#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:06:50 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236177 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/74/4037457.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_4037457
loop_
_publ_author_name
'Shirasaki, Yoshinao'
'Okamoto, Yuta'
'Muranaka, Atsuya'
'Kamino, Shinichiro'
'Sawada, Daisuke'
'Hashizume, Daisuke'
'Uchiyama, Masanobu'
_publ_section_title
;
 Fused-Fluoran Leuco Dyes with Large Color-Change Derived from Two-Step
 Equilibrium: iso-Aminobenzopyranoxanthenes.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12046
_journal_page_last               12051
_journal_paper_doi               10.1021/acs.joc.6b02403
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C42 H38 N2 O6, 2(B F4), 4(H2 O)'
_chemical_formula_sum            'C42 H46 B2 F8 N2 O10'
_chemical_formula_weight         912.43
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                110.621(9)
_cell_angle_beta                 90.220(16)
_cell_angle_gamma                98.167(12)
_cell_formula_units_Z            1
_cell_length_a                   7.7150(18)
_cell_length_b                   10.5292(18)
_cell_length_c                   13.990(4)
_cell_measurement_reflns_used    20496
_cell_measurement_temperature    90
_cell_measurement_theta_max      25.754
_cell_measurement_theta_min      1.558
_cell_volume                     1051.1(4)
_computing_cell_refinement       HKL2000
_computing_data_collection       CrystalClear
_computing_data_reduction        HKL2000
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20476
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.754
_diffrn_reflns_theta_min         1.558
_diffrn_source                   'Fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       plate
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     404
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0757
_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)+(0.1043P)²+1.2703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1997
_refine_ls_wR_factor_ref         0.2354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2438
_reflns_number_total             3941
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b02403_si_004.cif
_cod_data_source_block           iso-ABPX01_colored-form
_cod_database_code               4037457
_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_min   0.922
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2014-3
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
O1 O 0.2213(3) 0.6110(2) 0.0980(2) 0.0474(7) Uani 1 1 d . . . . .
N1 N -0.2078(4) 0.6454(3) 0.3399(2) 0.0444(7) Uani 1 1 d . . . . .
C1 C 0.5447(5) 0.3781(4) 0.0045(3) 0.0472(9) Uani 1 1 d . . . . .
H1 H 0.5772 0.2962 0.0082 0.057 Uiso 1 1 calc R U . . .
C2 C 0.3988(5) 0.4295(4) 0.0535(3) 0.0446(9) Uani 1 1 d . . . . .
C3 C 0.1271(5) 0.5550(4) 0.1587(3) 0.0431(8) Uani 1 1 d . . . . .
C4 C 0.0039(5) 0.6253(4) 0.2126(3) 0.0450(9) Uani 1 1 d . . . . .
H4 H -0.0161 0.7085 0.2053 0.054 Uiso 1 1 calc R U . . .
C5 C -0.0943(4) 0.5743(4) 0.2794(3) 0.0425(8) Uani 1 1 d . . . . .
C6 C -0.0707(5) 0.4423(4) 0.2817(3) 0.0471(9) Uani 1 1 d . . . . .
H6 H -0.1422 0.4034 0.3225 0.056 Uiso 1 1 calc R U . . .
C7 C 0.0510(5) 0.3732(4) 0.2268(3) 0.0497(10) Uani 1 1 d . . . . .
H7 H 0.0646 0.2866 0.2303 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1597(5) 0.4262(4) 0.1638(3) 0.0452(9) Uani 1 1 d . . . . .
C9 C 0.2887(5) 0.3618(4) 0.1092(3) 0.0489(9) Uani 1 1 d D . . . .
C10 C 0.3594(5) 0.5521(4) 0.0490(3) 0.0438(9) Uani 1 1 d . . . . .
