#------------------------------------------------------------------------------
#$Date: 2020-11-06 23:34:01 +0200 (Fri, 06 Nov 2020) $
#$Revision: 259013 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/94/1559483.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_1559483
loop_
_publ_author_name
'Kranjc, Krištof'
'Juranovič, Amadej'
'Kočevar, Marijan'
'Perdih, Franc'
_publ_section_title
;
 Supramolecular Diversity of Oxabicyclo[2.2.2]octenes Formed between
 Substituted 2H-Pyran-2-ones and Vinyl-Moiety-Containing Dienophiles
;
_journal_issue                   10
_journal_name_full               Symmetry
_journal_page_first              1714
_journal_paper_doi               10.3390/sym12101714
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C17 H19 N O6'
_chemical_formula_sum            'C17 H19 N O6'
_chemical_formula_weight         333.33
_space_group_IT_number           61
_space_group_name_Hall           '-P 2bc 2ac'
_space_group_name_H-M_alt        'P c a b'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_space_group_name_H-M   'P c a b'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.2171(2)
_cell_length_b                   14.2221(3)
_cell_length_c                   17.1809(4)
_cell_measurement_reflns_used    4078
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.55
_cell_volume                     3229.58(11)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.055
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'φ scans + ω 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  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6922
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9496
_exptl_absorpt_correction_T_min  0.9304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0471
_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)+(0.0718P)²+0.9777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                2876
_reflns_number_total             3663
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            endo-3c.cif
_cod_data_source_block           endo-3c
_cod_original_sg_symbol_H-M      Pcab
_cod_database_code               1559483
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, 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
N1 N 0.52276(9) 0.08719(10) -0.08419(7) 0.0421(3) Uani 1 1 d . . .
H1 H 0.5568 0.1013 -0.0432 0.063 Uiso 1 1 calc R . .
O1 O 0.25710(8) 0.02155(8) -0.10134(7) 0.0466(3) Uani 1 1 d . . .
O2 O 0.39180(10) -0.06879(8) -0.08355(7) 0.0532(3) Uani 1 1 d . . .
O3 O 0.14496(12) 0.25421(12) -0.21824(10) 0.0777(4) Uani 1 1 d . . .
O4 O 0.42746(8) 0.22864(8) 0.00602(6) 0.0462(3) Uani 1 1 d . . .
O5 O 0.52530(9) 0.02670(10) -0.20610(7) 0.0573(4) Uani 1 1 d . . .
O6 O 0.73057(9) 0.08426(10) -0.08172(7) 0.0575(3) Uani 1 1 d . . .
C1 C 0.35639(12) 0.00861(11) -0.09118(8) 0.0415(3) Uani 1 1 d . . .
C2 C 0.41512(11) 0.10163(11) -0.08605(8) 0.0381(3) Uani 1 1 d . . .
C3 C 0.37563(11) 0.14380(11) -0.00830(8) 0.0395(3) Uani 1 1 d . . .
H3 H 0.3899 0.0996 0.0340 0.047 Uiso 1 1 calc R . .
C4 C 0.25994(12) 0.15578(13) -0.01602(9) 0.0471(4) Uani 1 1 d . . .
H4A H 0.2264 0.1201 0.0246 0.057 Uiso 1 1 calc R . .
H4B H 0.2424 0.2215 -0.0093 0.057 Uiso 1 1 calc R . .
C5 C 0.22299(11) 0.12181(12) -0.09605(9) 0.0447(4) Uani 1 1 d . . .
C6 C 0.28129(12) 0.17540(11) -0.15828(8) 0.0420(3) Uani 1 1 d . . .
C7 C 0.38074(11) 0.16414(11) -0.15141(8) 0.0401(3) Uani 1 1 d . . .
H7 H 0.4262 0.1932 -0.1850 0.048 Uiso 1 1 calc R . .
C8 C 0.10902(13) 0.11573(16) -0.10197(13) 0.0618(5) Uani 1 1 d . . .
H8A H 0.0906 0.0926 -0.1525 0.093 Uiso 1 1 calc R . .
H8B H 0.0803 0.1770 -0.0944 0.093 Uiso 1 1 calc R . .
