#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/87/1518703.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_1518703
loop_
_publ_author_name
'Kim, Sung Kuk'
'Lynch, Vincent M.'
'Sessler, Jonathan L.'
_publ_section_title
;
 Cone Calix[4]arene Diethyl Ester Strapped Calix[4]pyrrole:
 A Selective Receptor for the Fluoride Anion.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6128
_journal_paper_doi               10.1021/ol502991t
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety
'C78 H80 N4 O10, C8 H20 N 1+, F 1-, H2 O, 2 C H2 Cl2'
_chemical_formula_sum            'C144 H96 Cl4 F N14 O8'
_chemical_formula_weight         2311.14
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 116.015(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9315(9)
_cell_length_b                   23.719(3)
_cell_length_c                   20.4020(16)
_cell_measurement_reflns_used    15592
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.2
_cell_measurement_theta_min      1.5
_cell_volume                     8667.9(14)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            73755
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.031
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_description       plate
_exptl_crystal_F_000             4796
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         7607
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0546
_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)+(0.0802P)²+17.8643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1549
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6467
_reflns_number_total             7607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol502991t_si_004.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        8667.9(13)
_cod_database_code               1518703
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
F1 F 0.7500 0.81212(7) 0.5000 0.0214(4) Uani 1 2 d S T P . .
O1 O 0.56084(9) 0.62482(6) 0.35837(9) 0.0237(4) Uani 1 1 d . . . . .
O2 O 0.61326(9) 0.51251(6) 0.37777(8) 0.0221(3) Uani 1 1 d . . . . .
O3 O 0.69906(9) 0.50158(6) 0.54643(8) 0.0217(3) Uani 1 1 d . . . . .
O4 O 0.74590(10) 0.59665(8) 0.64457(10) 0.0339(4) Uani 1 1 d . . . . .
O5 O 0.63037(11) 0.62846(8) 0.58349(12) 0.0259(4) Uani 0.83 1 d D . P A 1
C38 C 0.64495(18) 0.67121(13) 0.63895(18) 0.0281(7) Uani 0.83 1 d D . P A 1
H38A H 0.6778 0.7010 0.6351 0.034 Uiso 0.83 1 calc R U P A 1
H38B H 0.6695 0.6543 0.6883 0.034 Uiso 0.83 1 calc R U P A 1
C39 C 0.5702(2) 0.69532(14) 0.62524(19) 0.0337(8) Uani 0.83 1 d D . P A 1
H39A H 0.5466 0.7116 0.5762 0.051 Uiso 0.83 1 calc R U P A 1
H39B H 0.5770 0.7247 0.6613 0.051 Uiso 0.83 1 calc R U P A 1
H39C H 0.5384 0.6653 0.6293 0.051 Uiso 0.83 1 calc R U P A 1
O5A O 0.6383(6) 0.6390(4) 0.5514(6) 0.028 Uiso 0.17 1 d D U P A 2
C38A C 0.6547(8) 0.6900(5) 0.5954(8) 0.028 Uiso 0.17 1 d D U P A 2
H38C H 0.6345 0.7236 0.5641 0.034 Uiso 0.17 1 calc R U P A 2
H38D H 0.7092 0.6947 0.6244 0.034 Uiso 0.17 1 calc R U P A 2
C39A C 0.6172(12) 0.6819(8) 0.6444(9) 0.028 Uiso 0.17 1 d D U P A 2
H39D H 0.5634 0.6774 0.6147 0.042 Uiso 0.17 1 calc R U P A 2
H39E H 0.6265 0.7149 0.6761 0.042 Uiso 0.17 1 calc R U P A 2
H39F H 0.6373 0.6482 0.6744 0.042 Uiso 0.17 1 calc R U P A 2
N1 N 0.79432(11) 0.87549(8) 0.62399(10) 0.0206(4) Uani 1 1 d . . . . .
H1 H 0.7781 0.8521 0.5867 0.025 Uiso 1 1 calc R U . . .
N2 N 0.63009(11) 0.87623(8) 0.48737(10) 0.0202(4) Uani 1 1 d . . . . .
