#------------------------------------------------------------------------------
#$Date: 2025-10-06 10:06:17 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302561 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/55/1575559.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_1575559
loop_
_publ_author_name
'Liu, Hao'
'Scott, Harrison M.'
'Lin, Binzhou'
'Huang, Xiaolong'
'Smith, Mark D.'
'Shimizu, Ken D.'
_publ_section_title
;
 Solvent attenuation of dispersion interactions quantified in polar and
 nonpolar media using rigid CH-π balances.
;
_journal_issue                   38
_journal_name_full               'Chemical science'
_journal_page_first              17772
_journal_page_last               17778
_journal_paper_doi               10.1039/d5sc02852c
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C31 H22 F N O2, 0.732(C4 H8 O2)'
_chemical_formula_sum            'C33.93 H27.86 F N O3.46'
_chemical_formula_weight         523.98
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-01-08
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-11 deposited with the CCDC.	2025-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.1848(6)
_cell_length_b                   22.1848(6)
_cell_length_c                   11.2994(5)
_cell_measurement_reflns_used    9712
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.081
_cell_measurement_theta_min      2.597
_cell_volume                     5561.2(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'Bruker APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 PHOTON-II
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            85894
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.142
_diffrn_reflns_theta_min         2.732
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.4912
_exptl_absorpt_correction_T_min  0.4177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1300 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.8504.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       rod
_exptl_crystal_F_000             2201
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6167
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0383
_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)+(0.0625P)²+2.0225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5844
_reflns_number_total             6167
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc02852c2.cif
_cod_data_source_block           ch3_pi_4py
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1575557--1575563.cif.
;
_cod_original_cell_volume        5561.2(4)
_cod_database_code               1575559
_shelx_shelxl_version_number     2019/3
_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   0.988
_shelx_estimated_absorpt_t_min   0.977
_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. Uiso/Uaniso restraints and constraints
Uanis(C3S) = Uanis(C7S)
Uanis(C4S) = Uanis(C8S)
3. Rigid body (RIGU) restrains
 O3S, C6S, O4S, C5S, C7S, C8S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{O1S, O2S, C1S, C2S, C3S, C4S} sigma for 1-2: 0.015, 1-3: 0.04
as in
{O3S, O4S, C5S, C6S, C7S, C8S}
5. Others
 Sof(O1S)=Sof(O2S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=Sof(C2S)=Sof(C3S)=
 Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(H4SC)=FVAR(1)
 Sof(O3S)=Sof(O4S)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=Sof(H5SC)=Sof(C6S)=Sof(C7S)=
 Sof(H7SA)=Sof(H7SB)=Sof(C8S)=Sof(H8SA)=Sof(H8SB)=Sof(H8SC)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C9(H9A,H9B), C3S(H3SA,H3SB), C7S(H7SA,H7SB)
6.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C14(H14), C17(H17), C19(H19), C20(H20), C21(H21),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28)
6.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C4S(H4SA,H4SB,H4SC), C5S(H5SA,H5SB,H5SC), C8S(H8SA,H8SB,
 H8SC)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+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 0.36871(8) 0.12906(7) 0.62349(12) 0.0480(4) Uani 1 1 d . . . . .
O1 O 0.39767(7) 0.21373(7) 0.19307(15) 0.0340(3) Uani 1 1 d . . . . .
O2 O 0.39737(7) 0.00838(6) 0.18944(14) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.38493(8) 0.11106(8) 0.20451(15) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.46468(10) 0.11166(12) -0.13814(19) 0.0357(5) Uani 1 1 d . . . . .
H1A H 0.454411 0.112300 -0.223394 0.043 Uiso 1 1 calc R U . . .
H1B H 0.508959 0.110290 -0.127560 0.043 Uiso 1 1 calc R U . . .
C2 C 0.43477(10) 0.16344(11) -0.06831(19) 0.0332(5) Uani 1 1 d . . . . .
