#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:10:18 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/80/7248049.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_7248049
loop_
_publ_author_name
'Stirk, Alexander J.'
'Holmes, Sean T.'
'Souza, Fabio E. S.'
'Hung, Ivan'
'Gan, Zhehong'
'Britten, James F.'
'Rey, Allan W.'
'Schurko, Robert W.'
_publ_section_title
;
 An unusual ionic cocrystal of ponatinib hydrochloride: characterization
 by single-crystal X-ray diffraction and ultra-high field NMR
 spectroscopy.
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1219
_journal_page_last               1233
_journal_paper_doi               10.1039/d3ce01062g
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety
'C29 H29 F3 N6 O, C29 H28 F3 N6 O, 3(Cl), 3(H2 O)'
_chemical_formula_sum            'C58 H63 Cl3 F6 N12 O5'
_chemical_formula_weight         1228.55
_chemical_name_common            'Ponatinib HCl'
_chemical_name_systematic
'3-(imidazo[1,2-b]pyridazin-3-yylethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide hydrochloride'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-19 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                92.864(3)
_cell_angle_beta                 102.624(3)
_cell_angle_gamma                106.246(3)
_cell_formula_units_Z            2
_cell_length_a                   12.4408(7)
_cell_length_b                   15.1905(8)
_cell_length_c                   16.5411(9)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      23.95
_cell_measurement_theta_min      2.58
_cell_volume                     2907.9(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            97752
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.086
_diffrn_reflns_theta_min         1.270
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0650 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.8961. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_recrystallization_method Layering
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     782
_refine_ls_number_reflns         14060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0684P)²+4.1855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9882
_reflns_number_total             14060
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01062g2.cif
_cod_data_source_block           grtv1661_0m
_cod_depositor_comments          'Adding full bibliography for 7248049.cif.'
_cod_database_code               7248049
_shelx_shelxl_version_number     2017/1
_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   0.954
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3C,H3D), O2(H2C,H2D), O1(H1C,H1D)
2.b Secondary CH2 refined with riding coordinates:
 C24A(H24A,H24B), C25A(H25A,H25B), C26A(H26A,H26B), C27A(H27A,H27B), C28A(H28A,
 H28B), C24B(H24C,H24D), C25B(H25C,H25D), C26B(H26C,H26D), C27B(H27C,H27D),
 C28B(H28C,H28D)
2.c Aromatic/amide H refined with riding coordinates:
 N4A(H4A), C1A(H1AA), C2A(H2A), C3A(H3A), C5A(H5A), C10A(H10A), C12A(H12A),
 C13A(H13A), C18A(H18A), C19A(H19A), C22A(H22A), N4B(H4B), C1B(H1B), C2B(H2B),
 C3B(H3B), C5B(H5B), C10B(H10B), C12B(H12B), C13B(H13B), C18B(H18B), C19B(H19B),
  C22B(H22B)
2.d Idealised Me refined as rotating group:
 C15A(H15A,H15B,H15C), C29A(H29A,H29B,H29C), C15B(H15D,H15E,H15F), C29B(H29D,
 H29E,H29F)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
F1A F 0.92447(14) 0.66763(12) 1.18675(11) 0.0255(4) Uani 1 1 d . . . . .
F2A F 0.94622(14) 0.80306(11) 1.14550(11) 0.0250(4) Uani 1 1 d . . . . .
F3A F 0.91254(14) 0.68414(13) 1.05619(11) 0.0265(4) Uani 1 1 d . . . . .
O1A O 0.61360(17) 0.57345(16) 0.86440(13) 0.0271(5) Uani 1 1 d . . . . .
N1A N 0.5098(2) 0.30544(16) 0.34014(15) 0.0200(5) Uani 1 1 d . . . . .
H1A H 0.495(3) 0.280(3) 0.276(2) 0.042(11) Uiso 1 1 d . . . . .
N2A N 0.6784(2) 0.40835(17) 0.54005(15) 0.0226(5) Uani 1 1 d . . . . .
N3A N 0.5950(2) 0.36922(16) 0.46909(14) 0.0179(5) Uani 1 1 d . . . . .
N4A N 0.48581(19) 0.59044(15) 0.94086(14) 0.0172(5) Uani 1 1 d . . . . .
H4A H 0.411871 0.577275 0.939528 0.021 Uiso 1 1 calc R . . . .
N5A N 0.7737(2) 0.86808(16) 1.28419(14) 0.0178(5) Uani 1 1 d . . . . .
N6A N 0.8842(2) 1.06288(16) 1.34560(15) 0.0199(5) Uani 1 1 d . . . . .
