# Supplementary Information (SI) for Chemical Science.
# 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_amd-r855_1
_database_code_depnum_ccdc_archive 'CCDC 2193067'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2022-07-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H31 Cl Cu N'
_chemical_formula_sum            'C21 H31 Cl Cu N'
_chemical_formula_weight         396.46
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H31 Cl Cu N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.14215(12)
_cell_length_b                   11.39563(20)
_cell_length_c                   21.7386(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2017.01(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8921
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      76.3460
_cell_measurement_theta_min      4.3520
_shelx_estimated_absorpt_T_max   0.811
_shelx_estimated_absorpt_T_min   0.330
_exptl_absorpt_coefficient_mu    2.735
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.271
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.61a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0290
0 0 -1 0.0498
0 1 0 0.1578
0 -1 0 0.2001
1 0 0 0.2094
-1 0 0 0.2269
1 -5 -2 0.1515
-1 5 0 0.1635
-1 -1 -2 0.2498

_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -0.0000 1.0000 0.0012 -0.0677 -0.0210
-0.0000 0.0000 -1.0000 -0.0012 0.0677 0.0210
0.0000 1.0000 0.0000 -0.1081 -0.0258 0.0770
-0.0000 -1.0000 -0.0000 0.1081 0.0258 -0.0770
1.0000 0.0000 -0.0001 0.1135 -0.0430 0.1451
-1.0000 -0.0000 0.0001 -0.1135 0.0430 -0.1451
1.0000 -5.0000 -2.0002 0.6515 0.2213 -0.1977
-1.0000 5.0000 0.0002 -0.6539 -0.0859 0.2397
-1.0000 -1.0000 -2.0000 -0.0079 0.2042 -0.1801

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10571
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.540
_diffrn_reflns_theta_min         4.381
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  13.00   1.00    1.00    --   43.01 -75.00 -50.00   26
  2  ω    -25.00  33.00   1.00    1.00    --   43.01 -53.00  86.00   58
  3  ω     57.00  82.00   1.00    1.00    --  112.00 -75.00 -50.00   25
  4  ω     88.00 175.00   1.00    1.00    --  112.00  53.00-128.00   87
  5  ω     34.00  59.00   1.00    1.00    --  112.00-101.00-140.00   25
  6  ω    115.00 140.00   1.00    1.00    --  112.00  75.00  77.00   25
  7  ω    -84.00  -6.00   1.00    1.00    --  -43.01 125.00 120.00   78
  8  ω     35.00  93.00   1.00    1.00    --   43.01-125.00 -30.00   58
  9  ω     88.00 134.00   1.00    1.00    --  112.00  30.00-150.00   46
 10  ω    116.00 178.00   1.00    1.00    --  112.00  77.00  90.00   62
 11  ω     84.00 109.00   1.00    1.00    --  112.00-111.00 -90.00   25
 12  ω    120.00 176.00   1.00    1.00    --  112.00 111.00  60.00   56
 13  ω     72.00  97.00   1.00    1.00    --  112.00   0.00-150.00   25
 14  ω     41.00 108.00   1.00    1.00    --  112.00-111.00 150.00   67
 15  ω    121.00 169.00   1.00    1.00    --  112.00   0.00-150.00   48
 16  ω    148.00 178.00   1.00    1.00    --  112.00  30.00-150.00   30
 17  ω    137.00 176.00   1.00    1.00    --  112.00  77.00 120.00   39
 18  ω     44.00  98.00   1.00    1.00    --  112.00-111.00 -60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1134800000
_diffrn_orient_matrix_UB_12      -0.1080908000
_diffrn_orient_matrix_UB_13      0.0012334000
_diffrn_orient_matrix_UB_21      -0.0430043000
_diffrn_orient_matrix_UB_22      -0.0257693000
_diffrn_orient_matrix_UB_23      -0.0677073000
_diffrn_orient_matrix_UB_31      0.1450972000
_diffrn_orient_matrix_UB_32      0.0769601000
_diffrn_orient_matrix_UB_33      -0.0209916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4100
_reflns_number_total             4192
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_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, 2015)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(7)
_refine_ls_extinction_coef       0.00060(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      1.034
_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)+(0.0312P)²+0.3481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0544
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.41845(3) 0.45973(3) 0.70034(2) 0.02252(9) Uani 1 1 d . . . . .
Cl1 Cl 0.23426(6) 0.42552(5) 0.76624(2) 0.03564(13) Uani 1 1 d . . . . .
N1 N 0.75032(19) 0.47893(13) 0.66201(6) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.5967(2) 0.49715(15) 0.64872(8) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.5877(3) 0.56785(16) 0.58900(8) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.7654(3) 0.56306(19) 0.56367(9) 0.0297(4) Uani 1 1 d . . . . .
H3A H 0.773052 0.505745 0.529563 0.036 Uiso 1 1 calc R U . . .
H3B H 0.799011 0.641078 0.548076 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8761(2) 0.52559(19) 0.61717(8) 0.0242(4) Uani 1 1 d . . . . .
C5 C 0.8071(2) 0.41546(16) 0.71833(8) 0.0208(4) Uani 1 1 d . . . . .
H5 H 0.929088 0.424819 0.720791 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7342(2) 0.46639(16) 0.77755(8) 0.0196(3) Uani 1 1 d . . . . .
H6 H 0.613083 0.452041 0.776562 0.023 Uiso 1 1 calc R U . . .
C7 C 0.8032(2) 0.40339(18) 0.83414(9) 0.0253(4) Uani 1 1 d . . . . .
H7A H 0.923359 0.415814 0.836295 0.030 Uiso 1 1 calc R U . . .
H7B H 0.782785 0.318041 0.830407 0.030 Uiso 1 1 calc R U . . .
C8 C 0.7229(3) 0.4494(2) 0.89310(9) 0.0327(5) Uani 1 1 d . . . . .
H8A H 0.604267 0.430296 0.892495 0.039 Uiso 1 1 calc R U . . .
H8B H 0.772507 0.409633 0.929067 0.039 Uiso 1 1 calc R U . . .
C9 C 0.7441(3) 0.5809(2) 0.89981(9) 0.0366(5) Uani 1 1 d . . . . .
H9A H 0.861792 0.599280 0.905999 0.044 Uiso 1 1 calc R U . . .
H9B H 0.683082 0.608354 0.936478 0.044 Uiso 1 1 calc R U . . .
C10 C 0.6817(3) 0.6449(2) 0.84325(9) 0.0355(5) Uani 1 1 d . . . . .
H10A H 0.705913 0.729668 0.847332 0.043 Uiso 1 1 calc R U . . .
H10B H 0.561043 0.635561 0.840500 0.043 Uiso 1 1 calc R U . . .
C11 C 0.7606(3) 0.59843(17) 0.78430(8) 0.0283(4) Uani 1 1 d . . . . .
H11A H 0.712495 0.639279 0.748382 0.034 Uiso 1 1 calc R U . . .
H11B H 0.879889 0.615362 0.785012 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7713(3) 0.28461(17) 0.70978(9) 0.0308(4) Uani 1 1 d . . . . .
H12A H 0.652921 0.270859 0.713406 0.046 Uiso 1 1 calc R U . . .
H12B H 0.829281 0.239552 0.741457 0.046 Uiso 1 1 calc R U . . .
H12C H 0.808890 0.259630 0.668997 0.046 Uiso 1 1 calc R U . . .
C13 C 0.4682(2) 0.51649(17) 0.54228(9) 0.0233(4) Uani 1 1 d . . . . .
C14 C 0.4314(3) 0.39719(18) 0.54144(9) 0.0274(4) Uani 1 1 d . . . . .
H14 H 0.476124 0.347339 0.572202 0.033 Uiso 1 1 calc R U . . .
C15 C 0.3302(3) 0.3499(2) 0.49634(10) 0.0331(5) Uani 1 1 d . . . . .
H15 H 0.304419 0.268604 0.497328 0.040 Uiso 1 1 calc R U . . .
C16 C 0.2667(3) 0.4195(2) 0.45009(10) 0.0365(5) Uani 1 1 d . . . . .
H16 H 0.198116 0.386576 0.419229 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3043(3) 0.5373(2) 0.44940(11) 0.0429(6) Uani 1 1 d . . . . .
H17 H 0.262819 0.585872 0.417474 0.051 Uiso 1 1 calc R U . . .
C18 C 0.4027(3) 0.5855(2) 0.49517(11) 0.0371(5) Uani 1 1 d . . . . .
H18 H 0.425807 0.667235 0.494395 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5371(3) 0.69261(19) 0.60863(10) 0.0353(5) Uani 1 1 d . . . . .
H19A H 0.423418 0.691649 0.623418 0.053 Uiso 1 1 calc R U . . .
H19B H 0.545976 0.745722 0.573330 0.053 Uiso 1 1 calc R U . . .
H19C H 0.609732 0.719820 0.641630 0.053 Uiso 1 1 calc R U . . .
C20 C 0.9700(3) 0.6278(2) 0.64614(10) 0.0337(5) Uani 1 1 d . . . . .
H20A H 0.892558 0.689628 0.657948 0.051 Uiso 1 1 calc R U . . .
H20B H 1.048973 0.659130 0.616334 0.051 Uiso 1 1 calc R U . . .
H20C H 1.028826 0.600126 0.682711 0.051 Uiso 1 1 calc R U . . .
C21 C 0.9964(3) 0.4299(2) 0.59829(10) 0.0352(5) Uani 1 1 d . . . . .
H21A H 1.064123 0.407866 0.633730 0.053 Uiso 1 1 calc R U . . .
H21B H 1.067186 0.459049 0.565186 0.053 Uiso 1 1 calc R U . . .
H21C H 0.935394 0.361096 0.583793 0.053 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
Cu1 Cl1 2.1102(5) . ?
Cu1 C1 1.8836(19) . ?
N1 C1 1.300(3) . ?
N1 C4 1.510(2) . ?
N1 C5 1.495(2) . ?
C1 C2 1.530(2) . ?
C2 C3 1.549(3) . ?
C2 C13 1.523(3) . ?
C2 C19 1.541(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.532(3) . ?
C4 C20 1.529(3) . ?
C4 C21 1.523(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.532(2) . ?
C5 C12 1.531(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.531(2) . ?
C6 C11 1.527(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.531(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.516(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.517(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.528(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.392(3) . ?
C13 C18 1.397(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Cu1 Cl1 173.66(6) . . ?
C1 N1 C4 116.90(15) . . ?
C1 N1 C5 123.83(15) . . ?
C5 N1 C4 119.27(15) . . ?
N1 C1 Cu1 124.93(13) . . ?
N1 C1 C2 108.58(16) . . ?
C2 C1 Cu1 126.02(14) . . ?
C1 C2 C3 103.80(16) . . ?
C1 C2 C19 105.29(15) . . ?
C13 C2 C1 113.21(15) . . ?
C13 C2 C3 110.24(16) . . ?
C13 C2 C19 111.61(17) . . ?
C19 C2 C3 112.39(17) . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C4 C3 C2 106.81(15) . . ?
C4 C3 H3A 110.4 . . ?
C4 C3 H3B 110.4 . . ?
N1 C4 C3 100.93(14) . . ?
N1 C4 C20 109.97(15) . . ?
N1 C4 C21 110.98(17) . . ?
C20 C4 C3 113.24(19) . . ?
C21 C4 C3 111.92(17) . . ?
C21 C4 C20 109.55(17) . . ?
N1 C5 H5 107.4 . . ?
N1 C5 C6 112.64(15) . . ?
N1 C5 C12 108.23(15) . . ?
C6 C5 H5 107.4 . . ?
C12 C5 H5 107.4 . . ?
C12 C5 C6 113.41(16) . . ?
C5 C6 H6 107.6 . . ?
C7 C6 C5 110.82(15) . . ?
C7 C6 H6 107.6 . . ?
C11 C6 C5 113.54(15) . . ?
C11 C6 H6 107.6 . . ?
C11 C6 C7 109.47(15) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 C8 110.82(16) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 111.74(18) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C10 111.04(18) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 111.85(19) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C6 C11 C10 111.26(17) . . ?
C6 C11 H11A 109.4 . . ?
C6 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C2 121.43(17) . . ?
C14 C13 C18 117.2(2) . . ?
C18 C13 C2 121.08(19) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(2) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C21 H21A 109.5 . . ?
C4 C21 H21B 109.5 . . ?
C4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 C1 C2 C3 -175.73(13) . . . . ?
Cu1 C1 C2 C13 -56.2(2) . . . . ?
Cu1 C1 C2 C19 66.0(2) . . . . ?
N1 C1 C2 C3 11.82(19) . . . . ?
N1 C1 C2 C13 131.35(17) . . . . ?
N1 C1 C2 C19 -106.46(18) . . . . ?
N1 C5 C6 C7 -176.78(15) . . . . ?
N1 C5 C6 C11 -53.1(2) . . . . ?
C1 N1 C4 C3 -9.1(2) . . . . ?
C1 N1 C4 C20 110.73(19) . . . . ?
C1 N1 C4 C21 -127.89(18) . . . . ?
C1 N1 C5 C6 -53.1(2) . . . . ?
C1 N1 C5 C12 73.1(2) . . . . ?
C1 C2 C3 C4 -17.2(2) . . . . ?
C1 C2 C13 C14 -27.1(3) . . . . ?
C1 C2 C13 C18 158.7(2) . . . . ?
C2 C3 C4 N1 15.7(2) . . . . ?
C2 C3 C4 C20 -101.81(19) . . . . ?
C2 C3 C4 C21 133.76(18) . . . . ?
C2 C13 C14 C15 -175.98(19) . . . . ?
C2 C13 C18 C17 174.6(2) . . . . ?
C3 C2 C13 C14 88.7(2) . . . . ?
C3 C2 C13 C18 -85.5(2) . . . . ?
C4 N1 C1 Cu1 -174.31(12) . . . . ?
C4 N1 C1 C2 -1.8(2) . . . . ?
C4 N1 C5 C6 126.91(17) . . . . ?
C4 N1 C5 C12 -106.89(19) . . . . ?
C5 N1 C1 Cu1 5.7(2) . . . . ?
C5 N1 C1 C2 178.21(15) . . . . ?
C5 N1 C4 C3 170.91(15) . . . . ?
C5 N1 C4 C20 -69.2(2) . . . . ?
C5 N1 C4 C21 52.1(2) . . . . ?
C5 C6 C7 C8 -176.71(17) . . . . ?
C5 C6 C11 C10 178.53(17) . . . . ?
C6 C7 C8 C9 -56.7(2) . . . . ?
C7 C6 C11 C10 -57.0(2) . . . . ?
C7 C8 C9 C10 54.5(3) . . . . ?
C8 C9 C10 C11 -54.0(3) . . . . ?
C9 C10 C11 C6 56.0(3) . . . . ?
C11 C6 C7 C8 57.3(2) . . . . ?
C12 C5 C6 C7 59.9(2) . . . . ?
C12 C5 C6 C11 -176.46(17) . . . . ?
C13 C2 C3 C4 -138.69(17) . . . . ?
C13 C14 C15 C16 1.7(3) . . . . ?
C14 C13 C18 C17 0.2(4) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 -1.0(4) . . . . ?
C16 C17 C18 C13 1.1(4) . . . . ?
C18 C13 C14 C15 -1.5(3) . . . . ?
C19 C2 C3 C4 96.1(2) . . . . ?
C19 C2 C13 C14 -145.7(2) . . . . ?
C19 C2 C13 C18 40.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.532
_oxdiff_exptl_absorpt_empirical_full_min 0.758
####################################################################### 
# 
# 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_amd-r855_2
_database_code_depnum_ccdc_archive 'CCDC 2193068'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2022-07-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H31 Cl Cu N'
_chemical_formula_sum            'C21 H31 Cl Cu N'
_chemical_formula_weight         396.46
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H31 Cl Cu N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6227(3)
_cell_length_b                   8.2304(3)
_cell_length_c                   12.9158(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.352(2)
_cell_angle_gamma                90
_cell_volume                     1012.06(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6895
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      76.2390
_cell_measurement_theta_min      3.3950
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.266
_exptl_absorpt_coefficient_mu    2.725
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.61a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0251
-1 0 0 0.0100
0 0 1 0.0415
0 0 -1 0.0132
0 -1 0 0.2660
0 1 0 0.3952

_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -0.0000 -0.0000 0.0028 0.1593 0.0281
-1.0000 0.0000 0.0000 -0.0028 -0.1593 -0.0281
0.0000 -0.0000 1.0000 -0.1178 0.0165 0.0195
-0.0000 0.0000 -1.0000 0.1178 -0.0165 -0.0195
0.0000 -1.0000 0.0000 0.0256 -0.0328 0.1826
-0.0000 1.0000 -0.0000 -0.0256 0.0328 -0.1826

