#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/26/4102667.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_4102667
loop_
_publ_author_name
'Hirokazu Nishimaki'
'Takayuki Ishida'
_publ_contact_author_address
;
    Department of Applied Physics and Chemistry, The University of
    Electro-Communications, Chofu, Tokyo 182-8585, Japan
;
_publ_contact_author_email       ' ishi@pc.uec.ac.jp '
_publ_contact_author_fax         ' +81-424-43-5501 '
_publ_contact_author_name        ' Takayuki Ishida'
_publ_contact_author_phone       ' +81-424-43-5490 '
_publ_section_title
;
 Organic Two-Step Spin-Transition-Like Behavior in a Linear S = 1 Array:
 3'-Methylbiphenyl-3,5-diyl Bis(tert-butylnitroxide) and Related Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9598
_journal_page_last               9599
_journal_paper_doi               10.1021/ja102890g
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C21 H28 N2 O2 '
_chemical_formula_sum            'C21 H28 N2 O2'
_chemical_formula_weight         340.45
_chemical_melting_point          352
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                110.621(4)
_cell_angle_beta                 96.472(3)
_cell_angle_gamma                112.361(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2411(5)
_cell_length_b                   10.3875(2)
_cell_length_c                   11.7540(5)
_cell_measurement_reflns_used    2430
_cell_measurement_temperature    116.
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.3
_cell_volume                     936.09(9)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      116.
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.070
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8185
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             368.00
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.57
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4175
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.0012
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0050Fo² + 1.0000σ(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                2763
_reflns_number_total             4175
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja102890g_si_004_2.cif
_cod_data_source_block           '_Low_Temp_phase_3MeBPBN'
_cod_original_formula_sum        'C21 H28 N2 O2 '
_cod_database_code               4102667
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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
O(1) O -0.1299(2) 0.3597(2) 0.43799(17) 0.0164(4) Uani 1.00 1 d
O(2) O -0.1357(2) -0.0302(2) 0.03448(17) 0.0137(4) Uani 1.00 1 d
