# 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 2024

####################################################################### 
# 
# 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_swj-1
_database_code_depnum_ccdc_archive 'CCDC 2295513'
loop_
_audit_author_name
_audit_author_address
'JIanchun wang'
;Capital Normal University
China
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_audit_creation_date             2020-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H14 N6 O'
_chemical_formula_sum            'C14 H14 N6 O'
_chemical_formula_weight         282.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   8.18010(10)
_cell_length_b                   17.2524(2)
_cell_length_c                   9.19780(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.3620(10)
_cell_angle_gamma                90
_cell_volume                     1272.61(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6423
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1880
_cell_measurement_theta_min      5.1390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6457
_diffrn_reflns_point_group_measured_fraction_full 0.706
_diffrn_reflns_point_group_measured_fraction_max 0.728
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.572
_diffrn_reflns_theta_min         5.536
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  89.00   0.50    0.50    --    0.00  37.00-150.00  204
  2  ω    -89.00   9.00   0.50    0.50    --    0.00 -19.00-120.00  196
  3  ω    -29.00  89.00   0.50    0.50    --    0.00  82.00-180.00  236
  4  ω    -89.00  27.00   0.50    0.50    --    0.00 -77.00   0.00  232
  5  ω    -89.00  13.00   0.50    0.50    --    0.00 -37.00  60.00  204
  6  ω     62.00 123.00   0.50    1.00    --   94.00 -82.00-120.00  122
  7  ω      5.00 104.00   0.50    1.00    --   94.00 -30.00 -30.00  198
  8  ω      6.00 101.00   0.50    1.00    --   94.00 -61.00-150.00  190
  9  ω     76.00 168.00   0.50    1.00    --   94.00  55.00 -38.86  184
 10  ω     46.00 115.00   0.50    1.00    --   94.00 -82.00   0.00  138
 11  ω     12.00 122.00   0.50    1.00    --   94.00 -82.00 120.00  220
 12  ω      5.00  38.00   0.50    1.00    --   94.00 -77.00  90.00   66
 13  ω     61.00  87.00   0.50    1.00    --   94.00 -61.00 120.00   52
 14  ω      5.00 100.00   0.50    1.00    --   94.00 -82.00-150.00  190
 15  ω    121.00 182.00   0.50    1.00    --   94.00  30.00  60.00  122
 16  ω      5.00  50.00   0.50    1.00    --   94.00 -61.00 120.00   90
 17  ω     83.00 115.00   0.50    1.00    --   94.00 -61.00-120.00   64
 18  ω      6.00  97.00   0.50    1.00    --   94.00 -61.00   0.00  182
 19  ω     97.00 123.00   0.50    1.00    --   94.00 -82.00  30.00   52
 20  ω     79.00 180.00   0.50    1.00    --   94.00  45.00 -60.00  202
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0494204000
_diffrn_orient_matrix_UB_12      -0.0832998000
_diffrn_orient_matrix_UB_13      -0.0509861000
_diffrn_orient_matrix_UB_21      -0.0455446000
_diffrn_orient_matrix_UB_22      0.0280781000
_diffrn_orient_matrix_UB_23      -0.1619158000
_diffrn_orient_matrix_UB_31      0.1799428000
_diffrn_orient_matrix_UB_32      -0.0157612000
_diffrn_orient_matrix_UB_33      -0.0190950000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.474
_reflns_Friedel_fraction_full    0.456
_reflns_Friedel_fraction_max     0.471
_reflns_number_gt                1610
_reflns_number_total             1623
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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         0.185
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1623
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.056
_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)+(0.0777P)²+0.0863P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C8(H8), C9(H9), C7(H7)
;
_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 0.6248(2) 0.64275(9) 0.6597(2) 0.0172(4) Uani 1 1 d . . . . .
N6 N 0.4501(3) 0.23197(11) 0.4939(2) 0.0130(5) Uani 1 1 d . . . . .
N1 N 0.4984(3) 0.52793(12) 0.6889(2) 0.0172(5) Uani 1 1 d . . . . .
N2 N 0.4830(3) 0.45438(12) 0.6488(2) 0.0158(5) Uani 1 1 d . . . . .
N5 N 0.5339(3) 0.35255(12) 0.4963(2) 0.0139(5) Uani 1 1 d . . . . .
N3 N 0.6115(3) 0.47848(12) 0.4435(2) 0.0165(5) Uani 1 1 d . . . . .
N4 N 0.6312(3) 0.55262(12) 0.4808(2) 0.0177(5) Uani 1 1 d . . . . .
C4 C 0.5903(3) 0.23319(14) 0.4281(3) 0.0136(5) Uani 1 1 d . . . . .
C5 C 0.6447(3) 0.30999(14) 0.4278(3) 0.0136(5) Uani 1 1 d . . . . .
C6 C 0.7823(4) 0.33128(15) 0.3698(3) 0.0170(6) Uani 1 1 d . . . . .
H6 H 0.8179 0.3825 0.3700 0.020 Uiso 1 1 calc R . . . .
C1 C 0.5879(3) 0.57599(14) 0.6126(3) 0.0134(5) Uani 1 1 d . . . . .
C2 C 0.5469(3) 0.43303(14) 0.5336(3) 0.0136(5) Uani 1 1 d . . . . .
C10 C 0.3363(3) 0.16514(13) 0.4977(3) 0.0140(5) Uani 1 1 d . . . . .
H10 H 0.2760 0.1554 0.3962 0.017 Uiso 1 1 calc R . . . .
C3 C 0.4197(3) 0.30446(14) 0.5333(3) 0.0129(5) Uani 1 1 d . . . . .
H3 H 0.3329 0.3192 0.5791 0.015 Uiso 1 1 calc R . . . .
C8 C 0.8104(4) 0.19490(16) 0.3118(3) 0.0200(6) Uani 1 1 d . . . . .
H8 H 0.8687 0.1569 0.2714 0.024 Uiso 1 1 calc R . . . .
C9 C 0.6739(3) 0.17372(15) 0.3700(3) 0.0164(6) Uani 1 1 d . . . . .
H9 H 0.6394 0.1224 0.3707 0.020 Uiso 1 1 calc R . . . .
C11 C 0.4253(3) 0.08953(15) 0.5580(3) 0.0193(6) Uani 1 1 d . . . . .
H11A H 0.4600 0.0603 0.4792 0.023 Uiso 1 1 calc R . . . .
H11B H 0.5224 0.1005 0.6345 0.023 Uiso 1 1 calc R . . . .
