#------------------------------------------------------------------------------
#$Date: 2016-01-06 11:58:16 +0200 (Wed, 06 Jan 2016) $
#$Revision: 173579 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/47/4124751.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_4124751
loop_
_publ_author_name
'Zhou, Zhen'
'He, Cheng'
'Xiu, Jinghai'
'Yang, Lu'
'Duan, Chunying'
_publ_section_title
;
 Metal-Organic Polymers Containing Discrete Single-Walled Nanotube as a
 Heterogeneous Catalyst for the Cycloaddition of Carbon Dioxide to
 Epoxides.
;
_journal_issue                   48
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15066
_journal_page_last               15069
_journal_paper_doi               10.1021/jacs.5b07925
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C33 H31 N Ni2 O13'
_chemical_formula_weight         766.97
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           147
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_space_group_name_H-M   'P -3'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   27.593(3)
_cell_length_b                   27.593(3)
_cell_length_c                   13.6745(17)
_cell_measurement_temperature    220(2)
_cell_volume                     9016.5(18)
_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      220(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1345
_diffrn_reflns_av_sigmaI/netI    0.2008
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42001
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.8786
_exptl_absorpt_correction_T_min  0.8515
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    0.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_platon_squeeze_details
;
;
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         10603
_refine_ls_number_restraints     210
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1477
_refine_ls_R_factor_gt           0.0729
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0129P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1548
_reflns_number_gt                4203
_reflns_number_total             10603
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b07925_si_002.cif
_cod_data_source_block           Ni-TCPE1
_cod_depositor_comments
'Adding full bibliography for 4124750--4124752.cif.'
_cod_original_cell_volume        9016.5(16)
_cod_original_sg_symbol_H-M      P-3
_cod_original_formula_sum        'C33 H31 N1 Ni2 O13'
_cod_database_code               4124751
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -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
Ni1 Ni 0.18771(3) 0.75231(3) 0.49993(4) 0.04563(19) Uani 1 1 d . . .
Ni2 Ni 0.17941(3) 0.62276(3) 0.49996(4) 0.0470(2) Uani 1 1 d . . .
O1 O 0.13561(14) 0.70493(15) 0.3921(3) 0.0717(12) Uani 1 1 d . . .
O2 O 0.13324(15) 0.62519(16) 0.3901(3) 0.0817(13) Uani 1 1 d . . .
O10 O 0.22963(11) 0.70701(12) 0.49965(18) 0.0434(9) Uani 1 1 d . . .
H10 H 0.2534 0.7175 0.4422 0.052 Uiso 1 1 d R . .
H10B H 0.2538 0.7177 0.5566 0.052 Uiso 1 1 d R . .
O11 O 0.14760(15) 0.79891(16) 0.4987(3) 0.0921(13) Uani 1 1 d . . .
H11A H 0.1160 0.7857 0.5267 0.110 Uiso 1 1 d R . .
H11C H 0.1674 0.8223 0.5426 0.110 Uiso 1 1 d R . .
O12 O 0.23105(14) 0.61766(14) 0.6043(2) 0.0744(11) Uani 1 1 d . . .
H12A H 0.2191 0.6189 0.6609 0.112 Uiso 1 1 d R . .
H12B H 0.2308 0.5869 0.5974 0.112 Uiso 1 1 d R . .
O13 O 0.23192(13) 0.61837(15) 0.3957(2) 0.0741(11) Uani 1 1 d . . .
H13A H 0.2199 0.6197 0.3391 0.111 Uiso 1 1 d R . .
H13C H 0.2317 0.5876 0.4023 0.111 Uiso 1 1 d R . .
C1 C 0.1236(2) 0.6601(3) 0.3564(4) 0.0564(16) Uani 1 1 d . . .
C2 C 0.0895(2) 0.6442(2) 0.2643(4) 0.0599(16) Uani 1 1 d . . .
C3 C 0.0736(3) 0.5982(3) 0.2186(6) 0.150(3) Uani 1 1 d . . .
H3 H 0.0873 0.5751 0.2387 0.180 Uiso 1 1 d R . .
