#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/40/4024050.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_4024050
loop_
_publ_author_name
'Mateo Alajarín'
'Baltasar Bonillo'
'Pilar Sánchez-Andrada'
'Ángel Vidal'
'Delia Bautista'
_publ_section_title
;
 Intramolecular Ketenimine-Ketenimine [2 + 2] and [4 + 2] Cycloadditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5863
_journal_page_last               5866
_journal_paper_doi               10.1021/jo0704661
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C40 H28 N2 O2'
_chemical_formula_weight         568.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.497(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5954(9)
_cell_length_b                   13.0422(9)
_cell_length_c                   16.1307(11)
_cell_measurement_reflns_used    2413
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.01
_cell_measurement_theta_min      2.41
_cell_volume                     2828.8(3)
_computing_cell_refinement       'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       8.26
_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  0.0799
_diffrn_reflns_av_sigmaI/netI    0.1067
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17588
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    'OH free, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0269P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                4017
_reflns_number_total             6379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0704661si20070306_044319.cif
_cod_data_source_block           avg285cm
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024050
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17731(12) 0.58768(12) 0.54833(9) 0.0179(4) Uani 1 1 d . . .
N2 N 0.40813(12) 0.64762(11) 0.54176(9) 0.0172(4) Uani 1 1 d . . .
O1 O 0.09716(10) 0.74691(10) 0.62064(8) 0.0224(3) Uani 1 1 d . . .
O2 O 0.02646(11) 0.73298(12) 0.54328(9) 0.0295(4) Uani 1 1 d . . .
H02 H 0.043(2) 0.663(2) 0.5351(18) 0.100(12) Uiso 1 1 d . . .
C1 C 0.20735(15) 0.50017(14) 0.50458(12) 0.0191(5) Uani 1 1 d . . .
C2 C 0.13766(15) 0.46081(15) 0.44089(12) 0.0237(5) Uani 1 1 d . . .
H2 H 0.0742 0.4923 0.4283 0.028 Uiso 1 1 calc R . .
C3 C 0.16000(17) 0.37630(16) 0.39571(13) 0.0288(5) Uani 1 1 d . . .
H3 H 0.1127 0.3510 0.3512 0.035 Uiso 1 1 calc R . .
C4 C 0.25127(17) 0.32841(16) 0.41519(13) 0.0308(6) Uani 1 1 d . . .
H4 H 0.2673 0.2711 0.3833 0.037 Uiso 1 1 calc R . .
C5 C 0.31941(16) 0.36439(15) 0.48149(13) 0.0259(5) Uani 1 1 d . . .
H5 H 0.3811 0.3298 0.4958 0.031 Uiso 1 1 calc R . .
C6 C 0.29883(15) 0.45037(14) 0.52737(12) 0.0197(5) Uani 1 1 d . . .
C7 C 0.37077(14) 0.48038(15) 0.60218(12) 0.0188(5) Uani 1 1 d . . .
C8 C 0.39467(15) 0.41010(15) 0.66730(12) 0.0225(5) Uani 1 1 d . . .
H8 H 0.3633 0.3448 0.6635 0.027 Uiso 1 1 calc R . .
C9 C 0.46285(15) 0.43311(16) 0.73717(12) 0.0245(5) Uani 1 1 d . . .
H9 H 0.4770 0.3847 0.7813 0.029 Uiso 1 1 calc R . .
C10 C 0.51039(15) 0.52736(16) 0.74239(12) 0.0240(5) Uani 1 1 d . . .
H10 H 0.5559 0.5445 0.7909 0.029 Uiso 1 1 calc R . .
C11 C 0.49170(15) 0.59649(15) 0.67694(12) 0.0219(5) Uani 1 1 d . . .
H11 H 0.5275 0.6592 0.6791 0.026 Uiso 1 1 calc R . .
C12 C 0.42066(14) 0.57444(14) 0.60791(11) 0.0167(4) Uani 1 1 d . . .
C13 C 0.32344(14) 0.68840(14) 0.51860(11) 0.0149(4) Uani 1 1 d . . .
C14 C 0.30841(14) 0.76587(14) 0.44656(11) 0.0150(4) Uani 1 1 d . . .
C15 C 0.24596(13) 0.85632(14) 0.47104(11) 0.0148(4) Uani 1 1 d . . .
