# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mv3_lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2302025'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 Cl2 N4 O2 Tc'
_chemical_formula_sum            'C9 H11 Cl2 N4 O2 Tc'
_chemical_formula_weight         376.12
_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'
Tc Tc -1.4390 0.7593 '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                   7.0073(8)
_cell_length_b                   11.8847(12)
_cell_length_c                   15.9967(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.950(4)
_cell_angle_gamma                90
_cell_volume                     1303.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3707
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.456
_cell_measurement_theta_min      3.117
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.513
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0716 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.8799.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23680
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         4.266
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2885
_reflns_number_total             3791
_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       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3791
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.029
_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)+(0.0300P)²+0.8537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0784
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
1.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tc1 Tc 0.70028(4) 0.44626(2) 0.73461(2) 0.01002(7) Uani 1 1 d . . . . .
Cl2 Cl 0.97044(12) 0.35838(6) 0.82655(5) 0.01624(17) Uani 1 1 d . . . . .
Cl1 Cl 0.44107(11) 0.54488(6) 0.63839(5) 0.01567(16) Uani 1 1 d . . . . .
O2 O 0.5349(3) 0.39167(17) 0.78517(14) 0.0157(5) Uani 1 1 d . . . . .
O1 O 0.8626(3) 0.50986(17) 0.66931(13) 0.0133(4) Uani 1 1 d . . . . .
N1 N 0.7480(4) 0.58917(19) 0.81706(16) 0.0102(5) Uani 1 1 d . . . . .
N2 N 0.8346(4) 0.7724(2) 0.92723(18) 0.0199(6) Uani 1 1 d . . . . .
N3 N 0.6757(4) 0.30370(19) 0.64930(16) 0.0113(5) Uani 1 1 d . . . . .
N4 N 0.6998(4) 0.1206(2) 0.54267(18) 0.0195(6) Uani 1 1 d . . . . .
C9 C 0.9035(5) 0.5637(3) 0.5967(2) 0.0212(7) Uani 1 1 d . . . . .
H9A H 0.981722 0.629311 0.613974 0.032 Uiso 1 1 calc R U . . .
H9B H 0.783467 0.585639 0.559488 0.032 Uiso 1 1 calc R U . . .
H9C H 0.973075 0.513053 0.567040 0.032 Uiso 1 1 calc R U . . .
C1 C 0.7737(5) 0.6926(2) 0.7876(2) 0.0135(6) Uani 1 1 d . . . . .
H1 H 0.762222 0.704014 0.729221 0.016 Uiso 1 1 calc R U . . .
C2 C 0.8170(5) 0.7825(2) 0.8434(2) 0.0141(6) Uani 1 1 d . . . . .
H2 H 0.834551 0.853133 0.821080 0.017 Uiso 1 1 calc R U . . .
C3 C 0.8052(5) 0.6689(3) 0.9549(2) 0.0192(7) Uani 1 1 d . . . . .
H3 H 0.813626 0.658341 1.013197 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7629(5) 0.5772(2) 0.9016(2) 0.0146(6) Uani 1 1 d . . . . .
H4 H 0.744766 0.506829 0.924194 0.017 Uiso 1 1 calc R U . . .
C5 C 0.7022(4) 0.1986(2) 0.6809(2) 0.0128(6) Uani 1 1 d . . . . .
H5 H 0.712481 0.186059 0.738993 0.015 Uiso 1 1 calc R U . . .
C6 C 0.7144(5) 0.1085(2) 0.6262(2) 0.0167(7) Uani 1 1 d . . . . .
H6 H 0.733573 0.036644 0.649493 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6683(5) 0.2256(3) 0.5125(2) 0.0172(7) Uani 1 1 d . . . . .
H7 H 0.655133 0.237758 0.454132 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6548(5) 0.3168(3) 0.5648(2) 0.0143(6) Uani 1 1 d . . . . .
H8 H 0.630783 0.388093 0.540952 0.017 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
Tc1 Cl2 2.3843(8) . ?
Tc1 Cl1 2.4258(8) . ?
Tc1 O2 1.675(2) . ?
Tc1 O1 1.857(2) . ?
Tc1 N1 2.134(2) . ?
Tc1 N3 2.160(2) . ?
O1 C9 1.407(4) . ?
N1 C1 1.342(4) . ?
N1 C4 1.342(4) . ?
N2 C2 1.327(4) . ?
N2 C3 1.337(4) . ?
N3 C5 1.345(4) . ?
N3 C8 1.338(4) . ?
N4 C6 1.328(4) . ?
N4 C7 1.340(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C2 1.385(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.396(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.385(4) . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Tc1 Cl1 176.06(3) . . ?
O2 Tc1 Cl2 94.17(8) . . ?
O2 Tc1 Cl1 89.52(8) . . ?
O2 Tc1 O1 174.15(10) . . ?
O2 Tc1 N1 92.61(10) . . ?
O2 Tc1 N3 91.64(10) . . ?
O1 Tc1 Cl2 91.42(7) . . ?
O1 Tc1 Cl1 84.94(7) . . ?
O1 Tc1 N1 89.29(9) . . ?
O1 Tc1 N3 86.67(9) . . ?
N1 Tc1 Cl2 87.96(7) . . ?
N1 Tc1 Cl1 90.49(7) . . ?
N1 Tc1 N3 175.31(10) . . ?
N3 Tc1 Cl2 89.74(7) . . ?
N3 Tc1 Cl1 91.54(7) . . ?
C9 O1 Tc1 154.5(2) . . ?
C1 N1 Tc1 121.8(2) . . ?
C4 N1 Tc1 120.50(19) . . ?
C4 N1 C1 117.6(3) . . ?
C2 N2 C3 115.5(3) . . ?
C5 N3 Tc1 120.3(2) . . ?
C8 N3 Tc1 121.63(19) . . ?
C8 N3 C5 117.7(3) . . ?
C6 N4 C7 115.9(3) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C1 H1 119.8 . . ?
N1 C1 C2 120.5(3) . . ?
C2 C1 H1 119.8 . . ?
N2 C2 C1 122.9(3) . . ?
N2 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
N2 C3 H3 118.3 . . ?
N2 C3 C4 123.4(3) . . ?
C4 C3 H3 118.3 . . ?
N1 C4 C3 120.1(3) . . ?
N1 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N3 C5 H5 120.0 . . ?
N3 C5 C6 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
N4 C6 C5 123.0(3) . . ?
N4 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
N4 C7 H7 118.7 . . ?
N4 C7 C8 122.5(3) . . ?
C8 C7 H7 118.7 . . ?
N3 C8 C7 120.8(3) . . ?
N3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 N4 0.93 2.50 3.351(4) 152.8 4_566 yes

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
Tc1 N1 C1 C2 -175.8(2) . . . . ?
Tc1 N1 C4 C3 176.2(2) . . . . ?
Tc1 N3 C5 C6 -170.7(2) . . . . ?
Tc1 N3 C8 C7 170.3(2) . . . . ?
Cl2 Tc1 O1 C9 164.9(5) . . . . ?
Cl1 Tc1 O1 C9 -16.6(5) . . . . ?
N1 Tc1 O1 C9 -107.1(5) . . . . ?
N1 C1 C2 N2 -0.3(5) . . . . ?
N2 C3 C4 N1 -0.5(5) . . . . ?
N3 Tc1 O1 C9 75.3(5) . . . . ?
N3 C5 C6 N4 -0.4(5) . . . . ?
N4 C7 C8 N3 1.0(5) . . . . ?
C1 N1 C4 C3 -0.6(5) . . . . ?
C2 N2 C3 C4 1.2(5) . . . . ?
C3 N2 C2 C1 -0.8(5) . . . . ?
C4 N1 C1 C2 1.0(4) . . . . ?
C5 N3 C8 C7 -2.7(4) . . . . ?
C6 N4 C7 C8 1.0(5) . . . . ?
C7 N4 C6 C5 -1.3(5) . . . . ?
C8 N3 C5 C6 2.4(4) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT910_mv3_lt_0m_a         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 11 Note
RESPONSE: Closed by beamstop.
;
####################################################################### 
# 
# 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_mv14_lt_0m
_database_code_depnum_ccdc_archive 'CCDC 2302027'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C11 H15 Cl2 N4 O2 Tc)'
_chemical_formula_sum            'C22 H30 Cl4 N8 O4 Tc2'
_chemical_formula_weight         808.34
_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'
Tc Tc -1.4390 0.7593 '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                   8.0605(6)
_cell_length_b                   33.630(3)
_cell_length_c                   12.0796(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.857(3)
_cell_angle_gamma                90
_cell_volume                     3098.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3694
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.723
_cell_measurement_theta_min      3.564
_shelx_estimated_absorpt_T_max   0.862
_shelx_estimated_absorpt_T_min   0.831
_exptl_absorpt_coefficient_mu    1.279
_exptl_absorpt_correction_T_max  0.7396
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0741 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.9298.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            54400
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         4.086
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6048
_reflns_number_total             9011
_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       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         9011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+2.6433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0956
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C10(H10A,H10B), C9(H9A,H9B), C29(H29A,H29B)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C3(H3), C8(H8), C6(H6), C21(H21), C7(H7), C22(H22), C5(H5),
 C26(H26), C25(H25), C23(H23), C4(H4), C24(H24), C28(H28), C27(H27)
1.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tc1 Tc 0.74814(3) 0.69180(2) 0.25681(2) 0.01091(8) Uani 1 1 d . . . . .
Tc2 Tc 0.22258(3) 0.55840(2) 0.25315(2) 0.01115(7) Uani 1 1 d . . . . .
Cl21 Cl 0.52907(10) 0.55361(3) 0.37680(7) 0.01739(18) Uani 1 1 d . . . . .
Cl1 Cl 0.44228(10) 0.69351(3) 0.13240(7) 0.01712(18) Uani 1 1 d . . . . .
Cl2 Cl 1.04671(10) 0.69361(3) 0.38016(7) 0.01782(18) Uani 1 1 d . . . . .
Cl22 Cl -0.07539(10) 0.55970(3) 0.13012(7) 0.01809(18) Uani 1 1 d . . . . .
O1 O 0.7379(3) 0.74648(8) 0.24865(16) 0.0126(6) Uani 1 1 d . . . . .
O22 O 0.2478(3) 0.60791(8) 0.26515(19) 0.0160(5) Uani 1 1 d . . . . .
O21 O 0.2301(3) 0.50342(8) 0.25061(17) 0.0141(6) Uani 1 1 d . . . . .
O2 O 0.7311(3) 0.64213(8) 0.25478(17) 0.0157(6) Uani 1 1 d . . . . .
N21 N 0.1408(3) 0.55574(9) 0.4053(2) 0.0130(6) Uani 1 1 d . . . . .
N3 N 0.8285(3) 0.69152(9) 0.1040(2) 0.0128(6) Uani 1 1 d . . . . .
N1 N 0.6600(3) 0.69493(9) 0.4061(2) 0.0125(6) Uani 1 1 d . . . . .
N23 N 0.3077(3) 0.55828(9) 0.1024(2) 0.0138(6) Uani 1 1 d . . . . .
N4 N 0.9281(4) 0.69034(10) -0.0964(3) 0.0235(7) Uani 1 1 d . . . . .
N2 N 0.5293(4) 0.70133(10) 0.5933(3) 0.0214(7) Uani 1 1 d . . . . .
N22 N 0.0338(4) 0.55110(10) 0.6032(3) 0.0239(7) Uani 1 1 d . . . . .
N24 N 0.4262(4) 0.55682(11) -0.0908(3) 0.0287(8) Uani 1 1 d . . . . .
C2 C 0.6467(5) 0.72675(12) 0.5777(3) 0.0207(8) Uani 1 1 d . . . . .
H2 H 0.686667 0.747723 0.632560 0.025 Uiso 1 1 calc R U . . .
C1 C 0.7134(4) 0.72416(11) 0.4856(3) 0.0148(7) Uani 1 1 d . . . . .
H1 H 0.797000 0.743077 0.478626 0.018 Uiso 1 1 calc R U . . .
C3 C 0.4781(4) 0.67268(12) 0.5131(3) 0.0217(8) Uani 1 1 d . . . . .
H3 H 0.394099 0.653896 0.520129 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7484(5) 0.71426(11) 0.0108(3) 0.0183(8) Uani 1 1 d . . . . .
H8 H 0.655107 0.731218 0.012648 0.022 Uiso 1 1 calc R U . . .
C6 C 1.0057(5) 0.66724(12) -0.0038(3) 0.0216(8) Uani 1 1 d . . . . .
H6 H 1.096405 0.649773 -0.007416 0.026 Uiso 1 1 calc R U . . .
C21 C 0.2181(4) 0.53073(11) 0.4933(3) 0.0161(7) Uani 1 1 d . . . . .
H21 H 0.311370 0.514240 0.488756 0.019 Uiso 1 1 calc R U . . .
C7 C 0.7989(5) 0.71342(12) -0.0866(3) 0.0226(8) Uani 1 1 d . . . . .
H7 H 0.739164 0.730077 -0.150552 0.027 Uiso 1 1 calc R U . . .
C22 C 0.1636(5) 0.52864(12) 0.5911(3) 0.0198(8) Uani 1 1 d . . . . .
H22 H 0.220913 0.510534 0.651731 0.024 Uiso 1 1 calc R U . . .
C5 C 0.9591(4) 0.66774(11) 0.0970(3) 0.0171(7) Uani 1 1 d . . . . .
H5 H 1.019395 0.651278 0.161356 0.020 Uiso 1 1 calc R U . . .
C26 C 0.4832(5) 0.58360(12) -0.0050(3) 0.0242(9) Uani 1 1 d . . . . .
H26 H 0.567071 0.602722 -0.010268 0.029 Uiso 1 1 calc R U . . .
C25 C 0.4258(4) 0.58474(11) 0.0909(3) 0.0182(8) Uani 1 1 d . . . . .
H25 H 0.470332 0.604439 0.149409 0.022 Uiso 1 1 calc R U . . .
C23 C -0.0407(4) 0.57578(12) 0.5148(3) 0.0236(9) Uani 1 1 d . . . . .
H23 H -0.132898 0.592470 0.520045 0.028 Uiso 1 1 calc R U . . .
C30 C 0.2221(4) 0.43225(10) 0.2139(3) 0.0174(7) Uani 1 1 d . . . . .
H30A H 0.204025 0.435346 0.129268 0.021 Uiso 1 1 calc R U . . .
H30B H 0.105660 0.431094 0.224859 0.021 Uiso 1 1 calc R U . . .
C4 C 0.5416(4) 0.66908(11) 0.4202(3) 0.0175(8) Uani 1 1 d . . . . .
H4 H 0.500996 0.648038 0.365695 0.021 Uiso 1 1 calc R U . . .
C24 C 0.0094(4) 0.57838(11) 0.4155(3) 0.0173(7) Uani 1 1 d . . . . .
H24 H -0.049503 0.596243 0.354512 0.021 Uiso 1 1 calc R U . . .
C11 C 0.6781(5) 0.85719(11) 0.2325(3) 0.0254(8) Uani 1 1 d . . . . .
H11A H 0.662989 0.859695 0.148984 0.038 Uiso 1 1 calc R U . . .
H11B H 0.750040 0.879253 0.275300 0.038 Uiso 1 1 calc R U . . .
H11C H 0.563048 0.857910 0.243809 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7682(4) 0.81795(11) 0.2782(3) 0.0167(7) Uani 1 1 d . . . . .
H10A H 0.884123 0.816995 0.266368 0.020 Uiso 1 1 calc R U . . .
H10B H 0.786731 0.815621 0.363011 0.020 Uiso 1 1 calc R U . . .
C28 C 0.2500(5) 0.53103(11) 0.0181(3) 0.0205(8) Uani 1 1 d . . . . .
H28 H 0.167177 0.511700 0.023718 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6560(4) 0.78403(10) 0.2138(3) 0.0164(7) Uani 1 1 d . . . . .
H9A H 0.542417 0.784535 0.228968 0.020 Uiso 1 1 calc R U . . .
H9B H 0.631954 0.787539 0.128715 0.020 Uiso 1 1 calc R U . . .
C27 C 0.3099(5) 0.53067(12) -0.0778(3) 0.0280(9) Uani 1 1 d . . . . .
H27 H 0.266038 0.510956 -0.136268 0.034 Uiso 1 1 calc R U . . .
C29 C 0.3245(4) 0.46722(10) 0.2802(3) 0.0168(7) Uani 1 1 d . . . . .
H29A H 0.353331 0.462422 0.365238 0.020 Uiso 1 1 calc R U . . .
H29B H 0.436137 0.469561 0.262975 0.020 Uiso 1 1 calc R U . . .
C31 C 0.3224(5) 0.39421(11) 0.2585(3) 0.0291(9) Uani 1 1 d . . . . .
H31A H 0.256673 0.371491 0.215037 0.044 Uiso 1 1 calc R U . . .
H31B H 0.338020 0.391049 0.341889 0.044 Uiso 1 1 calc R U . . .
H31C H 0.437474 0.395512 0.247351 0.044 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
Tc1 Cl1 2.4382(8) . ?
Tc1 Cl2 2.3869(8) . ?
Tc1 O1 1.842(3) . ?
Tc1 O2 1.676(3) . ?
Tc1 N3 2.145(3) . ?
Tc1 N1 2.144(3) . ?
Tc2 Cl21 2.4443(8) . ?
Tc2 Cl22 2.3815(8) . ?
Tc2 O22 1.678(3) . ?
Tc2 O21 1.850(3) . ?
Tc2 N21 2.145(3) . ?
Tc2 N23 2.143(3) . ?
O1 C9 1.424(4) . ?
O21 C29 1.419(4) . ?
N21 C21 1.341(4) . ?
N21 C24 1.342(4) . ?
N3 C8 1.341(4) . ?
N3 C5 1.346(4) . ?
N1 C1 1.344(4) . ?
N1 C4 1.342(4) . ?
N23 C25 1.343(4) . ?
N23 C28 1.337(4) . ?
N4 C6 1.339(5) . ?
N4 C7 1.335(5) . ?
N2 C2 1.333(5) . ?
N2 C3 1.334(5) . ?
N22 C22 1.337(5) . ?
N22 C23 1.333(5) . ?
N24 C26 1.338(5) . ?
N24 C27 1.331(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.387(5) . ?
C1 H1 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.380(5) . ?
C8 H8 0.9500 . ?
C8 C7 1.363(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.386(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(5) . ?
C7 H7 0.9500 . ?
C22 H22 0.9500 . ?
C5 H5 0.9500 . ?
C26 H26 0.9500 . ?
C26 C25 1.380(5) . ?
C25 H25 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.386(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C29 1.510(5) . ?
C30 C31 1.517(5) . ?
C4 H4 0.9500 . ?
C24 H24 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C10 1.522(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.506(5) . ?
C28 H28 0.9500 . ?
C28 C27 1.391(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C27 H27 0.9500 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 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
Cl2 Tc1 Cl1 177.15(4) . . ?
O1 Tc1 Cl1 85.68(7) . . ?
O1 Tc1 Cl2 91.54(7) . . ?
O1 Tc1 N3 88.81(10) . . ?
O1 Tc1 N1 88.55(10) . . ?
O2 Tc1 Cl1 87.28(7) . . ?
O2 Tc1 Cl2 95.50(7) . . ?
O2 Tc1 O1 172.94(10) . . ?
O2 Tc1 N3 91.67(11) . . ?
O2 Tc1 N1 90.75(11) . . ?
N3 Tc1 Cl1 89.77(7) . . ?
N3 Tc1 Cl2 90.77(7) . . ?
N1 Tc1 Cl1 88.47(7) . . ?
N1 Tc1 Cl2 90.86(7) . . ?
N1 Tc1 N3 176.93(12) . . ?
Cl22 Tc2 Cl21 177.17(4) . . ?
O22 Tc2 Cl21 86.69(7) . . ?
O22 Tc2 Cl22 96.04(8) . . ?
O22 Tc2 O21 171.55(9) . . ?
