#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:32:58 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179850 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/46/7014672.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_7014672
loop_
_publ_author_name
'Kachi-Terajima, Chihiro'
'Yanagi, Katsuya'
'Kaziki, Toru'
'Kitazawa, Takafumi'
'Hasegawa, Miki'
_publ_section_title
;
 Luminescence tuning of imidazole-based lanthanide(iii) complexes [Ln =
 Sm, Eu, Gd, Tb, Dy].
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2249
_journal_page_last               2256
_journal_paper_doi               10.1039/c0dt01046d
_journal_volume                  40
_journal_year                    2011
_chemical_formula_sum            'C19 H28 N13 O10 Sm'
_chemical_formula_weight         748.89
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.252(2)
_cell_angle_beta                 107.393(2)
_cell_angle_gamma                103.955(2)
_cell_formula_units_Z            4
_cell_length_a                   11.0955(13)
_cell_length_b                   16.3259(19)
_cell_length_c                   17.628(2)
_cell_measurement_reflns_used    6718
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     2796.4(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18351
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.176
_exptl_absorpt_correction_T_max  0.5518
_exptl_absorpt_correction_T_min  0.3551
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS; Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1500
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         8.691
_refine_diff_density_min         -9.665
_refine_diff_density_rms         0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     779
_refine_ls_number_reflns         13501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0901
_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)+(0.1860P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2449
_refine_ls_wR_factor_ref         0.2640
_reflns_number_gt                9690
_reflns_number_total             13501
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0DT01046D.TXT
_cod_data_source_block           6_SmH3L
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7014672
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7127(10) 0.1882(6) 0.1062(6) 0.023(2) Uani 1 1 d . . .
H19A H 0.7268 0.1917 0.0540 0.027 Uiso 1 1 calc R . .
H19B H 0.6633 0.1252 0.0967 0.027 Uiso 1 1 calc R . .
C2 C 0.6299(10) 0.2451(6) 0.1248(6) 0.023(2) Uani 1 1 d . . .
H20A H 0.5420 0.2238 0.0778 0.027 Uiso 1 1 calc R . .
H20B H 0.6143 0.2419 0.1767 0.027 Uiso 1 1 calc R . .
C3 C 0.6506(9) 0.3790(6) 0.0890(6) 0.0177(19) Uani 1 1 d . . .
H21 H 0.5605 0.3521 0.0502 0.021 Uiso 1 1 calc R . .
C4 C 0.7303(9) 0.4678(6) 0.0971(5) 0.0162(18) Uani 1 1 d . . .
C5 C 0.6988(11) 0.5273(6) 0.0583(6) 0.025(2) Uani 1 1 d . . .
H23 H 0.6157 0.5189 0.0163 0.030 Uiso 1 1 calc R . .
C6 C 0.9043(9) 0.5859(6) 0.1494(6) 0.0198(19) Uani 1 1 d . . .
H24 H 0.9908 0.6284 0.1826 0.024 Uiso 1 1 calc R . .
C7 C 0.9372(9) 0.1822(6) 0.1437(5) 0.0175(18) Uani 1 1 d . . .
H25A H 0.9391 0.2007 0.0943 0.021 Uiso 1 1 calc R . .
H25B H 0.9026 0.1161 0.1249 0.021 Uiso 1 1 calc R . .
C8 C 1.0799(10) 0.2156(6) 0.2097(6) 0.0197(19) Uani 1 1 d . . .
H26A H 1.0832 0.1854 0.2527 0.024 Uiso 1 1 calc R . .
H26B H 1.1423 0.2019 0.1827 0.024 Uiso 1 1 calc R . .
C9 C 1.2434(9) 0.3543(6) 0.3011(5) 0.0176(19) Uani 1 1 d . . .
H27 H 1.3086 0.3252 0.3064 0.021 Uiso 1 1 calc R . .
C10 C 1.2787(10) 0.4457(6) 0.3497(6) 0.020(2) Uani 1 1 d . . .
C11 C 1.4011(10) 0.5039(6) 0.4082(6) 0.021(2) Uani 1 1 d . . .
H29 H 1.4848 0.4942 0.4220 0.025 Uiso 1 1 calc R . .
C12 C 1.2440(9) 0.5666(6) 0.4050(5) 0.0176(19) Uani 1 1 d . . .
H30 H 1.2024 0.6096 0.4178 0.021 Uiso 1 1 calc R . .
C13 C 0.8288(10) 0.1862(6) 0.2468(6) 0.021(2) Uani 1 1 d . . .
H31A H 0.8474 0.1293 0.2416 0.025 Uiso 1 1 calc R . .
H31B H 0.7339 0.1739 0.2408 0.025 Uiso 1 1 calc R . .
C14 C 0.9169(10) 0.2513(6) 0.3340(5) 0.0183(19) Uani 1 1 d . . .
H32A H 0.8876 0.2314 0.3765 0.022 Uiso 1 1 calc R . .
H32B H 1.0110 0.2539 0.3463 0.022 Uiso 1 1 calc R . .
