#------------------------------------------------------------------------------
#$Date: 2022-01-21 03:13:42 +0100 (vie 21 de ene de 2022) $
#$Revision: 272181 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/42/7244269.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_7244269
loop_
_publ_author_name
'Bao, Lihong'
'Jones, Leighton O.'
'Garrote Cañas, Ana M.'
'Yan, Yunhan'
'Pask, Christopher M.'
'Hardie, Michaele J.'
'Mosquera, Martin A.'
'Schatz, George C.'
'Sergeeva, Natalia N.'
_publ_section_title
;
 Multipurpose made colorimetric materials for amines, pH change and metal
 ion detection
;
_journal_issue                   5
_journal_name_full               'RSC Advances'
_journal_page_first              2684
_journal_page_last               2692
_journal_paper_doi               10.1039/D1RA07811A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'Cl O4, C23 H20 F6 N5 O2'
_chemical_formula_sum            'C23 H20 Cl F6 N5 O6'
_chemical_formula_weight         611.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-05-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-27 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.731(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2533(7)
_cell_length_b                   12.9873(5)
_cell_length_c                   13.5404(5)
_cell_measurement_reflns_used    4236
_cell_measurement_temperature    120.00(11)
_cell_measurement_theta_max      73.3930
_cell_measurement_theta_min      4.8230
_cell_volume                     2554.92(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  -60.0000 62

#__ type_ start__ end____ width___ exp.time_
  2 omega  -51.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000 -150.0000 63

#__ type_ start__ end____ width___ exp.time_
  3 omega  -68.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -37.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega -105.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   37.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -45.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega   77.00  150.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.9775    0.0000  150.0000 73

#__ type_ start__ end____ width___ exp.time_
  7 omega   60.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -30.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   52.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -30.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -45.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega   88.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -65.0000  -77.5236 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -64.0000  -89.7910 63

#__ type_ start__ end____ width___ exp.time_
 12 omega   32.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -30.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega   25.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.9775    0.0000  150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0980196000
_diffrn_orient_matrix_UB_12      -0.0412154000
_diffrn_orient_matrix_UB_13      -0.0520032000
_diffrn_orient_matrix_UB_21      0.0140688000
_diffrn_orient_matrix_UB_22      0.0124106000
_diffrn_orient_matrix_UB_23      -0.1073531000
_diffrn_orient_matrix_UB_31      0.0379131000
_diffrn_orient_matrix_UB_32      -0.1104903000
_diffrn_orient_matrix_UB_33      0.0073003000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10606
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.661
_diffrn_reflns_theta_min         3.042
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.192
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5017
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0584
_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)+(0.0751P)²+1.9671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4034
_reflns_number_total             5017
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra07811a2.cif
_cod_data_source_block           yy04_cu
_cod_original_cell_volume        2554.92(18)
_cod_database_code               7244269
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C92 H80 Cl4 F24 N20 O24'
_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.
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F6B-C23 = F6A-C23 = F4B-C23 = F4A-C23 = F5B-C23 = F5A-C23
 1.33 with sigma of 0.005
3. Rigid bond restraints
 F5A, F5B, F4A, F4B, F6A, F6B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F5A \\sim F5B \\sim F4A \\sim F4B \\sim F6B \\sim F6A: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Others
 Fixed Sof: F4A(0.6) F6A(0.6) F5A(0.6) F5B(0.4) F6B(0.4) F4B(0.4)
6.a Aromatic/amide H refined with riding coordinates:
 N5(H5), N3(H3), N1(H1), C10(H10), C12(H12), C4(H4), C13(H13), C3(H3A), C9(H9),
  C22(H22), C2(H2), C19(H19), C21(H21), C18(H18)
6.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C7(H7A,H7B,H7C)
;
_olex2_date_sample_data_collection 2016-04-11
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.41464(5) 0.35794(6) 0.09319(5) 0.0452(2) Uani 1 1 d . . . . .
O1 O -0.02318(14) 0.81214(19) -0.63741(16) 0.0520(5) Uani 1 1 d . . . . .
O4 O 0.32653(14) 0.30826(16) 0.07056(16) 0.0467(5) Uani 1 1 d . . . . .
F2 F 0.05998(14) 0.7772(2) -0.74139(15) 0.0739(7) Uani 1 1 d . . . . .
O6 O 0.42256(16) 0.43585(16) 0.17013(16) 0.0523(5) Uani 1 1 d . . . . .
N5 N 0.31946(18) 0.6112(2) -0.10311(18) 0.0444(6) Uani 1 1 d . . . . .
