# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1203
_database_code_depnum_ccdc_archive 'CCDC 1949701'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 N2, I, 2(H2 O)'
_chemical_formula_sum            'C24 H23 I N2 O2'
_chemical_formula_weight         498.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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

_cell_length_a                   10.7797(2)
_cell_length_b                   8.0018(2)
_cell_length_c                   25.0126(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.3810(10)
_cell_angle_gamma                90
_cell_volume                     2151.21(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    15486
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.511
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8185
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.005
_diffrn_reflns_theta_max         27.421
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4877
_reflns_number_gt                3361
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0220P)²+1.3362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4877
_refine_ls_number_parameters     279
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
I1 I 0.51191(2) 0.18266(3) 0.40559(2) 0.03874(10) Uani 1 1 d . . . . .
H1O2 H 0.700(6) 0.597(6) 0.454(3) 0.16(3) Uiso 1 1 d D . . . .
H1O1 H 0.393(4) 0.177(6) 0.5004(12) 0.068(16) Uiso 1 1 d D . . . .
N1 N 0.3071(2) 0.2817(3) 0.08092(10) 0.0268(6) Uani 1 1 d . . . . .
N2 N 0.9481(2) 0.3602(3) 0.29696(10) 0.0245(6) Uani 1 1 d . . . . .
H2O2 H 0.694(5) 0.443(7) 0.439(3) 0.16(3) Uiso 1 1 d D . . . .
H2O1 H 0.388(5) 0.101(6) 0.5469(18) 0.11(2) Uiso 1 1 d D . . . .
O1W O 0.3532(3) 0.1753(5) 0.52758(14) 0.0622(9) Uani 1 1 d D . . . .
C2 C 0.9640(3) 0.2887(4) 0.34863(12) 0.0219(7) Uani 1 1 d . . . . .
C3 C 0.6289(3) 0.3167(4) 0.18939(12) 0.0224(7) Uani 1 1 d . . . . .
C4 C 0.8815(3) 0.1957(4) 0.37665(13) 0.0269(7) Uani 1 1 d . . . . .
H4 H 0.801564 0.171990 0.361973 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7473(3) 0.2935(4) 0.17227(13) 0.0263(8) Uani 1 1 d . . . . .
H5 H 0.756364 0.267476 0.136538 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5172(3) 0.3024(4) 0.15146(12) 0.0216(7) Uani 1 1 d . . . . .
C7 C 0.4110(3) 0.1988(4) 0.07029(13) 0.0285(8) Uani 1 1 d . . . . .
H7 H 0.411116 0.134241 0.039373 0.034 Uiso 1 1 calc R U . . .
C8 C 1.0861(3) 0.3222(4) 0.37043(12) 0.0221(7) Uani 1 1 d . . . . .
C9 C 1.0425(3) 0.1736(4) 0.44938(13) 0.0333(8) Uani 1 1 d . . . . .
H9 H 1.067009 0.135267 0.483670 0.040 Uiso 1 1 calc R U . . .
C10 C 0.8409(3) 0.3463(4) 0.26133(13) 0.0236(7) Uani 1 1 d . . . . .
C11 C 0.7224(3) 0.3699(4) 0.27866(13) 0.0255(7) Uani 1 1 d . . . . .
H11 H 0.713206 0.396672 0.314321 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3049(3) 0.3751(4) 0.12569(13) 0.0285(8) Uani 1 1 d . . . . .
H13 H 0.232610 0.431795 0.132644 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4077(3) 0.3873(4) 0.16095(13) 0.0256(7) Uani 1 1 d . . . . .
H14 H 0.404801 0.452760 0.191549 0.031 Uiso 1 1 calc R U . . .
C15 C 0.8515(3) 0.3086(4) 0.20736(13) 0.0274(7) Uani 1 1 d . . . . .
H15 H 0.929883 0.293466 0.194974 0.033 Uiso 1 1 calc R U . . .
C16 C 1.1254(3) 0.2634(4) 0.42113(13) 0.0300(8) Uani 1 1 d . . . . .
H16 H 1.205784 0.284032 0.435791 0.036 Uiso 1 1 calc R U . . .
C17 C 0.5167(3) 0.2079(4) 0.10426(12) 0.0258(7) Uani 1 1 d . . . . .
H17 H 0.588201 0.151333 0.096002 0.031 Uiso 1 1 calc R U . . .
C18 C 1.0862(3) 0.5348(4) 0.24209(13) 0.0268(7) Uani 1 1 d . . . . .