C15 C 0.8690(9) 0.3807(6) 0.3914(5) 0.0163(18) Uani 1 1 d . . .
H33 H 0.8502 0.3561 0.4322 0.020 Uiso 1 1 calc R . .
C16 C 0.8560(10) 0.4664(6) 0.3886(5) 0.021(2) Uani 1 1 d . . .
C17 C 0.8180(10) 0.5268(6) 0.4373(6) 0.021(2) Uani 1 1 d . . .
H35 H 0.7950 0.5224 0.4844 0.025 Uiso 1 1 calc R . .
C18 C 0.8587(9) 0.5745(6) 0.3374(5) 0.0171(18) Uani 1 1 d . . .
H36 H 0.8672 0.6109 0.3031 0.021 Uiso 1 1 calc R . .
C19 C 0.6887(9) 0.3418(6) 0.8747(6) 0.0186(19) Uani 1 1 d . . .
H7A H 0.7228 0.4060 0.8815 0.022 Uiso 1 1 calc R . .
H7B H 0.6713 0.3368 0.9256 0.022 Uiso 1 1 calc R . .
C20 C 0.7921(9) 0.3002(6) 0.8660(6) 0.0171(19) Uani 1 1 d . . .
H8A H 0.8104 0.3049 0.8153 0.021 Uiso 1 1 calc R . .
H8B H 0.8766 0.3312 0.9158 0.021 Uiso 1 1 calc R . .
C21 C 0.8170(9) 0.1715(6) 0.9009(5) 0.0166(18) Uani 1 1 d . . .
H9 H 0.9084 0.2045 0.9346 0.020 Uiso 1 1 calc R . .
C22 C 0.7580(9) 0.0788(6) 0.8944(6) 0.0166(18) Uani 1 1 d . . .
C23 C 0.8154(10) 0.0205(7) 0.9251(6) 0.024(2) Uani 1 1 d . . .
H11 H 0.9071 0.0322 0.9568 0.029 Uiso 1 1 calc R . .
C24 C 0.6002(10) -0.0459(7) 0.8556(6) 0.024(2) Uani 1 1 d . . .
H12 H 0.5148 -0.0913 0.8305 0.029 Uiso 1 1 calc R . .
C25 C 0.4494(10) 0.3169(6) 0.8206(6) 0.020(2) Uani 1 1 d . . .
H1A H 0.4653 0.3818 0.8344 0.024 Uiso 1 1 calc R . .
H1B H 0.4487 0.3007 0.8713 0.024 Uiso 1 1 calc R . .
C26 C 0.3128(9) 0.2664(6) 0.7494(6) 0.0174(18) Uani 1 1 d . . .
H2A H 0.2403 0.2700 0.7705 0.021 Uiso 1 1 calc R . .
H2B H 0.3032 0.2930 0.7037 0.021 Uiso 1 1 calc R . .
C27 C 0.1925(10) 0.1171(6) 0.6618(6) 0.021(2) Uani 1 1 d . . .
H3 H 0.1154 0.1346 0.6458 0.026 Uiso 1 1 calc R . .
C28 C 0.1878(10) 0.0261(6) 0.6234(6) 0.022(2) Uani 1 1 d . . .
C29 C 0.0817(10) -0.0475(6) 0.5654(6) 0.023(2) Uani 1 1 d . . .
H5 H -0.0093 -0.0514 0.5416 0.027 Uiso 1 1 calc R . .
C30 C 0.2685(10) -0.0805(6) 0.5970(5) 0.0182(19) Uani 1 1 d . . .
H6 H 0.3283 -0.1135 0.5976 0.022 Uiso 1 1 calc R . .
C31 C 0.5742(10) 0.3280(6) 0.7275(5) 0.020(2) Uani 1 1 d . . .
H13A H 0.6707 0.3523 0.7383 0.024 Uiso 1 1 calc R . .
H13B H 0.5370 0.3772 0.7259 0.024 Uiso 1 1 calc R . .
C32 C 0.5048(9) 0.2553(6) 0.6417(6) 0.0162(18) Uani 1 1 d . . .
H14A H 0.4066 0.2415 0.6230 0.019 Uiso 1 1 calc R . .
H14B H 0.5347 0.2762 0.5997 0.019 Uiso 1 1 calc R . .
C33 C 0.5909(9) 0.1404(6) 0.6013(5) 0.0161(18) Uani 1 1 d . . .
H15 H 0.6049 0.1634 0.5586 0.019 Uiso 1 1 calc R . .
C34 C 0.6290(9) 0.0638(6) 0.6142(5) 0.0166(18) Uani 1 1 d . . .
C35 C 0.6851(11) 0.0123(7) 0.5737(6) 0.023(2) Uani 1 1 d . . .
H17 H 0.7104 0.0186 0.5278 0.028 Uiso 1 1 calc R . .
C36 C 0.6493(10) -0.0352(6) 0.6746(6) 0.022(2) Uani 1 1 d . . .
H18A H 0.6469 -0.0694 0.7115 0.026 Uiso 1 1 calc R . .
C37 C 0.4894(12) 0.4423(7) 0.2071(7) 0.032(3) Uani 1 1 d . . .
