#------------------------------------------------------------------------------
#$Date: 2024-12-06 19:44:57 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296483 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/95/7249529.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249529
loop_
_publ_author_name
'Zhang, Jinliang'
'Zhang, Zhiqiang'
'Gao, Congli'
'Li, Xi-Li'
_publ_section_title
;
 Two chiral EuIII and SmIII enantiomeric pairs with enantiopure N-donor
 ligands: showing strong third-harmonic generation and photoluminescence
 properties
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              6757
_journal_page_last               6764
_journal_paper_doi               10.1039/D4CE01052C
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C61 H50 N3 O6 Sm'
_chemical_formula_sum            'C61 H50 N3 O6 Sm'
_chemical_formula_weight         1071.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-09-06 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.576(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5481(2)
_cell_length_b                   20.9561(4)
_cell_length_c                   12.6388(4)
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.201
_cell_measurement_theta_min      1.269
_cell_volume                     2523.99(11)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9671
_diffrn_reflns_point_group_measured_fraction_full 0.699
_diffrn_reflns_point_group_measured_fraction_max 0.670
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.937
_diffrn_reflns_theta_min         3.504
_exptl_absorpt_coefficient_mu    9.181
_exptl_absorpt_correction_T_max  0.230
_exptl_absorpt_correction_T_min  0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2012'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1094
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.321
_refine_diff_density_min         -1.436
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.014(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     642
_refine_ls_number_reflns         6743
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0491
_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)+(0.0735P)²+0.3769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.341
_reflns_Friedel_fraction_full    0.383
_reflns_Friedel_fraction_max     0.351
_reflns_number_gt                5989
_reflns_number_total             6743
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01052c2.cif
_cod_data_source_block           L-2-Sm
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'RMAD' was changed
to 'rmad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7249528--7249531.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7249529
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C25 C 0.1849(12) 1.0780(6) 0.1320(9) 0.052(3) Uani 1 1 d . . . . .
C56 C 0.1949(11) 0.8176(7) 0.0220(10) 0.053(3) Uani 1 1 d . . . . .
C55 C 0.1983(11) 0.8326(6) 0.1359(10) 0.050(3) Uani 1 1 d . . . . .
C26 C 0.1765(14) 1.0933(7) 0.0143(11) 0.060(3) Uani 1 1 d . . . . .
C59 C 0.1955(18) 0.7936(14) -0.1949(12) 0.098(7) Uani 1 1 d . . . . .
H59 H 0.1951 0.7859 -0.2674 0.117 Uiso 1 1 calc R U . . .
C5 C 0.5400(10) 0.9106(5) 0.3463(8) 0.054(2) Uani 1 1 d . . . . .
C23 C 0.1617(9) 1.1179(4) 0.3143(7) 0.0472(19) Uani 1 1 d . . . . .
C4 C 0.5023(11) 0.9238(6) 0.4552(9) 0.062(2) Uani 1 1 d . . . . .
C22 C 0.1274(10) 1.1744(5) 0.3823(8) 0.052(2) Uani 1 1 d . . . . .
C17 C 0.0777(13) 1.1637(5) 0.4805(9) 0.066(3) Uani 1 1 d . . . . .
H17 H 0.0688 1.1221 0.5049 0.080 Uiso 1 1 calc R U . . .
C31 C 0.2569(18) 1.0582(8) -0.0521(11) 0.084(4) Uani 1 1 d . . . . .
H31 H 0.3151 1.0258 -0.0249 0.101 Uiso 1 1 calc R U . . .
C57 C 0.1942(12) 0.7558(6) -0.0173(10) 0.064(3) Uani 1 1 d . . . . .
H57 H 0.1940 0.7217 0.0298 0.077 Uiso 1 1 calc R U . . .
C53 C 0.2683(10) 0.8017(5) 0.3208(8) 0.054(2) Uani 1 1 d . . . . .
C60 C 0.198(2) 0.8549(10) -0.1567(14) 0.100(6) Uani 1 1 d . . . . .
H60 H 0.1994 0.8889 -0.2039 0.120 Uiso 1 1 calc R U . . .
C24 C 0.1469(10) 1.1241(5) 0.2049(8) 0.053(2) Uani 1 1 d . . . . .