H2 H 0.447649 0.204743 -0.093150 0.040 Uiso 1 1 calc R U . . .
C3 C 0.45292(10) 0.14604(9) 0.05999(18) 0.0279(4) Uani 1 1 d . . . . .
H3 H 0.494392 0.161080 0.078153 0.034 Uiso 1 1 calc R U . . .
C4 C 0.40979(9) 0.16364(10) 0.15739(18) 0.0267(4) Uani 1 1 d . . . . .
C5 C 0.40945(9) 0.05855(9) 0.15585(17) 0.0254(4) Uani 1 1 d . . . . .
C6 C 0.45208(9) 0.07660(9) 0.05831(18) 0.0266(4) Uani 1 1 d . . . . .
H6 H 0.493336 0.060246 0.073865 0.032 Uiso 1 1 calc R U . . .
C7 C 0.43183(10) 0.06143(10) -0.07013(19) 0.0320(4) Uani 1 1 d . . . . .
H7 H 0.441564 0.019566 -0.096833 0.038 Uiso 1 1 calc R U . . .
C8 C 0.36540(10) 0.08016(11) -0.0866(2) 0.0352(5) Uani 1 1 d . . . . .
H8A H 0.340179 0.065205 -0.020571 0.042 Uiso 1 1 calc R U . . .
H8B H 0.349092 0.064478 -0.162145 0.042 Uiso 1 1 calc R U . . .
C9 C 0.36776(10) 0.15006(11) -0.08743(19) 0.0358(5) Uani 1 1 d . . . . .
H9A H 0.353573 0.166422 -0.164040 0.043 Uiso 1 1 calc R U . . .
H9B H 0.342963 0.167205 -0.022833 0.043 Uiso 1 1 calc R U . . .
C10 C 0.34844(9) 0.10969(9) 0.30992(18) 0.0274(4) Uani 1 1 d . . . . .
C11 C 0.37636(11) 0.12142(10) 0.41701(19) 0.0315(4) Uani 1 1 d . . . . .
H11 H 0.417807 0.132030 0.420612 0.038 Uiso 1 1 calc R U . . .
C12 C 0.34194(12) 0.11718(11) 0.51830(19) 0.0355(5) Uani 1 1 d . . . . .
C13 C 0.28221(12) 0.10112(12) 0.5173(2) 0.0404(6) Uani 1 1 d . . . . .
H13 H 0.259938 0.097668 0.588777 0.048 Uiso 1 1 calc R U . . .
C14 C 0.25541(11) 0.09010(11) 0.4086(2) 0.0392(5) Uani 1 1 d . . . . .
H14 H 0.214002 0.079260 0.406024 0.047 Uiso 1 1 calc R U . . .
C15 C 0.28762(10) 0.09449(10) 0.3030(2) 0.0322(4) Uani 1 1 d . . . . .
C16 C 0.25842(10) 0.08295(11) 0.1862(2) 0.0346(5) Uani 1 1 d . . . . .
C17 C 0.24973(11) 0.02539(12) 0.1475(3) 0.0432(6) Uani 1 1 d . . . . .
H17 H 0.260882 -0.007151 0.197607 0.052 Uiso 1 1 calc R U . . .
C18 C 0.22437(12) 0.01248(13) 0.0340(3) 0.0471(6) Uani 1 1 d . . . . .
C19 C 0.21695(18) -0.04646(15) -0.0078(3) 0.0669(10) Uani 1 1 d . . . . .
H19 H 0.228949 -0.079513 0.040172 0.080 Uiso 1 1 calc R U . . .
C20 C 0.1925(2) -0.05699(18) -0.1176(4) 0.0900(15) Uani 1 1 d . . . . .
H20 H 0.186986 -0.097251 -0.144060 0.108 Uiso 1 1 calc R U . . .
C21 C 0.17580(19) -0.00943(18) -0.1900(4) 0.0746(11) Uani 1 1 d . . . . .