O2 O 0.1278(4) 0.1985(3) -0.0651(2) 0.0510(8) Uani 0.872(3) 1 d . . P A 4
O3 O 0.1292(4) -0.0273(3) -0.1183(3) 0.0567(9) Uani 0.872(3) 1 d . . P A 4
H3H H 0.0910 -0.0262 -0.1742 0.085 Uiso 0.872(3) 1 calc R U P A 4
C11 C 0.3288(5) 0.2303(4) 0.1177(4) 0.0416(10) Uani 0.872(3) 1 d D . P A 4
C12 C 0.4252(6) 0.2331(5) 0.2014(4) 0.0502(12) Uani 0.872(3) 1 d . . P A 4
H12 H 0.4701 0.3191 0.2524 0.060 Uiso 0.872(3) 1 calc R U P A 4
C13 C 0.4581(7) 0.1137(5) 0.2131(4) 0.0538(12) Uani 0.872(3) 1 d . . P A 4
H13 H 0.5257 0.1176 0.2712 0.065 Uiso 0.872(3) 1 calc R U P A 4
C14 C 0.3923(6) -0.0108(5) 0.1398(4) 0.0513(11) Uani 0.872(3) 1 d . . P A 4
H14 H 0.4105 -0.0937 0.1481 0.062 Uiso 0.872(3) 1 calc R U P A 4
C15 C 0.2995(6) -0.0147(4) 0.0542(4) 0.0459(11) Uani 0.872(3) 1 d . . P A 4
H15 H 0.2563 -0.1008 0.0029 0.055 Uiso 0.872(3) 1 calc R U P A 4
C16 C 0.2684(5) 0.1058(4) 0.0419(4) 0.0423(10) Uani 0.872(3) 1 d . . P A 4
C17 C 0.1667(6) 0.0991(5) -0.0527(4) 0.0381(13) Uani 0.872(3) 1 d . . P A 4
O2B O 0.486(2) 0.3389(13) 0.2356(13) 0.0510(8) Uani 0.128(3) 1 d G . P A 5
O3B O 0.482(3) 0.1441(16) 0.2663(13) 0.0567(9) Uani 0.128(3) 1 d G . P A 5
H3HB H 0.3880 0.1071 0.2823 0.085 Uiso 0.128(3) 1 calc R U P A 5
C11B C 0.263(4) 0.2062(11) 0.061(2) 0.0416(10) Uani 0.128(3) 1 d D . P A 5
C12B C 0.199(7) 0.111(5) -0.017(4) 0.0502(12) Uani 0.128(3) 1 d . . P A 5
H12B H 0.1602 0.1518 -0.0620 0.060 Uiso 0.128(3) 1 calc R U P A 5
C13B C 0.157(3) -0.036(2) -0.0695(13) 0.0538(12) Uani 0.128(3) 1 d G . P A 5
H13B H 0.0969 -0.0827 -0.1346 0.065 Uiso 0.128(3) 1 calc R U P A 5
C14B C 0.222(3) -0.0947(16) -0.0056(13) 0.0513(11) Uani 0.128(3) 1 d G . P A 5
H14B H 0.2022 -0.1917 -0.0240 0.062 Uiso 0.128(3) 1 calc R U P A 5
C15B C 0.313(2) -0.0146(13) 0.0833(13) 0.0459(11) Uani 0.128(3) 1 d G . P A 5
H15B H 0.3557 -0.0563 0.1269 0.055 Uiso 0.128(3) 1 calc R U P A 5
C16B C 0.3452(17) 0.1299(13) 0.1122(10) 0.0423(10) Uani 0.128(3) 1 d G . P A 5
C17B C 0.4446(18) 0.2159(13) 0.2106(11) 0.0381(13) Uani 0.128(3) 1 d G . P A 5
C18 C -0.2276(5) 0.7843(4) 0.3458(3) 0.0505(10) Uani 1 1 d . . . . .
H18A H -0.1136 0.8315 0.3341 0.061 Uiso 1 1 calc R U . . .
H18B H -0.2606 0.8369 0.4154 0.061 Uiso 1 1 calc R U . . .
C19 C -0.3636(6) 0.7832(5) 0.2690(4) 0.0657(12) Uani 1 1 d . . . . .
