#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:20:45 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179056 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/18/4301810.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_4301810
loop_
_publ_author_name
'Kyra Lunstroot'
'Peter Nockemann'
'Kristof Van Hecke'
'Luc Van Meervelt'
'Christiane Görller-Walrand'
'Koen Binnemans'
'Kris Driesen'
_publ_section_title
;
Visible and Near-Infrared Emission by Samarium(III)-Containing Ionic Liquid
Mixtures
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3018
_journal_page_last               3026
_journal_paper_doi               10.1021/ic8020782
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C56 H32 F12 O8 Sm, C10 H19 N2'
_chemical_formula_sum            'C66 H51 F12 N2 O8 Sm'
_chemical_formula_weight         1378.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.030(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.3645(11)
_cell_length_b                   17.1989(14)
_cell_length_c                   23.5340(15)
_cell_measurement_temperature    100(2)
_cell_volume                     5900.2(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  Platon
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'SMART 6000'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'crossed Goebel mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1245
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            48651
_diffrn_reflns_theta_full        65.14
_diffrn_reflns_theta_max         65.14
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    8.320
_exptl_absorpt_correction_T_max  0.287
_exptl_absorpt_correction_T_min  0.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2780
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.157
_refine_diff_density_min         -1.743
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         9810
_refine_ls_number_restraints     295
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0703
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1080P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1995
_reflns_number_gt                5906
_reflns_number_total             9810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic8020782_si_003.cif
_cod_data_source_block           wg101
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4301810
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24068(19) 0.5559(3) 0.03703(16) 0.0316(16) Uani 1 1 d D . .
C2 C 0.1476(2) 0.5588(3) 0.00935(16) 0.0363(17) Uani 1 1 d D . .
H2 H 0.1179 0.5751 0.0339 0.044 Uiso 1 1 calc R . .
C3 C 0.09356(18) 0.5378(3) -0.05614(14) 0.0290(16) Uani 1 1 d D . .
C4 C 0.13948(19) 0.5166(4) -0.09198(15) 0.0444(19) Uani 1 1 d D . .
C5 C 0.2337(2) 0.5155(4) -0.06487(16) 0.0450(19) Uani 1 1 d D . .
H5 H 0.2639 0.5035 -0.0900 0.054 Uiso 1 1 calc R . .
C6 C 0.2846(2) 0.5324(4) 0.00013(16) 0.0404(19) Uani 1 1 d D . .
H6 H 0.3495 0.5279 0.0197 0.049 Uiso 1 1 calc R . .
C7 C -0.0022(2) 0.5382(3) -0.08470(17) 0.0355(18) Uani 1 1 d D . .
H7 H -0.0326 0.5538 -0.0605 0.043 Uiso 1 1 calc R . .
C8 C -0.0540(2) 0.5160(4) -0.14815(17) 0.049(2) Uani 1 1 d D . .
H8 H -0.1191 0.5157 -0.1676 0.059 Uiso 1 1 calc R . .
C9 C -0.0057(2) 0.4940(4) -0.18254(19) 0.066(3) Uani 1 1 d D . .
H9 H -0.0401 0.4780 -0.2256 0.079 Uiso 1 1 calc R . .
C10 C 0.0846(2) 0.4945(4) -0.15787(18) 0.062(2) Uani 1 1 d D . .
H10 H 0.1135 0.4803 -0.1834 0.074 Uiso 1 1 calc R . .
C11 C 0.2980(4) 0.5655(4) 0.1068(3) 0.0357(17) Uani 1 1 d . . .
C12 C 0.2574(3) 0.5931(4) 0.1456(3) 0.0380(18) Uani 1 1 d . . .
H12 H 0.1960 0.6115 0.1254 0.046 Uiso 1 1 calc R . .
C13 C 0.3049(3) 0.5940(4) 0.2116(3) 0.0350(17) Uani 1 1 d . . .
C14 C 0.2540(4) 0.6268(4) 0.2466(3) 0.0371(17) Uani 1 1 d . . .
C15 C 0.2151(3) 0.3415(3) 0.1367(2) 0.0491(11) Uani 1 1 d DU . .
C16 C 0.1564(3) 0.2926(3) 0.1452(2) 0.0613(12) Uani 1 1 d DU . .
H16 H 0.1679 0.2775 0.1870 0.074 Uiso 1 1 calc R . .
C17 C 0.0770(3) 0.2637(3) 0.09079(18) 0.0653(11) Uani 1 1 d DU . .
C18 C 0.0594(3) 0.2884(3) 0.02928(19) 0.0673(11) Uani 1 1 d DU . .
