# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_ic10201
_audit_block_doi                 10.5517/ccdc.csd.cc23vb8l
_database_code_depnum_ccdc_archive 'CCDC 1961719'
loop_
_audit_author_name
_audit_author_address
'Ya-Fan Lin'
;Department of Fragrance and Cosmetic Science, Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-10-27 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C14 H13 N7'
_chemical_formula_weight         279.31
_chemical_melting_point          ?
_chemical_compound_source        ?

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   9.5910(2)
_cell_length_b                   9.3160(2)
_cell_length_c                   15.9820(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.5140(10)
_cell_angle_gamma                90.00
_cell_volume                     1415.73(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    20139
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.987

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ-ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10643
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3242
_reflns_number_observed          1997
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       'Denzo-SMN & Scalepack'
_computing_data_reduction        'Denzo-SMN & Scalepack'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    SHELX
_computing_publication_material  SHELX

_refine_special_details          
; 
 Refinement on F² for ALL reflections except for 45 with very negative F² 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses of fit S are based on F², conventional R-factors R 
 are based on F, with F set to zero for negative F². The observed criterion 
 of F² > 2sigma(F²) is used only for calculating _R_factor_obs etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.1927P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0105(23)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3197
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_obs          0.0497
_refine_ls_wR_factor_all         0.1565
_refine_ls_wR_factor_obs         0.1254
_refine_ls_goodness_of_fit_all   1.034
_refine_ls_goodness_of_fit_obs   1.105
_refine_ls_restrained_S_all      1.065
_refine_ls_restrained_S_obs      1.105
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.9275(2) 0.3264(2) 0.17171(14) 0.0824(6) Uani 1 d . .
N2 N 0.6277(2) 0.1541(2) 0.04543(10) 0.0482(4) Uani 1 d . .
N3 N 0.5113(2) 0.3604(2) 0.07456(10) 0.0462(4) Uani 1 d . .
N4 N 0.3873(2) 0.1431(2) 0.03353(10) 0.0527(4) Uani 1 d . .
N5 N 0.8627(2) 0.1515(2) 0.01602(9) 0.0456(4) Uani 1 d . .
N6 N 0.7980(2) 0.2861(2) -0.10385(10) 0.0595(5) Uani 1 d . .
N7 N 0.9689(2) 0.0993(2) -0.10068(9) 0.0505(4) Uani 1 d . .
C1 C 0.7627(2) 0.2254(2) 0.06102(11) 0.0416(4) Uani 1 d . .
H1A H 0.7515(2) 0.3233(2) 0.03877(11) 0.050 Uiso 1 calc R .
C2 C 0.8201(2) 0.2346(2) 0.15413(11) 0.0445(5) Uani 1 d . .
C3 C 0.7680(2) 0.1567(3) 0.21388(14) 0.0664(6) Uani 1 d . .
H3A H 0.6939(2) 0.0932(3) 0.19950(14) 0.080 Uiso 1 calc R .
C4 C 0.8274(3) 0.1731(4) 0.2978(2) 0.0954(10) Uani 1 d . .
H4A H 0.7935(3) 0.1207(4) 0.3404(2) 0.114 Uiso 1 calc R .
C5 C 0.9355(4) 0.2668(4) 0.3165(2) 0.1000(11) Uani 1 d . .
H5A H 0.9765(4) 0.2804(4) 0.3719(2) 0.120 Uiso 1 calc R .
C6 C 0.9813(3) 0.3389(4) 0.2533(2) 0.1048(11) Uani 1 d . .
H6A H 1.0559(3) 0.4023(4) 0.2667(2) 0.126 Uiso 1 calc R .
C7 C 0.5049(2) 0.2219(2) 0.05138(10) 0.0399(4) Uani 1 d . .
C8 C 0.3871(2) 0.4248(2) 0.07545(13) 0.0548(5) Uani 1 d . .
H8A H 0.3862(2) 0.5220(2) 0.08853(13) 0.066 Uiso 1 calc R .
C9 C 0.2611(2) 0.3553(2) 0.05817(15) 0.0627(6) Uani 1 d . .
H9A H 0.1761(2) 0.4023(2) 0.06017(15) 0.075 Uiso 1 calc R .
C10 C 0.2666(2) 0.2128(3) 0.03775(14) 0.0619(6) Uani 1 d . .
H10A H 0.1827(2) 0.1623(3) 0.02632(14) 0.074 Uiso 1 calc R .
C11 C 0.8762(2) 0.1803(2) -0.06548(11) 0.0411(4) Uani 1 d . .
C12 C 0.8193(3) 0.3152(3) -0.18255(13) 0.0705(7) Uani 1 d . .
H12A H 0.7673(3) 0.3884(3) -0.21121(13) 0.085 Uiso 1 calc R .
C13 C 0.9138(3) 0.2429(3) -0.22312(14) 0.0746(7) Uani 1 d . .
H13A H 0.9286(3) 0.2664(3) -0.27783(14) 0.089 Uiso 1 calc R .
C14 C 0.9859(2) 0.1342(2) -0.17954(13) 0.0656(6) Uani 1 d . .
H14A H 1.0500(2) 0.0820(2) -0.20619(13) 0.079 Uiso 1 calc R .
H5 H 0.9158(21) 0.0834(23) 0.0412(12) 0.051(5) Uiso 1 d . .
H2 H 0.6250(20) 0.0703(23) 0.0282(12) 0.047(6) Uiso 1 d . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0725(13) 0.0893(15) 0.0794(14) 0.0016(12) -0.0122(10) -0.0141(12)
N2 0.0391(8) 0.0453(10) 0.0605(10) -0.0142(8) 0.0072(7) 0.0101(7)
N3 0.0452(9) 0.0426(9) 0.0530(9) -0.0010(7) 0.0141(7) 0.0086(7)
N4 0.0383(8) 0.0557(10) 0.0634(10) -0.0169(8) 0.0036(7) 0.0074(7)
N5 0.0430(9) 0.0538(10) 0.0416(8) 0.0047(7) 0.0112(6) 0.0192(7)
N6 0.0675(11) 0.0654(11) 0.0476(9) 0.0092(8) 0.0155(8) 0.0296(9)
N7 0.0501(9) 0.0570(10) 0.0467(9) -0.0009(7) 0.0152(7) 0.0166(8)
C1 0.0383(9) 0.0453(10) 0.0424(9) -0.0015(8) 0.0101(7) 0.0104(7)
C2 0.0398(9) 0.0480(11) 0.0463(10) -0.0048(8) 0.0078(8) 0.0110(8)
C3 0.0635(13) 0.084(2) 0.0536(12) 0.0104(11) 0.0166(10) 0.0051(12)
C4 0.098(2) 0.134(3) 0.059(2) 0.024(2) 0.0291(15) 0.041(2)
C5 0.109(3) 0.131(3) 0.053(2) -0.020(2) -0.013(2) 0.037(2)
C6 0.102(2) 0.105(2) 0.094(2) -0.018(2) -0.038(2) -0.007(2)
C7 0.0390(9) 0.0471(10) 0.0338(9) -0.0033(7) 0.0054(7) 0.0100(8)
C8 0.0522(12) 0.0466(11) 0.0683(13) -0.0003(9) 0.0182(9) 0.0155(9)
C9 0.0432(11) 0.0646(14) 0.0806(15) -0.0070(11) 0.0091(10) 0.0205(10)
C10 0.0358(10) 0.0689(14) 0.0798(15) -0.0189(12) 0.0031(9) 0.0064(9)
C11 0.0384(9) 0.0452(10) 0.0402(9) -0.0027(8) 0.0065(7) 0.0075(8)
C12 0.089(2) 0.075(2) 0.0498(12) 0.0149(11) 0.0168(11) 0.0310(13)
C13 0.098(2) 0.082(2) 0.0493(12) 0.0100(11) 0.0284(12) 0.0268(14)
C14 0.0738(14) 0.076(2) 0.0520(12) -0.0019(11) 0.0261(10) 0.0249(12)

