#------------------------------------------------------------------------------
#$Date: 2019-11-10 06:39:37 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225724 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/55/4515573.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_4515573
loop_
_publ_author_name
'Shirase, Satoru'
'Shinohara, Koichi'
'Tsurugi, Hayato'
'Mashima, Kazushi'
_publ_section_title
;
 Oxidation of Alcohols to Carbonyl Compounds Catalyzed by Oxo-Bridged
 Dinuclear Cerium Complexes with Pentadentate Schiff-Base Ligands under a
 Dioxygen Atmosphere
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              6939
_journal_paper_doi               10.1021/acscatal.8b01718
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C68 H102 Ce2 N8 O11'
_chemical_formula_sum            'C68 H102 Ce2 N8 O11'
_chemical_formula_weight         1487.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 122.0441(16)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   27.711(3)
_cell_length_b                   19.4594(18)
_cell_length_c                   15.5984(17)
_cell_measurement_reflns_used    7392
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      4.10
_cell_volume                     7129.7(13)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29813
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         4.080
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.321
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3080.00
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.07
_refine_diff_density_min         -0.73
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     435
_refine_ls_number_reflns         8098
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0463P)²+0.6727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6102
_reflns_number_total             8098
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cs8b01718_si_001.cif
_cod_data_source_block           complex7a
_cod_database_code               4515573
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
CE1 Ce 0.98859(2) 0.67998(2) 0.10761(2) 0.01899(6) Uani 1 1 d . . . . .
O1 O 0.91298(9) 0.61265(11) 0.04508(17) 0.0257(5) Uani 1 1 d . . . . .
O2 O 0.93810(9) 0.77420(10) 0.04510(16) 0.0238(5) Uani 1 1 d . . . . .
O3 O 1.03415(11) 0.72416(14) 0.0147(2) 0.0432(7) Uani 1 1 d . . . . .
O4 O 0.96511(11) 0.65304(12) -0.06927(19) 0.0358(6) Uani 1 1 d . . . . .
O5 O 1.00089(15) 0.70794(16) -0.1447(2) 0.0612(9) Uani 1 1 d . . . . .
O6 O 1.000000 0.66972(15) 0.250000 0.0294(7) Uani 1 2 d S T P . .
N1 N 1.02195(11) 0.55156(13) 0.1327(2) 0.0265(6) Uani 1 1 d . . . . .
N2 N 1.09773(13) 0.65637(16) 0.2167(4) 0.0555(11) Uani 1 1 d . . . . .
H2 H 1.103518 0.640516 0.282473 0.22(5) Uiso 1 1 calc R . . . .
N3 N 1.05005(11) 0.78672(13) 0.20417(18) 0.0237(6) Uani 1 1 d . . . . .
N4 N 1.00010(14) 0.69565(14) -0.0695(2) 0.0331(7) Uani 1 1 d . . . . .
C1 C 0.89344(14) 0.54900(18) 0.0400(3) 0.0300(8) Uani 1 1 d . . . . .
C2 C 0.83391(15) 0.53464(19) -0.0138(3) 0.0369(9) Uani 1 1 d . . . . .
C3 C 0.81753(19) 0.4681(2) -0.0060(3) 0.0516(13) Uani 1 1 d . . . . .
H3 H 0.777903 0.458596 -0.040425 0.040(10) Uiso 1 1 calc R . . . .
C4 C 0.8549(2) 0.4147(2) 0.0485(4) 0.0518(13) Uani 1 1 d . . . . .
C5 C 0.91211(19) 0.42835(18) 0.0937(3) 0.0440(11) Uani 1 1 d . . . . .
H5 H 0.938883 0.392700 0.129192 0.021(9) Uiso 1 1 calc R . . . .
C6 C 0.93203(16) 0.49453(16) 0.0885(3) 0.0318(8) Uani 1 1 d . . . . .
C7 C 0.99255(15) 0.49956(17) 0.1304(3) 0.0312(8) Uani 1 1 d . . . . .
