#------------------------------------------------------------------------------
#$Date: 2024-12-06 19:44:57 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296483 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/95/7249531.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_7249531
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                 93.560(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5520(2)
_cell_length_b                   20.9501(5)
_cell_length_c                   12.6405(3)
_cell_measurement_reflns_used    4776
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.319
_cell_measurement_theta_min      1.752
_cell_volume                     2524.68(10)
_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 0.971
_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  0.0659
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9639
_diffrn_reflns_point_group_measured_fraction_full 0.682
_diffrn_reflns_point_group_measured_fraction_max 0.657
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.637
_diffrn_reflns_theta_min         3.503
_exptl_absorpt_coefficient_mu    9.178
_exptl_absorpt_correction_T_max  0.175
_exptl_absorpt_correction_T_min  0.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2012'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1094
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         3.262
_refine_diff_density_min         -2.460
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.006(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     642
_refine_ls_number_reflns         6581
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0833
_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)+(0.1524P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2166
_refine_ls_wR_factor_ref         0.2257
_reflns_Friedel_coverage         0.314
_reflns_Friedel_fraction_full    0.348
_reflns_Friedel_fraction_max     0.323
_reflns_number_gt                5776
_reflns_number_total             6581
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01052c2.cif
_cod_data_source_block           22
_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               7249531
_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
C1 C 0.1475(18) 0.0790(15) 0.4328(13) 0.082(6) Uani 1 1 d . . . . .
H1 H 0.2303 0.0574 0.4215 0.098 Uiso 1 1 calc R U . . .
C2 C 0.065(3) 0.0963(19) 0.3484(16) 0.106(10) Uani 1 1 d . . . . .
H2 H 0.0865 0.0822 0.2816 0.127 Uiso 1 1 calc R U . . .
C3 C -0.081(2) 0.1438(14) 0.4570(16) 0.090(6) Uani 1 1 d . . . . .
H3 H -0.1638 0.1659 0.4671 0.108 Uiso 1 1 calc R U . . .
C4 C -0.0037(15) 0.1248(8) 0.5442(14) 0.062(4) Uani 1 1 d . . . . .
C5 C -0.0409(14) 0.1364(7) 0.6541(12) 0.055(3) Uani 1 1 d . U . . .
C6 C -0.1610(18) 0.1707(10) 0.6743(15) 0.070(4) Uani 1 1 d . . . . .
H6 H -0.2192 0.1868 0.6188 0.084 Uiso 1 1 calc R U . . .
C7 C -0.1924(18) 0.1805(9) 0.7786(15) 0.062(4) Uani 1 1 d . . . . .
C8 C -0.1046(16) 0.1555(7) 0.8592(13) 0.058(3) Uani 1 1 d . . . . .
C9 C 0.0134(18) 0.1224(8) 0.8303(13) 0.062(3) Uani 1 1 d . . . . .
H9 H 0.0719 0.1048 0.8842 0.074 Uiso 1 1 calc R U . . .
C10 C -0.3143(15) 0.2213(12) 0.8109(18) 0.081(6) Uani 1 1 d . . . . .
H10A H -0.3043 0.2642 0.7836 0.097 Uiso 1 1 calc R U . . .
H10B H -0.4015 0.2038 0.7800 0.097 Uiso 1 1 calc R U . . .
C11 C -0.3200(19) 0.2239(9) 0.9278(19) 0.078(5) Uani 1 1 d . . . . .
H11 H -0.3987 0.2482 0.9534 0.094 Uiso 1 1 calc R U . . .
C12 C -0.307(2) 0.1565(12) 0.969(2) 0.091(7) Uani 1 1 d . . . . .
H12A H -0.3426 0.1242 0.9195 0.110 Uiso 1 1 calc R U . . .
H12B H -0.3412 0.1503 1.0388 0.110 Uiso 1 1 calc R U . . .
C13 C -0.142(2) 0.1674(9) 0.9690(16) 0.077(5) Uani 1 1 d . . . . .
H13 H -0.0841 0.1466 1.0256 0.092 Uiso 1 1 calc R U . . .