H18 H 1.027666 0.550175 0.213225 0.032 Uiso 1 1 calc R U . . .
C19 C 1.2920(3) 0.5816(4) 0.28604(15) 0.0327(8) Uani 1 1 d . . . . .
H19 H 1.370506 0.629079 0.284906 0.039 Uiso 1 1 calc R U . . .
C20 C 1.0601(3) 0.4404(4) 0.28683(12) 0.0228(7) Uani 1 1 d . . . . .
C21 C 0.6186(3) 0.3537(4) 0.24329(13) 0.0251(7) Uani 1 1 d . . . . .
H21 H 0.540128 0.367819 0.255654 0.030 Uiso 1 1 calc R U . . .
C22 C 1.1466(3) 0.4188(4) 0.33065(12) 0.0227(7) Uani 1 1 d . . . . .
C23 C 1.2040(3) 0.6043(4) 0.24306(14) 0.0309(8) Uani 1 1 d . . . . .
H23 H 1.224983 0.668134 0.214020 0.037 Uiso 1 1 calc R U . . .
C24 C 1.2648(3) 0.4897(4) 0.33037(13) 0.0270(8) Uani 1 1 d . . . . .
H24 H 1.323617 0.475410 0.359212 0.032 Uiso 1 1 calc R U . . .
C25 C 0.9228(3) 0.1399(4) 0.42711(13) 0.0313(8) Uani 1 1 d . . . . .
H25 H 0.869212 0.077969 0.446785 0.038 Uiso 1 1 calc R U . . .
O2W O 0.7468(3) 0.5169(5) 0.44664(16) 0.0674(9) Uani 1 1 d D . . . .
C27 C 0.1936(3) 0.2668(6) 0.04386(16) 0.0454(10) Uani 1 1 d . . . . .
H27A H 0.167057 0.375995 0.031939 0.068 Uiso 1 1 calc R U . . .
H27B H 0.128749 0.214588 0.062157 0.068 Uiso 1 1 calc R U . . .
H27C H 0.211503 0.200097 0.013480 0.068 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.345(4) . ?
N1 C13 1.348(4) . ?
N1 C27 1.482(4) . ?
N2 C20 1.408(4) . ?
N2 C10 1.409(4) . ?
N2 C2 1.412(4) . ?
O1W H1O1 0.831(18) . ?
O1W H2O1 0.834(19) . ?
C2 C4 1.389(4) . ?
C2 C8 1.412(4) . ?
C3 C5 1.389(4) . ?
C3 C21 1.393(4) . ?
C3 C6 1.480(4) . ?
C4 C25 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C15 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C14 1.398(4) . ?
C6 C17 1.402(4) . ?
C7 C17 1.370(5) . ?
C7 H7 0.9300 . ?
C8 C16 1.388(5) . ?
C8 C22 1.453(4) . ?
C9 C16 1.382(5) . ?
C9 C25 1.392(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.393(4) . ?
C10 C15 1.396(4) . ?
C11 C21 1.378(5) . ?
C11 H11 0.9300 . ?
C13 C14 1.366(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.385(5) . ?
C18 C20 1.396(4) . ?
C18 H18 0.9300 . ?
C19 C24 1.381(5) . ?
C19 C23 1.390(5) . ?
C19 H19 0.9300 . ?
C20 C22 1.394(4) . ?
C21 H21 0.9300 . ?
C22 C24 1.396(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
O2W H1O2 0.842(19) . ?
O2W H2O2 0.83(2) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C7 N1 C13 120.3(3) . . ?
C7 N1 C27 119.8(3) . . ?
C13 N1 C27 119.9(3) . . ?
C20 N2 C10 126.5(3) . . ?
C20 N2 C2 107.7(3) . . ?
C10 N2 C2 125.7(2) . . ?
H1O1 O1W H2O1 105(4) . . ?
C4 C2 N2 129.9(3) . . ?
C4 C2 C8 121.4(3) . . ?
N2 C2 C8 108.7(3) . . ?
C5 C3 C21 118.0(3) . . ?
C5 C3 C6 120.9(3) . . ?
C21 C3 C6 121.0(3) . . ?
C25 C4 C2 117.4(3) . . ?
C25 C4 H4 121.3 . . ?
C2 C4 H4 121.3 . . ?
C15 C5 C3 121.0(3) . . ?
C15 C5 H5 119.5 . . ?
C3 C5 H5 119.5 . . ?
C14 C6 C17 117.2(3) . . ?
C14 C6 C3 120.7(3) . . ?