C19 C 0.1181(3) 0.3373(3) 0.0199(2) 0.0608(12) Uani 1 1 d DU . .
H19 H 0.1067 0.3530 -0.0218 0.073 Uiso 1 1 calc R . .
C20 C 0.1959(3) 0.3636(3) 0.0740(2) 0.0542(12) Uani 1 1 d DU . .
H20 H 0.2374 0.3975 0.0683 0.065 Uiso 1 1 calc R . .
C21 C 0.0158(3) 0.2142(4) 0.0989(2) 0.0840(14) Uani 1 1 d DU . .
H21 H 0.0296 0.1955 0.1403 0.101 Uiso 1 1 calc R . .
C22 C -0.0657(3) 0.1918(4) 0.0466(2) 0.0935(15) Uani 1 1 d DU . .
H22 H -0.1089 0.1595 0.0517 0.112 Uiso 1 1 calc R . .
C23 C -0.0816(3) 0.2192(4) -0.0144(2) 0.0909(15) Uani 1 1 d DU . .
H23 H -0.1376 0.2051 -0.0500 0.109 Uiso 1 1 calc R . .
C24 C -0.0240(3) 0.2627(4) -0.0250(2) 0.0724(14) Uani 1 1 d DU . .
H24 H -0.0366 0.2769 -0.0672 0.087 Uiso 1 1 calc R . .
C25 C 0.2993(4) 0.3762(4) 0.1930(3) 0.0474(13) Uani 1 1 d U . .
C26 C 0.3030(4) 0.3841(4) 0.2522(3) 0.0448(15) Uani 1 1 d U . .
H26 H 0.2495 0.3731 0.2568 0.054 Uiso 1 1 calc R . .
C27 C 0.3820(4) 0.4075(4) 0.3056(3) 0.0437(18) Uani 1 1 d . . .
C28 C 0.3787(4) 0.4120(5) 0.3690(3) 0.059(2) Uani 1 1 d . . .
C29 C 0.5761(3) 0.3659(4) 0.0822(3) 0.0330(16) Uani 1 1 d . . .
C30 C 0.6307(4) 0.3093(4) 0.0770(3) 0.0414(18) Uani 1 1 d . . .
H30 H 0.6775 0.2870 0.1147 0.050 Uiso 1 1 calc R . .
C31 C 0.6192(3) 0.2823(4) 0.0159(3) 0.0371(16) Uani 1 1 d . . .
C32 C 0.5517(4) 0.3182(4) -0.0404(3) 0.0385(17) Uani 1 1 d . . .
C33 C 0.4986(3) 0.3787(4) -0.0329(3) 0.0372(18) Uani 1 1 d . . .
H33 H 0.4545 0.4045 -0.0698 0.045 Uiso 1 1 calc R . .
C34 C 0.5087(3) 0.4014(4) 0.0259(3) 0.0342(16) Uani 1 1 d . . .
H34 H 0.4704 0.4410 0.0290 0.041 Uiso 1 1 calc R . .
C35 C 0.6743(4) 0.2236(4) 0.0088(3) 0.059(2) Uani 1 1 d . . .
H35 H 0.7207 0.1996 0.0457 0.070 Uiso 1 1 calc R . .
C36 C 0.6627(5) 0.2012(5) -0.0483(3) 0.066(2) Uani 1 1 d . . .
H36 H 0.7007 0.1614 -0.0515 0.079 Uiso 1 1 calc R . .
C37 C 0.5948(4) 0.2353(4) -0.1045(3) 0.050(2) Uani 1 1 d . . .
H37 H 0.5861 0.2175 -0.1450 0.059 Uiso 1 1 calc R . .
C38 C 0.5418(4) 0.2940(4) -0.1003(3) 0.0394(18) Uani 1 1 d . . .
H38 H 0.4980 0.3186 -0.1380 0.047 Uiso 1 1 calc R . .
C39 C 0.5834(3) 0.3918(3) 0.1452(3) 0.0333(17) Uani 1 1 d . . .
C40 C 0.6682(3) 0.3763(3) 0.2014(3) 0.0324(16) Uani 1 1 d . . .
H40 H 0.7208 0.3614 0.1968 0.039 Uiso 1 1 calc R . .
C41 C 0.6745(3) 0.3828(3) 0.2623(3) 0.0344(18) Uani 1 1 d . . .
C42 C 0.7606(4) 0.3518(4) 0.3169(3) 0.0423(19) Uani 1 1 d . . .
C43 C 0.7285(3) 0.5459(3) 0.4260(3) 0.0314(16) Uani 1 1 d . . .
