# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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. 
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data_1-LTP
_database_code_depnum_ccdc_archive 'CCDC 2101550'
loop_
_audit_author_name
_audit_author_address
'Yu-hui Tan'
;Jiangxi University of Science and Technology
China
;
_audit_update_record             
;
2021-10-22 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;
_audit_creation_date             2021-07-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B F4, C12 H24 O6, C5 H10 N'
_chemical_formula_sum            'C17 H34 B F4 N O6'
_chemical_formula_weight         435.26
_chemical_absolute_configuration ?
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.4079(3)
_cell_length_b                   12.3389(3)
_cell_length_c                   12.8405(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2124.32(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8189
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.442
_cell_measurement_theta_min      3.171
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29486
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.741
_diffrn_reflns_theta_min         2.243
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.788
_reflns_number_gt                5000
_reflns_number_total             6080
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1973 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6080
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.049
_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)+(0.0459P)²+0.2514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0933
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C12(H12A,H12B), C9(H9A,H9B), C7(H7A,H7B), C14(H14A,H14B),
 C15(H15A,H15B), C11(H11A,H11B), C17(H17A,H17B), C13(H13A,H13B), C10(H10A,H10B),
  C8(H8A,H8B), C6(H6A,H6B), C5(H5A,H5B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_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
F1 F 0.70711(9) -0.14799(10) 0.34654(11) 0.0307(3) Uani 1 1 d . . . . .
F4 F 0.82166(10) -0.24173(11) 0.44195(11) 0.0330(3) Uani 1 1 d . . . . .
F2 F 0.69934(9) -0.33233(10) 0.35442(12) 0.0323(3) Uani 1 1 d . . . . .
O1 O 0.91727(10) 0.19098(11) 0.49348(11) 0.0214(3) Uani 1 1 d . . . . .
F3 F 0.82552(12) -0.25098(11) 0.26482(13) 0.0395(4) Uani 1 1 d . . . . .
O2 O 0.79693(10) 0.03705(11) 0.59797(11) 0.0230(3) Uani 1 1 d . . . . .
O6 O 0.87256(10) 0.41094(11) 0.52876(11) 0.0232(3) Uani 1 1 d . . . . .
O5 O 0.67181(10) 0.46330(11) 0.58234(12) 0.0228(3) Uani 1 1 d . . . . .
O3 O 0.59703(10) 0.08500(12) 0.65745(11) 0.0218(3) Uani 1 1 d . . . . .
O4 O 0.56129(10) 0.30586(12) 0.69349(12) 0.0217(3) Uani 1 1 d . . . . .
N1 N 0.70490(12) 0.23773(13) 0.51996(14) 0.0202(3) Uani 1 1 d . . . . .
H1A H 0.687532 0.307272 0.523091 0.024 Uiso 1 1 calc R U . . .
H1B H 0.771025 0.232157 0.522670 0.024 Uiso 1 1 calc R U . . .
H1C H 0.678144 0.202294 0.573477 0.024 Uiso 1 1 calc R U . . .
C16 C 0.95288(14) 0.08797(16) 0.52723(18) 0.0234(4) Uani 1 1 d . . . . .
H16A H 0.977852 0.093520 0.597931 0.028 Uiso 1 1 calc R U . . .
H16B H 1.007281 0.064661 0.482763 0.028 Uiso 1 1 calc R U . . .
C12 C 0.74910(16) 0.54251(15) 0.56966(17) 0.0241(4) Uani 1 1 d . . . . .
H12A H 0.783797 0.553245 0.635142 0.029 Uiso 1 1 calc R U . . .
H12B H 0.720436 0.611210 0.548393 0.029 Uiso 1 1 calc R U . . .
C9 C 0.48305(15) 0.22810(17) 0.70126(18) 0.0234(4) Uani 1 1 d . . . . .
H9A H 0.450249 0.219812 0.634404 0.028 Uiso 1 1 calc R U . . .
H9B H 0.433911 0.251920 0.751759 0.028 Uiso 1 1 calc R U . . .
C7 C 0.65212(15) -0.00676(17) 0.69451(17) 0.0225(4) Uani 1 1 d . . . . .
H7A H 0.606494 -0.064750 0.712709 0.027 Uiso 1 1 calc R U . . .
H7B H 0.689283 0.013074 0.756457 0.027 Uiso 1 1 calc R U . . .
C14 C 0.95329(16) 0.37747(18) 0.46374(17) 0.0234(4) Uani 1 1 d . . . . .
H14A H 1.005434 0.431969 0.464099 0.028 Uiso 1 1 calc R U . . .
H14B H 0.930281 0.368170 0.392680 0.028 Uiso 1 1 calc R U . . .
C15 C 0.99288(15) 0.27235(17) 0.50504(18) 0.0240(4) Uani 1 1 d . . . . .
H15A H 1.052241 0.251459 0.466807 0.029 Uiso 1 1 calc R U . . .
H15B H 1.010497 0.280168 0.577918 0.029 Uiso 1 1 calc R U . . .
C11 C 0.60871(15) 0.48957(17) 0.66793(17) 0.0238(4) Uani 1 1 d . . . . .
H11A H 0.583563 0.562845 0.660233 0.029 Uiso 1 1 calc R U . . .
H11B H 0.646167 0.485615 0.732445 0.029 Uiso 1 1 calc R U . . .
C17 C 0.87015(14) 0.00668(16) 0.52300(17) 0.0229(4) Uani 1 1 d . . . . .
H17A H 0.840916 0.005422 0.453910 0.027 Uiso 1 1 calc R U . . .
H17B H 0.895628 -0.065096 0.538554 0.027 Uiso 1 1 calc R U . . .
C1 C 0.66757(16) 0.18935(18) 0.41930(17) 0.0242(4) Uani 1 1 d . . . . .
H1 H 0.679920 0.111084 0.417793 0.029 Uiso 1 1 calc R U . . .
C13 C 0.82085(15) 0.50287(17) 0.48806(17) 0.0242(4) Uani 1 1 d . . . . .
H13A H 0.784897 0.482873 0.425393 0.029 Uiso 1 1 calc R U . . .
H13B H 0.867959 0.559698 0.470579 0.029 Uiso 1 1 calc R U . . .
C10 C 0.52347(16) 0.41108(17) 0.67099(17) 0.0239(4) Uani 1 1 d . . . . .
H10A H 0.476088 0.432653 0.724173 0.029 Uiso 1 1 calc R U . . .