_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 C2 1.340(3) . ?
N1 C6 1.343(4) . ?
N2 C7 1.350(2) . ?
N2 C1 1.448(2) . ?
N3 C8 1.336(2) . ?
N3 C7 1.341(2) . ?
N4 C10 1.336(2) . ?
N4 C7 1.345(2) . ?
N5 C11 1.353(2) . ?
N5 C1 1.446(2) . ?
N6 C12 1.329(3) . ?
N6 C11 1.337(2) . ?
N7 C14 1.332(2) . ?
N7 C11 1.344(2) . ?
C1 C2 1.520(2) . ?
C2 C3 1.346(3) . ?
C3 C4 1.396(4) . ?
C4 C5 1.358(4) . ?
C5 C6 1.335(5) . ?
C8 C9 1.366(3) . ?
C9 C10 1.369(3) . ?
C12 C13 1.360(3) . ?
C13 C14 1.365(3) . ?

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
C2 N1 C6 116.5(2) . . ?
C7 N2 C1 122.8(2) . . ?
C8 N3 C7 115.2(2) . . ?
C10 N4 C7 115.6(2) . . ?
C11 N5 C1 122.52(15) . . ?
C12 N6 C11 116.0(2) . . ?
C14 N7 C11 115.3(2) . . ?
N5 C1 N2 109.43(15) . . ?
N5 C1 C2 109.57(14) . . ?
N2 C1 C2 113.30(15) . . ?
N1 C2 C3 122.8(2) . . ?
N1 C2 C1 114.3(2) . . ?
C3 C2 C1 122.9(2) . . ?
C2 C3 C4 118.7(3) . . ?
C5 C4 C3 119.0(3) . . ?
C6 C5 C4 118.3(3) . . ?
C5 C6 N1 124.6(3) . . ?
N3 C7 N4 126.17(15) . . ?
N3 C7 N2 117.4(2) . . ?
N4 C7 N2 116.4(2) . . ?
N3 C8 C9 123.5(2) . . ?
C8 C9 C10 116.5(2) . . ?
N4 C10 C9 122.9(2) . . ?
N6 C11 N7 125.7(2) . . ?
N6 C11 N5 117.98(15) . . ?
N7 C11 N5 116.3(2) . . ?
N6 C12 C13 123.0(2) . . ?
C12 C13 C14 116.7(2) . . ?
N7 C14 C13 123.2(2) . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_ic9369
_database_code_depnum_ccdc_archive 'CCDC 1961718'
loop_
_audit_author_name
_audit_author_address
'Ya-Fan Lin'
;Department of Fragrance and Cosmetic Science, Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-10-27 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C16 H16 N5'
_chemical_formula_weight         278.34
_chemical_melting_point          ?
_chemical_compound_source        ?

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.8760(3)
_cell_length_b                   8.68900(10)
_cell_length_c                   19.6210(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2877.14(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    21664
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.988

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ-ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20084
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3263
_reflns_number_observed          2245
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       'Denzo-SMN & Scalepack'
_computing_data_reduction        'Denzo-SMN & Scalepack'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    SHELX
_computing_publication_material  SHELX

