#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:31:53 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286079 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/68/7246889.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_7246889
loop_
_publ_author_name
'Wang, Zhi-Qing'
'Dai, Xia-Lin'
'Gu, Dai-Lin'
'Wu, Chao'
'Lu, Tong-Bu'
'Long, Xiang-Tian'
'Chen, Jia-Mei'
_publ_section_title
;
 Cocrystallization of lenvatinib and temozolomide to improve the
 performance in terms of stability, dissolution, and tabletability
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              4189
_journal_page_last               4198
_journal_paper_doi               10.1039/D3CE00473B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C21 H19 Cl N4 O4, C6 H6 N6 O2, C H4 O'
_chemical_formula_sum            'C28 H29 Cl N10 O7'
_chemical_formula_weight         653.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-06-18 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                68.871(3)
_cell_angle_beta                 78.281(3)
_cell_angle_gamma                79.368(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1842(3)
_cell_length_b                   14.4765(5)
_cell_length_c                   15.9555(4)
_cell_measurement_reflns_used    6838
_cell_measurement_temperature    297.24(10)
_cell_measurement_theta_max      78.5070
_cell_measurement_theta_min      2.9780
_cell_volume                     1504.29(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297.24(10)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -10.00   0.50    0.50    --    0.00 -36.00 -90.17  158
  2  ω    -89.00 -60.00   0.50    0.50    --    0.00 -57.00 -30.00   58
  3  ω    -25.00   0.00   0.50    0.50    --    0.00  57.00 -90.00   50
  4  ω    -87.00 -31.00   0.50    0.50    --    0.00 -57.00  30.00  112
  5  ω    -52.00  28.00   0.50    0.50    --    0.00 -57.00 -30.00  160
  6  ω      5.00  66.00   0.50    0.50    --    0.00  57.00 -90.00  122
  7  ω    110.00 135.00   0.50    5.00    --  106.20 -45.00 150.00   50
  8  ω     73.00  99.00   0.50    5.00    --  106.20 -45.00 150.00   52
  9  ω    144.00 170.00   0.50    5.00    --  106.20  15.00  90.00   52
 10  ω     20.00  97.00   0.50    5.00    --  106.20 -82.00-120.00  154
 11  ω     19.00 142.00   0.50    5.00    --  106.20 -82.00  90.00  246
 12  ω     17.00  98.00   0.50    5.00    --  106.20 -30.00  90.00  162
 13  ω    103.00 134.00   0.50    5.00    --  106.20 -30.00  90.00   62
 14  ω     19.00 110.00   0.50    5.00    --  106.20 -61.00 -90.00  182
 15  ω     23.00  49.00   0.50    5.00    --  106.20 -45.00 150.00   52
 16  ω    123.00 196.00   0.50    5.00    --  106.20  30.00 -60.00  146
 17  ω     73.00 112.00   0.50    5.00    --  106.20  30.00 -60.00   78
 18  ω     90.00 135.00   0.50    5.00    --  106.20 -82.00   0.00   90
 19  ω     51.00 142.00   0.50    5.00    --  106.20 -82.00 -90.00  182
 20  ω     92.00 117.00   0.50    5.00    --  106.20  61.00 -60.00   50
 21  ω     58.00 117.00   0.50    5.00    --  106.20 -82.00 150.00  118
 22  ω     18.00  74.00   0.50    5.00    --  106.20 -30.00  60.00  112
 23  ω    111.00 140.00   0.50    5.00    --  106.20 -30.00  60.00   58
 24  ω     49.00  90.00   0.50    5.00    --  106.20 -82.00  30.00   82
 25  ω    103.00 129.00   0.50    5.00    --  106.20 -82.00  30.00   52
 26  ω     30.00 138.00   0.50    5.00    --  106.20 -30.00 -60.00  216
 27  ω     76.00 101.00   0.50    5.00    --  106.20 -77.00-180.00   50
 28  ω     76.00 106.00   0.50    5.00    --  106.20 -82.00  60.00   60
 29  ω     19.00 133.00   0.50    5.00    --  106.20  15.00  90.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12610
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        63.999
_diffrn_reflns_theta_max         63.999
_diffrn_reflns_theta_min         3.003
_exptl_absorpt_coefficient_mu    1.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         4849
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0500
_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)+(0.0886P)²+0.0253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1482
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3764
_reflns_number_total             4849
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00473b2.cif
_cod_data_source_block           211006-tmz-len
_cod_depositor_comments          'Adding full bibliography for 7246889.cif.'
