# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_123
_database_code_depnum_ccdc_archive 'CCDC 2171263'
loop_
_audit_author_name
_audit_author_address
'Yuntian Xiao'
;Tianjin University
China
;
_audit_update_record             
;
2022-05-07 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-11-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Metamitron-Cinnamic acid'
_chemical_formula_moiety         'C10 H10 N4 O, C9 H8 O2'
_chemical_formula_sum            'C19 H18 N4 O3'
_chemical_formula_weight         350.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        P21/n
_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                   9.5056(5)
_cell_length_b                   28.8708(9)
_cell_length_c                   13.6219(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.812(5)
_cell_angle_gamma                90
_cell_volume                     3393.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.1290
_cell_measurement_theta_min      2.1630
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29169
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_min         2.349
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    2.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  40.00   1.00    2.00    --  -30.00  45.00  90.00  160
  3  ω   -120.00  40.00   1.00    2.00    --  -30.00  45.00 180.00  160
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0083137000
_diffrn_orient_matrix_UB_12      -0.0244113000
_diffrn_orient_matrix_UB_13      -0.0037666000
_diffrn_orient_matrix_UB_21      -0.0186448000
_diffrn_orient_matrix_UB_22      0.0014912000
_diffrn_orient_matrix_UB_23      -0.0571574000
_diffrn_orient_matrix_UB_31      0.0753592000
_diffrn_orient_matrix_UB_32      -0.0023291000
_diffrn_orient_matrix_UB_33      0.0028839000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5073
_reflns_number_total             7000
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0042(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         7000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.038
_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)+(0.0497P)²+1.5680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1361
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N00D(H00C,H00D)
2.b Rotating group:
 N00E(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P), C00R(H00R), C00T(H00T),
 C00V(H00V), C00X(H00X), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C019(H019), C01B(H01D), C01C(H01H), C01D(H01I), C01F(H01J), C01G(H01K)
2.d Idealised Me refined as rotating group:
 C01A(H01A,H01B,H01C), C01E(H01E,H01F,H01G)
2.e Idealised tetrahedral OH refined as rotating group:
 O004(H004), O006(H006)
;
_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
O001 O 0.20317(17) 0.32705(5) 0.74155(11) 0.0279(3) Uani 1 1 d . . . . .
O002 O 1.03946(16) 0.28602(5) -0.06536(12) 0.0300(3) Uani 1 1 d . . . . .
O003 O 0.55499(16) 0.21208(4) 0.44011(11) 0.0273(3) Uani 1 1 d . . . . .
O004 O 1.00578(19) 0.33791(5) 0.04541(12) 0.0326(4) Uani 1 1 d . . . . .
H004 H 0.974325 0.315199 0.066370 0.049 Uiso 1 1 calc R U . . .
O005 O 0.68665(17) 0.17630(5) 0.24007(11) 0.0305(4) Uani 1 1 d . . . . .
O006 O 0.48740(19) 0.16151(5) 0.53689(12) 0.0317(4) Uani 1 1 d . . . . .
H006 H 0.456757 0.185031 0.555542 0.048 Uiso 1 1 calc R U . . .
N007 N 0.77162(19) 0.24977(5) 0.24269(12) 0.0215(4) Uani 1 1 d . . . . .
N008 N 0.28761(18) 0.25366(5) 0.74125(12) 0.0195(3) Uani 1 1 d . . . . .
N009 N 0.36196(19) 0.27424(5) 0.57416(12) 0.0207(4) Uani 1 1 d . . . . .
N00A N 0.86456(19) 0.22987(5) 0.08523(13) 0.0228(4) Uani 1 1 d . . . . .
N00B N 0.38420(19) 0.23051(5) 0.61781(13) 0.0222(4) Uani 1 1 d . . . . .
N00C N 0.88530(19) 0.27327(5) 0.12933(13) 0.0239(4) Uani 1 1 d . . . . .
N00D N 0.7246(2) 0.26199(6) 0.32531(13) 0.0265(4) Uani 1 1 d . . . . .
H00C H 0.662767 0.248133 0.352904 0.032 Uiso 1 1 d R U . . .
H00D H 0.828637 0.252033 0.368504 0.032 Uiso 1 1 d R U . . .
N00E N 0.2462(2) 0.24089(5) 0.82576(13) 0.0237(4) Uani 1 1 d . . . . .
H00A H 0.327149 0.240842 0.887250 0.028 Uiso 1 1 d R U . . .
H00B H 0.179382 0.260443 0.829502 0.028 Uiso 1 1 d R U . . .
C00F C 0.3062(2) 0.30684(6) 0.61392(14) 0.0182(4) Uani 1 1 d . . . . .
C00G C 0.5673(2) 0.04863(6) 0.36735(15) 0.0209(4) Uani 1 1 d . . . . .
C00H C 0.2615(2) 0.29881(6) 0.70288(14) 0.0189(4) Uani 1 1 d . . . . .
C00I C 0.7989(2) 0.19736(6) 0.11793(15) 0.0203(4) Uani 1 1 d . . . . .
C00J C 0.7856(2) 0.15120(6) 0.06697(14) 0.0198(4) Uani 1 1 d . . . . .
C00K C 0.2886(2) 0.35352(6) 0.56543(15) 0.0193(4) Uani 1 1 d . . . . .
C00L C 0.2646(2) 0.44104(6) 0.47324(16) 0.0241(4) Uani 1 1 d . . . . .
H00L H 0.256576 0.470207 0.442383 0.029 Uiso 1 1 calc R U . . .
C00M C 0.2425(2) 0.35821(6) 0.45440(15) 0.0222(4) Uani 1 1 d . . . . .
H00M H 0.220784 0.331999 0.410826 0.027 Uiso 1 1 calc R U . . .
C00N C 0.2288(2) 0.40171(6) 0.40877(16) 0.0233(4) Uani 1 1 d . . . . .
H00N H 0.195498 0.404617 0.334377 0.028 Uiso 1 1 calc R U . . .
C00O C 0.3488(2) 0.22116(6) 0.69855(15) 0.0209(4) Uani 1 1 d . . . . .
C00P C 0.8932(2) 0.13947(7) 0.02678(15) 0.0225(4) Uani 1 1 d . . . . .
H00P H 0.971752 0.160206 0.033762 0.027 Uiso 1 1 calc R U . . .
C00Q C 0.7459(2) 0.20470(6) 0.20282(15) 0.0217(4) Uani 1 1 d . . . . .
C00R C 0.5379(2) 0.08932(6) 0.42096(15) 0.0227(4) Uani 1 1 d . . . . .
H00R H 0.480308 0.084575 0.460889 0.027 Uiso 1 1 calc R U . . .
C00S C 0.8376(2) 0.28253(6) 0.20437(15) 0.0222(4) Uani 1 1 d . . . . .
C00T C 1.0724(2) 0.40926(7) -0.06430(16) 0.0242(4) Uani 1 1 d . . . . .
H00T H 1.066018 0.414861 0.000942 0.029 Uiso 1 1 calc R U . . .
C00U C 1.0891(2) 0.44979(7) -0.12325(16) 0.0225(4) Uani 1 1 d . . . . .
C00V C 0.6678(2) 0.04970(7) 0.31630(15) 0.0250(4) Uani 1 1 d . . . . .
H00V H 0.718788 0.077019 0.314908 0.030 Uiso 1 1 calc R U . . .
C00W C 0.5421(2) 0.17238(6) 0.46523(15) 0.0223(4) Uani 1 1 d . . . . .
C00X C 0.3214(2) 0.39321(6) 0.62980(15) 0.0231(4) Uani 1 1 d . . . . .
H00X H 0.349487 0.390591 0.703705 0.028 Uiso 1 1 calc R U . . .
C00Y C 1.0365(2) 0.32605(7) -0.03748(16) 0.0254(4) Uani 1 1 d . . . . .
C00Z C 1.1171(2) 0.49300(7) -0.07281(16) 0.0240(4) Uani 1 1 d . . . . .
H00Z H 1.131647 0.495153 -0.001054 0.029 Uiso 1 1 calc R U . . .