H2 H 0.6673 0.8533 0.4942 0.024 Uiso 1 1 calc R U . . .
C1 C 0.86781(13) 0.88954(9) 0.66528(12) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.87000(14) 0.92715(10) 0.71749(13) 0.0252(5) Uani 1 1 d . . . . .
H2A H 0.9135 0.9442 0.7539 0.030 Uiso 1 1 calc R U . . .
C3 C 0.79599(14) 0.93593(10) 0.70745(13) 0.0258(5) Uani 1 1 d . . . . .
H3 H 0.7810 0.9601 0.7357 0.031 Uiso 1 1 calc R U . . .
C4 C 0.74948(14) 0.90331(10) 0.64938(12) 0.0227(5) Uani 1 1 d . . . . .
C5 C 0.66734(14) 0.88977(10) 0.62218(13) 0.0258(5) Uani 1 1 d . . . . .
C6 C 0.61959(13) 0.90279(10) 0.54227(13) 0.0224(5) Uani 1 1 d . . . . .
C7 C 0.55640(14) 0.93473(10) 0.50936(14) 0.0284(5) Uani 1 1 d . . . . .
H7 H 0.5354 0.9579 0.5336 0.034 Uiso 1 1 calc R U . . .
C8 C 0.52762(14) 0.92730(10) 0.43310(14) 0.0267(5) Uani 1 1 d . . . . .
H8 H 0.4840 0.9445 0.3970 0.032 Uiso 1 1 calc R U . . .
C9 C 0.57423(13) 0.89063(9) 0.42066(12) 0.0211(5) Uani 1 1 d . . . . .
C10 C 0.57074(13) 0.86542(9) 0.35098(12) 0.0217(5) Uani 1 1 d . . . . .
C11 C 0.63668(16) 0.92307(13) 0.66746(14) 0.0362(6) Uani 1 1 d . . . . .
H11A H 0.6394 0.9635 0.6591 0.054 Uiso 1 1 calc R U . . .
H11B H 0.6665 0.9147 0.7193 0.054 Uiso 1 1 calc R U . . .
H11C H 0.5846 0.9123 0.6529 0.054 Uiso 1 1 calc R U . . .
C12 C 0.65985(15) 0.82615(11) 0.63428(15) 0.0324(6) Uani 1 1 d . . . . .
H12A H 0.6072 0.8169 0.6194 0.049 Uiso 1 1 calc R U . . .
H12B H 0.6891 0.8171 0.6860 0.049 Uiso 1 1 calc R U . . .
H12C H 0.6785 0.8042 0.6051 0.049 Uiso 1 1 calc R U . . .
C13 C 0.49487(14) 0.88073(10) 0.28779(13) 0.0279(5) Uani 1 1 d . . . . .
H13A H 0.4897 0.9218 0.2838 0.042 Uiso 1 1 calc R U . . .
H13B H 0.4546 0.8648 0.2972 0.042 Uiso 1 1 calc R U . . .
H13C H 0.4921 0.8653 0.2421 0.042 Uiso 1 1 calc R U . . .
C14 C 0.57466(12) 0.80069(9) 0.35655(12) 0.0201(5) Uani 1 1 d . . . . .
C15 C 0.54323(13) 0.77202(10) 0.39592(13) 0.0229(5) Uani 1 1 d . . . . .
H15 H 0.5232 0.7930 0.4230 0.027 Uiso 1 1 calc R U . . .
C16 C 0.54045(13) 0.71371(10) 0.39653(13) 0.0236(5) Uani 1 1 d . . . . .
H16 H 0.5191 0.6951 0.4242 0.028 Uiso 1 1 calc R U . . .
C17 C 0.56881(13) 0.68219(9) 0.35676(12) 0.0210(5) Uani 1 1 d . . . . .
C18 C 0.60242(14) 0.70970(10) 0.31903(13) 0.0257(5) Uani 1 1 d . . . . .
H18 H 0.6236 0.6887 0.2931 0.031 Uiso 1 1 calc R U . . .
C19 C 0.60491(14) 0.76838(10) 0.31935(12) 0.0245(5) Uani 1 1 d . . . . .