H37A H 0.5781 0.4884 0.2352 0.049 Uiso 1 1 calc R . .
H37B H 0.4985 0.3836 0.2048 0.049 Uiso 1 1 calc R . .
H37C H 0.4325 0.4539 0.2385 0.049 Uiso 1 1 calc R . .
C38 C 0.9741(13) 0.8840(8) 0.1957(8) 0.042(3) Uani 1 1 d . . .
H38A H 0.9180 0.9019 0.2255 0.062 Uiso 1 1 calc R . .
H38B H 0.9412 0.8874 0.1387 0.062 Uiso 1 1 calc R . .
H38C H 1.0669 0.9242 0.2260 0.062 Uiso 1 1 calc R . .
N1 N 0.8467(8) 0.2173(5) 0.1770(5) 0.0169(16) Uani 1 1 d . . .
N2 N 0.7053(8) 0.3380(5) 0.1357(5) 0.0225(19) Uani 1 1 d . . .
N3 N 0.8632(8) 0.5043(5) 0.1551(5) 0.0160(16) Uani 1 1 d . . .
N4 N 0.8108(8) 0.6012(5) 0.0920(5) 0.0214(17) Uani 1 1 d . . .
H15A H 0.8198 0.6502 0.0782 0.026 Uiso 1 1 calc R . .
N5 N 1.1191(8) 0.3115(5) 0.2490(5) 0.0172(16) Uani 1 1 d . . .
N6 N 1.1803(8) 0.4863(5) 0.3483(5) 0.0180(16) Uani 1 1 d . . .
N7 N 1.3750(9) 0.5796(5) 0.4424(5) 0.0231(19) Uani 1 1 d . . .
H18 H 1.4345 0.6283 0.4822 0.028 Uiso 1 1 calc R . .
N8 N 0.9065(8) 0.3398(5) 0.3375(5) 0.0156(15) Uani 1 1 d . . .
N9 N 0.8828(8) 0.4974(5) 0.3266(5) 0.0160(15) Uani 1 1 d . . .
N10 N 0.8207(8) 0.5940(5) 0.4031(5) 0.0190(16) Uani 1 1 d . . .
H39 H 0.8010 0.6421 0.4211 0.023 Uiso 1 1 calc R . .
N11 N 1.0525(8) 0.4222(5) 0.0939(5) 0.0191(17) Uani 1 1 d . . .
N12 N 0.5595(8) 0.2969(5) 0.7986(4) 0.0145(15) Uani 1 1 d . . .
N13 N 0.7404(8) 0.2068(5) 0.8592(4) 0.0174(16) Uani 1 1 d . . .
N14 N 0.6217(8) 0.0355(5) 0.8505(4) 0.0169(16) Uani 1 1 d . . .
N15 N 0.7120(8) -0.0572(6) 0.8999(5) 0.0236(18) Uani 1 1 d . . .
H7 H 0.7179 -0.1063 0.9110 0.028 Uiso 1 1 calc R . .
N16 N 0.3039(7) 0.1721(5) 0.7175(5) 0.0159(15) Uani 1 1 d . . .
N17 N 0.3033(7) 0.0040(5) 0.6426(4) 0.0163(16) Uani 1 1 d . . .
N18 N 0.1356(8) -0.1135(5) 0.5494(4) 0.0187(17) Uani 1 1 d . . .
H4 H 0.0915 -0.1681 0.5141 0.022 Uiso 1 1 calc R . .
N19 N 0.5390(8) 0.1751(5) 0.6486(4) 0.0161(16) Uani 1 1 d . . .
N20 N 0.6069(8) 0.0327(5) 0.6768(5) 0.0184(16) Uani 1 1 d . . .
N21 N 0.6976(9) -0.0505(5) 0.6124(5) 0.0230(18) Uani 1 1 d . . .
H10 H 0.7308 -0.0931 0.5993 0.028 Uiso 1 1 calc R . .
N22 N 0.3931(9) 0.0944(6) 0.8943(5) 0.026(2) Uani 1 1 d . . .
N23 N 0.4440(8) 0.7416(6) 0.6235(5) 0.0225(18) Uani 1 1 d . . .
N24 N 0.7959(9) 0.7742(5) 0.9577(5) 0.0240(18) Uani 1 1 d . . .
N25 N 0.7808(9) 0.7557(6) 0.5319(5) 0.029(2) Uani 1 1 d . . .
N26 N 0.1027(8) 0.7389(6) 0.3749(5) 0.0220(18) Uani 1 1 d . . .
O1 O 1.1210(7) 0.4693(4) 0.1714(4) 0.0198(14) Uani 1 1 d . . .
O2 O 0.9505(7) 0.3557(4) 0.0802(4) 0.0198(14) Uani 1 1 d . . .
O3 O 1.0797(8) 0.4418(5) 0.0370(4) 0.0294(18) Uani 1 1 d . . .
O4 O 0.3427(7) 0.0390(4) 0.8199(4) 0.0206(15) Uani 1 1 d . . .