C010 C 0.7677(2) 0.06664(7) -0.03552(17) 0.0292(5) Uani 1 1 d . . . . .
H010 H 0.760757 0.038576 -0.070796 0.035 Uiso 1 1 calc R U . . .
C011 C 0.5861(2) 0.13223(7) 0.41764(16) 0.0238(4) Uani 1 1 d . . . . .
H011 H 0.651297 0.137182 0.383353 0.029 Uiso 1 1 calc R U . . .
C012 C 0.3120(2) 0.43660(6) 0.58343(16) 0.0253(4) Uani 1 1 d . . . . .
H012 H 0.337871 0.462870 0.626964 0.030 Uiso 1 1 calc R U . . .
C013 C 0.4910(2) 0.00736(7) 0.36685(16) 0.0260(4) Uani 1 1 d . . . . .
H013 H 0.422890 0.006255 0.399807 0.031 Uiso 1 1 calc R U . . .
C014 C 1.0697(2) 0.44742(7) -0.23080(16) 0.0273(5) Uani 1 1 d . . . . .
H014 H 1.052747 0.418917 -0.265686 0.033 Uiso 1 1 calc R U . . .
C015 C 0.6698(2) 0.11967(7) 0.05671(17) 0.0288(5) Uani 1 1 d . . . . .
H015 H 0.598189 0.126704 0.084557 0.035 Uiso 1 1 calc R U . . .
C016 C 1.1237(2) 0.53283(7) -0.12772(17) 0.0273(5) Uani 1 1 d . . . . .
H016 H 1.142586 0.561371 -0.092901 0.033 Uiso 1 1 calc R U . . .
C017 C 1.1020(2) 0.52989(7) -0.23445(17) 0.0283(5) Uani 1 1 d . . . . .
H017 H 1.105153 0.556515 -0.271878 0.034 Uiso 1 1 calc R U . . .
C018 C 1.0754(2) 0.48718(7) -0.28554(16) 0.0296(5) Uani 1 1 d . . . . .
H018 H 1.061439 0.485254 -0.357212 0.035 Uiso 1 1 calc R U . . .
C019 C 0.8848(2) 0.09743(7) -0.02333(16) 0.0265(5) Uani 1 1 d . . . . .
H019 H 0.958375 0.089808 -0.049006 0.032 Uiso 1 1 calc R U . . .
C01A C 0.3775(3) 0.17381(7) 0.74591(17) 0.0306(5) Uani 1 1 d . . . . .
H01A H 0.452445 0.175334 0.819848 0.046 Uiso 1 1 calc R U . . .
H01B H 0.416226 0.154384 0.705577 0.046 Uiso 1 1 calc R U . . .
H01C H 0.282383 0.161155 0.742878 0.046 Uiso 1 1 calc R U . . .
C01B C 0.6610(3) 0.07769(7) 0.00488(19) 0.0331(5) Uani 1 1 d . . . . .
H01D H 0.582600 0.056829 -0.002669 0.040 Uiso 1 1 calc R U . . .
C01C C 1.0655(2) 0.36537(7) -0.09474(17) 0.0276(5) Uani 1 1 d . . . . .
H01H H 1.080031 0.359072 -0.156804 0.033 Uiso 1 1 calc R U . . .
C01D C 0.6916(2) 0.01013(7) 0.26781(16) 0.0289(5) Uani 1 1 d . . . . .
H01I H 0.759301 0.010965 0.234560 0.035 Uiso 1 1 calc R U . . .
C01E C 0.8570(3) 0.33011(7) 0.24926(17) 0.0319(5) Uani 1 1 d . . . . .
H01E H 0.758167 0.341938 0.240723 0.048 Uiso 1 1 calc R U . . .
H01F H 0.899227 0.349753 0.211411 0.048 Uiso 1 1 calc R U . . .
H01G H 0.926270 0.329447 0.324681 0.048 Uiso 1 1 calc R U . . .
C01F C 0.5150(3) -0.03198(7) 0.31801(18) 0.0328(5) Uani 1 1 d . . . . .
H01J H 0.463672 -0.059333 0.318531 0.039 Uiso 1 1 calc R U . . .
C01G C 0.6155(3) -0.03063(7) 0.26840(18) 0.0332(5) Uani 1 1 d . . . . .
H01K H 0.631866 -0.057050 0.235534 0.040 Uiso 1 1 calc R U . . .


_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
O001 C00H 1.223(2) . ?
O002 C00Y 1.220(2) . ?
O003 C00W 1.217(2) . ?
O004 H004 0.8200 . ?
O004 C00Y 1.325(2) . ?
O005 C00Q 1.219(2) . ?
O006 H006 0.8200 . ?
O006 C00W 1.322(2) . ?
N007 N00D 1.419(2) . ?
N007 C00Q 1.392(2) . ?
N007 C00S 1.355(2) . ?
N008 N00E 1.413(2) . ?
N008 C00H 1.388(2) . ?
N008 C00O 1.357(2) . ?
N009 N00B 1.374(2) . ?
N009 C00F 1.304(2) . ?
N00A N00C 1.368(2) . ?
N00A C00I 1.305(2) . ?
N00B C00O 1.306(2) . ?
N00C C00S 1.308(3) . ?
N00D H00C 0.9121 . ?
N00D H00D 0.9586 . ?
N00E H00A 0.8676 . ?
N00E H00B 0.8671 . ?
C00F C00H 1.461(3) . ?
C00F C00K 1.479(2) . ?
C00G C00R 1.470(3) . ?
C00G C00V 1.398(3) . ?
C00G C013 1.394(3) . ?
C00I C00J 1.483(2) . ?
C00I C00Q 1.458(3) . ?
C00J C00P 1.390(3) . ?
C00J C015 1.390(3) . ?
C00K C00M 1.393(3) . ?
C00K C00X 1.396(3) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.388(3) . ?
C00L C012 1.380(3) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.383(3) . ?
C00N H00N 0.9300 . ?
C00O C01A 1.487(3) . ?
C00P H00P 0.9300 . ?
C00P C019 1.378(3) . ?
C00R H00R 0.9300 . ?
C00R C011 1.328(3) . ?
C00S C01E 1.483(3) . ?
C00T H00T 0.9300 . ?
C00T C00U 1.465(3) . ?
C00T C01C 1.326(3) . ?
C00U C00Z 1.395(3) . ?
C00U C014 1.399(3) . ?
C00V H00V 0.9300 . ?
C00V C01D 1.385(3) . ?
C00W C011 1.472(3) . ?
C00X H00X 0.9300 . ?
C00X C012 1.389(3) . ?
C00Y C01C 1.467(3) . ?
C00Z H00Z 0.9300 . ?
C00Z C016 1.387(3) . ?
C010 H010 0.9300 . ?
C010 C019 1.379(3) . ?
C010 C01B 1.379(3) . ?
C011 H011 0.9300 . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C013 C01F 1.383(3) . ?
C014 H014 0.9300 . ?
C014 C018 1.382(3) . ?
C015 H015 0.9300 . ?
C015 C01B 1.388(3) . ?
C016 H016 0.9300 . ?
C016 C017 1.383(3) . ?
C017 H017 0.9300 . ?
C017 C018 1.386(3) . ?
C018 H018 0.9300 . ?
C019 H019 0.9300 . ?
C01A H01A 0.9600 . ?
C01A H01B 0.9600 . ?
C01A H01C 0.9600 . ?
C01B H01D 0.9300 . ?
C01C H01H 0.9300 . ?
C01D H01I 0.9300 . ?
C01D C01G 1.383(3) . ?
C01E H01E 0.9600 . ?
C01E H01F 0.9600 . ?
C01E H01G 0.9600 . ?
C01F H01J 0.9300 . ?
C01F C01G 1.383(3) . ?
C01G H01K 0.9300 . ?

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
C00Y O004 H004 109.5 . . ?
C00W O006 H006 109.5 . . ?
C00Q N007 N00D 118.67(15) . . ?
C00S N007 N00D 118.88(16) . . ?
C00S N007 C00Q 122.44(16) . . ?