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11385
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.457
_diffrn_reflns_theta_min         3.459
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -25.00   1.00    1.00    --  -43.01  17.00-148.00   25
  2  ω   -112.00   4.00   1.00    1.00    --  -43.01 -17.00  42.00  116
  3  ω     36.00  63.00   1.00    1.00    --   43.01  17.00-148.00   27
  4  ω     97.00 122.00   1.00    3.00    --  112.00  17.00-148.00   25
  5  ω     79.00 104.00   1.00    3.00    --  112.00 -17.00  42.00   25
  6  ω   -108.00 -15.00   1.00    1.00    --  -43.01 -57.00 -60.00   93
  7  ω    -82.00 -15.00   1.00    1.00    --  -43.01 -57.00-120.00   67
  8  ω   -114.00 -28.00   1.00    1.00    --  -43.01 -57.00-150.00   86
  9  ω     22.00  65.00   1.00    1.00    --   43.01  37.00-120.00   43
 10  ω     29.00  96.00   1.00    1.00    --   43.01-125.00  60.00   67
 11  ω      7.00  58.00   1.00    1.00    --   43.01 -99.00   0.00   51
 12  ω     83.00 112.00   1.00    3.00    --  112.00  61.00   0.00   29
 13  ω     41.00 140.00   1.00    3.00    --  112.00 -61.00  90.00   99
 14  ω    147.00 178.00   1.00    3.00    --  112.00  61.00-120.00   31
 15  ω     40.00 104.00   1.00    3.00    --  112.00-111.00 -30.00   64
 16  ω     84.00 110.00   1.00    3.00    --  112.00  61.00 -30.00   26
 17  ω    121.00 178.00   1.00    3.00    --  112.00  61.00 -30.00   57
 18  ω     84.00 109.00   1.00    3.00    --  112.00  61.00 -53.98   25
 19  ω    152.00 177.00   1.00    3.00    --  112.00  61.00 -53.98   25
 20  ω    117.00 170.00   1.00    3.00    --  112.00  45.00 -90.00   53
 21  ω     84.00 109.00   1.00    3.00    --  112.00  61.00 -90.00   25
 22  ω     87.00 112.00   1.00    3.00    --  112.00  45.00 -90.00   25
 23  ω     84.00 125.00   1.00    3.00    --  112.00  66.00  48.83   41
 24  ω     86.00 113.00   1.00    3.00    --  112.00  58.00 -77.30   27
 25  ω     84.00 110.00   1.00    3.00    --  112.00  58.00  -9.49   26
 26  ω     83.00 109.00   1.00    3.00    --  112.00  61.00  30.00   26
 27  ω    119.00 178.00   1.00    3.00    --  112.00  61.00  30.00   59
 28  ω     83.00 109.00   1.00    3.00    --  112.00  61.00 -60.00   26
 29  ω     78.00 118.00   1.00    3.00    --  112.00 -61.00 -90.00   40
 30  ω     88.00 148.00   1.00    3.00    --  112.00  45.00  30.00   60
 31  ω    127.00 154.00   1.00    3.00    --  112.00  30.00 -90.00   27
 32  ω     61.00 125.00   1.00    3.00    --  112.00 178.00   0.00   64
 33  ω     90.00 117.00   1.00    3.00    --  112.00  45.00-120.00   27
 34  ω     84.00 110.00   1.00    3.00    --  112.00  30.00   0.00   26
 35  ω     87.00 112.00   1.00    3.00    --  112.00  45.00   0.00   25
 36  ω     87.00 114.00   1.00    3.00    --  112.00  30.00 -90.00   27
 37  ω     39.00 106.00   1.00    3.00    --  112.00-111.00 -90.00   67
 38  ω     88.00 178.00   1.00    3.00    --  112.00  30.00 -60.00   90
 39  ω    102.00 127.00   1.00    3.00    --  112.00  30.00 -30.00   25
 40  ω    142.00 167.00   1.00    3.00    --  112.00  61.00   0.00   25
 41  ω     83.00 110.00   1.00    3.00    --  112.00  61.00-120.00   27
 42  ω     41.00  66.00   1.00    3.00    --  112.00-111.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0028014000
_diffrn_orient_matrix_UB_12      -0.0255556000
_diffrn_orient_matrix_UB_13      -0.1177898000
_diffrn_orient_matrix_UB_21      0.1593102000
_diffrn_orient_matrix_UB_22      0.0328099000
_diffrn_orient_matrix_UB_23      0.0164581000
_diffrn_orient_matrix_UB_31      0.0281350000
_diffrn_orient_matrix_UB_32      -0.1825855000
_diffrn_orient_matrix_UB_33      0.0194902000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                3671
_reflns_number_total             3906
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_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, 2015)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.046
_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)+(0.0363P)²+0.2887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0777
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.40793(5) 0.69425(6) 0.81369(4) 0.02803(13) Uani 1 1 d . . . . .
Cl1 Cl 0.55455(9) 0.88636(11) 0.82679(7) 0.0365(2) Uani 1 1 d . . . . .
N1 N 0.3209(3) 0.3637(4) 0.8025(2) 0.0251(6) Uani 1 1 d . . . . .
C1 C 0.2852(3) 0.5144(5) 0.8114(2) 0.0268(7) Uani 1 1 d . . . . .
C2 C 0.1326(3) 0.5228(5) 0.8302(3) 0.0307(8) Uani 1 1 d . . . . .
C3 C 0.0799(4) 0.3468(5) 0.8126(3) 0.0363(9) Uani 1 1 d . . . . .
H3A H 0.024926 0.314295 0.868312 0.044 Uiso 1 1 calc R U . . .
H3B H 0.019042 0.337163 0.744176 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2101(4) 0.2373(4) 0.8151(3) 0.0294(8) Uani 1 1 d . . . . .
C5 C 0.4691(3) 0.3103(5) 0.7961(2) 0.0268(7) Uani 1 1 d . . . . .
H5 H 0.468675 0.189078 0.791045 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5206(3) 0.3767(4) 0.6973(2) 0.0250(6) Uani 1 1 d . . . . .
H6 H 0.507048 0.497189 0.696062 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6770(4) 0.3424(6) 0.6979(3) 0.0410(10) Uani 1 1 d . . . . .
H7A H 0.693732 0.223795 0.703483 0.049 Uiso 1 1 calc R U . . .
H7B H 0.731819 0.394822 0.759711 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7273(4) 0.4061(6) 0.5984(3) 0.0449(10) Uani 1 1 d . . . . .
H8A H 0.716491 0.525720 0.595294 0.054 Uiso 1 1 calc R U . . .
H8B H 0.828281 0.380725 0.600732 0.054 Uiso 1 1 calc R U . . .
C9 C 0.6454(4) 0.3317(5) 0.5010(3) 0.0339(8) Uani 1 1 d . . . . .
H9A H 0.663448 0.213268 0.500368 0.041 Uiso 1 1 calc R U . . .
H9B H 0.677209 0.379615 0.438132 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4883(4) 0.3620(6) 0.4977(3) 0.0369(9) Uani 1 1 d . . . . .
H10A H 0.436149 0.302962 0.437412 0.044 Uiso 1 1 calc R U . . .
H10B H 0.468996 0.479418 0.487157 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4360(3) 0.3066(5) 0.5982(3) 0.0291(7) Uani 1 1 d . . . . .
H11A H 0.336483 0.339194 0.595336 0.035 Uiso 1 1 calc R U . . .
H11B H 0.440112 0.186475 0.601947 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5624(4) 0.3562(5) 0.8978(3) 0.0351(8) Uani 1 1 d . . . . .
H12A H 0.580458 0.473394 0.898554 0.053 Uiso 1 1 calc R U . . .
H12B H 0.651678 0.297360 0.902638 0.053 Uiso 1 1 calc R U . . .
H12C H 0.515009 0.327231 0.957424 0.053 Uiso 1 1 calc R U . . .
C13 C 0.0498(3) 0.6407(4) 0.7536(3) 0.0291(7) Uani 1 1 d . . . . .
C14 C 0.0798(3) 0.6499(5) 0.6507(3) 0.0370(9) Uani 1 1 d . . . . .
H14 H 0.153187 0.585083 0.630710 0.044 Uiso 1 1 calc R U . . .
C15 C 0.0046(4) 0.7517(6) 0.5776(3) 0.0439(11) Uani 1 1 d . . . . .
H15 H 0.026970 0.756418 0.508376 0.053 Uiso 1 1 calc R U . . .
C16 C -0.1029(4) 0.8465(6) 0.6051(4) 0.0442(10) Uani 1 1 d . . . . .
H16 H -0.153575 0.917738 0.555338 0.053 Uiso 1 1 calc R U . . .
C17 C -0.1360(4) 0.8370(6) 0.7050(4) 0.0434(10) Uani 1 1 d . . . . .
H17 H -0.211329 0.899749 0.723822 0.052 Uiso 1 1 calc R U . . .
C18 C -0.0590(4) 0.7349(5) 0.7789(3) 0.0354(9) Uani 1 1 d . . . . .
H18 H -0.082076 0.730544 0.847946 0.042 Uiso 1 1 calc R U . . .
C19 C 0.1364(4) 0.5785(6) 0.9448(3) 0.0396(9) Uani 1 1 d . . . . .
H19A H 0.203470 0.511541 0.990677 0.059 Uiso 1 1 calc R U . . .
H19B H 0.042659 0.566706 0.965192 0.059 Uiso 1 1 calc R U . . .
H19C H 0.165309 0.692662 0.951329 0.059 Uiso 1 1 calc R U . . .
C20 C 0.2507(4) 0.1505(5) 0.9197(3) 0.0372(9) Uani 1 1 d . . . . .
H20A H 0.338678 0.090906 0.918693 0.056 Uiso 1 1 calc R U . . .
H20B H 0.176193 0.074202 0.931006 0.056 Uiso 1 1 calc R U . . .
H20C H 0.263278 0.230678 0.976339 0.056 Uiso 1 1 calc R U . . .
C21 C 0.1931(4) 0.1151(5) 0.7261(3) 0.0368(8) Uani 1 1 d . . . . .
H21A H 0.175477 0.172824 0.659080 0.055 Uiso 1 1 calc R U . . .
H21B H 0.113725 0.043190 0.732749 0.055 Uiso 1 1 calc R U . . .
H21C H 0.279099 0.050488 0.728952 0.055 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
Cu1 Cl1 2.1095(10) . ?
Cu1 C1 1.891(4) . ?
N1 C1 1.296(5) . ?
N1 C4 1.515(4) . ?
N1 C5 1.507(4) . ?
C1 C2 1.524(4) . ?
C2 C3 1.540(6) . ?
C2 C13 1.525(5) . ?
C2 C19 1.546(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.539(5) . ?
C4 C20 1.528(5) . ?
C4 C21 1.518(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.535(4) . ?
C5 C12 1.526(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.530(4) . ?
C6 C11 1.527(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.530(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.513(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.527(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.529(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.403(5) . ?
C13 C18 1.379(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.375(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.401(6) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Cu1 Cl1 175.41(11) . . ?
C1 N1 C4 116.6(3) . . ?
C1 N1 C5 123.3(3) . . ?
C5 N1 C4 119.5(3) . . ?
N1 C1 Cu1 125.3(2) . . ?
N1 C1 C2 109.3(3) . . ?
C2 C1 Cu1 125.2(3) . . ?
C1 C2 C3 103.8(3) . . ?
C1 C2 C13 110.5(3) . . ?
C1 C2 C19 106.1(3) . . ?
C3 C2 C19 112.4(3) . . ?
C13 C2 C3 111.9(3) . . ?
C13 C2 C19 111.7(3) . . ?
C2 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 C2 107.3(3) . . ?
C4 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
N1 C4 C3 100.3(3) . . ?
N1 C4 C20 108.8(3) . . ?
N1 C4 C21 112.0(3) . . ?
C20 C4 C3 113.3(3) . . ?
C21 C4 C3 112.0(3) . . ?
C21 C4 C20 110.2(3) . . ?
N1 C5 H5 107.4 . . ?
N1 C5 C6 111.3(3) . . ?
N1 C5 C12 108.9(3) . . ?
C6 C5 H5 107.4 . . ?
C12 C5 H5 107.4 . . ?
C12 C5 C6 114.0(3) . . ?
C5 C6 H6 108.0 . . ?
C7 C6 C5 111.5(3) . . ?
C7 C6 H6 108.0 . . ?
C11 C6 C5 111.4(3) . . ?
C11 C6 H6 108.0 . . ?
C11 C6 C7 109.8(3) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C6 C7 C8 111.3(3) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 111.7(3) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 C10 110.5(3) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 112.0(3) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C6 C11 C10 113.4(3) . . ?
C6 C11 H11A 108.9 . . ?
C6 C11 H11B 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C2 119.2(3) . . ?
C18 C13 C2 123.2(3) . . ?
C18 C13 C14 117.5(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.3(4) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.5(4) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 121.3(4) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C21 H21A 109.5 . . ?
C4 C21 H21B 109.5 . . ?
C4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 C1 C2 C3 176.5(2) . . . . ?
Cu1 C1 C2 C13 56.4(4) . . . . ?
Cu1 C1 C2 C19 -64.8(4) . . . . ?
N1 C1 C2 C3 -8.8(3) . . . . ?
N1 C1 C2 C13 -128.9(3) . . . . ?
N1 C1 C2 C19 109.9(3) . . . . ?
N1 C5 C6 C7 172.3(3) . . . . ?
N1 C5 C6 C11 -64.7(4) . . . . ?
C1 N1 C4 C3 11.1(4) . . . . ?
C1 N1 C4 C20 -108.0(3) . . . . ?
C1 N1 C4 C21 130.0(3) . . . . ?
C1 N1 C5 C6 -63.7(4) . . . . ?
C1 N1 C5 C12 62.9(4) . . . . ?
C1 C2 C3 C4 15.4(4) . . . . ?
C1 C2 C13 C14 36.7(5) . . . . ?
C1 C2 C13 C18 -146.4(3) . . . . ?
C2 C3 C4 N1 -15.6(3) . . . . ?
C2 C3 C4 C20 100.2(3) . . . . ?
C2 C3 C4 C21 -134.5(3) . . . . ?
C2 C13 C14 C15 178.1(4) . . . . ?
C2 C13 C18 C17 -177.4(4) . . . . ?
C3 C2 C13 C14 -78.4(4) . . . . ?
C3 C2 C13 C18 98.5(4) . . . . ?
C4 N1 C1 Cu1 173.1(2) . . . . ?
C4 N1 C1 C2 -1.6(4) . . . . ?
C4 N1 C5 C6 125.6(3) . . . . ?
C4 N1 C5 C12 -107.9(3) . . . . ?
C5 N1 C1 Cu1 2.1(4) . . . . ?
C5 N1 C1 C2 -172.6(3) . . . . ?
C5 N1 C4 C3 -177.6(3) . . . . ?
C5 N1 C4 C20 63.4(4) . . . . ?
C5 N1 C4 C21 -58.7(4) . . . . ?
C5 C6 C7 C8 179.0(3) . . . . ?
C5 C6 C11 C10 -176.9(3) . . . . ?
C6 C7 C8 C9 -58.2(5) . . . . ?
C7 C6 C11 C10 -52.9(4) . . . . ?
C7 C8 C9 C10 56.3(5) . . . . ?
C8 C9 C10 C11 -53.2(5) . . . . ?
C9 C10 C11 C6 52.7(5) . . . . ?
C11 C6 C7 C8 55.1(5) . . . . ?
C12 C5 C6 C7 48.6(4) . . . . ?
C12 C5 C6 C11 171.6(3) . . . . ?
C13 C2 C3 C4 134.6(3) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C14 C13 C18 C17 -0.4(6) . . . . ?
C14 C15 C16 C17 -1.0(6) . . . . ?
C15 C16 C17 C18 1.6(7) . . . . ?
C16 C17 C18 C13 -0.8(6) . . . . ?
C18 C13 C14 C15 1.0(6) . . . . ?
C19 C2 C3 C4 -98.8(3) . . . . ?
C19 C2 C13 C14 154.5(3) . . . . ?
C19 C2 C13 C18 -28.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.741
####################################################################### 
# 
# 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_amd-r1097-dia1
_database_code_depnum_ccdc_archive 'CCDC 2366137'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2023-01-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H35 Cl Cu N'
_chemical_formula_sum            'C23 H35 Cl Cu N'
_chemical_formula_weight         424.51
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H35 N1 Cl1 Cu1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.5297(5)
_cell_length_b                   13.2008(7)
_cell_length_c                   16.3003(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2265.75(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5635
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      72.4760
_cell_measurement_theta_min      4.2570
_shelx_estimated_absorpt_T_max   0.622
_shelx_estimated_absorpt_T_min   0.464
_exptl_absorpt_coefficient_mu    2.467
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.490
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.78a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             904
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 -1 0.1576
0 -2 1 0.2134
0 -1 0 0.1779
0 1 -2 0.1400
0 -1 2 0.2045
0 1 2 0.0879
0 0 1 0.1517
0 1 1 0.1205
1 -2 2 0.2089
-1 2 -2 0.1254
1 0 2 0.1443
1 1 2 0.1247
-1 -1 -2 0.1151
-1 0 -2 0.1017
2 -1 2 0.1441
2 1 2 0.1446
-2 1 -2 0.0710
-6 0 -4 0.0721
6 4 4 0.1452
6 4 1 0.1464
-2 1 0 0.0858
-1 1 0 0.0905
-4 -6 -1 0.1298
-6 -4 -1 0.1202
2 0 -1 0.1236
1 -2 -1 0.1307
2 -1 -2 0.1100
1 0 -1 0.1057
-2 -1 2 0.1492
1 2 -1 0.1437
2 1 -2 0.1038
-1 1 1 0.0941
-1 0 -1 0.0607
-2 -8 -3 0.1188

_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.213
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0011 2.0005 -1.0042 -0.1044 0.0564 0.2217
0.0011 -2.0005 1.0042 0.1044 -0.0564 -0.2217
0.0003 -1.0005 0.0019 0.0085 -0.0111 -0.1159
-0.0011 0.9996 -2.0027 -0.1835 0.0796 0.0957
0.0011 -0.9996 2.0027 0.1835 -0.0796 -0.0957
0.0005 1.0013 1.9989 0.1665 -0.0575 0.1360
0.0004 0.0004 1.0004 0.0875 -0.0343 0.0101
0.0001 1.0009 0.9985 0.0790 -0.0232 0.1259
1.0014 -1.9990 2.0034 0.2463 0.0450 -0.2204
-1.0014 1.9990 -2.0034 -0.2463 -0.0450 0.2204
1.0008 0.0019 1.9996 0.2293 0.0672 0.0114
1.0005 1.0024 1.9977 0.2209 0.0783 0.1272
-1.0005 -1.0024 -1.9977 -0.2209 -0.0783 -0.1272
-1.0008 -0.0019 -1.9996 -0.2293 -0.0672 -0.0114
2.0011 -0.9975 2.0002 0.2921 0.1918 -0.1133
2.0005 1.0035 1.9964 0.2752 0.2140 0.1185
-2.0011 0.9975 -2.0002 -0.2921 -0.1918 0.1133
-6.3388 -0.0272 -3.9230 -0.6879 -0.7257 0.0138
5.5112 3.8490 4.0123 0.6190 0.6525 0.4371
6.1374 3.6389 1.0801 0.3985 0.8358 0.3778
-2.0003 0.9983 0.0006 -0.1171 -0.2604 0.1334
-1.0003 0.9994 -0.0007 -0.0628 -0.1246 0.1246
-4.4642 -6.3914 -1.2778 -0.3019 -0.6324 -0.7134
-5.9051 -4.1913 -1.1299 -0.3856 -0.8086 -0.4443
1.9996 0.0017 -1.0029 0.0212 0.3057 -0.0276
1.0002 -2.0003 -0.9978 -0.0162 0.1478 -0.2506
1.9995 -0.9992 -2.0014 -0.0579 0.3289 -0.1535
0.9996 0.0006 -1.0017 -0.0332 0.1700 -0.0188
-1.9989 -1.0018 2.0052 0.0748 -0.3510 -0.0782
0.9989 2.0016 -1.0055 -0.0501 0.1921 0.2129
1.9989 1.0018 -2.0052 -0.0748 0.3510 0.0782
-0.9999 0.9998 0.9998 0.0247 -0.1589 0.1347
-1.0004 -0.0015 -0.9992 -0.1418 -0.1015 -0.0013
-2.0137 -7.6818 -3.4514 -0.3478 -0.2396 -0.9064

