# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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. 
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#######################################################################

data_Sm2n
_database_code_depnum_ccdc_archive 'CCDC 2012636'
loop_
_audit_author_name
_audit_author_address
'Kun Zhang'
;Department of Chemistry, Zhejiang Sci Tech University
China
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-01-14 downloaded from the CCDC.
;
_audit_creation_date             2020-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H29 Cl2 F N5 O10 Sm'
_chemical_formula_sum            'C29 H29 Cl2 F N5 O10 Sm'
_chemical_formula_weight         847.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   19.968(6)
_cell_length_b                   8.587(3)
_cell_length_c                   19.820(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.046(9)
_cell_angle_gamma                90
_cell_volume                     3396.4(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.384
_cell_measurement_theta_min      3.062
_shelx_estimated_absorpt_T_max   0.758
_shelx_estimated_absorpt_T_min   0.631
_exptl_absorpt_coefficient_mu    1.953
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1340 before and 0.0913 after correction.
The Ratio of minimum to maximum transmission is 0.7209.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1692
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38406
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.064
_diffrn_reflns_theta_min         3.062
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5734
_reflns_number_total             7713
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         4.132
_refine_diff_density_min         -2.255
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7713
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0894
_refine_ls_restrained_S_all      1.086
_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)+(0.0390P)²+65.2627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C19(H19A,H19B), C8(H8A,H8B), C7(H7A,H7B), C17(H17A,H17B),
 C20(H20A,H20B), C29(H29A,H29B), C18(H18A,H18B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C10(H10), C5(H5), C24(H24), C26(H26), C22(H22), C1(H1A),
 C2(H2), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Sm1 Sm 0.31641(3) 0.28445(6) 0.46695(3) 0.03567(17) Uani 1 1 d . . . . .
Cl1 Cl 0.37565(17) -0.3801(4) 0.21380(18) 0.0666(9) Uani 1 1 d . . . . .
Cl2 Cl 0.0912(2) -0.2986(5) 0.67594(18) 0.0801(11) Uani 1 1 d . . . . .
O4 O 0.2449(4) 0.0768(10) 0.4897(3) 0.050(2) Uani 1 1 d . . . . .
O1 O 0.2814(3) 0.1575(8) 0.3672(3) 0.0341(15) Uani 1 1 d . . . . .
F1 F -0.1242(4) -0.3014(12) 0.3052(6) 0.108(4) Uani 1 1 d . . . . .
O2 O 0.3985(4) 0.5211(8) 0.4470(4) 0.0487(19) Uani 1 1 d . . . . .
O6 O 0.4204(4) 0.2683(9) 0.5435(4) 0.055(2) Uani 1 1 d . . . . .
O9 O 0.2667(6) 0.4831(11) 0.3777(7) 0.098(4) Uani 1 1 d . . . . .
N1 N 0.1655(4) -0.0263(9) 0.3919(4) 0.0321(17) Uani 1 1 d . . . . .
H1 H 0.198842 0.048041 0.409917 0.038 Uiso 1 1 calc R . . . .
O3 O 0.2979(4) 0.5563(9) 0.5309(5) 0.058(2) Uani 1 1 d . . . . .
O7 O 0.4670(6) 0.0594(15) 0.5840(7) 0.120(5) Uani 1 1 d . . . . .
C13 C 0.3733(5) 0.0159(12) 0.3224(5) 0.036(2) Uani 1 1 d . . . . .
O5 O 0.3837(5) 0.0445(9) 0.5100(5) 0.065(2) Uani 1 1 d . . . . .
C14 C 0.3037(5) 0.0369(11) 0.3350(4) 0.0294(19) Uani 1 1 d . . . . .
C12 C 0.3943(5) -0.1140(13) 0.2849(5) 0.040(2) Uani 1 1 d . . . . .
H12 H 0.439250 -0.125643 0.275195 0.048 Uiso 1 1 calc R . . . .