C44 C 0.8207(4) 0.5565(4) 0.4583(3) 0.0423(19) Uani 1 1 d . . .
H44 H 0.8523 0.5798 0.4374 0.051 Uiso 1 1 calc R . .
C45 C 0.8711(4) 0.5327(4) 0.5242(3) 0.0362(17) Uani 1 1 d . . .
C46 C 0.8196(4) 0.4973(4) 0.5532(3) 0.0442(19) Uani 1 1 d . . .
C47 C 0.7247(4) 0.4890(4) 0.5183(3) 0.0421(18) Uani 1 1 d . . .
H47 H 0.6909 0.4677 0.5385 0.050 Uiso 1 1 calc R . .
C48 C 0.6793(4) 0.5108(4) 0.4558(3) 0.0385(17) Uani 1 1 d . . .
H48 H 0.6151 0.5026 0.4323 0.046 Uiso 1 1 calc R . .
C49 C 0.9662(4) 0.5382(4) 0.5578(3) 0.047(2) Uani 1 1 d . . .
H49 H 0.9999 0.5619 0.5385 0.057 Uiso 1 1 calc R . .
C50 C 1.0115(4) 0.5095(4) 0.6189(3) 0.056(2) Uani 1 1 d . . .
H50 H 1.0765 0.5130 0.6411 0.067 Uiso 1 1 calc R . .
C51 C 0.9642(4) 0.4755(5) 0.6489(3) 0.061(2) Uani 1 1 d . . .
H51 H 0.9966 0.4564 0.6912 0.073 Uiso 1 1 calc R . .
C52 C 0.8704(4) 0.4697(5) 0.6169(3) 0.059(2) Uani 1 1 d . . .
H52 H 0.8385 0.4467 0.6377 0.070 Uiso 1 1 calc R . .
C53 C 0.6751(3) 0.5597(4) 0.3548(3) 0.0337(17) Uani 1 1 d . . .
C54 C 0.7209(3) 0.5851(4) 0.3183(3) 0.0332(17) Uani 1 1 d . . .
H54 H 0.7841 0.5984 0.3401 0.040 Uiso 1 1 calc R . .
C55 C 0.6762(3) 0.5906(3) 0.2530(3) 0.0280(15) Uani 1 1 d . . .
C56 C 0.7277(4) 0.6231(4) 0.2187(3) 0.047(2) Uani 1 1 d . . .
C57 C 0.4014(4) 0.2674(4) 1.0998(3) 0.0355(17) Uani 1 1 d . . .
H57 H 0.3730 0.3124 1.1063 0.043 Uiso 1 1 calc R . .
C58 C 0.4903(4) 0.1641(4) 1.1174(3) 0.0396(17) Uani 1 1 d . . .
H58 H 0.5336 0.1241 1.1388 0.048 Uiso 1 1 calc R . .
C59 C 0.4441(4) 0.1764(4) 1.0541(3) 0.0436(19) Uani 1 1 d . . .
H59 H 0.4500 0.1466 1.0222 0.052 Uiso 1 1 calc R . .
C60 C 0.3226(4) 0.2708(4) 0.9801(3) 0.0411(15) Uani 1 1 d U . .
H60A H 0.3532 0.2738 0.9522 0.049 Uiso 1 1 calc R . .
H60B H 0.3044 0.3241 0.9856 0.049 Uiso 1 1 calc R . .
C61 C 0.2367(4) 0.2189(4) 0.9486(3) 0.0443(14) Uani 1 1 d U B .
H61A H 0.2024 0.2200 0.9741 0.053 Uiso 1 1 calc R . .
H61B H 0.2550 0.1645 0.9466 0.053 Uiso 1 1 calc R . .
C62 C 0.1749(3) 0.2493(4) 0.8803(2) 0.0534(13) Uani 1 1 d DU . .