H5 H 0.3364 0.5667 -0.0539 0.053 Uiso 1 1 calc R . . . .
N2 N 0.26371(18) 1.0045(2) -0.23541(17) 0.0441(6) Uani 1 1 d . . . . .
F1 F -0.06323(16) 0.69429(19) -0.75475(16) 0.0704(6) Uani 1 1 d . . . . .
N3 N 0.22365(18) 1.0436(2) -0.33027(18) 0.0457(6) Uani 1 1 d . . . . .
H3 H 0.2340 1.1063 -0.3438 0.055 Uiso 1 1 calc R . . . .
N4 N 0.32983(15) 0.71190(19) -0.08201(17) 0.0383(5) Uani 1 1 d . . . . .
N1 N 0.34930(17) 0.91120(19) -0.06065(17) 0.0405(5) Uani 1 1 d . . . . .
H1 H 0.3212 0.8802 -0.1176 0.049 Uiso 1 1 calc R . . . .
C10 C 0.0629(2) 0.8382(3) -0.4579(2) 0.0479(7) Uani 1 1 d . . . . .
H10 H 0.0348 0.7800 -0.4410 0.057 Uiso 1 1 calc R . . . .
C11 C 0.04423(19) 0.8683(3) -0.5606(2) 0.0448(7) Uani 1 1 d . . . . .
C5 C 0.38372(19) 0.8520(2) 0.0249(2) 0.0378(6) Uani 1 1 d . . . . .
C12 C 0.0843(2) 0.9545(3) -0.5875(2) 0.0475(7) Uani 1 1 d . . . . .
H12 H 0.0704 0.9741 -0.6566 0.057 Uiso 1 1 calc R . . . .
C1 C 0.3556(2) 1.0154(2) -0.0638(2) 0.0447(7) Uani 1 1 d . . . . .
C4 C 0.4307(2) 0.9021(2) 0.1166(2) 0.0416(6) Uani 1 1 d . . . . .
H4 H 0.4554 0.8648 0.1774 0.050 Uiso 1 1 calc R . . . .
C15 C 0.37065(18) 0.7408(2) 0.0126(2) 0.0379(6) Uani 1 1 d . . . . .
C8 C 0.16529(19) 0.9821(2) -0.4065(2) 0.0432(7) Uani 1 1 d . . . . .
C13 C 0.1452(2) 1.0116(3) -0.5108(2) 0.0465(7) Uani 1 1 d . . . . .
H13 H 0.1729 1.0697 -0.5283 0.056 Uiso 1 1 calc R . . . .
C3 C 0.4403(2) 1.0077(2) 0.1162(2) 0.0483(7) Uani 1 1 d . . . . .
H3A H 0.4723 1.0412 0.1773 0.058 Uiso 1 1 calc R . . . .
C6 C 0.3108(2) 1.0659(2) -0.1631(2) 0.0457(7) Uani 1 1 d . . . . .
O2 O 0.1743(2) 0.4854(3) -0.5136(2) 0.0805(9) Uani 1 1 d . . . . .
F4A F 0.0717(5) 0.4165(7) -0.6458(4) 0.109(3) Uani 0.6 1 d D U P A 1
C17 C 0.2809(2) 0.5789(2) -0.2055(2) 0.0462(7) Uani 1 1 d . . . . .
F3 F 0.0578(2) 0.6678(2) -0.62623(17) 0.1076(11) Uani 1 1 d . . . . .
C16 C 0.4045(2) 0.6695(2) 0.1026(2) 0.0477(7) Uani 1 1 d . . . . .
H16A H 0.3563 0.6224 0.1038 0.072 Uiso 1 1 calc GR . . . .
H16B H 0.4223 0.7086 0.1658 0.072 Uiso 1 1 calc GR . . . .
H16C H 0.4565 0.6317 0.0962 0.072 Uiso 1 1 calc GR . . . .
F6A F 0.1626(7) 0.3202(5) -0.5279(9) 0.091(3) Uani 0.6 1 d D U P A 1
C9 C 0.12373(19) 0.8955(3) -0.3809(2) 0.0460(7) Uani 1 1 d . . . . .
H9 H 0.1368 0.8759 -0.3119 0.055 Uiso 1 1 calc R . . . .
C22 C 0.2431(2) 0.6495(3) -0.2853(2) 0.0473(7) Uani 1 1 d . . . . .
H22 H 0.2434 0.7196 -0.2709 0.057 Uiso 1 1 calc R . . . .
O5 O 0.48558(17) 0.2829(2) 0.1330(2) 0.0749(8) Uani 1 1 d . . . . .
