# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_25mna18c6pf6_ht
_database_code_depnum_ccdc_archive 'CCDC 1982636'
loop_
_audit_author_name
_audit_author_address
'Huang Rui-Kang'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-03-05 downloaded from the CCDC.
;
_audit_creation_date             2019-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(F3 P0.5), C7 H9 N2 O3, C12 H24 O6'
_chemical_formula_sum            'C19 H33 F6 N2 O9 P'
_chemical_formula_weight         578.44
_chemical_melting_point          ?
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'
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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   17.7788(4)
_cell_length_b                   19.7210(3)
_cell_length_c                   15.0786(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5286.79(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10535
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7890
_cell_measurement_theta_min      3.3150
_shelx_estimated_absorpt_T_max   0.719
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    1.767
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26161
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.992
_diffrn_reflns_theta_min         3.347
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  43.00   1.00   10.00    --  -32.00   0.00-108.00  115
  2  ω    -78.00 -18.00   1.00   10.00    --  -32.00 -72.00-180.00   60
  3  ω   -200.00 -38.00   1.00   50.00    -- -110.00   0.00 -36.00  162
  4  ω   -125.00 -60.00   1.00   50.00    -- -110.00  72.00 -36.00   65
  5  ω   -200.00-125.00   1.00   50.00    -- -110.00 -72.00 108.00   75
  6  ω    -80.00 -20.00   1.00   50.00    -- -110.00  72.00  36.00   60
  7  ω   -106.00 -20.00   1.00   50.00    -- -110.00  72.00 108.00   86
  8  ω    -80.00 -20.00   1.00   50.00    -- -110.00  72.00-180.00   60
  9  ω    -98.00 -38.00   1.00   50.00    -- -110.00  72.00-108.00   60
 10  ω   -200.00-130.00   1.00   50.00    -- -110.00 -72.00-180.00   70
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4136
_reflns_number_total             4998
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         4998
_refine_ls_number_restraints     191
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0867
_refine_ls_restrained_S_all      1.210
_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)+(0.3000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2941
_refine_ls_wR_factor_ref         0.3198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F7-F10 \\sim F7-F11 \\sim F7-F8 \\sim F8-F9 \\sim F11-F8 \\sim F10-F11 \\sim
F7-F9 \\sim F9-F10
 with sigma of 0.02
 F3-F4 \\sim F5-F3 \\sim F1-F5 \\sim F4-F1 \\sim F2-F4 \\sim F2-F3 \\sim F2-F5
\\sim F2-F1 \\sim F6-F1 \\sim F6-F3
 \\sim F6-F5 \\sim F6-F4
 with sigma of 0.02
 P1-F2 \\sim P1-F6 \\sim P1-F4 \\sim P1-F5 \\sim P1-F1 \\sim P1-F3 \\sim P2-F7
\\sim P2-F8 \\sim P2-F9 \\sim P2-
 F10 \\sim P2-F11
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C11A \\sim C10: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
F3 \\sim F2 \\sim F4 \\sim F5 \\sim F6 \\sim F1: within 1.7A with sigma of 0.01
and sigma for terminal atoms of 0.02
F8 \\sim F9 \\sim F10 \\sim F7 \\sim F11: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F6) \\sim Ueq, Uanis(F5) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(C8A)=Sof(H8Aa)=Sof(H8Ab)=Sof(C1A)=Sof(H1Aa)=Sof(H1Ab)=Sof(O1A)=Sof(C2A)=
 Sof(H2Aa)=Sof(H2Ab)=Sof(C12A)=Sof(H12c)=Sof(H12d)=Sof(O2A)=Sof(C11A)=Sof(H11c)=
 Sof(H11d)=Sof(C3A)=Sof(H3Aa)=Sof(H3Ab)=Sof(O6A)=Sof(C10A)=Sof(H10c)=Sof(H10d)=
 Sof(C4A)=Sof(H4Aa)=Sof(H4Ab)=Sof(C9A)=Sof(H9Aa)=Sof(H9Ab)=Sof(O3A)=Sof(O5A)=
 Sof(C5A)=Sof(H5Aa)=Sof(H5Ab)=Sof(C6A)=Sof(H6Aa)=Sof(H6Ab)=Sof(C7A)=Sof(H7Aa)=
 Sof(H7Ab)=Sof(O4A)=1-FVAR(1)
 Sof(C1)=Sof(H1a)=Sof(H1b)=Sof(O1)=Sof(C4)=Sof(H4a)=Sof(H4b)=Sof(O6)=Sof(O4)=
 Sof(C3)=Sof(H3a)=Sof(H3b)=Sof(C10)=Sof(H10a)=Sof(H10b)=Sof(C7)=Sof(H7a)=
 Sof(H7b)=Sof(O3)=Sof(O2)=Sof(O5)=Sof(C11)=Sof(H11a)=Sof(H11b)=Sof(C8)=Sof(H8a)=
 Sof(H8b)=Sof(C6)=Sof(H6a)=Sof(H6b)=Sof(C9)=Sof(H9a)=Sof(H9b)=Sof(C5)=Sof(H5a)=
 Sof(H5b)=Sof(C12)=Sof(H12a)=Sof(H12b)=Sof(C2)=Sof(H2a)=Sof(H2b)=FVAR(1)
 Fixed Sof: F9(0.5) F6(0.5) F11(0.5) F4(0.5) F5(0.5) F3(0.5) F2(0.5) F1(0.5)
 F10(0.5) F8(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C4(H4a,H4b), C3(H3a,H3b), C10(H10a,H10b), C7(H7a,H7b), C11(H11a,
 H11b), C8(H8a,H8b), C6(H6a,H6b), C9(H9a,H9b), C5(H5a,H5b), C12(H12a,H12b),
 C2(H2a,H2b), C8A(H8Aa,H8Ab), C1A(H1Aa,H1Ab), C2A(H2Aa,H2Ab), C12A(H12c,H12d),
 C11A(H11c,H11d), C3A(H3Aa,H3Ab), C10A(H10c,H10d), C4A(H4Aa,H4Ab), C9A(H9Aa,
 H9Ab), C5A(H5Aa,H5Ab), C6A(H6Aa,H6Ab), C7A(H7Aa,H7Ab)
5.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C15(H15), C16(H16)
5.c Idealised Me refined as rotating group:
 N1(H1c,H1d,H1e), C19(H19a,H19b,H19c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
P2 P 0.2500 0.2500 0.46752(7) 0.0917(4) Uani 1 2 d DS T P . .
P1 P 0.2500 0.7500 0.58125(10) 0.1538(9) Uani 1 2 d DS T P . .
O7 O 0.38599(10) 0.41958(7) 0.20179(10) 0.0771(5) Uani 1 1 d . . . . .
N1 N 0.46045(10) 0.52676(8) 0.26681(9) 0.0644(5) Uani 1 1 d . . . . .
H1C H 0.4857 0.4891 0.2799 0.077 Uiso 1 1 calc GR . . . .
H1D H 0.4197 0.5295 0.3010 0.077 Uiso 1 1 calc GR . . . .
H1E H 0.4897 0.5626 0.2763 0.077 Uiso 1 1 calc GR . . . .
C14 C 0.40038(11) 0.46793(9) 0.14149(12) 0.0622(5) Uani 1 1 d . . . . .
N2 N 0.45242(18) 0.63085(14) -0.02655(15) 0.0994(7) Uani 1 1 d . . . . .
C13 C 0.43784(10) 0.52509(9) 0.17380(11) 0.0587(5) Uani 1 1 d . . . . .
O8 O 0.4907(2) 0.67591(13) 0.00130(16) 0.1274(9) Uani 1 1 d . . . . .
C18 C 0.45420(12) 0.57922(10) 0.11996(13) 0.0666(5) Uani 1 1 d . . . . .
H18 H 0.4783 0.6175 0.1421 0.080 Uiso 1 1 calc R . . . .
C15 C 0.38041(13) 0.46553(11) 0.05224(14) 0.0734(6) Uani 1 1 d . . . . .
H15 H 0.3556 0.4277 0.0299 0.088 Uiso 1 1 calc R . . . .
C17 C 0.43349(14) 0.57490(11) 0.03150(13) 0.0739(6) Uani 1 1 d . . . . .
F7 F 0.2250(2) 0.32594(13) 0.4702(2) 0.1646(13) Uani 1 1 d D U . A -1
O9 O 0.4315(3) 0.62888(16) -0.10283(15) 0.1573(14) Uani 1 1 d . . . . .
C1 C 0.5075(11) 0.7094(8) 0.3228(11) 0.119(7) Uani 0.528(3) 1 d . . . B 1
H1A H 0.5256 0.7539 0.3056 0.143 Uiso 0.528(3) 1 calc R . . B 1
H1B H 0.5214 0.7021 0.3843 0.143 Uiso 0.528(3) 1 calc R . . B 1
O1 O 0.5430(3) 0.6594(2) 0.2690(2) 0.0838(10) Uani 0.528(3) 1 d . . . B 1
C16 C 0.39734(14) 0.51910(12) -0.00299(13) 0.0774(6) Uani 1 1 d . . . . .
H16 H 0.3845 0.5176 -0.0627 0.093 Uiso 1 1 calc R . . . .
C19 C 0.34902(17) 0.35933(11) 0.1733(2) 0.0884(7) Uani 1 1 d . . . . .
H19A H 0.3781 0.3381 0.1273 0.133 Uiso 1 1 calc GR . . . .
H19B H 0.3000 0.3705 0.1508 0.133 Uiso 1 1 calc GR . . . .
H19C H 0.3440 0.3287 0.2224 0.133 Uiso 1 1 calc GR . . . .
F9 F 0.1777(6) 0.2321(6) 0.4186(8) 0.266(9) Uani 0.5 1 d D U . A -1
C4 C 0.3091(13) 0.5795(11) 0.4159(16) 0.127(7) Uani 0.528(3) 1 d . . . B 1
H4A H 0.3406 0.5838 0.4681 0.153 Uiso 0.528(3) 1 calc R . . B 1
H4B H 0.2568 0.5794 0.4343 0.153 Uiso 0.528(3) 1 calc R . . B 1
O6 O 0.6289(2) 0.5437(2) 0.2213(2) 0.0857(10) Uani 0.528(3) 1 d . . . B 1
F6 F 0.3300(5) 0.7327(6) 0.5472(6) 0.222(4) Uani 0.5 1 d D U . C -1
O4 O 0.4378(2) 0.4237(2) 0.4011(2) 0.0960(11) Uani 0.528(3) 1 d . . . B 1
F11 F 0.3276(4) 0.2654(3) 0.5175(6) 0.160(3) Uani 0.5 1 d D U . A -1
C3 C 0.3248(5) 0.6391(5) 0.3487(7) 0.107(2) Uani 0.528(3) 1 d . . . B 1
H3A H 0.3062 0.6283 0.2899 0.129 Uiso 0.528(3) 1 calc R . . B 1
H3B H 0.3019 0.6811 0.3686 0.129 Uiso 0.528(3) 1 calc R . . B 1
C10 C 0.6741(10) 0.5145(10) 0.2814(9) 0.128(6) Uani 0.528(3) 1 d . U . B 1
H10A H 0.6706 0.5393 0.3368 0.154 Uiso 0.528(3) 1 calc R . . B 1
H10B H 0.7257 0.5173 0.2609 0.154 Uiso 0.528(3) 1 calc R . . B 1
C7 C 0.4947(8) 0.3925(7) 0.4378(9) 0.117(4) Uani 0.528(3) 1 d . . . B 1
H7A H 0.4783 0.3488 0.4600 0.140 Uiso 0.528(3) 1 calc R . . B 1
H7B H 0.5129 0.4189 0.4876 0.140 Uiso 0.528(3) 1 calc R . . B 1
O3 O 0.3264(2) 0.51991(19) 0.3692(3) 0.0992(11) Uani 0.528(3) 1 d . . . B 1
O2 O 0.4042(2) 0.64357(17) 0.3497(3) 0.0880(10) Uani 0.528(3) 1 d . . . B 1
O5 O 0.5853(2) 0.4438(2) 0.3441(3) 0.0962(11) Uani 0.528(3) 1 d . . . B 1
F4 F 0.2205(5) 0.7401(7) 0.4825(4) 0.225(5) Uani 0.5 1 d D U . C -1
C11 C 0.6497(9) 0.6110(7) 0.1990(8) 0.110(4) Uani 0.528(3) 1 d . . . B 1
H11A H 0.6290 0.6221 0.1413 0.132 Uiso 0.528(3) 1 calc R . . B 1
H11B H 0.7040 0.6137 0.1948 0.132 Uiso 0.528(3) 1 calc R . . B 1
C8 C 0.5597(5) 0.3821(4) 0.3697(6) 0.108(2) Uani 0.528(3) 1 d . . . B 1
H8A H 0.6001 0.3563 0.3967 0.130 Uiso 0.528(3) 1 calc R . . B 1
H8B H 0.5415 0.3571 0.3186 0.130 Uiso 0.528(3) 1 calc R . . B 1
F5 F 0.2767(5) 0.7407(5) 0.6777(4) 0.179(4) Uani 0.5 1 d D U . C -1
C6 C 0.3806(6) 0.4322(7) 0.4578(8) 0.126(4) Uani 0.528(3) 1 d . . . B 1
H6A H 0.3978 0.4607 0.5062 0.151 Uiso 0.528(3) 1 calc R . . B 1
H6B H 0.3678 0.3884 0.4827 0.151 Uiso 0.528(3) 1 calc R . . B 1
C9 C 0.6540(4) 0.4414(5) 0.2975(5) 0.0955(19) Uani 0.528(3) 1 d . . . B 1
H9A H 0.6482 0.4173 0.2418 0.115 Uiso 0.528(3) 1 calc R . . B 1
H9B H 0.6926 0.4191 0.3325 0.115 Uiso 0.528(3) 1 calc R . . B 1
C5 C 0.3153(5) 0.4610(6) 0.4221(8) 0.132(3) Uani 0.528(3) 1 d . . . B 1
H5A H 0.2818 0.4726 0.4706 0.158 Uiso 0.528(3) 1 calc R . . B 1
H5B H 0.2902 0.4270 0.3863 0.158 Uiso 0.528(3) 1 calc R . . B 1
C12 C 0.6225(4) 0.6621(3) 0.2658(4) 0.0926(14) Uani 0.528(3) 1 d . . . B 1
H12A H 0.6433 0.6519 0.3237 0.111 Uiso 0.528(3) 1 calc R . . B 1
H12B H 0.6388 0.7072 0.2487 0.111 Uiso 0.528(3) 1 calc R . . B 1
C2 C 0.4274(5) 0.7079(3) 0.3152(5) 0.0948(15) Uani 0.528(3) 1 d . . . B 1
H2A H 0.4124 0.7124 0.2536 0.114 Uiso 0.528(3) 1 calc R . . B 1
H2B H 0.4051 0.7445 0.3490 0.114 Uiso 0.528(3) 1 calc R . . B 1
C8A C 0.4726(13) 0.3758(8) 0.4172(12) 0.151(7) Uani 0.472(3) 1 d . . . B 2
H8AA H 0.5051 0.3502 0.4566 0.182 Uiso 0.472(3) 1 calc R . . B 2
H8AB H 0.4445 0.3439 0.3811 0.182 Uiso 0.472(3) 1 calc R . . B 2
C1A C 0.5772(6) 0.6857(4) 0.2680(5) 0.0960(18) Uani 0.472(3) 1 d . . . B 2
H1AA H 0.5674 0.6949 0.2058 0.115 Uiso 0.472(3) 1 calc R . . B 2
H1AB H 0.6227 0.7096 0.2848 0.115 Uiso 0.472(3) 1 calc R . . B 2
O1A O 0.5870(2) 0.6174(2) 0.2801(3) 0.0857(11) Uani 0.472(3) 1 d . . . B 2
C2A C 0.5125(6) 0.7105(4) 0.3230(9) 0.071(3) Uani 0.472(3) 1 d . . . B 2
H2AA H 0.5224 0.7029 0.3855 0.086 Uiso 0.472(3) 1 calc R . . B 2
H2AB H 0.5049 0.7587 0.3137 0.086 Uiso 0.472(3) 1 calc R . . B 2
C12A C 0.6484(6) 0.5921(8) 0.2285(9) 0.109(4) Uani 0.472(3) 1 d . . . B 2
H12C H 0.6896 0.6244 0.2293 0.131 Uiso 0.472(3) 1 calc R . . B 2
H12D H 0.6327 0.5858 0.1674 0.131 Uiso 0.472(3) 1 calc R . . B 2
O2A O 0.4467(3) 0.6730(3) 0.2953(3) 0.0876(11) Uani 0.472(3) 1 d . . . B 2
C11A C 0.6763(6) 0.5196(7) 0.2703(10) 0.098(4) Uani 0.472(3) 1 d . U . B 2
H11C H 0.7205 0.5024 0.2400 0.118 Uiso 0.472(3) 1 calc R . . B 2
H11D H 0.6868 0.5234 0.3332 0.118 Uiso 0.472(3) 1 calc R . . B 2
C3A C 0.3808(5) 0.6968(3) 0.3387(5) 0.1031(19) Uani 0.472(3) 1 d . . . B 2
H3AA H 0.3719 0.7440 0.3241 0.124 Uiso 0.472(3) 1 calc R . . B 2
H3AB H 0.3862 0.6928 0.4025 0.124 Uiso 0.472(3) 1 calc R . . B 2
O6A O 0.6127(3) 0.4786(2) 0.2541(3) 0.0957(12) Uani 0.472(3) 1 d . . . B 2
C10A C 0.6276(7) 0.4126(5) 0.2918(9) 0.117(3) Uani 0.472(3) 1 d . . . B 2
H10C H 0.6551 0.3856 0.2488 0.140 Uiso 0.472(3) 1 calc R . . B 2
H10D H 0.6594 0.4180 0.3436 0.140 Uiso 0.472(3) 1 calc R . . B 2
C4A C 0.3149(7) 0.6524(6) 0.3059(8) 0.108(3) Uani 0.472(3) 1 d . . . B 2
H4AA H 0.2680 0.6705 0.3287 0.130 Uiso 0.472(3) 1 calc R . . B 2
H4AB H 0.3128 0.6540 0.2416 0.130 Uiso 0.472(3) 1 calc R . . B 2
C9A C 0.5607(5) 0.3767(4) 0.3169(8) 0.110(2) Uani 0.472(3) 1 d . . . B 2
H9AA H 0.5347 0.3624 0.2635 0.132 Uiso 0.472(3) 1 calc R . . B 2
H9AB H 0.5753 0.3361 0.3489 0.132 Uiso 0.472(3) 1 calc R . . B 2
O3A O 0.3234(2) 0.5826(2) 0.3346(3) 0.0918(12) Uani 0.472(3) 1 d . . . B 2
O5A O 0.5116(5) 0.4129(3) 0.3685(4) 0.143(3) Uani 0.472(3) 1 d . . . B 2
C5A C 0.2971(13) 0.5721(14) 0.4162(13) 0.113(6) Uani 0.472(3) 1 d . . . B 2
H5AA H 0.2427 0.5767 0.4160 0.136 Uiso 0.472(3) 1 calc R . . B 2
H5AB H 0.3174 0.6061 0.4559 0.136 Uiso 0.472(3) 1 calc R . . B 2
C6A C 0.3186(7) 0.5004(6) 0.4506(5) 0.127(4) Uani 0.472(3) 1 d . . . B 2
H6AA H 0.3087 0.4986 0.5139 0.152 Uiso 0.472(3) 1 calc R . . B 2
H6AB H 0.2860 0.4674 0.4224 0.152 Uiso 0.472(3) 1 calc R . . B 2
C7A C 0.4166(12) 0.4204(7) 0.4734(7) 0.146(7) Uani 0.472(3) 1 d . . . B 2
H7AA H 0.3730 0.3926 0.4870 0.175 Uiso 0.472(3) 1 calc R . . B 2
H7AB H 0.4410 0.4309 0.5293 0.175 Uiso 0.472(3) 1 calc R . . B 2
O4A O 0.3904(4) 0.4819(3) 0.4366(4) 0.1203(18) Uani 0.472(3) 1 d . . . B 2
F3 F 0.2409(6) 0.6647(4) 0.5832(7) 0.203(5) Uani 0.5 1 d D U . C -1
F2 F 0.1661(5) 0.7482(5) 0.6127(7) 0.230(5) Uani 0.5 1 d D U . C -1
F1 F 0.2557(8) 0.8219(5) 0.5767(10) 0.268(9) Uani 0.5 1 d D U . C -1
F10 F 0.2888(5) 0.2702(4) 0.3796(4) 0.155(3) Uani 0.5 1 d D U . A -1
F8 F 0.2177(4) 0.2313(4) 0.5581(5) 0.192(4) Uani 0.5 1 d D U . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
P2 F7 1.563(2) . ?