H6A H 0.960(4) 1.061(3) 1.354(2) 0.043(11) Uiso 1 1 d . . . . .
C1A C 0.7835(3) 0.4128(2) 0.53373(19) 0.0254(6) Uani 1 1 d . . . . .
H1AA H 0.845166 0.439174 0.581393 0.030 Uiso 1 1 calc R . . . .
C2A C 0.8118(3) 0.3809(2) 0.46039(19) 0.0248(6) Uani 1 1 d . . . . .
H2A H 0.889937 0.386737 0.460570 0.030 Uiso 1 1 calc R . . . .
C3A C 0.7264(3) 0.3422(2) 0.39026(18) 0.0215(6) Uani 1 1 d . . . . .
H3A H 0.742514 0.320182 0.340823 0.026 Uiso 1 1 calc R . . . .
C4A C 0.6128(2) 0.33664(19) 0.39515(17) 0.0190(6) Uani 1 1 d . . . . .
C5A C 0.4265(3) 0.3190(2) 0.37815(17) 0.0214(6) Uani 1 1 d . . . . .
H5A H 0.346388 0.303400 0.352350 0.026 Uiso 1 1 calc R . . . .
C6A C 0.4771(2) 0.35838(19) 0.45907(17) 0.0194(6) Uani 1 1 d . . . . .
C7A C 0.4317(2) 0.3855(2) 0.52468(18) 0.0206(6) Uani 1 1 d . . . . .
C8A C 0.3962(2) 0.40939(19) 0.58154(17) 0.0187(6) Uani 1 1 d . . . . .
C9A C 0.3590(2) 0.44193(19) 0.65144(17) 0.0176(5) Uani 1 1 d . . . . .
C10A C 0.4434(2) 0.48480(18) 0.72457(17) 0.0174(5) Uani 1 1 d . . . . .
H10A H 0.522086 0.491109 0.726604 0.021 Uiso 1 1 calc R . . . .
C11A C 0.4143(2) 0.51846(18) 0.79452(17) 0.0168(5) Uani 1 1 d . . . . .
C12A C 0.2976(2) 0.50971(19) 0.78935(17) 0.0199(6) Uani 1 1 d . . . . .
H12A H 0.275668 0.532684 0.835696 0.024 Uiso 1 1 calc R . . . .
C13A C 0.2135(2) 0.4675(2) 0.71654(18) 0.0207(6) Uani 1 1 d . . . . .
H13A H 0.135140 0.462870 0.714363 0.025 Uiso 1 1 calc R . . . .
C14A C 0.2410(2) 0.4318(2) 0.64684(17) 0.0199(6) Uani 1 1 d . . . . .
C15A C 0.1479(3) 0.3829(2) 0.57012(19) 0.0266(6) Uani 1 1 d . . . . .
H15A H 0.169372 0.407405 0.520315 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.074678 0.392938 0.574116 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.139243 0.316550 0.566206 0.040 Uiso 1 1 calc GR . . . .
C16A C 0.5133(2) 0.56257(19) 0.86957(17) 0.0188(5) Uani 1 1 d . . . . .
C17A C 0.5645(2) 0.63839(18) 1.01667(17) 0.0167(5) Uani 1 1 d . . . . .
C18A C 0.5188(2) 0.67461(19) 1.07640(17) 0.0187(5) Uani 1 1 d . . . . .
H18A H 0.438617 0.668489 1.064706 0.022 Uiso 1 1 calc R . . . .
C19A C 0.5907(2) 0.71957(19) 1.15286(17) 0.0194(6) Uani 1 1 d . . . . .
H19A H 0.557650 0.742412 1.192868 0.023 Uiso 1 1 calc R . . . .
C20A C 0.7100(2) 0.73230(18) 1.17289(17) 0.0170(5) Uani 1 1 d . . . . .
C21A C 0.7546(2) 0.69851(18) 1.11073(17) 0.0172(5) Uani 1 1 d . . . . .
C22A C 0.6836(2) 0.65120(18) 1.03399(17) 0.0177(5) Uani 1 1 d . . . . .
H22A H 0.716146 0.627949 0.993926 0.021 Uiso 1 1 calc R . . . .
C23A C 0.8828(2) 0.71220(19) 1.12473(17) 0.0200(6) Uani 1 1 d . . . . .
C24A C 0.7803(2) 0.77507(19) 1.26076(17) 0.0189(6) Uani 1 1 d . . . . .
H24A H 0.752617 0.733862 1.301223 0.023 Uiso 1 1 calc R . . . .
H24B H 0.862037 0.778692 1.264996 0.023 Uiso 1 1 calc R . . . .