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9478
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.975
_diffrn_reflns_theta_min         4.310
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  33.00   1.00    2.50    --  -42.88  -9.00-139.00  129
  2  ω    137.00 164.00   1.00   10.00    --  103.18 126.00 106.00   27
  3  ω     35.00 101.00   1.00   10.00    --  103.18   9.00  33.00   66
  4  ω    105.00 134.00   1.00   10.00    --  103.18 122.00-160.00   29
  5  ω    -86.00 -28.00   1.00    2.50    --  -42.88 126.00 106.00   58
  6  ω     30.00 127.00   1.00   10.00    --  103.18 -45.00 -90.00   97
  7  ω     34.00  66.00   1.00   10.00    --  103.18-111.00  90.00   32
  8  ω     67.00 106.00   1.00   10.00    --  103.18-111.00  90.00   39
  9  ω    110.00 158.00   1.00   10.00    --  103.18  77.00-120.00   48
 10  ω     34.00 133.00   1.00   10.00    --  103.18 -77.00  90.00   99
 11  ω    138.00 176.00   1.00   10.00    --  103.18   9.00  33.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0544436000
_diffrn_orient_matrix_UB_12      -0.0082787000
_diffrn_orient_matrix_UB_13      0.0874434000
_diffrn_orient_matrix_UB_21      0.1356657000
_diffrn_orient_matrix_UB_22      0.0110439000
_diffrn_orient_matrix_UB_23      -0.0343119000
_diffrn_orient_matrix_UB_31      -0.0088817000
_diffrn_orient_matrix_UB_32      0.1158228000
_diffrn_orient_matrix_UB_33      0.0100201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                3876
_reflns_number_total             4349
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.78a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.78a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.78a (Rigaku OD, 2022)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4349
_refine_ls_number_restraints     250
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0855
_refine_ls_restrained_S_all      1.039
_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)+(0.1671P)²+0.7776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2395
_refine_ls_wR_factor_ref         0.2470
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.88(7)
 0.12(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C22-C21 \\sim C24-C21 \\sim C23-C21
 with sigma of 0.02
 C22-C23 \\sim C23-C24
 with sigma of 0.02
 C27-C26 \\sim C28-C27 \\sim C29-C28 \\sim C30-C29 \\sim C30-C25 \\sim C26-C25
\\sim C7-C6 \\sim C8-C7 ~
 C9-C8 \\sim C9-C10 \\sim C11-C10 \\sim C6-C11
 with sigma of 0.02
 C5-C25 \\sim C6-C5
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C25 \\sim C26 \\sim C27
\\sim C28 \\sim C29 \\sim C30: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
5. Others
 Sof(H21A)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=1-FVAR(1)
 Sof(H21)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
 Sof(H5B)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=
 Sof(H30A)=Sof(H30B)=1-FVAR(2)
 Sof(H5A)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C5(H5A), C5(H5B), C6(H6), C21(H21), C21(H21A), C25(H25)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B),
 C30(H30A,H30B)
6.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
6.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.28155(12) 0.47908(10) 0.42742(7) 0.0649(4) Uani 1 1 d . . . . .
Cl1 Cl 0.1231(2) 0.5074(2) 0.50232(15) 0.0854(7) Uani 1 1 d . . . . .
N1 N 0.4278(6) 0.4471(5) 0.2827(4) 0.0526(13) Uani 1 1 d . . . . .
C1 C 0.4262(7) 0.4502(6) 0.3607(5) 0.0565(16) Uani 1 1 d . . . . .
C2 C 0.5557(7) 0.4237(6) 0.2441(5) 0.0588(17) Uani 1 1 d . . . . .
C3 C 0.6283(9) 0.3852(8) 0.3196(6) 0.072(2) Uani 1 1 d . . . . .
H3A H 0.628174 0.310224 0.321024 0.086 Uiso 1 1 calc R U . . .
H3B H 0.717352 0.409102 0.318340 0.086 Uiso 1 1 calc R U . . .
C4 C 0.5588(9) 0.4281(7) 0.3947(5) 0.0621(19) Uani 1 1 d . . . . .
C5 C 0.3176(7) 0.4765(7) 0.2289(5) 0.0563(16) Uani 1 1 d D . . . .
H5A H 0.345477 0.463575 0.171237 0.068 Uiso 0.56(3) 1 calc R U P A 1
H5B H 0.341745 0.461258 0.170906 0.068 Uiso 0.44(3) 1 calc R U P A 2
C6 C 0.2066(19) 0.4049(19) 0.245(2) 0.066(5) Uani 0.56(3) 1 d D U P A 1
H6 H 0.180547 0.414601 0.303137 0.079 Uiso 0.56(3) 1 calc R U P A 1
C7 C 0.238(2) 0.293(2) 0.2342(18) 0.071(5) Uani 0.56(3) 1 d D U P A 1
H7A H 0.269187 0.280704 0.177586 0.085 Uiso 0.56(3) 1 calc R U P A 1
H7B H 0.307575 0.274072 0.272458 0.085 Uiso 0.56(3) 1 calc R U P A 1
C8 C 0.123(2) 0.225(2) 0.2504(18) 0.092(6) Uani 0.56(3) 1 d D U P A 1
H8A H 0.148023 0.153153 0.241326 0.110 Uiso 0.56(3) 1 calc R U P A 1
H8B H 0.097838 0.231821 0.308589 0.110 Uiso 0.56(3) 1 calc R U P A 1
C9 C 0.011(2) 0.250(2) 0.1959(19) 0.095(6) Uani 0.56(3) 1 d D U P A 1
H9A H -0.062218 0.206467 0.210289 0.114 Uiso 0.56(3) 1 calc R U P A 1
H9B H 0.033109 0.237735 0.137750 0.114 Uiso 0.56(3) 1 calc R U P A 1
C10 C -0.024(2) 0.361(3) 0.2082(18) 0.083(5) Uani 0.56(3) 1 d D U P A 1
H10A H -0.093623 0.379637 0.170283 0.100 Uiso 0.56(3) 1 calc R U P A 1
H10B H -0.054088 0.371614 0.265043 0.100 Uiso 0.56(3) 1 calc R U P A 1
C11 C 0.090(2) 0.428(2) 0.1920(19) 0.068(5) Uani 0.56(3) 1 d D U P A 1
H11A H 0.065543 0.499386 0.201139 0.082 Uiso 0.56(3) 1 calc R U P A 1
H11B H 0.114615 0.421069 0.133527 0.082 Uiso 0.56(3) 1 calc R U P A 1
C12 C 0.2988(11) 0.5906(8) 0.2359(7) 0.078(3) Uani 1 1 d . . . . .
H12A H 0.249786 0.605894 0.285529 0.117 Uiso 1 1 calc R U . . .
H12B H 0.252694 0.615334 0.187667 0.117 Uiso 1 1 calc R U . . .
H12C H 0.381719 0.624076 0.239068 0.117 Uiso 1 1 calc R U . . .
C13 C 0.6078(10) 0.5173(9) 0.2064(8) 0.082(3) Uani 1 1 d . . . . .
H13A H 0.549418 0.541718 0.163980 0.124 Uiso 1 1 calc R U . . .
H13B H 0.690603 0.502488 0.181632 0.124 Uiso 1 1 calc R U . . .
H13C H 0.617942 0.569428 0.248691 0.124 Uiso 1 1 calc R U . . .
C14 C 0.5434(10) 0.3409(7) 0.1790(6) 0.071(2) Uani 1 1 d . . . . .
H14A H 0.488464 0.286650 0.199767 0.107 Uiso 1 1 calc R U . . .
H14B H 0.627557 0.313222 0.166562 0.107 Uiso 1 1 calc R U . . .
H14C H 0.506155 0.369584 0.129075 0.107 Uiso 1 1 calc R U . . .
C15 C 0.6216(8) 0.5236(7) 0.4266(5) 0.0622(17) Uani 1 1 d . . . . .
C16 C 0.7513(9) 0.5315(9) 0.4373(8) 0.091(3) Uani 1 1 d . . . . .
H16 H 0.803236 0.475776 0.421933 0.110 Uiso 1 1 calc R U . . .
C17 C 0.8089(13) 0.6168(13) 0.4692(11) 0.114(5) Uani 1 1 d . . . . .
H17 H 0.898163 0.617681 0.477442 0.137 Uiso 1 1 calc R U . . .
C18 C 0.7386(13) 0.6989(10) 0.4887(8) 0.089(3) Uani 1 1 d . . . . .
H18 H 0.779351 0.758089 0.508956 0.107 Uiso 1 1 calc R U . . .
C19 C 0.6112(11) 0.6978(9) 0.4799(7) 0.078(2) Uani 1 1 d . . . . .
H19 H 0.562253 0.755494 0.494396 0.094 Uiso 1 1 calc R U . . .
C20 C 0.5511(9) 0.6100(8) 0.4488(6) 0.073(2) Uani 1 1 d . . . . .
H20 H 0.461343 0.609375 0.442695 0.087 Uiso 1 1 calc R U . . .
C21 C 0.5518(13) 0.3472(9) 0.4634(8) 0.091(3) Uani 1 1 d D . . . .
H21 H 0.504459 0.381888 0.508553 0.110 Uiso 0.49(3) 1 calc R U P B 1
H21A H 0.640067 0.321061 0.471435 0.110 Uiso 0.51(3) 1 calc R U P B 2
C22 C 0.472(2) 0.2596(11) 0.4437(12) 0.130(6) Uani 1 1 d D . . . .
H22A H 0.384059 0.281473 0.437260 0.195 Uiso 1 1 calc R U . . .
H22B H 0.477971 0.209856 0.488199 0.195 Uiso 1 1 calc R U . . .
H22C H 0.502083 0.228777 0.392483 0.195 Uiso 1 1 calc R U . . .
C23 C 0.674(2) 0.318(2) 0.5020(16) 0.097(9) Uani 0.49(3) 1 d D . P B 1
H23A H 0.731051 0.290321 0.460124 0.145 Uiso 0.49(3) 1 calc R U P B 1
H23B H 0.658455 0.266517 0.544196 0.145 Uiso 0.49(3) 1 calc R U P B 1
H23C H 0.713101 0.377677 0.527204 0.145 Uiso 0.49(3) 1 calc R U P B 1
C24 C 0.509(4) 0.382(2) 0.5417(12) 0.121(13) Uani 0.51(3) 1 d D . P B 2
H24A H 0.569294 0.430965 0.563790 0.182 Uiso 0.51(3) 1 calc R U P B 2
H24B H 0.502149 0.323904 0.579288 0.182 Uiso 0.51(3) 1 calc R U P B 2
H24C H 0.425268 0.413614 0.535764 0.182 Uiso 0.51(3) 1 calc R U P B 2
C25 C 0.191(2) 0.425(3) 0.246(3) 0.063(6) Uani 0.44(3) 1 d D U P A 2
H25 H 0.160219 0.448716 0.300390 0.076 Uiso 0.44(3) 1 calc R U P A 2
C26 C 0.207(3) 0.310(3) 0.249(2) 0.077(6) Uani 0.44(3) 1 d D U P A 2
H26A H 0.266048 0.292903 0.294555 0.093 Uiso 0.44(3) 1 calc R U P A 2
H26B H 0.245409 0.286296 0.197413 0.093 Uiso 0.44(3) 1 calc R U P A 2
C27 C 0.081(3) 0.256(3) 0.263(2) 0.091(6) Uani 0.44(3) 1 d D U P A 2
H27A H 0.092180 0.182105 0.255085 0.109 Uiso 0.44(3) 1 calc R U P A 2
H27B H 0.051210 0.267447 0.319911 0.109 Uiso 0.44(3) 1 calc R U P A 2
C28 C -0.018(3) 0.295(3) 0.203(2) 0.090(6) Uani 0.44(3) 1 d D U P A 2
H28A H 0.001537 0.267030 0.148020 0.108 Uiso 0.44(3) 1 calc R U P A 2
H28B H -0.101905 0.268355 0.219396 0.108 Uiso 0.44(3) 1 calc R U P A 2
C29 C -0.031(3) 0.409(3) 0.194(2) 0.078(6) Uani 0.44(3) 1 d D U P A 2
H29A H -0.086344 0.424740 0.146565 0.093 Uiso 0.44(3) 1 calc R U P A 2
H29B H -0.071109 0.437387 0.243737 0.093 Uiso 0.44(3) 1 calc R U P A 2
C30 C 0.097(3) 0.460(3) 0.181(2) 0.069(6) Uani 0.44(3) 1 d D U P A 2
H30A H 0.086682 0.534719 0.184657 0.082 Uiso 0.44(3) 1 calc R U P A 2
H30B H 0.129768 0.443671 0.125848 0.082 Uiso 0.44(3) 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
Cu1 Cl1 2.101(3) . ?
Cu1 C1 1.910(8) . ?
N1 C1 1.272(11) . ?
N1 C2 1.518(9) . ?
N1 C5 1.505(10) . ?
C1 C4 1.530(11) . ?
C2 C3 1.535(13) . ?
C2 C13 1.485(14) . ?
C2 C14 1.529(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.535(12) . ?
C4 C15 1.514(13) . ?
C4 C21 1.550(15) . ?
C5 H5A 1.0000 . ?
C5 H5B 1.0000 . ?
C5 C6 1.525(18) . ?
C5 C12 1.524(13) . ?
C5 C25 1.517(19) . ?
C6 H6 1.0000 . ?
C6 C7 1.530(18) . ?
C6 C11 1.525(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.528(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.519(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.517(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.380(13) . ?
C15 C20 1.409(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.35(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.350(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.414(16) . ?
C20 H20 0.9500 . ?
C21 H21 1.0000 . ?
C21 H21A 1.0000 . ?
C21 C22 1.462(18) . ?
C21 C23 1.48(2) . ?
C21 C24 1.43(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25 1.0000 . ?
C25 C26 1.53(2) . ?
C25 C30 1.519(19) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.529(19) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.52(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.52(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.516(19) . ?
C30 H30A 0.9900 . ?
C30 H30B 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
C1 Cu1 Cl1 178.6(3) . . ?
C1 N1 C2 115.6(6) . . ?
C1 N1 C5 124.3(6) . . ?
C5 N1 C2 119.6(6) . . ?
N1 C1 Cu1 125.9(6) . . ?
N1 C1 C4 110.1(7) . . ?
C4 C1 Cu1 124.0(6) . . ?
N1 C2 C3 100.1(6) . . ?
N1 C2 C14 111.0(7) . . ?
C13 C2 N1 109.3(7) . . ?
C13 C2 C3 115.0(8) . . ?
C13 C2 C14 109.9(8) . . ?
C14 C2 C3 111.2(7) . . ?
C2 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 C2 106.3(7) . . ?
C4 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C1 C4 C3 102.4(7) . . ?
C1 C4 C21 110.4(8) . . ?
C3 C4 C21 110.2(8) . . ?
C15 C4 C1 111.4(6) . . ?
C15 C4 C3 111.9(8) . . ?
C15 C4 C21 110.3(8) . . ?
N1 C5 H5A 106.1 . . ?
N1 C5 H5B 107.6 . . ?
N1 C5 C6 109.4(12) . . ?
N1 C5 C12 108.2(7) . . ?
N1 C5 C25 117.1(16) . . ?
C6 C5 H5A 106.1 . . ?
C12 C5 H5A 106.1 . . ?
C12 C5 H5B 107.6 . . ?
C12 C5 C6 120.1(13) . . ?
C25 C5 H5B 107.6 . . ?
C25 C5 C12 108.3(15) . . ?
C5 C6 H6 106.9 . . ?
C5 C6 C7 114.5(18) . . ?
C5 C6 C11 113.3(19) . . ?
C7 C6 H6 106.9 . . ?
C11 C6 H6 106.9 . . ?
C11 C6 C7 107.8(19) . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 112.1(18) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.7(19) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C8 C9 C10 109(2) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.2(18) . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C6 C11 H11A 108.5 . . ?
C6 C11 H11B 108.5 . . ?
C10 C11 C6 115.0(17) . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C4 122.6(8) . . ?
C16 C15 C20 115.3(9) . . ?
C20 C15 C4 122.1(8) . . ?
C15 C16 H16 118.5 . . ?
C15 C16 C17 122.9(11) . . ?
C17 C16 H16 118.5 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(12) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.7(12) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.5(10) . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 121.3(9) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C4 C21 H21 103.8 . . ?
C4 C21 H21A 106.7 . . ?
C22 C21 C4 114.5(10) . . ?
C22 C21 H21 103.8 . . ?
C22 C21 H21A 106.7 . . ?
C22 C21 C23 112.5(17) . . ?
C23 C21 C4 116.4(14) . . ?
C23 C21 H21 103.8 . . ?
C24 C21 C4 116.2(14) . . ?
C24 C21 H21A 106.7 . . ?
C24 C21 C22 105(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C5 C25 H25 108.0 . . ?
C5 C25 C26 111(2) . . ?
C5 C25 C30 108(2) . . ?
C26 C25 H25 108.0 . . ?
C30 C25 H25 108.0 . . ?
C30 C25 C26 114(3) . . ?
C25 C26 H26A 109.2 . . ?
C25 C26 H26B 109.2 . . ?
C25 C26 C27 112(2) . . ?
H26A C26 H26B 107.9 . . ?
C27 C26 H26A 109.2 . . ?
C27 C26 H26B 109.2 . . ?
C26 C27 H27A 109.7 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C28 C27 C26 110(3) . . ?
C28 C27 H27A 109.7 . . ?
C28 C27 H27B 109.7 . . ?
C27 C28 H28A 107.9 . . ?
C27 C28 H28B 107.9 . . ?
H28A C28 H28B 107.2 . . ?
C29 C28 C27 117(3) . . ?
C29 C28 H28A 107.9 . . ?
C29 C28 H28B 107.9 . . ?
C28 C29 H29A 109.2 . . ?
C28 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 C28 112(2) . . ?
C30 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
C25 C30 H30A 109.6 . . ?
C25 C30 H30B 109.6 . . ?
C29 C30 C25 110(2) . . ?
C29 C30 H30A 109.6 . . ?
C29 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 C1 C4 C3 166.6(7) . . . . ?
Cu1 C1 C4 C15 -73.7(9) . . . . ?
Cu1 C1 C4 C21 49.2(10) . . . . ?
N1 C1 C4 C3 -13.9(10) . . . . ?
N1 C1 C4 C15 105.8(8) . . . . ?
N1 C1 C4 C21 -131.3(8) . . . . ?
N1 C2 C3 C4 -21.7(9) . . . . ?
N1 C5 C6 C7 -55(3) . . . . ?
N1 C5 C6 C11 -179.3(18) . . . . ?
N1 C5 C25 C26 -51(3) . . . . ?
N1 C5 C25 C30 -176.1(18) . . . . ?
C1 N1 C2 C3 14.2(9) . . . . ?
C1 N1 C2 C13 -107.0(9) . . . . ?
C1 N1 C2 C14 131.7(8) . . . . ?
C1 N1 C5 C6 -63.7(17) . . . . ?
C1 N1 C5 C12 68.8(10) . . . . ?
C1 N1 C5 C25 -54(2) . . . . ?
C1 C4 C15 C16 -160.0(10) . . . . ?
C1 C4 C15 C20 21.1(12) . . . . ?
C1 C4 C21 C22 45.7(16) . . . . ?
C1 C4 C21 C23 179.8(16) . . . . ?
C1 C4 C21 C24 -78(2) . . . . ?
C2 N1 C1 Cu1 179.2(6) . . . . ?
C2 N1 C1 C4 -0.3(10) . . . . ?
C2 N1 C5 C6 124.0(16) . . . . ?
C2 N1 C5 C12 -103.5(8) . . . . ?
C2 N1 C5 C25 133.8(19) . . . . ?
C2 C3 C4 C1 22.2(10) . . . . ?
C2 C3 C4 C15 -97.3(8) . . . . ?
C2 C3 C4 C21 139.7(9) . . . . ?
C3 C4 C15 C16 -46.0(13) . . . . ?
C3 C4 C15 C20 135.1(9) . . . . ?
C3 C4 C21 C22 -66.7(16) . . . . ?
C3 C4 C21 C23 67.4(18) . . . . ?
C3 C4 C21 C24 170(2) . . . . ?
C4 C15 C16 C17 -177.5(13) . . . . ?
C4 C15 C20 C19 178.8(9) . . . . ?
C5 N1 C1 Cu1 6.7(11) . . . . ?
C5 N1 C1 C4 -172.8(7) . . . . ?
C5 N1 C2 C3 -172.8(7) . . . . ?
C5 N1 C2 C13 66.0(10) . . . . ?
C5 N1 C2 C14 -55.3(9) . . . . ?
C5 C6 C7 C8 -180(2) . . . . ?
C5 C6 C11 C10 -178(2) . . . . ?
C5 C25 C26 C27 -178(3) . . . . ?
C5 C25 C30 C29 179(3) . . . . ?
C6 C7 C8 C9 57(3) . . . . ?
C7 C6 C11 C10 55(3) . . . . ?
C7 C8 C9 C10 -57(3) . . . . ?
C8 C9 C10 C11 56(3) . . . . ?
C9 C10 C11 C6 -57(3) . . . . ?
C11 C6 C7 C8 -53(3) . . . . ?
C12 C5 C6 C7 179.0(18) . . . . ?
C12 C5 C6 C11 55(3) . . . . ?
C12 C5 C25 C26 -173(2) . . . . ?
C12 C5 C25 C30 61(3) . . . . ?
C13 C2 C3 C4 95.3(10) . . . . ?
C14 C2 C3 C4 -139.0(8) . . . . ?
C15 C4 C21 C22 169.3(13) . . . . ?
C15 C4 C21 C23 -56.6(18) . . . . ?
C15 C4 C21 C24 46(2) . . . . ?
C15 C16 C17 C18 -3(3) . . . . ?
C16 C15 C20 C19 -0.2(16) . . . . ?
C16 C17 C18 C19 2(3) . . . . ?
C17 C18 C19 C20 -1(2) . . . . ?
C18 C19 C20 C15 -0.2(18) . . . . ?
C20 C15 C16 C17 2(2) . . . . ?
C21 C4 C15 C16 77.0(13) . . . . ?
C21 C4 C15 C20 -101.9(10) . . . . ?
C25 C26 C27 C28 49(4) . . . . ?
C26 C25 C30 C29 55(3) . . . . ?
C26 C27 C28 C29 -48(4) . . . . ?
C27 C28 C29 C30 49(4) . . . . ?
C28 C29 C30 C25 -50(4) . . . . ?
C30 C25 C26 C27 -56(4) . . . . ?

