# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_l1
_database_code_depnum_ccdc_archive 'CCDC 2076146'
loop_
_audit_author_name
_audit_author_address
'Ksenia Isakovskaya'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-01-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N4 O2'
_chemical_formula_sum            'C22 H22 N4 O2'
_chemical_formula_weight         374.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5010(9)
_cell_length_b                   22.943(3)
_cell_length_c                   21.104(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.869(3)
_cell_angle_gamma                90
_cell_volume                     3627.3(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3828
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.14
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1242 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.8838.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            41677
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         1.775
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5714
_reflns_number_total             8741
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         8741
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+1.0941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1268
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C20-C21 \\sim C21'-C20'
 with sigma of 0.02
 C20-C19 \\sim C20'-C19
 with sigma of 0.02
 C21'-C22 \\sim C21-C22
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(C21') = Uanis(C21)
Uanis(C20') = Uanis(C20)
3. Others
 Sof(H19C)=Sof(H19D)=Sof(C20')=Sof(H20C)=Sof(H20D)=Sof(C21')=Sof(H21C)=
 Sof(H21D)=Sof(H22C)=Sof(H22D)=1-FVAR(1)
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=
 Sof(H22A)=Sof(H22B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,
 H19B), C19(H19C,H19D), C20(H20A,H20B), C20'(H20C,H20D), C21(H21A,H21B),
 C21'(H21C,H21D), C22(H22A,H22B), C22(H22C,H22D), C14A(H14C,H14D), C15A(H15C,
 H15D), C16A(H16C,H16D), C17A(H17C,H17D), C19A(H19E,H19F), C20A(H20E,H20F),
 C21A(H21E,H21F), C22A(H22E,H22F)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C2A(H2A), C3A(H3A), C5A(H5A),
 C6A(H6A), C8A(H8A), C9A(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5275(2) 0.11792(8) 0.73387(8) 0.0177(4) Uani 1 1 d . . . . .
O1 O 0.34557(17) 0.04302(6) 0.68811(6) 0.0226(3) Uani 1 1 d . . . . .
N1 N 0.5313(2) 0.17577(6) 0.73264(7) 0.0171(3) Uani 1 1 d . . . . .
N2 N 0.5240(2) 0.29732(6) 0.73663(7) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.5879(3) 0.08328(8) 0.78583(9) 0.0196(4) Uani 1 1 d . . . . .
H2 H 0.5791 0.0420 0.7844 0.023 Uiso 1 1 calc R U . . .
O2 O 0.4075(2) 0.44211(6) 0.69269(7) 0.0292(3) Uani 1 1 d . . . . .
N3 N 0.4650(2) 0.10556(6) 0.61875(7) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.6598(3) 0.11131(8) 0.83845(9) 0.0211(4) Uani 1 1 d . . . . .
H3 H 0.7067 0.0895 0.8737 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6638(2) 0.17267(8) 0.84005(8) 0.0187(4) Uani 1 1 d . . . . .
N4 N 0.4429(2) 0.36801(7) 0.62465(7) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.7349(3) 0.20344(8) 0.89468(9) 0.0225(4) Uani 1 1 d . . . . .
H5 H 0.7848 0.1822 0.9300 0.027 Uiso 1 1 calc R U . . .
C6 C 0.7318(3) 0.26233(8) 0.89659(9) 0.0227(4) Uani 1 1 d . . . . .
H6 H 0.7789 0.2820 0.9333 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6583(2) 0.29564(8) 0.84391(8) 0.0184(4) Uani 1 1 d . . . . .
C8 C 0.6539(3) 0.35701(8) 0.84507(9) 0.0221(4) Uani 1 1 d . . . . .
H8 H 0.6982 0.3774 0.8817 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5859(2) 0.38723(8) 0.79342(9) 0.0209(4) Uani 1 1 d . . . . .
H9 H 0.5812 0.4286 0.7937 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5230(2) 0.35518(8) 0.73961(8) 0.0182(4) Uani 1 1 d . . . . .
C11 C 0.5912(2) 0.26729(8) 0.78808(8) 0.0167(4) Uani 1 1 d . . . . .
C12 C 0.5954(2) 0.20362(8) 0.78597(8) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.4395(2) 0.08623(7) 0.67791(9) 0.0176(4) Uani 1 1 d . . . . .
C14 C 0.3873(3) 0.07384(9) 0.56353(9) 0.0234(4) Uani 1 1 d . . . . .
H14A H 0.2691 0.0900 0.5499 0.028 Uiso 1 1 calc R U . . .
H14B H 0.3741 0.0319 0.5731 0.028 Uiso 1 1 calc R U . . .
C15 C 0.5214(3) 0.08333(9) 0.51320(9) 0.0310(5) Uani 1 1 d . . . . .
H15A H 0.4633 0.0815 0.4701 0.037 Uiso 1 1 calc R U . . .
H15B H 0.6182 0.0540 0.5167 0.037 Uiso 1 1 calc R U . . .
C16 C 0.5927(3) 0.14440(10) 0.52804(10) 0.0378(6) Uani 1 1 d . . . . .
H16A H 0.5132 0.1744 0.5082 0.045 Uiso 1 1 calc R U . . .
H16B H 0.7139 0.1493 0.5123 0.045 Uiso 1 1 calc R U . . .
C17 C 0.5970(3) 0.14916(9) 0.60029(9) 0.0252(4) Uani 1 1 d . . . . .
H17A H 0.7172 0.1399 0.6192 0.030 Uiso 1 1 calc R U . . .
H17B H 0.5626 0.1888 0.6137 0.030 Uiso 1 1 calc R U . . .
C18 C 0.4519(2) 0.39081(8) 0.68358(9) 0.0200(4) Uani 1 1 d . . . . .
C19 C 0.3917(3) 0.40653(9) 0.57092(9) 0.0284(5) Uani 1 1 d D . . . .
H19A H 0.4841 0.4365 0.5646 0.034 Uiso 0.728(5) 1 calc R U P A 1
H19B H 0.2762 0.4260 0.5773 0.034 Uiso 0.728(5) 1 calc R U P A 1
H19C H 0.4446 0.4457 0.5776 0.034 Uiso 0.272(5) 1 calc R U P A 2
H19D H 0.2602 0.4106 0.5666 0.034 Uiso 0.272(5) 1 calc R U P A 2
C20 C 0.3766(5) 0.36331(14) 0.51390(13) 0.0279(7) Uani 0.728(5) 1 d D . P A 1
H20A H 0.2532 0.3484 0.5075 0.033 Uiso 0.728(5) 1 calc R U P A 1
H20B H 0.4116 0.3825 0.4744 0.033 Uiso 0.728(5) 1 calc R U P A 1
C20' C 0.4604(14) 0.3791(4) 0.5128(4) 0.0279(7) Uani 0.272(5) 1 d D . P A 2
H20C H 0.5888 0.3872 0.5082 0.033 Uiso 0.272(5) 1 calc R U P A 2
H20D H 0.3910 0.3908 0.4738 0.033 Uiso 0.272(5) 1 calc R U P A 2
C21 C 0.5055(5) 0.31409(15) 0.53271(15) 0.0273(7) Uani 0.728(5) 1 d D . P A 1
H21A H 0.4721 0.2775 0.5103 0.033 Uiso 0.728(5) 1 calc R U P A 1
H21B H 0.6297 0.3244 0.5235 0.033 Uiso 0.728(5) 1 calc R U P A 1
C21' C 0.4262(14) 0.3160(5) 0.5312(4) 0.0273(7) Uani 0.272(5) 1 d D . P A 2
H21C H 0.4960 0.2894 0.5050 0.033 Uiso 0.272(5) 1 calc R U P A 2
H21D H 0.2980 0.3065 0.5240 0.033 Uiso 0.272(5) 1 calc R U P A 2
C22 C 0.4842(3) 0.30840(8) 0.60351(9) 0.0230(4) Uani 1 1 d D . . . .
H22A H 0.3858 0.2813 0.6123 0.028 Uiso 0.728(5) 1 calc R U P A 1
H22B H 0.5957 0.2939 0.6252 0.028 Uiso 0.728(5) 1 calc R U P A 1
H22C H 0.4119 0.2786 0.6244 0.028 Uiso 0.272(5) 1 calc R U P A 2
H22D H 0.6126 0.2990 0.6100 0.028 Uiso 0.272(5) 1 calc R U P A 2
O1A O 0.0653(2) 0.35109(6) 0.96494(6) 0.0310(4) Uani 1 1 d . . . . .
C1A C 0.1260(2) 0.31160(8) 0.86447(9) 0.0186(4) Uani 1 1 d . . . . .
N1A N 0.0812(2) 0.31639(6) 0.80279(7) 0.0170(3) Uani 1 1 d . . . . .
O2A O -0.0756(2) 0.38223(6) 0.51539(6) 0.0299(3) Uani 1 1 d . . . . .
C2A C 0.1854(3) 0.25959(8) 0.89385(9) 0.0231(4) Uani 1 1 d . . . . .
H2A H 0.2244 0.2590 0.9374 0.028 Uiso 1 1 calc R U . . .
N2A N 0.0067(2) 0.32294(6) 0.67102(7) 0.0184(3) Uani 1 1 d . . . . .
N3A N 0.0920(2) 0.41715(6) 0.88754(7) 0.0175(3) Uani 1 1 d . . . . .
C3A C 0.1854(3) 0.20996(8) 0.85820(9) 0.0235(4) Uani 1 1 d . . . . .
H3A H 0.2238 0.1742 0.8769 0.028 Uiso 1 1 calc R U . . .
C4A C 0.1287(2) 0.21191(8) 0.79402(9) 0.0203(4) Uani 1 1 d . . . . .
N4A N -0.0889(2) 0.43132(7) 0.60741(7) 0.0199(3) Uani 1 1 d . . . . .
C5A C 0.1166(3) 0.16014(8) 0.75604(10) 0.0242(4) Uani 1 1 d . . . . .
H5A H 0.1391 0.1233 0.7754 0.029 Uiso 1 1 calc R U . . .
C6A C 0.0737(3) 0.16295(8) 0.69332(10) 0.0244(4) Uani 1 1 d . . . . .
H6A H 0.0653 0.1281 0.6691 0.029 Uiso 1 1 calc R U . . .
C7A C 0.0408(2) 0.21799(8) 0.66274(9) 0.0205(4) Uani 1 1 d . . . . .
C8A C 0.0113(3) 0.22196(8) 0.59660(9) 0.0241(4) Uani 1 1 d . . . . .
H8A H 0.0131 0.1878 0.5712 0.029 Uiso 1 1 calc R U . . .
C9A C -0.0198(3) 0.27507(8) 0.56906(9) 0.0232(4) Uani 1 1 d . . . . .
H9A H -0.0388 0.2785 0.5244 0.028 Uiso 1 1 calc R U . . .
C10A C -0.0233(2) 0.32486(8) 0.60826(9) 0.0196(4) Uani 1 1 d . . . . .
C11A C 0.0418(2) 0.27022(8) 0.69873(9) 0.0179(4) Uani 1 1 d . . . . .
C12A C 0.0847(2) 0.26707(8) 0.76692(9) 0.0173(4) Uani 1 1 d . . . . .
C13A C 0.0945(3) 0.36216(8) 0.90860(9) 0.0202(4) Uani 1 1 d . . . . .
C14A C 0.0480(3) 0.46426(8) 0.93144(8) 0.0207(4) Uani 1 1 d . . . . .
H14C H 0.1372 0.4665 0.9675 0.025 Uiso 1 1 calc R U . . .
H14D H -0.0718 0.4583 0.9481 0.025 Uiso 1 1 calc R U . . .
C15A C 0.0522(3) 0.51908(8) 0.89073(9) 0.0213(4) Uani 1 1 d . . . . .
H15C H 0.0962 0.5530 0.9160 0.026 Uiso 1 1 calc R U . . .
H15D H -0.0677 0.5282 0.8715 0.026 Uiso 1 1 calc R U . . .
C16A C 0.1817(3) 0.50310(8) 0.83994(9) 0.0247(4) Uani 1 1 d . . . . .
H16C H 0.1643 0.5284 0.8021 0.030 Uiso 1 1 calc R U . . .
H16D H 0.3072 0.5062 0.8565 0.030 Uiso 1 1 calc R U . . .
C17A C 0.1316(3) 0.44022(8) 0.82465(8) 0.0217(4) Uani 1 1 d . . . . .
H17C H 0.0257 0.4381 0.7948 0.026 Uiso 1 1 calc R U . . .
H17D H 0.2319 0.4190 0.8065 0.026 Uiso 1 1 calc R U . . .
C18A C -0.0643(3) 0.38206(8) 0.57448(9) 0.0209(4) Uani 1 1 d . . . . .
C19A C -0.1344(3) 0.48585(8) 0.57280(9) 0.0266(5) Uani 1 1 d . . . . .
H19E H -0.2270 0.4789 0.5385 0.032 Uiso 1 1 calc R U . . .
H19F H -0.0278 0.5031 0.5543 0.032 Uiso 1 1 calc R U . . .
C20A C -0.2041(3) 0.52473(9) 0.62394(9) 0.0327(5) Uani 1 1 d . . . . .
H20E H -0.3319 0.5171 0.6302 0.039 Uiso 1 1 calc R U . . .
H20F H -0.1886 0.5664 0.6135 0.039 Uiso 1 1 calc R U . . .
C21A C -0.0881(3) 0.50754(8) 0.68271(9) 0.0269(5) Uani 1 1 d . . . . .
H21E H 0.0297 0.5271 0.6829 0.032 Uiso 1 1 calc R U . . .
H21F H -0.1472 0.5179 0.7221 0.032 Uiso 1 1 calc R U . . .
C22A C -0.0683(3) 0.44174(8) 0.67656(8) 0.0211(4) Uani 1 1 d . . . . .
H22E H 0.0504 0.4287 0.6937 0.025 Uiso 1 1 calc R U . . .
H22F H -0.1619 0.4211 0.6993 0.025 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
C1 N1 1.328(2) . ?
C1 C2 1.411(2) . ?
C1 C13 1.510(2) . ?
O1 C13 1.241(2) . ?
N1 C12 1.361(2) . ?
N2 C10 1.329(2) . ?
N2 C11 1.361(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.370(3) . ?
O2 C18 1.241(2) . ?
N3 C13 1.347(2) . ?
N3 C14 1.469(2) . ?
N3 C17 1.473(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.409(3) . ?
C4 C5 1.432(3) . ?
C4 C12 1.418(2) . ?
N4 C18 1.348(2) . ?
N4 C19 1.473(2) . ?
N4 C22 1.476(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.352(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.436(3) . ?
C7 C8 1.409(3) . ?
C7 C11 1.416(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.369(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.414(2) . ?
C10 C18 1.513(3) . ?
C11 C12 1.462(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.515(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.527(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.527(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 H19C 0.9900 . ?
C19 H19D 0.9900 . ?
C19 C20 1.559(4) . ?
C19 C20' 1.493(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.526(4) . ?
C20' H20C 0.9900 . ?
C20' H20D 0.9900 . ?
C20' C21' 1.525(12) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.516(4) . ?
C21' H21C 0.9900 . ?
C21' H21D 0.9900 . ?
C21' C22 1.576(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
O1A C13A 1.246(2) . ?
C1A N1A 1.333(2) . ?
C1A C2A 1.407(3) . ?
C1A C13A 1.513(3) . ?
N1A C12A 1.362(2) . ?
O2A C18A 1.245(2) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.365(3) . ?
N2A C10A 1.333(2) . ?
N2A C11A 1.363(2) . ?
N3A C13A 1.337(2) . ?
N3A C14A 1.472(2) . ?
N3A C17A 1.473(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.400(3) . ?
C4A C5A 1.433(3) . ?
C4A C12A 1.421(2) . ?
N4A C18A 1.344(2) . ?
N4A C19A 1.480(2) . ?
N4A C22A 1.479(2) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.348(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.434(3) . ?
C7A C8A 1.405(3) . ?
C7A C11A 1.419(2) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.365(3) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.411(2) . ?
C10A C18A 1.518(3) . ?
C11A C12A 1.461(3) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C14A C15A 1.524(2) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C16A 1.527(3) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C16A C17A 1.521(3) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C19A H19E 0.9900 . ?
C19A H19F 0.9900 . ?
C19A C20A 1.513(3) . ?
C20A H20E 0.9900 . ?
C20A H20F 0.9900 . ?
C20A C21A 1.531(3) . ?
C21A H21E 0.9900 . ?
C21A H21F 0.9900 . ?
C21A C22A 1.523(3) . ?
C22A H22E 0.9900 . ?
C22A H22F 0.9900 . ?

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
N1 C1 C2 124.89(16) . . ?
N1 C1 C13 118.35(15) . . ?
C2 C1 C13 116.58(16) . . ?
C1 N1 C12 117.40(15) . . ?
C10 N2 C11 118.07(15) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.62(17) . . ?
C3 C2 H2 121.2 . . ?
C13 N3 C14 120.18(15) . . ?
C13 N3 C17 126.63(15) . . ?
C14 N3 C17 111.82(14) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.71(17) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 121.24(17) . . ?
C3 C4 C12 118.33(16) . . ?
C12 C4 C5 120.43(17) . . ?
C18 N4 C19 118.46(16) . . ?
C18 N4 C22 129.57(16) . . ?
C19 N4 C22 111.94(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.68(17) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.02(17) . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 121.79(17) . . ?
C8 C7 C11 117.77(17) . . ?
C11 C7 C6 120.42(17) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.04(17) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.18(17) . . ?
C10 C9 H9 120.9 . . ?
N2 C10 C9 123.70(17) . . ?
N2 C10 C18 120.37(16) . . ?
C9 C10 C18 115.93(16) . . ?
N2 C11 C7 122.23(16) . . ?
N2 C11 C12 119.28(15) . . ?
C7 C11 C12 118.49(16) . . ?
N1 C12 C4 121.95(16) . . ?
N1 C12 C11 119.15(16) . . ?
C4 C12 C11 118.89(16) . . ?
O1 C13 C1 118.59(16) . . ?
O1 C13 N3 122.11(16) . . ?
N3 C13 C1 119.30(16) . . ?
N3 C14 H14A 111.1 . . ?
N3 C14 H14B 111.1 . . ?
N3 C14 C15 103.52(15) . . ?
H14A C14 H14B 109.0 . . ?
C15 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C14 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C14 C15 C16 103.07(16) . . ?
H15A C15 H15B 109.1 . . ?
C16 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
C15 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
C15 C16 C17 105.07(16) . . ?
H16A C16 H16B 108.8 . . ?
C17 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
N3 C17 C16 103.58(15) . . ?
N3 C17 H17A 111.0 . . ?
N3 C17 H17B 111.0 . . ?
C16 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
O2 C18 N4 120.65(17) . . ?
O2 C18 C10 118.58(16) . . ?
N4 C18 C10 120.73(16) . . ?
N4 C19 H19A 111.2 . . ?
N4 C19 H19B 111.2 . . ?
N4 C19 H19C 110.3 . . ?
N4 C19 H19D 110.3 . . ?
N4 C19 C20 102.62(18) . . ?
N4 C19 C20' 106.9(4) . . ?
H19A C19 H19B 109.2 . . ?
H19C C19 H19D 108.6 . . ?
C20 C19 H19A 111.2 . . ?
C20 C19 H19B 111.2 . . ?
C20' C19 H19C 110.3 . . ?
C20' C19 H19D 110.3 . . ?
C19 C20 H20A 110.9 . . ?
C19 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
C21 C20 C19 104.4(2) . . ?
C21 C20 H20A 110.9 . . ?
C21 C20 H20B 110.9 . . ?
C19 C20' H20C 112.4 . . ?
C19 C20' H20D 112.4 . . ?
C19 C20' C21' 97.0(6) . . ?
H20C C20' H20D 109.9 . . ?
C21' C20' H20C 112.4 . . ?
C21' C20' H20D 112.4 . . ?
C20 C21 H21A 111.2 . . ?
C20 C21 H21B 111.2 . . ?
H21A C21 H21B 109.1 . . ?
C22 C21 C20 102.9(2) . . ?
C22 C21 H21A 111.2 . . ?
C22 C21 H21B 111.2 . . ?
C20' C21' H21C 110.1 . . ?
C20' C21' H21D 110.1 . . ?
C20' C21' C22 108.0(7) . . ?
H21C C21' H21D 108.4 . . ?
C22 C21' H21C 110.1 . . ?
C22 C21' H21D 110.1 . . ?
N4 C22 C21 104.60(19) . . ?
N4 C22 C21' 98.0(4) . . ?
N4 C22 H22A 110.8 . . ?
N4 C22 H22B 110.8 . . ?
N4 C22 H22C 112.2 . . ?
N4 C22 H22D 112.2 . . ?
C21 C22 H22A 110.8 . . ?
C21 C22 H22B 110.8 . . ?
C21' C22 H22C 112.2 . . ?
C21' C22 H22D 112.2 . . ?
H22A C22 H22B 108.9 . . ?
H22C C22 H22D 109.8 . . ?
N1A C1A C2A 124.01(17) . . ?
N1A C1A C13A 119.89(16) . . ?
C2A C1A C13A 115.76(16) . . ?
C1A N1A C12A 117.59(15) . . ?
C1A C2A H2A 120.9 . . ?
C3A C2A C1A 118.26(18) . . ?
C3A C2A H2A 120.9 . . ?
C10A N2A C11A 118.34(15) . . ?
C13A N3A C14A 118.91(15) . . ?
C13A N3A C17A 129.67(15) . . ?
C14A N3A C17A 111.41(14) . . ?
C2A C3A H3A 120.1 . . ?
C2A C3A C4A 119.89(17) . . ?
C4A C3A H3A 120.1 . . ?
C3A C4A C5A 121.49(17) . . ?
C3A C4A C12A 118.10(17) . . ?
C12A C4A C5A 120.40(17) . . ?
C18A N4A C19A 119.32(15) . . ?
C18A N4A C22A 129.47(16) . . ?
C22A N4A C19A 111.12(14) . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A C4A 120.99(18) . . ?
C6A C5A H5A 119.5 . . ?
C5A C6A H6A 119.6 . . ?
C5A C6A C7A 120.76(17) . . ?
C7A C6A H6A 119.6 . . ?
C8A C7A C6A 121.28(17) . . ?
C8A C7A C11A 118.26(17) . . ?
C11A C7A C6A 120.44(17) . . ?