C14 C -0.174(2) 0.2397(11) 0.9834(16) 0.078(5) Uani 1 1 d . . . . .
C15 C -0.0821(19) 0.2890(10) 0.933(2) 0.085(6) Uani 1 1 d . . . . .
H15A H -0.1337 0.3280 0.9223 0.128 Uiso 1 1 calc R U . . .
H15B H -0.0542 0.2733 0.8663 0.128 Uiso 1 1 calc R U . . .
H15C H -0.0002 0.2968 0.9794 0.128 Uiso 1 1 calc R U . . .
C16 C -0.179(4) 0.2570(18) 1.100(2) 0.129(12) Uani 1 1 d . . . . .
H16A H -0.2329 0.2953 1.1072 0.193 Uiso 1 1 calc R U . . .
H16B H -0.0853 0.2637 1.1303 0.193 Uiso 1 1 calc R U . . .
H16C H -0.2218 0.2228 1.1373 0.193 Uiso 1 1 calc R U . . .
C17 C 0.162(3) 0.2888(14) 0.5000(16) 0.093(7) Uani 1 1 d . . . . .
H17 H 0.2200 0.2577 0.4733 0.112 Uiso 1 1 calc R U . . .
C18 C 0.090(3) 0.3287(15) 0.430(2) 0.108(9) Uani 1 1 d . . . . .
H18 H 0.0988 0.3249 0.3572 0.130 Uiso 1 1 calc R U . . .
C19 C 0.001(2) 0.3754(13) 0.470(2) 0.095(7) Uani 1 1 d . . . . .
H19 H -0.0487 0.4032 0.4245 0.114 Uiso 1 1 calc R U . . .
C20 C -0.009(3) 0.3791(13) 0.573(2) 0.102(7) Uani 1 1 d . . . . .
H20 H -0.0691 0.4093 0.5996 0.122 Uiso 1 1 calc R U . . .
C21 C 0.067(2) 0.3397(11) 0.6452(17) 0.081(5) Uani 1 1 d . . . . .
H21 H 0.0593 0.3447 0.7178 0.098 Uiso 1 1 calc R U . . .
C22 C 0.1537(16) 0.2926(7) 0.6067(14) 0.059(3) Uani 1 1 d . . . . .
C23 C 0.2300(15) 0.2468(6) 0.6787(11) 0.050(3) Uani 1 1 d . . . . .
C24 C 0.2462(15) 0.2579(7) 0.7870(12) 0.054(3) Uani 1 1 d . . . . .
H24 H 0.2179 0.2975 0.8110 0.065 Uiso 1 1 calc R U . . .
C25 C 0.3012(14) 0.2151(8) 0.8631(15) 0.050(3) Uani 1 1 d . . . . .
C26 C 0.3044(15) 0.2300(8) 0.9802(14) 0.053(3) Uani 1 1 d . . . . .
C27 C 0.3046(18) 0.2912(9) 1.0152(14) 0.065(4) Uani 1 1 d . . . . .
H27 H 0.3032 0.3248 0.9670 0.079 Uiso 1 1 calc R U . . .
C28 C 0.307(2) 0.3037(12) 1.1239(16) 0.086(6) Uani 1 1 d . . . . .
H28 H 0.3094 0.3457 1.1480 0.103 Uiso 1 1 calc R U . . .
C29 C 0.305(2) 0.253(2) 1.1968(16) 0.092(10) Uani 1 1 d . . . . .
H29 H 0.3058 0.2612 1.2692 0.110 Uiso 1 1 calc R U . . .
C30 C 0.303(3) 0.1912(15) 1.159(2) 0.093(7) Uani 1 1 d . . . . .
H30 H 0.2995 0.1571 1.2053 0.112 Uiso 1 1 calc R U . . .
C31 C 0.305(2) 0.1802(11) 1.0504(16) 0.075(5) Uani 1 1 d . . . . .
H31 H 0.3063 0.1385 1.0253 0.090 Uiso 1 1 calc R U . . .
C32 C 0.5385(17) 0.0878(13) 0.3447(12) 0.070(4) Uani 1 1 d . . . . .