H24 H 0.1085 1.1620 0.1778 0.063 Uiso 1 1 calc R U . . .
C61 C 0.1970(15) 0.8669(7) -0.0502(11) 0.074(3) Uani 1 1 d . . . . .
H61 H 0.1980 0.9089 -0.0263 0.088 Uiso 1 1 calc R U . . .
C58 C 0.1938(15) 0.7438(8) -0.1244(11) 0.082(4) Uani 1 1 d . . . . .
H58 H 0.1925 0.7019 -0.1490 0.099 Uiso 1 1 calc R U . . .
C2 C 0.4353(14) 0.9505(14) 0.6528(9) 0.100(5) Uani 1 1 d . . . . .
H2 H 0.4109 0.9627 0.7200 0.120 Uiso 1 1 calc R U . . .
C52 C 0.3472(10) 0.7541(5) 0.3939(9) 0.058(2) Uani 1 1 d . . . . .
C9 C 0.4838(11) 0.9254(5) 0.1680(8) 0.058(2) Uani 1 1 d . . . . .
H9 H 0.4241 0.9420 0.1139 0.069 Uiso 1 1 calc R U . . .
C1 C 0.3518(14) 0.9691(7) 0.5650(10) 0.081(4) Uani 1 1 d . . . . .
H1 H 0.2708 0.9923 0.5754 0.097 Uiso 1 1 calc R U . . .
C20 C 0.1034(15) 1.2866(6) 0.4120(12) 0.081(3) Uani 1 1 d . . . . .
H20 H 0.1148 1.3283 0.3886 0.097 Uiso 1 1 calc R U . . .
C54 C 0.2523(11) 0.7891(4) 0.2137(8) 0.052(2) Uani 1 1 d . . . . .
H54 H 0.2790 0.7489 0.1909 0.063 Uiso 1 1 calc R U . . .
C27 C 0.0884(13) 1.1406(6) -0.0300(9) 0.066(3) Uani 1 1 d . . . . .
H27 H 0.0340 1.1648 0.0134 0.079 Uiso 1 1 calc R U . . .
C47 C 0.3393(17) 0.7596(8) 0.4995(11) 0.088(4) Uani 1 1 d . . . . .
H47 H 0.2830 0.7912 0.5264 0.105 Uiso 1 1 calc R U . . .
C21 C 0.1395(14) 1.2362(5) 0.3481(10) 0.068(3) Uani 1 1 d . . . . .
H21 H 0.1720 1.2443 0.2815 0.082 Uiso 1 1 calc R U . . .
C28 C 0.0814(16) 1.1517(7) -0.1367(10) 0.081(3) Uani 1 1 d . . . . .
H28 H 0.0197 1.1823 -0.1655 0.097 Uiso 1 1 calc R U . . .
C51 C 0.4330(15) 0.7078(6) 0.3548(12) 0.082(4) Uani 1 1 d . . . . .
H51 H 0.4412 0.7036 0.2822 0.098 Uiso 1 1 calc R U . . .
C8 C 0.6054(11) 0.8922(5) 0.1408(9) 0.060(3) Uani 1 1 d . . . . .
C3 C 0.5843(16) 0.9031(9) 0.5453(11) 0.096(5) Uani 1 1 d . . . . .
H3 H 0.6654 0.8798 0.5353 0.115 Uiso 1 1 calc R U . . .
C50 C 0.5073(17) 0.6673(9) 0.4259(16) 0.101(5) Uani 1 1 d . . . . .
H50 H 0.5645 0.6359 0.3994 0.121 Uiso 1 1 calc R U . . .
C13 C 0.6419(15) 0.8798(7) 0.0303(11) 0.076(3) Uani 1 1 d . . . . .
H13 H 0.5821 0.8997 -0.0264 0.092 Uiso 1 1 calc R U . . .
N3 N 0.5518(16) 0.9150(9) 0.6429(10) 0.116(5) Uani 1 1 d . . . . .
C12 C 0.8063(15) 0.8921(7) 0.0288(13) 0.090(4) Uani 1 1 d . . . . .
H12A H 0.8402 0.8976 -0.0414 0.108 Uiso 1 1 calc R U . . .
H12B H 0.8419 0.9250 0.0773 0.108 Uiso 1 1 calc R U . . .