H21 H 0.159057 -0.017606 -0.265741 0.089 Uiso 1 1 calc R U . . .
C22 C 0.18315(14) 0.05013(15) -0.1538(3) 0.0536(7) Uani 1 1 d . . . . .
C23 C 0.16644(13) 0.10035(16) -0.2261(3) 0.0543(7) Uani 1 1 d . . . . .
H23 H 0.149593 0.093206 -0.302157 0.065 Uiso 1 1 calc R U . . .
C24 C 0.17412(12) 0.15821(14) -0.1885(3) 0.0487(6) Uani 1 1 d . . . . .
H24 H 0.162604 0.190550 -0.238800 0.058 Uiso 1 1 calc R U . . .
C25 C 0.19932(11) 0.17118(13) -0.0742(2) 0.0419(6) Uani 1 1 d . . . . .
C26 C 0.20754(13) 0.22979(13) -0.0326(3) 0.0474(6) Uani 1 1 d . . . . .
H26 H 0.197061 0.262863 -0.081884 0.057 Uiso 1 1 calc R U . . .
C27 C 0.23050(14) 0.24060(13) 0.0783(3) 0.0518(7) Uani 1 1 d . . . . .
H27 H 0.235079 0.280913 0.105179 0.062 Uiso 1 1 calc R U . . .
C28 C 0.24709(11) 0.19298(13) 0.1515(2) 0.0420(6) Uani 1 1 d . . . . .
H28 H 0.263058 0.201108 0.227871 0.050 Uiso 1 1 calc R U . . .
C29 C 0.24055(10) 0.13364(11) 0.1141(2) 0.0354(5) Uani 1 1 d . . . . .
C30 C 0.21544(10) 0.12168(12) -0.0004(2) 0.0368(5) Uani 1 1 d . . . . .
C31 C 0.20770(11) 0.06168(12) -0.0392(3) 0.0426(6) Uani 1 1 d . . . . .
O1S O 0.5531(3) 0.3936(3) -0.0189(5) 0.0538(16) Uani 0.390(5) 1 d D . P A 1
O2S O 0.5821(2) 0.4075(2) 0.1663(5) 0.0483(15) Uani 0.390(5) 1 d D . P A 1
C1S C 0.6578(7) 0.4036(9) 0.019(2) 0.065(5) Uani 0.390(5) 1 d D . P A 1
H1SA H 0.665803 0.374337 -0.044498 0.097 Uiso 0.390(5) 1 calc R U P A 1
H1SB H 0.682413 0.393671 0.087996 0.097 Uiso 0.390(5) 1 calc R U P A 1
H1SC H 0.667993 0.444154 -0.009130 0.097 Uiso 0.390(5) 1 calc R U P A 1
C2S C 0.5917(3) 0.4013(3) 0.0518(6) 0.0419(16) Uani 0.390(5) 1 d D . P A 1
C3S C 0.520(2) 0.407(2) 0.204(2) 0.0627(19) Uani 0.390(5) 1 d D . P A 1
H3SA H 0.502195 0.366614 0.187117 0.075 Uiso 0.390(5) 1 calc R U P A 1
H3SB H 0.496897 0.437483 0.159933 0.075 Uiso 0.390(5) 1 calc R U P A 1
C4S C 0.519(3) 0.419(3) 0.333(2) 0.084(6) Uani 0.390(5) 1 d D . P A 1
H4SA H 0.526758 0.462202 0.346774 0.126 Uiso 0.390(5) 1 calc R U P A 1
H4SB H 0.549155 0.394987 0.373420 0.126 Uiso 0.390(5) 1 calc R U P A 1
H4SC H 0.478592 0.409265 0.364489 0.126 Uiso 0.390(5) 1 calc R U P A 1
O3S O 0.5160(4) 0.3759(5) -0.0074(8) 0.085(3) Uani 0.342(6) 1 d D . P B 2
O4S O 0.4700(4) 0.3789(4) 0.1627(7) 0.076(2) Uani 0.342(6) 1 d D . P B 2