H10B H 0.489388 0.410543 0.604356 0.029 Uiso 1 1 calc R U . . .
C8 C 0.52766(16) 0.12219(18) 0.73479(16) 0.0235(4) Uani 1 1 d . . . . .
H8A H 0.561691 0.131319 0.800872 0.028 Uiso 1 1 calc R U . . .
H8B H 0.475248 0.068857 0.744059 0.028 Uiso 1 1 calc R U . . .
C6 C 0.72269(15) -0.04486(16) 0.61150(17) 0.0227(4) Uani 1 1 d . . . . .
H6A H 0.753621 -0.112589 0.632191 0.027 Uiso 1 1 calc R U . . .
H6B H 0.687031 -0.056612 0.546745 0.027 Uiso 1 1 calc R U . . .
C5 C 0.71665(16) 0.24483(19) 0.32503(17) 0.0297(5) Uani 1 1 d . . . . .
H5A H 0.779289 0.278623 0.344375 0.036 Uiso 1 1 calc R U . . .
H5B H 0.728655 0.193378 0.269306 0.036 Uiso 1 1 calc R U . . .
C4 C 0.64156(18) 0.3276(2) 0.29347(19) 0.0340(5) Uani 1 1 d . . . . .
H4 H 0.654698 0.384486 0.247995 0.041 Uiso 1 1 calc R U . . .
C2 C 0.55589(16) 0.2130(2) 0.40793(19) 0.0310(5) Uani 1 1 d . . . . .
H2A H 0.521226 0.152250 0.376444 0.037 Uiso 1 1 calc R U . . .
H2B H 0.525782 0.228981 0.474874 0.037 Uiso 1 1 calc R U . . .
C3 C 0.55406(18) 0.3104(2) 0.3379(2) 0.0358(5) Uani 1 1 d . . . . .
H3 H 0.498094 0.353499 0.327044 0.043 Uiso 1 1 calc R U . . .
B1 B 0.76350(17) -0.24339(19) 0.3523(2) 0.0244(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
F1 B1 1.401(3) . ?
F4 B1 1.391(3) . ?
F2 B1 1.395(3) . ?
O1 C16 1.425(2) . ?
O1 C15 1.434(2) . ?
F3 B1 1.401(3) . ?
O2 C17 1.425(2) . ?
O2 C6 1.429(2) . ?
O6 C14 1.428(2) . ?
O6 C13 1.428(2) . ?
O5 C12 1.434(2) . ?
O5 C11 1.424(2) . ?
O3 C7 1.433(2) . ?
O3 C8 1.436(3) . ?
O4 C9 1.425(2) . ?
O4 C10 1.423(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.509(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.496(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.504(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.500(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.501(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.499(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.499(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C1 H1 0.9800 . ?
C1 C5 1.539(3) . ?
C1 C2 1.532(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.490(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.321(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.502(3) . ?
C3 H3 0.9300 . ?

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
C16 O1 C15 110.86(15) . . ?
C17 O2 C6 112.08(15) . . ?
C14 O6 C13 112.56(16) . . ?
C11 O5 C12 111.21(16) . . ?
C7 O3 C8 110.90(15) . . ?
C10 O4 C9 111.47(15) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
O1 C16 H16A 109.7 . . ?
O1 C16 H16B 109.7 . . ?
O1 C16 C17 109.78(15) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
O5 C12 H12A 110.0 . . ?
O5 C12 H12B 110.0 . . ?
O5 C12 C13 108.65(16) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
O4 C9 H9A 110.0 . . ?
O4 C9 H9B 110.0 . . ?
O4 C9 C8 108.25(16) . . ?
H9A C9 H9B 108.4 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
O3 C7 H7A 109.7 . . ?
O3 C7 H7B 109.7 . . ?
O3 C7 C6 109.67(16) . . ?
H7A C7 H7B 108.2 . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
O6 C14 H14A 110.1 . . ?
O6 C14 H14B 110.1 . . ?
O6 C14 C15 108.18(17) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
O1 C15 C14 108.60(16) . . ?
O1 C15 H15A 110.0 . . ?
O1 C15 H15B 110.0 . . ?
C14 C15 H15A 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
O5 C11 H11A 109.9 . . ?
O5 C11 H11B 109.9 . . ?
O5 C11 C10 109.04(17) . . ?
H11A C11 H11B 108.3 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
O2 C17 C16 108.05(17) . . ?
O2 C17 H17A 110.1 . . ?
O2 C17 H17B 110.1 . . ?
C16 C17 H17A 110.1 . . ?
C16 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
N1 C1 H1 110.5 . . ?
N1 C1 C5 110.86(17) . . ?
N1 C1 C2 109.29(18) . . ?
C5 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
C2 C1 C5 104.97(17) . . ?
O6 C13 C12 108.29(17) . . ?
O6 C13 H13A 110.0 . . ?
O6 C13 H13B 110.0 . . ?
C12 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
O4 C10 C11 108.85(16) . . ?
O4 C10 H10A 109.9 . . ?
O4 C10 H10B 109.9 . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O3 C8 C9 109.76(17) . . ?
O3 C8 H8A 109.7 . . ?
O3 C8 H8B 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O2 C6 C7 107.69(16) . . ?
O2 C6 H6A 110.2 . . ?
O2 C6 H6B 110.2 . . ?
C7 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C1 C5 H5A 111.1 . . ?
C1 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C4 C5 C1 103.29(17) . . ?
C4 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
C5 C4 H4 124.1 . . ?
C3 C4 C5 111.9(2) . . ?
C3 C4 H4 124.1 . . ?
C1 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 C1 103.02(19) . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C4 C3 C2 111.9(2) . . ?
C4 C3 H3 124.1 . . ?
C2 C3 H3 124.1 . . ?
F4 B1 F1 109.5(2) . . ?
F4 B1 F2 109.97(19) . . ?
F4 B1 F3 109.38(17) . . ?
F2 B1 F1 109.23(17) . . ?
F2 B1 F3 109.2(2) . . ?
F3 B1 F1 109.51(19) . . ?

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
O1 C16 C17 O2 -65.9(2) . . . . ?
O6 C14 C15 O1 65.6(2) . . . . ?
O5 C12 C13 O6 -68.3(2) . . . . ?
O5 C11 C10 O4 65.7(2) . . . . ?
O3 C7 C6 O2 67.6(2) . . . . ?
O4 C9 C8 O3 -62.3(2) . . . . ?
N1 C1 C5 C4 -96.6(2) . . . . ?