C32 C -0.0373(11) 0.9596(9) 0.6569(7) 0.068(3) Uani 1 1 d . . . . .
H32 H 0.0263 0.9290 0.6367 0.082 Uiso 1 1 calc R U . . .
C14 C 0.6765(15) 0.8073(8) 0.0173(13) 0.079(4) Uani 1 1 d . . . . .
C7 C 0.6919(11) 0.8665(5) 0.2207(10) 0.060(3) Uani 1 1 d . . . . .
C39 C -0.1459(10) 1.0252(5) 0.3907(8) 0.057(2) Uani 1 1 d . . . . .
H39 H -0.2168 1.0513 0.4135 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6614(11) 0.8767(6) 0.3245(10) 0.065(3) Uani 1 1 d . . . . .
H6 H 0.7210 0.8613 0.3796 0.078 Uiso 1 1 calc R U . . .
C11 C 0.8200(12) 0.8235(6) 0.0729(12) 0.075(3) Uani 1 1 d . . . . .
H11 H 0.8989 0.7991 0.0476 0.089 Uiso 1 1 calc R U . . .
C38 C -0.0600(10) 0.9948(5) 0.4691(8) 0.053(2) Uani 1 1 d . . . . .
C37 C -0.0956(11) 1.0024(5) 0.5814(8) 0.060(2) Uani 1 1 d . . . . .
C19 C 0.0515(14) 1.2762(6) 0.5086(11) 0.077(3) Uani 1 1 d . . . . .
H19 H 0.0242 1.3103 0.5498 0.093 Uiso 1 1 calc R U . . .
C36 C -0.1825(17) 1.0494(7) 0.6173(10) 0.086(4) Uani 1 1 d . . . . .
H36 H -0.2195 1.0799 0.5700 0.103 Uiso 1 1 calc R U . . .
C15 C 0.5822(13) 0.7589(7) 0.0675(13) 0.085(4) Uani 1 1 d . . . . .
H15A H 0.6237 0.7173 0.0645 0.128 Uiso 1 1 calc R U . . .
H15B H 0.4919 0.7586 0.0297 0.128 Uiso 1 1 calc R U . . .
H15C H 0.5716 0.7703 0.1402 0.128 Uiso 1 1 calc R U . . .
C40 C -0.1348(9) 1.0199(5) 0.2827(8) 0.050(2) Uani 1 1 d . . . . .
C33 C -0.0724(16) 0.9622(11) 0.7598(9) 0.096(5) Uani 1 1 d . . . . .
H33 H -0.0343 0.9328 0.8085 0.116 Uiso 1 1 calc R U . . .
C10 C 0.8168(10) 0.8273(7) 0.1891(11) 0.073(3) Uani 1 1 d . . . . .
H10A H 0.9030 0.8467 0.2184 0.088 Uiso 1 1 calc R U . . .
H10B H 0.8109 0.7846 0.2182 0.088 Uiso 1 1 calc R U . . .
C41 C -0.2373(11) 1.0518(5) 0.2072(9) 0.052(2) Uani 1 1 d . . . . .
C42 C -0.3651(11) 1.0762(6) 0.2371(10) 0.067(3) Uani 1 1 d . . . . .
H42 H -0.3888 1.0725 0.3070 0.081 Uiso 1 1 calc R U . . .
C49 C 0.4988(15) 0.6724(8) 0.5319(13) 0.091(4) Uani 1 1 d . . . . .
H49 H 0.5490 0.6450 0.5781 0.109 Uiso 1 1 calc R U . . .
C16 C 0.679(2) 0.7892(9) -0.1009(15) 0.114(6) Uani 1 1 d . . . . .
H16A H 0.6978 0.7443 -0.1070 0.172 Uiso 1 1 calc R U . . .
H16B H 0.7517 0.8129 -0.1327 0.172 Uiso 1 1 calc R U . . .
H16C H 0.5901 0.7990 -0.1365 0.172 Uiso 1 1 calc R U . . .
C34 C -0.162(2) 1.0071(10) 0.7918(12) 0.126(7) Uani 1 1 d . . . . .
H34 H -0.1870 1.0075 0.8617 0.151 Uiso 1 1 calc R U . . .
C48 C 0.415(2) 0.7187(11) 0.5692(12) 0.115(7) Uani 1 1 d . . . . .