C5S C 0.4158(10) 0.3344(9) 0.007(3) 0.081(6) Uani 0.342(6) 1 d D . P B 2
H5SA H 0.387465 0.365472 -0.019361 0.121 Uiso 0.342(6) 1 calc R U P B 2
H5SB H 0.397762 0.311651 0.072749 0.121 Uiso 0.342(6) 1 calc R U P B 2
H5SC H 0.424760 0.306991 -0.058270 0.121 Uiso 0.342(6) 1 calc R U P B 2
C6S C 0.4728(5) 0.3636(6) 0.0486(9) 0.076(3) Uani 0.342(6) 1 d D . P B 2
C7S C 0.518(3) 0.410(3) 0.214(3) 0.0627(19) Uani 0.342(6) 1 d D . P B 2
H7SA H 0.524396 0.448595 0.171818 0.075 Uiso 0.342(6) 1 calc R U P B 2
H7SB H 0.555494 0.385749 0.205427 0.075 Uiso 0.342(6) 1 calc R U P B 2
C8S C 0.507(4) 0.422(3) 0.342(3) 0.084(6) Uani 0.342(6) 1 d D . P B 2
H8SA H 0.472718 0.449320 0.350639 0.126 Uiso 0.342(6) 1 calc R U P B 2
H8SB H 0.543231 0.441638 0.376434 0.126 Uiso 0.342(6) 1 calc R U P B 2
H8SC H 0.499422 0.384443 0.383579 0.126 Uiso 0.342(6) 1 calc R U P B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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
C4 N1 C5 113.11(17) . . ?
C4 N1 C10 123.71(17) . . ?
C5 N1 C10 121.76(17) . . ?
H1A C1 H1B 110.3 . . ?
C2 C1 H1A 112.8 . . ?
C2 C1 H1B 112.8 . . ?
C7 C1 H1A 112.8 . . ?
C7 C1 H1B 112.8 . . ?
C7 C1 C2 94.60(17) . . ?
C1 C2 H2 114.6 . . ?
C1 C2 C3 100.41(17) . . ?
C3 C2 H2 114.6 . . ?
C9 C2 C1 101.59(19) . . ?
C9 C2 H2 114.6 . . ?
C9 C2 C3 109.58(18) . . ?
C2 C3 H3 110.3 . . ?
C4 C3 C2 116.86(17) . . ?
C4 C3 H3 110.3 . . ?
C4 C3 C6 105.07(17) . . ?
C6 C3 C2 103.53(17) . . ?
C6 C3 H3 110.3 . . ?
O1 C4 N1 123.47(19) . . ?
O1 C4 C3 128.3(2) . . ?
N1 C4 C3 108.20(17) . . ?
O2 C5 N1 123.96(19) . . ?
O2 C5 C6 127.95(19) . . ?
N1 C5 C6 108.09(17) . . ?
C3 C6 H6 110.5 . . ?
C3 C6 C7 103.37(16) . . ?
C5 C6 C3 105.33(16) . . ?
C5 C6 H6 110.5 . . ?
C5 C6 C7 116.33(17) . . ?
C7 C6 H6 110.5 . . ?
C1 C7 C6 99.93(17) . . ?
C1 C7 H7 114.8 . . ?
C1 C7 C8 101.37(19) . . ?
C6 C7 H7 114.8 . . ?
C8 C7 C6 109.28(18) . . ?
C8 C7 H7 114.8 . . ?
C7 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C7 C8 C9 103.75(18) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
C2 C9 C8 103.05(18) . . ?
C2 C9 H9A 111.2 . . ?
C2 C9 H9B 111.2 . . ?
C8 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
C11 C10 N1 117.87(18) . . ?
C11 C10 C15 121.9(2) . . ?