H62A H 0.1603 0.3043 0.8843 0.064 Uiso 1 1 calc R A 1
H62B H 0.2126 0.2493 0.8571 0.064 Uiso 1 1 calc R A 1
C63 C 0.0856(3) 0.2092(4) 0.8380(2) 0.0572(16) Uani 0.597(8) 1 d PRDU B 1
H63A H 0.0465 0.2088 0.8600 0.069 Uiso 0.597(8) 1 d PR B 1
H63B H 0.0987 0.1545 0.8319 0.069 Uiso 0.597(8) 1 d PR B 1
C64 C 0.0329(6) 0.2465(5) 0.7732(3) 0.063(2) Uani 0.597(8) 1 d PDU B 1
H64A H 0.0081 0.2972 0.7779 0.076 Uiso 0.597(8) 1 calc PR B 1
H64B H 0.0748 0.2560 0.7540 0.076 Uiso 0.597(8) 1 calc PR B 1
C65 C -0.0446(6) 0.1950(6) 0.7298(5) 0.066(3) Uani 0.597(8) 1 d PDU B 1
H65A H -0.0196 0.1488 0.7188 0.100 Uiso 0.597(8) 1 calc PR B 1
H65B H -0.0839 0.2235 0.6908 0.100 Uiso 0.597(8) 1 calc PR B 1
H65C H -0.0807 0.1790 0.7515 0.100 Uiso 0.597(8) 1 calc PR B 1
C66 C 0.0965(10) 0.1862(12) 0.8525(8) 0.0570(18) Uani 0.403(8) 1 d PU B 2
H66C H 0.1249 0.1340 0.8634 0.068 Uiso 0.403(8) 1 calc PR B 2
H66D H 0.0567 0.1921 0.8738 0.068 Uiso 0.403(8) 1 calc PR B 2
C67 C 0.0358(11) 0.1903(13) 0.7797(8) 0.0620(19) Uani 0.403(8) 1 d PU B 2
H67C H 0.0736 0.1788 0.7577 0.074 Uiso 0.403(8) 1 calc PR B 2
H67D H -0.0129 0.1503 0.7668 0.074 Uiso 0.403(8) 1 calc PR B 2
C68 C -0.0071(11) 0.2683(13) 0.7596(8) 0.068(4) Uani 0.403(8) 1 d PU B 2
H68D H -0.0420 0.2810 0.7830 0.102 Uiso 0.403(8) 1 calc PR B 2
H68E H -0.0485 0.2679 0.7137 0.102 Uiso 0.403(8) 1 calc PR B 2
H68F H 0.0409 0.3074 0.7689 0.102 Uiso 0.403(8) 1 calc PR B 2
C69 C 0.4924(4) 0.2332(4) 1.2134(3) 0.042(2) Uani 1 1 d . . .
H69A H 0.4674 0.2820 1.2205 0.064 Uiso 1 1 calc R . .
H69B H 0.5596 0.2353 1.2354 0.064 Uiso 1 1 calc R . .
H69C H 0.4711 0.1897 1.2300 0.064 Uiso 1 1 calc R . .
F1 F 0.2469(2) 0.5727(2) 0.28520(17) 0.0578(12) Uani 1 1 d . . .
F2 F 0.29978(19) 0.6857(2) 0.28453(15) 0.0460(10) Uani 1 1 d . . .
F3 F 0.16902(19) 0.6516(2) 0.21028(16) 0.0514(11) Uani 1 1 d . . .
F4 F 0.4164(3) 0.4781(3) 0.40005(19) 0.0817(15) Uani 1 1 d . . .
F5 F 0.2942(2) 0.4147(3) 0.3642(2) 0.0842(15) Uani 1 1 d . . .
F6 F 0.4205(4) 0.3557(4) 0.4064(2) 0.143(2) Uani 1 1 d . . .
F7 F 0.7900(2) 0.4004(2) 0.36668(17) 0.0516(12) Uani 1 1 d . . .
F8 F 0.8325(2) 0.3410(2) 0.30421(17) 0.0545(12) Uani 1 1 d . . .
F9 F 0.7450(2) 0.2825(2) 0.33736(16) 0.0523(12) Uani 1 1 d . . .
F10 F 0.7158(2) 0.5817(3) 0.16845(17) 0.0608(13) Uani 1 1 d . . .
F11 F 0.6979(2) 0.6941(3) 0.19696(18) 0.0630(13) Uani 1 1 d . . .
F12 F 0.81806(19) 0.6288(2) 0.25497(17) 0.0548(12) Uani 1 1 d . . .
N1 N 0.4612(3) 0.2224(3) 1.1449(2) 0.0348(14) Uani 1 1 d . . .
N2 N 0.3877(3) 0.2385(3) 1.0434(2) 0.0375(14) Uani 1 1 d . . .
O1 O 0.3813(2) 0.5456(2) 0.13069(17) 0.0314(11) Uani 1 1 d . . .
O2 O 0.3851(2) 0.5719(2) 0.24778(16) 0.0337(11) Uani 1 1 d . . .
O3 O 0.3627(2) 0.3981(2) 0.17925(19) 0.0388(12) Uani 1 1 d . . .
O4 O 0.4591(2) 0.4262(3) 0.30933(19) 0.0453(13) Uani 1 1 d . . .