N1 C1 C2 C3 98.0(2) . . . . ?
C16 O1 C15 C14 177.29(17) . . . . ?
C12 O5 C11 C10 174.20(16) . . . . ?
C9 O4 C10 C11 177.83(17) . . . . ?
C7 O3 C8 C9 170.96(17) . . . . ?
C14 O6 C13 C12 -170.86(16) . . . . ?
C15 O1 C16 C17 175.18(17) . . . . ?
C11 O5 C12 C13 172.47(16) . . . . ?
C17 O2 C6 C7 177.82(16) . . . . ?
C1 C5 C4 C3 -14.0(3) . . . . ?
C1 C2 C3 C4 13.4(3) . . . . ?
C13 O6 C14 C15 -172.11(16) . . . . ?
C10 O4 C9 C8 -174.77(17) . . . . ?
C8 O3 C7 C6 179.07(16) . . . . ?
C6 O2 C17 C16 -170.66(16) . . . . ?
C5 C1 C2 C3 -21.0(3) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C2 C1 C5 C4 21.3(2) . . . . ?

_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_2-RTP
_database_code_depnum_ccdc_archive 'CCDC 2102307'
loop_
_audit_author_name
_audit_author_address
'Yu-hui Tan'
;Jiangxi University of Science and Technology
China
;
_audit_update_record             
;
2021-10-22 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;
_audit_creation_date             2021-08-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl O4, C12 H23 O6, C5 H10 N'
_chemical_formula_sum            'C17 H33 Cl N O10'
_chemical_formula_weight         446.89
_chemical_absolute_configuration ?
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.2086(7)
_cell_length_b                   12.6507(7)
_cell_length_c                   13.4674(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2250.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7146
_cell_measurement_temperature    300
_cell_measurement_theta_max      25.732
_cell_measurement_theta_min      2.694
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0550 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.9183.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20992
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.694
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                3465
_reflns_number_total             4861
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4861
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.031
_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)+(0.0805P)²+0.7351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1620
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C11(H11A,H11B), C10(H10A,H10B), C16(H16A,H16B), C9(H9A,H9B),
 C12(H12A,H12B), C17(H17A,H17B), C14(H14A,H14B), C13(H13A,H13B), C7(H7A,H7B),
 C6(H6A,H6B), C5(H5A,H5B), C2(H2A,H2B)
1.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C3(H3)
1.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_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
Cl1 Cl 0.72562(10) 0.76109(8) 0.34236(11) 0.0681(4) Uani 1 1 d . . . . .
O10 O 0.4138(3) 0.9079(3) 0.6384(2) 0.0618(8) Uani 1 1 d . . . . .
N1 N 0.3181(3) 0.7512(3) 0.5087(2) 0.0473(8) Uani 1 1 d . . . . .
H1A H 0.256860 0.753488 0.481200 0.057 Uiso 1 1 calc R U . . .
H1B H 0.324834 0.804682 0.551121 0.057 Uiso 1 1 calc R U . . .
H1C H 0.325675 0.690314 0.540942 0.057 Uiso 1 1 calc R U . . .
O6 O 0.3393(3) 0.5295(2) 0.5808(2) 0.0630(9) Uani 1 1 d . . . . .
O5 O 0.4461(2) 0.6892(3) 0.6786(2) 0.0611(8) Uani 1 1 d . . . . .
O7 O 0.1451(3) 0.5896(3) 0.5158(3) 0.0656(9) Uani 1 1 d . . . . .
O9 O 0.2183(2) 0.9537(2) 0.5743(2) 0.0622(9) Uani 1 1 d . . . . .
O8 O 0.0994(2) 0.8039(3) 0.4728(3) 0.0628(8) Uani 1 1 d . . . . .
O2 O 0.6692(5) 0.7610(4) 0.4315(4) 0.1138(19) Uani 1 1 d . . . . .
O3 O 0.7837(3) 0.8552(3) 0.3329(3) 0.0936(12) Uani 1 1 d . . . . .
C15 C 0.4000(4) 0.5097(4) 0.6655(4) 0.0686(13) Uani 1 1 d . . . . .
H15A H 0.426271 0.438169 0.662702 0.082 Uiso 1 1 calc R U . . .
H15B H 0.359310 0.516445 0.725085 0.082 Uiso 1 1 calc R U . . .
C11 C 0.3603(4) 0.9986(4) 0.6712(4) 0.0692(14) Uani 1 1 d . . . . .
H11A H 0.407766 1.054632 0.687089 0.083 Uiso 1 1 calc R U . . .
H11B H 0.322204 0.981814 0.730664 0.083 Uiso 1 1 calc R U . . .
C10 C 0.2900(4) 1.0347(3) 0.5916(4) 0.0673(13) Uani 1 1 d . . . . .
H10A H 0.255837 1.099011 0.612079 0.081 Uiso 1 1 calc R U . . .
H10B H 0.327541 1.049408 0.531253 0.081 Uiso 1 1 calc R U . . .
C1 C 0.3983(4) 0.7600(5) 0.4281(4) 0.0721(15) Uani 1 1 d . . . . .
H1 H 0.463609 0.774747 0.459597 0.086 Uiso 1 1 calc R U . . .
O4 O 0.7891(3) 0.6702(3) 0.3371(4) 0.1156(18) Uani 1 1 d . . . . .
C16 C 0.2574(5) 0.4577(3) 0.5711(4) 0.0726(14) Uani 1 1 d . . . . .
H16A H 0.219162 0.454954 0.632566 0.087 Uiso 1 1 calc R U . . .
H16B H 0.282922 0.387314 0.557128 0.087 Uiso 1 1 calc R U . . .
C9 C 0.1429(4) 0.9836(4) 0.5039(4) 0.0710(14) Uani 1 1 d . . . . .
H9A H 0.172347 0.987891 0.438032 0.085 Uiso 1 1 calc R U . . .
H9B H 0.115320 1.052287 0.520878 0.085 Uiso 1 1 calc R U . . .
C12 C 0.4805(4) 0.8687(5) 0.7124(4) 0.0771(15) Uani 1 1 d . . . . .
H12A H 0.443825 0.859911 0.774284 0.093 Uiso 1 1 calc R U . . .
H12B H 0.534448 0.919314 0.723530 0.093 Uiso 1 1 calc R U . . .
C17 C 0.1907(4) 0.4939(4) 0.4881(4) 0.0710(14) Uani 1 1 d . . . . .
