# 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 2023

####################################################################### 
# 
# 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_Sm2l
_database_code_depnum_ccdc_archive 'CCDC 2117308'
loop_
_audit_author_name
_audit_author_address
'Kun Zhang'
;Zhejiang Sci Tech University
China
;
_audit_update_record             
;
2021-12-06 deposited with the CCDC.	2023-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-05-22
_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         'C30 H31 Br Cl2 N5 O10 Sm'
_chemical_formula_sum            'C30 H31 Br Cl2 N5 O10 Sm'
_chemical_formula_weight         922.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   43.493(3)
_cell_length_b                   8.4563(6)
_cell_length_c                   18.8102(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.291(2)
_cell_angle_gamma                90
_cell_volume                     6906.8(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.730
_cell_measurement_theta_min      2.949
_shelx_estimated_absorpt_T_max   0.673
_shelx_estimated_absorpt_T_min   0.502
_exptl_absorpt_coefficient_mu    3.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0889 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.7698.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3656
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            52484
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.763
_diffrn_reflns_theta_min         3.022
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_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                5878
_reflns_number_total             8050
_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         1.053
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         8050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.002
_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)+(0.0373P)²+20.3563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0906
_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:
 C30(H30A,H30B), C22(H22A,H22B), C8(H8A,H8B), C21(H21A,H21B), C18(H18A,H18B),
 C17(H17A,H17B), C7(H7A,H7B), C20(H20A,H20B), C19(H19A,H19B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C23(H23), C5(H5), C25(H25), C11(H11), C16(H16), C2(H2), C13(H13),
 C3(H3), 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 0.33547(2) 0.51617(2) 0.48614(2) 0.02780(7) Uani 1 1 d . . . . .
Br1 Br 0.49699(2) 0.20289(8) 0.56783(4) 0.0788(2) Uani 1 1 d . . . . .
Cl2 Cl 0.30695(3) -0.16361(16) 0.21620(7) 0.0606(4) Uani 1 1 d . . . . .
Cl1 Cl 0.45496(4) 0.0120(2) 0.72499(8) 0.0841(5) Uani 1 1 d . . . . .
O6 O 0.39036(7) 0.5973(4) 0.46718(17) 0.0442(8) Uani 1 1 d . . . . .
O1 O 0.36604(6) 0.3021(3) 0.52105(15) 0.0376(7) Uani 1 1 d . . . . .
O4 O 0.35178(6) 0.3768(3) 0.38666(14) 0.0327(6) Uani 1 1 d . . . . .
O3 O 0.29680(7) 0.7555(3) 0.45497(17) 0.0428(8) Uani 1 1 d . . . . .
O9 O 0.28999(8) 0.5268(4) 0.5614(2) 0.0552(9) Uani 1 1 d . . . . .
O5 O 0.35711(7) 0.7076(4) 0.39454(17) 0.0465(8) Uani 1 1 d . . . . .
O2 O 0.34508(7) 0.8056(3) 0.54689(16) 0.0418(7) Uani 1 1 d . . . . .
O10 O 0.26257(9) 0.3312(6) 0.5944(3) 0.1075(19) Uani 1 1 d . . . . .
O7 O 0.40547(9) 0.7161(5) 0.3737(2) 0.0739(12) Uani 1 1 d . . . . .
O8 O 0.30123(8) 0.2917(4) 0.5302(2) 0.0589(10) Uani 1 1 d . . . . .
C28 C 0.36141(9) 0.1342(5) 0.3302(2) 0.0311(9) Uani 1 1 d . . . . .
N3 N 0.28981(7) 0.4643(4) 0.39291(19) 0.0339(8) Uani 1 1 d . . . . .
N5 N 0.28398(9) 0.3793(6) 0.5627(2) 0.0556(12) Uani 1 1 d . . . . .
N4 N 0.38466(9) 0.6745(4) 0.4107(2) 0.0433(9) Uani 1 1 d . . . . .
N1 N 0.40358(7) 0.1967(4) 0.42203(17) 0.0303(8) Uani 1 1 d . . . . .
H1 H 0.388336 0.275286 0.435105 0.036 Uiso 1 1 calc R . . . .