_refine_special_details          
; 
 Refinement on F² for ALL reflections except for 20 with very negative F² 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses of fit S are based on F², conventional R-factors R 
 are based on F, with F set to zero for negative F². The observed criterion 
 of F² > 2sigma(F²) is used only for calculating _R_factor_obs etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0966P)^2^+0.1890P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0926(87)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3243
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_obs          0.0578
_refine_ls_wR_factor_all         0.1778
_refine_ls_wR_factor_obs         0.1471
_refine_ls_goodness_of_fit_all   1.112
_refine_ls_goodness_of_fit_obs   1.129
_refine_ls_restrained_S_all      1.120
_refine_ls_restrained_S_obs      1.129
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.08440(9) 0.4202(2) 0.35818(8) 0.0610(4) Uani 1 d . .
N2 N 0.07540(10) 0.7143(2) 0.29367(8) 0.0653(4) Uani 1 d . .
N3 N -0.04911(8) 0.4967(2) 0.33183(8) 0.0614(4) Uani 1 d . .
N4 N 0.10546(9) 0.3563(2) 0.47188(7) 0.0663(4) Uani 1 d . .
H4A H 0.06205(9) 0.4019(2) 0.48289(7) 0.080 Uiso 1 calc R .
N5 N -0.15059(9) 0.3438(2) 0.29321(8) 0.0640(4) Uani 1 d . .
C1 C 0.02082(9) 0.5284(2) 0.37187(9) 0.0555(4) Uani 1 d . .
H1A H 0.00684(9) 0.5218(2) 0.42026(9) 0.067 Uiso 1 calc R .
C2 C 0.04650(9) 0.6915(2) 0.35632(8) 0.0538(4) Uani 1 d . .
C3 C 0.13104(9) 0.3558(2) 0.40796(8) 0.0531(4) Uani 1 d . .
C3 C 0.04056(11) 0.8085(2) 0.40372(10) 0.0681(5) Uani 1 d . .
H3A H 0.02099(11) 0.7887(2) 0.44715(10) 0.082 Uiso 1 calc R .
C4 C 0.06398(13) 0.9548(2) 0.38586(13) 0.0834(6) Uani 1 d . .
H4B H 0.06145(13) 1.0348(2) 0.41729(13) 0.100 Uiso 1 calc R .
C5 C 0.09099(13) 0.9807(2) 0.32122(13) 0.0838(6) Uani 1 d . .
H5B H 0.10538(13) 1.0791(2) 0.30728(13) 0.101 Uiso 1 calc R .
C6 C 0.09644(13) 0.8574(2) 0.27703(11) 0.0754(6) Uani 1 d . .
H6A H 0.11581(13) 0.8751(2) 0.23335(11) 0.091 Uiso 1 calc R .
C8 C 0.20292(10) 0.2865(2) 0.38992(10) 0.0656(5) Uani 1 d . .
H8A H 0.22161(10) 0.2917(2) 0.34539(10) 0.079 Uiso 1 calc R .
C9 C 0.24516(12) 0.2108(2) 0.43927(12) 0.0771(6) Uani 1 d . .
H9A H 0.29221(12) 0.1611(2) 0.42814(12) 0.092 Uiso 1 calc R .
C10 C 0.21789(12) 0.2087(3) 0.50509(12) 0.0791(6) Uani 1 d . .
H10A H 0.24551(12) 0.1573(3) 0.53922(12) 0.095 Uiso 1 calc R .
C11 C 0.14947(12) 0.2837(3) 0.51876(11) 0.0779(6) Uani 1 d . .
H11A H 0.13181(12) 0.2850(3) 0.56365(11) 0.093 Uiso 1 calc R .
C12 C -0.09428(9) 0.3670(2) 0.34015(8) 0.0551(4) Uani 1 d . .
