# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1938798'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2019-07-06 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H6 Cl2 N2 O4, C3 H7 N O, H2 O'
_chemical_formula_sum            'C17 H15 Cl2 N3 O6'
_chemical_formula_weight         428.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0046 0.0021 '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 0.0084 0.0041 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0146 0.0077 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1730 0.1957 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.1583(14)
_cell_length_b                   8.3520(17)
_cell_length_c                   15.356(3)
_cell_angle_alpha                81.10(3)
_cell_angle_beta                 82.92(3)
_cell_angle_gamma                78.62(3)
_cell_volume                     885.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      30.0

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.538
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'Scala (Evans, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.78790
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15682
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.495
_diffrn_reflns_theta_max         30.758
_diffrn_reflns_theta_full        28.212
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4025
_reflns_number_gt                3711
_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL

_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)+(0.0509P)²+0.2561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4025
_refine_ls_number_parameters     268
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.074
_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
Cl1 Cl 0.18535(4) 0.58423(4) -0.07673(2) 0.02607(11) Uani 1 1 d . . . . .
Cl2 Cl 0.64634(5) -0.17930(4) 0.19810(2) 0.02966(11) Uani 1 1 d . . . . .
O1 O 0.13949(16) 0.85758(12) 0.28587(7) 0.0356(2) Uani 1 1 d . . . . .
O2 O 0.05353(14) 0.99517(11) 0.15649(6) 0.0284(2) Uani 1 1 d D . . . .
H2 H 0.029(3) 1.0835(18) 0.1877(12) 0.043 Uiso 1 1 d D U . . .
O3 O 0.69352(14) 0.06871(12) 0.48891(6) 0.0311(2) Uani 1 1 d . . . . .
O4 O 0.51821(14) 0.32315(12) 0.47479(6) 0.0291(2) Uani 1 1 d D . . . .
H4 H 0.554(3) 0.331(2) 0.5286(8) 0.044 Uiso 1 1 d D U . . .
N1 N 0.27531(15) 0.57921(13) 0.20933(7) 0.0231(2) Uani 1 1 d . . . . .
C2 C 0.19078(17) 0.71284(15) 0.16039(8) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.16099(17) 0.71999(16) 0.07140(8) 0.0245(2) Uani 1 1 d . . . . .
H3 H 0.1016 0.8192 0.0388 0.029 Uiso 1 1 calc R U . . .
C4 C 0.22054(17) 0.57880(16) 0.03302(8) 0.0237(2) Uani 1 1 d . . . . .
C4A C 0.30832(17) 0.43190(16) 0.08191(8) 0.0233(2) Uani 1 1 d . . . . .
C5 C 0.36784(19) 0.27986(17) 0.04627(9) 0.0260(3) Uani 1 1 d . . . . .
H5 H 0.3483 0.2747 -0.0132 0.031 Uiso 1 1 calc R U . . .
C6 C 0.45163(19) 0.14341(16) 0.09627(9) 0.0260(3) Uani 1 1 d . . . . .
H6 H 0.4886 0.0431 0.0715 0.031 Uiso 1 1 calc R U . . .
C6A C 0.48592(17) 0.14638(15) 0.18557(8) 0.0234(2) Uani 1 1 d . . . . .
C7 C 0.57508(18) 0.00704(16) 0.23963(9) 0.0249(3) Uani 1 1 d . . . . .
C8 C 0.60662(18) 0.01680(16) 0.32432(9) 0.0262(3) Uani 1 1 d . . . . .
H8 H 0.6661 -0.0769 0.3610 0.031 Uiso 1 1 calc R U . . .
C9 C 0.54807(17) 0.17030(15) 0.35524(8) 0.0235(2) Uani 1 1 d . . . . .
N10 N 0.46182(14) 0.30540(13) 0.30806(7) 0.0225(2) Uani 1 1 d . . . . .
C10A C 0.43019(17) 0.29393(15) 0.22424(8) 0.0222(2) Uani 1 1 d . . . . .
C10B C 0.33486(17) 0.44082(15) 0.17095(8) 0.0220(2) Uani 1 1 d . . . . .
C11 C 0.12530(18) 0.86312(16) 0.20722(9) 0.0251(3) Uani 1 1 d . . . . .
C12 C 0.59361(18) 0.18180(16) 0.44752(8) 0.0245(3) Uani 1 1 d . . . . .
O5 O -0.03009(14) 0.23564(11) 0.24261(6) 0.0284(2) Uani 1 1 d . . . . .
N11 N -0.02162(15) 0.32975(13) 0.37265(7) 0.0251(2) Uani 1 1 d . . . . .
C13 C 0.01432(18) 0.21408(16) 0.32044(9) 0.0256(3) Uani 1 1 d . . . . .
H13 H 0.0779 0.1077 0.3432 0.031 Uiso 1 1 calc R U . . .
C14 C -0.1175(2) 0.49645(16) 0.34283(10) 0.0299(3) Uani 1 1 d . . . . .
H14A H -0.0289 0.5732 0.3403 0.045 Uiso 1 1 calc R U . . .
H14B H -0.2295 0.5277 0.3844 0.045 Uiso 1 1 calc R U . . .
H14C H -0.1586 0.5007 0.2838 0.045 Uiso 1 1 calc R U . . .
C15 C 0.0415(2) 0.29744(17) 0.46137(9) 0.0299(3) Uani 1 1 d . . . . .
H15A H 0.1002 0.1810 0.4740 0.045 Uiso 1 1 calc R U . . .
H15B H -0.0688 0.3231 0.5047 0.045 Uiso 1 1 calc R U . . .
H15C H 0.1354 0.3665 0.4651 0.045 Uiso 1 1 calc R U . . .
O6 O 0.62183(18) 0.37063(13) 0.61630(7) 0.0407(3) Uani 1 1 d D . . . .
H6A H 0.697(3) 0.301(2) 0.6526(12) 0.061 Uiso 1 1 d D U . . .
H6B H 0.593(3) 0.4693(16) 0.6337(14) 0.061 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.7269(13) . ?
Cl2 C7 1.7328(14) . ?
O1 C11 1.2175(16) . ?
O2 C11 1.3024(16) . ?
O2 H2 0.92(2) . ?
O3 C12 1.2114(17) . ?
O4 C12 1.3063(16) . ?
O4 H4 0.91(2) . ?
N1 C2 1.3276(17) . ?
N1 C10B 1.3489(17) . ?
C2 C3 1.3994(17) . ?
C2 C11 1.5088(17) . ?
C3 C4 1.3690(19) . ?
C3 H3 0.9500 . ?
C4 C4A 1.4110(18) . ?
C4A C10B 1.4186(17) . ?
C4A C5 1.4275(18) . ?
C5 C6 1.350(2) . ?
C5 H5 0.9500 . ?
C6 C6A 1.4273(18) . ?
C6 H6 0.9500 . ?
C6A C7 1.4104(18) . ?
C6A C10A 1.4159(17) . ?
C7 C8 1.3643(18) . ?
C8 C9 1.4043(18) . ?
C8 H8 0.9500 . ?
C9 N10 1.3273(17) . ?
C9 C12 1.5139(18) . ?
N10 C10A 1.3549(16) . ?
C10A C10B 1.4618(18) . ?
O5 C13 1.2516(16) . ?
N11 C13 1.3165(17) . ?
N11 C14 1.4569(17) . ?
N11 C15 1.4569(17) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O6 H6A 0.89(2) . ?
O6 H6B 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 H2 109.4(13) . . ?
C12 O4 H4 112.1(12) . . ?
C2 N1 C10B 117.83(11) . . ?
N1 C2 C3 124.32(12) . . ?
N1 C2 C11 115.39(11) . . ?
C3 C2 C11 120.29(11) . . ?
C4 C3 C2 117.56(12) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C4A 120.88(12) . . ?
C3 C4 Cl1 118.49(10) . . ?
C4A C4 Cl1 120.62(10) . . ?
C4 C4A C10B 116.41(12) . . ?
C4 C4A C5 123.36(12) . . ?
C10B C4A C5 120.22(12) . . ?
C6 C5 C4A 120.64(12) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C6A 121.46(12) . . ?
C5 C6 H6 119.3 . . ?
C6A C6 H6 119.3 . . ?
C7 C6A C10A 116.52(11) . . ?
C7 C6A C6 123.20(12) . . ?
C10A C6A C6 120.28(12) . . ?
C8 C7 C6A 120.93(12) . . ?
C8 C7 Cl2 119.37(10) . . ?
C6A C7 Cl2 119.70(10) . . ?
C7 C8 C9 117.61(12) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
N10 C9 C8 124.37(12) . . ?
N10 C9 C12 118.51(11) . . ?
C8 C9 C12 117.08(11) . . ?
C9 N10 C10A 117.48(11) . . ?
N10 C10A C6A 123.08(12) . . ?
N10 C10A C10B 118.57(11) . . ?
C6A C10A C10B 118.34(11) . . ?
N1 C10B C4A 122.97(12) . . ?
N1 C10B C10A 118.03(11) . . ?
C4A C10B C10A 119.00(11) . . ?
O1 C11 O2 124.22(12) . . ?
O1 C11 C2 121.54(12) . . ?
O2 C11 C2 114.24(11) . . ?
O3 C12 O4 125.47(12) . . ?
O3 C12 C9 121.15(12) . . ?
O4 C12 C9 113.37(11) . . ?
C13 N11 C14 121.56(12) . . ?
C13 N11 C15 120.97(11) . . ?
C14 N11 C15 117.41(11) . . ?
O5 C13 N11 124.03(12) . . ?
O5 C13 H13 118.0 . . ?
N11 C13 H13 118.0 . . ?
N11 C14 H14A 109.5 . . ?
N11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N11 C15 H15A 109.5 . . ?
N11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H6A O6 H6B 111(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10B N1 C2 C3 -0.62(18) . . . . ?
C10B N1 C2 C11 179.32(10) . . . . ?
N1 C2 C3 C4 1.07(19) . . . . ?
C11 C2 C3 C4 -178.87(11) . . . . ?
C2 C3 C4 C4A 0.11(18) . . . . ?
C2 C3 C4 Cl1 179.96(9) . . . . ?
C3 C4 C4A C10B -1.55(17) . . . . ?
Cl1 C4 C4A C10B 178.60(9) . . . . ?
C3 C4 C4A C5 177.99(11) . . . . ?
Cl1 C4 C4A C5 -1.87(17) . . . . ?
C4 C4A C5 C6 179.81(12) . . . . ?
C10B C4A C5 C6 -0.68(19) . . . . ?
C4A C5 C6 C6A -0.8(2) . . . . ?
C5 C6 C6A C7 -179.23(12) . . . . ?
C5 C6 C6A C10A 0.68(19) . . . . ?
C10A C6A C7 C8 -0.68(18) . . . . ?
C6 C6A C7 C8 179.22(12) . . . . ?
C10A C6A C7 Cl2 179.48(9) . . . . ?
C6 C6A C7 Cl2 -0.61(17) . . . . ?
C6A C7 C8 C9 -0.31(19) . . . . ?
Cl2 C7 C8 C9 179.53(9) . . . . ?
C7 C8 C9 N10 1.03(19) . . . . ?
C7 C8 C9 C12 -176.74(11) . . . . ?
C8 C9 N10 C10A -0.64(18) . . . . ?
C12 C9 N10 C10A 177.11(10) . . . . ?
C9 N10 C10A C6A -0.49(17) . . . . ?
C9 N10 C10A C10B 179.80(11) . . . . ?
C7 C6A C10A N10 1.12(18) . . . . ?
C6 C6A C10A N10 -178.79(11) . . . . ?
C7 C6A C10A C10B -179.16(11) . . . . ?
C6 C6A C10A C10B 0.93(17) . . . . ?
C2 N1 C10B C4A -1.02(18) . . . . ?
C2 N1 C10B C10A 179.24(11) . . . . ?
C4 C4A C10B N1 2.06(17) . . . . ?
C5 C4A C10B N1 -177.49(11) . . . . ?
C4 C4A C10B C10A -178.19(10) . . . . ?
C5 C4A C10B C10A 2.26(17) . . . . ?
N10 C10A C10B N1 -2.87(17) . . . . ?
C6A C10A C10B N1 177.40(10) . . . . ?
N10 C10A C10B C4A 177.37(10) . . . . ?
C6A C10A C10B C4A -2.35(17) . . . . ?
N1 C2 C11 O1 -4.26(18) . . . . ?
C3 C2 C11 O1 175.68(12) . . . . ?
N1 C2 C11 O2 176.00(11) . . . . ?
C3 C2 C11 O2 -4.06(17) . . . . ?
N10 C9 C12 O3 -170.34(12) . . . . ?
C8 C9 C12 O3 7.57(18) . . . . ?
N10 C9 C12 O4 8.52(16) . . . . ?
C8 C9 C12 O4 -173.57(11) . . . . ?
C14 N11 C13 O5 -0.4(2) . . . . ?
C15 N11 C13 O5 -177.43(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O5 0.92(2) 1.59(2) 2.5086(15) 175.6(19) 1_565
O4 H4 O6 0.91(2) 1.59(2) 2.4919(15) 171.4(19) .
C13 H13 O1 0.95 2.33 3.0445(18) 131.2 1_545
C15 H15A O3 0.98 2.34 3.298(2) 165.4 2_656
O6 H6A O1 0.89(2) 1.81(2) 2.6964(18) 172(2) 2_666
O6 H6B O4 0.88(2) 2.30(2) 2.7802(17) 113.9(17) 2_666
O6 H6B N10 0.88(2) 2.15(2) 3.0316(17) 172(2) 2_666

