# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 1973645'
loop_
_audit_author_name
_audit_author_address
'Yafang Gao'
;Southeast University
China
;
_audit_update_record             
;
2019-12-23 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 O6, Cl O4, C2 H7 Cl N'
_chemical_formula_sum            'C14 H31 Cl2 N O10'
_chemical_formula_weight         444.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121
_space_group_name_Hall           P2ac2ab
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9191(6)
_cell_length_b                   10.9587(6)
_cell_length_c                   20.2561(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2201.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2735
_cell_measurement_theta_min      2.3200
_cell_measurement_theta_max      21.5530

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9348
_exptl_absorpt_correction_T_max  0.9410
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11886
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3842
_reflns_number_gt                2733
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1964P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.01(16)
_refine_ls_number_reflns         3842
_refine_ls_number_parameters     245
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_ref         0.2679
_refine_ls_wR_factor_gt          0.2445
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.19947(13) 0.75359(11) 0.10929(6) 0.0934(4) Uani 1 1 d . . .
O7 O 0.2186(9) 0.8643(6) 0.1415(3) 0.240(3) Uani 1 1 d . . .
O8 O 0.2899(7) 0.7582(5) 0.0539(4) 0.199(3) Uani 1 1 d . . .
O9 O 0.2155(9) 0.6556(6) 0.1474(4) 0.294(4) Uani 1 1 d . . .
O10 O 0.0748(7) 0.7441(6) 0.0800(7) 0.264(5) Uani 1 1 d . . .
N1 N 0.6636(3) 0.2571(3) 0.14601(14) 0.0516(7) Uani 1 1 d . . .
H1B H 0.6661 0.1759 0.1455 0.077 Uiso 1 1 calc R . .
H1C H 0.7420 0.2865 0.1319 0.077 Uiso 1 1 calc R . .
H1A H 0.5977 0.2831 0.1197 0.077 Uiso 1 1 calc R . .
Cl2 Cl 0.39803(13) 0.19198(18) 0.23312(7) 0.1099(5) Uani 1 1 d . . .
O1 O 0.4802(3) 0.3966(3) 0.06053(13) 0.0695(8) Uani 1 1 d . . .
O2 O 0.4772(3) 0.1418(3) 0.05131(15) 0.0737(9) Uani 1 1 d . . .
O4 O 0.9069(3) 0.1021(3) 0.15699(15) 0.0775(9) Uani 1 1 d . . .
O5 O 0.9341(3) 0.3551(3) 0.15816(16) 0.0744(8) Uani 1 1 d . . .
O3 O 0.6562(3) -0.0071(2) 0.12727(15) 0.0739(9) Uani 1 1 d . . .
O6 O 0.7367(3) 0.4884(2) 0.08577(15) 0.0719(8) Uani 1 1 d . . .
C1 C 0.3917(5) 0.3342(5) 0.0186(2) 0.0843(14) Uani 1 1 d . . .
H1D H 0.4334 0.3234 -0.0243 0.101 Uiso 1 1 calc R . .
H1E H 0.3102 0.3818 0.0127 0.101 Uiso 1 1 calc R . .
C11 C 0.6248(7) 0.5670(4) 0.0784(2) 0.0890(17) Uani 1 1 d . . .
H11A H 0.6541 0.6448 0.0605 0.107 Uiso 1 1 calc R . .
H11B H 0.5834 0.5817 0.1211 0.107 Uiso 1 1 calc R . .
C5 C 0.7782(6) -0.0737(4) 0.1348(3) 0.0938(17) Uani 1 1 d U . .
H5A H 0.8242 -0.0789 0.0926 0.113 Uiso 1 1 calc R . .
H5B H 0.7582 -0.1560 0.1494 0.113 Uiso 1 1 calc R . .
C4 C 0.5748(6) -0.0526(4) 0.0757(3) 0.0852(15) Uani 1 1 d . . .
H4A H 0.5546 -0.1379 0.0838 0.102 Uiso 1 1 calc R . .
H4B H 0.6234 -0.0469 0.0343 0.102 Uiso 1 1 calc R . .
C13 C 0.6386(5) 0.2996(5) 0.2136(2) 0.0896(16) Uani 1 1 d D . .
H13A H 0.6741 0.2388 0.2437 0.108 Uiso 1 1 calc R . .
H13B H 0.6902 0.3738 0.2203 0.108 Uiso 1 1 calc R . .
C2 C 0.3572(5) 0.2139(5) 0.0466(3) 0.0853(15) Uani 1 1 d . . .
H2A H 0.3176 0.2241 0.0901 0.102 Uiso 1 1 calc R . .
H2B H 0.2919 0.1732 0.0186 0.102 Uiso 1 1 calc R . .
C3 C 0.4476(5) 0.0174(4) 0.0710(3) 0.0833(14) Uani 1 1 d . . .
H3A H 0.3884 -0.0204 0.0388 0.100 Uiso 1 1 calc R . .
H3B H 0.4022 0.0172 0.1134 0.100 Uiso 1 1 calc R . .
C8 C 1.0460(5) 0.2771(5) 0.1616(3) 0.0906(16) Uani 1 1 d . . .
H8A H 1.1186 0.3169 0.1854 0.109 Uiso 1 1 calc R . .
H8B H 1.0777 0.2586 0.1174 0.109 Uiso 1 1 calc R . .
C12 C 0.5270(6) 0.5101(4) 0.0336(3) 0.0839(15) Uani 1 1 d . . .
H12A H 0.4511 0.5647 0.0271 0.101 Uiso 1 1 calc R . .
H12B H 0.5688 0.4958 -0.0089 0.101 Uiso 1 1 calc R . .
C9 C 0.9615(5) 0.4660(4) 0.1205(3) 0.0914(16) Uani 1 1 d . . .
H9A H 1.0376 0.5083 0.1400 0.110 Uiso 1 1 calc R . .
H9B H 0.9852 0.4443 0.0756 0.110 Uiso 1 1 calc R . .
C6 C 0.8669(6) -0.0129(4) 0.1837(3) 0.0870(15) Uani 1 1 d U . .
H6A H 0.8188 -0.0010 0.2249 0.104 Uiso 1 1 calc R . .
H6B H 0.9456 -0.0630 0.1924 0.104 Uiso 1 1 calc R . .
C7 C 1.0074(5) 0.1627(6) 0.1959(3) 0.0996(17) Uani 1 1 d . . .
H7A H 1.0857 0.1105 0.2011 0.120 Uiso 1 1 calc R . .
H7B H 0.9718 0.1812 0.2394 0.120 Uiso 1 1 calc R . .
C10 C 0.8457(6) 0.5463(4) 0.1198(3) 0.0914(16) Uani 1 1 d . . .
H10A H 0.8188 0.5652 0.1647 0.110 Uiso 1 1 calc R . .
H10B H 0.8689 0.6221 0.0978 0.110 Uiso 1 1 calc R . .
