#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:25:53 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/55/7245547.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_7245547
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, C9 H8 O2'
_chemical_formula_sum            'C19 H18 N4 O3'
_chemical_formula_weight         350.37
_chemical_name_systematic        'Metamitron-Cinnamic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-07 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.812(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5056(5)
_cell_length_b                   28.8708(9)
_cell_length_c                   13.6219(8)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.1290
_cell_measurement_theta_min      2.1630
_cell_volume                     3393.2(3)
_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)'
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_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_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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_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_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_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_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_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0517
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5073
_reflns_number_total             7000
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc02949a2.cif
_cod_data_source_block           123
_cod_depositor_comments
'Adding full bibliography for 7245547--7245549.cif.'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7245547
_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   0.991
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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)
;
_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
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'
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 . . .
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
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_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_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) . . . . ?