C14 C 0.2089(4) 0.17869(14) 0.5946(3) 0.0172(6) Uani 1 1 d . . . . .
H14A H 0.1231 0.2148 0.5489 0.021 Uiso 1 1 calc R . . . .
H14B H 0.2611 0.1978 0.6919 0.021 Uiso 1 1 calc R . . . .
C13 C 0.1384(3) 0.09680(15) 0.6035(3) 0.0193(6) Uani 1 1 d . . . . .
H13A H 0.0592 0.0840 0.5136 0.023 Uiso 1 1 calc R . . . .
H13B H 0.0839 0.0919 0.6877 0.023 Uiso 1 1 calc R . . . .
C12 C 0.2934(4) 0.04482(16) 0.6220(3) 0.0242(7) Uani 1 1 d . . . . .
H12A H 0.2665 -0.0036 0.5692 0.029 Uiso 1 1 calc R . . . .
H12B H 0.3345 0.0333 0.7260 0.029 Uiso 1 1 calc R . . . .
C7 C 0.8634(3) 0.27215(16) 0.3117(3) 0.0207(6) Uani 1 1 d . . . . .
H7 H 0.9560 0.2839 0.2714 0.025 Uiso 1 1 calc R . . . .


_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 C1 1.247(3) . ?
N6 C4 1.399(3) . ?
N6 C10 1.486(3) . ?
N6 C3 1.339(3) . ?
N1 N2 1.320(3) . ?
N1 C1 1.385(3) . ?
N2 C2 1.323(3) . ?
N5 C5 1.408(3) . ?
N5 C2 1.429(3) . ?
N5 C3 1.342(3) . ?
N3 N4 1.326(3) . ?
N3 C2 1.324(4) . ?
N4 C1 1.388(4) . ?
C4 C5 1.398(3) . ?
C4 C9 1.396(4) . ?
C5 C6 1.386(4) . ?
C6 C7 1.381(4) . ?
C10 C11 1.543(3) . ?
C10 C14 1.517(4) . ?
C8 C9 1.379(4) . ?
C8 C7 1.402(4) . ?
C11 C12 1.535(4) . ?
C14 C13 1.534(4) . ?
C13 C12 1.535(4) . ?

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
C4 N6 C10 126.3(2) . . ?
C3 N6 C4 108.3(2) . . ?
C3 N6 C10 124.6(2) . . ?
N2 N1 C1 117.7(2) . . ?
N1 N2 C2 117.4(2) . . ?
C5 N5 C2 126.2(2) . . ?
C3 N5 C5 109.4(2) . . ?
C3 N5 C2 124.2(2) . . ?
C2 N3 N4 116.9(2) . . ?
N3 N4 C1 117.9(2) . . ?
C5 C4 N6 107.7(2) . . ?
C9 C4 N6 131.3(2) . . ?
C9 C4 C5 121.1(2) . . ?
C4 C5 N5 105.1(2) . . ?
C6 C5 N5 132.6(2) . . ?
C6 C5 C4 122.3(2) . . ?
C7 C6 C5 116.2(2) . . ?
O1 C1 N1 119.5(2) . . ?
O1 C1 N4 119.1(2) . . ?
N1 C1 N4 121.3(2) . . ?
N2 C2 N5 116.1(2) . . ?
N2 C2 N3 127.3(2) . . ?
N3 C2 N5 116.5(2) . . ?
N6 C10 C11 114.3(2) . . ?
N6 C10 C14 113.6(2) . . ?
C14 C10 C11 104.4(2) . . ?
N6 C3 N5 109.5(2) . . ?
C9 C8 C7 121.7(2) . . ?
C8 C9 C4 116.7(2) . . ?
C12 C11 C10 104.2(2) . . ?
C10 C14 C13 101.5(2) . . ?
C14 C13 C12 103.5(2) . . ?
C13 C12 C11 107.0(2) . . ?
C6 C7 C8 122.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.892
_oxdiff_exptl_absorpt_empirical_full_min 0.377
####################################################################### 
# 
# 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_swj-3
_database_code_depnum_ccdc_archive 'CCDC 2295519'
loop_
_audit_author_name
_audit_author_address
'JIanchun wang'
;Capital Normal University
China
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_audit_creation_date             2021-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H10 N6 O, C4 H8 O'
_chemical_formula_sum            'C19 H18 N6 O2'
_chemical_formula_weight         362.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 H1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.0018(9)
_cell_length_b                   10.3586(5)
_cell_length_c                   12.8117(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.501(7)
_cell_angle_gamma                90
_cell_volume                     1790.61(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4187
_cell_measurement_temperature    294.61(10)
_cell_measurement_theta_max      69.7760
_cell_measurement_theta_min      5.3610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.22a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9859
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.559
_diffrn_reflns_theta_min         5.384
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.61(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  20.00   0.50    1.00    --    0.00 -57.00 -30.00  218
  2  ω     21.00  88.00   0.50    1.00    --    0.00  19.00 -30.00  134
  3  ω     23.00  88.00   0.50    1.00    --    0.00  19.00-120.00  130
  4  ω     20.00  46.00   0.50    1.00    --    0.00  37.00   0.00   52
  5  ω      5.00  50.00   0.50    7.00    --   94.00 -15.00   0.00   90
  6  ω     21.00  46.00   0.50    7.00    --   94.00 -61.00 150.00   50
  7  ω     81.00 183.00   0.50    7.00    --   94.00  45.00 -90.00  204
  8  ω     79.00 174.00   0.50    7.00    --   94.00  61.00 120.00  190
  9  ω     39.00 104.00   0.50    7.00    --   94.00 -30.00   0.00  130
 10  ω     85.00 120.00   0.50    7.00    --   94.00  15.00 -90.00   70
 11  ω     61.00 109.00   0.50    7.00    --   94.00 -61.00 150.00   96
 12  ω      5.00 101.00   0.50    7.00    --   94.00 -45.00   0.00  192
 13  ω    104.00 129.00   0.50    7.00    --   94.00  77.00 -30.00   50
 14  ω     77.00 102.00   0.50    7.00    --   94.00  77.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1114107000
_diffrn_orient_matrix_UB_12      0.0270713000
_diffrn_orient_matrix_UB_13      -0.0468164000
_diffrn_orient_matrix_UB_21      0.0246878000
_diffrn_orient_matrix_UB_22      0.1133886000
_diffrn_orient_matrix_UB_23      -0.0660527000
_diffrn_orient_matrix_UB_31      -0.0023710000
_diffrn_orient_matrix_UB_32      -0.0923475000
_diffrn_orient_matrix_UB_33      -0.0950244000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2127
_reflns_number_total             3158
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_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         0.477
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0954
_refine_ls_restrained_S_all      1.056
_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)+(0.1493P)²+0.9538P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2801
_refine_ls_wR_factor_ref         0.2988
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O6-C3
 2.1 with sigma of 0.002
 C3-C0AA
 1.4 with sigma of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B), C0AA(H0AA,H0AB), C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00F(H00F), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M)
;
_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
N001 N 0.5366(2) 0.2221(3) 0.3741(2) 0.0699(8) Uani 1 1 d . . . . .