H48 H 0.4075 0.7231 0.6418 0.138 Uiso 1 1 calc R U . . .
N1 N 0.3821(8) 0.9553(7) 0.4669(6) 0.0631(17) Uani 1 1 d . . . . .
N2 N 0.4513(8) 0.9337(4) 0.2675(6) 0.0549(19) Uani 1 1 d . . . . .
O3 O 0.0430(6) 0.9595(5) 0.4492(5) 0.0573(14) Uani 1 1 d . . . . .
O4 O -0.0365(6) 0.9880(3) 0.2413(5) 0.0537(15) Uani 1 1 d . . . . .
O5 O 0.2245(9) 0.8512(4) 0.3646(7) 0.057(2) Uani 1 1 d . . . . .
O6 O 0.1582(8) 0.8894(3) 0.1610(6) 0.0539(16) Uani 1 1 d . . . . .
O1 O 0.2012(9) 1.0669(4) 0.3632(7) 0.0546(19) Uani 1 1 d . . . . .
O2 O 0.2325(8) 1.0232(4) 0.1565(6) 0.0569(17) Uani 1 1 d . . . . .
Sm1 Sm 0.19034(4) 0.95896(3) 0.30581(3) 0.04609(14) Uani 1 1 d . . . . .
C46 C -0.2068(14) 1.0576(5) 0.1013(9) 0.064(3) Uani 1 1 d . . . . .
H46 H -0.1233 1.0408 0.0793 0.076 Uiso 1 1 calc R U . . .
C43 C -0.4567(13) 1.1060(7) 0.1635(15) 0.092(5) Uani 1 1 d . . . . .
H43 H -0.5409 1.1226 0.1847 0.110 Uiso 1 1 calc R U . . .
C44 C -0.4238(19) 1.1112(8) 0.0586(14) 0.099(5) Uani 1 1 d . . . . .
H44 H -0.4865 1.1306 0.0093 0.118 Uiso 1 1 calc R U . . .
C18 C 0.0403(16) 1.2151(8) 0.5439(11) 0.089(4) Uani 1 1 d . . . . .
H18 H 0.0077 1.2074 0.6106 0.107 Uiso 1 1 calc R U . . .
C35 C -0.216(2) 1.0520(10) 0.7224(12) 0.118(7) Uani 1 1 d . . . . .
H35 H -0.2739 1.0840 0.7454 0.142 Uiso 1 1 calc R U . . .
C30 C 0.250(3) 1.0720(11) -0.1609(13) 0.114(7) Uani 1 1 d . . . . .
H30 H 0.3044 1.0489 -0.2055 0.137 Uiso 1 1 calc R U . . .
C45 C -0.299(2) 1.0878(8) 0.0277(13) 0.090(5) Uani 1 1 d . . . . .
H45 H -0.2753 1.0922 -0.0422 0.107 Uiso 1 1 calc R U . . .
C29 C 0.164(2) 1.1181(12) -0.2018(11) 0.101(7) Uani 1 1 d . . . . .
H29 H 0.1617 1.1272 -0.2739 0.122 Uiso 1 1 calc R U . . .
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'
Sm Sm -5.3236 12.2178 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O2 C25 C24 124.7(11) . . ?
O2 C25 C26 115.3(11) . . ?
C24 C25 C26 120.0(11) . . ?
C61 C56 C57 117.5(12) . . ?
C61 C56 C55 119.2(12) . . ?
C57 C56 C55 123.2(13) . . ?
O6 C55 C54 121.5(10) . . ?
O6 C55 C56 116.5(11) . . ?
C54 C55 C56 121.9(11) . . ?
C31 C26 C27 118.5(12) . . ?
C31 C26 C25 119.0(12) . . ?
C27 C26 C25 122.5(11) . . ?
C58 C59 C60 119.0(15) . . ?
C58 C59 H59 120.5 . . ?
C60 C59 H59 120.5 . . ?
N2 C5 C6 121.5(10) . . ?
N2 C5 C4 116.2(8) . . ?
C6 C5 C4 122.3(10) . . ?
O1 C23 C24 124.6(9) . . ?
O1 C23 C22 116.6(8) . . ?
C24 C23 C22 118.7(9) . . ?
N1 C4 C3 119.9(11) . . ?
