#------------------------------------------------------------------------------
#$Date: 2019-11-23 22:47:51 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235428 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/69/4036928.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_4036928
loop_
_publ_author_name
'Niu, Guangle'
'Liu, Weimin'
'Zhou, Bingjiang'
'Xiao, Hongyan'
'Zhang, Hongyan'
'Wu, Jiasheng'
'Ge, Jiechao'
'Wang, Pengfei'
_publ_section_title
;
 Deep-Red and Near-Infrared Xanthene Dyes for Rapid Live Cell Imaging.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7393
_journal_page_last               7399
_journal_paper_doi               10.1021/acs.joc.6b00981
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C24 H26 F3 N2 O, Cl O4'
_chemical_formula_sum            'C24 H26 Cl F3 N2 O5'
_chemical_formula_weight         514.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.89(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.165(4)
_cell_length_b                   7.1874(14)
_cell_length_c                   34.207(7)
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4805
_cell_measurement_theta_min      1.2320
_cell_volume                     4791.3(18)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'

;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1064
	          2theta: -19.9311
scan:
	Number of images: 270
	           Slice: -76.2500 - 58.7500
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1064
	          2theta: -19.9311
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0501
_diffrn_orient_matrix_UB_12      0.0072
_diffrn_orient_matrix_UB_13      0.0083
_diffrn_orient_matrix_UB_21      0.0297
_diffrn_orient_matrix_UB_22      -0.0914
_diffrn_orient_matrix_UB_23      -0.1006
_diffrn_orient_matrix_UB_31      0.0077
_diffrn_orient_matrix_UB_32      0.0227
_diffrn_orient_matrix_UB_33      -0.0184
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            15566
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.686
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       rod
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5441
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0751
_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)+(0.1035P)²+7.3976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2019
_refine_ls_wR_factor_ref         0.2096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4837
_reflns_number_total             5441
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b00981_si_002.cif
_cod_data_source_block           sa4192
_cod_original_cell_volume        4791.2(18)
_cod_database_code               4036928
_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.
;
_diffrn_number_total             5882
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-O7 = Cl2-O4 = Cl2-O5 = Cl2-O6
 1.43 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: Cl2(0.5) O4(0.5) O5(0.5) O6(0.5) O7(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C16(H16A,H16B), C17(H17A,H17B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C18(H18), C19(H19), C21(H21)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
F1 F 0.64434(9) 0.9192(2) 0.36378(6) 0.0479(5) Uani 1 1 d . . . . .
F2 F 0.61167(10) 0.6383(3) 0.35262(6) 0.0554(5) Uani 1 1 d . . . . .
F3 F 0.56881(10) 0.8494(4) 0.31002(6) 0.0704(7) Uani 1 1 d . . . . .
O1 O 0.79397(8) 0.7068(2) 0.28128(5) 0.0254(4) Uani 1 1 d . . . . .
N1 N 0.95541(11) 0.6167(3) 0.40683(6) 0.0315(5) Uani 1 1 d . . . . .
N2 N 0.71347(12) 0.7321(3) 0.09129(6) 0.0365(5) Uani 1 1 d . . . . .
C1 C 1.03545(16) 0.7868(5) 0.37456(10) 0.0511(8) Uani 1 1 d . . . . .
H1A H 1.0668 0.7666 0.3581 0.077 Uiso 1 1 calc GR . . . .
H1B H 1.0584 0.8531 0.3986 0.077 Uiso 1 1 calc GR . . . .
H1C H 0.9970 0.8584 0.3597 0.077 Uiso 1 1 calc GR . . . .
C2 C 1.01029(14) 0.5998(4) 0.38621(8) 0.0381(6) Uani 1 1 d . . . . .
H2A H 0.9939 0.5257 0.3620 0.046 Uiso 1 1 calc R . . . .
H2B H 1.0486 0.5342 0.4037 0.046 Uiso 1 1 calc R . . . .