N(1) N -0.0986(2) 0.4514(2) 0.3835(2) 0.0121(5) Uani 1.00 1 d
N(2) N -0.0846(2) 0.0785(2) -0.0021(2) 0.0121(5) Uani 1.00 1 d
C(1) C -0.0215(3) 0.4166(3) 0.2839(2) 0.0129(6) Uani 1.00 1 d
C(2) C -0.0871(3) 0.2667(3) 0.1919(2) 0.0133(6) Uani 1.00 1 d
C(3) C -0.0123(3) 0.2331(3) 0.0966(2) 0.0122(6) Uani 1.00 1 d
C(4) C 0.1305(3) 0.3469(3) 0.0978(2) 0.0133(6) Uani 1.00 1 d
C(5) C 0.1986(3) 0.4969(3) 0.1917(2) 0.0122(6) Uani 1.00 1 d
C(6) C 0.1197(3) 0.5315(3) 0.2845(2) 0.0125(6) Uani 1.00 1 d
C(7) C 0.3558(3) 0.6183(3) 0.1973(2) 0.0128(6) Uani 1.00 1 d
C(8) C 0.4031(3) 0.6122(3) 0.0875(2) 0.0155(6) Uani 1.00 1 d
C(9) C 0.5494(3) 0.7271(3) 0.0947(2) 0.0185(7) Uani 1.00 1 d
C(10) C 0.6491(3) 0.8488(3) 0.2090(2) 0.0177(6) Uani 1.00 1 d
C(11) C 0.6050(3) 0.8578(3) 0.3209(2) 0.0172(6) Uani 1.00 1 d
C(12) C 0.4585(3) 0.7412(3) 0.3126(2) 0.0147(6) Uani 1.00 1 d
C(13) C -0.2158(3) 0.5175(3) 0.3702(2) 0.0152(6) Uani 1.00 1 d
C(14) C -0.1407(4) 0.6499(4) 0.3343(4) 0.0363(11) Uani 1.00 1 d
C(15) C -0.2574(5) 0.5704(5) 0.4934(3) 0.0356(11) Uani 1.00 1 d
C(16) C -0.3689(4) 0.3902(4) 0.2655(3) 0.0357(9) Uani 1.00 1 d
C(17) C -0.1849(3) 0.0452(3) -0.1286(2) 0.0153(6) Uani 1.00 1 d
C(18) C -0.0984(4) 0.1709(3) -0.1704(2) 0.0233(7) Uani 1.00 1 d
C(19) C -0.3479(3) 0.0401(3) -0.1103(2) 0.0225(7) Uani 1.00 1 d
C(20) C -0.2105(3) -0.1089(3) -0.2258(2) 0.0201(7) Uani 1.00 1 d
C(21) C 0.7131(4) 0.9892(3) 0.4461(3) 0.0266(8) Uani 1.00 1 d
H(1) H -0.182(3) 0.188(3) 0.190(2) 0.015(7) Uiso 1.00 1 d
H(2) H 0.185(4) 0.321(3) 0.040(3) 0.020(7) Uiso 1.00 1 d
H(3) H 0.160(3) 0.629(3) 0.346(2) 0.015(7) Uiso 1.00 1 d
H(4) H 0.338(4) 0.532(4) 0.005(3) 0.028(9) Uiso 1.00 1 d
H(5) H 0.579(4) 0.720(4) 0.019(3) 0.021(8) Uiso 1.00 1 d
H(6) H 0.750(4) 0.926(4) 0.215(3) 0.023(8) Uiso 1.00 1 d
H(7) H 0.429(4) 0.744(3) 0.388(3) 0.019(8) Uiso 1.00 1 d
H(8) H -0.060(5) 0.726(5) 0.402(4) 0.048(12) Uiso 1.00 1 d
H(9) H -0.212(5) 0.699(4) 0.333(3) 0.037(10) Uiso 1.00 1 d
H(10) H -0.100(7) 0.625(6) 0.258(5) 0.062(17) Uiso 1.00 1 d
H(11) H -0.305(4) 0.487(4) 0.519(3) 0.031(9) Uiso 1.00 1 d
H(12) H -0.327(4) 0.617(4) 0.487(3) 0.027(9) Uiso 1.00 1 d
H(13) H -0.161(7) 0.646(6) 0.560(5) 0.056(15) Uiso 1.00 1 d
H(14) H -0.344(6) 0.355(5) 0.182(4) 0.053(13) Uiso 1.00 1 d
H(15) H -0.450(5) 0.432(4) 0.252(3) 0.039(10) Uiso 1.00 1 d
H(16) H -0.412(6) 0.304(6) 0.292(4) 0.060(16) Uiso 1.00 1 d
H(17) H -0.090(4) 0.271(4) -0.114(3) 0.032(9) Uiso 1.00 1 d
H(18) H -0.173(5) 0.138(5) -0.254(4) 0.043(11) Uiso 1.00 1 d
H(19) H 0.014(5) 0.186(5) -0.177(3) 0.041(11) Uiso 1.00 1 d
H(20) H -0.403(4) -0.042(4) -0.083(3) 0.034(9) Uiso 1.00 1 d