N2 N 0.35507(8) 0.5227(4) 0.62424(19) 0.0371(8) Uani 1 1 d . . . . .
C30 C 0.39539(9) 0.1546(6) 0.3455(2) 0.0381(10) Uani 1 1 d . . . . .
H30A H 0.402768 0.237338 0.315019 0.046 Uiso 1 1 calc R . . . .
H30B H 0.405784 0.057260 0.333937 0.046 Uiso 1 1 calc R . . . .
C24 C 0.30929(9) 0.2377(5) 0.3296(2) 0.0309(9) Uani 1 1 d . . . . .
C29 C 0.34097(9) 0.2543(5) 0.3510(2) 0.0284(9) Uani 1 1 d . . . . .
C27 C 0.35060(10) 0.0064(5) 0.2909(2) 0.0359(10) Uani 1 1 d . . . . .
H27 H 0.364160 -0.072976 0.278917 0.043 Uiso 1 1 calc R . . . .
C14 C 0.38798(10) 0.2907(5) 0.6398(2) 0.0347(10) Uani 1 1 d . . . . .
C22 C 0.26335(9) 0.5710(5) 0.3988(3) 0.0434(11) Uani 1 1 d . . . . .
H22A H 0.253492 0.550130 0.442848 0.052 Uiso 1 1 calc R . . . .
H22B H 0.248377 0.552911 0.359447 0.052 Uiso 1 1 calc R . . . .
C15 C 0.38475(9) 0.2378(5) 0.5684(2) 0.0322(9) Uani 1 1 d . . . . .
C12 C 0.42714(10) 0.0956(6) 0.6656(2) 0.0469(12) Uani 1 1 d . . . . .
C26 C 0.31968(10) -0.0051(5) 0.2692(2) 0.0370(10) Uani 1 1 d . . . . .
C23 C 0.28673(9) 0.3563(5) 0.3466(2) 0.0331(9) Uani 1 1 d . . . . .
H23 H 0.267909 0.352247 0.320623 0.040 Uiso 1 1 calc R . . . .
C8 C 0.43434(9) 0.2770(5) 0.4316(2) 0.0342(10) Uani 1 1 d . . . . .
H8A H 0.437246 0.313877 0.480332 0.041 Uiso 1 1 calc R . . . .
H8B H 0.434440 0.368824 0.400654 0.041 Uiso 1 1 calc R . . . .
C21 C 0.27419(11) 0.7385(5) 0.3978(3) 0.0483(12) Uani 1 1 d . . . . .
H21A H 0.283022 0.762165 0.352853 0.058 Uiso 1 1 calc R . . . .
H21B H 0.257142 0.810268 0.403968 0.058 Uiso 1 1 calc R . . . .
C5 C 0.50184(14) 0.3219(9) 0.3564(4) 0.086(2) Uani 1 1 d . . . . .
H5 H 0.489863 0.313376 0.313999 0.103 Uiso 1 1 calc R . . . .
C25 C 0.29941(10) 0.1092(5) 0.2884(2) 0.0363(10) Uani 1 1 d . . . . .
H25 H 0.278709 0.100551 0.273556 0.044 Uiso 1 1 calc R . . . .
C18 C 0.35854(12) 0.8033(5) 0.6179(3) 0.0529(13) Uani 1 1 d . . . . .
H18A H 0.354314 0.902443 0.641402 0.063 Uiso 1 1 calc R . . . .
H18B H 0.380700 0.791757 0.616824 0.063 Uiso 1 1 calc R . . . .
C17 C 0.34568(12) 0.6691(5) 0.6587(3) 0.0521(13) Uani 1 1 d . . . . .
H17A H 0.353693 0.671737 0.707914 0.062 Uiso 1 1 calc R . . . .
H17B H 0.323403 0.676141 0.657859 0.062 Uiso 1 1 calc R . . . .
C7 C 0.46103(10) 0.1699(6) 0.4151(3) 0.0552(14) Uani 1 1 d . . . . .
H7A H 0.457228 0.124469 0.368058 0.066 Uiso 1 1 calc R . . . .
H7B H 0.462407 0.083987 0.449268 0.066 Uiso 1 1 calc R . . . .