C14 C 0.5084(7) 0.3228(7) 0.2313(3) 0.128(2) Uani 1 1 d D . .
H14A H 0.4714 0.3821 0.2006 0.154 Uiso 1 1 calc R . .
H14B H 0.5085 0.3600 0.2747 0.154 Uiso 1 1 calc R . .


_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 O9 1.333(7) . ?
Cl1 O10 1.375(8) . ?
Cl1 O7 1.391(6) . ?
Cl1 O8 1.437(7) . ?
N1 C13 1.468(5) . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 H1A 0.8900 . ?
Cl2 C14 1.804(8) . ?
O1 C1 1.400(6) . ?
O1 C12 1.435(6) . ?
O2 C2 1.431(6) . ?
O2 C3 1.451(5) . ?
O4 C6 1.428(6) . ?
O4 C7 1.434(6) . ?
O5 C8 1.403(6) . ?
O5 C9 1.460(6) . ?
O3 C4 1.411(6) . ?
O3 C5 1.422(6) . ?
O6 C11 1.413(6) . ?
O6 C10 1.431(6) . ?
C1 C2 1.475(8) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C11 C12 1.468(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 C6 1.483(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C3 1.479(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C13 C14 1.364(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C8 C7 1.484(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 C10 1.447(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
O9 Cl1 O10 107.2(5) . . ?
O9 Cl1 O7 114.6(4) . . ?
O10 Cl1 O7 113.0(5) . . ?
O9 Cl1 O8 114.0(5) . . ?
O10 Cl1 O8 103.2(7) . . ?
O7 Cl1 O8 104.5(4) . . ?
C13 N1 H1B 109.5 . . ?
C13 N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C13 N1 H1A 109.5 . . ?
H1B N1 H1A 109.5 . . ?
H1C N1 H1A 109.5 . . ?
C1 O1 C12 113.3(3) . . ?
C2 O2 C3 111.7(4) . . ?
C6 O4 C7 113.2(4) . . ?
C8 O5 C9 112.7(4) . . ?
C4 O3 C5 112.6(4) . . ?
C11 O6 C10 112.0(3) . . ?
O1 C1 C2 110.4(4) . . ?
O1 C1 H1D 109.6 . . ?
C2 C1 H1D 109.6 . . ?
O1 C1 H1E 109.6 . . ?
C2 C1 H1E 109.6 . . ?
H1D C1 H1E 108.1 . . ?
O6 C11 C12 109.0(3) . . ?
O6 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
O6 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O3 C5 C6 110.2(4) . . ?
O3 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
O3 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
O3 C4 C3 110.6(4) . . ?
O3 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C14 C13 N1 117.6(4) . . ?
C14 C13 H13A 107.9 . . ?
N1 C13 H13A 107.9 . . ?
C14 C13 H13B 107.9 . . ?
N1 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
O2 C2 C1 109.0(4) . . ?
O2 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
O2 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O2 C3 C4 109.4(4) . . ?
O2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
O2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
O5 C8 C7 109.5(4) . . ?
O5 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
O5 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O1 C12 C11 110.3(4) . . ?
O1 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
O1 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C10 C9 O5 111.4(4) . . ?
C10 C9 H9A 109.4 . . ?
O5 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
O5 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O4 C6 C5 107.9(4) . . ?
O4 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
O4 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
O4 C7 C8 108.3(4) . . ?
O4 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
O4 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
O6 C10 C9 109.6(3) . . ?
O6 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
O6 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C13 C14 Cl2 115.6(5) . . ?
C13 C14 H14A 108.4 . . ?
Cl2 C14 H14A 108.4 . . ?
C13 C14 H14B 108.4 . . ?
Cl2 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?

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
C12 O1 C1 C2 175.0(4) . . . . ?
C10 O6 C11 C12 170.3(4) . . . . ?
C4 O3 C5 C6 173.0(4) . . . . ?
C5 O3 C4 C3 178.4(4) . . . . ?
C3 O2 C2 C1 -173.0(4) . . . . ?
O1 C1 C2 O2 -62.7(5) . . . . ?
C2 O2 C3 C4 -179.4(4) . . . . ?
O3 C4 C3 O2 65.8(5) . . . . ?
C9 O5 C8 C7 -175.6(4) . . . . ?
C1 O1 C12 C11 -176.9(4) . . . . ?
O6 C11 C12 O1 61.1(5) . . . . ?
C8 O5 C9 C10 -178.1(4) . . . . ?
C7 O4 C6 C5 -172.2(4) . . . . ?
O3 C5 C6 O4 -65.9(5) . . . . ?
C6 O4 C7 C8 177.0(4) . . . . ?
O5 C8 C7 O4 63.5(5) . . . . ?
C11 O6 C10 C9 -174.8(4) . . . . ?
O5 C9 C10 O6 -64.3(6) . . . . ?
N1 C13 C14 Cl2 65.6(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C O6 0.89 2.40 2.905(4) 116.1 .
N1 H1C O5 0.89 2.12 2.901(4) 146.6 .
N1 H1B O4 0.89 2.53 2.960(4) 110.2 .
N1 H1B O3 0.89 2.04 2.921(4) 169.3 .
N1 H1A O2 0.89 2.40 2.949(4) 120.4 .
N1 H1A O1 0.89 2.08 2.940(4) 161.1 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1973647'
loop_
_audit_author_name
_audit_author_address
'Yafang Gao'
;Southeast University
China
;
_audit_update_record             
;
2019-12-23 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 O6, F6 P, C2 H7 Cl N'
_chemical_formula_sum            'C14 H31 Cl F6 N O6 P'
_chemical_formula_weight         489.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121
_space_group_name_Hall           P2ac2ab
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9996(5)
_cell_length_b                   11.1621(8)
_cell_length_c                   20.7524(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2316.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2484
_cell_measurement_theta_min      2.0980
_cell_measurement_theta_max      20.3450

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9407
_exptl_absorpt_correction_T_max  0.9464
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10585
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0985
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4964
_reflns_number_gt                2185
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.80(19)
_refine_ls_number_reflns         4964
_refine_ls_number_parameters     263
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1791
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2970
_refine_ls_wR_factor_gt          0.2479
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.29808(14) 0.24768(13) 0.10386(7) 0.0724(4) Uani 1 1 d . . .
N1 N 0.8349(3) 0.7463(3) 0.14514(14) 0.0535(9) Uani 1 1 d . . .
H1A H 0.8829 0.7934 0.1194 0.080 Uiso 1 1 calc R . .
H1B H 0.7486 0.7539 0.1357 0.080 Uiso 1 1 calc R . .
H1C H 0.8598 0.6704 0.1395 0.080 Uiso 1 1 calc R . .
Cl1 Cl 1.10348(16) 0.6838(2) 0.22809(8) 0.1411(8) Uani 1 1 d . . .