C17 C6 C3 122.1(3) . . ?
N1 C7 C17 121.1(3) . . ?
N1 C7 H7 119.4 . . ?
C17 C7 H7 119.4 . . ?
C16 C8 C2 119.9(3) . . ?
C16 C8 C22 133.2(3) . . ?
C2 C8 C22 106.9(3) . . ?
C16 C9 C25 120.8(3) . . ?
C16 C9 H9 119.6 . . ?
C25 C9 H9 119.6 . . ?
C11 C10 C15 118.4(3) . . ?
C11 C10 N2 121.3(3) . . ?
C15 C10 N2 120.3(3) . . ?
C21 C11 C10 120.4(3) . . ?
C21 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N1 C13 C14 120.8(3) . . ?
N1 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C6 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C6 C14 H14 119.7 . . ?
C5 C15 C10 120.8(3) . . ?
C5 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C9 C16 C8 118.7(3) . . ?
C9 C16 H16 120.7 . . ?
C8 C16 H16 120.7 . . ?
C7 C17 C6 120.0(3) . . ?
C7 C17 H17 120.0 . . ?
C6 C17 H17 120.0 . . ?
C23 C18 C20 116.3(3) . . ?
C23 C18 H18 121.8 . . ?
C20 C18 H18 121.8 . . ?
C24 C19 C23 121.1(3) . . ?
C24 C19 H19 119.4 . . ?
C23 C19 H19 119.4 . . ?
C22 C20 C18 122.3(3) . . ?
C22 C20 N2 109.5(3) . . ?
C18 C20 N2 128.2(3) . . ?
C11 C21 C3 121.4(3) . . ?
C11 C21 H21 119.3 . . ?
C3 C21 H21 119.3 . . ?
C20 C22 C24 120.1(3) . . ?
C20 C22 C8 107.2(3) . . ?
C24 C22 C8 132.6(3) . . ?
C18 C23 C19 122.1(3) . . ?
C18 C23 H23 118.9 . . ?
C19 C23 H23 118.9 . . ?
C19 C24 C22 118.1(3) . . ?
C19 C24 H24 121.0 . . ?
C22 C24 H24 121.0 . . ?
C4 C25 C9 121.8(3) . . ?
C4 C25 H25 119.1 . . ?
C9 C25 H25 119.1 . . ?
H1O2 O2W H2O2 100(4) . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C20 N2 C2 C4 -179.3(3) . . . . ?
C10 N2 C2 C4 -2.0(5) . . . . ?
C20 N2 C2 C8 -0.8(3) . . . . ?
C10 N2 C2 C8 176.6(3) . . . . ?
N2 C2 C4 C25 179.6(3) . . . . ?
C8 C2 C4 C25 1.2(5) . . . . ?
C21 C3 C5 C15 -0.7(5) . . . . ?
C6 C3 C5 C15 179.3(3) . . . . ?
C5 C3 C6 C14 -153.9(3) . . . . ?
C21 C3 C6 C14 26.1(5) . . . . ?
C5 C3 C6 C17 24.5(5) . . . . ?
C21 C3 C6 C17 -155.5(3) . . . . ?
C13 N1 C7 C17 -0.4(5) . . . . ?
C27 N1 C7 C17 -178.9(3) . . . . ?
C4 C2 C8 C16 -0.7(5) . . . . ?
N2 C2 C8 C16 -179.5(3) . . . . ?
C4 C2 C8 C22 179.1(3) . . . . ?
N2 C2 C8 C22 0.4(3) . . . . ?
C20 N2 C10 C11 -137.3(3) . . . . ?
C2 N2 C10 C11 45.8(5) . . . . ?
C20 N2 C10 C15 42.6(5) . . . . ?
C2 N2 C10 C15 -134.3(3) . . . . ?
C15 C10 C11 C21 0.9(5) . . . . ?
N2 C10 C11 C21 -179.2(3) . . . . ?
C7 N1 C13 C14 0.0(5) . . . . ?
C27 N1 C13 C14 178.5(3) . . . . ?
N1 C13 C14 C6 -0.4(5) . . . . ?
C17 C6 C14 C13 1.0(4) . . . . ?
C3 C6 C14 C13 179.5(3) . . . . ?
C3 C5 C15 C10 0.5(5) . . . . ?
C11 C10 C15 C5 -0.6(5) . . . . ?
N2 C10 C15 C5 179.5(3) . . . . ?
C25 C9 C16 C8 1.2(5) . . . . ?