H7 H 1.013640 0.458718 0.160441 0.028(9) Uiso 1 1 calc R . . . .
C8 C 1.08323(15) 0.53626(17) 0.1767(3) 0.0347(8) Uani 1 1 d . . . . .
H8A H 1.099489 0.515568 0.244583 0.054(12) Uiso 1 1 calc R . . . .
H8B H 1.087394 0.502731 0.133301 0.072(15) Uiso 1 1 calc R . . . .
C9 C 1.11452(19) 0.6001(2) 0.1848(6) 0.0755(19) Uani 1 1 d . . . . .
H9A H 1.155705 0.592196 0.232968 0.054(12) Uiso 1 1 calc R . . . .
H9B H 1.108914 0.610398 0.117988 0.27(6) Uiso 1 1 calc R . . . .
C10 C 1.13307(14) 0.71925(18) 0.2455(3) 0.0366(9) Uani 1 1 d . . . . .
H10A H 1.132250 0.738520 0.186024 0.037(10) Uiso 1 1 calc R . . . .
H10B H 1.173038 0.708473 0.298194 0.027(9) Uiso 1 1 calc R . . . .
C11 C 1.10865(14) 0.77030(17) 0.2855(2) 0.0317(8) Uani 1 1 d . . . . .
H11A H 1.108742 0.750454 0.344044 0.033(9) Uiso 1 1 calc R . . . .
H11B H 1.132064 0.812603 0.308156 0.038(10) Uiso 1 1 calc R . . . .
C12 C 1.03649(14) 0.85035(16) 0.1934(2) 0.0240(7) Uani 1 1 d . . . . .
H12 H 1.064715 0.880869 0.241325 0.031(9) Uiso 1 1 calc R . . . .
C13 C 0.98308(14) 0.88157(15) 0.1167(2) 0.0236(7) Uani 1 1 d . . . . .
C14 C 0.98136(15) 0.95427(17) 0.1171(2) 0.0282(7) Uani 1 1 d . . . . .
H14 H 1.013492 0.979119 0.167611 0.021(8) Uiso 1 1 calc R . . . .
C15 C 0.93351(17) 0.98961(16) 0.0450(2) 0.0336(9) Uani 1 1 d . . . . .
C16 C 0.88883(16) 0.95052(18) -0.0295(2) 0.0358(9) Uani 1 1 d . . . . .
H16 H 0.856169 0.974433 -0.080266 0.030(9) Uiso 1 1 calc R . . . .
C17 C 0.88819(15) 0.87903(17) -0.0354(2) 0.0301(8) Uani 1 1 d . . . . .
C18 C 0.93636(14) 0.84316(16) 0.0419(2) 0.0236(7) Uani 1 1 d . . . . .
C19 C 0.78932(15) 0.5894(2) -0.0752(3) 0.0448(10) Uani 1 1 d . . . . .
C20 C 0.80028(17) 0.6196(2) -0.1540(3) 0.0504(11) Uani 1 1 d . . . . .
H20A H 0.771619 0.654751 -0.193543 0.060 Uiso 1 1 calc R U . . .
H20B H 0.838291 0.640271 -0.119749 0.060 Uiso 1 1 calc R U . . .
H20C H 0.797935 0.582940 -0.199231 0.060 Uiso 1 1 calc R U . . .
C21 C 0.79142(16) 0.6448(2) -0.0021(3) 0.0412(9) Uani 1 1 d . . . . .
H21A H 0.762866 0.680302 -0.040955 0.049 Uiso 1 1 calc R U . . .
H21B H 0.783372 0.623563 0.045916 0.049 Uiso 1 1 calc R U . . .
H21C H 0.829355 0.665790 0.034888 0.049 Uiso 1 1 calc R U . . .
C22 C 0.72799(18) 0.5617(3) -0.1332(4) 0.0751(17) Uani 1 1 d . . . . .