C20 C 0.30763(11) 0.9146(5) 0.4654(3) 0.0471(12) Uani 1 1 d . . . . .
H20A H 0.290661 0.988666 0.459056 0.057 Uiso 1 1 calc R . . . .
H20B H 0.322805 0.939909 0.431305 0.057 Uiso 1 1 calc R . . . .
C11 C 0.42465(10) 0.0420(5) 0.5960(3) 0.0427(11) Uani 1 1 d . . . . .
H11 H 0.437147 -0.040099 0.581800 0.051 Uiso 1 1 calc R . . . .
C16 C 0.37205(10) 0.4291(5) 0.6634(2) 0.0394(10) Uani 1 1 d . . . . .
H16 H 0.374300 0.453010 0.711679 0.047 Uiso 1 1 calc R . . . .
C2 C 0.53804(12) 0.3506(6) 0.4805(4) 0.0640(16) Uani 1 1 d . . . . .
H2 H 0.550109 0.360057 0.522677 0.077 Uiso 1 1 calc R . . . .
C19 C 0.32149(11) 0.9242(5) 0.5384(3) 0.0495(13) Uani 1 1 d . . . . .
H19A H 0.330310 1.028296 0.546982 0.059 Uiso 1 1 calc R . . . .
H19B H 0.305884 0.906582 0.572392 0.059 Uiso 1 1 calc R . . . .
C13 C 0.40917(11) 0.2176(6) 0.6875(2) 0.0450(11) Uani 1 1 d . . . . .
H13 H 0.411156 0.251721 0.734528 0.054 Uiso 1 1 calc R . . . .
C1 C 0.50999(11) 0.2772(6) 0.4802(3) 0.0549(14) Uani 1 1 d . . . . .
C6 C 0.49139(11) 0.2596(6) 0.4178(3) 0.0544(14) Uani 1 1 d . . . . .
C10 C 0.40363(9) 0.1102(5) 0.5476(2) 0.0322(9) Uani 1 1 d . . . . .
C9 C 0.40001(10) 0.0584(5) 0.4719(2) 0.0369(10) Uani 1 1 d . . . . .
H9A H 0.379829 0.011277 0.462890 0.044 Uiso 1 1 calc R . . . .
H9B H 0.415372 -0.021209 0.463000 0.044 Uiso 1 1 calc R . . . .
C3 C 0.54809(14) 0.4090(8) 0.4194(4) 0.080(2) Uani 1 1 d . . . . .
H3 H 0.567309 0.457224 0.419708 0.095 Uiso 1 1 calc R . . . .
C4 C 0.53044(16) 0.3985(10) 0.3570(4) 0.097(2) Uani 1 1 d . . . . .
H4 H 0.537362 0.441777 0.315372 0.116 Uiso 1 1 calc R . . . .


_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 O6 2.529(3) . ?
Sm1 O1 2.319(3) . ?
Sm1 O4 2.355(3) . ?
Sm1 O3 2.675(3) . ?
Sm1 O9 2.500(3) . ?
Sm1 O5 2.581(3) . ?
Sm1 O2 2.723(3) . ?
Sm1 O8 2.579(3) . ?
Sm1 N3 2.610(3) . ?
Sm1 N5 2.967(4) . ?
Sm1 N4 2.955(4) . ?
Sm1 N2 2.688(4) . ?
Br1 C1 1.882(6) . ?
Cl2 C26 1.741(4) . ?
Cl1 C12 1.749(4) . ?
O6 N4 1.259(5) . ?
O1 C15 1.292(5) . ?
O4 C29 1.306(5) . ?
O3 C21 1.422(5) . ?
O3 C20 1.436(5) . ?
O9 N5 1.275(5) . ?
O5 N4 1.251(5) . ?
O2 C18 1.428(6) . ?
O2 C19 1.437(5) . ?
O10 N5 1.204(5) . ?
O7 N4 1.225(5) . ?
O8 N5 1.241(5) . ?
C28 C30 1.499(5) . ?
C28 C29 1.420(5) . ?
C28 C27 1.376(5) . ?
N3 C22 1.472(5) . ?
N3 C23 1.263(5) . ?