_olex2_date_sample_data_collection 2022-12-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.021
_oxdiff_exptl_absorpt_empirical_full_min 0.595
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.88(7)
2 0.12(7)

####################################################################### 
# 
# 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_amd-r1398-dia2
_database_code_depnum_ccdc_archive 'CCDC 2366138'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2023-11-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H35 Cl Cu N S'
_chemical_formula_sum            'C23 H35 Cl Cu N S'
_chemical_formula_weight         456.57
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H35 N1 S1 Cl1 Cu1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5182(2)
_cell_length_b                   15.3074(5)
_cell_length_c                   9.1646(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.104(3)
_cell_angle_gamma                90
_cell_volume                     1163.87(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6828
_cell_measurement_temperature    140.0(3)
_cell_measurement_theta_max      72.7060
_cell_measurement_theta_min      4.9370
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.357
_exptl_absorpt_coefficient_mu    3.255
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.309
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 -1 0.2262
-2 -1 1 0.1587
-2 1 1 0.1578
2 -1 -1 0.2262
2 0 -1 0.2326
1 0 -1 0.2079
0 -1 -1 0.0411
1 -10 0 0.0649
-1 10 0 0.0639
5 5 0 0.2125
0 4 5 0.0443
1 -1 5 0.0554
1 -9 2 0.0551
4 1 3 0.1589
-1 2 -5 0.0305
1 9 -3 0.1122
2 -4 5 0.0637

_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.087
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.9983 1.0012 -1.0005 -0.1095 0.3110 0.1995
-1.9983 -1.0012 1.0005 0.1095 -0.3110 -0.1995
-1.9993 0.9990 1.0012 0.0872 -0.3753 -0.0100
1.9993 -0.9990 -1.0012 -0.0872 0.3753 0.0100
1.9988 0.0011 -1.0009 -0.0984 0.3432 0.1047
0.9997 0.0010 -1.0009 -0.1350 0.1724 0.0426
0.0011 -0.9993 -1.0013 -0.1604 0.0337 -0.1143
1.2269 -9.6817 -0.1719 0.1238 0.5205 -0.8448
-1.0947 9.7338 0.1764 -0.1187 -0.4996 0.8581
4.6722 4.7801 0.2190 0.1553 0.6453 0.7480
0.1710 4.1518 5.2202 0.8548 -0.1115 0.5068
0.9663 -0.7730 5.4518 0.9788 0.1821 0.0939
1.2410 -8.9119 1.8977 0.4705 0.4952 -0.7303
4.0950 1.3102 2.8224 0.6193 0.6541 0.4343
-0.7100 2.1545 -5.4338 -0.9817 -0.1826 0.0533
0.9871 8.6479 -2.8922 -0.5564 -0.1043 0.8243
1.5401 -3.7842 4.7325 0.9102 0.3778 -0.1699

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10462
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.322
_diffrn_reflns_theta_min         4.955
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -54.00   1.00    6.50    --  -40.29 -26.00 -11.00   33
  2  ω     10.00 117.00   1.00    6.50    --   40.29  26.00 152.00  107
  3  ω     14.00  40.00   1.00    6.50    --   40.29 -26.00 -11.00   26
  4  ω     62.00 108.00   1.00   26.00    --  105.78 -26.00 -11.00   46
  5  ω    102.00 127.00   1.00   26.00    --  105.78  26.00 152.00   25
  6  ω     33.00  60.00   1.00   26.00    --  105.78 -26.00 -11.00   27
  7  ω   -110.00 -13.00   1.00    6.50    --  -40.29 -57.00 150.00   97
  8  ω    -51.00 -17.00   1.00    6.50    --  -40.29 -38.00-120.00   34
  9  ω    -42.00 -17.00   1.00    6.50    --  -40.29  26.00 152.00   25
 10  ω   -112.00 -12.00   1.00    6.50    --  -40.29 -57.00-120.00  100
 11  ω     14.00  41.00   1.00    6.50    --   40.29  57.00 -30.00   27
 12  ω     29.00  89.00   1.00    6.50    --   40.29-125.00-150.00   60
 13  ω     21.00  46.00   1.00    6.50    --   40.29  57.00 -90.00   25
 14  ω      6.00  78.00   1.00    6.50    --   40.29 -99.00   0.00   72
 15  ω     78.00 105.00   1.00   26.00    --  105.78  61.00-120.00   27
 16  ω     61.00  91.00   1.00   26.00    --  105.78 178.00   0.00   30
 17  ω     77.00 103.00   1.00   26.00    --  105.78  61.00 -60.00   26
 18  ω    109.00 141.00   1.00   26.00    --  105.78 178.00   0.00   32
 19  ω    121.00 158.00   1.00   26.00    --  105.78  61.00 -30.00   37
 20  ω     85.00 147.00   1.00   26.00    --  105.78  45.00-180.00   62
 21  ω     72.00 105.00   1.00   26.00    --  105.78 -94.00 -60.00   33
 22  ω     78.00 109.00   1.00   26.00    --  105.78  61.00-180.00   31
 23  ω     82.00 107.00   1.00   26.00    --  105.78  45.00 -60.00   25
 24  ω    113.00 174.00   1.00   26.00    --  105.78  61.00 -90.00   61
 25  ω     77.00 112.00   1.00   26.00    --  105.78  30.00-120.00   35
 26  ω     81.00 108.00   1.00   26.00    --  105.78  45.00 -30.00   27
 27  ω    105.00 167.00   1.00   26.00    --  105.78 111.00-180.00   62
 28  ω     82.00 109.00   1.00   26.00    --  105.78  45.00-120.00   27
 29  ω     80.00 122.00   1.00   26.00    --  105.78  45.00 -90.00   42
 30  ω     83.00 110.00   1.00   26.00    --  105.78  45.00-150.00   27
 31  ω     81.00 108.00   1.00   26.00    --  105.78  38.00 -69.63   27
 32  ω     78.00 106.00   1.00   26.00    --  105.78  61.00 -30.00   28
 33  ω     77.00 104.00   1.00   26.00    --  105.78  61.00 -90.00   27
 34  ω     78.00 103.00   1.00   26.00    --  105.78  61.00-150.00   25
 35  ω     83.00 110.00   1.00   26.00    --  105.78  30.00 -30.00   27
 36  ω     86.00 126.00   1.00   26.00    --  105.78  30.00 -90.00   40
 37  ω    112.00 170.00   1.00   26.00    --  105.78 111.00  90.00   58
 38  ω     26.00 106.00   1.00   26.00    --  105.78 -94.00  30.00   80
 39  ω     31.00  71.00   1.00   26.00    --  105.78 -94.00 -60.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0366484000
_diffrn_orient_matrix_UB_12      -0.0111847000
_diffrn_orient_matrix_UB_13      0.1714515000
_diffrn_orient_matrix_UB_21      0.1709877000
_diffrn_orient_matrix_UB_22      -0.0320690000
_diffrn_orient_matrix_UB_23      -0.0014574000
_diffrn_orient_matrix_UB_31      0.0621914000
_diffrn_orient_matrix_UB_32      0.0947931000
_diffrn_orient_matrix_UB_33      0.0196493000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.859
_reflns_number_gt                4127
_reflns_number_total             4323
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.344
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 1729 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.040
_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)+(0.0892P)²+0.0102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1234
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.51511(7) 0.33796(4) 0.44866(7) 0.02280(19) Uani 1 1 d . . . . .
Cl1 Cl 0.71653(13) 0.25666(8) 0.45532(13) 0.0284(3) Uani 1 1 d . . . . .
S1 S 0.4357(3) 0.58860(11) 0.06324(19) 0.0518(5) Uani 1 1 d . . . . .
N1 N 0.1899(5) 0.3868(3) 0.4407(4) 0.0213(8) Uani 1 1 d . . . . .
C1 C 0.3382(6) 0.4113(3) 0.4511(5) 0.0218(9) Uani 1 1 d . . . . .
C2 C 0.3531(5) 0.5086(3) 0.4803(5) 0.0232(9) Uani 1 1 d . . . . .
C3 C 0.1798(6) 0.5400(3) 0.4763(6) 0.0268(10) Uani 1 1 d . . . . .
H3A H 0.176938 0.573531 0.568024 0.032 Uiso 1 1 calc R U . . .
H3B H 0.140117 0.577857 0.388135 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0748(5) 0.4571(3) 0.4668(6) 0.0251(9) Uani 1 1 d . . . . .
C5 C 0.4635(7) 0.5230(4) 0.6359(6) 0.0373(12) Uani 1 1 d . . . . .
H5A H 0.423270 0.489018 0.710350 0.056 Uiso 1 1 calc R U . . .
H5B H 0.464656 0.585166 0.661640 0.056 Uiso 1 1 calc R U . . .
H5C H 0.573168 0.503989 0.634918 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4331(5) 0.5527(4) 0.3640(6) 0.0282(10) Uani 1 1 d . . . . .
H6A H 0.447148 0.615630 0.388289 0.034 Uiso 1 1 calc R U . . .
H6B H 0.541614 0.527149 0.372965 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3390(7) 0.5434(4) 0.2027(6) 0.0326(11) Uani 1 1 d . . . . .
H7A H 0.233015 0.572178 0.192699 0.039 Uiso 1 1 calc R U . . .
H7B H 0.318701 0.480513 0.180893 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3955(6) 0.7022(4) 0.0608(6) 0.0303(10) Uani 1 1 d . . . . .
C9 C 0.3334(6) 0.7470(4) 0.1689(5) 0.0299(10) Uani 1 1 d . . . . .
H9 H 0.307519 0.715865 0.250023 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3100(6) 0.8359(4) 0.1576(5) 0.0302(9) Uani 1 1 d . . . . .
H10 H 0.267315 0.865626 0.231041 0.036 Uiso 1 1 calc R U . . .
C11 C 0.3478(7) 0.8830(4) 0.0405(6) 0.0331(11) Uani 1 1 d . . . . .
H11 H 0.333045 0.944528 0.034451 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4079(6) 0.8385(5) -0.0679(6) 0.0346(10) Uani 1 1 d . . . . .
H12 H 0.434006 0.869794 -0.148648 0.042 Uiso 1 1 calc R U . . .
C13 C 0.4295(6) 0.7490(4) -0.0585(6) 0.0342(11) Uani 1 1 d . . . . .
H13 H 0.468084 0.719195 -0.134272 0.041 Uiso 1 1 calc R U . . .
C14 C 0.0262(7) 0.4376(4) 0.6145(7) 0.0356(12) Uani 1 1 d . . . . .
H14A H -0.029571 0.381209 0.606992 0.053 Uiso 1 1 calc R U . . .
H14B H -0.045848 0.483694 0.634769 0.053 Uiso 1 1 calc R U . . .
H14C H 0.122831 0.435410 0.696229 0.053 Uiso 1 1 calc R U . . .
C15 C -0.0739(6) 0.4621(4) 0.3376(7) 0.0339(11) Uani 1 1 d . . . . .
H15A H -0.040201 0.471162 0.243359 0.051 Uiso 1 1 calc R U . . .
H15B H -0.142081 0.510939 0.354451 0.051 Uiso 1 1 calc R U . . .
H15C H -0.134827 0.407444 0.332173 0.051 Uiso 1 1 calc R U . . .
C16 C 0.1363(6) 0.2937(3) 0.4238(5) 0.0245(9) Uani 1 1 d . . . . .
H16 H 0.016904 0.293246 0.413478 0.029 Uiso 1 1 calc R U . . .
C17 C 0.2111(7) 0.2438(4) 0.5665(6) 0.0349(11) Uani 1 1 d . . . . .
H17A H 0.325784 0.233771 0.570996 0.052 Uiso 1 1 calc R U . . .
H17B H 0.156277 0.187478 0.566377 0.052 Uiso 1 1 calc R U . . .
H17C H 0.199482 0.277928 0.653834 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1693(5) 0.2537(3) 0.2793(5) 0.0232(9) Uani 1 1 d . . . . .
H18 H 0.287973 0.257054 0.285899 0.028 Uiso 1 1 calc R U . . .
C19 C 0.0841(6) 0.3028(4) 0.1385(5) 0.0287(10) Uani 1 1 d . . . . .
H19A H -0.033450 0.303045 0.132460 0.034 Uiso 1 1 calc R U . . .
H19B H 0.121539 0.364222 0.145237 0.034 Uiso 1 1 calc R U . . .
C20 C 0.1164(7) 0.2614(4) -0.0034(6) 0.0375(12) Uani 1 1 d . . . . .
H20A H 0.054424 0.293159 -0.091997 0.045 Uiso 1 1 calc R U . . .
H20B H 0.232364 0.267243 -0.002615 0.045 Uiso 1 1 calc R U . . .
C21 C 0.0701(7) 0.1657(5) -0.0164(7) 0.0453(14) Uani 1 1 d . . . . .
H21A H 0.101380 0.140071 -0.104941 0.054 Uiso 1 1 calc R U . . .
H21B H -0.048169 0.160006 -0.030888 0.054 Uiso 1 1 calc R U . . .
C22 C 0.1531(7) 0.1162(4) 0.1234(7) 0.0391(13) Uani 1 1 d . . . . .
H22A H 0.270765 0.115624 0.130257 0.047 Uiso 1 1 calc R U . . .
H22B H 0.114944 0.054916 0.115518 0.047 Uiso 1 1 calc R U . . .
C23 C 0.1203(6) 0.1568(4) 0.2653(7) 0.0325(11) Uani 1 1 d . . . . .
H23A H 0.181334 0.124502 0.353682 0.039 Uiso 1 1 calc R U . . .
H23B H 0.004129 0.151545 0.263745 0.039 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
Cu1 Cl1 2.1092(12) . ?
Cu1 C1 1.883(5) . ?
S1 C7 1.808(5) . ?
S1 C8 1.772(6) . ?
N1 C1 1.301(6) . ?
N1 C4 1.511(6) . ?
N1 C16 1.494(6) . ?
C1 C2 1.514(7) . ?
C2 C3 1.545(6) . ?
C2 C5 1.536(7) . ?
C2 C6 1.544(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.543(7) . ?
C4 C14 1.532(7) . ?
C4 C15 1.527(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.520(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.403(7) . ?
C8 C13 1.392(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(10) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.524(7) . ?
C16 C18 1.541(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 1.0000 . ?
C18 C19 1.528(7) . ?
C18 C23 1.538(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.526(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.515(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.518(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.523(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 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
C1 Cu1 Cl1 177.68(14) . . ?
C8 S1 C7 105.5(2) . . ?
C1 N1 C4 115.9(4) . . ?
C1 N1 C16 123.5(4) . . ?
C16 N1 C4 120.2(4) . . ?
N1 C1 Cu1 126.4(4) . . ?
N1 C1 C2 109.8(4) . . ?
C2 C1 Cu1 123.6(3) . . ?
C1 C2 C3 105.1(4) . . ?
C1 C2 C5 108.3(4) . . ?
C1 C2 C6 109.9(4) . . ?
C5 C2 C3 111.0(4) . . ?
C5 C2 C6 107.8(4) . . ?
C6 C2 C3 114.6(4) . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C4 C3 C2 106.5(4) . . ?
C4 C3 H3A 110.4 . . ?
C4 C3 H3B 110.4 . . ?
N1 C4 C3 101.9(4) . . ?
N1 C4 C14 108.4(4) . . ?
N1 C4 C15 111.5(4) . . ?
C14 C4 C3 112.3(4) . . ?
C15 C4 C3 111.8(4) . . ?
C15 C4 C14 110.6(4) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 108.7 . . ?
C2 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 C2 114.4(4) . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
S1 C7 H7A 108.4 . . ?
S1 C7 H7B 108.4 . . ?
C6 C7 S1 115.3(4) . . ?
C6 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 S1 125.0(4) . . ?
C13 C8 S1 116.2(4) . . ?
C13 C8 C9 118.8(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.1(5) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.9(5) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.7(5) . . ?
C12 C13 H13 119.6 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16 107.2 . . ?
N1 C16 C17 109.3(4) . . ?
N1 C16 C18 110.9(4) . . ?
C17 C16 H16 107.2 . . ?
C17 C16 C18 114.6(4) . . ?
C18 C16 H16 107.2 . . ?
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 . . ?
C16 C18 H18 107.8 . . ?
C19 C18 C16 112.7(4) . . ?
C19 C18 H18 107.8 . . ?
C19 C18 C23 109.6(4) . . ?
C23 C18 C16 110.8(4) . . ?
C23 C18 H18 107.8 . . ?
C18 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 C18 111.8(4) . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 C19 112.0(5) . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 C22 110.7(5) . . ?
H21A C21 H21B 108.1 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C21 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C21 C22 C23 112.1(5) . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C18 C23 H23A 109.3 . . ?
C18 C23 H23B 109.3 . . ?
C22 C23 C18 111.5(5) . . ?
C22 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 C1 C2 C3 -178.2(3) . . . . ?
Cu1 C1 C2 C5 -59.6(5) . . . . ?
Cu1 C1 C2 C6 57.9(5) . . . . ?
S1 C8 C9 C10 178.6(4) . . . . ?
S1 C8 C13 C12 -177.7(4) . . . . ?
N1 C1 C2 C3 -3.2(5) . . . . ?
N1 C1 C2 C5 115.4(5) . . . . ?
N1 C1 C2 C6 -127.0(4) . . . . ?
N1 C16 C18 C19 -59.0(5) . . . . ?
N1 C16 C18 C23 177.7(4) . . . . ?
C1 N1 C4 C3 7.6(5) . . . . ?
C1 N1 C4 C14 -111.0(5) . . . . ?
C1 N1 C4 C15 127.0(5) . . . . ?
C1 N1 C16 C17 66.7(6) . . . . ?
C1 N1 C16 C18 -60.6(6) . . . . ?
C1 C2 C3 C4 7.7(5) . . . . ?
C1 C2 C6 C7 61.5(5) . . . . ?
C2 C3 C4 N1 -8.8(5) . . . . ?
C2 C3 C4 C14 107.0(5) . . . . ?
C2 C3 C4 C15 -128.0(4) . . . . ?
C2 C6 C7 S1 -176.4(3) . . . . ?
C3 C2 C6 C7 -56.6(6) . . . . ?
C4 N1 C1 Cu1 171.9(3) . . . . ?
C4 N1 C1 C2 -2.9(6) . . . . ?
C4 N1 C16 C17 -105.3(5) . . . . ?
C4 N1 C16 C18 127.4(4) . . . . ?
C5 C2 C3 C4 -109.1(5) . . . . ?
C5 C2 C6 C7 179.3(5) . . . . ?
C6 C2 C3 C4 128.5(5) . . . . ?
C7 S1 C8 C9 12.7(6) . . . . ?
C7 S1 C8 C13 -167.5(4) . . . . ?
C8 S1 C7 C6 -81.0(5) . . . . ?
C8 C9 C10 C11 -0.4(8) . . . . ?
C9 C8 C13 C12 2.2(8) . . . . ?
C9 C10 C11 C12 1.1(8) . . . . ?
C10 C11 C12 C13 -0.1(8) . . . . ?
C11 C12 C13 C8 -1.5(8) . . . . ?
C13 C8 C9 C10 -1.3(8) . . . . ?
C16 N1 C1 Cu1 -0.3(7) . . . . ?
C16 N1 C1 C2 -175.2(4) . . . . ?
C16 N1 C4 C3 -179.8(4) . . . . ?
C16 N1 C4 C14 61.6(6) . . . . ?
C16 N1 C4 C15 -60.5(6) . . . . ?
C16 C18 C19 C20 -179.2(4) . . . . ?
C16 C18 C23 C22 -179.7(4) . . . . ?
C17 C16 C18 C19 176.7(4) . . . . ?
C17 C16 C18 C23 53.4(5) . . . . ?
C18 C19 C20 C21 55.8(6) . . . . ?
C19 C18 C23 C22 55.3(5) . . . . ?
C19 C20 C21 C22 -54.4(6) . . . . ?
C20 C21 C22 C23 54.7(7) . . . . ?
C21 C22 C23 C18 -55.9(6) . . . . ?
C23 C18 C19 C20 -55.2(5) . . . . ?