H32 H 0.4780 0.1194 0.3660 0.085 Uiso 1 1 calc R U . . .
C33 C 0.571(2) 0.0856(19) 0.2394(14) 0.094(5) Uani 1 1 d . . . . .
H33 H 0.5309 0.1148 0.1912 0.113 Uiso 1 1 calc R U . . .
C34 C 0.662(4) 0.0407(16) 0.2065(17) 0.134(13) Uani 1 1 d . . . . .
H34 H 0.6873 0.0397 0.1367 0.160 Uiso 1 1 calc R U . . .
C35 C 0.716(3) -0.0035(15) 0.280(2) 0.114(10) Uani 1 1 d . . . . .
H35 H 0.7781 -0.0343 0.2578 0.137 Uiso 1 1 calc R U . . .
C36 C 0.681(3) -0.0032(11) 0.3824(15) 0.088(6) Uani 1 1 d . . . . .
H36 H 0.7152 -0.0348 0.4288 0.106 Uiso 1 1 calc R U . . .
C37 C 0.5923(18) 0.0451(8) 0.4184(13) 0.062(3) Uani 1 1 d . . . . .
C38 C 0.5610(14) 0.0524(7) 0.5310(10) 0.049(3) Uani 1 1 d . . . . .
C39 C 0.6456(17) 0.0231(8) 0.6084(13) 0.062(4) Uani 1 1 d . . . . .
H39 H 0.7174 -0.0023 0.5853 0.075 Uiso 1 1 calc R U . . .
C40 C 0.6359(14) 0.0273(6) 0.7179(12) 0.051(3) Uani 1 1 d . . . . .
C41 C 0.7375(17) -0.0045(7) 0.7940(14) 0.058(3) Uani 1 1 d . . . . .
C42 C 0.8639(19) -0.0293(9) 0.7644(18) 0.072(4) Uani 1 1 d . . . . .
H42 H 0.8874 -0.0263 0.6943 0.086 Uiso 1 1 calc R U . . .
C43 C 0.954(2) -0.0580(11) 0.837(2) 0.090(6) Uani 1 1 d . . . . .
H43 H 1.0383 -0.0739 0.8161 0.108 Uiso 1 1 calc R U . . .
C44 C 0.924(3) -0.0642(10) 0.941(2) 0.091(7) Uani 1 1 d . . . . .
H44 H 0.9855 -0.0845 0.9899 0.109 Uiso 1 1 calc R U . . .
C45 C 0.798(3) -0.0395(11) 0.9703(16) 0.083(6) Uani 1 1 d . . . . .
H45 H 0.7764 -0.0424 1.0407 0.100 Uiso 1 1 calc R U . . .
C46 C 0.7056(19) -0.0107(7) 0.8986(13) 0.062(4) Uani 1 1 d . . . . .
H46 H 0.6208 0.0048 0.9203 0.075 Uiso 1 1 calc R U . . .
C47 C 0.421(2) -0.1161(9) 0.5178(14) 0.071(4) Uani 1 1 d . . . . .
H47 H 0.4288 -0.0748 0.4917 0.085 Uiso 1 1 calc R U . . .
C48 C 0.460(2) -0.1681(12) 0.4565(16) 0.088(6) Uani 1 1 d . . . . .
H48 H 0.4930 -0.1611 0.3899 0.105 Uiso 1 1 calc R U . . .
C49 C 0.449(2) -0.2289(10) 0.4931(18) 0.078(5) Uani 1 1 d . . . . .
H49 H 0.4778 -0.2631 0.4529 0.094 Uiso 1 1 calc R U . . .
C50 C 0.397(3) -0.2390(9) 0.588(2) 0.088(6) Uani 1 1 d . . . . .
H50 H 0.3850 -0.2807 0.6101 0.106 Uiso 1 1 calc R U . . .
C51 C 0.360(2) -0.1894(9) 0.6530(17) 0.075(5) Uani 1 1 d . . . . .
H51 H 0.3281 -0.1976 0.7196 0.090 Uiso 1 1 calc R U . . .