C13 C -0.08280(11) 0.2657(2) 0.39518(10) 0.0689(5) Uani 1 d . .
H13A H -0.04303(11) 0.2837(2) 0.42701(10) 0.083 Uiso 1 calc R .
C14 C -0.13117(13) 0.1403(2) 0.40098(11) 0.0789(6) Uani 1 d . .
H14A H -0.12427(13) 0.0715(2) 0.43678(11) 0.095 Uiso 1 calc R .
C15 C -0.19011(13) 0.1162(2) 0.35375(11) 0.0780(6) Uani 1 d . .
H15A H -0.22392(13) 0.0320(2) 0.35709(11) 0.094 Uiso 1 calc R .
C16 C -0.19733(11) 0.2194(2) 0.30201(10) 0.0719(5) Uani 1 d . .
H16A H -0.23746(11) 0.2030(2) 0.27036(10) 0.086 Uiso 1 calc R .
H1 H 0.1039(11) 0.4181(24) 0.3152(10) 0.067(5) Uiso 1 d . .
H3 H -0.0578(10) 0.5540(23) 0.2970(10) 0.061(5) Uiso 1 d . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0696(9) 0.0554(9) 0.0578(9) 0.0022(7) 0.0031(7) 0.0099(7)
N2 0.0779(9) 0.0504(8) 0.0675(9) 0.0002(7) 0.0065(7) -0.0079(7)
N3 0.0665(9) 0.0517(8) 0.0661(9) 0.0115(7) -0.0094(7) -0.0084(7)
N4 0.0578(8) 0.0773(11) 0.0637(9) 0.0060(7) -0.0004(6) 0.0082(7)
N5 0.0623(8) 0.0610(9) 0.0685(9) -0.0052(7) 0.0015(7) -0.0071(7)
C1 0.0584(9) 0.0498(9) 0.0583(9) 0.0020(7) 0.0013(7) 0.0006(7)
C2 0.0513(8) 0.0489(9) 0.0610(9) -0.0021(7) -0.0018(7) -0.0007(6)
C3 0.0553(8) 0.0398(8) 0.0644(10) 0.0002(6) 0.0003(7) -0.0062(7)
C3 0.0706(11) 0.0607(11) 0.0731(11) -0.0103(8) 0.0031(8) -0.0028(9)
C4 0.0911(14) 0.0562(12) 0.103(2) -0.0225(11) 0.0049(12) -0.0121(10)
C5 0.0936(14) 0.0505(11) 0.107(2) -0.0003(11) 0.0026(12) -0.0182(10)
C6 0.0870(13) 0.0588(11) 0.0806(13) 0.0049(9) 0.0080(10) -0.0152(9)
C8 0.0587(10) 0.0612(11) 0.0768(12) -0.0057(9) 0.0037(8) -0.0010(8)
C9 0.0568(10) 0.0648(12) 0.110(2) -0.0030(11) -0.0081(10) 0.0069(8)
C10 0.0665(11) 0.0792(13) 0.0916(14) 0.0185(11) -0.0176(10) -0.0001(10)
C11 0.0696(11) 0.095(2) 0.0694(12) 0.0166(10) -0.0077(9) -0.0032(10)
C12 0.0554(9) 0.0467(9) 0.0631(10) -0.0018(7) 0.0055(7) -0.0014(7)
C13 0.0703(11) 0.0614(11) 0.0749(11) 0.0113(9) -0.0017(9) -0.0083(9)
C14 0.0868(13) 0.0620(12) 0.0879(14) 0.0140(10) 0.0112(11) -0.0102(10)
C15 0.0872(13) 0.0656(12) 0.0811(13) -0.0075(10) 0.0207(10) -0.0241(10)
C16 0.0682(11) 0.0730(12) 0.0746(12) -0.0150(10) 0.0077(9) -0.0164(9)

_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 C3 1.374(2) . ?
N1 C1 1.452(2) . ?
N2 C6 1.333(2) . ?
N2 C2 1.337(2) . ?
N3 C12 1.370(2) . ?
N3 C1 1.444(2) . ?
N4 C3 1.326(2) . ?
N4 C11 1.340(2) . ?
N5 C12 1.339(2) . ?
N5 C16 1.349(2) . ?
C1 C2 1.513(2) . ?
C2 C3 1.381(2) . ?
C3 C8 1.400(2) . ?
C3 C4 1.377(3) . ?
C4 C5 1.366(3) . ?
C5 C6 1.381(3) . ?
C8 C9 1.370(3) . ?
C9 C10 1.371(3) . ?
C10 C11 1.353(3) . ?
C12 C13 1.407(3) . ?
C13 C14 1.366(3) . ?
C14 C15 1.376(3) . ?
C15 C16 1.360(3) . ?