C16 C 0.23930(14) 0.94330(14) 0.42003(11) 0.0171(4) Uani 1 1 d . . .
H16 H 0.2757 0.9451 0.3741 0.021 Uiso 1 1 calc R . .
C17 C 0.18162(14) 1.02663(15) 0.43423(11) 0.0182(4) Uani 1 1 d . . .
H17 H 0.1783 1.0847 0.3984 0.022 Uiso 1 1 calc R . .
C18 C 0.12877(14) 1.02494(15) 0.50107(12) 0.0194(5) Uani 1 1 d . . .
H18 H 0.0885 1.0818 0.5113 0.023 Uiso 1 1 calc R . .
C19 C 0.13474(14) 0.94031(14) 0.55284(12) 0.0191(5) Uani 1 1 d . . .
H19 H 0.0987 0.9396 0.5990 0.023 Uiso 1 1 calc R . .
C20 C 0.19288(14) 0.85550(14) 0.53866(11) 0.0163(4) Uani 1 1 d . . .
C21 C 0.19432(14) 0.76372(14) 0.59761(11) 0.0167(4) Uani 1 1 d . . .
C22 C 0.23011(14) 0.66909(14) 0.55526(11) 0.0147(4) Uani 1 1 d . . .
C31 C 0.25114(14) 0.70452(14) 0.37287(11) 0.0155(4) Uani 1 1 d . . .
C32 C 0.15317(14) 0.72596(15) 0.33886(11) 0.0189(5) Uani 1 1 d . . .
H32 H 0.1198 0.7823 0.3595 0.023 Uiso 1 1 calc R . .
C33 C 0.10369(15) 0.66529(15) 0.27468(12) 0.0221(5) Uani 1 1 d . . .
H33 H 0.0370 0.6811 0.2516 0.026 Uiso 1 1 calc R . .
C34 C 0.15044(15) 0.58292(15) 0.24449(12) 0.0235(5) Uani 1 1 d . . .
H34 H 0.1167 0.5422 0.2004 0.028 Uiso 1 1 calc R . .
C35 C 0.24742(15) 0.55970(15) 0.27904(12) 0.0226(5) Uani 1 1 d . . .
H35 H 0.2799 0.5024 0.2588 0.027 Uiso 1 1 calc R . .
C36 C 0.29711(15) 0.61939(15) 0.34264(12) 0.0206(5) Uani 1 1 d . . .
H36 H 0.3633 0.6023 0.3661 0.025 Uiso 1 1 calc R . .
C41 C 0.40877(14) 0.80752(14) 0.42834(12) 0.0182(4) Uani 1 1 d . . .
C42 C 0.43630(15) 0.80964(15) 0.34899(12) 0.0232(5) Uani 1 1 d . . .
H42 H 0.3925 0.7826 0.3028 0.028 Uiso 1 1 calc R . .
C43 C 0.52720(16) 0.85093(16) 0.33605(14) 0.0303(5) Uani 1 1 d . . .
H43 H 0.5451 0.8520 0.2813 0.036 Uiso 1 1 calc R . .
C44 C 0.59135(16) 0.89032(15) 0.40290(15) 0.0309(6) Uani 1 1 d . . .
H44 H 0.6540 0.9173 0.3945 0.037 Uiso 1 1 calc R . .
C45 C 0.56388(15) 0.89017(15) 0.48189(14) 0.0270(5) Uani 1 1 d . . .
H45 H 0.6076 0.9180 0.5278 0.032 Uiso 1 1 calc R . .
C46 C 0.47347(14) 0.84996(14) 0.49473(12) 0.0210(5) Uani 1 1 d . . .
H46 H 0.4551 0.8512 0.5493 0.025 Uiso 1 1 calc R . .
C51 C 0.25784(14) 0.77898(15) 0.68371(11) 0.0179(4) Uani 1 1 d . . .
C52 C 0.26876(15) 0.69605(15) 0.73907(12) 0.0233(5) Uani 1 1 d . . .
H52 H 0.2413 0.6312 0.7215 0.028 Uiso 1 1 calc R . .
C53 C 0.31951(16) 0.70803(17) 0.81952(12) 0.0297(5) Uani 1 1 d . . .
H53 H 0.3268 0.6512 0.8568 0.036 Uiso 1 1 calc R . .
C54 C 0.35939(15) 0.80125(17) 0.84587(13) 0.0293(5) Uani 1 1 d . . .
