle_gamma                100.110(6)
_cell_volume                     733.32(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1425
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.3363
_cell_measurement_theta_min      2.9382
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.944
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -79.00    9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   77.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -74.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000  150.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0264107000
_diffrn_orient_matrix_UB_12      -0.0450985000
_diffrn_orient_matrix_UB_13      0.0348096000
_diffrn_orient_matrix_UB_21      -0.0332988000
_diffrn_orient_matrix_UB_22      0.0552582000
_diffrn_orient_matrix_UB_23      0.0441742000
_diffrn_orient_matrix_UB_31      -0.0932916000
_diffrn_orient_matrix_UB_32      -0.0265533000
_diffrn_orient_matrix_UB_33      -0.0410421000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2027
_reflns_number_total             2690
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.028
_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)+(0.0597P)²+0.1632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1312
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.9770(2) 0.71848(16) 0.57390(14) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.81516(19) 0.55909(15) 0.64467(13) 0.0301(4) Uani 1 1 d . . . . .
N1 N 0.5101(2) 0.15874(18) 0.40385(16) 0.0284(4) Uani 1 1 d . . . . .
N2 N 0.4419(2) 0.19212(18) 0.19843(16) 0.0278(4) Uani 1 1 d . . . . .
N3 N 0.6298(2) 0.38111(17) 0.39314(15) 0.0236(4) Uani 1 1 d . . . . .
N4 N 0.5718(2) 0.42786(18) 0.20952(16) 0.0263(4) Uani 1 1 d . . . . .
N5 N 0.3286(2) -0.02503(18) 0.21569(17) 0.0317(5) Uani 1 1 d . . . . .
C1 C 0.6087(3) 0.2893(2) 0.4593(2) 0.0270(5) Uani 1 1 d . . . . .
H1 H 0.669086 0.323334 0.549313 0.032 Uiso 1 1 calc R . . . .
C2 C 0.4286(3) 0.1118(2) 0.2721(2) 0.0268(5) Uani 1 1 d . . . . .
C3 C 0.5422(3) 0.3281(2) 0.26083(19) 0.0244(5) Uani 1 1 d . . . . .
C4 C 0.7265(3) 0.5254(2) 0.42495(19) 0.0243(5) Uani 1 1 d . . . . .
C5 C 0.6831(3) 0.5497(2) 0.30937(19) 0.0246(5) Uani 1 1 d . . . . .
C6 C 0.7274(3) 0.6822(2) 0.2805(2) 0.0255(5) Uani 1 1 d . . . . .
C7 C 0.6967(3) 0.6699(2) 0.1495(2) 0.0296(5) Uani 1 1 d . . . . .
H7 H 0.654593 0.577465 0.081839 0.036 Uiso 1 1 calc R . . . .
C8 C 0.7268(3) 0.7906(2) 0.1166(2) 0.0329(5) Uani 1 1 d . . . . .
H8 H 0.704901 0.780650 0.026999 0.040 Uiso 1 1 calc R . . . .
C9 C 0.7889(3) 0.9261(2) 0.2146(2) 0.0325(5) Uani 1 1 d . . . . .
H9 H 0.811942 1.008951 0.192481 0.039 Uiso 1 1 calc R . . . .
C10 C 0.8172(3) 0.9396(2) 0.3445(2) 0.0302(5) Uani 1 1 d . . . . .
H10 H 0.857738 1.032330 0.411837 0.036 Uiso 1 1 calc R . . . .
C11 C 0.7867(3) 0.8190(2) 0.3775(2) 0.0272(5) Uani 1 1 d . . . . .
H11 H 0.806581 0.829866 0.467358 0.033 Uiso 1 1 calc R . . . .
C12 C 0.3059(3) -0.1225(2) 0.2858(2) 0.0348(5) Uani 1 1 d . . . . .
H12A H 0.370068 -0.200203 0.249290 0.052 Uiso 1 1 calc GR . . . .
H12B H 0.168099 -0.162941 0.276457 0.052 Uiso 1 1 calc GR . . . .