H19 H 0.6280 0.7869 0.2933 0.029 Uiso 1 1 calc R U . . .
C20 C 0.57174(14) 0.59347(9) 0.30378(13) 0.0225(5) Uani 1 1 d . . . . .
H20A H 0.6237 0.5981 0.3105 0.027 Uiso 1 1 calc R U . . .
H20B H 0.5376 0.6075 0.2547 0.027 Uiso 1 1 calc R U . . .
C21 C 0.55618(13) 0.53234(9) 0.31065(13) 0.0232(5) Uani 1 1 d . . . . .
H21A H 0.5066 0.5280 0.3103 0.028 Uiso 1 1 calc R U . . .
H21B H 0.5564 0.5106 0.2694 0.028 Uiso 1 1 calc R U . . .
C22 C 0.62458(12) 0.45444(9) 0.38463(12) 0.0195(5) Uani 1 1 d . . . . .
C23 C 0.59692(12) 0.42416(9) 0.42594(12) 0.0206(5) Uani 1 1 d . . . . .
C24 C 0.55199(13) 0.45203(10) 0.46083(13) 0.0237(5) Uani 1 1 d . . . . .
H24A H 0.5029 0.4332 0.4440 0.028 Uiso 1 1 calc R U . . .
H24B H 0.5432 0.4921 0.4460 0.028 Uiso 1 1 calc R U . . .
C25 C 0.59422(13) 0.44794(9) 0.54346(13) 0.0221(5) Uani 1 1 d . . . . .
C26 C 0.66688(13) 0.46863(9) 0.58134(12) 0.0207(5) Uani 1 1 d . . . . .
C27 C 0.71269(13) 0.45235(10) 0.65258(12) 0.0225(5) Uani 1 1 d . . . . .
C28 C 0.68146(14) 0.42045(10) 0.68941(13) 0.0266(5) Uani 1 1 d . . . . .
H28 H 0.7114 0.4097 0.7386 0.032 Uiso 1 1 calc R U . . .
C29 C 0.60731(14) 0.40409(10) 0.65537(14) 0.0287(6) Uani 1 1 d . . . . .
H29 H 0.5857 0.3845 0.6820 0.034 Uiso 1 1 calc R U . . .
C30 C 0.56492(14) 0.41649(10) 0.58241(14) 0.0264(5) Uani 1 1 d . . . . .
H30 H 0.5149 0.4033 0.5585 0.032 Uiso 1 1 calc R U . . .
C31 C 0.79538(13) 0.46386(10) 0.68393(12) 0.0228(5) Uani 1 1 d . . . . .
H31A H 0.8194 0.4538 0.7363 0.027 Uiso 1 1 calc R U . . .
H31B H 0.8039 0.5045 0.6795 0.027 Uiso 1 1 calc R U . . .
C32 C 0.83005(12) 0.42949(9) 0.64345(12) 0.0200(5) Uani 1 1 d . . . . .
C33 C 0.81282(13) 0.37276(10) 0.62856(13) 0.0241(5) Uani 1 1 d . . . . .
H33 H 0.7823 0.3547 0.6473 0.029 Uiso 1 1 calc R U . . .
C34 C 0.83896(14) 0.34206(10) 0.58722(14) 0.0275(5) Uani 1 1 d . . . . .
H34 H 0.8259 0.3034 0.5771 0.033 Uiso 1 1 calc R U . . .
C35 C 0.88423(14) 0.36762(10) 0.56048(13) 0.0249(5) Uani 1 1 d . . . . .
H35 H 0.9026 0.3462 0.5325 0.030 Uiso 1 1 calc R U . . .
C36 C 0.66724(14) 0.55655(10) 0.52650(13) 0.0254(5) Uani 1 1 d . . . . .
H36A H 0.6122 0.5531 0.5012 0.030 Uiso 1 1 calc R U . . .
H36B H 0.6840 0.5734 0.4918 0.030 Uiso 1 1 calc R U . . .
C37 C 0.68814(13) 0.59538(10) 0.59082(14) 0.0248(5) Uani 1 1 d . . . . .