O22 Tc2 N21 91.69(11) . . ?
O22 Tc2 N23 90.70(11) . . ?
O21 Tc2 Cl21 84.96(7) . . ?
O21 Tc2 Cl22 92.29(7) . . ?
O21 Tc2 N21 89.62(10) . . ?
O21 Tc2 N23 87.87(10) . . ?
N21 Tc2 Cl21 90.21(7) . . ?
N21 Tc2 Cl22 90.46(7) . . ?
N23 Tc2 Cl21 88.91(7) . . ?
N23 Tc2 Cl22 90.30(7) . . ?
N23 Tc2 N21 177.40(12) . . ?
C9 O1 Tc1 155.5(2) . . ?
C29 O21 Tc2 150.6(2) . . ?
C21 N21 Tc2 120.8(2) . . ?
C21 N21 C24 117.5(3) . . ?
C24 N21 Tc2 121.7(2) . . ?
C8 N3 Tc1 121.5(2) . . ?
C8 N3 C5 117.4(3) . . ?
C5 N3 Tc1 121.1(2) . . ?
C1 N1 Tc1 121.3(2) . . ?
C4 N1 Tc1 121.2(2) . . ?
C4 N1 C1 117.4(3) . . ?
C25 N23 Tc2 121.3(2) . . ?
C28 N23 Tc2 121.4(2) . . ?
C28 N23 C25 117.3(3) . . ?
C7 N4 C6 115.5(3) . . ?
C2 N2 C3 115.3(3) . . ?
C23 N22 C22 115.4(3) . . ?
C27 N24 C26 115.6(3) . . ?
N2 C2 H2 118.3 . . ?
N2 C2 C1 123.4(3) . . ?
C1 C2 H2 118.3 . . ?
N1 C1 C2 120.1(3) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
N2 C3 H3 118.5 . . ?
N2 C3 C4 123.0(3) . . ?
C4 C3 H3 118.5 . . ?
N3 C8 H8 119.5 . . ?
N3 C8 C7 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
N4 C6 H6 118.6 . . ?
N4 C6 C5 122.7(3) . . ?
C5 C6 H6 118.6 . . ?
N21 C21 H21 119.6 . . ?
N21 C21 C22 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
N4 C7 C8 123.2(3) . . ?
N4 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
N22 C22 C21 122.6(3) . . ?
N22 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
N3 C5 C6 120.1(3) . . ?
N3 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
N24 C26 H26 118.5 . . ?
N24 C26 C25 123.0(3) . . ?
C25 C26 H26 118.5 . . ?
N23 C25 C26 120.6(3) . . ?
N23 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
N22 C23 H23 118.3 . . ?
N22 C23 C24 123.5(3) . . ?
C24 C23 H23 118.3 . . ?
H30A C30 H30B 108.3 . . ?
C29 C30 H30A 109.8 . . ?
C29 C30 H30B 109.8 . . ?
C29 C30 C31 109.3(3) . . ?
C31 C30 H30A 109.8 . . ?
C31 C30 H30B 109.8 . . ?
N1 C4 C3 120.8(3) . . ?
N1 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N21 C24 C23 120.2(3) . . ?
N21 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C9 C10 C11 109.5(3) . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
N23 C28 H28 119.6 . . ?
N23 C28 C27 120.8(3) . . ?
C27 C28 H28 119.6 . . ?
O1 C9 C10 112.1(3) . . ?
O1 C9 H9A 109.2 . . ?
O1 C9 H9B 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N24 C27 C28 122.7(4) . . ?
N24 C27 H27 118.7 . . ?
C28 C27 H27 118.7 . . ?
O21 C29 C30 112.2(3) . . ?
O21 C29 H29A 109.2 . . ?
O21 C29 H29B 109.2 . . ?
C30 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 O22 0.95 2.37 3.246(4) 153.9 1_655 yes
C25 H25 O2 0.95 2.43 3.248(4) 143.8 . yes
C4 H4 O22 0.95 2.42 3.238(4) 144.0 . yes
C24 H24 O2 0.95 2.36 3.253(4) 155.8 1_455 yes

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
Tc1 O1 C9 C10 168.9(3) . . . . ?
Tc1 N3 C8 C7 -179.0(3) . . . . ?
Tc1 N3 C5 C6 178.2(3) . . . . ?
Tc1 N1 C1 C2 176.3(2) . . . . ?
Tc1 N1 C4 C3 -176.3(3) . . . . ?
Tc2 O21 C29 C30 -166.7(3) . . . . ?
Tc2 N21 C21 C22 -179.2(3) . . . . ?
Tc2 N21 C24 C23 179.7(3) . . . . ?
Tc2 N23 C25 C26 178.1(3) . . . . ?
Tc2 N23 C28 C27 -178.3(3) . . . . ?
Cl21 Tc2 O21 C29 -4.7(4) . . . . ?
Cl1 Tc1 O1 C9 1.4(5) . . . . ?
Cl2 Tc1 O1 C9 -178.0(5) . . . . ?
Cl22 Tc2 O21 C29 174.6(4) . . . . ?
N21 Tc2 O21 C29 -94.9(4) . . . . ?
N21 C21 C22 N22 -0.3(6) . . . . ?
N3 Tc1 O1 C9 91.2(5) . . . . ?
N3 C8 C7 N4 0.3(6) . . . . ?
N1 Tc1 O1 C9 -87.2(5) . . . . ?
N23 Tc2 O21 C29 84.4(4) . . . . ?
N23 C28 C27 N24 0.2(6) . . . . ?
N4 C6 C5 N3 1.4(6) . . . . ?
N2 C2 C1 N1 0.0(6) . . . . ?
N2 C3 C4 N1 -0.2(6) . . . . ?
N22 C23 C24 N21 -0.9(6) . . . . ?
N24 C26 C25 N23 0.2(6) . . . . ?
C2 N2 C3 C4 0.3(5) . . . . ?
C1 N1 C4 C3 0.0(5) . . . . ?
C3 N2 C2 C1 -0.2(5) . . . . ?
C8 N3 C5 C6 -0.3(5) . . . . ?
C6 N4 C7 C8 0.8(6) . . . . ?
C21 N21 C24 C23 0.7(5) . . . . ?
C7 N4 C6 C5 -1.6(6) . . . . ?
C22 N22 C23 C24 0.5(5) . . . . ?
C5 N3 C8 C7 -0.5(5) . . . . ?
C26 N24 C27 C28 0.4(6) . . . . ?
C25 N23 C28 C27 -0.5(5) . . . . ?
C23 N22 C22 C21 0.1(5) . . . . ?
C4 N1 C1 C2 0.1(5) . . . . ?
C24 N21 C21 C22 -0.1(5) . . . . ?
C11 C10 C9 O1 177.0(3) . . . . ?
C28 N23 C25 C26 0.4(5) . . . . ?
C27 N24 C26 C25 -0.5(6) . . . . ?
C31 C30 C29 O21 -174.3(3) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT910_mv14_lt_0m          
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 29 Note
RESPONSE: Closed by beamstop. 
;
####################################################################### 
# 
# 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_mv44_lt_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2302030'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H21 Cl2 N4 O2 Tc'
_chemical_formula_sum            'C14 H21 Cl2 N4 O2 Tc'
_chemical_formula_weight         446.25
_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'
Tc Tc -1.4390 0.7593 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0399(5)
_cell_length_b                   14.1450(8)
_cell_length_c                   14.9860(8)
_cell_angle_alpha                69.993(2)
_cell_angle_beta                 84.129(2)
_cell_angle_gamma                83.815(2)
_cell_volume                     1785.73(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4539
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.474
_cell_measurement_theta_min      2.608
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.663
_exptl_absorpt_coefficient_mu    1.119
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0638 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.9018.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24202
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         4.102
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_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                6372
_reflns_number_total             8008
_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       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.807
_refine_diff_density_min         -2.129
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         8008
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.048
_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)+(0.0253P)²+2.2487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0886
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C11(H11A,H11B), C10(H10A,H10B), C30(H30A,
 H30B), C9(H9A,H9B), C29(H29A,H29B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,
 H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C22(H22), C23(H23), C21(H21), C4(H4), C26(H26), C2(H2), C3(H3),
 C5(H5), C28(H28), C6(H6), C1(H1), C27(H27), C25(H25), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tc1 Tc 0.97313(3) 0.30464(2) 0.36869(2) 0.00860(8) Uani 1 1 d . . . . .
Tc2 Tc 0.51722(3) 0.21643(2) 0.13754(2) 0.00940(8) Uani 1 1 d . . . . .
Cl1 Cl 0.78666(9) 0.44835(6) 0.33502(6) 0.01352(18) Uani 1 1 d . . . . .
Cl2 Cl 1.15589(9) 0.16650(6) 0.41217(7) 0.01601(19) Uani 1 1 d . . . . .
Cl22 Cl 0.65636(9) 0.36091(6) 0.09664(7) 0.01542(19) Uani 1 1 d . . . . .
Cl21 Cl 0.37901(10) 0.06949(7) 0.16510(7) 0.0181(2) Uani 1 1 d . . . . .
O21 O 0.6028(3) 0.18899(18) 0.03003(17) 0.0129(5) Uani 1 1 d . . . . .
O1 O 0.9823(3) 0.32856(18) 0.48327(17) 0.0122(5) Uani 1 1 d . . . . .
O22 O 0.4442(3) 0.22282(19) 0.24248(18) 0.0159(6) Uani 1 1 d . . . . .
N21 N 0.3389(3) 0.3073(2) 0.0612(2) 0.0091(6) Uani 1 1 d . . . . .
O2 O 0.9338(3) 0.29157(18) 0.26685(17) 0.0135(5) Uani 1 1 d . . . . .
N1 N 0.8020(3) 0.2064(2) 0.4419(2) 0.0094(6) Uani 1 1 d . . . . .
N22 N 0.0995(3) 0.4153(2) -0.0434(2) 0.0145(7) Uani 1 1 d . . . . .
N3 N 1.1450(3) 0.4031(2) 0.3001(2) 0.0106(6) Uani 1 1 d . . . . .
N2 N 0.5763(3) 0.0825(2) 0.5421(2) 0.0178(7) Uani 1 1 d . . . . .
N24 N 0.9362(4) -0.0020(2) 0.3094(2) 0.0195(7) Uani 1 1 d . . . . .
N23 N 0.7001(3) 0.1203(2) 0.2105(2) 0.0110(6) Uani 1 1 d . . . . .
N4 N 1.3737(3) 0.5271(2) 0.2053(2) 0.0197(7) Uani 1 1 d . . . . .
C12 C 1.0535(4) 0.2462(3) 0.7953(3) 0.0180(8) Uani 1 1 d . . . . .
H12A H 0.971240 0.278994 0.825897 0.022 Uiso 1 1 calc R U . . .
H12B H 1.141981 0.285015 0.785988 0.022 Uiso 1 1 calc R U . . .
C24 C 0.1974(4) 0.3035(3) 0.1011(3) 0.0115(7) Uani 1 1 d . . . . .
H24 H 0.178377 0.262790 0.165587 0.014 Uiso 1 1 calc R U . . .
C13 C 1.0895(4) 0.1393(3) 0.8627(3) 0.0177(8) Uani 1 1 d . . . . .
H13A H 1.005872 0.097853 0.866989 0.021 Uiso 1 1 calc R U . . .
H13B H 1.179754 0.108922 0.836371 0.021 Uiso 1 1 calc R U . . .
C11 C 1.0088(4) 0.2521(3) 0.6982(3) 0.0162(8) Uani 1 1 d . . . . .
H11A H 0.921298 0.212588 0.706877 0.019 Uiso 1 1 calc R U . . .
H11B H 1.091852 0.221406 0.666188 0.019 Uiso 1 1 calc R U . . .
C22 C 0.2406(4) 0.4190(3) -0.0809(3) 0.0143(8) Uani 1 1 d . . . . .
H22 H 0.259461 0.459436 -0.145519 0.017 Uiso 1 1 calc R U . . .
C23 C 0.0803(4) 0.3583(3) 0.0490(3) 0.0132(8) Uani 1 1 d . . . . .
H23 H -0.017316 0.355717 0.079530 0.016 Uiso 1 1 calc R U . . .
C21 C 0.3596(4) 0.3667(3) -0.0298(3) 0.0126(7) Uani 1 1 d . . . . .
H21 H 0.457713 0.372860 -0.059503 0.015 Uiso 1 1 calc R U . . .
C4 C 0.6707(4) 0.2125(3) 0.4046(3) 0.0129(7) Uani 1 1 d . . . . .
H4 H 0.653863 0.259718 0.343175 0.015 Uiso 1 1 calc R U . . .
C26 C 0.7932(4) -0.0153(3) 0.3407(3) 0.0181(8) Uani 1 1 d . . . . .
H26 H 0.771806 -0.068216 0.398630 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7084(4) 0.0767(3) 0.5773(3) 0.0154(8) Uani 1 1 d . . . . .
H2 H 0.725482 0.028806 0.638364 0.019 Uiso 1 1 calc R U . . .
C3 C 0.5595(4) 0.1504(3) 0.4549(3) 0.0160(8) Uani 1 1 d . . . . .
H3 H 0.468131 0.156208 0.426521 0.019 Uiso 1 1 calc R U . . .
C5 C 1.1300(4) 0.4719(3) 0.2125(2) 0.0122(7) Uani 1 1 d . . . . .
H5 H 1.040230 0.478999 0.182125 0.015 Uiso 1 1 calc R U . . .
C28 C 0.8431(4) 0.1340(3) 0.1782(3) 0.0139(8) Uani 1 1 d . . . . .
H28 H 0.865135 0.186922 0.120470 0.017 Uiso 1 1 calc R U . . .
C6 C 1.2452(4) 0.5324(3) 0.1665(3) 0.0191(9) Uani 1 1 d . . . . .
H6 H 1.231806 0.579692 0.104596 0.023 Uiso 1 1 calc R U . . .
C1 C 0.8215(4) 0.1375(3) 0.5289(3) 0.0126(7) Uani 1 1 d . . . . .
H1 H 0.913230 0.130653 0.557093 0.015 Uiso 1 1 calc R U . . .
C14 C 1.1159(5) 0.1375(3) 0.9616(3) 0.0271(10) Uani 1 1 d . . . . .
H14A H 1.202488 0.174997 0.958241 0.041 Uiso 1 1 calc R U . . .
H14B H 1.134557 0.067434 1.003155 0.041 Uiso 1 1 calc R U . . .
H14C H 1.027604 0.168743 0.987479 0.041 Uiso 1 1 calc R U . . .
C27 C 0.9583(4) 0.0731(3) 0.2268(3) 0.0179(8) Uani 1 1 d . . . . .
H27 H 1.057670 0.084837 0.200771 0.021 Uiso 1 1 calc R U . . .
C25 C 0.6757(4) 0.0441(3) 0.2930(3) 0.0155(8) Uani 1 1 d . . . . .
H25 H 0.576387 0.031288 0.318419 0.019 Uiso 1 1 calc R U . . .
C34 C 0.4523(5) 0.3538(4) -0.4267(3) 0.0338(11) Uani 1 1 d . . . . .
H34A H 0.509064 0.308173 -0.456553 0.051 Uiso 1 1 calc R U . . .
H34B H 0.502995 0.416018 -0.443090 0.051 Uiso 1 1 calc R U . . .
H34C H 0.351853 0.370082 -0.449643 0.051 Uiso 1 1 calc R U . . .
C10 C 0.9705(5) 0.3610(3) 0.6344(3) 0.0200(9) Uani 1 1 d . . . . .
H10A H 0.905386 0.396093 0.672483 0.024 Uiso 1 1 calc R U . . .
H10B H 1.063739 0.395835 0.614489 0.024 Uiso 1 1 calc R U . . .
C7 C 1.3859(4) 0.4598(3) 0.2928(3) 0.0209(9) Uani 1 1 d . . . . .
H7 H 1.474631 0.454396 0.323750 0.025 Uiso 1 1 calc R U . . .
C8 C 1.2735(4) 0.3976(3) 0.3399(3) 0.0167(8) Uani 1 1 d . . . . .
H8 H 1.287777 0.350069 0.401523 0.020 Uiso 1 1 calc R U . . .
C30 C 0.6665(5) 0.1618(3) -0.1206(3) 0.0265(10) Uani 1 1 d . . . . .
H30A H 0.723166 0.222567 -0.139292 0.032 Uiso 1 1 calc R U . . .
H30B H 0.723473 0.112855 -0.147514 0.032 Uiso 1 1 calc R U . . .
C9 C 0.8936(4) 0.3710(3) 0.5465(3) 0.0192(8) Uani 1 1 d . . . . .
H9A H 0.799390 0.337270 0.566044 0.023 Uiso 1 1 calc R U . . .
H9B H 0.867826 0.443446 0.512258 0.023 Uiso 1 1 calc R U . . .
C29 C 0.6562(5) 0.1161(3) -0.0137(3) 0.0241(9) Uani 1 1 d . . . . .
H29A H 0.588282 0.061006 0.006185 0.029 Uiso 1 1 calc R U . . .
H29B H 0.756026 0.086596 0.008005 0.029 Uiso 1 1 calc R U . . .
C31 C 0.5191(7) 0.1908(4) -0.1633(3) 0.0522(16) Uani 1 1 d . . . . .
H31A H 0.457519 0.236280 -0.134083 0.063 Uiso 1 1 calc R U . . .
H31B H 0.465198 0.129938 -0.151529 0.063 Uiso 1 1 calc R U . . .
C32 C 0.5476(10) 0.2457(6) -0.2728(5) 0.106(3) Uani 1 1 d . U . . .
H32A H 0.633483 0.286752 -0.281792 0.127 Uiso 1 1 calc R U . . .
H32B H 0.579646 0.192999 -0.301861 0.127 Uiso 1 1 calc R U . . .
C33 C 0.4417(8) 0.3045(5) -0.3225(4) 0.070(2) Uani 1 1 d . . . . .
H33A H 0.416059 0.359337 -0.295287 0.085 Uiso 1 1 calc R U . . .
H33B H 0.353568 0.264368 -0.307503 0.085 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
Tc1 Cl1 2.4418(9) . ?
Tc1 Cl2 2.3718(9) . ?
Tc1 O1 1.872(2) . ?
Tc1 O2 1.676(3) . ?
Tc1 N1 2.145(3) . ?
Tc1 N3 2.138(3) . ?
Tc2 Cl22 2.3819(8) . ?
Tc2 Cl21 2.4327(9) . ?
Tc2 O21 1.858(2) . ?
Tc2 O22 1.670(2) . ?
Tc2 N21 2.117(3) . ?
Tc2 N23 2.155(3) . ?
O21 C29 1.420(4) . ?
O1 C9 1.426(4) . ?
N21 C24 1.354(4) . ?
N21 C21 1.342(4) . ?
N1 C4 1.346(4) . ?
N1 C1 1.348(4) . ?
N22 C22 1.339(4) . ?
N22 C23 1.347(5) . ?
N3 C5 1.350(4) . ?
N3 C8 1.342(5) . ?
N2 C2 1.338(5) . ?
N2 C3 1.343(5) . ?
N24 C26 1.340(5) . ?
N24 C27 1.340(5) . ?
N23 C28 1.344(4) . ?
N23 C25 1.350(4) . ?
N4 C6 1.336(5) . ?
N4 C7 1.338(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.525(5) . ?
C12 C11 1.523(5) . ?
C24 H24 0.9500 . ?
C24 C23 1.381(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.517(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.533(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.379(5) . ?
C23 H23 0.9500 . ?
C21 H21 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.391(5) . ?
C26 H26 0.9500 . ?
C26 C25 1.378(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.386(5) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.391(5) . ?
C28 H28 0.9500 . ?
C28 C27 1.374(5) . ?
C6 H6 0.9500 . ?
C1 H1 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C27 H27 0.9500 . ?
C25 H25 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C34 C33 1.474(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.509(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(5) . ?
C8 H8 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C29 1.505(6) . ?