H19A H -0.3747 0.8778 0.2767 0.099 Uiso 1 1 calc R U . . .
H19B H -0.4765 0.7361 0.2800 0.099 Uiso 1 1 calc R U . . .
H19C H -0.3287 0.7349 0.1999 0.099 Uiso 1 1 calc R U . . .
C20 C -0.3175(5) 0.5929(4) 0.4078(3) 0.0490(9) Uani 1 1 d . . . . .
H20A H -0.3444 0.4916 0.3766 0.059 Uiso 1 1 calc R U . . .
H20B H -0.4298 0.6297 0.4144 0.059 Uiso 1 1 calc R U . . .
C21 C -0.2303(6) 0.6317(5) 0.5124(3) 0.0649(12) Uani 1 1 d . . . . .
H21A H -0.3075 0.5935 0.5543 0.097 Uiso 1 1 calc R U . . .
H21B H -0.2070 0.7319 0.5448 0.097 Uiso 1 1 calc R U . . .
H21C H -0.1194 0.5948 0.5065 0.097 Uiso 1 1 calc R U . . .
F1 F -0.2729(10) 0.3002(8) 0.4291(5) 0.0608(7) Uani 0.367(3) 1 d D . P B 1
F2 F -0.4524(7) 0.1363(8) 0.4654(6) 0.0608(7) Uani 0.367(3) 1 d D . P B 1
F3 F -0.2735(9) 0.2992(7) 0.5903(4) 0.0608(7) Uani 0.367(3) 1 d D . P B 1
F4 F -0.1599(9) 0.1351(6) 0.4660(5) 0.0608(7) Uani 0.367(3) 1 d D . P B 1
B1 B -0.2896(6) 0.2177(5) 0.4877(4) 0.0469(14) Uani 0.367(3) 1 d D . P B 1
F1B F -0.2454(11) 0.2651(8) 0.4066(4) 0.0608(7) Uani 0.302(3) 1 d D . P C 2
F2B F -0.4295(8) 0.1482(8) 0.4827(7) 0.0608(7) Uani 0.302(3) 1 d D . P C 2
F3B F -0.2665(10) 0.3499(7) 0.5779(4) 0.0608(7) Uani 0.302(3) 1 d D . P C 2
F4B F -0.1364(9) 0.1622(7) 0.5056(6) 0.0608(7) Uani 0.302(3) 1 d D . P C 2
B1B B -0.2694(7) 0.2314(5) 0.4932(4) 0.0469(14) Uani 0.302(3) 1 d D . P C 2
F1C F -0.3157(14) 0.2961(10) 0.4213(8) 0.0608(7) Uani 0.253(3) 1 d D . P D 3
F2C F -0.4809(8) 0.1490(11) 0.4816(9) 0.0608(7) Uani 0.253(3) 1 d D . P D 3
F3C F -0.2364(13) 0.2813(9) 0.5723(6) 0.0608(7) Uani 0.253(3) 1 d D . P D 3
F4C F -0.2140(11) 0.1066(8) 0.4244(7) 0.0608(7) Uani 0.253(3) 1 d D . P D 3
B1C B -0.3116(7) 0.2083(7) 0.4749(5) 0.0469(14) Uani 0.253(3) 1 d D . P D 3
F1D F -0.351(3) 0.3165(16) 0.4580(18) 0.0608(7) Uani 0.078(2) 1 d D . P E 4
F2D F -0.380(2) 0.0941(16) 0.4441(17) 0.0608(7) Uani 0.078(2) 1 d D . P E 4
F3D F -0.154(3) 0.247(2) 0.5410(11) 0.0608(7) Uani 0.078(2) 1 d D . P E 4
F4D F -0.159(2) 0.182(2) 0.3689(12) 0.0608(7) Uani 0.078(2) 1 d D . P E 4
B1D B -0.2609(17) 0.2098(13) 0.4530(10) 0.0469(14) Uani 0.078(2) 1 d D . P E 4
O1W O -0.0225(4) -0.0657(4) -0.2886(3) 0.0763(10) Uani 1 1 d D . . . .