C3 C 0.9965(2) 0.7975(5) 0.47108(9) 0.0552(9) Uani 1 1 d . . . . .
H3A H 0.9592 0.8838 0.4625 0.083 Uiso 1 1 calc GR . . . .
H3B H 1.0359 0.8434 0.4633 0.083 Uiso 1 1 calc GR . . . .
H3C H 1.0074 0.7839 0.5000 0.083 Uiso 1 1 calc GR . . . .
C4 C 0.97581(15) 0.6106(4) 0.45131(7) 0.0368(6) Uani 1 1 d . . . . .
H4A H 1.0140 0.5251 0.4599 0.044 Uiso 1 1 calc R . . . .
H4B H 0.9379 0.5619 0.4608 0.044 Uiso 1 1 calc R . . . .
C5 C 0.89047(12) 0.6599(3) 0.38559(7) 0.0265(5) Uani 1 1 d . . . . .
C6 C 0.83660(14) 0.6911(4) 0.40497(7) 0.0309(5) Uani 1 1 d . . . . .
H6 H 0.8468 0.6887 0.4331 0.037 Uiso 1 1 calc R . . . .
C7 C 0.77076(13) 0.7242(3) 0.38353(7) 0.0302(5) Uani 1 1 d . . . . .
H7 H 0.7374 0.7439 0.3975 0.036 Uiso 1 1 calc R . . . .
C8 C 0.75132(12) 0.7299(3) 0.34063(7) 0.0261(5) Uani 1 1 d . . . . .
C9 C 0.80613(12) 0.7024(3) 0.32249(7) 0.0242(5) Uani 1 1 d . . . . .
C10 C 0.87316(12) 0.6719(3) 0.34304(7) 0.0261(5) Uani 1 1 d . . . . .
H10 H 0.9068 0.6594 0.3291 0.031 Uiso 1 1 calc R . . . .
C11 C 0.68428(12) 0.7540(3) 0.31449(8) 0.0281(5) Uani 1 1 d . . . . .
C12 C 0.67197(12) 0.7398(3) 0.27271(7) 0.0259(5) Uani 1 1 d . . . . .
C13 C 0.73031(11) 0.7197(3) 0.25706(7) 0.0238(5) Uani 1 1 d . . . . .
C14 C 0.72718(12) 0.7202(3) 0.21515(7) 0.0250(5) Uani 1 1 d . . . . .
C15 C 0.66325(12) 0.6886(3) 0.18661(7) 0.0273(5) Uani 1 1 d . . . . .
C16 C 0.60297(12) 0.6447(4) 0.20338(8) 0.0327(5) Uani 1 1 d . . . . .
H16A H 0.6033 0.5130 0.2096 0.039 Uiso 1 1 calc R . . . .
H16B H 0.5609 0.6713 0.1830 0.039 Uiso 1 1 calc R . . . .
C17 C 0.60392(12) 0.7562(4) 0.24135(8) 0.0322(5) Uani 1 1 d . . . . .
H17A H 0.5950 0.8861 0.2342 0.039 Uiso 1 1 calc R . . . .
H17B H 0.5676 0.7122 0.2528 0.039 Uiso 1 1 calc R . . . .
C18 C 0.78605(12) 0.7518(3) 0.20100(7) 0.0266(5) Uani 1 1 d . . . . .
H18 H 0.8285 0.7678 0.2194 0.032 Uiso 1 1 calc R . . . .
C19 C 0.78130(13) 0.7590(3) 0.16043(7) 0.0287(5) Uani 1 1 d . . . . .
H19 H 0.8203 0.7852 0.1517 0.034 Uiso 1 1 calc R . . . .
C20 C 0.71780(13) 0.7270(3) 0.13138(7) 0.0293(5) Uani 1 1 d . . . . .
C21 C 0.65935(13) 0.6893(3) 0.14615(8) 0.0301(5) Uani 1 1 d . . . . .
H21 H 0.6175 0.6646 0.1278 0.036 Uiso 1 1 calc R . . . .