C9 C 0.2579(5) -0.0782(12) 0.3105(5) 0.035(2) Uani 1 1 d . . . . .
N3 N 0.2829(5) 0.2661(11) 0.5971(5) 0.046(2) Uani 1 1 d . . . . .
O8 O 0.1934(5) 0.3774(15) 0.4397(7) 0.085(3) Uani 1 1 d . . . . .
N4 N 0.4244(5) 0.1200(13) 0.5465(6) 0.057(3) Uani 1 1 d . . . . .
C11 C 0.3484(6) -0.2225(13) 0.2629(5) 0.043(2) Uani 1 1 d . . . . .
N2 N 0.4168(4) 0.2392(10) 0.3856(4) 0.0364(19) Uani 1 1 d . . . . .
C15 C 0.4239(5) 0.1296(12) 0.3419(5) 0.039(2) Uani 1 1 d . . . . .
H15 H 0.464901 0.123032 0.321265 0.047 Uiso 1 1 calc R . . . .
C10 C 0.2803(5) -0.2060(12) 0.2754(5) 0.036(2) Uani 1 1 d . . . . .
H10 H 0.249962 -0.281304 0.260069 0.043 Uiso 1 1 calc R . . . .
C21 C 0.3053(7) 0.4068(15) 0.6344(6) 0.060(3) Uani 1 1 d . . . . .
H21A H 0.353735 0.415623 0.634571 0.072 Uiso 1 1 calc R . . . .
H21B H 0.291285 0.402521 0.680676 0.072 Uiso 1 1 calc R . . . .
C19 C 0.3467(6) 0.6800(13) 0.5257(7) 0.058(4) Uani 1 1 d . . . . .
H19A H 0.382567 0.665551 0.559373 0.070 Uiso 1 1 calc R . . . .
H19B H 0.325557 0.779660 0.533809 0.070 Uiso 1 1 calc R . . . .
C6 C 0.0383(5) -0.0443(13) 0.3747(6) 0.041(2) Uani 1 1 d . . . . .
C23 C 0.2156(5) 0.0277(13) 0.6027(5) 0.041(2) Uani 1 1 d . . . . .
C8 C 0.1831(5) -0.0540(13) 0.3192(5) 0.039(2) Uani 1 1 d . . . . .
H8A H 0.168240 0.034597 0.292215 0.047 Uiso 1 1 calc R . . . .
H8B H 0.159047 -0.145043 0.302371 0.047 Uiso 1 1 calc R . . . .
C27 C 0.1734(5) -0.1326(12) 0.5083(5) 0.038(2) Uani 1 1 d . . . . .
C28 C 0.2135(5) -0.0060(13) 0.5323(5) 0.038(2) Uani 1 1 d . . . . .
C7 C 0.0973(5) 0.0525(12) 0.3994(6) 0.041(2) Uani 1 1 d . . . . .
H7A H 0.091830 0.077053 0.446672 0.049 Uiso 1 1 calc R . . . .
H7B H 0.097031 0.149869 0.374632 0.049 Uiso 1 1 calc R . . . .
C17 C 0.4461(6) 0.5131(14) 0.3935(7) 0.059(3) Uani 1 1 d . . . . .
H17A H 0.482085 0.587557 0.401236 0.070 Uiso 1 1 calc R . . . .
H17B H 0.424213 0.534600 0.350006 0.070 Uiso 1 1 calc R . . . .
C5 C 0.0143(6) -0.0311(15) 0.3091(6) 0.050(3) Uani 1 1 d . . . . .
H5 H 0.034798 0.038242 0.280273 0.060 Uiso 1 1 calc R . . . .
C24 C 0.1782(6) -0.0643(14) 0.6456(5) 0.049(3) Uani 1 1 d . . . . .
H24 H 0.179578 -0.043203 0.691629 0.058 Uiso 1 1 calc R . . . .
C26 C 0.1368(5) -0.2200(13) 0.5529(6) 0.044(2) Uani 1 1 d . . . . .