C25A C 0.8372(3) 0.89873(19) 1.37195(17) 0.0203(6) Uani 1 1 d . . . . .
H25A H 0.918527 0.899594 1.378447 0.024 Uiso 1 1 calc R . . . .
H25B H 0.802879 0.854309 1.407848 0.024 Uiso 1 1 calc R . . . .
C26A C 0.8335(3) 0.9945(2) 1.40008(18) 0.0226(6) Uani 1 1 d . . . . .
H26A H 0.752660 0.993111 1.396821 0.027 Uiso 1 1 calc R . . . .
H26B H 0.877782 1.013625 1.458821 0.027 Uiso 1 1 calc R . . . .
C27A C 0.8204(3) 1.0309(2) 1.25589(18) 0.0228(6) Uani 1 1 d . . . . .
H27A H 0.855495 1.074407 1.219599 0.027 Uiso 1 1 calc R . . . .
H27B H 0.738918 1.029990 1.248370 0.027 Uiso 1 1 calc R . . . .
C28A C 0.8256(3) 0.93507(19) 1.23117(18) 0.0219(6) Uani 1 1 d . . . . .
H28A H 0.783767 0.914790 1.172038 0.026 Uiso 1 1 calc R . . . .
H28B H 0.907045 0.936828 1.236625 0.026 Uiso 1 1 calc R . . . .
C29A C 0.8838(3) 1.1592(2) 1.3716(2) 0.0266(6) Uani 1 1 d . . . . .
H29A H 0.804622 1.159154 1.370093 0.040 Uiso 1 1 calc GR . . . .
H29B H 0.914533 1.200845 1.333231 0.040 Uiso 1 1 calc GR . . . .
H29C H 0.932000 1.180169 1.428381 0.040 Uiso 1 1 calc GR . . . .
F1B F 0.15361(16) -0.16406(16) -0.69066(12) 0.0380(5) Uani 1 1 d . . . . .
F2B F 0.12966(16) -0.27681(14) -0.61893(15) 0.0435(5) Uani 1 1 d . . . . .
F3B F 0.15596(18) -0.14087(17) -0.56124(13) 0.0494(6) Uani 1 1 d . . . . .
O1B O 0.40714(17) -0.09279(16) -0.33276(13) 0.0276(5) Uani 1 1 d . . . . .
N1B N 0.4691(2) 0.23331(16) 0.18094(15) 0.0213(5) Uani 1 1 d . . . . .
N2B N 0.2853(2) 0.10562(17) -0.00859(15) 0.0236(5) Uani 1 1 d . . . . .
N3B N 0.3741(2) 0.15219(16) 0.05678(14) 0.0188(5) Uani 1 1 d . . . . .
N4B N 0.5570(2) -0.08668(16) -0.39388(14) 0.0196(5) Uani 1 1 d . . . . .
H4B H 0.632647 -0.072833 -0.383258 0.024 Uiso 1 1 calc R . . . .
N5B N 0.25462(19) -0.31712(15) -0.75587(14) 0.0166(5) Uani 1 1 d . . . . .
N6B N 0.1641(2) -0.49682(16) -0.85401(14) 0.0172(5) Uani 1 1 d . . . . .
H6B H 0.212(3) -0.483(3) -0.886(2) 0.040(11) Uiso 1 1 d . . . . .
C1B C 0.1828(3) 0.1057(2) 0.00111(19) 0.0261(6) Uani 1 1 d . . . . .
H1B H 0.117762 0.073588 -0.042555 0.031 Uiso 1 1 calc R . . . .
C2B C 0.1613(3) 0.1496(2) 0.07131(19) 0.0268(7) Uani 1 1 d . . . . .
H2B H 0.084818 0.147198 0.073198 0.032 Uiso 1 1 calc R . . . .
C3B C 0.2532(3) 0.1957(2) 0.13651(19) 0.0237(6) Uani 1 1 d . . . . .
H3B H 0.242037 0.225764 0.184387 0.028 Uiso 1 1 calc R . . . .
C4B C 0.3642(2) 0.19648(19) 0.12947(17) 0.0193(6) Uani 1 1 d . . . . .
C5B C 0.5461(3) 0.21251(19) 0.14067(18) 0.0212(6) Uani 1 1 d . . . . .
H5B H 0.627178 0.229924 0.163212 0.025 Uiso 1 1 calc R . . . .
C6B C 0.4905(2) 0.1629(2) 0.06300(18) 0.0207(6) Uani 1 1 d . . . . .
C7B C 0.5340(3) 0.12758(19) 0.00011(17) 0.0208(6) Uani 1 1 d . . . . .
