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

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

data_kl1223
_database_code_depnum_ccdc_archive 'CCDC 1988911'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Insitute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N2, C H4 O, Cl'
_chemical_formula_sum            'C24 H21 Cl1 N2 O1'
_chemical_formula_weight         388.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2977(7)
_cell_length_b                   18.1902(10)
_cell_length_c                   23.3996(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.702(7)
_cell_angle_gamma                90.00
_cell_volume                     3888.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5139
_cell_measurement_theta_min      0.9
_cell_measurement_theta_max      75.0

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    1.864
_exptl_absorpt_correction_T_min  0.7184
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8211
_diffrn_reflns_av_R_equivalents  0.0048
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         77.84
_reflns_number_total             8200
_reflns_number_gt                5584
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'DETMAX (Mishnev & Belyakov, 1988)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1513P)²+1.5043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8200
_refine_ls_number_parameters     511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0897
_refine_ls_wR_factor_ref         0.2553
_refine_ls_wR_factor_gt          0.2275
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2A Cl 0.51054(10) 1.07046(5) 0.57408(4) 0.0449(3) Uani 1 1 d . . .
Cl1A Cl 0.83986(11) 0.56260(5) 0.57366(5) 0.0483(3) Uani 1 1 d . . .
N9 N 1.0397(3) -0.05363(17) 0.62264(13) 0.0369(7) Uani 1 1 d . . .
N19 N 0.9293(4) 0.40498(18) 0.58233(16) 0.0441(8) Uani 1 1 d . . .
H19 H 0.9155 0.4516 0.5783 0.053 Uiso 1 1 calc R . .
N69 N 0.4308(4) 0.91258(19) 0.58058(16) 0.0466(8) Uani 1 1 d . . .
H69 H 0.445(5) 0.960(3) 0.578(2) 0.048(12) Uiso 1 1 d . . .
N59 N 0.3489(3) 0.45651(18) 0.62872(14) 0.0396(7) Uani 1 1 d . . .
C54A C 0.3979(4) 0.3344(2) 0.62450(15) 0.0351(7) Uani 1 1 d . . .
C4B C 0.9829(4) -0.1753(2) 0.62461(15) 0.0352(7) Uani 1 1 d . . .
C8 C 0.8197(4) -0.1014(2) 0.55265(16) 0.0393(8) Uani 1 1 d . . .
H8 H 0.7915 -0.0563 0.5353 0.047 Uiso 1 1 calc R . .
C54B C 0.3111(4) 0.3454(2) 0.66882(15) 0.0358(7) Uani 1 1 d . . .
C59A C 0.4206(4) 0.4043(2) 0.60123(16) 0.0373(8) Uani 1 1 d . . .
C10 C 1.0218(4) 0.0239(2) 0.61436(16) 0.0369(8) Uani 1 1 d . . .
C8A C 0.9410(4) -0.1073(2) 0.59782(16) 0.0356(7) Uani 1 1 d . . .
C66 C 0.3940(4) 0.7658(2) 0.60009(16) 0.0367(8) Uani 1 1 d . . .
C16 C 0.9694(4) 0.2563(2) 0.59488(16) 0.0359(7) Uani 1 1 d . . .
C13 C 0.9884(4) 0.1759(2) 0.60056(16) 0.0364(7) Uani 1 1 d . . .
C58A C 0.2814(4) 0.4214(2) 0.66979(16) 0.0376(8) Uani 1 1 d . . .
C3 C 1.3101(4) -0.1749(2) 0.74873(17) 0.0435(9) Uani 1 1 d . . .
H3 H 1.3680 -0.2042 0.7765 0.052 Uiso 1 1 calc R . .
C4A C 1.1112(4) -0.1616(2) 0.66880(15) 0.0353(7) Uani 1 1 d . . .
C60 C 0.3594(4) 0.5343(2) 0.62124(16) 0.0385(8) Uani 1 1 d . . .
C54 C 0.4579(4) 0.2717(2) 0.60281(16) 0.0380(8) Uani 1 1 d . . .
H54 H 0.4450 0.2253 0.6177 0.046 Uiso 1 1 calc R . .
C61 C 0.2327(4) 0.5767(2) 0.60699(17) 0.0393(8) Uani 1 1 d . . .
H61 H 0.1411 0.5545 0.6019 0.047 Uiso 1 1 calc R . .
C51 C 0.5015(4) 0.4130(2) 0.55738(17) 0.0434(9) Uani 1 1 d . . .
H51 H 0.5176 0.4592 0.5427 0.052 Uiso 1 1 calc R . .
C56 C 0.1807(4) 0.3281(2) 0.74686(17) 0.0439(9) Uani 1 1 d . . .
H56 H 0.1458 0.2974 0.7730 0.053 Uiso 1 1 calc R . .
C63 C 0.3798(4) 0.6859(2) 0.60823(16) 0.0375(8) Uani 1 1 d . . .
C62 C 0.2438(4) 0.6520(2) 0.60045(16) 0.0389(8) Uani 1 1 d . . .
H62 H 0.1593 0.6801 0.5907 0.047 Uiso 1 1 calc R . .
C5 C 0.9017(4) -0.2388(2) 0.60578(16) 0.0378(8) Uani 1 1 d . . .
H5 H 0.9273 -0.2841 0.6232 0.045 Uiso 1 1 calc R . .
C9A C 1.1427(4) -0.0867(2) 0.66636(16) 0.0372(8) Uani 1 1 d . . .
C15 C 1.1362(4) 0.0664(2) 0.60152(17) 0.0396(8) Uani 1 1 d . . .
H15 H 1.2239 0.0442 0.5975 0.047 Uiso 1 1 calc R . .
C17 C 0.8954(4) 0.2957(2) 0.63128(17) 0.0421(8) Uani 1 1 d . . .
H17 H 0.8586 0.2716 0.6605 0.051 Uiso 1 1 calc R . .
C14 C 1.1196(4) 0.1419(2) 0.59475(17) 0.0408(8) Uani 1 1 d . . .
H14 H 1.1964 0.1701 0.5863 0.049 Uiso 1 1 calc R . .
C21 C 1.0264(4) 0.2953(2) 0.55225(16) 0.0408(8) Uani 1 1 d . . .
H21 H 1.0796 0.2709 0.5281 0.049 Uiso 1 1 calc R . .
C71 C 0.5009(4) 0.8074(2) 0.63590(18) 0.0441(9) Uani 1 1 d . . .
H71 H 0.5618 0.7852 0.6671 0.053 Uiso 1 1 calc R . .
C11 C 0.8894(4) 0.0569(2) 0.61915(17) 0.0410(8) Uani 1 1 d . . .
H11 H 0.8121 0.0285 0.6268 0.049 Uiso 1 1 calc R . .
C20 C 1.0033(4) 0.3695(2) 0.54636(17) 0.0451(9) Uani 1 1 d . . .
H20 H 1.0387 0.3953 0.5176 0.054 Uiso 1 1 calc R . .
C4 C 1.1955(4) -0.2063(2) 0.71057(16) 0.0400(8) Uani 1 1 d . . .
H4 H 1.1750 -0.2562 0.7126 0.048 Uiso 1 1 calc R . .
C64 C 0.5060(4) 0.6426(2) 0.62218(17) 0.0403(8) Uani 1 1 d . . .
H64 H 0.5976 0.6648 0.6274 0.048 Uiso 1 1 calc R . .
C55 C 0.2608(4) 0.2988(2) 0.70787(16) 0.0407(8) Uani 1 1 d . . .
H55 H 0.2806 0.2487 0.7079 0.049 Uiso 1 1 calc R . .
C7 C 0.7438(4) -0.1646(2) 0.53486(17) 0.0414(8) Uani 1 1 d . . .
H7 H 0.6638 -0.1619 0.5045 0.050 Uiso 1 1 calc R . .
C68 C 0.3239(5) 0.8771(2) 0.54554(18) 0.0464(9) Uani 1 1 d . . .
H68 H 0.2646 0.9018 0.5152 0.056 Uiso 1 1 calc R . .
C2 C 1.3402(4) -0.1001(3) 0.74619(17) 0.0452(9) Uani 1 1 d . . .
H2 H 1.4170 -0.0803 0.7729 0.054 Uiso 1 1 calc R . .
C6 C 0.7823(4) -0.2325(2) 0.56057(16) 0.0392(8) Uani 1 1 d . . .
H6 H 0.7277 -0.2740 0.5474 0.047 Uiso 1 1 calc R . .
C57 C 0.1524(4) 0.4035(2) 0.74702(17) 0.0434(9) Uani 1 1 d . . .
H57 H 0.0992 0.4221 0.7737 0.052 Uiso 1 1 calc R . .
C12 C 0.8733(4) 0.1318(2) 0.61245(17) 0.0389(8) Uani 1 1 d . . .
H12 H 0.7848 0.1536 0.6158 0.047 Uiso 1 1 calc R . .
C67 C 0.3020(4) 0.8029(2) 0.55488(17) 0.0420(8) Uani 1 1 d . . .
H67 H 0.2265 0.7778 0.5312 0.050 Uiso 1 1 calc R . .
C53 C 0.5372(4) 0.2809(2) 0.55839(17) 0.0445(9) Uani 1 1 d . . .
H53 H 0.5773 0.2401 0.5432 0.053 Uiso 1 1 calc R . .
C52 C 0.5570(4) 0.3503(2) 0.53650(17) 0.0443(9) Uani 1 1 d . . .
H52 H 0.6098 0.3547 0.5066 0.053 Uiso 1 1 calc R . .
C65 C 0.4961(4) 0.5677(2) 0.62826(18) 0.0422(8) Uani 1 1 d . . .
H65 H 0.5806 0.5394 0.6370 0.051 Uiso 1 1 calc R . .
C58 C 0.2009(4) 0.4515(2) 0.70884(17) 0.0415(8) Uani 1 1 d . . .
H58 H 0.1807 0.5015 0.7092 0.050 Uiso 1 1 calc R . .
C18 C 0.8768(4) 0.3697(2) 0.62406(18) 0.0457(9) Uani 1 1 d . . .
H18 H 0.8270 0.3959 0.6485 0.055 Uiso 1 1 calc R . .
C70 C 0.5162(5) 0.8802(2) 0.62532(19) 0.0479(9) Uani 1 1 d . . .
H70 H 0.5871 0.9075 0.6496 0.057 Uiso 1 1 calc R . .
C1 C 1.2588(4) -0.0540(2) 0.70486(17) 0.0423(8) Uani 1 1 d . . .
H1 H 1.2803 -0.0042 0.7029 0.051 Uiso 1 1 calc R . .
O2M O 1.0014(5) 0.6137(2) 0.69962(18) 0.0776(11) Uani 1 1 d . . .
H2M H 0.9616 0.6024 0.6645 0.093 Uiso 1 1 d R . .
C1M C 0.8941(7) 0.6156(4) 0.7336(2) 0.0798(17) Uani 1 1 d . . .
H1MA H 0.8160 0.6473 0.7158 0.120 Uiso 1 1 calc R . .
H1MB H 0.9353 0.6340 0.7716 0.120 Uiso 1 1 calc R . .
H1MC H 0.8567 0.5670 0.7369 0.120 Uiso 1 1 calc R . .
O52M O 0.4443(5) 1.1183(3) 0.69620(18) 0.0840(12) Uani 1 1 d . . .
H52M H 0.4466 1.0980 0.6585 0.126 Uiso 1 1 d R . .
C51M C 0.5863(7) 1.1200(4) 0.7284(3) 0.0863(19) Uani 1 1 d . . .
H51A H 0.6509 1.1411 0.7053 0.129 Uiso 1 1 calc R . .
H51B H 0.6175 1.0709 0.7394 0.129 Uiso 1 1 calc R . .
H51C H 0.5882 1.1492 0.7627 0.129 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N9 C8A 1.391(5) . ?
N9 C9A 1.401(4) . ?
N9 C10 1.429(5) . ?
N19 C18 1.334(5) . ?
N19 C20 1.347(5) . ?
N19 H19 0.8600 . ?
N69 C70 1.329(6) . ?
N69 C68 1.332(6) . ?
N69 H69 0.88(5) . ?
N59 C59A 1.385(5) . ?
N59 C58A 1.396(5) . ?
N59 C60 1.431(5) . ?
C54A C54 1.405(5) . ?
C54A C59A 1.415(5) . ?
C54A C54B 1.441(5) . ?
C4B C5 1.406(5) . ?
C4B C8A 1.409(5) . ?
C4B C4A 1.448(5) . ?
C8 C7 1.373(5) . ?
C8 C8A 1.399(5) . ?
C8 H8 0.9300 . ?
C54B C55 1.389(5) . ?
C54B C58A 1.411(5) . ?
C59A C51 1.389(5) . ?
C10 C15 1.392(5) . ?
C10 C11 1.393(5) . ?
C66 C71 1.398(5) . ?
C66 C67 1.403(5) . ?
C66 C63 1.474(5) . ?
C16 C17 1.389(5) . ?
C16 C21 1.406(5) . ?
C16 C13 1.477(5) . ?
C13 C14 1.396(5) . ?
C13 C12 1.406(5) . ?
C58A C58 1.395(5) . ?
C3 C4 1.380(6) . ?
C3 C2 1.394(6) . ?
C3 H3 0.9300 . ?
C4A C9A 1.396(5) . ?
C4A C4 1.396(5) . ?
C60 C65 1.391(5) . ?
C60 C61 1.396(5) . ?
C54 C53 1.391(5) . ?
C54 H54 0.9300 . ?
C61 C62 1.383(5) . ?
C61 H61 0.9300 . ?
C51 C52 1.378(6) . ?
C51 H51 0.9300 . ?
C56 C55 1.387(6) . ?
C56 C57 1.397(6) . ?
C56 H56 0.9300 . ?
C63 C62 1.388(5) . ?
C63 C64 1.401(5) . ?
C62 H62 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9300 . ?
C9A C1 1.404(5) . ?
C15 C14 1.388(5) . ?
C15 H15 0.9300 . ?
C17 C18 1.364(6) . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?
C21 C20 1.369(6) . ?
C21 H21 0.9300 . ?
C71 C70 1.358(6) . ?
C71 H71 0.9300 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C20 H20 0.9300 . ?
C4 H4 0.9300 . ?
C64 C65 1.376(5) . ?
C64 H64 0.9300 . ?
C55 H55 0.9300 . ?
C7 C6 1.391(6) . ?
C7 H7 0.9300 . ?
C68 C67 1.389(6) . ?
C68 H68 0.9300 . ?
C2 C1 1.392(6) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C57 C58 1.382(5) . ?
C57 H57 0.9300 . ?
C12 H12 0.9300 . ?
C67 H67 0.9300 . ?
C53 C52 1.387(6) . ?
C53 H53 0.9300 . ?
C52 H52 0.9300 . ?
C65 H65 0.9300 . ?
C58 H58 0.9300 . ?
C18 H18 0.9300 . ?
C70 H70 0.9300 . ?
C1 H1 0.9300 . ?
O2M C1M 1.387(7) . ?