C00H N008 N00E 119.02(15) . . ?
C00O N008 N00E 119.02(15) . . ?
C00O N008 C00H 121.95(16) . . ?
C00F N009 N00B 119.93(16) . . ?
C00I N00A N00C 120.69(16) . . ?
C00O N00B N009 120.47(16) . . ?
C00S N00C N00A 119.83(16) . . ?
N007 N00D H00C 133.6 . . ?
N007 N00D H00D 79.9 . . ?
H00C N00D H00D 107.0 . . ?
N008 N00E H00A 110.5 . . ?
N008 N00E H00B 109.8 . . ?
H00A N00E H00B 108.6 . . ?
N009 C00F C00H 122.71(16) . . ?
N009 C00F C00K 117.47(16) . . ?
C00H C00F C00K 119.82(16) . . ?
C00V C00G C00R 122.75(18) . . ?
C013 C00G C00R 118.59(18) . . ?
C013 C00G C00V 118.65(18) . . ?
O001 C00H N008 120.39(17) . . ?
O001 C00H C00F 126.43(17) . . ?
N008 C00H C00F 113.16(15) . . ?
N00A C00I C00J 116.43(17) . . ?
N00A C00I C00Q 122.72(17) . . ?
C00Q C00I C00J 120.81(16) . . ?
C00P C00J C00I 118.12(17) . . ?
C00P C00J C015 118.94(17) . . ?
C015 C00J C00I 122.93(17) . . ?
C00M C00K C00F 119.89(16) . . ?
C00M C00K C00X 119.18(17) . . ?
C00X C00K C00F 120.91(16) . . ?
C00N C00L H00L 120.2 . . ?
C012 C00L H00L 120.2 . . ?
C012 C00L C00N 119.60(17) . . ?
C00K C00M H00M 119.9 . . ?
C00N C00M C00K 120.24(18) . . ?
C00N C00M H00M 119.9 . . ?
C00L C00N H00N 119.8 . . ?
C00M C00N C00L 120.44(18) . . ?
C00M C00N H00N 119.8 . . ?
N008 C00O C01A 118.89(17) . . ?
N00B C00O N008 121.76(17) . . ?
N00B C00O C01A 119.34(17) . . ?
C00J C00P H00P 119.7 . . ?
C019 C00P C00J 120.69(18) . . ?
C019 C00P H00P 119.7 . . ?
O005 C00Q N007 120.18(17) . . ?
O005 C00Q C00I 127.31(18) . . ?
N007 C00Q C00I 112.51(16) . . ?
C00G C00R H00R 117.0 . . ?
C011 C00R C00G 126.03(19) . . ?
C011 C00R H00R 117.0 . . ?
N007 C00S C01E 119.03(18) . . ?
N00C C00S N007 121.78(17) . . ?
N00C C00S C01E 119.19(18) . . ?
C00U C00T H00T 116.8 . . ?
C01C C00T H00T 116.8 . . ?
C01C C00T C00U 126.46(19) . . ?
C00Z C00U C00T 119.12(18) . . ?
C00Z C00U C014 118.25(18) . . ?
C014 C00U C00T 122.54(17) . . ?
C00G C00V H00V 120.0 . . ?
C01D C00V C00G 120.08(19) . . ?
C01D C00V H00V 120.0 . . ?
O003 C00W O006 123.23(18) . . ?
O003 C00W C011 122.50(18) . . ?
O006 C00W C011 114.27(16) . . ?
C00K C00X H00X 120.0 . . ?
C012 C00X C00K 119.99(18) . . ?
C012 C00X H00X 120.0 . . ?
O002 C00Y O004 123.51(19) . . ?
O002 C00Y C01C 122.23(19) . . ?
O004 C00Y C01C 114.26(17) . . ?
C00U C00Z H00Z 119.4 . . ?
C016 C00Z C00U 121.21(19) . . ?
C016 C00Z H00Z 119.4 . . ?
C019 C010 H010 120.2 . . ?
C01B C010 H010 120.2 . . ?
C01B C010 C019 119.62(19) . . ?
C00R C011 C00W 123.62(19) . . ?
C00R C011 H011 118.2 . . ?
C00W C011 H011 118.2 . . ?
C00L C012 C00X 120.51(18) . . ?
C00L C012 H012 119.7 . . ?
C00X C012 H012 119.7 . . ?
C00G C013 H013 119.6 . . ?
C01F C013 C00G 120.90(19) . . ?
C01F C013 H013 119.6 . . ?
C00U C014 H014 119.8 . . ?
C018 C014 C00U 120.44(19) . . ?
C018 C014 H014 119.8 . . ?
C00J C015 H015 120.0 . . ?
C01B C015 C00J 119.94(19) . . ?
C01B C015 H015 120.0 . . ?
C00Z C016 H016 120.1 . . ?
C017 C016 C00Z 119.70(19) . . ?
C017 C016 H016 120.1 . . ?
C016 C017 H017 120.1 . . ?
C016 C017 C018 119.87(19) . . ?
C018 C017 H017 120.1 . . ?
C014 C018 C017 120.52(19) . . ?
C014 C018 H018 119.7 . . ?
C017 C018 H018 119.7 . . ?
C00P C019 C010 120.24(19) . . ?
C00P C019 H019 119.9 . . ?
C010 C019 H019 119.9 . . ?
C00O C01A H01A 109.5 . . ?
C00O C01A H01B 109.5 . . ?
C00O C01A H01C 109.5 . . ?
H01A C01A H01B 109.5 . . ?
H01A C01A H01C 109.5 . . ?
H01B C01A H01C 109.5 . . ?
C010 C01B C015 120.54(19) . . ?
C010 C01B H01D 119.7 . . ?
C015 C01B H01D 119.7 . . ?
C00T C01C C00Y 124.66(19) . . ?
C00T C01C H01H 117.7 . . ?
C00Y C01C H01H 117.7 . . ?
C00V C01D H01I 119.7 . . ?
C01G C01D C00V 120.6(2) . . ?
C01G C01D H01I 119.7 . . ?
C00S C01E H01E 109.5 . . ?
C00S C01E H01F 109.5 . . ?
C00S C01E H01G 109.5 . . ?
H01E C01E H01F 109.5 . . ?
H01E C01E H01G 109.5 . . ?
H01F C01E H01G 109.5 . . ?
C013 C01F H01J 120.0 . . ?
C01G C01F C013 120.0(2) . . ?
C01G C01F H01J 120.0 . . ?
C01D C01G H01K 120.1 . . ?
C01F C01G C01D 119.80(19) . . ?
C01F C01G H01K 120.1 . . ?

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
O002 C00Y C01C C00T -176.0(2) . . . . ?
O003 C00W C011 C00R -161.9(2) . . . . ?
O004 C00Y C01C C00T 4.7(3) . . . . ?
O006 C00W C011 C00R 17.9(3) . . . . ?
N009 N00B C00O N008 0.8(3) . . . . ?
N009 N00B C00O C01A -178.59(17) . . . . ?
N009 C00F C00H O001 -177.02(18) . . . . ?
N009 C00F C00H N008 1.2(3) . . . . ?
N009 C00F C00K C00M 37.2(3) . . . . ?
N009 C00F C00K C00X -141.21(19) . . . . ?
N00A N00C C00S N007 2.0(3) . . . . ?
N00A N00C C00S C01E -178.32(17) . . . . ?
N00A C00I C00J C00P 26.6(2) . . . . ?
N00A C00I C00J C015 -152.60(19) . . . . ?
N00A C00I C00Q O005 -178.28(19) . . . . ?
N00A C00I C00Q N007 0.8(3) . . . . ?
N00B N009 C00F C00H -1.5(3) . . . . ?
N00B N009 C00F C00K 178.45(16) . . . . ?
N00C N00A C00I C00J -178.44(16) . . . . ?
N00C N00A C00I C00Q -0.8(3) . . . . ?
N00D N007 C00Q O005 -1.4(3) . . . . ?
N00D N007 C00Q C00I 179.52(15) . . . . ?
N00D N007 C00S N00C 179.07(17) . . . . ?