N002 N 0.6272(2) 0.2258(3) 0.2624(2) 0.0743(8) Uani 1 1 d . . . . .
N003 N 0.4616(2) 0.1798(3) 0.5123(3) 0.0826(10) Uani 1 1 d . . . . .
O004 O 0.3696(3) 0.3988(3) 0.6583(3) 0.1130(12) Uani 1 1 d . . . . .
N005 N 0.4136(2) 0.2207(3) 0.5820(3) 0.0849(10) Uani 1 1 d . . . . .
N006 N 0.4364(3) 0.3766(3) 0.4215(3) 0.1091(14) Uani 1 1 d . . . . .
C007 C 0.4774(3) 0.2630(3) 0.4422(3) 0.0707(9) Uani 1 1 d . . . . .
C008 C 0.5763(3) 0.2975(3) 0.3144(3) 0.0743(10) Uani 1 1 d . . . . .
H008 H 0.5696 0.3868 0.3094 0.089 Uiso 1 1 calc R . . . .
C009 C 0.3914(3) 0.3492(4) 0.5805(3) 0.0808(11) Uani 1 1 d . . . . .
N00A N 0.3889(4) 0.4208(4) 0.4902(3) 0.1152(15) Uani 1 1 d . . . . .
C00B C 0.6817(3) 0.2713(4) 0.1890(3) 0.0762(10) Uani 1 1 d . . . . .
C00C C 0.6188(3) 0.0982(3) 0.2918(4) 0.0861(12) Uani 1 1 d . . . . .
H00C H 0.6470 0.0271 0.2672 0.103 Uiso 1 1 calc R . . . .
C00D C 0.5637(3) 0.0957(3) 0.3609(4) 0.0855(12) Uani 1 1 d . . . . .
H00D H 0.5463 0.0230 0.3943 0.103 Uiso 1 1 calc R . . . .
C00E C 0.7738(3) 0.2331(5) 0.0592(3) 0.0873(12) Uani 1 1 d . . . . .
C00F C 0.7166(3) 0.1879(4) 0.1272(3) 0.0814(11) Uani 1 1 d . . . . .
H00F H 0.7031 0.1002 0.1295 0.098 Uiso 1 1 calc R . . . .
C00G C 0.7939(4) 0.3637(5) 0.0561(3) 0.0970(13) Uani 1 1 d . . . . .
C00H C 0.7534(4) 0.4485(5) 0.1191(4) 0.1129(16) Uani 1 1 d . . . . .
H00H H 0.7641 0.5368 0.1152 0.136 Uiso 1 1 calc R . . . .
C00I C 0.6995(4) 0.4047(4) 0.1853(4) 0.0999(14) Uani 1 1 d . . . . .
H00I H 0.6746 0.4619 0.2275 0.120 Uiso 1 1 calc R . . . .
C00J C 0.8116(4) 0.1484(5) -0.0075(4) 0.1101(16) Uani 1 1 d . . . . .
H00J H 0.7969 0.0608 -0.0081 0.132 Uiso 1 1 calc R . . . .
C00K C 0.8682(4) 0.1928(7) -0.0697(4) 0.1169(17) Uani 1 1 d . . . . .
H00K H 0.8930 0.1356 -0.1120 0.140 Uiso 1 1 calc R . . . .
C00L C 0.8530(4) 0.4087(6) -0.0105(4) 0.1189(17) Uani 1 1 d . . . . .
H00L H 0.8668 0.4963 -0.0129 0.143 Uiso 1 1 calc R . . . .
C00M C 0.8897(4) 0.3231(7) -0.0711(4) 0.125(2) Uani 1 1 d . . . . .
H00M H 0.9295 0.3527 -0.1137 0.150 Uiso 1 1 calc R . . . .
O6 O 1.1412(13) 0.1254(11) -0.2340(15) 0.508(17) Uani 1 1 d D . . . .
C3 C 1.0572(6) 0.2954(12) -0.2708(11) 0.240(5) Uani 1 1 d D . . . .
H3A H 1.0428 0.3858 -0.2623 0.287 Uiso 1 1 calc R . . . .
H3B H 0.9956 0.2509 -0.3035 0.287 Uiso 1 1 calc R . . . .
C1 C 1.1249(8) 0.2822(13) -0.3374(7) 0.220(4) Uani 1 1 d . . . . .
H1A H 1.1541 0.3647 -0.3472 0.264 Uiso 1 1 calc R . . . .
H1B H 1.0915 0.2469 -0.4079 0.264 Uiso 1 1 calc R . . . .
C0AA C 1.1038(10) 0.2407(18) -0.1702(8) 0.378(15) Uani 1 1 d D . . . .
H0AA H 1.0583 0.2132 -0.1292 0.454 Uiso 1 1 calc R . . . .
H0AB H 1.1570 0.2930 -0.1261 0.454 Uiso 1 1 calc R . . . .
C2 C 1.2005(9) 0.1922(13) -0.2758(13) 0.254(6) Uani 1 1 d . . . . .
H2A H 1.2299 0.1406 -0.3223 0.305 Uiso 1 1 calc R . . . .
H2B H 1.2520 0.2355 -0.2213 0.305 Uiso 1 1 calc R . . . .


_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
N001 C007 1.419(4) . ?
N001 C008 1.316(4) . ?
N001 C00D 1.386(4) . ?
N002 C008 1.327(4) . ?
N002 C00B 1.440(5) . ?
N002 C00C 1.387(5) . ?
N003 N005 1.322(4) . ?
N003 C007 1.306(5) . ?
O004 C009 1.230(4) . ?
N005 C009 1.366(5) . ?
N006 C007 1.305(5) . ?
N006 N00A 1.319(5) . ?
C009 N00A 1.366(5) . ?