O2M H2M 0.8621 . ?
C1M H1MA 0.9600 . ?
C1M H1MB 0.9600 . ?
C1M H1MC 0.9600 . ?
O52M C51M 1.393(7) . ?
O52M H52M 0.9602 . ?
C51M H51A 0.9600 . ?
C51M H51B 0.9600 . ?
C51M H51C 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
C8A N9 C9A 108.2(3) . . ?
C8A N9 C10 125.8(3) . . ?
C9A N9 C10 124.7(3) . . ?
C18 N19 C20 121.7(4) . . ?
C18 N19 H19 119.1 . . ?
C20 N19 H19 119.1 . . ?
C70 N69 C68 122.6(4) . . ?
C70 N69 H69 114(3) . . ?
C68 N69 H69 123(3) . . ?
C59A N59 C58A 108.9(3) . . ?
C59A N59 C60 124.8(3) . . ?
C58A N59 C60 125.8(3) . . ?
C54 C54A C59A 119.5(3) . . ?
C54 C54A C54B 133.3(4) . . ?
C59A C54A C54B 107.2(3) . . ?
C5 C4B C8A 119.6(3) . . ?
C5 C4B C4A 133.5(3) . . ?
C8A C4B C4A 106.8(3) . . ?
C7 C8 C8A 117.5(4) . . ?
C7 C8 H8 121.3 . . ?
C8A C8 H8 121.3 . . ?
C55 C54B C58A 119.7(4) . . ?
C55 C54B C54A 133.6(4) . . ?
C58A C54B C54A 106.6(3) . . ?
N59 C59A C51 129.7(4) . . ?
N59 C59A C54A 108.6(3) . . ?
C51 C59A C54A 121.7(3) . . ?
C15 C10 C11 119.9(3) . . ?
C15 C10 N9 120.2(3) . . ?
C11 C10 N9 119.8(3) . . ?
N9 C8A C8 129.7(3) . . ?
N9 C8A C4B 108.9(3) . . ?
C8 C8A C4B 121.4(3) . . ?
C71 C66 C67 117.2(4) . . ?
C71 C66 C63 121.8(3) . . ?
C67 C66 C63 121.0(3) . . ?
C17 C16 C21 118.0(4) . . ?
C17 C16 C13 121.3(3) . . ?
C21 C16 C13 120.6(3) . . ?
C14 C13 C12 118.6(4) . . ?
C14 C13 C16 121.5(3) . . ?
C12 C13 C16 120.0(3) . . ?
C58 C58A N59 129.5(4) . . ?
C58 C58A C54B 121.6(3) . . ?
N59 C58A C54B 108.8(3) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C9A C4A C4 120.2(3) . . ?
C9A C4A C4B 106.9(3) . . ?
C4 C4A C4B 132.9(4) . . ?
C65 C60 C61 119.9(4) . . ?
C65 C60 N59 119.9(3) . . ?
C61 C60 N59 120.2(3) . . ?
C53 C54 C54A 118.2(4) . . ?
C53 C54 H54 120.9 . . ?
C54A C54 H54 120.9 . . ?
C62 C61 C60 119.8(4) . . ?
C62 C61 H61 120.1 . . ?
C60 C61 H61 120.1 . . ?
C52 C51 C59A 117.3(4) . . ?
C52 C51 H51 121.4 . . ?
C59A C51 H51 121.4 . . ?
C55 C56 C57 120.2(4) . . ?
C55 C56 H56 119.9 . . ?
C57 C56 H56 119.9 . . ?
C62 C63 C64 118.9(4) . . ?
C62 C63 C66 121.5(3) . . ?
C64 C63 C66 119.5(3) . . ?
C61 C62 C63 120.7(3) . . ?
C61 C62 H62 119.6 . . ?
C63 C62 H62 119.6 . . ?
C6 C5 C4B 118.5(3) . . ?
C6 C5 H5 120.8 . . ?
C4B C5 H5 120.8 . . ?
C4A C9A N9 109.2(3) . . ?
C4A C9A C1 122.0(3) . . ?
N9 C9A C1 128.8(4) . . ?
C14 C15 C10 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C20 C21 C16 119.8(4) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
C70 C71 C66 120.4(4) . . ?
C70 C71 H71 119.8 . . ?
C66 C71 H71 119.8 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N19 C20 C21 119.9(4) . . ?
N19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C3 C4 C4A 118.5(4) . . ?
C3 C4 H4 120.7 . . ?
C4A C4 H4 120.7 . . ?
C65 C64 C63 120.8(4) . . ?
C65 C64 H64 119.6 . . ?
C63 C64 H64 119.6 . . ?
C56 C55 C54B 119.1(4) . . ?
C56 C55 H55 120.5 . . ?
C54B C55 H55 120.5 . . ?
C8 C7 C6 122.4(4) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
N69 C68 C67 119.2(4) . . ?
N69 C68 H68 120.4 . . ?
C67 C68 H68 120.4 . . ?
C1 C2 C3 122.0(4) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C5 C6 C7 120.6(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C58 C57 C56 122.2(4) . . ?
C58 C57 H57 118.9 . . ?
C56 C57 H57 118.9 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C68 C67 C66 120.0(4) . . ?
C68 C67 H67 120.0 . . ?
C66 C67 H67 120.0 . . ?
C52 C53 C54 120.7(4) . . ?
C52 C53 H53 119.7 . . ?
C54 C53 H53 119.7 . . ?
C51 C52 C53 122.5(4) . . ?
C51 C52 H52 118.7 . . ?
C53 C52 H52 118.7 . . ?
C64 C65 C60 119.9(4) . . ?
C64 C65 H65 120.1 . . ?
C60 C65 H65 120.1 . . ?
C57 C58 C58A 117.1(4) . . ?
C57 C58 H58 121.5 . . ?
C58A C58 H58 121.5 . . ?
N19 C18 C17 120.6(4) . . ?
N19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N69 C70 C71 120.6(4) . . ?
N69 C70 H70 119.7 . . ?
C71 C70 H70 119.7 . . ?
C2 C1 C9A 116.4(4) . . ?
C2 C1 H1 121.8 . . ?
C9A C1 H1 121.8 . . ?
C1M O2M H2M 109.0 . . ?
O2M C1M H1MA 109.5 . . ?
O2M C1M H1MB 109.5 . . ?
H1MA C1M H1MB 109.5 . . ?
O2M C1M H1MC 109.5 . . ?
H1MA C1M H1MC 109.5 . . ?
H1MB C1M H1MC 109.5 . . ?
C51M O52M H52M 109.0 . . ?
O52M C51M H51A 109.5 . . ?
O52M C51M H51B 109.5 . . ?
H51A C51M H51B 109.5 . . ?
O52M C51M H51C 109.5 . . ?
H51A C51M H51C 109.5 . . ?
H51B C51M H51C 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
C54 C54A C54B C55 3.4(7) . . . . ?
C59A C54A C54B C55 -176.5(4) . . . . ?
C54 C54A C54B C58A -178.7(4) . . . . ?
C59A C54A C54B C58A 1.4(4) . . . . ?
C58A N59 C59A C51 179.5(4) . . . . ?
C60 N59 C59A C51 -7.9(6) . . . . ?
C58A N59 C59A C54A 0.6(4) . . . . ?
C60 N59 C59A C54A 173.1(3) . . . . ?
C54 C54A C59A N59 178.9(3) . . . . ?
C54B C54A C59A N59 -1.2(4) . . . . ?
C54 C54A C59A C51 -0.2(5) . . . . ?
C54B C54A C59A C51 179.7(3) . . . . ?
C8A N9 C10 C15 -132.9(4) . . . . ?
C9A N9 C10 C15 61.7(5) . . . . ?
C8A N9 C10 C11 47.1(5) . . . . ?
C9A N9 C10 C11 -118.3(4) . . . . ?
C9A N9 C8A C8 -179.7(4) . . . . ?
C10 N9 C8A C8 12.9(6) . . . . ?
C9A N9 C8A C4B -1.6(4) . . . . ?
C10 N9 C8A C4B -168.9(3) . . . . ?
C7 C8 C8A N9 177.2(4) . . . . ?
C7 C8 C8A C4B -0.8(5) . . . . ?
C5 C4B C8A N9 -178.3(3) . . . . ?
C4A C4B C8A N9 1.5(4) . . . . ?
C5 C4B C8A C8 0.0(5) . . . . ?
C4A C4B C8A C8 179.8(3) . . . . ?
C17 C16 C13 C14 -139.9(4) . . . . ?
C21 C16 C13 C14 40.0(5) . . . . ?
C17 C16 C13 C12 39.6(5) . . . . ?
C21 C16 C13 C12 -140.5(4) . . . . ?
C59A N59 C58A C58 177.9(4) . . . . ?
C60 N59 C58A C58 5.5(6) . . . . ?
C59A N59 C58A C54B 0.4(4) . . . . ?
C60 N59 C58A C54B -172.1(3) . . . . ?
C55 C54B C58A C58 -0.6(6) . . . . ?
C54A C54B C58A C58 -178.9(3) . . . . ?
C55 C54B C58A N59 177.2(3) . . . . ?
C54A C54B C58A N59 -1.1(4) . . . . ?
C5 C4B C4A C9A 178.9(4) . . . . ?
C8A C4B C4A C9A -0.9(4) . . . . ?
C5 C4B C4A C4 -3.9(7) . . . . ?
C8A C4B C4A C4 176.3(4) . . . . ?
C59A N59 C60 C65 -51.9(5) . . . . ?
C58A N59 C60 C65 119.4(4) . . . . ?
C59A N59 C60 C61 128.2(4) . . . . ?
C58A N59 C60 C61 -60.6(5) . . . . ?
C59A C54A C54 C53 -0.6(5) . . . . ?
C54B C54A C54 C53 179.5(4) . . . . ?
C65 C60 C61 C62 -0.6(6) . . . . ?
N59 C60 C61 C62 179.3(3) . . . . ?
N59 C59A C51 C52 -177.7(4) . . . . ?
C54A C59A C51 C52 1.2(6) . . . . ?
C71 C66 C63 C62 142.3(4) . . . . ?
C67 C66 C63 C62 -39.2(5) . . . . ?
C71 C66 C63 C64 -40.0(5) . . . . ?
C67 C66 C63 C64 138.6(4) . . . . ?
C60 C61 C62 C63 -0.4(6) . . . . ?
C64 C63 C62 C61 0.8(6) . . . . ?
C66 C63 C62 C61 178.5(3) . . . . ?
C8A C4B C5 C6 0.6(5) . . . . ?
C4A C4B C5 C6 -179.2(4) . . . . ?
C4 C4A C9A N9 -177.7(3) . . . . ?
C4B C4A C9A N9 0.0(4) . . . . ?
C4 C4A C9A C1 0.3(5) . . . . ?
C4B C4A C9A C1 178.0(3) . . . . ?
C8A N9 C9A C4A 1.0(4) . . . . ?
C10 N9 C9A C4A 168.5(3) . . . . ?
C8A N9 C9A C1 -176.9(4) . . . . ?
C10 N9 C9A C1 -9.3(6) . . . . ?
C11 C10 C15 C14 1.4(6) . . . . ?
N9 C10 C15 C14 -178.6(3) . . . . ?
C21 C16 C17 C18 1.6(6) . . . . ?
C13 C16 C17 C18 -178.5(4) . . . . ?
C10 C15 C14 C13 -0.2(6) . . . . ?
C12 C13 C14 C15 -1.0(6) . . . . ?
C16 C13 C14 C15 178.6(3) . . . . ?
C17 C16 C21 C20 -2.4(5) . . . . ?
C13 C16 C21 C20 177.7(3) . . . . ?
C67 C66 C71 C70 -2.2(6) . . . . ?
C63 C66 C71 C70 176.4(4) . . . . ?
C15 C10 C11 C12 -1.5(6) . . . . ?
N9 C10 C11 C12 178.6(3) . . . . ?
C18 N19 C20 C21 -0.1(6) . . . . ?
C16 C21 C20 N19 1.6(6) . . . . ?
C2 C3 C4 C4A 0.7(6) . . . . ?
C9A C4A C4 C3 -0.3(5) . . . . ?
C4B C4A C4 C3 -177.2(4) . . . . ?
C62 C63 C64 C65 -0.2(6) . . . . ?
C66 C63 C64 C65 -178.0(4) . . . . ?
C57 C56 C55 C54B -0.6(6) . . . . ?
C58A C54B C55 C56 0.6(5) . . . . ?
C54A C54B C55 C56 178.3(4) . . . . ?
C8A C8 C7 C6 1.0(6) . . . . ?
C70 N69 C68 C67 -1.6(6) . . . . ?
C4 C3 C2 C1 -1.1(6) . . . . ?
C4B C5 C6 C7 -0.4(5) . . . . ?
C8 C7 C6 C5 -0.4(6) . . . . ?
C55 C56 C57 C58 0.5(6) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C14 C13 C12 C11 1.0(6) . . . . ?
C16 C13 C12 C11 -178.6(4) . . . . ?
N69 C68 C67 C66 -1.3(6) . . . . ?
C71 C66 C67 C68 3.1(5) . . . . ?
C63 C66 C67 C68 -175.5(3) . . . . ?
C54A C54 C53 C52 0.4(5) . . . . ?
C59A C51 C52 C53 -1.3(6) . . . . ?
C54 C53 C52 C51 0.6(6) . . . . ?
C63 C64 C65 C60 -0.8(6) . . . . ?
C61 C60 C65 C64 1.2(6) . . . . ?
N59 C60 C65 C64 -178.7(3) . . . . ?
C56 C57 C58 C58A -0.5(6) . . . . ?
N59 C58A C58 C57 -176.7(4) . . . . ?
C54B C58A C58 C57 0.6(6) . . . . ?
C20 N19 C18 C17 -0.7(6) . . . . ?
C16 C17 C18 N19 -0.1(6) . . . . ?
C68 N69 C70 C71 2.5(6) . . . . ?
C66 C71 C70 N69 -0.5(6) . . . . ?
C3 C2 C1 C9A 1.1(6) . . . . ?
C4A C9A C1 C2 -0.7(6) . . . . ?