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
C3 N1 C1 123.77(15) . . ?
C6 N2 C2 117.4(2) . . ?
C12 N3 C1 123.15(14) . . ?
C3 N4 C11 117.8(2) . . ?
C12 N5 C16 116.6(2) . . ?
N3 C1 N1 112.30(14) . . ?
N3 C1 C2 107.65(13) . . ?
N1 C1 C2 110.96(13) . . ?
N2 C2 C3 122.4(2) . . ?
N2 C2 C1 115.39(14) . . ?
C3 C2 C1 122.2(2) . . ?
N4 C3 N1 118.97(15) . . ?
N4 C3 C8 121.5(2) . . ?
N1 C3 C8 119.5(2) . . ?
C4 C3 C2 119.2(2) . . ?
C5 C4 C3 118.9(2) . . ?
C4 C5 C6 118.5(2) . . ?
N2 C6 C5 123.5(2) . . ?
C9 C8 C3 118.6(2) . . ?
C8 C9 C10 119.8(2) . . ?
C11 C10 C9 117.8(2) . . ?
N4 C11 C10 124.3(2) . . ?
N5 C12 N3 115.89(15) . . ?
N5 C12 C13 122.1(2) . . ?
N3 C12 C13 122.0(2) . . ?
C14 C13 C12 118.7(2) . . ?
C13 C14 C15 119.9(2) . . ?
C16 C15 C14 117.8(2) . . ?
N5 C16 C15 124.9(2) . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.104
####################################################################### 
# 
# 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_d21627
_database_code_depnum_ccdc_archive 'CCDC 1961720'
loop_
_audit_author_name
_audit_author_address
'Ya-Fan Lin'
;Department of Fragrance and Cosmetic Science, Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-10-27 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N4'
_chemical_formula_sum            'C10 H10 N4'
_chemical_formula_weight         186.22

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.8629(17)
_cell_length_b                   7.7228(7)
_cell_length_c                   14.8431(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.655(3)
_cell_angle_gamma                90.00
_cell_volume                     1870.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6474
_cell_measurement_theta_min      2.837
_cell_measurement_theta_max      25.356

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9466
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14202
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.37
_reflns_number_total             1705
_reflns_number_gt                1486
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0386P)²+1.0910P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1705
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23420(9) 0.70813(19) 0.72890(10) 0.0404(4) Uani 1 1 d . . .
H1 H 0.1827 0.7505 0.7341 0.048 Uiso 1 1 calc R . .
C2 C 0.29725(9) 0.70074(18) 0.80858(10) 0.0406(4) Uani 1 1 d . . .
H2 H 0.2893 0.7360 0.8670 0.049 Uiso 1 1 calc R . .
C3 C 0.37216(8) 0.64069(18) 0.80101(9) 0.0376(3) Uani 1 1 d . . .
H3 H 0.4171 0.6331 0.8544 0.045 Uiso 1 1 calc R . .
C4 C 0.38095(8) 0.59166(17) 0.71448(9) 0.0320(3) Uani 1 1 d . . .
H4 H 0.4323 0.5513 0.7076 0.038 Uiso 1 1 calc R . .
C5 C 0.31424(7) 0.60191(15) 0.63792(8) 0.0260(3) Uani 1 1 d . . .
C6 C 0.31747(7) 0.54891(17) 0.54076(8) 0.0312(3) Uani 1 1 d . . .
H6A H 0.2757 0.4582 0.5182 0.037 Uiso 1 1 calc R . .
H6AB H 0.3028 0.6502 0.4990 0.037 Uiso 1 1 calc R . .
C7 C 0.42342(7) 0.32422(16) 0.56322(8) 0.0271(3) Uani 1 1 d . . .
C8 C 0.40328(9) 0.06668(18) 0.62677(10) 0.0413(4) Uani 1 1 d . . .
H8 H 0.3696 -0.0108 0.6502 0.050 Uiso 1 1 calc R . .
C9 C 0.48088(9) 0.01412(19) 0.62641(10) 0.0431(4) Uani 1 1 d . . .
H9 H 0.5017 -0.0955 0.6502 0.052 Uiso 1 1 calc R . .
C10 C 0.52707(8) 0.12838(19) 0.58979(9) 0.0384(3) Uani 1 1 d . . .
H10 H 0.5808 0.0948 0.5877 0.046 Uiso 1 1 calc R . .
N1 N 0.24094(6) 0.65935(14) 0.64459(7) 0.0337(3) Uani 1 1 d . . .
N2 N 0.39631(6) 0.48404(14) 0.53422(7) 0.0316(3) Uani 1 1 d . . .
H2A H 0.4267 0.5524 0.5087 0.038 Uiso 1 1 d R . .
N3 N 0.37281(7) 0.22083(15) 0.59589(8) 0.0353(3) Uani 1 1 d . . .
N4 N 0.49995(6) 0.28387(14) 0.55719(7) 0.0315(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0433(8) 0.0424(8) 0.0422(8) 0.0031(6) 0.0235(6) 0.0130(6)
C2 0.0568(9) 0.0364(8) 0.0339(7) -0.0029(6) 0.0210(7) 0.0010(6)
C3 0.0406(8) 0.0400(8) 0.0305(7) 0.0006(6) 0.0060(6) -0.0067(6)
C4 0.0261(6) 0.0376(7) 0.0335(7) 0.0021(5) 0.0095(5) 0.0001(5)
C5 0.0266(6) 0.0240(6) 0.0300(6) 0.0062(5) 0.0117(5) 0.0027(5)
C6 0.0280(7) 0.0396(7) 0.0277(6) 0.0067(5) 0.0100(5) 0.0099(5)
C7 0.0266(6) 0.0341(7) 0.0220(6) -0.0012(5) 0.0086(5) 0.0035(5)
C8 0.0503(9) 0.0361(8) 0.0412(8) 0.0057(6) 0.0184(7) 0.0014(6)
C9 0.0536(9) 0.0374(8) 0.0396(8) 0.0063(6) 0.0141(7) 0.0160(7)
C10 0.0340(7) 0.0459(8) 0.0346(7) -0.0038(6) 0.0073(6) 0.0135(6)
N1 0.0309(6) 0.0391(6) 0.0343(6) 0.0066(5) 0.0144(5) 0.0112(5)
N2 0.0296(6) 0.0362(6) 0.0346(6) 0.0087(5) 0.0183(5) 0.0069(4)
N3 0.0328(6) 0.0373(6) 0.0392(6) 0.0057(5) 0.0155(5) 0.0020(5)
N4 0.0261(6) 0.0383(6) 0.0316(6) -0.0028(5) 0.0097(4) 0.0054(5)