H8C H 0.0839 0.0737 -0.0628 0.093 Uiso 1 1 calc R . .
C9 C 0.23428(14) 0.23655(12) -0.21866(10) 0.0524(4) Uani 1 1 d . . .
C10 C 0.30188(19) 0.27470(17) -0.28161(12) 0.0734(6) Uani 1 1 d . . .
H10A H 0.3219 0.2245 -0.3156 0.110 Uiso 1 1 calc R . .
H10B H 0.3609 0.3025 -0.2585 0.110 Uiso 1 1 calc R . .
H10C H 0.2660 0.3215 -0.3109 0.110 Uiso 1 1 calc R . .
C11 C 0.42650(19) 0.25120(17) 0.08728(11) 0.0731(6) Uani 1 1 d . . .
H11A H 0.4645 0.2040 0.1157 0.088 Uiso 1 1 calc R . .
H11B H 0.3573 0.2501 0.1062 0.088 Uiso 1 1 calc R . .
C12 C 0.4701(2) 0.34298(18) 0.10201(13) 0.0851(7) Uani 1 1 d . . .
H12A H 0.5386 0.3442 0.0835 0.128 Uiso 1 1 calc R . .
H12B H 0.4692 0.3555 0.1569 0.128 Uiso 1 1 calc R . .
H12C H 0.4313 0.3901 0.0754 0.128 Uiso 1 1 calc R . .
C13 C 0.57025(11) 0.05120(11) -0.14741(9) 0.0423(3) Uani 1 1 d . . .
C14 C 0.68079(12) 0.04330(11) -0.14229(9) 0.0428(3) Uani 1 1 d . . .
C15 C 0.74681(14) 0.00493(13) -0.19232(11) 0.0540(4) Uani 1 1 d . . .
H15 H 0.7316 -0.0272 -0.2380 0.065 Uiso 1 1 calc R . .
C16 C 0.84514(14) 0.02325(16) -0.16149(13) 0.0651(5) Uani 1 1 d . . .
H16 H 0.9066 0.0052 -0.1832 0.078 Uiso 1 1 calc R . .
C17 C 0.83185(14) 0.07106(17) -0.09584(13) 0.0646(5) Uani 1 1 d . . .
H17 H 0.8838 0.0925 -0.0640 0.078 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
C13 N1 C2 119.64(12) . . ?
C13 N1 H1 120.2 . . ?
C2 N1 H1 120.2 . . ?
C1 O1 C5 114.74(12) . . ?
C3 O4 C11 110.96(13) . . ?
C14 O6 C17 106.11(14) . . ?
O2 C1 O1 121.47(15) . . ?
O2 C1 C2 125.80(15) . . ?
O1 C1 C2 112.65(13) . . ?
N1 C2 C7 113.60(12) . . ?
N1 C2 C1 112.22(13) . . ?
C7 C2 C1 108.29(12) . . ?
N1 C2 C3 111.61(11) . . ?
C7 C2 C3 108.20(12) . . ?
C1 C2 C3 102.23(11) . . ?
O4 C3 C4 113.70(13) . . ?
O4 C3 C2 108.49(11) . . ?
C4 C3 C2 107.53(12) . . ?
O4 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C5 C4 C3 110.90(12) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
O1 C5 C8 103.96(13) . . ?
O1 C5 C6 106.36(12) . . ?
C8 C5 C6 119.05(15) . . ?
O1 C5 C4 104.94(12) . . ?
C8 C5 C4 113.24(14) . . ?
C6 C5 C4 108.07(13) . . ?
C7 C6 C9 123.00(15) . . ?
C7 C6 C5 112.19(13) . . ?
C9 C6 C5 124.77(14) . . ?
C6 C7 C2 115.89(14) . . ?
C6 C7 H7 122.1 . . ?
C2 C7 H7 122.1 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 C6 121.69(18) . . ?
O3 C9 C10 120.68(17) . . ?
C6 C9 C10 117.62(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 C12 111.62(18) . . ?
O4 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O4 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 N1 122.98(14) . . ?
O5 C13 C14 120.79(14) . . ?
N1 C13 C14 116.23(13) . . ?
C15 C14 O6 110.45(15) . . ?