N9 C9A C1 C2 176.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        77.84
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.974
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.186
####################################################################### 
# 
# 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_kl1302
_database_code_depnum_ccdc_archive 'CCDC 1988913'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Insitute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2019-09-11
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '(Cl), 2(H2 O), (C11 H10 N)'
_chemical_formula_sum            'C11 H14 Cl1 N1 O2'
_chemical_formula_weight         227.64
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44 H56 Cl4 N4 O8'
_chemical_oxdiff_usercomment     'from Kaspars'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.0110(1)
_cell_length_b                   9.8156(1)
_cell_length_c                   17.0473(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1173.15(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5289
_cell_measurement_temperature    160.0(1)
_cell_measurement_theta_max      76.3540
_cell_measurement_theta_min      5.1840
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    2.734
_exptl_absorpt_correction_T_max  0.96849
_exptl_absorpt_correction_T_min  0.87927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (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    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6367
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.324
_diffrn_reflns_theta_min         5.200
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -47.00   0.50    0.26    --  -47.95 -43.00  77.00  144
  2  ω    -91.00 -65.00   0.50    0.93    --  -86.25 -82.00-112.00   52
  3  ω    -74.00 -49.00   0.50    0.93    --  -86.25 112.00  91.00   50
  4  ω    -48.00 -23.00   0.50    0.93    --  -86.25  43.00-130.00   50
  5  ω    140.00 178.00   0.50    0.93    --  107.75  43.00-130.00   76
  6  ω    128.00 170.00   0.50    0.93    --  107.75 112.00  91.00   84
  7  ω    -16.00  28.00   0.50    0.26    --  -47.95  19.00   0.00   88
  8  ω   -118.00 -92.00   0.50    0.26    --  -47.95-125.00-150.00   52
  9  ω     89.00 115.00   0.50    0.26    --   47.95  77.00-120.00   52
 10  ω     41.00  71.00   0.50    0.93    --  107.75 -61.00  90.00   60
 11  ω     39.00  87.00   0.50    0.93    --  107.75 -77.00  90.00   96
 12  ω     98.00 171.00   0.50    0.93    --  107.75  15.00-150.00  146
 13  ω     42.00 104.00   0.50    0.93    --  107.75 -77.00  30.00  124
 14  ω     35.00  71.00   0.50    0.93    --  107.75 -61.00-150.00   72
 15  ω    127.00 175.00   0.50    0.93    --  107.75 125.00  60.00   96
 16  ω     40.00  69.00   0.50    0.93    --  107.75 -77.00 -90.00   58
 17  ω     38.00  67.00   0.50    0.93    --  107.75 -61.00 -30.00   58
 18  ω     43.00  69.00   0.50    0.93    --  107.75 -77.00   0.00   52
 19  ω     39.00  67.00   0.50    0.93    --  107.75 -61.00  30.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1049042000
_diffrn_orient_matrix_UB_12      0.1091829000
_diffrn_orient_matrix_UB_13      0.0484741000
_diffrn_orient_matrix_UB_21      0.0532309000
_diffrn_orient_matrix_UB_22      0.1085009000
_diffrn_orient_matrix_UB_23      -0.0615263000
_diffrn_orient_matrix_UB_31      -0.1856013000
_diffrn_orient_matrix_UB_32      -0.0306940000
_diffrn_orient_matrix_UB_33      -0.0450593000
_diffrn_oxdiff_digest_frames     
;
01ad9fdcb0a3fa4ce6d1f3d2207c18e3ef000846fc7
;
_diffrn_oxdiff_digest_hkl        
;
017fa11c97174a96961fb9093d4a0d5b27cd0b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                2275
_reflns_number_total             2351
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 
;
 Flack x determined using 843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.083(34)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0678
_refine_ls_restrained_S_all      1.101
_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)+(0.1281P)²+1.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1990
_refine_ls_wR_factor_ref         0.2025
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C8(H8), C12(H12), C2(H2), C6(H6), C9(H9), C3(H3), C11(H11),
 C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.8436(2) 0.89501(15) 0.82825(8) 0.0520(5) Uani 1 1 d . . . . .
O1W O 0.5201(6) 0.8585(3) 0.9279(2) 0.0422(9) Uani 1 1 d . . . . .
H1WA H 0.629230 0.868891 0.900229 0.051 Uiso 1 1 d R . . . .
H1WB H 0.559220 0.819091 0.976239 0.051 Uiso 1 1 d R . . . .
N1 N 0.8592(6) 0.8142(4) 0.6592(2) 0.0334(9) Uani 1 1 d . . . . .
H1 H 0.863838 0.842887 0.706837 0.040 Uiso 1 1 calc R . . . .
O2W O 0.1494(7) 0.7262(4) 0.9124(3) 0.0552(10) Uani 1 1 d . . . . .
H2WA H 0.242981 0.779972 0.916987 0.066 Uiso 1 1 d R . . . .
H2WB H 0.056831 0.776342 0.894687 0.066 Uiso 1 1 d R . . . .
C4 C 0.8426(6) 0.7216(4) 0.5070(2) 0.0243(8) Uani 1 1 d . . . . .
C7 C 0.8384(6) 0.6717(4) 0.4252(2) 0.0242(8) Uani 1 1 d . . . . .
C5 C 0.8809(6) 0.6331(5) 0.5690(3) 0.0277(9) Uani 1 1 d . . . . .
H5 H 0.900337 0.540872 0.559220 0.033 Uiso 1 1 calc R . . . .
C8 C 0.8724(6) 0.7618(5) 0.3624(3) 0.0287(9) Uani 1 1 d . . . . .
H8 H 0.892758 0.853797 0.372273 0.034 Uiso 1 1 calc R . . . .
C12 C 0.8059(6) 0.5344(4) 0.4084(3) 0.0291(9) Uani 1 1 d . . . . .
H12 H 0.781404 0.473537 0.448922 0.035 Uiso 1 1 calc R . . . .
C2 C 0.8219(6) 0.9021(5) 0.6024(3) 0.0327(9) Uani 1 1 d . . . . .
H2 H 0.801619 0.993317 0.614532 0.039 Uiso 1 1 calc R . . . .
C6 C 0.8899(6) 0.6821(5) 0.6449(3) 0.0331(10) Uani 1 1 d . . . . .
H6 H 0.917360 0.623112 0.686040 0.040 Uiso 1 1 calc R . . . .
C9 C 0.8756(7) 0.7139(5) 0.2860(3) 0.0338(10) Uani 1 1 d . . . . .
H9 H 0.897341 0.773999 0.244800 0.041 Uiso 1 1 calc R . . . .
C3 C 0.8128(6) 0.8593(5) 0.5248(3) 0.0279(9) Uani 1 1 d . . . . .
H3 H 0.787068 0.921553 0.485088 0.034 Uiso 1 1 calc R . . . .
C11 C 0.8101(7) 0.4887(5) 0.3316(3) 0.0354(10) Uani 1 1 d . . . . .
H11 H 0.787997 0.397115 0.320963 0.042 Uiso 1 1 calc R . . . .
C10 C 0.8467(7) 0.5777(5) 0.2707(3) 0.0352(10) Uani 1 1 d . . . . .
H10 H 0.851834 0.545701 0.219362 0.042 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1W H1WA 0.9041 . ?
O1W H1WB 0.9512 . ?
N1 H1 0.8600 . ?
N1 C2 1.323(7) . ?
N1 C6 1.337(6) . ?
O2W H2WA 0.8460 . ?
O2W H2WB 0.8686 . ?
C4 C7 1.479(6) . ?
C4 C5 1.394(6) . ?
C4 C3 1.401(6) . ?
C7 C8 1.408(6) . ?
C7 C12 1.396(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.384(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(6) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.377(7) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.382(7) . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1WA O1W H1WB 104.7 . . ?
C2 N1 H1 119.0 . . ?
C2 N1 C6 122.0(4) . . ?
C6 N1 H1 119.0 . . ?
H2WA O2W H2WB 104.9 . . ?
C5 C4 C7 120.8(4) . . ?
C5 C4 C3 117.8(4) . . ?
C3 C4 C7 121.4(4) . . ?
C8 C7 C4 120.4(4) . . ?
C12 C7 C4 121.1(4) . . ?
C12 C7 C8 118.5(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 120.0 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.3(4) . . ?
C11 C12 H12 119.9 . . ?
N1 C2 H2 119.7 . . ?
N1 C2 C3 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
N1 C6 C5 120.1(4) . . ?
N1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C4 C3 H3 120.3 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C9 C10 C11 119.9(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?

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
N1 C2 C3 C4 0.3(6) . . . . ?
C4 C7 C8 C9 177.5(4) . . . . ?
C4 C7 C12 C11 -177.4(4) . . . . ?
C4 C5 C6 N1 1.0(6) . . . . ?
C7 C4 C5 C6 178.1(4) . . . . ?
C7 C4 C3 C2 -178.7(4) . . . . ?
C7 C8 C9 C10 -0.4(7) . . . . ?
C7 C12 C11 C10 0.1(7) . . . . ?
C5 C4 C7 C8 -155.7(4) . . . . ?
C5 C4 C7 C12 22.5(6) . . . . ?
C5 C4 C3 C2 -0.1(6) . . . . ?
C8 C7 C12 C11 0.9(7) . . . . ?
C8 C9 C10 C11 1.5(8) . . . . ?
C12 C7 C8 C9 -0.8(6) . . . . ?
C12 C11 C10 C9 -1.3(8) . . . . ?
C2 N1 C6 C5 -0.8(7) . . . . ?
C6 N1 C2 C3 0.2(7) . . . . ?
C3 C4 C7 C8 22.8(6) . . . . ?
C3 C4 C7 C12 -158.9(4) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.593
####################################################################### 
# 
# 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_kl_lt4aie1
_database_code_depnum_ccdc_archive 'CCDC 1988915'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Insitute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2018-12-07
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N S, Cl O4 '
_chemical_formula_sum            'C21 H16 Cl N O4 S'
_chemical_formula_weight         413.86
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H B F N S'
_chemical_oxdiff_usercomment     'from Kaspars'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.7267(2)
_cell_length_b                   13.0423(3)
_cell_length_c                   36.8750(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3716.04(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    21151
_cell_measurement_temperature    140.0(10)
_cell_measurement_theta_max      76.7950
_cell_measurement_theta_min      3.5860
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.517
_exptl_absorpt_coefficient_mu    3.121
_exptl_absorpt_correction_T_max  0.98143
_exptl_absorpt_correction_T_min  0.62335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.21a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Plate '
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1173
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            53801
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.622
_diffrn_reflns_theta_min         3.595
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -9.00   0.50    1.60    --  -49.16 121.00   1.00  156
  2  ω    -91.00 -66.00   0.50    1.60    --  -84.25 153.00 160.00   50
  3  ω     73.00  98.00   0.50    1.60    --   49.66 153.00 160.00   50
  4  ω     97.00 122.00   0.50    1.60    --  105.75 153.00 160.00   50
  5  ω     93.00 137.00   0.50    1.60    --  105.75 125.00 150.00   88
  6  ω    143.00 169.00   0.50    1.60    --  105.75 125.00 150.00   52
  7  ω    145.00 177.00   0.50    1.60    --  105.75  77.00  90.00   64
  8  ω    136.00 162.00   0.50    1.60    --  105.75  77.00  60.00   52
  9  ω    128.00 164.00   0.50    1.60    --  105.75  77.00   0.00   72
 10  ω    129.00 154.00   0.50    1.60    --  105.75  15.00 -30.00   50
 11  ω    120.00 146.00   0.50    1.60    --  105.75  15.00  30.00   52
 12  ω    130.00 156.00   0.50    1.60    --  105.75  61.00  90.00   52
 13  ω    116.00 141.00   0.50    1.60    --  105.75 121.00   1.00   50
 14  ω    111.00 174.00   0.50    1.60    --  105.75 125.00 -30.00  126
 15  ω    106.00 146.00   0.50    1.60    --  105.75 125.00  90.00   80
 16  ω    112.00 177.00   0.50    1.60    --  105.75  45.00 120.00  130
 17  ω     97.00 143.00   0.50    1.60    --  105.75  45.00  60.00   92
 18  ω     89.00 122.00   0.50    1.60    --  105.75  77.00   0.00   66
 19  ω     93.00 119.00   0.50    1.60    --  105.75  61.00  60.00   52
 20  ω     89.00 137.00   0.50    1.60    --  105.75  77.00  30.00   96
 21  ω     93.00 124.00   0.50    1.60    --  105.75  61.00  90.00   62
 22  ω     37.00  68.00   0.50    1.60    --  105.75 -61.00 -30.00   62
 23  ω     63.00  89.00   0.50    1.60    --  105.75 -77.00  30.00   52
 24  ω     58.00  84.00   0.50    1.60    --  105.75 -77.00  90.00   52
 25  ω     75.00 107.00   0.50    1.60    --  105.75 -94.00  90.00   64
 26  ω     67.00  92.00   0.50    1.60    --  105.75-153.00 119.00   50
 27  ω     54.00  93.00   0.50    1.60    --  105.75 -94.00 120.00   78
 28  ω     55.00  80.00   0.50    1.60    --   49.66-153.00 119.00   50
 29  ω     35.00  85.00   0.50    1.60    --  105.75-125.00  60.00  100
 30  ω     42.00 104.00   0.50    1.60    --  105.75 -94.00  60.00  124
 31  ω     45.00  70.00   0.50    1.60    --  105.75 -61.00 120.00   50
 32  ω     37.00  71.00   0.50    1.60    --  105.75 -61.00 150.00   68
 33  ω     36.00  65.00   0.50    1.60    --  105.75 -61.00  90.00   58
 34  ω     43.00  68.00   0.50    1.60    --  105.75-125.00  90.00   50
 35  ω     42.00  98.00   0.50    1.60    --  105.75-125.00 -30.00  112
 36  ω     70.00 109.00   0.50    1.60    --  105.75 -94.00 -60.00   78
 37  ω     65.00 104.00   0.50    1.60    --  105.75 -77.00-150.00   78
 38  ω     68.00  93.00   0.50    1.60    --  105.75-125.00-180.00   50
 39  ω     64.00 107.00   0.50    1.60    --  105.75 -94.00-120.00   86
 40  ω     50.00  75.00   0.50    1.60    --  105.75-121.00 -81.00   50
 41  ω     36.00 104.00   0.50    1.60    --  105.75 -77.00 -60.00  136
 42  ω     35.00  71.00   0.50    1.60    --  105.75 -61.00-150.00   72
 43  ω     41.00  84.00   0.50    1.60    --  105.75 -94.00-180.00   86
 44  ω     33.00  59.00   0.50    1.60    --   49.66-121.00 -81.00   52
 45  ω    101.00 126.00   0.50    1.60    --  105.75  45.00-180.00   50
 46  ω     94.00 119.00   0.50    1.60    --  105.75  61.00-180.00   50
 47  ω     88.00 121.00   0.50    1.60    --   49.66  77.00-180.00   66
 48  ω    102.00 177.00   0.50    1.60    --  105.75  45.00 -90.00  150
 49  ω    -50.00 -13.00   0.50    1.60    --  -84.25  45.00-150.00   74
 50  ω   -118.00 -88.00   0.50    1.60    --  -49.16 -77.00  30.00   60
 51  ω   -116.00 -91.00   0.50    1.60    --  -49.16 -77.00  90.00   50
 52  ω   -120.00 -52.00   0.50    1.60    --  -49.16-153.00 119.00  136
 53  ω   -110.00 -85.00   0.50    1.60    --  -49.16-121.00 -81.00   50
 54  ω   -139.00-114.00   0.50    1.60    --  -84.25-121.00 -81.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0732448000
_diffrn_orient_matrix_UB_12      -0.0638532000
_diffrn_orient_matrix_UB_13      -0.0316375000
_diffrn_orient_matrix_UB_21      -0.0558105000
_diffrn_orient_matrix_UB_22      -0.0842591000
_diffrn_orient_matrix_UB_23      0.0268917000
_diffrn_orient_matrix_UB_31      -0.1766449000
_diffrn_orient_matrix_UB_32      0.0529105000
_diffrn_orient_matrix_UB_33      0.0046384000
_diffrn_oxdiff_ac4_digest_frames 
;
01888d5de93e12e774e315a110b766598700030997a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                7012
_reflns_number_total             7836
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 
;
 Flack x determined using 2701 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(9)
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         7836
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1095P)²+3.2213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1724
_refine_ls_wR_factor_ref         0.1832
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C67(H67), C63(H63), C11(H11), C54(H54), C7(H7), C64(H64), C4(H4), C71(H71),
 C65(H65), C19(H19), C66(H66), C61(H61), C73(H73), C13(H13), C20(H20), C23(H23),
  C17(H17), C69(H69), C10(H10), C22(H22), C8(H8), C72(H72), C15(H15), C60(H60),
 C14(H14), C16(H16), C21(H21), C57(H57), C70(H70), C58(H58)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.16733(18) 0.40165(10) 0.36808(4) 0.0380(3) Uani 1 1 d . . . . .
