# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_211006-tmz-len
_database_code_depnum_ccdc_archive 'CCDC 2258403'
loop_
_audit_author_name
_audit_author_address
'zhiqing wang'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2023-06-18 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_audit_creation_date             2023-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_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
_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 0.0181 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1842(3)
_cell_length_b                   14.4765(5)
_cell_length_c                   15.9555(4)
_cell_angle_alpha                68.871(3)
_cell_angle_beta                 78.281(3)
_cell_angle_gamma                79.368(3)
_cell_volume                     1504.29(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6838
_cell_measurement_temperature    297.24(10)
_cell_measurement_theta_max      78.5070
_cell_measurement_theta_min      2.9780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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
_diffrn_ambient_temperature      297.24(10)
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3764
_reflns_number_total             4849
_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 1.171.39.46e (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)'
_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_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.101
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
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


_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
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_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_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) . . . . ?

_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
;