N00D N007 C00S C01E -0.6(3) . . . . ?
N00E N008 C00H O001 -0.2(3) . . . . ?
N00E N008 C00H C00F -178.56(15) . . . . ?
N00E N008 C00O N00B 177.55(17) . . . . ?
N00E N008 C00O C01A -3.0(3) . . . . ?
C00F N009 N00B C00O 0.5(3) . . . . ?
C00F C00K C00M C00N -178.68(17) . . . . ?
C00F C00K C00X C012 176.61(18) . . . . ?
C00G C00R C011 C00W 174.59(18) . . . . ?
C00G C00V C01D C01G 0.6(3) . . . . ?
C00G C013 C01F C01G -0.3(3) . . . . ?
C00H N008 C00O N00B -1.1(3) . . . . ?
C00H N008 C00O C01A 178.33(18) . . . . ?
C00H C00F C00K C00M -142.84(18) . . . . ?
C00H C00F C00K C00X 38.8(3) . . . . ?
C00I N00A N00C C00S -0.6(3) . . . . ?
C00I C00J C00P C019 -178.71(17) . . . . ?
C00I C00J C015 C01B 177.83(19) . . . . ?
C00J C00I C00Q O005 -0.7(3) . . . . ?
C00J C00I C00Q N007 178.34(16) . . . . ?
C00J C00P C019 C010 0.9(3) . . . . ?
C00J C015 C01B C010 0.8(3) . . . . ?
C00K C00F C00H O001 3.0(3) . . . . ?
C00K C00F C00H N008 -178.76(16) . . . . ?
C00K C00M C00N C00L 1.6(3) . . . . ?
C00K C00X C012 C00L 2.5(3) . . . . ?
C00M C00K C00X C012 -1.8(3) . . . . ?
C00N C00L C012 C00X -1.2(3) . . . . ?
C00O N008 C00H O001 178.46(17) . . . . ?
C00O N008 C00H C00F 0.1(2) . . . . ?
C00P C00J C015 C01B -1.4(3) . . . . ?
C00Q N007 C00S N00C -2.0(3) . . . . ?
C00Q N007 C00S C01E 178.33(18) . . . . ?
C00Q C00I C00J C00P -151.11(18) . . . . ?
C00Q C00I C00J C015 29.7(3) . . . . ?
C00R C00G C00V C01D 179.54(18) . . . . ?
C00R C00G C013 C01F -179.68(19) . . . . ?
C00S N007 C00Q O005 179.70(18) . . . . ?
C00S N007 C00Q C00I 0.6(2) . . . . ?
C00T C00U C00Z C016 -175.75(18) . . . . ?
C00T C00U C014 C018 175.29(19) . . . . ?
C00U C00T C01C C00Y -174.97(19) . . . . ?
C00U C00Z C016 C017 0.1(3) . . . . ?
C00U C014 C018 C017 0.6(3) . . . . ?
C00V C00G C00R C011 8.2(3) . . . . ?
C00V C00G C013 C01F 0.7(3) . . . . ?
C00V C01D C01G C01F -0.1(3) . . . . ?
C00X C00K C00M C00N -0.3(3) . . . . ?
C00Z C00U C014 C018 -1.2(3) . . . . ?
C00Z C016 C017 C018 -0.7(3) . . . . ?
C012 C00L C00N C00M -0.9(3) . . . . ?
C013 C00G C00R C011 -171.43(19) . . . . ?
C013 C00G C00V C01D -0.9(3) . . . . ?
C013 C01F C01G C01D 0.0(3) . . . . ?
C014 C00U C00Z C016 0.8(3) . . . . ?
C015 C00J C00P C019 0.5(3) . . . . ?
C016 C017 C018 C014 0.4(3) . . . . ?
C019 C010 C01B C015 0.6(3) . . . . ?
C01B C010 C019 C00P -1.5(3) . . . . ?
C01C C00T C00U C00Z -170.7(2) . . . . ?
C01C C00T C00U C014 12.8(3) . . . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.831
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_r20211203a
_database_code_depnum_ccdc_archive 'CCDC 2171265'
loop_
_audit_author_name
_audit_author_address
'Yuntian Xiao'
;Tianjin University
China
;
_audit_update_record             
;
2022-05-07 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-12-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.16 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Metamitron-Naringenin
_chemical_formula_moiety         'C10 H10 N4 O, C15 H12 O5'
_chemical_formula_sum            'C25 H22 N4 O6'
_chemical_formula_weight         474.46
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        Pc
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.8352(12)
_cell_length_b                   14.4349(12)
_cell_length_c                   6.7368(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.770(12)
_cell_angle_gamma                90
_cell_volume                     1107.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4761
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.6800
_cell_measurement_theta_min      2.2610
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.16
_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  0.0689
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10628
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         2.278
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00   25.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00   25.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00   25.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0026418000
_diffrn_orient_matrix_UB_12      -0.0489391000
_diffrn_orient_matrix_UB_13      0.0094520000
_diffrn_orient_matrix_UB_21      -0.0618443000
_diffrn_orient_matrix_UB_22      -0.0024868000
_diffrn_orient_matrix_UB_23      -0.0403646000
_diffrn_orient_matrix_UB_31      0.0066708000
_diffrn_orient_matrix_UB_32      -0.0035781000
_diffrn_orient_matrix_UB_33      -0.1012611000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2848
_reflns_number_total             3759
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.046
_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)+(0.0594P)²+0.5791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1459
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.947(2)
 0.053(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Rotating group:
 N1(H1A,H1B)
3.b Ternary CH refined with riding coordinates:
 C17(H17)
3.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C1(H1), C5(H5), C4(H4), C3(H3A), C12(H12), C19(H19), C21(H21),
 C22(H22), C24(H24), C25(H25)
3.e Fitted hexagon refined as free rotating group:
 C2(C1,C6,C5,C4,C3)
3.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
3.g Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.5977(4) 0.8049(3) 0.5800(7) 0.0297(12) Uani 1 1 d . . . . .
N1 N 0.8290(5) 0.8132(4) 0.7355(10) 0.0314(14) Uani 1 1 d . . . . .
H1A H 0.891560 0.810067 0.692776 0.038 Uiso 1 1 d R U . . .
H1B H 0.784090 0.856557 0.668530 0.038 Uiso 1 1 d R U . . .
N2 N 0.7699(5) 0.7277(4) 0.7037(9) 0.0232(13) Uani 1 1 d . . . . .
N3 N 0.7747(5) 0.5677(4) 0.7512(9) 0.0294(15) Uani 1 1 d . . . . .
N4 N 0.6551(5) 0.5639(4) 0.6868(10) 0.0307(14) Uani 1 1 d . . . . .
C2 C 0.2865(4) 0.5761(4) 0.6335(9) 0.062(3) Uani 1 1 d G . . . .
H2A H 0.248163 0.543709 0.719438 0.074 Uiso 1 1 calc R U . . .
C1 C 0.4080(4) 0.5848(4) 0.6922(7) 0.047(2) Uani 1 1 d G . . . .
H1 H 0.452764 0.558401 0.818195 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4641(3) 0.6323(3) 0.5665(8) 0.0308(17) Uani 1 1 d G . . . .
C5 C 0.3987(4) 0.6710(3) 0.3821(7) 0.0359(18) Uani 1 1 d G . . . .
H5 H 0.436984 0.703384 0.296144 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2771(4) 0.6622(4) 0.3234(8) 0.054(3) Uani 1 1 d G . . . .
H4 H 0.232383 0.688692 0.197383 0.064 Uiso 1 1 calc R U . . .
C3 C 0.2210(3) 0.6148(4) 0.4491(10) 0.059(3) Uani 1 1 d G . . . .
H3A H 0.137971 0.608855 0.409028 0.071 Uiso 1 1 calc R U . . .
C7 C 0.5938(6) 0.6396(5) 0.6281(11) 0.0259(16) Uani 1 1 d . . . . .
C8 C 0.6487(6) 0.7304(5) 0.6310(10) 0.0255(17) Uani 1 1 d . . . . .