C4 C 0.0403(3) 0.5835(3) 0.1380(5) 0.154(3) Uani 1 1 d . . .
H4 H 0.0233 0.5462 0.1191 0.185 Uiso 1 1 d R . .
C5 C 0.0270(2) 0.6152(3) 0.0924(4) 0.0623(17) Uani 1 1 d . . .
C6 C 0.0456(4) 0.6625(3) 0.1345(6) 0.189(4) Uani 1 1 d . . .
H6 H 0.0431 0.6908 0.1017 0.227 Uiso 1 1 d R . .
C7 C 0.0779(4) 0.6782(3) 0.2204(6) 0.180(4) Uani 1 1 d . . .
H7 H 0.0879 0.7125 0.2490 0.216 Uiso 1 1 d R . .
C11 C 0.0480(4) 0.6643(3) -0.1314(6) 0.193(4) Uani 1 1 d . . .
H11 H 0.0457 0.6923 -0.0977 0.231 Uiso 1 1 d R . .
C12 C 0.0270(2) 0.6157(3) -0.0932(4) 0.0600(17) Uani 1 1 d . . .
C13 C 0.0411(3) 0.5836(3) -0.1350(5) 0.143(3) Uani 1 1 d . . .
H13 H 0.0271 0.5477 -0.1103 0.171 Uiso 1 1 d R . .
C18 C -0.1209(3) 0.5139(3) -0.1274(5) 0.127(3) Uani 1 1 d . . .
H18 H -0.1155 0.4861 -0.1000 0.153 Uiso 1 1 d R . .
C19 C -0.0941(2) 0.5647(2) -0.0922(3) 0.0494(15) Uani 1 1 d . . .
C20 C -0.0999(3) 0.6030(3) -0.1397(5) 0.150(3) Uani 1 1 d . . .
H20 H -0.0788 0.6401 -0.1198 0.180 Uiso 1 1 d R . .
C25 C -0.1207(3) 0.5147(3) 0.1270(5) 0.127(3) Uani 1 1 d . . .
H25 H -0.1175 0.4863 0.0962 0.152 Uiso 1 1 d R . .
C26 C -0.09454(19) 0.5650(2) 0.0925(3) 0.0468(14) Uani 1 1 d . . .
C27 C -0.0985(3) 0.6031(3) 0.1424(6) 0.150(4) Uani 1 1 d . . .
H27 H -0.0750 0.6407 0.1275 0.180 Uiso 1 1 d R . .
C29 C -0.0071(2) 0.6001(2) 0.0010(4) 0.0687(18) Uani 1 1 d . . .
C30 C -0.0614(2) 0.5778(2) 0.0002(3) 0.0588(17) Uani 1 1 d . . .
O9 O 0.13526(16) 0.53762(17) 0.5001(3) 0.0849(14) Uani 1 1 d U . .