C22 C 0.77293(16) 0.7738(5) 0.07565(8) 0.0446(7) Uani 1 1 d . . . . .
H22A H 0.7947 0.8854 0.0881 0.067 Uiso 1 1 calc GR . . . .
H22B H 0.7582 0.7908 0.0469 0.067 Uiso 1 1 calc GR . . . .
H22C H 0.8049 0.6724 0.0817 0.067 Uiso 1 1 calc GR . . . .
C23 C 0.64962(17) 0.6934(5) 0.06134(9) 0.0474(7) Uani 1 1 d . . . . .
H23A H 0.6364 0.5666 0.0639 0.071 Uiso 1 1 calc GR . . . .
H23B H 0.6558 0.7130 0.0347 0.071 Uiso 1 1 calc GR . . . .
H23C H 0.6144 0.7750 0.0655 0.071 Uiso 1 1 calc GR . . . .
C24 C 0.62644(13) 0.7913(4) 0.33453(8) 0.0345(6) Uani 1 1 d . . . . .
Cl2 Cl 0.81127(11) 0.7149(3) 0.51678(5) 0.0600(5) Uani 0.5 1 d D . . A -1
O4 O 0.7880(6) 0.8396(14) 0.4837(3) 0.108(3) Uani 0.5 1 d D U . A -1
O5 O 0.8520(3) 0.5760(8) 0.50865(16) 0.0701(16) Uani 0.5 1 d D U . A -1
O6 O 0.8580(6) 0.7933(17) 0.5507(3) 0.174(5) Uani 0.5 1 d D . . A -1
O7 O 0.7527(5) 0.6441(19) 0.5273(4) 0.142(5) Uani 0.5 1 d D . . A -1
Cl1 Cl 0.5000 0.28789(12) 0.2500 0.0331(2) Uani 1 2 d S T P . .
O2 O 0.54601(13) 0.4031(4) 0.27881(7) 0.0608(7) Uani 1 1 d . . . . .
O3 O 0.46189(14) 0.1769(4) 0.27089(8) 0.0629(7) Uani 1 1 d . . . . .
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
C13 O1 C9 121.89(18) . .
C2 N1 C4 116.8(2) . .
C5 N1 C2 120.4(2) . .
C5 N1 C4 122.3(2) . .
C20 N2 C22 122.1(2) . .
C20 N2 C23 121.7(3) . .
C23 N2 C22 116.3(2) . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
N1 C2 C1 113.4(3) . .
N1 C2 H2A 108.9 . .
N1 C2 H2B 108.9 . .
C1 C2 H2A 108.9 . .
C1 C2 H2B 108.9 . .
H2A C2 H2B 107.7 . .
H3A C3 H3B 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C4 C3 H3A 109.5 . .
C4 C3 H3B 109.5 . .
C4 C3 H3C 109.5 . .
N1 C4 C3 114.0(2) . .
N1 C4 H4A 108.7 . .
N1 C4 H4B 108.7 . .
C3 C4 H4A 108.7 . .
C3 C4 H4B 108.7 . .
H4A C4 H4B 107.6 . .
N1 C5 C6 122.0(2) . .
N1 C5 C10 121.0(2) . .
C10 C5 C6 117.0(2) . .
C5 C6 H6 119.0 . .
C7 C6 C5 122.0(2) . .
C7 C6 H6 119.0 . .
C6 C7 H7 118.9 . .
C6 C7 C8 122.2(2) . .
C8 C7 H7 118.9 . .
C7 C8 C11 128.1(2) . .
C9 C8 C7 114.3(2) . .
C9 C8 C11 117.6(2) . .
O1 C9 C8 119.7(2) . .
O1 C9 C10 115.1(2) . .
C10 C9 C8 125.2(2) . .
C5 C10 H10 120.4 . .
C9 C10 C5 119.3(2) . .
C9 C10 H10 120.4 . .