_cod_database_code               7246889
_shelx_shelxl_version_number     2016/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C3-C1B \\sim C3-C1A
 with sigma of 0.04
 C1B-C2B \\sim C1A-C2A
 with sigma of 0.02
 C3-C2B \\sim C3-C2A
 with sigma of 0.04
 C2B-C3 \\sim C3-C2A
 with sigma of 0.01
 C1B-C3 \\sim C3-C1A
 with sigma of 0.01
 C2A-C1A \\sim C1B-C2B
 with sigma of 0.01
3. Rigid bond restraints
 C3, C1B, C2B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C3, C2A, C1A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C3 \\sim C1B \\sim C2B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C3 \\sim C2A \\sim C1A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C3) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C2B) \\sim Ueq: with sigma of
0.04 and sigma for terminal atoms of 0.06
Uanis(C3) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C1A) \\sim Ueq: with sigma of
0.04 and sigma for terminal atoms of 0.06
5. Rigid body (RIGU) restrains
 C3, C1B, C2B
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
 C3, C2A, C1A
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
6. Others
 Sof(H3B)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(H3A)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C3(H3A), C3(H3B)
7.b Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB), C2B(H2BA,H2BB), C2A(H2AA,H2AB), C1A(H1AA,H1AB)
7.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C17(H17), C16(H16), C9(H9), C25(H25), C11(H11), C12(H12),
 C6(H6), C8(H8)
7.d X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N4(H4A,H4B)
7.e Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
7.f Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_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
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.19823(8) 1.02994(5) 0.34459(5) 0.0629(2) Uani 1 1 d . . . . .
O4 O 0.7486(3) 0.46218(11) 0.95105(10) 0.0509(4) Uani 1 1 d . . . . .
O2 O 0.6062(3) 0.80538(11) 0.58179(10) 0.0483(4) Uani 1 1 d . . . . .
O6 O 0.8973(3) 0.23388(12) 1.40129(12) 0.0558(4) Uani 1 1 d . . . . .
O3 O 0.6699(3) 0.77131(12) 0.88195(12) 0.0587(5) Uani 1 1 d . . . . .
O1 O 0.8161(3) 0.95470(12) 0.15124(12) 0.0589(5) Uani 1 1 d . . . . .
N7 N 0.8515(2) 0.40332(12) 1.33132(12) 0.0380(4) Uani 1 1 d . . . . .
N8 N 0.7926(3) 0.46925(13) 1.17645(13) 0.0424(4) Uani 1 1 d . . . . .
N10 N 0.8328(3) 0.30063(12) 1.25493(13) 0.0417(4) Uani 1 1 d . . . . .
O5 O 0.7310(3) 0.69619(12) 1.14335(13) 0.0647(5) Uani 1 1 d . . . . .
N2 N 0.5685(3) 1.03988(13) 0.21923(12) 0.0422(4) Uani 1 1 d . . . . .
H2 H 0.478034 1.088769 0.209227 0.051 Uiso 1 1 calc R . . . .
N3 N 0.6658(3) 0.49520(13) 0.65161(13) 0.0443(4) Uani 1 1 d . . . . .
N6 N 0.8479(3) 0.53940(14) 1.36359(13) 0.0434(4) Uani 1 1 d . . . . .
O7 O 1.1328(3) 0.68482(14) 0.37825(17) 0.0741(6) Uani 1 1 d . . . . .