N1 N 0.0578(3) 0.4614(4) 0.5003(9) 0.110(4) Uani 0.50 1 d PDU A 1
N1' N 0.0548(4) 0.4578(4) 0.5046(7) 0.109(5) Uani 0.50 1 d PDU B 2
C31 C 0.0960(5) 0.5161(4) 0.4727(10) 0.094(4) Uani 0.50 1 d PDU A 1
H31 H 0.0780 0.5339 0.4457 0.112 Uiso 0.50 1 d PR A 1
C32 C 0.0006(4) 0.4326(6) 0.4698(13) 0.162(6) Uani 0.50 1 d PDU A 1
H32A H -0.0233 0.4187 0.5261 0.243 Uiso 0.50 1 calc PR A 1
H32B H -0.0060 0.4018 0.4282 0.243 Uiso 0.50 1 calc PR A 1
H32C H -0.0074 0.4578 0.4344 0.243 Uiso 0.50 1 calc PR A 1
C33 C 0.0749(6) 0.4230(5) 0.5306(13) 0.166(6) Uani 0.50 1 d PDU A 1
H33A H 0.0693 0.3976 0.4780 0.249 Uiso 0.50 1 calc PR A 1
H33B H 0.0532 0.4023 0.5862 0.249 Uiso 0.50 1 calc PR A 1
H33C H 0.1138 0.4431 0.5479 0.249 Uiso 0.50 1 calc PR A 1
C31' C 0.0986(6) 0.5109(5) 0.5274(10) 0.106(5) Uani 0.50 1 d PDU B 2
H31' H 0.0964 0.5173 0.5936 0.127 Uiso 0.50 1 d PR B 2
C32' C 0.0116(6) 0.4255(6) 0.5738(11) 0.168(7) Uani 0.50 1 d PDU B 2
H32D H -0.0004 0.4489 0.6050 0.253 Uiso 0.50 1 calc PR B 2
H32E H 0.0257 0.4105 0.6222 0.253 Uiso 0.50 1 calc PR B 2
H32F H -0.0196 0.3954 0.5406 0.253 Uiso 0.50 1 calc PR B 2
C33' C 0.0445(7) 0.4316(6) 0.4121(9) 0.177(7) Uani 0.50 1 d PDU B 2
H33D H 0.0066 0.4012 0.4095 0.266 Uiso 0.50 1 calc PR B 2
H33E H 0.0697 0.4175 0.4022 0.266 Uiso 0.50 1 calc PR B 2
H33F H 0.0503 0.4582 0.3619 0.266 Uiso 0.50 1 calc PR B 2
C24 C -0.1542(3) 0.5037(3) 0.2090(6) 0.142(3) Uani 1 1 d . . .
C23 C -0.16173(19) 0.5415(2) 0.2572(3) 0.0464(14) Uani 1 1 d . . .
H24 H -0.1767 0.4658 0.2279 0.056 Uiso 1 1 d R . .
C22 C -0.1985(2) 0.5269(2) 0.3434(4) 0.0586(16) Uani 1 1 d . . .
C28 C -0.1346(3) 0.5905(3) 0.2212(6) 0.125(3) Uani 1 1 d . . .
O7 O -0.19385(13) 0.56714(14) 0.3933(2) 0.0571(10) Uani 1 1 d . . .
O8 O -0.23584(15) 0.47599(15) 0.3554(2) 0.0693(11) Uani 1 1 d . . .
H28 H -0.1400 0.6179 0.2479 0.083 Uiso 1 1 d R . .
C21 C -0.1348(3) 0.5907(3) -0.2225(6) 0.131(3) Uani 1 1 d . . .
C16 C -0.16211(19) 0.5402(2) -0.2576(3) 0.0488(15) Uani 1 1 d . . .
H21 H -0.1383 0.6196 -0.2522 0.059 Uiso 1 1 d R . .
C15 C -0.1985(2) 0.5267(2) -0.3421(4) 0.0599(17) Uani 1 1 d . . .
C17 C -0.1549(4) 0.5031(3) -0.2102(5) 0.140(3) Uani 1 1 d . . .
O5 O -0.19424(13) 0.56644(14) -0.3934(2) 0.0582(11) Uani 1 1 d . . .
O6 O -0.23532(15) 0.47584(15) -0.3559(2) 0.0697(11) Uani 1 1 d . . .
H17 H -0.1783 0.4651 -0.2292 0.084 Uiso 1 1 d R . .
C14 C 0.0749(3) 0.5992(3) -0.2173(6) 0.156(3) Uani 1 1 d . . .
C9 C 0.0894(2) 0.6449(2) -0.2645(4) 0.0553(16) Uani 1 1 d . . .
H14 H 0.0892 0.5765 -0.2346 0.066 Uiso 1 1 d R . .
C8 C 0.1227(2) 0.6598(2) -0.3576(4) 0.0548(16) Uani 1 1 d . . .
C10 C 0.0788(4) 0.6786(3) -0.2184(6) 0.174(4) Uani 1 1 d . . .
O3 O 0.13572(14) 0.70565(16) -0.3926(3) 0.0720(12) Uani 1 1 d . . .