N1 H1 0.9800 . ?
N1 C30 1.506(5) . ?
N1 C8 1.502(5) . ?
N1 C9 1.513(5) . ?
N2 C17 1.466(5) . ?
N2 C16 1.285(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C24 C29 1.420(5) . ?
C24 C23 1.451(6) . ?
C24 C25 1.389(6) . ?
C27 H27 0.9300 . ?
C27 C26 1.387(6) . ?
C14 C15 1.415(6) . ?
C14 C16 1.443(6) . ?
C14 C13 1.393(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.494(6) . ?
C15 C10 1.424(5) . ?
C12 C11 1.384(7) . ?
C12 C13 1.372(7) . ?
C26 C25 1.370(6) . ?
C23 H23 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.518(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.371(8) . ?
C5 C4 1.402(9) . ?
C25 H25 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.496(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.521(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.471(7) . ?
C11 H11 0.9300 . ?
C11 C10 1.378(6) . ?
C16 H16 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.369(7) . ?
C2 C3 1.345(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C13 H13 0.9300 . ?
C1 C6 1.394(7) . ?
C10 C9 1.490(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.368(9) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Sm1 O3 110.53(10) . . ?
O6 Sm1 O5 49.63(10) . . ?
O6 Sm1 O2 72.06(9) . . ?
O6 Sm1 O8 144.33(11) . . ?
O6 Sm1 N3 129.71(10) . . ?
O6 Sm1 N5 156.84(11) . . ?
O6 Sm1 N4 25.03(10) . . ?
O6 Sm1 N2 83.18(11) . . ?
O1 Sm1 O6 73.82(11) . . ?
O1 Sm1 O4 68.91(9) . . ?
O1 Sm1 O3 174.81(10) . . ?
O1 Sm1 O9 109.10(11) . . ?
O1 Sm1 O5 116.98(10) . . ?
O1 Sm1 O2 120.75(9) . . ?
O1 Sm1 O8 70.52(11) . . ?
O1 Sm1 N3 117.43(10) . . ?
O1 Sm1 N5 89.68(11) . . ?
O1 Sm1 N4 94.05(11) . . ?
O1 Sm1 N2 66.27(10) . . ?
O4 Sm1 O6 72.18(9) . . ?
O4 Sm1 O3 114.77(10) . . ?
O4 Sm1 O9 138.80(11) . . ?
O4 Sm1 O5 69.24(10) . . ?
O4 Sm1 O2 137.50(9) . . ?
O4 Sm1 O8 95.32(11) . . ?
O4 Sm1 N3 68.55(10) . . ?
O4 Sm1 N5 117.45(12) . . ?
O4 Sm1 N4 65.54(10) . . ?
O4 Sm1 N2 133.23(10) . . ?
O3 Sm1 O2 59.43(9) . . ?
O3 Sm1 N5 85.34(10) . . ?
O3 Sm1 N4 90.89(10) . . ?
O3 Sm1 N2 110.90(10) . . ?
O9 Sm1 O6 148.68(11) . . ?
O9 Sm1 O3 65.71(10) . . ?
O9 Sm1 O5 133.34(10) . . ?
O9 Sm1 O2 80.63(10) . . ?
O9 Sm1 O8 49.77(11) . . ?
O9 Sm1 N3 77.90(12) . . ?
O9 Sm1 N5 25.16(11) . . ?
O9 Sm1 N4 150.92(10) . . ?
O9 Sm1 N2 70.67(12) . . ?
O5 Sm1 O3 68.16(9) . . ?
O5 Sm1 O2 70.33(10) . . ?
O5 Sm1 N3 87.10(10) . . ?
O5 Sm1 N5 152.04(10) . . ?
O5 Sm1 N4 24.96(10) . . ?
O5 Sm1 N2 121.65(10) . . ?
O2 Sm1 N5 104.40(12) . . ?
O2 Sm1 N4 72.32(10) . . ?
O8 Sm1 O3 105.06(10) . . ?
O8 Sm1 O5 156.31(11) . . ?
O8 Sm1 O2 127.18(11) . . ?
O8 Sm1 N3 70.18(11) . . ?
O8 Sm1 N5 24.61(11) . . ?