C8 C11 C24 116.9(2) . .
C12 C11 C8 121.7(2) . .
C12 C11 C24 121.4(2) . .
C11 C12 C13 116.7(2) . .
C11 C12 C17 127.8(2) . .
C13 C12 C17 115.4(2) . .
O1 C13 C12 121.9(2) . .
O1 C13 C14 114.3(2) . .
C14 C13 C12 123.7(2) . .
C13 C14 C15 119.4(2) . .
C18 C14 C13 121.6(2) . .
C18 C14 C15 119.0(2) . .
C14 C15 C16 116.8(2) . .
C21 C15 C14 120.1(2) . .
C21 C15 C16 123.0(2) . .
C15 C16 H16A 109.1 . .
C15 C16 H16B 109.1 . .
C15 C16 C17 112.4(2) . .
H16A C16 H16B 107.9 . .
C17 C16 H16A 109.1 . .
C17 C16 H16B 109.1 . .
C12 C17 C16 112.0(2) . .
C12 C17 H17A 109.2 . .
C12 C17 H17B 109.2 . .
C16 C17 H17A 109.2 . .
C16 C17 H17B 109.2 . .
H17A C17 H17B 107.9 . .
C14 C18 H18 119.7 . .
C19 C18 C14 120.6(2) . .
C19 C18 H18 119.7 . .
C18 C19 H19 119.4 . .
C18 C19 C20 121.2(2) . .
C20 C19 H19 119.4 . .
N2 C20 C19 121.0(2) . .
N2 C20 C21 121.5(2) . .
C21 C20 C19 117.5(2) . .
C15 C21 C20 121.6(2) . .
C15 C21 H21 119.2 . .
C20 C21 H21 119.2 . .
N2 C22 H22A 109.5 . .
N2 C22 H22B 109.5 . .
N2 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
N2 C23 H23A 109.5 . .
N2 C23 H23B 109.5 . .
N2 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
F1 C24 C11 111.5(2) . .
F2 C24 F1 105.6(2) . .
F2 C24 C11 110.7(2) . .
F3 C24 F1 106.4(2) . .
F3 C24 F2 107.0(2) . .
F3 C24 C11 115.0(2) . .
O5 Cl2 O4 113.0(4) . .
O5 Cl2 O6 98.6(6) . .
O5 Cl2 O7 112.0(6) . .
O6 Cl2 O4 114.6(8) . .
O6 Cl2 O7 111.1(9) . .
O7 Cl2 O4 107.6(5) . .
O2 Cl1 O2 109.3(2) . 2_655
O3 Cl1 O2 109.40(17) . 2_655
O3 Cl1 O2 109.40(17) 2_655 .
O3 Cl1 O2 108.49(15) 2_655 2_655
O3 Cl1 O2 108.49(15) . .
O3 Cl1 O3 111.7(2) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C24 1.338(3) .
F2 C24 1.333(3) .
F3 C24 1.314(3) .
O1 C9 1.368(3) .
O1 C13 1.340(3) .
N1 C2 1.462(3) .
N1 C4 1.471(3) .
N1 C5 1.360(3) .
N2 C20 1.352(3) .
N2 C22 1.464(4) .
N2 C23 1.452(4) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C1 C2 1.525(5) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
C3 C4 1.514(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.428(3) .
C5 C10 1.409(3) .
C6 H6 0.9300 .
C6 C7 1.363(4) .
C7 H7 0.9300 .
C7 C8 1.419(3) .
C8 C9 1.413(3) .
C8 C11 1.427(3) .
C9 C10 1.371(3) .
C10 H10 0.9300 .
C11 C12 1.390(3) .
C11 C24 1.521(3) .
C12 C13 1.420(3) .
C12 C17 1.514(3) .
C13 C14 1.419(3) .
C14 C15 1.421(3) .
C14 C18 1.411(3) .
C15 C16 1.505(3) .
C15 C21 1.366(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 C17 1.522(4) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 H18 0.9300 .