_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
C1 N1 1.3390(17) . ?
C1 C2 1.377(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.3825(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3843(18) . ?
C4 H4 0.9500 . ?
C5 N1 1.3403(15) . ?
C5 C6 1.5133(17) . ?
C6 N2 1.4468(15) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 N3 1.3456(16) . ?
C7 N2 1.3483(16) . ?
C7 N4 1.3524(15) . ?
C8 N3 1.3312(18) . ?
C8 C9 1.371(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(2) . ?
C9 H9 0.9500 . ?
C10 N4 1.3316(18) . ?
C10 H10 0.9500 . ?
N2 H2A 0.8848 . ?

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
N1 C1 C2 124.15(12) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 117.97(12) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 118.97(12) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 119.41(12) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.10(11) . . ?
N1 C5 C6 114.59(10) . . ?
C4 C5 C6 123.30(11) . . ?
N2 C6 C5 114.39(10) . . ?
N2 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
N2 C6 H6AB 108.7 . . ?
C5 C6 H6AB 108.7 . . ?
H6A C6 H6AB 107.6 . . ?
N3 C7 N2 117.61(11) . . ?
N3 C7 N4 126.15(11) . . ?
N2 C7 N4 116.23(11) . . ?
N3 C8 C9 123.29(13) . . ?
N3 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C8 C9 C10 116.59(13) . . ?
C8 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
N4 C10 C9 123.02(12) . . ?
N4 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C1 N1 C5 117.39(11) . . ?
C7 N2 C6 122.59(10) . . ?
C7 N2 H2A 119.8 . . ?
C6 N2 H2A 117.6 . . ?
C8 N3 C7 115.47(11) . . ?
C10 N4 C7 115.43(11) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.029
####################################################################### 
# 
# 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_d20810
_database_code_depnum_ccdc_archive 'CCDC 1961721'
loop_
_audit_author_name
_audit_author_address
'Ya-Fan Lin'
;Department of Fragrance and Cosmetic Science, Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-10-27 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 Cl2 Cu N8 O10'
_chemical_formula_sum            'C20 H18 Cl2 Cu N8 O10'
_chemical_formula_weight         664.86

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'
Cu Cu 0.3201 1.2651 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1377(5)
_cell_length_b                   9.0021(6)
_cell_length_c                   9.7827(7)
_cell_angle_alpha                106.504(2)
_cell_angle_beta                 94.684(2)
_cell_angle_gamma                93.115(2)
_cell_volume                     682.57(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.715
_cell_measurement_theta_max      24.983