H(21) H -0.418(4) 0.026(4) -0.188(3) 0.022(8) Uiso 1.00 1 d
H(22) H -0.322(4) 0.143(4) -0.049(3) 0.020(7) Uiso 1.00 1 d
H(23) H -0.097(4) -0.102(3) -0.237(2) 0.015(7) Uiso 1.00 1 d
H(24) H -0.285(4) -0.132(3) -0.306(3) 0.019(8) Uiso 1.00 1 d
H(25) H -0.262(4) -0.189(4) -0.199(3) 0.020(8) Uiso 1.00 1 d
H(26) H 0.795(5) 0.968(4) 0.475(3) 0.031(10) Uiso 1.00 1 d
H(27) H 0.656(5) 0.999(5) 0.507(4) 0.045(12) Uiso 1.00 1 d
H(28) H 0.757(5) 1.086(5) 0.436(4) 0.049(12) Uiso 1.00 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 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, 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_publ_flag
O(1) N(1) C(1) 115.2(2) yes
O(1) N(1) C(13) 117.4(2) yes
C(1) N(1) C(13) 118.4(2) yes
O(2) N(2) C(3) 115.8(2) yes
O(2) N(2) C(17) 115.73(17) yes
C(3) N(2) C(17) 118.4(2) yes
N(1) C(1) C(2) 118.7(2) yes
N(1) C(1) C(6) 120.2(2) yes
C(2) C(1) C(6) 121.0(2) yes
C(1) C(2) C(3) 118.7(2) yes
N(2) C(3) C(2) 118.7(2) yes
N(2) C(3) C(4) 120.9(2) yes
C(2) C(3) C(4) 120.5(2) yes
C(3) C(4) C(5) 120.9(2) yes
C(4) C(5) C(6) 118.5(2) yes
C(4) C(5) C(7) 121.3(2) yes
C(6) C(5) C(7) 120.2(2) yes
C(1) C(6) C(5) 120.4(2) yes
C(5) C(7) C(8) 121.10(19) yes
C(5) C(7) C(12) 120.6(2) yes
C(8) C(7) C(12) 118.3(2) yes
C(7) C(8) C(9) 120.2(2) yes
C(8) C(9) C(10) 121.0(3) yes
C(9) C(10) C(11) 120.1(2) yes
C(10) C(11) C(12) 118.4(2) yes
C(10) C(11) C(21) 120.6(2) yes
C(12) C(11) C(21) 121.0(2) yes
C(7) C(12) C(11) 122.0(2) yes
N(1) C(13) C(14) 110.1(2) yes
N(1) C(13) C(15) 109.1(3) yes
N(1) C(13) C(16) 107.6(2) yes
C(14) C(13) C(15) 110.9(3) yes
C(14) C(13) C(16) 109.4(3) yes
C(15) C(13) C(16) 109.8(2) yes
N(2) C(17) C(18) 110.62(19) yes
N(2) C(17) C(19) 106.2(2) yes
N(2) C(17) C(20) 109.0(2) yes
C(18) C(17) C(19) 110.7(3) yes
C(18) C(17) C(20) 109.6(2) yes
C(19) C(17) C(20) 110.7(2) yes
C(1) C(2) H(1) 122(2) no
C(3) C(2) H(1) 119(2) no
C(3) C(4) H(2) 119.8(18) no
C(5) C(4) H(2) 119.2(17) no
C(1) C(6) H(3) 119(2) no
C(5) C(6) H(3) 121(2) no
C(7) C(8) H(4) 123(2) no
C(9) C(8) H(4) 117(2) no
C(8) C(9) H(5) 118.6(17) no
C(10) C(9) H(5) 120.5(17) no
C(9) C(10) H(6) 121(2) no
C(11) C(10) H(6) 119(2) no
C(7) C(12) H(7) 118.8(16) no
C(11) C(12) H(7) 119.2(16) no
C(13) C(14) H(8) 107(3) no
C(13) C(14) H(9) 110(2) no
C(13) C(14) H(10) 115(4) no
H(8) C(14) H(9) 98(4) no
H(8) C(14) H(10) 111(4) no
H(9) C(14) H(10) 115(5) no
C(13) C(15) H(11) 112(2) no
C(13) C(15) H(12) 109(2) no
C(13) C(15) H(13) 110(3) no
H(11) C(15) H(12) 112(3) no
H(11) C(15) H(13) 105(4) no
H(12) C(15) H(13) 108(4) no
C(13) C(16) H(14) 111(2) no
C(13) C(16) H(15) 109.9(18) no
C(13) C(16) H(16) 107(2) no
H(14) C(16) H(15) 104(4) no