N1 C4 C5 117.2(9) . . ?
C3 C4 C5 122.8(10) . . ?
C21 C22 C17 118.7(10) . . ?
C21 C22 C23 122.3(9) . . ?
C17 C22 C23 118.9(9) . . ?
C22 C17 C18 120.3(11) . . ?
C22 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C26 C31 C30 119.3(15) . . ?
C26 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C58 C57 C56 121.5(13) . . ?
C58 C57 H57 119.2 . . ?
C56 C57 H57 119.2 . . ?
O5 C53 C54 124.8(10) . . ?
O5 C53 C52 115.9(10) . . ?
C54 C53 C52 119.3(9) . . ?
C61 C60 C59 121.1(18) . . ?
C61 C60 H60 119.5 . . ?
C59 C60 H60 119.5 . . ?
C23 C24 C25 125.3(10) . . ?
C23 C24 H24 117.4 . . ?
C25 C24 H24 117.4 . . ?
C60 C61 C56 121.0(16) . . ?
C60 C61 H61 119.5 . . ?
C56 C61 H61 119.5 . . ?
C59 C58 C57 119.9(15) . . ?
C59 C58 H58 120.0 . . ?
C57 C58 H58 120.0 . . ?
N3 C2 C1 121.3(13) . . ?
N3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C47 C52 C51 119.1(11) . . ?
C47 C52 C53 119.2(10) . . ?
C51 C52 C53 121.6(11) . . ?
N2 C9 C8 122.7(10) . . ?
N2 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
N1 C1 C2 122.8(13) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C19 C20 C21 121.1(12) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C53 C54 C55 124.9(9) . . ?
C53 C54 H54 117.5 . . ?
C55 C54 H54 117.5 . . ?
C28 C27 C26 120.5(12) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C52 C47 C48 120.9(14) . . ?
C52 C47 H47 119.6 . . ?
C48 C47 H47 119.6 . . ?
C22 C21 C20 120.4(11) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C27 C28 C29 120.8(14) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C52 C51 C50 119.0(14) . . ?
C52 C51 H51 120.5 . . ?
C50 C51 H51 120.5 . . ?
C7 C8 C9 118.7(10) . . ?
C7 C8 C13 117.2(10) . . ?
C9 C8 C13 124.0(11) . . ?
N3 C3 C4 123.2(14) . . ?
N3 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C49 C50 C51 122.0(15) . . ?
C49 C50 H50 119.0 . . ?
C51 C50 H50 119.0 . . ?
C8 C13 C14 109.4(11) . . ?
C8 C13 C12 105.8(12) . . ?
C14 C13 C12 86.6(10) . . ?
C8 C13 H13 116.9 . . ?
C14 C13 H13 116.9 . . ?
C12 C13 H13 116.9 . . ?
C3 N3 C2 115.8(13) . . ?
C11 C12 C13 84.6(9) . . ?
C11 C12 H12A 114.5 . . ?
C13 C12 H12A 114.5 . . ?
C11 C12 H12B 114.5 . . ?
C13 C12 H12B 114.5 . . ?
H12A C12 H12B 111.6 . . ?
C33 C32 C37 120.8(15) . . ?
C33 C32 H32 119.6 . . ?
C37 C32 H32 119.6 . . ?
C15 C14 C11 119.3(15) . . ?
C15 C14 C16 106.6(14) . . ?
C11 C14 C16 115.3(12) . . ?
C15 C14 C13 118.0(11) . . ?
C11 C14 C13 85.8(11) . . ?
C16 C14 C13 110.9(15) . . ?
C6 C7 C8 119.0(10) . . ?
C6 C7 C10 123.4(11) . . ?
C8 C7 C10 117.7(11) . . ?
C40 C39 C38 125.9(9) . . ?
C40 C39 H39 117.1 . . ?
C38 C39 H39 117.1 . . ?
C7 C6 C5 119.6(11) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C10 C11 C14 113.2(10) . . ?
C10 C11 C12 107.6(12) . . ?
C14 C11 C12 89.3(12) . . ?
C10 C11 H11 114.6 . . ?
C14 C11 H11 114.6 . . ?
C12 C11 H11 114.6 . . ?
O3 C38 C39 123.5(9) . . ?
O3 C38 C37 118.5(9) . . ?