C52 C 0.3727(14) -0.1259(6) 0.6164(11) 0.052(3) Uani 1 1 d D . . . .
C53 C 0.3394(14) -0.0702(6) 0.6840(11) 0.052(3) Uani 1 1 d D U . . .
C54 C 0.3506(18) -0.0771(7) 0.7949(12) 0.059(3) Uani 1 1 d . . . . .
H54 H 0.3849 -0.1158 0.8218 0.071 Uiso 1 1 calc R U . . .
C55 C 0.3144(17) -0.0307(8) 0.8686(13) 0.052(3) Uani 1 1 d . . . . .
C56 C 0.3259(19) -0.0465(9) 0.9836(14) 0.057(4) Uani 1 1 d . . . . .
C57 C 0.4121(19) -0.0923(8) 1.0290(12) 0.065(4) Uani 1 1 d . . . . .
H57 H 0.4686 -0.1157 0.9859 0.078 Uiso 1 1 calc R U . . .
C58 C 0.419(3) -0.1049(12) 1.1336(17) 0.088(6) Uani 1 1 d . . . . .
H58 H 0.4770 -0.1373 1.1606 0.105 Uiso 1 1 calc R U . . .
C59 C 0.340(4) -0.071(2) 1.2012(17) 0.113(11) Uani 1 1 d . . . . .
H59 H 0.3476 -0.0782 1.2739 0.136 Uiso 1 1 calc R U . . .
C60 C 0.249(4) -0.0246(16) 1.1582(17) 0.112(11) Uani 1 1 d . . . . .
H60 H 0.1916 -0.0024 1.2023 0.134 Uiso 1 1 calc R U . . .
C61 C 0.242(3) -0.0110(11) 1.0507(17) 0.083(6) Uani 1 1 d . . . . .
H61 H 0.1837 0.0211 1.0231 0.100 Uiso 1 1 calc R U . . .
N1 N 0.1169(14) 0.0912(10) 0.5331(10) 0.065(3) Uani 1 1 d . . . . .
N2 N 0.0483(13) 0.1141(7) 0.7324(11) 0.059(3) Uani 1 1 d . U . . .
N3 N -0.049(3) 0.1332(15) 0.3571(16) 0.121(9) Uani 1 1 d . . . . .
O1 O 0.2754(14) 0.1960(6) 0.6332(10) 0.063(3) Uani 1 1 d . . . . .
O2 O 0.3418(12) 0.1582(5) 0.8383(9) 0.057(2) Uani 1 1 d . . . . .
O3 O 0.4566(10) 0.0886(8) 0.5484(6) 0.058(2) Uani 1 1 d . . . . .
O4 O 0.5355(10) 0.0605(5) 0.7590(7) 0.056(2) Uani 1 1 d . . . . .
O5 O 0.2997(13) -0.0206(5) 0.6385(10) 0.057(3) Uani 1 1 d . U . . .
O6 O 0.2655(13) 0.0239(5) 0.8432(8) 0.061(3) Uani 1 1 d . . . . .
Sm1 Sm 0.30959(6) 0.08840(5) 0.69409(4) 0.0469(2) Uani 1 1 d . . . . .
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
C2 C1 N1 123.2(19) . . ?
C2 C1 H1 118.4 . . ?
N1 C1 H1 118.4 . . ?
C1 C2 N3 122(2) . . ?
C1 C2 H2 119.0 . . ?
N3 C2 H2 119.0 . . ?
N3 C3 C4 125.0(19) . . ?
N3 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
C3 C4 N1 119.5(16) . . ?
C3 C4 C5 124.7(14) . . ?
N1 C4 C5 115.8(13) . . ?
N2 C5 C6 122.4(15) . . ?
N2 C5 C4 117.1(12) . . ?
C6 C5 C4 120.4(14) . . ?
C7 C6 C5 118.7(16) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C8 C7 C6 119.3(16) . . ?
C8 C7 C10 117.1(17) . . ?
C6 C7 C10 123.6(17) . . ?
C7 C8 C9 117.3(15) . . ?