H54 H 0.3933 0.8092 0.9014 0.035 Uiso 1 1 calc R . .
C55 C 0.35002(15) 0.88361(17) 0.79122(13) 0.0278(5) Uani 1 1 d . . .
H55 H 0.3780 0.9481 0.8091 0.033 Uiso 1 1 calc R . .
C56 C 0.29979(14) 0.87245(15) 0.71019(12) 0.0226(5) Uani 1 1 d . . .
H56 H 0.2942 0.9291 0.6728 0.027 Uiso 1 1 calc 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'
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
C22 N1 C1 120.52(16) . . ?
C13 N2 C12 120.20(16) . . ?
C21 O1 O2 108.02(12) . . ?
C2 C1 C6 120.27(18) . . ?
C2 C1 N1 116.48(18) . . ?
C6 C1 N1 123.09(17) . . ?
C3 C2 C1 120.4(2) . . ?
C2 C3 C4 120.1(2) . . ?
C3 C4 C5 119.7(2) . . ?
C4 C5 C6 121.1(2) . . ?
C5 C6 C1 118.22(18) . . ?
C5 C6 C7 118.83(18) . . ?
C1 C6 C7 122.77(17) . . ?
C8 C7 C12 118.01(18) . . ?
C8 C7 C6 119.30(18) . . ?
C12 C7 C6 122.57(17) . . ?
C9 C8 C7 121.63(19) . . ?
C8 C9 C10 119.52(18) . . ?
C11 C10 C9 120.04(19) . . ?
C10 C11 C12 120.23(19) . . ?
C11 C12 C7 120.44(18) . . ?
C11 C12 N2 116.96(17) . . ?
C7 C12 N2 122.39(17) . . ?
N2 C13 C22 126.58(17) . . ?
N2 C13 C14 120.80(16) . . ?
C22 C13 C14 112.63(15) . . ?
C13 C14 C41 110.84(15) . . ?
C13 C14 C15 109.16(15) . . ?
C41 C14 C15 108.50(15) . . ?
C13 C14 C31 103.76(14) . . ?
C41 C14 C31 113.38(15) . . ?
C15 C14 C31 111.11(15) . . ?
C20 C15 C16 118.12(17) . . ?
C20 C15 C14 124.33(17) . . ?
C16 C15 C14 117.51(16) . . ?
C17 C16 C15 122.09(18) . . ?
C16 C17 C18 119.42(18) . . ?
C19 C18 C17 119.64(19) . . ?
C18 C19 C20 121.23(18) . . ?
C15 C20 C19 119.50(17) . . ?
C15 C20 C21 122.19(17) . . ?
C19 C20 C21 118.29(16) . . ?
O1 C21 C22 110.97(15) . . ?
O1 C21 C20 110.61(15) . . ?
C22 C21 C20 109.34(15) . . ?
O1 C21 C51 101.59(14) . . ?
C22 C21 C51 109.63(15) . . ?
C20 C21 C51 114.54(15) . . ?
N1 C22 C13 127.08(17) . . ?
N1 C22 C21 119.97(17) . . ?
C13 C22 C21 112.69(16) . . ?
C32 C31 C36 118.27(18) . . ?
C32 C31 C14 122.92(17) . . ?
C36 C31 C14 118.67(17) . . ?
C31 C32 C33 120.48(18) . . ?
C34 C33 C32 120.61(19) . . ?
C33 C34 C35 119.38(19) . . ?
C36 C35 C34 120.45(19) . . ?
C35 C36 C31 120.80(19) . . ?
C42 C41 C46 118.36(19) . . ?
C42 C41 C14 123.52(18) . . ?
C46 C41 C14 118.04(17) . . ?
C41 C42 C43 120.9(2) . . ?
C44 C43 C42 119.9(2) . . ?
C45 C44 C43 119.6(2) . . ?
C44 C45 C46 120.5(2) . . ?
C45 C46 C41 120.66(19) . . ?
C56 C51 C52 118.95(18) . . ?
C56 C51 C21 122.90(17) . . ?
C52 C51 C21 118.05(17) . . ?
C53 C52 C51 120.18(19) . . ?
C54 C53 C52 120.6(2) . . ?
C53 C54 C55 119.7(2) . . ?
C54 C55 C56 120.3(2) . . ?
C51 C56 C55 120.29(19) . . ?