H26 H 0.110271 -0.302047 0.536930 0.053 Uiso 1 1 calc R . . . .
C25 C 0.1397(6) -0.1850(14) 0.6212(6) 0.049(3) Uani 1 1 d . . . . .
C20 C 0.2732(8) 0.5425(16) 0.5981(8) 0.072(4) Uani 1 1 d . . . . .
H20A H 0.225016 0.528446 0.595599 0.086 Uiso 1 1 calc R . . . .
H20B H 0.282939 0.637412 0.623133 0.086 Uiso 1 1 calc R . . . .
C29 C 0.1745(5) -0.1710(11) 0.4339(5) 0.037(2) Uani 1 1 d . . . . .
H29A H 0.216937 -0.219674 0.424072 0.044 Uiso 1 1 calc R . . . .
H29B H 0.138971 -0.244235 0.422373 0.044 Uiso 1 1 calc R . . . .
N5 N 0.2074(8) 0.4519(15) 0.3845(9) 0.090(5) Uani 1 1 d . . . . .
C22 C 0.2519(6) 0.1631(15) 0.6300(6) 0.049(3) Uani 1 1 d . . . . .
H22 H 0.252442 0.175184 0.676651 0.059 Uiso 1 1 calc R . . . .
C18 C 0.3740(7) 0.6780(12) 0.4577(7) 0.059(4) Uani 1 1 d . . . . .
H18A H 0.339385 0.704083 0.423977 0.071 Uiso 1 1 calc R . . . .
H18B H 0.410201 0.752715 0.454706 0.071 Uiso 1 1 calc R . . . .
C1 C 0.0049(6) -0.1426(16) 0.4175(7) 0.058(3) Uani 1 1 d . . . . .
H1A H 0.019142 -0.151989 0.462523 0.069 Uiso 1 1 calc R . . . .
C2 C -0.0489(7) -0.2256(17) 0.3932(8) 0.072(4) Uani 1 1 d . . . . .
H2 H -0.071727 -0.290056 0.422232 0.087 Uiso 1 1 calc R . . . .
C3 C -0.0694(6) -0.2162(16) 0.3291(8) 0.060(3) Uani 1 1 d . . . . .
C4 C -0.0402(6) -0.1195(18) 0.2845(7) 0.065(4) Uani 1 1 d . . . . .
H4 H -0.055698 -0.112378 0.239784 0.078 Uiso 1 1 calc R . . . .
C16 C 0.4727(6) 0.3483(15) 0.3961(7) 0.055(3) Uani 1 1 d . . . . .
H16A H 0.505046 0.333652 0.361273 0.066 Uiso 1 1 calc R . . . .
H16B H 0.494946 0.328955 0.439549 0.066 Uiso 1 1 calc R . . . .
O10 O 0.1621(7) 0.4909(16) 0.3454(9) 0.156(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O4 2.338(7) . ?
Sm1 O1 2.343(6) . ?
Sm1 O2 2.649(7) . ?
Sm1 O6 2.532(7) . ?
Sm1 O9 2.627(10) . ?
Sm1 O3 2.688(8) . ?
Sm1 O5 2.588(8) . ?
Sm1 N3 2.692(10) . ?
Sm1 O8 2.621(10) . ?
Sm1 N4 2.981(10) . ?
Sm1 N2 2.647(9) . ?
Cl1 C11 1.765(11) . ?
Cl2 C25 1.771(11) . ?
O4 C28 1.284(12) . ?
O1 C14 1.304(11) . ?
F1 C3 1.385(15) . ?
O2 C17 1.450(15) . ?
O2 C18 1.452(13) . ?
O6 N4 1.277(13) . ?
O9 N5 1.225(19) . ?
N1 H1 0.9800 . ?
N1 C8 1.515(12) . ?
N1 C7 1.533(12) . ?
N1 C29 1.502(12) . ?
O3 C19 1.447(14) . ?
O3 C20 1.441(17) . ?