O5 O 0.4843(7) 0.1665(4) 0.9063(4) 0.0216(15) Uani 1 1 d . . .
O6 O 0.3576(9) 0.0796(6) 0.9502(5) 0.046(3) Uani 1 1 d . . .
O7 O 0.4489(10) 0.7585(5) 0.5588(5) 0.046(2) Uani 1 1 d . . .
O8 O 0.4266(9) 0.7958(5) 0.6779(5) 0.037(2) Uani 1 1 d . . .
O9 O 0.4542(9) 0.6693(5) 0.6315(5) 0.041(2) Uani 1 1 d . . .
O10 O 0.8917(7) 0.8441(5) 0.9836(5) 0.0334(18) Uani 1 1 d . . .
O11 O 0.6867(7) 0.7668(5) 0.9045(6) 0.037(2) Uani 1 1 d . . .
O12 O 0.8105(10) 0.7072(5) 0.9789(5) 0.047(2) Uani 1 1 d . . .
O13 O 0.8178(8) 0.7691(5) 0.4730(4) 0.0288(17) Uani 1 1 d . . .
O14 O 0.7130(10) 0.6795(5) 0.5236(6) 0.043(2) Uani 1 1 d . . .
O15 O 0.8131(10) 0.8197(6) 0.5974(5) 0.048(2) Uani 1 1 d . . .
O16 O 0.1288(8) 0.7285(5) 0.4461(4) 0.0297(17) Uani 1 1 d . . .
O17 O 0.0317(8) 0.7858(6) 0.3563(5) 0.0365(19) Uani 1 1 d . . .
O18 O 0.1489(8) 0.7048(5) 0.3240(5) 0.0301(17) Uani 1 1 d . . .
O19 O 0.4302(8) 0.4436(5) 0.1239(5) 0.0329(18) Uani 1 1 d . . .
H19 H 0.3606 0.3988 0.0970 0.049 Uiso 1 1 calc R . .
O20 O 0.9684(9) 0.7953(5) 0.1912(6) 0.041(2) Uani 1 1 d . . .
H20 H 0.8887 0.7610 0.1657 0.062 Uiso 1 1 calc R . .
Sm1 Sm 0.95492(4) 0.39934(3) 0.22568(3) 0.01314(15) Uani 1 1 d . . .
Sm2 Sm 0.50286(4) 0.11960(3) 0.76633(2) 0.01213(15) 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 0.0033 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'
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'
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 111.9(8) . . ?
C2 C1 H19A 109.2 . . ?
N1 C1 H19A 109.2 . . ?
C2 C1 H19B 109.2 . . ?
N1 C1 H19B 109.2 . . ?
H19A C1 H19B 107.9 . . ?
N2 C2 C1 107.5(8) . . ?
N2 C2 H20A 110.2 . . ?
C1 C2 H20A 110.2 . . ?
N2 C2 H20B 110.2 . . ?
C1 C2 H20B 110.2 . . ?
H20A C2 H20B 108.5 . . ?
N2 C3 C4 118.2(8) . . ?
N2 C3 H21 120.9 . . ?
C4 C3 H21 120.9 . . ?
C5 C4 N3 110.1(8) . . ?
C5 C4 C3 131.3(8) . . ?
N3 C4 C3 118.6(8) . . ?
C4 C5 N4 106.1(9) . . ?
C4 C5 H23 126.9 . . ?
N4 C5 H23 126.9 . . ?
N4 C6 N3 112.8(8) . . ?
N4 C6 H24 123.6 . . ?
N3 C6 H24 123.6 . . ?
N1 C7 C8 111.8(7) . . ?
N1 C7 H25A 109.3 . . ?
C8 C7 H25A 109.3 . . ?
N1 C7 H25B 109.3 . . ?
C8 C7 H25B 109.3 . . ?
H25A C7 H25B 107.9 . . ?
N5 C8 C7 108.6(8) . . ?
N5 C8 H26A 110.0 . . ?
C7 C8 H26A 110.0 . . ?
N5 C8 H26B 110.0 . . ?
C7 C8 H26B 110.0 . . ?
H26A C8 H26B 108.4 . . ?
N5 C9 C10 118.5(9) . . ?
N5 C9 H27 120.8 . . ?
C10 C9 H27 120.8 . . ?
C11 C10 N6 109.6(9) . . ?
C11 C10 C9 129.2(10) . . ?
N6 C10 C9 120.9(8) . . ?
C10 C11 N7 104.8(9) . . ?
C10 C11 H29 127.6 . . ?
N7 C11 H29 127.6 . . ?
N6 C12 N7 111.3(9) . . ?
N6 C12 H30 124.3 . . ?
N7 C12 H30 124.3 . . ?
N1 C13 C14 114.7(7) . . ?
N1 C13 H31A 108.6 . . ?
C14 C13 H31A 108.6 . . ?
N1 C13 H31B 108.6 . . ?
C14 C13 H31B 108.6 . . ?
H31A C13 H31B 107.6 . . ?
N8 C14 C13 108.8(7) . . ?
N8 C14 H32A 109.9 . . ?
C13 C14 H32A 109.9 . . ?