H7 H 1.175765 0.638096 0.359575 0.111 Uiso 1 1 calc GR . . . .
N9 N 0.8016(3) 0.38039(13) 1.17683(13) 0.0443(4) Uani 1 1 d . . . . .
N1 N 0.6564(3) 1.09609(15) 0.06504(13) 0.0532(5) Uani 1 1 d . . . . .
H1 H 0.562936 1.142864 0.064334 0.064 Uiso 1 1 calc R . . . .
N5 N 0.8227(3) 0.73872(14) 1.24973(15) 0.0550(5) Uani 1 1 d . . . . .
H5A H 0.809270 0.801368 1.218834 0.066 Uiso 1 1 calc R . . . .
H5B H 0.860502 0.718598 1.301916 0.066 Uiso 1 1 calc R . . . .
N4 N 0.7342(3) 0.62754(15) 0.99137(13) 0.0561(6) Uani 1 1 d . . . . .
H4A H 0.735654 0.657792 1.028723 0.067 Uiso 1 1 calc R . . . .
H4B H 0.754926 0.563485 1.008423 0.067 Uiso 1 1 calc R . . . .
C15 C 0.6738(3) 0.54019(15) 0.71237(14) 0.0358(4) Uani 1 1 d . . . . .
C14 C 0.6547(3) 0.64487(14) 0.69027(14) 0.0334(4) Uani 1 1 d . . . . .
C5 C 0.5820(3) 0.98132(14) 0.31002(14) 0.0373(5) Uani 1 1 d . . . . .
C17 C 0.6658(3) 0.68453(14) 0.75759(14) 0.0341(4) Uani 1 1 d . . . . .
H17 H 0.652859 0.753446 0.742908 0.041 Uiso 1 1 calc R . . . .
C19 C 0.6952(3) 0.62495(15) 0.84418(14) 0.0352(4) Uani 1 1 d . . . . .
C24 C 0.8149(3) 0.48384(14) 1.25378(14) 0.0349(4) Uani 1 1 d . . . . .
C18 C 0.7159(3) 0.51903(15) 0.86530(14) 0.0380(5) Uani 1 1 d . . . . .
C13 C 0.6272(3) 0.70471(15) 0.60004(14) 0.0379(5) Uani 1 1 d . . . . .
C20 C 0.7001(3) 0.67925(15) 0.90812(14) 0.0397(5) Uani 1 1 d . . . . .
C16 C 0.7034(3) 0.47890(15) 0.80144(15) 0.0397(5) Uani 1 1 d . . . . .
H16 H 0.714486 0.409940 0.816901 0.048 Uiso 1 1 calc R . . . .
C23 C 0.8136(3) 0.56745(15) 1.27562(14) 0.0378(5) Uani 1 1 d . . . . .
C7 C 0.4194(3) 0.97019(15) 0.37523(15) 0.0384(5) Uani 1 1 d . . . . .
C26 C 0.8642(3) 0.30468(15) 1.33511(15) 0.0401(5) Uani 1 1 d . . . . .
C4 C 0.6883(3) 1.02526(15) 0.14509(15) 0.0418(5) Uani 1 1 d . . . . .
C9 C 0.4249(3) 0.91245(15) 0.46587(14) 0.0410(5) Uani 1 1 d . . . . .
H9 H 0.314147 0.905918 0.508429 0.049 Uiso 1 1 calc R . . . .
C25 C 0.8706(3) 0.44129(16) 1.39528(15) 0.0433(5) Uani 1 1 d . . . . .
H25 H 0.896190 0.403034 1.453520 0.052 Uiso 1 1 calc R . . . .
C22 C 0.7853(3) 0.67329(16) 1.21699(16) 0.0433(5) Uani 1 1 d . . . . .
C11 C 0.6214(3) 0.65901(17) 0.53903(15) 0.0463(5) Uani 1 1 d . . . . .