O7 N4 1.225(13) . ?
C13 C14 1.432(13) . ?
C13 C12 1.412(14) . ?
C13 C15 1.447(13) . ?
O5 N4 1.249(13) . ?
C14 C9 1.420(13) . ?
C12 H12 0.9300 . ?
C12 C11 1.367(15) . ?
C9 C10 1.382(14) . ?
C9 C8 1.525(14) . ?
N3 C21 1.478(13) . ?
N3 C22 1.273(16) . ?
O8 N5 1.307(19) . ?
C11 C10 1.399(15) . ?
N2 C15 1.289(13) . ?
N2 C16 1.466(13) . ?
C15 H15 0.9300 . ?
C10 H10 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.500(19) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.473(19) . ?
C6 C7 1.509(14) . ?
C6 C5 1.374(15) . ?
C6 C1 1.385(17) . ?
C23 C28 1.424(14) . ?
C23 C24 1.396(16) . ?
C23 C22 1.465(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C27 C28 1.422(14) . ?
C27 C26 1.387(15) . ?
C27 C29 1.512(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.512(18) . ?
C5 H5 0.9300 . ?
C5 C4 1.400(17) . ?
C24 H24 0.9300 . ?
C24 C25 1.369(17) . ?
C26 H26 0.9300 . ?
C26 C25 1.387(16) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
N5 O10 1.216(15) . ?
C22 H22 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C1 H1A 0.9300 . ?
C1 C2 1.364(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.323(19) . ?
C3 C4 1.36(2) . ?
C4 H4 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Sm1 O1 69.0(2) . . ?
O4 Sm1 O2 177.5(2) . . ?
O4 Sm1 O6 109.6(3) . . ?
O4 Sm1 O9 114.0(3) . . ?
O4 Sm1 O3 118.4(3) . . ?
O4 Sm1 O5 69.1(3) . . ?
O4 Sm1 N3 66.2(3) . . ?
O4 Sm1 O8 72.4(4) . . ?
O4 Sm1 N4 88.4(3) . . ?
O4 Sm1 N2 119.1(3) . . ?
O1 Sm1 O2 113.5(2) . . ?
O1 Sm1 O6 134.0(3) . . ?
O1 Sm1 O9 68.9(3) . . ?
O1 Sm1 O3 139.5(2) . . ?
O1 Sm1 O5 92.5(3) . . ?
O1 Sm1 N3 134.8(3) . . ?
O1 Sm1 O8 73.6(3) . . ?
O1 Sm1 N4 114.5(3) . . ?
O1 Sm1 N2 68.1(2) . . ?
O2 Sm1 O3 60.0(3) . . ?
O2 Sm1 N3 111.4(3) . . ?
O2 Sm1 N4 90.2(3) . . ?
O6 Sm1 O2 68.5(2) . . ?
O6 Sm1 O9 136.2(3) . . ?
O6 Sm1 O3 83.6(3) . . ?
O6 Sm1 O5 49.7(3) . . ?
O6 Sm1 N3 69.5(3) . . ?
O6 Sm1 O8 152.0(3) . . ?
O6 Sm1 N4 25.1(3) . . ?
O6 Sm1 N2 74.6(3) . . ?
O9 Sm1 O2 67.8(3) . . ?
O9 Sm1 O3 72.5(3) . . ?
O9 Sm1 N3 125.6(4) . . ?
O9 Sm1 N4 155.9(4) . . ?
O9 Sm1 N2 87.8(4) . . ?
O3 Sm1 N3 63.6(3) . . ?
O3 Sm1 N4 105.7(3) . . ?
O5 Sm1 O2 110.1(3) . . ?
O5 Sm1 O9 156.7(4) . . ?
O5 Sm1 O3 127.9(3) . . ?
O5 Sm1 N3 77.4(3) . . ?
O5 Sm1 O8 141.5(4) . . ?
O5 Sm1 N4 24.7(3) . . ?
O5 Sm1 N2 71.8(3) . . ?