C2 C8 C16 C9 -0.5(5) . . . . ?
C22 C8 C16 C9 179.7(3) . . . . ?
N1 C7 C17 C6 1.1(5) . . . . ?
C14 C6 C17 C7 -1.4(4) . . . . ?
C3 C6 C17 C7 -179.8(3) . . . . ?
C23 C18 C20 C22 1.0(5) . . . . ?
C23 C18 C20 N2 178.2(3) . . . . ?
C10 N2 C20 C22 -176.5(3) . . . . ?
C2 N2 C20 C22 0.9(3) . . . . ?
C10 N2 C20 C18 6.0(5) . . . . ?
C2 N2 C20 C18 -176.6(3) . . . . ?
C10 C11 C21 C3 -1.2(5) . . . . ?
C5 C3 C21 C11 1.1(5) . . . . ?
C6 C3 C21 C11 -179.0(3) . . . . ?
C18 C20 C22 C24 -1.4(5) . . . . ?
N2 C20 C22 C24 -179.0(3) . . . . ?
C18 C20 C22 C8 177.0(3) . . . . ?
N2 C20 C22 C8 -0.6(3) . . . . ?
C16 C8 C22 C20 180.0(3) . . . . ?
C2 C8 C22 C20 0.2(3) . . . . ?
C16 C8 C22 C24 -1.9(6) . . . . ?
C2 C8 C22 C24 178.3(3) . . . . ?
C20 C18 C23 C19 0.1(5) . . . . ?
C24 C19 C23 C18 -0.9(5) . . . . ?
C23 C19 C24 C22 0.5(5) . . . . ?
C20 C22 C24 C19 0.5(4) . . . . ?
C8 C22 C24 C19 -177.4(3) . . . . ?
C2 C4 C25 C9 -0.4(5) . . . . ?
C16 C9 C25 C4 -0.8(5) . . . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_KL1256
_database_code_depnum_ccdc_archive 'CCDC 1949703'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;
_audit_creation_date             2019-03-12
_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, C12 H12 N'
_chemical_formula_sum            'C12 H12 Cl N O4'
_chemical_formula_weight         269.69
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                   11.7674(10)
_cell_length_b                   5.8992(5)
_cell_length_c                   17.3999(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.609(8)
_cell_angle_gamma                90
_cell_volume                     1199.84(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2107
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      75.0
_cell_measurement_theta_min      3.0
_exptl_absorpt_coefficient_mu    2.906
_exptl_crystal_density_diffrn    1.4928
_exptl_absorpt_correction_type   none
_exptl_crystal_F_000             560
_exptl_crystal_colour            'Colourless '
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4414
_diffrn_reflns_theta_full        78.2351
_diffrn_reflns_theta_max         78.24
_diffrn_reflns_theta_min         3.78
_diffrn_measured_fraction_theta_full 0.9805
_diffrn_measured_fraction_theta_max 0.9805
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                2239
_reflns_number_total             2520
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.8817
_refine_diff_density_min         -0.9476
_refine_diff_density_rms         0.1507
_refine_ls_d_res_high            0.7875
_refine_ls_d_res_low             11.6892
_refine_ls_goodness_of_fit_ref   1.0188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0967
_refine_ls_restrained_S_all      1.0188
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+6.5400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2119
_refine_ls_wR_factor_ref         0.2219
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C6(H6), C5(H5), C10(H10), C13(H13), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c)
;
_atom_sites_solution_primary     iterative
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 0.32790(9) 0.3375(2) 0.61386(6) 0.0351(3) Uani 1.000000 .
O1 O 0.4097(3) 0.3391(8) 0.5587(2) 0.0516(11) Uani 1.000000 .
N1 N 0.6195(3) 0.0404(8) 0.6257(2) 0.0366(10) Uani 1.000000 .
O4 O 0.3817(4) 0.2592(9) 0.6871(2) 0.0571(12) Uani 1.000000 .
O3 O 0.2861(6) 0.5568(10) 0.6235(2) 0.091(2) Uani 1.000000 .
C2 C 0.6399(4) 0.1597(9) 0.6919(2) 0.0334(10) Uani 1.000000 .
H2 H 0.6042(4) 0.1181(9) 0.7348(2) 0.0401(12) Uiso 1.000000 R
C3 C 0.7135(4) 0.3437(9) 0.6967(3) 0.0341(10) Uani 1.000000 .
