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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_023XB102A_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2144103'
loop_
_audit_author_name
_audit_author_address
'Merce Font Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-03-30 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Tipiracil hydrochloride methanol solvate - hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C9 H12 Cl N4 O2), C H4 O, 4(Cl), 3(H2 O)'
_chemical_formula_sum            'C37 H58 Cl8 N16 O12'
_chemical_formula_weight         1202.59

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.1291(2)
_cell_length_b                   13.5358(5)
_cell_length_c                   27.2056(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2625.29(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9869
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      33.78

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.502
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6558
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29776
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.704
_diffrn_reflns_theta_max         33.782
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             10351
_reflns_number_gt                9186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.996

_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.
 
The hydrogen atoms of the water molecules were found in a Fourier difference map.
These hydrogen positions were then refined and subjected to O-H distance constraints of
0.80(5) Angstroms and H-O-H angle constraints of 105(1) degrees and refined with an
isotropic temperature factor equal to 1.2, the equivalent temperature factor of the
atoms to which they are bonded.

All the remaining hydrogens were computed and refined, using a riding model, 
with an isotropic temperature factor equal to 1.2, the equivalent temperature 
factor of the atoms to which are linked.

Two individual Q peaks per each atomic position of the C8, C17 and Cl3 atoms were observed 
evidencing static disorder for each atom, then occupancy factors of 0.5 were used
and refined with good results. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+2.0267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3473 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(14)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         10351
_refine_ls_number_parameters     374
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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 0.96886(10) 0.22882(5) 0.50546(3) 0.02312(13) Uani 1 1 d . . . . .
O1 O 0.8675(3) 0.25921(15) 0.40084(8) 0.0261(4) Uani 1 1 d . . . . .
O2 O 0.9298(3) 0.59398(15) 0.39791(8) 0.0230(4) Uani 1 1 d . . . . .
N1 N 0.8999(3) 0.42611(17) 0.39994(9) 0.0195(4) Uani 1 1 d . . . . .
H1N H 0.867731 0.426189 0.368712 0.023 Uiso 1 1 calc R U . . .
N2 N 0.9881(3) 0.51235(17) 0.46947(8) 0.0175(4) Uani 1 1 d . . . . .
H2N H 1.010934 0.568413 0.484717 0.021 Uiso 1 1 calc R U . . .
N3 N 0.9070(3) 0.42853(16) 0.58213(9) 0.0186(4) Uani 1 1 d . . . . .