O1 O 1.0148(4) 0.8898(3) 0.06366(16) 0.0809(11) Uani 1 1 d . . .
O4 O 0.5668(3) 0.8431(4) 0.15758(18) 0.0884(12) Uani 1 1 d . . .
O5 O 1.0187(3) 0.6404(3) 0.04885(17) 0.0787(10) Uani 1 1 d . . .
O3 O 0.5930(4) 0.5940(4) 0.15302(17) 0.0877(12) Uani 1 1 d . . .
O6 O 0.8423(4) 0.4901(3) 0.12284(19) 0.0865(12) Uani 1 1 d . . .
F1 F 0.3661(5) 0.2146(5) 0.16784(19) 0.196(2) Uani 1 1 d . . .
O2 O 0.7619(4) 0.9787(3) 0.09252(19) 0.0861(12) Uani 1 1 d . . .
F2 F 0.4379(4) 0.2383(5) 0.0696(2) 0.1608(19) Uani 1 1 d . . .
F3 F 0.2292(5) 0.2763(4) 0.03762(17) 0.1365(15) Uani 1 1 d . . .
F5 F 0.3129(5) 0.3842(4) 0.1130(4) 0.226(3) Uani 1 1 d . . .
C13 C 0.8781(7) 1.0544(5) 0.0836(3) 0.093(2) Uani 1 1 d . . .
H13A H 0.8503 1.1316 0.0668 0.112 Uiso 1 1 calc R . .
H13B H 0.9215 1.0675 0.1248 0.112 Uiso 1 1 calc R . .
C10 C 0.4535(5) 0.7704(6) 0.1577(3) 0.106(2) Uani 1 1 d U . .
H10A H 0.4242 0.7558 0.1138 0.128 Uiso 1 1 calc R . .
H10B H 0.3814 0.8096 0.1808 0.128 Uiso 1 1 calc R . .
C14 C 0.9712(7) 0.9994(5) 0.0394(3) 0.095(2) Uani 1 1 d . . .
H14A H 0.9282 0.9872 -0.0019 0.114 Uiso 1 1 calc R . .
H14B H 1.0473 1.0519 0.0330 0.114 Uiso 1 1 calc R . .
C6 C 0.9237(8) 0.4505(5) 0.0723(3) 0.103(2) Uani 1 1 d . . .
H6A H 0.8747 0.4569 0.0321 0.123 Uiso 1 1 calc R . .
H6B H 0.9456 0.3668 0.0790 0.123 Uiso 1 1 calc R . .
C3 C 1.1054(7) 0.8304(6) 0.0180(3) 0.102(2) Uani 1 1 d . . .
H3A H 1.1870 0.8765 0.0133 0.122 Uiso 1 1 calc R . .
H3B H 1.0631 0.8239 -0.0240 0.122 Uiso 1 1 calc R . .
C5 C 1.0478(7) 0.5200(5) 0.0674(4) 0.104(2) Uani 1 1 d . . .
H5A H 1.0935 0.5198 0.1086 0.125 Uiso 1 1 calc R . .
H5B H 1.1063 0.4836 0.0357 0.125 Uiso 1 1 calc R . .
C1 C 0.8571(5) 0.7807(6) 0.2120(2) 0.0824(18) Uani 1 1 d . . .
H1D H 0.8278 0.7155 0.2395 0.099 Uiso 1 1 calc R . .
H1E H 0.8014 0.8495 0.2216 0.099 Uiso 1 1 calc R . .
F6 F 0.2859(5) 0.1108(4) 0.0866(3) 0.1574(19) Uani 1 1 d . . .
C7 C 0.7223(7) 0.4236(5) 0.1307(4) 0.111(2) Uani 1 1 d U . .
H7A H 0.7432 0.3432 0.1452 0.133 Uiso 1 1 calc R . .
H7B H 0.6761 0.4177 0.0897 0.133 Uiso 1 1 calc R . .
F4 F 0.1579(4) 0.2576(5) 0.1327(2) 0.176(2) Uani 1 1 d . . .
C4 C 1.1359(6) 0.7101(6) 0.0435(3) 0.101(2) Uani 1 1 d . . .
H4A H 1.1987 0.6703 0.0151 0.121 Uiso 1 1 calc R . .
H4B H 1.1774 0.7177 0.0856 0.121 Uiso 1 1 calc R . .
C2 C 0.9962(8) 0.8105(6) 0.2288(3) 0.112(2) Uani 1 1 d . . .
H2A H 0.9980 0.8463 0.2714 0.134 Uiso 1 1 calc R . .
H2B H 1.0297 0.8694 0.1985 0.134 Uiso 1 1 calc R . .
C9 C 0.4888(6) 0.6532(8) 0.1902(3) 0.114(2) Uani 1 1 d U . .
H9A H 0.5201 0.6683 0.2336 0.137 Uiso 1 1 calc R . .
H9B H 0.4104 0.6024 0.1926 0.137 Uiso 1 1 calc R . .
C8 C 0.6346(7) 0.4840(6) 0.1787(4) 0.106(2) Uani 1 1 d U . .
H8A H 0.5575 0.4341 0.1880 0.127 Uiso 1 1 calc R . .
H8B H 0.6833 0.4969 0.2185 0.127 Uiso 1 1 calc R . .
C12 C 0.6565(7) 1.0326(5) 0.1273(3) 0.104(2) Uani 1 1 d U . .
H12A H 0.6352 1.1097 0.1083 0.125 Uiso 1 1 calc R . .
H12B H 0.6843 1.0458 0.1715 0.125 Uiso 1 1 calc R . .
C11 C 0.5374(7) 0.9554(6) 0.1262(4) 0.100(2) Uani 1 1 d U . .
H11A H 0.4642 0.9951 0.1482 0.120 Uiso 1 1 calc R . .
H11B H 0.5105 0.9409 0.0820 0.120 Uiso 1 1 calc R . .


_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
P1 F4 1.529(4) . ?
P1 F1 1.537(4) . ?
P1 F5 1.543(4) . ?
P1 F3 1.570(4) . ?
P1 F2 1.572(4) . ?
P1 F6 1.574(5) . ?
N1 C1 1.457(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
Cl1 C2 1.774(8) . ?
O1 C14 1.392(7) . ?
O1 C3 1.469(7) . ?
O4 C10 1.393(7) . ?
O4 C11 1.443(7) . ?
O5 C4 1.411(7) . ?
O5 C5 1.428(7) . ?
O3 C8 1.402(7) . ?
O3 C9 1.454(7) . ?
O6 C6 1.399(8) . ?
O6 C7 1.420(8) . ?
O2 C12 1.411(7) . ?
O2 C13 1.449(7) . ?
C13 C14 1.444(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C10 C9 1.513(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C6 C5 1.467(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 C4 1.476(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 C2 1.472(9) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C7 C8 1.488(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 C11 1.470(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
F4 P1 F1 94.9(3) . . ?