C7 C 0.3172(3) 1.1802(2) -0.1739(2) 0.0542(8) Uani 1 1 d . . . . .
H7A H 0.3647 1.1960 -0.2044 0.081 Uiso 1 1 calc GR . . . .
H7B H 0.3315 1.2117 -0.1067 0.081 Uiso 1 1 calc GR . . . .
H7C H 0.2594 1.2062 -0.2173 0.081 Uiso 1 1 calc GR . . . .
C14 C 0.0075(2) 0.7389(3) -0.6877(2) 0.0560(8) Uani 1 1 d . . . . .
C2 C 0.4032(2) 1.0650(2) 0.0268(2) 0.0519(8) Uani 1 1 d . . . . .
H2 H 0.4103 1.1362 0.0279 0.062 Uiso 1 1 calc R . . . .
O3 O 0.4228(3) 0.4057(3) 0.0016(2) 0.0969(11) Uani 1 1 d . . . . .
F5A F 0.0530(3) 0.4011(5) -0.4968(5) 0.094(2) Uani 0.6 1 d D U P A 1
C19 C 0.2427(3) 0.4399(3) -0.3291(3) 0.0701(11) Uani 1 1 d . . . . .
H19 H 0.2431 0.3701 -0.3445 0.084 Uiso 1 1 calc R . . . .
C21 C 0.2055(2) 0.6143(3) -0.3856(2) 0.0519(8) Uani 1 1 d . . . . .
H21 H 0.1801 0.6607 -0.4389 0.062 Uiso 1 1 calc R . . . .
C20 C 0.2054(2) 0.5108(3) -0.4067(3) 0.0608(9) Uani 1 1 d . . . . .
C18 C 0.2795(3) 0.4741(3) -0.2281(3) 0.0621(9) Uani 1 1 d . . . . .
H18 H 0.3034 0.4269 -0.1750 0.075 Uiso 1 1 calc R . . . .
C23 C 0.1169(2) 0.4080(3) -0.5462(3) 0.0725(12) Uani 1 1 d D . . . .
F5B F 0.0372(4) 0.4312(8) -0.5345(7) 0.070(2) Uani 0.4 1 d D U P A 2
F6B F 0.1380(9) 0.3131(5) -0.5103(12) 0.084(5) Uani 0.4 1 d D U P A 2
F4B F 0.1040(7) 0.4034(14) -0.6484(4) 0.100(5) Uani 0.4 1 d D U 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'
F F 0.0727 0.0534 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4 5 -7 0.0946 3.9899 5.0058 -6.9855 -0.2341 0.8682 -0.4528
-4 -5 7 0.0946 -3.9899 -5.0058 6.9855 0.2341 -0.8682 0.4528
2 -7 -5 0.0846 2.0302 -6.9986 -5.0077 0.3499 0.4793 0.8137
-2 7 5 0.0846 -2.0302 6.9986 5.0077 -0.3499 -0.4793 -0.8137
2 8 -2 0.0931 1.9731 8.0034 -1.9839 -0.4201 0.3401 -0.8240
-2 -8 2 0.0931 -1.9731 -8.0034 1.9839 0.4201 -0.3401 0.8240
-4 6 -4 0.1182 -4.0025 6.0040 -4.0016 0.3530 0.4478 -0.8443
-7 -5 0 0.0923 -6.9677 -5.0015 -0.0240 0.8904 -0.1575 0.2883
5 -5 4 0.1189 4.9969 -5.0037 4.0055 -0.4919 -0.4218 0.7716
8 3 1 0.1036 7.9700 3.0003 1.0236 -0.9581 0.0395 -0.0219
-7 3 7 0.0653 -7.0101 2.9962 6.9907 0.2001 -0.8119 -0.5458
7 -3 -7 0.0653 7.0101 -2.9962 -6.9907 -0.2001 0.8119 0.5458
0 -4 8 0.1088 -0.0043 -4.0061 7.9968 -0.2503 -0.9083 0.5009
-9 2 2 0.0720 -8.9913 1.9991 1.9827 0.6958 -0.3145 -0.5473
9 3 -4 0.0787 8.9789 3.0035 -3.9758 -0.7971 0.5904 -0.0205
-9 -4 4 0.0724 -8.9755 -4.0038 3.9743 0.8381 -0.6026 0.1311
-2 5 -6 0.1147 -1.9991 5.0050 -5.9992 0.3016 0.6780 -0.6726
7 5 -5 0.0741 6.9788 5.0046 -4.9778 -0.6315 0.6947 -0.3247
-6 -5 5 0.0770 -5.9810 -5.0046 4.9802 0.5335 -0.6809 0.3626
10 -2 -2 0.0764 9.9891 -1.9991 -1.9804 -0.7937 0.3283 0.5851
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
O6 Cl1 O4 109.81(13) . . ?