N3 N 0.7500 1.05157(12) 0.5000 0.0291(7) Uani 1 2 d S T P . .
C40 C 0.68945(15) 1.01297(10) 0.44713(14) 0.0300(6) Uani 1 1 d . . . . .
H40A H 0.7116 0.9889 0.4221 0.036 Uiso 1 1 calc R U . . .
H40B H 0.6723 0.9878 0.4755 0.036 Uiso 1 1 calc R U . . .
C41 C 0.62201(17) 1.04310(12) 0.38977(16) 0.0419(7) Uani 1 1 d . . . . .
H41A H 0.5992 1.0669 0.4138 0.063 Uiso 1 1 calc R U . . .
H41B H 0.5855 1.0152 0.3590 0.063 Uiso 1 1 calc R U . . .
H41C H 0.6378 1.0667 0.3596 0.063 Uiso 1 1 calc R U . . .
C42 C 0.71930(17) 1.09003(11) 0.53972(15) 0.0368(6) Uani 1 1 d . . . . .
H42A H 0.6813 1.1150 0.5034 0.044 Uiso 1 1 calc R U . . .
H42B H 0.7604 1.1143 0.5734 0.044 Uiso 1 1 calc R U . . .
C43 C 0.68433(19) 1.06049(12) 0.58304(17) 0.0446(7) Uani 1 1 d . . . . .
H43A H 0.6443 1.0355 0.5507 0.067 Uiso 1 1 calc R U . . .
H43B H 0.6636 1.0886 0.6043 0.067 Uiso 1 1 calc R U . . .
H43C H 0.7224 1.0382 0.6222 0.067 Uiso 1 1 calc R U . . .
O1W O 0.7398(5) 0.69636(16) 0.5147(4) 0.066(2) Uani 0.5 1 d . . P B -1
H1WA H 0.7468 0.7277 0.5048 0.098 Uiso 0.5 1 d R U P B -1
H1WB H 0.7167 0.7072 0.5359 0.098 Uiso 0.5 1 d R U P B -1
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'
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'
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'
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
C17 O1 C20 115.94(17) . .
C22 O2 C21 116.71(17) . .
C26 O3 C36 114.34(17) . .
C37 O5 C38 116.9(2) . .
O5 C38 C39 106.1(2) . .
O5 C38 H38A 110.5 . .
C39 C38 H38A 110.5 . .
O5 C38 H38B 110.5 . .
C39 C38 H38B 110.5 . .
H38A C38 H38B 108.7 . .
C38 C39 H39A 109.5 . .
C38 C39 H39B 109.5 . .
H39A C39 H39B 109.5 . .
C38 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
C37 O5A C38A 110.2(9) . .
O5A C38A C39A 105.2(10) . .
O5A C38A H38C 110.7 . .
C39A C38A H38C 110.7 . .
O5A C38A H38D 110.7 . .
C39A C38A H38D 110.7 . .
H38C C38A H38D 108.8 . .
C38A C39A H39D 109.5 . .
C38A C39A H39E 109.5 . .
H39D C39A H39E 109.5 . .
C38A C39A H39F 109.5 . .
H39D C39A H39F 109.5 . .
H39E C39A H39F 109.5 . .
C1 N1 C4 110.23(19) . .
C1 N1 H1 124.9 . .
C4 N1 H1 124.9 . .
C9 N2 C6 110.25(19) . .
C9 N2 H2 124.9 . .
C6 N2 H2 124.9 . .
N1 C1 C2 107.2(2) . .
N1 C1 C10 121.46(19) . 2_656
C2 C1 C10 131.4(2) . 2_656
C1 C2 C3 107.9(2) . .
C1 C2 H2A 126.1 . .
C3 C2 H2A 126.1 . .
C4 C3 C2 107.9(2) . .
C4 C3 H3 126.0 . .
C2 C3 H3 126.0 . .
C3 C4 N1 106.8(2) . .
C3 C4 C5 130.2(2) . .
N1 C4 C5 122.3(2) . .
C4 C5 C6 114.75(19) . .