C30 C31 1.493(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.564(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.309(9) . ?
C33 H33A 0.9900 . ?
C33 H33B 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
Cl2 Tc1 Cl1 175.85(3) . . ?
O1 Tc1 Cl1 84.05(8) . . ?
O1 Tc1 Cl2 91.80(8) . . ?
O1 Tc1 N1 86.21(10) . . ?
O1 Tc1 N3 91.89(10) . . ?
O2 Tc1 Cl1 87.19(9) . . ?
O2 Tc1 Cl2 96.94(9) . . ?
O2 Tc1 O1 169.96(11) . . ?
O2 Tc1 N1 88.84(11) . . ?
O2 Tc1 N3 93.08(11) . . ?
N1 Tc1 Cl1 89.61(8) . . ?
N1 Tc1 Cl2 90.08(8) . . ?
N3 Tc1 Cl1 90.44(8) . . ?
N3 Tc1 Cl2 89.73(8) . . ?
N3 Tc1 N1 178.08(12) . . ?
Cl22 Tc2 Cl21 175.07(3) . . ?
O21 Tc2 Cl22 90.20(7) . . ?
O21 Tc2 Cl21 85.15(7) . . ?
O21 Tc2 N21 91.61(11) . . ?
O21 Tc2 N23 85.99(11) . . ?
O22 Tc2 Cl22 96.04(9) . . ?
O22 Tc2 Cl21 88.76(9) . . ?
O22 Tc2 O21 171.56(11) . . ?
O22 Tc2 N21 94.07(12) . . ?
O22 Tc2 N23 88.20(12) . . ?
N21 Tc2 Cl22 89.96(7) . . ?
N21 Tc2 Cl21 88.53(8) . . ?
N21 Tc2 N23 177.36(11) . . ?
N23 Tc2 Cl22 91.14(8) . . ?
N23 Tc2 Cl21 90.17(8) . . ?
C29 O21 Tc2 148.4(2) . . ?
C9 O1 Tc1 140.9(2) . . ?
C24 N21 Tc2 121.1(2) . . ?
C21 N21 Tc2 121.7(2) . . ?
C21 N21 C24 117.1(3) . . ?
C4 N1 Tc1 121.7(2) . . ?
C4 N1 C1 117.5(3) . . ?
C1 N1 Tc1 120.7(2) . . ?
C22 N22 C23 115.7(3) . . ?
C5 N3 Tc1 120.7(2) . . ?
C8 N3 Tc1 122.2(2) . . ?
C8 N3 C5 117.1(3) . . ?
C2 N2 C3 115.8(3) . . ?
C26 N24 C27 115.3(3) . . ?
C28 N23 Tc2 122.4(2) . . ?
C28 N23 C25 116.6(3) . . ?
C25 N23 Tc2 121.0(2) . . ?
C6 N4 C7 116.0(3) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C11 C12 C13 114.6(3) . . ?
N21 C24 H24 119.6 . . ?
N21 C24 C23 120.8(3) . . ?
C23 C24 H24 119.6 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.2(3) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C12 C11 C10 112.3(3) . . ?
H11A C11 H11B 107.9 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
N22 C22 H22 118.6 . . ?
N22 C22 C21 122.8(3) . . ?
C21 C22 H22 118.6 . . ?
N22 C23 C24 122.4(3) . . ?
N22 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
N21 C21 C22 121.0(3) . . ?
N21 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
N1 C4 H4 119.6 . . ?
N1 C4 C3 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
N24 C26 H26 118.5 . . ?
N24 C26 C25 123.1(3) . . ?
C25 C26 H26 118.5 . . ?
N2 C2 H2 118.5 . . ?
N2 C2 C1 123.0(4) . . ?
C1 C2 H2 118.5 . . ?
N2 C3 C4 122.5(4) . . ?
N2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
N3 C5 H5 119.8 . . ?
N3 C5 C6 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
N23 C28 H28 119.3 . . ?
N23 C28 C27 121.5(3) . . ?
C27 C28 H28 119.3 . . ?
N4 C6 C5 123.0(4) . . ?
N4 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
N1 C1 C2 120.4(3) . . ?
N1 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N24 C27 C28 122.7(3) . . ?
N24 C27 H27 118.6 . . ?
C28 C27 H27 118.6 . . ?
N23 C25 C26 120.8(3) . . ?
N23 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C9 C10 C11 114.8(3) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
N4 C7 H7 118.9 . . ?
N4 C7 C8 122.2(4) . . ?
C8 C7 H7 118.9 . . ?
N3 C8 C7 121.4(4) . . ?
N3 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
H30A C30 H30B 107.6 . . ?
C29 C30 H30A 108.7 . . ?
C29 C30 H30B 108.7 . . ?
C31 C30 H30A 108.7 . . ?
C31 C30 H30B 108.7 . . ?
C31 C30 C29 114.3(4) . . ?
O1 C9 C10 113.2(3) . . ?
O1 C9 H9A 108.9 . . ?
O1 C9 H9B 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
O21 C29 C30 111.6(3) . . ?
O21 C29 H29A 109.3 . . ?
O21 C29 H29B 109.3 . . ?
C30 C29 H29A 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
C30 C31 H31A 110.0 . . ?
C30 C31 H31B 110.0 . . ?
C30 C31 C32 108.3(5) . . ?
H31A C31 H31B 108.4 . . ?
C32 C31 H31A 110.0 . . ?
C32 C31 H31B 110.0 . . ?
C31 C32 H32A 107.2 . . ?
C31 C32 H32B 107.2 . . ?
H32A C32 H32B 106.8 . . ?
C33 C32 C31 120.6(6) . . ?
C33 C32 H32A 107.2 . . ?
C33 C32 H32B 107.2 . . ?
C34 C33 H33A 106.0 . . ?
C34 C33 H33B 106.0 . . ?
C32 C33 C34 125.2(5) . . ?
C32 C33 H33A 106.0 . . ?
C32 C33 H33B 106.0 . . ?
H33A C33 H33B 106.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C24 H24 O2 0.95 2.63 3.235(4) 122.3 1_455 yes
C23 H23 O2 0.95 2.64 3.252(4) 122.3 1_455 yes
C3 H3 O22 0.95 2.62 3.238(5) 123.5 . yes
C5 H5 N22 0.95 2.48 3.297(5) 143.9 2_665 yes
C1 H1 N24 0.95 2.59 3.369(5) 139.7 2_756 yes
C25 H25 N2 0.95 2.54 3.347(4) 142.9 2_656 yes

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
Tc1 O1 C9 C10 176.9(2) . . . . ?
Tc1 N1 C4 C3 -177.7(3) . . . . ?
Tc1 N1 C1 C2 177.7(3) . . . . ?
Tc1 N3 C5 C6 -176.9(3) . . . . ?
Tc1 N3 C8 C7 177.7(3) . . . . ?
Tc2 O21 C29 C30 161.1(3) . . . . ?
Tc2 N21 C24 C23 -176.0(3) . . . . ?
Tc2 N21 C21 C22 174.6(3) . . . . ?
Tc2 N23 C28 C27 178.7(3) . . . . ?
Tc2 N23 C25 C26 -178.2(3) . . . . ?
Cl1 Tc1 O1 C9 26.0(3) . . . . ?
Cl2 Tc1 O1 C9 -154.0(3) . . . . ?
Cl22 Tc2 O21 C29 146.6(5) . . . . ?
Cl21 Tc2 O21 C29 -35.1(5) . . . . ?
N21 Tc2 O21 C29 -123.5(5) . . . . ?
N21 C24 C23 N22 1.8(6) . . . . ?
O2 Tc1 O1 C9 -3.4(8) . . . . ?
N1 Tc1 O1 C9 -64.0(3) . . . . ?
N1 C4 C3 N2 0.3(6) . . . . ?
N22 C22 C21 N21 1.1(6) . . . . ?
N3 Tc1 O1 C9 116.2(3) . . . . ?
N3 C5 C6 N4 -0.6(6) . . . . ?
N2 C2 C1 N1 -0.2(6) . . . . ?
N24 C26 C25 N23 -0.1(6) . . . . ?
N23 Tc2 O21 C29 55.4(5) . . . . ?
N23 C28 C27 N24 -1.0(6) . . . . ?
N4 C7 C8 N3 -1.1(6) . . . . ?
C12 C11 C10 C9 -167.2(3) . . . . ?
C24 N21 C21 C22 -2.0(5) . . . . ?
C13 C12 C11 C10 178.7(3) . . . . ?
C11 C12 C13 C14 -173.5(3) . . . . ?
C11 C10 C9 O1 -62.1(4) . . . . ?
C22 N22 C23 C24 -2.7(5) . . . . ?
C23 N22 C22 C21 1.3(5) . . . . ?
C21 N21 C24 C23 0.6(5) . . . . ?
C4 N1 C1 C2 -0.7(5) . . . . ?
C26 N24 C27 C28 1.3(6) . . . . ?
C2 N2 C3 C4 -1.1(5) . . . . ?
C3 N2 C2 C1 1.1(5) . . . . ?
C5 N3 C8 C7 -0.1(5) . . . . ?
C28 N23 C25 C26 0.4(5) . . . . ?
C6 N4 C7 C8 1.3(6) . . . . ?
C1 N1 C4 C3 0.6(5) . . . . ?
C27 N24 C26 C25 -0.7(6) . . . . ?
C25 N23 C28 C27 0.1(5) . . . . ?
C7 N4 C6 C5 -0.5(6) . . . . ?
C8 N3 C5 C6 0.9(5) . . . . ?
C30 C31 C32 C33 -159.6(8) . . . . ?
C29 C30 C31 C32 174.9(5) . . . . ?
C31 C30 C29 O21 -70.3(5) . . . . ?
C31 C32 C33 C34 -175.3(6) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT220_mv44_lt_2_0m        
;
PROBLEM: NonSolvent Resd 2 C Ueq(max)/Ueq(min) Range 9.1 Ratio
RESPONSE: Large nonspheric displacement ellipsoids of several CH~2~ groups
seem to be physically significant.
;
_vrf_PLAT360_mv44_lt_2_0m        
;
PROBLEM: Short C(sp3)-C(sp3) Bond C32 - C33 . 1.31 Ang.
RESPONSE: This atoms have large displacement ellipsoids.
;
_vrf_PLAT910_mv44_lt_2_0m        
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 29 Note
RESPONSE: Closed by beamstop.
;
_vrf_PLAT971_mv44_lt_2_0m        
;
PROBLEM: Check Calcd Resid. Dens. 1.02Ang From C32 2.58 eA-3
RESPONSE: The structure is better refined with a non-disordered C32.
;
####################################################################### 
# 
# 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_mv8_lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2302026'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 Cl2 N4 O2 Tc'
_chemical_formula_sum            'C10 H13 Cl2 N4 O2 Tc'
_chemical_formula_weight         390.14
_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'
Tc Tc -1.4390 0.7593 '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                   11.6629(6)
_cell_length_b                   9.0674(5)
_cell_length_c                   14.0443(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.197(2)
_cell_angle_gamma                90
_cell_volume                     1433.28(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6848
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.046
_cell_measurement_theta_min      2.885
_shelx_estimated_absorpt_T_max   0.799
_shelx_estimated_absorpt_T_min   0.733
_exptl_absorpt_coefficient_mu    1.379
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0556 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.9298.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21488
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_min         4.192
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3561
_reflns_number_total             4174
_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       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0228
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+0.7229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0456
_refine_ls_wR_factor_ref         0.0488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C9-C10 \\sim C9-C10A
 with sigma of 0.02
2. Others
 Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
3.a Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tc1 Tc 0.42435(2) 0.50518(2) 0.71353(2) 0.00973(4) Uani 1 1 d . . . . .
Cl1 Cl 0.45084(4) 0.66587(5) 0.58131(3) 0.01795(9) Uani 1 1 d . . . . .
Cl2 Cl 0.41712(4) 0.34883(5) 0.84702(3) 0.01907(9) Uani 1 1 d . . . . .
O1 O 0.58097(10) 0.44915(13) 0.72397(8) 0.0134(2) Uani 1 1 d . . . . .
O2 O 0.28381(11) 0.56346(13) 0.68683(9) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.57655(13) 0.91781(16) 0.93744(10) 0.0160(3) Uani 1 1 d . . . . .
N1 N 0.48457(12) 0.68214(15) 0.81362(9) 0.0107(3) Uani 1 1 d . . . . .
N4 N 0.29566(15) 0.07538(18) 0.49563(12) 0.0258(4) Uani 1 1 d . . . . .
N3 N 0.37081(13) 0.32170(15) 0.61525(10) 0.0133(3) Uani 1 1 d . . . . .
C3 C 0.47525(16) 0.92910(19) 0.86580(13) 0.0157(3) Uani 1 1 d . . . . .
H3 H 0.4396(19) 1.018(2) 0.8595(15) 0.019 Uiso 1 1 d . U . . .
C2 C 0.62929(16) 0.78621(19) 0.94777(12) 0.0145(3) Uani 1 1 d . . . . .
H2 H 0.7005(18) 0.776(2) 0.9974(14) 0.017 Uiso 1 1 d . U . . .
C1 C 0.58404(15) 0.66764(19) 0.88688(12) 0.0131(3) Uani 1 1 d . . . . .
H1 H 0.6208(18) 0.582(2) 0.8941(14) 0.016 Uiso 1 1 d . U . . .
C6 C 0.39363(18) 0.0731(2) 0.57046(14) 0.0225(4) Uani 1 1 d . . . . .
H6 H 0.435(2) -0.015(2) 0.5844(16) 0.027 Uiso 1 1 d . U . . .
C7 C 0.23670(18) 0.2028(2) 0.48134(14) 0.0234(4) Uani 1 1 d . . . . .
H7 H 0.169(2) 0.207(2) 0.4290(16) 0.028 Uiso 1 1 d . U . . .
C4 C 0.42845(15) 0.81364(18) 0.80320(12) 0.0128(3) Uani 1 1 d . . . . .
H4 H 0.3554(18) 0.823(2) 0.7521(14) 0.015 Uiso 1 1 d . U . . .
C5 C 0.43159(17) 0.19418(19) 0.63054(13) 0.0186(4) Uani 1 1 d . . . . .
H5 H 0.4982(19) 0.194(2) 0.6857(15) 0.022 Uiso 1 1 d . U . . .
C8 C 0.27306(16) 0.32644(19) 0.53985(13) 0.0167(3) Uani 1 1 d . . . . .
H8 H 0.2280(18) 0.413(2) 0.5282(14) 0.020 Uiso 1 1 d . U . . .
C9 C 0.67861(17) 0.4548(3) 0.68118(15) 0.0237(4) Uani 1 1 d D . . . .
H9A H 0.652(2) 0.488(2) 0.6175(17) 0.028 Uiso 1 1 d . U . . .
H9B H 0.705(2) 0.361(3) 0.6767(15) 0.028 Uiso 1 1 d . U . . .
C10 C 0.7658(8) 0.5636(11) 0.7312(6) 0.0371(17) Uani 0.60(2) 1 d D . P A 1
H10A H 0.728669 0.661333 0.725087 0.056 Uiso 0.60(2) 1 calc R U P A 1
H10B H 0.832605 0.564985 0.701054 0.056 Uiso 0.60(2) 1 calc R U P A 1
H10C H 0.794628 0.537607 0.801165 0.056 Uiso 0.60(2) 1 calc R U P A 1
C10A C 0.7923(8) 0.486(3) 0.7572(10) 0.060(5) Uani 0.40(2) 1 d D . P A 2
H10D H 0.782103 0.573506 0.795438 0.090 Uiso 0.40(2) 1 calc R U P A 2
H10E H 0.855551 0.504604 0.724589 0.090 Uiso 0.40(2) 1 calc R U P A 2
H10F H 0.813560 0.401390 0.801537 0.090 Uiso 0.40(2) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tc1 Cl1 2.4429(4) . ?
Tc1 Cl2 2.3695(4) . ?
Tc1 O1 1.8643(12) . ?
Tc1 O2 1.6687(12) . ?
Tc1 N1 2.1275(13) . ?
Tc1 N3 2.1474(14) . ?
O1 C9 1.421(2) . ?
N2 C3 1.340(2) . ?
N2 C2 1.333(2) . ?
N1 C1 1.340(2) . ?
N1 C4 1.349(2) . ?
N4 C6 1.335(2) . ?
N4 C7 1.333(2) . ?
N3 C5 1.344(2) . ?
N3 C8 1.338(2) . ?
C3 H3 0.90(2) . ?
C3 C4 1.384(2) . ?
C2 H2 0.94(2) . ?
C2 C1 1.389(2) . ?
C1 H1 0.88(2) . ?
C6 H6 0.93(2) . ?
C6 C5 1.385(2) . ?
C7 H7 0.93(2) . ?
C7 C8 1.389(2) . ?
C4 H4 0.96(2) . ?
C5 H5 0.94(2) . ?
C8 H8 0.94(2) . ?
C9 H9A 0.92(2) . ?
C9 H9B 0.91(2) . ?
C9 C10 1.458(5) . ?
C9 C10A 1.496(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 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
Cl2 Tc1 Cl1 174.958(16) . . ?
O1 Tc1 Cl1 84.59(4) . . ?
O1 Tc1 Cl2 90.69(4) . . ?
O1 Tc1 N1 90.38(5) . . ?
O1 Tc1 N3 87.32(5) . . ?
O2 Tc1 Cl1 87.30(5) . . ?
O2 Tc1 Cl2 97.51(5) . . ?
O2 Tc1 O1 171.28(6) . . ?
O2 Tc1 N1 92.54(5) . . ?
O2 Tc1 N3 89.88(6) . . ?
N1 Tc1 Cl1 88.10(4) . . ?
N1 Tc1 Cl2 90.15(4) . . ?
N1 Tc1 N3 177.49(5) . . ?
N3 Tc1 Cl1 92.69(4) . . ?
N3 Tc1 Cl2 88.87(4) . . ?
C9 O1 Tc1 146.52(12) . . ?
C2 N2 C3 116.17(15) . . ?
C1 N1 Tc1 120.18(11) . . ?
C1 N1 C4 117.88(14) . . ?
C4 N1 Tc1 121.87(11) . . ?
C7 N4 C6 115.70(16) . . ?
C5 N3 Tc1 120.77(11) . . ?
C8 N3 Tc1 121.86(11) . . ?
C8 N3 C5 117.29(15) . . ?
N2 C3 H3 115.9(14) . . ?
N2 C3 C4 122.85(16) . . ?
C4 C3 H3 121.3(13) . . ?
N2 C2 H2 117.3(13) . . ?
N2 C2 C1 122.41(16) . . ?
C1 C2 H2 120.3(12) . . ?
N1 C1 C2 120.63(16) . . ?
N1 C1 H1 118.2(13) . . ?
C2 C1 H1 121.2(13) . . ?
N4 C6 H6 117.8(14) . . ?
N4 C6 C5 122.57(17) . . ?
C5 C6 H6 119.5(14) . . ?
N4 C7 H7 117.0(14) . . ?
N4 C7 C8 123.04(17) . . ?
C8 C7 H7 120.0(14) . . ?
N1 C4 C3 120.01(15) . . ?
N1 C4 H4 118.1(12) . . ?
C3 C4 H4 121.9(12) . . ?
N3 C5 C6 120.93(16) . . ?
N3 C5 H5 114.5(13) . . ?
C6 C5 H5 124.5(13) . . ?
N3 C8 C7 120.47(16) . . ?
N3 C8 H8 119.1(12) . . ?
C7 C8 H8 120.4(12) . . ?
O1 C9 H9A 108.9(14) . . ?
O1 C9 H9B 108.7(14) . . ?
O1 C9 C10 110.8(3) . . ?
O1 C9 C10A 111.3(4) . . ?
H9A C9 H9B 105.6(18) . . ?
C10 C9 H9A 105.3(14) . . ?
C10 C9 H9B 117.1(15) . . ?
C10A C9 H9A 130.0(17) . . ?
C10A C9 H9B 88.5(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10A H10D 109.5 . . ?