O6 Cl1 O5 108.68(15) . . ?
O5 Cl1 O4 108.93(15) . . ?
O3 Cl1 O4 109.46(17) . . ?
O3 Cl1 O6 108.40(17) . . ?
O3 Cl1 O5 111.5(2) . . ?
C14 O1 C11 116.8(2) . . ?
N4 N5 H5 120.2 . . ?
N4 N5 C17 119.5(2) . . ?
C17 N5 H5 120.2 . . ?
C6 N2 N3 118.4(3) . . ?
N2 N3 H3 120.2 . . ?
N2 N3 C8 119.7(3) . . ?
C8 N3 H3 120.2 . . ?
C15 N4 N5 118.9(2) . . ?
C5 N1 H1 117.3 . . ?
C5 N1 C1 125.3(2) . . ?
C1 N1 H1 117.3 . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.3(3) . . ?
C10 C11 O1 118.1(3) . . ?
C12 C11 O1 120.3(2) . . ?
C12 C11 C10 121.5(3) . . ?
N1 C5 C4 117.3(3) . . ?
N1 C5 C15 117.3(2) . . ?
C4 C5 C15 125.4(2) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.3(3) . . ?
C13 C12 H12 120.3 . . ?
N1 C1 C6 117.2(3) . . ?
N1 C1 C2 117.4(3) . . ?
C2 C1 C6 125.4(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
N4 C15 C5 114.0(2) . . ?
N4 C15 C16 124.7(3) . . ?
C5 C15 C16 121.2(2) . . ?
N3 C8 C13 119.0(3) . . ?
C9 C8 N3 121.2(2) . . ?
C9 C8 C13 119.7(3) . . ?
C12 C13 C8 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C4 C3 H3A 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C2 C3 H3A 119.3 . . ?
N2 C6 C1 114.4(3) . . ?
N2 C6 C7 125.0(3) . . ?
C1 C6 C7 120.4(3) . . ?
C23 O2 C20 120.1(3) . . ?
N5 C17 C22 121.3(3) . . ?
C18 C17 N5 119.0(3) . . ?
C18 C17 C22 119.7(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C17 C22 H22 120.3 . . ?
C21 C22 C17 119.4(3) . . ?
C21 C22 H22 120.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
F2 C14 O1 112.1(3) . . ?
F1 C14 O1 109.0(3) . . ?
F1 C14 F2 106.9(2) . . ?
F1 C14 F3 108.9(3) . . ?
F3 C14 O1 113.8(3) . . ?
F3 C14 F2 105.9(3) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C20 C19 H19 120.5 . . ?
C20 C19 C18 119.1(4) . . ?
C18 C19 H19 120.5 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C19 C20 O2 123.6(4) . . ?
C21 C20 O2 114.8(3) . . ?
C21 C20 C19 121.3(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.8 . . ?
O2 C23 F4A 111.5(5) . . ?
O2 C23 F6A 109.7(6) . . ?
O2 C23 F5A 113.1(4) . . ?
O2 C23 F6B 121.5(7) . . ?
O2 C23 F4B 104.7(7) . . ?
F4A C23 F6A 110.2(7) . . ?
F4A C23 F5A 106.4(5) . . ?
F6A C23 F5A 105.7(6) . . ?
F5B C23 O2 109.3(5) . . ?
F5B C23 F6B 107.5(8) . . ?
F5B C23 F4B 106.7(7) . . ?
F6B C23 F4B 106.3(11) . . ?
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 O4 1.437(2) . ?
Cl1 O6 1.431(2) . ?
Cl1 O5 1.434(3) . ?
Cl1 O3 1.425(3) . ?
O1 C11 1.421(4) . ?
O1 C14 1.334(4) . ?
F2 C14 1.331(4) . ?
N5 H5 0.8600 . ?
N5 N4 1.338(3) . ?
N5 C17 1.395(4) . ?
N2 N3 1.343(3) . ?
N2 C6 1.297(4) . ?
F1 C14 1.314(4) . ?
N3 H3 0.8600 . ?
N3 C8 1.391(4) . ?
N4 C15 1.297(4) . ?
N1 H1 0.8600 . ?
N1 C5 1.356(3) . ?
N1 C1 1.359(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(4) . ?
C10 C9 1.383(5) . ?
C11 C12 1.376(5) . ?
C5 C4 1.391(4) . ?
C5 C15 1.461(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(5) . ?
C1 C6 1.465(4) . ?