N4 N 1.0137(5) 0.3018(2) 0.63384(10) 0.0329(6) Uani 1 1 d . . . . .
H4A H 1.117217 0.292693 0.616809 0.040 Uiso 1 1 calc R U . . .
H4B H 0.991422 0.265527 0.660047 0.040 Uiso 1 1 calc R U . . .
C1 C 0.9609(4) 0.33945(19) 0.47459(10) 0.0183(4) Uani 1 1 d . . . . .
C2 C 0.9058(4) 0.33597(19) 0.42313(10) 0.0193(5) Uani 1 1 d . . . . .
C3 C 0.9394(4) 0.51614(19) 0.42087(10) 0.0178(4) Uani 1 1 d . . . . .
C4 C 1.0034(3) 0.42633(19) 0.49589(10) 0.0176(4) Uani 1 1 d . . . . .
C5 C 1.0663(4) 0.4369(2) 0.54877(10) 0.0192(5) Uani 1 1 d . . . . .
H5A H 1.159368 0.384978 0.556533 0.023 Uiso 1 1 calc R U . . .
H5B H 1.127326 0.501988 0.553333 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8934(4) 0.3689(2) 0.62024(10) 0.0221(5) Uani 1 1 d . . . . .
C7 C 0.7123(5) 0.3868(3) 0.64719(12) 0.0291(6) Uani 1 1 d . . . . .
H7A H 0.735608 0.415978 0.680001 0.035 Uiso 0.5 1 calc R U P A 1
H7B H 0.640599 0.324705 0.651171 0.035 Uiso 0.5 1 calc R U P A 1
H7A' H 0.730703 0.382614 0.683201 0.035 Uiso 0.5 1 calc R U P B 2
H7B' H 0.615269 0.338528 0.637194 0.035 Uiso 0.5 1 calc R U P B 2
C8 C 0.6074(14) 0.4600(7) 0.6135(4) 0.048(2) Uani 0.5 1 d . . P C 1
H8A H 0.506018 0.425988 0.595350 0.058 Uiso 0.5 1 calc R U P C 1
H8B H 0.551678 0.514253 0.633128 0.058 Uiso 0.5 1 calc R U P C 1
C8' C 0.6589(10) 0.4901(5) 0.6319(3) 0.0238(13) Uani 0.5 1 d . . P C 2
H8'A H 0.711220 0.539927 0.654754 0.029 Uiso 0.5 1 calc R U P C 2
H8'B H 0.520921 0.498006 0.630342 0.029 Uiso 0.5 1 calc R U P C 2
C9 C 0.7504(4) 0.4991(2) 0.57906(13) 0.0252(6) Uani 1 1 d . . . . .
H9A H 0.700116 0.502277 0.545179 0.030 Uiso 1 1 calc R U . C 1
H9B H 0.791333 0.566086 0.589064 0.030 Uiso 1 1 calc R U . C 1
Cl2 Cl 0.90685(11) 1.05062(5) 0.61594(3) 0.02855(16) Uani 1 1 d . . . . .
O3 O 1.0655(3) 0.68159(14) 0.52105(7) 0.0229(4) Uani 1 1 d . . . . .
O4 O 0.9095(3) 1.00562(15) 0.50806(8) 0.0233(4) Uani 1 1 d . . . . .
N5 N 0.9888(3) 0.84431(16) 0.51512(8) 0.0169(4) Uani 1 1 d . . . . .
H5N H 0.986337 0.839160 0.482878 0.020 Uiso 1 1 calc R U . . .
N6 N 1.0436(3) 0.77217(16) 0.59082(8) 0.0167(4) Uani 1 1 d . . . . .
H6N H 1.073714 0.720414 0.608733 0.020 Uiso 1 1 calc R U . . .
N7 N 0.8681(4) 0.8574(2) 0.69660(9) 0.0261(5) Uani 1 1 d . . . . .
N9 N 0.9596(7) 0.9647(2) 0.75938(11) 0.0530(12) Uani 1 1 d . . . . .
H9NA H 1.066529 0.978629 0.744798 0.064 Uiso 1 1 calc R U . . .
H9NB H 0.931770 0.992235 0.787763 0.064 Uiso 1 1 calc R U . . .
C10 C 0.9564(4) 0.93938(19) 0.58827(10) 0.0175(4) Uani 1 1 d . . . . .
C11 C 0.9472(3) 0.93632(19) 0.53481(10) 0.0167(4) Uani 1 1 d . . . . .
C12 C 1.0332(4) 0.76097(19) 0.54094(9) 0.0164(4) Uani 1 1 d . . . . .
C13 C 1.0093(4) 0.86012(19) 0.61442(9) 0.0171(4) Uani 1 1 d . . . . .
C14 C 1.0445(4) 0.8589(2) 0.66923(10) 0.0222(5) Uani 1 1 d . . . . .
H14A H 1.119534 0.799918 0.677874 0.027 Uiso 1 1 calc R U . . .
H14B H 1.117382 0.918262 0.678601 0.027 Uiso 1 1 calc R U . . .
C15 C 0.8425(6) 0.9033(2) 0.73897(12) 0.0345(8) Uani 1 1 d . . . . .
C16 C 0.6606(7) 0.8723(3) 0.76109(15) 0.0488(12) Uani 1 1 d . . . . .
H16A H 0.583409 0.930530 0.769853 0.059 Uiso 1 1 calc R U . D 1
H16B H 0.681310 0.831981 0.790952 0.059 Uiso 1 1 calc R U . D 1