C9 C10A H10E 109.5 . . ?
C9 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 O2 0.90(2) 2.55(2) 3.160(2) 125.8(16) 2_556 yes
C1 H1 N4 0.88(2) 2.59(2) 3.362(2) 147.0(16) 4_666 yes
C8 H8 N2 0.94(2) 2.43(2) 3.312(2) 156.6(16) 4_575 yes

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
Tc1 O1 C9 C10 101.4(6) . . . . ?
Tc1 O1 C9 C10A 135.7(13) . . . . ?
Tc1 N1 C1 C2 174.84(12) . . . . ?
Tc1 N1 C4 C3 -175.48(12) . . . . ?
Tc1 N3 C5 C6 176.47(15) . . . . ?
Tc1 N3 C8 C7 -175.94(14) . . . . ?
Cl1 Tc1 O1 C9 -10.7(2) . . . . ?
Cl2 Tc1 O1 C9 171.1(2) . . . . ?
N2 C3 C4 N1 0.8(3) . . . . ?
N2 C2 C1 N1 0.7(3) . . . . ?
N1 Tc1 O1 C9 -98.8(2) . . . . ?
N4 C6 C5 N3 -0.5(3) . . . . ?
N4 C7 C8 N3 -0.5(3) . . . . ?
N3 Tc1 O1 C9 82.2(2) . . . . ?
C3 N2 C2 C1 1.3(3) . . . . ?
C2 N2 C3 C4 -2.0(3) . . . . ?
C1 N1 C4 C3 1.3(2) . . . . ?
C6 N4 C7 C8 -0.2(3) . . . . ?
C7 N4 C6 C5 0.7(3) . . . . ?
C4 N1 C1 C2 -2.0(2) . . . . ?
C5 N3 C8 C7 0.7(3) . . . . ?
C8 N3 C5 C6 -0.2(3) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT910_mv8_lt_0m_a         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 11 Note
RESPONSE: Closed by beamstop.
;
####################################################################### 
# 
# 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_mv88_a
_database_code_depnum_ccdc_archive 'CCDC 2302031'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H23 Cl2 N4 O2 Tc'
_chemical_formula_sum            'C15 H23 Cl2 N4 O2 Tc'
_chemical_formula_weight         460.27
_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'
Tc Tc -1.4390 0.7593 '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                   14.089(2)
_cell_length_b                   9.1069(15)
_cell_length_c                   16.009(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.149(6)
_cell_angle_gamma                90
_cell_volume                     1888.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1144
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.590
_cell_measurement_theta_min      2.590
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    1.060
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0961 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.7846.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2009
_diffrn_reflns_av_unetI/netI     0.1649
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         4.310
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_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                2036
_reflns_number_total             4324
_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       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.730
_refine_diff_density_min         -1.325
_refine_diff_density_rms         0.168
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      0.965
_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)+(0.0495P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1478
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C9(H9A,H9B),
 C14(H14A,H14B)
1.b Me refined with riding coordinates:
 C15(H15A,H15B,H15C)
1.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C7(H7), C6(H6), C1(H1), C5(H5), C2(H2), C3(H3)
;
_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
Tc1 Tc 0.84917(5) 0.49997(9) 0.64965(4) 0.01911(17) Uani 1 1 d . . . . .
Cl1 Cl 0.72666(15) 0.3528(2) 0.68749(12) 0.0261(5) Uani 1 1 d . . . . .
Cl2 Cl 0.95613(15) 0.6481(2) 0.60144(13) 0.0273(5) Uani 1 1 d . . . . .
O1 O 0.7321(4) 0.5617(5) 0.5508(3) 0.0198(12) Uani 1 1 d . . . . .
O2 O 0.9407(4) 0.4421(5) 0.7466(3) 0.0221(12) Uani 1 1 d . . . . .
N1 N 0.8223(5) 0.6833(6) 0.7217(4) 0.0188(14) Uani 1 1 d . . . . .
N3 N 0.8689(5) 0.3188(7) 0.5747(4) 0.0204(15) Uani 1 1 d . . . . .
N4 N 0.8839(5) 0.0814(7) 0.4715(4) 0.0268(16) Uani 1 1 d . . . . .
N2 N 0.7909(5) 0.9224(7) 0.8195(4) 0.0298(17) Uani 1 1 d . . . . .
C11 C 0.5554(6) 0.5641(8) 0.3488(5) 0.0257(18) Uani 1 1 d . . . . .
H11A H 0.504004 0.488991 0.347208 0.031 Uiso 1 1 calc R U . . .
H11B H 0.619586 0.512678 0.354404 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8419(6) 0.3314(8) 0.4843(5) 0.0222(18) Uani 1 1 d . . . . .
H8 H 0.818249 0.423063 0.455157 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5777(6) 0.6627(8) 0.4309(5) 0.0243(18) Uani 1 1 d . . . . .
H10A H 0.512447 0.709869 0.426095 0.029 Uiso 1 1 calc R U . . .
H10B H 0.625433 0.741577 0.429462 0.029 Uiso 1 1 calc R U . . .
C12 C 0.5138(6) 0.6526(8) 0.2590(5) 0.0293(19) Uani 1 1 d . . . . .
H12A H 0.459987 0.721277 0.260301 0.035 Uiso 1 1 calc R U . . .
H12B H 0.570799 0.711895 0.255018 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8303(6) 0.6690(8) 0.8089(5) 0.0252(19) Uani 1 1 d . . . . .
H4 H 0.846444 0.576160 0.838164 0.030 Uiso 1 1 calc R U . . .
C13 C 0.4686(7) 0.5576(8) 0.1748(5) 0.029(2) Uani 1 1 d . . . . .
H13A H 0.411226 0.498541 0.178132 0.035 Uiso 1 1 calc R U . . .
H13B H 0.522239 0.488814 0.172985 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6248(6) 0.5837(9) 0.5221(5) 0.0279(19) Uani 1 1 d . . . . .
H9A H 0.611504 0.642000 0.568518 0.034 Uiso 1 1 calc R U . . .
H9B H 0.590555 0.487288 0.517064 0.034 Uiso 1 1 calc R U . . .
C7 C 0.8483(6) 0.2114(9) 0.4337(5) 0.0255(19) Uani 1 1 d . . . . .
H7 H 0.826637 0.221917 0.369850 0.031 Uiso 1 1 calc R U . . .
C6 C 0.9150(6) 0.0741(8) 0.5621(5) 0.0259(19) Uani 1 1 d . . . . .
H6 H 0.943427 -0.015447 0.591850 0.031 Uiso 1 1 calc R U . . .
C1 C 0.7988(6) 0.8175(8) 0.6848(5) 0.0230(18) Uani 1 1 d . . . . .
H1 H 0.791506 0.831980 0.623838 0.028 Uiso 1 1 calc R U . . .
C5 C 0.9076(6) 0.1896(8) 0.6131(5) 0.0212(18) Uani 1 1 d . . . . .
H5 H 0.930150 0.178429 0.677025 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7846(6) 0.9369(9) 0.7339(5) 0.0285(19) Uani 1 1 d . . . . .
H2 H 0.770201 1.030868 0.705895 0.034 Uiso 1 1 calc R U . . .
C3 C 0.8150(6) 0.7893(9) 0.8551(5) 0.0271(19) Uani 1 1 d . . . . .
H3 H 0.822193 0.775477 0.916116 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4288(6) 0.6482(9) 0.0881(5) 0.031(2) Uani 1 1 d . . . . .
H14A H 0.488224 0.696472 0.080975 0.037 Uiso 1 1 calc R U . . .
H14B H 0.383246 0.726489 0.094214 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3695(7) 0.5602(9) 0.0025(5) 0.035(2) Uani 1 1 d . . . . .
H15A H 0.346494 0.625712 -0.050247 0.052 Uiso 1 1 calc R U . . .
H15B H 0.414544 0.484000 -0.005213 0.052 Uiso 1 1 calc R U . . .
H15C H 0.309414 0.514060 0.008046 0.052 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
Tc1 Cl1 2.442(2) . ?
Tc1 Cl2 2.367(2) . ?
Tc1 O1 1.867(5) . ?
Tc1 O2 1.667(5) . ?
Tc1 N1 2.146(6) . ?
Tc1 N3 2.121(6) . ?
O1 C9 1.411(8) . ?
N1 C4 1.362(9) . ?
N1 C1 1.341(8) . ?
N3 C8 1.349(8) . ?
N3 C5 1.340(9) . ?
N4 C7 1.334(9) . ?
N4 C6 1.341(9) . ?
N2 C2 1.345(10) . ?
N2 C3 1.326(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.519(10) . ?
C11 C12 1.548(10) . ?
C8 H8 0.9500 . ?
C8 C7 1.384(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.526(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.515(10) . ?
C4 H4 0.9500 . ?
C4 C3 1.385(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.521(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.361(10) . ?
C1 H1 0.9500 . ?
C1 C2 1.401(10) . ?
C5 H5 0.9500 . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.522(10) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
Cl2 Tc1 Cl1 175.15(7) . . ?
O1 Tc1 Cl1 84.28(16) . . ?
O1 Tc1 Cl2 90.90(16) . . ?
O1 Tc1 N1 86.4(2) . . ?
O1 Tc1 N3 91.3(2) . . ?
O2 Tc1 Cl1 87.66(18) . . ?
O2 Tc1 Cl2 97.18(18) . . ?
O2 Tc1 O1 170.7(2) . . ?
O2 Tc1 N1 88.9(2) . . ?
O2 Tc1 N3 93.2(2) . . ?
N1 Tc1 Cl1 90.13(17) . . ?
N1 Tc1 Cl2 90.08(17) . . ?
N3 Tc1 Cl1 88.63(16) . . ?
N3 Tc1 Cl2 90.97(17) . . ?
N3 Tc1 N1 177.5(2) . . ?
C9 O1 Tc1 142.7(4) . . ?
C4 N1 Tc1 121.0(5) . . ?
C1 N1 Tc1 122.5(5) . . ?
C1 N1 C4 116.4(6) . . ?
C8 N3 Tc1 119.7(5) . . ?
C5 N3 Tc1 122.9(5) . . ?
C5 N3 C8 117.3(6) . . ?
C7 N4 C6 116.1(7) . . ?
C3 N2 C2 115.5(7) . . ?
H11A C11 H11B 107.9 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C10 C11 C12 111.7(6) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
N3 C8 H8 119.9 . . ?
N3 C8 C7 120.3(7) . . ?
C7 C8 H8 119.9 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C11 C10 C9 114.4(6) . . ?
H10A C10 H10B 107.6 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.7(6) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
N1 C4 H4 119.9 . . ?
N1 C4 C3 120.3(7) . . ?
C3 C4 H4 119.9 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C12 C13 C14 112.2(6) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
O1 C9 C10 112.8(6) . . ?
O1 C9 H9A 109.0 . . ?
O1 C9 H9B 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N4 C7 C8 122.3(7) . . ?
N4 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
N4 C6 H6 118.6 . . ?
N4 C6 C5 122.8(7) . . ?
C5 C6 H6 118.6 . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.7(7) . . ?
C2 C1 H1 119.2 . . ?
N3 C5 C6 121.1(7) . . ?
N3 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
N2 C2 C1 121.9(7) . . ?
N2 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N2 C3 C4 124.1(7) . . ?
N2 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C13 C14 C15 114.2(7) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 O2 0.95 2.49 3.172(9) 129.1 2_746 yes

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
Tc1 O1 C9 C10 171.1(5) . . . . ?
Tc1 N1 C4 C3 178.5(5) . . . . ?
Tc1 N1 C1 C2 -178.0(5) . . . . ?
Tc1 N3 C8 C7 -176.0(5) . . . . ?
Tc1 N3 C5 C6 177.2(6) . . . . ?
Cl1 Tc1 O1 C9 27.9(8) . . . . ?
Cl2 Tc1 O1 C9 -152.6(8) . . . . ?
N1 Tc1 O1 C9 -62.6(8) . . . . ?
N1 C4 C3 N2 0.9(13) . . . . ?
N1 C1 C2 N2 -2.0(12) . . . . ?
N3 Tc1 O1 C9 116.4(8) . . . . ?
N3 C8 C7 N4 -2.1(12) . . . . ?
N4 C6 C5 N3 -0.6(12) . . . . ?
C11 C10 C9 O1 81.0(9) . . . . ?
C11 C12 C13 C14 -179.9(7) . . . . ?
C8 N3 C5 C6 -2.7(11) . . . . ?
C10 C11 C12 C13 -167.3(7) . . . . ?
C12 C11 C10 C9 -176.7(7) . . . . ?
C12 C13 C14 C15 -172.0(7) . . . . ?
C4 N1 C1 C2 0.9(11) . . . . ?
C7 N4 C6 C5 2.5(12) . . . . ?
C6 N4 C7 C8 -1.1(11) . . . . ?
C1 N1 C4 C3 -0.3(11) . . . . ?
C5 N3 C8 C7 3.9(11) . . . . ?
C2 N2 C3 C4 -1.9(12) . . . . ?
C3 N2 C2 C1 2.4(12) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT910_mv88_a              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 15 Note
RESPONSE: Closed by beamstop.
;
# start Validation Reply Form
_vrf_RINTA01_mv88_a              
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal was small in size and weakly absorbed.
;
####################################################################### 
# 
# 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_mv45_lt_0m
_database_code_depnum_ccdc_archive 'CCDC 2302032'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H25 Cl2 N4 O2 Tc'
_chemical_formula_sum            'C16 H25 Cl2 N4 O2 Tc'
_chemical_formula_weight         474.30
_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'
Tc Tc -1.4390 0.7593 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8651(6)
_cell_length_b                   7.6286(7)
_cell_length_c                   19.7846(18)
_cell_angle_alpha                86.031(3)
_cell_angle_beta                 89.719(4)
_cell_angle_gamma                72.288(4)
_cell_volume                     984.52(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2268
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.939
_cell_measurement_theta_min      3.062
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.8559.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17271
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_min         4.131
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4138
_reflns_number_total             5723
_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       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      0.984
_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)+(0.0276P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0886
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C9(H9A,H9B), C13(H13A,H13B), C14(H14A,H14B), C11(H11A,H11B),
 C10(H10A,H10B), C12(H12A,H12B)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C1(H1), C6(H6), C2(H2), C8(H8), C5(H5)
1.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tc1 Tc 0.58688(4) 0.30937(4) 0.15345(2) 0.01001(8) Uani 1 1 d . . . . .
Cl2 Cl 0.46746(11) 0.10151(11) 0.09432(4) 0.01576(17) Uani 1 1 d . . . . .
Cl1 Cl 0.68740(11) 0.52463(11) 0.22179(4) 0.01478(17) Uani 1 1 d . . . . .
O1 O 0.4299(3) 0.2830(3) 0.22852(11) 0.0123(5) Uani 1 1 d . . . . .
O2 O 0.7470(3) 0.3517(3) 0.09499(11) 0.0132(5) Uani 1 1 d . . . . .
N1 N 0.3393(4) 0.5312(4) 0.11001(13) 0.0109(5) Uani 1 1 d . . . . .
N2 N 0.0139(4) 0.8188(4) 0.05188(14) 0.0153(6) Uani 1 1 d . . . . .
N4 N 1.1457(4) -0.2135(4) 0.25728(14) 0.0174(6) Uani 1 1 d . . . . .
N3 N 0.8307(4) 0.0824(4) 0.19777(13) 0.0119(6) Uani 1 1 d . . . . .
C15 C -0.3683(5) 0.2695(5) 0.57706(17) 0.0199(8) Uani 1 1 d . . . . .
H15A H -0.399550 0.401482 0.580159 0.024 Uiso 1 1 calc R U . . .
H15B H -0.251268 0.209347 0.606610 0.024 Uiso 1 1 calc R U . . .
C3 C 0.2087(5) 0.8062(4) 0.03892(16) 0.0138(7) Uani 1 1 d . . . . .
H3 H 0.236505 0.895662 0.009469 0.017 Uiso 1 1 calc R U . . .
C16 C -0.5507(5) 0.2108(5) 0.60291(19) 0.0257(9) Uani 1 1 d . . . . .
H16A H -0.669119 0.273130 0.575146 0.039 Uiso 1 1 calc R U . . .
H16B H -0.576872 0.242462 0.648916 0.039 Uiso 1 1 calc R U . . .
H16C H -0.520805 0.079879 0.600908 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3709(4) 0.6646(4) 0.06778(15) 0.0121(7) Uani 1 1 d . . . . .
H4 H 0.504091 0.662107 0.057652 0.014 Uiso 1 1 calc R U . . .
C9 C 0.3760(5) 0.3246(4) 0.29615(16) 0.0135(7) Uani 1 1 d . . . . .
H9A H 0.343764 0.456400 0.299976 0.016 Uiso 1 1 calc R U . . .
H9B H 0.490908 0.262664 0.326349 0.016 Uiso 1 1 calc R U . . .
C7 C 0.9502(5) -0.1858(5) 0.27287(17) 0.0165(7) Uani 1 1 d . . . . .
H7 H 0.918750 -0.267491 0.305009 0.020 Uiso 1 1 calc R U . . .
C13 C -0.1272(5) 0.2861(5) 0.48179(16) 0.0168(7) Uani 1 1 d . . . . .
H13A H -0.160019 0.417728 0.486302 0.020 Uiso 1 1 calc R U . . .
H13B H -0.012258 0.224790 0.512025 0.020 Uiso 1 1 calc R U . . .
C1 C 0.1445(4) 0.5407(4) 0.12306(16) 0.0123(6) Uani 1 1 d . . . . .
H1 H 0.116311 0.449814 0.151684 0.015 Uiso 1 1 calc R U . . .
C14 C -0.3098(5) 0.2251(5) 0.50487(16) 0.0167(7) Uani 1 1 d . . . . .
H14A H -0.425678 0.285794 0.474926 0.020 Uiso 1 1 calc R U . . .
H14B H -0.277450 0.093158 0.501415 0.020 Uiso 1 1 calc R U . . .
C6 C 1.1817(4) -0.0918(4) 0.21076(17) 0.0146(7) Uani 1 1 d . . . . .
H6 H 1.316031 -0.106267 0.198072 0.018 Uiso 1 1 calc R U . . .
C11 C 0.1244(5) 0.3070(5) 0.38885(16) 0.0152(7) Uani 1 1 d . . . . .
H11A H 0.236862 0.245787 0.420067 0.018 Uiso 1 1 calc R U . . .
H11B H 0.092388 0.438849 0.392508 0.018 Uiso 1 1 calc R U . . .
C2 C -0.0145(5) 0.6844(5) 0.09431(17) 0.0159(7) Uani 1 1 d . . . . .
H2 H -0.147731 0.688003 0.104921 0.019 Uiso 1 1 calc R U . . .
C10 C 0.1924(4) 0.2626(5) 0.31679(16) 0.0137(7) Uani 1 1 d . . . . .
H10A H 0.226468 0.130518 0.313252 0.016 Uiso 1 1 calc R U . . .
H10B H 0.079522 0.322440 0.285571 0.016 Uiso 1 1 calc R U . . .
C12 C -0.0616(5) 0.2476(5) 0.40966(16) 0.0157(7) Uani 1 1 d . . . . .
H12A H -0.174861 0.311425 0.379098 0.019 Uiso 1 1 calc R U . . .
H12B H -0.030674 0.116425 0.404657 0.019 Uiso 1 1 calc R U . . .
C8 C 0.7916(5) -0.0420(5) 0.24378(17) 0.0165(7) Uani 1 1 d . . . . .
H8 H 0.657481 -0.030741 0.255871 0.020 Uiso 1 1 calc R U . . .
C5 C 1.0272(4) 0.0554(4) 0.18056(16) 0.0125(6) Uani 1 1 d . . . . .
H5 H 1.059779 0.135917 0.148200 0.015 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
Tc1 Cl2 2.3690(9) . ?
Tc1 Cl1 2.4510(9) . ?
Tc1 O1 1.866(2) . ?