C1 C2 1.380(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.380(4) . ?
C15 C16 1.492(4) . ?
C8 C13 1.404(4) . ?
C8 C9 1.386(5) . ?
C13 H13 0.9300 . ?
C3 H3A 0.9300 . ?
C3 C2 1.386(4) . ?
C6 C7 1.497(4) . ?
O2 C20 1.417(4) . ?
O2 C23 1.318(4) . ?
F4A C23 1.319(4) . ?
C17 C22 1.401(5) . ?
C17 C18 1.393(5) . ?
F3 C14 1.322(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
F6A C23 1.320(4) . ?
C9 H9 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.381(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C2 H2 0.9300 . ?
F5A C23 1.343(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(6) . ?
C19 C18 1.384(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.374(5) . ?
C18 H18 0.9300 . ?
C23 F5B 1.309(5) . ?
C23 F6B 1.329(5) . ?
C23 F4B 1.339(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
O1 C11 C12 C13 175.9(2) . . . . ?
N5 N4 C15 C5 175.9(2) . . . . ?
N5 N4 C15 C16 -2.6(4) . . . . ?
N5 C17 C22 C21 -179.8(3) . . . . ?
N5 C17 C18 C19 -179.2(3) . . . . ?
N2 N3 C8 C13 -161.8(2) . . . . ?
N2 N3 C8 C9 21.2(4) . . . . ?
N3 N2 C6 C1 -177.2(2) . . . . ?
N3 N2 C6 C7 6.1(4) . . . . ?
N3 C8 C13 C12 -177.1(3) . . . . ?
N3 C8 C9 C10 177.2(3) . . . . ?
N4 N5 C17 C22 -7.4(4) . . . . ?
N4 N5 C17 C18 173.2(3) . . . . ?
N1 C5 C4 C3 -0.2(4) . . . . ?
N1 C5 C15 N4 2.6(3) . . . . ?
N1 C5 C15 C16 -178.8(2) . . . . ?
N1 C1 C6 N2 5.1(4) . . . . ?
N1 C1 C6 C7 -178.0(3) . . . . ?
N1 C1 C2 C3 -1.4(5) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 O1 C14 F2 -62.4(3) . . . . ?
C11 O1 C14 F1 179.4(3) . . . . ?
C11 O1 C14 F3 57.7(4) . . . . ?
C11 C10 C9 C8 0.1(4) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C5 N1 C1 C6 -177.7(3) . . . . ?
C5 N1 C1 C2 2.0(4) . . . . ?
C5 C4 C3 C2 0.7(5) . . . . ?
C1 N1 C5 C4 -1.2(4) . . . . ?
C1 N1 C5 C15 -179.5(3) . . . . ?
C4 C5 C15 N4 -175.6(3) . . . . ?
C4 C5 C15 C16 3.1(4) . . . . ?
C4 C3 C2 C1 0.1(5) . . . . ?
C15 C5 C4 C3 177.9(3) . . . . ?
C13 C8 C9 C10 0.2(4) . . . . ?
C6 N2 N3 C8 -173.6(2) . . . . ?
C6 C1 C2 C3 178.4(3) . . . . ?
C17 N5 N4 C15 -176.0(2) . . . . ?
C17 C22 C21 C20 -0.2(5) . . . . ?
C9 C10 C11 O1 -175.8(2) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C9 C8 C13 C12 0.0(4) . . . . ?
C22 C17 C18 C19 1.3(5) . . . . ?
C22 C21 C20 O2 -173.3(3) . . . . ?
C22 C21 C20 C19 -0.1(5) . . . . ?
C14 O1 C11 C10 -97.4(3) . . . . ?
C14 O1 C11 C12 87.4(3) . . . . ?
C2 C1 C6 N2 -174.6(3) . . . . ?
C2 C1 C6 C7 2.3(5) . . . . ?
C20 O2 C23 F4A 158.4(5) . . . . ?
C20 O2 C23 F6A -79.2(7) . . . . ?
C20 O2 C23 F5A 38.6(5) . . . . ?
C20 O2 C23 F5B 67.8(6) . . . . ?
C20 O2 C23 F6B -58.2(9) . . . . ?
C20 O2 C23 F4B -178.3(7) . . . . ?
C20 C19 C18 C17 -1.6(6) . . . . ?
C18 C17 C22 C21 -0.4(4) . . . . ?
C18 C19 C20 O2 173.6(4) . . . . ?
C18 C19 C20 C21 1.0(6) . . . . ?
C23 O2 C20 C19 51.1(5) . . . . ?
C23 O2 C20 C21 -135.9(3) . . . . ?