C7A C8A H8A 120.1 . . ?
C9A C8A C7A 119.73(17) . . ?
C9A C8A H8A 120.1 . . ?
C8A C9A H9A 120.6 . . ?
C8A C9A C10A 118.72(18) . . ?
C10A C9A H9A 120.6 . . ?
N2A C10A C9A 123.27(18) . . ?
N2A C10A C18A 121.03(16) . . ?
C9A C10A C18A 115.70(16) . . ?
N2A C11A C7A 121.61(17) . . ?
N2A C11A C12A 119.65(15) . . ?
C7A C11A C12A 118.73(16) . . ?
N1A C12A C4A 121.79(16) . . ?
N1A C12A C11A 119.79(16) . . ?
C4A C12A C11A 118.42(16) . . ?
O1A C13A C1A 118.12(16) . . ?
O1A C13A N3A 120.61(17) . . ?
N3A C13A C1A 121.24(16) . . ?
N3A C14A H14C 111.0 . . ?
N3A C14A H14D 111.0 . . ?
N3A C14A C15A 103.86(14) . . ?
H14C C14A H14D 109.0 . . ?
C15A C14A H14C 111.0 . . ?
C15A C14A H14D 111.0 . . ?
C14A C15A H15C 111.1 . . ?
C14A C15A H15D 111.1 . . ?
C14A C15A C16A 103.26(15) . . ?
H15C C15A H15D 109.1 . . ?
C16A C15A H15C 111.1 . . ?
C16A C15A H15D 111.1 . . ?
C15A C16A H16C 111.3 . . ?
C15A C16A H16D 111.3 . . ?
H16C C16A H16D 109.2 . . ?
C17A C16A C15A 102.56(15) . . ?
C17A C16A H16C 111.3 . . ?
C17A C16A H16D 111.3 . . ?
N3A C17A C16A 102.04(14) . . ?
N3A C17A H17C 111.4 . . ?
N3A C17A H17D 111.4 . . ?
C16A C17A H17C 111.4 . . ?
C16A C17A H17D 111.4 . . ?
H17C C17A H17D 109.2 . . ?
O2A C18A N4A 120.72(18) . . ?
O2A C18A C10A 118.35(17) . . ?
N4A C18A C10A 120.92(16) . . ?
N4A C19A H19E 111.2 . . ?
N4A C19A H19F 111.2 . . ?
N4A C19A C20A 103.05(15) . . ?
H19E C19A H19F 109.1 . . ?
C20A C19A H19E 111.2 . . ?
C20A C19A H19F 111.2 . . ?
C19A C20A H20E 111.2 . . ?
C19A C20A H20F 111.2 . . ?
C19A C20A C21A 102.91(16) . . ?
H20E C20A H20F 109.1 . . ?
C21A C20A H20E 111.2 . . ?
C21A C20A H20F 111.2 . . ?
C20A C21A H21E 111.0 . . ?
C20A C21A H21F 111.0 . . ?
H21E C21A H21F 109.0 . . ?
C22A C21A C20A 103.90(16) . . ?
C22A C21A H21E 111.0 . . ?
C22A C21A H21F 111.0 . . ?
N4A C22A C21A 103.79(14) . . ?
N4A C22A H22E 111.0 . . ?
N4A C22A H22F 111.0 . . ?
C21A C22A H22E 111.0 . . ?
C21A C22A H22F 111.0 . . ?
H22E C22A H22F 109.0 . . ?

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
C1 N1 C12 C4 2.9(3) . . . . ?
C1 N1 C12 C11 -176.09(16) . . . . ?
C1 C2 C3 C4 2.7(3) . . . . ?
N1 C1 C2 C3 -1.6(3) . . . . ?
N1 C1 C13 O1 -139.46(18) . . . . ?
N1 C1 C13 N3 40.5(2) . . . . ?
N2 C10 C18 O2 160.74(18) . . . . ?
N2 C10 C18 N4 -21.6(3) . . . . ?
N2 C11 C12 N1 -0.3(3) . . . . ?
N2 C11 C12 C4 -179.32(16) . . . . ?
C2 C1 N1 C12 -1.2(3) . . . . ?
C2 C1 C13 O1 35.9(2) . . . . ?
C2 C1 C13 N3 -144.11(17) . . . . ?
C2 C3 C4 C5 178.86(18) . . . . ?
C2 C3 C4 C12 -1.2(3) . . . . ?
N3 C14 C15 C16 -33.4(2) . . . . ?
C3 C4 C5 C6 -177.45(18) . . . . ?
C3 C4 C12 N1 -1.8(3) . . . . ?
C3 C4 C12 C11 177.22(17) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
N4 C19 C20 C21 -27.8(3) . . . . ?
N4 C19 C20' C21' 36.8(7) . . . . ?
C5 C4 C12 N1 178.20(17) . . . . ?
C5 C4 C12 C11 -2.8(3) . . . . ?
C5 C6 C7 C8 179.99(18) . . . . ?
C5 C6 C7 C11 -1.5(3) . . . . ?
C6 C7 C8 C9 178.73(18) . . . . ?
C6 C7 C11 N2 -178.56(17) . . . . ?
C6 C7 C11 C12 1.2(3) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C7 C11 C12 N1 179.98(16) . . . . ?
C7 C11 C12 C4 0.9(3) . . . . ?
C8 C7 C11 N2 0.0(3) . . . . ?
C8 C7 C11 C12 179.76(16) . . . . ?
C8 C9 C10 N2 0.9(3) . . . . ?
C8 C9 C10 C18 -179.12(17) . . . . ?
C9 C10 C18 O2 -19.3(3) . . . . ?
C9 C10 C18 N4 158.38(17) . . . . ?
C10 N2 C11 C7 0.2(3) . . . . ?
C10 N2 C11 C12 -179.50(16) . . . . ?
C11 N2 C10 C9 -0.7(3) . . . . ?
C11 N2 C10 C18 179.31(16) . . . . ?
C11 C7 C8 C9 0.2(3) . . . . ?
C12 C4 C5 C6 2.6(3) . . . . ?
C13 C1 N1 C12 173.76(16) . . . . ?
C13 C1 C2 C3 -176.68(17) . . . . ?
C13 N3 C14 C15 -147.55(17) . . . . ?
C13 N3 C17 C16 168.53(18) . . . . ?
C14 N3 C13 C1 177.24(16) . . . . ?
C14 N3 C13 O1 -2.8(3) . . . . ?
C14 N3 C17 C16 2.0(2) . . . . ?
C14 C15 C16 C17 35.4(2) . . . . ?
C15 C16 C17 N3 -23.2(2) . . . . ?
C17 N3 C13 C1 11.7(3) . . . . ?
C17 N3 C13 O1 -168.30(18) . . . . ?
C17 N3 C14 C15 20.0(2) . . . . ?
C18 N4 C19 C20 -174.0(2) . . . . ?
C18 N4 C19 C20' 157.9(4) . . . . ?
C18 N4 C22 C21 -162.7(2) . . . . ?
C18 N4 C22 C21' 175.7(4) . . . . ?
C19 N4 C18 O2 4.3(3) . . . . ?
C19 N4 C18 C10 -173.28(17) . . . . ?
C19 N4 C22 C21 14.8(2) . . . . ?
C19 N4 C22 C21' -6.7(4) . . . . ?
C19 C20 C21 C22 37.0(4) . . . . ?
C19 C20' C21' C22 -42.4(9) . . . . ?
C20 C21 C22 N4 -31.7(3) . . . . ?
C20' C21' C22 N4 31.2(8) . . . . ?
C22 N4 C18 O2 -178.30(18) . . . . ?
C22 N4 C18 C10 4.1(3) . . . . ?
C22 N4 C19 C20 8.1(2) . . . . ?
C22 N4 C19 C20' -19.9(5) . . . . ?
C1A N1A C12A C4A 2.0(3) . . . . ?
C1A N1A C12A C11A -178.24(16) . . . . ?
C1A C2A C3A C4A 0.5(3) . . . . ?
N1A C1A C2A C3A -4.9(3) . . . . ?
N1A C1A C13A O1A 150.62(18) . . . . ?
N1A C1A C13A N3A -27.1(3) . . . . ?
C2A C1A N1A C12A 3.5(3) . . . . ?
C2A C1A C13A O1A -23.0(3) . . . . ?
C2A C1A C13A N3A 159.25(18) . . . . ?
C2A C3A C4A C5A -176.19(18) . . . . ?
C2A C3A C4A C12A 4.5(3) . . . . ?
N2A C10A C18A O2A 173.68(17) . . . . ?
N2A C10A C18A N4A -6.7(3) . . . . ?
N2A C11A C12A N1A 3.1(3) . . . . ?
N2A C11A C12A C4A -177.13(17) . . . . ?
N3A C14A C15A C16A -26.75(19) . . . . ?
C3A C4A C5A C6A -175.37(19) . . . . ?
C3A C4A C12A N1A -5.9(3) . . . . ?
C3A C4A C12A C11A 174.29(17) . . . . ?
C4A C5A C6A C7A 0.7(3) . . . . ?
N4A C19A C20A C21A 35.2(2) . . . . ?
C5A C4A C12A N1A 174.73(17) . . . . ?
C5A C4A C12A C11A -5.0(3) . . . . ?
C5A C6A C7A C8A 174.40(19) . . . . ?
C5A C6A C7A C11A -4.0(3) . . . . ?
C6A C7A C8A C9A 179.91(18) . . . . ?
C6A C7A C11A N2A -178.44(17) . . . . ?
C6A C7A C11A C12A 2.7(3) . . . . ?
C7A C8A C9A C10A -0.6(3) . . . . ?
C7A C11A C12A N1A -178.04(17) . . . . ?
C7A C11A C12A C4A 1.7(3) . . . . ?
C8A C7A C11A N2A 3.1(3) . . . . ?
C8A C7A C11A C12A -175.74(17) . . . . ?
C8A C9A C10A N2A 1.7(3) . . . . ?
C8A C9A C10A C18A -178.20(17) . . . . ?
C9A C10A C18A O2A -6.4(3) . . . . ?
C9A C10A C18A N4A 173.26(17) . . . . ?
C10A N2A C11A C7A -2.1(3) . . . . ?
C10A N2A C11A C12A 176.73(16) . . . . ?
C11A N2A C10A C9A -0.3(3) . . . . ?
C11A N2A C10A C18A 179.58(16) . . . . ?
C11A C7A C8A C9A -1.7(3) . . . . ?
C12A C4A C5A C6A 3.9(3) . . . . ?
C13A C1A N1A C12A -169.53(16) . . . . ?
C13A C1A C2A C3A 168.46(17) . . . . ?
C13A N3A C14A C15A -178.17(16) . . . . ?
C13A N3A C17A C16A -156.75(19) . . . . ?
C14A N3A C13A O1A -2.1(3) . . . . ?
C14A N3A C13A C1A 175.62(16) . . . . ?
C14A N3A C17A C16A 21.9(2) . . . . ?
C14A C15A C16A C17A 40.30(19) . . . . ?
C15A C16A C17A N3A -37.67(18) . . . . ?
C17A N3A C13A O1A 176.42(18) . . . . ?
C17A N3A C13A C1A -5.9(3) . . . . ?
C17A N3A C14A C15A 3.1(2) . . . . ?
C18A N4A C19A C20A 163.62(18) . . . . ?
C18A N4A C22A C21A 171.93(19) . . . . ?
C19A N4A C18A O2A 1.6(3) . . . . ?
C19A N4A C18A C10A -178.03(17) . . . . ?
C19A N4A C22A C21A -4.7(2) . . . . ?
C19A C20A C21A C22A -38.8(2) . . . . ?
C20A C21A C22A N4A 26.7(2) . . . . ?
C22A N4A C18A O2A -174.79(18) . . . . ?
C22A N4A C18A C10A 5.6(3) . . . . ?
C22A N4A C19A C20A -19.3(2) . . . . ?

_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_l4
_database_code_depnum_ccdc_archive 'CCDC 2072997'
loop_
_audit_author_name
_audit_author_address
'Ksenia Isakovskaya'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_l4                  
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01286 Ang.
RESPONSE: The best available crystal was small and of a low reflective power.
;
_audit_creation_date             2022-01-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 Cl2 N4 O2'
_chemical_formula_sum            'C24 H24 Cl2 N4 O2'
_chemical_formula_weight         471.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.326(3)
_cell_length_b                   10.620(3)
_cell_length_c                   22.479(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2226.3(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2665
_cell_measurement_temperature    120
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1168
_diffrn_reflns_av_unetI/netI     0.1533
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10767
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.121
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2175
_reflns_number_total             4385
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.40(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1512
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1604
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.60(17)
 0.40(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C23-C22 \\sim C22'-C23'
 with sigma of 0.02
 C20-C21 \\sim C21'-C20'
 with sigma of 0.02
 C22'-C21' \\sim C21-C22
 with sigma of 0.02
 C24'-C23' \\sim C24-C23
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C19') = Uanis(C19)
Uanis(C15) = Uanis(C15')
Uanis(C16) = Uanis(C16')
Uanis(C18') = Uanis(C18)
Uanis(C17) = Uanis(C17')
Uanis(C20) = Uanis(C20')
Uanis(C24) = Uanis(C24')
Uanis(C23) = Uanis(C23')
Uanis(C21) = Uanis(C21')
Uanis(C22') = Uanis(C22)
5. Others
 Sof(C15')=Sof(H15')=Sof(C16')=Sof(H16C)=Sof(H16D)=Sof(C17')=Sof(H17D)=
 Sof(H17C)=Sof(C18')=Sof(H18C)=Sof(H18D)=Sof(C19')=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
 Sof(C20')=Sof(H20A)=Sof(H20B)=Sof(C21')=Sof(H21A)=Sof(H21B)=Sof(C22')=
 Sof(H22A)=Sof(H22B)=Sof(C23')=Sof(H23')=Sof(C24')=Sof(H24A)=Sof(H24B)=
 Sof(H24C)=1-FVAR(2)
 Sof(C20)=Sof(H20C)=Sof(H20D)=Sof(C21)=Sof(H21C)=Sof(H21D)=Sof(C22)=Sof(H22C)=
 Sof(H22D)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24D)=Sof(H24E)=Sof(H24F)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C15'(H15'), C23'(H23'), C23(H23)
6.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16'(H16C,H16D), C17(H17A,H17B), C17'(H17D,H17C), C18(H18A,
 H18B), C18'(H18C,H18D), C20'(H20A,H20B), C20(H20C,H20D), C21'(H21A,H21B),
 C21(H21C,H21D), C22'(H22A,H22B), C22(H22C,H22D)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C11(H11)
6.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C19'(H19D,H19E,H19F), C24'(H24A,H24B,H24C), C24(H24D,
 H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5020(3) 0.8218(2) 0.71880(8) 0.0616(7) Uani 1 1 d . . . . .
O1 O 0.8503(6) 0.4355(6) 0.7568(2) 0.0588(18) Uani 1 1 d . . . . .
N1 N 0.6987(7) 0.4945(6) 0.6179(2) 0.0375(16) Uani 1 1 d . . . . .
C1 C 0.7020(9) 0.5021(7) 0.6775(3) 0.038(2) Uani 1 1 d . . . . .
O2 O 0.8630(7) 0.3898(5) 0.3724(2) 0.0546(16) Uani 1 1 d . . . . .
Cl2 Cl 0.4678(3) 0.7747(2) 0.38465(8) 0.0597(7) Uani 1 1 d . . . . .
N2 N 0.6918(7) 0.4812(6) 0.4979(2) 0.0349(16) Uani 1 1 d . . . . .
C2 C 0.6425(8) 0.6027(8) 0.7101(3) 0.041(2) Uani 1 1 d . . . . .
H2 H 0.6485 0.6042 0.7523 0.049 Uiso 1 1 calc R U . . .
C3 C 0.5765(8) 0.6973(7) 0.6802(3) 0.040(2) Uani 1 1 d . . . . .
N3 N 0.7878(7) 0.2830(7) 0.6911(2) 0.0403(17) Uani 1 1 d . . . . .
C4 C 0.5655(8) 0.6934(7) 0.6174(3) 0.0376(19) Uani 1 1 d . . . . .
N4 N 0.7361(9) 0.2499(6) 0.4271(3) 0.055(2) Uani 1 1 d . . . . .
C5 C 0.6313(8) 0.5895(7) 0.5887(3) 0.0331(18) Uani 1 1 d . . . . .
C6 C 0.4929(9) 0.7881(7) 0.5827(3) 0.0419(19) Uani 1 1 d . . . . .
H6 H 0.4489 0.8575 0.6021 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4867(9) 0.7791(7) 0.5224(3) 0.0413(19) Uani 1 1 d . . . . .
H7 H 0.4365 0.8416 0.5005 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5547(8) 0.6768(7) 0.4911(3) 0.0366(19) Uani 1 1 d . . . . .
C9 C 0.6269(8) 0.5817(7) 0.5240(3) 0.0336(18) Uani 1 1 d . . . . .
C10 C 0.5562(8) 0.6636(7) 0.4277(3) 0.039(2) Uani 1 1 d . . . . .
C11 C 0.6266(8) 0.5663(7) 0.4015(3) 0.037(2) Uani 1 1 d . . . . .
H11 H 0.6326 0.5602 0.3594 0.044 Uiso 1 1 calc R U . . .
C12 C 0.6901(8) 0.4749(7) 0.4381(3) 0.0341(18) Uani 1 1 d . . . . .
C13 C 0.7700(10) 0.3666(8) 0.4097(3) 0.042(2) Uani 1 1 d . . . . .
C14 C 0.7842(9) 0.4010(9) 0.7107(3) 0.046(2) Uani 1 1 d . . . . .
C15 C 0.802(2) 0.1357(18) 0.4137(7) 0.048(4) Uani 0.571(9) 1 d . . P A 1
H15 H 0.9080 0.1445 0.4181 0.057 Uiso 0.571(9) 1 calc R U P A 1
C15' C 0.654(3) 0.199(2) 0.4696(12) 0.048(4) Uani 0.429(9) 1 d . . P A 2
H15' H 0.6669 0.2469 0.5074 0.057 Uiso 0.429(9) 1 calc R U P A 2
C16 C 0.744(8) 0.037(5) 0.461(3) 0.077(12) Uani 0.571(9) 1 d . . P A 1
H16A H 0.7987 0.0420 0.4984 0.092 Uiso 0.571(9) 1 calc R U P A 1
H16B H 0.7490 -0.0497 0.4450 0.092 Uiso 0.571(9) 1 calc R U P A 1
C16' C 0.715(12) 0.064(7) 0.478(4) 0.077(12) Uani 0.429(9) 1 d . . P A 2
H16C H 0.7984 0.0632 0.5049 0.092 Uiso 0.429(9) 1 calc R U P A 2
H16D H 0.6410 0.0053 0.4930 0.092 Uiso 0.429(9) 1 calc R U P A 2
C17 C 0.580(2) 0.0814(15) 0.4700(8) 0.065(4) Uani 0.571(9) 1 d . . P A 1
H17A H 0.5191 0.0520 0.4368 0.079 Uiso 0.571(9) 1 calc R U P A 1
H17B H 0.5412 0.0482 0.5078 0.079 Uiso 0.571(9) 1 calc R U P A 1
C17' C 0.759(3) 0.030(2) 0.4146(11) 0.065(4) Uani 0.429(9) 1 d . . P A 2
H17D H 0.8214 -0.0455 0.4144 0.079 Uiso 0.429(9) 1 calc R U P A 2
H17C H 0.6733 0.0124 0.3898 0.079 Uiso 0.429(9) 1 calc R U P A 2
C18 C 0.588(2) 0.226(2) 0.4713(10) 0.062(6) Uani 0.571(9) 1 d . . P A 1
H18A H 0.6030 0.2588 0.5122 0.074 Uiso 0.571(9) 1 calc R U P A 1
H18B H 0.5009 0.2654 0.4541 0.074 Uiso 0.571(9) 1 calc R U P A 1
C18' C 0.839(4) 0.144(3) 0.3914(12) 0.062(6) Uani 0.429(9) 1 d . . P A 2
H18C H 0.8337 0.1523 0.3475 0.074 Uiso 0.429(9) 1 calc R U P A 2
H18D H 0.9404 0.1462 0.4045 0.074 Uiso 0.429(9) 1 calc R U P A 2
C19 C 0.767(2) 0.0938(19) 0.3524(8) 0.091(6) Uani 0.571(9) 1 d . . P A 1
H19A H 0.6639 0.0793 0.3489 0.136 Uiso 0.571(9) 1 calc R U P A 1
H19B H 0.8189 0.0155 0.3437 0.136 Uiso 0.571(9) 1 calc R U P A 1
H19C H 0.7966 0.1590 0.3240 0.136 Uiso 0.571(9) 1 calc R U P A 1
C19' C 0.507(3) 0.204(3) 0.4518(11) 0.091(6) Uani 0.429(9) 1 d . . P A 2
H19D H 0.4880 0.1371 0.4230 0.136 Uiso 0.429(9) 1 calc R U P A 2
H19E H 0.4878 0.2862 0.4336 0.136 Uiso 0.429(9) 1 calc R U P A 2
H19F H 0.4458 0.1930 0.4868 0.136 Uiso 0.429(9) 1 calc R U P A 2
C20' C 0.71(2) 0.219(7) 0.639(9) 0.045(4) Uani 0.234(9) 1 d D . P B 1
H20A H 0.7677 0.2230 0.6026 0.054 Uiso 0.234(9) 1 calc R U P B 1
H20B H 0.6158 0.2594 0.6321 0.054 Uiso 0.234(9) 1 calc R U P B 1
C20 C 0.700(6) 0.228(2) 0.643(3) 0.045(4) Uani 0.766(9) 1 d D . P B 2
H20C H 0.7172 0.2711 0.6049 0.054 Uiso 0.766(9) 1 calc R U P B 2
H20D H 0.5969 0.2313 0.6530 0.054 Uiso 0.766(9) 1 calc R U P B 2
C21' C 0.690(4) 0.082(5) 0.659(2) 0.060(4) Uani 0.234(9) 1 d D . P B 1
H21A H 0.6474 0.0276 0.6283 0.071 Uiso 0.234(9) 1 calc R U P B 1
H21B H 0.6352 0.0740 0.6971 0.071 Uiso 0.234(9) 1 calc R U P B 1
C21 C 0.7549(18) 0.0916(14) 0.6416(5) 0.060(4) Uani 0.766(9) 1 d D . P B 2
H21C H 0.8352 0.0824 0.6131 0.071 Uiso 0.766(9) 1 calc R U P B 2
H21D H 0.6772 0.0326 0.6304 0.071 Uiso 0.766(9) 1 calc R U P B 2
C22' C 0.856(4) 0.061(4) 0.6677(19) 0.062(4) Uani 0.234(9) 1 d D . P B 1
H22A H 0.8807 -0.0262 0.6792 0.075 Uiso 0.234(9) 1 calc R U P B 1
H22B H 0.9124 0.0866 0.6323 0.075 Uiso 0.234(9) 1 calc R U P B 1
C22 C 0.8057(15) 0.0678(12) 0.7062(5) 0.062(4) Uani 0.766(9) 1 d D . P B 2
H22C H 0.7244 0.0411 0.7315 0.075 Uiso 0.766(9) 1 calc R U P B 2
H22D H 0.8803 0.0015 0.7072 0.075 Uiso 0.766(9) 1 calc R U P B 2
C23' C 0.871(10) 0.154(5) 0.719(2) 0.043(4) Uani 0.234(9) 1 d D . P B 1
H23' H 0.9744 0.1722 0.7276 0.052 Uiso 0.234(9) 1 calc R U P B 1
C23 C 0.867(3) 0.1930(11) 0.7278(7) 0.043(4) Uani 0.766(9) 1 d D . P B 2
H23 H 0.8418 0.2058 0.7707 0.052 Uiso 0.766(9) 1 calc R U P B 2
C24' C 0.795(4) 0.115(4) 0.7749(15) 0.063(3) Uani 0.234(9) 1 d D . P B 1
H24A H 0.7754 0.1890 0.7994 0.095 Uiso 0.234(9) 1 calc R U P B 1
H24B H 0.8549 0.0556 0.7972 0.095 Uiso 0.234(9) 1 calc R U P B 1
H24C H 0.7040 0.0737 0.7644 0.095 Uiso 0.234(9) 1 calc R U P B 1
C24 C 1.0264(13) 0.2080(11) 0.7190(4) 0.063(3) Uani 0.766(9) 1 d D . P B 2
H24D H 1.0489 0.2033 0.6765 0.095 Uiso 0.766(9) 1 calc R U P B 2
H24E H 1.0769 0.1406 0.7401 0.095 Uiso 0.766(9) 1 calc R U P B 2
H24F H 1.0570 0.2898 0.7346 0.095 Uiso 0.766(9) 1 calc R U P B 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 C3 1.727(8) . ?