P2 F9 1.524(8) . ?
P2 F11 1.600(6) . ?
P2 F10 1.547(5) . ?
P2 F8 1.527(5) . ?
P1 F6 1.551(7) . ?
P1 F4 1.591(7) . ?
P1 F5 1.541(5) . ?
P1 F3 1.690(9) . ?
P1 F2 1.565(8) . ?
P1 F1 1.424(9) . ?
O7 C14 1.342(2) . ?
O7 C19 1.424(3) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
N1 C13 1.459(2) . ?
C14 C13 1.397(3) . ?
C14 C15 1.393(3) . ?
N2 O8 1.196(4) . ?
N2 C17 1.448(3) . ?
N2 O9 1.209(4) . ?
C13 C18 1.372(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.386(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(4) . ?
C17 C16 1.376(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 O1 1.425(17) . ?
C1 C2 1.43(2) . ?
O1 C12 1.415(8) . ?
C16 H16 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.58(3) . ?
C4 O3 1.40(2) . ?
O6 C10 1.340(16) . ?
O6 C11 1.418(12) . ?
O4 C7 1.307(14) . ?
O4 C6 1.338(14) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 O2 1.415(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.51(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.56(2) . ?
O3 C5 1.423(10) . ?
O2 C2 1.431(7) . ?
O5 C8 1.355(9) . ?
O5 C9 1.410(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.505(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.400(15) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A O5A 1.246(18) . ?
C8A C7A 1.58(3) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1A O1A 1.370(9) . ?
C1A C2A 1.501(15) . ?
O1A C12A 1.431(13) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A O2A 1.447(11) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A C11A 1.64(2) . ?
O2A C3A 1.421(9) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A O6A 1.410(15) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A C4A 1.543(15) . ?
O6A C10A 1.444(11) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C9A 1.436(16) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A O3A 1.451(13) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A O5A 1.370(11) . ?
O3A C5A 1.33(2) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.55(3) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6A O4A 1.345(13) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A O4A 1.414(16) . ?

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
F7 P2 F11 92.9(3) . . ?
F9 P2 F7 89.7(5) . . ?
F9 P2 F11 177.3(7) . . ?
F9 P2 F10 91.2(5) . . ?
F9 P2 F8 93.4(5) . . ?
F10 P2 F7 84.4(3) . . ?
F10 P2 F11 88.3(4) . . ?
F8 P2 F7 95.8(3) . . ?
F8 P2 F11 87.1(5) . . ?
F8 P2 F10 175.4(5) . . ?
F6 P1 F4 88.0(5) . . ?
F6 P1 F3 82.8(5) . . ?
F6 P1 F2 165.8(6) . . ?
F4 P1 F3 82.1(5) . . ?
F5 P1 F6 90.2(5) . . ?
F5 P1 F4 166.1(6) . . ?
F5 P1 F3 84.0(4) . . ?
F5 P1 F2 90.3(5) . . ?
F2 P1 F4 88.1(5) . . ?
F2 P1 F3 83.2(5) . . ?
F1 P1 F6 97.9(7) . . ?
F1 P1 F4 95.8(6) . . ?
F1 P1 F5 98.1(6) . . ?
F1 P1 F3 177.8(6) . . ?
F1 P1 F2 96.0(6) . . ?
C14 O7 C19 118.43(18) . . ?
H1C N1 H1D 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C13 N1 H1C 109.5 . . ?
C13 N1 H1D 109.5 . . ?
C13 N1 H1E 109.5 . . ?
O7 C14 C13 115.33(16) . . ?
O7 C14 C15 125.59(18) . . ?
C15 C14 C13 119.07(18) . . ?
O8 N2 C17 119.1(2) . . ?
O8 N2 O9 122.2(3) . . ?
O9 N2 C17 118.6(3) . . ?
C14 C13 N1 118.99(15) . . ?
C18 C13 N1 119.52(16) . . ?
C18 C13 C14 121.49(17) . . ?
C13 C18 H18 121.1 . . ?
C13 C18 C17 117.72(19) . . ?
C17 C18 H18 121.1 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C18 C17 N2 118.2(2) . . ?
C16 C17 N2 119.3(2) . . ?
C16 C17 C18 122.46(19) . . ?
H1A C1 H1B 107.9 . . ?
O1 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
O1 C1 C2 112.4(12) . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C12 O1 C1 115.8(9) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.10(18) . . ?
C17 C16 H16 120.4 . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H4A C4 H4B 108.8 . . ?
C3 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
O3 C4 H4A 110.7 . . ?
O3 C4 H4B 110.7 . . ?
O3 C4 C3 105.2(15) . . ?
C10 O6 C11 113.9(11) . . ?
C7 O4 C6 112.1(9) . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
O2 C3 C4 102.5(11) . . ?
O2 C3 H3A 111.3 . . ?
O2 C3 H3B 111.3 . . ?
O6 C10 H10A 109.2 . . ?
O6 C10 H10B 109.2 . . ?
O6 C10 C9 112.3(11) . . ?
H10A C10 H10B 107.9 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
O4 C7 H7A 109.4 . . ?
O4 C7 H7B 109.4 . . ?
O4 C7 C8 111.0(9) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C4 O3 C5 111.7(12) . . ?
C3 O2 C2 109.8(6) . . ?
C8 O5 C9 113.8(6) . . ?
O6 C11 H11A 109.1 . . ?
O6 C11 H11B 109.1 . . ?
O6 C11 C12 112.6(7) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
O5 C8 C7 108.5(8) . . ?
O5 C8 H8A 110.0 . . ?
O5 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
O4 C6 H6A 108.3 . . ?
O4 C6 H6B 108.3 . . ?
O4 C6 C5 115.8(9) . . ?
H6A C6 H6B 107.4 . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
O5 C9 C10 104.7(8) . . ?
O5 C9 H9A 110.8 . . ?
O5 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
O3 C5 H5A 108.4 . . ?
O3 C5 H5B 108.4 . . ?
C6 C5 O3 115.5(7) . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
O1 C12 C11 108.5(7) . . ?
O1 C12 H12A 110.0 . . ?
O1 C12 H12B 110.0 . . ?
C11 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C1 C2 O2 106.1(8) . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
O2 C2 H2A 110.5 . . ?
O2 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
H8AA C8A H8AB 108.2 . . ?
O5A C8A H8AA 109.7 . . ?
O5A C8A H8AB 109.7 . . ?
O5A C8A C7A 109.9(12) . . ?
C7A C8A H8AA 109.7 . . ?
C7A C8A H8AB 109.7 . . ?
H1AA C1A H1AB 108.1 . . ?
O1A C1A H1AA 109.6 . . ?
O1A C1A H1AB 109.6 . . ?
O1A C1A C2A 110.2(7) . . ?
C2A C1A H1AA 109.6 . . ?
C2A C1A H1AB 109.6 . . ?
C1A O1A C12A 111.6(8) . . ?
C1A C2A H2AA 110.3 . . ?
C1A C2A H2AB 110.3 . . ?
H2AA C2A H2AB 108.6 . . ?
O2A C2A C1A 107.0(7) . . ?
O2A C2A H2AA 110.3 . . ?
O2A C2A H2AB 110.3 . . ?
O1A C12A H12C 109.9 . . ?
O1A C12A H12D 109.9 . . ?
O1A C12A C11A 109.0(9) . . ?
H12C C12A H12D 108.3 . . ?
C11A C12A H12C 109.9 . . ?
C11A C12A H12D 109.9 . . ?
C3A O2A C2A 111.4(6) . . ?
C12A C11A H11C 111.6 . . ?
C12A C11A H11D 111.6 . . ?
H11C C11A H11D 109.4 . . ?
O6A C11A C12A 101.1(10) . . ?
O6A C11A H11C 111.6 . . ?
O6A C11A H11D 111.6 . . ?
O2A C3A H3AA 110.3 . . ?
O2A C3A H3AB 110.3 . . ?
O2A C3A C4A 106.9(6) . . ?
H3AA C3A H3AB 108.6 . . ?
C4A C3A H3AA 110.3 . . ?
C4A C3A H3AB 110.3 . . ?
C11A O6A C10A 107.6(9) . . ?
O6A C10A H10C 108.9 . . ?
O6A C10A H10D 108.9 . . ?
H10C C10A H10D 107.7 . . ?
C9A C10A O6A 113.4(8) . . ?
C9A C10A H10C 108.9 . . ?
C9A C10A H10D 108.9 . . ?
C3A C4A H4AA 109.4 . . ?
C3A C4A H4AB 109.4 . . ?
H4AA C4A H4AB 108.0 . . ?
O3A C4A C3A 111.3(8) . . ?
O3A C4A H4AA 109.4 . . ?
O3A C4A H4AB 109.4 . . ?
C10A C9A H9AA 108.5 . . ?
C10A C9A H9AB 108.5 . . ?
H9AA C9A H9AB 107.5 . . ?
O5A C9A C10A 114.9(8) . . ?
O5A C9A H9AA 108.5 . . ?
O5A C9A H9AB 108.5 . . ?
C5A O3A C4A 112.8(13) . . ?
C8A O5A C9A 112.5(11) . . ?
O3A C5A H5AA 109.4 . . ?
O3A C5A H5AB 109.4 . . ?
O3A C5A C6A 111.4(17) . . ?
H5AA C5A H5AB 108.0 . . ?
C6A C5A H5AA 109.4 . . ?
C6A C5A H5AB 109.4 . . ?
C5A C6A H6AA 108.5 . . ?
C5A C6A H6AB 108.5 . . ?
H6AA C6A H6AB 107.5 . . ?
O4A C6A C5A 115.3(11) . . ?
O4A C6A H6AA 108.5 . . ?
O4A C6A H6AB 108.5 . . ?
C8A C7A H7AA 107.7 . . ?
C8A C7A H7AB 107.7 . . ?
H7AA C7A H7AB 107.1 . . ?
O4A C7A C8A 118.4(10) . . ?
O4A C7A H7AA 107.7 . . ?
O4A C7A H7AB 107.7 . . ?
C6A O4A C7A 118.9(10) . . ?

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
O7 C14 C13 N1 2.3(3) . . . . ?
O7 C14 C13 C18 -178.12(18) . . . . ?
O7 C14 C15 C16 178.9(2) . . . . ?
N1 C13 C18 C17 178.37(18) . . . . ?
C14 C13 C18 C17 -1.2(3) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
N2 C17 C16 C15 179.1(2) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C13 C18 C17 N2 -178.2(2) . . . . ?
C13 C18 C17 C16 0.4(3) . . . . ?
O8 N2 C17 C18 6.5(4) . . . . ?
O8 N2 C17 C16 -172.1(3) . . . . ?
C18 C17 C16 C15 0.5(4) . . . . ?
C15 C14 C13 N1 -178.43(18) . . . . ?
C15 C14 C13 C18 1.1(3) . . . . ?
O9 N2 C17 C18 -176.6(3) . . . . ?
O9 N2 C17 C16 4.7(5) . . . . ?
C1 O1 C12 C11 -174.0(10) . . . . ?
O1 C1 C2 O2 64.4(13) . . . . ?
C19 O7 C14 C13 -179.0(2) . . . . ?
C19 O7 C14 C15 1.8(3) . . . . ?
C4 C3 O2 C2 -161.7(9) . . . . ?
C4 O3 C5 C6 -101.6(15) . . . . ?
O6 C10 C9 O5 -70.9(12) . . . . ?
O6 C11 C12 O1 -60.8(12) . . . . ?
O4 C7 C8 O5 63.3(10) . . . . ?
O4 C6 C5 O3 -47.4(17) . . . . ?
C3 C4 O3 C5 179.6(10) . . . . ?
C3 O2 C2 C1 177.1(9) . . . . ?
C10 O6 C11 C12 -81.3(14) . . . . ?