Cl2 Cl 0.9146(2) 0.14270(11) 0.48749(4) 0.0465(4) Uani 1 1 d . . . . .
S1 S 0.71897(18) 0.79644(11) 0.39902(4) 0.0385(3) Uani 1 1 d . . . . .
S51 S 0.1403(2) -0.05855(10) 0.33537(4) 0.0417(3) Uani 1 1 d . . . . .
O1 O 1.2083(7) 0.4156(4) 0.40545(12) 0.0525(11) Uani 1 1 d . . . . .
O3 O 1.1581(9) 0.4992(4) 0.35067(15) 0.0648(14) Uani 1 1 d . . . . .
O2 O 1.2993(7) 0.3419(5) 0.35198(14) 0.0646(14) Uani 1 1 d . . . . .
N9 N 0.7782(8) 0.4051(5) 0.43632(16) 0.0528(13) Uani 1 1 d . . . . .
H9 H 0.787(12) 0.346(7) 0.449(3) 0.07(3) Uiso 1 1 d . . . . .
O4 O 1.0059(7) 0.3510(5) 0.36464(17) 0.0717(16) Uani 1 1 d . . . . .
C3 C 0.6418(7) 0.6874(4) 0.34328(15) 0.0372(11) Uani 1 1 d . . . . .
C68 C 0.0206(7) -0.2151(4) 0.29052(16) 0.0365(11) Uani 1 1 d . . . . .
C67 C 0.2787(7) -0.3356(4) 0.42485(16) 0.0364(11) Uani 1 1 d . . . . .
H67 H 0.323737 -0.365637 0.404025 0.044 Uiso 1 1 calc R . . . .
N59 N 0.3979(11) 0.1470(5) 0.44683(17) 0.066(2) Uani 1 1 d . . . . .
H59 H 0.407(14) 0.198(9) 0.459(3) 0.09(3) Uiso 1 1 d . . . . .
C2 C 0.6894(7) 0.6776(4) 0.37864(16) 0.0369(11) Uani 1 1 d . . . . .
C63 C 0.1301(7) -0.1974(4) 0.45476(15) 0.0370(11) Uani 1 1 d . . . . .
H63 H 0.074356 -0.134241 0.453868 0.044 Uiso 1 1 calc R . . . .
C62 C 0.1988(7) -0.2400(4) 0.42247(15) 0.0328(11) Uani 1 1 d . . . . .
C56 C 0.2682(9) -0.0050(4) 0.40257(17) 0.0436(14) Uani 1 1 d . . . . .
C5 C 0.6649(7) 0.8600(4) 0.35996(16) 0.0386(12) Uani 1 1 d . . . . .
C6 C 0.7167(7) 0.5840(5) 0.40010(16) 0.0391(12) Uani 1 1 d . . . . .
C55 C 0.0876(7) -0.1846(4) 0.32631(15) 0.0353(11) Uani 1 1 d . . . . .
C11 C 0.6157(8) 0.4971(4) 0.39382(16) 0.0398(12) Uani 1 1 d . . . . .
H11 H 0.525795 0.499349 0.377068 0.048 Uiso 1 1 calc R . . . .
C52 C 0.1989(8) -0.0861(4) 0.37921(16) 0.0386(12) Uani 1 1 d . . . . .
C54 C 0.1188(7) -0.2448(4) 0.35612(15) 0.0343(11) Uani 1 1 d . . . . .
H54 H 0.102475 -0.315443 0.356064 0.041 Uiso 1 1 calc R . . . .
C7 C 0.8458(8) 0.5775(5) 0.42654(16) 0.0445(13) Uani 1 1 d . . . . .
H7 H 0.910847 0.635107 0.432475 0.053 Uiso 1 1 calc R . . . .
C64 C 0.1442(8) -0.2473(5) 0.48702(17) 0.0425(13) Uani 1 1 d . . . . .
H64 H 0.097935 -0.217876 0.507859 0.051 Uiso 1 1 calc R . . . .
C18 C 0.6683(8) 0.9732(5) 0.35732(17) 0.0406(13) Uani 1 1 d . . . . .
C4 C 0.6258(7) 0.7914(5) 0.33285(16) 0.0394(12) Uani 1 1 d . . . . .
H4 H 0.591936 0.811599 0.309723 0.047 Uiso 1 1 calc R . . . .
C12 C 0.6166(7) 0.6031(5) 0.31683(16) 0.0391(12) Uani 1 1 d . . . . .
C53 C 0.1785(7) -0.1898(4) 0.38736(15) 0.0349(11) Uani 1 1 d . . . . .
C71 C -0.1114(10) -0.2731(5) 0.22338(19) 0.0533(16) Uani 1 1 d . . . . .
H71 H -0.153299 -0.292555 0.200763 0.064 Uiso 1 1 calc R . . . .
C65 C 0.2276(8) -0.3423(5) 0.48919(17) 0.0421(12) Uani 1 1 d . . . . .
H65 H 0.239738 -0.375396 0.511379 0.051 Uiso 1 1 calc R . . . .
C19 C 0.5835(9) 1.0217(5) 0.32864(19) 0.0488(15) Uani 1 1 d . . . . .
H19 H 0.522171 0.982740 0.311862 0.059 Uiso 1 1 calc R . . . .
C66 C 0.2921(8) -0.3865(5) 0.45763(17) 0.0415(13) Uani 1 1 d . . . . .
H66 H 0.344520 -0.450589 0.458582 0.050 Uiso 1 1 calc R . . . .
C61 C 0.3830(9) -0.0269(5) 0.43101(17) 0.0471(15) Uani 1 1 d . . . . .
H61 H 0.415794 -0.094447 0.435256 0.057 Uiso 1 1 calc R . . . .
C73 C -0.0593(9) -0.1437(5) 0.26776(17) 0.0463(14) Uani 1 1 d . . . . .
H73 H -0.069967 -0.075980 0.275316 0.056 Uiso 1 1 calc R . . . .
C13 C 0.7298(8) 0.5193(5) 0.31526(17) 0.0438(13) Uani 1 1 d . . . . .
H13 H 0.824785 0.516261 0.330704 0.053 Uiso 1 1 calc R . . . .
C20 C 0.5898(11) 1.1281(6) 0.3249(2) 0.0593(18) Uani 1 1 d . . . . .
H20 H 0.534258 1.159421 0.305492 0.071 Uiso 1 1 calc R . . . .
C23 C 0.7568(9) 1.0337(5) 0.38219(19) 0.0486(15) Uani 1 1 d . . . . .
H23 H 0.812325 1.003139 0.401786 0.058 Uiso 1 1 calc R . . . .
C17 C 0.4777(9) 0.6068(5) 0.29247(18) 0.0470(14) Uani 1 1 d . . . . .
H17 H 0.403055 0.662723 0.292686 0.056 Uiso 1 1 calc R . . . .
C69 C 0.0272(9) -0.3161(5) 0.27961(18) 0.0484(14) Uani 1 1 d . . . . .
H69 H 0.075800 -0.365232 0.294791 0.058 Uiso 1 1 calc R . . . .
C10 C 0.6495(10) 0.4084(5) 0.41245(17) 0.0497(15) Uani 1 1 d . . . . .
H10 H 0.582160 0.350451 0.408385 0.060 Uiso 1 1 calc R . . . .
C22 C 0.7631(11) 1.1396(5) 0.3780(2) 0.0589(18) Uani 1 1 d . . . . .
H22 H 0.825706 1.178939 0.394463 0.071 Uiso 1 1 calc R . . . .
C8 C 0.8761(9) 0.4862(6) 0.44366(18) 0.0506(15) Uani 1 1 d . . . . .
H8 H 0.965412 0.480975 0.460468 0.061 Uiso 1 1 calc R . . . .
C72 C -0.1225(9) -0.1721(5) 0.23431(18) 0.0487(14) Uani 1 1 d . . . . .
H72 H -0.172456 -0.123430 0.219152 0.058 Uiso 1 1 calc R . . . .
C15 C 0.5625(11) 0.4449(6) 0.2670(2) 0.0588(18) Uani 1 1 d . . . . .
H15 H 0.544629 0.392228 0.250425 0.071 Uiso 1 1 calc R . . . .
C60 C 0.4477(11) 0.0497(6) 0.4527(2) 0.0577(18) Uani 1 1 d . . . . .
H60 H 0.525082 0.034403 0.471259 0.069 Uiso 1 1 calc R . . . .
O5 O 0.9048(15) 0.2185(7) 0.4616(2) 0.125(4) Uani 1 1 d . . . . .
C14 C 0.7003(10) 0.4410(5) 0.29075(18) 0.0517(15) Uani 1 1 d . . . . .
H14 H 0.774458 0.384893 0.290258 0.062 Uiso 1 1 calc R . . . .
C16 C 0.4508(9) 0.5280(5) 0.2682(2) 0.0533(16) Uani 1 1 d . . . . .
H16 H 0.356930 0.530734 0.252387 0.064 Uiso 1 1 calc R . . . .
C21 C 0.6774(11) 1.1870(5) 0.3498(2) 0.0600(18) Uani 1 1 d . . . . .
H21 H 0.679022 1.258059 0.347547 0.072 Uiso 1 1 calc R . . . .
C57 C 0.2260(12) 0.0980(5) 0.39724(19) 0.0571(18) Uani 1 1 d . . . . .
H57 H 0.154413 0.116880 0.378094 0.069 Uiso 1 1 calc R . . . .
C70 C -0.0385(11) -0.3449(6) 0.2459(2) 0.0606(19) Uani 1 1 d . . . . .
H70 H -0.032868 -0.413074 0.238692 0.073 Uiso 1 1 calc R . . . .
C58 C 0.2907(14) 0.1720(5) 0.4204(2) 0.070(2) Uani 1 1 d . . . . .
H58 H 0.258283 0.240151 0.417356 0.085 Uiso 1 1 calc R . . . .
O8 O 0.7479(15) 0.1257(10) 0.5026(4) 0.186(6) Uani 1 1 d . . . . .
O6 O 0.9915(17) 0.1745(8) 0.5174(3) 0.174(6) Uani 1 1 d . . . . .
O7 O 0.987(2) 0.0562(5) 0.4752(2) 0.187(7) 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
Cl1 O1 1.426(4) . ?
Cl1 O3 1.427(5) . ?
Cl1 O2 1.414(5) . ?
Cl1 O4 1.417(5) . ?
Cl2 O5 1.377(6) . ?
Cl2 O8 1.420(11) . ?
Cl2 O6 1.319(7) . ?
Cl2 O7 1.340(7) . ?
S1 C2 1.738(6) . ?
S1 C5 1.713(6) . ?
S51 C55 1.726(6) . ?
S51 C52 1.717(6) . ?
N9 H9 0.90(10) . ?
N9 C10 1.329(9) . ?
N9 C8 1.329(9) . ?
C3 C2 1.361(8) . ?
C3 C4 1.415(8) . ?
C3 C12 1.483(8) . ?
C68 C55 1.473(8) . ?
C68 C73 1.397(8) . ?
C68 C69 1.378(9) . ?
C67 H67 0.9300 . ?
C67 C62 1.393(8) . ?
C67 C66 1.383(8) . ?
N59 H59 0.81(11) . ?
N59 C60 1.343(11) . ?
N59 C58 1.320(12) . ?
C2 C6 1.470(8) . ?
C63 H63 0.9300 . ?
C63 C62 1.417(7) . ?
C63 C64 1.360(9) . ?
C62 C53 1.459(8) . ?
C56 C52 1.466(8) . ?
C56 C61 1.403(10) . ?
C56 C57 1.396(9) . ?
C5 C18 1.480(8) . ?
C5 C4 1.374(8) . ?
C6 C11 1.395(8) . ?
C6 C7 1.397(9) . ?
C55 C54 1.372(8) . ?
C11 H11 0.9300 . ?
C11 C10 1.370(9) . ?
C52 C53 1.395(7) . ?
C54 H54 0.9300 . ?
C54 C53 1.433(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(10) . ?
C64 H64 0.9300 . ?
C64 C65 1.399(9) . ?
C18 C19 1.396(10) . ?
C18 C23 1.390(9) . ?
C4 H4 0.9300 . ?
C12 C13 1.402(9) . ?
C12 C17 1.400(9) . ?
C71 H71 0.9300 . ?
C71 C72 1.380(10) . ?
C71 C70 1.373(10) . ?
C65 H65 0.9300 . ?
C65 C66 1.391(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.396(10) . ?
C66 H66 0.9300 . ?
C61 H61 0.9300 . ?
C61 C60 1.375(9) . ?
C73 H73 0.9300 . ?
C73 C72 1.377(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(11) . ?
C23 H23 0.9300 . ?
C23 C22 1.390(10) . ?
C17 H17 0.9300 . ?
C17 C16 1.379(9) . ?
C69 H69 0.9300 . ?
C69 C70 1.393(10) . ?
C10 H10 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.381(11) . ?
C8 H8 0.9300 . ?
C72 H72 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.379(11) . ?
C15 C16 1.387(10) . ?
C60 H60 0.9300 . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C21 H21 0.9300 . ?
C57 H57 0.9300 . ?
C57 C58 1.382(11) . ?
C70 H70 0.9300 . ?
C58 H58 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cl1 O3 109.4(3) . . ?
O2 Cl1 O1 108.4(3) . . ?
O2 Cl1 O3 109.8(4) . . ?
O2 Cl1 O4 109.9(4) . . ?
O4 Cl1 O1 110.0(3) . . ?
O4 Cl1 O3 109.3(4) . . ?
O5 Cl2 O8 109.5(7) . . ?
O6 Cl2 O5 112.3(8) . . ?
O6 Cl2 O8 97.5(10) . . ?
O6 Cl2 O7 111.0(8) . . ?
O7 Cl2 O5 113.1(5) . . ?
O7 Cl2 O8 112.5(8) . . ?
C5 S1 C2 92.1(3) . . ?
C52 S51 C55 92.6(3) . . ?