H17A H 0.230404 0.503876 0.428300 0.085 Uiso 1 1 calc R U . . .
H17B H 0.139107 0.441222 0.474766 0.085 Uiso 1 1 calc R U . . .
C8 C 0.0620(4) 0.9030(4) 0.5056(5) 0.0767(16) Uani 1 1 d . . . . .
H8 H -0.004405 0.915508 0.525397 0.092 Uiso 1 1 calc R U . . .
C14 C 0.4842(4) 0.5850(4) 0.6690(4) 0.0741(15) Uani 1 1 d . . . . .
H14A H 0.527707 0.568687 0.724971 0.089 Uiso 1 1 calc R U . . .
H14B H 0.524050 0.579359 0.608776 0.089 Uiso 1 1 calc R U . . .
C13 C 0.5245(4) 0.7662(4) 0.6822(4) 0.0719(14) Uani 1 1 d . . . . .
H13A H 0.555910 0.772819 0.617360 0.086 Uiso 1 1 calc R U . . .
H13B H 0.575974 0.744713 0.729392 0.086 Uiso 1 1 calc R U . . .
C7 C 0.0255(4) 0.7242(4) 0.4822(5) 0.0777(16) Uani 1 1 d . . . . .
H7A H -0.033443 0.742045 0.442646 0.093 Uiso 1 1 calc R U . . .
H7B H 0.004520 0.718164 0.550992 0.093 Uiso 1 1 calc R U . . .
C6 C 0.0686(5) 0.6222(5) 0.4478(5) 0.0842(17) Uani 1 1 d . . . . .
H6A H 0.015753 0.569082 0.444406 0.101 Uiso 1 1 calc R U . . .
H6B H 0.097407 0.630538 0.382039 0.101 Uiso 1 1 calc R U . . .
C5 C 0.4089(6) 0.6643(5) 0.3660(5) 0.110(3) Uani 1 1 d . . . . .
H5A H 0.479109 0.651917 0.348425 0.132 Uiso 1 1 calc R U . . .
H5B H 0.382502 0.602461 0.399788 0.132 Uiso 1 1 calc R U . . .
C2 C 0.3756(10) 0.8440(6) 0.3606(7) 0.172(5) Uani 1 1 d . . . . .
H2A H 0.436614 0.881025 0.340529 0.206 Uiso 1 1 calc R U . . .
H2B H 0.328716 0.894172 0.389820 0.206 Uiso 1 1 calc R U . . .
C4 C 0.3487(6) 0.6899(9) 0.2788(7) 0.133(4) Uani 1 1 d . . . . .
H4 H 0.327731 0.640668 0.231842 0.160 Uiso 1 1 calc R U . . .
O1 O 0.6588(7) 0.7557(5) 0.2614(7) 0.166(3) Uani 1 1 d . . . . .
C3 C 0.3286(9) 0.7870(12) 0.2751(7) 0.198(7) Uani 1 1 d . . . . .
H3 H 0.289890 0.818967 0.225841 0.238 Uiso 1 1 calc R U . . .


_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
Cl1 O2 1.413(5) . ?
Cl1 O3 1.422(4) . ?
Cl1 O4 1.425(4) . ?
Cl1 O1 1.405(8) . ?
O10 C11 1.418(6) . ?
O10 C12 1.420(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.521(6) . ?
O6 C15 1.416(6) . ?
O6 C16 1.419(6) . ?
O5 C14 1.417(6) . ?
O5 C13 1.422(6) . ?
O7 C17 1.402(6) . ?
O7 C6 1.424(6) . ?
O9 C10 1.415(5) . ?
O9 C9 1.426(6) . ?
O8 C8 1.417(6) . ?
O8 C7 1.410(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.464(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.489(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C1 H1 0.9800 . ?
C1 C5 1.477(8) . ?
C1 C2 1.430(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.496(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.478(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.478(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C8 H8 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.484(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.454(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.494(17) . ?
C4 H4 0.9300 . ?
C4 C3 1.258(16) . ?
C3 H3 0.9300 . ?

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
O2 Cl1 O3 111.2(3) . . ?
O2 Cl1 O4 110.6(3) . . ?
O3 Cl1 O4 110.7(3) . . ?
O1 Cl1 O2 109.2(4) . . ?
O1 Cl1 O3 108.0(3) . . ?
O1 Cl1 O4 106.9(4) . . ?
C11 O10 C12 111.9(4) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C15 O6 C16 113.1(4) . . ?
C14 O5 C13 112.5(4) . . ?
C17 O7 C6 112.6(4) . . ?
C10 O9 C9 112.6(4) . . ?
C7 O8 C8 111.3(4) . . ?
O6 C15 H15A 109.7 . . ?
O6 C15 H15B 109.7 . . ?
O6 C15 C14 110.0(4) . . ?
H15A C15 H15B 108.2 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
O10 C11 H11A 109.8 . . ?
O10 C11 H11B 109.8 . . ?
O10 C11 C10 109.6(4) . . ?
H11A C11 H11B 108.2 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
O9 C10 C11 108.3(4) . . ?
O9 C10 H10A 110.0 . . ?
O9 C10 H10B 110.0 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
N1 C1 H1 108.5 . . ?
C5 C1 N1 114.2(5) . . ?
C5 C1 H1 108.5 . . ?
C2 C1 N1 111.2(5) . . ?
C2 C1 H1 108.5 . . ?
C2 C1 C5 105.7(6) . . ?
O6 C16 H16A 109.9 . . ?
O6 C16 H16B 109.9 . . ?
O6 C16 C17 108.7(4) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
O9 C9 H9A 110.1 . . ?
O9 C9 H9B 110.1 . . ?
O9 C9 C8 108.2(4) . . ?
H9A C9 H9B 108.4 . . ?
C8 C9 H9A 110.1 . . ?
C8 C9 H9B 110.1 . . ?
O10 C12 H12A 109.5 . . ?
O10 C12 H12B 109.5 . . ?
O10 C12 C13 110.9(4) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
O7 C17 C16 108.6(4) . . ?
O7 C17 H17A 110.0 . . ?
O7 C17 H17B 110.0 . . ?
C16 C17 H17A 110.0 . . ?
C16 C17 H17B 110.0 . . ?
H17A C17 H17B 108.3 . . ?
O8 C8 C9 110.7(4) . . ?
O8 C8 H8 124.7 . . ?
C9 C8 H8 124.7 . . ?
O5 C14 C15 109.8(4) . . ?