H11 H 0.604798 0.696305 0.479320 0.056 Uiso 1 1 calc R . . . .
C10 C 0.6008(3) 0.86509(15) 0.49047(15) 0.0422(5) Uani 1 1 d . . . . .
C12 C 0.6409(3) 0.55525(17) 0.56892(16) 0.0459(5) Uani 1 1 d . . . . .
H12 H 0.635920 0.525499 0.526714 0.055 Uiso 1 1 calc R . . . .
C6 C 0.7558(3) 0.93526(17) 0.33965(16) 0.0467(5) Uani 1 1 d . . . . .
H6 H 0.868082 0.943508 0.298139 0.056 Uiso 1 1 calc R . . . .
C8 C 0.7656(3) 0.87762(18) 0.42920(17) 0.0496(6) Uani 1 1 d . . . . .
H8 H 0.883266 0.847517 0.447770 0.059 Uiso 1 1 calc R . . . .
C27 C 0.8357(4) 0.20415(17) 1.2444(2) 0.0577(7) Uani 1 1 d . . . . .
H27A H 0.734685 0.207853 1.211648 0.087 Uiso 1 1 calc GR . . . .
H27B H 0.817366 0.153829 1.303245 0.087 Uiso 1 1 calc GR . . . .
H27C H 0.956791 0.187395 1.211380 0.087 Uiso 1 1 calc GR . . . .
C21 C 0.7855(4) 0.35570(17) 0.97218(18) 0.0593(7) Uani 1 1 d . . . . .
H21A H 0.893955 0.339856 0.931228 0.089 Uiso 1 1 calc GR . . . .
H21B H 0.675322 0.331364 0.965916 0.089 Uiso 1 1 calc GR . . . .
H21C H 0.811968 0.324857 1.033488 0.089 Uiso 1 1 calc GR . . . .
C3 C 0.7744(4) 1.0953(2) -0.01876(17) 0.0582(6) Uani 1 1 d D U . . .
H3A H 0.904653 1.112064 -0.027442 0.070 Uiso 0.402(14) 1 calc R . P A 1
H3B H 0.912639 1.085142 -0.017477 0.070 Uiso 0.598(14) 1 calc R . P A 2
C28 C 1.2718(5) 0.7492(3) 0.3557(2) 0.0796(9) Uani 1 1 d . . . . .
H28A H 1.271209 0.770761 0.406026 0.119 Uiso 1 1 calc GR . . . .
H28B H 1.244211 0.806121 0.303639 0.119 Uiso 1 1 calc GR . . . .
H28C H 1.395569 0.714899 0.341900 0.119 Uiso 1 1 calc GR . . . .
C1B C 0.6821(18) 1.1281(11) -0.1023(6) 0.078(2) Uani 0.402(14) 1 d D U P A 1
H1BA H 0.754242 1.164749 -0.159378 0.093 Uiso 0.402(14) 1 calc R . P A 1
H1BB H 0.544928 1.148114 -0.096373 0.093 Uiso 0.402(14) 1 calc R . P A 1
C2B C 0.7515(14) 1.0202(8) -0.0587(8) 0.0618(18) Uani 0.402(14) 1 d D U P A 1
H2BA H 0.656199 0.975060 -0.026471 0.074 Uiso 0.402(14) 1 calc R . P A 1
H2BB H 0.865494 0.991693 -0.089470 0.074 Uiso 0.402(14) 1 calc R . P A 1
C2A C 0.7144(13) 1.0593(7) -0.0842(4) 0.0709(16) Uani 0.598(14) 1 d D U P A 2
H2AA H 0.592146 1.033110 -0.067663 0.085 Uiso 0.598(14) 1 calc R . P A 2
H2AB H 0.813110 1.026717 -0.119115 0.085 Uiso 0.598(14) 1 calc R . P A 2
C1A C 0.7122(9) 1.1681(5) -0.1045(3) 0.0613(14) Uani 0.598(14) 1 d D U P A 2
H1AA H 0.588706 1.208057 -0.100251 0.074 Uiso 0.598(14) 1 calc R . P A 2
H1AB H 0.809705 1.201663 -0.151712 0.074 Uiso 0.598(14) 1 calc R . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C18 O4 C21 117.84(17) . . ?