F4 P1 F5 88.2(3) . . ?
F1 P1 F5 95.0(3) . . ?
F4 P1 F3 85.7(2) . . ?
F1 P1 F3 177.8(3) . . ?
F5 P1 F3 87.1(3) . . ?
F4 P1 F2 176.2(3) . . ?
F1 P1 F2 88.9(3) . . ?
F5 P1 F2 92.0(3) . . ?
F3 P1 F2 90.5(3) . . ?
F4 P1 F6 95.1(3) . . ?
F1 P1 F6 89.9(3) . . ?
F5 P1 F6 173.8(4) . . ?
F3 P1 F6 87.9(3) . . ?
F2 P1 F6 84.3(3) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C14 O1 C3 110.9(4) . . ?
C10 O4 C11 109.9(4) . . ?
C4 O5 C5 111.8(5) . . ?
C8 O3 C9 114.2(5) . . ?
C6 O6 C7 114.4(5) . . ?
C12 O2 C13 114.6(4) . . ?
C14 C13 O2 110.5(5) . . ?
C14 C13 H13A 109.6 . . ?
O2 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
O2 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
O4 C10 C9 108.3(5) . . ?
O4 C10 H10A 110.0 . . ?
C9 C10 H10A 110.0 . . ?
O4 C10 H10B 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
O1 C14 C13 110.3(5) . . ?
O1 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
O1 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
O6 C6 C5 112.1(5) . . ?
O6 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
O6 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O1 C3 C4 107.8(5) . . ?
O1 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
O1 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.5 . . ?
O5 C5 C6 110.1(5) . . ?
O5 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
O5 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N1 C1 C2 115.4(4) . . ?
N1 C1 H1D 108.4 . . ?
C2 C1 H1D 108.4 . . ?
N1 C1 H1E 108.4 . . ?
C2 C1 H1E 108.4 . . ?
H1D C1 H1E 107.5 . . ?
O6 C7 C8 109.8(5) . . ?
O6 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
O6 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O5 C4 C3 111.0(5) . . ?
O5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
O5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C1 C2 Cl1 112.9(5) . . ?
C1 C2 H2A 109.0 . . ?
Cl1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
Cl1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O3 C9 C10 108.9(5) . . ?
O3 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
O3 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
O3 C8 C7 108.5(5) . . ?
O3 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
O3 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
O2 C12 C11 110.4(5) . . ?
O2 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
O2 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O4 C11 C12 109.7(5) . . ?
O4 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
O4 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?

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
C12 O2 C13 C14 -171.1(5) . . . . ?
C11 O4 C10 C9 179.3(5) . . . . ?
C3 O1 C14 C13 177.7(5) . . . . ?
O2 C13 C14 O1 -60.8(6) . . . . ?
C7 O6 C6 C5 -178.5(5) . . . . ?
C14 O1 C3 C4 -174.1(5) . . . . ?
C4 O5 C5 C6 -179.9(5) . . . . ?
O6 C6 C5 O5 -66.7(7) . . . . ?
C6 O6 C7 C8 -171.5(5) . . . . ?
C5 O5 C4 C3 174.2(5) . . . . ?
O1 C3 C4 O5 61.6(6) . . . . ?
N1 C1 C2 Cl1 -69.4(6) . . . . ?
C8 O3 C9 C10 179.8(5) . . . . ?
O4 C10 C9 O3 -62.1(6) . . . . ?
C9 O3 C8 C7 170.1(5) . . . . ?
O6 C7 C8 O3 66.4(7) . . . . ?
C13 O2 C12 C11 172.4(5) . . . . ?
C10 O4 C11 C12 179.0(5) . . . . ?
O2 C12 C11 O4 62.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 2.06 2.943(5) 172.6 .
N1 H1A O2 0.89 2.46 2.908(5) 111.6 .
N1 H1B O3 0.89 2.40 2.961(5) 121.7 .
N1 H1B O4 0.89 2.12 2.902(5) 146.0 .
N1 H1C O5 0.89 2.48 2.960(5) 114.0 .
N1 H1C O6 0.89 2.05 2.898(5) 158.8 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2018031'
loop_
_audit_author_name
_audit_author_address
'Ya-fang Gao'
;Southeast University
China
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 O6, F6 P, C2 H7 Cl N'
_chemical_formula_sum            'C14 H7 Cl F6 N O6 P'
_chemical_formula_weight         465.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_space_group_name_Hall           P2c-2n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.9318(8)
_cell_length_b                   21.1187(17)
_cell_length_c                   11.0870(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2325.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    350(2)
_cell_measurement_reflns_used    2396
_cell_measurement_theta_min      2.8010
_cell_measurement_theta_max      22.8730

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.16298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      350(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11375
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3540
_reflns_number_gt                1803
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_number_reflns         3540
_refine_ls_number_parameters     457
_refine_ls_number_restraints     1267
_refine_ls_R_factor_all          0.1887
_refine_ls_R_factor_gt           0.1209
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.2158
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.221
_refine_ls_shift/su_max          0.094
_refine_ls_shift/su_mean         0.007

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38015(14) 0.02741(8) 0.6676(6) 0.4175(18) Uani 1 1 d U . .
N1 N 0.6546(2) 0.10365(9) 0.6937(3) 0.0811(8) Uani 1 1 d U . .
H1B H 0.7403 0.1124 0.6770 0.122 Uiso 1 1 calc R . .
H1C H 0.6356 0.1162 0.7683 0.122 Uiso 1 1 calc R . .
H1A H 0.6015 0.1238 0.6417 0.122 Uiso 1 1 calc R . .