O8 Sm1 N4 159.28(11) . . ?
O8 Sm1 N2 82.04(11) . . ?
N3 Sm1 O3 62.31(10) . . ?
N3 Sm1 O2 121.71(10) . . ?
N3 Sm1 N5 72.20(11) . . ?
N3 Sm1 N4 107.31(11) . . ?
N3 Sm1 N2 147.11(11) . . ?
N4 Sm1 N5 175.95(12) . . ?
N2 Sm1 O2 62.83(10) . . ?
N2 Sm1 N5 75.22(12) . . ?
N2 Sm1 N4 104.86(11) . . ?
N4 O6 Sm1 96.8(2) . . ?
C15 O1 Sm1 148.4(3) . . ?
C29 O4 Sm1 133.5(2) . . ?
C21 O3 Sm1 119.2(2) . . ?
C21 O3 C20 113.9(3) . . ?
C20 O3 Sm1 118.8(2) . . ?
N5 O9 Sm1 98.4(3) . . ?
N4 O5 Sm1 94.5(2) . . ?
C18 O2 Sm1 115.2(2) . . ?
C18 O2 C19 111.4(3) . . ?
C19 O2 Sm1 119.3(3) . . ?
N5 O8 Sm1 95.5(3) . . ?
C29 C28 C30 119.4(4) . . ?
C27 C28 C30 119.7(4) . . ?
C27 C28 C29 120.6(4) . . ?
C22 N3 Sm1 114.5(3) . . ?
C23 N3 Sm1 129.1(3) . . ?
C23 N3 C22 116.3(4) . . ?
O9 N5 Sm1 56.5(2) . . ?
O10 N5 Sm1 176.8(4) . . ?
O10 N5 O9 120.4(5) . . ?
O10 N5 O8 123.2(5) . . ?
O8 N5 Sm1 59.9(2) . . ?
O8 N5 O9 116.4(4) . . ?
O6 N4 Sm1 58.19(19) . . ?
O5 N4 Sm1 60.6(2) . . ?
O5 N4 O6 117.4(4) . . ?
O7 N4 Sm1 169.1(3) . . ?
O7 N4 O6 120.8(4) . . ?
O7 N4 O5 121.7(4) . . ?
C30 N1 H1 105.9 . . ?
C30 N1 C9 112.6(3) . . ?
C8 N1 H1 105.9 . . ?
C8 N1 C30 112.4(3) . . ?
C8 N1 C9 113.5(3) . . ?
C9 N1 H1 105.9 . . ?
C17 N2 Sm1 111.3(3) . . ?
C16 N2 Sm1 132.9(3) . . ?
C16 N2 C17 115.6(4) . . ?
C28 C30 N1 112.7(3) . . ?
C28 C30 H30A 109.0 . . ?
C28 C30 H30B 109.0 . . ?
N1 C30 H30A 109.0 . . ?
N1 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
C29 C24 C23 121.8(4) . . ?
C25 C24 C29 120.0(4) . . ?
C25 C24 C23 118.2(4) . . ?
O4 C29 C28 119.7(3) . . ?
O4 C29 C24 122.6(4) . . ?
C28 C29 C24 117.6(4) . . ?
C28 C27 H27 119.7 . . ?
C28 C27 C26 120.6(4) . . ?
C26 C27 H27 119.7 . . ?
C15 C14 C16 121.7(4) . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 C16 118.3(4) . . ?
N3 C22 H22A 109.8 . . ?
N3 C22 H22B 109.8 . . ?
N3 C22 C21 109.4(4) . . ?
H22A C22 H22B 108.2 . . ?
C21 C22 H22A 109.8 . . ?
C21 C22 H22B 109.8 . . ?
O1 C15 C14 123.1(4) . . ?
O1 C15 C10 118.7(4) . . ?
C14 C15 C10 118.2(4) . . ?
C11 C12 Cl1 119.1(4) . . ?
C13 C12 Cl1 119.8(4) . . ?
C13 C12 C11 121.0(4) . . ?
C27 C26 Cl2 119.6(3) . . ?
C25 C26 Cl2 120.4(3) . . ?