C13 O2 C10 116.19(16) . . ?
C24 N7 C26 122.35(17) . . ?
C25 N7 C24 107.21(16) . . ?
C25 N7 C26 130.44(18) . . ?
N9 N8 C24 118.98(18) . . ?
N9 N10 C27 112.84(18) . . ?
C26 N10 N9 127.08(17) . . ?
C26 N10 C27 120.06(19) . . ?
C5 N2 H2 117.4 . . ?
C4 N2 H2 117.4 . . ?
C4 N2 C5 125.12(18) . . ?
C12 N3 C15 116.13(18) . . ?
C25 N6 C23 107.01(17) . . ?
C28 O7 H7 109.5 . . ?
N8 N9 N10 119.80(17) . . ?
C4 N1 H1 119.2 . . ?
C4 N1 C3 121.7(2) . . ?
C3 N1 H1 119.2 . . ?
H5A N5 H5B 120.0 . . ?
C22 N5 H5A 120.0 . . ?
C22 N5 H5B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C20 N4 H4A 120.0 . . ?
C20 N4 H4B 120.0 . . ?
N3 C15 C14 123.10(19) . . ?
N3 C15 C16 118.19(18) . . ?
C16 C15 C14 118.71(18) . . ?
C15 C14 C13 117.56(18) . . ?
C17 C14 C15 119.01(18) . . ?
C17 C14 C13 123.42(18) . . ?
C7 C5 N2 120.38(18) . . ?
C7 C5 C6 117.1(2) . . ?
C6 C5 N2 122.5(2) . . ?
C14 C17 H17 118.8 . . ?
C19 C17 C14 122.32(18) . . ?
C19 C17 H17 118.8 . . ?
C17 C19 C18 118.00(18) . . ?
C17 C19 C20 115.55(17) . . ?
C18 C19 C20 126.45(18) . . ?
N8 C24 N7 120.95(17) . . ?
N8 C24 C23 133.49(19) . . ?
C23 C24 N7 105.54(17) . . ?
O4 C18 C19 116.52(18) . . ?
O4 C18 C16 122.77(18) . . ?
C16 C18 C19 120.71(18) . . ?
O2 C13 C14 115.79(17) . . ?
O2 C13 C11 125.15(19) . . ?
C11 C13 C14 119.05(19) . . ?
O3 C20 N4 121.27(19) . . ?
O3 C20 C19 119.49(18) . . ?
N4 C20 C19 119.24(18) . . ?
C15 C16 H16 119.4 . . ?
C18 C16 C15 121.24(18) . . ?
C18 C16 H16 119.4 . . ?
N6 C23 C22 122.49(18) . . ?
C24 C23 N6 109.41(18) . . ?
C24 C23 C22 128.08(19) . . ?
C5 C7 Cl1 119.90(16) . . ?
C5 C7 C9 122.63(19) . . ?
C9 C7 Cl1 117.48(17) . . ?
O6 C26 N7 123.4(2) . . ?
O6 C26 N10 125.8(2) . . ?
N10 C26 N7 110.76(17) . . ?
O1 C4 N2 122.9(2) . . ?
O1 C4 N1 122.9(2) . . ?
N1 C4 N2 114.22(19) . . ?
C7 C9 H9 121.2 . . ?
C10 C9 C7 117.6(2) . . ?
C10 C9 H9 121.2 . . ?
N7 C25 H25 124.6 . . ?
N6 C25 N7 110.83(18) . . ?
N6 C25 H25 124.6 . . ?
O5 C22 N5 123.8(2) . . ?
O5 C22 C23 120.69(19) . . ?
N5 C22 C23 115.5(2) . . ?