P1 P 0.18552(18) 0.14602(9) 0.2058(3) 0.1021(6) Uani 0.50 1 d PDU A 1
F5 F 0.3197(4) 0.1162(3) 0.2322(7) 0.219(2) Uani 0.50 1 d PDU A 1
F6 F 0.0659(5) 0.1827(2) 0.1656(8) 0.220(2) Uani 0.50 1 d PDU A 1
F7 F 0.1088(5) 0.08427(17) 0.2144(6) 0.1577(16) Uani 0.50 1 d PDU A 1
F8 F 0.1662(5) 0.1649(2) 0.3337(4) 0.1529(17) Uani 0.50 1 d PDU A 1
F9 F 0.2760(5) 0.2049(2) 0.1844(7) 0.1979(18) Uani 0.50 1 d PDU A 1
F10 F 0.2096(6) 0.1288(3) 0.0742(4) 0.195(2) Uani 0.50 1 d PDU A 1
P1' P 0.2051(2) 0.13853(11) 0.1905(3) 0.1305(8) Uani 0.50 1 d PDU B 2
F14 F 0.3501(4) 0.1185(3) 0.1630(8) 0.218(2) Uani 0.50 1 d PDU B 2
F11 F 0.0607(4) 0.1491(3) 0.2115(8) 0.223(2) Uani 0.50 1 d PDU B 2
F12 F 0.2181(6) 0.1025(3) 0.3066(5) 0.192(2) Uani 0.50 1 d PDU B 2
F13 F 0.2037(7) 0.1722(3) 0.0667(5) 0.199(2) Uani 0.50 1 d PDU B 2
F15 F 0.2408(8) 0.2020(3) 0.2426(7) 0.245(2) Uani 0.50 1 d PDU B 2
F16 F 0.1910(7) 0.0779(2) 0.1154(6) 0.212(2) Uani 0.50 1 d PDU B 2
O1 O 0.4621(7) 0.1857(3) 0.5427(7) 0.170(2) Uani 0.50 1 d PDU C 1
O2 O 0.6866(2) 0.12403(15) 0.4263(7) 0.194(2) Uani 0.50 1 d PDU C 1
O3 O 0.8958(4) 0.0976(2) 0.56425(18) 0.1612(18) Uani 0.50 1 d PDU C 1
O4 O 0.9742(8) 0.0771(4) 0.8510(7) 0.1865(11) Uani 0.50 1 d PDU C 1
O5 O 0.6877(2) 0.1508(3) 0.9293(5) 0.1560(19) Uani 0.50 1 d PDU C 1
O6 O 0.4476(7) 0.2110(4) 0.8244(7) 0.180(2) Uani 0.50 1 d PDU C 1
C1 C 0.5244(4) 0.1948(2) 0.4377(10) 0.1865(11) Uani 0.50 1 d PDU C 1
C2 C 0.6187(3) 0.1719(3) 0.3686(9) 0.182(3) Uani 0.50 1 d PDU C 1
C3 C 0.8261(3) 0.1379(2) 0.3924(3) 0.195(2) Uani 0.50 1 d PDU C 1
C4 C 0.8901(3) 0.0835(3) 0.4400(9) 0.195(2) Uani 0.50 1 d PDU C 1
C5 C 1.0145(8) 0.0708(5) 0.6110(8) 0.185(3) Uani 0.50 1 d PDU C 1
C6 C 0.9919(5) 0.0692(4) 0.7346(3) 0.178(3) Uani 0.50 1 d PDU C 1
C7 C 0.8721(10) 0.0829(5) 0.9501(9) 0.155(3) Uani 0.50 1 d PDU C 1
C8 C 0.7908(3) 0.1287(2) 1.0087(7) 0.130(2) Uani 0.50 1 d PDU C 1
C9 C 0.5886(3) 0.1710(3) 1.0041(6) 0.147(2) Uani 0.50 1 d PDU C 1
C10 C 0.4690(3) 0.1681(5) 0.9331(8) 0.171(3) Uani 0.50 1 d PDU C 1
C11 C 0.3504(9) 0.2122(5) 0.7264(10) 0.181(3) Uani 0.50 1 d PDU C 1
C12 C 0.3788(9) 0.2311(4) 0.6079(9) 0.158(2) Uani 0.50 1 d PDU C 1
O1' O 0.4631(6) 0.2058(3) 0.6176(7) 0.160(2) Uani 0.50 1 d PDU D 2
O2' O 0.7382(5) 0.16474(13) 0.4367(8) 0.208(2) Uani 0.50 1 d PDU D 2
O3' O 0.9260(3) 0.1155(3) 0.4969(3) 0.196(2) Uani 0.50 1 d PDU D 2
O4' O 0.9103(5) 0.0978(3) 0.8109(6) 0.1342(18) Uani 0.50 1 d PDU D 2
O5' O 0.6228(7) 0.1270(3) 0.9548(6) 0.165(2) Uani 0.50 1 d PDU D 2
O6' O 0.5037(3) 0.1842(3) 0.84016(18) 0.1492(17) Uani 0.50 1 d PDU D 2
C1' C 0.4705(12) 0.2080(5) 0.4747(11) 0.190(3) Uani 0.50 1 d PDU D 2
C2' C 0.5813(3) 0.1621(3) 0.4418(6) 0.1865(11) Uani 0.50 1 d PDU D 2
C3' C 0.7620(3) 0.1179(3) 0.3636(3) 0.183(3) Uani 0.50 1 d PDU D 2
C4' C 0.8247(6) 0.06908(15) 0.4481(11) 0.201(3) Uani 0.50 1 d PDU D 2
C5' C 0.9405(11) 0.0858(6) 0.6373(9) 0.1865(11) Uani 0.50 1 d PDU D 2
C6' C 1.0362(8) 0.0962(4) 0.7306(10) 0.153(2) Uani 0.50 1 d PDU D 2
C7' C 0.8229(10) 0.1252(5) 0.9067(9) 0.142(3) Uani 0.50 1 d PDU D 2
C8' C 0.7515(4) 0.09708(15) 1.0057(11) 0.1865(11) Uani 0.50 1 d PDU D 2
C9' C 0.6258(3) 0.18283(17) 1.0059(3) 0.1865(11) Uani 0.50 1 d PDU D 2
C10' C 0.5219(3) 0.2168(4) 0.9449(3) 0.155(2) Uani 0.50 1 d PDU D 2
C11' C 0.3580(4) 0.1991(6) 0.8157(4) 0.213(3) Uani 0.50 1 d PDU D 2
C12' C 0.3814(5) 0.2024(4) 0.6781(3) 0.191(3) Uani 0.50 1 d PDU D 2
C13 C 0.6329(2) 0.03682(15) 0.6838(5) 0.175(2) Uani 1 1 d DU . .
H13A H 0.6280 0.0258 0.5990 0.210 Uiso 1 1 calc R . .
H13B H 0.7103 0.0151 0.7176 0.210 Uiso 1 1 calc R . .
C14 C 0.5098(3) 0.0129(2) 0.7445(5) 0.257(3) Uani 1 1 d DU . .
H14A H 0.5013 0.0326 0.8231 0.308 Uiso 1 1 calc R . .
H14B H 0.5176 -0.0325 0.7564 0.308 Uiso 1 1 calc R . .


_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 C14 1.575(5) . ?
N1 C13 1.432(4) . ?
P1 F8 1.486(6) . ?
P1 F6 1.487(5) . ?
P1 F5 1.502(5) . ?
P1 F7 1.513(4) . ?
P1 F10 1.523(6) . ?
P1 F9 1.553(5) . ?
P1' F11 1.470(5) . ?
P1' F12 1.501(7) . ?
P1' F15 1.502(6) . ?
P1' F14 1.532(5) . ?
P1' F16 1.534(6) . ?
P1' F13 1.546(6) . ?
O1 C1 1.332(12) . ?
O1 C12 1.459(11) . ?
O2 C2 1.373(8) . ?
O2 C3 1.465(4) . ?
O3 C4 1.411(10) . ?
O3 C5 1.406(9) . ?
O4 C6 1.313(8) . ?