_olex2_date_sample_data_collection 2023-09-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 6.570
_oxdiff_exptl_absorpt_empirical_full_min 0.400
####################################################################### 
# 
# 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_amd-r713
_database_code_depnum_ccdc_archive 'CCDC 2355628'
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-05-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H45 Cl2 N O Ru, 2[C6H12]'
_chemical_formula_sum            'C48 H69 Cl2 N O Ru'
_chemical_formula_weight         848.01
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C48 H69 Cl2 N O Ru'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   18.5489(9)
_cell_length_b                   8.9270(4)
_cell_length_c                   27.5267(11)
_cell_angle_alpha                90
_cell_angle_beta                 109.441(5)
_cell_angle_gamma                90
_cell_volume                     4298.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19113
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      74.3700
_cell_measurement_theta_min      2.4920
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.365
_exptl_absorpt_coefficient_mu    4.357
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.318
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense green'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0094
1 0 0 0.0241
0 0 -1 0.0096
0 0 1 0.0096
0 -1 0 0.1162
0 1 0 0.1737

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9991 0.0005 0.0000 0.0009 -0.0681 -0.0557
0.9991 -0.0005 -0.0000 -0.0009 0.0681 0.0557
0.0002 -0.0001 -1.0009 0.0560 -0.0120 -0.0155
-0.0002 0.0001 1.0009 -0.0560 0.0120 0.0155
-0.0009 -0.9998 0.0027 0.0136 -0.1097 0.1325
0.0009 0.9998 -0.0027 -0.0136 0.1097 -0.1325