O5 C14 H14A 109.7 . . ?
O5 C14 H14B 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O5 C13 C12 108.9(4) . . ?
O5 C13 H13A 109.9 . . ?
O5 C13 H13B 109.9 . . ?
C12 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
O8 C7 H7A 109.8 . . ?
O8 C7 H7B 109.8 . . ?
O8 C7 C6 109.2(5) . . ?
H7A C7 H7B 108.3 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
O7 C6 C7 108.9(5) . . ?
O7 C6 H6A 109.9 . . ?
O7 C6 H6B 109.9 . . ?
C7 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C1 C5 H5A 111.2 . . ?
C1 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C4 C5 C1 102.9(6) . . ?
C4 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
C1 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C1 C2 C3 102.6(7) . . ?
H2A C2 H2B 109.2 . . ?
C3 C2 H2A 111.3 . . ?
C3 C2 H2B 111.3 . . ?
C5 C4 H4 124.3 . . ?
C3 C4 C5 111.4(8) . . ?
C3 C4 H4 124.3 . . ?
C2 C3 H3 124.7 . . ?
C4 C3 C2 110.7(7) . . ?
C4 C3 H3 124.7 . . ?

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
O10 C11 C10 O9 62.8(5) . . . . ?
O10 C12 C13 O5 -66.6(6) . . . . ?
N1 C1 C5 C4 97.8(7) . . . . ?
N1 C1 C2 C3 -99.3(7) . . . . ?
O6 C15 C14 O5 62.5(5) . . . . ?
O6 C16 C17 O7 -66.8(5) . . . . ?
O9 C9 C8 O8 -64.6(6) . . . . ?
O8 C7 C6 O7 68.2(6) . . . . ?
C15 O6 C16 C17 172.5(4) . . . . ?
C11 O10 C12 C13 172.1(4) . . . . ?
C10 O9 C9 C8 -169.3(4) . . . . ?
C1 C5 C4 C3 14.6(11) . . . . ?
C1 C2 C3 C4 -17.1(13) . . . . ?
C16 O6 C15 C14 178.5(4) . . . . ?
C9 O9 C10 C11 175.9(4) . . . . ?
C12 O10 C11 C10 -178.7(4) . . . . ?
C17 O7 C6 C7 -179.4(5) . . . . ?
C8 O8 C7 C6 -179.5(5) . . . . ?
C14 O5 C13 C12 -168.6(4) . . . . ?
C13 O5 C14 C15 -179.8(4) . . . . ?
C7 O8 C8 C9 174.8(5) . . . . ?
C6 O7 C17 C16 -171.1(4) . . . . ?
C5 C1 C2 C3 25.2(10) . . . . ?
C5 C4 C3 C2 1.3(14) . . . . ?
C2 C1 C5 C4 -24.8(9) . . . . ?

_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_1-ITP
_database_code_depnum_ccdc_archive 'CCDC 2117262'
loop_
_audit_author_name
_audit_author_address
'Yu-hui Tan'
;Jiangxi University of Science and Technology
China
;
_audit_update_record             
;
2021-10-22 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;
_audit_creation_date             2021-08-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H24 O6, C5 H10 N, B F4'
_chemical_formula_sum            'C17 H34 B F4 N O6'
_chemical_formula_weight         435.26
_chemical_absolute_configuration ?
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.2433(11)
_cell_length_b                   12.4686(10)
_cell_length_c                   13.4680(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2223.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7326
_cell_measurement_temperature    300
_cell_measurement_theta_max      25.217
_cell_measurement_theta_min      3.394
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0588 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.8970.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19734
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.475
_diffrn_reflns_theta_min         3.428
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                3157
_reflns_number_total             4307
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1163 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4307
_refine_ls_number_restraints     488
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.070
_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)+(0.0753P)²+0.8530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1662
_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
2. Restrained distances
 C3A-C4A
 1.2 with sigma of 0.02
 C3B-C4B
 1.2 with sigma of 0.02
 C5A-C1A \\sim C2A-C1A
 with sigma of 0.02
 C5A-C4A \\sim C3A-C2A
 with sigma of 0.02
 C7-C6 \\sim C9-C8 \\sim C11-C10 \\sim C13-C12 \\sim C15-C14 \\sim C17-C16
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1B \\sim C1B \\sim C2B \\sim C5B \\sim C3B \\sim C5A \\sim N1A \\sim C1A \\sim
C2A \\sim C3A \\sim C4A \\sim C4B: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
N1B \\sim C1B \\sim C2B \\sim C5B \\sim C3B \\sim C4B \\sim N1A \\sim C1A \\sim
C2A \\sim C3A \\sim C4A \\sim C5A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
F4B \\sim F1B \\sim F3B \\sim F2B \\sim B1B \\sim F2A \\sim F1A \\sim B1A \\sim
F4A \\sim F3A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
F2B \\sim F2A \\sim F1B \\sim F1A \\sim F4B \\sim F4A \\sim F3A \\sim F3B:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 F4B, F1B, F3B, F2B, B1B, F2A, F1A, B1A, F4A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B, C2B, C5B, C3B, C4B, C5A, C1A, C2A, C3A, C4A, N1B, N1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F4B)=Sof(F1B)=Sof(F3B)=Sof(F2B)=Sof(B1B)=1-FVAR(1)
 Sof(F2A)=Sof(F1A)=Sof(B1A)=Sof(F4A)=Sof(F3A)=FVAR(1)
 Sof(N1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2BA)=
 Sof(H2BB)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=1-
 FVAR(2)
 Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(N1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1A)=
 Sof(H1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 FVAR(2)
6.a Riding coordinates:
 N1B(H1BA,H1BB,H1BC), N1A(H1AA,H1AB,H1AC)
6.b Ternary CH refined with riding coordinates:
 C1B(H1B), C1A(H1A)
6.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B), C11(H11A,H11B), C6(H6A,H6B), C13(H13A,H13B),
 C16(H16A,H16B), C17(H17A,H17B), C9(H9A,H9B), C7(H7A,H7B), C10(H10A,H10B),
 C12(H12A,H12B), C14(H14A,H14B), C2B(H2BA,H2BB), C5B(H5BA,H5BB), C5A(H5AA,H5AB),
  C2A(H2AA,H2AB)
6.d Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C4B(H4B), C3A(H3A), C4A(H4A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O1 O 0.4169(3) 0.9101(3) 0.6520(2) 0.0615(8) Uani 1 1 d . . . . .