C9 C 0.8297(6) 0.6474(5) 0.7609(10) 0.0258(16) Uani 1 1 d . . . . .
C10 C 0.9599(6) 0.6498(5) 0.8331(12) 0.0327(18) Uani 1 1 d . . . . .
H10A H 0.989595 0.587797 0.878858 0.049 Uiso 1 1 calc R U . . .
H10B H 0.984537 0.693399 0.948264 0.049 Uiso 1 1 calc R U . . .
H10C H 0.991508 0.669746 0.719810 0.049 Uiso 1 1 calc R U . . .
O2 O 0.9029(4) 0.4157(3) 0.8298(8) 0.0308(12) Uani 1 1 d . . . . .
H2 H 0.851442 0.457390 0.805728 0.046 Uiso 1 1 calc R U . . .
O3 O 0.9598(4) 0.0988(3) 0.7599(8) 0.0296(12) Uani 1 1 d . . . . .
H3 H 0.924663 0.052497 0.696452 0.044 Uiso 1 1 calc R U . . .
O4 O 0.7794(4) -0.0012(3) 0.5829(8) 0.0311(12) Uani 1 1 d . . . . .
O5 O 0.5672(4) 0.2262(3) 0.5641(7) 0.0239(11) Uani 1 1 d . . . . .
O6 O 0.0374(4) 0.0955(3) 0.1808(8) 0.0338(13) Uani 1 1 d . . . . .
H6 H 0.025940 0.098928 0.052402 0.051 Uiso 1 1 calc R U . . .
C11 C 0.8520(5) 0.3336(4) 0.7717(9) 0.0213(15) Uani 1 1 d . . . . .
C12 C 0.9272(6) 0.2576(4) 0.7970(11) 0.0238(15) Uani 1 1 d . . . . .
H12 H 1.009307 0.265743 0.853769 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8827(6) 0.1712(5) 0.7401(10) 0.0239(16) Uani 1 1 d . . . . .
C14 C 0.7610(6) 0.1562(4) 0.6595(10) 0.0207(15) Uani 1 1 d . . . . .
C15 C 0.7166(6) 0.0676(5) 0.5837(10) 0.0247(16) Uani 1 1 d . . . . .
C16 C 0.5855(6) 0.0623(5) 0.4895(12) 0.0302(17) Uani 1 1 d . . . . .
H16A H 0.557446 -0.000338 0.512546 0.036 Uiso 1 1 calc R U . . .
H16B H 0.567824 0.072351 0.338794 0.036 Uiso 1 1 calc R U . . .
C17 C 0.5203(6) 0.1346(5) 0.5825(11) 0.0269(16) Uani 1 1 d . . . . .
H17 H 0.532453 0.120210 0.732049 0.032 Uiso 1 1 calc R U . . .
C18 C 0.6870(5) 0.2348(5) 0.6436(10) 0.0211(15) Uani 1 1 d . . . . .
C19 C 0.7310(5) 0.3223(4) 0.6957(9) 0.0194(14) Uani 1 1 d . . . . .
H19 H 0.679801 0.374045 0.680079 0.023 Uiso 1 1 calc R U . . .
C20 C 0.3906(6) 0.1343(5) 0.4778(11) 0.0252(16) Uani 1 1 d . . . . .
C21 C 0.3118(6) 0.1079(5) 0.5857(12) 0.0314(17) Uani 1 1 d . . . . .
H21 H 0.339171 0.095412 0.729295 0.038 Uiso 1 1 calc R U . . .
C22 C 0.1923(6) 0.0994(5) 0.4854(11) 0.0278(17) Uani 1 1 d . . . . .
H22 H 0.137646 0.085834 0.561780 0.033 Uiso 1 1 calc R U . . .
C23 C 0.1547(5) 0.1109(5) 0.2770(10) 0.0243(16) Uani 1 1 d . . . . .
C24 C 0.2323(6) 0.1408(5) 0.1660(12) 0.0317(18) Uani 1 1 d . . . . .
H24 H 0.204490 0.153846 0.022773 0.038 Uiso 1 1 calc R U . . .
C25 C 0.3492(6) 0.1510(5) 0.2674(11) 0.0292(17) Uani 1 1 d . . . . .
H25 H 0.402560 0.169889 0.192335 0.035 Uiso 1 1 calc R U . . .


_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 C8 1.235(8) . ?
N1 H1A 0.8652 . ?
N1 H1B 0.8651 . ?
N1 N2 1.406(8) . ?
N2 C8 1.384(8) . ?
N2 C9 1.358(8) . ?
N3 N4 1.364(8) . ?
N3 C9 1.315(9) . ?
N4 C7 1.312(8) . ?
C2 H2A 0.9500 . ?
C2 C1 1.3900 . ?
C2 C3 1.3900 . ?
C1 H1 0.9500 . ?
C1 C6 1.3900 . ?
C6 C5 1.3900 . ?
C6 C7 1.481(8) . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3A 0.9500 . ?
C7 C8 1.461(9) . ?
C9 C10 1.485(10) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O2 H2 0.8400 . ?
O2 C11 1.338(8) . ?
O3 H3 0.8400 . ?
O3 C13 1.369(8) . ?
O4 C15 1.241(8) . ?
O5 C17 1.453(8) . ?
O5 C18 1.378(7) . ?
O6 H6 0.8400 . ?
O6 C23 1.382(8) . ?
C11 C12 1.394(9) . ?
C11 C19 1.394(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.367(9) . ?
C13 C14 1.410(9) . ?
C14 C15 1.424(9) . ?
C14 C18 1.419(9) . ?
C15 C16 1.510(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.530(10) . ?
C17 H17 1.0000 . ?
C17 C20 1.505(9) . ?
C18 C19 1.375(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(10) . ?
C20 C25 1.389(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.398(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.363(10) . ?
C23 C24 1.400(10) . ?
C24 H24 0.9500 . ?
C24 C25 1.374(10) . ?
C25 H25 0.9500 . ?

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
H1A N1 H1B 108.9 . . ?
N2 N1 H1A 109.8 . . ?
N2 N1 H1B 110.2 . . ?
C8 N2 N1 117.0(5) . . ?
C9 N2 N1 120.4(5) . . ?
C9 N2 C8 122.3(6) . . ?
C9 N3 N4 120.6(6) . . ?
C7 N4 N3 120.2(6) . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C2 C1 H1 120.0 . . ?
C6 C1 C2 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C6 C5 120.0 . . ?
C1 C6 C7 119.6(4) . . ?
C5 C6 C7 120.3(4) . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3A 120.0 . . ?
N4 C7 C6 118.1(6) . . ?
N4 C7 C8 122.4(6) . . ?
C8 C7 C6 119.5(5) . . ?
O1 C8 N2 120.3(6) . . ?
O1 C8 C7 126.5(6) . . ?
N2 C8 C7 113.2(6) . . ?
N2 C9 C10 119.2(6) . . ?
N3 C9 N2 121.3(6) . . ?
N3 C9 C10 119.5(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 O2 H2 109.5 . . ?
C13 O3 H3 109.5 . . ?
C18 O5 C17 115.2(5) . . ?
C23 O6 H6 109.5 . . ?
O2 C11 C12 116.1(5) . . ?
O2 C11 C19 123.2(6) . . ?
C19 C11 C12 120.7(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(6) . . ?
C13 C12 H12 120.0 . . ?
O3 C13 C14 120.3(6) . . ?
C12 C13 O3 118.2(6) . . ?
C12 C13 C14 121.5(6) . . ?
C13 C14 C15 121.0(6) . . ?
C13 C14 C18 116.8(6) . . ?
C18 C14 C15 122.1(6) . . ?
O4 C15 C14 123.8(6) . . ?
O4 C15 C16 120.4(6) . . ?
C14 C15 C16 115.6(6) . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C15 C16 C17 111.6(6) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
O5 C17 C16 109.8(6) . . ?
O5 C17 H17 108.7 . . ?
O5 C17 C20 109.1(5) . . ?
C16 C17 H17 108.7 . . ?
C20 C17 C16 111.7(6) . . ?
