# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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 2212389'
loop_
_audit_author_name
_audit_author_address
'Mengmeng Lun'
;Southeast University
China
;
_audit_update_record             
;
2022-10-12 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_audit_creation_date             2022-09-17
_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         '2(C12 H24 O6), 2(C4 H14 N2), 4(Cl O4)'
_chemical_formula_sum            'C32 H76 Cl4 N4 O28'
_chemical_formula_weight         1106.76
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7728(5)
_cell_length_b                   27.5589(9)
_cell_length_c                   16.5361(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.487(4)
_cell_angle_gamma                90
_cell_volume                     5340.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9116
_cell_measurement_temperature    291
_cell_measurement_theta_max      22.7890
_cell_measurement_theta_min      2.1720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.73233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            52559
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.112
_diffrn_reflns_theta_min         1.888
_diffrn_ambient_temperature      291
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.841
_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                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5058
_reflns_number_total             14448
_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         0.642
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         14448
_refine_ls_number_restraints     396
_refine_ls_R_factor_all          0.2864
_refine_ls_R_factor_gt           0.1485
_refine_ls_restrained_S_all      1.128
_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)+(0.0100P)²+15.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2258
_refine_ls_wR_factor_ref         0.2652
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14-C13
 1.54 with sigma of 0.01
 C30-C29
 1.54 with sigma of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: O25(0.5) O27(0.5)
5.a Ternary CH refined with riding coordinates:
 N2(H2), N4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C17(H17A,H17B), C18(H18A,H18B),
  C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,
 H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), N1(H1C,H1D,H1E), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), N3(H3C,H3D,H3E)
;
_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
C1 C -0.2211(10) 0.2558(3) 0.1492(5) 0.151(3) Uani 1 1 d . . . . .
H1A H -0.189780 0.273074 0.105398 0.181 Uiso 1 1 calc R U . . .
H1B H -0.216440 0.276830 0.196428 0.181 Uiso 1 1 calc R U . . .
C2 C -0.3394(11) 0.2438(4) 0.1255(8) 0.186(4) Uani 1 1 d . . . . .
H2A H -0.370403 0.226680 0.169668 0.223 Uiso 1 1 calc R U . . .
H2B H -0.382567 0.273560 0.115797 0.223 Uiso 1 1 calc R U . . .
C3 C -0.4265(9) 0.2192(5) -0.0018(7) 0.202(5) Uani 1 1 d . . . . .
H3A H -0.427464 0.253237 -0.016618 0.243 Uiso 1 1 calc R U . . .
H3B H -0.498531 0.212775 0.020149 0.243 Uiso 1 1 calc R U . . .
C4 C -0.4297(9) 0.1930(5) -0.0753(7) 0.176(3) Uani 1 1 d . . . . .
H4A H -0.505933 0.179992 -0.087229 0.211 Uiso 1 1 calc R U . . .
H4B H -0.416517 0.215651 -0.118394 0.211 Uiso 1 1 calc R U . . .
C5 C -0.3451(9) 0.1316(5) -0.1535(6) 0.180(3) Uani 1 1 d . . . . .
H5A H -0.302976 0.151467 -0.188806 0.216 Uiso 1 1 calc R U . . .
H5B H -0.420582 0.125515 -0.180395 0.216 Uiso 1 1 calc R U . . .
C6 C -0.2818(11) 0.0833(5) -0.1335(7) 0.190(4) Uani 1 1 d . . . . .
H6A H -0.322749 0.064896 -0.095582 0.228 Uiso 1 1 calc R U . . .
H6B H -0.280619 0.064333 -0.182758 0.228 Uiso 1 1 calc R U . . .
C7 C -0.1119(11) 0.0482(4) -0.0911(6) 0.169(3) Uani 1 1 d . . . . .
H7A H -0.105847 0.032657 -0.143212 0.203 Uiso 1 1 calc R U . . .
H7B H -0.148275 0.025617 -0.056674 0.203 Uiso 1 1 calc R U . . .
C8 C 0.0010(10) 0.0606(4) -0.0538(6) 0.157(3) Uani 1 1 d . . . . .
H8A H 0.050455 0.032461 -0.052754 0.189 Uiso 1 1 calc R U . . .
H8B H 0.034012 0.085950 -0.084967 0.189 Uiso 1 1 calc R U . . .
C9 C 0.0991(9) 0.0912(4) 0.0616(6) 0.159(3) Uani 1 1 d . . . . .
H9A H 0.149778 0.063375 0.067769 0.191 Uiso 1 1 calc R U . . .
H9B H 0.133015 0.114882 0.027884 0.191 Uiso 1 1 calc R U . . .
C10 C 0.0873(9) 0.1113(4) 0.1378(7) 0.163(3) Uani 1 1 d . . . . .
H10A H 0.054637 0.087384 0.171825 0.195 Uiso 1 1 calc R U . . .
H10B H 0.161947 0.120159 0.163526 0.195 Uiso 1 1 calc R U . . .
C11 C 0.0211(8) 0.1801(4) 0.2015(6) 0.153(3) Uani 1 1 d . . . . .
H11A H 0.099383 0.187285 0.221516 0.184 Uiso 1 1 calc R U . . .
H11B H -0.014298 0.162701 0.243503 0.184 Uiso 1 1 calc R U . . .
C12 C -0.0400(9) 0.2243(4) 0.1816(6) 0.152(3) Uani 1 1 d . . . . .
H12A H -0.027088 0.247251 0.226014 0.183 Uiso 1 1 calc R U . . .
H12B H -0.013186 0.238761 0.133430 0.183 Uiso 1 1 calc R U . . .
O1 O -0.1571(6) 0.21371(18) 0.1676(3) 0.1226(16) Uani 1 1 d . . . . .
O2 O -0.3526(8) 0.2150(2) 0.0554(6) 0.225(4) Uani 1 1 d . . . . .
O3 O -0.3528(5) 0.1554(3) -0.0775(4) 0.176(3) Uani 1 1 d . . . . .
O4 O -0.1777(7) 0.0905(3) -0.1020(4) 0.163(2) Uani 1 1 d . . . . .
O5 O -0.0086(6) 0.0763(2) 0.0228(4) 0.1383(19) Uani 1 1 d . . . . .
O6 O 0.0185(5) 0.1517(2) 0.1313(4) 0.140(2) Uani 1 1 d . . . . .
C13 C -0.2562(8) 0.0860(3) 0.1067(6) 0.146(3) Uani 1 1 d D . . . .
H13A H -0.261551 0.058533 0.069861 0.175 Uiso 1 1 calc R U . . .
H13B H -0.199583 0.077917 0.151220 0.175 Uiso 1 1 calc R U . . .
C14 C -0.3636(9) 0.0913(3) 0.1390(7) 0.183(4) Uani 1 1 d D . . . .
H14A H -0.420574 0.100292 0.095322 0.220 Uiso 1 1 calc R U . . .
H14B H -0.358112 0.117648 0.178147 0.220 Uiso 1 1 calc R U . . .
C15 C -0.5236(9) 0.0451(4) 0.1712(6) 0.170(4) Uani 1 1 d . . . . .
H15A H -0.553325 0.073729 0.194764 0.254 Uiso 1 1 calc R U . . .
H15B H -0.548113 0.016934 0.198940 0.254 Uiso 1 1 calc R U . . .
H15C H -0.551190 0.043337 0.114786 0.254 Uiso 1 1 calc R U . . .
C16 C -0.3663(9) 0.0485(5) 0.2678(8) 0.212(5) Uani 1 1 d . . . . .
H16A H -0.286213 0.055520 0.276312 0.318 Uiso 1 1 calc R U . . .
H16B H -0.381076 0.017558 0.291426 0.318 Uiso 1 1 calc R U . . .
H16C H -0.408411 0.073207 0.292879 0.318 Uiso 1 1 calc R U . . .
N1 N -0.2146(5) 0.12707(18) 0.0641(3) 0.1011(18) Uani 1 1 d . . . . .
H1C H -0.234798 0.123940 0.011114 0.121 Uiso 1 1 calc R U . . .
H1D H -0.138866 0.128366 0.072856 0.121 Uiso 1 1 calc R U . . .
H1E H -0.244429 0.154237 0.082074 0.121 Uiso 1 1 calc R U . . .
N2 N -0.4024(8) 0.0471(3) 0.1790(6) 0.170(3) Uani 1 1 d . . . . .
H2 H -0.371287 0.018183 0.154657 0.204 Uiso 1 1 calc R U . . .
C17 C -0.1430(9) 0.3927(3) 0.1083(6) 0.140(2) Uani 1 1 d . . . . .
H17A H -0.163091 0.425083 0.124700 0.167 Uiso 1 1 calc R U . . .
H17B H -0.187054 0.369759 0.137013 0.167 Uiso 1 1 calc R U . . .
C18 C -0.1741(8) 0.3872(3) 0.0196(6) 0.141(3) Uani 1 1 d . . . . .
H18A H -0.255378 0.392494 0.007369 0.170 Uiso 1 1 calc R U . . .
H18B H -0.133900 0.411309 -0.009581 0.170 Uiso 1 1 calc R U . . .
C19 C -0.1854(7) 0.3295(3) -0.0851(5) 0.134(2) Uani 1 1 d . . . . .
H19A H -0.149069 0.350342 -0.122272 0.161 Uiso 1 1 calc R U . . .
H19B H -0.267087 0.334814 -0.093280 0.161 Uiso 1 1 calc R U . . .
C20 C -0.1594(8) 0.2779(4) -0.1019(5) 0.142(3) Uani 1 1 d . . . . .
H20A H -0.193921 0.257304 -0.063489 0.171 Uiso 1 1 calc R U . . .
H20B H -0.192164 0.269463 -0.156104 0.171 Uiso 1 1 calc R U . . .
C21 C -0.0128(9) 0.2209(3) -0.0965(5) 0.146(3) Uani 1 1 d . . . . .
H21A H -0.045033 0.205997 -0.146673 0.175 Uiso 1 1 calc R U . . .
H21B H -0.042661 0.204314 -0.051312 0.175 Uiso 1 1 calc R U . . .
C22 C 0.1161(10) 0.2176(3) -0.0895(6) 0.160(3) Uani 1 1 d . . . . .
H22A H 0.139568 0.184841 -0.101455 0.192 Uiso 1 1 calc R U . . .
H22B H 0.146575 0.239539 -0.127869 0.192 Uiso 1 1 calc R U . . .