N8 C14 H32B 109.9 . . ?
C13 C14 H32B 109.9 . . ?
H32A C14 H32B 108.3 . . ?
N8 C15 C16 117.5(8) . . ?
N8 C15 H33 121.3 . . ?
C16 C15 H33 121.3 . . ?
N9 C16 C17 109.9(8) . . ?
N9 C16 C15 118.2(9) . . ?
C17 C16 C15 131.8(9) . . ?
N10 C17 C16 105.0(8) . . ?
N10 C17 H35 127.5 . . ?
C16 C17 H35 127.5 . . ?
N9 C18 N10 111.3(8) . . ?
N9 C18 H36 124.4 . . ?
N10 C18 H36 124.4 . . ?
C20 C19 N12 111.1(8) . . ?
C20 C19 H7A 109.4 . . ?
N12 C19 H7A 109.4 . . ?
C20 C19 H7B 109.4 . . ?
N12 C19 H7B 109.4 . . ?
H7A C19 H7B 108.0 . . ?
N13 C20 C19 107.9(7) . . ?
N13 C20 H8A 110.1 . . ?
C19 C20 H8A 110.1 . . ?
N13 C20 H8B 110.1 . . ?
C19 C20 H8B 110.1 . . ?
H8A C20 H8B 108.4 . . ?
N13 C21 C22 117.4(8) . . ?
N13 C21 H9 121.3 . . ?
C22 C21 H9 121.3 . . ?
N14 C22 C23 109.3(8) . . ?
N14 C22 C21 119.5(8) . . ?
C23 C22 C21 131.2(9) . . ?
N15 C23 C22 105.3(9) . . ?
N15 C23 H11 127.4 . . ?
C22 C23 H11 127.4 . . ?
N14 C24 N15 112.3(9) . . ?
N14 C24 H12 123.8 . . ?
N15 C24 H12 123.8 . . ?
N12 C25 C26 112.3(8) . . ?
N12 C25 H1A 109.1 . . ?
C26 C25 H1A 109.1 . . ?
N12 C25 H1B 109.1 . . ?
C26 C25 H1B 109.1 . . ?
H1A C25 H1B 107.9 . . ?
N16 C26 C25 108.1(7) . . ?
N16 C26 H2A 110.1 . . ?
C25 C26 H2A 110.1 . . ?
N16 C26 H2B 110.1 . . ?
C25 C26 H2B 110.1 . . ?
H2A C26 H2B 108.4 . . ?
N16 C27 C28 117.7(9) . . ?
N16 C27 H3 121.1 . . ?
C28 C27 H3 121.1 . . ?
N17 C28 C29 109.4(9) . . ?
N17 C28 C27 120.2(8) . . ?
C29 C28 C27 130.4(10) . . ?
N18 C29 C28 105.4(9) . . ?
N18 C29 H5 127.3 . . ?
C28 C29 H5 127.3 . . ?
N17 C30 N18 110.6(9) . . ?
N17 C30 H6 124.7 . . ?
N18 C30 H6 124.7 . . ?
N12 C31 C32 114.1(7) . . ?
N12 C31 H13A 108.7 . . ?
C32 C31 H13A 108.7 . . ?
N12 C31 H13B 108.7 . . ?
C32 C31 H13B 108.7 . . ?
H13A C31 H13B 107.6 . . ?
N19 C32 C31 108.8(7) . . ?
N19 C32 H14A 109.9 . . ?
C31 C32 H14A 109.9 . . ?
N19 C32 H14B 109.9 . . ?
C31 C32 H14B 109.9 . . ?
H14A C32 H14B 108.3 . . ?
N19 C33 C34 117.6(8) . . ?
N19 C33 H15 121.2 . . ?
C34 C33 H15 121.2 . . ?
C35 C34 N20 109.2(8) . . ?
C35 C34 C33 131.4(9) . . ?
N20 C34 C33 119.3(9) . . ?
C34 C35 N21 105.9(9) . . ?
C34 C35 H17 127.1 . . ?
N21 C35 H17 127.1 . . ?
N20 C36 N21 110.6(9) . . ?
N20 C36 H18A 124.7 . . ?
N21 C36 H18A 124.7 . . ?
O19 C37 H37A 109.5 . . ?
O19 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O19 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O20 C38 H38A 109.5 . . ?
O20 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O20 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C7 N1 C13 112.9(8) . . ?
C7 N1 C1 108.3(7) . . ?
C13 N1 C1 109.3(7) . . ?
C7 N1 Sm1 105.8(5) . . ?
C13 N1 Sm1 112.1(5) . . ?
C1 N1 Sm1 108.3(5) . . ?
C3 N2 C2 119.5(8) . . ?
C3 N2 Sm1 121.4(6) . . ?
C2 N2 Sm1 118.0(6) . . ?
C6 N3 C4 103.2(7) . . ?
C6 N3 Sm1 140.4(6) . . ?
C4 N3 Sm1 116.2(5) . . ?
C6 N4 C5 107.8(8) . . ?
C6 N4 H15A 126.1 . . ?