C4 C5 C11 108.8(2) . .
C6 C5 C11 108.4(2) . .
C4 C5 C12 108.2(2) . .
C6 C5 C12 108.1(2) . .
C11 C5 C12 108.3(2) . .
C7 C6 N2 106.8(2) . .
C7 C6 C5 130.5(2) . .
N2 C6 C5 122.2(2) . .
C6 C7 C8 108.2(2) . .
C6 C7 H7 125.9 . .
C8 C7 H7 125.9 . .
C9 C8 C7 107.5(2) . .
C9 C8 H8 126.2 . .
C7 C8 H8 126.2 . .
N2 C9 C8 107.1(2) . .
N2 C9 C10 121.1(2) . .
C8 C9 C10 131.8(2) . .
C1 C10 C9 110.34(18) 2_656 .
C1 C10 C14 111.92(19) 2_656 .
C9 C10 C14 110.14(18) . .
C1 C10 C13 108.61(19) 2_656 .
C9 C10 C13 108.46(19) . .
C14 C10 C13 107.25(18) . .
C5 C11 H11A 109.5 . .
C5 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C5 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C5 C12 H12A 109.5 . .
C5 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C5 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C19 C14 C15 117.3(2) . .
C19 C14 C10 122.0(2) . .
C15 C14 C10 120.5(2) . .
C16 C15 C14 121.5(2) . .
C16 C15 H15 119.2 . .
C14 C15 H15 119.2 . .
C15 C16 C17 120.2(2) . .
C15 C16 H16 119.9 . .
C17 C16 H16 119.9 . .
O1 C17 C18 124.7(2) . .
O1 C17 C16 115.9(2) . .
C18 C17 C16 119.3(2) . .
C17 C18 C19 119.5(2) . .
C17 C18 H18 120.2 . .
C19 C18 H18 120.2 . .
C14 C19 C18 122.1(2) . .
C14 C19 H19 119.0 . .
C18 C19 H19 119.0 . .
O1 C20 C21 108.70(18) . .
O1 C20 H20A 109.9 . .
C21 C20 H20A 109.9 . .
O1 C20 H20B 109.9 . .
C21 C20 H20B 109.9 . .
H20A C20 H20B 108.3 . .
O2 C21 C20 107.35(18) . .
O2 C21 H21A 110.2 . .
C20 C21 H21A 110.2 . .
O2 C21 H21B 110.2 . .
C20 C21 H21B 110.2 . .
H21A C21 H21B 108.5 . .
C23 C22 O2 118.8(2) . .
C23 C22 C32 122.0(2) . 2_656
O2 C22 C32 118.9(2) . 2_656
C35 C23 C22 118.4(2) 2_656 .
C35 C23 C24 119.4(2) 2_656 .
C22 C23 C24 122.1(2) . .
C23 C24 C25 109.78(18) . .
C23 C24 H24A 109.7 . .
C25 C24 H24A 109.7 . .
C23 C24 H24B 109.7 . .
C25 C24 H24B 109.7 . .
H24A C24 H24B 108.2 . .
C30 C25 C26 117.7(2) . .
C30 C25 C24 120.0(2) . .
C26 C25 C24 121.7(2) . .
O3 C26 C27 116.9(2) . .
O3 C26 C25 120.9(2) . .
C27 C26 C25 121.8(2) . .
C26 C27 C28 118.1(2) . .
C26 C27 C31 119.2(2) . .
C28 C27 C31 122.3(2) . .
C29 C28 C27 120.9(2) . .
C29 C28 H28 119.5 . .
C27 C28 H28 119.5 . .
C30 C29 C28 119.6(2) . .
C30 C29 H29 120.2 . .
C28 C29 H29 120.2 . .
C29 C30 C25 121.2(2) . .
C29 C30 H30 119.4 . .
C25 C30 H30 119.4 . .
C27 C31 C32 110.12(18) . .
C27 C31 H31A 109.6 . .
C32 C31 H31A 109.6 . .
C27 C31 H31B 109.6 . .
C32 C31 H31B 109.6 . .
H31A C31 H31B 108.2 . .