H1W H -0.1011(10) -0.0188(10) -0.3033(11) 0.114 Uiso 1 1 d D U . . .
H2W H 0.0402(11) -0.0897(13) -0.3446(6) 0.114 Uiso 1 1 d D U . . .
O2W O -0.2689(4) 0.0487(4) -0.3542(3) 0.0840(11) Uani 1 1 d D . . . .
H3W H -0.2338(18) 0.1098(9) -0.3844(8) 0.126 Uiso 1 1 d D U . . .
H4W H -0.3509(14) -0.0130(8) -0.3991(10) 0.126 Uiso 1 1 d D U . . .
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'
B B 0.0013 0.0007 '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
C3 O1 C10 120.0(3) . .
C5 N1 C18 122.0(3) . .
C5 N1 C20 123.0(3) . .
C18 N1 C20 114.9(3) . .
C10 C1 C2 119.0(3) 2_665 .
C10 C1 H1 120.5 2_665 .
C2 C1 H1 120.5 . .
C10 C2 C1 118.6(3) . .
C10 C2 C9 118.6(3) . .
C1 C2 C9 122.8(3) . .
C4 C3 O1 116.9(3) . .
C4 C3 C8 122.9(3) . .
O1 C3 C8 120.1(3) . .
C3 C4 C5 119.5(3) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
N1 C5 C4 121.6(3) . .
N1 C5 C6 119.9(3) . .
C4 C5 C6 118.5(3) . .
C7 C6 C5 121.0(3) . .
C7 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
C6 C7 C8 121.6(3) . .
C6 C7 H7 119.2 . .
C8 C7 H7 119.2 . .
C9 C8 C7 123.7(3) . .
C9 C8 C3 120.0(3) . .
C7 C8 C3 116.2(3) . .
C8 C9 C2 119.0(3) . .
C8 C9 C11 120.3(3) . .
C2 C9 C11 120.3(3) . .
C8 C9 C11B 120.2(11) . .
C2 C9 C11B 113.4(11) . .
O1 C10 C1 115.8(3) . 2_665
O1 C10 C2 121.8(3) . .
C1 C10 C2 122.4(3) 2_665 .
C17 O3 H3H 109.5 . .
C12 C11 C16 119.3(4) . .
C12 C11 C9 120.2(4) . .
C16 C11 C9 120.4(4) . .
C11 C12 C13 121.5(5) . .
C11 C12 H12 119.3 . .
C13 C12 H12 119.3 . .
C14 C13 C12 119.4(5) . .
C14 C13 H13 120.3 . .
C12 C13 H13 120.3 . .
C13 C14 C15 119.6(4) . .
C13 C14 H14 120.2 . .
C15 C14 H14 120.2 . .
C14 C15 C16 120.9(4) . .
C14 C15 H15 119.6 . .
C16 C15 H15 119.6 . .
C11 C16 C15 119.2(5) . .
C11 C16 C17 120.8(4) . .
C15 C16 C17 120.0(4) . .
O2 C17 O3 125.2(4) . .
O2 C17 C16 123.1(4) . .
O3 C17 C16 111.7(4) . .
C17B O3B H3HB 109.5 . .
C12B C11B C16B 100(3) . .
C12B C11B C9 142(4) . .
C16B C11B C9 118(2) . .
C11B C12B C13B 148(5) . .
C11B C12B H12B 106.2 . .
C13B C12B H12B 106.2 . .
C14B C13B C12B 106(2) . .
C14B C13B H13B 127.1 . .
C12B C13B H13B 127.1 . .
C15B C14B C13B 120.3 . .
C15B C14B H14B 119.8 . .
C13B C14B H14B 119.8 . .
C14B C15B C16B 121.1 . .
C14B C15B H15B 119.5 . .
C16B C15B H15B 119.5 . .
C15B C16B C11B 124.2(10) . .
C15B C16B C17B 120.2 . .
C11B C16B C17B 114.9(10) . .
O2B C17B O3B 124.2 . .
O2B C17B C16B 122.7 . .