C7 C8 C13 117.2(16) . . ?
C9 C8 C13 125.4(17) . . ?
N2 C9 C8 124.8(16) . . ?
N2 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C11 C10 C7 111.3(17) . . ?
C11 C10 H10A 109.4 . . ?
C7 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C7 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 107.6(18) . . ?
C10 C11 C14 111.7(14) . . ?
C12 C11 C14 89.4(19) . . ?
C10 C11 H11 115.1 . . ?
C12 C11 H11 115.1 . . ?
C14 C11 H11 115.1 . . ?
C11 C12 C13 85.9(15) . . ?
C11 C12 H12A 114.3 . . ?
C13 C12 H12A 114.3 . . ?
C11 C12 H12B 114.3 . . ?
C13 C12 H12B 114.3 . . ?
H12A C12 H12B 111.5 . . ?
C8 C13 C14 109.5(16) . . ?
C8 C13 C12 105.9(18) . . ?
C14 C13 C12 86.5(16) . . ?
C8 C13 H13 116.9 . . ?
C14 C13 H13 116.9 . . ?
C12 C13 H13 116.9 . . ?
C15 C14 C16 107(2) . . ?
C15 C14 C11 118.8(19) . . ?
C16 C14 C11 114(2) . . ?
C15 C14 C13 119.3(16) . . ?
C16 C14 C13 111(2) . . ?
C11 C14 C13 85.2(17) . . ?
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 . . ?
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 . . ?
C22 C17 C18 123(2) . . ?
C22 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C17 C18 C19 119(2) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C20 C19 C18 119(2) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C21 123(2) . . ?
C19 C20 H20 118.6 . . ?
C21 C20 H20 118.6 . . ?
C20 C21 C22 119(2) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C21 117.5(18) . . ?
C17 C22 C23 120.9(17) . . ?
C21 C22 C23 121.5(16) . . ?
O1 C23 C24 123.6(12) . . ?
O1 C23 C22 115.1(13) . . ?
C24 C23 C22 121.2(13) . . ?
C23 C24 C25 126.0(13) . . ?
C23 C24 H24 117.0 . . ?
C25 C24 H24 117.0 . . ?
O2 C25 C24 122.0(16) . . ?
O2 C25 C26 115.9(15) . . ?
C24 C25 C26 121.8(14) . . ?
C27 C26 C31 120.5(17) . . ?
C27 C26 C25 121.0(16) . . ?
C31 C26 C25 118.5(16) . . ?
C26 C27 C28 120(2) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C29 120(2) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 119(2) . . ?
C30 C29 H29 120.7 . . ?
C28 C29 H29 120.7 . . ?
C29 C30 C31 120(2) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C26 C31 C30 121(2) . . ?
C26 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C37 C32 C33 122(2) . . ?
C37 C32 H32 118.9 . . ?
C33 C32 H32 118.9 . . ?
C34 C33 C32 120(2) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 118(2) . . ?
C33 C34 H34 120.8 . . ?
C35 C34 H34 120.8 . . ?
C36 C35 C34 122(2) . . ?
C36 C35 H35 119.0 . . ?
C34 C35 H35 119.0 . . ?
C35 C36 C37 119.9(19) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C32 C37 C36 117.2(16) . . ?
C32 C37 C38 119.8(15) . . ?
C36 C37 C38 123.0(15) . . ?
O3 C38 C39 124.8(13) . . ?
O3 C38 C37 115.6(12) . . ?
C39 C38 C37 119.6(13) . . ?
C38 C39 C40 127.4(14) . . ?
C38 C39 H39 116.3 . . ?
C40 C39 H39 116.3 . . ?
O4 C40 C39 121.2(13) . . ?
O4 C40 C41 116.5(13) . . ?
C39 C40 C41 122.3(13) . . ?
C46 C41 C42 118.1(16) . . ?
C46 C41 C40 119.2(15) . . ?
C42 C41 C40 122.7(17) . . ?
C43 C42 C41 120(2) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C42 C43 C44 122.2(19) . . ?