O4 C7 1.500(12) . ?
O5 C9 1.356(6) . ?
O5 C8 1.429(7) . ?
O6 C11 1.455(12) . ?
O6 C10 1.522(11) . ?
C1 C2 1.303(10) . ?
C3 C4 1.414(7) . ?
C5 C6 1.389(10) . ?
C7 C8 1.417(11) . ?
C9 C10 1.426(7) . ?
C11 C12 1.401(14) . ?
O1' C12' 1.055(8) . ?
O1' C1' 1.587(14) . ?
O2' C3' 1.301(7) . ?
O2' C2' 1.560(6) . ?
O3' C4' 1.505(8) . ?
O3' C5' 1.684(11) . ?
O4' C7' 1.489(11) . ?
O4' C6' 1.535(11) . ?
O5' C9' 1.309(8) . ?
O5' C8' 1.533(9) . ?
O6' C10' 1.362(6) . ?
O6' C11' 1.506(6) . ?
C1' C2' 1.511(12) . ?
C3' C4' 1.525(9) . ?
C5' C6' 1.422(14) . ?
C7' C8' 1.436(13) . ?
C9' C10' 1.428(6) . ?
C11' C12' 1.544(6) . ?
C13 C14 1.484(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F8 P1 F6 92.5(4) . . ?
F8 P1 F5 92.4(4) . . ?
F6 P1 F5 170.2(4) . . ?
F8 P1 F7 96.1(3) . . ?
F6 P1 F7 93.7(3) . . ?
F5 P1 F7 94.2(3) . . ?
F8 P1 F10 177.6(3) . . ?
F6 P1 F10 87.8(4) . . ?
F5 P1 F10 87.0(4) . . ?
F7 P1 F10 86.2(3) . . ?
F8 P1 F9 90.3(4) . . ?
F6 P1 F9 90.0(3) . . ?
F5 P1 F9 81.5(3) . . ?
F7 P1 F9 172.4(4) . . ?
F10 P1 F9 87.3(4) . . ?
F11 P1' F12 91.5(4) . . ?
F11 P1' F15 91.9(4) . . ?
F12 P1' F15 95.9(4) . . ?
F11 P1' F14 172.2(4) . . ?
F12 P1' F14 87.1(4) . . ?
F15 P1' F14 95.8(4) . . ?
F11 P1' F16 97.1(4) . . ?
F12 P1' F16 92.9(4) . . ?
F15 P1' F16 167.3(5) . . ?
F14 P1' F16 75.4(4) . . ?
F11 P1' F13 93.5(4) . . ?
F12 P1' F13 174.5(4) . . ?
F15 P1' F13 86.2(4) . . ?
F14 P1' F13 87.7(4) . . ?
F16 P1' F13 84.3(4) . . ?
C1 O1 C12 127.0(6) . . ?
C2 O2 C3 101.5(4) . . ?
C4 O3 C5 108.0(5) . . ?
C6 O4 C7 145.1(8) . . ?
C9 O5 C8 104.3(5) . . ?
C11 O6 C10 134.0(7) . . ?
C2 C1 O1 142.5(7) . . ?
C1 C2 O2 110.6(8) . . ?
C4 C3 O2 99.6(4) . . ?
O3 C4 C3 102.2(5) . . ?
C6 C5 O3 103.8(6) . . ?
O4 C6 C5 171.2(9) . . ?
C8 C7 O4 141.0(9) . . ?
C7 C8 O5 110.4(7) . . ?
O5 C9 C10 104.7(5) . . ?
C9 C10 O6 121.8(6) . . ?
C12 C11 O6 124.9(8) . . ?
C11 C12 O1 113.0(8) . . ?
C12' O1' C1' 132.3(7) . . ?
C3' O2' C2' 100.2(4) . . ?
C4' O3' C5' 98.5(7) . . ?
C7' O4' C6' 153.8(7) . . ?
C9' O5' C8' 101.1(5) . . ?
C10' O6' C11' 100.1(4) . . ?
C2' C1' O1' 104.8(8) . . ?
C1' C2' O2' 135.5(6) . . ?
O2' C3' C4' 101.9(5) . . ?
O3' C4' C3' 93.1(4) . . ?
C6' C5' O3' 132.2(9) . . ?
C5' C6' O4' 83.2(6) . . ?
C8' C7' O4' 132.3(8) . . ?
C7' C8' O5' 87.7(7) . . ?
O5' C9' C10' 103.4(5) . . ?
O6' C10' C9' 104.2(5) . . ?
C12' C11' O6' 92.4(3) . . ?
O1' C12' C11' 138.3(5) . . ?
C14 C13 N1 115.2(3) . . ?
C13 C14 Cl1 111.2(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 2.20 3.075(7) 169.0 .
N1 H1A O1' 0.89 2.23 2.997(7) 144.7 .
N1 H1A O2 0.89 2.53 3.012(9) 114.4 .
N1 H1B O3 0.89 2.01 2.795(4) 146.1 .
N1 H1B O4' 0.89 2.27 2.855(6) 123.2 .
N1 H1C O5 0.89 2.00 2.815(6) 152.4 .
N1 H1C O5' 0.89 2.08 2.954(8) 165.6 .
N1 H1C O6' 0.89 2.10 2.789(5) 133.6 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.059

# start Validation Reply Form
_vrf_PLAT089_1                   
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.73 Note  
RESPONSE: Poor quality of crystal in high temperature environments.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1973646'
loop_
_audit_author_name
_audit_author_address
'Yafang Gao'
;Southeast University
China
;
_audit_update_record             
;
2020-07-22 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 O6, Cl O4, C2 H7 Cl N'
_chemical_formula_sum            'C14 H7 Cl2 N O10'
_chemical_formula_weight         420.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_space_group_name_Hall           P2c-2n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.8711(9)
_cell_length_b                   20.732(3)
_cell_length_c                   10.8819(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2226.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    368(2)
_cell_measurement_reflns_used    1873
_cell_measurement_theta_min      2.8280
_cell_measurement_theta_max      30.0580

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      368(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10454
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3345
_reflns_number_gt                1764
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_number_reflns         3345
_refine_ls_number_parameters     421
_refine_ls_number_restraints     811
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.1024
_refine_ls_wR_factor_ref         0.2047
_refine_ls_wR_factor_gt          0.1861
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_restrained_S_all      0.844
_refine_ls_shift/su_max          0.099
_refine_ls_shift/su_mean         0.011

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.39319(10) 0.01997(5) 0.6812(4) 0.3464(11) Uani 1 1 d U . .
N1 N 0.66022(17) 0.10219(7) 0.6955(3) 0.1103(8) Uani 1 1 d U . .
H1B H 0.7371 0.1111 0.6563 0.165 Uiso 1 1 calc R . .
H1C H 0.6657 0.1160 0.7727 0.165 Uiso 1 1 calc R . .