O3B C17B C16B 113.0 . .
N1 C18 C19 112.1(4) . .
N1 C18 H18A 109.2 . .
C19 C18 H18A 109.2 . .
N1 C18 H18B 109.2 . .
C19 C18 H18B 109.2 . .
H18A C18 H18B 107.9 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
N1 C20 C21 112.6(3) . .
N1 C20 H20A 109.1 . .
C21 C20 H20A 109.1 . .
N1 C20 H20B 109.1 . .
C21 C20 H20B 109.1 . .
H20A C20 H20B 107.8 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
F1 B1 F3 109.52(13) . .
F1 B1 F4 109.55(13) . .
F3 B1 F4 109.48(13) . .
F1 B1 F2 109.43(13) . .
F3 B1 F2 109.41(13) . .
F4 B1 F2 109.44(13) . .
F1B B1B F3B 109.54(13) . .
F1B B1B F4B 109.48(13) . .
F3B B1B F4B 109.43(13) . .
F1B B1B F2B 109.48(13) . .
F3B B1B F2B 109.43(13) . .
F4B B1B F2B 109.47(13) . .
F1C B1C F3C 109.54(13) . .
F1C B1C F4C 109.53(13) . .
F3C B1C F4C 109.52(13) . .
F1C B1C F2C 109.41(13) . .
F3C B1C F2C 109.40(13) . .
F4C B1C F2C 109.42(13) . .
F1D B1D F3D 109.50(13) . .
F1D B1D F4D 109.46(13) . .
F3D B1D F4D 109.46(13) . .
F1D B1D F2D 109.48(13) . .
F3D B1D F2D 109.47(13) . .
F4D B1D F2D 109.46(13) . .
H1W O1W H2W 104.0(2) . .
H3W O2W H4W 104.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.354(4) .
O1 C10 1.372(4) .
N1 C5 1.338(4) .
N1 C18 1.466(5) .
N1 C20 1.472(5) .
C1 C10 1.373(5) 2_665
C1 C2 1.395(5) .
C1 H1 0.9500 .
C2 C10 1.390(5) .
C2 C9 1.436(5) .
C3 C4 1.354(5) .
C3 C8 1.439(5) .
C4 C5 1.408(5) .
C4 H4 0.9500 .
C5 C6 1.438(5) .
C6 C7 1.345(5) .
C6 H6 0.9500 .
C7 C8 1.418(5) .
C7 H7 0.9500 .
C8 C9 1.366(5) .
C9 C11 1.505(5) .
C9 C11B 1.519(11) .
C10 C1 1.373(5) 2_665
O2 C17 1.197(5) .
O3 C17 1.314(6) .
O3 H3H 0.8400 .
C11 C12 1.375(7) .
C11 C16 1.380(6) .
C12 C13 1.381(6) .
C12 H12 0.9500 .
C13 C14 1.374(7) .
C13 H13 0.9500 .
C14 C15 1.378(7) .
C14 H14 0.9500 .
C15 C16 1.391(6) .
C15 H15 0.9500 .
C16 C17 1.511(6) .
O2B C17B 1.2107 .
O3B C17B 1.3172 .
O3B H3HB 0.8400 .
C11B C12B 1.23(5) .
C11B C16B 1.46(3) .
C12B C13B 1.45(5) .
C12B H12B 0.9500 .
C13B C14B 1.3782 .
C13B H13B 0.9500 .
C14B C15B 1.3564 .
C14B H14B 0.9500 .
C15B C16B 1.4137 .
C15B H15B 0.9500 .
C16B C17B 1.4899 .
C18 C19 1.495(6) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 C21 1.502(6) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
F1 B1 1.383(2) .
F2 B1 1.383(2) .
F3 B1 1.383(2) .
F4 B1 1.383(2) .
F1B B1B 1.383(2) .
F2B B1B 1.383(2) .
F3B B1B 1.383(2) .
F4B B1B 1.383(2) .
F1C B1C 1.383(2) .
F2C B1C 1.383(2) .