Tc1 O2 1.674(2) . ?
Tc1 N1 2.134(2) . ?
Tc1 N3 2.147(3) . ?
O1 C9 1.418(3) . ?
N1 C4 1.340(4) . ?
N1 C1 1.342(4) . ?
N2 C3 1.336(4) . ?
N2 C2 1.339(4) . ?
N4 C7 1.331(4) . ?
N4 C6 1.338(4) . ?
N3 C8 1.355(4) . ?
N3 C5 1.347(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.528(4) . ?
C15 C14 1.515(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C4 H4 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.520(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.522(4) . ?
C13 C12 1.516(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.390(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.526(4) . ?
C11 C12 1.525(4) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 H8 0.9300 . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Tc1 Cl1 175.05(3) . . ?
O1 Tc1 Cl2 91.44(7) . . ?
O1 Tc1 Cl1 83.71(7) . . ?
O1 Tc1 N1 90.83(9) . . ?
O1 Tc1 N3 88.15(9) . . ?
O2 Tc1 Cl2 98.29(8) . . ?
O2 Tc1 Cl1 86.59(8) . . ?
O2 Tc1 O1 170.07(10) . . ?
O2 Tc1 N1 91.26(10) . . ?
O2 Tc1 N3 89.92(10) . . ?
N1 Tc1 Cl2 89.05(7) . . ?
N1 Tc1 Cl1 90.04(7) . . ?
N1 Tc1 N3 178.56(10) . . ?
N3 Tc1 Cl2 89.97(7) . . ?
N3 Tc1 Cl1 90.85(7) . . ?
C9 O1 Tc1 148.04(19) . . ?
C4 N1 Tc1 121.75(19) . . ?
C4 N1 C1 117.2(3) . . ?
C1 N1 Tc1 121.1(2) . . ?
C3 N2 C2 115.5(3) . . ?
C7 N4 C6 115.6(3) . . ?
C8 N3 Tc1 120.8(2) . . ?
C5 N3 Tc1 122.0(2) . . ?
C5 N3 C8 117.2(3) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C14 C15 C16 114.7(3) . . ?
N2 C3 H3 118.8 . . ?
N2 C3 C4 122.4(3) . . ?
C4 C3 H3 118.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C4 C3 121.2(3) . . ?
N1 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
O1 C9 H9A 109.6 . . ?
O1 C9 H9B 109.6 . . ?
O1 C9 C10 110.4(3) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
N4 C7 H7 118.3 . . ?
N4 C7 C8 123.4(3) . . ?
C8 C7 H7 118.3 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C12 C13 C14 115.3(3) . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.5(3) . . ?
C2 C1 H1 119.7 . . ?
C15 C14 C13 112.5(3) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
N4 C6 H6 118.6 . . ?
N4 C6 C5 122.9(3) . . ?
C5 C6 H6 118.6 . . ?
H11A C11 H11B 107.7 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C12 C11 C10 113.2(3) . . ?
N2 C2 C1 123.2(3) . . ?
N2 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C9 C10 C11 112.9(3) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C13 C12 C11 113.8(3) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N3 C8 C7 120.3(3) . . ?
N3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
N3 C5 C6 120.6(3) . . ?
N3 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 N2 0.93 2.56 3.225(4) 128.9 2_575 yes

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
Tc1 O1 C9 C10 170.7(3) . . . . ?
Tc1 N1 C4 C3 178.8(2) . . . . ?
Tc1 N1 C1 C2 -179.6(2) . . . . ?
Tc1 N3 C8 C7 -178.9(2) . . . . ?
Tc1 N3 C5 C6 179.3(2) . . . . ?
Cl2 Tc1 O1 C9 174.7(4) . . . . ?
Cl1 Tc1 O1 C9 -6.3(4) . . . . ?
O1 C9 C10 C11 -178.9(3) . . . . ?
N1 Tc1 O1 C9 -96.2(4) . . . . ?
N1 C1 C2 N2 1.0(5) . . . . ?
N2 C3 C4 N1 0.7(5) . . . . ?
N4 C7 C8 N3 -1.4(5) . . . . ?
N4 C6 C5 N3 0.5(5) . . . . ?
N3 Tc1 O1 C9 84.8(4) . . . . ?
C3 N2 C2 C1 -0.3(5) . . . . ?
C16 C15 C14 C13 -179.9(3) . . . . ?
C4 N1 C1 C2 -0.8(4) . . . . ?
C7 N4 C6 C5 0.4(5) . . . . ?
C1 N1 C4 C3 0.0(4) . . . . ?
C14 C13 C12 C11 -178.8(3) . . . . ?
C6 N4 C7 C8 0.0(5) . . . . ?
C2 N2 C3 C4 -0.5(5) . . . . ?
C10 C11 C12 C13 178.4(3) . . . . ?
C12 C13 C14 C15 -179.4(3) . . . . ?
C12 C11 C10 C9 179.2(3) . . . . ?
C8 N3 C5 C6 -1.8(4) . . . . ?
C5 N3 C8 C7 2.2(5) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT910_mv45_lt_0m          
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 18 Note
RESPONSE: Closed by beamstop.
;
####################################################################### 
# 
# 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_mv49_lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2302034'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H29 Cl2 N4 O2 Tc'
_chemical_formula_sum            'C18 H29 Cl2 N4 O2 Tc'
_chemical_formula_weight         502.35
_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'
Tc Tc -1.4390 0.7593 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8766(4)
_cell_length_b                   7.6359(5)
_cell_length_c                   21.6350(13)
_cell_angle_alpha                92.223(2)
_cell_angle_beta                 94.493(2)
_cell_angle_gamma                107.672(2)
_cell_volume                     1076.75(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5380
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.925
_cell_measurement_theta_min      2.840
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.937
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0537 before and 0.0447 after correction.
The Ratio of minimum to maximum transmission is 0.9091.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6253
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         4.123
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_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                5094
_reflns_number_total             6253
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.033
_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)+(0.0200P)²+0.4886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0654
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.90864
 0.09136
;
_atom_sites_solution_hydrogens   difmap
_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
Tc1 Tc 0.62275(3) 0.68776(3) 0.14068(2) 0.00830(5) Uani 1 1 d . . . . .
Cl2 Cl 0.48976(8) 0.89659(8) 0.08658(3) 0.01458(12) Uani 1 1 d . . . . .
Cl1 Cl 0.73937(8) 0.47145(7) 0.20316(3) 0.01346(11) Uani 1 1 d . . . . .
O1 O 0.4832(2) 0.7129(2) 0.20947(7) 0.0104(3) Uani 1 1 d . . . . .
O2 O 0.7692(2) 0.6471(2) 0.08702(7) 0.0118(3) Uani 1 1 d . . . . .
N3 N 0.3654(3) 0.4672(2) 0.10070(8) 0.0102(4) Uani 1 1 d . . . . .
N1 N 0.8770(3) 0.9144(2) 0.18114(8) 0.0100(4) Uani 1 1 d . . . . .
N4 N 0.0267(3) 0.1810(3) 0.04756(9) 0.0140(4) Uani 1 1 d . . . . .
N2 N 1.2054(3) 1.2088(3) 0.23543(9) 0.0152(4) Uani 1 1 d . . . . .
C6 C 0.2181(3) 0.1934(3) 0.03570(10) 0.0121(4) Uani 1 1 d . . . . .
C5 C 0.3871(3) 0.3342(3) 0.06188(11) 0.0121(4) Uani 1 1 d . . . . .
C16 C -0.4267(4) 0.7856(4) 0.54705(11) 0.0161(5) Uani 1 1 d . . . . .
C9 C 0.4459(3) 0.6703(3) 0.27186(10) 0.0121(4) Uani 1 1 d . . . . .
C10 C 0.2668(4) 0.7319(3) 0.29046(11) 0.0134(4) Uani 1 1 d . . . . .
C12 C 0.0309(4) 0.7453(4) 0.37398(11) 0.0159(5) Uani 1 1 d . . . . .
C13 C -0.0187(4) 0.7103(4) 0.44051(11) 0.0158(5) Uani 1 1 d . . . . .
C17 C -0.4695(4) 0.7386(4) 0.61286(12) 0.0216(5) Uani 1 1 d . . . . .
C15 C -0.2471(4) 0.7291(4) 0.52590(12) 0.0169(5) Uani 1 1 d . . . . .
C14 C -0.1988(4) 0.7698(4) 0.45941(11) 0.0181(5) Uani 1 1 d . . . . .
C11 C 0.2138(4) 0.6875(4) 0.35634(11) 0.0146(5) Uani 1 1 d . . . . .
C18 C -0.6460(4) 0.7931(4) 0.63675(14) 0.0240(6) Uani 1 1 d . . . . .
C1 C 0.8504(4) 1.0373(3) 0.22310(11) 0.0145(5) Uani 1 1 d . . . . .
C8 C 0.1727(3) 0.4571(3) 0.11294(11) 0.0125(4) Uani 1 1 d . . . . .
H8 H 0.155(4) 0.552(3) 0.1383(12) 0.015 Uiso 1 1 d . U . . .
C2 C 1.0132(4) 1.1811(3) 0.24999(11) 0.0163(5) Uani 1 1 d . . . . .
C4 C 1.0697(3) 0.9419(3) 0.16567(11) 0.0112(4) Uani 1 1 d . . . . .
H4 H 1.089(4) 0.860(3) 0.1372(12) 0.013 Uiso 1 1 d . U . . .
C3 C 1.2302(3) 1.0885(3) 0.19281(11) 0.0137(5) Uani 1 1 d . . . . .
H3 H 1.362(4) 1.107(3) 0.1829(12) 0.016 Uiso 1 1 d . U . . .
C7 C 0.0075(4) 0.3141(3) 0.08640(11) 0.0142(5) Uani 1 1 d . . . . .
H11A H 0.333(4) 0.744(4) 0.3834(12) 0.018(7) Uiso 1 1 d . . . . .
H17A H -0.355(5) 0.790(4) 0.6378(14) 0.035(9) Uiso 1 1 d . . . . .
H12A H 0.051(4) 0.874(4) 0.3671(12) 0.018(7) Uiso 1 1 d . . . . .
H5 H 0.523(4) 0.343(3) 0.0530(11) 0.012(6) Uiso 1 1 d . . . . .
H12B H -0.078(4) 0.681(4) 0.3477(13) 0.022(7) Uiso 1 1 d . . . . .
H2 H 0.987(4) 1.266(3) 0.2789(11) 0.012(6) Uiso 1 1 d . . . . .
H9A H 0.415(4) 0.538(3) 0.2732(11) 0.010(6) Uiso 1 1 d . . . . .
H14A H -0.325(4) 0.710(4) 0.4310(14) 0.030(8) Uiso 1 1 d . . . . .
H18A H -0.624(4) 0.930(4) 0.6376(14) 0.037(9) Uiso 1 1 d . . . . .
H18B H -0.665(4) 0.773(4) 0.6787(15) 0.035(9) Uiso 1 1 d . . . . .
H16A H -0.550(4) 0.730(4) 0.5194(13) 0.023(7) Uiso 1 1 d . . . . .
H18C H -0.775(5) 0.731(4) 0.6126(15) 0.044(10) Uiso 1 1 d . . . . .
H6 H 0.237(4) 0.102(4) 0.0094(12) 0.022(7) Uiso 1 1 d . . . . .
H16B H -0.408(4) 0.910(4) 0.5415(13) 0.029(8) Uiso 1 1 d . . . . .
H9B H 0.571(4) 0.739(4) 0.2998(13) 0.023(7) Uiso 1 1 d . . . . .
H10A H 0.294(4) 0.863(4) 0.2867(12) 0.015(6) Uiso 1 1 d . . . . .
H11B H 0.188(4) 0.560(4) 0.3623(12) 0.017(7) Uiso 1 1 d . . . . .
H14B H -0.176(4) 0.906(4) 0.4534(13) 0.029(8) Uiso 1 1 d . . . . .
H1 H 0.720(4) 1.022(3) 0.2339(12) 0.015(6) Uiso 1 1 d . . . . .
H17B H -0.489(4) 0.616(4) 0.6172(14) 0.033(8) Uiso 1 1 d . . . . .
H13A H 0.095(4) 0.769(4) 0.4655(13) 0.025(8) Uiso 1 1 d . . . . .
H15A H -0.128(5) 0.791(4) 0.5557(15) 0.042(9) Uiso 1 1 d . . . . .
H7 H -0.117(4) 0.300(3) 0.0950(12) 0.018(7) Uiso 1 1 d . . . . .
H13B H -0.046(4) 0.578(4) 0.4486(12) 0.022(7) Uiso 1 1 d . . . . .
H10B H 0.153(4) 0.678(4) 0.2637(13) 0.020(7) Uiso 1 1 d . . . . .
H15B H -0.270(4) 0.601(4) 0.5292(13) 0.031(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tc1 Cl2 2.3689(6) . ?
Tc1 Cl1 2.4508(6) . ?
Tc1 O1 1.8673(14) . ?
Tc1 O2 1.6743(14) . ?
Tc1 N3 2.1340(19) . ?
Tc1 N1 2.1501(19) . ?
O1 C9 1.425(3) . ?
N3 C5 1.344(3) . ?
N3 C8 1.351(3) . ?
N1 C1 1.343(3) . ?
N1 C4 1.348(3) . ?
N4 C6 1.336(3) . ?
N4 C7 1.337(3) . ?
N2 C2 1.339(3) . ?
N2 C3 1.333(3) . ?
C6 C5 1.385(3) . ?
C6 H6 0.93(3) . ?
C5 H5 0.95(2) . ?
C16 C17 1.511(3) . ?
C16 C15 1.523(3) . ?
C16 H16A 0.97(3) . ?
C16 H16B 0.93(3) . ?
C9 C10 1.521(3) . ?
C9 H9A 0.97(2) . ?
C9 H9B 1.00(3) . ?
C10 C11 1.524(3) . ?
C10 H10A 0.97(3) . ?
C10 H10B 0.91(3) . ?
C12 C13 1.520(3) . ?
C12 C11 1.523(3) . ?
C12 H12A 0.97(3) . ?
C12 H12B 0.90(3) . ?
C13 C14 1.522(3) . ?
C13 H13A 0.90(3) . ?
C13 H13B 1.00(3) . ?
C17 C18 1.517(3) . ?
C17 H17A 0.89(3) . ?
C17 H17B 0.91(3) . ?
C15 C14 1.524(3) . ?
C15 H15A 0.98(3) . ?
C15 H15B 0.95(3) . ?
C14 H14A 1.00(3) . ?
C14 H14B 1.02(3) . ?
C11 H11A 0.95(3) . ?
C11 H11B 0.95(3) . ?
C18 H18A 1.01(3) . ?
C18 H18B 0.94(3) . ?
C18 H18C 0.97(3) . ?
C1 C2 1.378(3) . ?
C1 H1 0.92(2) . ?
C8 H8 0.94(2) . ?
C8 C7 1.382(3) . ?
C2 H2 0.95(2) . ?
C4 H4 0.91(2) . ?
C4 C3 1.383(3) . ?
C3 H3 0.92(3) . ?
C7 H7 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Tc1 Cl1 175.11(2) . . ?
O1 Tc1 Cl2 91.36(5) . . ?
O1 Tc1 Cl1 83.85(5) . . ?
O1 Tc1 N3 90.79(7) . . ?
O1 Tc1 N1 88.36(7) . . ?
O2 Tc1 Cl2 98.18(5) . . ?
O2 Tc1 Cl1 86.65(5) . . ?
O2 Tc1 O1 170.25(7) . . ?
O2 Tc1 N3 91.38(7) . . ?
O2 Tc1 N1 89.66(7) . . ?
N3 Tc1 Cl2 89.01(5) . . ?
N3 Tc1 Cl1 90.11(5) . . ?
N3 Tc1 N1 178.53(7) . . ?
N1 Tc1 Cl2 89.81(5) . . ?
N1 Tc1 Cl1 91.00(5) . . ?
C9 O1 Tc1 147.84(13) . . ?
C5 N3 Tc1 121.74(14) . . ?
C5 N3 C8 117.19(19) . . ?
C8 N3 Tc1 121.07(15) . . ?
C1 N1 Tc1 121.12(15) . . ?
C1 N1 C4 116.5(2) . . ?
C4 N1 Tc1 122.33(15) . . ?
C6 N4 C7 115.8(2) . . ?
C3 N2 C2 115.8(2) . . ?
N4 C6 C5 122.6(2) . . ?
N4 C6 H6 118.0(16) . . ?
C5 C6 H6 119.4(16) . . ?
N3 C5 C6 120.9(2) . . ?
N3 C5 H5 116.7(15) . . ?
C6 C5 H5 122.3(15) . . ?
C17 C16 C15 112.9(2) . . ?
C17 C16 H16A 109.3(16) . . ?
C17 C16 H16B 111.7(17) . . ?
C15 C16 H16A 111.4(15) . . ?
C15 C16 H16B 110.8(17) . . ?
H16A C16 H16B 100(2) . . ?
O1 C9 C10 109.95(18) . . ?
O1 C9 H9A 106.7(14) . . ?
O1 C9 H9B 108.5(16) . . ?
C10 C9 H9A 110.9(14) . . ?
C10 C9 H9B 108.7(15) . . ?
H9A C9 H9B 112(2) . . ?
C9 C10 C11 113.29(19) . . ?
C9 C10 H10A 110.9(14) . . ?
C9 C10 H10B 110.4(16) . . ?
C11 C10 H10A 108.7(15) . . ?
C11 C10 H10B 108.5(17) . . ?
H10A C10 H10B 105(2) . . ?
C13 C12 C11 113.8(2) . . ?
C13 C12 H12A 109.4(15) . . ?
C13 C12 H12B 109.2(18) . . ?
C11 C12 H12A 110.8(15) . . ?
C11 C12 H12B 107.4(16) . . ?
H12A C12 H12B 106(2) . . ?
C12 C13 C14 114.7(2) . . ?
C12 C13 H13A 107.3(18) . . ?
C12 C13 H13B 111.3(15) . . ?
C14 C13 H13A 110.2(17) . . ?
C14 C13 H13B 108.4(15) . . ?
H13A C13 H13B 105(2) . . ?
C16 C17 C18 115.3(2) . . ?
C16 C17 H17A 108(2) . . ?
C16 C17 H17B 110.4(19) . . ?
C18 C17 H17A 110.0(19) . . ?
C18 C17 H17B 110.0(18) . . ?
H17A C17 H17B 102(3) . . ?
C16 C15 C14 115.3(2) . . ?
C16 C15 H15A 106.7(18) . . ?
C16 C15 H15B 110.7(17) . . ?
C14 C15 H15A 111.0(19) . . ?
C14 C15 H15B 107.0(18) . . ?
H15A C15 H15B 106(2) . . ?
C13 C14 C15 113.3(2) . . ?
C13 C14 H14A 111.1(16) . . ?
C13 C14 H14B 111.3(15) . . ?
C15 C14 H14A 108.4(17) . . ?
C15 C14 H14B 109.7(16) . . ?
H14A C14 H14B 102(2) . . ?
C10 C11 H11A 107.3(16) . . ?
C10 C11 H11B 111.5(15) . . ?
C12 C11 C10 112.91(19) . . ?
C12 C11 H11A 112.3(15) . . ?
C12 C11 H11B 109.2(15) . . ?
H11A C11 H11B 103(2) . . ?
C17 C18 H18A 113.2(17) . . ?
C17 C18 H18B 115.1(18) . . ?
C17 C18 H18C 112.3(19) . . ?
H18A C18 H18B 100(2) . . ?
H18A C18 H18C 108(3) . . ?
H18B C18 H18C 107(3) . . ?
N1 C1 C2 121.4(2) . . ?
N1 C1 H1 117.8(16) . . ?
C2 C1 H1 120.8(16) . . ?
N3 C8 H8 118.1(15) . . ?
N3 C8 C7 120.4(2) . . ?
C7 C8 H8 121.4(15) . . ?
N2 C2 C1 122.5(2) . . ?