H22A H 0.701546 0.599312 -0.170972 0.090 Uiso 1 1 calc R U . . .
H22B H 0.724312 0.525885 -0.180492 0.090 Uiso 1 1 calc R U . . .
H22C H 0.719028 0.542392 -0.085280 0.090 Uiso 1 1 calc R U . . .
C23 C 0.8325(2) 0.3435(2) 0.0550(4) 0.0651(15) Uani 1 1 d . . . . .
C24 C 0.8338(3) 0.2963(3) -0.0291(5) 0.0149(12) Uiso 0.5 1 d . . P A 1
H24A H 0.817492 0.251071 -0.031592 0.022 Uiso 0.5 1 calc R U P A 1
H24B H 0.873205 0.290752 -0.011278 0.022 Uiso 0.5 1 calc R U P A 1
H24C H 0.811405 0.318427 -0.095477 0.022 Uiso 0.5 1 calc R U P A 1
C25 C 0.8869(3) 0.2946(4) 0.1578(7) 0.044(2) Uani 0.5 1 d . . P A 1
H25A H 0.902357 0.320906 0.220593 0.065 Uiso 0.5 1 calc R U P A 1
H25B H 0.917329 0.284710 0.145383 0.065 Uiso 0.5 1 calc R U P A 1
H25C H 0.870767 0.251343 0.163760 0.065 Uiso 0.5 1 calc R U P A 1
C36 C 0.7938(5) 0.3458(6) 0.0945(12) 0.098(5) Uani 0.5 1 d . . P A 1
H36A H 0.814302 0.364931 0.163032 0.147 Uiso 0.5 1 calc R U P A 1
H36B H 0.780866 0.299167 0.096021 0.147 Uiso 0.5 1 calc R U P A 1
H36C H 0.760783 0.374759 0.050292 0.147 Uiso 0.5 1 calc R U P A 1
C35 C 0.8166(7) 0.3039(8) -0.0302(13) 0.108(6) Uiso 0.5 1 d . . P A 2
H35A H 0.838111 0.318771 -0.060455 0.161 Uiso 0.5 1 calc R U P A 2
H35B H 0.775779 0.309708 -0.079358 0.161 Uiso 0.5 1 calc R U P A 2
H35C H 0.824759 0.255448 -0.010741 0.161 Uiso 0.5 1 calc R U P A 2
C26 C 0.7624(4) 0.3531(4) 0.0048(8) 0.044(2) Uani 0.5 1 d . . P A 2
H26A H 0.746615 0.310494 0.013555 0.066 Uiso 0.5 1 calc R U P A 2
H26B H 0.743806 0.363407 -0.067519 0.066 Uiso 0.5 1 calc R U P A 2
H26C H 0.755822 0.390891 0.038796 0.066 Uiso 0.5 1 calc R U P A 2
C37 C 0.8588(4) 0.3217(5) 0.1446(7) 0.049(2) Uiso 0.5 1 d . . P A 2
H37A H 0.842700 0.277436 0.147151 0.073 Uiso 0.5 1 calc R U P A 2
H37B H 0.854994 0.354869 0.187926 0.073 Uiso 0.5 1 calc R U P A 2
H37C H 0.899124 0.315784 0.168427 0.073 Uiso 0.5 1 calc R U P A 2
C27 C 0.9283(2) 1.06865(17) 0.0458(3) 0.0448(11) Uani 1 1 d . . . . .
C28 C 0.9870(2) 1.10310(19) 0.1053(3) 0.0576(13) Uani 1 1 d . . . . .
H28A H 1.008745 1.091552 0.074174 0.069 Uiso 1 1 calc R U . . .
H28B H 0.982210 1.153055 0.104318 0.069 Uiso 1 1 calc R U . . .
H28C H 1.007457 1.086719 0.175360 0.069 Uiso 1 1 calc R U . . .
C29 C 0.8965(2) 1.0977(2) -0.0629(3) 0.0550(12) Uani 1 1 d . . . . .