C8B C 0.5742(2) 0.0989(2) -0.05169(17) 0.0203(6) Uani 1 1 d . . . . .
C9B C 0.6241(2) 0.06354(18) -0.11259(17) 0.0175(5) Uani 1 1 d . . . . .
C10B C 0.5518(2) 0.01310(18) -0.18751(17) 0.0174(5) Uani 1 1 d . . . . .
H10B H 0.470774 0.002089 -0.197102 0.021 Uiso 1 1 calc R . . . .
C11B C 0.5969(2) -0.02151(18) -0.24875(17) 0.0181(5) Uani 1 1 d . . . . .
C12B C 0.7174(2) -0.00571(19) -0.23280(17) 0.0198(6) Uani 1 1 d . . . . .
H12B H 0.749741 -0.029016 -0.272974 0.024 Uiso 1 1 calc R . . . .
C13B C 0.7889(2) 0.0443(2) -0.15783(18) 0.0203(6) Uani 1 1 d . . . . .
H13B H 0.869720 0.053881 -0.147754 0.024 Uiso 1 1 calc R . . . .
C14B C 0.7455(2) 0.08057(19) -0.09722(17) 0.0203(6) Uani 1 1 d . . . . .
C15B C 0.8238(3) 0.1368(2) -0.01745(19) 0.0260(6) Uani 1 1 d . . . . .
H15D H 0.807832 0.196004 -0.010707 0.039 Uiso 1 1 calc GR . . . .
H15E H 0.904468 0.147950 -0.019888 0.039 Uiso 1 1 calc GR . . . .
H15F H 0.810001 0.102956 0.030025 0.039 Uiso 1 1 calc GR . . . .
C16B C 0.5117(2) -0.07071(19) -0.32843(17) 0.0192(6) Uani 1 1 d . . . . .
C17B C 0.4954(2) -0.12319(18) -0.47727(17) 0.0178(5) Uani 1 1 d . . . . .
C18B C 0.5596(2) -0.1401(2) -0.53292(18) 0.0213(6) Uani 1 1 d . . . . .
H18B H 0.640336 -0.130014 -0.513880 0.026 Uiso 1 1 calc R . . . .
C19B C 0.5041(2) -0.1719(2) -0.61675(18) 0.0213(6) Uani 1 1 d . . . . .
H19B H 0.548786 -0.182336 -0.653962 0.026 Uiso 1 1 calc R . . . .
C20B C 0.3849(2) -0.18882(18) -0.64781(17) 0.0177(5) Uani 1 1 d . . . . .
C21B C 0.3220(2) -0.17197(18) -0.59066(17) 0.0180(5) Uani 1 1 d . . . . .
C22B C 0.3757(2) -0.14001(19) -0.50644(17) 0.0189(6) Uani 1 1 d . . . . .
H22B H 0.331166 -0.129714 -0.469062 0.023 Uiso 1 1 calc R . . . .
C23B C 0.1916(2) -0.1874(2) -0.61580(17) 0.0211(6) Uani 1 1 d . . . . .
C24B C 0.3321(2) -0.22115(19) -0.74001(17) 0.0189(6) Uani 1 1 d . . . . .
H24C H 0.287960 -0.179547 -0.763788 0.023 Uiso 1 1 calc R . . . .
H24D H 0.394791 -0.216776 -0.768987 0.023 Uiso 1 1 calc R . . . .
C25B C 0.1765(2) -0.33162(19) -0.83933(17) 0.0195(6) Uani 1 1 d . . . . .
H25C H 0.222259 -0.320437 -0.881813 0.023 Uiso 1 1 calc R . . . .
H25D H 0.131244 -0.287098 -0.842585 0.023 Uiso 1 1 calc R . . . .
C26B C 0.0945(2) -0.4299(2) -0.85758(18) 0.0207(6) Uani 1 1 d . . . . .
H26C H 0.047397 -0.441148 -0.815887 0.025 Uiso 1 1 calc R . . . .
H26D H 0.041694 -0.438659 -0.913586 0.025 Uiso 1 1 calc R . . . .
C27B C 0.2433(2) -0.48207(19) -0.76789(17) 0.0178(5) Uani 1 1 d . . . . .
H27C H 0.290410 -0.525203 -0.764577 0.021 Uiso 1 1 calc R . . . .
H27D H 0.196979 -0.494772 -0.725819 0.021 Uiso 1 1 calc R . . . .
C28B C 0.3220(2) -0.38294(18) -0.74959(17) 0.0173(5) Uani 1 1 d . . . . .