N1B N 0.317(3) 0.753(3) 0.518(3) 0.052(5) Uani 0.503(12) 1 d . U P A 2
H1BA H 0.267450 0.703724 0.505142 0.062 Uiso 0.503(12) 1 d R U P A 2
H1BB H 0.290490 0.813724 0.542122 0.062 Uiso 0.503(12) 1 d R U P A 2
H1BC H 0.356130 0.723294 0.570692 0.062 Uiso 0.503(12) 1 d R U P A 2
O3 O 0.3435(3) 0.5264(2) 0.5917(3) 0.0647(9) Uani 1 1 d . . . . .
O4 O 0.1502(3) 0.5875(3) 0.5256(3) 0.0683(9) Uani 1 1 d . . . . .
O6 O 0.2220(2) 0.9567(2) 0.5873(3) 0.0631(9) Uani 1 1 d . . . . .
O5 O 0.1036(2) 0.8055(3) 0.4844(3) 0.0644(9) Uani 1 1 d . . . . .
O2 O 0.4496(2) 0.6881(3) 0.6913(3) 0.0628(8) Uani 1 1 d . . . . .
F4B F 0.774(2) 0.8558(18) 0.333(2) 0.098(5) Uani 0.48(3) 1 d . U P B 2
F1B F 0.6614(16) 0.7687(18) 0.424(2) 0.132(6) Uani 0.48(3) 1 d . U P B 2
F3B F 0.775(2) 0.6725(14) 0.3339(18) 0.117(6) Uani 0.48(3) 1 d . U P B 2
C8 C 0.0664(4) 0.9043(4) 0.5189(5) 0.0765(15) Uani 1 1 d D . . . .
H8A H 0.041555 0.896124 0.586241 0.092 Uiso 1 1 calc R U . . .
H8B H 0.010587 0.927305 0.477395 0.092 Uiso 1 1 calc R U . . .
C15 C 0.4015(4) 0.5061(4) 0.6774(4) 0.0703(14) Uani 1 1 d D . . . .
H15A H 0.426784 0.433079 0.675904 0.084 Uiso 1 1 calc R U . . .
H15B H 0.359953 0.514477 0.736177 0.084 Uiso 1 1 calc R U . . .
C11 C 0.3634(4) 1.0020(4) 0.6853(4) 0.0679(13) Uani 1 1 d D . . . .
H11A H 0.410475 1.058880 0.701724 0.081 Uiso 1 1 calc R U . . .
H11B H 0.324894 0.984606 0.744479 0.081 Uiso 1 1 calc R U . . .
C6 C 0.0740(5) 0.6209(5) 0.4581(5) 0.0839(17) Uani 1 1 d D . . . .
H6A H 0.021463 0.566830 0.454216 0.101 Uiso 1 1 calc R U . . .
H6B H 0.102685 0.630070 0.392370 0.101 Uiso 1 1 calc R U . . .
C13 C 0.5275(4) 0.7656(4) 0.6952(5) 0.0722(14) Uani 1 1 d D . . . .
H13A H 0.558603 0.773158 0.630383 0.087 Uiso 1 1 calc R U . . .
H13B H 0.579062 0.743372 0.742090 0.087 Uiso 1 1 calc R U . . .
C16 C 0.2612(4) 0.4532(3) 0.5804(5) 0.0728(14) Uani 1 1 d D . . . .
H16A H 0.222921 0.449536 0.641703 0.087 Uiso 1 1 calc R U . . .
H16B H 0.286866 0.382085 0.565763 0.087 Uiso 1 1 calc R U . . .
C1B C 0.3918(17) 0.7783(13) 0.4359(15) 0.074(3) Uani 0.503(12) 1 d . U P A 2
H1B H 0.449553 0.817912 0.462883 0.089 Uiso 0.503(12) 1 calc R U P A 2
C17 C 0.1954(4) 0.4897(4) 0.4991(4) 0.0731(15) Uani 1 1 d D . . . .
H17A H 0.234810 0.498897 0.438949 0.088 Uiso 1 1 calc R U . . .
H17B H 0.143637 0.436398 0.486273 0.088 Uiso 1 1 calc R U . . .
C9 C 0.1475(4) 0.9862(4) 0.5167(4) 0.0717(14) Uani 1 1 d D . . . .
H9A H 0.177096 0.989795 0.450893 0.086 Uiso 1 1 calc R U . . .
H9B H 0.120038 1.056127 0.532937 0.086 Uiso 1 1 calc R U . . .
C7 C 0.0304(4) 0.7241(4) 0.4932(5) 0.0791(16) Uani 1 1 d D . . . .
H7A H -0.028464 0.742253 0.453766 0.095 Uiso 1 1 calc R U . . .
H7B H 0.009485 0.717384 0.561950 0.095 Uiso 1 1 calc R U . . .
C10 C 0.2940(4) 1.0381(3) 0.6047(4) 0.0684(14) Uani 1 1 d D . . . .
H10A H 0.260162 1.103784 0.624317 0.082 Uiso 1 1 calc R U . . .
H10B H 0.332059 1.052106 0.544617 0.082 Uiso 1 1 calc R U . . .
C12 C 0.4831(5) 0.8694(5) 0.7268(4) 0.0788(17) Uani 1 1 d D . . . .
H12A H 0.445899 0.859511 0.788199 0.095 Uiso 1 1 calc R U . . .
H12B H 0.536650 0.920807 0.739073 0.095 Uiso 1 1 calc R U . . .
C14 C 0.4870(4) 0.5824(4) 0.6807(4) 0.0731(14) Uani 1 1 d D . . . .
H14A H 0.530800 0.565127 0.736181 0.088 Uiso 1 1 calc R U . . .
H14B H 0.526179 0.576882 0.620072 0.088 Uiso 1 1 calc R U . . .