C23 C 0.2703(9) 0.2222(4) 0.0033(6) 0.168(3) Uani 1 1 d . . . . .
H23A H 0.312052 0.245155 -0.027160 0.201 Uiso 1 1 calc R U . . .
H23B H 0.289699 0.189690 -0.013098 0.201 Uiso 1 1 calc R U . . .
C24 C 0.3022(9) 0.2285(4) 0.0907(7) 0.160(3) Uani 1 1 d . . . . .
H24A H 0.257277 0.206722 0.120927 0.192 Uiso 1 1 calc R U . . .
H24B H 0.382034 0.220298 0.103227 0.192 Uiso 1 1 calc R U . . .
C25 C 0.3095(9) 0.2825(5) 0.1952(7) 0.171(3) Uani 1 1 d . . . . .
H25A H 0.390867 0.278039 0.208785 0.205 Uiso 1 1 calc R U . . .
H25B H 0.270135 0.258371 0.224851 0.205 Uiso 1 1 calc R U . . .
C26 C 0.2770(9) 0.3312(4) 0.2213(6) 0.168(3) Uani 1 1 d . . . . .
H26A H 0.297166 0.334945 0.279252 0.202 Uiso 1 1 calc R U . . .
H26B H 0.317413 0.355707 0.193208 0.202 Uiso 1 1 calc R U . . .
C27 C 0.1266(10) 0.3817(4) 0.2295(6) 0.154(3) Uani 1 1 d . . . . .
H27A H 0.164810 0.407176 0.201957 0.184 Uiso 1 1 calc R U . . .
H27B H 0.147259 0.385191 0.287401 0.184 Uiso 1 1 calc R U . . .
C28 C 0.0005(9) 0.3874(3) 0.2121(5) 0.143(2) Uani 1 1 d . . . . .
H28A H -0.038663 0.361973 0.238902 0.171 Uiso 1 1 calc R U . . .
H28B H -0.023404 0.418514 0.232176 0.171 Uiso 1 1 calc R U . . .
O7 O -0.1453(4) 0.3407(2) -0.0052(3) 0.1208(16) Uani 1 1 d . . . . .
O8 O -0.0403(5) 0.26976(19) -0.0956(3) 0.1195(16) Uani 1 1 d . . . . .
O9 O 0.1554(6) 0.2297(2) -0.0130(4) 0.1354(19) Uani 1 1 d . . . . .
O10 O 0.2843(5) 0.2750(3) 0.1137(4) 0.148(2) Uani 1 1 d . . . . .
O11 O 0.1634(5) 0.3368(2) 0.2040(3) 0.1362(19) Uani 1 1 d . . . . .
O12 O -0.0252(6) 0.38477(18) 0.1310(3) 0.1238(17) Uani 1 1 d . . . . .
C29 C 0.1654(9) 0.3581(3) -0.0259(5) 0.157(4) Uani 1 1 d D . . . .
H29A H 0.236661 0.341463 -0.031961 0.188 Uiso 1 1 calc R U . . .
H29B H 0.124510 0.360963 -0.079437 0.188 Uiso 1 1 calc R U . . .
C30 C 0.1902(9) 0.4050(3) 0.0044(5) 0.151(4) Uani 1 1 d D . . . .
H30A H 0.217051 0.401405 0.061429 0.181 Uiso 1 1 calc R U . . .
H30B H 0.118383 0.422383 0.002280 0.181 Uiso 1 1 calc R U . . .
C31 C 0.2578(7) 0.4836(3) 0.0007(5) 0.130(3) Uani 1 1 d . . . . .
H31A H 0.182640 0.495630 -0.015941 0.195 Uiso 1 1 calc R U . . .
H31B H 0.313492 0.504703 -0.019670 0.195 Uiso 1 1 calc R U . . .
H31C H 0.269245 0.482683 0.058912 0.195 Uiso 1 1 calc R U . . .
C32 C 0.2960(8) 0.4328(3) -0.1102(5) 0.145(3) Uani 1 1 d . . . . .
H32A H 0.339510 0.403897 -0.116897 0.218 Uiso 1 1 calc R U . . .
H32B H 0.339920 0.460664 -0.122954 0.218 Uiso 1 1 calc R U . . .
H32C H 0.226767 0.431724 -0.145857 0.218 Uiso 1 1 calc R U . . .
N3 N 0.0981(4) 0.32863(16) 0.0246(3) 0.0769(13) Uani 1 1 d . . . . .
H3C H 0.107820 0.297403 0.013322 0.092 Uiso 1 1 calc R U . . .
H3D H 0.024708 0.336325 0.014575 0.092 Uiso 1 1 calc R U . . .
H3E H 0.120638 0.334085 0.076684 0.092 Uiso 1 1 calc R U . . .
N4 N 0.2699(6) 0.4360(2) -0.0310(4) 0.1123(19) Uani 1 1 d . . . . .
H4 H 0.342008 0.425747 -0.001410 0.135 Uiso 1 1 calc R U . . .
Cl1 Cl -0.0393(2) 0.02873(9) 0.31386(15) 0.1112(6) Uani 1 1 d . . . . .
O13 O -0.0517(7) 0.0762(2) 0.3149(5) 0.200(3) Uani 1 1 d . . . . .
O14 O -0.1069(9) 0.0092(3) 0.2576(7) 0.284(5) Uani 1 1 d . . . . .
O15 O 0.0640(7) 0.0148(3) 0.2873(5) 0.210(3) Uani 1 1 d . . . . .
O16 O -0.0411(9) 0.0107(3) 0.3865(5) 0.246(4) Uani 1 1 d . . . . .
Cl2 Cl -0.5470(3) 0.17651(10) 0.3194(2) 0.1385(9) Uani 1 1 d . . . . .
O17 O -0.6450(11) 0.1950(4) 0.3362(7) 0.296(6) Uani 1 1 d . . . . .
O18 O -0.5863(11) 0.1542(3) 0.2527(7) 0.287(5) Uani 1 1 d . . . . .
O19 O -0.5020(8) 0.1465(4) 0.3732(7) 0.297(6) Uani 1 1 d . . . . .
O20 O -0.4779(9) 0.2114(4) 0.2991(6) 0.274(5) Uani 1 1 d . . . . .
Cl3 Cl -0.47054(18) 0.07851(8) -0.37439(14) 0.1028(6) Uani 1 1 d . . . . .
O21 O -0.5815(6) 0.0723(3) -0.3539(4) 0.175(3) Uani 1 1 d . . . . .
O22 O -0.4663(5) 0.0688(3) -0.4568(4) 0.157(2) Uani 1 1 d . . . . .
O23 O -0.4016(6) 0.0449(2) -0.3320(4) 0.171(2) Uani 1 1 d . . . . .
O24 O -0.4296(6) 0.1241(2) -0.3541(4) 0.175(3) Uani 1 1 d . . . . .
Cl4 Cl -0.6413(2) 0.06419(8) -0.06450(18) 0.1240(8) Uani 1 1 d . . . . .
O25 O -0.6404(17) 0.0545(6) -0.1565(12) 0.242(6) Uani 0.5 1 d . . P . .
O26 O -0.6961(8) 0.1034(3) -0.0797(5) 0.208(3) Uani 1 1 d . . . . .
O27 O -0.6230(14) 0.0949(5) 0.0105(11) 0.193(4) Uani 0.5 1 d . . P . .
O28 O -0.5304(6) 0.0543(3) -0.0533(5) 0.204(3) Uani 1 1 d . . . . .
O29 O -0.6985(6) 0.0261(2) -0.0399(6) 0.217(4) 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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.448(13) . ?
C1 O1 1.399(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 O2 1.402(12) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.411(14) . ?
C3 O2 1.227(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 O3 1.378(12) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.546(15) . ?
C5 O3 1.428(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 O4 1.299(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.452(13) . ?
C7 O4 1.402(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 O5 1.353(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.396(12) . ?
C9 O5 1.425(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 O6 1.375(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.438(12) . ?
C11 O6 1.396(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 O1 1.407(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.426(7) . ?
C13 N1 1.444(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 N2 1.479(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 N2 1.421(11) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 N2 1.489(13) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
N2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.484(11) . ?
C17 O12 1.418(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 O7 1.398(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.484(11) . ?
C19 O7 1.395(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 O8 1.414(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.513(12) . ?
C21 O8 1.386(9) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 O9 1.346(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.469(13) . ?
C23 O9 1.370(10) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 O10 1.358(11) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.472(13) . ?
C25 O10 1.367(11) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 O11 1.350(11) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.493(12) . ?
C27 O11 1.391(10) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 O12 1.348(9) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.405(7) . ?
C29 N3 1.452(8) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 N4 1.435(8) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C31 N4 1.426(8) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C32 N4 1.376(8) . ?
N3 H3C 0.8900 . ?
N3 H3D 0.8900 . ?
N3 H3E 0.8900 . ?
N4 H4 0.9800 . ?
Cl1 O13 1.317(6) . ?
Cl1 O14 1.283(8) . ?
Cl1 O15 1.387(7) . ?
Cl1 O16 1.302(7) . ?
Cl2 O17 1.315(10) . ?
Cl2 O18 1.307(9) . ?
Cl2 O19 1.291(8) . ?
Cl2 O20 1.323(9) . ?
Cl3 O21 1.391(6) . ?
Cl3 O22 1.395(6) . ?
Cl3 O23 1.377(6) . ?
Cl3 O24 1.375(6) . ?
Cl4 O25 1.545(19) . ?
Cl4 O26 1.270(7) . ?
Cl4 O27 1.499(18) . ?
Cl4 O28 1.330(7) . ?
Cl4 O29 1.331(7) . ?

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
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 C2 110.7(8) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
O2 C2 C1 112.4(11) . . ?
O2 C2 H2A 109.1 . . ?
O2 C2 H2B 109.1 . . ?
H3A C3 H3B 106.3 . . ?
C4 C3 H3A 106.1 . . ?
C4 C3 H3B 106.1 . . ?
O2 C3 H3A 106.1 . . ?
O2 C3 H3B 106.1 . . ?
O2 C3 C4 125.0(12) . . ?
C3 C4 H4A 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
O3 C4 C3 116.3(10) . . ?
O3 C4 H4A 108.2 . . ?
O3 C4 H4B 108.2 . . ?
H5A C5 H5B 108.7 . . ?
C6 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
O3 C5 H5A 110.5 . . ?