C18 C19 1.367(3) .
C19 H19 0.9300 .
C19 C20 1.424(3) .
C20 C21 1.423(4) .
C21 H21 0.9300 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
Cl2 O4 1.425(7) .
Cl2 O5 1.367(4) .
Cl2 O6 1.411(7) .
Cl2 O7 1.415(7) .
Cl1 O2 1.431(2) 2_655
Cl1 O2 1.431(2) .
Cl1 O3 1.421(2) .
Cl1 O3 1.421(2) 2_655
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
O1 C9 C10 C5 -178.3(2)
O1 C13 C14 C15 165.1(2)
O1 C13 C14 C18 -15.0(3)
N1 C5 C6 C7 -176.3(2)
N1 C5 C10 C9 175.3(2)
N2 C20 C21 C15 -178.4(2)
C2 N1 C4 C3 86.5(3)
C2 N1 C5 C6 -175.3(2)
C2 N1 C5 C10 6.1(4)
C4 N1 C2 C1 -96.6(3)
C4 N1 C5 C6 -4.0(4)
C4 N1 C5 C10 177.4(2)
C5 N1 C2 C1 75.2(3)
C5 N1 C4 C3 -85.2(3)
C5 C6 C7 C8 0.1(4)
C6 C5 C10 C9 -3.4(3)
C6 C7 C8 C9 -1.3(4)
C6 C7 C8 C11 176.7(2)
C7 C8 C9 O1 -179.3(2)
C7 C8 C9 C10 0.1(3)
C7 C8 C11 C12 -174.0(2)
C7 C8 C11 C24 4.4(4)
C8 C9 C10 C5 2.3(4)
C8 C11 C12 C13 -6.5(3)
C8 C11 C12 C17 178.1(2)
C8 C11 C24 F1 45.6(3)
C8 C11 C24 F2 -71.7(3)
C8 C11 C24 F3 166.9(2)
C9 O1 C13 C12 3.6(3)
C9 O1 C13 C14 -179.3(2)
C9 C8 C11 C12 4.0(3)
C9 C8 C11 C24 -177.6(2)
C10 C5 C6 C7 2.4(4)
C11 C8 C9 O1 2.5(3)
C11 C8 C9 C10 -178.1(2)
C11 C12 C13 O1 2.8(3)
C11 C12 C13 C14 -174.1(2)
C11 C12 C17 C16 -151.9(2)
C12 C11 C24 F1 -136.0(2)
C12 C11 C24 F2 106.8(3)
C12 C11 C24 F3 -14.6(4)
C12 C13 C14 C15 -17.8(3)
C12 C13 C14 C18 162.1(2)
C13 O1 C9 C8 -6.2(3)
C13 O1 C9 C10 174.3(2)
C13 C12 C17 C16 32.6(3)
C13 C14 C15 C16 -3.5(3)
C13 C14 C15 C21 179.8(2)
C13 C14 C18 C19 -177.4(2)
C14 C15 C16 C17 37.8(3)
C14 C15 C21 C20 -2.0(4)
C14 C18 C19 C20 -2.8(4)
C15 C14 C18 C19 2.5(3)
C15 C16 C17 C12 -51.8(3)
C16 C15 C21 C20 -178.4(2)
C17 C12 C13 O1 178.8(2)
C17 C12 C13 C14 1.9(3)
C18 C14 C15 C16 176.6(2)
C18 C14 C15 C21 -0.1(3)
C18 C19 C20 N2 -179.3(2)
C18 C19 C20 C21 0.7(4)
C19 C20 C21 C15 1.7(4)
C21 C15 C16 C17 -145.6(2)
C22 N2 C20 C19 -1.1(4)
C22 N2 C20 C21 179.0(3)
C23 N2 C20 C19 177.8(2)
C23 N2 C20 C21 -2.1(4)
C24 C11 C12 C13 175.1(2)
C24 C11 C12 C17 -0.3(4)