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1988714'
loop_
_audit_author_name
_audit_author_address
'Alexandr Yatsenko'
;Moscow State University
Russia
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;

####################################################################

# start Validation Reply Form
_vrf_PLAT029_3a                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.972 Why?
RESPONSE: Some reflectance positions were hindered by the goniometer
details. Since the crystal belongs to P-1 space group, it was
impossible to use equivalent reflections instead.
;
_vrf_PLAT241_3a                  
;
PROBLEM: High MainMol Ueq as Compared to Neighbors of C12 Check
RESPONSE: Both pyrrolidine rings are involved in strong thermal
motion and one of them is disordered
;
# end Validation Reply Form 

####################################################################

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
1,10-phenantroline-4,7-dichloro-2,9-diylbis(pirrolidin-1-yl-methanone)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 Cl2 N4 O2'
_chemical_formula_sum            'C22 H20 Cl2 N4 O2'
_chemical_formula_weight         443.32

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'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.7488(3)
_cell_length_b                   10.1002(4)
_cell_length_c                   13.5780(5)
_cell_angle_alpha                79.974(3)
_cell_angle_beta                 76.276(3)
_cell_angle_gamma                83.821(3)
_cell_volume                     1014.12(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5958
_cell_measurement_theta_min      4.46
_cell_measurement_theta_max      69.24