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             337
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5775
_exptl_absorpt_correction_T_max  0.7769
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17191
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         25.07
_reflns_number_total             2400
_reflns_number_gt                2207
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+1.1303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2400
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1832(4) 0.6190(4) -0.0715(4) 0.0346(7) Uani 1 1 d . . .
H1 H 0.1962 0.5627 -0.1676 0.042 Uiso 1 1 calc R . .
C2 C 0.0434(4) 0.6979(4) -0.0422(4) 0.0459(9) Uani 1 1 d . . .
H2 H -0.0398 0.6957 -0.1169 0.055 Uiso 1 1 calc R . .
C3 C 0.0268(5) 0.7802(4) 0.0980(5) 0.0499(10) Uani 1 1 d . . .
H3 H -0.0684 0.8354 0.1204 0.060 Uiso 1 1 calc R . .
C4 C 0.1460(5) 0.7821(4) 0.2033(4) 0.0429(8) Uani 1 1 d . . .
H4 H 0.1348 0.8372 0.3001 0.051 Uiso 1 1 calc R . .
C5 C 0.2842(4) 0.7029(3) 0.1684(3) 0.0337(7) Uani 1 1 d . . .
C6 C 0.4279(5) 0.6994(4) 0.2793(3) 0.0414(8) Uani 1 1 d . . .
H6 H 0.4374 0.7997 0.3578 0.050 Uiso 1 1 calc R . .
C7 C 0.3848(4) 0.4236(4) 0.2678(3) 0.0315(7) Uani 1 1 d . . .
C8 C 0.3106(4) 0.1796(4) 0.2801(4) 0.0412(8) Uani 1 1 d . . .
H8 H 0.2759 0.1122 0.3332 0.049 Uiso 1 1 calc R . .
C9 C 0.3370(4) 0.1166(4) 0.1393(4) 0.0373(7) Uani 1 1 d . . .
H9 H 0.3182 0.0080 0.0939 0.045 Uiso 1 1 calc R . .
C10 C 0.3914(4) 0.2159(3) 0.0671(3) 0.0282(6) Uani 1 1 d . . .
H10 H 0.4119 0.1747 -0.0301 0.034 Uiso 1 1 calc R . .
Cu1 Cu 0.5000 0.5000 0.0000 0.02357(17) Uani 1 2 d S . .
N1 N 0.3002(3) 0.6204(3) 0.0323(3) 0.0274(5) Uani 1 1 d . . .
N2 N 0.4029(4) 0.5750(3) 0.3410(3) 0.0414(7) Uani 1 1 d . . .
N3 N 0.3315(4) 0.3304(4) 0.3445(3) 0.0408(7) Uani 1 1 d . . .
N4 N 0.4170(3) 0.3709(3) 0.1292(2) 0.0258(5) Uani 1 1 d . . .
O1 O 0.5781(3) 0.6862(3) 0.2131(2) 0.0356(5) Uani 1 1 d . . .
O2 O 1.2565(4) 0.7103(3) 0.6186(3) 0.0650(8) Uani 1 1 d . . .
O3 O 1.2565(4) 0.9404(3) 0.8025(3) 0.0615(8) Uani 1 1 d . . .
O4 O 1.0711(5) 0.8967(5) 0.6025(5) 0.1022(14) Uani 1 1 d . . .
O5 O 1.3495(6) 0.9429(4) 0.5863(4) 0.0919(13) Uani 1 1 d . . .
Cl1 Cl 1.23085(10) 0.87218(10) 0.65299(8) 0.0396(2) Uani 1 1 d . . .
H1' H 0.6750 0.7037 0.2791 0.048 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0339(16) 0.0396(18) 0.0307(16) 0.0102(14) 0.0046(13) 0.0030(13)
C2 0.0307(17) 0.047(2) 0.063(2) 0.0209(18) -0.0010(16) 0.0078(15)
C3 0.040(2) 0.043(2) 0.069(3) 0.0125(18) 0.0254(19) 0.0147(16)
C4 0.053(2) 0.0306(17) 0.047(2) 0.0068(15) 0.0282(17) 0.0066(15)
C5 0.0507(19) 0.0231(15) 0.0289(16) 0.0074(12) 0.0134(14) 0.0036(13)
C6 0.056(2) 0.0392(18) 0.0237(16) 0.0001(13) 0.0102(14) -0.0040(16)
C7 0.0323(16) 0.0381(17) 0.0209(14) 0.0032(12) -0.0013(11) 0.0089(13)
C8 0.0458(19) 0.045(2) 0.0398(19) 0.0224(16) 0.0114(15) 0.0044(15)
C9 0.0405(18) 0.0334(17) 0.0396(18) 0.0123(14) 0.0060(14) 0.0038(14)
C10 0.0271(14) 0.0308(15) 0.0252(14) 0.0044(12) 0.0048(11) 0.0047(12)
Cu1 0.0247(3) 0.0278(3) 0.0174(3) 0.00366(19) 0.00606(18) 0.00437(19)
N1 0.0309(13) 0.0296(13) 0.0220(12) 0.0067(10) 0.0069(10) 0.0039(10)
N2 0.0525(18) 0.0389(16) 0.0284(14) 0.0031(12) 0.0029(12) 0.0045(13)
N3 0.0472(17) 0.0520(18) 0.0266(14) 0.0152(13) 0.0083(12) 0.0067(13)
N4 0.0249(12) 0.0309(13) 0.0205(12) 0.0051(10) 0.0023(9) 0.0047(10)
O1 0.0317(11) 0.0444(13) 0.0230(10) -0.0021(9) 0.0059(8) -0.0044(9)
O2 0.096(2) 0.0444(16) 0.0509(17) 0.0005(13) 0.0300(16) 0.0131(15)
O3 0.084(2) 0.0602(18) 0.0299(14) -0.0046(12) 0.0034(13) 0.0106(15)
O4 0.066(2) 0.105(3) 0.108(3) -0.005(2) -0.034(2) 0.019(2)
O5 0.135(3) 0.065(2) 0.077(2) 0.0086(18) 0.063(2) -0.003(2)
Cl1 0.0463(5) 0.0410(5) 0.0258(4) -0.0016(3) 0.0082(3) 0.0070(4)