C15 C10 N1 120.17(19) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 H11 121.1 . . ?
F1 C12 C11 118.2(2) . . ?
F1 C12 C13 118.8(2) . . ?
C13 C12 C11 123.1(2) . . ?
C12 C13 H13 121.1 . . ?
C12 C13 C14 117.9(2) . . ?
C14 C13 H13 121.1 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.8(2) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 C14 117.7(2) . . ?
C10 C15 C16 120.8(2) . . ?
C14 C15 C16 121.5(2) . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 C29 120.7(2) . . ?
C29 C16 C15 119.0(2) . . ?
C16 C17 H17 119.0 . . ?
C16 C17 C18 122.0(2) . . ?
C18 C17 H17 119.0 . . ?
C19 C18 C17 122.4(3) . . ?
C19 C18 C31 119.4(3) . . ?
C31 C18 C17 118.2(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.1(3) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C23 122.7(3) . . ?
C21 C22 C31 118.8(3) . . ?
C31 C22 C23 118.5(3) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.5(3) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.2(3) . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 122.7(2) . . ?
C26 C25 C30 119.2(3) . . ?
C30 C25 C24 118.0(3) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.2(2) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.5(3) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.7(3) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C16 122.5(2) . . ?
C28 C29 C30 119.4(2) . . ?
C30 C29 C16 118.1(2) . . ?
C25 C30 C29 118.9(2) . . ?
C31 C30 C25 120.9(2) . . ?
C31 C30 C29 120.1(2) . . ?
C18 C31 C22 119.4(3) . . ?
C30 C31 C18 120.8(2) . . ?
C30 C31 C22 119.8(2) . . ?
C2S O2S C3S 116.2(13) . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
O1S C2S O2S 124.0(7) . . ?
O1S C2S C1S 122.6(12) . . ?
O2S C2S C1S 113.4(11) . . ?
O2S C3S H3SA 110.1 . . ?
O2S C3S H3SB 110.1 . . ?
O2S C3S C4S 108(4) . . ?
H3SA C3S H3SB 108.4 . . ?
C4S C3S H3SA 110.1 . . ?
C4S C3S H3SB 110.1 . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
C6S O4S C7S 119.3(16) . . ?
H5SA C5S H5SB 109.5 . . ?
H5SA C5S H5SC 109.5 . . ?
H5SB C5S H5SC 109.5 . . ?
C6S C5S H5SA 109.5 . . ?
C6S C5S H5SB 109.5 . . ?
C6S C5S H5SC 109.5 . . ?
O3S C6S O4S 119.8(12) . . ?
O3S C6S C5S 128.2(16) . . ?
O4S C6S C5S 111.8(15) . . ?
O4S C7S H7SA 109.3 . . ?
O4S C7S H7SB 109.3 . . ?
O4S C7S C8S 112(4) . . ?
H7SA C7S H7SB 107.9 . . ?
C8S C7S H7SA 109.3 . . ?
C8S C7S H7SB 109.3 . . ?
C7S C8S H8SA 109.5 . . ?
C7S C8S H8SB 109.5 . . ?
C7S C8S H8SC 109.5 . . ?
H8SA C8S H8SB 109.5 . . ?
H8SA C8S H8SC 109.5 . . ?
H8SB C8S H8SC 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
F1 C12 1.355(3) . ?
O1 C4 1.212(3) . ?
O2 C5 1.206(3) . ?
N1 C4 1.396(3) . ?
N1 C5 1.398(3) . ?
N1 C10 1.440(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.544(3) . ?
C1 C7 1.537(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.553(3) . ?
C2 C9 1.531(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.510(3) . ?
C3 C6 1.541(3) . ?
C5 C6 1.507(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.556(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.543(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.552(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.384(3) . ?
C10 C15 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(3) . ?
C12 C13 1.372(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(3) . ?
C15 C16 1.492(3) . ?
C16 C17 1.363(4) . ?