C5 N4 H15A 126.1 . . ?
C9 N5 C8 117.8(8) . . ?
C9 N5 Sm1 118.9(6) . . ?
C8 N5 Sm1 123.3(6) . . ?
C12 N6 C10 105.4(8) . . ?
C12 N6 Sm1 139.4(7) . . ?
C10 N6 Sm1 114.0(6) . . ?
C12 N7 C11 108.9(8) . . ?
C12 N7 H18 125.6 . . ?
C11 N7 H18 125.6 . . ?
C15 N8 C14 120.8(8) . . ?
C15 N8 Sm1 123.2(6) . . ?
C14 N8 Sm1 116.0(6) . . ?
C18 N9 C16 105.1(8) . . ?
C18 N9 Sm1 137.7(6) . . ?
C16 N9 Sm1 117.2(6) . . ?
C18 N10 C17 108.6(8) . . ?
C18 N10 H39 125.7 . . ?
C17 N10 H39 125.7 . . ?
O3 N11 O2 122.2(7) . . ?
O3 N11 O1 122.0(7) . . ?
O2 N11 O1 115.7(7) . . ?
O3 N11 Sm1 168.2(7) . . ?
O2 N11 Sm1 58.3(4) . . ?
O1 N11 Sm1 58.3(4) . . ?
C25 N12 C31 111.7(7) . . ?
C25 N12 C19 109.1(7) . . ?
C31 N12 C19 109.5(7) . . ?
C25 N12 Sm2 105.1(5) . . ?
C31 N12 Sm2 114.1(5) . . ?
C19 N12 Sm2 107.0(5) . . ?
C21 N13 C20 119.9(8) . . ?
C21 N13 Sm2 121.7(6) . . ?
C20 N13 Sm2 118.4(6) . . ?
C24 N14 C22 104.9(8) . . ?
C24 N14 Sm2 139.0(6) . . ?
C22 N14 Sm2 114.7(5) . . ?
C24 N15 C23 108.2(8) . . ?
C24 N15 H7 125.9 . . ?
C23 N15 H7 125.9 . . ?
C27 N16 C26 117.7(8) . . ?
C27 N16 Sm2 120.1(7) . . ?
C26 N16 Sm2 122.2(5) . . ?
C30 N17 C28 106.3(8) . . ?
C30 N17 Sm2 137.6(6) . . ?
C28 N17 Sm2 115.0(6) . . ?
C30 N18 C29 108.4(8) . . ?
C30 N18 H4 125.8 . . ?
C29 N18 H4 125.8 . . ?
C33 N19 C32 120.3(8) . . ?
C33 N19 Sm2 123.0(6) . . ?
C32 N19 Sm2 116.5(6) . . ?
C36 N20 C34 106.6(8) . . ?
C36 N20 Sm2 137.2(6) . . ?
C34 N20 Sm2 116.1(6) . . ?
C36 N21 C35 107.6(9) . . ?
C36 N21 H10 126.2 . . ?
C35 N21 H10 126.2 . . ?
O6 N22 O4 122.4(8) . . ?
O6 N22 O5 122.2(8) . . ?
O4 N22 O5 115.4(8) . . ?
O6 N22 Sm2 173.0(9) . . ?
O4 N22 Sm2 57.9(4) . . ?
O5 N22 Sm2 58.0(4) . . ?
O8 N23 O7 119.8(9) . . ?
O8 N23 O9 121.3(9) . . ?
O7 N23 O9 119.0(10) . . ?
O10 N24 O11 119.9(8) . . ?
O10 N24 O12 120.6(9) . . ?
O11 N24 O12 119.3(8) . . ?
O14 N25 O15 121.0(10) . . ?
O14 N25 O13 119.4(9) . . ?
O15 N25 O13 119.6(9) . . ?
O18 N26 O17 120.0(8) . . ?
O18 N26 O16 121.0(9) . . ?
O17 N26 O16 119.0(9) . . ?
N11 O1 Sm1 95.5(5) . . ?
N11 O2 Sm1 95.6(5) . . ?
N22 O4 Sm2 96.5(5) . . ?
N22 O5 Sm2 96.3(5) . . ?
C37 O19 H19 109.5 . . ?
C38 O20 H20 109.5 . . ?
O1 Sm1 O2 51.97(19) . . ?
O1 Sm1 N8 149.1(2) . . ?
O2 Sm1 N8 144.0(2) . . ?
O1 Sm1 N2 120.9(2) . . ?
O2 Sm1 N2 76.9(2) . . ?
N8 Sm1 N2 89.7(2) . . ?
O1 Sm1 N9 119.9(2) . . ?
O2 Sm1 N9 144.1(2) . . ?
N8 Sm1 N9 64.0(2) . . ?
N2 Sm1 N9 83.4(3) . . ?
O1 Sm1 N3 72.8(2) . . ?
O2 Sm1 N3 72.9(2) . . ?
N8 Sm1 N3 130.9(3) . . ?
N2 Sm1 N3 64.6(2) . . ?
N9 Sm1 N3 71.6(2) . . ?
O1 Sm1 N6 70.6(2) . . ?