H29A H 0.858799 1.076401 -0.102480 0.066 Uiso 1 1 calc R U . . .
H29B H 0.892262 1.147567 -0.060706 0.066 Uiso 1 1 calc R U . . .
H29C H 0.918271 1.087617 -0.094486 0.066 Uiso 1 1 calc R U . . .
C30 C 0.8934(2) 1.0861(2) 0.0933(4) 0.0649(15) Uani 1 1 d . . . . .
H30A H 0.856084 1.063765 0.054557 0.078 Uiso 1 1 calc R U . . .
H30B H 0.913562 1.069644 0.163329 0.078 Uiso 1 1 calc R U . . .
H30C H 0.888314 1.135980 0.092288 0.078 Uiso 1 1 calc R U . . .
C31 C 0.83724(15) 0.8422(2) -0.1230(2) 0.0371(9) Uani 1 1 d . . . . .
C32 C 0.85645(16) 0.79988(19) -0.1830(3) 0.0366(9) Uani 1 1 d . . . . .
H32A H 0.873796 0.830473 -0.209183 0.044 Uiso 1 1 calc R U . . .
H32B H 0.884364 0.765410 -0.138522 0.044 Uiso 1 1 calc R U . . .
H32C H 0.823420 0.776827 -0.239564 0.044 Uiso 1 1 calc R U . . .
C33 C 0.81017(16) 0.7953(2) -0.0818(3) 0.0473(10) Uani 1 1 d . . . . .
H33A H 0.777436 0.771626 -0.138005 0.057 Uiso 1 1 calc R U . . .
H33B H 0.838177 0.761368 -0.036075 0.057 Uiso 1 1 calc R U . . .
H33C H 0.797460 0.822859 -0.044756 0.057 Uiso 1 1 calc R U . . .
C34 C 0.79040(19) 0.8920(2) -0.1975(3) 0.0667(15) Uani 1 1 d . . . . .
H34A H 0.806088 0.923284 -0.225942 0.080 Uiso 1 1 calc R U . . .
H34B H 0.758880 0.865818 -0.252189 0.080 Uiso 1 1 calc R U . . .
H34C H 0.776439 0.918737 -0.161690 0.080 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 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Ce Ce -0.2486 2.6331
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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_3
O6 CE1 O2 104.73(9) .
O6 CE1 O1 89.18(7) .
O2 CE1 O1 93.87(8) .
O6 CE1 O3 143.75(7) .
O2 CE1 O3 81.70(8) .
O1 CE1 O3 126.44(8) .
O6 CE1 O4 161.72(9) .
O2 CE1 O4 87.38(8) .
O1 CE1 O4 76.18(8) .
O3 CE1 O4 50.39(8) .
O6 CE1 N3 77.08(9) .
O2 CE1 N3 69.97(8) .
O1 CE1 N3 154.81(8) .
O3 CE1 N3 71.77(8) .
O4 CE1 N3 120.50(8) .
O6 CE1 N2 79.62(11) .
O2 CE1 N2 133.03(9) .
O1 CE1 N2 133.10(9) .
O3 CE1 N2 70.98(12) .
O4 CE1 N2 102.30(12) .
N3 CE1 N2 65.55(9) .
O6 CE1 N1 84.68(10) .
O2 CE1 N1 162.47(8) .
O1 CE1 N1 71.19(8) .
O3 CE1 N1 99.57(8) .
O4 CE1 N1 80.30(8) .
N3 CE1 N1 127.19(8) .
N2 CE1 N1 62.56(9) .
O6 CE1 N4 167.35(6) .
O2 CE1 N4 81.86(8) .
O1 CE1 N4 101.27(8) .
O3 CE1 N4 25.16(8) .
O4 CE1 N4 25.39(8) .
N3 CE1 N4 95.54(8) .
N2 CE1 N4 87.99(13) .
N1 CE1 N4 91.92(8) .