H28C H 0.372774 -0.373311 -0.692731 0.021 Uiso 1 1 calc R . . . .
H28D H 0.371509 -0.371725 -0.789703 0.021 Uiso 1 1 calc R . . . .
C29B C 0.0904(3) -0.59514(19) -0.87586(18) 0.0221(6) Uani 1 1 d . . . . .
H29D H 0.139472 -0.635128 -0.878602 0.033 Uiso 1 1 calc GR . . . .
H29E H 0.036055 -0.602005 -0.930150 0.033 Uiso 1 1 calc GR . . . .
H29F H 0.047448 -0.612710 -0.833139 0.033 Uiso 1 1 calc GR . . . .
Cl1 Cl 1.00433(6) 0.40245(5) 0.33255(5) 0.02551(16) Uani 1 1 d . . . . .
Cl1B Cl 0.21733(6) -0.43646(5) -1.02546(4) 0.02288(16) Uani 1 1 d . . . . .
Cl1A Cl 1.15009(6) 1.09296(5) 1.39255(5) 0.02704(17) Uani 1 1 d . . . . .
O3 O 1.1561(2) 0.27408(17) 0.30377(15) 0.0323(5) Uani 1 1 d . . . . .
H3C H 1.121951 0.309725 0.321087 0.048 Uiso 1 1 d G . . . .
H3D H 1.146691 0.226501 0.329439 0.048 Uiso 1 1 d G . . . .
O2 O 0.9747(2) 0.18818(17) 0.16269(15) 0.0358(5) Uani 1 1 d . . . . .
H2C H 1.027768 0.212320 0.206425 0.054 Uiso 1 1 d G . . . .
H2D H 0.926211 0.218129 0.162023 0.054 Uiso 1 1 d G . . . .
O1 O 0.8220(2) 0.29864(16) 0.16776(15) 0.0329(5) Uani 1 1 d . . . . .
H1C H 0.806544 0.330993 0.128885 0.049 Uiso 1 1 d G . . . .
H1D H 0.867099 0.333801 0.210602 0.049 Uiso 1 1 d G . . . .
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'
F F 0.0171 0.0103 '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
C4A N1A H1A 126(2) . . ?
C4A N1A C5A 108.6(2) . . ?
C5A N1A H1A 125(2) . . ?
C1A N2A N3A 113.8(2) . . ?
N2A N3A C4A 125.9(2) . . ?
N2A N3A C6A 125.0(2) . . ?
C4A N3A C6A 109.1(2) . . ?
C16A N4A H4A 116.5 . . ?
C16A N4A C17A 126.9(2) . . ?
C17A N4A H4A 116.5 . . ?
C24A N5A C28A 111.1(2) . . ?
C25A N5A C24A 108.8(2) . . ?
C25A N5A C28A 108.9(2) . . ?
C26A N6A H6A 103(2) . . ?
C26A N6A C27A 109.4(2) . . ?
C26A N6A C29A 112.2(2) . . ?
C27A N6A H6A 110(2) . . ?
C27A N6A C29A 111.4(2) . . ?
C29A N6A H6A 110(2) . . ?
N2A C1A H1AA 117.5 . . ?
N2A C1A C2A 124.9(3) . . ?
C2A C1A H1AA 117.5 . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A C1A 119.9(3) . . ?
C3A C2A H2A 120.1 . . ?
C2A C3A H3A 121.8 . . ?
C2A C3A C4A 116.4(3) . . ?
C4A C3A H3A 121.8 . . ?
N1A C4A N3A 107.7(2) . . ?
N1A C4A C3A 133.3(3) . . ?
N3A C4A C3A 119.0(3) . . ?
N1A C5A H5A 125.3 . . ?
C6A C5A N1A 109.5(3) . . ?
C6A C5A H5A 125.3 . . ?
N3A C6A C7A 122.3(2) . . ?
C5A C6A N3A 105.1(2) . . ?
C5A C6A C7A 132.5(3) . . ?
C8A C7A C6A 178.2(3) . . ?
C7A C8A C9A 177.1(3) . . ?
C10A C9A C8A 118.3(2) . . ?
C10A C9A C14A 120.2(2) . . ?
C14A C9A C8A 121.5(2) . . ?
C9A C10A H10A 119.2 . . ?
C11A C10A C9A 121.6(3) . . ?
C11A C10A H10A 119.2 . . ?
C10A C11A C12A 118.0(3) . . ?
C10A C11A C16A 116.4(2) . . ?
C12A C11A C16A 125.6(2) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.5(3) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 119.0 . . ?
C14A C13A C12A 122.1(3) . . ?
C14A C13A H13A 119.0 . . ?