N2 C2 H2 118.8(15) . . ?
C1 C2 H2 118.6(15) . . ?
N1 C4 H4 117.0(16) . . ?
N1 C4 C3 120.9(2) . . ?
C3 C4 H4 122.1(16) . . ?
N2 C3 C4 122.8(2) . . ?
N2 C3 H3 115.9(16) . . ?
C4 C3 H3 121.3(16) . . ?
N4 C7 C8 123.1(2) . . ?
N4 C7 H7 114.3(17) . . ?
C8 C7 H7 122.5(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9A N2 0.97(2) 2.55(2) 3.438(3) 151.6(19) 1_445 yes
C6 H6 N4 0.93(3) 2.56(3) 3.233(3) 130(2) 2 yes

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
Tc1 O1 C9 C10 -170.83(19) . . . . ?
Tc1 N3 C5 C6 -179.12(16) . . . . ?
Tc1 N3 C8 C7 179.60(17) . . . . ?
Tc1 N1 C1 C2 178.87(18) . . . . ?
Tc1 N1 C4 C3 -179.63(16) . . . . ?
Cl2 Tc1 O1 C9 -174.2(3) . . . . ?
Cl1 Tc1 O1 C9 6.7(3) . . . . ?
O1 C9 C10 C11 178.8(2) . . . . ?
N3 Tc1 O1 C9 96.7(3) . . . . ?
N3 C8 C7 N4 -0.6(4) . . . . ?
N1 Tc1 O1 C9 -84.5(3) . . . . ?
N1 C1 C2 N2 1.2(4) . . . . ?
N1 C4 C3 N2 0.4(3) . . . . ?
N4 C6 C5 N3 -0.4(3) . . . . ?
C6 N4 C7 C8 0.3(3) . . . . ?
C5 N3 C8 C7 0.4(3) . . . . ?
C16 C15 C14 C13 -179.8(2) . . . . ?
C9 C10 C11 C12 -178.6(2) . . . . ?
C12 C13 C14 C15 178.8(2) . . . . ?
C13 C12 C11 C10 -177.4(2) . . . . ?
C17 C16 C15 C14 178.9(2) . . . . ?
C15 C16 C17 C18 179.5(2) . . . . ?
C11 C12 C13 C14 179.1(2) . . . . ?
C1 N1 C4 C3 0.9(3) . . . . ?
C8 N3 C5 C6 0.1(3) . . . . ?
C2 N2 C3 C4 -1.0(3) . . . . ?
C4 N1 C1 C2 -1.7(3) . . . . ?
C3 N2 C2 C1 0.2(3) . . . . ?
C7 N4 C6 C5 0.2(3) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.90864
2 0.09136

# start Validation Reply Form
_vrf_PLAT910_mv49_lt_0m_a        
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 21 Note
RESPONSE: Closed by beamstop.
;
####################################################################### 
# 
# 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_mv39_lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2302029'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H19 Cl2 N4 O2 Tc'
_chemical_formula_sum            'C13 H19 Cl2 N4 O2 Tc'
_chemical_formula_weight         432.22
_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'
Tc Tc -1.4390 0.7593 '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                   14.0797(10)
_cell_length_b                   8.8218(6)
_cell_length_c                   14.5189(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.072(2)
_cell_angle_gamma                90
_cell_volume                     1704.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4540
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.866
_cell_measurement_theta_min      3.062
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.721
_exptl_absorpt_coefficient_mu    1.169
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0741 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.8682.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28302
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         4.195
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3650
_reflns_number_total             4961
_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       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4961
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.006
_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)+(0.0188P)²+0.5294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0628
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C9(H9A,H9B)
1.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C2(H2), C6(H6), C4(H4), C8(H8), C1(H1), C5(H5)
1.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
Tc1 Tc 0.28783(2) 0.49639(2) 0.62547(2) 0.00756(5) Uani 1 1 d . . . . .
Cl1 Cl 0.43748(4) 0.64630(6) 0.64204(4) 0.01339(12) Uani 1 1 d . . . . .
Cl2 Cl 0.14112(4) 0.34542(6) 0.59493(4) 0.01367(12) Uani 1 1 d . . . . .
O1 O 0.30286(11) 0.43039(17) 0.50963(11) 0.0104(3) Uani 1 1 d . . . . .
O2 O 0.28949(12) 0.56292(17) 0.73395(11) 0.0133(3) Uani 1 1 d . . . . .
N3 N 0.19726(14) 0.6797(2) 0.55022(13) 0.0097(4) Uani 1 1 d . . . . .
N4 N 0.08387(15) 0.9232(2) 0.44821(14) 0.0146(4) Uani 1 1 d . . . . .
N1 N 0.38231(14) 0.3115(2) 0.69596(13) 0.0098(4) Uani 1 1 d . . . . .
N2 N 0.50916(15) 0.0730(2) 0.78660(15) 0.0162(4) Uani 1 1 d . . . . .
C7 C 0.08145(17) 0.7869(3) 0.40740(17) 0.0145(5) Uani 1 1 d . . . . .
H7 H 0.040303 0.772775 0.341581 0.017 Uiso 1 1 calc R U . . .
C3 C 0.51842(17) 0.2114(3) 0.82533(17) 0.0161(5) Uani 1 1 d . . . . .
H3 H 0.569585 0.228869 0.885925 0.019 Uiso 1 1 calc R U . . .
C2 C 0.43475(18) 0.0544(3) 0.70208(18) 0.0149(5) Uani 1 1 d . . . . .
H2 H 0.425292 -0.042525 0.671983 0.018 Uiso 1 1 calc R U . . .
C6 C 0.14297(18) 0.9354(3) 0.54115(17) 0.0132(5) Uani 1 1 d . . . . .
H6 H 0.145588 1.029941 0.573254 0.016 Uiso 1 1 calc R U . . .
C4 C 0.45661(16) 0.3305(3) 0.78093(16) 0.0122(5) Uani 1 1 d . . . . .
H4 H 0.466893 0.427483 0.811074 0.015 Uiso 1 1 calc R U . . .
C8 C 0.13698(16) 0.6651(3) 0.45782(16) 0.0115(5) Uani 1 1 d . . . . .
H8 H 0.132112 0.569694 0.426210 0.014 Uiso 1 1 calc R U . . .
C1 C 0.37100(17) 0.1716(2) 0.65688(17) 0.0128(5) Uani 1 1 d . . . . .
H1 H 0.318495 0.152821 0.597399 0.015 Uiso 1 1 calc R U . . .
C10 C 0.29730(18) 0.3399(3) 0.35160(16) 0.0166(5) Uani 1 1 d . . . . .
H10A H 0.333685 0.345589 0.303754 0.020 Uiso 1 1 calc R U . . .
H10B H 0.232407 0.393290 0.323231 0.020 Uiso 1 1 calc R U . . .
C11 C 0.27623(18) 0.1731(3) 0.36712(17) 0.0159(5) Uani 1 1 d . . . . .
H11A H 0.250543 0.165884 0.422820 0.019 Uiso 1 1 calc R U . . .
H11B H 0.222844 0.135802 0.308479 0.019 Uiso 1 1 calc R U . . .
C5 C 0.20034(17) 0.8170(2) 0.59253(16) 0.0114(5) Uani 1 1 d . . . . .
H5 H 0.242219 0.831997 0.657996 0.014 Uiso 1 1 calc R U . . .
C13 C 0.3491(2) -0.0915(3) 0.41106(19) 0.0236(6) Uani 1 1 d . . . . .
H13A H 0.290131 -0.131798 0.360155 0.035 Uiso 1 1 calc R U . . .
H13B H 0.337215 -0.094184 0.473891 0.035 Uiso 1 1 calc R U . . .
H13C H 0.408029 -0.153451 0.414842 0.035 Uiso 1 1 calc R U . . .
C12 C 0.36752(19) 0.0713(3) 0.3866(2) 0.0214(6) Uani 1 1 d . . . . .
H12A H 0.422999 0.114024 0.441485 0.026 Uiso 1 1 calc R U . . .
H12B H 0.389391 0.071116 0.328401 0.026 Uiso 1 1 calc R U . . .
C9 C 0.35844(18) 0.4219(3) 0.44387(17) 0.0155(5) Uani 1 1 d . . . . .
H9A H 0.422211 0.366867 0.474903 0.019 Uiso 1 1 calc R U . . .
H9B H 0.374950 0.525334 0.427475 0.019 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
Tc1 Cl1 2.4321(6) . ?
Tc1 Cl2 2.3746(6) . ?
Tc1 O1 1.8562(15) . ?
Tc1 O2 1.6737(16) . ?
Tc1 N3 2.1268(18) . ?
Tc1 N1 2.1416(18) . ?
O1 C9 1.421(3) . ?
N3 C8 1.339(3) . ?
N3 C5 1.352(3) . ?
N4 C7 1.337(3) . ?
N4 C6 1.338(3) . ?
N1 C4 1.342(3) . ?
N1 C1 1.347(3) . ?
N2 C3 1.333(3) . ?
N2 C2 1.338(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.385(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C8 H8 0.9500 . ?
C1 H1 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.532(3) . ?
C10 C9 1.518(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.517(3) . ?
C5 H5 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C12 1.522(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 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
Cl2 Tc1 Cl1 174.93(2) . . ?
O1 Tc1 Cl1 84.75(5) . . ?
O1 Tc1 Cl2 90.27(5) . . ?
O1 Tc1 N3 89.98(7) . . ?
O1 Tc1 N1 87.55(7) . . ?
O2 Tc1 Cl1 88.34(6) . . ?
O2 Tc1 Cl2 96.67(6) . . ?
O2 Tc1 O1 172.74(7) . . ?
O2 Tc1 N3 92.21(7) . . ?
O2 Tc1 N1 90.11(7) . . ?
N3 Tc1 Cl1 89.55(5) . . ?
N3 Tc1 Cl2 89.51(5) . . ?
N3 Tc1 N1 177.28(7) . . ?
N1 Tc1 Cl1 89.08(5) . . ?
N1 Tc1 Cl2 91.65(5) . . ?
C9 O1 Tc1 151.24(14) . . ?
C8 N3 Tc1 121.26(15) . . ?
C8 N3 C5 117.20(19) . . ?
C5 N3 Tc1 121.51(14) . . ?
C7 N4 C6 115.90(19) . . ?
C4 N1 Tc1 121.33(15) . . ?
C4 N1 C1 116.82(19) . . ?
C1 N1 Tc1 121.84(15) . . ?
C3 N2 C2 116.0(2) . . ?
N4 C7 H7 118.8 . . ?
N4 C7 C8 122.3(2) . . ?
C8 C7 H7 118.8 . . ?
N2 C3 H3 118.7 . . ?
N2 C3 C4 122.7(2) . . ?
C4 C3 H3 118.7 . . ?
N2 C2 H2 118.8 . . ?
N2 C2 C1 122.4(2) . . ?
C1 C2 H2 118.8 . . ?
N4 C6 H6 118.5 . . ?
N4 C6 C5 123.0(2) . . ?
C5 C6 H6 118.5 . . ?
N1 C4 C3 121.1(2) . . ?
N1 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N3 C8 C7 121.1(2) . . ?
N3 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
N1 C1 C2 121.0(2) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C9 C10 C11 114.1(2) . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.8(2) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
N3 C5 C6 120.4(2) . . ?
N3 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
C11 C12 C13 113.8(2) . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O1 C9 C10 109.89(19) . . ?
O1 C9 H9A 109.7 . . ?
O1 C9 H9B 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 O2 0.95 2.66 3.287(3) 123.8 2_556 yes
C4 H4 N4 0.95 2.50 3.314(3) 143.3 4_676 yes
C8 H8 N2 0.95 2.53 3.302(3) 138.6 4_565 yes
C5 H5 O2 0.95 2.70 3.292(3) 121.4 2_556 yes

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
Tc1 O1 C9 C10 -175.4(2) . . . . ?
Tc1 N3 C8 C7 -176.98(17) . . . . ?
Tc1 N3 C5 C6 178.09(17) . . . . ?
Tc1 N1 C4 C3 -178.94(17) . . . . ?
Tc1 N1 C1 C2 178.05(17) . . . . ?
Cl1 Tc1 O1 C9 8.2(3) . . . . ?
Cl2 Tc1 O1 C9 -172.8(3) . . . . ?
N3 Tc1 O1 C9 97.7(3) . . . . ?
N4 C7 C8 N3 -1.0(4) . . . . ?
N4 C6 C5 N3 -1.4(4) . . . . ?
N1 Tc1 O1 C9 -81.1(3) . . . . ?
N2 C3 C4 N1 0.9(4) . . . . ?
N2 C2 C1 N1 1.0(4) . . . . ?
C7 N4 C6 C5 1.4(4) . . . . ?
C3 N2 C2 C1 0.2(4) . . . . ?
C2 N2 C3 C4 -1.1(4) . . . . ?
C6 N4 C7 C8 -0.2(4) . . . . ?
C4 N1 C1 C2 -1.2(3) . . . . ?
C8 N3 C5 C6 0.0(3) . . . . ?
C1 N1 C4 C3 0.3(3) . . . . ?
C10 C11 C12 C13 174.8(2) . . . . ?
C11 C10 C9 O1 -65.0(3) . . . . ?
C5 N3 C8 C7 1.1(3) . . . . ?
C9 C10 C11 C12 -72.6(3) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT910_mv39_lt_0m_a        
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 13 Note
RESPONSE: Closed by beamstop.
;
####################################################################### 
# 
# 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_mv15_lt_0m
_database_code_depnum_ccdc_archive 'CCDC 2302028'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H17 Cl2 N4 O2 Tc)'
_chemical_formula_sum            'C24 H34 Cl4 N8 O4 Tc2'
_chemical_formula_weight         836.39
_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'
Tc Tc -1.4390 0.7593 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0647(11)
_cell_length_b                   12.8136(15)
_cell_length_c                   14.4134(17)
_cell_angle_alpha                74.521(5)
_cell_angle_beta                 82.598(6)
_cell_angle_gamma                83.057(5)
_cell_volume                     1593.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1135
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.292
_cell_measurement_theta_min      3.477
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0842 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.8957.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1220
_diffrn_reflns_av_unetI/netI     0.1631
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28315
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         4.141
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5523
_reflns_number_total             9273
_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       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.924
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.217
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         9273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      0.949
_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)+(0.0183P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1238
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C31(H31A,H31B), C10(H10A,H10B), C30(H30A,H30B),
 C29(H29A,H29B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C7(H7), C22(H22), C23(H23), C27(H27), C24(H24), C26(H26),
 C5(H5), C2(H2), C4(H4), C21(H21), C3(H3), C28(H28), C25(H25), C1(H1)
1.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tc1 Tc 0.52265(5) 0.11015(4) 0.22759(3) 0.00979(11) Uani 1 1 d . . . . .
Tc2 Tc 0.96367(5) 0.40335(4) 0.29422(3) 0.01000(11) Uani 1 1 d . . . . .
Cl1 Cl 0.37486(14) 0.13305(11) 0.09288(9) 0.0151(3) Uani 1 1 d . . . . .
Cl21 Cl 0.78404(14) 0.41222(11) 0.43415(9) 0.0165(3) Uani 1 1 d . . . . .
Cl2 Cl 0.66931(15) 0.07320(11) 0.35976(9) 0.0158(3) Uani 1 1 d . . . . .
Cl22 Cl 1.14257(14) 0.40785(11) 0.15806(9) 0.0161(3) Uani 1 1 d . . . . .
O1 O 0.5975(4) -0.0203(3) 0.1989(2) 0.0111(8) Uani 1 1 d . . . . .
O21 O 0.9975(4) 0.5435(3) 0.2951(3) 0.0131(8) Uani 1 1 d . . . . .
O2 O 0.4454(4) 0.2312(3) 0.2397(3) 0.0148(8) Uani 1 1 d . . . . .
O22 O 0.9259(4) 0.2742(3) 0.3119(3) 0.0160(8) Uani 1 1 d . . . . .
N4 N 0.1056(5) -0.0744(4) 0.4323(3) 0.0156(10) Uani 1 1 d . . . . .
N24 N 0.5619(5) 0.5558(4) 0.0840(3) 0.0159(10) Uani 1 1 d . . . . .
N3 N 0.3446(5) 0.0318(4) 0.3204(3) 0.0106(9) Uani 1 1 d . . . . .
N21 N 1.1400(5) 0.3453(3) 0.3864(3) 0.0110(9) Uani 1 1 d . . . . .
N2 N 0.9357(5) 0.2875(4) 0.0064(3) 0.0200(11) Uani 1 1 d . . . . .
N22 N 1.3781(5) 0.2603(4) 0.4982(3) 0.0175(11) Uani 1 1 d . . . . .
N23 N 0.7925(5) 0.4649(3) 0.2006(3) 0.0112(9) Uani 1 1 d . . . . .
N1 N 0.7027(5) 0.1852(4) 0.1307(3) 0.0140(10) Uani 1 1 d . . . . .
C6 C 0.0859(6) 0.0232(4) 0.3710(4) 0.0144(12) Uani 1 1 d . . . . .
H6 H -0.012893 0.057209 0.365695 0.017 Uiso 1 1 calc R U . . .
C11 C 0.5876(6) -0.2662(4) 0.2668(4) 0.0165(12) Uani 1 1 d . . . . .
H11A H 0.617424 -0.225457 0.309771 0.020 Uiso 1 1 calc R U . . .
H11B H 0.679769 -0.301239 0.238882 0.020 Uiso 1 1 calc R U . . .
C8 C 0.3673(6) -0.0659(4) 0.3836(4) 0.0120(11) Uani 1 1 d . . . . .
H8 H 0.466004 -0.099099 0.391138 0.014 Uiso 1 1 calc R U . . .
C7 C 0.2469(6) -0.1179(4) 0.4376(4) 0.0156(12) Uani 1 1 d . . . . .
H7 H 0.265620 -0.187676 0.480275 0.019 Uiso 1 1 calc R U . . .
C22 C 1.3789(6) 0.3562(5) 0.4328(4) 0.0168(12) Uani 1 1 d . . . . .
H22 H 1.463027 0.396586 0.424444 0.020 Uiso 1 1 calc R U . . .
C23 C 1.2529(6) 0.2088(5) 0.5091(4) 0.0172(12) Uani 1 1 d . . . . .
H23 H 1.246082 0.140816 0.555673 0.021 Uiso 1 1 calc R U . . .
C27 C 0.6954(6) 0.5953(4) 0.0674(4) 0.0143(12) Uani 1 1 d . . . . .
H27 H 0.712443 0.656419 0.014262 0.017 Uiso 1 1 calc R U . . .
C24 C 1.1342(6) 0.2516(4) 0.4547(4) 0.0142(11) Uani 1 1 d . . . . .
H24 H 1.047086 0.213706 0.466139 0.017 Uiso 1 1 calc R U . . .
C26 C 0.5471(6) 0.4674(4) 0.1583(4) 0.0163(12) Uani 1 1 d . . . . .
H26 H 0.455501 0.434687 0.170582 0.020 Uiso 1 1 calc R U . . .
C5 C 0.2030(6) 0.0777(4) 0.3143(4) 0.0122(11) Uani 1 1 d . . . . .
H5 H 0.183338 0.147200 0.271378 0.015 Uiso 1 1 calc R U . . .
C9 C 0.5988(6) -0.0892(4) 0.1358(4) 0.0167(12) Uani 1 1 d . . . . .
H9A H 0.703183 -0.114973 0.117431 0.020 Uiso 1 1 calc R U . . .
H9B H 0.554431 -0.047716 0.075996 0.020 Uiso 1 1 calc R U . . .
C31 C 0.9880(6) 0.7947(5) 0.2123(4) 0.0210(13) Uani 1 1 d . . . . .
H31A H 0.895311 0.827695 0.241523 0.025 Uiso 1 1 calc R U . . .
H31B H 0.958932 0.751264 0.171226 0.025 Uiso 1 1 calc R U . . .