C7 O4 C6 C5 -175.7(11) . . . . ?
O3 C4 C3 O2 -76.6(14) . . . . ?
C11 O6 C10 C9 -175.2(9) . . . . ?
C8 O5 C9 C10 -176.3(7) . . . . ?
C6 O4 C7 C8 178.9(9) . . . . ?
C9 O5 C8 C7 167.3(6) . . . . ?
C2 C1 O1 C12 173.7(9) . . . . ?
C8A C7A O4A C6A 141.9(14) . . . . ?
C1A O1A C12A C11A 160.3(9) . . . . ?
C1A C2A O2A C3A -175.2(7) . . . . ?
O1A C1A C2A O2A -59.0(10) . . . . ?
O1A C12A C11A O6A 65.8(12) . . . . ?
C2A C1A O1A C12A -179.9(9) . . . . ?
C2A O2A C3A C4A -178.8(8) . . . . ?
C12A C11A O6A C10A -177.3(8) . . . . ?
O2A C3A C4A O3A 65.6(10) . . . . ?
C11A O6A C10A C9A 153.2(10) . . . . ?
C3A C4A O3A C5A 84.5(14) . . . . ?
O6A C10A C9A O5A -50.4(14) . . . . ?
C10A C9A O5A C8A -152.7(13) . . . . ?
C4A O3A C5A C6A -170.7(11) . . . . ?
O3A C5A C6A O4A 45.3(18) . . . . ?
O5A C8A C7A O4A 30(2) . . . . ?
C5A C6A O4A C7A 173.9(11) . . . . ?
C7A C8A O5A C9A -179.1(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_25mna18c6pf6_lt
_database_code_depnum_ccdc_archive 'CCDC 1982637'
loop_
_audit_author_name
_audit_author_address
'Huang Rui-Kang'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-03-05 downloaded from the CCDC.
;
_audit_creation_date             2019-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(F3 P0.5), C7 H9 N2 O3, C12 H24 O6'
_chemical_formula_sum            'C19 H33 F6 N2 O9 P'
_chemical_formula_weight         578.44
_chemical_melting_point          ?
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'
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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   16.774(3)
_cell_length_b                   20.000(3)
_cell_length_c                   15.122(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5073.0(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3698
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      32.4
_shelx_estimated_absorpt_T_max   0.710
_shelx_estimated_absorpt_T_min   0.608
_exptl_absorpt_coefficient_mu    1.842
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24568
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.977
_diffrn_reflns_theta_min         6.794
_diffrn_ambient_temperature      213
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4410
_reflns_number_total             4776
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4776
_refine_ls_number_restraints     209
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.305
_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)+(0.0842P)²+1.6517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1568
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F7-F10 \\sim F7-F11 \\sim F7-F8 \\sim F8-F9 \\sim F11-F8 \\sim F10-F11 \\sim
F7-F9 \\sim F9-F10
 with sigma of 0.02
 F3-F4 \\sim F5-F3 \\sim F1-F5 \\sim F4-F1 \\sim F2-F4 \\sim F2-F3 \\sim F2-F5
\\sim F2-F1 \\sim F6-F1 \\sim F6-F3
 \\sim F6-F5 \\sim F6-F4
 with sigma of 0.02
 P1-F2 \\sim P1-F6 \\sim P1-F4 \\sim P1-F5 \\sim P1-F1 \\sim P1-F3 \\sim P2-F7
\\sim P2-F8 \\sim P2-F9 \\sim P2-
 F10 \\sim P2-F11
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C11A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
F3 \\sim F2 \\sim F4 \\sim F5 \\sim F6 \\sim F1: within 1.7A with sigma of 0.01
and sigma for terminal atoms of 0.02
F8 \\sim F9 \\sim F10 \\sim F7 \\sim F11: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F6) \\sim Ueq, Uanis(F5) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F9) \\sim Ueq, Uanis(F11) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F8)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: F9(0.5) F6(0.5) F11(0.5) F4(0.5) F5(0.5) F3(0.5) F2(0.5) F1(0.5)
 F10(0.5) F8(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C8A(H8Aa,H8Ab), C1A(H1Aa,H1Ab), C2A(H2Aa,H2Ab), C12A(H12a,H12b), C11A(H11a,
 H11b), C3A(H3Aa,H3Ab), C10A(H10a,H10b), C4A(H4Aa,H4Ab), C9A(H9Aa,H9Ab),
 C5A(H5Aa,H5Ab), C6A(H6Aa,H6Ab), C7A(H7Aa,H7Ab)
5.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C15(H15), C16(H16)
5.c Idealised Me refined as rotating group:
 N1(H1a,H1b,H1c), C19(H19a,H19b,H19c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
P2 P 0.2500 0.2500 0.46502(5) 0.0428(2) Uani 1 2 d DS T P . .
P1 P 0.2500 0.7500 0.59486(6) 0.0627(3) Uani 1 2 d DS T P . .
O7 O 0.38231(8) 0.42061(6) 0.20247(8) 0.0414(3) Uani 1 1 d . . . . .
N1 N 0.45957(9) 0.52661(7) 0.27488(9) 0.0338(3) Uani 1 1 d . . . . .
H1A H 0.4821 0.4871 0.2883 0.041 Uiso 1 1 calc GR . . . .
H1B H 0.4162 0.5329 0.3090 0.041 Uiso 1 1 calc GR . . . .
H1C H 0.4948 0.5597 0.2847 0.041 Uiso 1 1 calc GR . . . .
C14 C 0.39798(10) 0.47114(8) 0.14572(11) 0.0345(4) Uani 1 1 d . . . . .
N2 N 0.45093(13) 0.64000(9) -0.01029(11) 0.0542(5) Uani 1 1 d . . . . .
C13 C 0.43616(10) 0.52691(8) 0.18215(10) 0.0322(3) Uani 1 1 d . . . . .
O8 O 0.49158(14) 0.68407(10) 0.02183(12) 0.0770(6) Uani 1 1 d . . . . .
C18 C 0.45253(11) 0.58244(9) 0.13157(11) 0.0362(4) Uani 1 1 d . . . . .
H18 H 0.4773 0.6201 0.1565 0.043 Uiso 1 1 calc R . . . .
C15 C 0.37850(12) 0.47140(9) 0.05601(12) 0.0424(4) Uani 1 1 d . . . . .
H15 H 0.3536 0.4340 0.0305 0.051 Uiso 1 1 calc R . . . .
C17 C 0.43155(12) 0.58132(9) 0.04318(11) 0.0405(4) Uani 1 1 d . . . . .
F7 F 0.22930(15) 0.32727(8) 0.46611(12) 0.0913(6) Uani 1 1 d D U . A -1
O9 O 0.42602(19) 0.64164(9) -0.08589(11) 0.0896(8) Uani 1 1 d . . . . .
C16 C 0.39583(12) 0.52677(10) 0.00461(12) 0.0439(4) Uani 1 1 d . . . . .
H16 H 0.3833 0.5271 -0.0560 0.053 Uiso 1 1 calc R . . . .
C19 C 0.34437(14) 0.36185(9) 0.16696(15) 0.0498(5) Uani 1 1 d . . . . .
H19A H 0.3786 0.3418 0.1226 0.075 Uiso 1 1 calc GR . . . .
H19B H 0.2939 0.3742 0.1402 0.075 Uiso 1 1 calc GR . . . .
H19C H 0.3350 0.3300 0.2142 0.075 Uiso 1 1 calc GR . . . .
F9 F 0.1704(4) 0.2392(3) 0.4180(6) 0.167(4) Uani 0.5 1 d D U . A -1
F6 F 0.3365(3) 0.7210(3) 0.5717(3) 0.0914(14) Uani 0.5 1 d D U . B -1
F11 F 0.3310(3) 0.2615(2) 0.5109(6) 0.141(3) Uani 0.5 1 d D U . A -1
F4 F 0.2326(5) 0.7461(5) 0.4935(2) 0.131(3) Uani 0.5 1 d D U . B -1
F5 F 0.2739(3) 0.7408(3) 0.69582(19) 0.0891(17) Uani 0.5 1 d D U . B -1
C8A C 0.46187(16) 0.37128(11) 0.40315(14) 0.0553(5) Uani 1 1 d . . . . .
H8AA H 0.4825 0.3295 0.4281 0.066 Uiso 1 1 calc R . . . .
H8AB H 0.4221 0.3601 0.3580 0.066 Uiso 1 1 calc R . . . .
C1A C 0.59403(13) 0.68299(10) 0.26615(14) 0.0492(5) Uani 1 1 d . . . . .
H1AA H 0.5775 0.6930 0.2054 0.059 Uiso 1 1 calc R . . . .
H1AB H 0.6437 0.7071 0.2781 0.059 Uiso 1 1 calc R . . . .
O1A O 0.60642(9) 0.61293(7) 0.27601(9) 0.0450(3) Uani 1 1 d . . . . .
C2A C 0.53068(13) 0.70491(9) 0.32981(13) 0.0446(4) Uani 1 1 d . . . . .
H2AA H 0.5477 0.6958 0.3906 0.054 Uiso 1 1 calc R . . . .
H2AB H 0.5214 0.7531 0.3239 0.054 Uiso 1 1 calc R . . . .
C12A C 0.65994(13) 0.58728(11) 0.21122(13) 0.0500(5) Uani 1 1 d . . . . .
H12A H 0.7065 0.6166 0.2060 0.060 Uiso 1 1 calc R . . . .
H12B H 0.6335 0.5851 0.1535 0.060 Uiso 1 1 calc R . . . .
O2A O 0.45939(8) 0.66932(7) 0.31092(9) 0.0452(3) Uani 1 1 d . . . . .
C11A C 0.68562(13) 0.51851(12) 0.23936(15) 0.0519(5) Uani 1 1 d . U . . .
H11A H 0.7251 0.5009 0.1976 0.062 Uiso 1 1 calc R . . . .
H11B H 0.7102 0.5205 0.2981 0.062 Uiso 1 1 calc R . . . .
C3A C 0.39230(13) 0.69527(10) 0.35712(15) 0.0493(5) Uani 1 1 d . . . . .
H3AA H 0.3815 0.7412 0.3378 0.059 Uiso 1 1 calc R . . . .
H3AB H 0.4031 0.6959 0.4208 0.059 Uiso 1 1 calc R . . . .
O6A O 0.61802(8) 0.47602(7) 0.24157(9) 0.0465(3) Uani 1 1 d . . . . .
C10A C 0.63782(14) 0.41010(11) 0.27159(14) 0.0506(5) Uani 1 1 d . . . . .
H10A H 0.6720 0.4128 0.3240 0.061 Uiso 1 1 calc R . . . .
H10B H 0.6669 0.3860 0.2253 0.061 Uiso 1 1 calc R . . . .
C4A C 0.32113(13) 0.65156(10) 0.33826(15) 0.0503(5) Uani 1 1 d . . . . .
H4AA H 0.2744 0.6706 0.3679 0.060 Uiso 1 1 calc R . . . .
H4AB H 0.3107 0.6521 0.2745 0.060 Uiso 1 1 calc R . . . .
C9A C 0.56267(14) 0.37371(10) 0.29360(14) 0.0491(5) Uani 1 1 d . . . . .
H9AA H 0.5274 0.3724 0.2420 0.059 Uiso 1 1 calc R . . . .
H9AB H 0.5747 0.3277 0.3113 0.059 Uiso 1 1 calc R . . . .
O3A O 0.33037(8) 0.58365(7) 0.36619(9) 0.0459(3) Uani 1 1 d . . . . .
O5A O 0.52534(10) 0.40860(7) 0.36435(9) 0.0520(4) Uani 1 1 d . . . . .
C5A C 0.33074(18) 0.57547(13) 0.45944(15) 0.0636(6) Uani 1 1 d . . . . .
H5AA H 0.2823 0.5951 0.4847 0.076 Uiso 1 1 calc R . . . .
H5AB H 0.3769 0.5986 0.4848 0.076 Uiso 1 1 calc R . . . .
C6A C 0.33456(16) 0.50325(12) 0.48161(15) 0.0594(6) Uani 1 1 d . . . . .
H6AA H 0.3412 0.4977 0.5456 0.071 Uiso 1 1 calc R . . . .
H6AB H 0.2848 0.4813 0.4641 0.071 Uiso 1 1 calc R . . . .
C7A C 0.42465(17) 0.41224(12) 0.47387(15) 0.0580(6) Uani 1 1 d . . . . .
H7AA H 0.3792 0.3882 0.4993 0.070 Uiso 1 1 calc R . . . .
H7AB H 0.4634 0.4206 0.5211 0.070 Uiso 1 1 calc R . . . .
O4A O 0.39874(11) 0.47387(8) 0.43725(11) 0.0639(5) Uani 1 1 d . . . . .
F3 F 0.2226(3) 0.6692(3) 0.5989(4) 0.0760(15) Uani 0.5 1 d D U . B -1
F2 F 0.1644(4) 0.7653(4) 0.6181(6) 0.180(4) Uani 0.5 1 d D U . B -1
F1 F 0.2749(6) 0.8211(4) 0.5913(7) 0.148(4) Uani 0.5 1 d D U . B -1
F10 F 0.2877(3) 0.2674(3) 0.3750(3) 0.122(3) Uani 0.5 1 d D U . A -1
F8 F 0.2126(3) 0.2345(3) 0.5549(3) 0.129(3) Uani 0.5 1 d D U . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
P2 F7 1.5840(16) . ?
P2 F9 1.528(5) . ?
P2 F11 1.542(4) . ?
P2 F10 1.540(3) . ?
P2 F8 1.528(3) . ?
P1 F6 1.602(5) . ?
P1 F4 1.562(4) . ?
P1 F5 1.589(3) . ?
P1 F3 1.682(6) . ?
P1 F2 1.510(5) . ?
P1 F1 1.483(7) . ?
O7 C14 1.351(2) . ?
O7 C19 1.440(2) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
N1 C13 1.456(2) . ?
C14 C13 1.399(2) . ?
C14 C15 1.395(3) . ?
N2 O8 1.216(3) . ?
N2 C17 1.462(3) . ?
N2 O9 1.217(3) . ?
C13 C18 1.376(2) . ?
C18 H18 0.9400 . ?
C18 C17 1.382(2) . ?
C15 H15 0.9400 . ?
C15 C16 1.384(3) . ?
C17 C16 1.375(3) . ?
C16 H16 0.9400 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A O5A 1.426(3) . ?
C8A C7A 1.485(3) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A O1A 1.424(2) . ?
C1A C2A 1.499(3) . ?
O1A C12A 1.424(2) . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A O2A 1.421(2) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A C11A 1.503(3) . ?
O2A C3A 1.423(3) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A O6A 1.418(3) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A C4A 1.507(3) . ?
O6A C10A 1.433(3) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A C9A 1.493(3) . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A O3A 1.431(3) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A O5A 1.423(3) . ?
O3A C5A 1.420(3) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A C6A 1.484(3) . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A O4A 1.398(3) . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A O4A 1.419(3) . ?

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
F9 P2 F7 87.2(3) . . ?
F9 P2 F11 178.9(5) . . ?
F9 P2 F10 88.8(4) . . ?
F9 P2 F8 91.5(4) . . ?
F11 P2 F7 92.4(2) . . ?
F10 P2 F7 83.0(2) . . ?
F10 P2 F11 90.1(4) . . ?
F8 P2 F7 95.7(2) . . ?
F8 P2 F11 89.6(5) . . ?
F8 P2 F10 178.7(3) . . ?
F6 P1 F3 84.7(3) . . ?
F4 P1 F6 86.3(3) . . ?
F4 P1 F5 169.7(4) . . ?
F4 P1 F3 86.3(4) . . ?
F5 P1 F6 86.5(2) . . ?
F5 P1 F3 85.6(3) . . ?
F2 P1 F6 170.5(5) . . ?
F2 P1 F4 93.5(4) . . ?
F2 P1 F5 92.3(4) . . ?
F2 P1 F3 85.8(4) . . ?
F1 P1 F6 94.8(5) . . ?
F1 P1 F4 93.8(5) . . ?
F1 P1 F5 94.3(4) . . ?
F1 P1 F3 179.5(6) . . ?
F1 P1 F2 94.7(5) . . ?
C14 O7 C19 117.35(15) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C13 N1 H1A 109.5 . . ?
C13 N1 H1B 109.5 . . ?