C39 C38 C37 117.9(8) . . ?
C36 C37 C32 117.0(10) . . ?
C36 C37 C38 124.5(10) . . ?
C32 C37 C38 118.4(9) . . ?
C20 C19 C18 118.9(12) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C37 C36 C35 121.4(13) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C40 C39 123.1(9) . . ?
O4 C40 C41 116.1(8) . . ?
C39 C40 C41 120.8(9) . . ?
C34 C33 C32 120.8(16) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C11 C10 C7 110.9(11) . . ?
C11 C10 H10A 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C46 C41 C42 117.8(10) . . ?
C46 C41 C40 119.3(9) . . ?
C42 C41 C40 122.9(10) . . ?
C43 C42 C41 120.6(13) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C50 C49 C48 118.2(14) . . ?
C50 C49 H49 120.9 . . ?
C48 C49 H49 120.9 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C33 C34 C35 120.5(13) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C49 C48 C47 120.8(15) . . ?
C49 C48 H48 119.6 . . ?
C47 C48 H48 119.6 . . ?
C1 N1 C4 116.7(10) . . ?
C1 N1 Sm1 122.2(8) . . ?
C4 N1 Sm1 118.9(7) . . ?
C9 N2 C5 118.5(8) . . ?
C9 N2 Sm1 118.9(7) . . ?
C5 N2 Sm1 119.6(6) . . ?
C38 O3 Sm1 131.4(7) . . ?
C40 O4 Sm1 132.3(6) . . ?
C53 O5 Sm1 133.1(7) . . ?
C55 O6 Sm1 137.4(7) . . ?
C23 O1 Sm1 129.9(7) . . ?
C25 O2 Sm1 129.3(7) . . ?
O6 Sm1 O4 79.4(2) . . ?
O6 Sm1 O3 123.2(3) . . ?
O4 Sm1 O3 71.6(2) . . ?
O6 Sm1 O2 75.6(2) . . ?
O4 Sm1 O2 77.0(3) . . ?
O3 Sm1 O2 138.3(3) . . ?
O6 Sm1 O1 146.2(3) . . ?
O4 Sm1 O1 83.2(3) . . ?
O3 Sm1 O1 77.2(3) . . ?
O2 Sm1 O1 72.3(3) . . ?
O6 Sm1 O5 70.4(3) . . ?
O4 Sm1 O5 117.2(3) . . ?
O3 Sm1 O5 81.0(3) . . ?
O2 Sm1 O5 139.1(2) . . ?
O1 Sm1 O5 143.3(2) . . ?
O6 Sm1 N2 79.0(3) . . ?
O4 Sm1 N2 148.8(2) . . ?
O3 Sm1 N2 139.5(2) . . ?
O2 Sm1 N2 75.9(3) . . ?
O1 Sm1 N2 103.0(3) . . ?
O5 Sm1 N2 75.8(3) . . ?
O6 Sm1 N1 129.2(3) . . ?
O4 Sm1 N1 148.4(3) . . ?
O3 Sm1 N1 80.0(2) . . ?
O2 Sm1 N1 118.9(3) . . ?
O1 Sm1 N1 77.2(4) . . ?
O5 Sm1 N1 70.2(4) . . ?
N2 Sm1 N1 61.2(3) . . ?
C45 C46 C41 121.4(13) . . ?
C45 C46 H46 119.3 . . ?
C41 C46 H46 119.3 . . ?
C42 C43 C44 120.4(13) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C45 C44 C43 119.9(13) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C19 C18 C17 120.4(13) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C34 C35 C36 119.3(14) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C29 C30 C31 121.2(16) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C44 C45 C46 119.8(16) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C30 C29 C28 119.7(14) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
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
C25 O2 1.267(15) . ?
C25 C24 1.399(15) . ?
C25 C26 1.519(17) . ?
C56 C61 1.379(19) . ?
C56 C57 1.388(18) . ?
C56 C55 1.471(17) . ?
C55 O6 1.297(15) . ?
C55 C54 1.414(16) . ?
C26 C31 1.384(18) . ?
C26 C27 1.395(19) . ?
C59 C58 1.37(3) . ?
C59 C60 1.37(3) . ?
C59 H59 0.9300 . ?
C5 N2 1.356(14) . ?
C5 C6 1.401(14) . ?