O6 CE1 CE1 5.51(8) 2_755
O2 CE1 CE1 100.08(5) 2_755
O1 CE1 CE1 92.45(6) 2_755
O3 CE1 CE1 141.02(6) 2_755
O4 CE1 CE1 166.88(5) 2_755
N3 CE1 CE1 72.44(6) 2_755
N2 CE1 CE1 80.56(11) 2_755
N1 CE1 CE1 89.93(6) 2_755
N4 CE1 CE1 166.01(6) 2_755
C1 O1 CE1 146.5(2) .
C18 O2 CE1 148.52(19) .
N4 O3 CE1 96.95(18) .
N4 O4 CE1 96.41(18) .
CE1 O6 CE1 168.99(16) 2_755
C7 N1 C8 114.0(3) .
C7 N1 CE1 125.3(2) .
C8 N1 CE1 119.10(19) .
C9 N2 C10 118.1(3) .
C9 N2 CE1 113.6(3) .
C10 N2 CE1 113.8(2) .
C9 N2 H2 102.9 .
C10 N2 H2 102.9 .
CE1 N2 H2 102.9 .
C12 N3 C11 115.9(3) .
C12 N3 CE1 129.9(2) .
C11 N3 CE1 114.23(19) .
O5 N4 O3 122.1(3) .
O5 N4 O4 122.4(3) .
O3 N4 O4 115.5(3) .
O5 N4 CE1 173.0(2) .
O3 N4 CE1 57.89(16) .
O4 N4 CE1 58.20(15) .
O1 C1 C6 119.8(3) .
O1 C1 C2 121.4(3) .
C6 C1 C2 118.7(3) .
C3 C2 C1 117.2(4) .
C3 C2 C19 120.6(3) .
C1 C2 C19 122.1(3) .
C4 C3 C2 125.0(4) .
C4 C3 H3 117.5 .
C2 C3 H3 117.5 .
C5 C4 C3 116.7(4) .
C5 C4 C23 122.3(5) .
C3 C4 C23 121.0(4) .
C4 C5 C6 121.5(4) .
C4 C5 H5 119.2 .
C6 C5 H5 119.2 .
C1 C6 C5 120.4(3) .
C1 C6 C7 124.1(3) .
C5 C6 C7 115.4(3) .
N1 C7 C6 129.2(3) .
N1 C7 H7 115.4 .
C6 C7 H7 115.4 .
C9 C8 N1 110.2(3) .
C9 C8 H8A 109.6 .
N1 C8 H8A 109.6 .
C9 C8 H8B 109.6 .
N1 C8 H8B 109.6 .
H8A C8 H8B 108.1 .
N2 C9 C8 113.7(4) .
N2 C9 H9A 108.8 .
C8 C9 H9A 108.8 .
N2 C9 H9B 108.8 .
C8 C9 H9B 108.8 .
H9A C9 H9B 107.7 .
N2 C10 C11 107.5(3) .
N2 C10 H10A 110.2 .
C11 C10 H10A 110.2 .
N2 C10 H10B 110.2 .
C11 C10 H10B 110.2 .
H10A C10 H10B 108.5 .
N3 C11 C10 108.5(3) .
N3 C11 H11A 110.0 .
C10 C11 H11A 110.0 .
N3 C11 H11B 110.0 .
C10 C11 H11B 110.0 .
H11A C11 H11B 108.4 .
N3 C12 C13 127.8(3) .
N3 C12 H12 116.1 .
C13 C12 H12 116.1 .
C18 C13 C14 121.0(3) .
C18 C13 C12 123.1(3) .
C14 C13 C12 115.8(3) .
C15 C14 C13 120.9(3) .
C15 C14 H14 119.6 .
C13 C14 H14 119.6 .
C14 C15 C16 116.9(3) .
C14 C15 C27 122.8(3) .
C16 C15 C27 120.4(3) .
C15 C16 C17 125.1(3) .
C15 C16 H16 117.4 .
C17 C16 H16 117.4 .
C16 C17 C18 117.5(3) .