H12C H 0.364284 -0.070079 0.378979 0.052 Uiso 1 1 calc GR . . . .
C13 C 0.2487(3) -0.0871(3) 0.0755(2) 0.0426(6) Uani 1 1 d . . . . .
H13A H 0.248059 -0.010127 0.041214 0.064 Uiso 1 1 calc GR . . . .
H13B H 0.116142 -0.143070 0.059780 0.064 Uiso 1 1 calc GR . . . .
H13C H 0.327940 -0.149820 0.030933 0.064 Uiso 1 1 calc GR . . . .
C14 C 0.8519(3) 0.6124(2) 0.5519(2) 0.0263(5) Uani 1 1 d . . . . .
C15 C 0.9357(3) 0.6344(2) 0.77479(19) 0.0292(5) Uani 1 1 d . . . . .
H15A H 0.896799 0.724108 0.820127 0.035 Uiso 1 1 calc R . . . .
H15B H 1.073044 0.659056 0.768653 0.035 Uiso 1 1 calc R . . . .
C16 C 0.9086(3) 0.5358(2) 0.8486(2) 0.0366(6) Uani 1 1 d . . . . .
H16A H 0.951532 0.448800 0.804240 0.055 Uiso 1 1 calc GR . . . .
H16B H 0.771581 0.509848 0.851568 0.055 Uiso 1 1 calc GR . . . .
H16C H 0.984865 0.584126 0.938178 0.055 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
O1 C14 1.208(2) . ?
O2 C14 1.346(2) . ?
O2 C15 1.452(2) . ?
N1 C1 1.286(3) . ?
N1 C2 1.380(3) . ?
N2 C2 1.337(2) . ?
N2 C3 1.338(2) . ?
N3 C1 1.369(2) . ?
N3 C3 1.392(2) . ?
N3 C4 1.413(2) . ?
N4 C3 1.321(2) . ?
N4 C5 1.377(3) . ?
N5 C2 1.339(3) . ?
N5 C12 1.453(3) . ?
N5 C13 1.454(3) . ?
C1 H1 0.9500 . ?
C4 C5 1.390(3) . ?
C4 C14 1.456(3) . ?
C5 C6 1.481(3) . ?
C6 C7 1.397(3) . ?
C6 C11 1.392(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.497(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C14 O2 C15 116.82(15) . . ?
C1 N1 C2 117.30(17) . . ?
C2 N2 C3 115.58(17) . . ?
C1 N3 C3 117.73(16) . . ?
C1 N3 C4 135.55(17) . . ?
C3 N3 C4 106.71(15) . . ?
C3 N4 C5 106.03(16) . . ?
C2 N5 C12 123.26(18) . . ?
C2 N5 C13 120.45(17) . . ?
C12 N5 C13 116.12(17) . . ?
N1 C1 N3 122.34(18) . . ?
N1 C1 H1 118.8 . . ?
N3 C1 H1 118.8 . . ?
N2 C2 N1 125.06(18) . . ?
N2 C2 N5 118.49(18) . . ?
N5 C2 N1 116.46(18) . . ?
N2 C3 N3 121.96(17) . . ?
N4 C3 N2 126.52(18) . . ?
N4 C3 N3 111.52(17) . . ?
N3 C4 C14 122.68(17) . . ?
C5 C4 N3 104.23(17) . . ?
C5 C4 C14 132.90(18) . . ?
N4 C5 C4 111.47(17) . . ?
N4 C5 C6 117.34(17) . . ?
C4 C5 C6 131.11(18) . . ?
C7 C6 C5 118.33(19) . . ?
C11 C6 C5 123.28(17) . . ?
C11 C6 C7 118.26(19) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.94(19) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.62(19) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.71(19) . . ?
C10 C11 H11 119.6 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 O2 122.74(19) . . ?
O1 C14 C4 125.45(18) . . ?
O2 C14 C4 111.79(16) . . ?
O2 C15 H15A 110.3 . . ?
O2 C15 H15B 110.3 . . ?
O2 C15 C16 107.04(16) . . ?
H15A C15 H15B 108.6 . . ?
C16 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