C13 C11 H11 120.9 . . ?
C13 C11 C12 118.1(2) . . ?
C12 C11 H11 120.9 . . ?
C9 C10 O2 117.7(2) . . ?
C8 C10 O2 120.68(19) . . ?
C8 C10 C9 121.6(2) . . ?
N3 C12 C11 126.01(19) . . ?
N3 C12 H12 117.0 . . ?
C11 C12 H12 117.0 . . ?
C5 C6 H6 119.2 . . ?
C8 C6 C5 121.5(2) . . ?
C8 C6 H6 119.2 . . ?
C10 C8 C6 119.5(2) . . ?
C10 C8 H8 120.3 . . ?
C6 C8 H8 120.3 . . ?
N10 C27 H27A 109.5 . . ?
N10 C27 H27B 109.5 . . ?
N10 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C3 H3A 116.1 . . ?
N1 C3 H3B 115.1 . . ?
N1 C3 C1B 118.4(5) . . ?
N1 C3 C2B 118.4(5) . . ?
N1 C3 C2A 122.7(4) . . ?
N1 C3 C1A 117.6(3) . . ?
C1B C3 H3A 116.1 . . ?
C2B C3 H3A 116.1 . . ?
C2B C3 C1B 60.3(4) . . ?
C2A C3 H3B 115.1 . . ?
C2A C3 C1A 60.0(3) . . ?
C1A C3 H3B 115.1 . . ?
O7 C28 H28A 109.5 . . ?
O7 C28 H28B 109.5 . . ?
O7 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C3 C1B H1BA 117.8 . . ?
C3 C1B H1BB 117.8 . . ?
C3 C1B C2B 59.8(4) . . ?
H1BA C1B H1BB 114.9 . . ?
C2B C1B H1BA 117.8 . . ?
C2B C1B H1BB 117.8 . . ?
C3 C2B C1B 59.9(4) . . ?
C3 C2B H2BA 117.8 . . ?
C3 C2B H2BB 117.8 . . ?
C1B C2B H2BA 117.8 . . ?
C1B C2B H2BB 117.8 . . ?
H2BA C2B H2BB 114.9 . . ?
C3 C2A H2AA 117.8 . . ?
C3 C2A H2AB 117.8 . . ?
C3 C2A C1A 60.1(3) . . ?
H2AA C2A H2AB 114.9 . . ?
C1A C2A H2AA 117.8 . . ?
C1A C2A H2AB 117.8 . . ?
C3 C1A H1AA 117.8 . . ?
C3 C1A H1AB 117.8 . . ?
C2A C1A C3 59.9(3) . . ?
C2A C1A H1AA 117.8 . . ?
C2A C1A H1AB 117.8 . . ?
H1AA C1A H1AB 114.9 . . ?
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
Cl1 C7 1.737(2) . ?
O4 C18 1.361(2) . ?
O4 C21 1.439(3) . ?
O2 C13 1.365(3) . ?
O2 C10 1.405(3) . ?
O6 C26 1.206(3) . ?
O3 C20 1.235(3) . ?
O1 C4 1.230(3) . ?
N7 C24 1.392(3) . ?
N7 C26 1.394(3) . ?
N7 C25 1.361(3) . ?
N8 N9 1.274(2) . ?
N8 C24 1.369(3) . ?
N10 N9 1.385(3) . ?
N10 C26 1.366(3) . ?
N10 C27 1.462(3) . ?
O5 C22 1.225(3) . ?
N2 H2 0.8600 . ?
N2 C5 1.403(3) . ?
N2 C4 1.373(3) . ?
N3 C15 1.364(3) . ?
N3 C12 1.319(3) . ?
N6 C23 1.374(3) . ?
N6 C25 1.315(3) . ?
O7 H7 0.8200 . ?
O7 C28 1.397(4) . ?
N1 H1 0.8600 . ?
N1 C4 1.350(3) . ?
N1 C3 1.433(3) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C22 1.323(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C20 1.316(3) . ?