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    3.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      '1146 frames, detector distance 42 mm'
_diffrn_reflns_number            8085
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.456
_diffrn_reflns_theta_max         67.977
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3593
_reflns_number_gt                2581
_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       'STOE X-AREA (Stoe & Cie, 2012)'
_computing_cell_refinement       'STOE X-AREA (Stoe & Cie, 2012)'
_computing_data_reduction        'STOE X-AREA (Stoe & Cie, 2012)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0783P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3593
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.10254(10) 0.90261(7) 0.59335(6) 0.0699(2) Uani 1 1 d . . . . .
Cl2 Cl 0.30763(9) 0.21091(7) 0.44355(5) 0.0605(2) Uani 1 1 d . . . . .
N1 N 0.4006(2) 0.57067(19) 0.76796(14) 0.0413(4) Uani 1 1 d . . . . .
N2 N 0.5645(3) 0.6753(2) 0.91141(15) 0.0496(5) Uani 1 1 d . . . . .
N10 N 0.4822(2) 0.32323(19) 0.71116(15) 0.0432(4) Uani 1 1 d . . . . .
N11 N 0.7470(3) 0.1310(2) 0.78510(17) 0.0545(5) Uani 1 1 d . . . . .
O1 O 0.2842(3) 0.7632(3) 0.95546(16) 0.0821(7) Uani 1 1 d . . . . .
O2 O 0.5727(3) -0.0203(2) 0.7639(2) 0.0872(7) Uani 1 1 d . . . . .
C2 C 0.3620(3) 0.6913(2) 0.79555(18) 0.0434(5) Uani 1 1 d . . . . .
C3 C 0.2687(3) 0.7969(3) 0.74367(19) 0.0477(6) Uani 1 1 d . . . . .
H3 H 0.245120 0.880686 0.765410 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2140(3) 0.7732(2) 0.66090(19) 0.0463(6) Uani 1 1 d . . . . .
C4A C 0.2465(3) 0.6453(2) 0.62865(18) 0.0419(5) Uani 1 1 d . . . . .
C5 C 0.1913(3) 0.6120(3) 0.54406(19) 0.0483(6) Uani 1 1 d . . . . .
H5 H 0.126239 0.676732 0.507286 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2308(3) 0.4888(3) 0.51577(18) 0.0467(6) Uani 1 1 d . . . . .
H6 H 0.193890 0.470333 0.459536 0.056 Uiso 1 1 calc R U . . .
C6A C 0.3288(3) 0.3864(2) 0.57104(17) 0.0413(5) Uani 1 1 d . . . . .
C7 C 0.3725(3) 0.2557(3) 0.54634(19) 0.0459(6) Uani 1 1 d . . . . .
C8 C 0.4656(3) 0.1617(3) 0.60311(19) 0.0484(6) Uani 1 1 d . . . . .
H8 H 0.491968 0.074319 0.588264 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5194(3) 0.2016(2) 0.68407(19) 0.0453(5) Uani 1 1 d . . . . .
C10A C 0.3866(3) 0.4141(2) 0.65544(17) 0.0393(5) Uani 1 1 d . . . . .
C10B C 0.3440(3) 0.5471(2) 0.68608(16) 0.0387(5) Uani 1 1 d . . . . .
C1 C 0.4036(3) 0.7132(3) 0.89398(19) 0.0492(6) Uani 1 1 d . . . . .
C10 C 0.6169(4) 0.0955(3) 0.7482(2) 0.0538(6) Uani 1 1 d . . . . .
C11 C 0.7239(3) 0.6334(3) 0.8376(2) 0.0614(7) Uani 1 1 d . . . . .
H11A H 0.763557 0.707763 0.784029 0.074 Uiso 1 1 calc R U . . .
H11B H 0.701529 0.559368 0.806452 0.074 Uiso 1 1 calc R U . . .
C12 C 0.8571(5) 0.5904(5) 0.9021(3) 0.0937(12) Uani 1 1 d . . . . .
H12A H 0.861044 0.493485 0.922795 0.112 Uiso 1 1 calc R U . . .
H12B H 0.974583 0.614851 0.863522 0.112 Uiso 1 1 calc R U . . .
C13 C 0.8041(5) 0.6577(4) 0.9915(3) 0.0901(11) Uani 1 1 d . . . . .
H13A H 0.867519 0.738604 0.980684 0.108 Uiso 1 1 calc R U . . .
H13B H 0.831298 0.598684 1.051170 0.108 Uiso 1 1 calc R U . . .
C14 C 0.6068(4) 0.6932(3) 1.0080(2) 0.0678(8) Uani 1 1 d . . . . .
H14A H 0.541823 0.633615 1.065482 0.081 Uiso 1 1 calc R U . . .
H14B H 0.578185 0.785589 1.020448 0.081 Uiso 1 1 calc R U . . .
C17 C 0.8400(4) 0.0302(3) 0.8502(3) 0.0704(8) Uani 1 1 d . . . . .
H17A H 0.884052 -0.048280 0.816942 0.085 Uiso 1 1 calc R U . . .
H17B H 0.761333 0.001743 0.915884 0.085 Uiso 1 1 calc R U . . .
C18 C 0.9914(5) 0.1015(4) 0.8636(4) 0.0916(12) Uani 1 1 d . . . . .
H181 H 1.103861 0.062375 0.828006 0.110 Uiso 0.29(2) 1 calc R U P A 1
H182 H 0.992230 0.091950 0.935774 0.110 Uiso 0.29(2) 1 calc R U P A 1
H183 H 0.963376 0.131743 0.929894 0.110 Uiso 0.71(2) 1 calc R U P A 2
H184 H 1.099351 0.042283 0.858226 0.110 Uiso 0.71(2) 1 calc R U P A 2
C191 C 0.966(3) 0.259(2) 0.8171(15) 0.061(4) Uani 0.29(2) 1 d . . P A 1
H191 H 0.926613 0.313677 0.871176 0.073 Uiso 0.29(2) 1 calc R U P A 1
H192 H 1.075423 0.290853 0.772319 0.073 Uiso 0.29(2) 1 calc R U P A 1
C192 C 1.0121(10) 0.2111(12) 0.7844(8) 0.075(2) Uani 0.71(2) 1 d . . P A 2
H193 H 1.093272 0.184720 0.723668 0.090 Uiso 0.71(2) 1 calc R U P A 2
H194 H 1.061627 0.283551 0.804835 0.090 Uiso 0.71(2) 1 calc R U P A 2
C20 C 0.8315(4) 0.2587(3) 0.7610(3) 0.0675(8) Uani 1 1 d . . . . .
H201 H 0.884361 0.275805 0.688116 0.081 Uiso 0.29(2) 1 calc R U P A 1
H202 H 0.741578 0.331131 0.776959 0.081 Uiso 0.29(2) 1 calc R U P A 1
H203 H 0.767898 0.323001 0.804605 0.081 Uiso 0.71(2) 1 calc R U P A 2
H204 H 0.841740 0.298174 0.689617 0.081 Uiso 0.71(2) 1 calc R U P A 2


_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 C4 1.735(2) . ?
Cl2 C7 1.734(2) . ?
N1 C2 1.319(3) . ?
N1 C10B 1.353(3) . ?
N2 C1 1.328(3) . ?
N2 C11 1.468(3) . ?
N2 C14 1.469(3) . ?
N10 C9 1.326(3) . ?
N10 C10A 1.357(3) . ?
N11 C10 1.332(3) . ?
N11 C20 1.461(4) . ?
N11 C17 1.473(3) . ?
O1 C1 1.220(3) . ?
O2 C10 1.223(3) . ?
C2 C3 1.404(3) . ?
C2 C1 1.504(3) . ?
C3 C4 1.357(3) . ?
C3 H3 0.9300 . ?
C4 C4A 1.414(3) . ?
C4A C10B 1.418(3) . ?
C4A C5 1.419(3) . ?
C5 C6 1.349(4) . ?
C5 H5 0.9300 . ?
C6 C6A 1.429(3) . ?
C6 H6 0.9300 . ?
C6A C7 1.404(3) . ?
C6A C10A 1.405(3) . ?
C7 C8 1.370(4) . ?
C8 C9 1.397(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.513(3) . ?
C10A C10B 1.456(3) . ?
C11 C12 1.490(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.448(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.505(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C17 C18 1.502(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C192 1.396(8) . ?
C18 C191 1.61(2) . ?
C18 H181 0.9700 . ?
C18 H182 0.9700 . ?
C18 H183 0.9700 . ?
C18 H184 0.9700 . ?
C191 C20 1.428(14) . ?
C191 H191 0.9700 . ?
C191 H192 0.9700 . ?
C192 C20 1.518(8) . ?
C192 H193 0.9700 . ?
C192 H194 0.9700 . ?
C20 H201 0.9700 . ?
C20 H202 0.9700 . ?
C20 H203 0.9700 . ?
C20 H204 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C10B 117.96(19) . . ?
C1 N2 C11 127.2(2) . . ?
C1 N2 C14 120.4(2) . . ?
C11 N2 C14 111.7(2) . . ?
C9 N10 C10A 117.1(2) . . ?
C10 N11 C20 128.7(2) . . ?
C10 N11 C17 120.1(2) . . ?
C20 N11 C17 110.8(2) . . ?
N1 C2 C3 123.7(2) . . ?
N1 C2 C1 118.3(2) . . ?
C3 C2 C1 117.7(2) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C4A 121.2(2) . . ?
C3 C4 Cl1 119.30(19) . . ?
C4A C4 Cl1 119.48(18) . . ?
C4 C4A C10B 115.6(2) . . ?
C4 C4A C5 124.6(2) . . ?
C10B C4A C5 119.8(2) . . ?
C6 C5 C4A 121.5(2) . . ?
C6 C5 H5 119.2 . . ?
C4A C5 H5 119.2 . . ?
C5 C6 C6A 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C6A C6 H6 119.6 . . ?
C7 C6A C10A 116.4(2) . . ?
C7 C6A C6 123.7(2) . . ?
C10A C6A C6 119.9(2) . . ?
C8 C7 C6A 120.8(2) . . ?
C8 C7 Cl2 119.02(19) . . ?
C6A C7 Cl2 120.19(19) . . ?
C7 C8 C9 117.7(2) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
N10 C9 C8 124.3(2) . . ?
N10 C9 C10 118.5(2) . . ?
C8 C9 C10 117.2(2) . . ?
N10 C10A C6A 123.6(2) . . ?
N10 C10A C10B 117.06(19) . . ?
C6A C10A C10B 119.3(2) . . ?
N1 C10B C4A 123.4(2) . . ?
N1 C10B C10A 118.02(19) . . ?
C4A C10B C10A 118.6(2) . . ?
O1 C1 N2 123.1(2) . . ?
O1 C1 C2 117.4(2) . . ?
N2 C1 C2 119.5(2) . . ?
O2 C10 N11 122.5(2) . . ?
O2 C10 C9 118.2(2) . . ?
N11 C10 C9 119.3(2) . . ?
N2 C11 C12 103.2(2) . . ?
N2 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
N2 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C13 C12 C11 107.9(3) . . ?
C13 C12 H12A 110.1 . . ?
C11 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C11 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 C14 107.5(2) . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
N2 C14 C13 103.9(3) . . ?
N2 C14 H14A 111.0 . . ?
C13 C14 H14A 111.0 . . ?
N2 C14 H14B 111.0 . . ?
C13 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
N11 C17 C18 104.6(3) . . ?
N11 C17 H17A 110.8 . . ?
C18 C17 H17A 110.8 . . ?
N11 C17 H17B 110.8 . . ?
C18 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C192 C18 C17 105.2(4) . . ?
C17 C18 C191 108.5(6) . . ?
C17 C18 H181 110.0 . . ?
C191 C18 H181 110.0 . . ?
C17 C18 H182 110.0 . . ?
C191 C18 H182 110.0 . . ?
H181 C18 H182 108.4 . . ?
C192 C18 H183 110.7 . . ?
C17 C18 H183 110.7 . . ?
C192 C18 H184 110.7 . . ?
C17 C18 H184 110.7 . . ?
H183 C18 H184 108.8 . . ?
C20 C191 C18 102.3(11) . . ?
C20 C191 H191 111.3 . . ?
C18 C191 H191 111.3 . . ?
C20 C191 H192 111.3 . . ?
C18 C191 H192 111.3 . . ?
H191 C191 H192 109.2 . . ?
C18 C192 C20 108.8(5) . . ?
C18 C192 H193 109.9 . . ?
C20 C192 H193 109.9 . . ?
C18 C192 H194 109.9 . . ?
C20 C192 H194 109.9 . . ?
H193 C192 H194 108.3 . . ?
C191 C20 N11 112.1(8) . . ?
N11 C20 C192 100.2(4) . . ?
C191 C20 H201 109.2 . . ?
N11 C20 H201 109.2 . . ?
C191 C20 H202 109.2 . . ?
N11 C20 H202 109.2 . . ?
H201 C20 H202 107.9 . . ?
N11 C20 H203 111.7 . . ?
C192 C20 H203 111.7 . . ?
N11 C20 H204 111.7 . . ?
C192 C20 H204 111.7 . . ?
H203 C20 H204 109.5 . . ?