C9A C14A C15A 121.4(3) . . ?
C13A C14A C9A 117.5(3) . . ?
C13A C14A C15A 121.1(3) . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O1A C16A N4A 123.0(3) . . ?
O1A C16A C11A 119.7(2) . . ?
N4A C16A C11A 117.3(2) . . ?
C18A C17A N4A 117.5(2) . . ?
C22A C17A N4A 123.6(2) . . ?
C22A C17A C18A 118.9(2) . . ?
C17A C18A H18A 119.9 . . ?
C19A C18A C17A 120.2(3) . . ?
C19A C18A H18A 119.9 . . ?
C18A C19A H19A 118.8 . . ?
C18A C19A C20A 122.4(2) . . ?
C20A C19A H19A 118.8 . . ?
C19A C20A C21A 116.4(2) . . ?
C19A C20A C24A 118.7(2) . . ?
C21A C20A C24A 124.8(2) . . ?
C20A C21A C23A 120.6(2) . . ?
C22A C21A C20A 122.2(2) . . ?
C22A C21A C23A 117.3(2) . . ?
C17A C22A C21A 119.8(2) . . ?
C17A C22A H22A 120.1 . . ?
C21A C22A H22A 120.1 . . ?
F1A C23A F2A 105.7(2) . . ?
F1A C23A F3A 106.7(2) . . ?
F1A C23A C21A 113.4(2) . . ?
F2A C23A C21A 112.3(2) . . ?
F3A C23A F2A 105.1(2) . . ?
F3A C23A C21A 113.0(2) . . ?
N5A C24A C20A 114.0(2) . . ?
N5A C24A H24A 108.8 . . ?
N5A C24A H24B 108.8 . . ?
C20A C24A H24A 108.8 . . ?
C20A C24A H24B 108.8 . . ?
H24A C24A H24B 107.6 . . ?
N5A C25A H25A 109.3 . . ?
N5A C25A H25B 109.3 . . ?
N5A C25A C26A 111.4(2) . . ?
H25A C25A H25B 108.0 . . ?
C26A C25A H25A 109.3 . . ?
C26A C25A H25B 109.3 . . ?
N6A C26A C25A 110.1(2) . . ?
N6A C26A H26A 109.6 . . ?
N6A C26A H26B 109.6 . . ?
C25A C26A H26A 109.6 . . ?
C25A C26A H26B 109.6 . . ?
H26A C26A H26B 108.1 . . ?
N6A C27A H27A 109.7 . . ?
N6A C27A H27B 109.7 . . ?
N6A C27A C28A 110.0(2) . . ?
H27A C27A H27B 108.2 . . ?
C28A C27A H27A 109.7 . . ?
C28A C27A H27B 109.7 . . ?
N5A C28A C27A 111.2(2) . . ?
N5A C28A H28A 109.4 . . ?
N5A C28A H28B 109.4 . . ?
C27A C28A H28A 109.4 . . ?
C27A C28A H28B 109.4 . . ?
H28A C28A H28B 108.0 . . ?
N6A C29A H29A 109.5 . . ?
N6A C29A H29B 109.5 . . ?
N6A C29A H29C 109.5 . . ?
H29A C29A H29B 109.5 . . ?
H29A C29A H29C 109.5 . . ?
H29B C29A H29C 109.5 . . ?
C4B N1B C5B 106.2(2) . . ?
C1B N2B N3B 113.8(2) . . ?
N2B N3B C4B 126.0(2) . . ?
N2B N3B C6B 125.9(2) . . ?
C6B N3B C4B 108.1(2) . . ?
C16B N4B H4B 116.4 . . ?
C16B N4B C17B 127.2(2) . . ?
C17B N4B H4B 116.4 . . ?
C25B N5B C24B 109.2(2) . . ?
C28B N5B C24B 110.5(2) . . ?
C28B N5B C25B 110.4(2) . . ?
C26B N6B H6B 110(3) . . ?
C26B N6B C27B 108.6(2) . . ?
C27B N6B H6B 103(3) . . ?
C29B N6B H6B 111(3) . . ?
C29B N6B C26B 112.8(2) . . ?
C29B N6B C27B 111.0(2) . . ?
N2B C1B H1B 117.2 . . ?
N2B C1B C2B 125.6(3) . . ?
C2B C1B H1B 117.2 . . ?
C1B C2B H2B 120.5 . . ?
C3B C2B C1B 119.0(3) . . ?
C3B C2B H2B 120.5 . . ?
C2B C3B H3B 121.3 . . ?
C2B C3B C4B 117.4(3) . . ?