O4 O 0.13246(15) 0.62446(17) -0.3897(3) 0.0800(13) Uani 1 1 d . . .
H10C H 0.0927 0.7138 -0.2431 0.096 Uiso 1 1 d R . .
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'
Ni Ni 0.3393 1.1124 '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
O3 Ni1 O1 94.04(15) 1_556 .
O3 Ni1 O5 174.73(15) 1_556 6_665
O1 Ni1 O5 87.73(14) . 6_665
O3 Ni1 O7 87.52(14) 1_556 6_666
O1 Ni1 O7 174.76(15) . 6_666
O5 Ni1 O7 90.29(14) 6_665 6_666
O3 Ni1 O11 88.40(16) 1_556 .
O1 Ni1 O11 88.14(16) . .
O5 Ni1 O11 86.69(14) 6_665 .
O7 Ni1 O11 86.90(14) 6_666 .
O3 Ni1 O10 92.84(14) 1_556 .
O1 Ni1 O10 92.26(14) . .
O5 Ni1 O10 92.05(12) 6_665 .
O7 Ni1 O10 92.66(12) 6_666 .
O11 Ni1 O10 178.67(13) . .
O2 Ni2 O4 97.76(17) . 1_556
O2 Ni2 O10 92.40(14) . .
O4 Ni2 O10 93.09(14) 1_556 .
O2 Ni2 O9 90.91(16) . .
O4 Ni2 O9 90.31(17) 1_556 .
O10 Ni2 O9 174.89(15) . .
O2 Ni2 O12 174.42(16) . .
O4 Ni2 O12 87.59(15) 1_556 .
O10 Ni2 O12 88.87(12) . .
O9 Ni2 O12 87.47(15) . .
O2 Ni2 O13 87.76(15) . .
O4 Ni2 O13 174.27(16) 1_556 .
O10 Ni2 O13 88.20(13) . .
O9 Ni2 O13 88.04(16) . .
O12 Ni2 O13 86.86(14) . .
C1 O1 Ni1 134.3(4) . .
C1 O2 Ni2 135.4(4) . .
Ni2 O10 Ni1 114.94(13) . .
O1 C1 O2 127.0(5) . .
O1 C1 C2 116.6(6) . .
O2 C1 C2 116.2(5) . .
C3 C2 C7 114.2(6) . .
C3 C2 C1 123.6(6) . .
C7 C2 C1 122.0(6) . .
C2 C3 C4 122.5(7) . .
C5 C4 C3 125.3(7) . .
C4 C5 C6 112.1(6) . .
C4 C5 C29 125.3(6) . .
C6 C5 C29 122.5(6) . .
C5 C6 C7 124.0(8) . .
C2 C7 C6 121.3(7) . .
C12 C11 C10 122.6(7) . .
C13 C12 C11 114.3(6) . .
C13 C12 C29 123.0(6) . .
C11 C12 C29 122.4(6) . .
C12 C13 C14 122.9(7) . .
C19 C18 C17 118.9(6) . .
C18 C19 C20 116.7(5) . .
C18 C19 C30 121.5(5) . .
C20 C19 C30 121.7(5) . .
C19 C20 C21 123.0(6) . .
C26 C25 C24 118.9(6) . .
C25 C26 C27 116.6(5) . .
C25 C26 C30 120.6(5) . .
C27 C26 C30 122.7(5) . .
C26 C27 C28 122.9(6) . .
C30 C29 C5 123.6(5) . .
C30 C29 C12 121.9(5) . .
C5 C29 C12 114.5(4) . .
C29 C30 C19 122.3(5) . .
C29 C30 C26 121.8(4) . .
C19 C30 C26 115.8(4) . .
C31' O9 C31 45.6(10) . .
C31' O9 Ni2 131.7(10) . .
C31 O9 Ni2 121.6(8) . .
C31 N1 C33 122.2(9) . .
C31 N1 C32 123.4(10) . .
C33 N1 C32 110.9(10) . .
C31' N1' C33' 125.9(9) . .
C31' N1' C32' 121.5(9) . .
C33' N1' C32' 112.3(10) . .