O1 C14 1.262(9) . ?
N1 C1 1.343(8) . ?
N1 C5 1.357(9) . ?
C1 C2 1.408(10) . ?
C1 C14 1.516(11) . ?
O2 C13 1.231(9) . ?
Cl2 C10 1.734(7) . ?
N2 C9 1.360(9) . ?
N2 C12 1.346(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.357(10) . ?
C3 C4 1.416(9) . ?
N3 C14 1.329(10) . ?
N3 C20' 1.5(2) . ?
N3 C20 1.47(6) . ?
N3 C23' 1.70(8) . ?
N3 C23 1.46(2) . ?
C4 C5 1.417(9) . ?
C4 C6 1.441(10) . ?
N4 C13 1.338(10) . ?
N4 C15 1.39(2) . ?
N4 C15' 1.34(3) . ?
N4 C18 1.72(2) . ?
N4 C18' 1.68(3) . ?
C5 C9 1.458(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.359(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.442(10) . ?
C8 C9 1.422(10) . ?
C8 C10 1.432(9) . ?
C10 C11 1.358(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.403(9) . ?
C12 C13 1.512(11) . ?
C15 H15 1.0000 . ?
C15 C16 1.58(7) . ?
C15 C19 1.48(2) . ?
C15' H15' 1.0000 . ?
C15' C16' 1.55(9) . ?
C15' C19' 1.43(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.61(7) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C16' C17' 1.52(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.54(3) . ?
C17' H17D 0.9900 . ?
C17' H17C 0.9900 . ?
C17' C18' 1.52(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18' H18C 0.9900 . ?
C18' H18D 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C20' H20A 0.9900 . ?
C20' H20B 0.9900 . ?
C20' C21' 1.53(3) . ?
C20 H20C 0.9900 . ?
C20 H20D 0.9900 . ?
C20 C21 1.53(2) . ?
C21' H21A 0.9900 . ?
C21' H21B 0.9900 . ?
C21' C22' 1.58(3) . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C21 C22 1.548(14) . ?
C22' H22A 0.9900 . ?
C22' H22B 0.9900 . ?
C22' C23' 1.53(3) . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
C22 C23 1.525(17) . ?
C23' H23' 1.0000 . ?
C23' C24' 1.50(4) . ?
C23 H23 1.0000 . ?
C23 C24 1.51(3) . ?
C24' H24A 0.9800 . ?
C24' H24B 0.9800 . ?
C24' H24C 0.9800 . ?
C24 H24D 0.9800 . ?
C24 H24E 0.9800 . ?
C24 H24F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.5(6) . . ?
N1 C1 C2 123.8(7) . . ?
N1 C1 C14 117.3(7) . . ?
C2 C1 C14 118.7(7) . . ?
C12 N2 C9 117.7(6) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(7) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 Cl1 120.0(6) . . ?
C2 C3 C4 120.3(7) . . ?
C4 C3 Cl1 119.6(6) . . ?
C14 N3 C20' 131(4) . . ?
C14 N3 C20 127.2(14) . . ?
C14 N3 C23' 130.5(19) . . ?
C14 N3 C23 116.2(8) . . ?
C20' N3 C23' 98(4) . . ?
C23 N3 C20 115.5(13) . . ?
C3 C4 C5 116.4(7) . . ?
C3 C4 C6 123.6(7) . . ?
C5 C4 C6 120.1(6) . . ?
C13 N4 C15 129.8(9) . . ?
C13 N4 C15' 136.1(12) . . ?
C13 N4 C18 119.6(10) . . ?
C13 N4 C18' 110.1(11) . . ?
C15 N4 C18 110.6(12) . . ?
C15' N4 C18' 113.3(15) . . ?
N1 C5 C4 124.1(6) . . ?
N1 C5 C9 116.9(6) . . ?
C4 C5 C9 119.0(7) . . ?
C4 C6 H6 119.7 . . ?
C7 C6 C4 120.7(7) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.4(7) . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 119.3(6) . . ?
C9 C8 C10 116.4(6) . . ?
C10 C8 C7 124.3(7) . . ?
N2 C9 C5 117.6(7) . . ?
N2 C9 C8 122.9(6) . . ?
C8 C9 C5 119.5(7) . . ?
C8 C10 Cl2 118.9(6) . . ?
C11 C10 Cl2 120.4(5) . . ?
C11 C10 C8 120.7(6) . . ?
C10 C11 H11 120.8 . . ?
C10 C11 C12 118.4(6) . . ?
C12 C11 H11 120.8 . . ?
N2 C12 C11 123.8(7) . . ?
N2 C12 C13 117.0(6) . . ?
C11 C12 C13 119.1(6) . . ?
O2 C13 N4 123.4(8) . . ?
O2 C13 C12 118.9(7) . . ?
N4 C13 C12 117.7(7) . . ?
O1 C14 C1 116.5(8) . . ?
O1 C14 N3 122.3(8) . . ?
N3 C14 C1 121.2(7) . . ?
N4 C15 H15 109.5 . . ?
N4 C15 C16 106.4(19) . . ?
N4 C15 C19 111.5(16) . . ?
C16 C15 H15 109.5 . . ?
C19 C15 H15 109.5 . . ?
C19 C15 C16 110(3) . . ?
N4 C15' H15' 109.3 . . ?
N4 C15' C16' 105(4) . . ?
N4 C15' C19' 109(2) . . ?
C16' C15' H15' 109.3 . . ?
C19' C15' H15' 109.3 . . ?
C19' C15' C16' 115(5) . . ?
C15 C16 H16A 111.3 . . ?
C15 C16 H16B 111.3 . . ?
C15 C16 C17 103(4) . . ?
H16A C16 H16B 109.2 . . ?
C17 C16 H16A 111.3 . . ?
C17 C16 H16B 111.3 . . ?
C15' C16' H16C 111.4 . . ?
C15' C16' H16D 111.4 . . ?
H16C C16' H16D 109.2 . . ?
C17' C16' C15' 102(6) . . ?
C17' C16' H16C 111.4 . . ?
C17' C16' H16D 111.4 . . ?
C16 C17 H17A 110.9 . . ?
C16 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C18 C17 C16 104(3) . . ?
C18 C17 H17A 110.9 . . ?
C18 C17 H17B 110.9 . . ?
C16' C17' H17D 110.7 . . ?
C16' C17' H17C 110.7 . . ?
H17D C17' H17C 108.8 . . ?
C18' C17' C16' 105(4) . . ?
C18' C17' H17D 110.7 . . ?
C18' C17' H17C 110.7 . . ?
N4 C18 H18A 111.8 . . ?
N4 C18 H18B 111.8 . . ?
C17 C18 N4 99.8(13) . . ?
C17 C18 H18A 111.8 . . ?
C17 C18 H18B 111.8 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18' H18C 112.7 . . ?
N4 C18' H18D 112.7 . . ?
C17' C18' N4 95.0(16) . . ?
C17' C18' H18C 112.7 . . ?
C17' C18' H18D 112.7 . . ?
H18C C18' H18D 110.2 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15' C19' H19D 109.5 . . ?
C15' C19' H19E 109.5 . . ?
C15' C19' H19F 109.5 . . ?
H19D C19' H19E 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
N3 C20' H20A 110.8 . . ?
N3 C20' H20B 110.8 . . ?
N3 C20' C21' 105(10) . . ?
H20A C20' H20B 108.8 . . ?
C21' C20' H20A 110.8 . . ?
C21' C20' H20B 110.8 . . ?
N3 C20 H20C 111.3 . . ?
N3 C20 H20D 111.3 . . ?
N3 C20 C21 102(3) . . ?
H20C C20 H20D 109.2 . . ?
C21 C20 H20C 111.3 . . ?
C21 C20 H20D 111.3 . . ?
C20' C21' H21A 113.2 . . ?
C20' C21' H21B 113.2 . . ?
C20' C21' C22' 93(9) . . ?
H21A C21' H21B 110.5 . . ?
C22' C21' H21A 113.2 . . ?
C22' C21' H21B 113.2 . . ?
C20 C21 H21C 111.1 . . ?
C20 C21 H21D 111.1 . . ?
C20 C21 C22 103(2) . . ?
H21C C21 H21D 109.0 . . ?
C22 C21 H21C 111.1 . . ?
C22 C21 H21D 111.1 . . ?
C21' C22' H22A 112.7 . . ?
C21' C22' H22B 112.7 . . ?
H22A C22' H22B 110.2 . . ?
C23' C22' C21' 95(5) . . ?
C23' C22' H22A 112.7 . . ?
C23' C22' H22B 112.7 . . ?
C21 C22 H22C 110.6 . . ?
C21 C22 H22D 110.6 . . ?
H22C C22 H22D 108.7 . . ?
C23 C22 C21 105.7(11) . . ?
C23 C22 H22C 110.6 . . ?
C23 C22 H22D 110.6 . . ?
N3 C23' H23' 110.8 . . ?
C22' C23' N3 101(4) . . ?
C22' C23' H23' 110.8 . . ?
C24' C23' N3 109(5) . . ?
C24' C23' C22' 114(5) . . ?
C24' C23' H23' 110.8 . . ?
N3 C23 C22 101.7(13) . . ?
N3 C23 H23 109.9 . . ?
N3 C23 C24 110.6(12) . . ?
C22 C23 H23 109.9 . . ?
C24 C23 C22 114.6(12) . . ?
C24 C23 H23 109.9 . . ?
C23' C24' H24A 109.5 . . ?
C23' C24' H24B 109.5 . . ?
C23' C24' H24C 109.5 . . ?
H24A C24' H24B 109.5 . . ?
H24A C24' H24C 109.5 . . ?
H24B C24' H24C 109.5 . . ?
C23 C24 H24D 109.5 . . ?
C23 C24 H24E 109.5 . . ?
C23 C24 H24F 109.5 . . ?
H24D C24 H24E 109.5 . . ?
H24D C24 H24F 109.5 . . ?
H24E C24 H24F 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
Cl1 C3 C4 C5 179.0(6) . . . . ?
Cl1 C3 C4 C6 -0.8(10) . . . . ?
N1 C1 C2 C3 0.7(12) . . . . ?
N1 C1 C14 O1 144.2(7) . . . . ?
N1 C1 C14 N3 -34.6(11) . . . . ?
N1 C5 C9 N2 -0.7(10) . . . . ?
N1 C5 C9 C8 178.5(7) . . . . ?
C1 N1 C5 C4 -0.2(11) . . . . ?
C1 N1 C5 C9 -179.8(7) . . . . ?
C1 C2 C3 Cl1 179.8(6) . . . . ?
C1 C2 C3 C4 1.2(12) . . . . ?
Cl2 C10 C11 C12 -176.6(6) . . . . ?
N2 C12 C13 O2 -124.6(8) . . . . ?
N2 C12 C13 N4 54.9(10) . . . . ?
C2 C1 C14 O1 -31.4(11) . . . . ?
C2 C1 C14 N3 149.8(7) . . . . ?
C2 C3 C4 C5 -2.4(11) . . . . ?
C2 C3 C4 C6 177.8(7) . . . . ?
C3 C4 C5 N1 1.9(11) . . . . ?
C3 C4 C5 C9 -178.4(7) . . . . ?
C3 C4 C6 C7 179.7(7) . . . . ?
N3 C20' C21' C22' -58(10) . . . . ?
N3 C20 C21 C22 28(3) . . . . ?
C4 C5 C9 N2 179.6(7) . . . . ?
C4 C5 C9 C8 -1.2(11) . . . . ?
C4 C6 C7 C8 -1.4(12) . . . . ?
N4 C15 C16 C17 36(4) . . . . ?
N4 C15' C16' C17' -35(7) . . . . ?
C5 N1 C1 C2 -1.2(11) . . . . ?
C5 N1 C1 C14 -176.5(7) . . . . ?
C5 C4 C6 C7 -0.1(11) . . . . ?
C6 C4 C5 N1 -178.3(7) . . . . ?
C6 C4 C5 C9 1.3(11) . . . . ?
C6 C7 C8 C9 1.5(12) . . . . ?
C6 C7 C8 C10 -178.0(7) . . . . ?
C7 C8 C9 N2 179.0(7) . . . . ?
C7 C8 C9 C5 -0.2(11) . . . . ?
C7 C8 C10 Cl2 -1.6(10) . . . . ?
C7 C8 C10 C11 178.0(8) . . . . ?
C8 C10 C11 C12 3.9(11) . . . . ?
C9 N2 C12 C11 0.6(10) . . . . ?
C9 N2 C12 C13 176.6(7) . . . . ?
C9 C8 C10 Cl2 178.9(6) . . . . ?
C9 C8 C10 C11 -1.5(11) . . . . ?
C10 C8 C9 N2 -1.5(11) . . . . ?
C10 C8 C9 C5 179.3(7) . . . . ?
C10 C11 C12 N2 -3.5(11) . . . . ?
C10 C11 C12 C13 -179.4(7) . . . . ?
C11 C12 C13 O2 51.6(11) . . . . ?
C11 C12 C13 N4 -129.0(8) . . . . ?
C12 N2 C9 C5 -178.9(6) . . . . ?
C12 N2 C9 C8 1.9(11) . . . . ?
C13 N4 C15 C16 164(3) . . . . ?
C13 N4 C15 C19 -75.6(19) . . . . ?
C13 N4 C15' C16' -158(4) . . . . ?
C13 N4 C15' C19' 78(3) . . . . ?
C13 N4 C18 C17 170.9(12) . . . . ?
C13 N4 C18' C17' -172.5(16) . . . . ?
C14 C1 C2 C3 176.0(7) . . . . ?
C14 N3 C20' C21' -149(4) . . . . ?
C14 N3 C20 C21 179.4(12) . . . . ?
C14 N3 C23' C22' -168(2) . . . . ?
C14 N3 C23' C24' 71(6) . . . . ?
C14 N3 C23 C22 160.7(9) . . . . ?
C14 N3 C23 C24 -77.1(11) . . . . ?
C15 N4 C13 O2 7.3(16) . . . . ?
C15 N4 C13 C12 -172.1(12) . . . . ?
C15 N4 C18 C17 -7(2) . . . . ?
C15 C16 C17 C18 -41(3) . . . . ?
C15' N4 C13 O2 171.3(19) . . . . ?
C15' N4 C13 C12 -8(2) . . . . ?
C15' N4 C18' C17' 14(3) . . . . ?
C15' C16' C17' C18' 46(7) . . . . ?
C16 C17 C18 N4 29(3) . . . . ?
C16' C17' C18' N4 -36(5) . . . . ?
C18 N4 C13 O2 -170.8(11) . . . . ?
C18 N4 C13 C12 9.8(14) . . . . ?
C18 N4 C15 C16 -18(4) . . . . ?
C18 N4 C15 C19 102.7(16) . . . . ?
C18' N4 C13 O2 0.6(18) . . . . ?
C18' N4 C13 C12 -178.8(14) . . . . ?
C18' N4 C15' C16' 12(5) . . . . ?
C18' N4 C15' C19' -111(2) . . . . ?
C19 C15 C16 C17 -85(3) . . . . ?
C19' C15' C16' C17' 85(6) . . . . ?
C20' N3 C14 O1 176(8) . . . . ?
C20' N3 C14 C1 -6(8) . . . . ?
C20' N3 C23' C22' 16(8) . . . . ?
C20' N3 C23' C24' -105(8) . . . . ?
C20' C21' C22' C23' 66(8) . . . . ?
C20 N3 C14 O1 171(2) . . . . ?
C20 N3 C14 C1 -10(3) . . . . ?
C20 N3 C23 C22 -8(3) . . . . ?
C20 N3 C23 C24 114(2) . . . . ?
C20 C21 C22 C23 -35(3) . . . . ?
C21' C22' C23' N3 -50(5) . . . . ?
C21' C22' C23' C24' 66(7) . . . . ?
C21 C22 C23 N3 26.2(15) . . . . ?
C21 C22 C23 C24 -93.2(14) . . . . ?
C23' N3 C14 O1 1(4) . . . . ?
C23' N3 C14 C1 180(3) . . . . ?
C23' N3 C20' C21' 27(10) . . . . ?
C23 N3 C14 O1 3.2(14) . . . . ?
C23 N3 C14 C1 -178.0(11) . . . . ?
C23 N3 C20 C21 -13(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.60(17)
2 0.40(17)

####################################################################### 
# 
# 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_l3
_database_code_depnum_ccdc_archive 'CCDC 2072998'
loop_
_audit_author_name
_audit_author_address
'Ksenia Isakovskaya'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-01-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 N4 O2'
_chemical_formula_sum            'C24 H26 N4 O2'
_chemical_formula_weight         402.49
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.6426(8)
_cell_length_b                   10.6697(10)
_cell_length_c                   22.304(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2056.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4188
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.65
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0683 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.8937.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21713
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         1.826
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3656
_reflns_number_total             4498
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+1.1710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1185
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7539
 0.2461
2. Restrained distances
 C18'-C14' \\sim C18-C14
 with sigma of 0.02
 N3-C14 \\sim N3'-C14'
 with sigma of 0.02
 C15'-C14' \\sim C15-C14
 with sigma of 0.02
 C16-C15 \\sim C15'-C16'
 with sigma of 0.02
 N3-C13 \\sim N3'-C13'
 with sigma of 0.02
 C17-C16 \\sim C17'-C16'
 with sigma of 0.02
 N3-C17 \\sim N3'-C17'
 with sigma of 0.02
 O1-C13 \\sim O1'-C13'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C18') \\sim Ueq, Uanis(C16') \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C15') \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0.001 and
sigma for terminal atoms of 0.002
Uanis(C14') \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C15') \\sim Ueq, Uanis(C16')
\\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(C18') = Uanis(C18)
Uanis(N3') = Uanis(N3)
Uanis(O1) = Uanis(O1')
Uanis(C13) = Uanis(C13')
Uanis(C16) = Uanis(C16')
Uanis(C17') = Uanis(C17)
Uanis(C14) = Uanis(C14')
Uanis(C15) = Uanis(C15')
4. Others
 Sof(O1')=Sof(N3')=Sof(C13')=Sof(C14')=Sof(H14')=Sof(C15')=Sof(H15C)=Sof(H15D)=
 Sof(C16')=Sof(H16C)=Sof(H16D)=Sof(C17')=Sof(H17C)=Sof(H17D)=Sof(C18')=
 Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(O1)=Sof(N3)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=
 Sof(H18B)=Sof(H18C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C14(H14), C14'(H14'), C20(H20)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15'(H15C,H15D), C16(H16A,H16B), C16'(H16C,H16D), C17(H17A,
 H17B), C17'(H17C,H17D), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18'(H18D,H18E,H18F), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3124(4) 0.5323(3) 0.30032(14) 0.0274(7) Uani 1 1 d . . . . .
N1 N 0.3093(3) 0.5286(2) 0.35980(11) 0.0246(6) Uani 1 1 d . . . . .
O1 O 0.2228(5) 0.6354(3) 0.21367(12) 0.0435(9) Uani 0.829(4) 1 d D . P A 1
O1' O 0.144(3) 0.5891(16) 0.2197(6) 0.0435(9) Uani 0.171(4) 1 d D . P A 2
O2 O 0.1187(3) 0.5955(2) 0.61042(10) 0.0314(5) Uani 1 1 d . . . . .
N2 N 0.3071(3) 0.5228(2) 0.48282(11) 0.0217(6) Uani 1 1 d . . . . .
C2 C 0.3738(4) 0.4353(3) 0.26467(15) 0.0324(8) Uani 1 1 d . . . . .
H2 H 0.3731 0.4412 0.2222 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4345(4) 0.3326(3) 0.29274(15) 0.0320(8) Uani 1 1 d . . . . .
H3 H 0.4763 0.2659 0.2696 0.038 Uiso 1 1 calc R U . . .