C2 C 0.9605(6) 0.2000(5) 0.0794(4) 0.0214(13) Uani 1 1 d . . . . .
H2 H 1.060706 0.171938 0.089524 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6758(6) 0.2723(4) 0.0579(4) 0.0175(12) Uani 1 1 d . . . . .
H4 H 0.575633 0.300564 0.047772 0.021 Uiso 1 1 calc R U . . .
C32 C 1.0803(7) 0.8858(5) 0.1485(4) 0.0284(15) Uani 1 1 d . . . . .
H32A H 1.020450 0.932311 0.098645 0.043 Uiso 1 1 calc R U . . .
H32B H 1.170538 0.853545 0.117637 0.043 Uiso 1 1 calc R U . . .
H32C H 1.108648 0.929389 0.188737 0.043 Uiso 1 1 calc R U . . .
C10 C 0.5109(6) -0.1861(4) 0.1849(4) 0.0166(12) Uani 1 1 d . . . . .
H10A H 0.496034 -0.224481 0.136059 0.020 Uiso 1 1 calc R U . . .
H10B H 0.411232 -0.159704 0.211034 0.020 Uiso 1 1 calc R U . . .
C21 C 1.2629(6) 0.3992(4) 0.3767(4) 0.0174(12) Uani 1 1 d . . . . .
H21 H 1.269451 0.467484 0.330629 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7925(7) 0.3221(5) -0.0031(4) 0.0223(14) Uani 1 1 d . . . . .
H3 H 0.769168 0.383925 -0.054136 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4910(7) -0.3545(5) 0.3273(4) 0.0232(14) Uani 1 1 d . . . . .
H12A H 0.453401 -0.391193 0.284659 0.035 Uiso 1 1 calc R U . . .
H12B H 0.406600 -0.321605 0.362695 0.035 Uiso 1 1 calc R U . . .
H12C H 0.550873 -0.407598 0.373334 0.035 Uiso 1 1 calc R U . . .
C28 C 0.8102(6) 0.5497(4) 0.1253(4) 0.0133(11) Uani 1 1 d . . . . .
H28 H 0.903544 0.580111 0.110391 0.016 Uiso 1 1 calc R U . . .
C25 C 0.6586(6) 0.4215(4) 0.2180(4) 0.0134(11) Uani 1 1 d . . . . .
H25 H 0.641762 0.359975 0.270790 0.016 Uiso 1 1 calc R U . . .
C30 C 1.0733(7) 0.7196(4) 0.2925(4) 0.0205(14) Uani 1 1 d . . . . .
H30A H 1.091967 0.761988 0.337455 0.025 Uiso 1 1 calc R U . . .
H30B H 1.171631 0.694461 0.263440 0.025 Uiso 1 1 calc R U . . .
C1 C 0.8467(6) 0.1492(5) 0.1404(4) 0.0177(12) Uani 1 1 d . . . . .
H1 H 0.870476 0.086834 0.190800 0.021 Uiso 1 1 calc R U . . .
C29 C 0.9946(6) 0.6204(4) 0.3506(4) 0.0184(13) Uani 1 1 d . . . . .
H29A H 1.044454 0.586047 0.409956 0.022 Uiso 1 1 calc R U . . .
H29B H 0.889672 0.643453 0.370393 0.022 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
Tc1 Cl1 2.4335(13) . ?
Tc1 Cl2 2.3748(13) . ?
Tc1 O1 1.857(3) . ?
Tc1 O2 1.667(4) . ?
Tc1 N3 2.126(4) . ?
Tc1 N1 2.148(4) . ?
Tc2 Cl21 2.4420(14) . ?
Tc2 Cl22 2.3721(14) . ?
Tc2 O21 1.861(3) . ?
Tc2 O22 1.677(3) . ?
Tc2 N21 2.146(4) . ?
Tc2 N23 2.127(4) . ?
O1 C9 1.425(5) . ?
O21 C29 1.422(6) . ?
N4 C6 1.332(7) . ?
N4 C7 1.336(7) . ?
N24 C27 1.336(6) . ?
N24 C26 1.341(7) . ?
N3 C8 1.347(6) . ?
N3 C5 1.350(6) . ?
N21 C24 1.336(6) . ?
N21 C21 1.353(6) . ?
N2 C2 1.336(7) . ?
N2 C3 1.332(7) . ?
N22 C22 1.335(7) . ?
N22 C23 1.353(6) . ?
N23 C28 1.324(6) . ?
N23 C25 1.363(6) . ?
N1 C4 1.335(7) . ?
N1 C1 1.343(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.524(7) . ?
C11 C12 1.524(7) . ?
C8 H8 0.9500 . ?
C8 C7 1.387(7) . ?
C7 H7 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.380(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.393(7) . ?
C24 H24 0.9500 . ?
C26 H26 0.9500 . ?
C26 C25 1.385(7) . ?
C5 H5 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.517(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.541(7) . ?
C31 C30 1.522(8) . ?
C2 H2 0.9500 . ?
C2 C1 1.372(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.387(7) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C21 H21 0.9500 . ?
C3 H3 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C28 H28 0.9500 . ?
C25 H25 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C29 1.525(7) . ?
C1 H1 0.9500 . ?
C29 H29A 0.9900 . ?
C29 H29B 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
Cl2 Tc1 Cl1 175.57(5) . . ?
O1 Tc1 Cl1 84.49(11) . . ?
O1 Tc1 Cl2 91.35(11) . . ?
O1 Tc1 N3 90.14(16) . . ?
O1 Tc1 N1 88.05(16) . . ?
O2 Tc1 Cl1 88.11(12) . . ?
O2 Tc1 Cl2 96.09(12) . . ?
O2 Tc1 O1 172.47(16) . . ?
O2 Tc1 N3 91.00(17) . . ?
O2 Tc1 N1 90.66(17) . . ?
N3 Tc1 Cl1 88.08(11) . . ?
N3 Tc1 Cl2 90.43(11) . . ?
N3 Tc1 N1 177.91(15) . . ?
N1 Tc1 Cl1 90.70(12) . . ?
N1 Tc1 Cl2 90.67(12) . . ?
Cl22 Tc2 Cl21 175.74(5) . . ?
O21 Tc2 Cl21 84.64(12) . . ?
O21 Tc2 Cl22 91.11(12) . . ?
O21 Tc2 N21 87.42(15) . . ?
O21 Tc2 N23 91.19(15) . . ?
O22 Tc2 Cl21 87.50(13) . . ?
O22 Tc2 Cl22 96.74(13) . . ?
O22 Tc2 O21 171.13(17) . . ?
O22 Tc2 N21 88.59(16) . . ?
O22 Tc2 N23 92.92(16) . . ?
N21 Tc2 Cl21 90.70(12) . . ?
N21 Tc2 Cl22 88.97(12) . . ?
N23 Tc2 Cl21 90.19(12) . . ?
N23 Tc2 Cl22 90.04(12) . . ?
N23 Tc2 N21 178.28(16) . . ?
C9 O1 Tc1 146.6(3) . . ?
C29 O21 Tc2 147.0(3) . . ?
C6 N4 C7 115.9(5) . . ?
C27 N24 C26 115.7(4) . . ?
C8 N3 Tc1 122.0(4) . . ?
C8 N3 C5 118.0(4) . . ?
C5 N3 Tc1 120.0(4) . . ?
C24 N21 Tc2 120.6(3) . . ?
C24 N21 C21 117.1(5) . . ?
C21 N21 Tc2 122.3(4) . . ?
C3 N2 C2 115.2(5) . . ?
C22 N22 C23 115.6(5) . . ?
C28 N23 Tc2 121.1(3) . . ?
C28 N23 C25 117.5(4) . . ?
C25 N23 Tc2 121.4(3) . . ?
C4 N1 Tc1 120.9(4) . . ?
C4 N1 C1 116.5(5) . . ?
C1 N1 Tc1 122.6(4) . . ?
N4 C6 H6 118.4 . . ?
N4 C6 C5 123.1(5) . . ?
C5 C6 H6 118.4 . . ?
H11A C11 H11B 107.6 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C10 C11 C12 114.0(4) . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
N3 C8 H8 119.9 . . ?
N3 C8 C7 120.2(5) . . ?
C7 C8 H8 119.9 . . ?
N4 C7 C8 122.9(5) . . ?
N4 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
N22 C22 H22 118.6 . . ?
N22 C22 C21 122.9(5) . . ?
C21 C22 H22 118.6 . . ?
N22 C23 H23 118.9 . . ?
N22 C23 C24 122.3(5) . . ?
C24 C23 H23 118.9 . . ?
N24 C27 H27 118.9 . . ?
N24 C27 C28 122.1(5) . . ?
C28 C27 H27 118.9 . . ?
N21 C24 C23 121.1(5) . . ?
N21 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
N24 C26 H26 118.4 . . ?
N24 C26 C25 123.3(5) . . ?
C25 C26 H26 118.4 . . ?
N3 C5 C6 119.8(5) . . ?
N3 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
O1 C9 H9A 109.6 . . ?
O1 C9 H9B 109.6 . . ?
O1 C9 C10 110.5(4) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H31A C31 H31B 107.8 . . ?
C32 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
C30 C31 H31A 109.1 . . ?
C30 C31 H31B 109.1 . . ?
C30 C31 C32 112.5(5) . . ?
N2 C2 H2 118.8 . . ?
N2 C2 C1 122.5(5) . . ?
C1 C2 H2 118.8 . . ?
N1 C4 H4 119.7 . . ?
N1 C4 C3 120.7(5) . . ?
C3 C4 H4 119.7 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 C11 113.1(4) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N21 C21 C22 120.9(5) . . ?
N21 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
N2 C3 C4 123.3(6) . . ?
N2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N23 C28 C27 121.6(5) . . ?
N23 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
N23 C25 C26 119.7(5) . . ?
N23 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C31 C30 H30A 108.6 . . ?
C31 C30 H30B 108.6 . . ?
C31 C30 C29 114.7(4) . . ?
H30A C30 H30B 107.6 . . ?
C29 C30 H30A 108.6 . . ?
C29 C30 H30B 108.6 . . ?
N1 C1 C2 121.8(5) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
O21 C29 C30 110.9(4) . . ?
O21 C29 H29A 109.5 . . ?
O21 C29 H29B 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 O22 0.95 2.69 3.301(7) 122.8 1_455 yes
C24 H24 N4 0.95 2.43 3.292(7) 150.2 2_656 yes
C26 H26 O2 0.95 2.54 3.144(7) 121.7 . yes
C4 H4 N24 0.95 2.60 3.355(7) 137.2 2_665 yes
C28 H28 N2 0.95 2.50 3.344(7) 147.3 2_765 yes

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
Tc1 O1 C9 C10 -106.1(6) . . . . ?
Tc1 N3 C8 C7 -175.1(3) . . . . ?
Tc1 N3 C5 C6 176.1(3) . . . . ?
Tc1 N1 C4 C3 178.4(4) . . . . ?
Tc1 N1 C1 C2 -178.1(4) . . . . ?
Tc2 O21 C29 C30 168.9(4) . . . . ?
Tc2 N21 C24 C23 174.5(4) . . . . ?
Tc2 N21 C21 C22 -175.7(4) . . . . ?
Tc2 N23 C28 C27 -175.6(4) . . . . ?
Tc2 N23 C25 C26 176.6(4) . . . . ?
Cl1 Tc1 O1 C9 3.7(6) . . . . ?
Cl21 Tc2 O21 C29 26.6(6) . . . . ?
Cl2 Tc1 O1 C9 -177.8(6) . . . . ?
Cl22 Tc2 O21 C29 -153.3(6) . . . . ?
O1 C9 C10 C11 -70.0(6) . . . . ?
N4 C6 C5 N3 -0.2(8) . . . . ?
N24 C27 C28 N23 -0.5(8) . . . . ?
N24 C26 C25 N23 -1.7(8) . . . . ?
N3 Tc1 O1 C9 91.8(6) . . . . ?
N3 C8 C7 N4 -1.8(8) . . . . ?
N21 Tc2 O21 C29 -64.4(6) . . . . ?
N2 C2 C1 N1 -0.6(9) . . . . ?
N22 C22 C21 N21 0.6(9) . . . . ?
N22 C23 C24 N21 2.0(8) . . . . ?
N23 Tc2 O21 C29 116.6(6) . . . . ?
N1 Tc1 O1 C9 -87.2(6) . . . . ?
N1 C4 C3 N2 -0.1(8) . . . . ?
C6 N4 C7 C8 0.3(7) . . . . ?
C8 N3 C5 C6 -1.2(7) . . . . ?
C7 N4 C6 C5 0.7(7) . . . . ?
C22 N22 C23 C24 1.1(8) . . . . ?
C23 N22 C22 C21 -2.4(8) . . . . ?
C27 N24 C26 C25 3.0(8) . . . . ?
C24 N21 C21 C22 2.5(8) . . . . ?
C26 N24 C27 C28 -1.9(7) . . . . ?
C5 N3 C8 C7 2.2(7) . . . . ?
C31 C30 C29 O21 72.5(6) . . . . ?
C2 N2 C3 C4 0.3(8) . . . . ?
C4 N1 C1 C2 0.8(8) . . . . ?
C32 C31 C30 C29 -173.2(5) . . . . ?
C21 N21 C24 C23 -3.7(7) . . . . ?
C3 N2 C2 C1 0.0(8) . . . . ?
C12 C11 C10 C9 170.9(4) . . . . ?
C28 N23 C25 C26 -0.9(7) . . . . ?
C25 N23 C28 C27 1.9(7) . . . . ?
C1 N1 C4 C3 -0.5(7) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT910_mv15_lt_0m          
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 26 Note
RESPONSE: Closed by beamstop.
;
####################################################################### 
# 
# 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_mv59
_database_code_depnum_ccdc_archive 'CCDC 2302033'
loop_
_audit_author_name
_audit_author_address
'Anton Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H27 Cl2 N4 O2 Tc)'
_chemical_formula_sum            'C34 H54 Cl4 N8 O4 Tc2'
_chemical_formula_weight         976.65
_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'
Tc Tc -1.4390 0.7593 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.612(4)
_cell_length_b                   10.482(4)
_cell_length_c                   21.517(8)
_cell_angle_alpha                101.141(17)
_cell_angle_beta                 99.638(16)
_cell_angle_gamma                90.665(16)
_cell_volume                     2094.9(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    302
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      16.262
_cell_measurement_theta_min      2.859
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_correction_T_min  0.8161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1064 before and 0.0877 after correction.
The Ratio of minimum to maximum transmission is 0.8308.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3360
_diffrn_reflns_av_unetI/netI     0.4121
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24079
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         4.133
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2376
_reflns_number_total             7336
_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       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.865
_refine_diff_density_min         -1.272
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         7336
_refine_ls_number_restraints     276
_refine_ls_R_factor_all          0.2912
_refine_ls_R_factor_gt           0.0925
_refine_ls_restrained_S_all      0.920
_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)+(0.0609P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.2352
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O22) \\sim Ueq, Uanis(O21)
\\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(N1) \\sim Ueq,
Uanis(N2) \\sim Ueq, Uanis(N23) \\sim Ueq, Uanis(N24) \\sim Ueq, Uanis(N21)
\\sim Ueq, Uanis(N22) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C2) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq,
Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq,
Uanis(C28) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq,
Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C34)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq:
with sigma of 0.005 and sigma for terminal atoms of 0.01
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C29(H29A,H29B), C30(H30A,H30B),
  C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B)
2.b Me refined with riding coordinates:
 C17(H17A,H17B,H17C), C37(H37A,H37B,H37C)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C6(H6), C5(H5), C4(H4), C3(H3), C2(H2), C1(H1), C25(H25),
 C26(H26), C27(H27), C28(H28), C21(H21), C22(H22), C23(H23), C24(H24)
;
_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
Tc1 Tc 0.49683(19) 0.55620(15) 0.13765(10) 0.0195(4) Uani 1 1 d . . . . .
Tc2 Tc 1.00728(19) -0.05388(15) 0.86432(9) 0.0190(4) Uani 1 1 d . . . . .
Cl1 Cl 0.4848(5) 0.7902(4) 0.1751(2) 0.0266(12) Uani 1 1 d . . . . .
Cl2 Cl 0.5227(4) 0.3283(4) 0.1106(2) 0.0233(12) Uani 1 1 d . . . . .
Cl21 Cl 1.0357(5) 0.1555(4) 0.8321(2) 0.0262(12) Uani 1 1 d . . . . .
Cl22 Cl 0.9668(4) -0.2618(4) 0.8883(2) 0.0219(12) Uani 1 1 d . . . . .
O2 O 0.3806(11) 0.5727(9) 0.0732(5) 0.019(3) Uani 1 1 d . U . . .
O1 O 0.6329(11) 0.5660(10) 0.2106(6) 0.019(3) Uani 1 1 d . U . . .
O22 O 1.1171(10) 0.0097(9) 0.9315(5) 0.017(3) Uani 1 1 d . U . . .
O21 O 0.8682(11) -0.0949(9) 0.7886(5) 0.010(3) Uani 1 1 d . U . . .
N3 N 0.6635(13) 0.5876(11) 0.0886(7) 0.017(3) Uani 1 1 d . U . . .
N4 N 0.8847(14) 0.6222(12) 0.0214(7) 0.019(3) Uani 1 1 d . U . . .
N1 N 0.3337(13) 0.5254(12) 0.1896(7) 0.017(3) Uani 1 1 d . U . . .
N2 N 0.1224(15) 0.4957(12) 0.2613(7) 0.026(4) Uani 1 1 d . U . . .
N23 N 0.8392(13) 0.0208(11) 0.9124(7) 0.016(3) Uani 1 1 d . U . . .
N24 N 0.6190(14) 0.1087(12) 0.9771(7) 0.024(4) Uani 1 1 d . U . . .
N21 N 1.1686(14) -0.1304(12) 0.8130(7) 0.019(3) Uani 1 1 d . U . . .
N22 N 1.3791(14) -0.2270(12) 0.7429(7) 0.023(4) Uani 1 1 d . U . . .
C8 C 0.7851(19) 0.5205(16) 0.0948(9) 0.028(5) Uani 1 1 d . U . . .
H8 H 0.797429 0.460464 0.122974 0.033 Uiso 1 1 calc R U . . .
C7 C 0.8887(18) 0.5396(15) 0.0605(9) 0.019(5) Uani 1 1 d . U . . .
H7 H 0.969969 0.489316 0.065416 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7652(16) 0.6886(14) 0.0152(8) 0.017(4) Uani 1 1 d . U . . .
H6 H 0.754061 0.747245 -0.013633 0.020 Uiso 1 1 calc R U . . .
C5 C 0.6598(18) 0.6742(15) 0.0491(8) 0.024(4) Uani 1 1 d . U . . .
H5 H 0.580544 0.727191 0.044790 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2190(19) 0.5950(16) 0.1876(9) 0.029(5) Uani 1 1 d . U . . .
H4 H 0.209244 0.657909 0.160965 0.035 Uiso 1 1 calc R U . . .
C3 C 0.1139(18) 0.5806(16) 0.2221(9) 0.022(5) Uani 1 1 d . U . . .
H3 H 0.033481 0.632213 0.217975 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2368(18) 0.4263(16) 0.2642(9) 0.030(5) Uani 1 1 d . U . . .
H2 H 0.245751 0.363998 0.291214 0.035 Uiso 1 1 calc R U . . .
C1 C 0.3441(18) 0.4401(15) 0.2299(8) 0.022(4) Uani 1 1 d . U . . .
H1 H 0.425202 0.389520 0.234663 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7341(17) 0.6502(14) 0.2593(8) 0.021(4) Uani 1 1 d . U . . .
H9A H 0.757886 0.728011 0.242734 0.025 Uiso 1 1 calc R U . . .
H9B H 0.821986 0.603458 0.268014 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6806(19) 0.6918(17) 0.3194(9) 0.037(5) Uani 1 1 d . U . . .
H10A H 0.658754 0.614045 0.336448 0.045 Uiso 1 1 calc R U . . .