O9 C31 N1 122.9(11) . .
O9 C31' N1' 137.2(14) . .
C23 C24 C25 125.2(6) . .
C28 C23 C24 113.6(5) . .
C28 C23 C22 124.0(6) . .
C24 C23 C22 122.4(5) . .
O7 C22 O8 125.1(5) . .
O7 C22 C23 116.2(5) . .
O8 C22 C23 118.3(5) . .
C23 C28 C27 122.2(6) . .
C22 O7 Ni1 127.1(3) . 5_456
C16 C21 C20 120.8(6) . .
C21 C16 C17 115.0(5) . .
C21 C16 C15 121.6(6) . .
C17 C16 C15 123.4(5) . .
O5 C15 O6 123.9(5) . .
O5 C15 C16 118.0(5) . .
O6 C15 C16 118.0(5) . .
C16 C17 C18 125.5(6) . .
C15 O5 Ni1 128.4(3) . 5_455
C9 C14 C13 122.9(7) . .
C10 C9 C14 113.2(6) . .
C10 C9 C8 123.6(6) . .
C14 C9 C8 122.7(6) . .
O4 C8 O3 128.2(5) . .
O4 C8 C9 116.0(5) . .
O3 C8 C9 115.7(5) . .
C9 C10 C11 122.9(7) . .
C8 O3 Ni1 133.9(4) . 1_554
C8 O4 Ni2 134.1(4) . 1_554
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O3 2.007(3) 1_556
Ni1 O1 2.018(3) .
Ni1 O5 2.056(3) 6_665
Ni1 O7 2.059(3) 6_666
Ni1 O11 2.074(4) .
Ni1 O10 2.085(3) .
Ni2 O2 1.992(4) .
Ni2 O4 2.005(4) 1_556
Ni2 O10 2.026(3) .
Ni2 O9 2.035(4) .
Ni2 O12 2.070(3) .
Ni2 O13 2.079(3) .
O1 C1 1.211(6) .
O2 C1 1.212(6) .
C1 C2 1.501(7) .
C2 C3 1.280(8) .
C2 C7 1.281(8) .
C3 C4 1.361(8) .
C4 C5 1.269(8) .
C5 C6 1.277(8) .
C5 C29 1.493(7) .
C6 C7 1.406(9) .
C11 C12 1.275(8) .
C11 C10 1.400(9) .
C12 C13 1.269(8) .
C12 C29 1.525(7) .
C13 C14 1.385(9) .
C18 C19 1.306(7) .
C18 C17 1.405(8) .
C19 C20 1.315(8) .
C19 C30 1.489(6) .
C20 C21 1.415(9) .
C25 C26 1.292(7) .
C25 C24 1.387(8) .
C26 C27 1.304(8) .
C26 C30 1.492(6) .
C27 C28 1.389(9) .
C29 C30 1.305(6) .
O9 C31' 0.981(11) .
O9 C31 1.012(11) .
N1 C31 1.393(8) .
N1 C33 1.422(9) .
N1 C32 1.430(8) .
N1' C31' 1.389(8) .
N1' C33' 1.414(9) .
N1' C32' 1.432(9) .
C24 C23 1.335(8) .
C23 C28 1.272(7) .
C23 C22 1.473(6) .
C22 O7 1.255(6) .
C22 O8 1.271(6) .
O7 Ni1 2.059(3) 5_456
C21 C16 1.299(7) .
C16 C17 1.308(8) .
C16 C15 1.453(7) .
C15 O5 1.255(6) .
C15 O6 1.270(6) .
O5 Ni1 2.056(3) 5_455
C14 C9 1.289(8) .
C9 C10 1.272(8) .
C9 C8 1.502(7) .
C8 O4 1.214(6) .
C8 O3 1.228(6) .
O3 Ni1 2.007(3) 1_554
O4 Ni2 2.005(4) 1_554
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.006 -0.004 -0.005 4833.3 552.4
2 0.333 0.667 0.500 8.5 8.0
3 0.667 0.333 0.500 8.5 7.3