F2B F 0.6453(18) 0.763(2) 0.289(2) 0.157(6) Uani 0.48(3) 1 d . U P B 2
C2B C 0.4274(13) 0.6726(16) 0.3902(12) 0.076(3) Uani 0.503(12) 1 d . U P A 2
H2BA H 0.497294 0.675889 0.368751 0.092 Uiso 0.503(12) 1 calc R U P A 2
H2BB H 0.418032 0.612400 0.434800 0.092 Uiso 0.503(12) 1 calc R U P A 2
B1B B 0.733(4) 0.764(3) 0.354(3) 0.082(6) Uani 0.48(3) 1 d . U P B 2
C5B C 0.3436(14) 0.8404(12) 0.3571(11) 0.088(3) Uani 0.503(12) 1 d . U P A 2
H5BA H 0.289376 0.884753 0.382805 0.106 Uiso 0.503(12) 1 calc R U P A 2
H5BB H 0.391869 0.885164 0.322345 0.106 Uiso 0.503(12) 1 calc R U P A 2
C3B C 0.3556(13) 0.6698(13) 0.3044(12) 0.083(3) Uani 0.503(12) 1 d D U P A 2
H3B H 0.348441 0.610719 0.262824 0.100 Uiso 0.503(12) 1 calc R U P A 2
C4B C 0.3053(14) 0.7556(13) 0.2939(13) 0.091(3) Uani 0.503(12) 1 d D U P A 2
H4B H 0.250723 0.763173 0.251012 0.110 Uiso 0.503(12) 1 calc R U P A 2
F2A F 0.694(2) 0.7473(14) 0.2631(14) 0.142(5) Uani 0.52(3) 1 d . U P B 1
F1A F 0.6842(16) 0.7596(10) 0.4488(12) 0.105(5) Uani 0.52(3) 1 d . U P B 1
B1A B 0.728(3) 0.764(2) 0.359(2) 0.074(5) Uani 0.52(3) 1 d . U P B 1
F4A F 0.7936(19) 0.8538(19) 0.358(2) 0.102(6) Uani 0.52(3) 1 d . U P B 1
F3A F 0.8040(13) 0.6811(17) 0.3699(17) 0.114(5) Uani 0.52(3) 1 d . U P B 1
C5A C 0.4046(12) 0.8498(10) 0.3836(9) 0.077(3) Uani 0.497(12) 1 d D U P A 1
H5AA H 0.471681 0.874963 0.366481 0.093 Uiso 0.497(12) 1 calc R U P A 1
H5AB H 0.368125 0.906097 0.418085 0.093 Uiso 0.497(12) 1 calc R U P A 1
N1A N 0.326(3) 0.750(2) 0.523(3) 0.045(4) Uani 0.497(12) 1 d . U P A 1
H1AA H 0.262008 0.767850 0.496342 0.054 Uiso 0.497(12) 1 d R U P A 1
H1AB H 0.342228 0.798550 0.568812 0.054 Uiso 0.497(12) 1 d R U P A 1
H1AC H 0.320138 0.685930 0.551432 0.054 Uiso 0.497(12) 1 d R U P A 1
C1A C 0.4078(15) 0.7487(11) 0.4421(14) 0.064(3) Uani 0.497(12) 1 d D U P A 1
H1A H 0.473883 0.743663 0.474535 0.077 Uiso 0.497(12) 1 calc R U P A 1
C2A C 0.3995(15) 0.6592(15) 0.3666(13) 0.082(3) Uani 0.497(12) 1 d D U P A 1
H2AA H 0.465718 0.632497 0.348252 0.098 Uiso 0.497(12) 1 calc R U P A 1
H2AB H 0.359476 0.600232 0.392371 0.098 Uiso 0.497(12) 1 calc R U P A 1
C3A C 0.3479(16) 0.7115(14) 0.2793(12) 0.088(3) Uani 0.497(12) 1 d D U P A 1
H3A H 0.321796 0.674959 0.224822 0.106 Uiso 0.497(12) 1 calc R U P A 1
C4A C 0.3454(13) 0.8080(13) 0.2903(11) 0.088(3) Uani 0.497(12) 1 d D U P A 1
H4A H 0.311176 0.853473 0.247090 0.106 Uiso 0.497(12) 1 calc R U P 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
O1 C11 1.420(6) . ?
O1 C12 1.428(6) . ?
N1B H1BA 0.9160 . ?
N1B H1BB 0.8901 . ?
N1B H1BC 0.9563 . ?
N1B C1B 1.52(4) . ?
O3 C15 1.409(6) . ?
O3 C16 1.429(6) . ?
O4 C6 1.422(6) . ?
O4 C17 1.405(6) . ?
O6 C9 1.419(6) . ?
O6 C10 1.412(6) . ?
O5 C8 1.406(6) . ?
O5 C7 1.409(6) . ?
O2 C13 1.415(6) . ?
O2 C14 1.416(6) . ?
F4B B1B 1.30(5) . ?
F1B B1B 1.35(4) . ?
F3B B1B 1.29(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.483(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.480(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.492(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.488(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.484(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.472(8) . ?
C1B H1B 0.9800 . ?
C1B C2B 1.53(2) . ?
C1B C5B 1.46(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
F2B B1B 1.46(5) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C2B C3B 1.497(19) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C5B C4B 1.45(2) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.268(17) . ?
C4B H4B 0.9300 . ?
F2A B1A 1.39(3) . ?
F1A B1A 1.34(4) . ?
B1A F4A 1.42(4) . ?
B1A F3A 1.44(4) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C1A 1.487(17) . ?
C5A C4A 1.571(18) . ?
N1A H1AA 0.9427 . ?
N1A H1AB 0.8900 . ?
N1A H1AC 0.8900 . ?
N1A C1A 1.54(4) . ?
C1A H1A 0.9800 . ?
C1A C2A 1.514(19) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.509(19) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.213(19) . ?
C4A H4A 0.9300 . ?

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
C11 O1 C12 111.7(4) . . ?
H1BA N1B H1BB 111.2 . . ?
H1BA N1B H1BC 105.4 . . ?
H1BB N1B H1BC 106.0 . . ?
C1B N1B H1BA 117.8 . . ?
C1B N1B H1BB 110.3 . . ?
C1B N1B H1BC 105.2 . . ?
C15 O3 C16 112.9(4) . . ?
C17 O4 C6 113.2(4) . . ?
C10 O6 C9 113.2(4) . . ?
C8 O5 C7 111.2(4) . . ?
C13 O2 C14 112.6(4) . . ?
O5 C8 H8A 109.7 . . ?
O5 C8 H8B 109.7 . . ?
O5 C8 C9 110.0(4) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
O3 C15 H15A 109.9 . . ?
O3 C15 H15B 109.9 . . ?
O3 C15 C14 109.1(4) . . ?
H15A C15 H15B 108.3 . . ?
C14 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
O1 C11 H11A 109.9 . . ?
O1 C11 H11B 109.9 . . ?
O1 C11 C10 108.7(4) . . ?
H11A C11 H11B 108.3 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
O4 C6 H6A 109.9 . . ?
O4 C6 H6B 109.9 . . ?