F3C B1C 1.383(2) .
F4C B1C 1.383(2) .
F1D B1D 1.383(2) .
F2D B1D 1.383(2) .
F3D B1D 1.383(2) .
F4D B1D 1.383(2) .
O1W H1W 0.900(2) .
O1W H2W 0.900(2) .
O2W H3W 0.900(2) .
O2W H4W 0.900(2) .
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
C6 H6 F1 0.95 2.29 3.235(7) 170.5 .
C6 H6 F1B 0.95 2.24 3.155(8) 161.2 .
C6 H6 F1C 0.95 2.38 3.329(10) 177.3 .
C6 H6 F4D 0.95 2.62 3.36(2) 135.5 .
O3 H3H O1W 0.84 1.71 2.525(5) 163.8 .
O3B H3HB O2W 0.84 2.30 3.03(2) 144.8 2
C18 H18B F2C 0.99 2.46 3.268(10) 138.9 2_466
C19 H19A F2D 0.98 2.63 3.347(19) 129.7 1_565
C20 H20A O2B 0.99 2.31 3.088(15) 134.8 1_455
C20 H20A F1 0.99 2.50 3.264(7) 133.5 .
C20 H20A F1C 0.99 2.39 3.199(9) 138.3 .
C20 H20A F1D 0.99 2.48 3.203(17) 129.5 .
C20 H20B F3 0.99 2.52 3.500(8) 172.9 2_466
C20 H20B F3B 0.99 2.38 3.343(8) 163.2 2_466
C20 H20B F2C 0.99 2.47 3.234(11) 133.7 2_466
C20 H20B F1D 0.99 2.44 3.234(19) 136.7 2_466
O1W H1W O2W 0.900(2) 1.816(6) 2.706(5) 169.6(13) .
O1W H2W F4 0.900(2) 1.879(8) 2.778(7) 176.0(12) 2
O1W H2W F1B 0.900(2) 2.527(12) 3.198(8) 131.8(11) 2
O1W H2W F4B 0.900(2) 2.273(9) 3.156(8) 166.7(9) 2
O1W H2W F4C 0.900(2) 1.737(8) 2.608(8) 162.0(10) 2
O1W H2W F4D 0.900(2) 1.39(2) 2.065(17) 127.5(14) 2
O2W H3W F3 0.900(2) 2.205(11) 3.005(9) 147.7(12) 1_554
O2W H3W F4 0.900(2) 2.266(11) 3.046(8) 144.8(10) 1_554
O2W H3W F2B 0.900(2) 2.565(15) 3.141(9) 122.5(10) 1_554
O2W H3W F4B 0.900(2) 1.931(10) 2.765(8) 153.4(12) 1_554
O2W H3W F3C 0.900(2) 2.100(12) 2.954(11) 158.0(13) 1_554
O2W H3W F2D 0.900(2) 2.59(2) 3.16(2) 121.9(10) 1_554
O2W H3W F3D 0.900(2) 2.09(2) 2.99(2) 178.2(12) 1_554
O2W H4W F2 0.900(2) 1.851(7) 2.736(6) 167.0(15) 2_455
O2W H4W F2B 0.900(2) 2.096(7) 2.987(7) 170.1(15) 2_455
O2W H4W F2C 0.900(2) 1.834(10) 2.730(10) 173.9(13) 2_455
O2W H4W F2D 0.900(2) 2.134(19) 2.947(17) 149.6(15) 2_455
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_4
C10 C1 C2 C10 -2.1(6) 2_665 .
C10 C1 C2 C9 178.6(4) 2_665 .
C10 O1 C3 C4 173.7(3) . .
C10 O1 C3 C8 -6.3(5) . .
O1 C3 C4 C5 -178.0(3) . .
C8 C3 C4 C5 2.1(6) . .
C18 N1 C5 C4 -4.5(5) . .
C20 N1 C5 C4 177.6(3) . .
C18 N1 C5 C6 175.6(3) . .
C20 N1 C5 C6 -2.3(5) . .
C3 C4 C5 N1 174.8(3) . .