C15 C14 1.413(3) . ?
C15 C16 1.413(3) . ?
C14 C17 1.409(3) . ?
C14 C13 1.420(3) . ?
C5 C7 1.388(3) . ?
C5 C6 1.390(3) . ?
C17 H17 0.9300 . ?
C17 C19 1.375(3) . ?
C19 C18 1.432(3) . ?
C19 C20 1.504(3) . ?
C24 C23 1.373(3) . ?
C18 C16 1.366(3) . ?
C13 C11 1.370(3) . ?
C16 H16 0.9300 . ?
C23 C22 1.481(3) . ?
C7 C9 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C25 H25 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.392(3) . ?
C10 C8 1.368(4) . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C6 C8 1.379(3) . ?
C8 H8 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 C1B 1.492(7) . ?
C3 C2B 1.490(7) . ?
C3 C2A 1.486(6) . ?
C3 C1A 1.489(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C1B C2B 1.497(8) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C1A 1.487(7) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O3 0.86 2.25 3.037(2) 152.4 2_676
O7 H7 N3 0.82 2.10 2.887(3) 161.1 2_766
N5 H5A O1 0.86 2.09 2.946(3) 170.8 1_556
N5 H5B O7 0.86 2.39 3.137(3) 144.7 1_556
N4 H4A O5 0.86 2.09 2.928(3) 165.7 .
N4 H4B O4 0.86 2.00 2.673(2) 134.4 .
N4 H4B N8 0.86 2.58 3.069(3) 117.3 .
C9 H9 O6 0.93 2.57 3.304(3) 135.8 2_667
C12 H12 N6 0.93 2.69 3.381(3) 131.3 1_554
C6 H6 O1 0.93 2.39 2.865(3) 111.4 .
C21 H21C N9 0.96 2.67 3.437(3) 137.5 .
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
Cl1 C7 C9 C10 -179.80(15) . . . . ?
O4 C18 C16 C15 -178.45(19) . . . . ?
O2 C13 C11 C12 -178.5(2) . . . . ?
O2 C10 C8 C6 178.90(19) . . . . ?
N7 C24 C23 N6 -0.1(2) . . . . ?
N7 C24 C23 C22 178.6(2) . . . . ?
N8 C24 C23 N6 -178.6(2) . . . . ?
N8 C24 C23 C22 0.1(4) . . . . ?
N2 C5 C7 Cl1 -0.6(3) . . . . ?
N2 C5 C7 C9 179.50(18) . . . . ?
N2 C5 C6 C8 -179.7(2) . . . . ?
N3 C15 C14 C17 -179.72(19) . . . . ?
N3 C15 C14 C13 -0.4(3) . . . . ?
N3 C15 C16 C18 179.0(2) . . . . ?
N6 C23 C22 O5 -170.6(2) . . . . ?
N6 C23 C22 N5 9.5(3) . . . . ?
N9 N8 C24 N7 1.6(3) . . . . ?
N9 N8 C24 C23 179.9(2) . . . . ?
N9 N10 C26 O6 -177.4(2) . . . . ?
N9 N10 C26 N7 3.0(3) . . . . ?
N1 C3 C1B C2B -108.3(6) . . . . ?
N1 C3 C2B C1B 108.3(6) . . . . ?
N1 C3 C2A C1A 105.4(4) . . . . ?
N1 C3 C1A C2A -113.7(4) . . . . ?
C15 N3 C12 C11 -0.4(3) . . . . ?
C15 C14 C17 C19 0.2(3) . . . . ?
C15 C14 C13 O2 178.97(18) . . . . ?
C15 C14 C13 C11 -0.3(3) . . . . ?
C14 C15 C16 C18 -0.8(3) . . . . ?
C14 C17 C19 C18 0.4(3) . . . . ?
C14 C17 C19 C20 -179.03(18) . . . . ?
C14 C13 C11 C12 0.6(3) . . . . ?