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_ligand
_database_code_depnum_ccdc_archive 'CCDC 1983770'
loop_
_audit_author_name
_audit_author_address
'Alexandr Yatsenko'
;Moscow State University
Russia
;
_audit_update_record             
;
2020-02-13 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;

####################################################################

# start Validation Reply Form
_vrf_PLAT230_ligand              
;
PROBLEM: Hirshfeld Test Diff for N2 --C15 . 11.0 s.u.
RESPONSE: All C atoms of two piperidine have large displacement
parameters. This may indicate some kind of disorder, but these 
atoms do not split, and the C-C distances are of normal value.
The same is valid for other N-C bond lengths.
;
_vrf_PLAT306_ligand              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O3 Check
RESPONSE: The structure contains disordered water molecule, and
we failed to locate the H atoms.
;
_vrf_PLAT041_ligand              
;
PROBLEM: Calc. and Reported SumFormula Strings Differ Please Check
RESPONSE: Because we failed to locate two H atoms of a disordered
water molecule
;
_vrf_PLAT043_ligand              
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 2.02 Check
RESPONSE: Because we failed to locate two H atoms of a disordered
water molecule
;
_vrf_PLAT068_ligand              
;
PROBLEM: Reported F000 Differs from Calcd (or Missing)... Please Check
RESPONSE: Because we failed to locate two H atoms of a disordered
water molecule
;
_vrf_PLAT260_ligand              
;
PROBLEM: Large Average Ueq of Residue Including O3 0.161 Check
RESPONSE: This is a disordered water molecule
;
_vrf_PLAT369_ligand              
;
PROBLEM: Long C(sp2)-C(sp2) Bond C9 - C10 . 1.53 Ang.
RESPONSE: In the absence of pi-pi conjugation, this bond is not
extremely long.
;

# end Validation Reply Form

####################################################################


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
1,10-phenantroline-4,7-dichloro-2,9-diylbis(piperidin-1-yl-methanone)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 Cl2 N4 O2, H2 O'
_chemical_formula_sum            'C24 H26 Cl2 N4 O3'
_chemical_formula_weight         489.39

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'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.3267(15)
_cell_length_b                   6.8415(2)
_cell_length_c                   22.1880(11)
_cell_angle_alpha                90
_cell_angle_beta                 122.928(3)
_cell_angle_gamma                90
_cell_volume                     4628.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    3438
_cell_measurement_theta_min      4.75
_cell_measurement_theta_max      65.15