H3 H 0.7276(4) 0.4220(9) 0.7432(3) 0.0409(13) Uiso 1.000000 R
C7 C 0.5409(4) -0.1567(10) 0.6227(3) 0.0401(12) Uani 1.000000 .
H7a H 0.563(2) -0.255(4) 0.6659(13) 0.0602(18) Uiso 1.000000 GR
H7b H 0.4641(6) -0.1045(11) 0.625(2) 0.0602(18) Uiso 1.000000 GR
H7c H 0.545(3) -0.239(4) 0.5754(11) 0.0602(18) Uiso 1.000000 GR
C4 C 0.7668(4) 0.4140(10) 0.6336(3) 0.0363(11) Uani 1.000000 .
C8 C 0.8480(4) 0.6056(9) 0.6385(3) 0.0376(11) Uani 1.000000 .
C9 C 0.8492(4) 0.7658(9) 0.6969(3) 0.0336(10) Uani 1.000000 .
H9 H 0.7977(4) 0.7523(9) 0.7334(3) 0.0403(12) Uiso 1.000000 R
C6 C 0.6701(4) 0.1004(10) 0.5635(3) 0.0392(12) Uani 1.000000 .
H6 H 0.6569(4) 0.0150(10) 0.5185(3) 0.0470(14) Uiso 1.000000 R
C5 C 0.7411(4) 0.2857(10) 0.5651(2) 0.0401(12) Uani 1.000000 .
H5 H 0.7726(4) 0.3273(10) 0.5206(2) 0.0482(14) Uiso 1.000000 R
C10 C 0.9254(4) 0.9453(10) 0.7021(3) 0.0420(12) Uani 1.000000 .
H10 H 0.9245(4) 1.0504(10) 0.7419(3) 0.0504(14) Uiso 1.000000 R
C13 C 0.9268(5) 0.6278(12) 0.5854(4) 0.0572(17) Uani 1.000000 .
H13 H 0.9286(5) 0.5217(12) 0.5460(4) 0.069(2) Uiso 1.000000 R
C11 C 1.0036(5) 0.9699(11) 0.6482(3) 0.0492(13) Uani 1.000000 .
H11 H 1.0545(5) 1.0911(11) 0.6509(3) 0.0591(16) Uiso 1.000000 R
O2 O 0.2405(5) 0.1762(17) 0.5885(4) 0.140(4) Uani 1.000000 .
C12 C 1.0030(6) 0.8089(13) 0.5910(4) 0.0646(19) Uani 1.000000 .
H12 H 1.0552(6) 0.8215(13) 0.5550(4) 0.077(2) 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 O1 1.435(3) . ?
Cl1 O4 1.433(4) . ?
Cl1 O3 1.401(5) . ?
Cl1 O2 1.433(6) . ?
N1 C2 1.348(6) . ?
N1 C7 1.483(7) . ?
N1 C6 1.341(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(6) . ?
C7 H7a 0.9600 . ?
C7 H7b 0.9600 . ?
C7 H7c 0.9600 . ?
C4 C8 1.476(8) . ?
C4 C5 1.414(7) . ?
C8 C9 1.387(7) . ?
C8 C13 1.389(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.374(8) . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.396(7) . ?
C13 H13 0.9300 . ?
C13 C12 1.391(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(9) . ?
C12 H12 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 O1 109.6(2) . . ?
O3 Cl1 O1 110.2(3) . . ?
O3 Cl1 O4 108.4(3) . . ?
O2 Cl1 O1 108.1(3) . . ?
O2 Cl1 O4 106.7(4) . . ?
O2 Cl1 O3 113.6(5) . . ?
C7 N1 C2 119.3(4) . . ?
C6 N1 C2 120.0(5) . . ?
C6 N1 C7 120.7(4) . . ?
H2 C2 N1 119.7(3) . . ?
C3 C2 N1 120.6(4) . . ?
C3 C2 H2 119.7(2) . . ?
H3 C3 C2 119.2(2) . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H3 119.2(3) . . ?
H7a C7 N1 109.5 . . ?
H7b C7 N1 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 N1 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
C8 C4 C3 122.0(4) . . ?
C5 C4 C3 115.7(5) . . ?
C5 C4 C8 122.2(4) . . ?
C9 C8 C4 121.1(4) . . ?
C13 C8 C4 120.7(5) . . ?
C13 C8 C9 118.2(5) . . ?
H9 C9 C8 119.3(3) . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9 119.3(3) . . ?
H6 C6 N1 119.4(3) . . ?
C5 C6 N1 121.3(5) . . ?
C5 C6 H6 119.4(3) . . ?