H1A H 0.5916 0.1218 0.6579 0.165 Uiso 1 1 calc R . .
Cl1 Cl 0.19903(11) 0.13940(6) 0.21294(15) 0.1539(7) Uani 0.50 1 d PDU A 1
O7 O 0.2368(5) 0.10188(17) 0.3145(3) 0.213(2) Uani 0.50 1 d PDU A 1
O8 O 0.0667(2) 0.1638(2) 0.2134(10) 0.236(3) Uani 0.50 1 d PDU A 1
O9 O 0.2843(3) 0.19351(12) 0.2102(8) 0.198(2) Uani 0.50 1 d PDU A 1
O10 O 0.2164(7) 0.09701(15) 0.1133(3) 0.219(2) Uani 0.50 1 d PDU A 1
Cl1' Cl 0.20942(15) 0.13707(7) 0.17702(16) 0.2173(11) Uani 0.50 1 d PDU B 2
O14 O 0.3451(2) 0.1247(3) 0.2060(8) 0.283(3) Uani 0.50 1 d PDU B 2
O11 O 0.1132(3) 0.08925(14) 0.2000(8) 0.223(2) Uani 0.50 1 d PDU B 2
O12 O 0.1643(5) 0.19236(12) 0.2380(4) 0.270(2) Uani 0.50 1 d PDU B 2
O13 O 0.1993(9) 0.1463(4) 0.0499(2) 0.314(3) Uani 0.50 1 d PDU B 2
O1 O 0.4274(6) 0.1783(3) 0.5175(6) 0.1896(17) Uani 0.50 1 d PDU C 1
O2 O 0.6601(2) 0.12228(15) 0.4456(4) 0.1491(14) Uani 0.50 1 d PDU C 1
O3 O 0.9176(3) 0.09684(15) 0.5656(2) 0.1093(11) Uani 0.50 1 d PDU C 1
O4 O 0.9579(6) 0.0797(3) 0.8200(5) 0.1847(8) Uani 0.50 1 d PDU C 1
O5 O 0.6446(5) 0.1228(2) 0.9454(4) 0.1528(15) Uani 0.50 1 d PDU C 1
O6 O 0.4618(4) 0.1977(2) 0.7988(4) 0.1607(15) Uani 0.50 1 d PDU C 1
C1 C 0.5217(8) 0.1811(4) 0.4433(8) 0.1847(8) Uani 0.50 1 d PDU C 1
C2 C 0.6099(2) 0.1702(3) 0.3559(6) 0.190(2) Uani 0.50 1 d PDU C 1
C3 C 0.8131(2) 0.1342(2) 0.4016(3) 0.1705(19) Uani 0.50 1 d PDU C 1
C4 C 0.8489(3) 0.0661(2) 0.4319(6) 0.167(2) Uani 0.50 1 d PDU C 1
C5 C 0.9981(6) 0.0448(3) 0.6144(7) 0.168(2) Uani 0.50 1 d PDU C 1
C6 C 1.0458(4) 0.0918(3) 0.7026(9) 0.1507(16) Uani 0.50 1 d PDU C 1
C7 C 0.9094(9) 0.1202(4) 0.9380(8) 0.192(2) Uani 0.50 1 d PDU C 1
C8 C 0.7674(3) 0.11662(17) 1.0219(7) 0.163(2) Uani 0.50 1 d PDU C 1
C9 C 0.5962(3) 0.18349(18) 0.9978(5) 0.1424(17) Uani 0.50 1 d PDU C 1
C10 C 0.4574(8) 0.1722(5) 0.9278(7) 0.181(2) Uani 0.50 1 d PDU C 1
C11 C 0.3539(5) 0.1934(3) 0.7107(9) 0.1555(18) Uani 0.50 1 d PDU C 1
C12 C 0.3947(7) 0.2343(3) 0.5997(7) 0.156(2) Uani 0.50 1 d PDU C 1
O1' O 0.4907(3) 0.19321(16) 0.5742(3) 0.1074(10) Uani 0.50 1 d PDU D 2
O2' O 0.7537(3) 0.16239(12) 0.4556(3) 0.1442(14) Uani 0.50 1 d PDU D 2
O3' O 0.9808(2) 0.1222(3) 0.4915(3) 0.1911(18) Uani 0.50 1 d PDU D 2
O4' O 0.9136(4) 0.0965(2) 0.8112(4) 0.1370(13) Uani 0.50 1 d PDU D 2
O5' O 0.7211(5) 0.1647(3) 0.9784(6) 0.1864(18) Uani 0.50 1 d PDU D 2
O6' O 0.4996(5) 0.1935(2) 0.8462(5) 0.1435(13) Uani 0.50 1 d PDU D 2
C1' C 0.5391(8) 0.2189(3) 0.4458(7) 0.164(2) Uani 0.50 1 d PDU D 2
C2' C 0.6322(3) 0.17715(16) 0.3853(9) 0.1847(8) Uani 0.50 1 d PDU D 2
C3' C 0.7966(2) 0.10548(16) 0.3823(4) 0.1629(19) Uani 0.50 1 d PDU D 2
C4' C 0.8779(4) 0.08183(16) 0.5232(5) 0.1681(19) Uani 0.50 1 d PDU D 2
C5' C 0.9888(9) 0.0928(4) 0.6333(7) 0.1847(8) Uani 0.50 1 d PDU D 2
C6' C 1.0366(8) 0.0626(3) 0.7474(8) 0.167(2) Uani 0.50 1 d PDU D 2
C7' C 0.8784(9) 0.0717(4) 0.9493(8) 0.175(2) Uani 0.50 1 d PDU D 2
C8' C 0.8514(9) 0.1351(4) 1.0130(9) 0.1847(8) Uani 0.50 1 d PDU D 2
C9' C 0.5629(9) 0.1558(4) 0.9962(10) 0.1847(8) Uani 0.50 1 d PDU D 2
C10' C 0.5039(9) 0.2193(4) 0.9703(8) 0.1783(19) Uani 0.50 1 d PDU D 2
C11' C 0.3895(7) 0.2278(3) 0.7815(7) 0.1643(19) Uani 0.50 1 d PDU D 2
C12' C 0.3791(7) 0.2098(3) 0.6537(8) 0.1489(18) Uani 0.50 1 d PU D 2
C13 C 0.6378(2) 0.03323(13) 0.6947(4) 0.299(3) Uani 1 1 d DU . .
H13A H 0.7184 0.0124 0.7267 0.359 Uiso 1 1 calc R . .
H13B H 0.6272 0.0195 0.6100 0.359 Uiso 1 1 calc R . .
C14 C 0.5191(3) 0.00970(19) 0.7660(4) 0.318(3) Uani 1 1 d DU . .
H14A H 0.5092 0.0340 0.8417 0.382 Uiso 1 1 calc R . .
H14B H 0.5296 -0.0356 0.7862 0.382 Uiso 1 1 calc R . .