H10B H 0.591703 0.736910 0.310539 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7908(19) 0.7867(16) 0.3724(9) 0.039(5) Uani 1 1 d . U . . .
H11A H 0.763303 0.793166 0.415207 0.046 Uiso 1 1 calc R U . . .
H11B H 0.886236 0.751583 0.374267 0.046 Uiso 1 1 calc R U . . .
C12 C 0.793(2) 0.9198(16) 0.3554(10) 0.042(5) Uani 1 1 d . U . . .
H12A H 0.696162 0.952653 0.352133 0.050 Uiso 1 1 calc R U . . .
H12B H 0.821461 0.912383 0.312765 0.050 Uiso 1 1 calc R U . . .
C13 C 0.8959(18) 1.0194(15) 0.4061(9) 0.033(5) Uani 1 1 d . U . . .
H13A H 0.864138 1.031783 0.448218 0.040 Uiso 1 1 calc R U . . .
H13B H 0.991821 0.985125 0.411212 0.040 Uiso 1 1 calc R U . . .
C14 C 0.9006(17) 1.1507(14) 0.3846(9) 0.027(4) Uani 1 1 d . U . . .
H14A H 0.805609 1.186871 0.382461 0.032 Uiso 1 1 calc R U . . .
H14B H 0.924062 1.135988 0.340764 0.032 Uiso 1 1 calc R U . . .
C15 C 1.010(2) 1.2526(16) 0.4303(9) 0.040(5) Uani 1 1 d . U . . .
H15A H 0.980303 1.277271 0.472631 0.048 Uiso 1 1 calc R U . . .
H15B H 1.103595 1.213447 0.436873 0.048 Uiso 1 1 calc R U . . .
C16 C 1.023(2) 1.3714(19) 0.4022(11) 0.054(6) Uani 1 1 d . U . . .
H16A H 0.931667 1.414640 0.399563 0.064 Uiso 1 1 calc R U . . .
H16B H 1.042778 1.344927 0.357983 0.064 Uiso 1 1 calc R U . . .
C17 C 1.138(2) 1.4667(19) 0.4412(11) 0.061(7) Uani 1 1 d . U . . .
H17A H 1.141601 1.542524 0.420990 0.092 Uiso 1 1 calc R U . . .
H17B H 1.117414 1.494788 0.484829 0.092 Uiso 1 1 calc R U . . .
H17C H 1.228538 1.425067 0.443243 0.092 Uiso 1 1 calc R U . . .
C25 C 0.8464(16) 0.1367(14) 0.9520(8) 0.014(4) Uani 1 1 d . U . . .
H25 H 0.930414 0.189682 0.958355 0.017 Uiso 1 1 calc R U . . .
C26 C 0.7375(17) 0.1848(15) 0.9846(8) 0.020(4) Uani 1 1 d . U . . .
H26 H 0.746792 0.268952 1.011437 0.024 Uiso 1 1 calc R U . . .
C27 C 0.6095(17) -0.0077(15) 0.9381(8) 0.017(4) Uani 1 1 d . U . . .
H27 H 0.525896 -0.061321 0.931761 0.020 Uiso 1 1 calc R U . . .
C28 C 0.7185(17) -0.0513(16) 0.9071(9) 0.018(4) Uani 1 1 d . U . . .
H28 H 0.708907 -0.135841 0.880650 0.022 Uiso 1 1 calc R U . . .
C21 C 1.1546(17) -0.2520(14) 0.7756(8) 0.016(4) Uani 1 1 d . U . . .
H21 H 1.072621 -0.306479 0.771714 0.019 Uiso 1 1 calc R U . . .
C22 C 1.2631(17) -0.2930(15) 0.7438(8) 0.021(4) Uani 1 1 d . U . . .
H22 H 1.252949 -0.379430 0.719405 0.025 Uiso 1 1 calc R U . . .
C23 C 1.386(2) -0.1082(17) 0.7801(9) 0.028(5) Uani 1 1 d . U . . .
H23 H 1.467257 -0.054529 0.782016 0.034 Uiso 1 1 calc R U . . .
C24 C 1.2869(18) -0.0557(17) 0.8159(9) 0.025(5) Uani 1 1 d . U . . .
H24 H 1.300769 0.029484 0.841675 0.031 Uiso 1 1 calc R U . . .
C29 C 0.7615(18) -0.0381(15) 0.7513(9) 0.027(5) Uani 1 1 d . U . . .
H29A H 0.730053 0.038626 0.779350 0.033 Uiso 1 1 calc R U . . .
H29B H 0.679795 -0.101356 0.736613 0.033 Uiso 1 1 calc R U . . .
C30 C 0.7991(19) 0.0033(17) 0.6952(9) 0.036(5) Uani 1 1 d . U . . .
H30A H 0.823007 -0.073753 0.665003 0.043 Uiso 1 1 calc R U . . .
H30B H 0.884080 0.062884 0.708939 0.043 Uiso 1 1 calc R U . . .
C31 C 0.6787(19) 0.0730(17) 0.6601(9) 0.036(5) Uani 1 1 d . U . . .
H31A H 0.594466 0.012606 0.646205 0.044 Uiso 1 1 calc R U . . .
H31B H 0.653796 0.148670 0.690939 0.044 Uiso 1 1 calc R U . . .
C32 C 0.7135(18) 0.1198(16) 0.6023(9) 0.033(5) Uani 1 1 d . U . . .
H32A H 0.748169 0.046852 0.573135 0.039 Uiso 1 1 calc R U . . .
H32B H 0.789395 0.189056 0.616312 0.039 Uiso 1 1 calc R U . . .
C33 C 0.5842(18) 0.1720(17) 0.5669(9) 0.034(5) Uani 1 1 d . U . . .
H33A H 0.558436 0.251889 0.594697 0.041 Uiso 1 1 calc R U . . .
H33B H 0.504622 0.106966 0.559668 0.041 Uiso 1 1 calc R U . . .
C34 C 0.6022(18) 0.2041(17) 0.5016(9) 0.032(5) Uani 1 1 d . U . . .
H34A H 0.673530 0.276769 0.508890 0.039 Uiso 1 1 calc R U . . .
H34B H 0.637487 0.127403 0.475127 0.039 Uiso 1 1 calc R U . . .
C35 C 0.464(2) 0.2420(18) 0.4649(10) 0.044(6) Uani 1 1 d . U . . .
H35A H 0.393613 0.168146 0.457167 0.053 Uiso 1 1 calc R U . . .
H35B H 0.427296 0.316498 0.492472 0.053 Uiso 1 1 calc R U . . .
C36 C 0.474(2) 0.2789(19) 0.4007(10) 0.054(6) Uani 1 1 d . U . . .
H36A H 0.522244 0.209718 0.375456 0.064 Uiso 1 1 calc R U . . .
H36B H 0.376602 0.281128 0.376616 0.064 Uiso 1 1 calc R U . . .
C37 C 0.549(2) 0.4061(17) 0.4050(10) 0.050(6) Uani 1 1 d . U . . .
H37A H 0.550129 0.421571 0.361612 0.075 Uiso 1 1 calc R U . . .
H37B H 0.500172 0.476005 0.428716 0.075 Uiso 1 1 calc R U . . .
H37C H 0.646145 0.404433 0.427553 0.075 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
Tc1 Cl1 2.439(4) . ?
Tc1 Cl2 2.373(4) . ?
Tc1 O2 1.668(11) . ?
Tc1 O1 1.853(12) . ?
Tc1 N3 2.116(13) . ?
Tc1 N1 2.128(13) . ?
Tc2 Cl21 2.451(4) . ?
Tc2 Cl22 2.376(4) . ?
Tc2 O22 1.658(11) . ?
Tc2 O21 1.901(11) . ?
Tc2 N23 2.138(12) . ?
Tc2 N21 2.127(13) . ?
O1 C9 1.451(18) . ?
O21 C29 1.405(18) . ?
N3 C8 1.37(2) . ?
N3 C5 1.36(2) . ?
N4 C7 1.32(2) . ?
N4 C6 1.351(18) . ?
N1 C4 1.33(2) . ?
N1 C1 1.35(2) . ?
N2 C3 1.33(2) . ?
N2 C2 1.32(2) . ?
N23 C25 1.335(17) . ?
N23 C28 1.353(19) . ?
N24 C26 1.352(19) . ?
N24 C27 1.333(19) . ?
N21 C21 1.362(18) . ?
N21 C24 1.36(2) . ?
N22 C22 1.311(19) . ?
N22 C23 1.34(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.37(2) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.37(2) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.37(2) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.39(2) . ?
C1 H1 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.46(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.60(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.51(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.56(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.54(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.56(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.50(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.50(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C25 H25 0.9500 . ?
C25 C26 1.40(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.37(2) . ?
C28 H28 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.37(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.38(2) . ?
C24 H24 0.9500 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.46(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.54(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.51(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.51(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.54(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.53(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.52(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.49(2) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 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
Cl2 Tc1 Cl1 174.6(2) . . ?
O2 Tc1 Cl1 86.9(4) . . ?
O2 Tc1 Cl2 98.5(4) . . ?
O2 Tc1 O1 170.8(5) . . ?
O2 Tc1 N3 89.5(5) . . ?
O2 Tc1 N1 92.2(5) . . ?
O1 Tc1 Cl1 84.7(3) . . ?
O1 Tc1 Cl2 90.0(3) . . ?
O1 Tc1 N3 87.1(5) . . ?
O1 Tc1 N1 91.2(5) . . ?
N3 Tc1 Cl1 90.7(3) . . ?
N3 Tc1 Cl2 89.8(3) . . ?
N3 Tc1 N1 178.3(6) . . ?
N1 Tc1 Cl1 89.0(3) . . ?
N1 Tc1 Cl2 90.3(3) . . ?
Cl22 Tc2 Cl21 175.6(2) . . ?
O22 Tc2 Cl21 86.4(4) . . ?
O22 Tc2 Cl22 97.9(4) . . ?
O22 Tc2 O21 169.3(5) . . ?
O22 Tc2 N23 87.2(5) . . ?
O22 Tc2 N21 95.0(5) . . ?
O21 Tc2 Cl21 85.0(3) . . ?
O21 Tc2 Cl22 90.7(3) . . ?
O21 Tc2 N23 86.3(5) . . ?
O21 Tc2 N21 91.4(5) . . ?
N23 Tc2 Cl21 89.7(4) . . ?
N23 Tc2 Cl22 90.2(4) . . ?
N21 Tc2 Cl21 90.2(4) . . ?
N21 Tc2 Cl22 89.7(4) . . ?
N21 Tc2 N23 177.7(6) . . ?
C9 O1 Tc1 145.7(10) . . ?
C29 O21 Tc2 141.4(10) . . ?
C8 N3 Tc1 121.8(11) . . ?
C5 N3 Tc1 123.5(11) . . ?
C5 N3 C8 114.7(15) . . ?
C7 N4 C6 114.7(15) . . ?
C4 N1 Tc1 121.8(12) . . ?
C4 N1 C1 115.7(15) . . ?
C1 N1 Tc1 122.3(11) . . ?
C2 N2 C3 116.1(16) . . ?
C25 N23 Tc2 123.8(10) . . ?
C25 N23 C28 114.9(14) . . ?
C28 N23 Tc2 121.2(11) . . ?
C27 N24 C26 118.8(15) . . ?
C21 N21 Tc2 121.5(10) . . ?
C24 N21 Tc2 119.7(11) . . ?
C24 N21 C21 118.8(15) . . ?
C22 N22 C23 111.7(15) . . ?
N3 C8 H8 119.9 . . ?
C7 C8 N3 120.3(16) . . ?
C7 C8 H8 119.9 . . ?
N4 C7 C8 125.2(16) . . ?
N4 C7 H7 117.4 . . ?
C8 C7 H7 117.4 . . ?
N4 C6 H6 118.9 . . ?
N4 C6 C5 122.2(15) . . ?
C5 C6 H6 118.9 . . ?
N3 C5 C6 122.7(15) . . ?
N3 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
N1 C4 H4 118.3 . . ?
N1 C4 C3 123.4(17) . . ?
C3 C4 H4 118.3 . . ?
N2 C3 C4 121.3(17) . . ?
N2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
N2 C2 H2 118.4 . . ?
N2 C2 C1 123.3(16) . . ?
C1 C2 H2 118.4 . . ?
N1 C1 C2 120.2(15) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
O1 C9 H9A 109.1 . . ?
O1 C9 H9B 109.1 . . ?
O1 C9 C10 112.5(14) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C9 C10 C11 112.4(15) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 C10 109.3(16) . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C11 C12 C13 112.3(16) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 C12 110.3(15) . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C13 C14 C15 113.4(15) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 C14 110.6(16) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C15 C16 C17 112.6(19) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N23 C25 H25 118.0 . . ?
N23 C25 C26 124.0(15) . . ?
C26 C25 H25 118.0 . . ?
N24 C26 C25 118.4(15) . . ?
N24 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
N24 C27 H27 119.5 . . ?
N24 C27 C28 121.0(16) . . ?
C28 C27 H27 119.5 . . ?
N23 C28 C27 122.9(16) . . ?
N23 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
N21 C21 H21 121.2 . . ?
N21 C21 C22 117.6(15) . . ?
C22 C21 H21 121.2 . . ?
N22 C22 C21 127.7(16) . . ?
N22 C22 H22 116.2 . . ?
C21 C22 H22 116.2 . . ?
N22 C23 H23 116.6 . . ?
N22 C23 C24 126.8(18) . . ?
C24 C23 H23 116.6 . . ?
N21 C24 C23 117.3(17) . . ?
N21 C24 H24 121.3 . . ?
C23 C24 H24 121.3 . . ?
O21 C29 H29A 108.2 . . ?
O21 C29 H29B 108.2 . . ?
O21 C29 C30 116.2(14) . . ?
H29A C29 H29B 107.4 . . ?
C30 C29 H29A 108.2 . . ?
C30 C29 H29B 108.2 . . ?
C29 C30 H30A 109.1 . . ?
C29 C30 H30B 109.1 . . ?
C29 C30 C31 112.4(15) . . ?
H30A C30 H30B 107.8 . . ?
C31 C30 H30A 109.1 . . ?
C31 C30 H30B 109.1 . . ?
C30 C31 H31A 108.6 . . ?
C30 C31 H31B 108.6 . . ?
H31A C31 H31B 107.6 . . ?
C32 C31 C30 114.4(15) . . ?
C32 C31 H31A 108.6 . . ?
C32 C31 H31B 108.6 . . ?
C31 C32 H32A 109.6 . . ?
C31 C32 H32B 109.6 . . ?
C31 C32 C33 110.3(14) . . ?
H32A C32 H32B 108.1 . . ?
C33 C32 H32A 109.6 . . ?
C33 C32 H32B 109.6 . . ?
C32 C33 H33A 108.6 . . ?
C32 C33 H33B 108.6 . . ?
C32 C33 C34 114.6(15) . . ?
H33A C33 H33B 107.6 . . ?
C34 C33 H33A 108.6 . . ?
C34 C33 H33B 108.6 . . ?
C33 C34 H34A 109.2 . . ?
C33 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C35 C34 C33 112.0(15) . . ?
C35 C34 H34A 109.2 . . ?
C35 C34 H34B 109.2 . . ?
C34 C35 H35A 108.5 . . ?
C34 C35 H35B 108.5 . . ?
H35A C35 H35B 107.5 . . ?
C36 C35 C34 115.2(17) . . ?
C36 C35 H35A 108.5 . . ?
C36 C35 H35B 108.5 . . ?
C35 C36 H36A 108.5 . . ?
C35 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
C37 C36 C35 115.2(18) . . ?
C37 C36 H36A 108.5 . . ?
C37 C36 H36B 108.5 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 N4 0.95 2.62 3.31(2) 129.5 2_765 yes
C27 H27 N24 0.95 2.70 3.36(2) 127.0 2_657 yes

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
Tc1 O1 C9 C10 99.5(19) . . . . ?
Tc1 N3 C8 C7 177.6(12) . . . . ?
Tc1 N3 C5 C6 -176.6(12) . . . . ?
Tc1 N1 C4 C3 -177.8(13) . . . . ?
Tc1 N1 C1 C2 178.0(12) . . . . ?
Tc2 O21 C29 C30 97.9(19) . . . . ?
Tc2 N23 C25 C26 -178.6(12) . . . . ?
Tc2 N23 C28 C27 178.8(13) . . . . ?
Tc2 N21 C21 C22 179.4(11) . . . . ?
Tc2 N21 C24 C23 -177.8(13) . . . . ?
Cl1 Tc1 O1 C9 -21.2(17) . . . . ?
Cl2 Tc1 O1 C9 159.5(17) . . . . ?
O1 C9 C10 C11 -178.8(14) . . . . ?
O21 C29 C30 C31 -176.0(15) . . . . ?
N3 Tc1 O1 C9 69.8(18) . . . . ?
N3 C8 C7 N4 2(3) . . . . ?
N4 C6 C5 N3 -4(3) . . . . ?
N1 Tc1 O1 C9 -110.1(18) . . . . ?
N1 C4 C3 N2 1(3) . . . . ?
N2 C2 C1 N1 -2(3) . . . . ?
N23 C25 C26 N24 2(3) . . . . ?
N24 C27 C28 N23 -2(3) . . . . ?
N21 C21 C22 N22 -3(3) . . . . ?
N22 C23 C24 N21 -1(3) . . . . ?
C8 N3 C5 C6 4(2) . . . . ?
C7 N4 C6 C5 2(2) . . . . ?
C6 N4 C7 C8 -2(3) . . . . ?
C5 N3 C8 C7 -3(2) . . . . ?
C4 N1 C1 C2 2(2) . . . . ?
C3 N2 C2 C1 1(3) . . . . ?
C2 N2 C3 C4 -1(3) . . . . ?
C1 N1 C4 C3 -2(3) . . . . ?
C9 C10 C11 C12 75.0(19) . . . . ?
C10 C11 C12 C13 178.7(15) . . . . ?
C11 C12 C13 C14 176.7(15) . . . . ?
C12 C13 C14 C15 -175.6(15) . . . . ?
C13 C14 C15 C16 172.7(15) . . . . ?
C14 C15 C16 C17 -174.3(16) . . . . ?
C25 N23 C28 C27 2(2) . . . . ?
C26 N24 C27 C28 1(3) . . . . ?
C27 N24 C26 C25 -1(2) . . . . ?
C28 N23 C25 C26 -2(2) . . . . ?
C21 N21 C24 C23 0(3) . . . . ?
C22 N22 C23 C24 0(3) . . . . ?
C23 N22 C22 C21 2(3) . . . . ?
C24 N21 C21 C22 1(2) . . . . ?
C29 C30 C31 C32 179.0(16) . . . . ?
C30 C31 C32 C33 173.3(16) . . . . ?
C31 C32 C33 C34 -171.6(15) . . . . ?
C32 C33 C34 C35 173.7(15) . . . . ?
C33 C34 C35 C36 178.4(16) . . . . ?
C34 C35 C36 C37 -71(2) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT020_mv59                
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.336 Report
RESPONSE: The investigated single crystal was a small-sized, brittle and
poorly diffracting plate. It was impossible to obtain a better quality 
experiment even at a low temperature (100K).
;
_vrf_PLAT026_mv59                
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PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 32% Check
RESPONSE: The investigated single crystal was a small-sized, brittle and
poorly diffracting plate. It was impossible to obtain a better quality 
experiment even at a low temperature (100K).
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_vrf_PLAT342_mv59                
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PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02667 Ang.
RESPONSE: The investigated single crystal was a small-sized, brittle and
poorly diffracting plate. It was impossible to obtain a better quality 
experiment even at a low temperature (100K).
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_vrf_PLAT910_mv59                
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PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 35 Note
RESPONSE: Closed by beamstop.
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# start Validation Reply Form
_vrf_RINTA01_mv59                
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PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The investigated single crystal was a small-sized, brittle and
poorly diffracting plate. It was impossible to obtain a better quality 
experiment even at a low temperature (100K).
;