O3 C5 H5B 110.5 . . ?
O3 C5 C6 106.1(8) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O4 C6 C5 111.8(11) . . ?
O4 C6 H6A 109.2 . . ?
O4 C6 H6B 109.2 . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
O4 C7 H7A 109.8 . . ?
O4 C7 H7B 109.8 . . ?
O4 C7 C8 109.2(10) . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
O5 C8 C7 108.6(9) . . ?
O5 C8 H8A 110.0 . . ?
O5 C8 H8B 110.0 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C10 C9 O5 111.1(10) . . ?
O5 C9 H9A 109.4 . . ?
O5 C9 H9B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O6 C10 C9 111.1(11) . . ?
O6 C10 H10A 109.4 . . ?
O6 C10 H10B 109.4 . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
O6 C11 H11A 110.0 . . ?
O6 C11 H11B 110.0 . . ?
O6 C11 C12 108.3(9) . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
O1 C12 C11 108.8(8) . . ?
O1 C12 H12A 109.9 . . ?
O1 C12 H12B 109.9 . . ?
C1 O1 C12 111.3(7) . . ?
C3 O2 C2 126.7(11) . . ?
C4 O3 C5 117.8(9) . . ?
C6 O4 C7 114.4(10) . . ?
C8 O5 C9 111.3(8) . . ?
C10 O6 C11 115.0(9) . . ?
H13A C13 H13B 107.3 . . ?
C14 C13 H13A 108.0 . . ?
C14 C13 H13B 108.0 . . ?
C14 C13 N1 117.1(7) . . ?
N1 C13 H13A 108.0 . . ?
N1 C13 H13B 108.0 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C13 C14 N2 113.9(7) . . ?
H14A C14 H14B 107.7 . . ?
N2 C14 H14A 108.8 . . ?
N2 C14 H14B 108.8 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
C13 N1 H1C 109.5 . . ?
C13 N1 H1D 109.5 . . ?
C13 N1 H1E 109.5 . . ?
H1C N1 H1D 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C14 N2 C16 110.4(10) . . ?
C14 N2 H2 110.1 . . ?
C15 N2 C14 110.0(9) . . ?
C15 N2 C16 106.2(8) . . ?
C15 N2 H2 110.1 . . ?
C16 N2 H2 110.1 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
O12 C17 H17A 109.0 . . ?
O12 C17 H17B 109.0 . . ?
O12 C17 C18 112.9(8) . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O7 C18 C17 109.8(7) . . ?
O7 C18 H18A 109.7 . . ?
O7 C18 H18B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
O7 C19 H19A 109.8 . . ?
O7 C19 H19B 109.8 . . ?
O7 C19 C20 109.4(8) . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
O8 C20 C19 111.0(7) . . ?
O8 C20 H20A 109.4 . . ?
O8 C20 H20B 109.4 . . ?
H21A C21 H21B 108.6 . . ?
C22 C21 H21A 110.3 . . ?
C22 C21 H21B 110.3 . . ?
O8 C21 H21A 110.3 . . ?
O8 C21 H21B 110.3 . . ?
O8 C21 C22 106.9(8) . . ?
C21 C22 H22A 110.1 . . ?
C21 C22 H22B 110.1 . . ?
H22A C22 H22B 108.4 . . ?
O9 C22 C21 108.0(9) . . ?
O9 C22 H22A 110.1 . . ?
O9 C22 H22B 110.1 . . ?
H23A C23 H23B 108.3 . . ?
C24 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
O9 C23 H23A 109.8 . . ?
O9 C23 H23B 109.8 . . ?
O9 C23 C24 109.3(9) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
O10 C24 C23 110.8(10) . . ?
O10 C24 H24A 109.5 . . ?
O10 C24 H24B 109.5 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
O10 C25 H25A 109.0 . . ?
O10 C25 H25B 109.0 . . ?
O10 C25 C26 112.9(10) . . ?
C25 C26 H26A 109.9 . . ?
C25 C26 H26B 109.9 . . ?
H26A C26 H26B 108.3 . . ?
O11 C26 C25 108.8(9) . . ?
O11 C26 H26A 109.9 . . ?
O11 C26 H26B 109.9 . . ?
H27A C27 H27B 108.0 . . ?
C28 C27 H27A 109.3 . . ?
C28 C27 H27B 109.3 . . ?
O11 C27 H27A 109.3 . . ?
O11 C27 H27B 109.3 . . ?
O11 C27 C28 111.6(8) . . ?
C27 C28 H28A 110.1 . . ?
C27 C28 H28B 110.1 . . ?
H28A C28 H28B 108.4 . . ?
O12 C28 C27 108.1(8) . . ?
O12 C28 H28A 110.1 . . ?
O12 C28 H28B 110.1 . . ?
C19 O7 C18 114.4(7) . . ?
C21 O8 C20 112.7(7) . . ?
C22 O9 C23 113.0(8) . . ?
C24 O10 C25 113.2(9) . . ?
C26 O11 C27 111.6(8) . . ?
C28 O12 C17 112.1(7) . . ?
H29A C29 H29B 107.6 . . ?
C30 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C30 C29 N3 114.5(7) . . ?
N3 C29 H29A 108.6 . . ?
N3 C29 H29B 108.6 . . ?
C29 C30 H30A 106.9 . . ?
C29 C30 H30B 106.9 . . ?
C29 C30 N4 121.6(7) . . ?
H30A C30 H30B 106.7 . . ?
N4 C30 H30A 106.9 . . ?
N4 C30 H30B 106.9 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N4 C31 H31A 109.5 . . ?
N4 C31 H31B 109.5 . . ?
N4 C31 H31C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N4 C32 H32A 109.5 . . ?
N4 C32 H32B 109.5 . . ?
N4 C32 H32C 109.5 . . ?
C29 N3 H3C 109.5 . . ?
C29 N3 H3D 109.5 . . ?
C29 N3 H3E 109.5 . . ?
H3C N3 H3D 109.5 . . ?
H3C N3 H3E 109.5 . . ?
H3D N3 H3E 109.5 . . ?
C30 N4 H4 101.2 . . ?
C31 N4 C30 107.9(6) . . ?
C31 N4 H4 101.2 . . ?
C32 N4 C30 124.4(7) . . ?
C32 N4 C31 116.5(6) . . ?
C32 N4 H4 101.2 . . ?
O13 Cl1 O15 112.4(5) . . ?
O14 Cl1 O13 111.4(6) . . ?
O14 Cl1 O15 99.0(6) . . ?
O14 Cl1 O16 116.5(8) . . ?
O16 Cl1 O13 110.8(6) . . ?
O16 Cl1 O15 106.2(6) . . ?
O17 Cl2 O20 110.3(7) . . ?
O18 Cl2 O17 96.5(8) . . ?
O18 Cl2 O20 107.7(8) . . ?
O19 Cl2 O17 114.4(8) . . ?
O19 Cl2 O18 111.7(7) . . ?
O19 Cl2 O20 114.7(6) . . ?
O21 Cl3 O22 109.7(4) . . ?
O23 Cl3 O21 108.3(5) . . ?
O23 Cl3 O22 107.1(4) . . ?
O24 Cl3 O21 111.6(4) . . ?
O24 Cl3 O22 111.6(5) . . ?
O24 Cl3 O23 108.3(4) . . ?
O26 Cl4 O25 90.2(7) . . ?
O26 Cl4 O27 73.4(6) . . ?
O26 Cl4 O28 132.4(6) . . ?
O26 Cl4 O29 118.0(6) . . ?
O27 Cl4 O25 153.8(10) . . ?
O28 Cl4 O25 90.1(8) . . ?
O28 Cl4 O27 86.5(7) . . ?
O28 Cl4 O29 108.4(5) . . ?
O29 Cl4 O25 102.5(9) . . ?
O29 Cl4 O27 103.2(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
C1 C2 O2 C3 -138.2(13) . . . . ?
C2 C1 O1 C12 173.2(9) . . . . ?
C3 C4 O3 C5 -173.3(10) . . . . ?
C4 C3 O2 C2 172.5(13) . . . . ?
C5 C6 O4 C7 -173.1(9) . . . . ?
C6 C5 O3 C4 -163.9(9) . . . . ?
C7 C8 O5 C9 -177.4(9) . . . . ?
C8 C7 O4 C6 -178.5(9) . . . . ?
C9 C10 O6 C11 -167.1(8) . . . . ?
C10 C9 O5 C8 174.6(9) . . . . ?
C11 C12 O1 C1 179.0(8) . . . . ?
C12 C11 O6 C10 171.1(9) . . . . ?
O1 C1 C2 O2 -61.7(12) . . . . ?
O2 C3 C4 O3 10(2) . . . . ?
O3 C5 C6 O4 -64.3(12) . . . . ?
O4 C7 C8 O5 67.4(12) . . . . ?
O5 C9 C10 O6 -60.8(12) . . . . ?
O6 C11 C12 O1 70.7(10) . . . . ?
C13 C14 N2 C15 -149.7(10) . . . . ?
C13 C14 N2 C16 93.4(12) . . . . ?
N1 C13 C14 N2 177.8(9) . . . . ?
C17 C18 O7 C19 171.5(7) . . . . ?
C18 C17 O12 C28 -176.9(7) . . . . ?
C19 C20 O8 C21 169.2(7) . . . . ?
C20 C19 O7 C18 -174.6(7) . . . . ?
C21 C22 O9 C23 172.4(8) . . . . ?
C22 C21 O8 C20 180.0(7) . . . . ?
C23 C24 O10 C25 178.2(8) . . . . ?
C24 C23 O9 C22 -170.6(9) . . . . ?
C25 C26 O11 C27 178.3(8) . . . . ?
C26 C25 O10 C24 -173.0(9) . . . . ?
C27 C28 O12 C17 -176.6(7) . . . . ?
C28 C27 O11 C26 -178.7(8) . . . . ?
O7 C19 C20 O8 -63.2(9) . . . . ?
O8 C21 C22 O9 72.0(10) . . . . ?
O9 C23 C24 O10 -64.4(12) . . . . ?
O10 C25 C26 O11 60.2(12) . . . . ?
O11 C27 C28 O12 -61.9(10) . . . . ?
O12 C17 C18 O7 58.5(10) . . . . ?
C29 C30 N4 C31 167.5(10) . . . . ?
C29 C30 N4 C32 25.3(15) . . . . ?