C00B C00F 1.349(5) . ?
C00B C00I 1.407(6) . ?
C00C C00D 1.322(6) . ?
C00E C00F 1.412(6) . ?
C00E C00G 1.385(7) . ?
C00E C00J 1.421(6) . ?
C00G C00H 1.410(6) . ?
C00G C00L 1.417(6) . ?
C00H C00I 1.356(6) . ?
C00J C00K 1.347(7) . ?
C00K C00M 1.384(8) . ?
C00L C00M 1.367(8) . ?
O6 C0AA 1.612(17) . ?
O6 C2 1.301(16) . ?
C3 C1 1.441(12) . ?
C3 C0AA 1.399(2) . ?
C1 C2 1.472(13) . ?

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
C008 N001 C007 125.9(3) . . ?
C008 N001 C00D 108.6(3) . . ?
C00D N001 C007 125.5(3) . . ?
C008 N002 C00B 126.5(3) . . ?
C008 N002 C00C 107.6(3) . . ?
C00C N002 C00B 126.0(3) . . ?
C007 N003 N005 117.6(3) . . ?
N003 N005 C009 117.2(3) . . ?
C007 N006 N00A 116.8(3) . . ?
N003 C007 N001 117.4(3) . . ?
N003 C007 N006 126.0(4) . . ?
N006 C007 N001 116.3(3) . . ?
N001 C008 N002 109.1(3) . . ?
O004 C009 N005 120.0(4) . . ?
O004 C009 N00A 120.2(4) . . ?
N00A C009 N005 119.7(4) . . ?
N006 N00A C009 118.2(3) . . ?
C00F C00B N002 120.8(3) . . ?
C00F C00B C00I 121.0(4) . . ?
C00I C00B N002 118.2(3) . . ?
C00D C00C N002 107.9(3) . . ?
C00C C00D N001 106.9(3) . . ?
C00F C00E C00J 122.0(4) . . ?
C00G C00E C00F 119.7(4) . . ?
C00G C00E C00J 118.4(4) . . ?
C00B C00F C00E 120.2(4) . . ?
C00E C00G C00H 118.5(4) . . ?
C00E C00G C00L 119.6(5) . . ?
C00H C00G C00L 121.9(5) . . ?
C00I C00H C00G 121.7(4) . . ?
C00H C00I C00B 118.9(4) . . ?
C00K C00J C00E 121.2(5) . . ?
C00J C00K C00M 120.3(5) . . ?
C00M C00L C00G 119.9(5) . . ?
C00L C00M C00K 120.6(5) . . ?
C2 O6 C0AA 98.3(13) . . ?
C0AA C3 C1 106.8(8) . . ?
C3 C1 C2 103.6(9) . . ?
C3 C0AA O6 88.1(7) . . ?
O6 C2 C1 96.3(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.063
_oxdiff_exptl_absorpt_empirical_full_min 0.311
####################################################################### 
# 
# 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_swj-10
_database_code_depnum_ccdc_archive 'CCDC 2295520'
loop_
_audit_author_name
_audit_author_address
'JIanchun wang'
;Capital Normal University
China
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_audit_creation_date             2021-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C15 H16 N6 O)'
_chemical_formula_sum            'C30 H32 N12 O2'
_chemical_formula_weight         592.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 H1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.2325(2)
_cell_length_b                   18.0052(2)
_cell_length_c                   18.4076(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5711.41(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12978
_cell_measurement_temperature    294.44(13)
_cell_measurement_theta_max      74.3310
_cell_measurement_theta_min      4.8030
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.752
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.22a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22144
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.678
_diffrn_reflns_theta_min         4.287
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.44(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  60.00   0.50    1.00    --    0.00  19.00 150.00  136
  2  ω     16.00  88.00   0.50    1.00    --    0.00  19.00-150.00  144
  3  ω    -89.00 -39.00   0.50    1.00    --    0.00 -82.00 150.00  100
  4  ω     10.00 110.00   0.50    3.00    --   94.00 -45.00-120.00  200
  5  ω    107.00 173.00   0.50    3.00    --   94.00  30.00  60.00  132
  6  ω     32.00 102.00   0.50    3.00    --   94.00 -15.00-120.00  140
  7  ω     86.00 120.00   0.50    3.00    --   94.00 -82.00  30.00   68
  8  ω     24.00  55.00   0.50    3.00    --   94.00 -82.00  30.00   62
  9  ω     93.00 121.00   0.50    3.00    --   94.00 -77.00  60.00   56
 10  ω     46.00  83.00   0.50    3.00    --   94.00 -77.00  60.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0236237000
_diffrn_orient_matrix_UB_12      -0.0290231000
_diffrn_orient_matrix_UB_13      -0.0755325000
_diffrn_orient_matrix_UB_21      -0.0703269000
_diffrn_orient_matrix_UB_22      0.0528312000
_diffrn_orient_matrix_UB_23      -0.0001227000
_diffrn_orient_matrix_UB_31      0.0498008000
_diffrn_orient_matrix_UB_32      0.0607549000
_diffrn_orient_matrix_UB_33      -0.0360916000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5071
_reflns_number_total             5712
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_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         0.234
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0640P)²+0.9345P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C30(H30A,H30B), C14(H14A,H14B), C15(H15A,H15B), C27(H27A,
 H27B), C29(H29A,H29B), C11(H11A,H11B), C28(H28A,H28B), C13(H13A,H13B),
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C20(H20), C23(H23), C18(H18), C21(H21), C22(H22), C5(H5), C8(H8),
 C6(H6), C7(H7)
;
_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
N9 N 0.38228(6) 0.59127(5) 0.46064(5) 0.0360(2) Uani 1 1 d . . . . .
O2 O 0.31071(7) 0.66328(6) 0.65089(6) 0.0640(3) Uani 1 1 d . . . . .
N11 N 0.34189(6) 0.41335(6) 0.78838(5) 0.0398(2) Uani 1 1 d . . . . .
N10 N 0.37016(6) 0.71186(6) 0.45245(5) 0.0400(2) Uani 1 1 d . . . . .
N12 N 0.36874(6) 0.29540(6) 0.80031(5) 0.0405(2) Uani 1 1 d . . . . .
N4 N 0.43269(7) 0.51927(6) 0.55432(6) 0.0449(3) Uani 1 1 d . . . . .
N6 N 0.29925(7) 0.47667(6) 0.68528(6) 0.0457(3) Uani 1 1 d . . . . .