N3 N 0.2241(5) 0.7559(3) 0.2961(2) 0.0272(10) Uani 0.829(4) 1 d D . P A 1
N3' N 0.184(3) 0.727(2) 0.2939(13) 0.0272(10) Uani 0.171(4) 1 d D . P A 2
C4 C 0.4352(4) 0.3252(3) 0.35588(15) 0.0268(7) Uani 1 1 d . . . . .
N4 N 0.2677(4) 0.7400(2) 0.56302(11) 0.0268(6) Uani 1 1 d . . . . .
C5 C 0.5005(4) 0.2211(3) 0.38771(16) 0.0329(8) Uani 1 1 d . . . . .
H5 H 0.5452 0.1534 0.3661 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4989(4) 0.2189(3) 0.44823(17) 0.0322(8) Uani 1 1 d . . . . .
H6 H 0.5429 0.1493 0.4686 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4325(4) 0.3188(3) 0.48243(15) 0.0259(7) Uani 1 1 d . . . . .
C8 C 0.4291(4) 0.3177(3) 0.54567(15) 0.0282(8) Uani 1 1 d . . . . .
H8 H 0.4726 0.2493 0.5671 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3629(4) 0.4153(3) 0.57609(15) 0.0271(7) Uani 1 1 d . . . . .
H9 H 0.3565 0.4147 0.6186 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3044(4) 0.5172(3) 0.54234(13) 0.0223(7) Uani 1 1 d . . . . .
C11 C 0.3677(4) 0.4237(3) 0.45287(14) 0.0224(6) Uani 1 1 d . . . . .
C12 C 0.3696(4) 0.4267(3) 0.38766(14) 0.0225(7) Uani 1 1 d . . . . .
C13 C 0.2495(6) 0.6470(5) 0.2682(2) 0.0291(13) Uani 0.829(4) 1 d D . P A 1
C13' C 0.213(4) 0.620(3) 0.2663(13) 0.0291(13) Uani 0.171(4) 1 d D . P A 2
C14 C 0.1752(5) 0.8656(4) 0.26079(19) 0.0363(10) Uani 0.829(4) 1 d D . P A 1
H14 H 0.2368 0.8698 0.2229 0.044 Uiso 0.829(4) 1 calc R U P A 1
C14' C 0.079(3) 0.8180(19) 0.2673(8) 0.0363(10) Uani 0.171(4) 1 d D U P A 2
H14' H -0.0201 0.7712 0.2609 0.044 Uiso 0.171(4) 1 calc R U P A 2
C15 C 0.2189(6) 0.9748(4) 0.30120(19) 0.0404(11) Uani 0.829(4) 1 d D U P A 1
H15A H 0.3254 1.0038 0.2924 0.048 Uiso 0.829(4) 1 calc R U P A 1
H15B H 0.1467 1.0458 0.2955 0.048 Uiso 0.829(4) 1 calc R U P A 1
C15' C 0.040(3) 0.919(2) 0.3134(9) 0.0404(11) Uani 0.171(4) 1 d D U P A 2
H15C H 0.0408 1.0037 0.2950 0.048 Uiso 0.171(4) 1 calc R U P A 2
H15D H -0.0625 0.9041 0.3320 0.048 Uiso 0.171(4) 1 calc R U P A 2
C16 C 0.2083(7) 0.9254(5) 0.3633(3) 0.0496(13) Uani 0.829(4) 1 d D U P A 1
H16A H 0.1006 0.9304 0.3782 0.059 Uiso 0.829(4) 1 calc R U P A 1
H16B H 0.2762 0.9736 0.3906 0.059 Uiso 0.829(4) 1 calc R U P A 1
C16' C 0.161(3) 0.906(3) 0.3559(13) 0.0496(13) Uani 0.171(4) 1 d D U P A 2
H16C H 0.1149 0.8984 0.3965 0.059 Uiso 0.171(4) 1 calc R U P A 2
H16D H 0.2254 0.9824 0.3553 0.059 Uiso 0.171(4) 1 calc R U P A 2
C17 C 0.2610(10) 0.7896(6) 0.35937(19) 0.0360(13) Uani 0.829(4) 1 d D . P A 1
H17A H 0.3732 0.7819 0.3675 0.043 Uiso 0.829(4) 1 calc R U P A 1
H17B H 0.2033 0.7360 0.3879 0.043 Uiso 0.829(4) 1 calc R U P A 1
C17' C 0.264(5) 0.792(3) 0.3444(15) 0.0360(13) Uani 0.171(4) 1 d D . P A 2
H17C H 0.3697 0.8182 0.3329 0.043 Uiso 0.171(4) 1 calc R U P A 2
H17D H 0.2697 0.7377 0.3803 0.043 Uiso 0.171(4) 1 calc R U P A 2
C18 C 0.0054(7) 0.8592(6) 0.2459(3) 0.0653(16) Uani 0.829(4) 1 d D U P A 1
H18A H -0.0175 0.7788 0.2265 0.098 Uiso 0.829(4) 1 calc R U P A 1
H18B H -0.0213 0.9279 0.2185 0.098 Uiso 0.829(4) 1 calc R U P A 1
H18C H -0.0555 0.8669 0.2827 0.098 Uiso 0.829(4) 1 calc R U P A 1
C18' C 0.123(4) 0.867(3) 0.2067(11) 0.0653(16) Uani 0.171(4) 1 d D U P A 2
H18D H 0.2037 0.9303 0.2109 0.098 Uiso 0.171(4) 1 calc R U P A 2
H18E H 0.0316 0.9044 0.1875 0.098 Uiso 0.171(4) 1 calc R U P A 2
H18F H 0.1609 0.7977 0.1818 0.098 Uiso 0.171(4) 1 calc R U P A 2
C19 C 0.2230(4) 0.6220(3) 0.57489(13) 0.0244(6) Uani 1 1 d . . . . .
C20 C 0.1867(4) 0.8484(3) 0.59028(14) 0.0294(7) Uani 1 1 d . . . . .
H20 H 0.0723 0.8391 0.5853 0.035 Uiso 1 1 calc R U . . .
C21 C 0.2467(5) 0.9572(3) 0.55120(17) 0.0377(8) Uani 1 1 d . . . . .
H21A H 0.1825 0.9672 0.5148 0.045 Uiso 1 1 calc R U . . .
H21B H 0.2465 1.0369 0.5739 0.045 Uiso 1 1 calc R U . . .
C22 C 0.4119(5) 0.9181(3) 0.5349(2) 0.0440(10) Uani 1 1 d . . . . .
H22A H 0.4486 0.9627 0.4987 0.053 Uiso 1 1 calc R U . . .
H22B H 0.4842 0.9345 0.5684 0.053 Uiso 1 1 calc R U . . .
C23 C 0.3955(5) 0.7781(3) 0.52322(16) 0.0362(9) Uani 1 1 d . . . . .
H23A H 0.3696 0.7617 0.4807 0.043 Uiso 1 1 calc R U . . .
H23B H 0.4920 0.7330 0.5335 0.043 Uiso 1 1 calc R U . . .
C24 C 0.2266(5) 0.8628(4) 0.65582(15) 0.0463(10) Uani 1 1 d . . . . .
H24A H 0.2011 0.7852 0.6772 0.069 Uiso 1 1 calc R U . . .
H24B H 0.1670 0.9323 0.6729 0.069 Uiso 1 1 calc R U . . .
H24C H 0.3374 0.8802 0.6600 0.069 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
C1 N1 1.328(4) . ?
C1 C2 1.409(5) . ?
C1 C13 1.519(7) . ?
C1 C13' 1.48(3) . ?
N1 C12 1.356(4) . ?
O1 C13 1.244(6) . ?
O1' C13' 1.24(2) . ?
O2 C19 1.233(4) . ?
N2 C10 1.329(4) . ?
N2 C11 1.355(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.367(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.410(5) . ?
N3 C13 1.336(6) . ?
N3 C14 1.474(6) . ?
N3 C17 1.491(6) . ?
N3' C13' 1.32(2) . ?
N3' C14' 1.46(2) . ?
N3' C17' 1.49(2) . ?
C4 C5 1.434(5) . ?
C4 C12 1.413(4) . ?
N4 C19 1.344(4) . ?
N4 C20 1.482(4) . ?
N4 C23 1.474(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.350(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.431(5) . ?
C7 C8 1.411(5) . ?
C7 C11 1.415(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.368(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.416(4) . ?
C10 C19 1.507(4) . ?
C11 C12 1.455(4) . ?
C14 H14 1.0000 . ?
C14 C15 1.521(6) . ?
C14 C18 1.506(8) . ?
C14' H14' 1.0000 . ?
C14' C15' 1.53(2) . ?
C14' C18' 1.50(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.485(7) . ?
C15' H15C 0.9900 . ?
C15' H15D 0.9900 . ?
C15' C16' 1.42(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.521(7) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C16' C17' 1.53(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 0.9800 . ?
C20 H20 1.0000 . ?
C20 C21 1.541(5) . ?
C20 C24 1.510(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.531(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.523(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
N1 C1 C2 123.3(3) . . ?
N1 C1 C13 119.3(3) . . ?
N1 C1 C13' 121.3(12) . . ?
C2 C1 C13 117.4(3) . . ?
C2 C1 C13' 113.3(11) . . ?
C1 N1 C12 118.3(3) . . ?
C10 N2 C11 117.6(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C13 N3 C14 119.3(5) . . ?
C13 N3 C17 128.0(5) . . ?
C14 N3 C17 112.1(4) . . ?
C13' N3' C14' 120(3) . . ?
C13' N3' C17' 132(2) . . ?
C14' N3' C17' 107(2) . . ?
C3 C4 C5 122.6(3) . . ?
C3 C4 C12 117.1(3) . . ?
C12 C4 C5 120.2(3) . . ?
C19 N4 C20 121.0(3) . . ?
C19 N4 C23 126.3(3) . . ?
C23 N4 C20 112.7(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 122.4(3) . . ?
C8 C7 C11 117.6(3) . . ?
C11 C7 C6 120.0(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 118.0(3) . . ?
C10 C9 H9 121.0 . . ?
N2 C10 C9 124.0(3) . . ?
N2 C10 C19 117.1(3) . . ?
C9 C10 C19 118.7(3) . . ?
N2 C11 C7 122.7(3) . . ?
N2 C11 C12 118.7(3) . . ?
C7 C11 C12 118.6(3) . . ?
N1 C12 C4 122.6(3) . . ?
N1 C12 C11 118.1(3) . . ?
C4 C12 C11 119.3(3) . . ?
O1 C13 C1 116.5(4) . . ?
O1 C13 N3 120.8(5) . . ?
N3 C13 C1 122.6(4) . . ?
O1' C13' C1 122(2) . . ?
O1' C13' N3' 122(3) . . ?
N3' C13' C1 115(2) . . ?
N3 C14 H14 109.5 . . ?
N3 C14 C15 102.8(3) . . ?
N3 C14 C18 111.2(4) . . ?
C15 C14 H14 109.5 . . ?
C18 C14 H14 109.5 . . ?
C18 C14 C15 114.1(5) . . ?
N3' C14' H14' 105.1 . . ?
N3' C14' C15' 109.5(18) . . ?
N3' C14' C18' 116(2) . . ?
C15' C14' H14' 105.1 . . ?
C18' C14' H14' 105.1 . . ?
C18' C14' C15' 115(2) . . ?
C14 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C16 C15 C14 105.4(4) . . ?
C16 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C14' C15' H15C 111.3 . . ?
C14' C15' H15D 111.3 . . ?
H15C C15' H15D 109.2 . . ?
C16' C15' C14' 103(2) . . ?
C16' C15' H15C 111.3 . . ?
C16' C15' H15D 111.3 . . ?
C15 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
C15 C16 C17 105.5(4) . . ?
H16A C16 H16B 108.8 . . ?
C17 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
C15' C16' H16C 108.9 . . ?
C15' C16' H16D 108.9 . . ?
C15' C16' C17' 113(2) . . ?
H16C C16' H16D 107.7 . . ?
C17' C16' H16C 108.9 . . ?
C17' C16' H16D 108.9 . . ?
N3 C17 C16 102.7(4) . . ?
N3 C17 H17A 111.2 . . ?
N3 C17 H17B 111.2 . . ?
C16 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
N3' C17' C16' 103(3) . . ?
N3' C17' H17C 111.1 . . ?
N3' C17' H17D 111.1 . . ?
C16' C17' H17C 111.1 . . ?
C16' C17' H17D 111.1 . . ?
H17C C17' H17D 109.1 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14' C18' H18D 109.5 . . ?
C14' C18' H18E 109.5 . . ?
C14' C18' H18F 109.5 . . ?
H18D C18' H18E 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
O2 C19 N4 123.5(3) . . ?
O2 C19 C10 118.8(3) . . ?
N4 C19 C10 117.8(3) . . ?
N4 C20 H20 110.1 . . ?
N4 C20 C21 101.3(3) . . ?
N4 C20 C24 111.6(3) . . ?
C21 C20 H20 110.1 . . ?
C24 C20 H20 110.1 . . ?
C24 C20 C21 113.2(3) . . ?
C20 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
H21A C21 H21B 109.0 . . ?
C22 C21 C20 104.0(3) . . ?
C22 C21 H21A 110.9 . . ?
C22 C21 H21B 110.9 . . ?
C21 C22 H22A 111.2 . . ?
C21 C22 H22B 111.2 . . ?
H22A C22 H22B 109.1 . . ?
C23 C22 C21 102.8(3) . . ?
C23 C22 H22A 111.2 . . ?
C23 C22 H22B 111.2 . . ?
N4 C23 C22 103.7(3) . . ?
N4 C23 H23A 111.0 . . ?
N4 C23 H23B 111.0 . . ?
C22 C23 H23A 111.0 . . ?
C22 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C1 N1 C12 C4 0.0(5) . . . . ?
C1 N1 C12 C11 179.3(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
N1 C1 C2 C3 -0.5(5) . . . . ?
N1 C1 C13 O1 -164.4(4) . . . . ?
N1 C1 C13 N3 16.0(6) . . . . ?
N1 C1 C13' O1' -138(3) . . . . ?
N1 C1 C13' N3' 32(3) . . . . ?
N2 C10 C19 O2 124.8(3) . . . . ?
N2 C10 C19 N4 -54.6(4) . . . . ?
N2 C11 C12 N1 -0.5(5) . . . . ?
N2 C11 C12 C4 178.8(3) . . . . ?
C2 C1 N1 C12 0.6(5) . . . . ?
C2 C1 C13 O1 16.6(6) . . . . ?
C2 C1 C13 N3 -163.1(4) . . . . ?
C2 C1 C13' O1' 26(4) . . . . ?
C2 C1 C13' N3' -164(2) . . . . ?
C2 C3 C4 C5 -178.5(3) . . . . ?
C2 C3 C4 C12 0.8(5) . . . . ?
C3 C4 C5 C6 179.7(4) . . . . ?
C3 C4 C12 N1 -0.7(5) . . . . ?
C3 C4 C12 C11 -179.9(3) . . . . ?
N3 C14 C15 C16 -29.1(5) . . . . ?
N3' C14' C15' C16' 19(3) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
N4 C20 C21 C22 -33.0(4) . . . . ?
C5 C4 C12 N1 178.6(3) . . . . ?
C5 C4 C12 C11 -0.6(5) . . . . ?
C5 C6 C7 C8 179.7(4) . . . . ?
C5 C6 C7 C11 -0.5(5) . . . . ?
C6 C7 C8 C9 -179.4(3) . . . . ?
C6 C7 C11 N2 -178.1(3) . . . . ?
C6 C7 C11 C12 0.3(5) . . . . ?
C7 C8 C9 C10 -2.2(5) . . . . ?
C7 C11 C12 N1 -179.0(3) . . . . ?
C7 C11 C12 C4 0.2(5) . . . . ?
C8 C7 C11 N2 1.7(5) . . . . ?
C8 C7 C11 C12 -179.8(3) . . . . ?
C8 C9 C10 N2 1.3(5) . . . . ?
C8 C9 C10 C19 176.5(3) . . . . ?
C9 C10 C19 O2 -50.7(4) . . . . ?
C9 C10 C19 N4 129.9(3) . . . . ?
C10 N2 C11 C7 -2.5(5) . . . . ?
C10 N2 C11 C12 179.0(3) . . . . ?
C11 N2 C10 C9 1.0(5) . . . . ?
C11 N2 C10 C19 -174.3(3) . . . . ?
C11 C7 C8 C9 0.8(5) . . . . ?
C12 C4 C5 C6 0.5(6) . . . . ?
C13 C1 N1 C12 -178.3(3) . . . . ?
C13 C1 C2 C3 178.4(4) . . . . ?
C13 N3 C14 C15 -158.9(4) . . . . ?
C13 N3 C14 C18 78.7(6) . . . . ?
C13 N3 C17 C16 178.7(5) . . . . ?
C13' C1 N1 C12 162.9(14) . . . . ?
C13' C1 C2 C3 -164.1(14) . . . . ?
C13' N3' C14' C15' 168(3) . . . . ?
C13' N3' C14' C18' -60(4) . . . . ?
C13' N3' C17' C16' -176(3) . . . . ?
C14 N3 C13 C1 175.0(4) . . . . ?
C14 N3 C13 O1 -4.6(7) . . . . ?
C14 N3 C17 C16 8.1(7) . . . . ?
C14 C15 C16 C17 35.2(6) . . . . ?
C14' N3' C13' C1 -175(2) . . . . ?
C14' N3' C13' O1' -6(5) . . . . ?
C14' N3' C17' C16' 17(4) . . . . ?
C14' C15' C16' C17' -7(3) . . . . ?
C15 C16 C17 N3 -26.4(7) . . . . ?
C15' C16' C17' N3' -6(4) . . . . ?
C17 N3 C13 C1 5.0(8) . . . . ?
C17 N3 C13 O1 -174.6(6) . . . . ?
C17 N3 C14 C15 12.7(6) . . . . ?
C17 N3 C14 C18 -109.8(6) . . . . ?
C17' N3' C13' C1 19(5) . . . . ?
C17' N3' C13' O1' -171(4) . . . . ?
C17' N3' C14' C15' -23(3) . . . . ?
C17' N3' C14' C18' 109(3) . . . . ?
C18 C14 C15 C16 91.4(5) . . . . ?
C18' C14' C15' C16' -114(3) . . . . ?
C19 N4 C20 C21 -165.2(3) . . . . ?
C19 N4 C20 C24 74.0(4) . . . . ?
C19 N4 C23 C22 -170.5(3) . . . . ?
C20 N4 C19 O2 -3.3(5) . . . . ?
C20 N4 C19 C10 176.1(3) . . . . ?
C20 N4 C23 C22 9.9(4) . . . . ?
C20 C21 C22 C23 39.8(4) . . . . ?
C21 C22 C23 N4 -30.2(4) . . . . ?
C23 N4 C19 O2 177.2(3) . . . . ?
C23 N4 C19 C10 -3.4(5) . . . . ?
C23 N4 C20 C21 14.4(4) . . . . ?
C23 N4 C20 C24 -106.4(4) . . . . ?
C24 C20 C21 C22 86.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7539
2 0.2461

####################################################################### 
# 
# 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_L3Nd
_database_code_depnum_ccdc_archive 'CCDC 2164120'
loop_
_audit_author_name
_audit_author_address
'Ksenia Isakovskaya'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-04-03 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-04-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 N7 Nd O11'
_chemical_formula_sum            'C24 H26 N7 Nd O11'
_chemical_formula_weight         732.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.3150(4)
_cell_length_b                   17.7540(7)
_cell_length_c                   16.6429(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.3520(10)
_cell_angle_gamma                90
_cell_volume                     2707.58(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.23
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.782
_shelx_estimated_absorpt_T_min   0.691
_exptl_absorpt_coefficient_mu    1.992
_exptl_absorpt_correction_T_max  0.1561
_exptl_absorpt_correction_T_min  0.0986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.6316.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1468
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29857
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.294
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5760
_reflns_number_total             6523
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.949
_refine_diff_density_min         -2.344
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6523
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.244
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0128P)²+23.6422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1403
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O11-N7 \\sim O11'-N7'
 with sigma of 0.02
 O10'-N7' \\sim O10-N7
 with sigma of 0.02
 O9-N7 \\sim O9'-N7'
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O10') \\sim Ueq, Uanis(N7') \\sim Ueq, Uanis(O11) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C20') = Uanis(C20)
Uanis(C21') = Uanis(C21)
Uanis(C22') = Uanis(C22)
Uanis(C24) = Uanis(C24')
Uanis(C23) = Uanis(C23')
Uanis(O9) = Uanis(O9')
Uanis(O11) = Uanis(O11')
Uanis(N7) = Uanis(N7')
Uanis(O10') = Uanis(O10)
3. Others
 Sof(C20')=Sof(H20')=Sof(C21')=Sof(H21C)=Sof(H21D)=Sof(C22')=Sof(H22C)=
 Sof(H22D)=Sof(C23')=Sof(H23C)=Sof(H23D)=Sof(C24')=Sof(H24D)=Sof(H24E)=
 Sof(H24F)=1-FVAR(1)
 Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
 Sof(N7')=Sof(O9')=Sof(O10')=Sof(O11')=1-FVAR(2)
 Sof(N7)=Sof(O9)=Sof(O10)=Sof(O11)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C20(H20), C20'(H20')
4.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C21(H21A,H21B), C21'(H21C,
 H21D), C22(H22A,H22B), C22'(H22C,H22D), C23(H23A,H23B), C23'(H23C,H23D)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C24(H24A,H24B,H24C), C24'(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5616(5) 0.6544(3) 0.6477(3) 0.0365(11) Uani 1 1 d . . . . .
C1 C 0.4500(8) 0.5527(4) 0.7038(4) 0.0356(15) Uani 1 1 d . . . . .
N1 N 0.3268(7) 0.5812(3) 0.6637(3) 0.0328(13) Uani 1 1 d . . . . .
Nd1 Nd 0.32869(4) 0.71186(2) 0.59304(2) 0.02966(11) Uani 1 1 d . . . . .
N2 N 0.0849(6) 0.6381(3) 0.5716(3) 0.0311(12) Uani 1 1 d . . . . .
O2 O 0.1324(6) 0.7519(3) 0.4798(3) 0.0420(12) Uani 1 1 d . . . . .
C2 C 0.4556(9) 0.4808(4) 0.7384(5) 0.0402(17) Uani 1 1 d . . . . .
H2 H 0.5460 0.4609 0.7657 0.048 Uiso 1 1 calc R U . . .