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            46618
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.351
_diffrn_reflns_theta_min         2.526
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00  53.00   0.50    4.00    --   20.00  67.00 -29.64   54
  2  ω     50.00  76.00   0.50    4.00    --   36.00  59.00 -33.75   52
  3  ω     43.00  68.00   0.50    4.00    --   40.00  73.00 -79.74   50
  4  ω     60.00  87.00   0.50    4.00    --   56.00  75.00 -87.12   54
  5  ω     11.00  37.00   0.50    4.00    --   59.19 -30.00 120.00   52
  6  ω     11.00  37.00   0.50    4.00    --   59.19 -30.00-180.00   52
  7  ω     10.00  36.00   0.50    4.00    --   59.19 -30.00  90.00   52
  8  ω     10.00  35.00   0.50    4.00    --   59.19 -30.00 -60.00   50
  9  ω   -108.00 -71.00   0.50    4.00    --  -60.00 -39.00 -88.43   74
 10  ω    -89.00 -63.00   0.50    4.00    --  -62.05 -30.00-180.00   52
 11  ω   -109.00 -82.00   0.50    4.00    --  -62.05 -30.00 120.00   54
 12  ω   -105.00 -76.00   0.50    4.00    --  -64.00 -67.00-101.28   58
 13  ω   -101.00 -73.00   0.50    4.00    --  -68.00 -75.00 -30.16   56
 14  ω   -116.00 -85.00   0.50    4.00    --  -71.12 -30.00  30.00   62
 15  ω     34.00 101.00   0.50    4.00    --   71.94   0.00-180.00  134
 16  ω     32.00  64.00   0.50    4.00    --   71.94 -95.00 -60.00   64
 17  ω     34.00  80.00   0.50    4.00    --   71.94 -95.00 120.00   92
 18  ω     74.00  99.00   0.50    4.00    --   71.94  30.00 -90.00   50
 19  ω     32.00  77.00   0.50    4.00    --   71.94 -95.00   0.00   90
 20  ω   -106.00 -75.00   0.50    4.00    --  -72.00 -73.00-108.87   62
 21  ω     51.00  80.00   0.50    4.00    --   73.16 -95.00-150.00   58
 22  ω     33.00  58.00   0.50    4.00    --   73.16 -95.00  90.00   50
 23  ω   -125.00 -81.00   0.50    4.00    --  -75.55 -30.00  30.00   88
 24  ω   -121.00 -78.00   0.50    4.00    --  -75.55-125.00-150.00   86
 25  ω   -119.00 -90.00   0.50    4.00    --  -75.55-125.00 -60.00   58
 26  ω    -55.00 -30.00   0.50    4.00    --  -75.55 125.00  30.00   50
 27  ω   -120.00 -95.00   0.50    4.00    --  -75.55-125.00 -30.00   50
 28  ω   -120.00 -42.00   0.50    4.00    --  -75.55 -15.00 -60.00  156
 29  ω   -106.00 -79.00   0.50    4.00    --  -76.57 -76.00 -36.36   54
 30  ω   -120.00 -85.00   0.50    4.00    --  -76.57 -51.00 -82.01   70
 31  ω     93.00 126.00   0.50    4.00    --   81.20  30.00-150.00   66
 32  ω     45.00 112.00   0.50    4.00    --   81.20-125.00-180.00  134
 33  ω     97.00 127.00   0.50    4.00    --   81.20 125.00-120.00   60
 34  ω     91.00 127.00   0.50    4.00    --   81.20 125.00-180.00   72
 35  ω     79.00 125.00   0.50    4.00    --   81.20 125.00 -30.00   92
 36  ω     82.00 127.00   0.50    4.00    --   81.20 125.00 -90.00   90
 37  ω     39.00 112.00   0.50    4.00    --   81.20-125.00   0.00  146
 38  ω     81.00 109.00   0.50    4.00    --   81.20 125.00-150.00   56
 39  ω     40.00  90.00   0.50    4.00    --   81.20-125.00 120.00  100
 40  ω     88.00 117.00   0.50    4.00    --   81.20 125.00  90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0009277000
_diffrn_orient_matrix_UB_12      -0.0137563000
_diffrn_orient_matrix_UB_13      -0.0559852000
_diffrn_orient_matrix_UB_21      0.0682118000
_diffrn_orient_matrix_UB_22      0.1097144000
_diffrn_orient_matrix_UB_23      0.0119397000
_diffrn_orient_matrix_UB_31      0.0557249000
_diffrn_orient_matrix_UB_32      -0.1324967000
_diffrn_orient_matrix_UB_33      0.0155610000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.910
_reflns_number_gt                13986
_reflns_number_total             16645
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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, 2015)'
_refine_diff_density_max         1.188
_refine_diff_density_min         -1.856
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.248(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     678
_refine_ls_number_reflns         16645
_refine_ls_number_restraints     1202
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0852
_refine_ls_restrained_S_all      1.074
_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)+(0.1092P)²+16.8801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2177
_refine_ls_wR_factor_ref         0.2261
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.752(18)
 0.248(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C36-C34 = C35-C34
 1.54 with sigma of 0.01
 C36-C35
 2.54 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 2A
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C34(H34), C41(H41), C43(H43), C70(H70)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C39(H39A,H39B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B),
  C47(H47A,H47B), C48(H48A,H48B)
6.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C33(H33), C32(H32), C31(H31), C30(H30),
  C52(H52), C53(H53), C54(H54), C55(H55), C56(H56), C62(H62), C61(H61),
 C60(H60), C59(H59), C58(H58), C63(H63), C66(H66), C67(H67), C68(H68), C69(H69)
6.d Fitted hexagon refined as free rotating group:
 C15(C16,C17,C18,C19,C20), C21(C22,C23,C24,C25,C26), C29(C28,C33,C32,C31,C30),
 C51(C52,C53,C54,C55,C56), C57(C62,C61,C60,C59,C58), C65(C66,C67,C68,C69,C64)
6.e Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C35(H35A,H35B,
 H35C), C36(H36A,H36B,H36C), C42(H42A,H42B,H42C), C49(H49A,H49B,H49C), C50(H50A,
 H50B,H50C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Ru1 Ru 0.52106(5) 0.37493(11) 0.80700(3) 0.0429(2) Uani 1 1 d . U . . .
Cl1 Cl 0.4552(2) 0.5214(4) 0.84802(13) 0.0534(8) Uani 1 1 d . . . . .
Cl2 Cl 0.61961(16) 0.2106(5) 0.80618(12) 0.0557(9) Uani 1 1 d . . . . .
O1 O 0.6156(7) 0.5480(15) 0.8328(5) 0.078(2) Uani 1 1 d . U . . .
N1 N 0.4399(6) 0.0936(14) 0.8121(4) 0.0488(18) Uani 1 1 d . U . . .
C1 C 0.4448(7) 0.2190(16) 0.7833(5) 0.0465(19) Uani 1 1 d . U . . .
C2 C 0.3830(8) -0.0244(17) 0.7833(5) 0.050(2) Uani 1 1 d . U . . .
C3 C 0.3289(7) 0.0714(17) 0.7442(5) 0.049(2) Uani 1 1 d . U . . .
H3A H 0.290060 0.113063 0.757985 0.059 Uiso 1 1 calc R U . . .
H3B H 0.302262 0.012243 0.713002 0.059 Uiso 1 1 calc R U . . .
C4 C 0.3749(7) 0.1988(16) 0.7310(5) 0.0482(18) Uani 1 1 d . U . . .
C5 C 0.4934(9) 0.0896(18) 0.8653(5) 0.056(2) Uani 1 1 d . U . . .
H5 H 0.524178 0.183681 0.869586 0.067 Uiso 1 1 calc R U . . .
C6 C 0.5517(10) -0.040(2) 0.8740(7) 0.068(4) Uani 1 1 d . U . . .
H6A H 0.526610 -0.134705 0.876252 0.103 Uiso 1 1 calc R U . . .
H6B H 0.594076 -0.022538 0.906180 0.103 Uiso 1 1 calc R U . . .
H6C H 0.571558 -0.043644 0.845197 0.103 Uiso 1 1 calc R U . . .
C7 C 0.4522(10) 0.099(2) 0.9059(6) 0.061(2) Uani 1 1 d . U . . .
H7 H 0.433673 -0.003387 0.910106 0.073 Uiso 1 1 calc R U . . .
C8 C 0.3861(9) 0.2030(18) 0.8949(6) 0.059(2) Uani 1 1 d . U . . .
H8A H 0.347876 0.176556 0.861230 0.071 Uiso 1 1 calc R U . . .
H8B H 0.403634 0.306582 0.892406 0.071 Uiso 1 1 calc R U . . .
C9 C 0.3481(10) 0.1965(19) 0.9370(6) 0.065(3) Uani 1 1 d . U . . .
H9A H 0.305232 0.268699 0.929159 0.078 Uiso 1 1 calc R U . . .
H9B H 0.327784 0.094752 0.938703 0.078 Uiso 1 1 calc R U . . .
C10 C 0.4087(10) 0.236(2) 0.9879(6) 0.072(3) Uani 1 1 d . U . . .
H10A H 0.419611 0.344163 0.987293 0.086 Uiso 1 1 calc R U . . .
H10B H 0.386326 0.219694 1.015482 0.086 Uiso 1 1 calc R U . . .
C11 C 0.4806(11) 0.157(2) 1.0022(6) 0.070(3) Uani 1 1 d . U . . .
H11A H 0.473216 0.055542 1.014233 0.084 Uiso 1 1 calc R U . . .
H11B H 0.517696 0.210182 1.031575 0.084 Uiso 1 1 calc R U . . .
C12 C 0.5162(11) 0.142(2) 0.9575(6) 0.068(3) Uani 1 1 d . U . . .
H12A H 0.540221 0.237603 0.953259 0.082 Uiso 1 1 calc R U . . .
H12B H 0.556220 0.063276 0.966574 0.082 Uiso 1 1 calc R U . . .
C13 C 0.3453(8) -0.1026(19) 0.8149(6) 0.057(3) Uani 1 1 d . U . . .
H13A H 0.341190 -0.035320 0.841931 0.085 Uiso 1 1 calc R U . . .
H13B H 0.375402 -0.190951 0.830630 0.085 Uiso 1 1 calc R U . . .
H13C H 0.294086 -0.134047 0.793170 0.085 Uiso 1 1 calc R U . . .
C14 C 0.4250(9) -0.1366(18) 0.7587(6) 0.058(3) Uani 1 1 d . U . . .
H14A H 0.395130 -0.150555 0.722191 0.087 Uiso 1 1 calc R U . . .
H14B H 0.430759 -0.233107 0.776557 0.087 Uiso 1 1 calc R U . . .
H14C H 0.475603 -0.096942 0.761754 0.087 Uiso 1 1 calc R U . . .
C15 C 0.3279(5) 0.3500(9) 0.7185(3) 0.051(2) Uani 1 1 d G U . . .
C16 C 0.3119(6) 0.4262(11) 0.6720(3) 0.057(2) Uani 1 1 d G U . . .
H16 H 0.331576 0.390327 0.646451 0.068 Uiso 1 1 calc R U . . .
C17 C 0.2673(6) 0.5550(11) 0.6630(3) 0.066(3) Uani 1 1 d G U . . .
H17 H 0.256384 0.607066 0.631312 0.080 Uiso 1 1 calc R U . . .
C18 C 0.2385(6) 0.6075(10) 0.7005(4) 0.069(3) Uani 1 1 d G U . . .
H18 H 0.207996 0.695534 0.694337 0.082 Uiso 1 1 calc R U . . .
C19 C 0.2544(6) 0.5313(12) 0.7469(3) 0.064(3) Uani 1 1 d G U . . .
H19 H 0.234799 0.567264 0.772500 0.077 Uiso 1 1 calc R U . . .
C20 C 0.2991(5) 0.4026(11) 0.7559(3) 0.058(2) Uani 1 1 d G U . . .
H20 H 0.309991 0.350525 0.787639 0.070 Uiso 1 1 calc R U . . .
C21 C 0.4010(5) 0.1462(12) 0.6834(3) 0.051(2) Uani 1 1 d G U . . .
C22 C 0.4758(4) 0.1547(12) 0.6834(3) 0.052(2) Uani 1 1 d G U . . .
H22 H 0.515328 0.188407 0.713239 0.062 Uiso 1 1 calc R U . . .
C23 C 0.4928(4) 0.1138(13) 0.6397(3) 0.057(2) Uani 1 1 d G U . . .
H23 H 0.543899 0.119666 0.639648 0.068 Uiso 1 1 calc R U . . .
C24 C 0.4349(5) 0.0645(13) 0.5960(3) 0.062(3) Uani 1 1 d G U . . .
H24 H 0.446534 0.036597 0.566111 0.075 Uiso 1 1 calc R U . . .
C25 C 0.3601(4) 0.0560(13) 0.5960(3) 0.060(2) Uani 1 1 d G U . . .
H25 H 0.320597 0.022269 0.566165 0.071 Uiso 1 1 calc R U . . .
C26 C 0.3432(4) 0.0968(13) 0.6397(3) 0.055(2) Uani 1 1 d G U . . .
H26 H 0.292024 0.091010 0.639756 0.066 Uiso 1 1 calc R U . . .
C27 C 0.5076(8) 0.4733(17) 0.7485(5) 0.053(2) Uani 1 1 d . U . . .
H27 H 0.467641 0.444042 0.718214 0.063 Uiso 1 1 calc R U . . .
C29 C 0.6131(7) 0.6312(14) 0.7925(4) 0.079(3) Uani 1 1 d G U . . .
C28 C 0.5562(7) 0.5959(12) 0.7464(5) 0.071(2) Uani 1 1 d G U . . .
C33 C 0.5476(7) 0.6817(15) 0.7027(4) 0.081(3) Uani 1 1 d G U . . .
H33 H 0.508693 0.657653 0.671136 0.097 Uiso 1 1 calc R U . . .
C32 C 0.5957(8) 0.8028(14) 0.7051(4) 0.091(3) Uani 1 1 d G U . . .
H32 H 0.589817 0.861477 0.675196 0.110 Uiso 1 1 calc R U . . .
C31 C 0.6526(8) 0.8381(13) 0.7512(5) 0.095(3) Uani 1 1 d G U . . .
H31 H 0.685537 0.920811 0.752847 0.114 Uiso 1 1 calc R U . . .
C30 C 0.6613(7) 0.7522(16) 0.7949(4) 0.090(3) Uani 1 1 d G U . . .
H30 H 0.700134 0.776320 0.826439 0.108 Uiso 1 1 calc R U . . .
C34 C 0.6753(10) 0.564(2) 0.8807(7) 0.089(3) Uani 1 1 d D U . . .
H34 H 0.681306 0.671195 0.891312 0.107 Uiso 1 1 calc R U . . .
C35 C 0.7515(10) 0.502(3) 0.8775(9) 0.096(5) Uani 1 1 d D U . . .
H35A H 0.741760 0.409555 0.857130 0.144 Uiso 1 1 calc R U . . .
H35B H 0.786447 0.480691 0.912335 0.144 Uiso 1 1 calc R U . . .
H35C H 0.774669 0.576501 0.861129 0.144 Uiso 1 1 calc R U . . .
C36 C 0.6507(10) 0.471(2) 0.9197(7) 0.085(4) Uani 1 1 d D U . . .
H36A H 0.613780 0.394439 0.901313 0.128 Uiso 1 1 calc R U . . .
H36B H 0.627133 0.537026 0.938509 0.128 Uiso 1 1 calc R U . . .
H36C H 0.695665 0.422230 0.943997 0.128 Uiso 1 1 calc R U . . .
Ru2 Ru 0.18278(5) 0.74655(11) 0.37798(3) 0.0427(2) Uani 1 1 d . U . . .
Cl3 Cl 0.28099(17) 0.8750(5) 0.43906(13) 0.0538(7) Uani 1 1 d . . . . .
Cl4 Cl 0.1395(3) 0.5901(5) 0.30712(14) 0.0812(14) Uani 1 1 d . . . . .
O2 O 0.1975(6) 0.9244(14) 0.3198(4) 0.069(2) Uani 1 1 d . U . . .
N2 N 0.2080(6) 0.4807(14) 0.4412(4) 0.0479(18) Uani 1 1 d . U . . .
C37 C 0.1604(7) 0.5974(17) 0.4230(5) 0.0472(19) Uani 1 1 d . U . . .
C38 C 0.1777(7) 0.3701(19) 0.4700(5) 0.052(2) Uani 1 1 d . U . . .
C39 C 0.0940(7) 0.4082(17) 0.4522(6) 0.054(2) Uani 1 1 d . U . . .
H39A H 0.071053 0.381359 0.478753 0.064 Uiso 1 1 calc R U . . .
H39B H 0.066166 0.354679 0.419862 0.064 Uiso 1 1 calc R U . . .
C40 C 0.0912(8) 0.5789(18) 0.4434(6) 0.0537(19) Uani 1 1 d . U . . .
C41 C 0.2810(8) 0.4640(18) 0.4325(5) 0.054(2) Uani 1 1 d . U . . .
H41 H 0.289760 0.562689 0.418123 0.064 Uiso 1 1 calc R U . . .
C42 C 0.2782(10) 0.3479(19) 0.3896(6) 0.068(4) Uani 1 1 d . U . . .
H42A H 0.278498 0.246294 0.403197 0.102 Uiso 1 1 calc R U . . .
H42B H 0.322944 0.361338 0.378663 0.102 Uiso 1 1 calc R U . . .
H42C H 0.231508 0.362928 0.360136 0.102 Uiso 1 1 calc R U . . .
C43 C 0.3490(8) 0.443(2) 0.4806(6) 0.065(2) Uani 1 1 d . U . . .
H43 H 0.341024 0.347182 0.496731 0.078 Uiso 1 1 calc R U . . .
C44 C 0.3556(9) 0.566(2) 0.5202(7) 0.076(3) Uani 1 1 d . U . . .
H44A H 0.307538 0.571903 0.528373 0.091 Uiso 1 1 calc R U . . .
H44B H 0.363368 0.664133 0.505717 0.091 Uiso 1 1 calc R U . . .
C45 C 0.4224(9) 0.535(3) 0.5694(8) 0.085(3) Uani 1 1 d . U . . .
H45A H 0.423723 0.612203 0.595526 0.102 Uiso 1 1 calc R U . . .
H45B H 0.415155 0.436258 0.583428 0.102 Uiso 1 1 calc R U . . .
C46 C 0.4935(10) 0.536(3) 0.5594(8) 0.090(3) Uani 1 1 d . U . . .
H46A H 0.536085 0.517660 0.591858 0.108 Uiso 1 1 calc R U . . .
H46B H 0.501393 0.635801 0.546209 0.108 Uiso 1 1 calc R U . . .
C47 C 0.4943(9) 0.413(2) 0.5187(7) 0.083(3) Uani 1 1 d . U . . .
H47A H 0.541753 0.421793 0.510012 0.099 Uiso 1 1 calc R U . . .
H47B H 0.493901 0.312054 0.533862 0.099 Uiso 1 1 calc R U . . .
C48 C 0.4249(8) 0.428(2) 0.4696(7) 0.074(3) Uani 1 1 d . U . . .
H48A H 0.422057 0.339004 0.447559 0.089 Uiso 1 1 calc R U . . .
H48B H 0.431889 0.517177 0.450217 0.089 Uiso 1 1 calc R U . . .
C49 C 0.1865(9) 0.1953(18) 0.4513(7) 0.064(4) Uani 1 1 d . U . . .
H49A H 0.238773 0.160006 0.468581 0.096 Uiso 1 1 calc R U . . .
H49B H 0.175284 0.193242 0.413891 0.096 Uiso 1 1 calc R U . . .
H49C H 0.150438 0.130039 0.460382 0.096 Uiso 1 1 calc R U . . .
C50 C 0.2121(7) 0.3647(19) 0.5266(5) 0.054(3) Uani 1 1 d . U . . .
H50A H 0.174565 0.325961 0.541408 0.082 Uiso 1 1 calc R U . . .
H50B H 0.227750 0.465783 0.539857 0.082 Uiso 1 1 calc R U . . .
H50C H 0.256952 0.298842 0.536182 0.082 Uiso 1 1 calc R U . . .
C51 C 0.1049(6) 0.6667(11) 0.4936(3) 0.057(2) Uani 1 1 d G U . . .
C52 C 0.1520(5) 0.7921(11) 0.5052(3) 0.059(2) Uani 1 1 d G U . . .
H52 H 0.178657 0.821940 0.482721 0.071 Uiso 1 1 calc R U . . .
C53 C 0.1600(5) 0.8739(10) 0.5497(4) 0.068(3) Uani 1 1 d G U . . .
H53 H 0.192184 0.959562 0.557592 0.082 Uiso 1 1 calc R U . . .
C54 C 0.1210(6) 0.8302(12) 0.5825(3) 0.070(3) Uani 1 1 d G U . . .
H54 H 0.126443 0.886096 0.612946 0.084 Uiso 1 1 calc R U . . .
C55 C 0.0739(6) 0.7048(12) 0.5710(4) 0.068(3) Uani 1 1 d G U . . .
H55 H 0.047174 0.675008 0.593428 0.082 Uiso 1 1 calc R U . . .
C56 C 0.0658(5) 0.6231(10) 0.5265(4) 0.063(3) Uani 1 1 d G U . . .
H56 H 0.033647 0.537384 0.518557 0.075 Uiso 1 1 calc R U . . .
C57 C 0.0148(4) 0.6196(13) 0.4018(4) 0.064(2) Uani 1 1 d G U . . .
C62 C -0.0056(5) 0.5509(12) 0.3538(4) 0.073(3) Uani 1 1 d G U . . .
H62 H 0.028485 0.482458 0.346295 0.088 Uiso 1 1 calc R U . . .
C61 C -0.0759(6) 0.5822(14) 0.3168(3) 0.078(3) Uani 1 1 d G U . . .
H61 H -0.089839 0.535265 0.283981 0.094 Uiso 1 1 calc R U . . .
C60 C -0.1258(5) 0.6824(14) 0.3278(4) 0.078(3) Uani 1 1 d G U . . .
H60 H -0.173814 0.703796 0.302456 0.093 Uiso 1 1 calc R U . . .
C59 C -0.1054(5) 0.7511(13) 0.3757(4) 0.069(3) Uani 1 1 d G U . . .
H59 H -0.139464 0.819523 0.383245 0.083 Uiso 1 1 calc R U . . .
C58 C -0.0351(5) 0.7197(13) 0.4128(3) 0.064(3) Uani 1 1 d G U . . .
H58 H -0.021140 0.766717 0.445560 0.077 Uiso 1 1 calc R U . . .
C63 C 0.1035(7) 0.8677(18) 0.3690(5) 0.046(2) Uani 1 1 d . U . . .
H63 H 0.071823 0.852302 0.389418 0.056 Uiso 1 1 calc R U . . .
C65 C 0.1385(5) 1.0181(12) 0.3086(4) 0.065(2) Uani 1 1 d G U . . .
C66 C 0.1266(6) 1.1377(14) 0.2744(4) 0.075(3) Uani 1 1 d G U . . .
H66 H 0.162952 1.159327 0.257959 0.089 Uiso 1 1 calc R U . . .
C67 C 0.0613(7) 1.2255(12) 0.2644(4) 0.078(3) Uani 1 1 d G U . . .
H67 H 0.053180 1.307248 0.241067 0.094 Uiso 1 1 calc R U . . .
C68 C 0.0081(5) 1.1939(12) 0.2885(4) 0.075(3) Uani 1 1 d G U . . .
H68 H -0.036474 1.253933 0.281639 0.089 Uiso 1 1 calc R U . . .
C69 C 0.0200(5) 1.0743(13) 0.3226(4) 0.069(3) Uani 1 1 d G U . . .
H69 H -0.016357 1.052698 0.339103 0.083 Uiso 1 1 calc R U . . .
C64 C 0.0852(6) 0.9865(11) 0.3327(4) 0.059(2) Uani 1 1 d G U . . .
C70 C 0.2569(10) 0.928(2) 0.2950(6) 0.075(3) Uani 1 1 d . U . . .
H70 H 0.278094 1.031177 0.296752 0.090 Uiso 1 1 calc R U . . .
C71 C 0.3186(11) 0.823(3) 0.3210(8) 0.090(5) Uani 1 1 d . U . . .
H71A H 0.346959 0.860834 0.355549 0.134 Uiso 1 1 calc R U . . .
H71B H 0.353394 0.813274 0.301087 0.134 Uiso 1 1 calc R U . . .
H71C H 0.296828 0.724667 0.323929 0.134 Uiso 1 1 calc R U . . .
C72 C 0.2143(11) 0.886(3) 0.2391(7) 0.091(5) Uani 1 1 d . U . . .
H72A H 0.210846 0.777117 0.235659 0.137 Uiso 1 1 calc R U . . .
H72B H 0.241969 0.926261 0.217155 0.137 Uiso 1 1 calc R U . . .
H72C H 0.162793 0.929258 0.228515 0.137 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
Ru1 Cl1 2.323(3) . ?
Ru1 Cl2 2.350(3) . ?
Ru1 O1 2.266(12) . ?
Ru1 C1 1.936(14) . ?
Ru1 C27 1.777(14) . ?
O1 C29 1.324(15) . ?
O1 C34 1.42(2) . ?
N1 C1 1.391(18) . ?
N1 C2 1.515(18) . ?
N1 C5 1.472(18) . ?
C1 C4 1.595(17) . ?
C2 C3 1.48(2) . ?
C2 C13 1.461(18) . ?
C2 C14 1.556(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.537(19) . ?
C4 C15 1.582(16) . ?
C4 C21 1.611(13) . ?
C5 H5 1.0000 . ?
C5 C6 1.54(2) . ?
C5 C7 1.552(19) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 1.0000 . ?
C7 C8 1.48(2) . ?
C7 C12 1.56(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.546(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.52(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.44(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.58(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 H16 0.9500 . ?
C16 C17 1.3900 . ?
C17 H17 0.9500 . ?
C17 C18 1.3900 . ?
C18 H18 0.9500 . ?
C18 C19 1.3900 . ?
C19 H19 0.9500 . ?
C19 C20 1.3900 . ?
C20 H20 0.9500 . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C22 H22 0.9500 . ?
C22 C23 1.3900 . ?
C23 H23 0.9500 . ?
C23 C24 1.3900 . ?
C24 H24 0.9500 . ?
C24 C25 1.3900 . ?
C25 H25 0.9500 . ?
C25 C26 1.3900 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.431(17) . ?
C29 C28 1.3900 . ?
C29 C30 1.3900 . ?
C28 C33 1.3900 . ?
C33 H33 0.9500 . ?
C33 C32 1.3900 . ?
C32 H32 0.9500 . ?
C32 C31 1.3900 . ?
C31 H31 0.9500 . ?
C31 C30 1.3900 . ?
C30 H30 0.9500 . ?
C34 H34 1.0000 . ?
C34 C35 1.547(13) . ?
C34 C36 1.539(13) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
Ru2 Cl3 2.328(4) . ?
Ru2 Cl4 2.315(4) . ?
Ru2 O2 2.336(11) . ?
Ru2 C37 1.955(14) . ?
Ru2 C63 1.775(12) . ?
O2 C65 1.330(13) . ?
O2 C70 1.477(18) . ?
N2 C37 1.350(17) . ?
N2 C38 1.487(17) . ?
N2 C41 1.460(16) . ?
C37 C40 1.571(18) . ?
C38 C39 1.504(18) . ?
C38 C49 1.67(2) . ?
C38 C50 1.476(18) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.54(2) . ?
C40 C51 1.535(17) . ?
C40 C57 1.540(15) . ?
C41 H41 1.0000 . ?
C41 C42 1.56(2) . ?
C41 C43 1.51(2) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43 1.0000 . ?
C43 C44 1.52(3) . ?
C43 C48 1.54(2) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C44 C45 1.53(2) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C45 C46 1.44(3) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C46 C47 1.57(3) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C48 1.53(2) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 C52 1.3900 . ?
C51 C56 1.3900 . ?
C52 H52 0.9500 . ?
C52 C53 1.3900 . ?
C53 H53 0.9500 . ?
C53 C54 1.3900 . ?
C54 H54 0.9500 . ?
C54 C55 1.3900 . ?
C55 H55 0.9500 . ?
C55 C56 1.3900 . ?
C56 H56 0.9500 . ?
C57 C62 1.3900 . ?
C57 C58 1.3900 . ?
C62 H62 0.9500 . ?
C62 C61 1.3900 . ?
C61 H61 0.9500 . ?
C61 C60 1.3900 . ?
C60 H60 0.9500 . ?
C60 C59 1.3900 . ?
C59 H59 0.9500 . ?
C59 C58 1.3900 . ?
C58 H58 0.9500 . ?
C63 H63 0.9500 . ?
C63 C64 1.418(16) . ?
C65 C66 1.3900 . ?
C65 C64 1.3900 . ?
C66 H66 0.9500 . ?
C66 C67 1.3900 . ?
C67 H67 0.9500 . ?
C67 C68 1.3900 . ?
C68 H68 0.9500 . ?
C68 C69 1.3900 . ?
C69 H69 0.9500 . ?
C69 C64 1.3900 . ?
C70 H70 1.0000 . ?
C70 C71 1.47(2) . ?
C70 C72 1.52(3) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 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
Cl1 Ru1 Cl2 153.23(12) . . ?
O1 Ru1 Cl1 86.6(3) . . ?
O1 Ru1 Cl2 84.6(4) . . ?
C1 Ru1 Cl1 97.2(4) . . ?
C1 Ru1 Cl2 91.8(4) . . ?
C1 Ru1 O1 176.2(5) . . ?
C27 Ru1 Cl1 103.0(5) . . ?
C27 Ru1 Cl2 100.1(5) . . ?
C27 Ru1 O1 78.9(6) . . ?
C27 Ru1 C1 100.6(6) . . ?
C29 O1 Ru1 108.2(9) . . ?
C29 O1 C34 121.5(13) . . ?
C34 O1 Ru1 129.9(11) . . ?
C1 N1 C2 115.4(10) . . ?
C1 N1 C5 115.9(11) . . ?
C5 N1 C2 128.7(12) . . ?
N1 C1 Ru1 124.4(9) . . ?
N1 C1 C4 103.6(11) . . ?
C4 C1 Ru1 132.0(10) . . ?
N1 C2 C14 108.2(11) . . ?
C3 C2 N1 99.4(12) . . ?
C3 C2 C14 112.0(11) . . ?
C13 C2 N1 114.2(11) . . ?
C13 C2 C3 111.5(12) . . ?
C13 C2 C14 111.1(13) . . ?
C2 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
C2 C3 C4 107.7(11) . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C1 C4 C21 113.1(9) . . ?
C3 C4 C1 102.6(11) . . ?
C3 C4 C15 112.0(10) . . ?
C3 C4 C21 108.5(10) . . ?
C15 C4 C1 108.9(10) . . ?
C15 C4 C21 111.4(10) . . ?
N1 C5 H5 105.4 . . ?
N1 C5 C6 112.2(13) . . ?
N1 C5 C7 112.6(12) . . ?
C6 C5 H5 105.4 . . ?
C6 C5 C7 114.7(13) . . ?
C7 C5 H5 105.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7 107.6 . . ?
C5 C7 C12 105.1(13) . . ?
C8 C7 C5 117.3(13) . . ?
C8 C7 H7 107.6 . . ?
C8 C7 C12 111.1(14) . . ?
C12 C7 H7 107.6 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C7 C8 C9 112.1(13) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C10 C9 C8 107.5(14) . . ?
C10 C9 H9A 110.2 . . ?
C10 C9 H9B 110.2 . . ?
C9 C10 H10A 107.7 . . ?
C9 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
C11 C10 C9 118.3(15) . . ?
C11 C10 H10A 107.7 . . ?
C11 C10 H10B 107.7 . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C10 C11 C12 114.6(14) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C7 C12 C11 109.9(14) . . ?
C7 C12 H12A 109.7 . . ?
C7 C12 H12B 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C4 123.5(7) . . ?
C16 C15 C20 120.0 . . ?
C20 C15 C4 116.5(7) . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C4 123.7(7) . . ?
C22 C21 C26 120.0 . . ?
C26 C21 C4 116.2(7) . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26 120.0 . . ?
Ru1 C27 H27 119.5 . . ?
C28 C27 Ru1 121.0(11) . . ?
C28 C27 H27 119.5 . . ?
O1 C29 C28 116.3(10) . . ?
O1 C29 C30 123.6(10) . . ?
C28 C29 C30 120.0 . . ?
C29 C28 C27 115.6(10) . . ?
C29 C28 C33 120.0 . . ?
C33 C28 C27 124.3(10) . . ?
C28 C33 H33 120.0 . . ?
C28 C33 C32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
O1 C34 H34 110.0 . . ?
O1 C34 C35 111.1(15) . . ?
O1 C34 C36 105.9(14) . . ?
C35 C34 H34 110.0 . . ?
C36 C34 H34 110.0 . . ?
C36 C34 C35 109.6(15) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Cl3 Ru2 O2 85.3(3) . . ?
Cl4 Ru2 Cl3 150.97(17) . . ?
Cl4 Ru2 O2 85.4(3) . . ?
C37 Ru2 Cl3 99.1(4) . . ?
C37 Ru2 Cl4 92.0(4) . . ?
C37 Ru2 O2 174.7(5) . . ?
C63 Ru2 Cl3 102.3(5) . . ?
C63 Ru2 Cl4 102.2(5) . . ?
C63 Ru2 O2 76.7(5) . . ?
C63 Ru2 C37 99.4(6) . . ?
C65 O2 Ru2 108.2(7) . . ?
C65 O2 C70 124.4(11) . . ?
C70 O2 Ru2 127.2(10) . . ?
C37 N2 C38 113.2(10) . . ?
C37 N2 C41 123.0(11) . . ?
C41 N2 C38 123.8(11) . . ?
N2 C37 Ru2 120.7(9) . . ?
N2 C37 C40 107.3(11) . . ?
C40 C37 Ru2 132.0(10) . . ?
N2 C38 C39 102.1(11) . . ?
N2 C38 C49 111.4(11) . . ?
C39 C38 C49 107.9(12) . . ?
C50 C38 N2 118.4(13) . . ?
C50 C38 C39 112.8(11) . . ?
C50 C38 C49 104.1(12) . . ?
C38 C39 H39A 110.8 . . ?
C38 C39 H39B 110.8 . . ?
C38 C39 C40 104.5(12) . . ?
H39A C39 H39B 108.9 . . ?
C40 C39 H39A 110.8 . . ?
C40 C39 H39B 110.8 . . ?
C39 C40 C37 99.9(11) . . ?
C51 C40 C37 111.0(11) . . ?
C51 C40 C39 112.1(11) . . ?
C51 C40 C57 112.6(11) . . ?
C57 C40 C37 111.7(11) . . ?
C57 C40 C39 108.9(12) . . ?
N2 C41 H41 104.9 . . ?
N2 C41 C42 113.2(13) . . ?
N2 C41 C43 114.7(12) . . ?
C42 C41 H41 104.9 . . ?
C43 C41 H41 104.9 . . ?
C43 C41 C42 113.1(13) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43 106.9 . . ?
C41 C43 C44 112.7(13) . . ?
C41 C43 C48 112.9(13) . . ?
C44 C43 H43 106.9 . . ?
C44 C43 C48 110.2(15) . . ?
C48 C43 H43 106.9 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 C45 110.5(15) . . ?
H44A C44 H44B 108.1 . . ?
C45 C44 H44A 109.5 . . ?
C45 C44 H44B 109.5 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
H45A C45 H45B 108.1 . . ?
C46 C45 C44 110.8(18) . . ?
C46 C45 H45A 109.5 . . ?
C46 C45 H45B 109.5 . . ?
C45 C46 H46A 109.4 . . ?
C45 C46 H46B 109.4 . . ?
C45 C46 C47 111.0(18) . . ?
H46A C46 H46B 108.0 . . ?
C47 C46 H46A 109.4 . . ?
C47 C46 H46B 109.4 . . ?
C46 C47 H47A 109.4 . . ?
C46 C47 H47B 109.4 . . ?
H47A C47 H47B 108.0 . . ?
C48 C47 C46 111.1(15) . . ?
C48 C47 H47A 109.4 . . ?
C48 C47 H47B 109.4 . . ?
C43 C48 H48A 109.0 . . ?
C43 C48 H48B 109.0 . . ?
C47 C48 C43 112.8(15) . . ?
C47 C48 H48A 109.0 . . ?
C47 C48 H48B 109.0 . . ?
H48A C48 H48B 107.8 . . ?
C38 C49 H49A 109.5 . . ?
C38 C49 H49B 109.5 . . ?
C38 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C38 C50 H50A 109.5 . . ?
C38 C50 H50B 109.5 . . ?
C38 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C52 C51 C40 121.4(8) . . ?
C52 C51 C56 120.0 . . ?
C56 C51 C40 118.6(8) . . ?
C51 C52 H52 120.0 . . ?
C51 C52 C53 120.0 . . ?
C53 C52 H52 120.0 . . ?
C52 C53 H53 120.0 . . ?
C54 C53 C52 120.0 . . ?
C54 C53 H53 120.0 . . ?
C53 C54 H54 120.0 . . ?
C53 C54 C55 120.0 . . ?
C55 C54 H54 120.0 . . ?
C54 C55 H55 120.0 . . ?
C54 C55 C56 120.0 . . ?
C56 C55 H55 120.0 . . ?
C51 C56 H56 120.0 . . ?
C55 C56 C51 120.0 . . ?
C55 C56 H56 120.0 . . ?
C62 C57 C40 119.6(8) . . ?
C62 C57 C58 120.0 . . ?
C58 C57 C40 120.3(8) . . ?
C57 C62 H62 120.0 . . ?
C57 C62 C61 120.0 . . ?
C61 C62 H62 120.0 . . ?
C62 C61 H61 120.0 . . ?
C62 C61 C60 120.0 . . ?
C60 C61 H61 120.0 . . ?
C61 C60 H60 120.0 . . ?
C59 C60 C61 120.0 . . ?
C59 C60 H60 120.0 . . ?
C60 C59 H59 120.0 . . ?
C58 C59 C60 120.0 . . ?
C58 C59 H59 120.0 . . ?
C57 C58 H58 120.0 . . ?
C59 C58 C57 120.0 . . ?
C59 C58 H58 120.0 . . ?
Ru2 C63 H63 118.4 . . ?
C64 C63 Ru2 123.2(9) . . ?
C64 C63 H63 118.4 . . ?
O2 C65 C66 125.0(8) . . ?
O2 C65 C64 115.0(8) . . ?
C66 C65 C64 120.0 . . ?
C65 C66 H66 120.0 . . ?
C65 C66 C67 120.0 . . ?
C67 C66 H66 120.0 . . ?
C66 C67 H67 120.0 . . ?
C68 C67 C66 120.0 . . ?
C68 C67 H67 120.0 . . ?
C67 C68 H68 120.0 . . ?
C69 C68 C67 120.0 . . ?
C69 C68 H68 120.0 . . ?
C68 C69 H69 120.0 . . ?
C68 C69 C64 120.0 . . ?
C64 C69 H69 120.0 . . ?
C65 C64 C63 116.5(8) . . ?
C69 C64 C63 123.4(8) . . ?
C69 C64 C65 120.0 . . ?
O2 C70 H70 109.6 . . ?
O2 C70 C72 104.2(14) . . ?
C71 C70 O2 110.1(13) . . ?
C71 C70 H70 109.6 . . ?
C71 C70 C72 113.5(18) . . ?
C72 C70 H70 109.6 . . ?
C70 C71 H71A 109.5 . . ?
C70 C71 H71B 109.5 . . ?
C70 C71 H71C 109.5 . . ?
H71A C71 H71B 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C70 C72 H72A 109.5 . . ?
C70 C72 H72B 109.5 . . ?
C70 C72 H72C 109.5 . . ?
H72A C72 H72B 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ru1 O1 C29 C28 0.3(12) . . . . ?
Ru1 O1 C29 C30 177.5(7) . . . . ?
Ru1 O1 C34 C35 100.9(16) . . . . ?
Ru1 O1 C34 C36 -18(2) . . . . ?
Ru1 C1 C4 C3 -167.0(10) . . . . ?
Ru1 C1 C4 C15 -48.2(14) . . . . ?
Ru1 C1 C4 C21 76.3(15) . . . . ?
Ru1 C27 C28 C29 -0.1(15) . . . . ?
Ru1 C27 C28 C33 -177.4(8) . . . . ?
Cl1 Ru1 C27 C28 84.1(11) . . . . ?
Cl2 Ru1 C27 C28 -82.2(12) . . . . ?
O1 Ru1 C27 C28 0.2(11) . . . . ?
O1 C29 C28 C27 -0.2(14) . . . . ?
O1 C29 C28 C33 177.3(13) . . . . ?
O1 C29 C30 C31 -177.0(14) . . . . ?
N1 C1 C4 C3 11.8(13) . . . . ?
N1 C1 C4 C15 130.6(10) . . . . ?
N1 C1 C4 C21 -104.9(12) . . . . ?
N1 C2 C3 C4 33.2(12) . . . . ?
N1 C5 C7 C8 -39(2) . . . . ?
N1 C5 C7 C12 -163.5(13) . . . . ?
C1 Ru1 C27 C28 -175.9(11) . . . . ?
C1 N1 C2 C3 -27.1(13) . . . . ?
C1 N1 C2 C13 -145.9(12) . . . . ?
C1 N1 C2 C14 89.9(14) . . . . ?
C1 N1 C5 C6 -114.8(14) . . . . ?
C1 N1 C5 C7 114.0(14) . . . . ?
C1 C4 C15 C16 125.3(9) . . . . ?
C1 C4 C15 C20 -57.5(11) . . . . ?
C1 C4 C21 C22 -15.9(15) . . . . ?
C1 C4 C21 C26 167.2(9) . . . . ?
C2 N1 C1 Ru1 -171.8(9) . . . . ?
C2 N1 C1 C4 9.3(14) . . . . ?
C2 N1 C5 C6 61.5(17) . . . . ?
C2 N1 C5 C7 -69.8(18) . . . . ?
C2 C3 C4 C1 -29.3(13) . . . . ?
C2 C3 C4 C15 -146.0(10) . . . . ?
C2 C3 C4 C21 90.6(12) . . . . ?
C3 C4 C15 C16 -121.9(10) . . . . ?
C3 C4 C15 C20 55.3(11) . . . . ?
C3 C4 C21 C22 -129.1(10) . . . . ?
C3 C4 C21 C26 54.0(12) . . . . ?
C4 C15 C16 C17 177.1(9) . . . . ?
C4 C15 C20 C19 -177.3(9) . . . . ?
C4 C21 C22 C23 -176.7(11) . . . . ?
C4 C21 C26 C25 177.0(10) . . . . ?
C5 N1 C1 Ru1 5.0(16) . . . . ?
C5 N1 C1 C4 -173.9(10) . . . . ?
C5 N1 C2 C3 156.6(12) . . . . ?
C5 N1 C2 C13 37.9(19) . . . . ?
C5 N1 C2 C14 -86.3(15) . . . . ?
C5 C7 C8 C9 177.3(14) . . . . ?
C5 C7 C12 C11 179.3(14) . . . . ?
C6 C5 C7 C8 -169.5(15) . . . . ?
C6 C5 C7 C12 66.5(18) . . . . ?
C7 C8 C9 C10 58.2(18) . . . . ?
C8 C7 C12 C11 51.4(18) . . . . ?
C8 C9 C10 C11 -51(2) . . . . ?
C9 C10 C11 C12 45(2) . . . . ?
C10 C11 C12 C7 -43(2) . . . . ?
C12 C7 C8 C9 -61.7(18) . . . . ?
C13 C2 C3 C4 154.0(12) . . . . ?
C14 C2 C3 C4 -80.9(14) . . . . ?
C15 C4 C21 C22 107.2(10) . . . . ?
C15 C4 C21 C26 -69.7(11) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C15 C20 C19 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C15 0.0 . . . . ?
C20 C15 C16 C17 0.0 . . . . ?
C21 C4 C15 C16 -0.2(12) . . . . ?
C21 C4 C15 C20 177.0(7) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C21 C26 C25 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C21 0.0 . . . . ?
C26 C21 C22 C23 0.0 . . . . ?
C27 C28 C33 C32 177.2(13) . . . . ?
C29 O1 C34 C35 -71(2) . . . . ?
C29 O1 C34 C36 170.0(14) . . . . ?
C29 C28 C33 C32 0.0 . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C28 C33 C32 C31 0.0 . . . . ?
C33 C32 C31 C30 0.0 . . . . ?
C32 C31 C30 C29 0.0 . . . . ?
C30 C29 C28 C27 -177.4(12) . . . . ?
C30 C29 C28 C33 0.0 . . . . ?
C34 O1 C29 C28 173.8(13) . . . . ?
C34 O1 C29 C30 -9(2) . . . . ?
Ru2 O2 C65 C66 -178.8(6) . . . . ?
Ru2 O2 C65 C64 -0.8(10) . . . . ?
Ru2 O2 C70 C71 -14(2) . . . . ?
Ru2 O2 C70 C72 108.2(15) . . . . ?
Ru2 C37 C40 C39 153.5(11) . . . . ?
Ru2 C37 C40 C51 -88.1(14) . . . . ?
Ru2 C37 C40 C57 38.5(19) . . . . ?
Ru2 C63 C64 C65 -8.4(15) . . . . ?
Ru2 C63 C64 C69 174.9(7) . . . . ?
Cl3 Ru2 C63 C64 87.9(11) . . . . ?
Cl4 Ru2 C63 C64 -76.4(12) . . . . ?
O2 Ru2 C63 C64 5.8(11) . . . . ?
O2 C65 C66 C67 177.9(13) . . . . ?
O2 C65 C64 C63 5.1(12) . . . . ?
O2 C65 C64 C69 -178.1(11) . . . . ?
N2 C37 C40 C39 -24.5(15) . . . . ?
N2 C37 C40 C51 93.9(13) . . . . ?
N2 C37 C40 C57 -139.5(12) . . . . ?
N2 C38 C39 C40 -33.0(15) . . . . ?
N2 C41 C43 C44 -53.8(19) . . . . ?
N2 C41 C43 C48 -179.4(14) . . . . ?
C37 Ru2 C63 C64 -170.6(11) . . . . ?
C37 N2 C38 C39 18.0(16) . . . . ?
C37 N2 C38 C49 132.9(12) . . . . ?
C37 N2 C38 C50 -106.5(14) . . . . ?
C37 N2 C41 C42 -102.3(16) . . . . ?
C37 N2 C41 C43 125.9(15) . . . . ?
C37 C40 C51 C52 26.3(13) . . . . ?
C37 C40 C51 C56 -157.1(9) . . . . ?
C37 C40 C57 C62 53.6(15) . . . . ?
C37 C40 C57 C58 -129.1(11) . . . . ?
C38 N2 C37 Ru2 -173.7(9) . . . . ?
C38 N2 C37 C40 4.6(16) . . . . ?
C38 N2 C41 C42 76.2(16) . . . . ?
C38 N2 C41 C43 -56(2) . . . . ?
C38 C39 C40 C37 35.0(14) . . . . ?
C38 C39 C40 C51 -82.7(13) . . . . ?
C38 C39 C40 C57 152.1(11) . . . . ?
C39 C40 C51 C52 137.1(9) . . . . ?
C39 C40 C51 C56 -46.3(13) . . . . ?
C39 C40 C57 C62 -55.8(13) . . . . ?
C39 C40 C57 C58 121.6(11) . . . . ?
C40 C51 C52 C53 176.6(10) . . . . ?
C40 C51 C56 C55 -176.7(10) . . . . ?
C40 C57 C62 C61 177.3(12) . . . . ?
C40 C57 C58 C59 -177.3(12) . . . . ?
C41 N2 C37 Ru2 5.1(19) . . . . ?
C41 N2 C37 C40 -176.7(13) . . . . ?
C41 N2 C38 C39 -160.7(13) . . . . ?
C41 N2 C38 C49 -45.8(17) . . . . ?
C41 N2 C38 C50 74.8(18) . . . . ?
C41 C43 C44 C45 176.6(15) . . . . ?
C41 C43 C48 C47 178.0(16) . . . . ?
C42 C41 C43 C44 174.4(14) . . . . ?
C42 C41 C43 C48 49(2) . . . . ?
C43 C44 C45 C46 63(2) . . . . ?
C44 C43 C48 C47 51(2) . . . . ?
C44 C45 C46 C47 -60(2) . . . . ?
C45 C46 C47 C48 54(2) . . . . ?
C46 C47 C48 C43 -49(2) . . . . ?
C48 C43 C44 C45 -56(2) . . . . ?
C49 C38 C39 C40 -150.4(12) . . . . ?
C50 C38 C39 C40 95.2(15) . . . . ?
C51 C40 C57 C62 179.3(8) . . . . ?
C51 C40 C57 C58 -3.4(15) . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C52 C51 C56 C55 0.0 . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C54 C55 C56 C51 0.0 . . . . ?
C56 C51 C52 C53 0.0 . . . . ?
C57 C40 C51 C52 -99.8(11) . . . . ?
C57 C40 C51 C56 76.9(12) . . . . ?
C57 C62 C61 C60 0.0 . . . . ?
C62 C57 C58 C59 0.0 . . . . ?
C62 C61 C60 C59 0.0 . . . . ?
C61 C60 C59 C58 0.0 . . . . ?
C60 C59 C58 C57 0.0 . . . . ?
C58 C57 C62 C61 0.0 . . . . ?
C65 O2 C70 C71 172.4(16) . . . . ?
C65 O2 C70 C72 -66(2) . . . . ?
C65 C66 C67 C68 0.0 . . . . ?
C66 C65 C64 C63 -176.8(11) . . . . ?
C66 C65 C64 C69 0.0 . . . . ?
C66 C67 C68 C69 0.0 . . . . ?
C67 C68 C69 C64 0.0 . . . . ?
C68 C69 C64 C63 176.6(12) . . . . ?
C68 C69 C64 C65 0.0 . . . . ?
C64 C65 C66 C67 0.0 . . . . ?
C70 O2 C65 C66 -4.1(19) . . . . ?
C70 O2 C65 C64 173.9(13) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 423 electrons were 
found in a volume of 1247Å³ in 1 void per unit cell. 
This is consistent with the presence of 
2[C6H12] per Asymmetric Unit 
which account for 384 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.545 0.000 1246.6 422.6 '8 C6H12'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.505
_oxdiff_exptl_absorpt_empirical_full_min 0.343
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.752(18)
2 0.248(18)