N8 N 0.32530(8) 0.54202(6) 0.79355(6) 0.0490(3) Uani 1 1 d . . . . .
N5 N 0.28743(7) 0.53946(7) 0.65052(6) 0.0499(3) Uani 1 1 d . . . . .
N3 N 0.44050(7) 0.45501(7) 0.58707(6) 0.0515(3) Uani 1 1 d . . . . .
N2 N 0.36438(8) 0.46269(6) 0.45746(6) 0.0501(3) Uani 1 1 d . . . . .
N7 N 0.31199(8) 0.60588(6) 0.76042(6) 0.0526(3) Uani 1 1 d . . . . .
O1 O 0.40431(11) 0.33435(6) 0.58987(6) 0.0918(5) Uani 1 1 d . . . . .
N1 N 0.37244(9) 0.39685(6) 0.48790(7) 0.0575(3) Uani 1 1 d . . . . .
C4 C 0.37263(7) 0.60734(7) 0.38677(6) 0.0371(3) Uani 1 1 d . . . . .
C19 C 0.33411(7) 0.39713(7) 0.86271(6) 0.0376(3) Uani 1 1 d . . . . .
C17 C 0.32433(7) 0.48182(7) 0.75328(6) 0.0378(3) Uani 1 1 d . . . . .
C2 C 0.39215(7) 0.52002(6) 0.49324(6) 0.0363(3) Uani 1 1 d . . . . .
C9 C 0.36474(7) 0.68404(7) 0.38205(6) 0.0383(3) Uani 1 1 d . . . . .
C24 C 0.35133(7) 0.32211(7) 0.86987(6) 0.0386(3) Uani 1 1 d . . . . .
C3 C 0.37996(8) 0.65516(7) 0.49759(6) 0.0400(3) Uani 1 1 d . . . . .
H3 H 0.3845 0.6593 0.5478 0.048 Uiso 1 1 calc R . . . .
C20 C 0.31134(8) 0.43979(8) 0.92202(6) 0.0426(3) Uani 1 1 d . . . . .
H20 H 0.2991 0.4899 0.9174 0.051 Uiso 1 1 calc R . . . .
C10 C 0.37256(8) 0.79188(7) 0.47074(7) 0.0429(3) Uani 1 1 d . . . . .
H10 H 0.3486 0.8193 0.4305 0.052 Uiso 1 1 calc R . . . .
C25 C 0.38987(7) 0.21735(7) 0.78524(6) 0.0397(3) Uani 1 1 d . . . . .
H25 H 0.3542 0.1857 0.8128 0.048 Uiso 1 1 calc R . . . .
C23 C 0.34791(8) 0.28592(8) 0.93660(7) 0.0444(3) Uani 1 1 d . . . . .
H23 H 0.3595 0.2357 0.9413 0.053 Uiso 1 1 calc R . . . .
C18 C 0.36260(8) 0.35110(7) 0.75349(7) 0.0424(3) Uani 1 1 d . . . . .
H18 H 0.3714 0.3475 0.7038 0.051 Uiso 1 1 calc R . . . .
C16 C 0.30523(8) 0.60504(7) 0.68565(7) 0.0449(3) Uani 1 1 d . . . . .
C21 C 0.30786(8) 0.40377(8) 0.98816(7) 0.0460(3) Uani 1 1 d . . . . .
H21 H 0.2928 0.4303 1.0291 0.055 Uiso 1 1 calc R . . . .
C22 C 0.32639(8) 0.32857(8) 0.99527(7) 0.0472(3) Uani 1 1 d . . . . .
H22 H 0.3241 0.3067 1.0410 0.057 Uiso 1 1 calc R . . . .
C5 C 0.37024(9) 0.56276(8) 0.32552(7) 0.0477(3) Uani 1 1 d . . . . .
H5 H 0.3761 0.5115 0.3284 0.057 Uiso 1 1 calc R . . . .
C8 C 0.35197(9) 0.71967(8) 0.31596(7) 0.0489(3) Uani 1 1 d . . . . .
H8 H 0.3458 0.7709 0.3129 0.059 Uiso 1 1 calc R . . . .
C26 C 0.47171(8) 0.20057(8) 0.81153(8) 0.0511(3) Uani 1 1 d . . . . .
H26A H 0.5087 0.2305 0.7847 0.061 Uiso 1 1 calc R . . . .
H26B H 0.4762 0.2130 0.8626 0.061 Uiso 1 1 calc R . . . .
C1 C 0.40537(10) 0.39336(8) 0.55636(7) 0.0527(4) Uani 1 1 d . . . . .
C30 C 0.38070(9) 0.19787(7) 0.70547(7) 0.0486(3) Uani 1 1 d . . . . .
H30A H 0.4153 0.2282 0.6764 0.058 Uiso 1 1 calc R . . . .
H30B H 0.3279 0.2078 0.6900 0.058 Uiso 1 1 calc R . . . .
C14 C 0.33234(9) 0.89259(8) 0.55448(8) 0.0516(3) Uani 1 1 d . . . . .
H14A H 0.3065 0.9196 0.5158 0.062 Uiso 1 1 calc R . . . .
H14B H 0.3054 0.9033 0.5996 0.062 Uiso 1 1 calc R . . . .
C15 C 0.32779(9) 0.80968(8) 0.53892(8) 0.0525(3) Uani 1 1 d . . . . .
H15A H 0.3492 0.7821 0.5795 0.063 Uiso 1 1 calc R . . . .
H15B H 0.2740 0.7950 0.5330 0.063 Uiso 1 1 calc R . . . .
C27 C 0.48963(9) 0.11872(9) 0.80048(8) 0.0567(4) Uani 1 1 d . . . . .
H27A H 0.5425 0.1088 0.8157 0.068 Uiso 1 1 calc R . . . .
H27B H 0.4552 0.0891 0.8305 0.068 Uiso 1 1 calc R . . . .
C29 C 0.39961(10) 0.11604(8) 0.69421(9) 0.0572(4) Uani 1 1 d . . . . .
H29A H 0.3615 0.0860 0.7196 0.069 Uiso 1 1 calc R . . . .
H29B H 0.3962 0.1044 0.6429 0.069 Uiso 1 1 calc R . . . .
C6 C 0.35868(10) 0.59818(9) 0.26002(7) 0.0567(4) Uani 1 1 d . . . . .
H6 H 0.3574 0.5701 0.2176 0.068 Uiso 1 1 calc R . . . .