C3 C4 C5 C6 -5.3(5) . .
N1 C5 C6 C7 -175.4(4) . .
C4 C5 C6 C7 4.7(6) . .
C5 C6 C7 C8 -0.7(6) . .
C6 C7 C8 C9 177.9(4) . .
C6 C7 C8 C3 -2.6(6) . .
C4 C3 C8 C9 -178.5(4) . .
O1 C3 C8 C9 1.5(6) . .
C4 C3 C8 C7 1.9(6) . .
O1 C3 C8 C7 -178.0(3) . .
C7 C8 C9 C2 -175.8(4) . .
C3 C8 C9 C2 4.7(6) . .
C7 C8 C9 C11 -3.1(6) . .
C3 C8 C9 C11 177.4(4) . .
C7 C8 C9 C11B 36.3(17) . .
C3 C8 C9 C11B -143.2(16) . .
C10 C2 C9 C8 -6.1(6) . .
C1 C2 C9 C8 173.2(4) . .
C10 C2 C9 C11 -178.8(4) . .
C1 C2 C9 C11 0.5(6) . .
C10 C2 C9 C11B 143.8(15) . .
C1 C2 C9 C11B -36.9(15) . .
C3 O1 C10 C1 -175.2(3) . 2_665
C3 O1 C10 C2 4.8(5) . .
C1 C2 C10 O1 -177.9(4) . .
C9 C2 C10 O1 1.5(6) . .
C1 C2 C10 C1 2.2(7) . 2_665
C9 C2 C10 C1 -178.5(4) . 2_665
C8 C9 C11 C12 -77.7(5) . .
C2 C9 C11 C12 94.9(5) . .
C11B C9 C11 C12 -178(2) . .
C8 C9 C11 C16 102.0(5) . .
C2 C9 C11 C16 -85.5(5) . .
C11B C9 C11 C16 2.0(19) . .
C16 C11 C12 C13 -2.2(7) . .
C9 C11 C12 C13 177.5(4) . .
C11 C12 C13 C14 -0.4(7) . .
C12 C13 C14 C15 2.2(7) . .
C13 C14 C15 C16 -1.4(7) . .
C12 C11 C16 C15 3.0(6) . .
C9 C11 C16 C15 -176.7(4) . .
C12 C11 C16 C17 -178.2(4) . .
C9 C11 C16 C17 2.2(6) . .
C14 C15 C16 C11 -1.2(6) . .
C14 C15 C16 C17 179.9(4) . .
C11 C16 C17 O2 -3.0(7) . .
C15 C16 C17 O2 175.9(4) . .
C11 C16 C17 O3 176.5(4) . .
C15 C16 C17 O3 -4.7(6) . .
C8 C9 C11B C12B 85(5) . .
C2 C9 C11B C12B -64(5) . .
C11 C9 C11B C12B -174(6) . .
C8 C9 C11B C16B -101(2) . .
C2 C9 C11B C16B 109.7(19) . .
C11 C9 C11B C16B -0.2(7) . .
C16B C11B C12B C13B 11(9) . .
C9 C11B C12B C13B -175(5) . .
C11B C12B C13B C14B -3(9) . .
C12B C13B C14B C15B -3(2) . .
C13B C14B C15B C16B -0.6 . .
C14B C15B C16B C11B 10.4(18) . .
C14B C15B C16B C17B 179.6 . .
C12B C11B C16B C15B -13(3) . .
C9 C11B C16B C15B 171.0(13) . .
C12B C11B C16B C17B 178(3) . .
C9 C11B C16B C17B 1(2) . .
C15B C16B C17B O2B 174.9 . .
C11B C16B C17B O2B -15.0(17) . .
C15B C16B C17B O3B -5.2 . .
C11B C16B C17B O3B 164.9(17) . .
C5 N1 C18 C19 89.9(4) . .
C20 N1 C18 C19 -92.1(4) . .
C5 N1 C20 C21 90.3(4) . .
C18 N1 C20 C21 -87.7(4) . .