C20 C17 H17 108.7 . . ?
O5 C18 C14 120.4(6) . . ?
C19 C18 O5 117.3(5) . . ?
C19 C18 C14 122.2(6) . . ?
C11 C19 H19 120.6 . . ?
C18 C19 C11 118.8(6) . . ?
C18 C19 H19 120.6 . . ?
C21 C20 C17 120.1(6) . . ?
C21 C20 C25 118.9(6) . . ?
C25 C20 C17 120.7(6) . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(7) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.4(7) . . ?
C23 C22 H22 120.3 . . ?
O6 C23 C24 121.4(6) . . ?
C22 C23 O6 117.9(6) . . ?
C22 C23 C24 120.7(6) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 119.0(7) . . ?
C25 C24 H24 120.5 . . ?
C20 C25 H25 119.4 . . ?
C24 C25 C20 121.1(7) . . ?
C24 C25 H25 119.4 . . ?

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
N1 N2 C8 O1 6.2(9) . . . . ?
N1 N2 C8 C7 -172.5(6) . . . . ?
N1 N2 C9 N3 173.2(6) . . . . ?
N1 N2 C9 C10 -7.5(10) . . . . ?
N3 N4 C7 C6 -177.9(6) . . . . ?
N3 N4 C7 C8 -0.9(11) . . . . ?
N4 N3 C9 N2 -1.2(10) . . . . ?
N4 N3 C9 C10 179.5(6) . . . . ?
N4 C7 C8 O1 -179.4(7) . . . . ?
N4 C7 C8 N2 -0.8(10) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 C7 -178.8(5) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C6 C7 N4 48.3(8) . . . . ?
C1 C6 C7 C8 -128.9(6) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C7 C8 O1 -2.4(11) . . . . ?
C6 C7 C8 N2 176.2(6) . . . . ?
C5 C6 C7 N4 -130.5(6) . . . . ?
C5 C6 C7 C8 52.4(7) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C7 C6 C5 C4 178.8(5) . . . . ?
C8 N2 C9 N3 -0.6(10) . . . . ?
C8 N2 C9 C10 178.7(6) . . . . ?
C9 N2 C8 O1 -179.8(7) . . . . ?
C9 N2 C8 C7 1.5(9) . . . . ?
C9 N3 N4 C7 1.9(10) . . . . ?
O2 C11 C12 C13 -179.5(6) . . . . ?
O2 C11 C19 C18 -178.8(6) . . . . ?
O3 C13 C14 C15 -4.5(10) . . . . ?
O3 C13 C14 C18 -179.9(6) . . . . ?
O4 C15 C16 C17 155.6(7) . . . . ?
O5 C17 C20 C21 -124.2(7) . . . . ?
O5 C17 C20 C25 62.5(8) . . . . ?
O5 C18 C19 C11 -178.4(6) . . . . ?
O6 C23 C24 C25 -177.1(6) . . . . ?
C11 C12 C13 O3 177.5(6) . . . . ?
C11 C12 C13 C14 -1.4(10) . . . . ?
C12 C11 C19 C18 -0.8(10) . . . . ?
C12 C13 C14 C15 174.3(7) . . . . ?
C12 C13 C14 C18 -1.1(10) . . . . ?
C13 C14 C15 O4 0.1(11) . . . . ?
C13 C14 C15 C16 -176.3(6) . . . . ?
C13 C14 C18 O5 179.2(6) . . . . ?
C13 C14 C18 C19 2.7(10) . . . . ?
C14 C15 C16 C17 -27.8(9) . . . . ?
C14 C18 C19 C11 -1.8(10) . . . . ?
C15 C14 C18 O5 3.9(10) . . . . ?
C15 C14 C18 C19 -172.7(6) . . . . ?
C15 C16 C17 O5 54.5(7) . . . . ?
C15 C16 C17 C20 175.7(6) . . . . ?
C16 C17 C20 C21 114.2(7) . . . . ?
C16 C17 C20 C25 -59.1(9) . . . . ?
C17 O5 C18 C14 25.1(9) . . . . ?
C17 O5 C18 C19 -158.2(6) . . . . ?
C17 C20 C21 C22 -174.3(7) . . . . ?
C17 C20 C25 C24 172.7(6) . . . . ?
C18 O5 C17 C16 -53.7(7) . . . . ?
C18 O5 C17 C20 -176.4(5) . . . . ?
C18 C14 C15 O4 175.2(7) . . . . ?
C18 C14 C15 C16 -1.2(10) . . . . ?
C19 C11 C12 C13 2.3(10) . . . . ?
C20 C21 C22 C23 4.7(10) . . . . ?
C21 C20 C25 C24 -0.7(11) . . . . ?
C21 C22 C23 O6 175.4(6) . . . . ?
C21 C22 C23 C24 -7.0(10) . . . . ?
C22 C23 C24 C25 5.4(10) . . . . ?
C23 C24 C25 C20 -1.5(10) . . . . ?
C25 C20 C21 C22 -0.8(11) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.159
_oxdiff_exptl_absorpt_empirical_full_min 0.841
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.947(2)
2 0.053(2)

####################################################################### 
# 
# 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_r20211130b
_database_code_depnum_ccdc_archive 'CCDC 2171266'
loop_
_audit_author_name
_audit_author_address
'Yuntian Xiao'
;Tianjin University
China
;
_audit_update_record             
;
2022-05-07 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-12-01
_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        Metamitron-Baicalein
_chemical_formula_moiety         'C10 H10 N4 O, C15 H10 O5'
_chemical_formula_sum            'C25 H20 N4 O6'
_chemical_formula_weight         472.45
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        P21/n
_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                   5.2165(2)
_cell_length_b                   13.1426(4)
_cell_length_c                   31.0132(10)
_cell_angle_alpha                90
_cell_angle_beta                 89.950(3)
_cell_angle_gamma                90
_cell_volume                     2126.21(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10188
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.0820
_cell_measurement_theta_min      2.4930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            21827
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         2.507
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00   10.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  60.00   1.00   10.00    --  -30.00  45.00  90.00  180
  3  ω   -120.00  60.00   1.00   10.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0019704000
_diffrn_orient_matrix_UB_12      -0.0517095000
_diffrn_orient_matrix_UB_13      -0.0065207000
_diffrn_orient_matrix_UB_21      0.0140002000
_diffrn_orient_matrix_UB_22      -0.0152372000
_diffrn_orient_matrix_UB_23      0.0218101000
_diffrn_orient_matrix_UB_31      -0.1352733000
_diffrn_orient_matrix_UB_32      -0.0022981000
_diffrn_orient_matrix_UB_33      0.0021783000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3901
_reflns_number_total             5417
_reflns_odcompleteness_completeness 92.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.19
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.321
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0105(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5417
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.026
_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)+(0.0580P)²+0.7257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1376
_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
2. Restrained distances
 C1-C7 \\sim C1A-C7
 with sigma of 0.01
3. Others
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4AA)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(H5)=Sof(C6)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C1A(H1A), C2A(H2A), C3A(H3A),
 C4A(H4AA), C5A(H5A), C14(H14), C18(H18), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25)
4.b Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C1A(C2A,C3A,C4A,C5A,C6A)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 1.2576(2) 0.88110(11) 0.72171(4) 0.0402(3) Uani 1 1 d . . . . .
N1 N 0.7042(3) 0.74862(11) 0.68509(5) 0.0314(3) Uani 1 1 d . . . . .
N2 N 0.6594(3) 0.69024(11) 0.72066(5) 0.0324(3) Uani 1 1 d . . . . .
N3 N 1.0091(3) 0.76333(11) 0.75512(4) 0.0304(3) Uani 1 1 d . . . . .
N4 N 1.1594(3) 0.76849(13) 0.79299(5) 0.0380(4) Uani 1 1 d . . . . .
C7 C 0.8994(3) 0.81143(12) 0.68378(5) 0.0278(4) Uani 1 1 d D . . . .
C8 C 1.0728(3) 0.82465(13) 0.72024(5) 0.0294(4) Uani 1 1 d . . . . .