C17 C 0.5517(13) 0.8023(7) 0.7148(4) 0.0293(17) Uani 0.5 1 d . . P E 1
H17A H 0.495135 0.740604 0.727562 0.035 Uiso 0.5 1 calc R U P E 1
H17B H 0.456891 0.840638 0.696274 0.035 Uiso 0.5 1 calc R U P E 1
C17' C 0.5692(13) 0.8393(7) 0.7214(3) 0.0278(17) Uani 0.5 1 d . . P E 2
H17C H 0.510406 0.895152 0.703643 0.033 Uiso 0.5 1 calc R U P E 2
H17D H 0.469474 0.792448 0.731245 0.033 Uiso 0.5 1 calc R U P E 2
C18 C 0.7221(5) 0.7841(4) 0.68610(13) 0.0398(9) Uani 1 1 d . . . . .
H18A H 0.691188 0.786078 0.650640 0.040(12) Uiso 1 1 calc R . . E 1
H18B H 0.770490 0.717300 0.693778 0.047(14) Uiso 1 1 calc R . . E 1
O2W O 0.9922(10) 0.2101(4) 0.7227(2) 0.0436(9) Uani 0.5 1 d . . P F 1
H2W H 1.050872 0.157049 0.718208 0.05(3) Uiso 0.5 1 calc R . P F 1
C1W C 0.8049(15) 0.1942(6) 0.7162(3) 0.0436(9) Uani 0.5 1 d . . P F 1
H1WA H 0.786388 0.133551 0.697061 0.065 Uiso 0.5 1 calc R U P F 1
H1WB H 0.749859 0.250170 0.698476 0.065 Uiso 0.5 1 calc R U P F 1
H1WC H 0.743952 0.187285 0.748265 0.065 Uiso 0.5 1 calc R U P F 1
O2W' O 0.6743(11) 0.1291(4) 0.7432(2) 0.0436(9) Uani 0.5 1 d D . P G 2
H2A' H 0.664(16) 0.075(2) 0.754(3) 0.052 Uiso 0.5 1 d D U P H 2
H2B' H 0.657(16) 0.159(5) 0.7681(18) 0.052 Uiso 0.5 1 d D U P I 2
O1W O 0.9923(3) 0.79911(15) 0.41596(7) 0.0218(4) Uani 1 1 d D . . . .
H1OA H 0.928(5) 0.822(2) 0.3947(11) 0.026 Uiso 1 1 d D U . . .
H1OB H 0.962(5) 0.7427(11) 0.4136(14) 0.026 Uiso 1 1 d D U . . .
Cl3 Cl 0.2667(4) 0.0875(2) 0.71371(8) 0.0496(7) Uani 0.5 1 d . . P J 1
Cl3' Cl 0.3566(3) 0.06814(13) 0.71616(7) 0.0278(3) Uani 0.5 1 d . . P K 2
Cl4 Cl 0.81833(11) 0.09316(6) 0.84877(3) 0.03077(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.718(3) . ?
O1 C2 1.234(3) . ?
O2 C3 1.227(3) . ?
N1 C2 1.374(4) . ?
N1 C3 1.374(3) . ?
N1 H1N 0.8800 . ?
N2 C3 1.368(3) . ?
N2 C4 1.373(3) . ?
N2 H2N 0.8800 . ?
N3 C6 1.317(4) . ?
N3 C5 1.458(3) . ?
N3 C9 1.472(4) . ?
N4 C6 1.303(4) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C1 C4 1.346(4) . ?
C1 C2 1.455(4) . ?
C4 C5 1.514(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.504(4) . ?
C7 C8' 1.508(8) . ?
C7 C8 1.543(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 H7A' 0.9900 . ?
C7 H7B' 0.9900 . ?
C8 C9 1.483(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8' C9 1.583(8) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
Cl2 C10 1.720(3) . ?
O3 C12 1.225(3) . ?
O4 C11 1.217(3) . ?
N5 C12 1.366(3) . ?
N5 C11 1.388(3) . ?
N5 H5N 0.8800 . ?
N6 C12 1.368(3) . ?
N6 C13 1.374(3) . ?
N6 H6N 0.8800 . ?
N7 C15 1.323(4) . ?
N7 C14 1.462(4) . ?
N7 C18 1.465(5) . ?
N9 C15 1.302(6) . ?
N9 H9NA 0.8800 . ?
N9 H9NB 0.8800 . ?
C10 C13 1.341(4) . ?
C10 C11 1.456(4) . ?
C13 C14 1.512(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.490(6) . ?
C16 C17' 1.338(10) . ?
C16 C17 1.757(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.465(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17' C18 1.634(10) . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
O2W C1W 1.364(12) . ?
O2W H2W 0.8400 . ?
C1W H1WA 0.9800 . ?
C1W H1WB 0.9800 . ?
C1W H1WC 0.9800 . ?
O2W' H2A' 0.799(14) . ?
O2W' H2B' 0.799(14) . ?
O1W H1OA 0.801(13) . ?
O1W H1OB 0.795(13) . ?