N3 Sm1 N4 70.4(3) . . ?
O8 Sm1 O2 108.4(3) . . ?
O8 Sm1 O9 48.3(4) . . ?
O8 Sm1 O3 71.9(3) . . ?
O8 Sm1 N3 87.3(4) . . ?
O8 Sm1 N4 155.3(4) . . ?
O8 Sm1 N2 130.1(4) . . ?
N2 Sm1 O2 62.3(2) . . ?
N2 Sm1 O3 122.3(3) . . ?
N2 Sm1 N3 142.7(3) . . ?
N2 Sm1 N4 72.8(3) . . ?
C28 O4 Sm1 149.9(6) . . ?
C14 O1 Sm1 133.3(6) . . ?
C17 O2 Sm1 119.9(6) . . ?
C17 O2 C18 112.6(9) . . ?
C18 O2 Sm1 118.5(7) . . ?
N4 O6 Sm1 97.5(6) . . ?
N5 O9 Sm1 97.3(10) . . ?
C8 N1 H1 105.7 . . ?
C8 N1 C7 113.4(7) . . ?
C7 N1 H1 105.7 . . ?
C29 N1 H1 105.7 . . ?
C29 N1 C8 111.7(8) . . ?
C29 N1 C7 113.6(8) . . ?
C19 O3 Sm1 120.0(7) . . ?
C20 O3 Sm1 114.9(7) . . ?
C20 O3 C19 112.3(10) . . ?
C14 C13 C15 122.8(9) . . ?
C12 C13 C14 119.9(9) . . ?
C12 C13 C15 117.1(9) . . ?
N4 O5 Sm1 95.5(6) . . ?
O1 C14 C13 122.4(9) . . ?
O1 C14 C9 119.5(8) . . ?
C9 C14 C13 118.0(9) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.9(10) . . ?
C11 C12 H12 120.1 . . ?
C14 C9 C8 119.2(9) . . ?
C10 C9 C14 120.6(9) . . ?
C10 C9 C8 120.1(9) . . ?
C21 N3 Sm1 110.5(8) . . ?
C22 N3 Sm1 132.4(7) . . ?
C22 N3 C21 117.1(10) . . ?
N5 O8 Sm1 95.4(9) . . ?
O6 N4 Sm1 57.4(5) . . ?
O7 N4 Sm1 174.5(11) . . ?
O7 N4 O6 119.5(13) . . ?
O7 N4 O5 123.6(12) . . ?
O5 N4 Sm1 59.8(5) . . ?
O5 N4 O6 116.9(9) . . ?
C12 C11 Cl1 118.9(9) . . ?
C12 C11 C10 121.3(10) . . ?
C10 C11 Cl1 119.7(8) . . ?
C15 N2 Sm1 128.3(7) . . ?
C15 N2 C16 117.4(9) . . ?
C16 N2 Sm1 114.1(7) . . ?
C13 C15 H15 117.3 . . ?
N2 C15 C13 125.4(9) . . ?
N2 C15 H15 117.3 . . ?
C9 C10 C11 120.3(9) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
N3 C21 H21A 110.5 . . ?
N3 C21 H21B 110.5 . . ?
N3 C21 C20 106.2(10) . . ?
H21A C21 H21B 108.7 . . ?
C20 C21 H21A 110.5 . . ?
C20 C21 H21B 110.5 . . ?
O3 C19 H19A 109.8 . . ?
O3 C19 H19B 109.8 . . ?
O3 C19 C18 109.2(10) . . ?
H19A C19 H19B 108.3 . . ?
C18 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C5 C6 C7 120.3(11) . . ?
C5 C6 C1 118.1(11) . . ?
C1 C6 C7 121.6(10) . . ?
C28 C23 C22 121.4(11) . . ?
C24 C23 C28 119.0(10) . . ?
C24 C23 C22 119.5(10) . . ?
N1 C8 C9 112.9(7) . . ?
N1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C28 C27 C29 117.7(9) . . ?