C13 N1 H1C 109.5 . . ?
O7 C14 C13 115.79(15) . . ?
O7 C14 C15 125.06(16) . . ?
C15 C14 C13 119.14(16) . . ?
O8 N2 C17 119.07(17) . . ?
O8 N2 O9 123.23(19) . . ?
O9 N2 C17 117.7(2) . . ?
C14 C13 N1 119.96(15) . . ?
C18 C13 N1 118.99(15) . . ?
C18 C13 C14 121.05(15) . . ?
C13 C18 H18 120.9 . . ?
C13 C18 C17 118.27(16) . . ?
C17 C18 H18 120.9 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.99(17) . . ?
C16 C15 H15 120.0 . . ?
C18 C17 N2 117.73(17) . . ?
C16 C17 N2 119.96(16) . . ?
C16 C17 C18 122.28(17) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.24(16) . . ?
C17 C16 H16 120.4 . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H8AA C8A H8AB 108.3 . . ?
O5A C8A H8AA 109.9 . . ?
O5A C8A H8AB 109.9 . . ?
O5A C8A C7A 108.75(19) . . ?
C7A C8A H8AA 109.9 . . ?
C7A C8A H8AB 109.9 . . ?
H1AA C1A H1AB 108.3 . . ?
O1A C1A H1AA 109.9 . . ?
O1A C1A H1AB 109.9 . . ?
O1A C1A C2A 108.89(16) . . ?
C2A C1A H1AA 109.9 . . ?
C2A C1A H1AB 109.9 . . ?
C12A O1A C1A 111.98(15) . . ?
C1A C2A H2AA 109.9 . . ?
C1A C2A H2AB 109.9 . . ?
H2AA C2A H2AB 108.3 . . ?
O2A C2A C1A 108.73(15) . . ?
O2A C2A H2AA 109.9 . . ?
O2A C2A H2AB 109.9 . . ?
O1A C12A H12A 110.0 . . ?
O1A C12A H12B 110.0 . . ?
O1A C12A C11A 108.40(16) . . ?
H12A C12A H12B 108.4 . . ?
C11A C12A H12A 110.0 . . ?
C11A C12A H12B 110.0 . . ?
C2A O2A C3A 112.61(15) . . ?
C12A C11A H11A 109.9 . . ?
C12A C11A H11B 109.9 . . ?
H11A C11A H11B 108.3 . . ?
O6A C11A C12A 109.03(17) . . ?
O6A C11A H11A 109.9 . . ?
O6A C11A H11B 109.9 . . ?
O2A C3A H3AA 109.9 . . ?
O2A C3A H3AB 109.9 . . ?
O2A C3A C4A 108.80(16) . . ?
H3AA C3A H3AB 108.3 . . ?
C4A C3A H3AA 109.9 . . ?
C4A C3A H3AB 109.9 . . ?
C11A O6A C10A 111.94(16) . . ?
O6A C10A H10A 109.9 . . ?
O6A C10A H10B 109.9 . . ?
O6A C10A C9A 108.87(17) . . ?
H10A C10A H10B 108.3 . . ?
C9A C10A H10A 109.9 . . ?
C9A C10A H10B 109.9 . . ?
C3A C4A H4AA 108.7 . . ?
C3A C4A H4AB 108.7 . . ?
H4AA C4A H4AB 107.6 . . ?
O3A C4A C3A 114.14(17) . . ?
O3A C4A H4AA 108.7 . . ?
O3A C4A H4AB 108.7 . . ?
C10A C9A H9AA 110.2 . . ?
C10A C9A H9AB 110.2 . . ?
H9AA C9A H9AB 108.5 . . ?
O5A C9A C10A 107.46(17) . . ?
O5A C9A H9AA 110.2 . . ?
O5A C9A H9AB 110.2 . . ?
C5A O3A C4A 113.77(17) . . ?
C9A O5A C8A 112.40(17) . . ?
O3A C5A H5AA 109.7 . . ?
O3A C5A H5AB 109.7 . . ?
O3A C5A C6A 109.68(19) . . ?
H5AA C5A H5AB 108.2 . . ?
C6A C5A H5AA 109.7 . . ?
C6A C5A H5AB 109.7 . . ?
C5A C6A H6AA 109.8 . . ?
C5A C6A H6AB 109.8 . . ?
H6AA C6A H6AB 108.2 . . ?
O4A C6A C5A 109.51(19) . . ?
O4A C6A H6AA 109.8 . . ?
O4A C6A H6AB 109.8 . . ?
C8A C7A H7AA 109.9 . . ?
C8A C7A H7AB 109.9 . . ?
H7AA C7A H7AB 108.3 . . ?
O4A C7A C8A 109.08(17) . . ?
O4A C7A H7AA 109.9 . . ?
O4A C7A H7AB 109.9 . . ?
C6A O4A C7A 114.43(17) . . ?

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
O7 C14 C13 N1 2.7(2) . . . . ?
O7 C14 C13 C18 -177.59(16) . . . . ?
O7 C14 C15 C16 178.45(18) . . . . ?
N1 C13 C18 C17 178.55(16) . . . . ?
C14 C13 C18 C17 -1.1(3) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
N2 C17 C16 C15 179.45(18) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C13 C18 C17 N2 -178.61(17) . . . . ?
C13 C18 C17 C16 -0.5(3) . . . . ?
O8 N2 C17 C18 7.6(3) . . . . ?
O8 N2 C17 C16 -170.5(2) . . . . ?
C18 C17 C16 C15 1.4(3) . . . . ?
C15 C14 C13 N1 -177.77(16) . . . . ?
C15 C14 C13 C18 1.9(3) . . . . ?
O9 N2 C17 C18 -173.4(2) . . . . ?
O9 N2 C17 C16 8.5(3) . . . . ?
C19 O7 C14 C13 -178.88(16) . . . . ?
C19 O7 C14 C15 1.6(3) . . . . ?
C8A C7A O4A C6A 152.9(2) . . . . ?
C1A O1A C12A C11A 165.97(17) . . . . ?
C1A C2A O2A C3A -169.34(17) . . . . ?
O1A C1A C2A O2A -59.6(2) . . . . ?
O1A C12A C11A O6A 63.0(2) . . . . ?
C2A C1A O1A C12A 173.89(16) . . . . ?
C2A O2A C3A C4A -175.92(17) . . . . ?
C12A C11A O6A C10A -177.55(16) . . . . ?
O2A C3A C4A O3A 61.0(2) . . . . ?
C11A O6A C10A C9A 166.11(17) . . . . ?
C3A C4A O3A C5A 69.7(2) . . . . ?
O6A C10A C9A O5A -62.8(2) . . . . ?
C10A C9A O5A C8A -167.94(17) . . . . ?
C4A O3A C5A C6A 175.8(2) . . . . ?
O3A C5A C6A O4A 52.7(3) . . . . ?
O5A C8A C7A O4A 56.7(3) . . . . ?
C5A C6A O4A C7A 160.4(2) . . . . ?
C7A C8A O5A C9A -178.00(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_25mna18c6so3cf3_rt
_database_code_depnum_ccdc_archive 'CCDC 1982638'
loop_
_audit_author_name
_audit_author_address
'Huang Rui-Kang'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-03-05 downloaded from the CCDC.
;
_audit_creation_date             2019-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H9 N2 O3, C12 H24 O6, C F3 O3 S'
_chemical_formula_sum            'C20 H33 F3 N2 O12 S'
_chemical_formula_weight         582.54
_chemical_melting_point          ?
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'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_cell_length_a                   10.0129(3)
_cell_length_b                   18.4433(5)
_cell_length_c                   14.9448(3)
_cell_angle_alpha                90.0
_cell_angle_beta                 98.440(2)
_cell_angle_gamma                90.0
_cell_volume                     2729.98(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11255
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0930
_cell_measurement_theta_min      2.3740
_cell_oxdiff_angle_alpha         89.9928(19)
_cell_oxdiff_angle_beta          98.418(2)
_cell_oxdiff_angle_gamma         89.921(3)
_cell_oxdiff_length_a            10.0097(3)
_cell_oxdiff_length_b            18.4460(6)
_cell_oxdiff_length_c            14.9465(3)
_cell_oxdiff_measurement_reflns_used 11255
_cell_oxdiff_volume              2729.98(13)
_shelx_estimated_absorpt_T_max   0.715
_shelx_estimated_absorpt_T_min   0.614
_exptl_absorpt_coefficient_mu    1.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21559
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        70.987
_diffrn_reflns_theta_max         70.987
_diffrn_reflns_theta_min         3.832
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -18.00   1.00   12.00    --  -32.00 -72.00-108.00   60
  2  ω    -47.00  15.00   1.00   12.00    --  -32.00  72.00-180.00   62
  3  ω    -47.00  15.00   1.00   12.00    --  -32.00  72.00-108.00   62
  4  ω    -78.00 -18.00   1.00   12.00    --  -32.00 -72.00 -36.00   60
  5  ω    -78.00 -18.00   1.00   12.00    --  -32.00 -72.00-180.00   60
  6  ω    -78.00 -18.00   1.00   12.00    --  -32.00 -72.00 108.00   60
  7  ω    -78.00 -18.00   1.00   12.00    --  -32.00 -72.00  36.00   60
  8  ω    -35.00  26.00   1.00   12.00    --  -32.00   0.00  36.00   61
  9  ω    -47.00  14.00   1.00   12.00    --  -32.00  72.00  36.00   61
 10  ω   -200.00 -47.00   1.00   50.00    -- -110.00   0.00-108.00  153
 11  ω   -125.00 -20.00   1.00   50.00    -- -110.00  72.00-108.00  105
 12  ω   -106.00 -46.00   1.00   50.00    -- -110.00  72.00  36.00   60
 13  ω   -113.00 -52.00   1.00   50.00    -- -110.00  72.00 -36.00   61
 14  ω    -80.00 -20.00   1.00   50.00    -- -110.00  72.00 108.00   60
 15  ω   -171.00-111.00   1.00   50.00    -- -110.00 -72.00-180.00   60
 16  ω   -200.00 -96.00   1.00   50.00    -- -110.00 -72.00-108.00  104
 17  ω   -173.00 -96.00   1.00   50.00    -- -110.00 -72.00 -36.00   77
 18  ω   -125.00 -61.00   1.00   50.00    -- -110.00  72.00-180.00   64
 19  ω   -200.00-139.00   1.00   50.00    -- -110.00 -72.00  36.00   61
 20  ω   -183.00-123.00   1.00   50.00    -- -110.00   0.00 -36.00   60
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0431366000
_diffrn_orient_matrix_UB_12      0.0432392000
_diffrn_orient_matrix_UB_13      0.0876200000
_diffrn_orient_matrix_UB_21      -0.0151799000
_diffrn_orient_matrix_UB_22      0.0712492000
_diffrn_orient_matrix_UB_23      -0.0543506000
_diffrn_orient_matrix_UB_31      -0.1487101000
_diffrn_orient_matrix_UB_32      0.0053935000
_diffrn_orient_matrix_UB_33      0.0150062000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4383
_reflns_number_total             5199
_reflns_odcompleteness_completeness 94.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         5199
_refine_ls_number_restraints     234
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.122
_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)+(0.1271P)²+0.4206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2038
_refine_ls_wR_factor_ref         0.2110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C11A \\sim C1 \\sim C12A \\sim C2 \\sim C1A \\sim C3 \\sim C2A \\sim C4 \\sim
C3A \\sim C4A \\sim C5 \\sim C6 \\sim C5A \\sim C6A \\sim C8 \\sim C7A \\sim C9
\\sim C8A \\sim C10 \\sim C9A \\sim C11 \\sim C10A \\sim C12: within 1.7A with
sigma of 0.03 and sigma for terminal atoms of 0.06
O10 \\sim O11A \\sim O12 \\sim O10A \\sim O12A \\sim O11: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
F2A \\sim F1 \\sim F3A \\sim F2 \\sim F1A \\sim F3: within 1.7A with sigma of
0.01 and sigma for terminal atoms of 0.02
C20A \\sim C20: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
3. Others
 Sof(F3A)=Sof(F1A)=Sof(F2A)=Sof(O11A)=Sof(O12A)=Sof(O10A)=Sof(S1A)=Sof(C20A)=1-
 FVAR(1)
 Sof(F3)=Sof(O11)=Sof(F1)=Sof(F2)=Sof(S1)=Sof(O12)=Sof(C20)=Sof(O10)=FVAR(1)
 Sof(C8A)=Sof(H8Aa)=Sof(H8Ab)=Sof(O1A)=Sof(C1A)=Sof(H1Aa)=Sof(H1Ab)=Sof(C12A)=
 Sof(H12c)=Sof(H12d)=Sof(C2A)=Sof(H2Aa)=Sof(H2Ab)=Sof(C11A)=Sof(H11c)=Sof(H11d)=
 Sof(O2A)=Sof(O6A)=Sof(C3A)=Sof(H3Aa)=Sof(H3Ab)=Sof(C10A)=Sof(H10c)=Sof(H10d)=
 Sof(C4A)=Sof(H4Aa)=Sof(H4Ab)=Sof(C9A)=Sof(H9Aa)=Sof(H9Ab)=Sof(O3A)=Sof(O5A)=
 Sof(C5A)=Sof(H5Aa)=Sof(H5Ab)=Sof(C6A)=Sof(H6Aa)=Sof(H6Ab)=Sof(C7A)=Sof(H7Aa)=
 Sof(H7Ab)=Sof(O4A)=1-FVAR(2)
 Sof(O1)=Sof(O5)=Sof(O2)=Sof(O4)=Sof(O6)=Sof(C9)=Sof(H9a)=Sof(H9b)=Sof(O3)=
 Sof(C7)=Sof(H7a)=Sof(H7b)=Sof(C1)=Sof(H1a)=Sof(H1b)=Sof(C12)=Sof(H12a)=
 Sof(H12b)=Sof(C2)=Sof(H2a)=Sof(H2b)=Sof(C8)=Sof(H8a)=Sof(H8b)=Sof(C5)=Sof(H5a)=
 Sof(H5b)=Sof(C3)=Sof(H3a)=Sof(H3b)=Sof(C11)=Sof(H11a)=Sof(H11b)=Sof(C6)=
 Sof(H6a)=Sof(H6b)=Sof(C4)=Sof(H4a)=Sof(H4b)=Sof(C10)=Sof(H10a)=Sof(H10b)=
 FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C7(H7a,H7b), C1(H1a,H1b), C12(H12a,H12b), C2(H2a,H2b), C8(H8a,
 H8b), C5(H5a,H5b), C3(H3a,H3b), C11(H11a,H11b), C6(H6a,H6b), C4(H4a,H4b),
 C10(H10a,H10b), C8A(H8Aa,H8Ab), C1A(H1Aa,H1Ab), C12A(H12c,H12d), C2A(H2Aa,
 H2Ab), C11A(H11c,H11d), C3A(H3Aa,H3Ab), C10A(H10c,H10d), C4A(H4Aa,H4Ab),
 C9A(H9Aa,H9Ab), C5A(H5Aa,H5Ab), C6A(H6Aa,H6Ab), C7A(H7Aa,H7Ab)
4.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C14(H14)
4.c Idealised Me refined as rotating group:
 N1(H1c,H1d,H1e), C19(H19a,H19b,H19c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O7 O 0.35581(14) 0.39170(8) 0.27732(9) 0.0727(4) Uani 1 1 d . . . . .
O9 O 0.8458(2) 0.50671(13) 0.54153(13) 0.1096(6) Uani 1 1 d . . . . .
N2 N 0.7606(2) 0.46556(14) 0.55845(12) 0.0860(6) Uani 1 1 d . . . . .
N1 N 0.55768(16) 0.47622(9) 0.24027(9) 0.0629(4) Uani 1 1 d . . . . .
H1C H 0.5216 0.4430 0.2008 0.076 Uiso 1 1 calc GR . . . .
H1D H 0.6424 0.4850 0.2318 0.076 Uiso 1 1 calc GR . . . .
H1E H 0.5098 0.5170 0.2322 0.076 Uiso 1 1 calc GR . . . .
C17 C 0.4470(2) 0.38105(11) 0.43763(13) 0.0694(5) Uani 1 1 d . . . . .
H17 H 0.3764 0.3519 0.4503 0.083 Uiso 1 1 calc R . . . .