C10 N9 H9 115(6) . . ?
C10 N9 C8 122.3(6) . . ?
C8 N9 H9 123(6) . . ?
C2 C3 C4 112.0(5) . . ?
C2 C3 C12 126.6(6) . . ?
C4 C3 C12 121.4(5) . . ?
C73 C68 C55 120.9(5) . . ?
C69 C68 C55 120.5(5) . . ?
C69 C68 C73 118.6(6) . . ?
C62 C67 H67 119.4 . . ?
C66 C67 H67 119.4 . . ?
C66 C67 C62 121.2(5) . . ?
C60 N59 H59 131(8) . . ?
C58 N59 H59 106(8) . . ?
C58 N59 C60 122.2(7) . . ?
C3 C2 S1 111.4(4) . . ?
C3 C2 C6 129.3(5) . . ?
C6 C2 S1 119.3(4) . . ?
C62 C63 H63 119.4 . . ?
C64 C63 H63 119.4 . . ?
C64 C63 C62 121.2(5) . . ?
C67 C62 C63 117.6(5) . . ?
C67 C62 C53 120.3(5) . . ?
C63 C62 C53 121.9(5) . . ?
C61 C56 C52 121.5(6) . . ?
C57 C56 C52 121.8(7) . . ?
C57 C56 C61 116.7(6) . . ?
C18 C5 S1 122.2(5) . . ?
C4 C5 S1 110.5(5) . . ?
C4 C5 C18 127.2(6) . . ?
C11 C6 C2 120.3(5) . . ?
C11 C6 C7 117.8(6) . . ?
C7 C6 C2 121.9(5) . . ?
C68 C55 S51 120.9(4) . . ?
C54 C55 S51 110.4(4) . . ?
C54 C55 C68 128.7(5) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 C6 119.7(6) . . ?
C10 C11 H11 120.1 . . ?
C56 C52 S51 119.9(4) . . ?
C53 C52 S51 112.1(4) . . ?
C53 C52 C56 127.9(6) . . ?
C55 C54 H54 122.8 . . ?
C55 C54 C53 114.4(5) . . ?
C53 C54 H54 122.8 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(6) . . ?
C8 C7 H7 120.1 . . ?
C63 C64 H64 119.7 . . ?
C63 C64 C65 120.7(5) . . ?
C65 C64 H64 119.7 . . ?
C19 C18 C5 119.5(6) . . ?
C23 C18 C5 122.1(6) . . ?
C23 C18 C19 118.3(6) . . ?
C3 C4 H4 123.0 . . ?
C5 C4 C3 114.0(6) . . ?
C5 C4 H4 123.0 . . ?
C13 C12 C3 121.6(5) . . ?
C17 C12 C3 119.8(6) . . ?
C17 C12 C13 118.6(6) . . ?
C52 C53 C62 127.9(5) . . ?
C52 C53 C54 110.4(5) . . ?
C54 C53 C62 121.5(5) . . ?
C72 C71 H71 120.0 . . ?
C70 C71 H71 120.0 . . ?
C70 C71 C72 119.9(6) . . ?
C64 C65 H65 120.5 . . ?
C66 C65 C64 119.0(6) . . ?
C66 C65 H65 120.5 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.5(7) . . ?
C20 C19 H19 119.7 . . ?
C67 C66 C65 120.4(6) . . ?
C67 C66 H66 119.8 . . ?
C65 C66 H66 119.8 . . ?
C56 C61 H61 119.4 . . ?
C60 C61 C56 121.1(7) . . ?
C60 C61 H61 119.4 . . ?
C68 C73 H73 119.5 . . ?
C72 C73 C68 121.0(6) . . ?
C72 C73 H73 119.5 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(6) . . ?
C14 C13 H13 120.0 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(8) . . ?
C21 C20 H20 119.7 . . ?
C18 C23 H23 119.7 . . ?
C18 C23 C22 120.5(7) . . ?
C22 C23 H23 119.7 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.5(6) . . ?
C16 C17 H17 119.8 . . ?
C68 C69 H69 119.9 . . ?
C68 C69 C70 120.3(6) . . ?
C70 C69 H69 119.9 . . ?
N9 C10 C11 120.2(6) . . ?
N9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C23 C22 H22 119.6 . . ?
C21 C22 C23 120.8(7) . . ?
C21 C22 H22 119.6 . . ?
N9 C8 C7 120.1(6) . . ?
N9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C71 C72 H72 120.1 . . ?
C73 C72 C71 119.7(6) . . ?
C73 C72 H72 120.1 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(6) . . ?
C16 C15 H15 120.3 . . ?
N59 C60 C61 119.2(8) . . ?
N59 C60 H60 120.4 . . ?
C61 C60 H60 120.4 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(7) . . ?
C15 C14 H14 119.5 . . ?
C17 C16 C15 120.5(7) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C20 C21 C22 119.2(7) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C56 C57 H57 120.0 . . ?
C58 C57 C56 120.0(8) . . ?
C58 C57 H57 120.0 . . ?
C71 C70 C69 120.4(6) . . ?
C71 C70 H70 119.8 . . ?
C69 C70 H70 119.8 . . ?
N59 C58 C57 120.7(7) . . ?
N59 C58 H58 119.7 . . ?
C57 C58 H58 119.7 . . ?

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
S1 C2 C6 C11 145.8(5) . . . . ?
S1 C2 C6 C7 -35.9(7) . . . . ?
S1 C5 C18 C19 -164.1(5) . . . . ?
S1 C5 C18 C23 17.3(9) . . . . ?
S1 C5 C4 C3 -0.9(6) . . . . ?
S51 C55 C54 C53 2.6(6) . . . . ?
S51 C52 C53 C62 -173.7(4) . . . . ?
S51 C52 C53 C54 1.8(6) . . . . ?
C3 C2 C6 C11 -34.1(9) . . . . ?
C3 C2 C6 C7 144.2(6) . . . . ?
C3 C12 C13 C14 178.7(6) . . . . ?
C3 C12 C17 C16 -178.9(6) . . . . ?
C68 C55 C54 C53 -177.8(5) . . . . ?
C68 C73 C72 C71 1.8(10) . . . . ?
C68 C69 C70 C71 -0.4(12) . . . . ?
C67 C62 C53 C52 -139.9(6) . . . . ?
C67 C62 C53 C54 45.2(7) . . . . ?
C2 S1 C5 C18 -177.9(5) . . . . ?
C2 S1 C5 C4 0.2(4) . . . . ?
C2 C3 C4 C5 1.4(7) . . . . ?
C2 C3 C12 C13 -41.2(9) . . . . ?
C2 C3 C12 C17 139.4(6) . . . . ?
C2 C6 C11 C10 176.0(6) . . . . ?
C2 C6 C7 C8 -174.4(6) . . . . ?
C63 C62 C53 C52 44.0(8) . . . . ?
C63 C62 C53 C54 -131.0(6) . . . . ?
C63 C64 C65 C66 -1.7(9) . . . . ?
C62 C67 C66 C65 -0.8(9) . . . . ?
C62 C63 C64 C65 0.1(9) . . . . ?
C56 C52 C53 C62 9.1(10) . . . . ?
C56 C52 C53 C54 -175.5(6) . . . . ?
C56 C61 C60 N59 1.0(11) . . . . ?
C56 C57 C58 N59 2.7(13) . . . . ?
C5 S1 C2 C3 0.6(4) . . . . ?
C5 S1 C2 C6 -179.3(5) . . . . ?
C5 C18 C19 C20 -177.9(7) . . . . ?
C5 C18 C23 C22 177.4(7) . . . . ?
C6 C11 C10 N9 -0.2(10) . . . . ?
C6 C7 C8 N9 -2.9(10) . . . . ?
C55 S51 C52 C56 177.2(5) . . . . ?
C55 S51 C52 C53 -0.3(5) . . . . ?
C55 C68 C73 C72 -179.8(6) . . . . ?
C55 C68 C69 C70 179.1(7) . . . . ?
C55 C54 C53 C62 172.9(5) . . . . ?
C55 C54 C53 C52 -2.9(7) . . . . ?
C11 C6 C7 C8 3.9(9) . . . . ?
C52 S51 C55 C68 179.0(5) . . . . ?
C52 S51 C55 C54 -1.3(4) . . . . ?
C52 C56 C61 C60 179.8(6) . . . . ?
C52 C56 C57 C58 178.4(7) . . . . ?
C7 C6 C11 C10 -2.4(9) . . . . ?
C64 C63 C62 C67 1.1(8) . . . . ?
C64 C63 C62 C53 177.3(5) . . . . ?
C64 C65 C66 C67 2.0(9) . . . . ?
C18 C5 C4 C3 177.1(6) . . . . ?
C18 C19 C20 C21 -1.0(12) . . . . ?
C18 C23 C22 C21 1.9(12) . . . . ?
C4 C3 C2 S1 -1.2(6) . . . . ?
C4 C3 C2 C6 178.7(5) . . . . ?
C4 C3 C12 C13 135.5(6) . . . . ?
C4 C3 C12 C17 -44.0(8) . . . . ?
C4 C5 C18 C19 18.2(10) . . . . ?
C4 C5 C18 C23 -160.4(6) . . . . ?
C12 C3 C2 S1 175.8(5) . . . . ?
C12 C3 C2 C6 -4.3(10) . . . . ?
C12 C3 C4 C5 -175.8(5) . . . . ?
C12 C13 C14 C15 1.5(11) . . . . ?
C12 C17 C16 C15 -1.1(11) . . . . ?
C19 C18 C23 C22 -1.3(10) . . . . ?
C19 C20 C21 C22 1.6(13) . . . . ?
C66 C67 C62 C63 -0.7(8) . . . . ?
C66 C67 C62 C53 -177.0(5) . . . . ?
C61 C56 C52 S51 -152.0(5) . . . . ?
C61 C56 C52 C53 25.0(9) . . . . ?
C61 C56 C57 C58 -2.8(11) . . . . ?
C73 C68 C55 S51 -22.9(8) . . . . ?
C73 C68 C55 C54 157.5(6) . . . . ?
C73 C68 C69 C70 2.5(10) . . . . ?
C13 C12 C17 C16 1.7(10) . . . . ?
C23 C18 C19 C20 0.8(10) . . . . ?
C23 C22 C21 C20 -2.1(13) . . . . ?
C17 C12 C13 C14 -1.9(9) . . . . ?
C69 C68 C55 S51 160.5(5) . . . . ?
C69 C68 C55 C54 -19.0(9) . . . . ?
C69 C68 C73 C72 -3.2(10) . . . . ?
C10 N9 C8 C7 0.2(11) . . . . ?
C8 N9 C10 C11 1.3(11) . . . . ?
C72 C71 C70 C69 -1.1(13) . . . . ?
C60 N59 C58 C57 -0.7(13) . . . . ?
C14 C15 C16 C17 0.7(12) . . . . ?
C16 C15 C14 C13 -0.8(12) . . . . ?
C57 C56 C52 S51 26.8(8) . . . . ?
C57 C56 C52 C53 -156.2(6) . . . . ?
C57 C56 C61 C60 1.0(10) . . . . ?
C70 C71 C72 C73 0.4(12) . . . . ?
C58 N59 C60 C61 -1.2(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.075
_oxdiff_exptl_absorpt_empirical_full_min 0.393
####################################################################### 
# 
# 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_KL_PyClO4
_database_code_depnum_ccdc_archive 'CCDC 1988912'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Insitute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2018-11-11
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl O4, C23 H17 N2'
_chemical_formula_sum            'C23 H17 Cl N2 O4'
_chemical_formula_weight         420.84
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C92 H68 Cl4 N8 O16 '
_chemical_oxdiff_usercomment     'from Kaspars'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.14553(5)
_cell_length_b                   8.93108(11)
_cell_length_c                   40.8075(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1875.31(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15904
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      77.0350
_cell_measurement_theta_min      4.3340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.108
_exptl_absorpt_correction_T_max  0.96017
_exptl_absorpt_correction_T_min  0.60332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.21a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            17540
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.175
_diffrn_reflns_theta_min         4.334
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  14.00   0.50    0.33    --  -49.35  33.00  38.00  104
  2  ω   -121.00 -63.00   0.50    0.33    --  -49.35 -33.00-120.00  116
  3  ω    -62.00 -23.00   0.50    0.33    --  -84.25 118.00 108.00   78
  4  ω     80.00 111.00   0.50    0.33    --  105.75-118.00  22.00   62
  5  ω    111.00 137.00   0.50    0.33    --  105.75  33.00  38.00   52
  6  ω    124.00 178.00   0.50    0.33    --  105.75  91.00-144.00  108
  7  ω    -13.00  20.00   0.50    0.33    --   49.91 -19.00  60.00   66
  8  ω    -10.00  22.00   0.50    0.33    --   49.91 -19.00-120.00   64
  9  ω     63.00  91.00   0.50    0.33    --  105.75 -77.00 -90.00   56
 10  ω     34.00  60.00   0.50    0.33    --  105.75 -61.00  90.00   52
 11  ω     71.00  98.00   0.50    0.33    --  105.75 -77.00  60.00   54
 12  ω     35.00  63.00   0.50    0.33    --  105.75 -61.00 -60.00   56
 13  ω     45.00  70.00   0.50    0.33    --  105.75 -61.00-120.00   50
 14  ω    141.00 166.00   0.50    0.33    --  105.75  15.00 120.00   50
 15  ω     34.00  66.00   0.50    0.33    --  105.75 -77.00-120.00   64
 16  ω     47.00  73.00   0.50    0.33    --  105.75 -77.00 -30.00   52
 17  ω    109.00 178.00   0.50    0.33    --  105.75  30.00  60.00  138
 18  ω    109.00 175.00   0.50    0.33    --  105.75  15.00  30.00  132
 19  ω     42.00  67.00   0.50    0.33    --  105.75 -61.00 120.00   50
 20  ω     45.00  70.00   0.50    0.33    --  105.75 -61.00 150.00   50
 21  ω     99.00 140.00   0.50    0.33    --  105.75  15.00 120.00   82
 22  ω     34.00  71.00   0.50    0.33    --  105.75 -61.00-180.00   74
 23  ω     51.00  76.00   0.50    0.33    --  105.75 -77.00 -60.00   50
 24  ω     34.00  59.00   0.50    0.33    --  105.75 -94.00  60.00   50
 25  ω     76.00 101.00   0.50    0.33    --  105.75 -94.00  60.00   50
 26  ω    110.00 153.00   0.50    0.33    --  105.75  30.00 150.00   86
 27  ω     78.00 105.00   0.50    0.33    --  105.75 -94.00 -90.00   54
 28  ω     82.00 107.00   0.50    0.33    --  105.75 -78.00-149.84   50
 29  ω     44.00  69.00   0.50    0.33    --  105.75 -77.00 150.00   50
 30  ω     81.00 106.00   0.50    0.33    --  105.75-125.00-180.00   50
 31  ω     60.00  85.00   0.50    0.33    --  105.75-125.00-150.00   50
 32  ω     66.00  91.00   0.50    0.33    --  105.75-125.00  30.00   50
 33  ω     94.00 120.00   0.50    0.33    --  105.75 125.00 -60.00   52
 34  ω    153.00 178.00   0.50    0.33    --  105.75 125.00 -60.00   50
 35  ω     35.00  61.00   0.50    0.33    --  105.75 -88.00  -7.24   52
 36  ω    119.00 167.00   0.50    0.33    --  105.75 125.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0937695000
_diffrn_orient_matrix_UB_12      0.1481687000
_diffrn_orient_matrix_UB_13      0.0153135000
_diffrn_orient_matrix_UB_21      0.0822650000
_diffrn_orient_matrix_UB_22      -0.0563846000
_diffrn_orient_matrix_UB_23      0.0341373000
_diffrn_orient_matrix_UB_31      0.2720755000
_diffrn_orient_matrix_UB_32      0.0681137000
_diffrn_orient_matrix_UB_33      -0.0050327000
_diffrn_oxdiff_ac4_digest_frames 
;
010cdae7b2916b057b2e4e753a0725d389000689b0c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3942
_reflns_number_total             3964
_reflns_odcompleteness_completeness 99.0
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_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.