O3 O 0.4647(6) 0.7080(3) 0.4754(3) 0.0434(13) Uani 1 1 d . . . . .
C3 C 0.3317(9) 0.4392(4) 0.7330(4) 0.0412(17) Uani 1 1 d . . . . .
H3 H 0.3348 0.3910 0.7579 0.049 Uiso 1 1 calc R U . . .
N3 N 0.6982(7) 0.6040(4) 0.7591(4) 0.0390(14) Uani 1 1 d . . . . .
O4 O 0.3450(5) 0.6074(3) 0.4930(3) 0.0367(11) Uani 1 1 d . . . . .
N4 N -0.0875(8) 0.8000(4) 0.4848(5) 0.0508(18) Uani 1 1 d . . . . .
C4 C 0.1979(9) 0.4681(4) 0.6901(4) 0.0365(16) Uani 1 1 d . . . . .
N5 N 0.4328(7) 0.6408(4) 0.4545(4) 0.0427(15) Uani 1 1 d . . . . .
C5 C 0.0622(9) 0.4278(4) 0.6793(5) 0.0414(17) Uani 1 1 d . . . . .
H5 H 0.0577 0.3799 0.7042 0.050 Uiso 1 1 calc R U . . .
O5 O 0.4817(8) 0.6097(4) 0.4011(4) 0.0670(19) Uani 1 1 d . . . . .
C6 C -0.0588(9) 0.4576(4) 0.6340(5) 0.0425(18) Uani 1 1 d . . . . .
H6 H -0.1476 0.4301 0.6281 0.051 Uiso 1 1 calc R U . . .
N6 N 0.2617(8) 0.7466(3) 0.7584(4) 0.0411(15) Uani 1 1 d . . . . .
O6 O 0.1620(7) 0.7341(4) 0.7000(4) 0.0541(16) Uani 1 1 d . . . . .
O7 O 0.3917(7) 0.7418(3) 0.7442(3) 0.0506(14) Uani 1 1 d . . . . .
C7 C -0.0584(8) 0.5297(4) 0.5943(4) 0.0344(15) Uani 1 1 d . . . . .
N7 N 0.448(3) 0.8709(13) 0.6220(18) 0.045(2) Uani 0.290(18) 1 d D . P A 1
N7' N 0.3883(14) 0.8805(6) 0.6055(7) 0.045(2) Uani 0.710(18) 1 d D U P A 2
O8 O 0.2378(8) 0.7656(3) 0.8254(3) 0.0541(16) Uani 1 1 d . . . . .
C8 C -0.1789(8) 0.5622(4) 0.5437(4) 0.0395(17) Uani 1 1 d . . . . .
H8 H -0.2689 0.5357 0.5326 0.047 Uiso 1 1 calc R U . . .
C9 C -0.1677(8) 0.6322(4) 0.5100(4) 0.0364(15) Uani 1 1 d . . . . .
H9 H -0.2493 0.6551 0.4765 0.044 Uiso 1 1 calc R U . . .
O9 O 0.312(3) 0.8484(17) 0.625(2) 0.049(2) Uani 0.290(18) 1 d D . P A 1
O9' O 0.2559(12) 0.8545(6) 0.6090(7) 0.049(2) Uani 0.710(18) 1 d D . P A 2
C10 C -0.0317(8) 0.6689(4) 0.5267(4) 0.0324(14) Uani 1 1 d . . . . .
O10 O 0.520(3) 0.8180(14) 0.6120(19) 0.055(2) Uani 0.290(18) 1 d D . P A 1
O10' O 0.4716(13) 0.8324(6) 0.5891(7) 0.055(2) Uani 0.710(18) 1 d D U P A 2
C11 C 0.0739(8) 0.5708(4) 0.6065(4) 0.0317(14) Uani 1 1 d . . . . .
O11 O 0.490(4) 0.9337(14) 0.630(2) 0.072(4) Uani 0.290(18) 1 d D U P A 1
O11' O 0.4191(17) 0.9453(6) 0.6139(9) 0.072(4) Uani 0.710(18) 1 d D . P A 2
C12 C 0.2023(8) 0.5395(4) 0.6554(4) 0.0314(14) Uani 1 1 d . . . . .
C13 C 0.5758(8) 0.6060(4) 0.7038(4) 0.0350(15) Uani 1 1 d . . . . .
C14 C 0.8169(8) 0.6622(4) 0.7573(5) 0.0424(18) Uani 1 1 d . . . . .
H14 H 0.8458 0.6629 0.7023 0.051 Uiso 1 1 calc R U . . .
C15 C 0.9412(10) 0.6307(6) 0.8210(6) 0.058(2) Uani 1 1 d . . . . .
H15A H 1.0063 0.6714 0.8468 0.069 Uiso 1 1 calc R U . . .
H15B H 0.9996 0.5934 0.7965 0.069 Uiso 1 1 calc R U . . .
C16 C 0.8595(10) 0.5932(5) 0.8833(5) 0.053(2) Uani 1 1 d . . . . .
H16A H 0.9238 0.5576 0.9189 0.064 Uiso 1 1 calc R U . . .
H16B H 0.8223 0.6314 0.9177 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7343(9) 0.5517(5) 0.8297(5) 0.0457(19) Uani 1 1 d . . . . .
H17A H 0.7658 0.5019 0.8125 0.055 Uiso 1 1 calc R U . . .
H17B H 0.6505 0.5450 0.8580 0.055 Uiso 1 1 calc R U . . .
C18 C 0.7699(10) 0.7394(5) 0.7789(6) 0.052(2) Uani 1 1 d . . . . .
H18A H 0.6902 0.7569 0.7364 0.078 Uiso 1 1 calc R U . . .
H18B H 0.8525 0.7742 0.7830 0.078 Uiso 1 1 calc R U . . .
H18C H 0.7364 0.7374 0.8314 0.078 Uiso 1 1 calc R U . . .
C19 C 0.0065(8) 0.7443(4) 0.4942(4) 0.0358(16) Uani 1 1 d . . . . .
C20 C -0.2209(17) 0.8099(10) 0.5040(9) 0.051(3) Uani 0.629(9) 1 d . . P B 1
H20 H -0.2970 0.7721 0.4813 0.061 Uiso 0.629(9) 1 calc R U P B 1
C20' C -0.062(3) 0.8810(15) 0.4785(15) 0.051(3) Uani 0.371(9) 1 d . . P B 2
H20' H 0.0452 0.8902 0.4920 0.061 Uiso 0.371(9) 1 calc R U P B 2
C21 C -0.259(2) 0.8901(10) 0.4861(10) 0.068(4) Uani 0.629(9) 1 d . . P B 1
H21A H -0.2210 0.9225 0.5337 0.081 Uiso 0.629(9) 1 calc R U P B 1
H21B H -0.3654 0.8970 0.4709 0.081 Uiso 0.629(9) 1 calc R U P B 1
C21' C -0.131(3) 0.9261(17) 0.5314(17) 0.068(4) Uani 0.371(9) 1 d . . P B 2
H21C H -0.1986 0.9618 0.4981 0.081 Uiso 0.371(9) 1 calc R U P B 2
H21D H -0.0555 0.9560 0.5672 0.081 Uiso 0.371(9) 1 calc R U P B 2
C22 C -0.183(2) 0.9075(10) 0.4151(13) 0.077(5) Uani 0.629(9) 1 d . . P B 1
H22A H -0.2392 0.8870 0.3635 0.093 Uiso 0.629(9) 1 calc R U P B 1
H22B H -0.1711 0.9624 0.4090 0.093 Uiso 0.629(9) 1 calc R U P B 1
C22' C -0.216(4) 0.8795(16) 0.585(2) 0.077(5) Uani 0.371(9) 1 d . . P B 2
H22C H -0.3121 0.9021 0.5874 0.093 Uiso 0.371(9) 1 calc R U P B 2
H22D H -0.1601 0.8725 0.6406 0.093 Uiso 0.371(9) 1 calc R U P B 2
C23 C -0.0385(15) 0.8689(8) 0.4380(10) 0.046(3) Uani 0.629(9) 1 d . U P B 1
H23A H 0.0336 0.9007 0.4737 0.055 Uiso 0.629(9) 1 calc R U P B 1
H23B H 0.0015 0.8532 0.3894 0.055 Uiso 0.629(9) 1 calc R U P B 1
C23' C -0.233(3) 0.8002(16) 0.5326(18) 0.046(3) Uani 0.371(9) 1 d . . P B 2
H23C H -0.3250 0.7992 0.4926 0.055 Uiso 0.371(9) 1 calc R U P B 2
H23D H -0.2298 0.7562 0.5694 0.055 Uiso 0.371(9) 1 calc R U P B 2
C24 C -0.172(3) 0.8103(15) 0.5992(14) 0.109(7) Uani 0.629(9) 1 d . . P B 1
H24A H -0.1007 0.7700 0.6153 0.163 Uiso 0.629(9) 1 calc R U P B 1
H24B H -0.2570 0.8022 0.6252 0.163 Uiso 0.629(9) 1 calc R U P B 1
H24C H -0.1273 0.8590 0.6166 0.163 Uiso 0.629(9) 1 calc R U P B 1
C24' C -0.110(5) 0.894(3) 0.391(2) 0.109(7) Uani 0.371(9) 1 d . . P B 2
H24D H -0.0478 0.8646 0.3605 0.163 Uiso 0.371(9) 1 calc R U P B 2
H24E H -0.1021 0.9474 0.3789 0.163 Uiso 0.371(9) 1 calc R U P B 2
H24F H -0.2115 0.8774 0.3748 0.163 Uiso 0.371(9) 1 calc R U P B 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
O1 Nd1 2.422(5) . ?
O1 C13 1.258(9) . ?
C1 N1 1.319(9) . ?
C1 C2 1.399(11) . ?
C1 C13 1.507(10) . ?
N1 Nd1 2.603(6) . ?
N1 C12 1.362(9) . ?
Nd1 N2 2.590(6) . ?
Nd1 O2 2.482(5) . ?
Nd1 O3 2.517(5) . ?
Nd1 O4 2.515(5) . ?
Nd1 O6 2.594(6) . ?
Nd1 O7 2.535(5) . ?
Nd1 O9 2.49(3) . ?
Nd1 O9' 2.647(11) . ?
Nd1 O10 2.57(3) . ?
Nd1 O10' 2.527(11) . ?
N2 C10 1.322(9) . ?
N2 C11 1.341(9) . ?
O2 C19 1.245(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.359(11) . ?
O3 N5 1.263(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.416(11) . ?
N3 C13 1.331(9) . ?
N3 C14 1.517(10) . ?
N3 C17 1.487(10) . ?
O4 N5 1.273(8) . ?
N4 C19 1.312(10) . ?
N4 C20 1.349(16) . ?
N4 C20' 1.47(3) . ?
N4 C23 1.562(16) . ?
N4 C23' 1.69(3) . ?
C4 C5 1.436(10) . ?
C4 C12 1.397(10) . ?
N5 O5 1.203(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.346(11) . ?
C6 H6 0.9500 . ?
C6 C7 1.443(10) . ?
N6 O6 1.237(9) . ?
N6 O7 1.278(9) . ?
N6 O8 1.223(8) . ?
C7 C8 1.401(11) . ?
C7 C11 1.414(9) . ?
N7 O9 1.337(19) . ?
N7 O10 1.181(19) . ?
N7 O11 1.179(18) . ?
N7' O9' 1.328(12) . ?
N7' O10' 1.218(13) . ?
N7' O11' 1.188(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.406(9) . ?
C10 C19 1.510(10) . ?
C11 C12 1.432(10) . ?
C14 H14 1.0000 . ?
C14 C15 1.528(11) . ?
C14 C18 1.502(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.542(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.524(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20 1.0000 . ?
C20 C21 1.48(2) . ?
C20 C24 1.57(3) . ?
C20' H20' 1.0000 . ?
C20' C21' 1.42(3) . ?
C20' C24' 1.46(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.51(3) . ?
C21' H21C 0.9900 . ?
C21' H21D 0.9900 . ?
C21' C22' 1.53(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.50(2) . ?
C22' H22C 0.9900 . ?
C22' H22D 0.9900 . ?
C22' C23' 1.65(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23' H23C 0.9900 . ?
C23' H23D 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24' H24D 0.9800 . ?
C24' H24E 0.9800 . ?
C24' H24F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 Nd1 122.3(5) . . ?
N1 C1 C2 121.5(7) . . ?
N1 C1 C13 111.4(6) . . ?
C2 C1 C13 127.0(7) . . ?
C1 N1 Nd1 119.6(5) . . ?
C1 N1 C12 119.4(6) . . ?
C12 N1 Nd1 120.9(5) . . ?
O1 Nd1 N1 62.17(18) . . ?
O1 Nd1 N2 122.88(18) . . ?
O1 Nd1 O2 153.37(17) . . ?
O1 Nd1 O3 74.86(18) . . ?
O1 Nd1 O4 77.39(16) . . ?
O1 Nd1 O6 114.34(19) . . ?
O1 Nd1 O7 71.53(18) . . ?
O1 Nd1 O9 114.5(6) . . ?
O1 Nd1 O9' 126.4(3) . . ?
O1 Nd1 O10 73.1(7) . . ?
O1 Nd1 O10' 85.7(3) . . ?
N1 Nd1 O9' 141.7(3) . . ?
N2 Nd1 N1 62.26(19) . . ?
N2 Nd1 O6 63.46(18) . . ?
N2 Nd1 O9' 105.3(3) . . ?
O2 Nd1 N1 122.32(18) . . ?
O2 Nd1 N2 62.12(18) . . ?
O2 Nd1 O3 79.77(18) . . ?
O2 Nd1 O4 80.37(18) . . ?
O2 Nd1 O6 91.57(19) . . ?
O2 Nd1 O7 134.49(19) . . ?
O2 Nd1 O9 79.5(7) . . ?
O2 Nd1 O9' 68.6(3) . . ?
O2 Nd1 O10 106.4(7) . . ?
O2 Nd1 O10' 93.3(3) . . ?
O3 Nd1 N1 111.88(18) . . ?
O3 Nd1 N2 115.52(17) . . ?
O3 Nd1 O6 170.1(2) . . ?
O3 Nd1 O7 135.95(19) . . ?
O3 Nd1 O9' 106.1(3) . . ?
O3 Nd1 O10 71.4(6) . . ?
O3 Nd1 O10' 70.2(3) . . ?
O4 Nd1 N1 69.39(17) . . ?
O4 Nd1 N2 72.06(17) . . ?
O4 Nd1 O3 50.67(17) . . ?
O4 Nd1 O6 132.94(18) . . ?
O4 Nd1 O7 141.34(18) . . ?
O4 Nd1 O9' 145.0(3) . . ?
O4 Nd1 O10 119.9(6) . . ?
O4 Nd1 O10' 120.8(3) . . ?
O6 Nd1 N1 76.81(19) . . ?
O6 Nd1 O9' 65.8(3) . . ?
O7 Nd1 N1 75.96(19) . . ?
O7 Nd1 N2 106.46(19) . . ?
O7 Nd1 O6 49.25(19) . . ?
O7 Nd1 O9' 73.6(3) . . ?
O7 Nd1 O10 72.1(7) . . ?
O9 Nd1 N1 139.9(7) . . ?
O9 Nd1 N2 115.8(6) . . ?
O9 Nd1 O3 104.5(7) . . ?
O9 Nd1 O4 150.6(7) . . ?
O9 Nd1 O6 68.9(7) . . ?
O9 Nd1 O7 66.2(7) . . ?
O9 Nd1 O10 47.8(7) . . ?
O10 Nd1 N1 131.2(7) . . ?
O10 Nd1 N2 163.3(6) . . ?
O10 Nd1 O6 106.9(6) . . ?
O10' Nd1 N1 144.4(3) . . ?
O10' Nd1 N2 151.3(3) . . ?
O10' Nd1 O6 105.8(3) . . ?
O10' Nd1 O7 79.6(3) . . ?
O10' Nd1 O9' 48.6(3) . . ?
C10 N2 Nd1 118.7(4) . . ?
C10 N2 C11 119.7(6) . . ?
C11 N2 Nd1 121.6(5) . . ?
C19 O2 Nd1 114.4(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(7) . . ?
C3 C2 H2 120.0 . . ?
N5 O3 Nd1 96.5(4) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(7) . . ?
C4 C3 H3 120.1 . . ?
C13 N3 C14 120.3(6) . . ?
C13 N3 C17 127.4(7) . . ?
C17 N3 C14 112.2(6) . . ?
N5 O4 Nd1 96.3(4) . . ?
C19 N4 C20 134.0(10) . . ?
C19 N4 C20' 129.6(12) . . ?
C19 N4 C23 113.7(8) . . ?
C19 N4 C23' 121.3(12) . . ?
C20 N4 C23 112.3(10) . . ?
C20' N4 C23' 100.6(15) . . ?
C3 C4 C5 124.0(7) . . ?
C12 C4 C3 116.6(7) . . ?
C12 C4 C5 119.4(7) . . ?
O3 N5 Nd1 58.2(3) . . ?
O3 N5 O4 116.3(6) . . ?
O4 N5 Nd1 58.2(3) . . ?
O5 N5 Nd1 176.1(6) . . ?
O5 N5 O3 122.3(7) . . ?
O5 N5 O4 121.4(7) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(7) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 118.8 . . ?
C5 C6 C7 122.3(7) . . ?
C7 C6 H6 118.8 . . ?
O6 N6 Nd1 59.5(4) . . ?
O6 N6 O7 116.5(6) . . ?
O7 N6 Nd1 57.0(3) . . ?
O8 N6 Nd1 175.7(5) . . ?
O8 N6 O6 122.1(7) . . ?
O8 N6 O7 121.4(7) . . ?
N6 O6 Nd1 96.3(4) . . ?
N6 O7 Nd1 98.0(4) . . ?
C8 C7 C6 124.9(7) . . ?
C8 C7 C11 117.3(7) . . ?
C11 C7 C6 117.7(7) . . ?
O10 N7 O9 109(2) . . ?
O11 N7 O9 125(3) . . ?
O11 N7 O10 126(3) . . ?
O10' N7' O9' 113.5(10) . . ?
O11' N7' O9' 122.6(12) . . ?
O11' N7' O10' 123.8(12) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.3(7) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 118.0(7) . . ?
C10 C9 H9 121.0 . . ?
N7 O9 Nd1 100.9(18) . . ?
N7' O9' Nd1 94.1(7) . . ?
N2 C10 C9 122.7(7) . . ?
N2 C10 C19 110.3(6) . . ?
C9 C10 C19 127.0(7) . . ?
N7 O10 Nd1 101.8(19) . . ?
N7' O10' Nd1 103.2(8) . . ?
N2 C11 C7 121.9(7) . . ?
N2 C11 C12 118.1(6) . . ?
C7 C11 C12 119.9(6) . . ?
N1 C12 C4 122.6(7) . . ?
N1 C12 C11 117.1(6) . . ?
C4 C12 C11 120.3(7) . . ?
O1 C13 C1 116.8(6) . . ?
O1 C13 N3 119.6(7) . . ?
N3 C13 C1 123.5(7) . . ?
N3 C14 H14 110.2 . . ?
N3 C14 C15 101.6(7) . . ?
C15 C14 H14 110.2 . . ?
C18 C14 N3 111.8(6) . . ?
C18 C14 H14 110.2 . . ?
C18 C14 C15 112.6(7) . . ?
C14 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C14 C15 C16 102.7(7) . . ?
H15A C15 H15B 109.1 . . ?
C16 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
C15 C16 H16A 111.1 . . ?
C15 C16 H16B 111.1 . . ?
H16A C16 H16B 109.0 . . ?
C17 C16 C15 103.5(7) . . ?
C17 C16 H16A 111.1 . . ?
C17 C16 H16B 111.1 . . ?
N3 C17 C16 101.6(7) . . ?
N3 C17 H17A 111.4 . . ?
N3 C17 H17B 111.4 . . ?
C16 C17 H17A 111.4 . . ?
C16 C17 H17B 111.4 . . ?
H17A C17 H17B 109.3 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 N4 121.7(7) . . ?
O2 C19 C10 117.2(7) . . ?
N4 C19 C10 121.0(7) . . ?
N4 C20 H20 116.3 . . ?
N4 C20 C21 105.8(13) . . ?
N4 C20 C24 97.3(13) . . ?
C21 C20 H20 116.3 . . ?
C21 C20 C24 102.4(15) . . ?
C24 C20 H20 116.3 . . ?
N4 C20' H20' 108.1 . . ?
C21' C20' N4 114(2) . . ?
C21' C20' H20' 108.1 . . ?
C21' C20' C24' 116(3) . . ?
C24' C20' N4 101(3) . . ?
C24' C20' H20' 108.2 . . ?
C20 C21 H21A 111.1 . . ?
C20 C21 H21B 111.1 . . ?
C20 C21 C22 103.1(13) . . ?
H21A C21 H21B 109.1 . . ?
C22 C21 H21A 111.1 . . ?
C22 C21 H21B 111.1 . . ?
C20' C21' H21C 109.0 . . ?
C20' C21' H21D 109.0 . . ?
C20' C21' C22' 113(3) . . ?
H21C C21' H21D 107.8 . . ?
C22' C21' H21C 109.0 . . ?
C22' C21' H21D 109.0 . . ?
C21 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.1 . . ?
C23 C22 C21 103.3(15) . . ?
C23 C22 H22A 111.1 . . ?
C23 C22 H22B 111.1 . . ?
C21' C22' H22C 111.9 . . ?
C21' C22' H22D 111.9 . . ?
C21' C22' C23' 100(3) . . ?
H22C C22' H22D 109.6 . . ?
C23' C22' H22C 111.9 . . ?
C23' C22' H22D 111.9 . . ?
N4 C23 H23A 112.0 . . ?
N4 C23 H23B 112.0 . . ?
C22 C23 N4 98.9(12) . . ?
C22 C23 H23A 112.0 . . ?
C22 C23 H23B 112.0 . . ?
H23A C23 H23B 109.7 . . ?
N4 C23' H23C 110.9 . . ?
N4 C23' H23D 110.9 . . ?
C22' C23' N4 104(2) . . ?
C22' C23' H23C 110.9 . . ?
C22' C23' H23D 110.9 . . ?
H23C C23' H23D 109.0 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20' C24' H24D 109.5 . . ?
C20' C24' H24E 109.5 . . ?