C18 C 0.44953(17) 0.40602(10) 0.34969(11) 0.0584(4) Uani 1 1 d . . . . .
C13 C 0.55649(17) 0.44960(9) 0.33222(10) 0.0548(4) Uani 1 1 d . . . . .
C16 C 0.5497(2) 0.39985(12) 0.50556(13) 0.0723(5) Uani 1 1 d . . . . .
H16 H 0.5486 0.3835 0.5643 0.087 Uiso 1 1 calc R . . . .
O1 O 0.8038(6) 0.5691(4) 0.2640(4) 0.0927(15) Uani 0.605(5) 1 d . . P A 1
C14 C 0.65946(18) 0.46845(10) 0.39960(11) 0.0599(4) Uani 1 1 d . . . . .
H14 H 0.7308 0.4974 0.3876 0.072 Uiso 1 1 calc R . . . .
C15 C 0.65325(19) 0.44273(11) 0.48618(11) 0.0649(5) Uani 1 1 d . . . . .
C19 C 0.2378(2) 0.35224(14) 0.29081(18) 0.0843(6) Uani 1 1 d . . . . .
H19A H 0.1852 0.3417 0.2333 0.126 Uiso 1 1 calc GR . . . .
H19B H 0.1851 0.3807 0.3265 0.126 Uiso 1 1 calc GR . . . .
H19C H 0.2638 0.3077 0.3218 0.126 Uiso 1 1 calc GR . . . .
O8 O 0.7560(3) 0.44342(18) 0.63416(12) 0.1445(10) Uani 1 1 d . . . . .
F3 F 1.1794(11) 0.7737(9) 0.0418(10) 0.148(4) Uani 0.581(5) 1 d . U P B 1
O5 O 0.3672(4) 0.5869(3) 0.1412(3) 0.1032(12) Uani 0.605(5) 1 d . . P A 1
O11 O 0.8106(10) 0.7579(7) 0.0155(9) 0.144(4) Uani 0.581(5) 1 d . U P B 1
O2 O 0.8046(4) 0.4347(2) 0.1816(4) 0.1030(13) Uani 0.605(5) 1 d . . P A 1
O4 O 0.3648(5) 0.4422(3) 0.0813(2) 0.1050(14) Uani 0.605(5) 1 d . . P A 1
O6 O 0.5557(5) 0.6368(2) 0.2859(3) 0.0993(12) Uani 0.605(5) 1 d . . P A 1
C9 C 0.3393(18) 0.6441(9) 0.1911(11) 0.129(5) Uani 0.605(5) 1 d . U P A 1
H9A H 0.3021 0.6285 0.2444 0.155 Uiso 0.605(5) 1 calc R . P A 1
H9B H 0.2759 0.6766 0.1561 0.155 Uiso 0.605(5) 1 calc R . P A 1
F1 F 1.0381(6) 0.8579(3) 0.0592(6) 0.147(2) Uani 0.581(5) 1 d . U P B 1
O3 O 0.5694(7) 0.3465(3) 0.1361(4) 0.1341(17) Uani 0.605(5) 1 d . . P A 1
C7 C 0.2669(19) 0.4969(9) 0.0451(9) 0.117(4) Uani 0.605(5) 1 d . . P A 1
H7A H 0.1815 0.4732 0.0242 0.140 Uiso 0.605(5) 1 calc R . P A 1
H7B H 0.2975 0.5196 -0.0068 0.140 Uiso 0.605(5) 1 calc R . P A 1
C1 C 0.9139(6) 0.5468(6) 0.2199(6) 0.092(2) Uani 0.605(5) 1 d . U P A 1
H1A H 0.9968 0.5696 0.2483 0.110 Uiso 0.605(5) 1 calc R . P A 1
H1B H 0.8980 0.5611 0.1568 0.110 Uiso 0.605(5) 1 calc R . P A 1
C12 C 0.7923(10) 0.6454(5) 0.2637(5) 0.117(3) Uani 0.605(5) 1 d . U P A 1
H12A H 0.7685 0.6631 0.2023 0.141 Uiso 0.605(5) 1 calc R . P A 1
H12B H 0.8772 0.6673 0.2898 0.141 Uiso 0.605(5) 1 calc R . P A 1
C2 C 0.9262(9) 0.4670(6) 0.2272(6) 0.122(3) Uani 0.605(5) 1 d . U P A 1
H2A H 1.0030 0.4506 0.1998 0.146 Uiso 0.605(5) 1 calc R . P A 1
H2B H 0.9402 0.4526 0.2903 0.146 Uiso 0.605(5) 1 calc R . P A 1
F2 F 1.0522(6) 0.8085(4) -0.0736(4) 0.186(2) Uani 0.581(5) 1 d . U P B 1
C8 C 0.2453(6) 0.5529(6) 0.1103(7) 0.139(3) Uani 0.605(5) 1 d . U P A 1
H8A H 0.1808 0.5882 0.0820 0.167 Uiso 0.605(5) 1 calc R . P A 1
H8B H 0.2090 0.5313 0.1608 0.167 Uiso 0.605(5) 1 calc R . P A 1
C5 C 0.4497(13) 0.3329(7) 0.0745(6) 0.123(3) Uani 0.605(5) 1 d . U P A 1
H5A H 0.4680 0.2938 0.0346 0.148 Uiso 0.605(5) 1 calc R . P A 1
H5B H 0.3808 0.3159 0.1088 0.148 Uiso 0.605(5) 1 calc R . P A 1
C3 C 0.8114(13) 0.3592(7) 0.1758(10) 0.142(4) Uani 0.605(5) 1 d . U P A 1
H3A H 0.8104 0.3376 0.2349 0.170 Uiso 0.605(5) 1 calc R . P A 1
H3B H 0.8941 0.3448 0.1540 0.170 Uiso 0.605(5) 1 calc R . P A 1
C11 C 0.6833(8) 0.6636(4) 0.3192(4) 0.109(2) Uani 0.605(5) 1 d . U P A 1
H11A H 0.7096 0.6448 0.3799 0.130 Uiso 0.605(5) 1 calc R . P A 1
H11B H 0.6775 0.7159 0.3237 0.130 Uiso 0.605(5) 1 calc R . P A 1
S1 S 0.9457(3) 0.73113(14) 0.0409(3) 0.1071(9) Uani 0.581(5) 1 d . . P B 1
O12 O 0.9795(9) 0.6675(4) -0.0059(8) 0.189(4) Uani 0.581(5) 1 d . U P B 1
C20 C 1.0537(10) 0.7961(4) 0.0102(6) 0.091(2) Uani 0.581(5) 1 d . U P B 1
O10 O 0.9824(8) 0.7280(4) 0.1385(5) 0.188(3) Uani 0.581(5) 1 d . U P B 1
C6 C 0.3978(10) 0.3906(5) 0.0218(5) 0.128(3) Uani 0.605(5) 1 d . U P A 1
H6A H 0.4643 0.4093 -0.0132 0.154 Uiso 0.605(5) 1 calc R . P A 1
H6B H 0.3183 0.3759 -0.0194 0.154 Uiso 0.605(5) 1 calc R . P A 1
C4 C 0.6946(11) 0.3351(5) 0.1132(7) 0.145(3) Uani 0.605(5) 1 d . U P A 1
H4A H 0.6978 0.3588 0.0556 0.174 Uiso 0.605(5) 1 calc R . P A 1
H4B H 0.7044 0.2835 0.1037 0.174 Uiso 0.605(5) 1 calc R . P A 1
C10 C 0.4842(11) 0.6826(4) 0.2188(4) 0.123(2) Uani 0.605(5) 1 d . U P A 1
H10A H 0.5316 0.6865 0.1668 0.148 Uiso 0.605(5) 1 calc R . P A 1
H10B H 0.4735 0.7308 0.2428 0.148 Uiso 0.605(5) 1 calc R . P A 1
F3A F 0.9990(11) 0.8558(4) -0.0116(11) 0.191(4) Uani 0.419(5) 1 d . U P B 2
F1A F 1.167(2) 0.7861(12) 0.0143(14) 0.162(5) Uani 0.419(5) 1 d . U P B 2
F2A F 1.0597(10) 0.8051(9) 0.1219(9) 0.245(5) Uani 0.419(5) 1 d . U P B 2
O11A O 0.9796(11) 0.6618(6) 0.0508(8) 0.160(5) Uani 0.419(5) 1 d . U P B 2
O12A O 0.8099(17) 0.7528(11) 0.0367(12) 0.163(6) Uani 0.419(5) 1 d . U P B 2
O10A O 0.9176(6) 0.7171(4) -0.0855(3) 0.128(2) Uani 0.419(5) 1 d . U P B 2
S1A S 0.9215(3) 0.72226(19) 0.00639(16) 0.0759(7) Uani 0.419(5) 1 d . . P B 2
C20A C 1.0401(19) 0.7999(14) 0.0391(11) 0.151(7) Uani 0.419(5) 1 d . U P B 2
C8A C 0.366(3) 0.6538(12) 0.1882(13) 0.107(5) Uani 0.395(5) 1 d . U P A 2
H8AA H 0.3882 0.6774 0.1342 0.128 Uiso 0.395(5) 1 calc R . P A 2
H8AB H 0.3180 0.6872 0.2220 0.128 Uiso 0.395(5) 1 calc R . P A 2
O1A O 0.8398(7) 0.4459(4) 0.2301(4) 0.1004(19) Uani 0.395(5) 1 d . . P A 2
C1A C 0.8734(14) 0.3799(11) 0.1855(13) 0.129(5) Uani 0.395(5) 1 d . U P A 2
H1AA H 0.9637 0.3640 0.2098 0.154 Uiso 0.395(5) 1 calc R . P A 2
H1AB H 0.8695 0.3881 0.1210 0.154 Uiso 0.395(5) 1 calc R . P A 2
C12A C 0.9224(12) 0.5029(9) 0.2146(8) 0.096(3) Uani 0.395(5) 1 d . U P A 2
H12C H 0.9083 0.5146 0.1506 0.116 Uiso 0.395(5) 1 calc R . P A 2
H12D H 1.0160 0.4887 0.2313 0.116 Uiso 0.395(5) 1 calc R . P A 2
C2A C 0.7720(13) 0.3243(7) 0.2026(11) 0.134(4) Uani 0.395(5) 1 d . U P A 2
H2AA H 0.7974 0.2794 0.1758 0.161 Uiso 0.395(5) 1 calc R . P A 2
H2AB H 0.7834 0.3166 0.2675 0.161 Uiso 0.395(5) 1 calc R . P A 2
C11A C 0.8947(15) 0.5677(7) 0.2670(9) 0.111(3) Uani 0.395(5) 1 d . U P A 2
H11C H 0.9143 0.5577 0.3313 0.133 Uiso 0.395(5) 1 calc R . P A 2
H11D H 0.9504 0.6079 0.2530 0.133 Uiso 0.395(5) 1 calc R . P A 2
O2A O 0.6417(9) 0.3333(3) 0.1757(5) 0.108(2) Uani 0.395(5) 1 d . . P A 2
O6A O 0.7557(10) 0.5848(6) 0.2424(7) 0.100(3) Uani 0.395(5) 1 d . . P A 2
C3A C 0.6023(17) 0.3129(6) 0.0895(7) 0.126(3) Uani 0.395(5) 1 d . U P A 2
H3AA H 0.6709 0.3287 0.0543 0.151 Uiso 0.395(5) 1 calc R . P A 2
H3AB H 0.6013 0.2603 0.0880 0.151 Uiso 0.395(5) 1 calc R . P A 2
C10A C 0.7267(16) 0.6492(7) 0.2818(13) 0.124(4) Uani 0.395(5) 1 d . U P A 2
H10C H 0.7946 0.6851 0.2735 0.149 Uiso 0.395(5) 1 calc R . P A 2
H10D H 0.7274 0.6423 0.3462 0.149 Uiso 0.395(5) 1 calc R . P A 2
C4A C 0.485(2) 0.3358(11) 0.0482(11) 0.121(4) Uani 0.395(5) 1 d . U P A 2
H4AA H 0.4154 0.3045 0.0660 0.145 Uiso 0.395(5) 1 calc R . P A 2
H4AB H 0.4835 0.3294 -0.0163 0.145 Uiso 0.395(5) 1 calc R . P A 2
C9A C 0.5873(14) 0.6757(5) 0.2379(8) 0.121(3) Uani 0.395(5) 1 d . U P A 2
H9AA H 0.5654 0.7199 0.2677 0.145 Uiso 0.395(5) 1 calc R . P A 2
H9AB H 0.5909 0.6872 0.1750 0.145 Uiso 0.395(5) 1 calc R . P A 2
O3A O 0.4489(10) 0.4068(4) 0.0630(5) 0.130(3) Uani 0.395(5) 1 d . . P A 2
O5A O 0.4830(8) 0.6241(3) 0.2424(5) 0.1051(18) Uani 0.395(5) 1 d . . P A 2
C5A C 0.3406(12) 0.4435(9) 0.0086(6) 0.124(4) Uani 0.395(5) 1 d . U P A 2
H5AA H 0.3761 0.4798 -0.0285 0.149 Uiso 0.395(5) 1 calc R . P A 2
H5AB H 0.2876 0.4092 -0.0311 0.149 Uiso 0.395(5) 1 calc R . P A 2
C6A C 0.260(3) 0.4763(16) 0.0652(15) 0.135(6) Uani 0.395(5) 1 d . U P A 2
H6AA H 0.2381 0.4421 0.1102 0.163 Uiso 0.395(5) 1 calc R . P A 2
H6AB H 0.1767 0.4937 0.0306 0.163 Uiso 0.395(5) 1 calc R . P A 2
C7A C 0.2763(14) 0.5708(11) 0.1631(8) 0.154(5) Uani 0.395(5) 1 d . U P A 2
H7AA H 0.2747 0.5429 0.2180 0.185 Uiso 0.395(5) 1 calc R . P A 2
H7AB H 0.1840 0.5807 0.1361 0.185 Uiso 0.395(5) 1 calc R . P A 2
O4A O 0.3378(7) 0.5360(4) 0.1081(4) 0.1109(19) Uani 0.395(5) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O7 C18 1.350(2) . ?
O7 C19 1.427(3) . ?
O9 N2 1.197(3) . ?
N2 C15 1.469(3) . ?
N2 O8 1.210(3) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
N1 C13 1.461(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.396(3) . ?
C17 C16 1.379(3) . ?
C18 C13 1.394(3) . ?
C13 C14 1.376(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.368(3) . ?
O1 C1 1.426(10) . ?
O1 C12 1.412(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
F3 C20 1.343(14) . ?
O5 C9 1.344(16) . ?
O5 C8 1.389(10) . ?
O11 S1 1.438(9) . ?
O2 C2 1.434(11) . ?
O2 C3 1.398(13) . ?
O4 C7 1.454(16) . ?
O4 C6 1.376(10) . ?
O6 C11 1.391(10) . ?
O6 C10 1.422(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.61(2) . ?
F1 C20 1.375(9) . ?
O3 C5 1.422(14) . ?
O3 C4 1.363(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.46(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.480(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.502(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
F2 C20 1.270(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.380(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.456(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
S1 O12 1.433(7) . ?
S1 C20 1.722(9) . ?
S1 O10 1.452(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
F3A C20A 1.31(2) . ?
F1A C20A 1.40(2) . ?
F2A C20A 1.227(19) . ?
O11A S1A 1.381(8) . ?
O12A S1A 1.386(14) . ?
O10A S1A 1.372(6) . ?
S1A C20A 1.88(2) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A O5A 1.43(2) . ?
C8A C7A 1.79(3) . ?
O1A C1A 1.45(2) . ?
O1A C12A 1.379(15) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1A C2A 1.49(2) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A C11A 1.476(19) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A O2A 1.318(16) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A O6A 1.422(15) . ?
O2A C3A 1.345(13) . ?
O6A C10A 1.377(19) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A C4A 1.32(3) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C9A 1.53(2) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A O3A 1.38(2) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A O5A 1.422(15) . ?
O3A C5A 1.427(15) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.39(3) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6A O4A 1.44(3) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A O4A 1.272(16) . ?

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
C18 O7 C19 118.64(16) . . ?
O9 N2 C15 119.60(19) . . ?
O9 N2 O8 122.5(2) . . ?
O8 N2 C15 117.8(2) . . ?