H(14) C(16) H(16) 112(4) no
H(15) C(16) H(16) 113(4) no
C(17) C(18) H(17) 112(2) no
C(17) C(18) H(18) 104(2) no
C(17) C(18) H(19) 114(3) no
H(17) C(18) H(18) 107(4) no
H(17) C(18) H(19) 108(3) no
H(18) C(18) H(19) 112(4) no
C(17) C(19) H(20) 110(3) no
C(17) C(19) H(21) 111(2) no
C(17) C(19) H(22) 106(2) no
H(20) C(19) H(21) 112(3) no
H(20) C(19) H(22) 114(3) no
H(21) C(19) H(22) 104(3) no
C(17) C(20) H(23) 109.2(15) no
C(17) C(20) H(24) 107(2) no
C(17) C(20) H(25) 110(2) no
H(23) C(20) H(24) 111(3) no
H(23) C(20) H(25) 110(3) no
H(24) C(20) H(25) 108(2) no
C(11) C(21) H(26) 108(2) no
C(11) C(21) H(27) 111(2) no
C(11) C(21) H(28) 109(2) no
H(26) C(21) H(27) 107(4) no
H(26) C(21) H(28) 112(4) no
H(27) C(21) H(28) 109(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) N(1) 1.289(3) yes
O(2) N(2) 1.290(3) yes
N(1) C(1) 1.447(3) yes
N(1) C(13) 1.507(4) yes
N(2) C(3) 1.438(2) yes
N(2) C(17) 1.508(3) yes
C(1) C(2) 1.382(3) yes
C(1) C(6) 1.391(3) yes
C(2) C(3) 1.392(4) yes
C(3) C(4) 1.391(3) yes
C(4) C(5) 1.388(3) yes
C(5) C(6) 1.398(4) yes
C(5) C(7) 1.493(3) yes
C(7) C(8) 1.397(4) yes
C(7) C(12) 1.392(2) yes
C(8) C(9) 1.391(4) yes
C(9) C(10) 1.375(3) yes
C(10) C(11) 1.403(4) yes
C(11) C(12) 1.396(3) yes
C(11) C(21) 1.498(3) yes
C(13) C(14) 1.516(6) yes
C(13) C(15) 1.508(5) yes
C(13) C(16) 1.518(3) yes
C(17) C(18) 1.527(4) yes
C(17) C(19) 1.529(5) yes
C(17) C(20) 1.512(4) yes
C(2) H(1) 0.93(3) no
C(4) H(2) 0.92(3) no
C(6) H(3) 0.91(2) no
C(8) H(4) 0.95(3) no
C(9) H(5) 0.94(4) no
C(10) H(6) 0.95(3) no
C(12) H(7) 0.95(4) no
C(14) H(8) 0.89(3) no
C(14) H(9) 0.97(5) no
C(14) H(10) 0.99(6) no
C(15) H(11) 0.98(4) no
C(15) H(12) 0.95(5) no
C(15) H(13) 0.95(4) no
C(16) H(14) 1.01(5) no
C(16) H(15) 1.02(5) no
C(16) H(16) 1.00(7) no
C(18) H(17) 0.99(4) no
C(18) H(18) 0.99(4) no
C(18) H(19) 1.01(5) no
C(19) H(20) 0.99(4) no
C(19) H(21) 0.99(4) no
C(19) H(22) 0.97(3) no
C(20) H(23) 1.05(3) no
C(20) H(24) 0.99(3) no
C(20) H(25) 0.97(4) no
C(21) H(26) 0.93(5) no
C(21) H(27) 0.93(5) no
C(21) H(28) 0.99(5) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) O(1) 2.697(2) 2_566
O(1) N(1) 2.379(2) 2_566
O(1) C(1) 3.030(2) 2_566
O(1) C(6) 3.030(3) 2_566
O(1) C(13) 3.188(3) 2_566
O(1) C(14) 3.507(5) 2_566
O(1) C(15) 3.308(5) 2_566
O(2) O(2) 2.638(3) 2_555
O(2) N(2) 2.315(3) 2_555
O(2) C(3) 3.011(4) 2_555
O(2) C(4) 3.126(3) 2_555
O(2) C(9) 3.386(3) 1_445
O(2) C(10) 3.252(4) 1_445
O(2) C(17) 3.124(4) 2_555
O(2) C(18) 3.555(5) 2_555
O(2) C(20) 3.155(3) 2_555
N(1) O(1) 2.379(2) 2_566
N(1) N(1) 2.714(3) 2_566
N(1) C(1) 3.532(3) 2_566
N(1) C(15) 3.562(6) 2_566
N(2) O(2) 2.315(3) 2_555
N(2) N(2) 2.662(4) 2_555