_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
Cl2 C14 1.562(4) . ?
N1 C13 1.447(3) . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 H1A 0.8900 . ?
Cl1 O8 1.401(3) . ?
Cl1 O7 1.402(3) . ?
Cl1 O9 1.403(3) . ?
Cl1 O10 1.406(3) . ?
Cl1' O11 1.395(3) . ?
Cl1' O12 1.398(3) . ?
Cl1' O14 1.400(3) . ?
Cl1' O13 1.401(3) . ?
O1 C1 1.234(10) . ?
O1 C12 1.501(9) . ?
O2 C2 1.479(7) . ?
O2 C3 1.604(4) . ?
O2 C1 1.832(9) . ?
O3 C5 1.442(7) . ?
O3 C4 1.728(6) . ?
O4 C6 1.564(10) . ?
O4 C7 1.607(10) . ?
O5 C8 1.476(7) . ?
O5 C9 1.462(6) . ?
O6 C11 1.436(9) . ?
O6 C10 1.501(9) . ?
C1 C2 1.309(10) . ?
C3 C4 1.492(6) . ?
C5 C6 1.447(10) . ?
C7 C8 1.674(10) . ?
C9 C10 1.585(9) . ?
C11 C12 1.529(11) . ?
O1' C12' 1.442(8) . ?
O1' C1' 1.570(8) . ?
O2' C2' 1.456(6) . ?
O2' C3' 1.486(5) . ?
O3' C4' 1.361(6) . ?
O3' C5' 1.660(9) . ?
O4' C6' 1.565(8) . ?
O4' C7' 1.626(9) . ?
O5' C8' 1.474(10) . ?
O5' C9' 1.585(10) . ?
O6' C10' 1.454(9) . ?
O6' C11' 1.478(8) . ?
O6' C9' 1.914(11) . ?
C1' C2' 1.423(9) . ?
C3' C4' 1.798(6) . ?
C4' C5' 1.639(10) . ?
C5' C6' 1.469(11) . ?
C7' C8' 1.511(11) . ?
C9' C10' 1.467(11) . ?
C11' C12' 1.443(11) . ?
C13 C14 1.488(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
C13 N1 H1B 109.5 . . ?
C13 N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C13 N1 H1A 109.5 . . ?
H1B N1 H1A 109.5 . . ?
H1C N1 H1A 109.5 . . ?
O8 Cl1 O7 116.4(5) . . ?
O8 Cl1 O9 105.8(2) . . ?
O7 Cl1 O9 107.5(4) . . ?
O8 Cl1 O10 110.0(5) . . ?
O7 Cl1 O10 103.2(2) . . ?
O9 Cl1 O10 114.2(4) . . ?
O11 Cl1' O12 106.3(3) . . ?
O11 Cl1' O14 118.7(3) . . ?
O12 Cl1' O14 110.4(4) . . ?
O11 Cl1' O13 103.1(5) . . ?
O12 Cl1' O13 109.5(4) . . ?
O14 Cl1' O13 108.4(5) . . ?
C1 O1 C12 121.0(6) . . ?
C2 O2 C3 90.9(3) . . ?
C2 O2 C1 45.0(3) . . ?
C3 O2 C1 126.6(4) . . ?
C5 O3 C4 104.5(4) . . ?
C6 O4 C7 137.2(5) . . ?
C8 O5 C9 97.1(3) . . ?
C11 O6 C10 125.5(5) . . ?
O1 C1 C2 165.7(9) . . ?
O1 C1 O2 121.4(7) . . ?
C2 C1 O2 53.1(4) . . ?
C1 C2 O2 81.9(5) . . ?
C4 C3 O2 90.7(3) . . ?
C3 C4 O3 86.0(3) . . ?
O3 C5 C6 85.4(5) . . ?
C5 C6 O4 104.7(5) . . ?
O4 C7 C8 131.5(6) . . ?
O5 C8 C7 112.1(6) . . ?
O5 C9 C10 88.2(4) . . ?
O6 C10 C9 111.8(6) . . ?
O6 C11 C12 107.3(5) . . ?
O1 C12 C11 95.6(5) . . ?
C12' O1' C1' 133.3(5) . . ?
C2' O2' C3' 96.8(3) . . ?
C4' O3' C5' 64.9(4) . . ?
C6' O4' C7' 115.7(5) . . ?
C8' O5' C9' 141.3(6) . . ?
C10' O6' C11' 106.6(5) . . ?
C10' O6' C9' 49.4(4) . . ?
C11' O6' C9' 147.5(5) . . ?
C2' C1' O1' 113.7(6) . . ?
C1' C2' O2' 114.6(7) . . ?
O2' C3' C4' 83.4(3) . . ?
O3' C4' C5' 66.4(4) . . ?
O3' C4' C3' 87.1(3) . . ?
C5' C4' C3' 152.0(4) . . ?
C6' C5' C4' 140.6(7) . . ?
C6' C5' O3' 163.2(7) . . ?
C4' C5' O3' 48.7(3) . . ?
C5' C6' O4' 86.2(5) . . ?
C8' C7' O4' 100.7(6) . . ?
O5' C8' C7' 113.5(7) . . ?
C10' C9' O5' 105.3(7) . . ?
C10' C9' O6' 48.7(4) . . ?
O5' C9' O6' 99.8(6) . . ?
O6' C10' C9' 81.9(6) . . ?
C12' C11' O6' 112.7(6) . . ?
O1' C12' C11' 125.8(6) . . ?
N1 C13 C14 116.2(3) . . ?
N1 C13 H13A 108.2 . . ?
C14 C13 H13A 108.2 . . ?
N1 C13 H13B 108.3 . . ?
C14 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 Cl2 105.9(3) . . ?
C13 C14 H14A 110.6 . . ?
Cl2 C14 H14A 110.5 . . ?
C13 C14 H14B 110.6 . . ?
Cl2 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 2.52 3.394(6) 169.2 .
N1 H1A O1' 0.89 2.00 2.847(4) 157.8 .
N1 H1A O2 0.89 2.41 2.750(6) 103.2 .
N1 H1B O2' 0.89 2.43 3.037(5) 125.3 .
N1 H1B O3 0.89 2.06 2.909(3) 159.7 .
N1 H1C O5 0.89 1.90 2.757(6) 162.4 .
N1 H1C O5' 0.89 2.51 3.394(7) 169.5 .
N1 H1A O6 0.89 2.54 3.004(5) 112.9 .
N1 H1C O6' 0.89 2.43 2.964(5) 118.9 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.048

# start Validation Reply Form
_vrf_PLAT089_1                   
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.91 Note  
RESPONSE: Poor quality of crystal in high temperature environments.
;
_vrf_PLAT315_1                   
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing).        C3' Check 
RESPONSE: The disordered motion in the high temperature phase is strong.
;
# end Validation Reply Form