C26 C27 C28 120.2(10) . . ?
C26 C27 C29 122.1(10) . . ?
O4 C28 C23 122.2(10) . . ?
O4 C28 C27 119.1(9) . . ?
C27 C28 C23 118.6(10) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 N1 114.3(8) . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O2 C17 H17A 110.8 . . ?
O2 C17 H17B 110.8 . . ?
O2 C17 C16 105.0(10) . . ?
H17A C17 H17B 108.8 . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
C6 C5 H5 119.2 . . ?
C6 C5 C4 121.7(13) . . ?
C4 C5 H5 119.2 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.3(10) . . ?
C25 C24 H24 119.4 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 C27 120.1(11) . . ?
C25 C26 H26 120.0 . . ?
C24 C25 Cl2 120.9(9) . . ?
C24 C25 C26 120.8(10) . . ?
C26 C25 Cl2 118.3(10) . . ?
O3 C20 C21 110.6(11) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
N1 C29 C27 110.7(8) . . ?
N1 C29 H29A 109.5 . . ?
N1 C29 H29B 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
O9 N5 O8 115.8(13) . . ?
O10 N5 O9 125(2) . . ?
O10 N5 O8 119.4(19) . . ?
N3 C22 C23 127.3(10) . . ?
N3 C22 H22 116.4 . . ?
C23 C22 H22 116.4 . . ?
O2 C18 C19 106.4(10) . . ?
O2 C18 H18A 110.4 . . ?
O2 C18 H18B 110.4 . . ?
C19 C18 H18A 110.4 . . ?
C19 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C6 C1 H1A 120.3 . . ?
C2 C1 C6 119.5(12) . . ?
C2 C1 H1A 120.3 . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(13) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 F1 120.6(15) . . ?
C2 C3 C4 122.4(13) . . ?
C4 C3 F1 116.9(13) . . ?
C5 C4 H4 121.6 . . ?
C3 C4 C5 116.8(12) . . ?
C3 C4 H4 121.6 . . ?
N2 C16 C17 109.2(9) . . ?
N2 C16 H16A 109.8 . . ?
N2 C16 H16B 109.8 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?

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
Sm1 O4 C28 C23 2(2) . . . . ?
Sm1 O4 C28 C27 -179.9(10) . . . . ?
Sm1 O1 C14 C13 -46.3(13) . . . . ?
Sm1 O1 C14 C9 134.5(7) . . . . ?
Sm1 O2 C17 C16 -40.9(11) . . . . ?
Sm1 O2 C18 C19 52.4(11) . . . . ?
Sm1 O6 N4 O7 -174.7(11) . . . . ?
Sm1 O6 N4 O5 5.6(11) . . . . ?
Sm1 O9 N5 O8 17.7(13) . . . . ?
Sm1 O9 N5 O10 -165.5(13) . . . . ?
Sm1 O3 C19 C18 35.2(12) . . . . ?
Sm1 O3 C20 C21 38.9(12) . . . . ?
Sm1 O5 N4 O6 -5.5(11) . . . . ?
Sm1 O5 N4 O7 174.9(12) . . . . ?
Sm1 N3 C21 C20 57.3(12) . . . . ?
Sm1 N3 C22 C23 -9.8(17) . . . . ?
Sm1 O8 N5 O9 -17.7(13) . . . . ?
Sm1 O8 N5 O10 165.3(12) . . . . ?
Sm1 N2 C15 C13 7.9(15) . . . . ?
Sm1 N2 C16 C17 -52.5(11) . . . . ?
Cl1 C11 C10 C9 -176.3(8) . . . . ?
O1 C14 C9 C10 179.1(9) . . . . ?
O1 C14 C9 C8 3.1(13) . . . . ?
F1 C3 C4 C5 178.7(10) . . . . ?
O2 C17 C16 N2 59.3(12) . . . . ?
O3 C19 C18 O2 -53.9(12) . . . . ?