C11 C 0.45650(9) 0.81672(8) 0.47655(10) 0.0611(4) Uani 1 1 d . . . . .
H11A H 0.4832 0.8064 0.4313 0.073 Uiso 1 1 calc R . . . .
H11B H 0.4821 0.7891 0.5149 0.073 Uiso 1 1 calc R . . . .
C7 C 0.34891(10) 0.67515(9) 0.25566(7) 0.0576(4) Uani 1 1 d . . . . .
H7 H 0.3401 0.6968 0.2105 0.069 Uiso 1 1 calc R . . . .
C28 C 0.47978(10) 0.09640(9) 0.72143(9) 0.0597(4) Uani 1 1 d . . . . .
H28A H 0.5184 0.1216 0.6921 0.072 Uiso 1 1 calc R . . . .
H28B H 0.4880 0.0433 0.7166 0.072 Uiso 1 1 calc R . . . .
C13 C 0.41539(11) 0.91867(9) 0.56031(10) 0.0666(4) Uani 1 1 d . . . . .
H13A H 0.4162 0.9720 0.5676 0.080 Uiso 1 1 calc R . . . .
H13B H 0.4396 0.8956 0.6022 0.080 Uiso 1 1 calc R . . . .
C12 C 0.46107(11) 0.89965(9) 0.49302(12) 0.0766(6) Uani 1 1 d . . . . .
H12A H 0.5149 0.9138 0.4999 0.092 Uiso 1 1 calc R . . . .
H12B H 0.4408 0.9275 0.4521 0.092 Uiso 1 1 calc R . . . .


_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
N9 C4 1.4001(14) . ?
N9 C2 1.4265(14) . ?
N9 C3 1.3371(15) . ?
O2 C16 1.2320(16) . ?
N11 C19 1.4054(14) . ?
N11 C17 1.4243(15) . ?
N11 C18 1.3402(16) . ?
N10 C9 1.3924(15) . ?
N10 C3 1.3270(15) . ?
N10 C10 1.4802(15) . ?
N12 C24 1.4002(15) . ?
N12 C25 1.4780(15) . ?
N12 C18 1.3264(15) . ?
N4 N3 1.3115(15) . ?
N4 C2 1.3236(16) . ?
N6 N5 1.3148(15) . ?
N6 C17 1.3275(15) . ?
N8 N7 1.3216(15) . ?
N8 C17 1.3134(16) . ?
N5 C16 1.3807(18) . ?
N3 C1 1.385(2) . ?
N2 N1 1.3185(15) . ?
N2 C2 1.3148(16) . ?
N7 C16 1.3813(17) . ?
O1 C1 1.2288(17) . ?
N1 C1 1.3836(19) . ?
C4 C9 1.3903(17) . ?
C4 C5 1.3845(17) . ?
C19 C24 1.3894(17) . ?
C19 C20 1.3913(17) . ?
C9 C8 1.3929(17) . ?
C24 C23 1.3917(16) . ?
C20 C21 1.3807(18) . ?
C10 C15 1.5078(18) . ?
C10 C11 1.518(2) . ?
C25 C26 1.5212(18) . ?
C25 C30 1.5180(17) . ?
C23 C22 1.3761(19) . ?
C21 C22 1.397(2) . ?
C5 C6 1.3786(19) . ?
C8 C7 1.370(2) . ?
C26 C27 1.520(2) . ?
C30 C29 1.5231(19) . ?
C14 C15 1.5219(19) . ?
C14 C13 1.510(2) . ?
C27 C28 1.519(2) . ?
C29 C28 1.511(2) . ?
C6 C7 1.398(2) . ?
C11 C12 1.526(2) . ?
C13 C12 1.507(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
C4 N9 C2 127.50(10) . . ?
C3 N9 C4 108.22(10) . . ?
C3 N9 C2 124.28(10) . . ?
C19 N11 C17 126.96(10) . . ?
C18 N11 C19 108.55(10) . . ?
C18 N11 C17 124.27(10) . . ?
C9 N10 C10 124.31(10) . . ?
C3 N10 C9 108.34(10) . . ?
C3 N10 C10 127.07(10) . . ?
C24 N12 C25 123.43(10) . . ?
C18 N12 C24 108.51(10) . . ?
C18 N12 C25 128.07(10) . . ?
N3 N4 C2 116.97(11) . . ?
N5 N6 C17 116.69(11) . . ?
C17 N8 N7 117.09(11) . . ?
N6 N5 C16 118.23(11) . . ?
N4 N3 C1 118.33(11) . . ?
C2 N2 N1 117.05(11) . . ?
N8 N7 C16 117.70(11) . . ?
N2 N1 C1 118.10(12) . . ?
C9 C4 N9 106.11(10) . . ?
C5 C4 N9 132.41(12) . . ?
C5 C4 C9 121.47(11) . . ?
C24 C19 N11 105.90(10) . . ?
C24 C19 C20 121.50(11) . . ?
C20 C19 N11 132.54(12) . . ?
N6 C17 N11 115.89(11) . . ?
N8 C17 N11 117.10(10) . . ?
N8 C17 N6 126.44(12) . . ?
N4 C2 N9 115.44(10) . . ?
N2 C2 N9 116.86(10) . . ?
N2 C2 N4 127.56(11) . . ?
N10 C9 C8 131.13(12) . . ?
C4 C9 N10 107.01(10) . . ?
C4 C9 C8 121.84(11) . . ?
C19 C24 N12 107.03(10) . . ?
C19 C24 C23 122.00(11) . . ?
C23 C24 N12 130.95(12) . . ?
N10 C3 N9 110.31(10) . . ?
C21 C20 C19 116.42(12) . . ?
N10 C10 C15 112.46(11) . . ?
N10 C10 C11 109.24(11) . . ?
C15 C10 C11 111.49(12) . . ?
N12 C25 C26 110.95(11) . . ?
N12 C25 C30 112.06(10) . . ?
C30 C25 C26 111.00(11) . . ?
C22 C23 C24 116.29(12) . . ?
N12 C18 N11 110.01(11) . . ?
O2 C16 N5 120.11(12) . . ?
O2 C16 N7 120.11(13) . . ?
N5 C16 N7 119.65(12) . . ?
C20 C21 C22 121.86(12) . . ?
C23 C22 C21 121.92(12) . . ?
C6 C5 C4 116.63(13) . . ?
C7 C8 C9 116.37(13) . . ?
C27 C26 C25 109.79(11) . . ?