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
N1 C22 1.277(2) . ?
N1 C1 1.433(2) . ?
N2 C13 1.273(2) . ?
N2 C12 1.423(2) . ?
O1 C21 1.441(2) . ?
O1 O2 1.4696(18) . ?
C1 C2 1.389(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.394(3) . ?
C6 C7 1.489(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.398(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.392(3) . ?
C13 C22 1.498(3) . ?
C13 C14 1.531(2) . ?
C14 C41 1.537(3) . ?
C14 C15 1.539(2) . ?
C14 C31 1.545(2) . ?
C15 C20 1.394(2) . ?
C15 C16 1.396(2) . ?
C16 C17 1.379(2) . ?
C17 C18 1.381(2) . ?
C18 C19 1.379(2) . ?
C19 C20 1.398(2) . ?
C20 C21 1.527(2) . ?
C21 C22 1.525(2) . ?
C21 C51 1.536(2) . ?
C31 C32 1.392(2) . ?
C31 C36 1.397(2) . ?
C32 C33 1.394(2) . ?
C33 C34 1.374(3) . ?
C34 C35 1.387(3) . ?
C35 C36 1.382(3) . ?
C41 C42 1.386(2) . ?
C41 C46 1.396(3) . ?
C42 C43 1.392(3) . ?
C43 C44 1.382(3) . ?
C44 C45 1.380(3) . ?
C45 C46 1.380(3) . ?
C51 C56 1.386(3) . ?
C51 C52 1.396(2) . ?
C52 C53 1.386(3) . ?
C53 C54 1.373(3) . ?
C54 C55 1.383(3) . ?
C55 C56 1.390(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H02 N1 0.95(3) 2.06(3) 2.785(2) 132(2) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 N1 C1 C2 -126.50(19) . . . . ?
C22 N1 C1 C6 58.2(3) . . . . ?
C6 C1 C2 C3 -4.2(3) . . . . ?
N1 C1 C2 C3 -179.66(17) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 174.93(18) . . . . ?
C2 C1 C6 C5 3.4(3) . . . . ?
N1 C1 C6 C5 178.55(17) . . . . ?
C2 C1 C6 C7 -171.58(18) . . . . ?
N1 C1 C6 C7 3.6(3) . . . . ?
C5 C6 C7 C8 -57.8(3) . . . . ?
C1 C6 C7 C8 117.2(2) . . . . ?
C5 C6 C7 C12 118.1(2) . . . . ?
C1 C6 C7 C12 -66.9(3) . . . . ?
C12 C7 C8 C9 2.3(3) . . . . ?
C6 C7 C8 C9 178.35(18) . . . . ?
C7 C8 C9 C10 -1.3(3) . . . . ?
C8 C9 C10 C11 -1.9(3) . . . . ?
C9 C10 C11 C12 4.0(3) . . . . ?
C10 C11 C12 C7 -2.9(3) . . . . ?
C10 C11 C12 N2 -177.81(17) . . . . ?
C8 C7 C12 C11 -0.2(3) . . . . ?
C6 C7 C12 C11 -176.09(18) . . . . ?
C8 C7 C12 N2 174.42(17) . . . . ?
C6 C7 C12 N2 -1.5(3) . . . . ?
C13 N2 C12 C11 -122.24(19) . . . . ?
C13 N2 C12 C7 63.0(2) . . . . ?
C12 N2 C13 C22 1.1(3) . . . . ?
C12 N2 C13 C14 -178.96(16) . . . . ?
N2 C13 C14 C41 -16.8(2) . . . . ?
C22 C13 C14 C41 163.16(15) . . . . ?
N2 C13 C14 C15 -136.27(17) . . . . ?
C22 C13 C14 C15 43.7(2) . . . . ?
N2 C13 C14 C31 105.21(19) . . . . ?
C22 C13 C14 C31 -74.81(18) . . . . ?
C13 C14 C15 C20 -13.8(2) . . . . ?
C41 C14 C15 C20 -134.65(18) . . . . ?
C31 C14 C15 C20 100.1(2) . . . . ?
C13 C14 C15 C16 168.76(16) . . . . ?
C41 C14 C15 C16 47.9(2) . . . . ?
C31 C14 C15 C16 -77.4(2) . . . . ?
C20 C15 C16 C17 -0.7(3) . . . . ?