C16 C17 C31 120.1(3) .
C18 C17 C31 122.4(3) .
O2 C18 C13 119.9(3) .
O2 C18 C17 121.5(3) .
C13 C18 C17 118.6(3) .
C2 C19 C20 109.4(3) .
C2 C19 C22 113.6(4) .
C20 C19 C22 106.8(4) .
C2 C19 C21 108.9(3) .
C20 C19 C21 112.2(3) .
C22 C19 C21 106.0(3) .
C19 C20 H20A 109.5 .
C19 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
C19 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
C19 C21 H21A 109.5 .
C19 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C19 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C19 C22 H22A 109.5 .
C19 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C19 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C37b C23 C35 125.3(9) .
C37b C23 C4 111.1(6) .
C35b C23 C4 111.6(8) .
C36a C23 C4 113.7(6) .
C36a C23 C24 133.0(7) .
C4 C23 C24 105.8(4) .
C37b C23 C26 113.7(6) .
C35b C23 C26 85.1(8) .
C4 C23 C26 106.0(5) .
C36a C23 C25 95.4(6) .
C4 C23 C25 111.1(4) .
C24a C23 C25 93.1(5) .
C23 C24a H24A 109.5 .
C23 C24a H24B 109.5 .
H24Aa C24a H24B 109.5 .
C23 C24a H24C 109.5 .
H24Aa C24a H24C 109.5 .
H24Ba C24a H24C 109.5 .
C23 C25a H25A 109.5 .
C23 C25a H25B 109.5 .
H25Aa C25a H25B 109.5 .
C23 C25a H25C 109.5 .
H25Aa C25a H25C 109.5 .
H25Ba C25a H25C 109.5 .
C23 C36a H36A 109.5 .
C23 C36a H36B 109.5 .
H36Aa C36a H36B 109.5 .
C23 C36a H36C 109.5 .
H36Aa C36a H36C 109.5 .
H36Ba C36a H36C 109.5 .
C23 C35b H35A 109.5 .
C23 C35b H35B 109.5 .
H35Ab C35b H35B 109.5 .
C23 C35b H35C 109.5 .
H35Ab C35b H35C 109.5 .
H35Bb C35b H35C 109.5 .
C23 C26b H26A 109.5 .
C23 C26b H26B 109.5 .
H26Ab C26b H26B 109.5 .
C23 C26b H26C 109.5 .
H26Ab C26b H26C 109.5 .
H26Bb C26b H26C 109.5 .
C23 C37b H37A 109.5 .
C23 C37b H37B 109.5 .
H37Ab C37b H37B 109.5 .
C23 C37b H37C 109.5 .
H37Ab C37b H37C 109.5 .
H37Bb C37b H37C 109.5 .
C28 C27 C30 110.4(4) .
C28 C27 C29 108.0(3) .
C30 C27 C29 108.0(4) .
C28 C27 C15 111.5(3) .
C30 C27 C15 108.0(3) .
C29 C27 C15 110.9(3) .
C27 C28 H28A 109.5 .
C27 C28 H28B 109.5 .
H28A C28 H28B 109.5 .
C27 C28 H28C 109.5 .
H28A C28 H28C 109.5 .
H28B C28 H28C 109.5 .
C27 C29 H29A 109.5 .
C27 C29 H29B 109.5 .
H29A C29 H29B 109.5 .
C27 C29 H29C 109.5 .
H29A C29 H29C 109.5 .
H29B C29 H29C 109.5 .
C27 C30 H30A 109.5 .
C27 C30 H30B 109.5 .
H30A C30 H30B 109.5 .
C27 C30 H30C 109.5 .
H30A C30 H30C 109.5 .
H30B C30 H30C 109.5 .
C33 C31 C17 109.4(3) .
C33 C31 C32 110.1(3) .
C17 C31 C32 110.0(3) .
C33 C31 C34 106.8(4) .
C17 C31 C34 112.8(3) .
C32 C31 C34 107.6(3) .