C16 C29 1.444(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.429(4) . ?
C18 C19 1.400(4) . ?
C18 C31 1.419(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.373(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(5) . ?
C22 C23 1.431(4) . ?
C22 C31 1.428(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.363(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.437(4) . ?
C25 C26 1.395(4) . ?
C25 C30 1.424(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.373(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.390(4) . ?
C29 C30 1.433(4) . ?
C30 C31 1.412(4) . ?
O1S C2S 1.185(8) . ?
O2S C2S 1.319(8) . ?
O2S C3S 1.44(5) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C1S C2S 1.514(16) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C3S C4S 1.493(14) . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
O3S C6S 1.182(12) . ?
O4S C6S 1.334(12) . ?
O4S C7S 1.40(5) . ?
C5S H5SA 0.9800 . ?
C5S H5SB 0.9800 . ?
C5S H5SC 0.9800 . ?
C5S C6S 1.495(17) . ?
C7S H7SA 0.9900 . ?
C7S H7SB 0.9900 . ?
C7S C8S 1.493(15) . ?
C8S H8SA 0.9800 . ?
C8S H8SB 0.9800 . ?
C8S H8SC 0.9800 . ?
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
F1 C12 C13 C14 179.0(2) . . . . ?
O2 C5 C6 C3 -176.3(2) . . . . ?
O2 C5 C6 C7 69.9(3) . . . . ?
N1 C5 C6 C3 3.4(2) . . . . ?
N1 C5 C6 C7 -110.4(2) . . . . ?
N1 C10 C11 C12 -176.89(19) . . . . ?
N1 C10 C15 C14 175.95(19) . . . . ?
N1 C10 C15 C16 -3.6(3) . . . . ?
C1 C2 C3 C4 -149.50(19) . . . . ?
C1 C2 C3 C6 -34.6(2) . . . . ?
C1 C2 C9 C8 36.0(2) . . . . ?
C1 C7 C8 C9 -33.9(2) . . . . ?
C2 C1 C7 C6 -57.51(19) . . . . ?
C2 C1 C7 C8 54.65(19) . . . . ?
C2 C3 C4 O1 -68.6(3) . . . . ?
C2 C3 C4 N1 112.2(2) . . . . ?
C2 C3 C6 C5 -123.99(17) . . . . ?
C2 C3 C6 C7 -1.5(2) . . . . ?
C3 C2 C9 C8 -69.5(2) . . . . ?
C3 C6 C7 C1 37.1(2) . . . . ?
C3 C6 C7 C8 -68.8(2) . . . . ?
C4 N1 C5 O2 174.83(19) . . . . ?
C4 N1 C5 C6 -4.9(2) . . . . ?
C4 N1 C10 C11 -69.3(3) . . . . ?
C4 N1 C10 C15 113.3(2) . . . . ?
C4 C3 C6 C5 -0.9(2) . . . . ?
C4 C3 C6 C7 121.64(17) . . . . ?
C5 N1 C4 O1 -174.93(19) . . . . ?
C5 N1 C4 C3 4.3(2) . . . . ?
C5 N1 C10 C11 96.1(2) . . . . ?
C5 N1 C10 C15 -81.3(2) . . . . ?
C5 C6 C7 C1 151.99(18) . . . . ?
C5 C6 C7 C8 46.1(3) . . . . ?
C6 C3 C4 O1 177.3(2) . . . . ?
C6 C3 C4 N1 -1.9(2) . . . . ?
C6 C7 C8 C9 71.0(2) . . . . ?
C7 C1 C2 C3 56.70(19) . . . . ?
C7 C1 C2 C9 -55.98(19) . . . . ?
C7 C8 C9 C2 -1.3(2) . . . . ?
C9 C2 C3 C4 -43.1(3) . . . . ?
C9 C2 C3 C6 71.8(2) . . . . ?
C10 N1 C4 O1 -8.4(3) . . . . ?