N3 C29 C30 N4 170.3(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT026_1                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        35% Check 
RESPONSE: Due to high collection temperature of 291 K, 
reflections at high resolution cannot be collected.
;
_vrf_PLAT340_1                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01557 Ang.  
RESPONSE: This alerts are generated because of many
 disordered parts in the structure.
;
# 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_sq
_database_code_depnum_ccdc_archive 'CCDC 2212392'
loop_
_audit_author_name
_audit_author_address
'Mengmeng Lun'
;Southeast University
China
;
_audit_update_record             
;
2022-10-12 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_audit_creation_date             2022-09-17
_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, Cl O4, C4 H13 N2'
_chemical_formula_sum            'C16 H37 Cl N2 O10'
_chemical_formula_weight         452.92
_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                   12.8215(7)
_cell_length_b                   13.3193(10)
_cell_length_c                   14.0006(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2390.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5022
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5890
_cell_measurement_theta_min      2.2040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.72806
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.822
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10420
_diffrn_reflns_point_group_measured_fraction_full 0.726
_diffrn_reflns_point_group_measured_fraction_max 0.557
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.296
_diffrn_reflns_theta_min         2.205
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.822
_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                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.305
_reflns_Friedel_fraction_full    0.425
_reflns_Friedel_fraction_max     0.271
_reflns_number_gt                3242
_reflns_number_total             3987
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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         0.339
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.02(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.069
_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)+(0.0791P)²+0.2338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1296
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.02(10)
 -0.02(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
3.b Idealised Me refined as rotating group:
 N1(H1C,H1D,H1E), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.79538(18) -0.55903(16) -0.37734(19) 0.0635(6) Uani 1 1 d . . . . .
C1 C -0.8668(3) -0.5320(3) -0.4499(3) 0.0727(10) Uani 1 1 d . . . . .
H1A H -0.830144 -0.522136 -0.509780 0.087 Uiso 1 1 calc R U . . .
H1B H -0.901479 -0.469675 -0.433198 0.087 Uiso 1 1 calc R U . . .
O2 O -0.58943(17) -0.59486(16) -0.31643(16) 0.0556(5) Uani 1 1 d . . . . .
C2 C -0.7229(3) -0.4802(2) -0.3555(3) 0.0676(10) Uani 1 1 d . . . . .
H2A H -0.760353 -0.421363 -0.333399 0.081 Uiso 1 1 calc R U . . .
H2B H -0.684179 -0.462053 -0.412399 0.081 Uiso 1 1 calc R U . . .
O3 O -0.52963(15) -0.79744(15) -0.30353(17) 0.0538(5) Uani 1 1 d . . . . .
C3 C -0.6506(3) -0.5147(3) -0.2809(3) 0.0628(9) Uani 1 1 d . . . . .
H3A H -0.605583 -0.459752 -0.261575 0.075 Uiso 1 1 calc R U . . .
H3B H -0.689599 -0.536813 -0.225415 0.075 Uiso 1 1 calc R U . . .
O4 O -0.62621(17) -0.94396(16) -0.42215(19) 0.0600(6) Uani 1 1 d . . . . .
C4 C -0.5155(3) -0.6294(3) -0.2485(3) 0.0652(9) Uani 1 1 d . . . . .
H4A H -0.550769 -0.649536 -0.190277 0.078 Uiso 1 1 calc R U . . .
H4B H -0.466854 -0.576047 -0.233044 0.078 Uiso 1 1 calc R U . . .
O5 O -0.83313(16) -0.90414(16) -0.47938(17) 0.0579(5) Uani 1 1 d . . . . .
C5 C -0.4581(2) -0.7170(3) -0.2903(3) 0.0618(9) Uani 1 1 d . . . . .
H5A H -0.427347 -0.698289 -0.351021 0.074 Uiso 1 1 calc R U . . .
H5B H -0.402468 -0.737654 -0.247584 0.074 Uiso 1 1 calc R U . . .
O6 O -0.89518(15) -0.69941(15) -0.49997(19) 0.0567(6) Uani 1 1 d . . . . .
C6 C -0.4782(3) -0.8859(3) -0.3362(3) 0.0644(9) Uani 1 1 d . . . . .
H6A H -0.424854 -0.905648 -0.290735 0.077 Uiso 1 1 calc R U . . .
H6B H -0.444737 -0.872998 -0.397108 0.077 Uiso 1 1 calc R U . . .
C7 C -0.5557(3) -0.9675(3) -0.3467(3) 0.0689(10) Uani 1 1 d . . . . .
H7A H -0.520271 -1.030139 -0.360571 0.083 Uiso 1 1 calc R U . . .
H7B H -0.593982 -0.975601 -0.287434 0.083 Uiso 1 1 calc R U . . .
C8 C -0.7008(3) -1.0207(2) -0.4365(3) 0.0672(9) Uani 1 1 d . . . . .
H8A H -0.738214 -1.033476 -0.377509 0.081 Uiso 1 1 calc R U . . .
H8B H -0.666116 -1.082256 -0.455634 0.081 Uiso 1 1 calc R U . . .
C9 C -0.7758(3) -0.9880(2) -0.5130(3) 0.0660(10) Uani 1 1 d . . . . .
H9A H -0.737798 -0.969974 -0.570437 0.079 Uiso 1 1 calc R U . . .
H9B H -0.823008 -1.042554 -0.528477 0.079 Uiso 1 1 calc R U . . .
C10 C -0.9072(3) -0.8704(3) -0.5470(3) 0.0651(9) Uani 1 1 d . . . . .
H10A H -0.956210 -0.923847 -0.561322 0.078 Uiso 1 1 calc R U . . .
H10B H -0.872320 -0.851507 -0.605774 0.078 Uiso 1 1 calc R U . . .
C11 C -0.9636(2) -0.7828(3) -0.5071(3) 0.0657(10) Uani 1 1 d . . . . .
H11A H -1.021957 -0.765829 -0.548155 0.079 Uiso 1 1 calc R U . . .
H11B H -0.990765 -0.799390 -0.444433 0.079 Uiso 1 1 calc R U . . .
C12 C -0.9450(3) -0.6139(3) -0.4602(3) 0.0717(10) Uani 1 1 d . . . . .
H12A H -0.974099 -0.630594 -0.398216 0.086 Uiso 1 1 calc R U . . .
H12B H -1.001372 -0.592194 -0.501459 0.086 Uiso 1 1 calc R U . . .
Cl1 Cl -0.76959(6) -0.28970(7) -0.58678(8) 0.0677(3) Uani 1 1 d . . . . .
O7 O -0.7386(4) -0.2045(3) -0.6342(4) 0.143(2) Uani 1 1 d . . . . .
O8 O -0.7964(6) -0.2629(4) -0.4937(4) 0.177(3) Uani 1 1 d . . . . .
O9 O -0.6941(2) -0.3667(3) -0.5940(3) 0.1067(11) Uani 1 1 d . . . . .
O10 O -0.8616(3) -0.3320(4) -0.6174(6) 0.190(3) Uani 1 1 d . . . . .
N1 N -0.67416(17) -0.73229(17) -0.45943(18) 0.0453(5) Uani 1 1 d . . . . .
H1C H -0.740477 -0.719053 -0.473376 0.054 Uiso 1 1 calc R U . . .
H1D H -0.659896 -0.710267 -0.400847 0.054 Uiso 1 1 calc R U . . .
H1E H -0.663462 -0.798245 -0.462167 0.054 Uiso 1 1 calc R U . . .
N2 N -0.6465(2) -0.8046(2) -0.6538(2) 0.0581(7) Uani 1 1 d . . . . .
C13 C -0.6058(3) -0.6815(3) -0.5287(3) 0.0710(10) Uani 1 1 d . . . . .
H13A H -0.534802 -0.704867 -0.519781 0.085 Uiso 1 1 calc R U . . .
H13B H -0.606868 -0.609846 -0.516393 0.085 Uiso 1 1 calc R U . . .
C14 C -0.6378(4) -0.7000(3) -0.6299(3) 0.0725(10) Uani 1 1 d . . . . .
H14A H -0.704575 -0.667830 -0.641144 0.087 Uiso 1 1 calc R U . . .
H14B H -0.587184 -0.669044 -0.672105 0.087 Uiso 1 1 calc R U . . .
C15 C -0.5459(3) -0.8538(4) -0.6560(4) 0.0906(13) Uani 1 1 d . . . . .
H15A H -0.502516 -0.822343 -0.703238 0.136 Uiso 1 1 calc R U . . .
H15B H -0.554989 -0.923403 -0.671847 0.136 Uiso 1 1 calc R U . . .
H15C H -0.513378 -0.848333 -0.594483 0.136 Uiso 1 1 calc R U . . .
C16 C -0.6988(4) -0.8142(5) -0.7451(4) 0.117(2) Uani 1 1 d . . . . .
H16A H -0.770732 -0.795524 -0.738255 0.176 Uiso 1 1 calc R U . . .
H16B H -0.694415 -0.882496 -0.766667 0.176 Uiso 1 1 calc R U . . .
H16C H -0.665911 -0.770918 -0.790934 0.176 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
O1 C1 1.414(4) . ?
O1 C2 1.435(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C12 1.489(5) . ?
O2 C3 1.415(4) . ?
O2 C4 1.419(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.470(6) . ?
O3 C5 1.422(4) . ?
O3 C6 1.426(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C7 1.426(5) . ?
O4 C8 1.414(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.499(5) . ?
O5 C9 1.418(4) . ?
O5 C10 1.415(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O6 C11 1.419(4) . ?
O6 C12 1.419(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.480(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.505(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.482(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
Cl1 O7 1.374(4) . ?
Cl1 O8 1.394(5) . ?
Cl1 O9 1.414(3) . ?
Cl1 O10 1.376(4) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
N1 C13 1.472(4) . ?
N2 C14 1.437(5) . ?
N2 C15 1.447(5) . ?
N2 C16 1.449(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.496(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C1 O1 C2 112.7(3) . . ?
O1 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
O1 C1 C12 108.6(3) . . ?
H1A C1 H1B 108.4 . . ?
C12 C1 H1A 110.0 . . ?
C12 C1 H1B 110.0 . . ?
C3 O2 C4 112.3(3) . . ?
O1 C2 H2A 109.8 . . ?
O1 C2 H2B 109.8 . . ?
O1 C2 C3 109.4(3) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C5 O3 C6 111.4(2) . . ?
