#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:25:53 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/55/7245548.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245548
loop_
_publ_author_name
'Xiao, Yuntian'
'Wu, Chuanhua'
'Zhou, Ling'
'Yin, Qiuxiang'
'Yang, Jingxiang'
_publ_section_title
;
 Cocrystal engineering strategy for sustained release and leaching
 reduction of herbicides: a case study of metamitron
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              8088
_journal_page_last               8099
_journal_paper_doi               10.1039/D2GC02949A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C10 H10 N4 O, C15 H12 O5'
_chemical_formula_sum            'C25 H22 N4 O6'
_chemical_formula_weight         474.46
_chemical_name_systematic        Metamitron-Naringenin
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-12-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.16 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2022-05-07 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.770(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8352(12)
_cell_length_b                   14.4349(12)
_cell_length_c                   6.7368(8)
_cell_measurement_reflns_used    4761
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.6800
_cell_measurement_theta_min      2.2610
_cell_volume                     1107.6(2)
_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)'
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_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_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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_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_crystal_density_diffrn    1.423
_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
_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_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0574
_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
_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_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc02949a2.cif
_cod_data_source_block           r20211203a
_cod_depositor_comments
'Adding full bibliography for 7245547--7245549.cif.'
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               7245548
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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.
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.984
_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)
;
_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_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
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 . . .
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'
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_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_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) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.947(2)
2 0.053(2)