C6 C5 C4 120.9(4) . . ?
H5 C5 C4 119.5(3) . . ?
H5 C5 C6 119.5(3) . . ?
H10 C10 C9 119.7(3) . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.7(4) . . ?
H13 C13 C8 120.0(4) . . ?
C12 C13 C8 120.0(6) . . ?
C12 C13 H13 120.0(3) . . ?
H11 C11 C10 121.1(4) . . ?
C12 C11 C10 117.8(6) . . ?
C12 C11 H11 121.1(4) . . ?
C11 C12 C13 122.1(5) . . ?
H12 C12 C13 119.0(3) . . ?
H12 C12 C11 119.0(4) . . ?

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

data_KL_1232
_database_code_depnum_ccdc_archive 'CCDC 1949702'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;
_audit_creation_date             2018-10-29
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_chemical_name_systematic        
;
 ? 
;
# start Validation Reply Form
_vrf_PLAT260_KL_1232             
;
PROBLEM: Large Average Ueq of Residue Including       Cl1      0.215 
RESPONSE: In the crystal structure there are considerable thermal libration 
motions for cloride anions and acetonitryle molecules.
;
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix

_chemical_formula_moiety         'Cl O4, C24 H19 N2, C2 H3 N'
_chemical_formula_sum            'C26 H22 Cl N3 O4'
_chemical_formula_weight         475.93
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/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   16.36790(12)
_cell_length_b                   7.39194(5)
_cell_length_c                   19.97192(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.1870(7)
_cell_angle_gamma                90
_cell_volume                     2342.72(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4409
_cell_measurement_theta_min      0.9
_cell_measurement_theta_max      75.0

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02

_exptl_absorpt_coefficient_mu    1.763
_exptl_crystal_density_diffrn    1.3493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             996.5506
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21192
_diffrn_reflns_theta_full        77.0970
_diffrn_reflns_theta_max         77.10
_diffrn_reflns_theta_min         4.01
_diffrn_measured_fraction_theta_full 0.9877
_diffrn_measured_fraction_theta_max 0.9877
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -20
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              -13
_reflns_number_gt                4573
_reflns_number_total             4901
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.7378
_refine_diff_density_min         -0.4791
_refine_diff_density_rms         0.0526
_refine_ls_d_res_high            0.7909
_refine_ls_d_res_low             11.0205
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0415
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.0415
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1566P)²+0.5898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2240
_refine_ls_wR_factor_ref         0.2271
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C21(H21), C1(H1), C17(H17), C2(H2),
 C8(H8), C7(H7), C18(H18), C5(H5), C20(H20), C4(H4), C3(H3), C6(H6)
2.b Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c), C1'(H1'a,H1'b,H1'c)
;
_atom_sites_solution_primary     iterative
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 0.44784(5) 0.11487(12) 0.23118(3) 0.0888(3) Uani 1.000000 .
N9 N 0.18351(9) 0.2331(2) 0.54949(8) 0.0489(4) Uani 1.000000 .
N19 N -0.34630(10) 0.3135(3) 0.43298(11) 0.0624(5) Uani 1.000000 .
C11 C 0.05503(11) 0.2989(2) 0.46048(9) 0.0468(4) Uani 1.000000 .
H11 H 0.08696(11) 0.3349(2) 0.43019(9) 0.0562(5) Uiso 1.000000 R
C12 C -0.03196(11) 0.3057(2) 0.44008(9) 0.0466(4) Uani 1.000000 .
H12 H -0.05818(11) 0.3417(2) 0.39535(9) 0.0559(5) Uiso 1.000000 R
C13 C -0.08105(11) 0.2595(2) 0.48574(10) 0.0461(4) Uani 1.000000 .
C10 C 0.09483(11) 0.2379(2) 0.52641(9) 0.0453(4) Uani 1.000000 .
C16 C -0.17344(11) 0.2786(2) 0.46669(10) 0.0473(4) Uani 1.000000 .
C14 C -0.04050(11) 0.1982(2) 0.55153(9) 0.0482(4) Uani 1.000000 .
H14 H -0.07227(11) 0.1673(2) 0.58257(9) 0.0578(5) Uiso 1.000000 R
C15 C 0.04567(11) 0.1828(2) 0.57111(9) 0.0483(4) Uani 1.000000 .
H15 H 0.07153(11) 0.1355(2) 0.61426(9) 0.0580(5) Uiso 1.000000 R
C9A C 0.22914(12) 0.2861(2) 0.61589(10) 0.0499(4) Uani 1.000000 .