C31 C32 H32A 109.5 .
C31 C32 H32B 109.5 .
H32A C32 H32B 109.5 .
C31 C32 H32C 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
C31 C33 H33A 109.5 .
C31 C33 H33B 109.5 .
H33A C33 H33B 109.5 .
C31 C33 H33C 109.5 .
H33A C33 H33C 109.5 .
H33B C33 H33C 109.5 .
C31 C34 H34A 109.5 .
C31 C34 H34B 109.5 .
H34A C34 H34B 109.5 .
C31 C34 H34C 109.5 .
H34A C34 H34C 109.5 .
H34B C34 H34C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
CE1 O6 2.0804(4) .
CE1 O2 2.196(2) .
CE1 O1 2.211(2) .
CE1 O3 2.525(2) .
CE1 O4 2.531(2) .
CE1 N3 2.600(3) .
CE1 N2 2.606(3) .
CE1 N1 2.621(3) .
CE1 N4 2.959(3) .
CE1 CE1 4.1416(6) 2_755
O1 C1 1.337(4) .
O2 C18 1.343(4) .
O3 N4 1.268(4) .
O4 N4 1.277(4) .
O5 N4 1.210(4) .
O6 CE1 2.0804(4) 2_755
N1 C7 1.288(4) .
N1 C8 1.485(4) .
N2 C9 1.382(6) .
N2 C10 1.480(4) .
N2 H2 1.0000 .
N3 C12 1.279(4) .
N3 C11 1.471(4) .
C1 C6 1.407(5) .
C1 C2 1.426(5) .
C2 C3 1.399(5) .
C2 C19 1.524(6) .
C3 C4 1.393(6) .
C3 H3 0.9500 .
C4 C5 1.377(6) .
C4 C23 1.544(5) .
C5 C6 1.420(4) .
C5 H5 0.9500 .
C6 C7 1.444(5) .
C7 H7 0.9500 .
C8 C9 1.481(5) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.511(5) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.454(4) .
C12 H12 0.9500 .
C13 C18 1.412(4) .
C13 C14 1.416(4) .
C14 C15 1.384(5) .
C14 H14 0.9500 .
C15 C16 1.391(5) .
C15 C27 1.545(4) .
C16 C17 1.394(5) .
C16 H16 0.9500 .
C17 C18 1.419(4) .
C17 C31 1.526(5) .
C19 C20 1.531(6) .
C19 C22 1.538(5) .
C19 C21 1.548(5) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 C37 1.258(10) .
C23 C35 1.389(16) .
C23 C36 1.494(11) .
C23 C24 1.618(8) .
C23 C26 1.674(10) .
C23 C25 1.784(10) .
C24a H24A 0.9800 .
C24a H24B 0.9800 .
C24a H24C 0.9800 .
C25a H25A 0.9800 .
C25a H25B 0.9800 .
C25a H25C 0.9800 .
C36a H36A 0.9800 .
C36a H36B 0.9800 .
C36a H36C 0.9800 .
C35b H35A 0.9800 .
C35b H35B 0.9800 .
C35b H35C 0.9800 .
C26b H26A 0.9800 .
C26b H26B 0.9800 .
C26b H26C 0.9800 .
C37b H37A 0.9800 .
C37b H37B 0.9800 .
C37b H37C 0.9800 .
C27 C28 1.534(6) .
C27 C30 1.536(6) .
C27 C29 1.544(5) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 C33 1.523(6) .
C31 C32 1.538(5) .