O2 C3 C2 109.6(3) . . ?
O2 C3 H3A 109.8 . . ?
O2 C3 H3B 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C8 O4 C7 112.0(3) . . ?
O2 C4 H4A 110.0 . . ?
O2 C4 H4B 110.0 . . ?
O2 C4 C5 108.6(3) . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C10 O5 C9 112.1(3) . . ?
O3 C5 C4 108.7(3) . . ?
O3 C5 H5A 110.0 . . ?
O3 C5 H5B 110.0 . . ?
C4 C5 H5A 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.3 . . ?
C11 O6 C12 112.2(3) . . ?
O3 C6 H6A 109.9 . . ?
O3 C6 H6B 109.9 . . ?
O3 C6 C7 109.1(3) . . ?
H6A C6 H6B 108.3 . . ?
C7 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
O4 C7 C6 109.8(3) . . ?
O4 C7 H7A 109.7 . . ?
O4 C7 H7B 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O4 C8 H8A 109.9 . . ?
O4 C8 H8B 109.9 . . ?
O4 C8 C9 108.9(3) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
O5 C9 C8 108.8(3) . . ?
O5 C9 H9A 109.9 . . ?
O5 C9 H9B 109.9 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
O5 C10 H10A 109.9 . . ?
O5 C10 H10B 109.9 . . ?
O5 C10 C11 109.0(3) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
O6 C11 C10 110.0(3) . . ?
O6 C11 H11A 109.7 . . ?
O6 C11 H11B 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C1 C12 H12A 109.9 . . ?
C1 C12 H12B 109.9 . . ?
O6 C12 C1 108.9(3) . . ?
O6 C12 H12A 109.9 . . ?
O6 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
O7 Cl1 O8 108.2(3) . . ?
O7 Cl1 O9 111.5(2) . . ?
O7 Cl1 O10 115.9(5) . . ?
O8 Cl1 O9 114.9(4) . . ?
O10 Cl1 O8 100.6(5) . . ?
O10 Cl1 O9 105.5(3) . . ?
H1C N1 H1D 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C13 N1 H1C 109.5 . . ?
C13 N1 H1D 109.5 . . ?
C13 N1 H1E 109.5 . . ?
C14 N2 C15 112.0(3) . . ?
C14 N2 C16 109.1(4) . . ?
C15 N2 C16 110.7(4) . . ?
N1 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
N1 C13 C14 112.6(3) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
N2 C14 C13 113.7(3) . . ?
N2 C14 H14A 108.8 . . ?
N2 C14 H14B 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C12 O6 -69.3(4) . . . . ?
O1 C2 C3 O2 64.7(4) . . . . ?
C1 O1 C2 C3 -179.0(3) . . . . ?
O2 C4 C5 O3 -65.2(4) . . . . ?
C2 O1 C1 C12 -174.2(3) . . . . ?
O3 C6 C7 O4 66.9(4) . . . . ?
C3 O2 C4 C5 177.3(3) . . . . ?
O4 C8 C9 O5 -65.5(4) . . . . ?
C4 O2 C3 C2 178.1(3) . . . . ?
O5 C10 C11 O6 68.5(4) . . . . ?
C5 O3 C6 C7 178.8(3) . . . . ?
C6 O3 C5 C4 -175.4(3) . . . . ?
C7 O4 C8 C9 176.8(3) . . . . ?
C8 O4 C7 C6 178.8(3) . . . . ?
C9 O5 C10 C11 -179.8(3) . . . . ?
C10 O5 C9 C8 -178.7(3) . . . . ?
C11 O6 C12 C1 176.8(3) . . . . ?
C12 O6 C11 C10 -178.8(3) . . . . ?
N1 C13 C14 N2 -54.3(5) . . . . ?
C15 N2 C14 C13 -69.3(5) . . . . ?
C16 N2 C14 C13 167.8(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.142 0.757 0.176 23.0 3.2 ?
2 0.358 0.757 0.676 23.0 3.1 ?
3 0.642 0.243 0.176 23.0 3.2 ?
4 0.858 0.243 0.676 23.0 3.2 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.02(10)
2 -0.02(10)

####################################################################### 
# 
# 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 2212391'
loop_
_audit_author_name
_audit_author_address
'Mengmeng Lun'
;Southeast University
China
;
_audit_update_record             
;
2022-10-12 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_audit_creation_date             2022-09-17
_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         'C10 H20 O5, C4 H13 N2, Cl O4'
_chemical_formula_sum            'C14 H33 Cl N2 O9'
_chemical_formula_weight         408.87
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   10.0923(12)
_cell_length_b                   13.1793(16)
_cell_length_c                   16.253(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2161.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1176
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.5090
_cell_measurement_theta_min      2.3660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.86488
_exptl_absorpt_correction_type   multi-scan
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.1421
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9117
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.989
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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         0.689
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                1340
_reflns_number_total             3670
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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         0.350
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.18(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     146
_refine_ls_R_factor_all          0.2427
_refine_ls_R_factor_gt           0.0983
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1621P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2394
_refine_ls_wR_factor_ref         0.2986
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.18(14)
 -0.18(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B)
4.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), N1(H1C,H1D,H1E)
;
_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
C1 C 0.8951(6) 0.6080(4) 0.2316(4) 0.1092(13) Uani 1 1 d . . . . .
H1A H 0.909241 0.595584 0.173466 0.131 Uiso 1 1 calc R U . . .
H1B H 0.980208 0.623036 0.256466 0.131 Uiso 1 1 calc R U . . .
C2 C 0.8050(7) 0.6969(5) 0.2420(4) 0.1317(13) Uani 1 1 d . . . . .
H2A H 0.841140 0.755211 0.213325 0.158 Uiso 1 1 calc R U . . .
H2B H 0.718849 0.681629 0.218572 0.158 Uiso 1 1 calc R U . . .
C3 C 0.7147(7) 0.8006(5) 0.3460(5) 0.1506(13) Uani 1 1 d . . . . .
H3A H 0.627619 0.792639 0.321563 0.181 Uiso 1 1 calc R U . . .
H3B H 0.754323 0.861915 0.323868 0.181 Uiso 1 1 calc R U . . .
C4 C 0.7030(7) 0.8089(6) 0.4314(5) 0.1551(14) Uani 1 1 d . . . . .
H4A H 0.665963 0.875060 0.443871 0.186 Uiso 1 1 calc R U . . .
H4B H 0.791279 0.806762 0.454853 0.186 Uiso 1 1 calc R U . . .
C5 C 0.6400(7) 0.7113(6) 0.5619(4) 0.1502(13) Uani 1 1 d . . . . .
H5A H 0.654335 0.774774 0.590698 0.180 Uiso 1 1 calc R U . . .
H5B H 0.556495 0.683749 0.581205 0.180 Uiso 1 1 calc R U . . .
C6 C 0.7488(6) 0.6387(6) 0.5869(4) 0.1447(14) Uani 1 1 d . . . . .
H6A H 0.834417 0.662192 0.567550 0.174 Uiso 1 1 calc R U . . .
H6B H 0.752032 0.631006 0.646197 0.174 Uiso 1 1 calc R U . . .
C7 C 0.8333(7) 0.4849(6) 0.5648(4) 0.1285(11) Uani 1 1 d . . . . .
H7A H 0.871627 0.501661 0.617805 0.154 Uiso 1 1 calc R U . . .
H7B H 0.800528 0.415866 0.568488 0.154 Uiso 1 1 calc R U . . .
C8 C 0.9332(7) 0.4863(5) 0.5077(4) 0.1156(18) Uani 1 1 d . . . . .
H8A H 0.970466 0.554044 0.505062 0.139 Uiso 1 1 calc R U . . .
H8B H 1.002807 0.440318 0.525067 0.139 Uiso 1 1 calc R U . . .
C9 C 0.9882(6) 0.4660(5) 0.3711(4) 0.1173(18) Uani 1 1 d . . . . .
H9A H 1.057491 0.417065 0.382635 0.141 Uiso 1 1 calc R U . . .
H9B H 1.027334 0.533204 0.372996 0.141 Uiso 1 1 calc R U . . .
C10 C 0.9375(6) 0.4483(5) 0.2918(4) 0.1102(11) Uani 1 1 d . . . . .
H10A H 0.896025 0.381910 0.290531 0.132 Uiso 1 1 calc R U . . .
H10B H 1.010054 0.447871 0.252715 0.132 Uiso 1 1 calc R U . . .
O1 O 0.8428(3) 0.5229(3) 0.2674(2) 0.0934(10) Uani 1 1 d . . . . .
O2 O 0.7914(4) 0.7193(3) 0.3270(3) 0.1133(10) Uani 1 1 d . . . . .
O3 O 0.6252(4) 0.7350(3) 0.4712(3) 0.1177(11) Uani 1 1 d . . . . .
O4 O 0.7158(4) 0.5537(4) 0.5514(2) 0.1070(10) Uani 1 1 d . . . . .
O5 O 0.8906(4) 0.4588(3) 0.4314(2) 0.1036(12) Uani 1 1 d . . . . .
C11 C 0.5752(5) 0.4353(4) 0.3490(3) 0.0860(10) Uani 1 1 d . . . . .
H11A H 0.562996 0.441119 0.289982 0.103 Uiso 1 1 calc R U . . .
H11B H 0.644342 0.385559 0.358625 0.103 Uiso 1 1 calc R U . . .
C12 C 0.4523(5) 0.3989(5) 0.3858(3) 0.0900(11) Uani 1 1 d . . . . .
H12A H 0.380156 0.443474 0.370080 0.108 Uiso 1 1 calc R U . . .
H12B H 0.432672 0.331566 0.364928 0.108 Uiso 1 1 calc R U . . .
C13 C 0.5259(7) 0.3015(5) 0.5000(5) 0.1577(17) Uani 1 1 d . . . . .
H13A H 0.470466 0.244900 0.486074 0.236 Uiso 1 1 calc R U . . .
H13B H 0.540043 0.302868 0.558374 0.236 Uiso 1 1 calc R U . . .
H13C H 0.609601 0.295015 0.472368 0.236 Uiso 1 1 calc R U . . .
C14 C 0.3383(7) 0.3979(7) 0.5165(5) 0.175(2) Uani 1 1 d . . . . .
H14A H 0.317877 0.466616 0.531559 0.262 Uiso 1 1 calc R U . . .
H14B H 0.343695 0.356917 0.565229 0.262 Uiso 1 1 calc R U . . .