O1 C1 N3 119.65(14) . . ?
O1 C1 N1 119.37(15) . . ?
N1 C1 N3 120.98(12) . . ?
C25 C30 C29 109.44(11) . . ?
C13 C14 C15 111.55(13) . . ?
C10 C15 C14 109.80(11) . . ?
C28 C27 C26 111.23(12) . . ?
C28 C29 C30 112.14(13) . . ?
C5 C6 C7 121.74(13) . . ?
C10 C11 C12 110.59(13) . . ?
C8 C7 C6 121.91(12) . . ?
C29 C28 C27 110.96(13) . . ?
C12 C13 C14 111.46(14) . . ?
C13 C12 C11 111.02(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.047
_oxdiff_exptl_absorpt_empirical_full_min 0.439
####################################################################### 
# 
# 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_20190422-1
_database_code_depnum_ccdc_archive 'CCDC 2295521'
loop_
_audit_author_name
_audit_author_address
'JIanchun wang'
;Capital Normal University
China
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C12 H12 N12 O2), 0.5(H4 O2)'
_chemical_formula_sum            'C6 H9 N6 O2'
_chemical_formula_weight         197.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 H1 Cl1 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   14.1035(3)
_cell_length_b                   6.3113(2)
_cell_length_c                   9.5102(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     846.52(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1522
_cell_measurement_temperature    298.68(10)
_cell_measurement_theta_max      72.2100
_cell_measurement_theta_min      7.8320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1243
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2220
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.568
_diffrn_reflns_theta_max         66.567
_diffrn_reflns_theta_min         5.611
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.68(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  89.00   0.50    3.00    --    0.00  37.00-150.00  212
  2  ω    -22.00  89.00   0.50    3.00    --    0.00  57.00   0.00  222
  3  ω     71.00 113.00   0.50   10.00    --   94.60 -61.00 150.00   84
  4  ω     93.00 180.00   0.50   10.00    --   94.60  45.00-150.00  174
  5  ω     66.00 146.00   0.50   10.00    --   94.60  77.00 -90.00  160
  6  ω      7.00  73.00   0.50   10.00    --   94.60 -45.00-180.00  132
  7  ω    119.00 155.00   0.50   10.00    --   94.60  45.00 150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0250408000
_diffrn_orient_matrix_UB_12      -0.1812086000
_diffrn_orient_matrix_UB_13      0.1020364000
_diffrn_orient_matrix_UB_21      -0.0348425000
_diffrn_orient_matrix_UB_22      -0.1350122000
_diffrn_orient_matrix_UB_23      -0.1245119000
_diffrn_orient_matrix_UB_31      0.1004691000
_diffrn_orient_matrix_UB_32      -0.0922814000
_diffrn_orient_matrix_UB_33      -0.0178721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                694
_reflns_number_total             817
_reflns_odcompleteness_completeness 97.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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         0.560
_refine_diff_density_min         -1.358
_refine_diff_density_rms         0.410
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.1170
_refine_ls_restrained_S_all      1.071
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2392
_refine_ls_wR_factor_ref         0.2478
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1C(0.5) H1B(0.5) H2A(0.5) H2B(0.5)
3.a Free rotating group:
 O2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1C,H1B)
;
_atom_sites_solution_hydrogens   mixed
_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 0.38014(18) 0.2500 0.7090(3) 0.0792(11) Uani 1 2 d S T P . .
N1 N 0.5404(2) 0.2500 0.7194(2) 0.0548(9) Uani 1 2 d S T P . .
N2 N 0.62048(18) 0.2500 0.6490(3) 0.0516(9) Uani 1 2 d S T P . .
N3 N 0.53632(16) 0.2500 0.4323(2) 0.0440(9) Uani 1 2 d S T P . .
N4 N 0.45505(18) 0.2500 0.5005(3) 0.0481(9) Uani 1 2 d S T P . .
N5 N 0.70148(16) 0.2500 0.4357(2) 0.0416(9) Uani 1 2 d S T P . .
N6 N 0.85103(16) 0.2500 0.3929(2) 0.0438(8) Uani 1 2 d S T P . .
C1 C 0.9534(2) 0.2500 0.4133(3) 0.0567(10) Uani 1 2 d S T P . .
H1A H 0.9799 0.1239 0.3728 0.085 Uiso 0.5 1 calc GR . . A -1
H1C H 0.9673 0.2539 0.5120 0.085 Uiso 0.5 1 calc GR . . A -1
H1B H 0.9803 0.3722 0.3684 0.085 Uiso 0.5 1 calc GR . . A -1
C2 C 0.78740(19) 0.2500 0.4951(3) 0.0432(9) Uani 1 2 d S T P . .
H2 H 0.8001 0.2500 0.5910 0.052 Uiso 1 2 calc RS T P . .
C3 C 0.8057(2) 0.2500 0.2646(3) 0.0462(9) Uani 1 2 d S T P . .
H3 H 0.8345 0.2500 0.1767 0.055 Uiso 1 2 calc RS T P . .
C4 C 0.7124(2) 0.2500 0.2903(3) 0.0453(10) Uani 1 2 d S T P . .
H4 H 0.6641 0.2500 0.2237 0.054 Uiso 1 2 calc RS T P . .
C5 C 0.61452(18) 0.2500 0.5099(3) 0.0382(9) Uani 1 2 d S T P . .
C6 C 0.4565(2) 0.2500 0.6457(4) 0.0496(10) Uani 1 2 d S T P . .
O2 O 0.2061(2) 0.2500 0.5464(2) 0.0724(10) Uani 1 2 d S T P . .
H2A H 0.2581 0.2272 0.5892 0.109 Uiso 0.5 1 d G . . . .
H2B H 0.1634 0.2816 0.6057 0.109 Uiso 0.5 1 d G . . . .


_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 C6 1.234(4) . ?
N1 N2 1.314(4) . ?
N1 C6 1.375(5) . ?
N2 C5 1.325(4) . ?
N3 N4 1.317(3) . ?
N3 C5 1.327(3) . ?
N4 C6 1.381(5) . ?
N5 C2 1.337(3) . ?
N5 C4 1.391(3) . ?
N5 C5 1.415(3) . ?
N6 C1 1.456(4) . ?
N6 C2 1.322(3) . ?
N6 C3 1.378(4) . ?
C1 H1A 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1B 0.9600 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.338(4) . ?
C4 H4 0.9300 . ?
O2 H2A 0.8502 . ?
O2 H2B 0.8498 . ?