O5 O 0.5158(2) 0.4224(2) 0.14667(17) 0.0335(11) Uani 1 1 d . . .
O6 O 0.6145(2) 0.4024(2) 0.27841(17) 0.0333(11) Uani 1 1 d . . .
O7 O 0.5904(2) 0.5473(2) 0.32887(17) 0.0324(11) Uani 1 1 d . . .
O8 O 0.5935(2) 0.5726(2) 0.21495(17) 0.0348(12) Uani 1 1 d . . .
Sm1 Sm 0.488274(17) 0.488136(19) 0.228583(14) 0.02832(8) 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'
F F 0.0727 0.0534 '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'
H H 0.0000 0.0000 '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 C6 119.2(3) . . ?
C2 C1 C11 122.3(4) . . ?
C6 C1 C11 118.0(3) . . ?
C1 C2 C3 121.1(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C7 C3 C4 120.0(3) . . ?
C7 C3 C2 121.7(3) . . ?
C4 C3 C2 118.3(3) . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 C10 120.9(4) . . ?
C3 C4 C10 118.0(3) . . ?
C4 C5 C6 119.3(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C3 121.2(4) . . ?
C8 C7 H7 119.4 . . ?
C3 C7 H7 119.4 . . ?
C7 C8 C9 117.3(3) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 H8 121.3 . . ?
C10 C9 C8 123.5(4) . . ?
C10 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C9 C10 C4 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C4 C10 H10 120.0 . . ?
O1 C11 C12 121.7(5) . . ?
O1 C11 C1 118.3(5) . . ?
C12 C11 C1 119.9(4) . . ?
C13 C12 C11 122.1(5) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
O2 C13 C12 129.7(6) . . ?
O2 C13 C14 113.9(5) . . ?
C12 C13 C14 116.4(5) . . ?
F3 C14 F2 107.0(5) . . ?
F3 C14 F1 105.7(5) . . ?
F2 C14 F1 105.5(4) . . ?
F3 C14 C13 116.2(5) . . ?
F2 C14 C13 111.5(5) . . ?
F1 C14 C13 110.3(5) . . ?
C16 C15 C20 119.0(4) . . ?
C16 C15 C25 122.1(5) . . ?
C20 C15 C25 118.9(4) . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C21 C17 C18 120.1(3) . . ?
C21 C17 C16 120.4(4) . . ?
C18 C17 C16 119.5(4) . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 C24 119.6(4) . . ?
C17 C18 C24 119.0(4) . . ?
C18 C19 C20 117.6(4) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C19 C20 C15 122.7(4) . . ?
C19 C20 H20 118.6 . . ?
C15 C20 H20 118.6 . . ?
C17 C21 C22 120.5(5) . . ?
C17 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 117.5(5) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 H22 121.2 . . ?
C24 C23 C22 124.4(4) . . ?
C24 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?
C23 C24 C18 118.3(5) . . ?
C23 C24 H24 120.8 . . ?
C18 C24 H24 120.8 . . ?
O3 C25 C26 124.2(5) . . ?
O3 C25 C15 114.2(6) . . ?
C26 C25 C15 121.6(5) . . ?
C25 C26 C27 122.7(6) . . ?
C25 C26 H26 118.7 . . ?
C27 C26 H26 118.7 . . ?
O4 C27 C26 128.6(7) . . ?
O4 C27 C28 113.4(5) . . ?
C26 C27 C28 118.0(6) . . ?
F6 C28 F5 107.2(7) . . ?
F6 C28 F4 107.3(6) . . ?
F5 C28 F4 102.6(6) . . ?
F6 C28 C27 113.1(7) . . ?
F5 C28 C27 114.6(5) . . ?
F4 C28 C27 111.4(6) . . ?
C30 C29 C34 119.2(6) . . ?
C30 C29 C39 122.6(5) . . ?
C34 C29 C39 118.3(5) . . ?
C29 C30 C31 121.7(5) . . ?
C29 C30 H30 119.2 . . ?
C31 C30 H30 119.2 . . ?
C35 C31 C32 117.8(6) . . ?
C35 C31 C30 123.2(5) . . ?
C32 C31 C30 119.0(6) . . ?
C38 C32 C33 123.0(5) . . ?
C38 C32 C31 119.4(6) . . ?
C33 C32 C31 117.5(5) . . ?
C34 C33 C32 122.3(5) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C33 C34 C29 120.3(6) . . ?
C33 C34 H34 119.9 . . ?
C29 C34 H34 119.9 . . ?