;
_vrf_PLAT927_KL_PyClO4           
;
PROBLEM: Reported and Calculated  wR2 Differ by .........     0.0080 Check 
RESPONSE: It has been performed correction on extinction. 
;

_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(7)
_refine_ls_extinction_coef       0.0089(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0521P)²+0.6378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C12(H12), C15(H15), C20(H20), C21(H21), C14(H14), C18(H18),
 C11(H11), C1(H1), C7(H7), C8(H8), C2(H2), C4(H4), C5(H5), C6(H6), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.12581(7) 0.65702(4) 0.790565(9) 0.01784(11) Uani 1 1 d . . .
O1 O 0.0059(3) 0.79097(13) 0.77938(3) 0.0256(3) Uani 1 1 d . . .
O2 O -0.1130(3) 0.54476(13) 0.76499(3) 0.0273(3) Uani 1 1 d . . .
O3 O -0.3934(2) 0.69185(14) 0.79732(3) 0.0291(3) Uani 1 1 d . . .
N19 N 0.3834(3) 0.74923(16) 0.72552(3) 0.0212(3) Uani 1 1 d . . .
H19 H 0.271(5) 0.789(3) 0.7388(6) 0.037(6) Uiso 1 1 d . . .
O4 O -0.0027(3) 0.60095(15) 0.81956(3) 0.0307(3) Uani 1 1 d . . .
N9 N 1.4090(3) 0.36853(15) 0.58595(3) 0.0195(3) Uani 1 1 d . . .
C17 C 0.7362(3) 0.77972(19) 0.68931(4) 0.0202(3) Uani 1 1 d . . .
H17 H 0.8629 0.8413 0.6802 0.024 Uiso 1 1 calc R . .
C12 C 1.0874(3) 0.65110(18) 0.63906(4) 0.0193(3) Uani 1 1 d . . .
H12 H 1.1031 0.7522 0.6442 0.023 Uiso 1 1 calc R . .
C15 C 1.0362(3) 0.35164(18) 0.62225(4) 0.0193(3) Uani 1 1 d . . .
H15 H 1.0153 0.2518 0.6164 0.023 Uiso 1 1 calc R . .
C13 C 0.8926(3) 0.56588(17) 0.65429(4) 0.0166(3) Uani 1 1 d . . .
C9A C 1.5085(3) 0.22208(18) 0.58898(4) 0.0200(3) Uani 1 1 d . . .
C20 C 0.3605(3) 0.60380(19) 0.71725(4) 0.0213(3) Uani 1 1 d . . .
H20 H 0.2329 0.5450 0.7270 0.026 Uiso 1 1 calc R . .
C4B C 1.7070(3) 0.3356(2) 0.54498(4) 0.0214(3) Uani 1 1 d . . .
C21 C 0.5250(3) 0.54239(18) 0.69451(4) 0.0208(3) Uani 1 1 d . . .
H21 H 0.5083 0.4419 0.6890 0.025 Uiso 1 1 calc R . .
C16 C 0.7181(3) 0.62927(17) 0.67951(4) 0.0167(3) Uani 1 1 d . . .
C10 C 1.2332(3) 0.43625(18) 0.60798(4) 0.0185(3) Uani 1 1 d . . .
C14 C 0.8713(3) 0.41506(18) 0.64512(4) 0.0184(3) Uani 1 1 d . . .
H14 H 0.7429 0.3562 0.6547 0.022 Uiso 1 1 calc R . .
C18 C 0.5670(3) 0.83643(18) 0.71234(4) 0.0229(3) Uani 1 1 d . . .
H18 H 0.5806 0.9360 0.7188 0.027 Uiso 1 1 calc R . .
C4A C 1.6906(3) 0.19844(19) 0.56357(4) 0.0209(3) Uani 1 1 d . . .
C11 C 1.2565(3) 0.58789(19) 0.61660(4) 0.0195(3) Uani 1 1 d . . .
H11 H 1.3863 0.6461 0.6072 0.023 Uiso 1 1 calc R . .
C8A C 1.5289(3) 0.43718(19) 0.55889(4) 0.0201(3) Uani 1 1 d . . .
C1 C 1.4681(3) 0.11393(19) 0.61310(4) 0.0225(3) Uani 1 1 d . . .
H1 H 1.3540 0.1307 0.6304 0.027 Uiso 1 1 calc R . .
C7 C 1.6354(4) 0.6152(2) 0.51759(4) 0.0280(4) Uani 1 1 d . . .
H7 H 1.6121 0.7086 0.5080 0.034 Uiso 1 1 calc R . .
C8 C 1.4876(4) 0.5777(2) 0.54473(4) 0.0256(4) Uani 1 1 d . . .
H8 H 1.3650 0.6436 0.5532 0.031 Uiso 1 1 calc R . .
C2 C 1.6041(4) -0.0195(2) 0.61038(4) 0.0280(4) Uani 1 1 d . . .
H2 H 1.5793 -0.0933 0.6262 0.034 Uiso 1 1 calc R . .
C4 C 1.8239(4) 0.0626(2) 0.56132(4) 0.0275(4) Uani 1 1 d . . .
H4 H 1.9418 0.0460 0.5444 0.033 Uiso 1 1 calc R . .
C5 C 1.8540(3) 0.3765(2) 0.51775(4) 0.0246(3) Uani 1 1 d . . .
H5 H 1.9741 0.3102 0.5088 0.030 Uiso 1 1 calc R . .
C6 C 1.8189(3) 0.5168(2) 0.50420(4) 0.0276(4) Uani 1 1 d . . .
H6 H 1.9172 0.5460 0.4862 0.033 Uiso 1 1 calc R . .
C3 C 1.7778(4) -0.0466(2) 0.58456(5) 0.0308(4) Uani 1 1 d . . .
H3 H 1.8622 -0.1385 0.5831 0.037 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 O4 1.4323(13) . ?
Cl1 O3 1.4384(13) . ?
Cl1 O1 1.4487(12) . ?
Cl1 O2 1.4488(12) . ?
N19 C18 1.337(2) . ?
N19 C20 1.347(2) . ?
N19 H19 0.87(3) . ?
N9 C8A 1.406(2) . ?
N9 C9A 1.410(2) . ?
N9 C10 1.411(2) . ?
C17 C18 1.377(2) . ?
C17 C16 1.405(2) . ?
C17 H17 0.9300 . ?
C12 C11 1.384(2) . ?
C12 C13 1.404(2) . ?
C12 H12 0.9300 . ?
C15 C14 1.382(2) . ?
C15 C10 1.392(2) . ?
C15 H15 0.9300 . ?
C13 C14 1.402(2) . ?
C13 C16 1.479(2) . ?
C9A C1 1.395(2) . ?
C9A C4A 1.413(2) . ?
C20 C21 1.370(2) . ?
C20 H20 0.9300 . ?
C4B C5 1.393(2) . ?
C4B C8A 1.408(2) . ?
C4B C4A 1.443(2) . ?
C21 C16 1.401(2) . ?
C21 H21 0.9300 . ?
C10 C11 1.404(2) . ?
C14 H14 0.9300 . ?
C18 H18 0.9300 . ?
C4A C4 1.396(2) . ?
C11 H11 0.9300 . ?
C8A C8 1.398(3) . ?
C1 C2 1.386(2) . ?
C1 H1 0.9300 . ?
C7 C8 1.385(3) . ?
C7 C6 1.401(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C2 C3 1.403(3) . ?
C2 H2 0.9300 . ?
C4 C3 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cl1 O3 109.91(9) . . ?
O4 Cl1 O1 110.00(9) . . ?
O3 Cl1 O1 109.25(8) . . ?
O4 Cl1 O2 109.45(8) . . ?
O3 Cl1 O2 109.36(8) . . ?
O1 Cl1 O2 108.86(7) . . ?
C18 N19 C20 121.49(15) . . ?
C18 N19 H19 119.0(18) . . ?
C20 N19 H19 119.4(18) . . ?
C8A N9 C9A 108.29(13) . . ?
C8A N9 C10 126.50(14) . . ?
C9A N9 C10 125.07(14) . . ?
C18 C17 C16 120.26(16) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C11 C12 C13 121.40(15) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C15 C10 120.45(15) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C14 C13 C12 117.29(15) . . ?
C14 C13 C16 120.41(14) . . ?
C12 C13 C16 122.29(14) . . ?
C1 C9A N9 130.54(15) . . ?
C1 C9A C4A 120.88(15) . . ?
N9 C9A C4A 108.37(15) . . ?
N19 C20 C21 120.11(16) . . ?
N19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C5 C4B C8A 120.40(16) . . ?
C5 C4B C4A 132.30(16) . . ?
C8A C4B C4A 107.28(14) . . ?
C20 C21 C16 120.79(15) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C21 C16 C17 116.89(15) . . ?
C21 C16 C13 121.50(14) . . ?
C17 C16 C13 121.60(14) . . ?
C15 C10 C11 118.75(15) . . ?
C15 C10 N9 120.04(15) . . ?
C11 C10 N9 121.19(15) . . ?
C15 C14 C13 121.72(16) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
N19 C18 C17 120.45(15) . . ?
N19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C4 C4A C9A 120.23(16) . . ?
C4 C4A C4B 132.40(16) . . ?
C9A C4A C4B 107.29(14) . . ?
C12 C11 C10 120.35(15) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C8 C8A N9 130.50(15) . . ?
C8 C8A C4B 120.70(16) . . ?
N9 C8A C4B 108.74(15) . . ?
C2 C1 C9A 117.60(16) . . ?
C2 C1 H1 121.2 . . ?
C9A C1 H1 121.2 . . ?
C8 C7 C6 122.03(17) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C8A 117.67(16) . . ?
C7 C8 H8 121.2 . . ?
C8A C8 H8 121.2 . . ?
C1 C2 C3 122.05(18) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C3 C4 C4A 118.97(17) . . ?
C3 C4 H4 120.5 . . ?
C4A C4 H4 120.5 . . ?
C6 C5 C4B 119.06(17) . . ?
C6 C5 H5 120.5 . . ?
C4B C5 H5 120.5 . . ?
C5 C6 C7 120.06(17) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C4 C3 C2 120.18(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?

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
C11 C12 C13 C14 -1.8(2) . . . . ?
C11 C12 C13 C16 176.97(15) . . . . ?
C8A N9 C9A C1 174.27(17) . . . . ?
C10 N9 C9A C1 -1.6(3) . . . . ?
C8A N9 C9A C4A -0.35(17) . . . . ?
C10 N9 C9A C4A -176.19(15) . . . . ?
C18 N19 C20 C21 -1.0(3) . . . . ?
N19 C20 C21 C16 -0.1(3) . . . . ?
C20 C21 C16 C17 1.0(2) . . . . ?
C20 C21 C16 C13 -178.34(15) . . . . ?
C18 C17 C16 C21 -0.8(2) . . . . ?
C18 C17 C16 C13 178.53(15) . . . . ?
C14 C13 C16 C21 -1.1(2) . . . . ?
C12 C13 C16 C21 -179.86(15) . . . . ?
C14 C13 C16 C17 179.60(15) . . . . ?
C12 C13 C16 C17 0.8(2) . . . . ?
C14 C15 C10 C11 -1.7(2) . . . . ?
C14 C15 C10 N9 176.68(14) . . . . ?
C8A N9 C10 C15 147.54(16) . . . . ?
C9A N9 C10 C15 -37.4(2) . . . . ?
C8A N9 C10 C11 -34.1(2) . . . . ?
C9A N9 C10 C11 140.98(16) . . . . ?
C10 C15 C14 C13 1.2(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C16 C13 C14 C15 -178.25(15) . . . . ?
C20 N19 C18 C17 1.2(3) . . . . ?
C16 C17 C18 N19 -0.3(3) . . . . ?
C1 C9A C4A C4 3.2(2) . . . . ?
N9 C9A C4A C4 178.47(15) . . . . ?
C1 C9A C4A C4B -173.89(15) . . . . ?
N9 C9A C4A C4B 1.35(18) . . . . ?
C5 C4B C4A C4 3.0(3) . . . . ?
C8A C4B C4A C4 -178.47(18) . . . . ?
C5 C4B C4A C9A 179.58(17) . . . . ?
C8A C4B C4A C9A -1.84(18) . . . . ?
C13 C12 C11 C10 1.3(2) . . . . ?
C15 C10 C11 C12 0.5(2) . . . . ?
N9 C10 C11 C12 -177.90(15) . . . . ?
C9A N9 C8A C8 176.16(17) . . . . ?
C10 N9 C8A C8 -8.1(3) . . . . ?
C9A N9 C8A C4B -0.82(18) . . . . ?
C10 N9 C8A C4B 174.95(15) . . . . ?
C5 C4B C8A C8 3.1(3) . . . . ?
C4A C4B C8A C8 -175.69(15) . . . . ?
C5 C4B C8A N9 -179.58(14) . . . . ?
C4A C4B C8A N9 1.64(18) . . . . ?
N9 C9A C1 C2 -176.85(17) . . . . ?
C4A C9A C1 C2 -2.8(2) . . . . ?
C6 C7 C8 C8A 0.7(3) . . . . ?
N9 C8A C8 C7 -179.41(17) . . . . ?
C4B C8A C8 C7 -2.7(3) . . . . ?
C9A C1 C2 C3 0.3(3) . . . . ?
C9A C4A C4 C3 -1.0(3) . . . . ?
C4B C4A C4 C3 175.24(18) . . . . ?
C8A C4B C5 C6 -1.3(3) . . . . ?
C4A C4B C5 C6 177.14(17) . . . . ?
C4B C5 C6 C7 -0.7(3) . . . . ?
C8 C7 C6 C5 1.1(3) . . . . ?