C20' C24' H24F 109.5 . . ?
H24D C24' H24E 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 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
C1 N1 C12 C4 2.2(10) . . . . ?
C1 N1 C12 C11 -175.7(6) . . . . ?
C1 C2 C3 C4 1.9(11) . . . . ?
N1 C1 C2 C3 -1.7(11) . . . . ?
N1 C1 C13 O1 -22.5(9) . . . . ?
N1 C1 C13 N3 157.5(7) . . . . ?
Nd1 O1 C13 C1 34.6(8) . . . . ?
Nd1 O1 C13 N3 -145.5(5) . . . . ?
Nd1 N1 C12 C4 177.8(5) . . . . ?
Nd1 N1 C12 C11 -0.1(8) . . . . ?
Nd1 N2 C10 C9 178.3(5) . . . . ?
Nd1 N2 C10 C19 1.4(7) . . . . ?
Nd1 N2 C11 C7 -179.1(5) . . . . ?
Nd1 N2 C11 C12 -1.1(8) . . . . ?
Nd1 O2 C19 N4 127.7(6) . . . . ?
Nd1 O2 C19 C10 -49.5(7) . . . . ?
Nd1 O3 N5 O4 4.7(7) . . . . ?
Nd1 O3 N5 O5 -175.5(7) . . . . ?
Nd1 O4 N5 O3 -4.7(7) . . . . ?
Nd1 O4 N5 O5 175.5(7) . . . . ?
N2 C10 C19 O2 31.6(9) . . . . ?
N2 C10 C19 N4 -145.7(7) . . . . ?
N2 C11 C12 N1 0.8(9) . . . . ?
N2 C11 C12 C4 -177.2(6) . . . . ?
C2 C1 N1 Nd1 -176.0(5) . . . . ?
C2 C1 N1 C12 -0.4(10) . . . . ?
C2 C1 C13 O1 155.7(7) . . . . ?
C2 C1 C13 N3 -24.3(11) . . . . ?
C2 C3 C4 C5 178.4(7) . . . . ?
C2 C3 C4 C12 -0.2(10) . . . . ?
C3 C4 C5 C6 -176.5(7) . . . . ?
C3 C4 C12 N1 -1.9(10) . . . . ?
C3 C4 C12 C11 176.0(6) . . . . ?
N3 C14 C15 C16 -33.1(8) . . . . ?
N4 C20 C21 C22 31.8(17) . . . . ?
N4 C20' C21' C22' 1(3) . . . . ?
C4 C5 C6 C7 0.4(12) . . . . ?
C5 C4 C12 N1 179.4(6) . . . . ?
C5 C4 C12 C11 -2.7(10) . . . . ?
C5 C6 C7 C8 177.2(8) . . . . ?
C5 C6 C7 C11 -2.3(11) . . . . ?
C6 C7 C8 C9 178.6(7) . . . . ?
C6 C7 C11 N2 179.6(6) . . . . ?
C6 C7 C11 C12 1.6(10) . . . . ?
O6 N6 O7 Nd1 2.0(7) . . . . ?
O7 N6 O6 Nd1 -1.9(7) . . . . ?
C7 C8 C9 C10 1.2(11) . . . . ?
C7 C11 C12 N1 178.9(6) . . . . ?
C7 C11 C12 C4 0.8(10) . . . . ?
O8 N6 O6 Nd1 175.4(6) . . . . ?
O8 N6 O7 Nd1 -175.3(6) . . . . ?
C8 C7 C11 N2 0.1(10) . . . . ?
C8 C7 C11 C12 -177.9(6) . . . . ?
C8 C9 C10 N2 1.4(11) . . . . ?
C8 C9 C10 C19 177.8(7) . . . . ?
C9 C10 C19 O2 -145.1(7) . . . . ?
C9 C10 C19 N4 37.6(11) . . . . ?
O9 N7 O10 Nd1 5(3) . . . . ?
O9' N7' O10' Nd1 -7.4(11) . . . . ?
C10 N2 C11 C7 2.5(10) . . . . ?
C10 N2 C11 C12 -179.5(6) . . . . ?
O10 N7 O9 Nd1 -5(3) . . . . ?
O10' N7' O9' Nd1 6.9(11) . . . . ?
C11 N2 C10 C9 -3.3(10) . . . . ?
C11 N2 C10 C19 179.8(6) . . . . ?
C11 C7 C8 C9 -1.9(10) . . . . ?
O11 N7 O9 Nd1 177(3) . . . . ?
O11 N7 O10 Nd1 -177(3) . . . . ?
O11' N7' O9' Nd1 -176.3(12) . . . . ?
O11' N7' O10' Nd1 175.8(12) . . . . ?
C12 C4 C5 C6 2.1(11) . . . . ?
C13 C1 N1 Nd1 2.3(7) . . . . ?
C13 C1 N1 C12 177.9(6) . . . . ?
C13 C1 C2 C3 -179.7(7) . . . . ?
C13 N3 C14 C15 -171.4(7) . . . . ?
C13 N3 C14 C18 68.2(9) . . . . ?
C13 N3 C17 C16 -161.9(7) . . . . ?
C14 N3 C13 O1 3.1(10) . . . . ?
C14 N3 C13 C1 -176.9(6) . . . . ?
C14 N3 C17 C16 14.7(8) . . . . ?
C14 C15 C16 C17 43.7(9) . . . . ?
C15 C16 C17 N3 -35.2(8) . . . . ?
C17 N3 C13 O1 179.5(7) . . . . ?
C17 N3 C13 C1 -0.6(11) . . . . ?
C17 N3 C14 C15 11.8(8) . . . . ?
C17 N3 C14 C18 -108.6(8) . . . . ?
C18 C14 C15 C16 86.7(9) . . . . ?
C19 N4 C20 C21 172.7(10) . . . . ?
C19 N4 C20 C24 67.6(18) . . . . ?
C19 N4 C20' C21' -130.1(19) . . . . ?
C19 N4 C20' C24' 104(2) . . . . ?
C19 N4 C23 C22 162.6(11) . . . . ?
C19 N4 C23' C22' 123.6(17) . . . . ?
C20 N4 C19 O2 -171.2(12) . . . . ?
C20 N4 C19 C10 6.0(16) . . . . ?
C20 N4 C23 C22 -15.0(16) . . . . ?
C20 C21 C22 C23 -41.4(17) . . . . ?
C20' N4 C19 O2 -17.5(18) . . . . ?
C20' N4 C19 C10 159.7(14) . . . . ?
C20' N4 C23' C22' -27(2) . . . . ?
C20' C21' C22' C23' -18(3) . . . . ?
C21 C22 C23 N4 33.3(15) . . . . ?
C21' C22' C23' N4 27(3) . . . . ?
C23 N4 C19 O2 12.0(11) . . . . ?
C23 N4 C19 C10 -170.9(8) . . . . ?
C23 N4 C20 C21 -10.4(16) . . . . ?
C23 N4 C20 C24 -115.5(14) . . . . ?
C23' N4 C19 O2 -159.1(13) . . . . ?
C23' N4 C19 C10 18.1(15) . . . . ?
C23' N4 C20' C21' 17(2) . . . . ?
C23' N4 C20' C24' -109(2) . . . . ?
C24 C20 C21 C22 133.1(15) . . . . ?
C24' C20' C21' C22' 118(3) . . . . ?

_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_L4Nd
_database_code_depnum_ccdc_archive 'CCDC 2164121'
loop_
_audit_author_name
_audit_author_address
'Ksenia Isakovskaya'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-04-03 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-04-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 Cl2 N7 Nd O11, 2(C2 H3 N)'
_chemical_formula_sum            'C28 H30 Cl2 N9 Nd O11'
_chemical_formula_weight         883.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.8774(4)
_cell_length_b                   17.5953(3)
_cell_length_c                   19.4525(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.0550(10)
_cell_angle_gamma                90
_cell_volume                     6890.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.819
_shelx_estimated_absorpt_T_min   0.681
_exptl_absorpt_coefficient_mu    1.734
_exptl_absorpt_correction_T_max  0.1561
_exptl_absorpt_correction_T_min  0.1103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1129 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.7066.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3544
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            84838
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.023
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                13227
_reflns_number_total             16627
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.300
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     927
_refine_ls_number_reflns         16627
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+31.2354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1100
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(N4S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
2.a Ternary CH refined with riding coordinates:
 C14A(H14A), C20A(H20A), C14(H14), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C21A(H21A,H21B), C22A(H22A,
 H22B), C23A(H23A,H23B), C15(H15C,H15D), C16(H16C,H16D), C17(H17C,H17D),
 C21(H21C,H21D), C22(H22C,H22D), C23(H23C,H23D)
2.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C5A(H5A), C6A(H6A), C9A(H9A), C2(H2), C5(H5), C6(H6), C9(H9)
2.d Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C24A(H24A,H24B,H24C), C18(H18D,H18E,H18F), C24(H24D,
 H24E,H24F), C8S(H8SA,H8SB,H8SC), C6S(H6SA,H6SB,H6SC), C4S(H4SA,H4SB,H4SC),
 C2S(H2SA,H2SB,H2SC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.00949(5) 0.41371(6) 0.69348(6) 0.0286(2) Uani 1 1 d . . . . .
Nd1A Nd -0.02947(2) 0.25881(2) 0.34200(2) 0.01819(6) Uani 1 1 d . . . . .
C1A C -0.05293(19) 0.2986(2) 0.5034(2) 0.0190(8) Uani 1 1 d . . . . .
O1A O -0.06444(14) 0.18790(15) 0.43165(16) 0.0221(6) Uani 1 1 d . . . . .
N1A N -0.01913(16) 0.32722(18) 0.46572(19) 0.0188(7) Uani 1 1 d . . . . .
C2A C -0.0472(2) 0.3255(2) 0.5732(2) 0.0222(8) Uani 1 1 d . . . . .
H2A H -0.0733 0.3046 0.5978 0.027 Uiso 1 1 calc R U . . .
O2A O 0.03643(15) 0.29795(16) 0.27168(16) 0.0236(6) Uani 1 1 d . . . . .
N2A N 0.04965(17) 0.37954(18) 0.38905(19) 0.0196(7) Uani 1 1 d . . . . .
Cl2A Cl 0.22008(5) 0.54101(6) 0.48953(6) 0.0256(2) Uani 1 1 d . . . . .
C3A C -0.0027(2) 0.3831(2) 0.6051(2) 0.0212(8) Uani 1 1 d . . . . .
O3A O -0.14425(15) 0.30210(16) 0.32767(17) 0.0259(6) Uani 1 1 d . . . . .
N3A N -0.14459(17) 0.20747(19) 0.4759(2) 0.0216(7) Uani 1 1 d . . . . .
O4A O -0.09067(15) 0.38233(16) 0.28782(18) 0.0273(7) Uani 1 1 d . . . . .
N4A N 0.06920(17) 0.39437(19) 0.21816(19) 0.0211(7) Uani 1 1 d . . . . .
C4A C 0.03551(19) 0.4149(2) 0.5680(2) 0.0194(8) Uani 1 1 d . . . . .
N5A N -0.14285(18) 0.3670(2) 0.2992(2) 0.0254(8) Uani 1 1 d . . . . .
C5A C 0.0850(2) 0.4724(2) 0.5985(2) 0.0229(8) Uani 1 1 d . . . . .
H5A H 0.0917 0.4944 0.6455 0.027 Uiso 1 1 calc R U . . .
O5A O -0.18855(16) 0.41201(18) 0.2842(2) 0.0346(8) Uani 1 1 d . . . . .
N6A N 0.0823(2) 0.1568(2) 0.4204(2) 0.0350(9) Uani 1 1 d . . . . .
C6A C 0.1224(2) 0.4959(2) 0.5610(2) 0.0214(8) Uani 1 1 d . . . . .
H6A H 0.1554 0.5336 0.5826 0.026 Uiso 1 1 calc R U . . .
O6A O 0.07952(17) 0.22263(19) 0.44473(19) 0.0335(7) Uani 1 1 d . . . . .
N7A N -0.12507(18) 0.1732(2) 0.2115(2) 0.0252(8) Uani 1 1 d . . . . .
C7A C 0.11324(19) 0.4651(2) 0.4901(2) 0.0198(8) Uani 1 1 d . . . . .
O7A O 0.03716(18) 0.13968(17) 0.35626(19) 0.0332(7) Uani 1 1 d . . . . .
O8A O 0.1246(2) 0.1113(2) 0.4549(2) 0.0592(12) Uani 1 1 d . . . . .
C8A C 0.15201(19) 0.4829(2) 0.4487(2) 0.0208(8) Uani 1 1 d . . . . .
O9A O -0.09807(16) 0.23521(17) 0.20402(17) 0.0268(6) Uani 1 1 d . . . . .
C9A C 0.1379(2) 0.4531(2) 0.3794(2) 0.0231(8) Uani 1 1 d . . . . .
H9A H 0.1635 0.4665 0.3515 0.028 Uiso 1 1 calc R U . . .
C10A C 0.0844(2) 0.4021(2) 0.3504(2) 0.0209(8) Uani 1 1 d . . . . .
O10A O -0.11023(16) 0.15066(17) 0.27766(17) 0.0291(7) Uani 1 1 d . . . . .
C11A C 0.06282(19) 0.4109(2) 0.4564(2) 0.0191(8) Uani 1 1 d . . . . .
O11A O -0.16272(18) 0.1378(2) 0.15794(18) 0.0386(8) Uani 1 1 d . . . . .
C12A C 0.02396(19) 0.3842(2) 0.4970(2) 0.0185(8) Uani 1 1 d . . . . .
C13A C -0.0900(2) 0.2271(2) 0.4670(2) 0.0197(8) Uani 1 1 d . . . . .
C14A C -0.1794(2) 0.1354(3) 0.4419(3) 0.0324(10) Uani 1 1 d . . . . .
H14A H -0.1824 0.1308 0.3894 0.039 Uiso 1 1 calc R U . . .
C15A C -0.2484(2) 0.1466(3) 0.4417(4) 0.0438(13) Uani 1 1 d . . . . .
H15A H -0.2516 0.1227 0.4863 0.053 Uiso 1 1 calc R U . . .
H15B H -0.2827 0.1243 0.3963 0.053 Uiso 1 1 calc R U . . .
C16A C -0.2568(2) 0.2322(3) 0.4431(3) 0.0390(12) Uani 1 1 d . . . . .
H16A H -0.2690 0.2545 0.3927 0.047 Uiso 1 1 calc R U . . .
H16B H -0.2911 0.2458 0.4623 0.047 Uiso 1 1 calc R U . . .
C17A C -0.1889(2) 0.2584(3) 0.4956(3) 0.0301(10) Uani 1 1 d . . . . .
H17A H -0.1812 0.3123 0.4868 0.036 Uiso 1 1 calc R U . . .
H17B H -0.1828 0.2519 0.5485 0.036 Uiso 1 1 calc R U . . .
C18A C -0.1428(3) 0.0669(3) 0.4877(4) 0.0477(14) Uani 1 1 d . . . . .
H18A H -0.0985 0.0635 0.4866 0.072 Uiso 1 1 calc R U . . .
H18B H -0.1678 0.0205 0.4664 0.072 Uiso 1 1 calc R U . . .
H18C H -0.1386 0.0727 0.5394 0.072 Uiso 1 1 calc R U . . .
C19A C 0.0626(2) 0.3624(2) 0.2763(2) 0.0216(8) Uani 1 1 d . . . . .
C20A C 0.0475(2) 0.3539(3) 0.1444(3) 0.0307(10) Uani 1 1 d . . . . .
H20A H 0.0000 0.3377 0.1275 0.037 Uiso 1 1 calc R U . . .
C21A C 0.0551(3) 0.4141(3) 0.0922(3) 0.0331(10) Uani 1 1 d . . . . .
H21A H 0.0208 0.4080 0.0411 0.040 Uiso 1 1 calc R U . . .
H21B H 0.0996 0.4114 0.0903 0.040 Uiso 1 1 calc R U . . .
C22A C 0.0459(3) 0.4888(3) 0.1266(3) 0.0400(12) Uani 1 1 d . . . . .
H22A H -0.0015 0.4985 0.1160 0.048 Uiso 1 1 calc R U . . .
H22B H 0.0642 0.5321 0.1082 0.048 Uiso 1 1 calc R U . . .
C23A C 0.0859(2) 0.4748(2) 0.2101(3) 0.0291(10) Uani 1 1 d . . . . .
H23A H 0.1341 0.4814 0.2235 0.035 Uiso 1 1 calc R U . . .
H23B H 0.0714 0.5090 0.2413 0.035 Uiso 1 1 calc R U . . .
C24A C 0.0927(3) 0.2843(3) 0.1494(3) 0.0396(12) Uani 1 1 d . . . . .
H24A H 0.0808 0.2623 0.0996 0.059 Uiso 1 1 calc R U . . .
H24B H 0.0866 0.2461 0.1829 0.059 Uiso 1 1 calc R U . . .
H24C H 0.1393 0.3005 0.1690 0.059 Uiso 1 1 calc R U . . .
C1 C 0.4826(2) 0.6825(2) 0.4710(2) 0.0218(8) Uani 1 1 d . . . . .
O1 O 0.46300(15) 0.79228(17) 0.52839(16) 0.0241(6) Uani 1 1 d . . . . .
Cl1 Cl 0.54003(6) 0.54359(8) 0.34642(6) 0.0389(3) Uani 1 1 d . . . . .
N1 N 0.51580(16) 0.65845(19) 0.54052(19) 0.0201(7) Uani 1 1 d . . . . .
Nd1 Nd 0.50751(2) 0.73732(2) 0.65414(2) 0.01814(6) Uani 1 1 d . . . . .
Cl2 Cl 0.74320(5) 0.43889(6) 0.74670(7) 0.0303(2) Uani 1 1 d . . . . .
C2 C 0.4888(2) 0.6476(2) 0.4093(2) 0.0243(9) Uani 1 1 d . . . . .
H2 H 0.4640 0.6656 0.3601 0.029 Uiso 1 1 calc R U . . .
O2 O 0.57707(15) 0.70645(17) 0.78670(16) 0.0260(6) Uani 1 1 d . . . . .
N2 N 0.57993(17) 0.61292(19) 0.68034(19) 0.0214(7) Uani 1 1 d . . . . .
O3 O 0.40017(16) 0.6681(2) 0.58358(19) 0.0357(8) Uani 1 1 d . . . . .
C3 C 0.5309(2) 0.5875(3) 0.4210(2) 0.0259(9) Uani 1 1 d . . . . .
N3 N 0.3902(2) 0.7734(2) 0.4105(2) 0.0323(9) Uani 1 1 d . . . . .
O4 O 0.4443(2) 0.6411(2) 0.6996(2) 0.0518(11) Uani 1 1 d . . . . .
C4 C 0.5682(2) 0.5605(2) 0.4939(2) 0.0238(8) Uani 1 1 d . . . . .
N4 N 0.5876(2) 0.6046(2) 0.8630(2) 0.0302(8) Uani 1 1 d . . . . .
C5 C 0.6168(2) 0.5006(3) 0.5129(3) 0.0289(9) Uani 1 1 d . . . . .
H5 H 0.6240 0.4742 0.4741 0.035 Uiso 1 1 calc R U . . .
N5 N 0.39503(19) 0.6345(2) 0.6380(2) 0.0309(9) Uani 1 1 d . . . . .
O5 O 0.34632(17) 0.5975(2) 0.6317(2) 0.0439(9) Uani 1 1 d . . . . .
N6 N 0.61335(19) 0.8404(2) 0.6565(2) 0.0303(8) Uani 1 1 d . . . . .
O6 O 0.61405(16) 0.77012(18) 0.64098(18) 0.0303(7) Uani 1 1 d . . . . .
C6 C 0.6522(2) 0.4811(2) 0.5842(3) 0.0267(9) Uani 1 1 d . . . . .
H6 H 0.6849 0.4423 0.5949 0.032 Uiso 1 1 calc R U . . .
O7 O 0.56838(16) 0.86167(18) 0.67817(19) 0.0328(7) Uani 1 1 d . . . . .
N7 N 0.42226(18) 0.83901(19) 0.7011(2) 0.0234(7) Uani 1 1 d . . . . .
C7 C 0.6417(2) 0.5175(2) 0.6443(2) 0.0212(8) Uani 1 1 d . . . . .
C8 C 0.6780(2) 0.5021(2) 0.7206(3) 0.0237(8) Uani 1 1 d . . . . .
O8 O 0.6534(2) 0.8847(2) 0.6500(2) 0.0471(10) Uani 1 1 d . . . . .
C9 C 0.6628(2) 0.5373(3) 0.7746(3) 0.0277(9) Uani 1 1 d . . . . .
H9 H 0.6858 0.5252 0.8260 0.033 Uiso 1 1 calc R U . . .
O9 O 0.4667(2) 0.7985(3) 0.7455(2) 0.0615(14) Uani 1 1 d . . . . .
C10 C 0.6121(2) 0.5916(2) 0.7513(2) 0.0248(9) Uani 1 1 d . . . . .
O10 O 0.41616(17) 0.8367(2) 0.63448(18) 0.0362(8) Uani 1 1 d . . . . .
O11 O 0.38690(17) 0.87908(19) 0.72206(18) 0.0332(7) Uani 1 1 d . . . . .
C11 C 0.59360(19) 0.5757(2) 0.6282(2) 0.0193(8) Uani 1 1 d . . . . .
C12 C 0.55750(19) 0.5989(2) 0.5517(2) 0.0188(8) Uani 1 1 d . . . . .
C13 C 0.4433(2) 0.7532(2) 0.4698(2) 0.0226(8) Uani 1 1 d . . . . .
C14 C 0.3465(3) 0.8369(3) 0.4171(3) 0.0478(14) Uani 1 1 d . . . . .
H14 H 0.3507 0.8431 0.4699 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2771(3) 0.8057(5) 0.3667(4) 0.066(2) Uani 1 1 d . . . . .
H15C H 0.2606 0.7697 0.3947 0.079 Uiso 1 1 calc R U . . .
H15D H 0.2446 0.8476 0.3473 0.079 Uiso 1 1 calc R U . . .
C16 C 0.2883(4) 0.7659(4) 0.3040(5) 0.081(3) Uani 1 1 d . . . . .
H16C H 0.2864 0.8026 0.2646 0.098 Uiso 1 1 calc R U . . .