H14C H 0.269880 0.372018 0.481250 0.262 Uiso 1 1 calc R U . . .
N1 N 0.6193(3) 0.5354(3) 0.3821(2) 0.0627(11) Uani 1 1 d . . . . .
H1C H 0.698731 0.550568 0.361809 0.075 Uiso 1 1 calc R U . . .
H1D H 0.623930 0.532172 0.436750 0.075 Uiso 1 1 calc R U . . .
H1E H 0.561456 0.583122 0.367581 0.075 Uiso 1 1 calc R U . . .
N2 N 0.4618(4) 0.3953(3) 0.4743(3) 0.0823(9) Uani 1 1 d . . . . .
Cl1 Cl 0.33457(11) 0.63675(10) 0.24212(8) 0.0686(4) Uani 1 1 d . . . . .
O6 O 0.3871(6) 0.6548(4) 0.3190(3) 0.1821(16) Uani 1 1 d . . . . .
O7 O 0.4318(7) 0.6163(6) 0.1938(4) 0.253(2) Uani 1 1 d . . . . .
O8 O 0.2485(4) 0.7162(3) 0.2161(3) 0.1354(14) Uani 1 1 d . . . . .
O9 O 0.2586(5) 0.5505(4) 0.2442(4) 0.215(2) 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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.493(8) . ?
C1 O1 1.369(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 O2 1.420(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.397(11) . ?
C3 O2 1.357(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 O3 1.408(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.512(10) . ?
C5 O3 1.514(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 O4 1.303(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.370(9) . ?
C7 O4 1.509(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 O5 1.362(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.406(9) . ?
C9 O5 1.393(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 O1 1.427(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.457(7) . ?
C11 N1 1.493(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 N2 1.444(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 N2 1.456(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 N2 1.423(8) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
Cl1 O6 1.378(5) . ?
Cl1 O7 1.286(6) . ?
Cl1 O8 1.425(5) . ?
Cl1 O9 1.372(6) . ?

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
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
O1 C1 C2 111.2(5) . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
O2 C2 C1 109.4(5) . . ?
O2 C2 H2A 109.8 . . ?
O2 C2 H2B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
O2 C3 H3A 109.8 . . ?
O2 C3 H3B 109.8 . . ?
O2 C3 C4 109.6(6) . . ?
C3 C4 H4A 108.1 . . ?
C3 C4 H4B 108.1 . . ?
C3 C4 O3 116.7(6) . . ?
H4A C4 H4B 107.3 . . ?
O3 C4 H4A 108.1 . . ?
O3 C4 H4B 108.1 . . ?
H5A C5 H5B 107.2 . . ?
C6 C5 H5A 107.9 . . ?
C6 C5 H5B 107.9 . . ?
C6 C5 O3 117.6(6) . . ?
O3 C5 H5A 107.9 . . ?
O3 C5 H5B 107.9 . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
O4 C6 C5 103.8(5) . . ?
O4 C6 H6A 111.0 . . ?
O4 C6 H6B 111.0 . . ?
H7A C7 H7B 107.1 . . ?
C8 C7 H7A 107.8 . . ?
C8 C7 H7B 107.8 . . ?
C8 C7 O4 118.2(6) . . ?
O4 C7 H7A 107.8 . . ?
O4 C7 H7B 107.8 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
O5 C8 C7 112.4(6) . . ?
O5 C8 H8A 109.1 . . ?
O5 C8 H8B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
O5 C9 H9A 109.2 . . ?
O5 C9 H9B 109.2 . . ?
O5 C9 C10 112.1(5) . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C9 C10 O1 112.6(5) . . ?
H10A C10 H10B 107.8 . . ?
O1 C10 H10A 109.1 . . ?
O1 C10 H10B 109.1 . . ?
C1 O1 C10 115.2(4) . . ?
C3 O2 C2 116.1(5) . . ?
C4 O3 C5 122.3(5) . . ?
C6 O4 C7 104.6(5) . . ?
C8 O5 C9 113.5(5) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C12 C11 N1 113.4(5) . . ?
N1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N2 C12 C11 111.3(4) . . ?
N2 C12 H12A 109.4 . . ?
N2 C12 H12B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
C11 N1 H1C 109.5 . . ?
C11 N1 H1D 109.5 . . ?
C11 N1 H1E 109.5 . . ?
H1C N1 H1D 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C12 N2 C13 110.0(5) . . ?
C14 N2 C12 114.9(5) . . ?
C14 N2 C13 105.8(5) . . ?
O6 Cl1 O8 112.1(3) . . ?
O7 Cl1 O6 107.3(4) . . ?
O7 Cl1 O8 116.0(4) . . ?
O7 Cl1 O9 105.5(5) . . ?
O9 Cl1 O6 109.6(4) . . ?
O9 Cl1 O8 106.0(3) . . ?

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
C1 C2 O2 C3 178.3(5) . . . . ?
C2 C1 O1 C10 -154.7(5) . . . . ?
C3 C4 O3 C5 158.5(6) . . . . ?
C4 C3 O2 C2 175.8(5) . . . . ?
C5 C6 O4 C7 171.7(5) . . . . ?
C6 C5 O3 C4 -83.0(8) . . . . ?
C7 C8 O5 C9 176.0(6) . . . . ?
C8 C7 O4 C6 -88.7(7) . . . . ?
C9 C10 O1 C1 86.5(6) . . . . ?
C10 C9 O5 C8 -173.3(5) . . . . ?
O1 C1 C2 O2 63.0(6) . . . . ?
O2 C3 C4 O3 -70.9(7) . . . . ?
O3 C5 C6 O4 -63.1(7) . . . . ?
O4 C7 C8 O5 -60.6(8) . . . . ?
O5 C9 C10 O1 64.0(7) . . . . ?
C11 C12 N2 C13 -83.0(6) . . . . ?
C11 C12 N2 C14 157.7(6) . . . . ?
N1 C11 C12 N2 -54.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.18(14)
2 -0.18(14)
# start Validation Reply Form
_vrf_PLAT026_1                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        37% Check 
RESPONSE: Due to high collection temperature of 293 K, 
reflections at high resolution cannot be collected.
;
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2212393'
loop_
_audit_author_name
_audit_author_address
'Mengmeng Lun'
;Southeast University
China
;
_audit_update_record             
;
2022-10-12 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_audit_creation_date             2022-09-17
_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 O6, 0.5(C8 N4), Cl O4'
_chemical_formula_sum            'C16 Cl N2 O10'
_chemical_formula_weight         415.63
_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'
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           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   12.29(3)
_cell_length_b                   13.24(3)
_cell_length_c                   14.95(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2433(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    293
_cell_measurement_temperature    368.0
_cell_measurement_theta_max      13.75
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1619
_diffrn_reflns_av_unetI/netI     0.2746
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6446
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        24.496
_diffrn_reflns_theta_max         24.496
_diffrn_reflns_theta_min         2.261
_diffrn_ambient_temperature      368.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                628
_reflns_number_total             2012
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.8(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2012
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.3059
_refine_ls_R_factor_gt           0.1932
_refine_ls_restrained_S_all      1.036
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4123
_refine_ls_wR_factor_ref         0.5018
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.2(7)
 0.8(7)
2. Restrained distances
 N2-C10
 1.47 with sigma of 0.03
 N2-C8
 1.47 with sigma of 0.03
 C10-C8
 3 with sigma of 0.05
 Cl1-O8
 1.4 with sigma of 0.04
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
5. Others
 Fixed Sof: C7(0.5) C8(0.5) C9(0.5) N2(0.5) O6(0.25) O8(0.25)
;
_atom_sites_solution_hydrogens   .
_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
C1 C 0.441(4) 0.763(4) 0.859(3) 0.267(15) Uani 1 1 d . U . . .
C2 C 0.340(5) 0.729(4) 0.855(4) 0.280(15) Uani 1 1 d . U . . .
C3 C 0.223(5) 0.597(4) 0.789(5) 0.294(17) Uani 1 1 d . U . . .
C4 C 0.210(4) 0.524(4) 0.719(5) 0.288(15) Uani 1 1 d . U . . .
C5 C 0.340(6) 0.354(4) 0.628(4) 0.291(15) Uani 1 1 d . U . . .
C6 C 0.407(6) 0.310(3) 0.652(4) 0.297(16) Uani 1 1 d . U . . .
O1 O 0.500000 0.704(2) 0.847(2) 0.209(11) Uani 1 2 d S TU P . .
O2 O 0.300(2) 0.653(2) 0.782(2) 0.245(10) Uani 1 1 d . U . . .
O3 O 0.300(2) 0.440(2) 0.6888(19) 0.251(10) Uani 1 1 d . U . . .
O4 O 0.500000 0.368(2) 0.629(2) 0.248(12) Uani 1 2 d S TU P . .
C7 C 0.456(3) 0.671(2) 0.606(3) 0.155(13) Uani 0.5 1 d . U P . .
C8 C 0.380(5) 0.684(4) 0.492(4) 0.219(15) Uani 0.5 1 d D U P . .
C9 C 0.439(5) 0.732(4) 0.446(4) 0.22(2) Uani 0.5 1 d . U P . .
C10 C 0.500000 0.534(4) 0.410(3) 0.267(19) Uani 1 2 d DS TU P . .
N1 N 0.500000 0.5841(14) 0.6846(14) 0.133(7) Uani 1 2 d S TU P . .
N2 N 0.461(3) 0.5994(19) 0.491(2) 0.181(13) Uani 0.5 1 d D U P . .
Cl1 Cl 0.000000 0.4866(6) 0.5056(6) 0.156(4) Uani 1 2 d DS TU P . .
O5 O 0.104(2) 0.5447(19) 0.4919(17) 0.252(9) Uani 1 1 d . U . . .
O6 O 0.000000 0.582(4) 0.550(3) 0.216(12) Uani 0.5 2 d S TU P . .
O7 O 0.000000 0.411(2) 0.5777(19) 0.205(9) Uani 1 2 d S TU P . .
O8 O 0.000000 0.443(4) 0.429(3) 0.219(14) Uani 0.5 2 d DS TU P . .


_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
C1 C2 1.33(7) . ?
C1 O1 1.08(4) . ?
C2 O2 1.56(7) . ?
C3 C4 1.45(8) . ?
C3 O2 1.21(6) . ?
C4 O3 1.63(6) . ?