####################################################################### 
# 
# 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_amd-r1392
_database_code_depnum_ccdc_archive 'CCDC 2366139'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-05-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H45 Cl2 N O Ru'
_chemical_formula_sum            'C35 H45 Cl2 N O Ru'
_chemical_formula_weight         667.69
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C35 H45 N1 O1 Cl2 Ru1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.5043(3)
_cell_length_b                   16.0340(4)
_cell_length_c                   17.8672(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3295.78(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16254
_cell_measurement_temperature    139.99(10)
_cell_measurement_theta_max      73.3690
_cell_measurement_theta_min      3.6770
_shelx_estimated_absorpt_T_max   0.747
_shelx_estimated_absorpt_T_min   0.460
_exptl_absorpt_coefficient_mu    5.538
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.120a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense green'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1392
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 -1 0.0530
-1 -1 0 0.0648
0 1 1 0.0458
1 2 1 0.0505
2 1 -1 0.0598
1 -1 -2 0.0574
-2 1 0 0.0551
2 -1 0 0.0437
1 -2 -1 0.0427
0 -9 -7 0.0362
0 -1 0 0.0267
0 1 0 0.0294
2 -1 11 0.0585
-2 0 -11 0.0648
-2 -2 1 0.0648
-1 6 9 0.0556
-3 8 6 0.0455
-6 5 -2 0.0511
1 0 1 0.0598
5 -8 -1 0.0381
-2 1 -2 0.0521

_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.056
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0001 -1.9976 -0.9997 0.1046 0.0360 0.2234
-1.0005 -1.0010 0.0010 0.1266 0.0431 0.0966
-0.0005 0.9966 1.0006 0.0220 0.0071 -0.1268
1.0001 1.9976 0.9997 -0.1046 -0.0360 -0.2234
2.0015 1.0053 -1.0026 -0.2751 -0.0933 -0.0663
1.0014 -0.9922 -2.0023 -0.1705 -0.0573 0.1571
-2.0007 0.9980 0.0050 0.1557 0.2358 -0.0333
2.0007 -0.9980 -0.0050 -0.1557 -0.2358 0.0333
1.0007 -1.9956 -1.0037 -0.0836 -0.1500 0.1812
-0.0007 -8.5282 -6.6436 -0.0834 -0.1424 0.9863
-0.0001 -1.0000 -0.0010 0.0325 -0.0499 0.0755
0.0001 1.0000 0.0010 -0.0325 0.0499 -0.0755
2.3999 -0.8191 10.9589 0.3964 -0.7315 -0.5548
-2.3921 0.3919 -10.9923 -0.3850 0.7109 0.5885
-2.0017 -2.0053 1.0016 0.3076 0.0434 0.1418
-1.3154 6.4892 8.8255 0.3918 0.0700 -0.9174
-2.5296 8.1573 6.0190 0.2991 0.3860 -0.8727
-6.4574 4.8698 -2.1613 0.3307 0.9362 -0.1194
0.9998 -0.0024 0.9976 -0.0396 -0.1357 -0.0724
4.8955 -7.7633 -1.3285 -0.2794 -0.7865 0.5508
-1.9995 1.0049 -1.9942 0.0468 0.3213 0.0694