H1C N1 H1D 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C13 N1 H1C 109.5 . . ?
C13 N1 H1D 109.5 . . ?
C13 N1 H1E 109.5 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.71(19) . . ?
O7 C18 C17 125.68(17) . . ?
O7 C18 C13 115.18(15) . . ?
C13 C18 C17 119.13(17) . . ?
C18 C13 N1 118.86(15) . . ?
C14 C13 N1 119.65(15) . . ?
C14 C13 C18 121.49(15) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.71(17) . . ?
C15 C16 H16 120.1 . . ?
C12 O1 C1 110.7(6) . . ?
C13 C14 H14 121.2 . . ?
C13 C14 C15 117.69(17) . . ?
C15 C14 H14 121.2 . . ?
C16 C15 N2 120.34(17) . . ?
C16 C15 C14 122.27(17) . . ?
C14 C15 N2 117.35(19) . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 O5 C8 107.2(10) . . ?
C3 O2 C2 113.4(7) . . ?
C6 O4 C7 116.8(8) . . ?
C11 O6 C10 112.5(7) . . ?
O5 C9 H9A 111.0 . . ?
O5 C9 H9B 111.0 . . ?
O5 C9 C10 103.7(11) . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C4 O3 C5 121.9(8) . . ?
O4 C7 H7A 108.9 . . ?
O4 C7 H7B 108.9 . . ?
O4 C7 C8 113.6(10) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
O1 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
O1 C1 C2 108.3(7) . . ?
H1A C1 H1B 108.4 . . ?
C2 C1 H1A 110.0 . . ?
C2 C1 H1B 110.0 . . ?
O1 C12 H12A 110.4 . . ?
O1 C12 H12B 110.4 . . ?
O1 C12 C11 106.6(6) . . ?
H12A C12 H12B 108.6 . . ?
C11 C12 H12A 110.4 . . ?
C11 C12 H12B 110.4 . . ?
O2 C2 C1 108.8(6) . . ?
O2 C2 H2A 109.9 . . ?
O2 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O5 C8 C7 109.5(10) . . ?
O5 C8 H8A 109.8 . . ?
O5 C8 H8B 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O3 C5 H5A 108.2 . . ?
O3 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C6 C5 O3 116.3(9) . . ?
C6 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
O2 C3 H3A 110.2 . . ?
O2 C3 H3B 110.2 . . ?
O2 C3 C4 107.6(9) . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
O6 C11 C12 115.3(5) . . ?
O6 C11 H11A 108.5 . . ?
O6 C11 H11B 108.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
O11 S1 C20 107.1(7) . . ?
O11 S1 O10 111.6(6) . . ?
O12 S1 O11 115.7(7) . . ?
O12 S1 C20 103.7(5) . . ?
O12 S1 O10 114.5(6) . . ?
O10 S1 C20 102.7(5) . . ?
F3 C20 F1 104.0(11) . . ?
F3 C20 S1 106.5(8) . . ?
F1 C20 S1 108.0(6) . . ?
F2 C20 F3 106.1(10) . . ?
F2 C20 F1 113.0(7) . . ?
F2 C20 S1 118.1(8) . . ?
O4 C6 C5 105.7(6) . . ?
O4 C6 H6A 110.6 . . ?
O4 C6 H6B 110.6 . . ?
C5 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
O3 C4 C3 118.2(9) . . ?
O3 C4 H4A 107.7 . . ?
O3 C4 H4B 107.7 . . ?
C3 C4 H4A 107.7 . . ?
C3 C4 H4B 107.8 . . ?
H4A C4 H4B 107.1 . . ?
O6 C10 C9 105.1(8) . . ?
O6 C10 H10A 110.7 . . ?
O6 C10 H10B 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
O11A S1A O12A 118.3(11) . . ?
O11A S1A C20A 106.6(9) . . ?
O12A S1A C20A 96.6(10) . . ?
O10A S1A O11A 111.9(7) . . ?
O10A S1A O12A 116.7(8) . . ?
O10A S1A C20A 103.8(6) . . ?
F3A C20A F1A 102.2(18) . . ?
F3A C20A S1A 108.5(13) . . ?
F1A C20A S1A 110.9(15) . . ?
F2A C20A F3A 120.8(19) . . ?
F2A C20A F1A 105.4(16) . . ?
F2A C20A S1A 108.9(17) . . ?
H8AA C8A H8AB 109.8 . . ?
O5A C8A H8AA 112.2 . . ?
O5A C8A H8AB 112.2 . . ?
O5A C8A C7A 97.8(14) . . ?
C7A C8A H8AA 112.2 . . ?
C7A C8A H8AB 112.2 . . ?
C12A O1A C1A 112.2(10) . . ?
O1A C1A H1AA 110.4 . . ?
O1A C1A H1AB 110.4 . . ?
O1A C1A C2A 106.8(13) . . ?
H1AA C1A H1AB 108.6 . . ?
C2A C1A H1AA 110.4 . . ?
C2A C1A H1AB 110.4 . . ?
O1A C12A H12C 109.4 . . ?
O1A C12A H12D 109.4 . . ?
O1A C12A C11A 111.3(10) . . ?
H12C C12A H12D 108.0 . . ?
C11A C12A H12C 109.4 . . ?
C11A C12A H12D 109.4 . . ?
C1A C2A H2AA 106.8 . . ?
C1A C2A H2AB 106.8 . . ?
H2AA C2A H2AB 106.7 . . ?
O2A C2A C1A 122.0(12) . . ?
O2A C2A H2AA 106.8 . . ?
O2A C2A H2AB 106.8 . . ?
C12A C11A H11C 110.3 . . ?
C12A C11A H11D 110.3 . . ?
H11C C11A H11D 108.5 . . ?
O6A C11A C12A 107.2(10) . . ?
O6A C11A H11C 110.3 . . ?
O6A C11A H11D 110.3 . . ?
C2A O2A C3A 113.2(11) . . ?
C10A O6A C11A 109.9(11) . . ?
O2A C3A H3AA 107.7 . . ?
O2A C3A H3AB 107.7 . . ?
H3AA C3A H3AB 107.1 . . ?
C4A C3A O2A 118.4(12) . . ?
C4A C3A H3AA 107.7 . . ?
C4A C3A H3AB 107.7 . . ?
O6A C10A H10C 109.9 . . ?
O6A C10A H10D 109.9 . . ?
O6A C10A C9A 109.1(11) . . ?
H10C C10A H10D 108.3 . . ?
C9A C10A H10C 109.9 . . ?
C9A C10A H10D 109.9 . . ?
C3A C4A H4AA 107.9 . . ?
C3A C4A H4AB 107.9 . . ?
C3A C4A O3A 117.7(15) . . ?
H4AA C4A H4AB 107.2 . . ?
O3A C4A H4AA 107.9 . . ?
O3A C4A H4AB 107.9 . . ?
C10A C9A H9AA 108.9 . . ?
C10A C9A H9AB 108.9 . . ?
H9AA C9A H9AB 107.7 . . ?
O5A C9A C10A 113.3(10) . . ?
O5A C9A H9AA 108.9 . . ?
O5A C9A H9AB 108.9 . . ?
C4A O3A C5A 123.4(13) . . ?
C9A O5A C8A 105.2(13) . . ?
O3A C5A H5AA 110.0 . . ?
O3A C5A H5AB 110.0 . . ?
H5AA C5A H5AB 108.4 . . ?
C6A C5A O3A 108.6(12) . . ?
C6A C5A H5AA 110.0 . . ?
C6A C5A H5AB 110.0 . . ?
C5A C6A H6AA 110.5 . . ?
C5A C6A H6AB 110.5 . . ?
C5A C6A O4A 106.2(18) . . ?
H6AA C6A H6AB 108.7 . . ?
O4A C6A H6AA 110.5 . . ?
O4A C6A H6AB 110.5 . . ?
C8A C7A H7AA 110.3 . . ?
C8A C7A H7AB 110.3 . . ?
H7AA C7A H7AB 108.6 . . ?
O4A C7A C8A 106.9(12) . . ?
O4A C7A H7AA 110.3 . . ?
O4A C7A H7AB 110.3 . . ?
C7A O4A C6A 113.1(16) . . ?

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
O7 C18 C13 N1 0.8(2) . . . . ?
O7 C18 C13 C14 -179.86(16) . . . . ?
O9 N2 C15 C16 -175.3(2) . . . . ?
O9 N2 C15 C14 2.5(3) . . . . ?
N1 C13 C14 C15 179.14(16) . . . . ?
C17 C18 C13 N1 -179.30(16) . . . . ?
C17 C18 C13 C14 0.0(3) . . . . ?
C17 C16 C15 N2 177.61(19) . . . . ?
C17 C16 C15 C14 -0.1(3) . . . . ?
C18 C17 C16 C15 -0.1(3) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 N2 -177.53(17) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C16 C17 C18 O7 180.00(18) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
O1 C1 C2 O2 62.0(10) . . . . ?
O1 C12 C11 O6 -62.2(10) . . . . ?
C19 O7 C18 C17 4.9(3) . . . . ?
C19 O7 C18 C13 -175.15(18) . . . . ?
O8 N2 C15 C16 2.2(3) . . . . ?
O8 N2 C15 C14 -180.0(2) . . . . ?
O5 C9 C10 O6 -73.9(10) . . . . ?
O11 S1 C20 F3 174.3(10) . . . . ?
O11 S1 C20 F1 63.2(9) . . . . ?
O11 S1 C20 F2 -66.6(9) . . . . ?
O2 C3 C4 O3 -64.1(12) . . . . ?
O4 C7 C8 O5 58.2(12) . . . . ?
C9 O5 C8 C7 171.7(9) . . . . ?
O3 C5 C6 O4 -62.2(10) . . . . ?
C7 O4 C6 C5 -159.0(9) . . . . ?
C1 O1 C12 C11 -174.5(7) . . . . ?
C12 O1 C1 C2 176.6(7) . . . . ?
C2 O2 C3 C4 -168.7(7) . . . . ?
C8 O5 C9 C10 -176.7(7) . . . . ?
C5 O3 C4 C3 172.2(10) . . . . ?
C3 O2 C2 C1 173.4(8) . . . . ?
C11 O6 C10 C9 -178.5(7) . . . . ?
O12 S1 C20 F3 -62.9(11) . . . . ?
O12 S1 C20 F1 -174.1(8) . . . . ?
O12 S1 C20 F2 56.2(9) . . . . ?
O10 S1 C20 F3 56.6(10) . . . . ?
O10 S1 C20 F1 -54.5(7) . . . . ?
O10 S1 C20 F2 175.8(7) . . . . ?
C6 O4 C7 C8 -175.4(8) . . . . ?
C4 O3 C5 C6 -91.9(11) . . . . ?
C10 O6 C11 C12 -83.9(9) . . . . ?
O11A S1A C20A F3A 170.8(12) . . . . ?
O11A S1A C20A F1A 59.4(16) . . . . ?
O11A S1A C20A F2A -56.0(16) . . . . ?
O12A S1A C20A F3A -67.0(15) . . . . ?
O12A S1A C20A F1A -178.4(16) . . . . ?
O12A S1A C20A F2A 66.1(17) . . . . ?
O10A S1A C20A F3A 52.5(12) . . . . ?
O10A S1A C20A F1A -58.8(16) . . . . ?
O10A S1A C20A F2A -174.3(13) . . . . ?
C8A C7A O4A C6A -166.2(13) . . . . ?
O1A C1A C2A O2A 60.2(18) . . . . ?
O1A C12A C11A O6A -57.1(14) . . . . ?
C1A O1A C12A C11A -174.9(11) . . . . ?
C1A C2A O2A C3A 84.9(16) . . . . ?
C12A O1A C1A C2A -176.5(11) . . . . ?
C12A C11A O6A C10A -173.6(12) . . . . ?
C2A O2A C3A C4A -163.0(15) . . . . ?
C11A O6A C10A C9A 167.0(11) . . . . ?
O2A C3A C4A O3A 40.5(19) . . . . ?
O6A C10A C9A O5A 56.0(16) . . . . ?
C3A C4A O3A C5A 165.7(13) . . . . ?
C10A C9A O5A C8A -172.4(12) . . . . ?
C4A O3A C5A C6A 131.1(18) . . . . ?
O3A C5A C6A O4A 71.0(17) . . . . ?
O5A C8A C7A O4A -71.5(14) . . . . ?
C5A C6A O4A C7A -179.3(13) . . . . ?
C7A C8A O5A C9A 156.8(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.961
_oxdiff_exptl_absorpt_empirical_full_min 0.485
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_25mna18c6so3cf3_lt
_database_code_depnum_ccdc_archive 'CCDC 1982639'
loop_
_audit_author_name
_audit_author_address
'Huang Rui-Kang'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-03-05 downloaded from the CCDC.
;
_audit_creation_date             2019-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C F3 O3 S, C7 H9 N2 O3, C12 H24 O6'
_chemical_formula_sum            'C20 H33 F3 N2 O12 S'
_chemical_formula_weight         582.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNFO
_chemical_oxdiff_usercomment     HRK-213K
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'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   20.31807(19)
_cell_length_b                   17.85897(16)
_cell_length_c                   14.64020(12)
_cell_angle_alpha                90.0
_cell_angle_beta                 96.2561(8)
_cell_angle_gamma                90.0
_cell_volume                     5280.70(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12230
_cell_measurement_temperature    212.99(10)
_cell_measurement_theta_max      73.9240
_cell_measurement_theta_min      4.2870
_cell_oxdiff_angle_alpha         89.9623(14)
_cell_oxdiff_angle_beta          96.2355(13)
_cell_oxdiff_angle_gamma         89.9898(14)
_cell_oxdiff_length_a            20.3249(3)
_cell_oxdiff_length_b            17.8530(3)
_cell_oxdiff_length_c            14.6396(2)
_cell_oxdiff_measurement_reflns_used 12230
_cell_oxdiff_volume              5280.70(16)
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.653
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20583
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.127
_diffrn_reflns_theta_min         3.918
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      212.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -20.00   1.00    3.00    --  -41.24 -38.00 -90.00   89
  2  ω    -92.00  -2.00   1.00    3.00    --  -41.24 125.00  60.00   90
  3  ω      5.00  34.00   1.00    3.00    --   41.24 -99.00-180.00   29
  4  ω     37.00 137.00   1.00   12.00    --  107.79 -77.00  60.00  100
  5  ω     82.00 174.00   1.00   12.00    --  107.79  45.00-150.00   92
  6  ω     55.00  96.00   1.00   12.00    --  107.79 -94.00   0.00   41
  7  ω     38.00 106.00   1.00   12.00    --  107.79-125.00 -30.00   68
  8  ω    109.00 137.00   1.00   12.00    --  107.79  94.00  45.00   28
  9  ω     44.00 114.00   1.00   12.00    --  107.79-125.00-120.00   70
 10  ω    110.00 166.00   1.00   12.00    --  107.79 125.00   0.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0309402000
_diffrn_orient_matrix_UB_12      -0.0788333000
_diffrn_orient_matrix_UB_13      0.0079107000
_diffrn_orient_matrix_UB_21      0.0325185000
_diffrn_orient_matrix_UB_22      0.0137960000
_diffrn_orient_matrix_UB_23      -0.0887891000
_diffrn_orient_matrix_UB_31      0.0616361000
_diffrn_orient_matrix_UB_32      0.0322673000
_diffrn_orient_matrix_UB_33      0.0570967000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9222
_reflns_number_total             10415
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         10415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0722P)²+1.8016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1294
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C1A(H1AA,H1AB), C12A(H12A,H12B), C11A(H11A,H11B), C7A(H7AA,
 H7AB), C3A(H3AA,H3AB), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10A,H10B),
 C5A(H5AA,H5AB), C6A(H6AA,H6AB), C4A(H4AA,H4AB), C8B(H8BA,H8BB), C12B(H12C,
 H12D), C11B(H11C,H11D), C9B(H9BA,H9BB), C1B(H1BA,H1BB), C5B(H5BA,H5BB),
 C6B(H6BA,H6BB), C10B(H10C,H10D), C2B(H2BA,H2BB), C4B(H4BA,H4BB), C7B(H7BA,
 H7BB), C3B(H3BA,H3BB)
2.b Aromatic/amide H refined with riding coordinates:
 C18B(H18B), C16A(H16A), C18A(H18A), C15B(H15B), C15A(H15A), C16B(H16B)
2.c Idealised Me refined as rotating group:
 N1B(H1BC,H1BD,H1BE), N1A(H1AC,H1AD,H1AE), C19A(H19A,H19B,H19C), C19B(H19D,
 H19E,H19F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S1A S 0.96499(2) 0.79093(3) 1.51025(3) 0.03735(11) Uani 1 1 d . . . . .