C5 C6 1.07(7) . ?
C5 O3 1.53(7) . ?
C6 O4 1.43(6) . ?
C7 C8 1.95(8) . ?
C7 N1 1.73(4) . ?
C8 N2 1.50(3) . ?
C9 N2 1.90(5) . ?
C10 N2 1.56(3) 3_655 ?
C10 N2 1.56(3) . ?
Cl1 O5 1.51(2) 3 ?
Cl1 O5 1.51(2) . ?
Cl1 O6 1.43(6) 3 ?
Cl1 O6 1.43(6) . ?
Cl1 O7 1.47(3) 3 ?
Cl1 O7 1.47(3) . ?
Cl1 O8 1.29(4) . ?
Cl1 O8 1.29(4) 3 ?
O6 O6 0.00(16) 3 ?
O7 O7 0.00(8) 3 ?
O8 O8 0.00(13) 3 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 112(4) . . ?
C1 C2 O2 123(4) . . ?
O2 C3 C4 116(6) . . ?
C3 C4 O3 126(5) . . ?
C6 C5 O3 117(7) . . ?
C5 C6 O4 104(5) . . ?
C1 O1 C1 84(5) 3_655 . ?
C3 O2 C2 125(6) . . ?
C5 O3 C4 152(4) . . ?
C6 O4 C6 107(5) 3_655 . ?
N1 C7 C8 144(3) . . ?
N2 C8 C7 68(3) . . ?
N2 C10 N2 36(3) 3_655 . ?
C7 N1 C7 36(3) 3_655 . ?
C8 N2 C9 39(3) . . ?
C8 N2 C10 129(3) . . ?
C10 N2 C9 107(3) . . ?
O5 Cl1 O5 116(2) 3 . ?
O6 Cl1 O5 67.2(14) . . ?
O6 Cl1 O5 67.2(14) 3 3 ?
O6 Cl1 O5 67.2(14) . 3 ?
O6 Cl1 O5 67.2(14) 3 . ?
O6 Cl1 O6 0(4) 3 . ?
O6 Cl1 O7 105(2) . . ?
O6 Cl1 O7 105(2) 3 3 ?
O6 Cl1 O7 105(2) 3 . ?
O6 Cl1 O7 105(2) . 3 ?
O7 Cl1 O5 116.5(10) . 3 ?
O7 Cl1 O5 116.5(10) . . ?
O7 Cl1 O5 116.5(10) 3 . ?
O7 Cl1 O5 116.5(10) 3 3 ?
O7 Cl1 O7 0.0(15) . 3 ?
O8 Cl1 O5 96.4(17) 3 . ?
O8 Cl1 O5 96.4(17) . 3 ?
O8 Cl1 O5 96.4(17) 3 3 ?
O8 Cl1 O5 96.4(17) . . ?
O8 Cl1 O6 145(3) 3 . ?
O8 Cl1 O6 145(3) . 3 ?
O8 Cl1 O6 145(3) . . ?
O8 Cl1 O6 145(3) 3 3 ?
O8 Cl1 O7 110(2) . . ?
O8 Cl1 O7 110(2) . 3 ?
O8 Cl1 O7 110(2) 3 3 ?
O8 Cl1 O7 110(2) 3 . ?
O8 Cl1 O8 0(4) 3 . ?
Cl1 O6 O5 59(2) . 3 ?
O6 O6 Cl1 0(10) 3 . ?
O6 O6 O5 0(10) 3 3 ?
O7 O7 Cl1 0(10) 3 . ?
O8 O8 Cl1 0(10) 3 . ?

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
C1 C2 O2 C3 156(6) . . . . ?
C2 C1 O1 C1 -178(3) . . . 3_655 ?
C3 C4 O3 C5 -176(6) . . . . ?
C4 C3 O2 C2 -172(4) . . . . ?
C5 C6 O4 C6 -176(4) . . . 3_655 ?
C6 C5 O3 C4 -165(6) . . . . ?
O1 C1 C2 O2 -42(8) . . . . ?
O2 C3 C4 O3 57(7) . . . . ?
O3 C5 C6 O4 -83(7) . . . . ?
C7 C8 N2 C9 -107(5) . . . . ?
C7 C8 N2 C10 -171(3) . . . . ?
C8 C7 N1 C7 114(4) . . . 3_655 ?
N2 C10 N2 C8 129(4) 3_655 . . . ?
N2 C10 N2 C9 93(3) 3_655 . . . ?
O5 Cl1 O6 O5 134(3) . . . 3 ?
O5 Cl1 O6 O6 0(8) . . . 3 ?
O5 Cl1 O6 O6 0(9) 3 . . 3 ?
O5 Cl1 O7 O7 0(4) . . . 3 ?
O5 Cl1 O7 O7 0(3) 3 . . 3 ?
O5 Cl1 O8 O8 0(6) 3 . . 3 ?
O5 Cl1 O8 O8 0(6) . . . 3 ?
O6 Cl1 O6 O5 0(100) 3 . . 3 ?
O6 Cl1 O7 O7 0(3) . . . 3 ?
O6 Cl1 O7 O7 0(3) 3 . . 3 ?
O6 Cl1 O8 O8 0(100) . . . 3 ?
O6 Cl1 O8 O8 0(100) 3 . . 3 ?
O7 Cl1 O6 O5 -112.9(13) 3 . . 3 ?
O7 Cl1 O6 O5 -112.9(13) . . . 3 ?
O7 Cl1 O6 O6 0(100) 3 . . 3 ?
O7 Cl1 O6 O6 0(100) . . . 3 ?
O7 Cl1 O8 O8 0(6) 3 . . 3 ?
O7 Cl1 O8 O8 0(6) . . . 3 ?
O8 Cl1 O6 O5 67.1(13) . . . 3 ?
O8 Cl1 O6 O5 67.1(13) 3 . . 3 ?
O8 Cl1 O6 O6 0(9) . . . 3 ?
O8 Cl1 O6 O6 0(9) 3 . . 3 ?
O8 Cl1 O7 O7 0(100) 3 . . 3 ?
O8 Cl1 O7 O7 0(100) . . . 3 ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.2(7)
2 0.8(7)
# start Validation Reply Form
_vrf_PLAT084_1                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.50 Report
RESPONSE: We made several attempts to obtain better quality for 
this structure, but failed. Due to the existence of many disordered parts 
and the weak X-ray diffraction at 368 K, the wR2  value is high. However, 
we are confident the structural characterization is valid. 
;
_vrf_PLAT340_1                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0825 Ang.  
RESPONSE: This alerts are generated because of many disordered 
parts in the structure. 
;
_vrf_PLAT082_1                   
;
PROBLEM: High R1 Value ..................................       0.19 Report
RESPONSE: We made several attempts to obtain better quality for 
this structure, but failed. Due to the existence of many disordered parts 
and the weak X-ray diffraction at 368 K, the wR2  value is high. However, 
we are confident the structural characterization is valid. 
;
# 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 2212390'
loop_
_audit_author_name
_audit_author_address
'Mengmeng Lun'
;Southeast University
China
;
_audit_update_record             
;
2022-10-12 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_audit_creation_date             2022-09-17
_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         'C10 O5, Cl2 O8, 0.5(C8 N4)'
_chemical_formula_sum            'C14 Cl2 N2 O13'
_chemical_formula_weight         475.06
_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'
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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   11.547(2)
_cell_length_b                   10.6358(17)
_cell_length_c                   20.726(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2545.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    963
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.0670
_cell_measurement_theta_min      2.7610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.76959
_exptl_absorpt_correction_type   none
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11652
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.965
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                745
_reflns_number_total             2369
_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         0.442
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.3131
_refine_ls_R_factor_gt           0.1598
_refine_ls_restrained_S_all      1.090
_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)+(0.0400P)²+14.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2942
_refine_ls_wR_factor_ref         0.3301
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N2-C8A
 1.47 with sigma of 0.02
 N2-C8
 1.47 with sigma of 0.05
 Cl1-O5_$2 \\sim Cl1-O5A_$2
 with sigma of 0.02
 Cl2-O7A_$1 \\sim Cl2-O7_$1
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(O10) \\sim Ueq, Uanis(O11) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(O4) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(O4A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(C8) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(O7A) = Uanis(O7)
Uanis(O5) = Uanis(O5A)
3. Rigid body (RIGU) restrains
 O1, C1, C1, O2, O2, C2, C2, O3, O3, C3, C3, C4, C4, C5, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
 O10, O11, O10, O6
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.04
 O4, O11, O10, O10, O4A, O4A, O6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: C7(0.5) O5(0.5) O7(0.5) C8(0.5) O4A(0.5) O5A(0.5) O7A(0.5)
 C8A(0.5) O10(0.25) O11(0.25) C6(0.5)
;
_atom_sites_solution_hydrogens   .
_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
O1 O -0.6970(6) -0.750000 0.2958(2) 0.221(2) Uani 1 2 d S T P . .
C1 C -0.6574(7) -0.6288(7) 0.2740(2) 0.2509(14) Uani 1 1 d . . . . .
O2 O -0.7270(3) -0.5241(3) 0.36158(16) 0.1820(10) Uani 1 1 d . . . . .
C2 C -0.7453(6) -0.5349(6) 0.2951(3) 0.2309(12) Uani 1 1 d . . . . .
O3 O -0.9011(3) -0.6160(3) 0.44410(18) 0.1746(10) Uani 1 1 d . . . . .
C3 C -0.8148(6) -0.4453(7) 0.3941(3) 0.2396(16) Uani 1 1 d . . . . .
C4 C -0.9269(6) -0.5170(6) 0.4012(4) 0.2335(11) Uani 1 1 d . . . . .
C5 C -0.9984(5) -0.7004(5) 0.4528(3) 0.227(2) Uani 1 1 d . U . . .
Cl1 Cl -1.11492(15) -0.250000 0.31559(8) 0.1213(7) Uani 1 2 d DS T P . .
O6 O -1.1985(5) -0.250000 0.2710(3) 0.253(3) Uani 1 2 d S T P A .
Cl2 Cl -0.35282(14) -0.750000 0.42675(9) 0.1633(10) Uani 1 2 d DS T P . .
N1 N -0.6800(3) -0.750000 0.43496(16) 0.0810(15) Uani 1 2 d S T P C .
N2 N -0.5987(4) -0.750000 0.61468(18) 0.138(2) Uani 1 2 d DS T P . .