C42 C43 H43 118.9 . . ?
C44 C43 H43 118.9 . . ?
C43 C44 C45 117.4(18) . . ?
C43 C44 H44 121.3 . . ?
C45 C44 H44 121.3 . . ?
C46 C45 C44 122(2) . . ?
C46 C45 H45 119.1 . . ?
C44 C45 H45 119.1 . . ?
C45 C46 C41 120.2(18) . . ?
C45 C46 H46 119.9 . . ?
C41 C46 H46 119.9 . . ?
C52 C47 C48 120.2(18) . . ?
C52 C47 H47 119.9 . . ?
C48 C47 H47 119.9 . . ?
C49 C48 C47 121(2) . . ?
C49 C48 H48 119.6 . . ?
C47 C48 H48 119.6 . . ?
C50 C49 C48 119.4(17) . . ?
C50 C49 H49 120.3 . . ?
C48 C49 H49 120.3 . . ?
C49 C50 C51 122(2) . . ?
C49 C50 H50 118.8 . . ?
C51 C50 H50 118.8 . . ?
C50 C51 C52 118.7(19) . . ?
C50 C51 H51 120.7 . . ?
C52 C51 H51 120.7 . . ?
C47 C52 C51 118.5(14) . . ?
C47 C52 C53 120.0(14) . . ?
C51 C52 C53 121.4(14) . . ?
O5 C53 C54 123.5(13) . . ?
O5 C53 C52 117.4(13) . . ?
C54 C53 C52 119.0(13) . . ?
C55 C54 C53 125.6(15) . . ?
C55 C54 H54 117.2 . . ?
C53 C54 H54 117.2 . . ?
O6 C55 C54 124.0(15) . . ?
O6 C55 C56 116.8(14) . . ?
C54 C55 C56 119.1(15) . . ?
C57 C56 C61 117.8(17) . . ?
C57 C56 C55 125.0(16) . . ?
C61 C56 C55 117.3(17) . . ?
C58 C57 C56 122.7(19) . . ?
C58 C57 H57 118.7 . . ?
C56 C57 H57 118.7 . . ?
C57 C58 C59 121(2) . . ?
C57 C58 H58 119.5 . . ?
C59 C58 H58 119.5 . . ?
C58 C59 C60 118(2) . . ?
C58 C59 H59 120.9 . . ?
C60 C59 H59 120.9 . . ?
C59 C60 C61 121(2) . . ?
C59 C60 H60 119.4 . . ?
C61 C60 H60 119.4 . . ?
C60 C61 C56 119(2) . . ?
C60 C61 H61 120.4 . . ?
C56 C61 H61 120.4 . . ?
C1 N1 C4 115.4(15) . . ?
C1 N1 Sm1 122.5(10) . . ?
C4 N1 Sm1 118.8(11) . . ?
C9 N2 C5 117.4(13) . . ?
C9 N2 Sm1 120.0(11) . . ?
C5 N2 Sm1 120.0(9) . . ?
C3 N3 C2 114(2) . . ?
C23 O1 Sm1 132.2(9) . . ?
C25 O2 Sm1 137.2(11) . . ?
C38 O3 Sm1 129.2(9) . . ?
C40 O4 Sm1 132.3(9) . . ?
C53 O5 Sm1 131.4(10) . . ?
C55 O6 Sm1 129.2(9) . . ?
O4 Sm1 O2 79.0(3) . . ?
O4 Sm1 O6 77.5(4) . . ?
O2 Sm1 O6 76.1(4) . . ?
O4 Sm1 O3 72.3(3) . . ?
O2 Sm1 O3 123.0(5) . . ?
O6 Sm1 O3 139.0(4) . . ?
O4 Sm1 O5 83.3(4) . . ?
O2 Sm1 O5 145.7(4) . . ?
O6 Sm1 O5 71.6(4) . . ?
O3 Sm1 O5 77.8(5) . . ?
O4 Sm1 O1 116.9(4) . . ?
O2 Sm1 O1 70.8(4) . . ?
O6 Sm1 O1 139.6(4) . . ?