O2 Sm1 N6 119.0(2) . . ?
N8 Sm1 N6 81.0(2) . . ?
N2 Sm1 N6 162.4(3) . . ?
N9 Sm1 N6 79.1(3) . . ?
N3 Sm1 N6 110.8(2) . . ?
O1 Sm1 N5 78.0(2) . . ?
O2 Sm1 N5 82.8(2) . . ?
N8 Sm1 N5 79.4(3) . . ?
N2 Sm1 N5 127.6(3) . . ?
N9 Sm1 N5 132.4(2) . . ?
N3 Sm1 N5 149.6(2) . . ?
N6 Sm1 N5 65.5(2) . . ?
O1 Sm1 N1 120.3(2) . . ?
O2 Sm1 N1 78.8(2) . . ?
N8 Sm1 N1 65.3(2) . . ?
N2 Sm1 N1 66.1(3) . . ?
N9 Sm1 N1 119.8(2) . . ?
N3 Sm1 N1 127.3(2) . . ?
N6 Sm1 N1 121.8(2) . . ?
N5 Sm1 N1 62.8(2) . . ?
O1 Sm1 N11 26.2(2) . . ?
O2 Sm1 N11 26.1(2) . . ?
N8 Sm1 N11 160.8(3) . . ?
N2 Sm1 N11 97.7(2) . . ?
N9 Sm1 N11 134.3(2) . . ?
N3 Sm1 N11 68.0(2) . . ?
N6 Sm1 N11 95.9(2) . . ?
N5 Sm1 N11 82.1(2) . . ?
N1 Sm1 N11 101.6(2) . . ?
N13 Sm2 O4 121.6(2) . . ?
N13 Sm2 O5 78.5(2) . . ?
O4 Sm2 O5 51.2(2) . . ?
N13 Sm2 N17 159.5(3) . . ?
O4 Sm2 N17 71.0(2) . . ?
O5 Sm2 N17 119.4(2) . . ?
N13 Sm2 N16 130.1(3) . . ?
O4 Sm2 N16 77.5(2) . . ?
O5 Sm2 N16 83.9(2) . . ?
N17 Sm2 N16 65.7(3) . . ?
N13 Sm2 N14 65.9(2) . . ?
O4 Sm2 N14 73.0(2) . . ?
O5 Sm2 N14 74.8(2) . . ?
N17 Sm2 N14 107.2(2) . . ?
N16 Sm2 N14 150.3(2) . . ?
N13 Sm2 N19 89.9(2) . . ?
O4 Sm2 N19 148.0(2) . . ?
O5 Sm2 N19 143.6(2) . . ?
N17 Sm2 N19 80.7(2) . . ?
N16 Sm2 N19 77.5(3) . . ?
N14 Sm2 N19 131.3(3) . . ?
N13 Sm2 N20 84.0(2) . . ?
O4 Sm2 N20 120.2(2) . . ?
O5 Sm2 N20 146.3(2) . . ?
N17 Sm2 N20 75.5(3) . . ?
N16 Sm2 N20 128.7(2) . . ?
N14 Sm2 N20 71.8(2) . . ?
N19 Sm2 N20 63.9(2) . . ?
N13 Sm2 N12 67.0(2) . . ?
O4 Sm2 N12 119.2(2) . . ?
O5 Sm2 N12 78.4(2) . . ?
N17 Sm2 N12 123.6(2) . . ?
N16 Sm2 N12 63.9(2) . . ?
N14 Sm2 N12 129.2(2) . . ?
N19 Sm2 N12 65.3(2) . . ?
N20 Sm2 N12 120.5(2) . . ?
N13 Sm2 N22 99.4(2) . . ?
O4 Sm2 N22 25.6(2) . . ?
O5 Sm2 N22 25.8(2) . . ?
N17 Sm2 N22 95.8(2) . . ?
N16 Sm2 N22 81.7(3) . . ?
N14 Sm2 N22 70.1(3) . . ?
N19 Sm2 N22 158.5(3) . . ?
N20 Sm2 N22 136.1(2) . . ?
N12 Sm2 N22 100.4(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
C1 C2 1.506(15) . ?
C1 N1 1.507(12) . ?
C1 H19A 0.9900 . ?
C1 H19B 0.9900 . ?
C2 N2 1.483(11) . ?
C2 H20A 0.9900 . ?
C2 H20B 0.9900 . ?
C3 N2 1.281(13) . ?
C3 C4 1.454(12) . ?
C3 H21 0.9500 . ?
C4 C5 1.363(13) . ?
C4 N3 1.404(11) . ?
C5 N4 1.364(12) . ?
C5 H23 0.9500 . ?
C6 N4 1.332(12) . ?
C6 N3 1.339(11) . ?
C6 H24 0.9500 . ?
C7 N1 1.468(12) . ?
C7 C8 1.533(12) . ?
C7 H25A 0.9900 . ?
C7 H25B 0.9900 . ?
C8 N5 1.455(11) . ?
C8 H26A 0.9900 . ?
C8 H26B 0.9900 . ?
C9 N5 1.311(11) . ?