O7A O 0.82433(6) 0.89639(7) 1.23017(8) 0.0358(3) Uani 1 1 d . . . . .
O6A O 0.67767(6) 0.82955(7) 1.32042(8) 0.0374(3) Uani 1 1 d . . . . .
O2A O 0.82136(6) 1.04285(8) 1.39266(9) 0.0418(3) Uani 1 1 d . . . . .
O3A O 0.75114(7) 1.12926(8) 1.25729(9) 0.0425(3) Uani 1 1 d . . . . .
O5A O 0.57807(6) 0.94329(7) 1.27260(9) 0.0413(3) Uani 1 1 d . . . . .
O1A O 0.76416(7) 0.90978(8) 1.44407(9) 0.0464(3) Uani 1 1 d . . . . .
O4A O 0.61744(6) 1.09011(7) 1.26086(9) 0.0426(3) Uani 1 1 d . . . . .
O7B O 0.67565(6) 1.09615(8) 0.78358(9) 0.0436(3) Uani 1 1 d . . . . .
N1B N 0.78044(6) 1.02047(8) 0.74357(9) 0.0291(3) Uani 1 1 d . . . . .
H1BC H 0.7455 1.0379 0.7066 0.035 Uiso 1 1 calc GR . . . .
H1BD H 0.7781 0.9702 0.7467 0.035 Uiso 1 1 calc GR . . . .
H1BE H 0.8182 1.0337 0.7208 0.035 Uiso 1 1 calc GR . . . .
N1A N 0.71578(6) 0.97289(8) 1.26667(8) 0.0296(3) Uani 1 1 d . . . . .
H1AC H 0.6729 0.9827 1.2716 0.035 Uiso 1 1 calc GR . . . .
H1AD H 0.7400 1.0146 1.2794 0.035 Uiso 1 1 calc GR . . . .
H1AE H 0.7300 0.9365 1.3065 0.035 Uiso 1 1 calc GR . . . .
O8A O 0.58469(8) 0.99684(10) 0.95833(10) 0.0575(4) Uani 1 1 d . . . . .
O11A O 0.90458(7) 0.77074(12) 1.54614(12) 0.0650(5) Uani 1 1 d . . . . .
F3A F 1.08396(8) 0.73359(11) 1.54203(15) 0.0935(6) Uani 1 1 d . . . . .
N2A N 0.62991(8) 0.95595(10) 0.94195(10) 0.0439(4) Uani 1 1 d . . . . .
O10A O 0.96575(9) 0.77750(11) 1.41422(10) 0.0664(5) Uani 1 1 d . . . . .
O12A O 0.99364(10) 0.86084(10) 1.53970(14) 0.0691(5) Uani 1 1 d . . . . .
C13B C 0.77967(8) 1.05216(9) 0.83532(10) 0.0283(3) Uani 1 1 d . . . . .
O9A O 0.63464(10) 0.92893(13) 0.86643(10) 0.0745(5) Uani 1 1 d . . . . .
N2B N 0.88404(9) 1.06256(12) 1.05767(11) 0.0507(4) Uani 1 1 d . . . . .
O8B O 0.92385(9) 1.01318(12) 1.04654(12) 0.0711(5) Uani 1 1 d . . . . .
C13A C 0.72310(8) 0.94845(9) 1.17345(10) 0.0280(3) Uani 1 1 d . . . . .
C18B C 0.83265(8) 1.04279(9) 0.90068(11) 0.0318(3) Uani 1 1 d . . . . .
H18B H 0.8705 1.0163 0.8876 0.038 Uiso 1 1 calc R . . . .
F1A F 1.00487(11) 0.65439(10) 1.54544(19) 0.1111(8) Uani 1 1 d . . . . .
O9B O 0.88813(9) 1.10394(14) 1.12504(10) 0.0801(6) Uani 1 1 d . . . . .
C14A C 0.77991(8) 0.90869(9) 1.15637(11) 0.0294(3) Uani 1 1 d . . . . .
F2A F 1.02660(10) 0.73005(15) 1.65558(12) 0.1089(8) Uani 1 1 d . . . . .
C14B C 0.72316(8) 1.09160(9) 0.85433(11) 0.0314(3) Uani 1 1 d . . . . .
C17A C 0.68206(9) 0.93888(10) 1.01614(11) 0.0337(3) Uani 1 1 d . . . . .
C16A C 0.73730(9) 0.90009(10) 0.99668(11) 0.0361(4) Uani 1 1 d . . . . .
H16A H 0.7416 0.8843 0.9364 0.043 Uiso 1 1 calc R . . . .
C18A C 0.67375(8) 0.96366(9) 1.10419(11) 0.0314(3) Uani 1 1 d . . . . .
H18A H 0.6355 0.9900 1.1159 0.038 Uiso 1 1 calc R . . . .
C15B C 0.72033(9) 1.12197(10) 0.94163(12) 0.0384(4) Uani 1 1 d . . . . .
H15B H 0.6826 1.1484 0.9553 0.046 Uiso 1 1 calc R . . . .
C15A C 0.78665(8) 0.88456(10) 1.06724(11) 0.0349(3) Uani 1 1 d . . . . .
H15A H 0.8246 0.8578 1.0550 0.042 Uiso 1 1 calc R . . . .
C17B C 0.82863(9) 1.07380(11) 0.98685(11) 0.0362(4) Uani 1 1 d . . . . .
C16B C 0.77366(9) 1.11279(11) 1.00790(12) 0.0392(4) Uani 1 1 d . . . . .
H16B H 0.7724 1.1330 1.0670 0.047 Uiso 1 1 calc R . . . .
C2A C 0.86135(9) 0.98586(11) 1.43881(12) 0.0403(4) Uani 1 1 d . . . . .
H2AA H 0.8990 1.0083 1.4766 0.048 Uiso 1 1 calc R . . . .
H2AB H 0.8784 0.9522 1.3940 0.048 Uiso 1 1 calc R . . . .
C19A C 0.88551(8) 0.86019(11) 1.21517(13) 0.0408(4) Uani 1 1 d . . . . .
H19A H 0.9105 0.8923 1.1780 0.061 Uiso 1 1 calc GR . . . .
H19B H 0.8761 0.8130 1.1836 0.061 Uiso 1 1 calc GR . . . .
H19C H 0.9113 0.8509 1.2738 0.061 Uiso 1 1 calc GR . . . .
C1A C 0.81904(9) 0.94352(11) 1.49787(12) 0.0413(4) Uani 1 1 d . . . . .
H1AA H 0.8456 0.9046 1.5316 0.050 Uiso 1 1 calc R . . . .
H1AB H 0.8028 0.9776 1.5428 0.050 Uiso 1 1 calc R . . . .
C12A C 0.76347(10) 0.83076(11) 1.44439(13) 0.0419(4) Uani 1 1 d . . . . .
H12A H 0.7768 0.8120 1.5066 0.050 Uiso 1 1 calc R . . . .
H12B H 0.7947 0.8115 1.4036 0.050 Uiso 1 1 calc R . . . .
C11A C 0.69501(10) 0.80509(11) 1.41217(13) 0.0425(4) Uani 1 1 d . . . . .
H11A H 0.6928 0.7503 1.4150 0.051 Uiso 1 1 calc R . . . .
H11B H 0.6638 0.8256 1.4521 0.051 Uiso 1 1 calc R . . . .
C7A C 0.54997(9) 1.06936(11) 1.23559(14) 0.0445(4) Uani 1 1 d . . . . .
H7AA H 0.5430 1.0568 1.1701 0.053 Uiso 1 1 calc R . . . .
H7AB H 0.5206 1.1110 1.2471 0.053 Uiso 1 1 calc R . . . .
C3A C 0.85526(9) 1.08652(12) 1.33156(13) 0.0448(4) Uani 1 1 d . . . . .
H3AA H 0.8627 1.0571 1.2771 0.054 Uiso 1 1 calc R . . . .
H3AB H 0.8983 1.1026 1.3619 0.054 Uiso 1 1 calc R . . . .
C8A C 0.53534(9) 1.00299(11) 1.29208(14) 0.0436(4) Uani 1 1 d . . . . .
H8AA H 0.5424 1.0157 1.3575 0.052 Uiso 1 1 calc R . . . .
H8AB H 0.4890 0.9879 1.2773 0.052 Uiso 1 1 calc R . . . .
C19B C 0.61529(9) 1.13457(12) 0.79537(16) 0.0480(5) Uani 1 1 d . . . . .
H19D H 0.5889 1.1394 0.7364 0.072 Uiso 1 1 calc GR . . . .
H19E H 0.6254 1.1840 0.8207 0.072 Uiso 1 1 calc GR . . . .
H19F H 0.5907 1.1064 0.8370 0.072 Uiso 1 1 calc GR . . . .
C9A C 0.56340(9) 0.87466(12) 1.31563(16) 0.0469(4) Uani 1 1 d . . . . .
H9AA H 0.5175 0.8600 1.2967 0.056 Uiso 1 1 calc R . . . .
H9AB H 0.5690 0.8805 1.3826 0.056 Uiso 1 1 calc R . . . .
C10A C 0.60998(9) 0.81557(11) 1.28718(15) 0.0458(4) Uani 1 1 d . . . . .
H10A H 0.5969 0.7669 1.3102 0.055 Uiso 1 1 calc R . . . .
H10B H 0.6058 0.8129 1.2199 0.055 Uiso 1 1 calc R . . . .
C5A C 0.70020(11) 1.18343(11) 1.26268(15) 0.0473(4) Uani 1 1 d . . . . .
H5AA H 0.7125 1.2304 1.2344 0.057 Uiso 1 1 calc R . . . .
H5AB H 0.6947 1.1934 1.3272 0.057 Uiso 1 1 calc R . . . .
C6A C 0.63639(11) 1.15496(12) 1.21393(15) 0.0491(5) Uani 1 1 d . . . . .
H6AA H 0.6020 1.1935 1.2137 0.059 Uiso 1 1 calc R . . . .
H6AB H 0.6422 1.1425 1.1501 0.059 Uiso 1 1 calc R . . . .
C4A C 0.81291(10) 1.15331(12) 1.30436(14) 0.0469(4) Uani 1 1 d . . . . .
H4AA H 0.8050 1.1819 1.3592 0.056 Uiso 1 1 calc R . . . .
H4AB H 0.8357 1.1860 1.2642 0.056 Uiso 1 1 calc R . . . .
C20A C 1.02288(11) 0.72353(14) 1.56481(19) 0.0597(6) Uani 1 1 d . . . . .
O5B O 0.79759(6) 0.86262(7) 0.79519(8) 0.0394(3) Uani 1 1 d . . . . .
O4B O 0.91174(6) 0.94732(7) 0.76420(9) 0.0396(3) Uani 1 1 d . . . . .
O1B O 0.67439(7) 1.04385(7) 0.59060(9) 0.0426(3) Uani 1 1 d . . . . .
O3B O 0.89139(6) 1.07834(7) 0.66324(9) 0.0386(3) Uani 1 1 d . . . . .
O6B O 0.70031(6) 0.89726(8) 0.64829(9) 0.0425(3) Uani 1 1 d . . . . .
O2B O 0.76783(7) 1.15817(8) 0.63358(9) 0.0443(3) Uani 1 1 d . . . . .
C8B C 0.86325(10) 0.84573(12) 0.83568(14) 0.0464(4) Uani 1 1 d . . . . .
H8BA H 0.8666 0.7918 0.8474 0.056 Uiso 1 1 calc R . . . .
H8BB H 0.8712 0.8715 0.8950 0.056 Uiso 1 1 calc R . . . .
C12B C 0.63566(9) 0.98313(11) 0.55376(13) 0.0418(4) Uani 1 1 d . . . . .
H12C H 0.6544 0.9631 0.4999 0.050 Uiso 1 1 calc R . . . .
H12D H 0.5904 1.0001 0.5343 0.050 Uiso 1 1 calc R . . . .
C11B C 0.63454(9) 0.92354(12) 0.62489(14) 0.0448(4) Uani 1 1 d . . . . .
H11C H 0.6169 0.9438 0.6795 0.054 Uiso 1 1 calc R . . . .
H11D H 0.6060 0.8822 0.6010 0.054 Uiso 1 1 calc R . . . .
C9B C 0.77294(11) 0.80953(11) 0.72707(13) 0.0437(4) Uani 1 1 d . . . . .
H9BA H 0.7761 0.7588 0.7528 0.052 Uiso 1 1 calc R . . . .
H9BB H 0.7992 0.8115 0.6748 0.052 Uiso 1 1 calc R . . . .
C1B C 0.68408(11) 1.09988(11) 0.52381(13) 0.0455(4) Uani 1 1 d . . . . .
H1BA H 0.6425 1.1097 0.4851 0.055 Uiso 1 1 calc R . . . .
H1BB H 0.7173 1.0833 0.4844 0.055 Uiso 1 1 calc R . . . .
C5B C 0.95530(9) 1.05807(12) 0.70565(14) 0.0446(4) Uani 1 1 d . . . . .
H5BA H 0.9622 1.0792 0.7677 0.054 Uiso 1 1 calc R . . . .
H5BB H 0.9894 1.0783 0.6700 0.054 Uiso 1 1 calc R . . . .
C6B C 0.96086(8) 0.97474(12) 0.71044(13) 0.0422(4) Uani 1 1 d . . . . .
H6BA H 0.9541 0.9534 0.6485 0.051 Uiso 1 1 calc R . . . .
H6BB H 1.0050 0.9603 0.7386 0.051 Uiso 1 1 calc R . . . .
C10B C 0.70222(10) 0.82808(11) 0.69608(14) 0.0445(4) Uani 1 1 d . . . . .
H10C H 0.6824 0.7885 0.6556 0.053 Uiso 1 1 calc R . . . .
H10D H 0.6770 0.8320 0.7493 0.053 Uiso 1 1 calc R . . . .
C2B C 0.70733(11) 1.16955(11) 0.57567(15) 0.0483(5) Uani 1 1 d . . . . .
H2BA H 0.7137 1.2095 0.5316 0.058 Uiso 1 1 calc R . . . .
H2BB H 0.6730 1.1859 0.6134 0.058 Uiso 1 1 calc R . . . .
C4B C 0.88512(10) 1.15760(11) 0.65266(16) 0.0494(5) Uani 1 1 d . . . . .
H4BA H 0.9243 1.1778 0.6278 0.059 Uiso 1 1 calc R . . . .
H4BB H 0.8817 1.1810 0.7125 0.059 Uiso 1 1 calc R . . . .
C7B C 0.91601(10) 0.86828(12) 0.77690(15) 0.0466(4) Uani 1 1 d . . . . .
H7BA H 0.9598 0.8546 0.8071 0.056 Uiso 1 1 calc R . . . .
H7BB H 0.9092 0.8427 0.7174 0.056 Uiso 1 1 calc R . . . .
C3B C 0.82467(11) 1.17465(12) 0.58890(15) 0.0486(5) Uani 1 1 d . . . . .
H3BA H 0.8245 1.2276 0.5714 0.058 Uiso 1 1 calc R . . . .
H3BB H 0.8244 1.1445 0.5330 0.058 Uiso 1 1 calc R . . . .
S1B S 0.52823(2) 1.22813(3) 0.44037(4) 0.04637(13) Uani 1 1 d . . . . .
F2B F 0.41305(7) 1.28363(11) 0.46857(12) 0.0784(5) Uani 1 1 d . . . . .
O12B O 0.50846(10) 1.23496(11) 0.34387(12) 0.0689(5) Uani 1 1 d . . . . .
O10B O 0.59415(8) 1.25433(11) 0.46863(15) 0.0734(6) Uani 1 1 d . . . . .
F1B F 0.48730(10) 1.36512(9) 0.45565(18) 0.1024(7) Uani 1 1 d . . . . .
O11B O 0.51011(10) 1.15979(11) 0.48160(17) 0.0799(6) Uani 1 1 d . . . . .