C4A C4 C3 C2 -1.4(3) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.806
_oxdiff_exptl_absorpt_empirical_full_min 0.582

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
_shelx_title                     ' KL_PyClO4 in P2(1)2(1)2(1)'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            150.28
_reflns_d_resolution_high        0.7906

_shelx_F_squared_multiplier      1.000
####################################################################### 
# 
# 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_KL1248
_database_code_depnum_ccdc_archive 'CCDC 1988916'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Insitute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2019-03-13
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_chemical_formula_moiety         'Cl O4, C11 H10 N'
_chemical_formula_sum            'C11 H10 Cl N O4'
_chemical_formula_weight         255.66
_chemical_oxdiff_formula         'C44 H40 Cl4 N4 O16 '
_chemical_oxdiff_usercomment     'from Kaspars'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.8571(1)
_cell_length_b                   18.2247(2)
_cell_length_c                   9.2749(1)
_cell_angle_alpha                90
_cell_angle_beta                 109.383(2)
_cell_angle_gamma                90
_cell_volume                     1093.38(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7507
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      77.1220
_cell_measurement_theta_min      4.8290
_exptl_absorpt_coefficient_mu    3.155
_exptl_absorpt_correction_T_max  0.91048
_exptl_absorpt_correction_T_min  0.69642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.5530
_exptl_crystal_F_000             528
_exptl_crystal_colour            Colourless
_exptl_crystal_description       Block
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10027
_diffrn_reflns_theta_full        77.2643
_diffrn_reflns_theta_max         77.26
_diffrn_reflns_theta_min         4.85
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  19.00   0.50    8.33    --  -49.35  96.00  83.00   96
  2  ω    -72.00 -47.00   0.50    8.33    --  -84.25  96.00  83.00   50
  3  ω    -78.00 -34.00   0.50    8.33    --  -49.35  96.00  83.00   88
  4  ω   -115.00 -90.00   0.50    8.33    --  -49.35 -77.00  30.00   50
  5  ω   -119.00 -92.00   0.50    8.33    --  -49.35 -77.00  90.00   54
  6  ω   -119.00 -94.00   0.50    8.33    --  -49.35 -77.00 120.00   50
  7  ω   -116.00 -81.00   0.50    8.33    --  -49.35-125.00 120.00   70
  8  ω   -117.00 -89.00   0.50    8.33    --  -49.35 -77.00   0.00   56
  9  ω   -143.00-118.00   0.50    8.33    --  -84.25 -96.00 -25.00   50
 10  ω     12.00  53.00   0.50    8.33    --   49.66 -96.00 -25.00   82
 11  ω     50.00  76.00   0.50    8.33    --  105.75 -96.00 -25.00   52
 12  ω     79.00 104.00   0.50    8.33    --  105.75 -94.00   0.00   50
 13  ω     70.00  96.00   0.50    8.33    --  105.75 -94.00  30.00   52
 14  ω     56.00  99.00   0.50    8.33    --  105.75 -77.00   0.00   86
 15  ω     43.00  68.00   0.50    8.33    --  105.75 -94.00  30.00   50
 16  ω     50.00  76.00   0.50    8.33    --  105.75 -79.00  -9.73   52
 17  ω     36.00  77.00   0.50    8.33    --  105.75 -77.00  60.00   82
 18  ω     35.00  71.00   0.50    8.33    --  105.75 -94.00   0.00   72
 19  ω     35.00  66.00   0.50    8.33    --  105.75 -77.00  30.00   62
 20  ω    132.00 158.00   0.50    8.33    --  105.75  15.00 -60.00   52
 21  ω    105.00 158.00   0.50    8.33    --  105.75  30.00-180.00  106
 22  ω    118.00 168.00   0.50    8.33    --  105.75 125.00-150.00  100
 23  ω     93.00 151.00   0.50    8.33    --  105.75  61.00 -60.00  116
 24  ω     98.00 124.00   0.50    8.33    --  105.75  45.00  30.00   52
 25  ω    100.00 155.00   0.50    8.33    --  105.75  45.00  90.00  110
 26  ω    107.00 133.00   0.50    8.33    --  105.75  96.00  83.00   52
 27  ω    101.00 128.00   0.50    8.33    --  105.75  61.00 120.00   54
 28  ω     76.00 113.00   0.50    8.33    --  105.75 154.00 117.47   74
 29  ω    142.00 167.00   0.50    8.33    --  105.75 154.00 117.47   50
 30  ω     98.00 174.00   0.50    8.33    --  105.75  61.00-150.00  152
 31  ω     74.00 100.00   0.50    8.33    --  105.75 -77.00-120.00   52
 32  ω     35.00  69.00   0.50    8.33    --  105.75 -61.00-120.00   68
 33  ω     45.00  71.00   0.50    8.33    --  105.75 -61.00-150.00   52
 34  ω     34.00  87.00   0.50    8.33    --  105.75 -94.00-150.00  106
 35  ω     45.00  85.00   0.50    8.33    --  105.75 -86.00 174.27   80
 36  ω     89.00 114.00   0.50    8.33    --  105.75 -86.00 174.27   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1322291000
_diffrn_orient_matrix_UB_12      -0.0694345000
_diffrn_orient_matrix_UB_13      0.0102302000
_diffrn_orient_matrix_UB_21      -0.1841707000
_diffrn_orient_matrix_UB_22      -0.0380788000
_diffrn_orient_matrix_UB_23      -0.1193012000
_diffrn_orient_matrix_UB_31      0.0727598000
_diffrn_orient_matrix_UB_32      0.0296713000
_diffrn_orient_matrix_UB_33      -0.1290902000
_diffrn_oxdiff_digest_frames     
;
0175de1edc245abbe347a256a32224d9c200026318a
;
_diffrn_oxdiff_digest_hkl        
;
01587f8538602881b2f95c1de280da1710bc93
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2098
_reflns_number_total             2308
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3367
_refine_diff_density_min         -0.6010
_refine_diff_density_rms         0.0929
_refine_ls_d_res_high            0.7904
_refine_ls_d_res_low             9.1123
_refine_ls_goodness_of_fit_ref   1.0242
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.0242
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+0.8907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1164
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Cl1 Cl 0.51332(7) 0.15878(2) 0.60789(5) 0.02630(17) Uani 1.000000 .
O4 O 0.4184(2) 0.08736(8) 0.58303(17) 0.0333(4) Uani 1.000000 .
O2 O 0.4964(2) 0.19236(8) 0.46341(15) 0.0312(3) Uani 1.000000 .
O3 O 0.7277(3) 0.15138(9) 0.69806(19) 0.0407(4) Uani 1.000000 .
O1 O 0.4097(3) 0.20448(9) 0.68687(19) 0.0434(4) Uani 1.000000 .
N1 N 0.3605(3) 0.36404(10) 0.6460(2) 0.0271(4) Uani 1.000000 .
H1 H 0.398(4) 0.3264(16) 0.702(3) 0.036(7) Uiso 1.000000 .
C7 C 0.1832(3) 0.55083(10) 0.3589(2) 0.0219(4) Uani 1.000000 .
C4 C 0.2411(3) 0.48498(10) 0.4580(2) 0.0210(4) Uani 1.000000 .
C5 C 0.2852(3) 0.49000(11) 0.6167(2) 0.0247(4) Uani 1.000000 .
H5 H 0.2743(3) 0.53506(11) 0.6604(2) 0.0296(5) Uiso 1.000000 R
C3 C 0.2584(3) 0.41541(11) 0.3995(2) 0.0274(4) Uani 1.000000 .
H3 H 0.2283(3) 0.40937(11) 0.2948(2) 0.0328(5) Uiso 1.000000 R
C12 C 0.1654(3) 0.61962(11) 0.4200(2) 0.0267(4) Uani 1.000000 .
H12 H 0.1887(3) 0.62412(11) 0.5243(2) 0.0320(5) Uiso 1.000000 R
C9 C 0.0970(3) 0.60797(13) 0.1097(2) 0.0335(5) Uani 1.000000 .
H9 H 0.0744(3) 0.60403(13) 0.0054(2) 0.0402(6) Uiso 1.000000 R
C6 C 0.3444(3) 0.42911(11) 0.7080(2) 0.0270(4) Uani 1.000000 .
H6 H 0.3733(3) 0.43309(11) 0.8130(2) 0.0324(5) Uiso 1.000000 R
C8 C 0.1483(3) 0.54608(12) 0.2017(2) 0.0281(4) Uani 1.000000 .
H8 H 0.1596(3) 0.50092(12) 0.1585(2) 0.0338(5) Uiso 1.000000 R
C11 C 0.1133(3) 0.68137(12) 0.3273(3) 0.0321(5) Uani 1.000000 .
H11 H 0.1012(3) 0.72671(12) 0.3695(3) 0.0385(5) Uiso 1.000000 R
C2 C 0.3194(3) 0.35595(11) 0.4949(2) 0.0296(4) Uani 1.000000 .
H2 H 0.3321(3) 0.31011(11) 0.4548(2) 0.0355(5) Uiso 1.000000 R
C10 C 0.0794(3) 0.67554(13) 0.1724(3) 0.0340(5) Uani 1.000000 .
H10 H 0.0449(3) 0.71691(13) 0.1103(3) 0.0409(6) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 O4 1.4392(15) . ?
Cl1 O2 1.4424(14) . ?
Cl1 O3 1.4363(18) . ?
Cl1 O1 1.4423(16) . ?
N1 H1 0.85(3) . ?
N1 C6 1.339(3) . ?
N1 C2 1.343(3) . ?
C7 C4 1.483(3) . ?
C7 C12 1.398(3) . ?
C7 C8 1.399(3) . ?
C4 C5 1.404(3) . ?
C4 C3 1.400(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.373(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.389(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.388(3) . ?
C9 C10 1.384(3) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.381(3) . ?
C2 H2 0.9300 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cl1 O4 110.00(9) . . ?
O3 Cl1 O4 109.24(10) . . ?
O3 Cl1 O2 109.40(10) . . ?
O1 Cl1 O4 109.32(10) . . ?
O1 Cl1 O2 108.99(9) . . ?
O1 Cl1 O3 109.88(11) . . ?
C6 N1 H1 120.1(19) . . ?
C2 N1 H1 118.1(19) . . ?
C2 N1 C6 121.81(18) . . ?
C12 C7 C4 121.06(17) . . ?
C8 C7 C4 120.90(17) . . ?
C8 C7 C12 118.04(17) . . ?
C5 C4 C7 121.14(17) . . ?
C3 C4 C7 122.17(17) . . ?
C3 C4 C5 116.67(17) . . ?
H5 C5 C4 119.63(11) . . ?
C6 C5 C4 120.74(18) . . ?
C6 C5 H5 119.63(12) . . ?
H3 C3 C4 119.60(11) . . ?
C2 C3 C4 120.80(18) . . ?
C2 C3 H3 119.60(12) . . ?
H12 C12 C7 119.51(11) . . ?
C11 C12 C7 120.98(19) . . ?
C11 C12 H12 119.51(13) . . ?
C8 C9 H9 119.86(13) . . ?
C10 C9 H9 119.86(12) . . ?
C10 C9 C8 120.3(2) . . ?
C5 C6 N1 120.02(18) . . ?
H6 C6 N1 119.99(11) . . ?
H6 C6 C5 119.99(12) . . ?
C9 C8 C7 120.8(2) . . ?
H8 C8 C7 119.62(11) . . ?
H8 C8 C9 119.62(13) . . ?
H11 C11 C12 119.94(13) . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 119.94(13) . . ?
C3 C2 N1 119.95(19) . . ?
H2 C2 N1 120.03(12) . . ?
H2 C2 C3 120.03(12) . . ?
C11 C10 C9 119.8(2) . . ?
H10 C10 C9 120.09(12) . . ?
H10 C10 C11 120.09(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.383
_oxdiff_exptl_absorpt_empirical_full_min 0.714
####################################################################### 
# 
# 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_kl1301
_database_code_depnum_ccdc_archive 'CCDC 1988914'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Insitute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2019-12-09
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_chemical_formula_moiety         '(C23 H17 N2), (Cl O4), (C H4 O)'
_chemical_formula_sum            'C24 H21 Cl1 N2 O5'
_chemical_formula_weight         452.89
_chemical_oxdiff_formula         'C96 H84 Cl4 N8 O20'
_chemical_oxdiff_usercomment     'from Kaspars'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.7838(1)
_cell_length_b                   7.8328(1)
_cell_length_c                   23.3380(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.889(1)
_cell_angle_gamma                90
_cell_volume                     2091.12(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14343
_cell_measurement_temperature    160.0(1)
_cell_measurement_theta_max      77.0990
_cell_measurement_theta_min      3.8550
_exptl_absorpt_coefficient_mu    1.966
_exptl_absorpt_correction_T_max  0.96012
_exptl_absorpt_correction_T_min  0.87141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4384
_exptl_crystal_F_000             944
_exptl_crystal_description       Needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24797
_diffrn_reflns_theta_full        77.3938
_diffrn_reflns_theta_max         77.39
_diffrn_reflns_theta_min         3.86
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -35.00   0.50    0.19    --  -47.95 -50.00-165.00  164
  2  ω    -57.00  25.00   0.50    0.19    --  -47.95  50.00 -19.00  164
  3  ω     -5.00  55.00   0.50    0.19    --   47.95 -50.00-165.00  120
  4  ω     55.00  80.00   0.50    0.19    --   47.95  50.00 -19.00   50
  5  ω   -120.00 -94.00   0.50    0.71    --  -86.25 -50.00-165.00   52
  6  ω    -57.00 -32.00   0.50    0.71    --  -86.25  50.00 -19.00   50
  7  ω     99.00 177.00   0.50    0.71    --  107.75  50.00 -19.00  156
  8  ω   -119.00 -81.00   0.50    0.19    --  -47.95-125.00 -30.00   76
  9  ω   -116.00 -88.00   0.50    0.19    --  -47.95 -77.00  60.00   56
 10  ω    -46.00 -18.00   0.50    0.71    --  -86.25  45.00 120.00   56
 11  ω    -51.00 -16.00   0.50    0.71    --  -86.25  45.00-180.00   70
 12  ω     36.00  65.00   0.50    0.71    --  107.75 -61.00 150.00   58
 13  ω     37.00  63.00   0.50    0.71    --  107.75 -61.00-180.00   52
 14  ω     38.00  63.00   0.50    0.71    --  107.75 -61.00  90.00   50
 15  ω    138.00 164.00   0.50    0.71    --  107.75 125.00-120.00   52
 16  ω    153.00 178.00   0.50    0.71    --  107.75  61.00  60.00   50
 17  ω     37.00  69.00   0.50    0.71    --  107.75 -61.00 -90.00   64
 18  ω    119.00 161.00   0.50    0.71    --  107.75  61.00   0.00   84
 19  ω     38.00  93.00   0.50    0.71    --  107.75 -94.00 120.00  110
 20  ω     43.00  69.00   0.50    0.71    --  107.75 -77.00 150.00   52
 21  ω     79.00 104.00   0.50    0.71    --  107.75 -77.00 150.00   50
 22  ω     54.00  93.00   0.50    0.71    --  107.75 -77.00 -30.00   78
 23  ω     92.00 119.00   0.50    0.71    --  107.75 125.00-120.00   54
 24  ω     35.00  60.00   0.50    0.71    --  107.75 -61.00  60.00   50
 25  ω     51.00  91.00   0.50    0.71    --  107.75 -77.00-180.00   80
 26  ω     96.00 178.00   0.50    0.71    --  107.75  15.00 120.00  164
 27  ω     95.00 149.00   0.50    0.71    --  107.75  45.00 120.00  108
 28  ω     35.00  70.00   0.50    0.71    --  107.75 -61.00-120.00   70
 29  ω     45.00  70.00   0.50    0.71    --  107.75 -77.00 -90.00   50
 30  ω     39.00  64.00   0.50    0.71    --  107.75 -61.00 -30.00   50
 31  ω     42.00  71.00   0.50    0.71    --  107.75 -61.00 120.00   58
 32  ω    105.00 143.00   0.50    0.71    --  107.75  61.00  60.00   76
 33  ω    140.00 166.00   0.50    0.71    --  107.75  61.00-120.00   52
 34  ω     97.00 127.00   0.50    0.71    --  107.75  45.00-120.00   60
 35  ω     90.00 132.00   0.50    0.71    --  107.75  77.00 -60.00   84
 36  ω    137.00 162.00   0.50    0.71    --  107.75  77.00 -60.00   50
 37  ω     96.00 121.00   0.50    0.71    --  107.75  30.00  90.00   50
 38  ω    136.00 161.00   0.50    0.71    --  107.75  30.00  90.00   50
 39  ω     35.00  68.00   0.50    0.71    --  107.75 -77.00   0.00   66
 40  ω     41.00  69.00   0.50    0.71    --  107.75 -61.00  30.00   56
 41  ω     95.00 121.00   0.50    0.71    --  107.75  15.00-150.00   52
 42  ω    152.00 177.00   0.50    0.71    --  107.75  15.00-150.00   50
 43  ω     74.00 100.00   0.50    0.71    --  107.75 -77.00-150.00   52
 44  ω     64.00  90.00   0.50    0.71    --  107.75 -77.00  30.00   52
 45  ω    113.00 139.00   0.50    0.71    --  107.75  61.00  30.00   52
 46  ω    124.00 149.00   0.50    0.71    --  107.75  77.00-180.00   50
 47  ω     92.00 118.00   0.50    0.71    --  107.75  77.00-150.00   52
 48  ω     91.00 119.00   0.50    0.71    --  107.75  61.00-120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0129422000
_diffrn_orient_matrix_UB_12      -0.0058916000
_diffrn_orient_matrix_UB_13      0.0640932000
_diffrn_orient_matrix_UB_21      -0.1052163000
_diffrn_orient_matrix_UB_22      -0.1213983000
_diffrn_orient_matrix_UB_23      -0.0189191000
_diffrn_orient_matrix_UB_31      0.0830937000
_diffrn_orient_matrix_UB_32      -0.1546569000
_diffrn_orient_matrix_UB_33      0.0124639000

# start Validation Reply Form
_vrf_PLAT420_kl1301              
;
PROBLEM: D-H Without Acceptor
RESPONSE: In the crystal structure there is disordered solvent 
(methanol). 