C9 C10 1.430(13) . ?
C9 H27 0.9500 . ?
C10 C11 1.379(12) . ?
C10 N6 1.404(13) . ?
C11 N7 1.381(13) . ?
C11 H29 0.9500 . ?
C12 N6 1.322(11) . ?
C12 N7 1.345(12) . ?
C12 H30 0.9500 . ?
C13 N1 1.483(11) . ?
C13 C14 1.516(12) . ?
C13 H31A 0.9900 . ?
C13 H31B 0.9900 . ?
C14 N8 1.466(11) . ?
C14 H32A 0.9900 . ?
C14 H32B 0.9900 . ?
C15 N8 1.265(12) . ?
C15 C16 1.453(14) . ?
C15 H33 0.9500 . ?
C16 N9 1.382(11) . ?
C16 C17 1.384(14) . ?
C17 N10 1.366(12) . ?
C17 H35 0.9500 . ?
C18 N9 1.332(12) . ?
C18 N10 1.345(12) . ?
C18 H36 0.9500 . ?
C19 C20 1.494(14) . ?
C19 N12 1.511(11) . ?
C19 H7A 0.9900 . ?
C19 H7B 0.9900 . ?
C20 N13 1.457(11) . ?
C20 H8A 0.9900 . ?
C20 H8B 0.9900 . ?
C21 N13 1.285(13) . ?
C21 C22 1.460(12) . ?
C21 H9 0.9500 . ?
C22 N14 1.385(11) . ?
C22 C23 1.388(13) . ?
C23 N15 1.362(12) . ?
C23 H11 0.9500 . ?
C24 N14 1.321(12) . ?
C24 N15 1.334(13) . ?
C24 H12 0.9500 . ?
C25 N12 1.473(13) . ?
C25 C26 1.529(12) . ?
C25 H1A 0.9900 . ?
C25 H1B 0.9900 . ?
C26 N16 1.481(11) . ?
C26 H2A 0.9900 . ?
C26 H2B 0.9900 . ?
C27 N16 1.278(12) . ?
C27 C28 1.465(14) . ?
C27 H3 0.9500 . ?
C28 N17 1.380(13) . ?
C28 C29 1.382(12) . ?
C29 N18 1.368(14) . ?
C29 H5 0.9500 . ?
C30 N17 1.322(12) . ?
C30 N18 1.356(12) . ?
C30 H6 0.9500 . ?
C31 N12 1.493(11) . ?
C31 C32 1.526(12) . ?
C31 H13A 0.9900 . ?
C31 H13B 0.9900 . ?
C32 N19 1.470(11) . ?
C32 H14A 0.9900 . ?
C32 H14B 0.9900 . ?
C33 N19 1.255(12) . ?
C33 C34 1.457(13) . ?
C33 H15 0.9500 . ?
C34 C35 1.360(14) . ?
C34 N20 1.377(11) . ?
C35 N21 1.367(13) . ?
C35 H17 0.9500 . ?
C36 N20 1.302(13) . ?
C36 N21 1.357(13) . ?
C36 H18A 0.9500 . ?
C37 O19 1.424(13) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 O20 1.417(14) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
N1 Sm1 2.739(7) . ?
N2 Sm1 2.549(8) . ?
N3 Sm1 2.565(8) . ?
N4 H15A 0.8800 . ?
N5 Sm1 2.573(8) . ?
N6 Sm1 2.567(8) . ?
N7 H18 0.8800 . ?
N8 Sm1 2.525(7) . ?
N9 Sm1 2.556(8) . ?
N10 H39 0.8800 . ?
N11 O3 1.217(10) . ?
N11 O2 1.281(9) . ?
N11 O1 1.286(9) . ?
N11 Sm1 2.902(8) . ?
N12 Sm2 2.693(7) . ?
N13 Sm2 2.489(8) . ?
N14 Sm2 2.543(8) . ?
N15 H7 0.8800 . ?
N16 Sm2 2.543(7) . ?
N17 Sm2 2.536(7) . ?
N18 H4 0.8800 . ?
N19 Sm2 2.544(7) . ?
N20 Sm2 2.586(9) . ?
N21 H10 0.8800 . ?
N22 O6 1.217(11) . ?
N22 O4 1.274(10) . ?
N22 O5 1.280(10) . ?
N22 Sm2 2.927(8) . ?
N23 O8 1.242(12) . ?
N23 O7 1.247(11) . ?
N23 O9 1.248(12) . ?
N24 O10 1.236(10) . ?
N24 O11 1.249(11) . ?
N24 O12 1.264(11) . ?
N25 O14 1.239(11) . ?
N25 O15 1.255(11) . ?
N25 O13 1.267(11) . ?
N26 O18 1.250(11) . ?
N26 O17 1.251(12) . ?
N26 O16 1.261(10) . ?
O1 Sm1 2.481(6) . ?
O2 Sm1 2.481(6) . ?
O4 Sm2 2.496(6) . ?
O5 Sm2 2.496(6) . ?
O19 H19 0.8400 . ?
O20 H20 0.8400 . ?