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38532
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.776
_diffrn_reflns_theta_min         3.704
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     50.00  75.00   0.50    2.00    --   63.42-167.00  34.00   50
  2  ω     45.00  70.00   0.50    2.00    --   63.42-116.00-179.00   50
  3  ω    -76.00 -51.00   0.50    2.00    --  -64.25-167.00  34.00   50
  4  ω    -96.00 -71.00   0.50    2.00    --  -64.25 167.00  54.00   50
  5  ω    -79.00 -54.00   0.50    2.00    --  -64.25 116.00 -91.00   50
  6  ω    -90.00 -58.00   0.50    2.00    --  -70.98 116.00 -91.00   64
  7  ω    -83.00 -43.00   0.50    2.00    --  -70.98 167.00  54.00   80
  8  ω     56.00  81.00   0.50    2.00    --   75.74-116.00-179.00   50
  9  ω     87.00 113.00   0.50    2.00    --   76.22-167.00  34.00   52
 10  ω     43.00  68.00   0.50    2.00    --   76.22-116.00-179.00   50
 11  ω     58.00  83.00   0.50    2.00    --   76.22 167.00  54.00   50
 12  ω     28.00  53.00   0.50    2.00    --   63.42 -95.00-120.00   50
 13  ω     44.00  69.00   0.50    2.00    --   63.42 -95.00 -90.00   50
 14  ω     33.00  72.00   0.50    2.00    --   63.42 -95.00  30.00   78
 15  ω     22.00  62.00   0.50    2.00    --   63.42-125.00 120.00   80
 16  ω    -63.00 -37.00   0.50    2.00    --  -70.98   0.00   0.00   52
 17  ω    -72.00 -42.00   0.50    2.00    --  -70.98   0.00 150.00   60
 18  ω    -69.00 -35.00   0.50    2.00    --  -70.98   0.00-180.00   68
 19  ω    -68.00 -35.00   0.50    2.00    --  -70.98   0.00-120.00   66
 20  ω     39.00  82.00   0.50    2.00    --   75.74 -95.00  30.00   86
 21  ω     38.00  63.00   0.50    2.00    --   75.74 -95.00-180.00   50
 22  ω     43.00  68.00   0.50    2.00    --   75.74 -95.00 150.00   50
 23  ω     98.00 123.00   0.50    2.00    --   76.00  23.00  43.15   50
 24  ω     38.00  63.00   0.50    2.00    --   76.22 -95.00  90.00   50
 25  ω     66.00  91.00   0.50    2.00    --   76.22-125.00 150.00   50
 26  ω     38.00  63.00   0.50    2.00    --   76.22 -95.00 -60.00   50
 27  ω     48.00  79.00   0.50    2.00    --   76.22 -95.00 -90.00   62
 28  ω     74.00  99.00   0.50    2.00    --   76.22-125.00  30.00   50
 29  ω     73.00  98.00   0.50    2.00    --   76.22-125.00  60.00   50
 30  ω   -108.00 -80.00   0.50    2.00    --  -76.25 -86.00 -73.87   56
 31  ω    -97.00 -71.00   0.50    2.00    --  -76.25 118.00-131.70   52
 32  ω    -70.00 -45.00   0.50    2.00    --  -76.25  78.00 -64.87   50
 33  ω   -109.00 -82.00   0.50    2.00    --  -76.25 -82.00 -26.89   54
 34  ω     46.00  78.00   0.50    2.00    --   79.75   6.00  90.86   64
 35  ω     62.00  87.00   0.50    2.00    --   79.75  21.00  61.24   50
 36  ω     66.00  93.00   0.50    2.00    --   79.75  21.00 -90.79   54
 37  ω     83.00 109.00   0.50    2.00    --   79.75   1.00 -67.96   52
 38  ω     73.00 125.00   0.50    2.00    --   79.75  22.00-139.63  104
 39  ω     43.00  74.00   0.50    2.00    --   79.75   1.00 -67.96   62
 40  ω     68.00  94.00   0.50    2.00    --   79.75  16.00 176.08   52
 41  ω     88.00 114.00   0.50    2.00    --   79.75   4.00-136.35   52
 42  ω    101.00 126.00   0.50    2.00    --   79.75  19.00   5.04   50
 43  ω     85.00 119.00   0.50    2.00    --   79.75   2.00 -41.19   68
 44  ω     53.00  79.00   0.50    2.00    --   79.75  19.00   5.04   52
 45  ω     88.00 116.00   0.50    2.00    --   79.75   4.00  21.81   56
 46  ω     89.00 121.00   0.50    2.00    --   79.75  20.00 -74.32   64
 47  ω     83.00 120.00   0.50    2.00    --   79.75  22.00 179.32   74
 48  ω     72.00 110.00   0.50    2.00    --   79.75  22.00  -2.27   76
 49  ω     87.00 116.00   0.50    2.00    --   79.75   6.00  90.86   58
 50  ω     59.00  86.00   0.50    2.00    --   79.75   4.00  21.81   54
 51  ω     95.00 123.00   0.50    2.00    --   79.75  54.00-115.13   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0939025000
_diffrn_orient_matrix_UB_12      -0.0325142000
_diffrn_orient_matrix_UB_13      0.0543017000
_diffrn_orient_matrix_UB_21      -0.0930516000
_diffrn_orient_matrix_UB_22      0.0499257000
_diffrn_orient_matrix_UB_23      -0.0426431000
_diffrn_orient_matrix_UB_31      -0.0211053000
_diffrn_orient_matrix_UB_32      -0.0754221000
_diffrn_orient_matrix_UB_33      -0.0516376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                5827
_reflns_number_total             6742
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.120a 64-bit (release 16-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.458
_refine_diff_density_min         -1.661
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 
;
 Flack x determined using 2227 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.037(7)
_refine_ls_extinction_coef       0.00039(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         6742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.065
_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)+(0.0802P)²+4.6774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1448
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C19(H19), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,
 H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C25(H25), C28(H28),
 C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C32(H32A,H32B,
 H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C)
;
_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
Ru1 Ru 0.81872(5) 0.43121(4) 0.45786(3) 0.03783(19) Uani 1 1 d . . . . .
Cl1 Cl 0.8392(2) 0.55130(13) 0.38536(12) 0.0499(5) Uani 1 1 d . . . . .
Cl2 Cl 0.8613(2) 0.34469(14) 0.55934(12) 0.0500(5) Uani 1 1 d . . . . .
O1 O 0.9900(5) 0.3870(4) 0.4029(3) 0.0443(14) Uani 1 1 d . . . . .
N1 N 0.6656(6) 0.5081(4) 0.5647(3) 0.0346(14) Uani 1 1 d . . . . .
C1 C 0.4085(7) 0.3783(6) 0.3013(5) 0.046(2) Uani 1 1 d . . . . .
C2 C 0.3553(9) 0.3116(7) 0.2616(5) 0.056(2) Uani 1 1 d . . . . .
H2 H 0.347585 0.258145 0.284046 0.067 Uiso 1 1 calc R U . . .
C3 C 0.3152(10) 0.3257(8) 0.1900(5) 0.064(3) Uani 1 1 d . . . . .
H3 H 0.283034 0.281235 0.161653 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3220(9) 0.4063(7) 0.1591(5) 0.062(3) Uani 1 1 d . . . . .
H4 H 0.290642 0.415991 0.110675 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3718(8) 0.4700(7) 0.1962(5) 0.053(2) Uani 1 1 d . . . . .
H5 H 0.375539 0.523611 0.173648 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4192(7) 0.4576(6) 0.2694(5) 0.046(2) Uani 1 1 d . . . . .
C7 C 0.4767(8) 0.5216(6) 0.3087(5) 0.048(2) Uani 1 1 d . . . . .
H7 H 0.485685 0.575136 0.286779 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5199(7) 0.5059(5) 0.3791(5) 0.0416(19) Uani 1 1 d . . . . .
H8 H 0.560001 0.549221 0.404638 0.050 Uiso 1 1 calc R U . . .
C9 C 0.5068(6) 0.4279(6) 0.4150(4) 0.0366(16) Uani 1 1 d . . . . .
C10 C 0.4511(8) 0.3649(6) 0.3762(5) 0.046(2) Uani 1 1 d . . . . .
H10 H 0.440844 0.311978 0.399232 0.055 Uiso 1 1 calc R U . . .
C11 C 0.5530(7) 0.4164(5) 0.4941(5) 0.0391(18) Uani 1 1 d . . . . .
C12 C 0.4728(7) 0.4679(5) 0.5480(5) 0.0428(18) Uani 1 1 d . . . . .
H12A H 0.434591 0.514080 0.520622 0.051 Uiso 1 1 calc R U . . .
H12B H 0.412143 0.431839 0.570200 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5537(7) 0.5023(5) 0.6091(4) 0.0370(17) Uani 1 1 d . . . . .
C14 C 0.6716(8) 0.4588(4) 0.5065(4) 0.0384(17) Uani 1 1 d . . . . .
C15 C 0.5592(9) 0.3244(5) 0.5176(5) 0.048(2) Uani 1 1 d . . . . .
H15A H 0.480505 0.301080 0.519619 0.072 Uiso 1 1 calc R U . . .
H15B H 0.595440 0.320112 0.567097 0.072 Uiso 1 1 calc R U . . .
H15C H 0.605606 0.293210 0.481092 0.072 Uiso 1 1 calc R U . . .
C16 C 0.5662(9) 0.4419(6) 0.6748(5) 0.049(2) Uani 1 1 d . . . . .
H16A H 0.606416 0.391393 0.657995 0.074 Uiso 1 1 calc R U . . .
H16B H 0.489002 0.427125 0.693756 0.074 Uiso 1 1 calc R U . . .
H16C H 0.611300 0.468550 0.714726 0.074 Uiso 1 1 calc R U . . .
C17 C 0.5090(7) 0.5853(5) 0.6397(5) 0.0421(19) Uani 1 1 d . . . . .
H17A H 0.558757 0.603599 0.681066 0.063 Uiso 1 1 calc R U . . .
H17B H 0.429132 0.578325 0.657785 0.063 Uiso 1 1 calc R U . . .
H17C H 0.510306 0.627341 0.599854 0.063 Uiso 1 1 calc R U . . .
C18 C 0.7696(6) 0.5556(5) 0.5905(4) 0.0370(17) Uani 1 1 d . . . . .
H18 H 0.834087 0.540180 0.555696 0.044 Uiso 1 1 calc R U . . .
C19 C 0.7562(7) 0.6504(5) 0.5845(5) 0.0380(17) Uani 1 1 d . . . . .
H19 H 0.712541 0.670052 0.629540 0.046 Uiso 1 1 calc R U . . .
C20 C 0.6924(8) 0.6825(5) 0.5148(5) 0.0411(18) Uani 1 1 d . . . . .
H20A H 0.735573 0.665388 0.469373 0.049 Uiso 1 1 calc R U . . .
H20B H 0.613991 0.657171 0.512457 0.049 Uiso 1 1 calc R U . . .
C21 C 0.6813(9) 0.7767(5) 0.5162(5) 0.0473(19) Uani 1 1 d . . . . .
H21A H 0.640624 0.795738 0.470455 0.057 Uiso 1 1 calc R U . . .
H21B H 0.634068 0.793638 0.560005 0.057 Uiso 1 1 calc R U . . .
C22 C 0.7996(9) 0.8180(6) 0.5206(6) 0.058(3) Uani 1 1 d . . . . .
H22A H 0.842790 0.807001 0.473684 0.070 Uiso 1 1 calc R U . . .
H22B H 0.789454 0.879031 0.525387 0.070 Uiso 1 1 calc R U . . .
C23 C 0.8688(9) 0.7865(6) 0.5855(6) 0.058(3) Uani 1 1 d . . . . .
H23A H 0.832148 0.805536 0.632634 0.069 Uiso 1 1 calc R U . . .
H23B H 0.948082 0.810407 0.583294 0.069 Uiso 1 1 calc R U . . .
C24 C 0.8774(8) 0.6905(6) 0.5862(6) 0.053(2) Uani 1 1 d . . . . .
H24A H 0.922607 0.671625 0.542246 0.064 Uiso 1 1 calc R U . . .
H24B H 0.919054 0.672291 0.631880 0.064 Uiso 1 1 calc R U . . .
C25 C 0.7671(8) 0.3584(6) 0.3870(5) 0.047(2) Uani 1 1 d . . . . .
H25 H 0.685993 0.348625 0.382094 0.056 Uiso 1 1 calc R U . . .
C26 C 0.8467(8) 0.3153(5) 0.3384(5) 0.0418(19) Uani 1 1 d . . . . .
C27 C 0.9654(8) 0.3318(5) 0.3464(4) 0.043(2) Uani 1 1 d . . . . .
C28 C 1.0478(9) 0.2935(5) 0.3008(5) 0.047(2) Uani 1 1 d . . . . .
H28 H 1.128337 0.305172 0.306201 0.056 Uiso 1 1 calc R U . . .
C29 C 1.0079(9) 0.2369(6) 0.2464(5) 0.051(2) Uani 1 1 d . . . . .
H29 H 1.062462 0.210875 0.214076 0.061 Uiso 1 1 calc R U . . .
C30 C 0.8929(9) 0.2186(5) 0.2391(5) 0.049(2) Uani 1 1 d . . . . .
H30 H 0.868170 0.178864 0.203059 0.058 Uiso 1 1 calc R U . . .
C31 C 0.8119(10) 0.2580(5) 0.2843(5) 0.050(2) Uani 1 1 d . . . . .
H31 H 0.731640 0.245801 0.278272 0.059 Uiso 1 1 calc R U . . .
C32 C 0.8098(9) 0.5295(6) 0.6687(5) 0.050(2) Uani 1 1 d . . . . .
H32A H 0.756862 0.552744 0.706315 0.074 Uiso 1 1 calc R U . . .
H32B H 0.888597 0.550506 0.677614 0.074 Uiso 1 1 calc R U . . .
H32C H 0.809696 0.468511 0.672384 0.074 Uiso 1 1 calc R U . . .
C33 C 1.1106(8) 0.4158(7) 0.4134(6) 0.055(3) Uani 1 1 d . . . . .
H33 H 1.164591 0.367382 0.407641 0.066 Uiso 1 1 calc R U . . .
C34 C 1.1398(10) 0.4806(7) 0.3557(7) 0.067(3) Uani 1 1 d . . . . .
H34A H 1.141146 0.454823 0.306019 0.101 Uiso 1 1 calc R U . . .
H34B H 1.216265 0.504529 0.366792 0.101 Uiso 1 1 calc R U . . .
H34C H 1.080960 0.524827 0.356755 0.101 Uiso 1 1 calc R U . . .
C35 C 1.1178(9) 0.4482(9) 0.4930(6) 0.072(4) Uani 1 1 d . . . . .
H35A H 1.062713 0.494288 0.499438 0.108 Uiso 1 1 calc R U . . .
H35B H 1.196822 0.468071 0.502997 0.108 Uiso 1 1 calc R U . . .
H35C H 1.098449 0.403208 0.527943 0.108 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
Ru1 Cl1 2.333(2) . ?
Ru1 Cl2 2.335(2) . ?
Ru1 O1 2.313(5) . ?
Ru1 C14 1.953(9) . ?
Ru1 C25 1.822(10) . ?
O1 C27 1.373(10) . ?
O1 C33 1.473(11) . ?
N1 C13 1.515(10) . ?
N1 C14 1.309(10) . ?
N1 C18 1.491(9) . ?
C1 C2 1.422(13) . ?
C1 C6 1.399(13) . ?
C1 C10 1.442(12) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.407(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.346(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.431(12) . ?
C6 C7 1.408(13) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.413(13) . ?
C9 C10 1.383(12) . ?
C9 C11 1.522(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.569(12) . ?
C11 C14 1.540(12) . ?
C11 C15 1.535(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.536(11) . ?
C13 C16 1.528(11) . ?
C13 C17 1.528(11) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 1.0000 . ?
C18 C19 1.531(11) . ?
C18 C32 1.530(11) . ?
C19 H19 1.0000 . ?
C19 C20 1.535(11) . ?
C19 C24 1.536(11) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.517(11) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.516(13) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.495(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.542(13) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25 0.9500 . ?
C25 C26 1.439(12) . ?
C26 C27 1.397(13) . ?
C26 C31 1.393(12) . ?
C27 C28 1.393(12) . ?
C28 H28 0.9500 . ?
C28 C29 1.405(13) . ?
C29 H29 0.9500 . ?
C29 C30 1.362(14) . ?
C30 H30 0.9500 . ?
C30 C31 1.385(13) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33 1.0000 . ?
C33 C34 1.501(15) . ?
C33 C35 1.516(15) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 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
Cl1 Ru1 Cl2 154.22(9) . . ?
O1 Ru1 Cl1 86.05(16) . . ?
O1 Ru1 Cl2 88.21(16) . . ?
C14 Ru1 Cl1 98.5(2) . . ?
C14 Ru1 Cl2 88.3(2) . . ?
C14 Ru1 O1 175.2(3) . . ?
C25 Ru1 Cl1 100.2(3) . . ?
C25 Ru1 Cl2 103.1(3) . . ?
C25 Ru1 O1 77.7(3) . . ?
C25 Ru1 C14 99.9(4) . . ?
C27 O1 Ru1 109.5(5) . . ?
C27 O1 C33 119.4(7) . . ?
C33 O1 Ru1 130.7(5) . . ?
C14 N1 C13 115.0(7) . . ?
C14 N1 C18 120.8(7) . . ?
C18 N1 C13 123.5(6) . . ?
C2 C1 C10 119.8(9) . . ?
C6 C1 C2 121.3(9) . . ?
C6 C1 C10 119.0(8) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(10) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(10) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(10) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(10) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 117.7(9) . . ?
C1 C6 C7 120.0(8) . . ?
C7 C6 C5 122.3(9) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.6(9) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 118.8 . . ?
C7 C8 C9 122.5(8) . . ?
C9 C8 H8 118.8 . . ?
C8 C9 C11 119.4(8) . . ?
C10 C9 C8 118.0(8) . . ?
C10 C9 C11 122.6(8) . . ?
C1 C10 H10 119.6 . . ?
C9 C10 C1 120.9(8) . . ?
C9 C10 H10 119.6 . . ?
C9 C11 C12 107.5(6) . . ?
C9 C11 C14 112.9(7) . . ?
C9 C11 C15 112.8(7) . . ?
C14 C11 C12 101.5(6) . . ?
C15 C11 C12 111.5(7) . . ?
C15 C11 C14 110.1(7) . . ?
C11 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 C11 105.6(7) . . ?
C13 C12 H12A 110.6 . . ?
C13 C12 H12B 110.6 . . ?
N1 C13 C12 99.5(6) . . ?
N1 C13 C16 111.1(7) . . ?
N1 C13 C17 114.8(6) . . ?
C16 C13 C12 112.1(7) . . ?
C17 C13 C12 111.3(7) . . ?
C17 C13 C16 108.0(7) . . ?
N1 C14 Ru1 122.4(7) . . ?
N1 C14 C11 109.5(8) . . ?
C11 C14 Ru1 127.2(5) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18 106.0 . . ?
N1 C18 C19 113.9(6) . . ?
N1 C18 C32 112.7(7) . . ?
C19 C18 H18 106.0 . . ?
C32 C18 H18 106.0 . . ?
C32 C18 C19 111.5(7) . . ?
C18 C19 H19 107.9 . . ?
C18 C19 C20 116.0(6) . . ?
C18 C19 C24 108.9(7) . . ?
C20 C19 H19 107.9 . . ?
C20 C19 C24 108.1(7) . . ?
C24 C19 H19 107.9 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 C19 111.2(7) . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 C20 111.1(8) . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 C21 111.8(8) . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C22 C23 C24 112.2(8) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C19 C24 C23 111.1(8) . . ?
C19 C24 H24A 109.4 . . ?
C19 C24 H24B 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
Ru1 C25 H25 119.4 . . ?
C26 C25 Ru1 121.3(7) . . ?
C26 C25 H25 119.4 . . ?
C27 C26 C25 118.0(8) . . ?
C31 C26 C25 123.5(9) . . ?
C31 C26 C27 118.4(8) . . ?
O1 C27 C26 113.5(7) . . ?
O1 C27 C28 125.0(9) . . ?
C28 C27 C26 121.5(8) . . ?
C27 C28 H28 121.1 . . ?
C27 C28 C29 117.8(9) . . ?
C29 C28 H28 121.1 . . ?
C28 C29 H29 119.2 . . ?
C30 C29 C28 121.5(9) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120.0(9) . . ?
C31 C30 H30 120.0 . . ?
C26 C31 H31 119.6 . . ?
C30 C31 C26 120.8(10) . . ?
C30 C31 H31 119.6 . . ?
C18 C32 H32A 109.5 . . ?
C18 C32 H32B 109.5 . . ?
C18 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O1 C33 H33 109.2 . . ?
O1 C33 C34 109.9(8) . . ?
O1 C33 C35 106.1(8) . . ?
C34 C33 H33 109.2 . . ?
C34 C33 C35 113.2(10) . . ?
C35 C33 H33 109.2 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ru1 O1 C27 C26 -1.7(8) . . . . ?
Ru1 O1 C27 C28 179.2(7) . . . . ?
Ru1 O1 C33 C34 -93.9(9) . . . . ?
Ru1 O1 C33 C35 28.9(12) . . . . ?
Ru1 C25 C26 C27 -0.8(11) . . . . ?
Ru1 C25 C26 C31 178.9(7) . . . . ?
Cl1 Ru1 C25 C26 83.5(7) . . . . ?
Cl2 Ru1 C25 C26 -85.3(7) . . . . ?
O1 Ru1 C25 C26 -0.1(6) . . . . ?
O1 C27 C28 C29 178.6(7) . . . . ?
N1 C18 C19 C20 -38.8(10) . . . . ?
N1 C18 C19 C24 -160.9(7) . . . . ?
C1 C2 C3 C4 -3.2(15) . . . . ?
C1 C6 C7 C8 -1.4(13) . . . . ?
C2 C1 C6 C5 1.8(13) . . . . ?
C2 C1 C6 C7 -177.3(9) . . . . ?
C2 C1 C10 C9 177.7(9) . . . . ?
C2 C3 C4 C5 3.1(17) . . . . ?
C3 C4 C5 C6 -0.4(16) . . . . ?
C4 C5 C6 C1 -2.0(14) . . . . ?
C4 C5 C6 C7 177.0(9) . . . . ?
C5 C6 C7 C8 179.6(8) . . . . ?
C6 C1 C2 C3 0.8(14) . . . . ?
C6 C1 C10 C9 -3.0(13) . . . . ?
C6 C7 C8 C9 -1.4(13) . . . . ?
C7 C8 C9 C10 1.8(12) . . . . ?
C7 C8 C9 C11 -177.7(8) . . . . ?
C8 C9 C10 C1 0.4(13) . . . . ?
C8 C9 C11 C12 70.8(9) . . . . ?
C8 C9 C11 C14 -40.4(10) . . . . ?
C8 C9 C11 C15 -166.0(8) . . . . ?
C9 C11 C12 C13 -144.4(7) . . . . ?
C9 C11 C14 Ru1 -64.4(9) . . . . ?
C9 C11 C14 N1 126.5(7) . . . . ?
C10 C1 C2 C3 -180.0(9) . . . . ?
C10 C1 C6 C5 -177.5(8) . . . . ?
C10 C1 C6 C7 3.5(13) . . . . ?
C10 C9 C11 C12 -108.8(9) . . . . ?
C10 C9 C11 C14 140.1(8) . . . . ?
C10 C9 C11 C15 14.5(11) . . . . ?
C11 C9 C10 C1 179.9(8) . . . . ?
C11 C12 C13 N1 28.8(8) . . . . ?
C11 C12 C13 C16 -88.7(8) . . . . ?
C11 C12 C13 C17 150.2(7) . . . . ?
C12 C11 C14 Ru1 -179.2(5) . . . . ?
C12 C11 C14 N1 11.8(8) . . . . ?
C13 N1 C14 Ru1 -162.2(5) . . . . ?
C13 N1 C14 C11 7.4(8) . . . . ?
C13 N1 C18 C19 -74.0(9) . . . . ?
C13 N1 C18 C32 54.3(10) . . . . ?
C14 Ru1 C25 C26 -175.9(7) . . . . ?
C14 N1 C13 C12 -23.4(8) . . . . ?
C14 N1 C13 C16 94.8(8) . . . . ?
C14 N1 C13 C17 -142.3(7) . . . . ?
C14 N1 C18 C19 115.8(8) . . . . ?
C14 N1 C18 C32 -116.0(8) . . . . ?
C14 C11 C12 C13 -25.7(8) . . . . ?
C15 C11 C12 C13 91.5(8) . . . . ?
C15 C11 C14 Ru1 62.6(9) . . . . ?
C15 C11 C14 N1 -106.5(7) . . . . ?
C18 N1 C13 C12 165.8(6) . . . . ?
C18 N1 C13 C16 -76.0(9) . . . . ?
C18 N1 C13 C17 46.9(10) . . . . ?
C18 N1 C14 Ru1 8.8(9) . . . . ?
C18 N1 C14 C11 178.5(6) . . . . ?
C18 C19 C20 C21 178.2(7) . . . . ?
C18 C19 C24 C23 -176.3(8) . . . . ?
C19 C20 C21 C22 58.5(10) . . . . ?
C20 C19 C24 C23 56.9(10) . . . . ?
C20 C21 C22 C23 -54.6(11) . . . . ?
C21 C22 C23 C24 53.0(12) . . . . ?
C22 C23 C24 C19 -55.1(12) . . . . ?
C24 C19 C20 C21 -59.3(9) . . . . ?
C25 C26 C27 O1 1.8(11) . . . . ?
C25 C26 C27 C28 -179.1(8) . . . . ?
C25 C26 C31 C30 179.9(8) . . . . ?
C26 C27 C28 C29 -0.4(12) . . . . ?
C27 O1 C33 C34 77.4(10) . . . . ?
C27 O1 C33 C35 -159.9(9) . . . . ?
C27 C26 C31 C30 -0.3(13) . . . . ?
C27 C28 C29 C30 -1.2(13) . . . . ?
C28 C29 C30 C31 2.0(14) . . . . ?
C29 C30 C31 C26 -1.2(13) . . . . ?
C31 C26 C27 O1 -178.0(7) . . . . ?
C31 C26 C27 C28 1.1(13) . . . . ?
C32 C18 C19 C20 -167.6(7) . . . . ?
C32 C18 C19 C24 70.3(9) . . . . ?
C33 O1 C27 C26 -174.7(8) . . . . ?
C33 O1 C27 C28 6.3(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.648
_oxdiff_exptl_absorpt_empirical_full_min 0.644