;
# end Validation Reply Form

_diffrn_oxdiff_digest_frames     
;
011d6af67644d2d31096c793c28705c2bd00098cbb7
;
_diffrn_oxdiff_digest_hkl        
;
014317260f68d9e621d3d1c72fe9ddcc5c1205
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                4025
_reflns_number_total             4427
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.5416
_refine_diff_density_min         -1.1223
_refine_diff_density_rms         0.0873
_refine_ls_d_res_high            0.7900
_refine_ls_d_res_low             11.4393
_refine_ls_goodness_of_fit_ref   1.0517
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0836
_refine_ls_restrained_S_all      1.0517
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1168P)²+3.9079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2264
_refine_ls_wR_factor_ref         0.2318
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: O1M(0.5) H1Ma(0.5) O2M(0.5) H2Ma(0.5) H1Mc(0.5) H2Mb(0.5)
 H1Md(0.5) H1Me(0.5) H1Mf(0.5) H1Mb(0.5)
3.a Riding coordinates:
 O1M(H1Ma), O2M(H2Ma), C1M(H1Mc,H2Mb,H1Md,H1Me,H1Mf,H1Mb)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11),
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), N19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
C1 C 0.8310(3) 0.4402(4) 0.27115(14) 0.0349(6) Uani 1.000000 .
H1 H 0.7930(3) 0.4276(4) 0.30154(14) 0.0419(8) Uiso 1.000000 R
C2 C 0.9398(3) 0.3672(4) 0.27425(17) 0.0438(8) Uani 1.000000 .
H2 H 0.9755(3) 0.3047(4) 0.30759(17) 0.0525(9) Uiso 1.000000 R
C3 C 0.9967(3) 0.3852(4) 0.22884(18) 0.0472(8) Uani 1.000000 .
H3 H 1.0697(3) 0.3355(4) 0.23257(18) 0.0566(10) Uiso 1.000000 R
C4 C 0.9466(3) 0.4754(4) 0.17837(17) 0.0429(8) Uani 1.000000 .
H4 H 0.9850(3) 0.4858(4) 0.14805(17) 0.0515(9) Uiso 1.000000 R
C4A C 0.8369(2) 0.5515(3) 0.17353(14) 0.0332(6) Uani 1.000000 .
C4B C 0.7593(3) 0.6471(3) 0.12780(13) 0.0330(6) Uani 1.000000 .
C5 C 0.7663(3) 0.7017(4) 0.07184(15) 0.0440(8) Uani 1.000000 .
H5 H 0.8327(3) 0.6799(4) 0.05808(15) 0.0528(9) Uiso 1.000000 R
C6 C 0.6722(4) 0.7890(5) 0.03718(14) 0.0488(9) Uani 1.000000 .
H6 H 0.6752(4) 0.8250(5) -0.00039(14) 0.0586(10) Uiso 1.000000 R
C7 C 0.5726(3) 0.8238(4) 0.05797(14) 0.0421(7) Uani 1.000000 .
H7 H 0.5110(3) 0.8832(4) 0.03385(14) 0.0505(9) Uiso 1.000000 R
C8 C 0.5632(3) 0.7721(3) 0.11348(12) 0.0333(6) Uani 1.000000 .
H8 H 0.4970(3) 0.7960(3) 0.12713(12) 0.0399(7) Uiso 1.000000 R
C8A C 0.6577(2) 0.6827(3) 0.14786(12) 0.0287(6) Uani 1.000000 .
N9 N 0.6723(2) 0.6149(3) 0.20469(10) 0.0278(5) Uani 1.000000 .
C9A C 0.7813(2) 0.5332(3) 0.22028(13) 0.0294(6) Uani 1.000000 .
C10 C 0.5937(2) 0.6337(3) 0.24171(11) 0.0259(5) Uani 1.000000 .
C11 C 0.4746(2) 0.6058(3) 0.21959(12) 0.0280(5) Uani 1.000000 .
H11 H 0.4462(2) 0.5740(3) 0.18037(12) 0.0336(7) Uiso 1.000000 R
C12 C 0.3984(2) 0.6254(3) 0.25583(12) 0.0284(6) Uani 1.000000 .
H12 H 0.3187(2) 0.6088(3) 0.24053(12) 0.0340(7) Uiso 1.000000 R
C13 C 0.4398(2) 0.6700(3) 0.31549(11) 0.0265(5) Uani 1.000000 .
C14 C 0.5598(2) 0.6969(3) 0.33688(11) 0.0288(6) Uani 1.000000 .
H14 H 0.5888(2) 0.7262(3) 0.37630(11) 0.0346(7) Uiso 1.000000 R
C15 C 0.6359(2) 0.6809(3) 0.30058(12) 0.0292(6) Uani 1.000000 .
H15 H 0.7153(2) 0.7015(3) 0.31535(12) 0.0350(7) Uiso 1.000000 R
C16 C 0.3587(2) 0.6855(3) 0.35441(12) 0.0276(5) Uani 1.000000 .
C17 C 0.2495(3) 0.6047(4) 0.34067(13) 0.0323(6) Uani 1.000000 .
H17 H 0.2263(3) 0.5431(4) 0.30574(13) 0.0388(7) Uiso 1.000000 R
C18 C 0.1768(3) 0.6156(4) 0.37827(14) 0.0370(7) Uani 1.000000 .
H18 H 0.1045(3) 0.5614(4) 0.36885(14) 0.0444(8) Uiso 1.000000 R
N19 N 0.2097(2) 0.7044(3) 0.42873(11) 0.0372(6) Uani 1.000000 .
H19 H 0.1634(2) 0.7092(3) 0.45212(11) 0.0446(7) Uiso 1.000000 R
C20 C 0.3126(3) 0.7857(4) 0.44366(13) 0.0361(6) Uani 1.000000 .
H20 H 0.3327(3) 0.8475(4) 0.47868(13) 0.0434(8) Uiso 1.000000 R
C21 C 0.3884(2) 0.7780(4) 0.40734(12) 0.0310(6) Uani 1.000000 .
H21 H 0.4598(2) 0.8344(4) 0.41789(12) 0.0372(7) Uiso 1.000000 R
Cl1 Cl 0.21700(9) 0.88795(18) 0.58004(4) 0.0684(4) Uani 1.000000 .
O1 O 0.1281(4) 0.9209(11) 0.52949(17) 0.164(3) Uani 1.000000 .
O2 O 0.2548(5) 0.7156(5) 0.5798(3) 0.132(2) Uani 1.000000 .
O3 O 0.3155(3) 0.9928(4) 0.57424(14) 0.0670(8) Uani 1.000000 .
O4 O 0.1898(3) 0.9339(7) 0.63255(14) 0.0985(15) Uani 1.000000 .
O1M O -0.0014(4) 0.6944(7) 0.4659(2) 0.0481(11) Uiso 0.500000 .
H1Ma H -0.0140(4) 0.8015(7) 0.4780(2) 0.0578(13) Uiso 0.500000 R
O2M O -0.0028(5) 0.5595(7) 0.4433(2) 0.0528(12) Uiso 0.500000 .
H2Ma H 0.0010(5) 0.4479(7) 0.4462(2) 0.0634(14) Uiso 0.500000 R
C1M C -0.0987(5) 0.6487(8) 0.4318(3) 0.0799(14) Uiso 1.000000 .
H1Mc H -0.1577(5) 0.6545(8) 0.4533(3) 0.120(2) Uiso 0.500000 R
H2Mb H -0.0905(5) 0.5359(8) 0.4185(3) 0.120(2) Uiso 0.500000 R
H1Md H -0.1159(5) 0.7266(8) 0.3992(3) 0.120(2) Uiso 0.500000 R
H1Me H -0.1639(5) 0.5762(8) 0.4278(3) 0.120(2) Uiso 0.500000 R
H1Mf H -0.1029(5) 0.7140(8) 0.3968(3) 0.120(2) Uiso 0.500000 R
H1Mb H -0.0960(5) 0.7279(8) 0.4645(3) 0.120(2) Uiso 0.500000 R


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 1.390(4) . ?
C1 C9A 1.396(4) . ?
C2 C3 1.390(5) . ?
C3 C4 1.379(6) . ?
C4 C4A 1.404(4) . ?
C4A C4B 1.438(4) . ?
C4A C9A 1.408(4) . ?
C4B C5 1.395(4) . ?
C4B C8A 1.414(4) . ?
C5 C6 1.386(6) . ?
C6 C7 1.399(5) . ?
C7 C8 1.387(4) . ?
C8 C8A 1.394(4) . ?
C8A N9 1.400(3) . ?
N9 C9A 1.402(3) . ?
N9 C10 1.418(3) . ?
C10 C11 1.391(4) . ?
C10 C15 1.394(4) . ?
C11 C12 1.382(4) . ?
C12 C13 1.404(4) . ?
C13 C14 1.398(4) . ?
C13 C16 1.473(4) . ?
C14 C15 1.380(4) . ?
C16 C17 1.400(4) . ?
C16 C21 1.402(4) . ?
C17 C18 1.368(4) . ?
C18 N19 1.342(4) . ?
N19 C20 1.339(4) . ?
C20 C21 1.372(4) . ?
Cl1 O1 1.401(4) . ?
Cl1 O2 1.422(5) . ?
Cl1 O3 1.454(3) . ?
Cl1 O4 1.387(3) . ?
O1M O2M 1.180(7) . ?
O1M C1M 1.280(7) . ?
O2M C1M 1.301(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
C9A C1 C2 116.9(3) . . ?
C3 C2 C1 121.7(3) . . ?
C4 C3 C2 121.2(3) . . ?
C4A C4 C3 118.9(3) . . ?
C4B C4A C4 133.6(3) . . ?
C9A C4A C4 119.1(3) . . ?
C9A C4A C4B 107.3(2) . . ?
C5 C4B C4A 133.2(3) . . ?
C8A C4B C4A 107.2(2) . . ?
C8A C4B C5 119.6(3) . . ?
C6 C5 C4B 118.6(3) . . ?
C7 C6 C5 120.9(3) . . ?
C8 C7 C6 121.9(3) . . ?
C8A C8 C7 116.9(3) . . ?
C8 C8A C4B 122.1(3) . . ?
N9 C8A C4B 108.5(2) . . ?
N9 C8A C8 129.4(3) . . ?
C9A N9 C8A 108.4(2) . . ?
C10 N9 C8A 126.0(2) . . ?
C10 N9 C9A 125.5(2) . . ?
C4A C9A C1 122.3(3) . . ?
N9 C9A C1 129.0(3) . . ?
N9 C9A C4A 108.6(2) . . ?
C11 C10 N9 120.4(2) . . ?
C15 C10 N9 119.8(2) . . ?
C15 C10 C11 119.8(2) . . ?
C12 C11 C10 120.1(2) . . ?
C13 C12 C11 120.8(2) . . ?
C14 C13 C12 118.2(2) . . ?
C16 C13 C12 120.6(2) . . ?
C16 C13 C14 121.2(2) . . ?
C15 C14 C13 121.2(2) . . ?
C14 C15 C10 119.9(2) . . ?
C17 C16 C13 121.2(2) . . ?
C21 C16 C13 121.6(2) . . ?
C21 C16 C17 117.2(3) . . ?
C18 C17 C16 120.5(3) . . ?
N19 C18 C17 120.1(3) . . ?
C20 N19 C18 121.8(3) . . ?
C21 C20 N19 120.1(3) . . ?
C20 C21 C16 120.3(3) . . ?
O2 Cl1 O1 110.1(5) . . ?
O3 Cl1 O1 105.6(3) . . ?
O3 Cl1 O2 106.2(2) . . ?
O4 Cl1 O1 114.3(3) . . ?
O4 Cl1 O2 112.9(3) . . ?
O4 Cl1 O3 107.1(3) . . ?
C1M O1M O2M 63.7(4) . . ?
C1M O2M O1M 61.9(4) . . ?
O2M C1M O1M 54.4(4) . . ?
C1M H2Mb O2M 79.9(4) . . ?
C1M H1Mb O1M 74.0(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.599