C4B C3B H3B 121.3 . . ?
N1B C4B N3B 109.7(2) . . ?
N1B C4B C3B 132.2(3) . . ?
N3B C4B C3B 118.1(3) . . ?
N1B C5B H5B 124.3 . . ?
N1B C5B C6B 111.4(3) . . ?
C6B C5B H5B 124.3 . . ?
N3B C6B C7B 124.2(3) . . ?
C5B C6B N3B 104.5(2) . . ?
C5B C6B C7B 131.3(3) . . ?
C8B C7B C6B 178.0(3) . . ?
C7B C8B C9B 178.7(3) . . ?
C10B C9B C8B 119.4(2) . . ?
C10B C9B C14B 120.1(2) . . ?
C14B C9B C8B 120.5(2) . . ?
C9B C10B H10B 119.4 . . ?
C9B C10B C11B 121.3(3) . . ?
C11B C10B H10B 119.4 . . ?
C10B C11B C12B 118.5(2) . . ?
C10B C11B C16B 116.6(2) . . ?
C12B C11B C16B 124.8(2) . . ?
C11B C12B H12B 120.1 . . ?
C13B C12B C11B 119.9(3) . . ?
C13B C12B H12B 120.1 . . ?
C12B C13B H13B 118.9 . . ?
C14B C13B C12B 122.1(3) . . ?
C14B C13B H13B 118.9 . . ?
C9B C14B C15B 120.2(3) . . ?
C13B C14B C9B 118.1(3) . . ?
C13B C14B C15B 121.7(3) . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
O1B C16B N4B 123.4(3) . . ?
O1B C16B C11B 120.3(2) . . ?
N4B C16B C11B 116.3(2) . . ?
C18B C17B N4B 117.3(2) . . ?
C18B C17B C22B 119.2(2) . . ?
C22B C17B N4B 123.4(2) . . ?
C17B C18B H18B 120.2 . . ?
C19B C18B C17B 119.6(3) . . ?
C19B C18B H18B 120.2 . . ?
C18B C19B H19B 118.8 . . ?
C18B C19B C20B 122.4(3) . . ?
C20B C19B H19B 118.8 . . ?
C19B C20B C21B 117.0(2) . . ?
C19B C20B C24B 119.0(2) . . ?
C21B C20B C24B 124.0(2) . . ?
C20B C21B C23B 122.6(2) . . ?
C22B C21B C20B 121.6(3) . . ?
C22B C21B C23B 115.7(2) . . ?
C17B C22B H22B 120.0 . . ?
C21B C22B C17B 120.1(3) . . ?
C21B C22B H22B 120.0 . . ?
F1B C23B F2B 104.6(2) . . ?
F1B C23B F3B 107.0(2) . . ?
F1B C23B C21B 114.4(2) . . ?
F2B C23B C21B 112.9(2) . . ?
F3B C23B F2B 105.1(2) . . ?
F3B C23B C21B 112.2(2) . . ?
N5B C24B C20B 112.9(2) . . ?
N5B C24B H24C 109.0 . . ?
N5B C24B H24D 109.0 . . ?
C20B C24B H24C 109.0 . . ?
C20B C24B H24D 109.0 . . ?
H24C C24B H24D 107.8 . . ?
N5B C25B H25C 109.5 . . ?
N5B C25B H25D 109.5 . . ?
N5B C25B C26B 110.6(2) . . ?
H25C C25B H25D 108.1 . . ?
C26B C25B H25C 109.5 . . ?
C26B C25B H25D 109.5 . . ?
N6B C26B C25B 109.0(2) . . ?
N6B C26B H26C 109.9 . . ?
N6B C26B H26D 109.9 . . ?
C25B C26B H26C 109.9 . . ?
C25B C26B H26D 109.9 . . ?
H26C C26B H26D 108.3 . . ?
N6B C27B H27C 109.7 . . ?
N6B C27B H27D 109.7 . . ?
N6B C27B C28B 109.7(2) . . ?
H27C C27B H27D 108.2 . . ?
C28B C27B H27C 109.7 . . ?
C28B C27B H27D 109.7 . . ?
N5B C28B C27B 111.1(2) . . ?
N5B C28B H28C 109.4 . . ?
N5B C28B H28D 109.4 . . ?
C27B C28B H28C 109.4 . . ?
C27B C28B H28D 109.4 . . ?
H28C C28B H28D 108.0 . . ?
N6B C29B H29D 109.5 . . ?
N6B C29B H29E 109.5 . . ?
N6B C29B H29F 109.5 . . ?
H29D C29B H29E 109.5 . . ?
H29D C29B H29F 109.5 . . ?