C36 C35 C31 121.5(6) . . ?
C36 C35 H35 119.3 . . ?
C31 C35 H35 119.3 . . ?
C35 C36 C37 121.2(7) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C38 C37 C36 119.7(6) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C37 C38 C32 120.3(5) . . ?
C37 C38 H38 119.8 . . ?
C32 C38 H38 119.8 . . ?
O5 C39 C40 123.5(6) . . ?
O5 C39 C29 118.8(4) . . ?
C40 C39 C29 117.6(5) . . ?
C41 C40 C39 121.3(5) . . ?
C41 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
O6 C41 C40 129.2(5) . . ?
O6 C41 C42 113.3(6) . . ?
C40 C41 C42 116.9(5) . . ?
F7 C42 F8 106.1(5) . . ?
F7 C42 F9 106.8(5) . . ?
F8 C42 F9 106.4(5) . . ?
F7 C42 C41 110.5(5) . . ?
F8 C42 C41 115.4(5) . . ?
F9 C42 C41 111.1(5) . . ?
C44 C43 C48 121.0(5) . . ?
C44 C43 C53 122.2(6) . . ?
C48 C43 C53 116.2(4) . . ?
C43 C44 C45 120.6(6) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 H44 119.7 . . ?
C49 C45 C46 120.2(5) . . ?
C49 C45 C44 122.4(6) . . ?
C46 C45 C44 117.2(5) . . ?
C47 C46 C52 123.1(6) . . ?
C47 C46 C45 119.9(5) . . ?
C52 C46 C45 117.0(5) . . ?
C48 C47 C46 121.3(6) . . ?
C48 C47 H47 119.3 . . ?
C46 C47 H47 119.3 . . ?
C47 C48 C43 119.8(5) . . ?
C47 C48 H48 120.1 . . ?
C43 C48 H48 120.1 . . ?
C50 C49 C45 120.2(7) . . ?
C50 C49 H49 119.9 . . ?
C45 C49 H49 119.9 . . ?
C49 C50 C51 121.4(6) . . ?
C49 C50 H50 119.3 . . ?
C51 C50 H50 119.3 . . ?
C52 C51 C50 119.6(6) . . ?
C52 C51 H51 120.2 . . ?
C50 C51 H51 120.2 . . ?
C51 C52 C46 121.7(7) . . ?
C51 C52 H52 119.2 . . ?
C46 C52 H52 119.2 . . ?
O7 C53 C54 121.4(5) . . ?
O7 C53 C43 117.7(5) . . ?
C54 C53 C43 120.8(4) . . ?
C55 C54 C53 122.1(5) . . ?
C55 C54 H54 118.9 . . ?
C53 C54 H54 118.9 . . ?
O8 C55 C54 128.7(6) . . ?
O8 C55 C56 112.6(5) . . ?
C54 C55 C56 118.7(5) . . ?
F10 C56 F11 105.8(5) . . ?
F10 C56 F12 106.5(5) . . ?
F11 C56 F12 106.6(5) . . ?
F10 C56 C55 112.9(5) . . ?
F11 C56 C55 110.4(5) . . ?
F12 C56 C55 114.2(5) . . ?
N1 C57 N2 108.0(5) . . ?
N1 C57 H57 126.0 . . ?
N2 C57 H57 126.0 . . ?
C59 C58 N1 105.2(5) . . ?
C59 C58 H58 127.4 . . ?
N1 C58 H58 127.4 . . ?
C58 C59 N2 108.7(6) . . ?
C58 C59 H59 125.6 . . ?
N2 C59 H59 125.6 . . ?
N2 C60 C61 110.3(5) . . ?
N2 C60 H60A 109.6 . . ?
C61 C60 H60A 109.6 . . ?
N2 C60 H60B 109.6 . . ?
C61 C60 H60B 109.6 . . ?
H60A C60 H60B 108.1 . . ?
C60 C61 C62 109.0(5) . . ?
C60 C61 H61A 109.9 . . ?
C62 C61 H61A 109.9 . . ?
C60 C61 H61B 109.9 . . ?
C62 C61 H61B 109.9 . . ?
H61A C61 H61B 108.3 . . ?
C63 C62 C61 120.5(3) . . ?
C61 C62 C66 102.8(8) . . ?
C63 C62 H62A 107.2 . . ?
C61 C62 H62A 107.2 . . ?
C66 C62 H62A 120.7 . . ?
C63 C62 H62B 107.2 . . ?
C61 C62 H62B 107.2 . . ?
C66 C62 H62B 111.4 . . ?
H62A C62 H62B 106.8 . . ?