C21 C -0.21615(13) 0.3372(3) 0.51506(11) 0.0567(5) Uani 1.000000 .
H21 H -0.18629(13) 0.3640(3) 0.55988(11) 0.0680(6) Uiso 1.000000 R
C4B C 0.32300(12) 0.1916(3) 0.55485(11) 0.0550(5) Uani 1.000000 .
C8A C 0.24118(11) 0.1789(2) 0.51207(10) 0.0502(4) Uani 1.000000 .
O3 O 0.4337(3) 0.0615(6) 0.29403(14) 0.1708(17) Uani 1.000000 .
C4A C 0.31558(12) 0.2596(3) 0.62080(11) 0.0558(5) Uani 1.000000 .
C1 C 0.20104(13) 0.3646(3) 0.66934(10) 0.0553(5) Uani 1.000000 .
H1 H 0.14383(13) 0.3810(3) 0.66590(10) 0.0663(5) Uiso 1.000000 R
C17 C -0.22167(12) 0.2391(3) 0.40057(11) 0.0547(4) Uani 1.000000 .
H17 H -0.19539(12) 0.2011(3) 0.36667(11) 0.0657(5) Uiso 1.000000 R
C2 C 0.26069(16) 0.4175(3) 0.72782(12) 0.0667(6) Uani 1.000000 .
H2 H 0.24343(16) 0.4742(3) 0.76359(12) 0.0801(7) Uiso 1.000000 R
C8 C 0.22735(13) 0.1167(3) 0.44444(12) 0.0589(5) Uani 1.000000 .
H8 H 0.17313(13) 0.1069(3) 0.41625(12) 0.0707(6) Uiso 1.000000 R
C7 C 0.29694(15) 0.0700(4) 0.42063(14) 0.0700(6) Uani 1.000000 .
H7 H 0.28911(15) 0.0282(4) 0.37558(14) 0.0840(7) Uiso 1.000000 R
C18 C -0.30764(13) 0.2560(3) 0.38522(12) 0.0620(5) Uani 1.000000 .
H18 H -0.33937(13) 0.2271(3) 0.34118(12) 0.0744(6) Uiso 1.000000 R
C5 C 0.39239(14) 0.1437(3) 0.52921(15) 0.0684(6) Uani 1.000000 .
H5 H 0.44683(14) 0.1523(3) 0.55709(15) 0.0821(7) Uiso 1.000000 R
C20 C -0.30217(14) 0.3554(3) 0.49675(13) 0.0644(5) Uani 1.000000 .
H20 H -0.33009(14) 0.3975(3) 0.52901(13) 0.0772(6) Uiso 1.000000 R
C4 C 0.37431(14) 0.3079(4) 0.68136(13) 0.0704(6) Uani 1.000000 .
H4 H 0.43144(14) 0.2867(4) 0.68601(13) 0.0845(7) Uiso 1.000000 R
C3 C 0.34674(17) 0.3870(4) 0.73408(13) 0.0767(7) Uani 1.000000 .
H3 H 0.38565(17) 0.4208(4) 0.77440(13) 0.0920(8) Uiso 1.000000 R
C6 C 0.37884(15) 0.0840(4) 0.46242(16) 0.0763(7) Uani 1.000000 .
H6 H 0.42445(15) 0.0524(4) 0.44476(16) 0.0915(8) Uiso 1.000000 R
N1' N 0.4081(2) 0.6376(6) 0.38352(18) 0.1159(11) Uani 1.000000 .
C22 C -0.43883(14) 0.3346(5) 0.41594(19) 0.0895(9) Uani 1.000000 .
H22a H -0.46447(16) 0.241(2) 0.3845(11) 0.1343(13) Uiso 1.000000 GR
H22b H -0.4583(2) 0.326(4) 0.4574(3) 0.1343(13) Uiso 1.000000 GR
H22c H -0.45385(18) 0.4505(16) 0.3948(13) 0.1343(13) Uiso 1.000000 GR
O1 O 0.5145(3) 0.2197(11) 0.2380(2) 0.261(4) Uani 1.000000 .
O2 O 0.4491(6) -0.0173(9) 0.1871(3) 0.287(4) Uani 1.000000 .
C2' C 0.3725(2) 0.6364(6) 0.3288(2) 0.0976(10) Uani 1.000000 .
O4 O 0.3821(4) 0.2003(13) 0.1947(3) 0.266(4) Uani 1.000000 .