C25 C26 C27 120.0(4) . . ?
N3 C23 C24 127.2(4) . . ?
N3 C23 H23 116.4 . . ?
C24 C23 H23 116.4 . . ?
N1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
N1 C8 C7 113.1(3) . . ?
H8A C8 H8B 107.8 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
O3 C21 C22 106.9(4) . . ?
O3 C21 H21A 110.3 . . ?
O3 C21 H21B 110.3 . . ?
C22 C21 H21A 110.3 . . ?
C22 C21 H21B 110.3 . . ?
H21A C21 H21B 108.6 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.5(6) . . ?
C4 C5 H5 119.7 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.1(4) . . ?
C26 C25 H25 119.5 . . ?
O2 C18 H18A 109.6 . . ?
O2 C18 H18B 109.6 . . ?
O2 C18 C17 110.2(4) . . ?
H18A C18 H18B 108.1 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
N2 C17 C18 107.0(4) . . ?
N2 C17 H17A 110.3 . . ?
N2 C17 H17B 110.3 . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.6 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C8 C7 C6 111.6(4) . . ?
H7A C7 H7B 108.0 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
O3 C20 H20A 110.3 . . ?
O3 C20 H20B 110.3 . . ?
O3 C20 C19 107.0(4) . . ?
H20A C20 H20B 108.6 . . ?
C19 C20 H20A 110.3 . . ?
C19 C20 H20B 110.3 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.0(4) . . ?
C10 C11 H11 120.0 . . ?
N2 C16 C14 126.4(4) . . ?
N2 C16 H16 116.8 . . ?
C14 C16 H16 116.8 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.7(6) . . ?
O2 C19 C20 108.5(4) . . ?
O2 C19 H19A 110.0 . . ?
O2 C19 H19B 110.0 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
C14 C13 H13 119.7 . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.7 . . ?
C2 C1 Br1 117.4(5) . . ?
C2 C1 C6 121.7(6) . . ?
C6 C1 Br1 120.8(4) . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 C1 117.6(5) . . ?
C1 C6 C7 122.8(5) . . ?
C15 C10 C9 117.0(4) . . ?
C11 C10 C15 120.5(4) . . ?
C11 C10 C9 122.5(4) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C10 C9 N1 110.9(3) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(6) . . ?
C4 C3 H3 119.5 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.4(7) . . ?
C3 C4 H4 120.3 . . ?

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 O6 N4 O5 13.2(4) . . . . ?
Sm1 O6 N4 O7 -167.3(4) . . . . ?
Sm1 O1 C15 C14 17.0(8) . . . . ?
Sm1 O1 C15 C10 -161.4(4) . . . . ?
Sm1 O4 C29 C28 -136.6(3) . . . . ?
Sm1 O4 C29 C24 45.6(5) . . . . ?
Sm1 O3 C21 C22 36.9(5) . . . . ?
Sm1 O3 C20 C19 -51.4(4) . . . . ?
Sm1 O9 N5 O10 -179.4(4) . . . . ?
Sm1 O9 N5 O8 0.6(4) . . . . ?
Sm1 O5 N4 O6 -12.9(4) . . . . ?
Sm1 O5 N4 O7 167.6(4) . . . . ?
Sm1 O2 C18 C17 -38.4(5) . . . . ?
Sm1 O2 C19 C20 -39.1(5) . . . . ?
Sm1 O8 N5 O9 -0.6(4) . . . . ?
Sm1 O8 N5 O10 179.4(5) . . . . ?
Sm1 N3 C22 C21 53.0(4) . . . . ?
Sm1 N3 C23 C24 -5.1(6) . . . . ?
Sm1 N2 C17 C18 -57.5(4) . . . . ?
Sm1 N2 C16 C14 5.0(7) . . . . ?
Br1 C1 C6 C5 177.5(4) . . . . ?
Br1 C1 C6 C7 -4.8(7) . . . . ?
Cl2 C26 C25 C24 -178.9(3) . . . . ?
Cl1 C12 C11 C10 -177.6(3) . . . . ?
Cl1 C12 C13 C14 176.8(3) . . . . ?
O1 C15 C10 C11 177.8(4) . . . . ?