C33 C32 C22 117.6(2) . 2_656
C33 C32 C31 120.6(2) . .
C22 C32 C31 121.6(2) 2_656 .
C34 C33 C32 121.5(2) . .
C34 C33 H33 119.3 . .
C32 C33 H33 119.3 . .
C33 C34 C35 119.8(2) . .
C33 C34 H34 120.1 . .
C35 C34 H34 120.1 . .
C34 C35 C23 120.8(2) . 2_656
C34 C35 H35 119.6 . .
C23 C35 H35 119.6 2_656 .
O3 C36 C37 113.07(19) . .
O3 C36 H36A 109.0 . .
C37 C36 H36A 109.0 . .
O3 C36 H36B 109.0 . .
C37 C36 H36B 109.0 . .
H36A C36 H36B 107.8 . .
O4 C37 O5 121.4(2) . .
O4 C37 O5A 131.1(4) . .
O4 C37 C36 127.2(2) . .
O5 C37 C36 111.3(2) . .
O5A C37 C36 95.5(4) . .
C42 N3 C42 106.0(3) 2_656 .
C42 N3 C40 111.32(14) 2_656 .
C42 N3 C40 111.12(15) . .
C42 N3 C40 111.12(15) 2_656 2_656
C42 N3 C40 111.32(14) . 2_656
C40 N3 C40 106.0(3) . 2_656
C41 C40 N3 114.9(2) . .
C41 C40 H40A 108.5 . .
N3 C40 H40A 108.5 . .
C41 C40 H40B 108.5 . .
N3 C40 H40B 108.5 . .
H40A C40 H40B 107.5 . .
C40 C41 H41A 109.5 . .
C40 C41 H41B 109.5 . .
H41A C41 H41B 109.5 . .
C40 C41 H41C 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
N3 C42 C43 115.5(2) . .
N3 C42 H42A 108.4 . .
C43 C42 H42A 108.4 . .
N3 C42 H42B 108.4 . .
C43 C42 H42B 108.4 . .
H42A C42 H42B 107.5 . .
C42 C43 H43A 109.5 . .
C42 C43 H43B 109.5 . .
H43A C43 H43B 109.5 . .
C42 C43 H43C 109.5 . .
H43A C43 H43C 109.5 . .
H43B C43 H43C 109.5 . .
H1WA O1W H1WB 92.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C17 1.372(3) .
O1 C20 1.433(3) .
O2 C22 1.393(3) .
O2 C21 1.423(3) .
O3 C26 1.390(3) .
O3 C36 1.429(3) .
O4 C37 1.192(3) .
O5 C37 1.346(3) .
O5 C38 1.451(4) .
C38 C39 1.502(4) .
C38 H38A 0.9900 .
C38 H38B 0.9900 .
C39 H39A 0.9800 .
C39 H39B 0.9800 .
C39 H39C 0.9800 .
O5A C37 1.415(11) .
O5A C38A 1.455(9) .
C38A C39A 1.499(10) .
C38A H38C 0.9900 .
C38A H38D 0.9900 .
C39A H39D 0.9800 .
C39A H39E 0.9800 .
C39A H39F 0.9800 .
N1 C1 1.373(3) .
N1 C4 1.381(3) .
N1 H1 0.8800 .
N2 C9 1.371(3) .
N2 C6 1.379(3) .
N2 H2 0.8800 .
C1 C2 1.375(3) .
C1 C10 1.514(3) 2_656
C2 C3 1.413(4) .
C2 H2A 0.9500 .
C3 C4 1.378(3) .
C3 H3 0.9500 .
C4 C5 1.515(4) .
C5 C6 1.516(3) .
C5 C11 1.532(3) .
C5 C12 1.547(3) .
C6 C7 1.367(3) .
C7 C8 1.413(4) .
C7 H7 0.9500 .
C8 C9 1.375(3) .
C8 H8 0.9500 .
C9 C10 1.515(3) .
C10 C1 1.514(3) 2_656
C10 C14 1.539(3) .
C10 C13 1.540(3) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C19 1.389(3) .
C14 C15 1.393(3) .