C13 C14 C9 C10 -0.1(13) . . . . ?
C13 C14 C9 C8 -176.1(8) . . . . ?
C13 C12 C11 Cl1 177.9(8) . . . . ?
C13 C12 C11 C10 1.5(16) . . . . ?
C14 C13 C12 C11 -2.4(15) . . . . ?
C14 C13 C15 N2 17.8(16) . . . . ?
C14 C9 C10 C11 -0.8(14) . . . . ?
C14 C9 C8 N1 -55.3(12) . . . . ?
C12 C13 C14 O1 -177.5(9) . . . . ?
C12 C13 C14 C9 1.7(14) . . . . ?
C12 C13 C15 N2 -167.1(10) . . . . ?
C12 C11 C10 C9 0.1(16) . . . . ?
N3 C21 C20 O3 -64.6(14) . . . . ?
C15 C13 C14 O1 -2.5(14) . . . . ?
C15 C13 C14 C9 176.7(9) . . . . ?
C15 C13 C12 C11 -177.7(10) . . . . ?
C15 N2 C16 C17 131.5(11) . . . . ?
C10 C9 C8 N1 128.7(10) . . . . ?
C21 N3 C22 C23 169.2(10) . . . . ?
C19 O3 C20 C21 -103.0(11) . . . . ?
C6 C5 C4 C3 1.6(18) . . . . ?
C6 C1 C2 C3 1(2) . . . . ?
C23 C24 C25 Cl2 -178.7(8) . . . . ?
C23 C24 C25 C26 0.3(16) . . . . ?
C8 N1 C7 C6 64.9(11) . . . . ?
C8 N1 C29 C27 166.2(8) . . . . ?
C8 C9 C10 C11 175.2(9) . . . . ?
C27 C26 C25 Cl2 179.2(8) . . . . ?
C27 C26 C25 C24 0.2(16) . . . . ?
C28 C23 C24 C25 -0.3(15) . . . . ?
C28 C23 C22 N3 2.4(17) . . . . ?
C28 C27 C26 C25 -0.6(15) . . . . ?
C28 C27 C29 N1 -47.8(12) . . . . ?
C7 N1 C8 C9 160.0(8) . . . . ?
C7 N1 C29 C27 -63.9(10) . . . . ?
C7 C6 C5 C4 179.8(10) . . . . ?
C7 C6 C1 C2 178.7(12) . . . . ?
C17 O2 C18 C19 -160.6(9) . . . . ?
C5 C6 C7 N1 -91.4(12) . . . . ?
C5 C6 C1 C2 1.8(18) . . . . ?
C24 C23 C28 O4 177.8(10) . . . . ?
C24 C23 C28 C27 -0.1(14) . . . . ?
C24 C23 C22 N3 -173.1(11) . . . . ?
C26 C27 C28 O4 -177.4(10) . . . . ?
C26 C27 C28 C23 0.5(14) . . . . ?
C26 C27 C29 N1 134.6(10) . . . . ?
C20 O3 C19 C18 175.0(10) . . . . ?
C29 N1 C8 C9 -70.0(10) . . . . ?
C29 N1 C7 C6 -64.2(11) . . . . ?
C29 C27 C28 O4 4.9(14) . . . . ?
C29 C27 C28 C23 -177.1(9) . . . . ?
C29 C27 C26 C25 176.9(9) . . . . ?
C22 N3 C21 C20 -121.9(12) . . . . ?
C22 C23 C28 O4 2.4(16) . . . . ?
C22 C23 C28 C27 -175.5(9) . . . . ?
C22 C23 C24 C25 175.2(10) . . . . ?
C18 O2 C17 C16 172.6(9) . . . . ?
C1 C6 C7 N1 91.7(12) . . . . ?
C1 C6 C5 C4 -3.1(17) . . . . ?
C1 C2 C3 F1 180.0(13) . . . . ?
C1 C2 C3 C4 -3(2) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C16 N2 C15 C13 -176.9(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