C1' C 0.3275(4) 0.6407(9) 0.2567(3) 0.154(2) Uani 1.000000 .
H1'a H 0.284(2) 0.550(5) 0.2482(7) 0.231(3) Uiso 1.000000 GR
H1'b H 0.302(3) 0.758(2) 0.2457(7) 0.231(3) Uiso 1.000000 GR
H1'c H 0.3661(8) 0.617(7) 0.2285(3) 0.231(3) Uiso 1.000000 GR


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 O3 1.388(3) . ?
Cl1 O1 1.319(4) . ?
Cl1 O2 1.318(5) . ?
Cl1 O4 1.305(5) . ?
N9 C10 1.412(2) . ?
N9 C9A 1.409(2) . ?
N9 C8A 1.398(2) . ?
N19 C18 1.337(3) . ?
N19 C20 1.338(3) . ?
N19 C22 1.477(3) . ?
C11 C12 1.383(2) . ?
C11 C10 1.393(2) . ?
C12 C13 1.398(2) . ?
C13 C16 1.473(2) . ?
C13 C14 1.394(3) . ?
C10 C15 1.401(2) . ?
C16 C21 1.393(3) . ?
C16 C17 1.393(3) . ?
C14 C15 1.373(2) . ?
C9A C4A 1.408(3) . ?
C9A C1 1.389(3) . ?
C21 C20 1.372(3) . ?
C4B C8A 1.404(3) . ?
C4B C4A 1.443(3) . ?
C4B C5 1.401(3) . ?
C8A C8 1.392(3) . ?
C4A C4 1.394(3) . ?
C1 C2 1.383(3) . ?
C17 C18 1.370(3) . ?
C2 C3 1.401(4) . ?
C8 C7 1.381(3) . ?
C7 C6 1.399(4) . ?
C5 C6 1.371(4) . ?
C4 C3 1.374(4) . ?
N1' C2' 1.105(4) . ?
C2' C1' 1.448(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cl1 O3 113.0(2) . . ?
O2 Cl1 O3 115.2(3) . . ?
O2 Cl1 O1 110.9(5) . . ?
O4 Cl1 O3 110.2(3) . . ?
O4 Cl1 O1 108.8(6) . . ?
O4 Cl1 O2 97.5(5) . . ?
C9A N9 C10 124.46(15) . . ?
C8A N9 C10 127.40(16) . . ?
C8A N9 C9A 108.13(15) . . ?
C20 N19 C18 120.90(18) . . ?
C22 N19 C18 120.5(2) . . ?
C22 N19 C20 118.6(2) . . ?
C10 C11 C12 119.97(16) . . ?
C13 C12 C11 120.93(16) . . ?
C16 C13 C12 121.73(16) . . ?
C14 C13 C12 118.50(16) . . ?
C14 C13 C16 119.74(16) . . ?
C11 C10 N9 121.47(16) . . ?
C15 C10 N9 119.32(16) . . ?
C15 C10 C11 119.21(16) . . ?
C21 C16 C13 120.59(17) . . ?
C17 C16 C13 122.14(17) . . ?
C17 C16 C21 117.28(17) . . ?
C15 C14 C13 120.93(16) . . ?
C14 C15 C10 120.30(16) . . ?
C4A C9A N9 108.59(17) . . ?
C1 C9A N9 129.85(17) . . ?
C1 C9A C4A 121.41(18) . . ?
C20 C21 C16 120.2(2) . . ?
C4A C4B C8A 107.31(17) . . ?
C5 C4B C8A 119.9(2) . . ?
C5 C4B C4A 132.8(2) . . ?
C4B C8A N9 108.89(17) . . ?
C8 C8A N9 130.00(18) . . ?
C8 C8A C4B 121.09(18) . . ?
C4B C4A C9A 107.03(17) . . ?
C4 C4A C9A 119.5(2) . . ?
C4 C4A C4B 133.4(2) . . ?
C2 C1 C9A 118.0(2) . . ?
C18 C17 C16 120.3(2) . . ?
C3 C2 C1 121.1(2) . . ?
C7 C8 C8A 117.7(2) . . ?
C6 C7 C8 121.8(2) . . ?
C17 C18 N19 120.6(2) . . ?
C6 C5 C4B 119.0(2) . . ?
C21 C20 N19 120.7(2) . . ?
C3 C4 C4A 119.2(2) . . ?
C4 C3 C2 120.8(2) . . ?
C5 C6 C7 120.5(2) . . ?
C1' C2' N1' 177.8(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