N(2) C(3) 3.522(4) 2_555
N(2) C(20) 3.437(4) 2_555
C(1) O(1) 3.030(2) 2_566
C(1) N(1) 3.532(3) 2_566
C(1) C(15) 3.387(5) 2_566
C(3) O(2) 3.011(4) 2_555
C(3) N(2) 3.522(4) 2_555
C(3) C(20) 3.302(5) 2_555
C(4) O(2) 3.126(3) 2_555
C(4) C(20) 3.561(5) 2_555
C(6) O(1) 3.030(3) 2_566
C(6) C(15) 3.431(6) 2_566
C(9) O(2) 3.386(3) 1_665
C(9) C(19) 3.542(5) 2_565
C(10) O(2) 3.252(4) 1_665
C(13) O(1) 3.188(3) 2_566
C(14) O(1) 3.507(5) 2_566
C(14) C(18) 3.523(6) 2_565
C(15) O(1) 3.308(5) 2_566
C(15) N(1) 3.562(6) 2_566
C(15) C(1) 3.387(5) 2_566
C(15) C(6) 3.431(6) 2_566
C(17) O(2) 3.124(4) 2_555
C(18) O(2) 3.555(5) 2_555
C(18) C(14) 3.523(6) 2_565
C(19) C(9) 3.542(5) 2_565
C(20) O(2) 3.155(3) 2_555
C(20) N(2) 3.437(4) 2_555
C(20) C(3) 3.302(5) 2_555
C(20) C(4) 3.561(5) 2_555
O(1) H(3) 2.55(3) 2_566
O(1) H(8) 3.01(6) 2_566
O(1) H(13) 2.71(7) 2_566
O(1) H(28) 2.62(5) 1_445
O(2) H(2) 2.67(3) 2_555
O(2) H(5) 2.84(3) 1_445
O(2) H(6) 2.57(4) 1_445
O(2) H(19) 3.08(6) 2_555
O(2) H(23) 2.55(3) 2_555
O(2) H(25) 3.37(3) 2_555
N(1) H(11) 3.51(4) 2_566
N(1) H(13) 3.03(7) 2_566
N(2) H(23) 2.99(3) 2_555
N(2) H(25) 3.28(3) 2_555
C(1) H(11) 3.16(4) 2_566
C(1) H(13) 2.76(7) 2_566
C(2) H(6) 3.41(4) 1_445
C(2) H(13) 3.10(6) 2_566
C(2) H(23) 2.96(4) 2_555
C(3) H(23) 2.80(4) 2_555
C(3) H(25) 2.94(4) 2_555
C(4) H(5) 3.34(4) 2_665
C(4) H(23) 3.42(4) 2_555
C(4) H(25) 2.85(4) 2_555
C(5) H(11) 3.36(4) 2_566
C(5) H(17) 3.29(5) 2_565
C(5) H(25) 3.49(4) 2_555
C(6) H(11) 2.83(4) 2_566
C(6) H(13) 3.10(7) 2_566
C(6) H(17) 3.39(5) 2_565
C(6) H(18) 3.43(5) 2_565
C(7) H(15) 3.26(5) 1_655
C(7) H(17) 3.27(5) 2_565
C(7) H(18) 3.47(5) 2_565
C(7) H(21) 3.57(4) 2_565
C(7) H(22) 3.57(4) 2_565
C(8) H(4) 3.37(5) 2_665
C(8) H(5) 3.31(4) 2_665
C(8) H(14) 3.31(6) 2_565
C(8) H(17) 3.54(5) 2_565
C(8) H(21) 3.47(4) 2_565
C(8) H(22) 3.06(4) 2_565
C(9) H(2) 3.17(3) 2_665
C(9) H(4) 3.15(5) 2_665
C(9) H(9) 3.53(5) 1_655
C(9) H(14) 3.21(5) 2_565
C(9) H(21) 3.16(4) 2_565
C(9) H(22) 2.99(4) 2_565
C(10) H(1) 3.37(3) 1_665
C(10) H(9) 2.98(5) 1_655
C(10) H(19) 3.31(5) 2_665
C(10) H(21) 2.93(5) 2_565
C(10) H(22) 3.42(4) 2_565
C(11) H(9) 2.80(5) 1_655
C(11) H(21) 3.03(5) 2_565
C(12) H(9) 3.23(5) 1_655
C(12) H(11) 3.60(4) 2_566
C(12) H(12) 3.56(5) 1_655
C(12) H(15) 3.49(5) 1_655
C(12) H(18) 3.43(6) 2_565
C(12) H(21) 3.35(5) 2_565
C(12) H(27) 3.40(5) 2_676
C(14) H(18) 3.37(4) 2_565
C(14) H(19) 2.99(5) 2_565
C(14) H(26) 3.44(4) 1_455
C(14) H(28) 3.55(3) 2_676
C(15) H(3) 3.52(4) 2_566
C(15) H(23) 3.36(2) 1_566
C(15) H(24) 3.28(3) 1_566
C(16) H(4) 3.56(4) 2_565
C(16) H(5) 3.23(3) 2_565
C(16) H(20) 3.14(3) 2_455
C(16) H(24) 3.52(3) 2_455
C(16) H(25) 3.07(3) 2_455