O3 Sm1 O1 79.9(5) . . ?
O5 Sm1 O1 143.3(3) . . ?
O4 Sm1 N2 148.7(4) . . ?
O2 Sm1 N2 79.0(4) . . ?
O6 Sm1 N2 75.7(4) . . ?
O3 Sm1 N2 138.9(4) . . ?
O5 Sm1 N2 103.2(4) . . ?
O1 Sm1 N2 75.8(4) . . ?
O4 Sm1 N1 148.8(4) . . ?
O2 Sm1 N1 129.3(5) . . ?
O6 Sm1 N1 118.1(5) . . ?
O3 Sm1 N1 79.7(3) . . ?
O5 Sm1 N1 77.5(5) . . ?
O1 Sm1 N1 70.1(6) . . ?
N2 Sm1 N1 61.0(4) . . ?
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
C1 C2 1.34(3) . ?
C1 N1 1.34(2) . ?
C1 H1 0.9300 . ?
C2 N3 1.34(4) . ?
C2 H2 0.9300 . ?
C3 N3 1.34(3) . ?
C3 C4 1.35(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.36(2) . ?
C4 C5 1.48(2) . ?
C5 N2 1.35(2) . ?
C5 C6 1.39(2) . ?
C6 C7 1.39(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.38(3) . ?
C7 C10 1.52(2) . ?
C8 C9 1.39(2) . ?
C8 C13 1.48(2) . ?
C9 N2 1.31(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.48(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.51(3) . ?
C11 C14 1.56(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.59(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.56(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.52(3) . ?
C14 C16 1.53(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.36(3) . ?
C17 C18 1.38(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.41(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.32(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.40(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.40(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.48(2) . ?
C23 O1 1.297(19) . ?
C23 C24 1.39(2) . ?
C24 C25 1.39(2) . ?
C24 H24 0.9300 . ?
C25 O2 1.298(18) . ?
C25 C26 1.51(2) . ?
C26 C27 1.36(2) . ?
C26 C31 1.37(3) . ?
C27 C28 1.40(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.40(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.38(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.39(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C37 1.37(3) . ?
C32 C33 1.39(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.36(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.38(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.36(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.41(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.48(2) . ?
C38 O3 1.284(18) . ?
C38 C39 1.37(2) . ?
C39 C40 1.40(2) . ?
C39 H39 0.9300 . ?
C40 O4 1.317(17) . ?
C40 C41 1.48(2) . ?
C41 C46 1.38(2) . ?
C41 C42 1.39(3) . ?
C42 C43 1.36(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.36(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.38(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.37(3) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 C52 1.37(2) . ?
C47 C48 1.40(3) . ?
C47 H47 0.9300 . ?
C48 C49 1.36(3) . ?
C48 H48 0.9300 . ?
C49 C50 1.34(3) . ?
C49 H49 0.9300 . ?
C50 C51 1.39(3) . ?
C50 H50 0.9300 . ?
C51 C52 1.42(2) . ?
C51 H51 0.9300 . ?
C52 C53 1.492(11) . ?
C53 O5 1.235(18) . ?
C53 C54 1.41(2) . ?
C54 C55 1.40(2) . ?
C54 H54 0.9300 . ?
C55 O6 1.27(2) . ?
C55 C56 1.49(2) . ?
C56 C57 1.37(3) . ?
C56 C61 1.41(3) . ?
C57 C58 1.35(3) . ?
C57 H57 0.9300 . ?
C58 C59 1.37(4) . ?
C58 H58 0.9300 . ?
C59 C60 1.39(5) . ?
C59 H59 0.9300 . ?
C60 C61 1.39(3) . ?
C60 H60 0.9300 . ?
C61 H61 0.9300 . ?
N1 Sm1 2.658(13) . ?
N2 Sm1 2.628(12) . ?
O1 Sm1 2.398(12) . ?
O2 Sm1 2.342(10) . ?
O3 Sm1 2.384(8) . ?
O4 Sm1 2.335(10) . ?
O5 Sm1 2.390(12) . ?
O6 Sm1 2.379(10) . ?