C9 C 0.8109(3) 0.69726(13) 0.75426(5) 0.0313(4) Uani 1 1 d . . . . .
C10 C 0.7614(4) 0.63107(16) 0.79199(6) 0.0447(5) Uani 1 1 d . . . . .
H10A H 0.718095 0.673258 0.817016 0.067 Uiso 1 1 calc GR . . . .
H10B H 0.915055 0.590905 0.798353 0.067 Uiso 1 1 calc GR . . . .
H10C H 0.618227 0.585233 0.785581 0.067 Uiso 1 1 calc GR . . . .
H4A H 1.315(5) 0.796(2) 0.7826(8) 0.076(8) Uiso 1 1 d . . . . .
H4B H 1.074(4) 0.8176(18) 0.8109(8) 0.059(7) Uiso 1 1 d . . . . .
C1 C 1.0808(5) 0.96326(19) 0.64420(7) 0.0359(9) Uani 0.502(3) 1 d D . P A 1
H1 H 1.154262 0.987947 0.670193 0.043 Uiso 0.502(3) 1 calc R . P A 1
C2 C 1.1133(5) 1.01713(17) 0.60601(9) 0.0415(10) Uani 0.502(3) 1 d G . P A 1
H2 H 1.208965 1.078628 0.605907 0.050 Uiso 0.502(3) 1 calc R . P A 1
C3 C 1.0058(6) 0.9810(2) 0.56798(7) 0.0384(15) Uani 0.502(3) 1 d G . P A 1
H3 H 1.027970 1.017823 0.541886 0.046 Uiso 0.502(3) 1 calc R . P A 1
C4 C 0.8658(6) 0.8910(2) 0.56814(7) 0.0371(9) Uani 0.502(3) 1 d G . P A 1
H4 H 0.792271 0.866337 0.542149 0.045 Uiso 0.502(3) 1 calc R . P A 1
C5 C 0.8333(5) 0.83716(17) 0.60633(8) 0.0312(8) Uani 0.502(3) 1 d G . P A 1
H5 H 0.737565 0.775654 0.606434 0.037 Uiso 0.502(3) 1 calc R . P A 1
C6 C 0.9408(5) 0.87327(18) 0.64436(7) 0.030(2) Uani 0.502(3) 1 d G . P A 1
C1A C 1.1707(4) 0.9029(2) 0.62920(8) 0.0349(9) Uani 0.498(3) 1 d D . P A 2
H1A H 1.315364 0.894800 0.647471 0.042 Uiso 0.498(3) 1 calc R . P A 2
C2A C 1.1965(4) 0.9525(2) 0.58984(9) 0.0430(11) Uani 0.498(3) 1 d G . P A 2
H2A H 1.358743 0.978222 0.581208 0.052 Uiso 0.498(3) 1 calc R . P A 2
C3A C 0.9848(6) 0.9643(3) 0.56312(8) 0.0481(19) Uani 0.498(3) 1 d G . P A 2
H3A H 1.002418 0.998196 0.536215 0.058 Uiso 0.498(3) 1 calc R . P A 2
C4A C 0.7474(5) 0.9266(3) 0.57575(9) 0.0462(11) Uani 0.498(3) 1 d G . P A 2
H4AA H 0.602712 0.934748 0.557484 0.055 Uiso 0.498(3) 1 calc R . P A 2
C5A C 0.7216(4) 0.8771(2) 0.61511(10) 0.0387(10) Uani 0.498(3) 1 d G . P A 2
H5A H 0.559327 0.851326 0.623746 0.046 Uiso 0.498(3) 1 calc R . P A 2
C6A C 0.9333(5) 0.8652(2) 0.64184(7) 0.028(2) Uani 0.498(3) 1 d G . P A 2
O2 O -0.4143(2) 0.40601(9) 0.64389(4) 0.0286(3) Uani 1 1 d . . . . .
O3 O -0.1250(2) 0.42812(9) 0.71647(4) 0.0299(3) Uani 1 1 d . . . . .
O4 O 0.2649(2) 0.56060(9) 0.71779(4) 0.0305(3) Uani 1 1 d . . . . .
O5 O 0.1224(2) 0.64865(8) 0.57105(3) 0.0267(3) Uani 1 1 d . . . . .
O6 O -0.5026(2) 0.46210(9) 0.56625(4) 0.0304(3) Uani 1 1 d . . . . .
C11 C -0.2152(3) 0.47250(11) 0.64394(5) 0.0235(3) Uani 1 1 d . . . . .
C12 C -0.0674(3) 0.48390(12) 0.68028(5) 0.0241(3) Uani 1 1 d . . . . .
C13 C 0.1376(3) 0.55299(11) 0.68009(5) 0.0240(3) Uani 1 1 d . . . . .
C14 C 0.2011(3) 0.60839(12) 0.64356(5) 0.0253(3) Uani 1 1 d . . . . .
H14 H 0.341957 0.654228 0.643546 0.030 Uiso 1 1 calc R . . . .
C15 C 0.0521(3) 0.59453(11) 0.60713(5) 0.0237(3) Uani 1 1 d . . . . .
C16 C -0.1576(3) 0.52910(11) 0.60634(5) 0.0232(3) Uani 1 1 d . . . . .
C17 C -0.3089(3) 0.51894(12) 0.56771(5) 0.0249(3) Uani 1 1 d . . . . .
C18 C -0.2217(3) 0.57689(12) 0.53141(5) 0.0275(4) Uani 1 1 d . . . . .
H18 H -0.313194 0.572906 0.504990 0.033 Uiso 1 1 calc R . . . .
C19 C -0.0126(3) 0.63697(12) 0.53395(5) 0.0256(3) Uani 1 1 d . . . . .
C20 C 0.0976(3) 0.69640(12) 0.49805(5) 0.0267(3) Uani 1 1 d . . . . .
C21 C 0.3115(3) 0.75838(13) 0.50443(6) 0.0329(4) Uani 1 1 d . . . . .
H21 H 0.384711 0.764464 0.532347 0.040 Uiso 1 1 calc R . . . .
C22 C 0.4171(4) 0.81106(14) 0.46998(6) 0.0391(4) Uani 1 1 d . . . . .
H22 H 0.563174 0.852937 0.474387 0.047 Uiso 1 1 calc R . . . .
C23 C 0.3116(4) 0.80309(14) 0.42943(6) 0.0405(5) Uani 1 1 d . . . . .
H23 H 0.385705 0.839011 0.405935 0.049 Uiso 1 1 calc R . . . .
C24 C 0.0986(4) 0.74298(14) 0.42293(6) 0.0370(4) Uani 1 1 d . . . . .
H24 H 0.024962 0.738141 0.394994 0.044 Uiso 1 1 calc R . . . .
C25 C -0.0085(3) 0.68962(13) 0.45699(5) 0.0314(4) Uani 1 1 d . . . . .
H25 H -0.155116 0.648196 0.452307 0.038 Uiso 1 1 calc R . . . .
H2B H -0.480(5) 0.4137(18) 0.6175(8) 0.064(7) Uiso 1 1 d . . . . .
H3B H 0.002(6) 0.438(2) 0.7353(9) 0.086(9) Uiso 1 1 d . . . . .
H4C H 0.408(5) 0.6057(19) 0.7167(7) 0.065(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.217(2) . ?
N1 N2 1.364(2) . ?
N1 C7 1.312(2) . ?
N2 C9 1.312(2) . ?
N3 N4 1.4143(19) . ?
N3 C8 1.389(2) . ?
N3 C9 1.350(2) . ?
N4 H4A 0.94(3) . ?
N4 H4B 0.96(2) . ?
C7 C8 1.459(2) . ?
C7 C6 1.484(2) . ?
C7 C6A 1.491(2) . ?
C9 C10 1.481(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 H2 0.9500 . ?
C2 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C5 1.3900 . ?
C5 H5 0.9500 . ?
C5 C6 1.3900 . ?
C1A H1A 0.9500 . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A H2A 0.9500 . ?
C2A C3A 1.3900 . ?
C3A H3A 0.9500 . ?
C3A C4A 1.3900 . ?