O4 C6 C7 109.0(4) . . ?
H6A C6 H6B 108.3 . . ?
C7 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
O2 C13 H13A 110.0 . . ?
O2 C13 H13B 110.0 . . ?
O2 C13 C12 108.5(4) . . ?
H13A C13 H13B 108.4 . . ?
C12 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
O3 C16 H16A 109.8 . . ?
O3 C16 H16B 109.8 . . ?
O3 C16 C17 109.5(4) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
N1B C1B H1B 110.1 . . ?
N1B C1B C2B 108.6(18) . . ?
C2B C1B H1B 110.1 . . ?
C5B C1B N1B 110.5(19) . . ?
C5B C1B H1B 110.1 . . ?
C5B C1B C2B 107.4(16) . . ?
O4 C17 C16 109.3(4) . . ?
O4 C17 H17A 109.8 . . ?
O4 C17 H17B 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
O6 C9 C8 108.2(4) . . ?
O6 C9 H9A 110.1 . . ?
O6 C9 H9B 110.1 . . ?
C8 C9 H9A 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
O5 C7 C6 109.2(5) . . ?
O5 C7 H7A 109.8 . . ?
O5 C7 H7B 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
O6 C10 C11 108.7(4) . . ?
O6 C10 H10A 110.0 . . ?
O6 C10 H10B 110.0 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
O1 C12 C13 110.5(4) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O2 C14 C15 109.5(4) . . ?
O2 C14 H14A 109.8 . . ?
O2 C14 H14B 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C1B C2B H2BA 112.2 . . ?
C1B C2B H2BB 112.2 . . ?
H2BA C2B H2BB 109.8 . . ?
C3B C2B C1B 97.8(15) . . ?
C3B C2B H2BA 112.2 . . ?
C3B C2B H2BB 112.2 . . ?
F4B B1B F1B 114(3) . . ?
F4B B1B F2B 102(3) . . ?
F1B B1B F2B 82(3) . . ?
F3B B1B F4B 124(4) . . ?
F3B B1B F1B 119(3) . . ?
F3B B1B F2B 102(2) . . ?
C1B C5B H5BA 111.5 . . ?
C1B C5B H5BB 111.5 . . ?
H5BA C5B H5BB 109.4 . . ?
C4B C5B C1B 101.2(13) . . ?
C4B C5B H5BA 111.5 . . ?
C4B C5B H5BB 111.5 . . ?
C2B C3B H3B 123.2 . . ?
C4B C3B C2B 113.6(15) . . ?
C4B C3B H3B 123.2 . . ?
C5B C4B H4B 124.3 . . ?
C3B C4B C5B 111.5(14) . . ?
C3B C4B H4B 124.3 . . ?
F2A B1A F4A 107(2) . . ?
F2A B1A F3A 102(3) . . ?
F1A B1A F2A 134(3) . . ?
F1A B1A F4A 108(3) . . ?
F1A B1A F3A 101.0(18) . . ?
F4A B1A F3A 98(3) . . ?
H5AA C5A H5AB 109.6 . . ?
C1A C5A H5AA 112.0 . . ?
C1A C5A H5AB 112.0 . . ?
C1A C5A C4A 99.0(12) . . ?
C4A C5A H5AA 112.0 . . ?
C4A C5A H5AB 112.0 . . ?
H1AA N1A H1AB 109.0 . . ?
H1AA N1A H1AC 107.5 . . ?
H1AB N1A H1AC 109.5 . . ?
C1A N1A H1AA 111.3 . . ?
C1A N1A H1AB 108.9 . . ?
C1A N1A H1AC 110.6 . . ?
C5A C1A N1A 110.2(15) . . ?
C5A C1A H1A 108.4 . . ?
C5A C1A C2A 105.5(16) . . ?
N1A C1A H1A 108.4 . . ?
C2A C1A N1A 115.6(19) . . ?
C2A C1A H1A 108.4 . . ?
C1A C2A H2AA 111.0 . . ?
C1A C2A H2AB 111.0 . . ?
H2AA C2A H2AB 109.0 . . ?
C3A C2A C1A 103.7(15) . . ?
C3A C2A H2AA 111.0 . . ?
C3A C2A H2AB 111.0 . . ?
C2A C3A H3A 124.9 . . ?
C4A C3A C2A 110.3(15) . . ?
C4A C3A H3A 124.9 . . ?
C5A C4A H4A 122.8 . . ?
C3A C4A C5A 114.4(13) . . ?
C3A C4A H4A 122.8 . . ?

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
O1 C11 C10 O6 63.6(5) . . . . ?
N1B C1B C2B C3B 96(2) . . . . ?
N1B C1B C5B C4B -88.9(19) . . . . ?
O3 C15 C14 O2 64.4(5) . . . . ?
O3 C16 C17 O4 -65.6(6) . . . . ?
O4 C6 C7 O5 68.2(6) . . . . ?
O5 C8 C9 O6 -66.4(6) . . . . ?
O2 C13 C12 O1 -67.3(6) . . . . ?
C8 O5 C7 C6 -178.7(5) . . . . ?
C15 O3 C16 C17 171.1(4) . . . . ?
C11 O1 C12 C13 172.4(4) . . . . ?
C6 O4 C17 C16 -171.2(4) . . . . ?
C13 O2 C14 C15 179.9(5) . . . . ?
C16 O3 C15 C14 177.7(4) . . . . ?
C1B C2B C3B C4B 9(2) . . . . ?
C1B C5B C4B C3B -25(2) . . . . ?
C17 O4 C6 C7 179.4(5) . . . . ?
C9 O6 C10 C11 175.6(4) . . . . ?
C7 O5 C8 C9 175.3(5) . . . . ?
C10 O6 C9 C8 -169.3(4) . . . . ?
C12 O1 C11 C10 -178.5(4) . . . . ?
C14 O2 C13 C12 -168.5(4) . . . . ?
C2B C1B C5B C4B 29(2) . . . . ?
C2B C3B C4B C5B 10(2) . . . . ?
C5B C1B C2B C3B -23.6(19) . . . . ?
C5A C1A C2A C3A -23.9(19) . . . . ?
N1A C1A C2A C3A 98(2) . . . . ?
C1A C5A C4A C3A -20.6(19) . . . . ?
C1A C2A C3A C4A 11(2) . . . . ?
C2A C3A C4A C5A 6(2) . . . . ?
C4A C5A C1A N1A -100.1(18) . . . . ?
C4A C5A C1A C2A 25.3(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