F3B F 0.48798(12) 1.30039(16) 0.57938(13) 0.1185(8) Uani 1 1 d . . . . .
C20B C 0.47722(12) 1.29798(14) 0.48831(16) 0.0573(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1A O11A 1.4327(16) . ?
S1A O10A 1.4279(16) . ?
S1A O12A 1.4244(17) . ?
S1A C20A 1.807(2) . ?
O7A C14A 1.348(2) . ?
O7A C19A 1.439(2) . ?
O6A C11A 1.420(2) . ?
O6A C10A 1.430(2) . ?
O2A C2A 1.426(2) . ?
O2A C3A 1.420(2) . ?
O3A C5A 1.425(2) . ?
O3A C4A 1.430(2) . ?
O5A C8A 1.423(2) . ?
O5A C9A 1.424(2) . ?
O1A C1A 1.427(2) . ?
O1A C12A 1.411(2) . ?
O4A C7A 1.429(2) . ?
O4A C6A 1.421(2) . ?
O7B C14B 1.339(2) . ?
O7B C19B 1.432(2) . ?
N1B H1BC 0.9000 . ?
N1B H1BD 0.9000 . ?
N1B H1BE 0.9000 . ?
N1B C13B 1.4591(19) . ?
N1A H1AC 0.9000 . ?
N1A H1AD 0.9000 . ?
N1A H1AE 0.9000 . ?
N1A C13A 1.4558(18) . ?
O8A N2A 1.218(2) . ?
F3A C20A 1.332(3) . ?
N2A O9A 1.220(2) . ?
N2A C17A 1.464(2) . ?
C13B C18B 1.370(2) . ?
C13B C14B 1.401(2) . ?
N2B O8B 1.220(3) . ?
N2B O9B 1.228(3) . ?
N2B C17B 1.459(2) . ?
C13A C14A 1.401(2) . ?
C13A C18A 1.373(2) . ?
C18B H18B 0.9400 . ?
C18B C17B 1.388(2) . ?
F1A C20A 1.310(3) . ?
C14A C15A 1.395(2) . ?
F2A C20A 1.328(3) . ?
C14B C15B 1.395(2) . ?
C17A C16A 1.375(3) . ?
C17A C18A 1.390(2) . ?
C16A H16A 0.9400 . ?
C16A C15A 1.387(3) . ?
C18A H18A 0.9400 . ?
C15B H15B 0.9400 . ?
C15B C16B 1.383(3) . ?
C15A H15A 0.9400 . ?
C17B C16B 1.379(3) . ?
C16B H16B 0.9400 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A C1A 1.490(3) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A H19C 0.9700 . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A C11A 1.492(3) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A C8A 1.494(3) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A C4A 1.499(3) . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C19B H19D 0.9700 . ?
C19B H19E 0.9700 . ?
C19B H19F 0.9700 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A C10A 1.506(3) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A C6A 1.499(3) . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
O5B C8B 1.432(2) . ?
O5B C9B 1.427(2) . ?
O4B C6B 1.424(2) . ?
O4B C7B 1.425(2) . ?
O1B C12B 1.412(2) . ?
O1B C1B 1.428(2) . ?
O3B C5B 1.424(2) . ?
O3B C4B 1.428(2) . ?
O6B C11B 1.423(2) . ?
O6B C10B 1.418(2) . ?
O2B C2B 1.430(2) . ?
O2B C3B 1.419(2) . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B C7B 1.501(3) . ?
C12B H12C 0.9800 . ?
C12B H12D 0.9800 . ?
C12B C11B 1.491(3) . ?
C11B H11C 0.9800 . ?
C11B H11D 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B C10B 1.496(3) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B C2B 1.506(3) . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B C6B 1.494(3) . ?
C6B H6BA 0.9800 . ?
C6B H6BB 0.9800 . ?
C10B H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C2B H2BA 0.9800 . ?
C2B H2BB 0.9800 . ?
C4B H4BA 0.9800 . ?
C4B H4BB 0.9800 . ?
C4B C3B 1.491(3) . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C3B H3BA 0.9800 . ?
C3B H3BB 0.9800 . ?
S1B O12B 1.4313(18) . ?
S1B O10B 1.4365(17) . ?
S1B O11B 1.4275(18) . ?
S1B C20B 1.811(2) . ?
F2B C20B 1.329(3) . ?
F1B C20B 1.315(3) . ?
F3B C20B 1.328(3) . ?

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
O11A S1A C20A 102.28(10) . . ?
O10A S1A O11A 114.86(11) . . ?
O10A S1A C20A 104.30(13) . . ?
O12A S1A O11A 116.60(12) . . ?
O12A S1A O10A 113.41(11) . . ?
O12A S1A C20A 103.01(12) . . ?
C14A O7A C19A 117.71(13) . . ?
C11A O6A C10A 113.49(15) . . ?
C3A O2A C2A 113.57(14) . . ?
C5A O3A C4A 111.95(16) . . ?
C8A O5A C9A 113.22(15) . . ?
C12A O1A C1A 115.34(14) . . ?
C6A O4A C7A 112.89(15) . . ?
C14B O7B C19B 119.37(15) . . ?
H1BC N1B H1BD 109.5 . . ?
H1BC N1B H1BE 109.5 . . ?
H1BD N1B H1BE 109.5 . . ?
C13B N1B H1BC 109.5 . . ?
C13B N1B H1BD 109.5 . . ?
C13B N1B H1BE 109.5 . . ?
H1AC N1A H1AD 109.5 . . ?
H1AC N1A H1AE 109.5 . . ?
H1AD N1A H1AE 109.5 . . ?
C13A N1A H1AC 109.5 . . ?
C13A N1A H1AD 109.5 . . ?
C13A N1A H1AE 109.5 . . ?
O8A N2A O9A 123.46(17) . . ?
O8A N2A C17A 118.63(16) . . ?
O9A N2A C17A 117.90(18) . . ?
C18B C13B N1B 120.60(14) . . ?
C18B C13B C14B 121.41(15) . . ?
C14B C13B N1B 117.98(14) . . ?
O8B N2B O9B 123.69(19) . . ?
O8B N2B C17B 118.44(18) . . ?
O9B N2B C17B 117.9(2) . . ?
C14A C13A N1A 119.32(14) . . ?
C18A C13A N1A 119.47(14) . . ?
C18A C13A C14A 121.20(14) . . ?
C13B C18B H18B 121.1 . . ?
C13B C18B C17B 117.80(15) . . ?
C17B C18B H18B 121.1 . . ?
O7A C14A C13A 115.62(14) . . ?
O7A C14A C15A 125.02(15) . . ?
C15A C14A C13A 119.36(15) . . ?
O7B C14B C13B 114.47(14) . . ?
O7B C14B C15B 125.92(15) . . ?
C15B C14B C13B 119.61(15) . . ?
C16A C17A N2A 119.48(15) . . ?
C16A C17A C18A 122.47(15) . . ?
C18A C17A N2A 118.05(16) . . ?
C17A C16A H16A 120.4 . . ?
C17A C16A C15A 119.12(15) . . ?
C15A C16A H16A 120.4 . . ?
C13A C18A C17A 117.97(15) . . ?
C13A C18A H18A 121.0 . . ?
C17A C18A H18A 121.0 . . ?
C14B C15B H15B 120.4 . . ?
C16B C15B C14B 119.27(16) . . ?
C16B C15B H15B 120.4 . . ?
C14A C15A H15A 120.1 . . ?
C16A C15A C14A 119.88(16) . . ?
C16A C15A H15A 120.1 . . ?
C18B C17B N2B 118.27(17) . . ?
C16B C17B N2B 119.45(16) . . ?
C16B C17B C18B 122.26(16) . . ?
C15B C16B H16B 120.2 . . ?
C17B C16B C15B 119.65(16) . . ?
C17B C16B H16B 120.2 . . ?
O2A C2A H2AA 110.2 . . ?
O2A C2A H2AB 110.2 . . ?
O2A C2A C1A 107.58(14) . . ?
H2AA C2A H2AB 108.5 . . ?
C1A C2A H2AA 110.2 . . ?
C1A C2A H2AB 110.2 . . ?
O7A C19A H19A 109.5 . . ?
O7A C19A H19B 109.5 . . ?
O7A C19A H19C 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
O1A C1A C2A 111.07(14) . . ?
O1A C1A H1AA 109.4 . . ?
O1A C1A H1AB 109.4 . . ?
C2A C1A H1AA 109.4 . . ?
C2A C1A H1AB 109.4 . . ?
H1AA C1A H1AB 108.0 . . ?
O1A C12A H12A 110.0 . . ?
O1A C12A H12B 110.0 . . ?
O1A C12A C11A 108.40(15) . . ?
H12A C12A H12B 108.4 . . ?
C11A C12A H12A 110.0 . . ?
C11A C12A H12B 110.0 . . ?
O6A C11A C12A 109.35(16) . . ?
O6A C11A H11A 109.8 . . ?
O6A C11A H11B 109.8 . . ?
C12A C11A H11A 109.8 . . ?
C12A C11A H11B 109.8 . . ?
H11A C11A H11B 108.3 . . ?
O4A C7A H7AA 110.1 . . ?
O4A C7A H7AB 110.1 . . ?
O4A C7A C8A 107.79(15) . . ?
H7AA C7A H7AB 108.5 . . ?
C8A C7A H7AA 110.1 . . ?
C8A C7A H7AB 110.1 . . ?
O2A C3A H3AA 110.2 . . ?
O2A C3A H3AB 110.2 . . ?
O2A C3A C4A 107.49(16) . . ?
H3AA C3A H3AB 108.5 . . ?
C4A C3A H3AA 110.2 . . ?
C4A C3A H3AB 110.2 . . ?
O5A C8A C7A 108.72(15) . . ?
O5A C8A H8AA 109.9 . . ?
O5A C8A H8AB 109.9 . . ?
C7A C8A H8AA 109.9 . . ?
C7A C8A H8AB 109.9 . . ?
H8AA C8A H8AB 108.3 . . ?
O7B C19B H19D 109.5 . . ?
O7B C19B H19E 109.5 . . ?
O7B C19B H19F 109.5 . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
O5A C9A H9AA 110.1 . . ?
O5A C9A H9AB 110.1 . . ?
O5A C9A C10A 108.21(16) . . ?
H9AA C9A H9AB 108.4 . . ?
C10A C9A H9AA 110.1 . . ?
C10A C9A H9AB 110.1 . . ?
O6A C10A C9A 113.17(15) . . ?
O6A C10A H10A 108.9 . . ?
O6A C10A H10B 108.9 . . ?
C9A C10A H10A 108.9 . . ?
C9A C10A H10B 108.9 . . ?
H10A C10A H10B 107.8 . . ?
O3A C5A H5AA 109.7 . . ?
O3A C5A H5AB 109.7 . . ?
O3A C5A C6A 109.82(17) . . ?
H5AA C5A H5AB 108.2 . . ?
C6A C5A H5AA 109.7 . . ?
C6A C5A H5AB 109.7 . . ?
O4A C6A C5A 108.18(15) . . ?
O4A C6A H6AA 110.1 . . ?
O4A C6A H6AB 110.1 . . ?
C5A C6A H6AA 110.1 . . ?
C5A C6A H6AB 110.1 . . ?
H6AA C6A H6AB 108.4 . . ?
O3A C4A C3A 109.70(16) . . ?
O3A C4A H4AA 109.7 . . ?
O3A C4A H4AB 109.7 . . ?
C3A C4A H4AA 109.7 . . ?
C3A C4A H4AB 109.7 . . ?
H4AA C4A H4AB 108.2 . . ?
F3A C20A S1A 112.27(16) . . ?
F1A C20A S1A 112.3(2) . . ?
F1A C20A F3A 108.6(2) . . ?
F1A C20A F2A 106.5(2) . . ?
F2A C20A S1A 110.32(18) . . ?
F2A C20A F3A 106.6(2) . . ?
C9B O5B C8B 112.94(15) . . ?
C6B O4B C7B 112.11(14) . . ?
C12B O1B C1B 112.92(14) . . ?
C5B O3B C4B 111.44(14) . . ?
C10B O6B C11B 112.37(15) . . ?
C3B O2B C2B 112.80(16) . . ?
O5B C8B H8BA 108.9 . . ?
O5B C8B H8BB 108.9 . . ?
O5B C8B C7B 113.42(15) . . ?
H8BA C8B H8BB 107.7 . . ?
C7B C8B H8BA 108.9 . . ?
C7B C8B H8BB 108.9 . . ?
O1B C12B H12C 109.8 . . ?
O1B C12B H12D 109.8 . . ?
O1B C12B C11B 109.38(14) . . ?
H12C C12B H12D 108.2 . . ?
C11B C12B H12C 109.8 . . ?
C11B C12B H12D 109.8 . . ?
O6B C11B C12B 108.56(15) . . ?
O6B C11B H11C 110.0 . . ?
O6B C11B H11D 110.0 . . ?
C12B C11B H11C 110.0 . . ?
C12B C11B H11D 110.0 . . ?
H11C C11B H11D 108.4 . . ?
O5B C9B H9BA 110.0 . . ?
O5B C9B H9BB 110.0 . . ?
O5B C9B C10B 108.49(15) . . ?
H9BA C9B H9BB 108.4 . . ?
C10B C9B H9BA 110.0 . . ?
C10B C9B H9BB 110.0 . . ?
O1B C1B H1BA 110.3 . . ?
O1B C1B H1BB 110.3 . . ?
O1B C1B C2B 107.02(15) . . ?
H1BA C1B H1BB 108.6 . . ?
C2B C1B H1BA 110.3 . . ?
C2B C1B H1BB 110.3 . . ?
O3B C5B H5BA 109.8 . . ?
O3B C5B H5BB 109.8 . . ?
O3B C5B C6B 109.54(15) . . ?
H5BA C5B H5BB 108.2 . . ?
C6B C5B H5BA 109.8 . . ?
C6B C5B H5BB 109.8 . . ?
O4B C6B C5B 108.34(15) . . ?
O4B C6B H6BA 110.0 . . ?
O4B C6B H6BB 110.0 . . ?
C5B C6B H6BA 110.0 . . ?
C5B C6B H6BB 110.0 . . ?
H6BA C6B H6BB 108.4 . . ?
O6B C10B C9B 108.43(15) . . ?
O6B C10B H10C 110.0 . . ?
O6B C10B H10D 110.0 . . ?
C9B C10B H10C 110.0 . . ?
C9B C10B H10D 110.0 . . ?
H10C C10B H10D 108.4 . . ?
O2B C2B C1B 112.57(15) . . ?
O2B C2B H2BA 109.1 . . ?
O2B C2B H2BB 109.1 . . ?
C1B C2B H2BA 109.1 . . ?
C1B C2B H2BB 109.1 . . ?
H2BA C2B H2BB 107.8 . . ?
O3B C4B H4BA 109.9 . . ?
O3B C4B H4BB 109.9 . . ?
O3B C4B C3B 109.15(16) . . ?
H4BA C4B H4BB 108.3 . . ?
C3B C4B H4BA 109.9 . . ?
C3B C4B H4BB 109.9 . . ?
O4B C7B C8B 107.66(15) . . ?
O4B C7B H7BA 110.2 . . ?
O4B C7B H7BB 110.2 . . ?
C8B C7B H7BA 110.2 . . ?
C8B C7B H7BB 110.2 . . ?
H7BA C7B H7BB 108.5 . . ?
O2B C3B C4B 108.99(16) . . ?
O2B C3B H3BA 109.9 . . ?
O2B C3B H3BB 109.9 . . ?
C4B C3B H3BA 109.9 . . ?
C4B C3B H3BB 109.9 . . ?
H3BA C3B H3BB 108.3 . . ?
O12B S1B O10B 114.15(12) . . ?
O12B S1B C20B 102.29(11) . . ?
O10B S1B C20B 102.65(12) . . ?
O11B S1B O12B 115.63(14) . . ?
O11B S1B O10B 115.60(11) . . ?
O11B S1B C20B 103.90(13) . . ?
F2B C20B S1B 111.84(16) . . ?
F1B C20B S1B 111.64(17) . . ?
F1B C20B F2B 106.5(2) . . ?
F1B C20B F3B 108.7(2) . . ?
F3B C20B S1B 111.9(2) . . ?
F3B C20B F2B 105.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.324
_oxdiff_exptl_absorpt_empirical_full_min 0.698