H16D H 0.2542 0.7263 0.2814 0.098 Uiso 1 1 calc R U . . .
C17 C 0.3568(3) 0.7306(3) 0.3393(3) 0.0512(16) Uani 1 1 d . . . . .
H17C H 0.3537 0.6759 0.3492 0.061 Uiso 1 1 calc R U . . .
H17D H 0.3815 0.7365 0.3064 0.061 Uiso 1 1 calc R U . . .
C18 C 0.3641(4) 0.9076(4) 0.3886(5) 0.070(2) Uani 1 1 d . . . . .
H18D H 0.4116 0.9177 0.4155 0.105 Uiso 1 1 calc R U . . .
H18E H 0.3384 0.9499 0.3963 0.105 Uiso 1 1 calc R U . . .
H18F H 0.3541 0.9021 0.3352 0.105 Uiso 1 1 calc R U . . .
C19 C 0.5913(2) 0.6379(3) 0.8039(2) 0.0263(9) Uani 1 1 d . . . . .
C20 C 0.5662(3) 0.6475(3) 0.9156(3) 0.0340(11) Uani 1 1 d . . . . .
H20 H 0.5226 0.6726 0.8869 0.041 Uiso 1 1 calc R U . . .
C21 C 0.5562(3) 0.5842(3) 0.9642(3) 0.0414(12) Uani 1 1 d . . . . .
H21C H 0.5976 0.5748 1.0086 0.050 Uiso 1 1 calc R U . . .
H21D H 0.5204 0.5977 0.9812 0.050 Uiso 1 1 calc R U . . .
C22 C 0.5370(3) 0.5146(3) 0.9134(3) 0.0427(13) Uani 1 1 d . . . . .
H22C H 0.5443 0.4670 0.9427 0.051 Uiso 1 1 calc R U . . .
H22D H 0.4901 0.5171 0.8777 0.051 Uiso 1 1 calc R U . . .
C23 C 0.5841(3) 0.5208(3) 0.8738(3) 0.0366(11) Uani 1 1 d . . . . .
H23C H 0.6284 0.4998 0.9049 0.044 Uiso 1 1 calc R U . . .
H23D H 0.5664 0.4938 0.8253 0.044 Uiso 1 1 calc R U . . .
C24 C 0.6160(3) 0.7069(3) 0.9584(3) 0.0364(11) Uani 1 1 d . . . . .
H24D H 0.6593 0.6828 0.9851 0.055 Uiso 1 1 calc R U . . .
H24E H 0.6012 0.7315 0.9943 0.055 Uiso 1 1 calc R U . . .
H24F H 0.6199 0.7450 0.9236 0.055 Uiso 1 1 calc R U . . .
N4S N 0.2445(5) 0.3407(5) 0.5241(5) 0.124(3) Uani 1 1 d . U . . .
C7S C 0.2395(5) 0.2823(6) 0.5551(6) 0.100(3) Uani 1 1 d . . . . .
C8S C 0.2396(4) 0.2099(6) 0.5988(6) 0.097(3) Uani 1 1 d . . . . .
H8SA H 0.2033 0.2123 0.6165 0.146 Uiso 1 1 calc R U . . .
H8SB H 0.2821 0.2055 0.6417 0.146 Uiso 1 1 calc R U . . .
H8SC H 0.2333 0.1656 0.5662 0.146 Uiso 1 1 calc R U . . .
N3S N 0.2698(3) 0.0426(5) 0.4815(5) 0.096(3) Uani 1 1 d . . . . .
C5S C 0.2319(4) 0.0389(4) 0.4207(5) 0.067(2) Uani 1 1 d . . . . .
C6S C 0.1824(4) 0.0355(5) 0.3431(4) 0.077(2) Uani 1 1 d . . . . .
H6SA H 0.1414 0.0606 0.3400 0.115 Uiso 1 1 calc R U . . .
H6SB H 0.1730 -0.0177 0.3278 0.115 Uiso 1 1 calc R U . . .
H6SC H 0.1999 0.0613 0.3101 0.115 Uiso 1 1 calc R U . . .
N2S N 0.7639(3) 0.6327(3) 0.6969(4) 0.0618(15) Uani 1 1 d . . . . .
C3S C 0.7686(2) 0.6887(3) 0.6718(3) 0.0430(13) Uani 1 1 d . . . . .
C4S C 0.7776(4) 0.7616(4) 0.6418(4) 0.0606(17) Uani 1 1 d . . . . .
H4SA H 0.8183 0.7857 0.6766 0.091 Uiso 1 1 calc R U . . .
H4SB H 0.7395 0.7945 0.6351 0.091 Uiso 1 1 calc R U . . .
H4SC H 0.7809 0.7538 0.5936 0.091 Uiso 1 1 calc R U . . .
C1S C 0.7511(4) 0.8974(5) 0.8064(5) 0.073(2) Uani 1 1 d . . . . .
N1S N 0.7903(4) 0.8539(4) 0.7988(4) 0.089(2) Uani 1 1 d . . . . .
C2S C 0.7056(3) 0.9466(5) 0.8200(4) 0.076(3) Uani 1 1 d . . . . .
H2SA H 0.7232 0.9985 0.8276 0.114 Uiso 1 1 calc R U . . .
H2SB H 0.6992 0.9296 0.8647 0.114 Uiso 1 1 calc R U . . .
H2SC H 0.6629 0.9456 0.7770 0.114 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
Cl1A C3A 1.720(4) . ?
Nd1A O1A 2.496(3) . ?
Nd1A N1A 2.620(3) . ?
Nd1A O2A 2.443(3) . ?
Nd1A N2A 2.666(3) . ?
Nd1A O3A 2.533(3) . ?
Nd1A O4A 2.554(3) . ?
Nd1A N5A 2.975(4) . ?
Nd1A N6A 2.933(4) . ?
Nd1A O6A 2.520(3) . ?
Nd1A O7A 2.506(3) . ?
Nd1A O9A 2.544(3) . ?
Nd1A O10A 2.565(3) . ?
C1A N1A 1.328(5) . ?
C1A C2A 1.397(6) . ?
C1A C13A 1.514(5) . ?
O1A C13A 1.250(5) . ?
N1A C12A 1.347(5) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.373(6) . ?
O2A C19A 1.257(5) . ?
N2A C10A 1.323(5) . ?
N2A C11A 1.346(5) . ?
Cl2A C8A 1.722(4) . ?
C3A C4A 1.417(6) . ?
O3A N5A 1.274(5) . ?
N3A C13A 1.318(5) . ?
N3A C14A 1.493(5) . ?
N3A C17A 1.476(5) . ?
O4A N5A 1.274(5) . ?
N4A C19A 1.321(5) . ?
N4A C20A 1.502(6) . ?
N4A C23A 1.484(5) . ?
C4A C5A 1.430(6) . ?
C4A C12A 1.411(5) . ?
N5A O5A 1.219(5) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.357(6) . ?
N6A O6A 1.262(5) . ?
N6A O7A 1.286(5) . ?
N6A O8A 1.210(5) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.422(6) . ?
N7A O9A 1.276(4) . ?
N7A O10A 1.261(5) . ?
N7A O11A 1.216(5) . ?
C7A C8A 1.414(5) . ?
C7A C11A 1.410(5) . ?
C8A C9A 1.364(6) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.406(6) . ?
C10A C19A 1.501(6) . ?
C11A C12A 1.445(5) . ?
C14A H14A 1.0000 . ?
C14A C15A 1.521(7) . ?
C14A C18A 1.527(7) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C15A C16A 1.519(7) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C16A C17A 1.509(7) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C20A H20A 1.0000 . ?
C20A C21A 1.521(6) . ?
C20A C24A 1.554(7) . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C21A C22A 1.522(7) . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
C22A C23A 1.534(7) . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C1 N1 1.329(5) . ?
C1 C2 1.401(6) . ?
C1 C13 1.509(6) . ?
O1 Nd1 2.450(3) . ?
O1 C13 1.254(5) . ?
Cl1 C3 1.723(4) . ?
N1 Nd1 2.675(3) . ?
N1 C12 1.350(5) . ?
Nd1 O2 2.487(3) . ?
Nd1 N2 2.632(3) . ?
Nd1 O3 2.522(3) . ?
Nd1 O4 2.553(4) . ?
Nd1 N5 2.970(4) . ?
Nd1 N6 2.927(4) . ?
Nd1 O6 2.510(3) . ?
Nd1 O7 2.508(3) . ?
Nd1 O9 2.522(4) . ?
Nd1 O10 2.569(3) . ?
Cl2 C8 1.721(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.363(6) . ?
O2 C19 1.257(5) . ?
N2 C10 1.335(5) . ?
N2 C11 1.336(5) . ?
O3 N5 1.256(5) . ?
C3 C4 1.412(6) . ?
N3 C13 1.326(6) . ?
N3 C14 1.508(7) . ?
N3 C17 1.492(6) . ?
O4 N5 1.265(5) . ?
C4 C5 1.440(6) . ?
C4 C12 1.408(5) . ?
N4 C19 1.320(6) . ?
N4 C20 1.487(6) . ?
N4 C23 1.495(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.341(6) . ?
N5 O5 1.213(5) . ?
N6 O6 1.274(5) . ?
N6 O7 1.269(5) . ?
N6 O8 1.216(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.430(6) . ?
N7 O9 1.241(5) . ?
N7 O10 1.251(5) . ?
N7 O11 1.228(4) . ?
C7 C8 1.408(6) . ?
C7 C11 1.412(5) . ?
C8 C9 1.368(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.398(6) . ?
C10 C19 1.511(6) . ?
C11 C12 1.443(6) . ?
C14 H14 1.0000 . ?
C14 C15 1.550(9) . ?
C14 C18 1.472(9) . ?
C15 H15C 0.9900 . ?
C15 H15D 0.9900 . ?
C15 C16 1.510(10) . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C16 C17 1.516(9) . ?
C17 H17C 0.9900 . ?
C17 H17D 0.9900 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 0.9800 . ?
C20 H20 1.0000 . ?
C20 C21 1.532(7) . ?
C20 C24 1.502(7) . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C21 C22 1.526(7) . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
C22 C23 1.512(7) . ?
C23 H23C 0.9900 . ?
C23 H23D 0.9900 . ?
C24 H24D 0.9800 . ?
C24 H24E 0.9800 . ?
C24 H24F 0.9800 . ?
N4S C7S 1.218(13) . ?
C7S C8S 1.531(14) . ?
C8S H8SA 0.9800 . ?
C8S H8SB 0.9800 . ?
C8S H8SC 0.9800 . ?
N3S C5S 1.150(11) . ?
C5S C6S 1.474(12) . ?
C6S H6SA 0.9800 . ?
C6S H6SB 0.9800 . ?
C6S H6SC 0.9800 . ?
N2S C3S 1.123(8) . ?
C3S C4S 1.453(9) . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
C1S N1S 1.201(10) . ?
C1S C2S 1.421(10) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?

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
O1A Nd1A N1A 61.81(10) . . ?
O1A Nd1A N2A 119.60(10) . . ?
O1A Nd1A O3A 70.44(9) . . ?
O1A Nd1A O4A 117.34(10) . . ?
O1A Nd1A N5A 93.72(10) . . ?
O1A Nd1A N6A 75.64(10) . . ?
O1A Nd1A O6A 76.90(10) . . ?
O1A Nd1A O7A 80.14(10) . . ?
O1A Nd1A O9A 116.10(9) . . ?
O1A Nd1A O10A 68.22(9) . . ?
N1A Nd1A N2A 60.51(10) . . ?
N1A Nd1A N5A 74.07(10) . . ?
N1A Nd1A N6A 92.83(11) . . ?
O2A Nd1A O1A 160.36(10) . . ?
O2A Nd1A N1A 121.82(10) . . ?
O2A Nd1A N2A 61.41(10) . . ?
O2A Nd1A O3A 129.10(10) . . ?
O2A Nd1A O4A 81.84(10) . . ?
O2A Nd1A N5A 105.87(10) . . ?
O2A Nd1A N6A 84.79(11) . . ?
O2A Nd1A O6A 86.14(11) . . ?
O2A Nd1A O7A 81.52(10) . . ?
O2A Nd1A O9A 71.88(10) . . ?
O2A Nd1A O10A 112.38(10) . . ?
N2A Nd1A N5A 86.82(10) . . ?
N2A Nd1A N6A 90.71(11) . . ?
O3A Nd1A N1A 71.83(10) . . ?
O3A Nd1A N2A 106.30(10) . . ?
O3A Nd1A O4A 50.34(9) . . ?
O3A Nd1A N5A 25.14(10) . . ?
O3A Nd1A N6A 146.07(10) . . ?
O3A Nd1A O9A 77.48(10) . . ?
O3A Nd1A O10A 72.87(10) . . ?
O4A Nd1A N1A 80.26(10) . . ?
O4A Nd1A N2A 68.19(10) . . ?
O4A Nd1A N5A 25.21(10) . . ?
O4A Nd1A N6A 158.58(11) . . ?
O4A Nd1A O10A 106.29(10) . . ?
N6A Nd1A N5A 166.11(11) . . ?
O6A Nd1A N1A 70.93(10) . . ?
O6A Nd1A N2A 69.12(11) . . ?
O6A Nd1A O3A 138.81(10) . . ?
O6A Nd1A O4A 136.26(10) . . ?
O6A Nd1A N5A 144.06(10) . . ?
O6A Nd1A N6A 25.35(11) . . ?
O6A Nd1A O9A 141.19(11) . . ?
O6A Nd1A O10A 117.17(11) . . ?
O7A Nd1A N1A 116.45(10) . . ?
O7A Nd1A N2A 110.93(11) . . ?
O7A Nd1A O3A 140.57(10) . . ?
O7A Nd1A O4A 161.06(11) . . ?
O7A Nd1A N5A 162.04(11) . . ?
O7A Nd1A N6A 25.86(11) . . ?
O7A Nd1A O6A 51.11(11) . . ?
O7A Nd1A O9A 93.29(11) . . ?
O7A Nd1A O10A 72.13(11) . . ?
O9A Nd1A N1A 147.88(10) . . ?
O9A Nd1A N2A 121.85(10) . . ?
O9A Nd1A O4A 72.92(10) . . ?
O9A Nd1A N5A 74.14(10) . . ?
O9A Nd1A N6A 118.39(11) . . ?
O9A Nd1A O10A 49.84(9) . . ?
O10A Nd1A N1A 125.75(10) . . ?
O10A Nd1A N2A 171.69(10) . . ?
O10A Nd1A N5A 89.91(10) . . ?
O10A Nd1A N6A 94.24(12) . . ?
N1A C1A C2A 123.4(4) . . ?
N1A C1A C13A 111.7(3) . . ?
C2A C1A C13A 124.3(4) . . ?
C13A O1A Nd1A 115.7(2) . . ?
C1A N1A Nd1A 117.8(3) . . ?
C1A N1A C12A 118.4(3) . . ?
C12A N1A Nd1A 123.3(3) . . ?
C1A C2A H2A 121.1 . . ?
C3A C2A C1A 117.8(4) . . ?
C3A C2A H2A 121.1 . . ?
C19A O2A Nd1A 124.5(3) . . ?
C10A N2A Nd1A 119.0(3) . . ?
C10A N2A C11A 118.7(3) . . ?
C11A N2A Nd1A 121.6(3) . . ?
C2A C3A Cl1A 119.2(3) . . ?
C2A C3A C4A 121.1(4) . . ?
C4A C3A Cl1A 119.6(3) . . ?
N5A O3A Nd1A 97.2(2) . . ?
C13A N3A C14A 119.7(4) . . ?
C13A N3A C17A 126.5(4) . . ?
C17A N3A C14A 111.0(3) . . ?
N5A O4A Nd1A 96.2(2) . . ?
C19A N4A C20A 121.1(3) . . ?
C19A N4A C23A 127.6(4) . . ?
C23A N4A C20A 110.5(3) . . ?
C3A C4A C5A 124.7(4) . . ?
C3A C4A C12A 115.7(4) . . ?
C12A C4A C5A 119.6(4) . . ?
O3A N5A Nd1A 57.65(19) . . ?
O3A N5A O4A 116.2(3) . . ?
O4A N5A Nd1A 58.6(2) . . ?
O5A N5A Nd1A 177.8(3) . . ?
O5A N5A O3A 122.0(4) . . ?
O5A N5A O4A 121.8(4) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A C4A 120.7(4) . . ?
C6A C5A H5A 119.7 . . ?
O6A N6A Nd1A 58.7(2) . . ?
O6A N6A O7A 116.6(4) . . ?
O7A N6A Nd1A 58.2(2) . . ?
O8A N6A Nd1A 174.2(4) . . ?
O8A N6A O6A 122.5(5) . . ?
O8A N6A O7A 120.9(4) . . ?
C5A C6A H6A 119.3 . . ?
C5A C6A C7A 121.3(4) . . ?
C7A C6A H6A 119.3 . . ?
N6A O6A Nd1A 95.9(3) . . ?
O9A N7A Nd1A 57.6(2) . . ?
O10A N7A Nd1A 58.48(19) . . ?
O10A N7A O9A 116.1(3) . . ?
O11A N7A Nd1A 178.4(3) . . ?
O11A N7A O9A 121.8(4) . . ?
O11A N7A O10A 122.0(4) . . ?
C8A C7A C6A 125.4(4) . . ?
C11A C7A C6A 119.7(4) . . ?
C11A C7A C8A 114.9(4) . . ?
N6A O7A Nd1A 96.0(2) . . ?
C7A C8A Cl2A 118.2(3) . . ?
C9A C8A Cl2A 120.3(3) . . ?
C9A C8A C7A 121.5(4) . . ?
N7A O9A Nd1A 97.3(2) . . ?
C8A C9A H9A 120.9 . . ?
C8A C9A C10A 118.2(4) . . ?
C10A C9A H9A 120.9 . . ?
N2A C10A C9A 122.4(4) . . ?
N2A C10A C19A 111.6(3) . . ?
C9A C10A C19A 125.8(4) . . ?
N7A O10A Nd1A 96.7(2) . . ?
N2A C11A C7A 124.0(4) . . ?
N2A C11A C12A 116.8(3) . . ?
C7A C11A C12A 119.2(4) . . ?
N1A C12A C4A 123.5(4) . . ?
N1A C12A C11A 117.0(4) . . ?
C4A C12A C11A 119.4(3) . . ?
O1A C13A C1A 116.2(3) . . ?
O1A C13A N3A 123.5(4) . . ?
N3A C13A C1A 120.2(4) . . ?
N3A C14A H14A 109.9 . . ?
N3A C14A C15A 103.0(4) . . ?
N3A C14A C18A 110.6(4) . . ?
C15A C14A H14A 109.9 . . ?
C15A C14A C18A 113.4(4) . . ?
C18A C14A H14A 109.9 . . ?
C14A C15A H15A 110.8 . . ?
C14A C15A H15B 110.8 . . ?
C14A C15A C16A 104.8(4) . . ?
H15A C15A H15B 108.9 . . ?
C16A C15A H15A 110.8 . . ?
C16A C15A H15B 110.8 . . ?
C15A C16A H16A 111.2 . . ?
C15A C16A H16B 111.2 . . ?
H16A C16A H16B 109.1 . . ?
C17A C16A C15A 102.7(4) . . ?
C17A C16A H16A 111.2 . . ?
C17A C16A H16B 111.2 . . ?
N3A C17A C16A 102.2(4) . . ?
N3A C17A H17A 111.3 . . ?
N3A C17A H17B 111.3 . . ?
C16A C17A H17A 111.3 . . ?
C16A C17A H17B 111.3 . . ?
H17A C17A H17B 109.2 . . ?
C14A C18A H18A 109.5 . . ?
C14A C18A H18B 109.5 . . ?
C14A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O2A C19A N4A 121.5(4) . . ?
O2A C19A C10A 116.9(4) . . ?
N4A C19A C10A 121.6(4) . . ?
N4A C20A H20A 110.4 . . ?
N4A C20A C21A 103.3(4) . . ?
N4A C20A C24A 111.0(4) . . ?
C21A C20A H20A 110.4 . . ?
C21A C20A C24A 111.0(4) . . ?
C24A C20A H20A 110.4 . . ?
C20A C21A H21A 111.0 . . ?
C20A C21A H21B 111.0 . . ?
C20A C21A C22A 103.9(4) . . ?
H21A C21A H21B 109.0 . . ?
C22A C21A H21A 111.0 . . ?
C22A C21A H21B 111.0 . . ?
C21A C22A H22A 111.4 . . ?
C21A C22A H22B 111.4 . . ?
C21A C22A C23A 102.0(4) . . ?
H22A C22A H22B 109.2 . . ?
C23A C22A H22A 111.4 . . ?
C23A C22A H22B 111.4 . . ?
N4A C23A C22A 101.7(4) . . ?
N4A C23A H23A 111.4 . . ?
N4A C23A H23B 111.4 . . ?
C22A C23A H23A 111.4 . . ?
C22A C23A H23B 111.4 . . ?
H23A C23A H23B 109.3 . . ?
C20A C24A H24A 109.5 . . ?
C20A C24A H24B 109.5 . . ?
C20A C24A H24C 109.5 . . ?
H24A C24A H24B 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
N1 C1 C2 122.4(4) . . ?
N1 C1 C13 111.0(4) . . ?
C2 C1 C13 126.4(4) . . ?
C13 O1 Nd1 123.5(3) . . ?
C1 N1 Nd1 119.3(3) . . ?
C1 N1 C12 118.4(4) . . ?
C12 N1 Nd1 122.0(3) . . ?
O1 Nd1 N1 60.58(10) . . ?
O1 Nd1 O2 164.57(10) . . ?
O1 Nd1 N2 119.69(10) . . ?
O1 Nd1 O3 74.09(11) . . ?
O1 Nd1 O4 123.40(11) . . ?
O1 Nd1 N5 98.41(11) . . ?
O1 Nd1 N6 76.93(10) . . ?
O1 Nd1 O6 80.16(10) . . ?
O1 Nd1 O7 79.41(11) . . ?
O1 Nd1 O9 115.05(10) . . ?
O1 Nd1 O10 66.47(10) . . ?
N1 Nd1 N5 85.32(10) . . ?
N1 Nd1 N6 91.45(11) . . ?
O2 Nd1 N1 122.09(10) . . ?
O2 Nd1 N2 62.62(10) . . ?
O2 Nd1 O3 121.34(11) . . ?