C62 C63 C64 114.1(4) . . ?
C62 C63 H63A 108.7 . . ?
C64 C63 H63A 108.8 . . ?
C62 C63 H63B 108.7 . . ?
C64 C63 H63B 108.6 . . ?
H63A C63 H63B 107.6 . . ?
C65 C64 C63 110.7(7) . . ?
C65 C64 H64A 109.5 . . ?
C63 C64 H64A 109.5 . . ?
C65 C64 H64B 109.5 . . ?
C63 C64 H64B 109.5 . . ?
H64A C64 H64B 108.1 . . ?
C67 C66 C62 114.8(15) . . ?
C67 C66 H63A 90.8 . . ?
C62 C66 H63A 103.8 . . ?
C67 C66 H63B 60.3 . . ?
C62 C66 H63B 120.3 . . ?
H63A C66 H63B 134.0 . . ?
C67 C66 H66C 108.6 . . ?
C62 C66 H66C 108.6 . . ?
H63A C66 H66C 129.7 . . ?
H63B C66 H66C 49.1 . . ?
C67 C66 H66D 108.6 . . ?
C62 C66 H66D 108.6 . . ?
H63B C66 H66D 130.2 . . ?
H66C C66 H66D 107.5 . . ?
C68 C67 C66 111.5(17) . . ?
C68 C67 H63B 139.4 . . ?
C68 C67 H67C 109.3 . . ?
C66 C67 H67C 109.3 . . ?
H63B C67 H67C 89.1 . . ?
C68 C67 H67D 109.3 . . ?
C66 C67 H67D 109.3 . . ?
H63B C67 H67D 97.9 . . ?
H67C C67 H67D 108.0 . . ?
C67 C68 H68D 109.5 . . ?
C67 C68 H68E 109.5 . . ?
H68D C68 H68E 109.5 . . ?
C67 C68 H68F 109.5 . . ?
H68D C68 H68F 109.5 . . ?
H68E C68 H68F 109.5 . . ?
N1 C69 H69A 109.5 . . ?
N1 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
N1 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C57 N1 C58 109.7(5) . . ?
C57 N1 C69 124.8(5) . . ?
C58 N1 C69 125.5(5) . . ?
C57 N2 C59 108.4(5) . . ?
C57 N2 C60 125.1(5) . . ?
C59 N2 C60 126.5(5) . . ?
C11 O1 Sm1 135.4(4) . . ?
C13 O2 Sm1 131.1(4) . . ?
C25 O3 Sm1 133.0(4) . . ?
C27 O4 Sm1 127.3(4) . . ?
C39 O5 Sm1 134.8(3) . . ?
C41 O6 Sm1 130.3(4) . . ?
C53 O7 Sm1 132.0(4) . . ?
C55 O8 Sm1 130.8(4) . . ?
O6 Sm1 O8 85.71(13) . . ?
O6 Sm1 O1 145.92(14) . . ?
O8 Sm1 O1 82.84(12) . . ?
O6 Sm1 O3 101.50(13) . . ?
O8 Sm1 O3 146.86(14) . . ?
O1 Sm1 O3 73.13(13) . . ?
O6 Sm1 O4 77.00(14) . . ?
O8 Sm1 O4 142.22(12) . . ?
O1 Sm1 O4 128.63(13) . . ?
O3 Sm1 O4 70.38(14) . . ?
O6 Sm1 O7 73.61(13) . . ?
O8 Sm1 O7 69.68(13) . . ?
O1 Sm1 O7 130.46(13) . . ?
O3 Sm1 O7 143.44(14) . . ?
O4 Sm1 O7 73.27(13) . . ?
O6 Sm1 O2 143.66(13) . . ?
O8 Sm1 O2 105.75(14) . . ?
O1 Sm1 O2 70.41(13) . . ?
O3 Sm1 O2 87.57(13) . . ?
O4 Sm1 O2 73.13(14) . . ?
O7 Sm1 O2 78.31(12) . . ?
O6 Sm1 O5 70.80(12) . . ?
O8 Sm1 O5 76.84(14) . . ?
O1 Sm1 O5 75.36(13) . . ?
O3 Sm1 O5 75.26(13) . . ?
O4 Sm1 O5 126.22(15) . . ?
O7 Sm1 O5 132.24(12) . . ?
O2 Sm1 O5 144.92(11) . . ?
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 1.358(4) . ?
C1 C6 1.414(5) . ?
C1 C11 1.485(6) . ?
C2 C3 1.432(4) . ?
C2 H2 0.9500 . ?