O1 C15 C10 C9 -0.8(5) . . . . ?
O3 C20 C19 O2 56.1(5) . . . . ?
O2 C18 C17 N2 64.0(5) . . . . ?
C28 C27 C26 Cl2 177.2(3) . . . . ?
C28 C27 C26 C25 -1.8(6) . . . . ?
N3 C22 C21 O3 -57.3(5) . . . . ?
N1 C8 C7 C6 174.1(4) . . . . ?
C30 C28 C29 O4 -3.8(6) . . . . ?
C30 C28 C29 C24 174.0(4) . . . . ?
C30 C28 C27 C26 -172.4(4) . . . . ?
C30 N1 C8 C7 -66.2(5) . . . . ?
C30 N1 C9 C10 -171.4(3) . . . . ?
C29 C28 C30 N1 51.1(5) . . . . ?
C29 C28 C27 C26 1.9(6) . . . . ?
C29 C24 C23 N3 -16.7(7) . . . . ?
C29 C24 C25 C26 1.6(6) . . . . ?
C27 C28 C30 N1 -134.5(4) . . . . ?
C27 C28 C29 O4 -178.2(4) . . . . ?
C27 C28 C29 C24 -0.3(6) . . . . ?
C27 C26 C25 C24 0.1(6) . . . . ?
C14 C15 C10 C11 -0.7(6) . . . . ?
C14 C15 C10 C9 -179.3(4) . . . . ?
C22 N3 C23 C24 179.2(4) . . . . ?
C15 C14 C16 N2 -3.8(7) . . . . ?
C15 C14 C13 C12 0.6(6) . . . . ?
C15 C10 C9 N1 53.4(5) . . . . ?
C12 C11 C10 C15 1.1(6) . . . . ?
C12 C11 C10 C9 179.6(4) . . . . ?
C23 N3 C22 C21 -130.7(4) . . . . ?
C23 C24 C29 O4 -0.5(6) . . . . ?
C23 C24 C29 C28 -178.4(4) . . . . ?
C23 C24 C25 C26 178.6(4) . . . . ?
C8 N1 C30 C28 -157.8(3) . . . . ?
C8 N1 C9 C10 59.6(4) . . . . ?
C8 C7 C6 C5 -93.9(6) . . . . ?
C8 C7 C6 C1 88.4(6) . . . . ?
C21 O3 C20 C19 160.1(4) . . . . ?
C25 C24 C29 O4 176.4(4) . . . . ?
C25 C24 C29 C28 -1.4(6) . . . . ?
C25 C24 C23 N3 166.3(4) . . . . ?
C18 O2 C19 C20 -177.2(4) . . . . ?
C17 N2 C16 C14 -170.2(4) . . . . ?
C20 O3 C21 C22 -174.7(4) . . . . ?
C11 C12 C13 C14 -0.2(7) . . . . ?
C11 C10 C9 N1 -125.1(4) . . . . ?
C16 N2 C17 C18 118.8(4) . . . . ?
C16 C14 C15 O1 -4.8(6) . . . . ?
C16 C14 C15 C10 173.6(4) . . . . ?
C16 C14 C13 C12 -173.4(4) . . . . ?
C2 C1 C6 C5 -1.5(8) . . . . ?
C2 C1 C6 C7 176.2(5) . . . . ?
C2 C3 C4 C5 -1.7(11) . . . . ?
C19 O2 C18 C17 101.5(4) . . . . ?
C13 C14 C15 O1 -178.6(4) . . . . ?
C13 C14 C15 C10 -0.2(6) . . . . ?
C13 C14 C16 N2 170.1(4) . . . . ?
C13 C12 C11 C10 -0.7(7) . . . . ?
C1 C2 C3 C4 1.1(10) . . . . ?
C6 C5 C4 C3 0.8(11) . . . . ?
C9 N1 C30 C28 72.6(4) . . . . ?
C9 N1 C8 C7 63.0(5) . . . . ?
C3 C2 C1 Br1 -178.5(4) . . . . ?
C3 C2 C1 C6 0.6(8) . . . . ?
C4 C5 C6 C7 -177.0(6) . . . . ?
C4 C5 C6 C1 0.8(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