C7 C -0.6657(5) -0.6987(6) 0.5071(3) 0.083(3) Uani 0.5 1 d . . P . .
O5 O -1.0057(5) -0.2933(8) 0.2958(4) 0.262(4) Uani 0.5 1 d . . P A 1
O7 O -0.4478(5) -0.8115(6) 0.4001(4) 0.221(3) Uani 0.5 1 d . . P B 1
C8 C -0.4964(9) -0.6744(10) 0.6218(5) 0.197(4) Uani 0.5 1 d D U P C 1
O4A O -1.1428(5) -0.3233(6) 0.3668(2) 0.177(2) Uani 0.5 1 d . U P A 2
O5A O -1.0708(8) -0.1271(6) 0.3023(5) 0.262(4) Uani 0.5 1 d . . P A 2
O7A O -0.3861(6) -0.6436(6) 0.4617(4) 0.221(3) Uani 0.5 1 d . . P B 2
C8A C -0.5800(7) -0.6162(6) 0.6485(3) 0.132(3) Uani 0.5 1 d D . P C 2
O10 O -0.2678(8) -0.6390(12) 0.4001(6) 0.145(5) Uani 0.25 1 d . U P B .
O11 O -0.3018(10) -0.750000 0.4836(5) 0.205(4) Uani 0.5 2 d S TU P B .
C6 C -0.6204(6) -0.6850(6) 0.5411(3) 0.088(3) Uani 0.5 1 d . . P C .
O4 O -0.2736(8) -0.750000 0.3820(4) 0.297(3) Uani 1 2 d S TU P B .


_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 C1 1.441(7) 8_545 ?
O1 C1 1.441(7) . ?
C1 C2 1.490(10) . ?
O2 C2 1.398(6) . ?
O2 C3 1.479(8) . ?
O3 C4 1.410(7) . ?
O3 C5 1.449(6) . ?
C3 C4 1.509(10) . ?
C5 C5 1.056(12) 8_545 ?
Cl1 O6 1.336(6) . ?
Cl1 O5 1.404(7) . ?
Cl1 O5 1.404(7) 8 ?
Cl1 O4A 1.356(5) 8 ?
Cl1 O4A 1.356(5) . ?
Cl1 O5A 1.430(7) . ?
Cl1 O5A 1.430(7) 8 ?
Cl2 O7 1.392(6) . ?
Cl2 O7 1.392(6) 8_545 ?
Cl2 O7A 1.398(6) . ?
Cl2 O7A 1.398(6) 8_545 ?
Cl2 O10 1.633(11) 8_545 ?
Cl2 O10 1.633(11) . ?
Cl2 O11 1.318(11) . ?
Cl2 O11 1.318(11) 8_545 ?
Cl2 O4 1.303(8) . ?
N1 C7 1.601(6) . ?
N1 C7 1.601(6) 8_545 ?
N2 C8 1.437(11) . ?
N2 C8 1.437(11) 8_545 ?
N2 C8A 1.602(7) 8_545 ?
N2 C8A 1.602(7) . ?
N2 C6 1.693(7) 8_545 ?
N2 C6 1.693(7) . ?
C7 C6 0.889(8) . ?
O4A O5A 1.661(10) 8 ?
O11 O11 0.00(2) 8_545 ?

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
C1 O1 C1 127.0(7) 8_545 . ?
O1 C1 C2 106.9(6) . . ?
C2 O2 C3 113.1(5) . . ?
O2 C2 C1 104.0(5) . . ?
C4 O3 C5 112.1(4) . . ?
O2 C3 C4 110.2(5) . . ?
O3 C4 C3 104.9(5) . . ?
C5 C5 O3 128.3(3) 8_545 . ?
O6 Cl1 O5 116.5(4) . 8 ?
O6 Cl1 O5 116.5(4) . . ?
O6 Cl1 O4A 111.7(3) . 8 ?
O6 Cl1 O4A 111.7(3) . . ?
O6 Cl1 O5A 97.2(4) . . ?
O6 Cl1 O5A 97.2(4) . 8 ?
O5 Cl1 O5 38.3(6) 8 . ?
O5 Cl1 O5A 47.5(5) . 8 ?
O5 Cl1 O5A 85.6(5) 8 8 ?
O4A Cl1 O4A 70.1(5) 8 . ?
O4A Cl1 O5A 139.5(5) . . ?
O4A Cl1 O5A 73.1(5) 8 . ?
O7 Cl2 O7 56.1(5) . 8_545 ?
O7 Cl2 O7A 111.7(4) 8_545 8_545 ?
O7 Cl2 O7A 67.0(4) . 8_545 ?
O7 Cl2 O10 90.0(5) . 8_545 ?
O7 Cl2 O10 90.0(5) 8_545 . ?
O7 Cl2 O10 132.8(5) . . ?
O7 Cl2 O10 132.8(5) 8_545 8_545 ?
O7A Cl2 O10 157.9(5) 8_545 . ?
O7A Cl2 O10 75.9(5) . . ?
O10 Cl2 O10 92.7(8) . 8_545 ?
O11 Cl2 O7 135.0(5) . 8_545 ?
O11 Cl2 O7 135.0(5) 8_545 . ?
O11 Cl2 O7 135.0(5) . . ?
O11 Cl2 O7 135.0(5) 8_545 8_545 ?
O11 Cl2 O7A 70.1(4) 8_545 . ?
O11 Cl2 O7A 70.1(4) 8_545 8_545 ?
O11 Cl2 O7A 70.1(4) . . ?
O11 Cl2 O7A 70.1(4) . 8_545 ?
O11 Cl2 O10 92.0(6) 8_545 . ?
O11 Cl2 O10 92.0(6) . 8_545 ?
O11 Cl2 O10 92.0(6) . . ?
O11 Cl2 O10 92.0(6) 8_545 8_545 ?
O11 Cl2 O11 0.0(10) 8_545 . ?
O4 Cl2 O7 105.7(4) . . ?
O4 Cl2 O7 105.7(4) . 8_545 ?
O4 Cl2 O7A 124.2(3) . . ?
O4 Cl2 O7A 124.2(3) . 8_545 ?
O4 Cl2 O10 48.4(4) . . ?
O4 Cl2 O10 48.4(4) . 8_545 ?
O4 Cl2 O11 108.8(6) . 8_545 ?
O4 Cl2 O11 108.8(6) . . ?
C7 N1 C7 39.9(5) . 8_545 ?
C8 N2 C8 68.0(9) . 8_545 ?
C8 N2 C8A 110.0(6) . 8_545 ?
C8 N2 C8A 49.2(5) 8_545 8_545 ?
C8 N2 C6 116.2(5) . 8_545 ?
C8 N2 C6 116.2(5) 8_545 . ?
C8 N2 C6 89.2(5) 8_545 8_545 ?
C8 N2 C6 89.2(5) . . ?
C8A N2 C8A 125.4(5) . 8_545 ?
C8A N2 C6 141.0(4) 8_545 . ?
C8A N2 C6 93.0(3) . . ?
C6 N2 C6 48.2(4) 8_545 . ?
C6 C7 N1 148.9(8) . . ?
Cl1 O4A O5A 55.5(3) . 8 ?
Cl2 O11 O7A 57.4(4) . 8_545 ?
O11 O11 Cl2 0(10) 8_545 . ?
O11 O11 O7A 0(10) 8_545 8_545 ?
C7 C6 N2 97.8(4) 8_545 . ?
C7 C6 N2 137.2(7) . . ?
C7 C6 C7 45.3(6) . 8_545 ?

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 C1 C2 O2 73.8(6) . . . . ?
C1 O1 C1 C2 163.6(6) 8_545 . . . ?
O2 C3 C4 O3 66.0(6) . . . . ?
C2 O2 C3 C4 75.8(6) . . . . ?
C3 O2 C2 C1 -173.4(5) . . . . ?
C4 O3 C5 C5 134.9(4) . . . 8_545 ?
C5 O3 C4 C3 -175.9(5) . . . . ?
O6 Cl1 O4A O5A 91.1(4) . . . 8 ?
N1 C7 C6 N2 -104.8(14) . . . . ?
N1 C7 C6 C7 -66.8(13) . . . 8_545 ?
C7 N1 C7 C6 74.7(14) 8_545 . . . ?
O7 Cl2 O11 O11 0.0(12) 8_545 . . 8_545 ?
O7 Cl2 O11 O11 0.0(5) . . . 8_545 ?
C8 N2 C6 C7 78.0(7) 8_545 . . 8_545 ?
C8 N2 C6 C7 142.9(6) . . . 8_545 ?
C8 N2 C6 C7 104.2(12) 8_545 . . . ?
C8 N2 C6 C7 169.1(12) . . . . ?
O4A Cl1 O4A O5A -162.7(4) 8 . . 8 ?
O5A Cl1 O4A O5A -136.6(9) . . . 8 ?
O7A Cl2 O11 O7A 118.9(7) . . . 8_545 ?
O7A Cl2 O11 O11 0.0(10) 8_545 . . 8_545 ?
O7A Cl2 O11 O11 0.0(7) . . . 8_545 ?
C8A N2 C6 C7 21.2(9) 8_545 . . 8_545 ?
C8A N2 C6 C7 -168.0(5) . . . 8_545 ?
C8A N2 C6 C7 47.4(15) 8_545 . . . ?
C8A N2 C6 C7 -141.8(11) . . . . ?
O10 Cl2 O11 O7A -74.2(5) 8_545 . . 8_545 ?
O10 Cl2 O11 O7A -166.9(5) . . . 8_545 ?
O10 Cl2 O11 O11 0.0(9) . . . 8_545 ?
O10 Cl2 O11 O11 0.0(9) 8_545 . . 8_545 ?
O11 Cl2 O11 O7A 0(13) 8_545 . . 8_545 ?
C6 N2 C6 C7 41.8(12) 8_545 . . . ?
C6 N2 C6 C7 15.5(5) 8_545 . . 8_545 ?
O4 Cl2 O11 O7A -120.6(3) . . . 8_545 ?
O4 Cl2 O11 O11 0(100) . . . 8_545 ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT082_1                   
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: : This problem asised from the existence of 
many disordered parts in this crystal and the weak
 X-ray diffraction at 293 K.
;
_vrf_PLAT242_1                   
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         O2 Check 
RESPONSE: This generated alert is due to the disordered 18-crown-6 molecule,
 to which this oxygen atom is part.
;
# end Validation Reply Form