_exptl_crystal_description       'platelike fragment'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             2048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.810
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      '1658 frames, detector distance 42 mm'
_diffrn_reflns_number            26181
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.998
_diffrn_reflns_theta_max         67.731
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4179
_reflns_number_gt                2196
_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       'STOE X-AREA (Stoe & Cie, 2012)'
_computing_cell_refinement       'STOE X-AREA (Stoe & Cie, 2012)'
_computing_data_reduction        'STOE X-AREA (Stoe & Cie, 2012)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0225P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4179
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0591
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_restrained_S_all      0.846
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.18627(2) 0.55958(11) 0.38512(4) 0.0670(2) Uani 1 1 d . . . . .
Cl2 Cl 0.22201(2) 0.57504(9) 0.08142(3) 0.05249(17) Uani 1 1 d . . . . .
O1 O 0.35201(5) 0.4399(3) 0.59385(9) 0.0635(5) Uani 1 1 d . . . . .
O2 O 0.39435(6) 0.3082(3) 0.28182(11) 0.0782(6) Uani 1 1 d . . . . .
O3 O 0.40127(9) 0.3332(5) 0.44530(16) 0.1613(13) Uani 1 1 d . . . . .
N1 N 0.32156(5) 0.5624(3) 0.42347(10) 0.0415(4) Uani 1 1 d . . . . .
N10 N 0.33397(6) 0.5415(3) 0.31380(9) 0.0406(5) Uani 1 1 d . . . . .
N2 N 0.38949(7) 0.6663(3) 0.57345(10) 0.0550(5) Uani 1 1 d . . . . .
N11 N 0.41575(6) 0.6245(3) 0.30129(11) 0.0565(6) Uani 1 1 d . . . . .
C2 C 0.31550(7) 0.5658(3) 0.47703(11) 0.0395(5) Uani 1 1 d . . . . .
C3 C 0.27399(7) 0.5624(3) 0.46680(12) 0.0452(6) Uani 1 1 d . . . . .
H3 H 0.271248 0.558893 0.506098 0.054 Uiso 1 1 calc R U . . .
C4 C 0.23817(7) 0.5642(3) 0.39994(13) 0.0450(6) Uani 1 1 d . . . . .
C4A C 0.24219(7) 0.5677(3) 0.33971(12) 0.0384(5) Uani 1 1 d . . . . .
C5 C 0.20586(7) 0.5764(3) 0.26624(13) 0.0446(6) Uani 1 1 d . . . . .
H5 H 0.177447 0.581981 0.256099 0.053 Uiso 1 1 calc R U . . .
C6 C 0.21221(7) 0.5767(3) 0.21142(13) 0.0432(6) Uani 1 1 d . . . . .
H6 H 0.188194 0.583356 0.164287 0.052 Uiso 1 1 calc R U . . .
C6A C 0.25582(7) 0.5669(3) 0.22560(11) 0.0372(5) Uani 1 1 d . . . . .
C7 C 0.26439(7) 0.5648(3) 0.17046(11) 0.0396(5) Uani 1 1 d . . . . .
C8 C 0.30660(7) 0.5485(3) 0.18775(12) 0.0433(6) Uani 1 1 d . . . . .
H8 H 0.312809 0.546386 0.152249 0.052 Uiso 1 1 calc R U . . .
C9 C 0.33995(7) 0.5352(3) 0.26000(13) 0.0423(6) Uani 1 1 d . . . . .
C10A C 0.29209(7) 0.5589(3) 0.29674(11) 0.0377(5) Uani 1 1 d . . . . .
C10B C 0.28566(7) 0.5628(3) 0.35610(12) 0.0373(5) Uani 1 1 d . . . . .
C1 C 0.35407(8) 0.5553(4) 0.55237(12) 0.0466(6) Uani 1 1 d . . . . .
C11 C 0.39365(9) 0.8236(4) 0.53256(14) 0.0649(8) Uani 1 1 d . . . . .
H111 H 0.367171 0.829155 0.484828 0.078 Uiso 1 1 calc R U . . .
H112 H 0.418003 0.794875 0.527525 0.078 Uiso 1 1 calc R U . . .
C12 C 0.40110(10) 1.0199(5) 0.56856(15) 0.0818(10) Uani 1 1 d . . . . .
H121 H 0.406262 1.117839 0.542349 0.098 Uiso 1 1 calc R U . . .
H122 H 0.375114 1.057522 0.567839 0.098 Uiso 1 1 calc R U . . .
C13 C 0.43992(11) 1.0116(5) 0.64513(16) 0.0945(11) Uani 1 1 d . . . . .
H131 H 0.442583 1.134963 0.668715 0.113 Uiso 1 1 calc R U . . .
H132 H 0.466501 0.991719 0.645561 0.113 Uiso 1 1 calc R U . . .
C14 C 0.43486(9) 0.8469(5) 0.68596(14) 0.0761(9) Uani 1 1 d . . . . .
H141 H 0.410376 0.874937 0.690703 0.091 Uiso 1 1 calc R U . . .
H142 H 0.461169 0.837884 0.733803 0.091 Uiso 1 1 calc R U . . .
C15 C 0.42699(9) 0.6515(4) 0.64696(14) 0.0675(8) Uani 1 1 d . . . . .
H151 H 0.452852 0.615870 0.647017 0.081 Uiso 1 1 calc R U . . .
H152 H 0.421716 0.550115 0.671938 0.081 Uiso 1 1 calc R U . . .
C10 C 0.38645(8) 0.4818(4) 0.28205(12) 0.0442(6) Uani 1 1 d . . . . .
C17 C 0.46174(8) 0.5771(5) 0.33125(14) 0.0704(8) Uani 1 1 d . . . . .
H171 H 0.472921 0.658752 0.308930 0.085 Uiso 1 1 calc R U . . .
H172 H 0.464148 0.441805 0.320771 0.085 Uiso 1 1 calc R U . . .
C18 C 0.48841(10) 0.6081(5) 0.41004(17) 0.0955(11) Uani 1 1 d . . . . .
H181 H 0.519050 0.584696 0.428068 0.115 Uiso 1 1 calc R U . . .
H182 H 0.479534 0.515039 0.432778 0.115 Uiso 1 1 calc R U . . .
C19 C 0.48326(11) 0.8106(6) 0.42944(19) 0.1072(12) Uani 1 1 d . . . . .
H191 H 0.496356 0.902576 0.413124 0.129 Uiso 1 1 calc R U . . .
H192 H 0.498677 0.821422 0.481257 0.129 Uiso 1 1 calc R U . . .
C20 C 0.43547(12) 0.8625(5) 0.3961(2) 0.1009(12) Uani 1 1 d . . . . .
H201 H 0.423565 0.785455 0.418402 0.121 Uiso 1 1 calc R U . . .
H202 H 0.433019 0.999469 0.404775 0.121 Uiso 1 1 calc R U . . .
C21 C 0.40944(10) 0.8239(4) 0.3163(2) 0.0841(10) Uani 1 1 d . . . . .
H211 H 0.378544 0.846234 0.296599 0.101 Uiso 1 1 calc R U . . .
H212 H 0.418656 0.913961 0.293156 0.101 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.729(2) . ?
Cl2 C7 1.724(2) . ?
O1 C1 1.245(3) . ?
O2 C10 1.222(3) . ?
N1 C2 1.321(3) . ?
N1 C10B 1.348(3) . ?
N10 C9 1.325(3) . ?
N10 C10A 1.359(3) . ?
N2 C1 1.341(3) . ?
N2 C15 1.453(3) . ?
N2 C11 1.468(3) . ?
N11 C10 1.332(3) . ?
N11 C21 1.452(3) . ?
N11 C17 1.460(3) . ?
C2 C3 1.398(3) . ?
C2 C1 1.489(3) . ?
C3 C4 1.340(3) . ?
C3 H3 0.9300 . ?
C4 C4A 1.421(3) . ?
C4A C10B 1.415(3) . ?
C4A C5 1.436(3) . ?
C5 C6 1.356(3) . ?
C5 H5 0.9300 . ?
C6 C6A 1.439(3) . ?
C6 H6 0.9300 . ?
C6A C10A 1.403(3) . ?
C6A C7 1.417(3) . ?
C7 C8 1.368(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.526(3) . ?
C10A C10B 1.458(3) . ?
C11 C12 1.510(4) . ?
C11 H111 0.9700 . ?
C11 H112 0.9700 . ?
C12 C13 1.508(4) . ?
C12 H121 0.9700 . ?
C12 H122 0.9700 . ?
C13 C14 1.518(4) . ?
C13 H131 0.9700 . ?
C13 H132 0.9700 . ?
C14 C15 1.532(4) . ?
C14 H141 0.9700 . ?
C14 H142 0.9700 . ?
C15 H151 0.9700 . ?
C15 H152 0.9700 . ?
C17 C18 1.483(4) . ?
C17 H171 0.9700 . ?
C17 H172 0.9700 . ?
C18 C19 1.492(4) . ?
C18 H181 0.9700 . ?
C18 H182 0.9700 . ?
C19 C20 1.514(5) . ?
C19 H191 0.9700 . ?
C19 H192 0.9700 . ?
C20 C21 1.511(4) . ?
C20 H201 0.9700 . ?
C20 H202 0.9700 . ?
C21 H211 0.9700 . ?
C21 H212 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C10B 117.61(18) . . ?
C9 N10 C10A 117.32(18) . . ?
C1 N2 C15 119.3(2) . . ?
C1 N2 C11 127.0(2) . . ?
C15 N2 C11 113.3(2) . . ?
C10 N11 C21 124.3(2) . . ?
C10 N11 C17 120.0(2) . . ?
C21 N11 C17 112.9(2) . . ?
N1 C2 C3 123.1(2) . . ?
N1 C2 C1 119.58(19) . . ?
C3 C2 C1 117.1(2) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C4A 120.5(2) . . ?
C3 C4 Cl1 120.82(18) . . ?
C4A C4 Cl1 118.69(18) . . ?
C10B C4A C4 115.4(2) . . ?
C10B C4A C5 120.1(2) . . ?
C4 C4A C5 124.6(2) . . ?
C6 C5 C4A 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C4A C5 H5 119.4 . . ?
C5 C6 C6A 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C6A C6 H6 119.7 . . ?
C10A C6A C7 117.26(19) . . ?
C10A C6A C6 119.8(2) . . ?
C7 C6A C6 123.0(2) . . ?
C8 C7 C6A 119.8(2) . . ?
C8 C7 Cl2 119.43(17) . . ?
C6A C7 Cl2 120.70(17) . . ?
C7 C8 C9 118.0(2) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
N10 C9 C8 124.7(2) . . ?
N10 C9 C10 114.5(2) . . ?
C8 C9 C10 120.3(2) . . ?
N10 C10A C6A 122.8(2) . . ?
N10 C10A C10B 117.07(19) . . ?
C6A C10A C10B 120.14(19) . . ?
N1 C10B C4A 123.9(2) . . ?
N1 C10B C10A 117.93(18) . . ?
C4A C10B C10A 118.21(19) . . ?
O1 C1 N2 122.2(2) . . ?
O1 C1 C2 117.5(2) . . ?
N2 C1 C2 120.2(2) . . ?
N2 C11 C12 112.0(2) . . ?
N2 C11 H111 109.2 . . ?
C12 C11 H111 109.2 . . ?
N2 C11 H112 109.2 . . ?
C12 C11 H112 109.2 . . ?
H111 C11 H112 107.9 . . ?
C13 C12 C11 110.6(3) . . ?
C13 C12 H121 109.5 . . ?
C11 C12 H121 109.5 . . ?
C13 C12 H122 109.5 . . ?
C11 C12 H122 109.5 . . ?
H121 C12 H122 108.1 . . ?
C12 C13 C14 111.0(2) . . ?
C12 C13 H131 109.4 . . ?
C14 C13 H131 109.4 . . ?
C12 C13 H132 109.4 . . ?
C14 C13 H132 109.4 . . ?
H131 C13 H132 108.0 . . ?
C13 C14 C15 110.9(2) . . ?
C13 C14 H141 109.5 . . ?
C15 C14 H141 109.5 . . ?
C13 C14 H142 109.5 . . ?
C15 C14 H142 109.5 . . ?
H141 C14 H142 108.1 . . ?
N2 C15 C14 110.3(2) . . ?
N2 C15 H151 109.6 . . ?
C14 C15 H151 109.6 . . ?
N2 C15 H152 109.6 . . ?
C14 C15 H152 109.6 . . ?
H151 C15 H152 108.1 . . ?
O2 C10 N11 124.4(2) . . ?
O2 C10 C9 116.9(2) . . ?
N11 C10 C9 118.7(2) . . ?
N11 C17 C18 111.0(2) . . ?
N11 C17 H171 109.4 . . ?
C18 C17 H171 109.4 . . ?
N11 C17 H172 109.4 . . ?
C18 C17 H172 109.4 . . ?
H171 C17 H172 108.0 . . ?
C17 C18 C19 111.7(3) . . ?
C17 C18 H181 109.3 . . ?
C19 C18 H181 109.3 . . ?
C17 C18 H182 109.3 . . ?
C19 C18 H182 109.3 . . ?
H181 C18 H182 108.0 . . ?
C18 C19 C20 111.6(3) . . ?
C18 C19 H191 109.3 . . ?
C20 C19 H191 109.3 . . ?
C18 C19 H192 109.3 . . ?
C20 C19 H192 109.3 . . ?
H191 C19 H192 108.0 . . ?
C21 C20 C19 110.6(3) . . ?
C21 C20 H201 109.5 . . ?
C19 C20 H201 109.5 . . ?
C21 C20 H202 109.5 . . ?
C19 C20 H202 109.5 . . ?
H201 C20 H202 108.1 . . ?
N11 C21 C20 110.9(3) . . ?
N11 C21 H211 109.5 . . ?
C20 C21 H211 109.5 . . ?
N11 C21 H212 109.5 . . ?
C20 C21 H212 109.5 . . ?
H211 C21 H212 108.0 . . ?