C5 C4 1.471(15) . ?
C23 O1 1.279(13) . ?
C23 C24 1.387(14) . ?
C23 C22 1.512(13) . ?
C4 N1 1.341(15) . ?
C4 C3 1.410(18) . ?
C22 C21 1.371(15) . ?
C22 C17 1.375(15) . ?
C17 C18 1.403(18) . ?
C17 H17 0.9300 . ?
C31 C30 1.40(2) . ?
C31 H31 0.9300 . ?
C57 C58 1.376(17) . ?
C57 H57 0.9300 . ?
C53 O5 1.259(13) . ?
C53 C54 1.378(15) . ?
C53 C52 1.527(14) . ?
C60 C61 1.37(2) . ?
C60 H60 0.9300 . ?
C24 H24 0.9300 . ?
C61 H61 0.9300 . ?
C58 H58 0.9300 . ?
C2 N3 1.35(2) . ?
C2 C1 1.381(19) . ?
C2 H2 0.9300 . ?
C52 C47 1.347(18) . ?
C52 C51 1.381(17) . ?
C9 N2 1.325(13) . ?
C9 C8 1.413(14) . ?
C9 H9 0.9300 . ?
C1 N1 1.323(14) . ?
C1 H1 0.9300 . ?
C20 C19 1.36(2) . ?
C20 C21 1.388(17) . ?
C20 H20 0.9300 . ?
C54 H54 0.9300 . ?
C27 C28 1.366(17) . ?
C27 H27 0.9300 . ?
C47 C48 1.40(2) . ?
C47 H47 0.9300 . ?
C21 H21 0.9300 . ?
C28 C29 1.37(2) . ?
C28 H28 0.9300 . ?
C51 C50 1.40(2) . ?
C51 H51 0.9300 . ?
C8 C7 1.375(17) . ?
C8 C13 1.484(16) . ?
C3 N3 1.314(19) . ?
C3 H3 0.9300 . ?
C50 C49 1.35(2) . ?
C50 H50 0.9300 . ?
C13 C14 1.57(2) . ?
C13 C12 1.592(19) . ?
C13 H13 0.9800 . ?
C12 C11 1.54(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C32 C33 1.364(14) . ?
C32 C37 1.399(17) . ?
C32 H32 0.9300 . ?
C14 C15 1.52(2) . ?
C14 C11 1.54(2) . ?
C14 C16 1.54(2) . ?
C7 C6 1.377(18) . ?
C7 C10 1.522(15) . ?
C39 C40 1.380(14) . ?
C39 C38 1.399(15) . ?
C39 H39 0.9300 . ?
C6 H6 0.9300 . ?
C11 C10 1.47(2) . ?
C11 H11 0.9800 . ?
C38 O3 1.268(12) . ?
C38 C37 1.489(13) . ?
C37 C36 1.382(16) . ?
C19 C18 1.36(2) . ?
C19 H19 0.9300 . ?
C36 C35 1.385(19) . ?
C36 H36 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C40 O4 1.290(11) . ?
C40 C41 1.483(14) . ?
C33 C34 1.35(2) . ?
C33 H33 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C41 C46 1.393(17) . ?
C41 C42 1.397(15) . ?
C42 C43 1.385(19) . ?
C42 H42 0.9300 . ?
C49 C48 1.36(3) . ?
C49 H49 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C34 C35 1.36(2) . ?
C34 H34 0.9300 . ?
C48 H48 0.9300 . ?
N1 Sm1 2.653(8) . ?
N2 Sm1 2.622(7) . ?
O3 Sm1 2.363(5) . ?
O4 Sm1 2.346(6) . ?
O5 Sm1 2.394(8) . ?
O6 Sm1 2.344(7) . ?
O1 Sm1 2.376(8) . ?
O2 Sm1 2.372(7) . ?
C46 C45 1.391(19) . ?
C46 H46 0.9300 . ?
C43 C44 1.39(2) . ?
C43 H43 0.9300 . ?
C44 C45 1.37(2) . ?
C44 H44 0.9300 . ?
C18 H18 0.9300 . ?
C35 H35 0.9300 . ?
C30 C29 1.35(3) . ?
C30 H30 0.9300 . ?
C45 H45 0.9300 . ?
C29 H29 0.9300 . ?