O2 Nd1 O4 71.96(11) . . ?
O2 Nd1 N5 96.99(11) . . ?
O2 Nd1 N6 87.70(10) . . ?
O2 Nd1 O6 86.58(11) . . ?
O2 Nd1 O7 86.14(11) . . ?
O2 Nd1 O9 66.69(11) . . ?
O2 Nd1 O10 115.31(10) . . ?
N2 Nd1 N1 59.88(11) . . ?
N2 Nd1 N5 85.70(11) . . ?
N2 Nd1 N6 95.72(11) . . ?
O3 Nd1 N1 69.49(11) . . ?
O3 Nd1 N2 93.74(11) . . ?
O3 Nd1 O4 49.69(11) . . ?
O3 Nd1 N5 24.75(11) . . ?
O3 Nd1 N6 150.49(11) . . ?
O3 Nd1 O9 94.50(15) . . ?
O3 Nd1 O10 75.15(12) . . ?
O4 Nd1 N1 99.41(12) . . ?
O4 Nd1 N2 75.40(13) . . ?
O4 Nd1 N5 25.05(12) . . ?
O4 Nd1 N6 159.65(11) . . ?
O4 Nd1 O10 90.46(14) . . ?
N6 Nd1 N5 175.23(11) . . ?
O6 Nd1 N1 70.66(10) . . ?
O6 Nd1 N2 72.44(11) . . ?
O6 Nd1 O3 139.43(11) . . ?
O6 Nd1 O4 146.96(13) . . ?
O6 Nd1 N5 153.31(10) . . ?
O6 Nd1 N6 25.66(11) . . ?
O6 Nd1 O9 124.98(15) . . ?
O6 Nd1 O10 121.84(11) . . ?
O7 Nd1 N1 113.80(11) . . ?
O7 Nd1 N2 116.99(11) . . ?
O7 Nd1 O3 146.74(11) . . ?
O7 Nd1 O4 146.49(12) . . ?
O7 Nd1 N5 155.29(11) . . ?
O7 Nd1 N6 25.54(11) . . ?
O7 Nd1 O6 51.09(11) . . ?
O7 Nd1 O9 78.77(15) . . ?
O7 Nd1 O10 76.06(12) . . ?
O9 Nd1 N1 163.94(14) . . ?
O9 Nd1 N2 124.82(11) . . ?
O9 Nd1 O4 69.47(16) . . ?
O9 Nd1 N5 80.02(15) . . ?
O9 Nd1 N6 102.76(15) . . ?
O9 Nd1 O10 49.06(11) . . ?
O10 Nd1 N1 122.05(10) . . ?
O10 Nd1 N2 165.72(12) . . ?
O10 Nd1 N5 80.51(12) . . ?
O10 Nd1 N6 98.33(12) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2 120.6 . . ?
C19 O2 Nd1 118.2(3) . . ?
C10 N2 Nd1 117.9(3) . . ?
C11 N2 Nd1 123.9(3) . . ?
C11 N2 C10 117.6(4) . . ?
N5 O3 Nd1 98.0(3) . . ?
C2 C3 Cl1 120.1(4) . . ?
C2 C3 C4 121.1(4) . . ?
C4 C3 Cl1 118.9(3) . . ?
C13 N3 C14 119.6(4) . . ?
C13 N3 C17 128.0(4) . . ?
C17 N3 C14 110.9(4) . . ?
N5 O4 Nd1 96.3(3) . . ?
C3 C4 C5 125.6(4) . . ?
C12 C4 C3 115.4(4) . . ?
C12 C4 C5 118.9(4) . . ?
C19 N4 C20 121.0(4) . . ?
C19 N4 C23 125.8(4) . . ?
C20 N4 C23 110.9(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.3 . . ?
O3 N5 Nd1 57.2(2) . . ?
O3 N5 O4 115.5(4) . . ?
O4 N5 Nd1 58.7(2) . . ?
O5 N5 Nd1 174.9(3) . . ?
O5 N5 O3 122.1(4) . . ?
O5 N5 O4 122.4(4) . . ?
O6 N6 Nd1 58.5(2) . . ?
O7 N6 Nd1 58.4(2) . . ?
O7 N6 O6 116.6(4) . . ?
O8 N6 Nd1 173.4(3) . . ?
O8 N6 O6 121.4(4) . . ?
O8 N6 O7 122.0(4) . . ?
N6 O6 Nd1 95.8(2) . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.3(4) . . ?
C7 C6 H6 119.4 . . ?
N6 O7 Nd1 96.0(2) . . ?
O9 N7 Nd1 56.9(2) . . ?
O9 N7 O10 116.1(3) . . ?
O10 N7 Nd1 59.2(2) . . ?
O11 N7 Nd1 177.9(3) . . ?
O11 N7 O9 121.5(4) . . ?
O11 N7 O10 122.4(4) . . ?
C8 C7 C6 124.8(4) . . ?
C8 C7 C11 116.0(4) . . ?
C11 C7 C6 119.2(4) . . ?
C7 C8 Cl2 119.7(3) . . ?
C9 C8 Cl2 119.2(3) . . ?
C9 C8 C7 121.1(4) . . ?
C8 C9 H9 121.3 . . ?
C8 C9 C10 117.4(4) . . ?
C10 C9 H9 121.3 . . ?
N7 O9 Nd1 98.7(3) . . ?
N2 C10 C9 123.9(4) . . ?
N2 C10 C19 111.8(4) . . ?
C9 C10 C19 124.1(4) . . ?
N7 O10 Nd1 96.1(2) . . ?
N2 C11 C7 123.7(4) . . ?
N2 C11 C12 116.7(3) . . ?
C7 C11 C12 119.5(4) . . ?
N1 C12 C4 123.8(4) . . ?
N1 C12 C11 116.6(3) . . ?
C4 C12 C11 119.6(4) . . ?
O1 C13 C1 116.6(4) . . ?
O1 C13 N3 121.1(4) . . ?
N3 C13 C1 122.4(4) . . ?
N3 C14 H14 111.2 . . ?
N3 C14 C15 100.4(5) . . ?
C15 C14 H14 111.2 . . ?
C18 C14 N3 109.0(5) . . ?
C18 C14 H14 111.2 . . ?
C18 C14 C15 113.4(6) . . ?
C14 C15 H15C 110.9 . . ?
C14 C15 H15D 110.9 . . ?
H15C C15 H15D 108.9 . . ?
C16 C15 C14 104.2(6) . . ?
C16 C15 H15C 110.9 . . ?
C16 C15 H15D 110.9 . . ?
C15 C16 H16C 110.6 . . ?
C15 C16 H16D 110.6 . . ?
C15 C16 C17 105.6(5) . . ?
H16C C16 H16D 108.7 . . ?
C17 C16 H16C 110.6 . . ?
C17 C16 H16D 110.6 . . ?
N3 C17 C16 104.5(5) . . ?
N3 C17 H17C 110.8 . . ?
N3 C17 H17D 110.8 . . ?
C16 C17 H17C 110.8 . . ?
C16 C17 H17D 110.8 . . ?
H17C C17 H17D 108.9 . . ?
C14 C18 H18D 109.5 . . ?
C14 C18 H18E 109.5 . . ?
C14 C18 H18F 109.5 . . ?
H18D C18 H18E 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
O2 C19 N4 124.4(4) . . ?
O2 C19 C10 116.5(4) . . ?
N4 C19 C10 119.1(4) . . ?
N4 C20 H20 109.2 . . ?
N4 C20 C21 102.4(4) . . ?
N4 C20 C24 112.3(4) . . ?
C21 C20 H20 109.2 . . ?
C24 C20 H20 109.2 . . ?
C24 C20 C21 114.3(4) . . ?
C20 C21 H21C 110.8 . . ?
C20 C21 H21D 110.8 . . ?
H21C C21 H21D 108.9 . . ?
C22 C21 C20 104.6(4) . . ?
C22 C21 H21C 110.8 . . ?
C22 C21 H21D 110.8 . . ?
C21 C22 H22C 111.4 . . ?
C21 C22 H22D 111.4 . . ?
H22C C22 H22D 109.3 . . ?
C23 C22 C21 101.7(4) . . ?
C23 C22 H22C 111.4 . . ?
C23 C22 H22D 111.4 . . ?
N4 C23 C22 103.0(4) . . ?
N4 C23 H23C 111.2 . . ?
N4 C23 H23D 111.2 . . ?
C22 C23 H23C 111.2 . . ?
C22 C23 H23D 111.2 . . ?
H23C C23 H23D 109.1 . . ?
C20 C24 H24D 109.5 . . ?
C20 C24 H24E 109.5 . . ?
C20 C24 H24F 109.5 . . ?
H24D C24 H24E 109.5 . . ?
H24D C24 H24F 109.5 . . ?
H24E C24 H24F 109.5 . . ?
N4S C7S C8S 175.0(12) . . ?
C7S C8S H8SA 109.5 . . ?
C7S C8S H8SB 109.5 . . ?
C7S C8S H8SC 109.5 . . ?
H8SA C8S H8SB 109.5 . . ?
H8SA C8S H8SC 109.5 . . ?
H8SB C8S H8SC 109.5 . . ?
N3S C5S C6S 178.6(9) . . ?
C5S C6S H6SA 109.5 . . ?
C5S C6S H6SB 109.5 . . ?
C5S C6S H6SC 109.5 . . ?
H6SA C6S H6SB 109.5 . . ?
H6SA C6S H6SC 109.5 . . ?
H6SB C6S H6SC 109.5 . . ?
N2S C3S C4S 177.6(7) . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
N1S C1S C2S 176.2(10) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 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
Cl1A C3A C4A C5A -0.3(6) . . . . ?
Cl1A C3A C4A C12A 177.6(3) . . . . ?
Nd1A O1A C13A C1A -48.5(4) . . . . ?
Nd1A O1A C13A N3A 134.3(3) . . . . ?
Nd1A N1A C12A C4A -171.9(3) . . . . ?
Nd1A N1A C12A C11A 4.0(5) . . . . ?
Nd1A O2A C19A N4A -147.1(3) . . . . ?
Nd1A O2A C19A C10A 31.4(5) . . . . ?
Nd1A N2A C10A C9A -165.1(3) . . . . ?
Nd1A N2A C10A C19A 10.9(4) . . . . ?
Nd1A N2A C11A C7A 167.7(3) . . . . ?
Nd1A N2A C11A C12A -9.7(5) . . . . ?
Nd1A O3A N5A O4A 2.1(4) . . . . ?
Nd1A O3A N5A O5A -177.5(3) . . . . ?
Nd1A O4A N5A O3A -2.1(3) . . . . ?
Nd1A O4A N5A O5A 177.5(3) . . . . ?
C1A N1A C12A C4A 0.4(6) . . . . ?
C1A N1A C12A C11A 176.4(3) . . . . ?
C1A C2A C3A Cl1A -176.0(3) . . . . ?
C1A C2A C3A C4A 0.8(6) . . . . ?
N1A C1A C2A C3A -2.0(6) . . . . ?
N1A C1A C13A O1A 29.7(5) . . . . ?
N1A C1A C13A N3A -153.0(4) . . . . ?
C2A C1A N1A Nd1A 174.2(3) . . . . ?
C2A C1A N1A C12A 1.4(6) . . . . ?
C2A C1A C13A O1A -142.0(4) . . . . ?
C2A C1A C13A N3A 35.3(6) . . . . ?
C2A C3A C4A C5A -177.0(4) . . . . ?
C2A C3A C4A C12A 0.8(6) . . . . ?
N2A C10A C19A O2A -26.2(5) . . . . ?
N2A C10A C19A N4A 152.4(4) . . . . ?
N2A C11A C12A N1A 3.8(5) . . . . ?
N2A C11A C12A C4A 179.9(3) . . . . ?
Cl2A C8A C9A C10A 175.9(3) . . . . ?
C3A C4A C5A C6A 175.5(4) . . . . ?
C3A C4A C12A N1A -1.5(6) . . . . ?
C3A C4A C12A C11A -177.4(3) . . . . ?
N3A C14A C15A C16A 23.8(6) . . . . ?
N4A C20A C21A C22A -27.6(5) . . . . ?
C4A C5A C6A C7A 0.9(6) . . . . ?
C5A C4A C12A N1A 176.4(4) . . . . ?
C5A C4A C12A C11A 0.6(6) . . . . ?
C5A C6A C7A C8A -176.5(4) . . . . ?
C5A C6A C7A C11A 2.2(6) . . . . ?
C6A C7A C8A Cl2A 5.3(6) . . . . ?
C6A C7A C8A C9A -177.1(4) . . . . ?
C6A C7A C11A N2A 178.9(4) . . . . ?
C6A C7A C11A C12A -3.8(6) . . . . ?
O6A N6A O7A Nd1A -6.4(4) . . . . ?
C7A C8A C9A C10A -1.7(6) . . . . ?
C7A C11A C12A N1A -173.7(3) . . . . ?
C7A C11A C12A C4A 2.4(6) . . . . ?
O7A N6A O6A Nd1A 6.4(4) . . . . ?
O8A N6A O6A Nd1A -173.3(4) . . . . ?
O8A N6A O7A Nd1A 173.2(4) . . . . ?
C8A C7A C11A N2A -2.3(6) . . . . ?
C8A C7A C11A C12A 175.0(3) . . . . ?
C8A C9A C10A N2A -3.1(6) . . . . ?
C8A C9A C10A C19A -178.5(4) . . . . ?
O9A N7A O10A Nd1A -1.5(4) . . . . ?
C9A C10A C19A O2A 149.6(4) . . . . ?
C9A C10A C19A N4A -31.9(6) . . . . ?
C10A N2A C11A C7A -2.2(6) . . . . ?
C10A N2A C11A C12A -179.6(4) . . . . ?
O10A N7A O9A Nd1A 1.5(4) . . . . ?
C11A N2A C10A C9A 5.0(6) . . . . ?
C11A N2A C10A C19A -179.0(3) . . . . ?
C11A C7A C8A Cl2A -173.5(3) . . . . ?
C11A C7A C8A C9A 4.2(6) . . . . ?
O11A N7A O9A Nd1A -178.2(4) . . . . ?
O11A N7A O10A Nd1A 178.2(4) . . . . ?
C12A C4A C5A C6A -2.3(6) . . . . ?
C13A C1A N1A Nd1A 2.4(4) . . . . ?
C13A C1A N1A C12A -170.4(3) . . . . ?
C13A C1A C2A C3A 168.7(4) . . . . ?
C13A N3A C14A C15A -161.8(4) . . . . ?
C13A N3A C14A C18A 76.8(5) . . . . ?
C13A N3A C17A C16A 136.4(4) . . . . ?
C14A N3A C13A C1A -177.9(4) . . . . ?
C14A N3A C13A O1A -0.8(6) . . . . ?
C14A N3A C17A C16A -24.4(5) . . . . ?
C14A C15A C16A C17A -39.1(6) . . . . ?
C15A C16A C17A N3A 38.1(5) . . . . ?
C17A N3A C13A C1A 22.8(6) . . . . ?
C17A N3A C13A O1A -160.0(4) . . . . ?
C17A N3A C14A C15A 0.4(5) . . . . ?
C17A N3A C14A C18A -121.0(4) . . . . ?
C18A C14A C15A C16A 143.3(5) . . . . ?
C19A N4A C20A C21A 172.6(4) . . . . ?
C19A N4A C20A C24A -68.4(5) . . . . ?
C19A N4A C23A C22A -146.1(4) . . . . ?
C20A N4A C19A O2A -1.9(6) . . . . ?
C20A N4A C19A C10A 179.7(4) . . . . ?
C20A N4A C23A C22A 23.3(5) . . . . ?
C20A C21A C22A C23A 42.1(5) . . . . ?
C21A C22A C23A N4A -39.5(5) . . . . ?
C23A N4A C19A O2A 166.5(4) . . . . ?
C23A N4A C19A C10A -12.0(6) . . . . ?
C23A N4A C20A C21A 2.4(5) . . . . ?
C23A N4A C20A C24A 121.4(4) . . . . ?
C24A C20A C21A C22A -146.6(4) . . . . ?
C1 N1 C12 C4 0.1(6) . . . . ?
C1 N1 C12 C11 178.7(3) . . . . ?
C1 C2 C3 Cl1 -179.6(3) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
Cl1 C3 C4 C5 3.3(6) . . . . ?
Cl1 C3 C4 C12 -179.4(3) . . . . ?
N1 C1 C2 C3 -0.9(6) . . . . ?
N1 C1 C13 O1 23.1(5) . . . . ?
N1 C1 C13 N3 -156.3(4) . . . . ?
Nd1 O1 C13 C1 -37.8(5) . . . . ?
Nd1 O1 C13 N3 141.6(4) . . . . ?
Nd1 N1 C12 C4 -173.6(3) . . . . ?
Nd1 N1 C12 C11 4.9(5) . . . . ?
Nd1 O2 C19 N4 -134.7(4) . . . . ?
Nd1 O2 C19 C10 43.8(5) . . . . ?
Nd1 N2 C10 C9 -165.8(3) . . . . ?
Nd1 N2 C10 C19 9.4(5) . . . . ?
Nd1 N2 C11 C7 168.2(3) . . . . ?
Nd1 N2 C11 C12 -10.3(5) . . . . ?
Nd1 O3 N5 O4 -6.8(4) . . . . ?
Nd1 O3 N5 O5 174.0(4) . . . . ?
Nd1 O4 N5 O3 6.7(4) . . . . ?
Nd1 O4 N5 O5 -174.1(4) . . . . ?
Cl2 C8 C9 C10 176.2(3) . . . . ?
C2 C1 N1 Nd1 174.8(3) . . . . ?
C2 C1 N1 C12 0.9(6) . . . . ?
C2 C1 C13 O1 -152.7(4) . . . . ?
C2 C1 C13 N3 28.0(7) . . . . ?
C2 C3 C4 C5 -176.1(4) . . . . ?
C2 C3 C4 C12 1.2(6) . . . . ?
N2 C10 C19 O2 -34.4(6) . . . . ?
N2 C10 C19 N4 144.1(4) . . . . ?
N2 C11 C12 N1 3.2(5) . . . . ?
N2 C11 C12 C4 -178.2(4) . . . . ?
C3 C4 C5 C6 176.8(4) . . . . ?
C3 C4 C12 N1 -1.2(6) . . . . ?
C3 C4 C12 C11 -179.6(4) . . . . ?
N3 C14 C15 C16 -36.5(7) . . . . ?
C4 C5 C6 C7 1.9(7) . . . . ?
N4 C20 C21 C22 -28.8(5) . . . . ?
C5 C4 C12 N1 176.3(4) . . . . ?
C5 C4 C12 C11 -2.2(6) . . . . ?
C5 C6 C7 C8 -178.0(4) . . . . ?
C5 C6 C7 C11 -0.7(6) . . . . ?
O6 N6 O7 Nd1 -6.9(4) . . . . ?
C6 C7 C8 Cl2 3.6(6) . . . . ?
C6 C7 C8 C9 -177.2(4) . . . . ?
C6 C7 C11 N2 179.7(4) . . . . ?
C6 C7 C11 C12 -1.9(6) . . . . ?
O7 N6 O6 Nd1 6.9(4) . . . . ?
C7 C8 C9 C10 -3.0(6) . . . . ?
C7 C11 C12 N1 -175.3(3) . . . . ?
C7 C11 C12 C4 3.3(6) . . . . ?
C8 C7 C11 N2 -2.8(6) . . . . ?
C8 C7 C11 C12 175.6(4) . . . . ?
C8 C9 C10 N2 -2.7(7) . . . . ?
C8 C9 C10 C19 -177.3(4) . . . . ?
O8 N6 O6 Nd1 -172.3(4) . . . . ?
O8 N6 O7 Nd1 172.3(4) . . . . ?
C9 C10 C19 O2 140.8(4) . . . . ?
C9 C10 C19 N4 -40.7(7) . . . . ?
O9 N7 O10 Nd1 2.0(5) . . . . ?
C10 N2 C11 C7 -2.5(6) . . . . ?
C10 N2 C11 C12 179.1(4) . . . . ?
O10 N7 O9 Nd1 -2.1(5) . . . . ?
O11 N7 O9 Nd1 178.3(3) . . . . ?
O11 N7 O10 Nd1 -178.4(4) . . . . ?
C11 N2 C10 C9 5.4(6) . . . . ?
C11 N2 C10 C19 -179.4(4) . . . . ?
C11 C7 C8 Cl2 -173.7(3) . . . . ?
C11 C7 C8 C9 5.5(6) . . . . ?
C12 C4 C5 C6 -0.4(6) . . . . ?
C13 C1 N1 Nd1 -1.1(4) . . . . ?
C13 C1 N1 C12 -175.1(3) . . . . ?
C13 C1 C2 C3 174.5(4) . . . . ?
C13 N3 C14 C15 -142.0(5) . . . . ?
C13 N3 C14 C18 98.6(6) . . . . ?
C13 N3 C17 C16 161.7(6) . . . . ?
C14 N3 C13 C1 169.7(4) . . . . ?
C14 N3 C13 O1 -9.7(7) . . . . ?
C14 N3 C17 C16 -4.2(7) . . . . ?
C14 C15 C16 C17 35.7(8) . . . . ?
C15 C16 C17 N3 -19.7(8) . . . . ?
C17 N3 C13 C1 4.9(8) . . . . ?
C17 N3 C13 O1 -174.4(5) . . . . ?
C17 N3 C14 C15 25.2(6) . . . . ?
C17 N3 C14 C18 -94.2(6) . . . . ?
C18 C14 C15 C16 79.7(8) . . . . ?
C19 N4 C20 C21 169.2(4) . . . . ?
C19 N4 C20 C24 -67.8(6) . . . . ?
C19 N4 C23 C22 -142.7(5) . . . . ?
C20 N4 C19 O2 -0.5(7) . . . . ?
C20 N4 C19 C10 -179.0(4) . . . . ?
C20 N4 C23 C22 20.1(5) . . . . ?
C20 C21 C22 C23 41.5(5) . . . . ?
C21 C22 C23 N4 -37.0(5) . . . . ?
C23 N4 C19 O2 160.7(4) . . . . ?
C23 N4 C19 C10 -17.8(7) . . . . ?
C23 N4 C20 C21 5.4(5) . . . . ?
C23 N4 C20 C24 128.5(4) . . . . ?
C24 C20 C21 C22 -150.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