C14 C15 C16 C17 176.99(17) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C16 C15 C20 C19 0.5(3) . . . . ?
C14 C15 C20 C19 -176.99(17) . . . . ?
C16 C15 C20 C21 179.35(16) . . . . ?
C14 C15 C20 C21 1.9(3) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C18 C19 C20 C21 -178.85(17) . . . . ?
O2 O1 C21 C22 -64.72(17) . . . . ?
O2 O1 C21 C20 56.81(18) . . . . ?
O2 O1 C21 C51 178.81(13) . . . . ?
C15 C20 C21 O1 -141.02(17) . . . . ?
C19 C20 C21 O1 37.9(2) . . . . ?
C15 C20 C21 C22 -18.5(2) . . . . ?
C19 C20 C21 C22 160.35(16) . . . . ?
C15 C20 C21 C51 104.9(2) . . . . ?
C19 C20 C21 C51 -76.2(2) . . . . ?
C1 N1 C22 C13 2.7(3) . . . . ?
C1 N1 C22 C21 176.51(16) . . . . ?
N2 C13 C22 N1 -71.0(3) . . . . ?
C14 C13 C22 N1 109.0(2) . . . . ?
N2 C13 C22 C21 114.9(2) . . . . ?
C14 C13 C22 C21 -65.12(19) . . . . ?
O1 C21 C22 N1 -3.4(2) . . . . ?
C20 C21 C22 N1 -125.65(18) . . . . ?
C51 C21 C22 N1 108.03(19) . . . . ?
O1 C21 C22 C13 171.24(14) . . . . ?
C20 C21 C22 C13 49.0(2) . . . . ?
C51 C21 C22 C13 -77.35(19) . . . . ?
C13 C14 C31 C32 112.75(19) . . . . ?
C41 C14 C31 C32 -126.93(19) . . . . ?
C15 C14 C31 C32 -4.4(2) . . . . ?
C13 C14 C31 C36 -62.8(2) . . . . ?
C41 C14 C31 C36 57.6(2) . . . . ?
C15 C14 C31 C36 -179.93(16) . . . . ?
C36 C31 C32 C33 -1.7(3) . . . . ?
C14 C31 C32 C33 -177.26(17) . . . . ?
C31 C32 C33 C34 0.6(3) . . . . ?
C32 C33 C34 C35 0.7(3) . . . . ?
C33 C34 C35 C36 -0.7(3) . . . . ?
C34 C35 C36 C31 -0.5(3) . . . . ?
C32 C31 C36 C35 1.7(3) . . . . ?
C14 C31 C36 C35 177.43(17) . . . . ?
C13 C14 C41 C42 129.34(19) . . . . ?
C15 C14 C41 C42 -110.8(2) . . . . ?
C31 C14 C41 C42 13.1(3) . . . . ?
C13 C14 C41 C46 -53.9(2) . . . . ?
C15 C14 C41 C46 66.0(2) . . . . ?
C31 C14 C41 C46 -170.10(16) . . . . ?
C46 C41 C42 C43 1.4(3) . . . . ?
C14 C41 C42 C43 178.22(17) . . . . ?
C41 C42 C43 C44 0.1(3) . . . . ?
C42 C43 C44 C45 -1.2(3) . . . . ?
C43 C44 C45 C46 0.8(3) . . . . ?
C44 C45 C46 C41 0.8(3) . . . . ?
C42 C41 C46 C45 -1.9(3) . . . . ?
C14 C41 C46 C45 -178.88(17) . . . . ?
O1 C21 C51 C56 -111.12(19) . . . . ?
C22 C21 C51 C56 131.44(19) . . . . ?
C20 C21 C51 C56 8.1(3) . . . . ?
O1 C21 C51 C52 65.2(2) . . . . ?
C22 C21 C51 C52 -52.2(2) . . . . ?
C20 C21 C51 C52 -175.53(17) . . . . ?
C56 C51 C52 C53 1.0(3) . . . . ?
C21 C51 C52 C53 -175.51(17) . . . . ?
C51 C52 C53 C54 0.2(3) . . . . ?
C52 C53 C54 C55 -0.9(3) . . . . ?
C53 C54 C55 C56 0.5(3) . . . . ?
C52 C51 C56 C55 -1.4(3) . . . . ?
C21 C51 C56 C55 174.95(18) . . . . ?
C54 C55 C56 C51 0.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20573999