H29E C29B H29F 109.5 . . ?
H3C O3 H3D 109.6 . . ?
H2C O2 H2D 104.5 . . ?
H1C O1 H1D 109.5 . . ?
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
F1A C23A 1.346(3) . ?
F2A C23A 1.368(3) . ?
F3A C23A 1.352(3) . ?
O1A C16A 1.235(3) . ?
N1A H1A 1.07(4) . ?
N1A C4A 1.342(4) . ?
N1A C5A 1.380(4) . ?
N2A N3A 1.364(3) . ?
N2A C1A 1.317(4) . ?
N3A C4A 1.382(3) . ?
N3A C6A 1.400(4) . ?
N4A H4A 0.8800 . ?
N4A C16A 1.376(3) . ?
N4A C17A 1.426(3) . ?
N5A C24A 1.475(3) . ?
N5A C25A 1.474(3) . ?
N5A C28A 1.480(4) . ?
N6A H6A 0.93(4) . ?
N6A C26A 1.505(4) . ?
N6A C27A 1.505(4) . ?
N6A C29A 1.506(4) . ?
C1A H1AA 0.9500 . ?
C1A C2A 1.433(4) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.365(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.412(4) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.374(4) . ?
C6A C7A 1.422(4) . ?
C7A C8A 1.203(4) . ?
C8A C9A 1.449(4) . ?
C9A C10A 1.404(4) . ?
C9A C14A 1.418(4) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.399(4) . ?
C11A C12A 1.403(4) . ?
C11A C16A 1.514(4) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.398(4) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.398(4) . ?
C14A C15A 1.512(4) . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C17A C18A 1.403(4) . ?
C17A C22A 1.401(4) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.394(4) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.403(4) . ?
C20A C21A 1.409(4) . ?
C20A C24A 1.527(4) . ?
C21A C22A 1.404(4) . ?
C21A C23A 1.513(4) . ?
C22A H22A 0.9500 . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C25A C26A 1.521(4) . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C27A H27A 0.9900 . ?
C27A H27B 0.9900 . ?
C27A C28A 1.515(4) . ?
C28A H28A 0.9900 . ?
C28A H28B 0.9900 . ?
C29A H29A 0.9800 . ?
C29A H29B 0.9800 . ?
C29A H29C 0.9800 . ?
F1B C23B 1.328(3) . ?
F2B C23B 1.353(4) . ?
F3B C23B 1.340(3) . ?
O1B C16B 1.233(3) . ?
N1B C4B 1.341(4) . ?
N1B C5B 1.374(4) . ?
N2B N3B 1.362(3) . ?
N2B C1B 1.320(4) . ?
N3B C4B 1.394(4) . ?
N3B C6B 1.391(4) . ?
N4B H4B 0.8800 . ?
N4B C16B 1.366(3) . ?
N4B C17B 1.422(3) . ?
N5B C24B 1.479(3) . ?
N5B C25B 1.471(3) . ?
N5B C28B 1.468(3) . ?
N6B H6B 0.87(4) . ?
N6B C26B 1.503(4) . ?
N6B C27B 1.511(3) . ?
N6B C29B 1.495(4) . ?
C1B H1B 0.9500 . ?
C1B C2B 1.422(4) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.377(4) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.408(4) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.385(4) . ?
C6B C7B 1.420(4) . ?
C7B C8B 1.203(4) . ?
C8B C9B 1.447(4) . ?
C9B C10B 1.402(4) . ?
C9B C14B 1.420(4) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.406(4) . ?
C11B C12B 1.412(4) . ?
C11B C16B 1.506(4) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.397(4) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.396(4) . ?
C14B C15B 1.510(4) . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C17B C18B 1.401(4) . ?
C17B C22B 1.406(4) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.400(4) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.404(4) . ?
C20B C21B 1.408(4) . ?
C20B C24B 1.518(4) . ?
C21B C22B 1.402(4) . ?
C21B C23B 1.530(4) . ?
C22B H22B 0.9500 . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C25B C26B 1.527(4) . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C27B H27C 0.9900 . ?
C27B H27D 0.9900 . ?
C27B C28B 1.522(4) . ?
C28B H28C 0.9900 . ?
C28B H28D 0.9900 . ?
C29B H29D 0.9800 . ?
C29B H29E 0.9800 . ?
C29B H29F 0.9800 . ?
O3 H3C 0.8501 . ?
O3 H3D 0.8494 . ?
O2 H2C 0.8503 . ?
O2 H2D 0.8498 . ?
O1 H1C 0.8501 . ?
O1 H1D 0.8501 . ?