C15 C16 1.384(3) .
C15 H15 0.9500 .
C16 C17 1.393(3) .
C16 H16 0.9500 .
C17 C18 1.385(3) .
C18 C19 1.393(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 C21 1.502(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.392(3) .
C22 C32 1.397(3) 2_656
C23 C35 1.387(3) 2_656
C23 C24 1.518(3) .
C24 C25 1.522(3) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C30 1.391(3) .
C25 C26 1.398(3) .
C26 C27 1.390(3) .
C27 C28 1.391(3) .
C27 C31 1.508(3) .
C28 C29 1.384(4) .
C28 H28 0.9500 .
C29 C30 1.383(4) .
C29 H29 0.9500 .
C30 H30 0.9500 .
C31 C32 1.525(3) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 C33 1.389(3) .
C32 C22 1.397(3) 2_656
C33 C34 1.378(3) .
C33 H33 0.9500 .
C34 C35 1.382(4) .
C34 H34 0.9500 .
C35 C23 1.387(3) 2_656
C35 H35 0.9500 .
C36 C37 1.505(3) .
C36 H36A 0.9900 .
C36 H36B 0.9900 .
N3 C42 1.516(3) 2_656
N3 C42 1.516(3) .
N3 C40 1.522(3) .
N3 C40 1.522(3) 2_656
C40 C41 1.519(4) .
C40 H40A 0.9900 .
C40 H40B 0.9900 .
C41 H41A 0.9800 .
C41 H41B 0.9800 .
C41 H41C 0.9800 .
C42 C43 1.516(4) .
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C43 H43A 0.9800 .
C43 H43B 0.9800 .
C43 H43C 0.9800 .
O1W H1WA 0.8001 .
O1W H1WB 0.8001 .
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
N1 H1 F1 0.88 1.86 2.735(2) 169.9
N2 H2 F1 0.88 1.87 2.748(2) 171.4
O1W H1WA F1 0.80 2.01 2.779(4) 162.5
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_4
C37 O5 C38 C39 -171.0(2) . .
C37 O5A C38A C39A -81.6(14) . .
C4 N1 C1 C2 -0.4(2) . .
C4 N1 C1 C10 -179.46(19) . 2_656
N1 C1 C2 C3 0.1(3) . .
C10 C1 C2 C3 179.0(2) 2_656 .
C1 C2 C3 C4 0.3(3) . .
C2 C3 C4 N1 -0.5(3) . .
C2 C3 C4 C5 169.8(2) . .
C1 N1 C4 C3 0.6(2) . .
C1 N1 C4 C5 -170.7(2) . .
C3 C4 C5 C6 126.1(3) . .
N1 C4 C5 C6 -64.9(3) . .
C3 C4 C5 C11 4.5(3) . .
N1 C4 C5 C11 173.5(2) . .
C3 C4 C5 C12 -113.1(3) . .
N1 C4 C5 C12 55.9(3) . .
C9 N2 C6 C7 -0.5(3) . .
C9 N2 C6 C5 172.7(2) . .
C4 C5 C6 C7 -126.0(3) . .
C11 C5 C6 C7 -4.1(4) . .
C12 C5 C6 C7 113.2(3) . .
C4 C5 C6 N2 62.6(3) . .
C11 C5 C6 N2 -175.5(2) . .
C12 C5 C6 N2 -58.3(3) . .
N2 C6 C7 C8 0.3(3) . .
C5 C6 C7 C8 -172.1(2) . .
C6 C7 C8 C9 0.0(3) . .
C6 N2 C9 C8 0.5(3) . .
C6 N2 C9 C10 -177.6(2) . .
C7 C8 C9 N2 -0.2(3) . .
C7 C8 C9 C10 177.5(2) . .
N2 C9 C10 C1 -71.8(3) . 2_656
C8 C9 C10 C1 110.7(3) . 2_656
N2 C9 C10 C14 52.2(3) . .
C8 C9 C10 C14 -125.3(3) . .
N2 C9 C10 C13 169.3(2) . .
C8 C9 C10 C13 -8.2(3) . .