C(18) H(3) 3.55(4) 2_565
C(18) H(8) 3.52(5) 2_565
C(18) H(10) 2.82(7) 2_565
C(18) H(27) 3.60(4) 1_444
C(19) H(16) 3.13(4) 2_455
C(19) H(20) 3.41(4) 2_455
C(20) H(12) 3.28(3) 1_544
C(20) H(13) 3.11(6) 1_544
C(20) H(15) 3.50(4) 2_455
C(20) H(16) 3.12(5) 2_455
C(21) H(3) 3.48(3) 2_676
C(21) H(7) 3.57(4) 2_676
C(21) H(8) 3.16(3) 2_676
C(21) H(9) 3.21(5) 1_655
C(21) H(18) 3.16(4) 1_666
C(21) H(24) 3.56(4) 1_666
C(21) H(27) 3.56(5) 2_676
H(1) C(10) 3.37(3) 1_445
H(1) H(6) 2.69(6) 1_445
H(1) H(13) 3.44(6) 2_566
H(1) H(20) 3.43(5) 2_455
H(1) H(21) 3.51(5) 2_455
H(1) H(23) 3.08(6) 2_555
H(1) H(28) 3.45(6) 1_445
H(2) O(2) 2.67(3) 2_555
H(2) C(9) 3.17(4) 2_665
H(2) H(5) 2.51(6) 2_665
H(2) H(6) 3.47(5) 2_665
H(2) H(15) 3.47(5) 1_655
H(2) H(25) 2.85(6) 2_555
H(3) O(1) 2.55(3) 2_566
H(3) C(15) 3.52(4) 2_566
H(3) C(18) 3.55(4) 2_565
H(3) C(21) 3.48(3) 2_676
H(3) H(11) 2.80(6) 2_566
H(3) H(13) 3.40(8) 2_566
H(3) H(17) 3.33(6) 2_565
H(3) H(18) 2.96(7) 2_565
H(3) H(27) 3.23(5) 2_676
H(3) H(28) 2.90(5) 2_676
H(4) C(8) 3.37(5) 2_665
H(4) C(9) 3.15(5) 2_665
H(4) C(16) 3.56(4) 2_565
H(4) H(4) 3.31(7) 2_665
H(4) H(5) 2.93(7) 2_665
H(4) H(10) 3.05(6) 2_565
H(4) H(14) 2.83(8) 2_565
H(4) H(15) 3.40(6) 2_565
H(4) H(22) 3.29(6) 2_565
H(5) O(2) 2.84(3) 1_665
H(5) C(4) 3.34(4) 2_665
H(5) C(8) 3.31(4) 2_665
H(5) C(16) 3.23(3) 2_565
H(5) H(2) 2.51(6) 2_665
H(5) H(4) 2.93(7) 2_665
H(5) H(14) 2.67(6) 2_565
H(5) H(15) 2.87(5) 2_565
H(5) H(19) 3.59(6) 2_665
H(5) H(20) 3.07(7) 1_665
H(5) H(22) 3.19(6) 2_565
H(5) H(25) 3.34(5) 1_665
H(6) O(2) 2.57(4) 1_665
H(6) C(2) 3.41(4) 1_665
H(6) H(1) 2.69(6) 1_665
H(6) H(2) 3.47(5) 2_665
H(6) H(9) 3.23(7) 1_655
H(6) H(19) 2.83(7) 2_665
H(6) H(21) 3.30(6) 2_565
H(6) H(23) 2.94(5) 2_665
H(7) C(21) 3.57(4) 2_676
H(7) H(11) 2.88(6) 2_566
H(7) H(12) 3.31(7) 1_655
H(7) H(18) 3.51(7) 2_565
H(7) H(27) 2.95(7) 2_676
H(7) H(28) 3.29(6) 2_676
H(8) O(1) 3.01(6) 2_566
H(8) C(18) 3.52(5) 2_565
H(8) C(21) 3.16(3) 2_676
H(8) H(18) 3.14(7) 2_565
H(8) H(19) 3.11(7) 2_565
H(8) H(26) 3.18(8) 1_455
H(8) H(26) 2.87(5) 2_676
H(8) H(27) 3.47(6) 2_676
H(8) H(28) 2.70(5) 2_676
H(9) C(9) 3.53(5) 1_455
H(9) C(10) 2.98(5) 1_455
H(9) C(11) 2.80(5) 1_455
H(9) C(12) 3.23(5) 1_455
H(9) C(21) 3.21(5) 1_455
H(9) H(6) 3.23(7) 1_455
H(9) H(19) 2.96(7) 2_565
H(9) H(26) 2.68(6) 1_455
H(10) C(18) 2.82(6) 2_565
H(10) H(4) 3.05(6) 2_565
H(10) H(17) 2.77(8) 2_565
H(10) H(18) 2.80(7) 2_565
H(10) H(19) 2.40(9) 2_565
H(11) N(1) 3.51(4) 2_566
H(11) C(1) 3.16(4) 2_566
H(11) C(5) 3.36(4) 2_566
H(11) C(6) 2.83(4) 2_566
H(11) C(12) 3.60(4) 2_566
H(11) H(3) 2.80(6) 2_566
H(11) H(7) 2.88(6) 2_566
H(11) H(12) 3.14(5) 2_466