C10 N1 C4 C3 170.85(18) . . . . ?
C10 N1 C5 O2 8.0(3) . . . . ?
C10 N1 C5 C6 -171.74(17) . . . . ?
C10 C11 C12 F1 -179.46(19) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C10 C15 C16 C17 99.6(3) . . . . ?
C10 C15 C16 C29 -79.4(3) . . . . ?
C11 C10 C15 C14 -1.3(3) . . . . ?
C11 C10 C15 C16 179.1(2) . . . . ?
C11 C12 C13 C14 -1.5(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C10 0.8(3) . . . . ?
C13 C14 C15 C16 -179.6(2) . . . . ?
C14 C15 C16 C17 -80.0(3) . . . . ?
C14 C15 C16 C29 101.1(3) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
C15 C16 C17 C18 -177.2(2) . . . . ?
C15 C16 C29 C28 -2.9(3) . . . . ?
C15 C16 C29 C30 176.84(19) . . . . ?
C16 C17 C18 C19 178.0(3) . . . . ?
C16 C17 C18 C31 -0.3(4) . . . . ?
C16 C29 C30 C25 -178.0(2) . . . . ?
C16 C29 C30 C31 1.1(3) . . . . ?
C17 C16 C29 C28 178.2(2) . . . . ?
C17 C16 C29 C30 -2.1(3) . . . . ?
C17 C18 C19 C20 -179.9(4) . . . . ?
C17 C18 C31 C22 179.0(3) . . . . ?
C17 C18 C31 C30 -0.6(4) . . . . ?
C18 C19 C20 C21 1.3(8) . . . . ?
C19 C18 C31 C22 0.6(5) . . . . ?
C19 C18 C31 C30 -179.1(3) . . . . ?
C19 C20 C21 C22 -0.2(8) . . . . ?
C20 C21 C22 C23 -180.0(4) . . . . ?
C20 C21 C22 C31 -0.8(6) . . . . ?
C21 C22 C23 C24 -180.0(4) . . . . ?
C21 C22 C31 C18 0.5(5) . . . . ?
C21 C22 C31 C30 -179.8(3) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C22 C31 C18 179.8(3) . . . . ?
C23 C22 C31 C30 -0.6(4) . . . . ?
C23 C24 C25 C26 -179.7(3) . . . . ?
C23 C24 C25 C30 -0.8(4) . . . . ?
C24 C25 C26 C27 178.5(3) . . . . ?
C24 C25 C30 C29 -179.9(2) . . . . ?
C24 C25 C30 C31 0.9(3) . . . . ?
C25 C26 C27 C28 1.0(4) . . . . ?
C25 C30 C31 C18 179.4(2) . . . . ?
C25 C30 C31 C22 -0.3(4) . . . . ?
C26 C25 C30 C29 -0.9(3) . . . . ?
C26 C25 C30 C31 179.9(2) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
C27 C28 C29 C16 178.6(2) . . . . ?
C27 C28 C29 C30 -1.1(4) . . . . ?
C28 C29 C30 C25 1.7(3) . . . . ?
C28 C29 C30 C31 -179.1(2) . . . . ?
C29 C16 C17 C18 1.7(4) . . . . ?
C29 C30 C31 C18 0.2(4) . . . . ?
C29 C30 C31 C22 -179.4(2) . . . . ?
C30 C25 C26 C27 -0.4(4) . . . . ?
C31 C18 C19 C20 -1.5(6) . . . . ?
C31 C22 C23 C24 0.8(4) . . . . ?
C2S O2S C3S C4S -175(3) . . . . ?
C3S O2S C2S O1S -2(3) . . . . ?
C3S O2S C2S C1S 179(3) . . . . ?
C6S O4S C7S C8S -179(4) . . . . ?
C7S O4S C6S O3S 1(4) . . . . ?
C7S O4S C6S C5S -176(3) . . . . ?