C1 C10 C14 C19 -27.8(3) 2_656 .
C9 C10 C14 C19 -150.9(2) . .
C13 C10 C14 C19 91.2(3) . .
C1 C10 C14 C15 156.4(2) 2_656 .
C9 C10 C14 C15 33.3(3) . .
C13 C10 C14 C15 -84.6(3) . .
C19 C14 C15 C16 -1.6(3) . .
C10 C14 C15 C16 174.4(2) . .
C14 C15 C16 C17 -0.6(4) . .
C20 O1 C17 C18 -15.6(3) . .
C20 O1 C17 C16 164.4(2) . .
C15 C16 C17 O1 -177.5(2) . .
C15 C16 C17 C18 2.6(4) . .
O1 C17 C18 C19 177.7(2) . .
C16 C17 C18 C19 -2.3(4) . .
C15 C14 C19 C18 1.9(4) . .
C10 C14 C19 C18 -174.1(2) . .
C17 C18 C19 C14 0.0(4) . .
C17 O1 C20 C21 -176.45(19) . .
C22 O2 C21 C20 -159.56(19) . .
O1 C20 C21 O2 -67.8(2) . .
C21 O2 C22 C23 -102.9(2) . .
C21 O2 C22 C32 83.9(2) . 2_656
O2 C22 C23 C35 -172.7(2) . 2_656
C32 C22 C23 C35 0.4(3) 2_656 2_656
O2 C22 C23 C24 2.8(3) . .
C32 C22 C23 C24 175.8(2) 2_656 .
C35 C23 C24 C25 59.3(3) 2_656 .
C22 C23 C24 C25 -116.1(2) . .
C23 C24 C25 C30 -115.2(2) . .
C23 C24 C25 C26 56.1(3) . .
C36 O3 C26 C27 -117.1(2) . .
C36 O3 C26 C25 69.7(3) . .
C30 C25 C26 O3 -178.3(2) . .
C24 C25 C26 O3 10.3(3) . .
C30 C25 C26 C27 8.8(3) . .
C24 C25 C26 C27 -162.6(2) . .
O3 C26 C27 C28 178.52(19) . .
C25 C26 C27 C28 -8.4(3) . .
O3 C26 C27 C31 -8.5(3) . .
C25 C26 C27 C31 164.6(2) . .
C26 C27 C28 C29 1.7(3) . .
C31 C27 C28 C29 -171.1(2) . .
C27 C28 C29 C30 4.2(4) . .
C28 C29 C30 C25 -3.6(4) . .
C26 C25 C30 C29 -2.7(3) . .
C24 C25 C30 C29 168.9(2) . .
C26 C27 C31 C32 -65.5(3) . .
C28 C27 C31 C32 107.2(2) . .
C27 C31 C32 C33 -45.9(3) . .
C27 C31 C32 C22 129.3(2) . 2_656
C22 C32 C33 C34 -0.4(3) 2_656 .
C31 C32 C33 C34 174.9(2) . .
C32 C33 C34 C35 0.9(4) . .
C33 C34 C35 C23 -0.7(4) . 2_656
C26 O3 C36 C37 72.6(2) . .
C38 O5 C37 O4 8.6(4) . .
C38 O5 C37 O5A -109.8(8) . .
C38 O5 C37 C36 -175.0(2) . .
C38A O5A C37 O4 -15.6(12) . .
C38A O5A C37 O5 69.7(9) . .
C38A O5A C37 C36 -168.4(8) . .
O3 C36 C37 O4 34.5(3) . .
O3 C36 C37 O5 -141.7(2) . .
O3 C36 C37 O5A -171.1(5) . .
C42 N3 C40 C41 -60.2(3) 2_656 .
C42 N3 C40 C41 57.7(3) . .
C40 N3 C40 C41 178.8(3) 2_656 .
C42 N3 C42 C43 179.3(3) 2_656 .
C40 N3 C42 C43 58.2(3) . .
C40 N3 C42 C43 -59.8(3) 2_656 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.250 0.250 -0.064 822 206 ' '
2 0.250 0.750 0.453 822 206 ' '