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
C10B N1 C2 C3 2.4(3) . . . . ?
C10B N1 C2 C1 176.9(2) . . . . ?
N1 C2 C3 C4 -2.9(4) . . . . ?
C1 C2 C3 C4 -177.6(2) . . . . ?
C2 C3 C4 C4A 0.6(4) . . . . ?
C2 C3 C4 Cl1 179.86(18) . . . . ?
C3 C4 C4A C10B 1.9(3) . . . . ?
Cl1 C4 C4A C10B -177.38(17) . . . . ?
C3 C4 C4A C5 -177.8(2) . . . . ?
Cl1 C4 C4A C5 2.9(3) . . . . ?
C10B C4A C5 C6 1.2(3) . . . . ?
C4 C4A C5 C6 -179.1(2) . . . . ?
C4A C5 C6 C6A 0.4(3) . . . . ?
C5 C6 C6A C10A -0.6(3) . . . . ?
C5 C6 C6A C7 179.3(2) . . . . ?
C10A C6A C7 C8 2.2(3) . . . . ?
C6 C6A C7 C8 -177.8(2) . . . . ?
C10A C6A C7 Cl2 -179.75(17) . . . . ?
C6 C6A C7 Cl2 0.3(3) . . . . ?
C6A C7 C8 C9 -0.2(3) . . . . ?
Cl2 C7 C8 C9 -178.27(18) . . . . ?
C10A N10 C9 C8 1.2(3) . . . . ?
C10A N10 C9 C10 -170.32(19) . . . . ?
C7 C8 C9 N10 -1.6(4) . . . . ?
C7 C8 C9 C10 169.4(2) . . . . ?
C9 N10 C10A C6A 1.0(3) . . . . ?
C9 N10 C10A C10B 179.1(2) . . . . ?
C7 C6A C10A N10 -2.7(3) . . . . ?
C6 C6A C10A N10 177.26(19) . . . . ?
C7 C6A C10A C10B 179.34(19) . . . . ?
C6 C6A C10A C10B -0.7(3) . . . . ?
C2 N1 C10B C4A 0.4(3) . . . . ?
C2 N1 C10B C10A -179.9(2) . . . . ?
C4 C4A C10B N1 -2.5(3) . . . . ?
C5 C4A C10B N1 177.2(2) . . . . ?
C4 C4A C10B C10A 177.9(2) . . . . ?
C5 C4A C10B C10A -2.4(3) . . . . ?
N10 C10A C10B N1 4.5(3) . . . . ?
C6A C10A C10B N1 -177.5(2) . . . . ?
N10 C10A C10B C4A -175.87(19) . . . . ?
C6A C10A C10B C4A 2.2(3) . . . . ?
C15 N2 C1 O1 0.4(4) . . . . ?
C11 N2 C1 O1 -171.8(2) . . . . ?
C15 N2 C1 C2 -179.1(2) . . . . ?
C11 N2 C1 C2 8.7(4) . . . . ?
N1 C2 C1 O1 -133.6(2) . . . . ?
C3 C2 C1 O1 41.2(3) . . . . ?
N1 C2 C1 N2 45.9(3) . . . . ?
C3 C2 C1 N2 -139.3(2) . . . . ?
C1 N2 C11 C12 116.0(3) . . . . ?
C15 N2 C11 C12 -56.5(3) . . . . ?
N2 C11 C12 C13 54.2(3) . . . . ?
C11 C12 C13 C14 -53.9(4) . . . . ?
C12 C13 C14 C15 54.7(4) . . . . ?
C1 N2 C15 C14 -116.9(3) . . . . ?
C11 N2 C15 C14 56.3(3) . . . . ?
C13 C14 C15 N2 -55.1(3) . . . . ?
C21 N11 C10 O2 -166.3(3) . . . . ?
C17 N11 C10 O2 -6.5(4) . . . . ?
C21 N11 C10 C9 12.4(4) . . . . ?
C17 N11 C10 C9 172.3(2) . . . . ?
N10 C9 C10 O2 90.1(3) . . . . ?
C8 C9 C10 O2 -81.8(3) . . . . ?
N10 C9 C10 N11 -88.7(3) . . . . ?
C8 C9 C10 N11 99.3(3) . . . . ?
C10 N11 C17 C18 -104.3(3) . . . . ?
C21 N11 C17 C18 57.7(3) . . . . ?
N11 C17 C18 C19 -54.9(4) . . . . ?
C17 C18 C19 C20 53.2(4) . . . . ?
C18 C19 C20 C21 -52.2(4) . . . . ?
C10 N11 C21 C20 103.8(3) . . . . ?
C17 N11 C21 C20 -57.3(3) . . . . ?
C19 C20 C21 N11 53.8(4) . . . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_3f
_database_code_depnum_ccdc_archive 'CCDC 1938799'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2019-07-06 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H20 Cl2 N4 O2'
_chemical_formula_sum            'C30 H20 Cl2 N4 O2'
_chemical_formula_weight         539.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0047 0.0021 '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 0.0086 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0148 0.0078 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1748 0.1985 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.2410(14)
_cell_length_b                   11.680(2)
_cell_length_c                   14.506(3)
_cell_angle_alpha                103.259(14)
_cell_angle_beta                 95.030(2)
_cell_angle_gamma                97.662(18)
_cell_volume                     1174.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      26.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.420
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   'Scala (Evans, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.79272
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18379
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.621
_diffrn_reflns_theta_max         30.956
_diffrn_reflns_theta_full        28.401
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             5233
_reflns_number_gt                3967
_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL

_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)+(0.08P)²+0.8P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5233
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.84793(9) 0.17513(5) 0.45254(5) 0.02828(18) Uani 1 1 d . . . . .
Cl2 Cl 0.65716(9) 0.77922(6) 0.70184(5) 0.02887(18) Uani 1 1 d . . . . .
O1 O 1.0198(3) 0.33112(18) 0.13047(14) 0.0323(4) Uani 1 1 d . . . . .
O2 O 0.4792(3) 0.91344(17) 0.36992(14) 0.0300(4) Uani 1 1 d . . . . .
N1 N 0.7817(3) 0.46367(19) 0.29701(16) 0.0255(5) Uani 1 1 d . . . . .
N2 N 0.7145(3) 0.3479(2) 0.08920(17) 0.0285(5) Uani 1 1 d . . . . .
C1 C 0.8616(4) 0.3437(2) 0.15152(19) 0.0265(5) Uani 1 1 d . . . . .
C2 C 0.8271(3) 0.3601(2) 0.25459(19) 0.0258(5) Uani 1 1 d . . . . .
C3 C 0.8543(4) 0.2696(2) 0.30096(19) 0.0265(5) Uani 1 1 d . . . . .
H3 H 0.8894 0.1972 0.2679 0.032 Uiso 1 1 calc R U . . .
C4 C 0.8290(3) 0.2888(2) 0.39475(19) 0.0262(5) Uani 1 1 d . . . . .
C4A C 0.7872(3) 0.3989(2) 0.44587(19) 0.0240(5) Uani 1 1 d . . . . .
C5 C 0.7711(3) 0.4278(2) 0.54566(19) 0.0255(5) Uani 1 1 d . . . . .
H5 H 0.7867 0.3701 0.5812 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7339(3) 0.5365(2) 0.59084(19) 0.0258(5) Uani 1 1 d . . . . .
H6 H 0.7244 0.5540 0.6574 0.031 Uiso 1 1 calc R U . . .
C6A C 0.7090(3) 0.6245(2) 0.53852(18) 0.0245(5) Uani 1 1 d . . . . .
C7 C 0.6674(3) 0.7390(2) 0.58045(19) 0.0253(5) Uani 1 1 d . . . . .
C8 C 0.6371(3) 0.8185(2) 0.52642(19) 0.0256(5) Uani 1 1 d . . . . .
H8 H 0.6040 0.8939 0.5537 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6574(3) 0.7833(2) 0.42877(19) 0.0246(5) Uani 1 1 d . . . . .
N10 N 0.6993(3) 0.67894(19) 0.38591(16) 0.0249(4) Uani 1 1 d . . . . .
C10A C 0.7216(3) 0.5999(2) 0.43940(19) 0.0246(5) Uani 1 1 d . . . . .
C10B C 0.7652(3) 0.4835(2) 0.39139(19) 0.0247(5) Uani 1 1 d . . . . .
C10 C 0.6221(4) 0.8663(2) 0.36572(19) 0.0254(5) Uani 1 1 d . . . . .
N11 N 0.7509(3) 0.88145(19) 0.30554(16) 0.0255(5) Uani 1 1 d . . . . .
C11 C 0.5170(4) 0.3430(3) 0.1118(2) 0.0307(6) Uani 1 1 d . . . . .
H11A H 0.5016 0.4174 0.1573 0.037 Uiso 1 1 calc R U . . .
H11B H 0.4814 0.2750 0.1402 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3971(4) 0.3276(3) 0.0170(2) 0.0366(6) Uani 1 1 d . . . . .
H12A H 0.3204 0.2473 -0.0034 0.044 Uiso 1 1 calc R U . . .
H12B H 0.3126 0.3881 0.0215 0.044 Uiso 1 1 calc R U . . .
C12A C 0.5367(4) 0.3439(2) -0.0511(2) 0.0295(6) Uani 1 1 d . . . . .
C13 C 0.5087(4) 0.3531(2) -0.1444(2) 0.0334(6) Uani 1 1 d . . . . .
H13 H 0.3851 0.3476 -0.1748 0.040 Uiso 1 1 calc R U . . .
C14 C 0.6624(4) 0.3704(2) -0.1935(2) 0.0351(6) Uani 1 1 d . . . . .
H14 H 0.6441 0.3769 -0.2577 0.042 Uiso 1 1 calc R U . . .
C15 C 0.8424(4) 0.3780(2) -0.1488(2) 0.0334(6) Uani 1 1 d . . . . .
H15 H 0.9466 0.3913 -0.1826 0.040 Uiso 1 1 calc R U . . .
C16 C 0.8742(4) 0.3668(2) -0.0555(2) 0.0309(6) Uani 1 1 d . . . . .
H16 H 0.9976 0.3696 -0.0259 0.037 Uiso 1 1 calc R U . . .
C16A C 0.7194(4) 0.3513(2) -0.00750(19) 0.0271(5) Uani 1 1 d . . . . .
C17 C 0.9368(4) 0.8404(3) 0.3084(2) 0.0325(6) Uani 1 1 d . . . . .
H17A H 0.9237 0.7543 0.2777 0.039 Uiso 1 1 calc R U . . .
H17B H 0.9963 0.8551 0.3750 0.039 Uiso 1 1 calc R U . . .
C18 C 1.0530(4) 0.9148(2) 0.2526(2) 0.0303(6) Uani 1 1 d . . . . .
H18A H 1.1396 0.9818 0.2964 0.036 Uiso 1 1 calc R U . . .
H18B H 1.1265 0.8651 0.2098 0.036 Uiso 1 1 calc R U . . .
C18A C 0.9052(4) 0.9594(2) 0.19635(19) 0.0269(5) Uani 1 1 d . . . . .
C19 C 0.9212(4) 1.0137(2) 0.1216(2) 0.0295(6) Uani 1 1 d . . . . .
H19 H 1.0379 1.0258 0.0972 0.035 Uiso 1 1 calc R U . . .
C20 C 0.7629(4) 1.0504(2) 0.0827(2) 0.0312(6) Uani 1 1 d . . . . .
H20 H 0.7713 1.0876 0.0312 0.037 Uiso 1 1 calc R U . . .
C21 C 0.5934(4) 1.0328(2) 0.1189(2) 0.0301(6) Uani 1 1 d . . . . .
H21 H 0.4871 1.0585 0.0916 0.036 Uiso 1 1 calc R U . . .
C22 C 0.5750(4) 0.9786(2) 0.1939(2) 0.0280(5) Uani 1 1 d . . . . .
H22 H 0.4585 0.9673 0.2187 0.034 Uiso 1 1 calc R U . . .
C22A C 0.7334(4) 0.9414(2) 0.23168(19) 0.0256(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.738(3) . ?
Cl2 C7 1.726(3) . ?
O1 C1 1.230(3) . ?
O2 C10 1.235(3) . ?
N1 C2 1.323(3) . ?
N1 C10B 1.354(3) . ?
N2 C1 1.349(4) . ?
N2 C16A 1.416(4) . ?
N2 C11 1.492(3) . ?
C1 C2 1.510(4) . ?
C2 C3 1.402(4) . ?
C3 C4 1.360(4) . ?
C3 H3 0.9500 . ?
C4 C4A 1.415(3) . ?
C4A C10B 1.416(4) . ?
C4A C5 1.428(4) . ?
C5 C6 1.362(4) . ?
C5 H5 0.9500 . ?
C6 C6A 1.431(4) . ?
C6 H6 0.9500 . ?
C6A C10A 1.414(4) . ?
C6A C7 1.419(3) . ?
C7 C8 1.372(4) . ?
C8 C9 1.408(4) . ?
C8 H8 0.9500 . ?
C9 N10 1.322(3) . ?
C9 C10 1.508(4) . ?
N10 C10A 1.352(3) . ?
C10A C10B 1.466(3) . ?
C10 N11 1.354(3) . ?
N11 C22A 1.414(3) . ?
N11 C17 1.488(3) . ?
C11 C12 1.522(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C12A 1.498(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12A C13 1.381(4) . ?
C12A C16A 1.399(4) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 C16A 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.537(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C18A 1.508(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18A C19 1.381(4) . ?
C18A C22A 1.395(4) . ?
C19 C20 1.395(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 C22A 1.392(4) . ?
C22 H22 0.9500 . ?