_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
C1 N1 1.331(4) . ?
C1 C2 1.381(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.352(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.348(4) . ?
C5 C6 1.537(5) . ?
C6 O1 1.425(4) . ?
C6 N2 1.428(5) . ?
C6 H6 1.0000 . ?
C7 N2 1.341(4) . ?
C7 N3 1.351(4) . ?
C7 N4 1.356(4) . ?
C8 N3 1.319(5) . ?
C8 C9 1.372(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.364(4) . ?
C9 H9 0.9500 . ?
C10 N4 1.351(4) . ?
C10 H10 0.9500 . ?
Cu1 N1 2.000(2) 2_665 ?
Cu1 N1 2.000(2) . ?
Cu1 N4 2.071(2) 2_665 ?
Cu1 N4 2.071(2) . ?
Cu1 O1 2.289(2) . ?
Cu1 O1 2.289(2) 2_665 ?
O1 H1' 0.9534 . ?
O2 Cl1 1.431(3) . ?
O3 Cl1 1.409(3) . ?
O4 Cl1 1.404(4) . ?
O5 Cl1 1.426(3) . ?

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
N1 C1 C2 121.3(3) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 118.7(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.3(3) . . ?
N1 C5 C6 115.4(3) . . ?
C4 C5 C6 123.3(3) . . ?
O1 C6 N2 109.8(3) . . ?
O1 C6 C5 109.3(2) . . ?
N2 C6 C5 112.3(3) . . ?
O1 C6 H6 108.4 . . ?
N2 C6 H6 108.4 . . ?
C5 C6 H6 108.4 . . ?
N2 C7 N3 113.9(3) . . ?
N2 C7 N4 122.3(3) . . ?
N3 C7 N4 123.8(3) . . ?
N3 C8 C9 122.4(3) . . ?
N3 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C10 C9 C8 117.4(3) . . ?
C10 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
N4 C10 C9 122.3(3) . . ?
N4 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
N1 Cu1 N1 180.00(7) 2_665 . ?
N1 Cu1 N4 88.95(9) 2_665 2_665 ?
N1 Cu1 N4 91.05(9) . 2_665 ?
N1 Cu1 N4 91.05(9) 2_665 . ?
N1 Cu1 N4 88.95(9) . . ?
N4 Cu1 N4 180.000(1) 2_665 . ?
N1 Cu1 O1 102.89(9) 2_665 . ?
N1 Cu1 O1 77.11(9) . . ?
N4 Cu1 O1 96.00(9) 2_665 . ?
N4 Cu1 O1 84.00(9) . . ?
N1 Cu1 O1 77.11(9) 2_665 2_665 ?
N1 Cu1 O1 102.89(9) . 2_665 ?
N4 Cu1 O1 84.00(9) 2_665 2_665 ?
N4 Cu1 O1 96.00(9) . 2_665 ?
O1 Cu1 O1 180.0 . 2_665 ?
C1 N1 C5 119.6(3) . . ?
C1 N1 Cu1 123.6(2) . . ?
C5 N1 Cu1 116.8(2) . . ?
C7 N2 C6 125.2(3) . . ?
C8 N3 C7 117.7(3) . . ?
C10 N4 C7 116.4(3) . . ?
C10 N4 Cu1 115.83(19) . . ?
C7 N4 Cu1 127.8(2) . . ?
C6 O1 Cu1 101.97(17) . . ?
C6 O1 H1' 113.9 . . ?
Cu1 O1 H1' 132.2 . . ?
O4 Cl1 O3 109.4(2) . . ?
O4 Cl1 O5 109.2(3) . . ?
O3 Cl1 O5 109.1(2) . . ?
O4 Cl1 O2 111.7(2) . . ?
O3 Cl1 O2 109.96(19) . . ?
O5 Cl1 O2 107.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.069