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
N2 N1 C6 118.7(2) . . ?
N1 N2 C5 117.0(2) . . ?
N4 N3 C5 116.7(2) . . ?
N3 N4 C6 118.7(3) . . ?
C2 N5 C4 108.6(2) . . ?
C2 N5 C5 125.1(2) . . ?
C4 N5 C5 126.3(2) . . ?
C2 N6 C1 125.1(2) . . ?
C2 N6 C3 109.6(2) . . ?
C3 N6 C1 125.3(2) . . ?
N6 C1 H1A 109.5 . . ?
N6 C1 H1C 109.5 . . ?
N6 C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
N5 C2 H2 126.1 . . ?
N6 C2 N5 107.7(2) . . ?
N6 C2 H2 126.1 . . ?
N6 C3 H3 126.4 . . ?
C4 C3 N6 107.2(2) . . ?
C4 C3 H3 126.4 . . ?
N5 C4 H4 126.6 . . ?
C3 C4 N5 106.8(2) . . ?
C3 C4 H4 126.6 . . ?
N2 C5 N3 127.4(2) . . ?
N2 C5 N5 116.3(2) . . ?
N3 C5 N5 116.3(2) . . ?
O1 C6 N1 120.1(3) . . ?
O1 C6 N4 118.4(3) . . ?
N1 C6 N4 121.5(3) . . ?
H2A O2 H2B 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.435
_oxdiff_exptl_absorpt_empirical_full_min 0.127
####################################################################### 
# 
# 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_bww19367
_database_code_depnum_ccdc_archive 'CCDC 2295522'
loop_
_audit_author_name
_audit_author_address
'JIanchun wang'
;Capital Normal University
China
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_audit_creation_date             2019-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Pd, 2(C5 H9 N2)'
_chemical_formula_sum            'C10 H18 Cl4 N4 Pd'
_chemical_formula_weight         442.48
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
Pd Pd -0.9988 1.0072 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6646(17)
_cell_length_b                   8.0989(16)
_cell_length_c                   12.187(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.52(3)
_cell_angle_gamma                90
_cell_volume                     831.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2961
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.7186
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    1.750
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5866
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.618
_diffrn_ambient_temperature      163.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1817
_reflns_number_total             1891
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         1.128
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1891
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+1.2573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_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
Pd1 Pd 0.000000 0.000000 0.500000 0.03073(15) Uani 1 2 d S T P . .
Cl1 Cl -0.00968(10) 0.28086(11) 0.46900(9) 0.0418(2) Uani 1 1 d . . . . .
Cl2 Cl 0.22948(13) -0.01060(10) 0.43478(10) 0.0445(3) Uani 1 1 d . . . . .
N2 N 0.4917(4) 0.4867(4) 0.6603(3) 0.0402(8) Uani 1 1 d . . . . .
N1 N 0.6781(3) 0.6346(4) 0.6272(2) 0.0393(7) Uani 1 1 d . . . . .
H1 H 0.734515 0.719617 0.620129 0.047 Uiso 1 1 d R . . . .
C1 C 0.5427(4) 0.6375(5) 0.6614(3) 0.0371(8) Uani 1 1 d . . . . .
C2 C 0.5960(6) 0.3832(5) 0.6264(3) 0.0518(11) Uani 1 1 d . . . . .
H2 H 0.586530 0.266666 0.619078 0.062 Uiso 1 1 calc R . . . .
C3 C 0.7129(5) 0.4748(6) 0.6054(3) 0.0484(10) Uani 1 1 d . . . . .
H3 H 0.802624 0.437074 0.580336 0.058 Uiso 1 1 calc R . . . .
C4 C 0.4658(5) 0.7902(5) 0.6929(3) 0.0491(9) Uani 1 1 d . . . . .
H4A H 0.358886 0.801018 0.644253 0.074 Uiso 1 1 calc GR . . . .
H4B H 0.529302 0.886869 0.683145 0.074 Uiso 1 1 calc GR . . . .
H4C H 0.458936 0.782635 0.771842 0.074 Uiso 1 1 calc GR . . . .
C5 C 0.3434(5) 0.4361(7) 0.6910(4) 0.0540(10) Uani 1 1 d . . . . .
H5A H 0.368899 0.383012 0.765306 0.081 Uiso 1 1 calc GR . . . .
H5B H 0.285584 0.358132 0.634608 0.081 Uiso 1 1 calc GR . . . .
H5C H 0.277195 0.533567 0.693360 0.081 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
Pd1 Cl1 2.3041(10) . ?
Pd1 Cl1 2.3041(10) 3_556 ?
Pd1 Cl2 2.3090(11) 3_556 ?
Pd1 Cl2 2.3091(11) . ?
N2 C1 1.297(5) . ?
N2 C2 1.365(6) . ?
N2 C5 1.478(5) . ?
N1 C1 1.334(5) . ?
N1 C3 1.369(5) . ?
C1 C4 1.497(5) . ?
C2 C3 1.328(7) . ?

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
Cl1 Pd1 Cl1 180.0 . 3_556 ?
Cl1 Pd1 Cl2 91.06(3) 3_556 . ?
Cl1 Pd1 Cl2 88.94(3) . . ?
Cl1 Pd1 Cl2 88.94(3) 3_556 3_556 ?
Cl1 Pd1 Cl2 91.06(3) . 3_556 ?
Cl2 Pd1 Cl2 180.0 3_556 . ?
C1 N2 C2 109.4(3) . . ?
C1 N2 C5 124.9(4) . . ?
C2 N2 C5 125.6(4) . . ?
C1 N1 C3 109.1(3) . . ?
N2 C1 N1 107.6(3) . . ?
N2 C1 C4 127.6(3) . . ?
N1 C1 C4 124.8(4) . . ?
C3 C2 N2 107.7(4) . . ?
C2 C3 N1 106.2(3) . . ?

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
N2 C2 C3 N1 0.1(5) . . . . ?
C1 N2 C2 C3 -0.5(5) . . . . ?
C1 N1 C3 C2 0.4(4) . . . . ?
C2 N2 C1 N1 0.7(4) . . . . ?
C2 N2 C1 C4 179.9(3) . . . . ?
C3 N1 C1 N2 -0.7(4) . . . . ?
C3 N1 C1 C4 -179.9(3) . . . . ?
C5 N2 C1 N1 -179.1(3) . . . . ?
C5 N2 C1 C4 0.1(6) . . . . ?
C5 N2 C2 C3 179.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