H(12) C(12) 3.56(5) 1_455
H(12) C(20) 3.28(3) 1_566
H(12) H(7) 3.31(7) 1_455
H(12) H(11) 3.14(5) 2_466
H(12) H(12) 3.33(5) 2_466
H(12) H(23) 3.26(3) 1_566
H(12) H(24) 2.73(5) 1_566
H(12) H(25) 3.38(4) 1_566
H(12) H(26) 3.44(6) 1_455
H(13) O(1) 2.71(7) 2_566
H(13) N(1) 3.03(7) 2_566
H(13) C(1) 2.76(7) 2_566
H(13) C(2) 3.10(6) 2_566
H(13) C(6) 3.10(7) 2_566
H(13) C(20) 3.11(6) 1_566
H(13) H(1) 3.44(6) 2_566
H(13) H(3) 3.40(8) 2_566
H(13) H(23) 2.64(6) 1_566
H(13) H(24) 2.99(8) 1_566
H(13) H(25) 3.19(7) 1_566
H(14) C(8) 3.31(5) 2_565
H(14) C(9) 3.21(5) 2_565
H(14) H(4) 2.83(8) 2_565
H(14) H(5) 2.67(6) 2_565
H(14) H(20) 2.89(5) 2_455
H(14) H(25) 3.45(6) 2_455
H(15) C(7) 3.26(5) 1_455
H(15) C(12) 3.49(5) 1_455
H(15) C(20) 3.50(4) 2_455
H(15) H(2) 3.47(5) 1_455
H(15) H(4) 3.40(6) 2_565
H(15) H(5) 2.87(5) 2_565
H(15) H(20) 3.42(5) 2_455
H(15) H(24) 3.47(6) 2_455
H(15) H(25) 2.69(5) 2_455
H(16) C(19) 3.13(4) 2_455
H(16) C(20) 3.12(5) 2_455
H(16) H(20) 2.68(5) 2_455
H(16) H(21) 2.87(6) 2_455
H(16) H(24) 2.75(6) 2_455
H(16) H(25) 2.70(6) 2_455
H(17) C(5) 3.29(5) 2_565
H(17) C(6) 3.39(5) 2_565
H(17) C(7) 3.27(5) 2_565
H(17) C(8) 3.54(5) 2_565
H(17) H(3) 3.33(6) 2_565
H(17) H(10) 2.77(8) 2_565
H(18) C(6) 3.43(5) 2_565
H(18) C(7) 3.47(5) 2_565
H(18) C(12) 3.43(6) 2_565
H(18) C(14) 3.37(4) 2_565
H(18) C(21) 3.16(4) 1_444
H(18) H(3) 2.96(7) 2_565
H(18) H(7) 3.51(7) 2_565
H(18) H(8) 3.14(7) 2_565
H(18) H(10) 2.80(7) 2_565
H(18) H(26) 2.96(5) 1_444
H(18) H(27) 2.63(6) 1_444
H(18) H(28) 3.44(7) 1_444
H(19) O(2) 3.08(6) 2_555
H(19) C(10) 3.31(5) 2_665
H(19) C(14) 2.99(5) 2_565
H(19) H(5) 3.59(6) 2_665
H(19) H(6) 2.83(7) 2_665
H(19) H(8) 3.11(7) 2_565
H(19) H(9) 2.96(7) 2_565
H(19) H(10) 2.40(9) 2_565
H(20) C(16) 3.14(3) 2_455
H(20) C(19) 3.41(4) 2_455
H(20) H(1) 3.43(5) 2_455
H(20) H(5) 3.07(7) 1_445
H(20) H(14) 2.89(5) 2_455
H(20) H(15) 3.42(5) 2_455
H(20) H(16) 2.68(5) 2_455
H(20) H(20) 2.92(6) 2_455
H(20) H(22) 3.16(6) 2_455
H(21) C(7) 3.57(4) 2_565
H(21) C(8) 3.47(4) 2_565
H(21) C(9) 3.16(4) 2_565
H(21) C(10) 2.93(5) 2_565
H(21) C(11) 3.03(5) 2_565
H(21) C(12) 3.35(5) 2_565
H(21) H(1) 3.51(5) 2_455
H(21) H(6) 3.30(6) 2_565
H(21) H(16) 2.87(6) 2_455
H(21) H(28) 3.53(6) 2_565
H(22) C(7) 3.57(4) 2_565
H(22) C(8) 3.06(4) 2_565
H(22) C(9) 2.99(4) 2_565
H(22) C(10) 3.42(4) 2_565
H(22) H(4) 3.29(6) 2_565
H(22) H(5) 3.19(6) 2_565
H(22) H(20) 3.16(6) 2_455
H(23) O(2) 2.55(3) 2_555
H(23) N(2) 2.99(3) 2_555
H(23) C(2) 2.96(4) 2_555
H(23) C(3) 2.80(4) 2_555
H(23) C(4) 3.42(4) 2_555
H(23) C(15) 3.36(2) 1_544
H(23) H(1) 3.08(6) 2_555
H(23) H(6) 2.94(5) 2_665
H(23) H(12) 3.26(3) 1_544
H(23) H(13) 2.64(6) 1_544