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
C2 N1 C3 126.2(2) . . ?
C2 N1 H1N 116.9 . . ?
C3 N1 H1N 116.9 . . ?
C3 N2 C4 123.9(2) . . ?
C3 N2 H2N 118.0 . . ?
C4 N2 H2N 118.0 . . ?
C6 N3 C5 126.5(2) . . ?
C6 N3 C9 112.8(2) . . ?
C5 N3 C9 120.3(2) . . ?
C6 N4 H4A 120.0 . . ?
C6 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C4 C1 C2 120.2(2) . . ?
C4 C1 Cl1 122.9(2) . . ?
C2 C1 Cl1 116.8(2) . . ?
O1 C2 N1 121.0(3) . . ?
O1 C2 C1 124.1(3) . . ?
N1 C2 C1 114.9(2) . . ?
O2 C3 N2 122.6(2) . . ?
O2 C3 N1 122.6(2) . . ?
N2 C3 N1 114.8(2) . . ?
C1 C4 N2 119.9(2) . . ?
C1 C4 C5 124.0(2) . . ?
N2 C4 C5 116.1(2) . . ?
N3 C5 C4 110.7(2) . . ?
N3 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N4 C6 N3 127.0(3) . . ?
N4 C6 C7 122.6(3) . . ?
N3 C6 C7 110.4(2) . . ?
C6 C7 C8' 103.4(4) . . ?
C6 C7 C8 103.3(4) . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C6 C7 H7A' 111.1 . . ?
C8' C7 H7A' 111.1 . . ?
C6 C7 H7B' 111.1 . . ?
C8' C7 H7B' 111.1 . . ?
H7A' C7 H7B' 109.0 . . ?
C9 C8 C7 105.7(6) . . ?
C9 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C7 C8' C9 102.6(4) . . ?
C7 C8' H8'A 111.3 . . ?
C9 C8' H8'A 111.3 . . ?
C7 C8' H8'B 111.3 . . ?
C9 C8' H8'B 111.3 . . ?
H8'A C8' H8'B 109.2 . . ?
N3 C9 C8 104.7(4) . . ?
N3 C9 C8' 102.2(3) . . ?
N3 C9 H9A 110.8 . . ?
C8 C9 H9A 110.8 . . ?
N3 C9 H9B 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C12 N5 C11 126.3(2) . . ?
C12 N5 H5N 116.9 . . ?
C11 N5 H5N 116.9 . . ?
C12 N6 C13 123.4(2) . . ?
C12 N6 H6N 118.3 . . ?
C13 N6 H6N 118.3 . . ?
C15 N7 C14 123.8(3) . . ?
C15 N7 C18 113.0(3) . . ?
C14 N7 C18 121.4(3) . . ?
C15 N9 H9NA 120.0 . . ?
C15 N9 H9NB 120.0 . . ?
H9NA N9 H9NB 120.0 . . ?
C13 C10 C11 121.3(2) . . ?
C13 C10 Cl2 121.7(2) . . ?
C11 C10 Cl2 116.91(19) . . ?
O4 C11 N5 120.5(2) . . ?
O4 C11 C10 125.8(3) . . ?
N5 C11 C10 113.7(2) . . ?
O3 C12 N5 122.7(2) . . ?
O3 C12 N6 121.7(2) . . ?
N5 C12 N6 115.6(2) . . ?
C10 C13 N6 119.7(2) . . ?
C10 C13 C14 125.3(2) . . ?
N6 C13 C14 115.0(2) . . ?
N7 C14 C13 111.1(2) . . ?
N7 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
N7 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N9 C15 N7 125.7(4) . . ?
N9 C15 C16 124.4(3) . . ?
N7 C15 C16 109.9(4) . . ?
C17' C16 C15 101.1(5) . . ?
C15 C16 C17 104.3(4) . . ?
C15 C16 H16A 110.9 . . ?
C17 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C18 C17 C16 96.1(5) . . ?
C18 C17 H17A 112.5 . . ?
C16 C17 H17A 112.5 . . ?
C18 C17 H17B 112.5 . . ?
C16 C17 H17B 112.5 . . ?
H17A C17 H17B 110.1 . . ?
C16 C17' C18 107.6(7) . . ?
C16 C17' H17C 110.2 . . ?
C18 C17' H17C 110.2 . . ?
C16 C17' H17D 110.2 . . ?
C18 C17' H17D 110.2 . . ?
H17C C17' H17D 108.5 . . ?
C17 C18 N7 111.8(5) . . ?
N7 C18 C17' 92.8(4) . . ?
C17 C18 H18A 109.3 . . ?
N7 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
N7 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C1W O2W H2W 109.5 . . ?
O2W C1W H1WA 109.5 . . ?
O2W C1W H1WB 109.5 . . ?
H1WA C1W H1WB 109.5 . . ?
O2W C1W H1WC 109.5 . . ?
H1WA C1W H1WC 109.5 . . ?
H1WB C1W H1WC 109.5 . . ?
H2A' O2W' H2B' 98(2) . . ?
H1OA O1W H1OB 98.8(19) . . ?

_refine_diff_density_max         1.507
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.079