C5 N2 C4 O1 3.8(3) . . . . ?
C5 N2 C4 N1 -174.89(18) . . . . ?
C5 C7 C9 C10 0.1(3) . . . . ?
C5 C6 C8 C10 0.1(3) . . . . ?
C17 C14 C13 O2 -1.8(3) . . . . ?
C17 C14 C13 C11 179.0(2) . . . . ?
C17 C19 C18 O4 178.71(18) . . . . ?
C17 C19 C18 C16 -1.1(3) . . . . ?
C17 C19 C20 O3 3.2(3) . . . . ?
C17 C19 C20 N4 -177.7(2) . . . . ?
C19 C18 C16 C15 1.4(3) . . . . ?
C24 N7 C26 O6 179.36(19) . . . . ?
C24 N7 C26 N10 -1.1(3) . . . . ?
C24 N7 C25 N6 0.2(2) . . . . ?
C24 N8 N9 N10 0.2(3) . . . . ?
C24 C23 C22 O5 10.9(4) . . . . ?
C24 C23 C22 N5 -169.0(2) . . . . ?
C18 C19 C20 O3 -176.1(2) . . . . ?
C18 C19 C20 N4 3.0(3) . . . . ?
C13 O2 C10 C9 104.2(2) . . . . ?
C13 O2 C10 C8 -77.6(3) . . . . ?
C13 C14 C17 C19 -179.08(19) . . . . ?
C13 C11 C12 N3 -0.3(4) . . . . ?
C20 C19 C18 O4 -2.0(3) . . . . ?
C20 C19 C18 C16 178.2(2) . . . . ?
C16 C15 C14 C17 0.1(3) . . . . ?
C16 C15 C14 C13 179.34(18) . . . . ?
C23 N6 C25 N7 -0.3(2) . . . . ?
C7 C5 C6 C8 2.6(3) . . . . ?
C7 C9 C10 O2 -179.00(17) . . . . ?
C7 C9 C10 C8 2.8(3) . . . . ?
C26 N7 C24 N8 -1.1(3) . . . . ?
C26 N7 C24 C23 -179.83(18) . . . . ?
C26 N7 C25 N6 179.9(2) . . . . ?
C26 N10 N9 N8 -2.8(3) . . . . ?
C4 N2 C5 C7 -151.0(2) . . . . ?
C4 N2 C5 C6 31.4(3) . . . . ?
C4 N1 C3 C1B 143.6(7) . . . . ?
C4 N1 C3 C2B 74.0(6) . . . . ?
C4 N1 C3 C2A 101.4(5) . . . . ?
C4 N1 C3 C1A 171.8(4) . . . . ?
C9 C10 C8 C6 -3.0(3) . . . . ?
C25 N7 C24 N8 178.63(19) . . . . ?
C25 N7 C24 C23 -0.1(2) . . . . ?
C25 N7 C26 O6 -0.3(4) . . . . ?
C25 N7 C26 N10 179.3(2) . . . . ?
C25 N6 C23 C24 0.2(2) . . . . ?
C25 N6 C23 C22 -178.5(2) . . . . ?
C10 O2 C13 C14 172.99(17) . . . . ?
C10 O2 C13 C11 -7.8(3) . . . . ?
C12 N3 C15 C14 0.7(3) . . . . ?
C12 N3 C15 C16 -179.04(19) . . . . ?
C6 C5 C7 Cl1 177.17(16) . . . . ?
C6 C5 C7 C9 -2.8(3) . . . . ?
C27 N10 N9 N8 179.0(2) . . . . ?
C27 N10 C26 O6 0.8(3) . . . . ?
C27 N10 C26 N7 -178.8(2) . . . . ?
C21 O4 C18 C19 -175.1(2) . . . . ?
C21 O4 C18 C16 4.8(3) . . . . ?
C3 N1 C4 O1 -1.9(3) . . . . ?
C3 N1 C4 N2 176.8(2) . . . . ?