C3 C7 1.396(4) . ?
C3 C4 1.409(5) . ?
C4 C5 1.375(4) . ?
C4 C10 1.446(4) . ?
C5 C6 1.400(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.394(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.417(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.319(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 O1 1.263(6) . ?
C11 C12 1.432(9) . ?
C12 C13 1.385(7) . ?
C12 H12 0.9500 . ?
C13 O2 1.255(6) . ?
C13 C14 1.522(9) . ?
C14 F3 1.329(6) . ?
C14 F2 1.333(7) . ?
C14 F1 1.342(7) . ?
C15 C16 1.358(5) . ?
C15 C20 1.412(6) . ?
C15 C25 1.534(7) . ?
C16 C17 1.436(5) . ?
C16 H16 0.9500 . ?
C17 C21 1.392(5) . ?
C17 C18 1.407(5) . ?
C18 C19 1.369(5) . ?
C18 C24 1.451(5) . ?
C19 C20 1.405(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.396(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.418(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.313(6) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 O3 1.276(8) . ?
C25 C26 1.372(10) . ?
C26 C27 1.391(8) . ?
C26 H26 0.9500 . ?
C27 O4 1.265(7) . ?
C27 C28 1.519(10) . ?
C28 F6 1.278(9) . ?
C28 F5 1.337(8) . ?
C28 F4 1.342(8) . ?
C29 C30 1.365(8) . ?
C29 C34 1.419(7) . ?
C29 C39 1.500(9) . ?
C30 C31 1.440(8) . ?
C30 H30 0.9500 . ?
C31 C35 1.414(9) . ?
C31 C32 1.424(7) . ?
C32 C38 1.406(9) . ?
C32 C33 1.417(9) . ?
C33 C34 1.374(9) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.325(10) . ?
C35 H35 0.9500 . ?
C36 C37 1.410(9) . ?
C36 H36 0.9500 . ?
C37 C38 1.363(9) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 O5 1.240(7) . ?
C39 C40 1.441(7) . ?
C40 C41 1.393(9) . ?
C40 H40 0.9500 . ?
C41 O6 1.250(7) . ?
C41 C42 1.508(7) . ?
C42 F7 1.338(7) . ?
C42 F8 1.351(7) . ?
C42 F9 1.352(8) . ?
C43 C44 1.358(7) . ?
C43 C48 1.420(9) . ?
C43 C53 1.515(8) . ?
C44 C45 1.446(8) . ?
C44 H44 0.9500 . ?
C45 C49 1.392(8) . ?
C45 C46 1.440(9) . ?
C46 C47 1.396(7) . ?
C46 C52 1.424(9) . ?
C47 C48 1.365(8) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 C50 1.375(9) . ?
C49 H49 0.9500 . ?
C50 C51 1.393(11) . ?
C50 H50 0.9500 . ?
C51 C52 1.372(9) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 O7 1.254(6) . ?
C53 C54 1.440(9) . ?
C54 C55 1.372(7) . ?
C54 H54 0.9500 . ?
C55 O8 1.275(5) . ?
C55 C56 1.515(9) . ?
C56 F10 1.316(8) . ?
C56 F11 1.328(8) . ?
C56 F12 1.333(6) . ?
C57 N1 1.319(7) . ?
C57 N2 1.338(8) . ?
C57 H57 0.9500 . ?
C58 C59 1.348(8) . ?
C58 N1 1.388(8) . ?
C58 H58 0.9500 . ?
C59 N2 1.359(8) . ?
C59 H59 0.9500 . ?
C60 N2 1.489(7) . ?
C60 C61 1.542(8) . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 C62 1.550(7) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 C63 1.5102 . ?
C62 C66 1.579(19) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.513(7) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 C65 1.502(8) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
C66 C67 1.54(2) . ?
C66 H63A 0.9914 . ?
C66 H63B 0.7417 . ?
C66 H66C 0.9900 . ?
C66 H66D 0.9900 . ?
C67 C68 1.49(3) . ?
C67 H67C 0.9900 . ?
C67 H67D 0.9900 . ?
C68 H68D 0.9800 . ?
C68 H68E 0.9800 . ?
C68 H68F 0.9800 . ?
C69 N1 1.465(7) . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
O1 Sm1 2.384(3) . ?
O2 Sm1 2.413(4) . ?
O3 Sm1 2.408(4) . ?
O4 Sm1 2.408(5) . ?
O5 Sm1 2.447(4) . ?
O6 Sm1 2.369(3) . ?
O7 Sm1 2.411(3) . ?
O8 Sm1 2.384(4) . ?