H(24) C(15) 3.28(3) 1_544
H(24) C(16) 3.52(3) 2_455
H(24) C(21) 3.56(4) 1_444
H(24) H(12) 2.73(5) 1_544
H(24) H(13) 2.99(8) 1_544
H(24) H(15) 3.47(6) 2_455
H(24) H(16) 2.75(6) 2_455
H(24) H(26) 3.16(6) 1_444
H(24) H(27) 3.07(7) 1_444
H(25) O(2) 3.37(3) 2_555
H(25) N(2) 3.28(3) 2_555
H(25) C(3) 2.94(4) 2_555
H(25) C(4) 2.85(4) 2_555
H(25) C(5) 3.49(4) 2_555
H(25) C(16) 3.07(3) 2_455
H(25) H(2) 2.85(6) 2_555
H(25) H(5) 3.34(5) 1_445
H(25) H(12) 3.38(4) 1_544
H(25) H(13) 3.19(7) 1_544
H(25) H(14) 3.45(6) 2_455
H(25) H(15) 2.69(5) 2_455
H(25) H(16) 2.70(6) 2_455
H(26) C(14) 3.44(4) 1_655
H(26) H(8) 3.18(8) 1_655
H(26) H(8) 2.87(5) 2_676
H(26) H(9) 2.68(6) 1_655
H(26) H(12) 3.44(6) 1_655
H(26) H(18) 2.96(5) 1_666
H(26) H(24) 3.16(6) 1_666
H(26) H(26) 3.52(6) 2_776
H(27) C(12) 3.40(5) 2_676
H(27) C(18) 3.60(4) 1_666
H(27) C(21) 3.56(5) 2_676
H(27) H(3) 3.23(5) 2_676
H(27) H(7) 2.95(7) 2_676
H(27) H(8) 3.47(6) 2_676
H(27) H(18) 2.63(6) 1_666
H(27) H(24) 3.07(7) 1_666
H(27) H(27) 2.87(7) 2_676
H(28) O(1) 2.62(5) 1_665
H(28) C(14) 3.55(3) 2_676
H(28) H(1) 3.45(6) 1_665
H(28) H(3) 2.90(5) 2_676
H(28) H(7) 3.29(6) 2_676
H(28) H(8) 2.70(5) 2_676
H(28) H(18) 3.44(7) 1_666
H(28) H(21) 3.53(6) 2_565
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
O(1) N(1) C(1) C(2) 48.5(3)
O(1) N(1) C(1) C(6) -129.0(3)
O(1) N(1) C(13) C(14) 166.4(2)
O(1) N(1) C(13) C(15) 44.4(2)
O(1) N(1) C(13) C(16) -74.6(3)
C(1) N(1) C(13) C(14) -48.1(2)
C(1) N(1) C(13) C(15) -170.0(2)
C(1) N(1) C(13) C(16) 71.0(3)
C(13) N(1) C(1) C(2) -97.8(3)
C(13) N(1) C(1) C(6) 84.7(3)
O(2) N(2) C(3) C(2) -42.8(4)
O(2) N(2) C(3) C(4) 136.6(3)
O(2) N(2) C(17) C(18) -171.3(2)
O(2) N(2) C(17) C(19) 68.6(3)
O(2) N(2) C(17) C(20) -50.7(3)
C(3) N(2) C(17) C(18) 44.7(3)
C(3) N(2) C(17) C(19) -75.5(3)
C(3) N(2) C(17) C(20) 165.2(2)
C(17) N(2) C(3) C(2) 101.2(3)
C(17) N(2) C(3) C(4) -79.4(4)
N(1) C(1) C(2) C(3) -179.6(3)
N(1) C(1) C(6) C(5) 177.2(3)
C(2) C(1) C(6) C(5) -0.3(5)
C(6) C(1) C(2) C(3) -2.1(5)
C(1) C(2) C(3) N(2) -177.4(3)
C(1) C(2) C(3) C(4) 3.2(5)
N(2) C(3) C(4) C(5) 178.7(3)
C(2) C(3) C(4) C(5) -1.9(5)
C(3) C(4) C(5) C(6) -0.6(5)
C(3) C(4) C(5) C(7) 177.2(3)
C(4) C(5) C(6) C(1) 1.6(5)
C(4) C(5) C(7) C(8) 28.9(5)
C(4) C(5) C(7) C(12) -151.5(3)
C(6) C(5) C(7) C(8) -153.4(3)
C(6) C(5) C(7) C(12) 26.2(5)
C(7) C(5) C(6) C(1) -176.2(3)
C(5) C(7) C(8) C(9) 179.5(3)
C(5) C(7) C(12) C(11) -179.0(3)
C(8) C(7) C(12) C(11) 0.6(5)
C(12) C(7) C(8) C(9) -0.1(4)
C(7) C(8) C(9) C(10) -0.6(6)
C(8) C(9) C(10) C(11) 0.7(6)
C(9) C(10) C(11) C(12) -0.2(5)
C(9) C(10) C(11) C(21) 179.5(3)
C(10) C(11) C(12) C(7) -0.5(5)
C(21) C(11) C(12) C(7) 179.8(3)