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
C2 N1 C10B 117.4(2) . . ?
C1 N2 C16A 126.4(2) . . ?
C1 N2 C11 124.0(2) . . ?
C16A N2 C11 109.5(2) . . ?
O1 C1 N2 124.7(3) . . ?
O1 C1 C2 118.9(2) . . ?
N2 C1 C2 116.4(2) . . ?
N1 C2 C3 124.0(2) . . ?
N1 C2 C1 116.7(2) . . ?
C3 C2 C1 119.3(2) . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C4A 121.3(2) . . ?
C3 C4 Cl1 119.10(19) . . ?
C4A C4 Cl1 119.5(2) . . ?
C4 C4A C10B 115.3(2) . . ?
C4 C4A C5 124.3(2) . . ?
C10B C4A C5 120.5(2) . . ?
C6 C5 C4A 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4A C5 H5 119.4 . . ?
C5 C6 C6A 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
C6A C6 H6 119.9 . . ?
C10A C6A C7 115.9(2) . . ?
C10A C6A C6 120.7(2) . . ?
C7 C6A C6 123.4(2) . . ?
C8 C7 C6A 121.2(2) . . ?
C8 C7 Cl2 119.5(2) . . ?
C6A C7 Cl2 119.3(2) . . ?
C7 C8 C9 117.0(2) . . ?
C7 C8 H8 121.5 . . ?
C9 C8 H8 121.5 . . ?
N10 C9 C8 124.7(2) . . ?
N10 C9 C10 116.1(2) . . ?
C8 C9 C10 119.2(2) . . ?
C9 N10 C10A 117.6(2) . . ?
N10 C10A C6A 123.6(2) . . ?
N10 C10A C10B 117.5(2) . . ?
C6A C10A C10B 118.9(2) . . ?
N1 C10B C4A 123.9(2) . . ?
N1 C10B C10A 117.6(2) . . ?
C4A C10B C10A 118.5(2) . . ?
O2 C10 N11 124.3(2) . . ?
O2 C10 C9 119.4(2) . . ?
N11 C10 C9 116.3(2) . . ?
C10 N11 C22A 125.7(2) . . ?
C10 N11 C17 125.3(2) . . ?
C22A N11 C17 108.9(2) . . ?
N2 C11 C12 105.5(2) . . ?
N2 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
N2 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
C12A C12 C11 104.2(2) . . ?
C12A C12 H12A 110.9 . . ?
C11 C12 H12A 110.9 . . ?
C12A C12 H12B 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C13 C12A C16A 119.5(3) . . ?
C13 C12A C12 130.0(3) . . ?
C16A C12A C12 110.5(2) . . ?
C12A C13 C14 119.6(3) . . ?
C12A C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C16A C16 C15 117.5(3) . . ?
C16A C16 H16 121.2 . . ?
C15 C16 H16 121.2 . . ?
C16 C16A C12A 121.8(3) . . ?
C16 C16A N2 128.6(3) . . ?
C12A C16A N2 109.5(2) . . ?
N11 C17 C18 104.6(2) . . ?
N11 C17 H17A 110.8 . . ?
C18 C17 H17A 110.8 . . ?
N11 C17 H17B 110.8 . . ?
C18 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C18A C18 C17 103.0(2) . . ?
C18A C18 H18A 111.2 . . ?
C17 C18 H18A 111.2 . . ?
C18A C18 H18B 111.2 . . ?
C17 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
C19 C18A C22A 120.4(2) . . ?
C19 C18A C18 129.6(2) . . ?
C22A C18A C18 110.0(2) . . ?
C18A C19 C20 118.7(3) . . ?
C18A C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 121.7(3) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C22A 117.5(3) . . ?
C21 C22 H22 121.2 . . ?
C22A C22 H22 121.2 . . ?
C22 C22A C18A 121.3(2) . . ?
C22 C22A N11 128.8(2) . . ?
C18A C22A N11 109.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16A N2 C1 O1 -7.1(4) . . . . ?
C11 N2 C1 O1 169.5(2) . . . . ?
C16A N2 C1 C2 170.7(2) . . . . ?
C11 N2 C1 C2 -12.7(4) . . . . ?
C10B N1 C2 C3 1.6(4) . . . . ?
C10B N1 C2 C1 -174.8(2) . . . . ?
O1 C1 C2 N1 115.4(3) . . . . ?
N2 C1 C2 N1 -62.6(3) . . . . ?
O1 C1 C2 C3 -61.2(3) . . . . ?
N2 C1 C2 C3 120.9(3) . . . . ?
N1 C2 C3 C4 1.3(4) . . . . ?
C1 C2 C3 C4 177.6(2) . . . . ?
C2 C3 C4 C4A -3.6(4) . . . . ?
C2 C3 C4 Cl1 176.23(19) . . . . ?
C3 C4 C4A C10B 2.9(4) . . . . ?
Cl1 C4 C4A C10B -176.89(18) . . . . ?
C3 C4 C4A C5 -175.7(2) . . . . ?
Cl1 C4 C4A C5 4.5(4) . . . . ?
C4 C4A C5 C6 178.8(2) . . . . ?
C10B C4A C5 C6 0.2(4) . . . . ?
C4A C5 C6 C6A 0.3(4) . . . . ?
C5 C6 C6A C10A 0.3(4) . . . . ?
C5 C6 C6A C7 179.1(2) . . . . ?
C10A C6A C7 C8 1.6(4) . . . . ?
C6 C6A C7 C8 -177.3(2) . . . . ?
C10A C6A C7 Cl2 -177.78(18) . . . . ?
C6 C6A C7 Cl2 3.4(3) . . . . ?
C6A C7 C8 C9 -2.7(4) . . . . ?
Cl2 C7 C8 C9 176.63(19) . . . . ?
C7 C8 C9 N10 1.4(4) . . . . ?
C7 C8 C9 C10 178.9(2) . . . . ?
C8 C9 N10 C10A 1.1(4) . . . . ?
C10 C9 N10 C10A -176.4(2) . . . . ?
C9 N10 C10A C6A -2.3(4) . . . . ?
C9 N10 C10A C10B 179.1(2) . . . . ?
C7 C6A C10A N10 1.1(4) . . . . ?
C6 C6A C10A N10 179.9(2) . . . . ?
C7 C6A C10A C10B 179.6(2) . . . . ?
C6 C6A C10A C10B -1.5(4) . . . . ?
C2 N1 C10B C4A -2.3(4) . . . . ?
C2 N1 C10B C10A 177.8(2) . . . . ?
C4 C4A C10B N1 0.1(4) . . . . ?
C5 C4A C10B N1 178.8(2) . . . . ?
C4 C4A C10B C10A 180.0(2) . . . . ?
C5 C4A C10B C10A -1.3(4) . . . . ?
N10 C10A C10B N1 0.5(3) . . . . ?
C6A C10A C10B N1 -178.2(2) . . . . ?
N10 C10A C10B C4A -179.4(2) . . . . ?
C6A C10A C10B C4A 2.0(4) . . . . ?
N10 C9 C10 O2 130.1(3) . . . . ?
C8 C9 C10 O2 -47.5(4) . . . . ?
N10 C9 C10 N11 -48.2(3) . . . . ?
C8 C9 C10 N11 134.1(2) . . . . ?
O2 C10 N11 C22A -7.5(4) . . . . ?
C9 C10 N11 C22A 170.8(2) . . . . ?
O2 C10 N11 C17 170.7(3) . . . . ?
C9 C10 N11 C17 -11.1(4) . . . . ?
C1 N2 C11 C12 -170.0(2) . . . . ?
C16A N2 C11 C12 7.1(3) . . . . ?
N2 C11 C12 C12A -8.6(3) . . . . ?
C11 C12 C12A C13 -171.7(3) . . . . ?
C11 C12 C12A C16A 7.5(3) . . . . ?
C16A C12A C13 C14 -0.4(4) . . . . ?
C12 C12A C13 C14 178.8(3) . . . . ?
C12A C13 C14 C15 0.1(4) . . . . ?
C13 C14 C15 C16 1.1(4) . . . . ?
C14 C15 C16 C16A -2.0(4) . . . . ?
C15 C16 C16A C12A 1.7(4) . . . . ?
C15 C16 C16A N2 -174.1(2) . . . . ?
C13 C12A C16A C16 -0.6(4) . . . . ?
C12 C12A C16A C16 -179.9(2) . . . . ?
C13 C12A C16A N2 176.0(2) . . . . ?
C12 C12A C16A N2 -3.3(3) . . . . ?
C1 N2 C16A C16 -9.3(4) . . . . ?
C11 N2 C16A C16 173.7(3) . . . . ?
C1 N2 C16A C12A 174.5(2) . . . . ?
C11 N2 C16A C12A -2.5(3) . . . . ?
C10 N11 C17 C18 -160.7(2) . . . . ?
C22A N11 C17 C18 17.7(3) . . . . ?
N11 C17 C18 C18A -18.4(3) . . . . ?
C17 C18 C18A C19 -167.8(3) . . . . ?
C17 C18 C18A C22A 13.7(3) . . . . ?
C22A C18A C19 C20 0.2(4) . . . . ?
C18 C18A C19 C20 -178.1(3) . . . . ?
C18A C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C21 C22 C22A -0.4(4) . . . . ?
C21 C22 C22A C18A 0.9(4) . . . . ?
C21 C22 C22A N11 -178.0(2) . . . . ?
C19 C18A C22A C22 -0.8(4) . . . . ?
C18 C18A C22A C22 177.8(2) . . . . ?
C19 C18A C22A N11 178.2(2) . . . . ?
C18 C18A C22A N11 -3.1(3) . . . . ?
C10 N11 C22A C22 -12.2(4) . . . . ?
C17 N11 C22A C22 169.4(3) . . . . ?
C10 N11 C22A C18A 168.8(2) . . . . ?
C17 N11 C22A C18A -9.5(3) . . . . ?

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-4