C31 C34 1.542(5) .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
CE1 O3 N4 O5 171.8(3)
CE1 O3 N4 O4 -8.5(3)
CE1 O4 N4 O5 -171.8(3)
CE1 O4 N4 O3 8.4(3)
CE1 O1 C1 C6 -3.4(5)
CE1 O1 C1 C2 176.6(2)
O1 C1 C2 C3 -173.4(3)
C6 C1 C2 C3 6.6(5)
O1 C1 C2 C19 4.8(5)
C6 C1 C2 C19 -175.1(3)
C1 C2 C3 C4 -1.4(5)
C19 C2 C3 C4 -179.7(3)
C2 C3 C4 C5 -3.2(6)
C2 C3 C4 C23 178.2(3)
C3 C4 C5 C6 2.5(5)
C23 C4 C5 C6 -178.8(3)
O1 C1 C6 C5 172.7(3)
C2 C1 C6 C5 -7.3(5)
O1 C1 C6 C7 -11.0(5)
C2 C1 C6 C7 169.0(3)
C4 C5 C6 C1 2.6(5)
C4 C5 C6 C7 -173.9(3)
C8 N1 C7 C6 -176.4(3)
CE1 N1 C7 C6 18.4(5)
C1 C6 C7 N1 0.6(6)
C5 C6 C7 N1 177.0(3)
C7 N1 C8 C9 -174.9(4)
CE1 N1 C8 C9 -8.7(5)
C10 N2 C9 C8 168.9(4)
CE1 N2 C9 C8 -54.0(6)
N1 C8 C9 N2 40.6(6)
C9 N2 C10 C11 -175.2(5)
CE1 N2 C10 C11 47.8(4)
C12 N3 C11 C10 -135.5(3)
CE1 N3 C11 C10 46.4(3)
N2 C10 C11 N3 -61.8(4)
C11 N3 C12 C13 176.5(3)
CE1 N3 C12 C13 -5.8(5)
N3 C12 C13 C18 1.8(5)
N3 C12 C13 C14 -174.6(3)
C18 C13 C14 C15 0.9(5)
C12 C13 C14 C15 177.4(3)
C13 C14 C15 C16 -2.7(5)
C13 C14 C15 C27 176.5(3)
C14 C15 C16 C17 1.5(5)
C27 C15 C16 C17 -177.7(3)
C15 C16 C17 C18 1.5(5)
C15 C16 C17 C31 -178.0(3)
CE1 O2 C18 C13 -13.9(6)
CE1 O2 C18 C17 166.4(3)
C14 C13 C18 O2 -177.5(3)
C12 C13 C18 O2 6.3(5)
C14 C13 C18 C17 2.2(5)
C12 C13 C18 C17 -174.0(3)
C16 C17 C18 O2 176.4(3)
C31 C17 C18 O2 -4.1(5)
C16 C17 C18 C13 -3.3(5)
C31 C17 C18 C13 176.2(3)
C3 C2 C19 C20 -125.2(3)
C1 C2 C19 C20 56.6(4)
C3 C2 C19 C22 -5.9(5)
C1 C2 C19 C22 175.9(3)
C3 C2 C19 C21 111.9(4)
C1 C2 C19 C21 -66.3(4)
C5 C4 C23 C37b 48.1(7)
C3 C4 C23 C37b -133.3(6)
C5 C4 C23 C35b -96.9(9)
C3 C4 C23 C35b 81.7(9)
C5 C4 C23 C36a 125.7(8)
C3 C4 C23 C36a -55.7(9)
C5 C4 C23 C24a -80.4(6)
C3 C4 C23 C24a 98.2(5)
C5 C4 C23 C26b 172.1(5)
C3 C4 C23 C26b -9.3(6)
C5 C4 C23 C25a 19.4(6)
C3 C4 C23 C25a -162.0(4)
C14 C15 C27 C28 22.2(5)
C16 C15 C27 C28 -158.6(3)
C14 C15 C27 C30 -99.2(5)
C16 C15 C27 C30 80.0(4)
C14 C15 C27 C29 142.6(4)
C16 C15 C27 C29 -38.2(5)
C16 C17 C31 C33 -118.9(4)
C18 C17 C31 C33 61.6(4)
C16 C17 C31 C32 120.0(4)
C18 C17 C31 C32 -59.5(5)
C16 C17 C31 C34 -0.2(5)
C18 C17 C31 C34 -179.7(4)