C4A H4AA 0.9500 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3900 . ?
O2 C11 1.3571(19) . ?
O2 H2B 0.89(2) . ?
O3 C12 1.3737(18) . ?
O3 H3B 0.89(3) . ?
O4 C13 1.3488(18) . ?
O4 H4C 0.95(3) . ?
O5 C15 1.3754(18) . ?
O5 C19 1.3585(18) . ?
O6 C17 1.2574(19) . ?
C11 C12 1.374(2) . ?
C11 C16 1.415(2) . ?
C12 C13 1.403(2) . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(2) . ?
C15 C16 1.392(2) . ?
C16 C17 1.441(2) . ?
C17 C18 1.433(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.349(2) . ?
C19 C20 1.476(2) . ?
C20 C21 1.396(2) . ?
C20 C25 1.392(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.378(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(2) . ?
C25 H25 0.9500 . ?

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
C7 N1 N2 120.76(14) . . ?
C9 N2 N1 120.01(15) . . ?
C8 N3 N4 119.12(15) . . ?
C9 N3 N4 118.16(15) . . ?
C9 N3 C8 122.71(14) . . ?
N3 N4 H4A 102.3(16) . . ?
N3 N4 H4B 104.8(14) . . ?
H4A N4 H4B 110(2) . . ?
N1 C7 C8 122.21(15) . . ?
N1 C7 C6 118.84(16) . . ?
N1 C7 C6A 114.62(17) . . ?
C8 C7 C6 118.92(17) . . ?
C8 C7 C6A 123.14(17) . . ?
O1 C8 N3 120.88(15) . . ?
O1 C8 C7 126.38(16) . . ?
N3 C8 C7 112.73(15) . . ?
N2 C9 N3 121.51(16) . . ?
N2 C9 C10 118.79(17) . . ?
N3 C9 C10 119.70(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 123.02(17) . . ?
C5 C6 C7 116.98(17) . . ?
C5 C6 C1 120.0 . . ?
C2A C1A H1A 120.0 . . ?
C2A C1A C6A 120.0 . . ?
C6A C1A H1A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C1A C2A C3A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A H4AA 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C5A C4A H4AA 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C1A C6A C7 121.31(17) . . ?
C5A C6A C7 118.69(17) . . ?
C5A C6A C1A 120.0 . . ?
C11 O2 H2B 102.8(16) . . ?
C12 O3 H3B 107.4(19) . . ?
C13 O4 H4C 113.6(14) . . ?
C19 O5 C15 119.51(13) . . ?
O2 C11 C12 120.07(14) . . ?
O2 C11 C16 119.96(14) . . ?
C12 C11 C16 119.96(14) . . ?
O3 C12 C11 119.28(14) . . ?
O3 C12 C13 121.02(14) . . ?
C11 C12 C13 119.70(14) . . ?
O4 C13 C12 114.84(14) . . ?
O4 C13 C14 123.47(15) . . ?
C14 C13 C12 121.68(14) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.62(15) . . ?
C15 C14 H14 121.2 . . ?
O5 C15 C14 116.51(14) . . ?
O5 C15 C16 120.95(14) . . ?
C14 C15 C16 122.54(14) . . ?
C11 C16 C17 121.35(14) . . ?
C15 C16 C11 118.46(14) . . ?
C15 C16 C17 120.19(14) . . ?
O6 C17 C16 121.70(14) . . ?
O6 C17 C18 122.81(14) . . ?
C18 C17 C16 115.49(14) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.42(15) . . ?
C19 C18 H18 119.3 . . ?
O5 C19 C20 112.15(14) . . ?
C18 C19 O5 122.37(14) . . ?
C18 C19 C20 125.47(15) . . ?
C21 C20 C19 120.85(15) . . ?
C25 C20 C19 120.07(15) . . ?
C25 C20 C21 119.07(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.95(17) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.46(18) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 119.99(17) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.21(17) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 119.8 . . ?
C24 C25 C20 120.32(17) . . ?
C24 C25 H25 119.8 . . ?

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
N1 N2 C9 N3 1.7(2) . . . . ?
N1 N2 C9 C10 -178.48(15) . . . . ?
N1 C7 C8 O1 -179.97(16) . . . . ?
N1 C7 C8 N3 0.8(2) . . . . ?
N1 C7 C6 C1 157.95(17) . . . . ?
N1 C7 C6 C5 -22.4(2) . . . . ?
N1 C7 C6A C1A -155.75(18) . . . . ?
N1 C7 C6A C5A 24.1(3) . . . . ?
N2 N1 C7 C8 -1.9(2) . . . . ?
N2 N1 C7 C6 179.89(17) . . . . ?
N2 N1 C7 C6A 176.34(17) . . . . ?
N4 N3 C8 O1 1.2(2) . . . . ?
N4 N3 C8 C7 -179.53(14) . . . . ?
N4 N3 C9 N2 178.22(15) . . . . ?
N4 N3 C9 C10 -1.6(2) . . . . ?
C7 N1 N2 C9 0.7(2) . . . . ?
C8 N3 C9 N2 -2.9(2) . . . . ?
C8 N3 C9 C10 177.31(15) . . . . ?
C8 C7 C6 C1 -20.3(3) . . . . ?
C8 C7 C6 C5 159.31(16) . . . . ?
C8 C7 C6A C1A 22.5(3) . . . . ?
C8 C7 C6A C5A -157.72(17) . . . . ?
C9 N3 C8 O1 -177.75(15) . . . . ?
C9 N3 C8 C7 1.6(2) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C1 C6 C7 179.6(2) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C6 C7 C8 O1 -1.8(3) . . . . ?
C6 C7 C8 N3 178.99(17) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C1A C6A C7 179.8(3) . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C7 -179.8(3) . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C6A C7 C8 O1 1.9(3) . . . . ?
C6A C7 C8 N3 -177.30(18) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
O2 C11 C12 O3 -0.6(2) . . . . ?
O2 C11 C12 C13 -179.83(14) . . . . ?
O2 C11 C16 C15 -178.26(13) . . . . ?
O2 C11 C16 C17 0.9(2) . . . . ?
O3 C12 C13 O4 -1.2(2) . . . . ?
O3 C12 C13 C14 178.76(14) . . . . ?
O4 C13 C14 C15 -178.99(14) . . . . ?
O5 C15 C16 C11 177.66(13) . . . . ?
O5 C15 C16 C17 -1.5(2) . . . . ?
O5 C19 C20 C21 -2.0(2) . . . . ?
O5 C19 C20 C25 176.80(14) . . . . ?
O6 C17 C18 C19 -179.78(15) . . . . ?
C11 C12 C13 O4 177.97(14) . . . . ?
C11 C12 C13 C14 -2.1(2) . . . . ?
C11 C16 C17 O6 2.4(2) . . . . ?
C11 C16 C17 C18 -177.04(14) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
C12 C11 C16 C17 -179.99(14) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C13 C14 C15 O5 -178.61(13) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C14 C15 C16 C11 -1.9(2) . . . . ?
C14 C15 C16 C17 178.91(14) . . . . ?
C15 O5 C19 C18 2.8(2) . . . . ?
C15 O5 C19 C20 -176.93(12) . . . . ?
C15 C16 C17 O6 -178.49(14) . . . . ?
C15 C16 C17 C18 2.1(2) . . . . ?
C16 C11 C12 O3 -179.73(14) . . . . ?
C16 C11 C12 C13 1.1(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 O5 -2.1(2) . . . . ?
C17 C18 C19 C20 177.58(15) . . . . ?
C18 C19 C20 C21 178.37(16) . . . . ?
C18 C19 C20 C25 -2.9(2) . . . . ?
C19 O5 C15 C14 178.67(13) . . . . ?
C19 O5 C15 C16 -0.9(2) . . . . ?
C19 C20 C21 C22 177.94(16) . . . . ?
C19 C20 C25 C24 -178.17(15) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C20 C25 C24 0.6(3) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C23 C24 C25 C20 0.1(3) . . . . ?
C25 C20 C21 C22 -0.8(3) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.804