C15 C14 C13 129.82(16) . . ?
O6 C14 C13 119.59(13) . . ?
C14 C15 C16 106.28(17) . . ?
C14 C15 H15 126.9 . . ?
C16 C15 H15 126.9 . . ?
C17 C16 C15 106.74(16) . . ?
C17 C16 H16 126.6 . . ?
C15 C16 H16 126.6 . . ?
C16 C17 O6 110.41(17) . . ?
C16 C17 H17 124.8 . . ?
O6 C17 H17 124.8 . . ?
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 C13 1.3549(19) . ?
N1 C2 1.4378(18) . ?
N1 H1 0.8600 . ?
O1 C1 1.3366(19) . ?
O1 C5 1.498(2) . ?
O2 C1 1.203(2) . ?
O3 C9 1.207(2) . ?
O4 C3 1.4091(18) . ?
O4 C11 1.4326(19) . ?
O5 C13 1.2211(18) . ?
O6 C14 1.3621(19) . ?
O6 C17 1.373(2) . ?
C1 C2 1.536(2) . ?
C2 C7 1.503(2) . ?
C2 C3 1.5544(19) . ?
C3 C4 1.544(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.537(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C8 1.512(2) . ?
C5 C6 1.522(2) . ?
C6 C7 1.329(2) . ?
C6 C9 1.489(2) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.504(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.449(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.468(2) . ?
C14 C15 1.341(2) . ?
C15 C16 1.427(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.329(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
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
C5 O1 C1 O2 169.88(14) . . . . ?
C5 O1 C1 C2 -6.91(17) . . . . ?
C13 N1 C2 C7 -57.03(19) . . . . ?
C13 N1 C2 C1 66.23(18) . . . . ?
C13 N1 C2 C3 -179.69(14) . . . . ?
O2 C1 C2 N1 10.1(2) . . . . ?
O1 C1 C2 N1 -173.27(12) . . . . ?
O2 C1 C2 C7 136.30(15) . . . . ?
O1 C1 C2 C7 -47.08(16) . . . . ?
O2 C1 C2 C3 -109.60(16) . . . . ?
O1 C1 C2 C3 67.02(15) . . . . ?
C11 O4 C3 C4 83.72(18) . . . . ?
C11 O4 C3 C2 -156.69(15) . . . . ?
N1 C2 C3 O4 57.06(16) . . . . ?
C7 C2 C3 O4 -68.64(15) . . . . ?
C1 C2 C3 O4 177.20(11) . . . . ?
N1 C2 C3 C4 -179.57(13) . . . . ?
C7 C2 C3 C4 54.73(15) . . . . ?
C1 C2 C3 C4 -59.42(14) . . . . ?
O4 C3 C4 C5 120.68(14) . . . . ?
C2 C3 C4 C5 0.55(17) . . . . ?
C1 O1 C5 C8 -174.94(14) . . . . ?
C1 O1 C5 C6 58.59(16) . . . . ?
C1 O1 C5 C4 -55.79(16) . . . . ?
C3 C4 C5 O1 57.15(16) . . . . ?
C3 C4 C5 C8 169.87(15) . . . . ?
C3 C4 C5 C6 -56.03(17) . . . . ?
O1 C5 C6 C7 -54.72(16) . . . . ?
C8 C5 C6 C7 -171.50(16) . . . . ?
C4 C5 C6 C7 57.50(17) . . . . ?
O1 C5 C6 C9 127.37(15) . . . . ?
C8 C5 C6 C9 10.6(2) . . . . ?
C4 C5 C6 C9 -120.40(16) . . . . ?
C9 C6 C7 C2 178.62(14) . . . . ?
C5 C6 C7 C2 0.68(19) . . . . ?
N1 C2 C7 C6 176.35(13) . . . . ?
C1 C2 C7 C6 50.97(17) . . . . ?
C3 C2 C7 C6 -59.13(17) . . . . ?
C7 C6 C9 O3 -171.35(17) . . . . ?
C5 C6 C9 O3 6.3(3) . . . . ?
C7 C6 C9 C10 9.7(2) . . . . ?
C5 C6 C9 C10 -172.63(17) . . . . ?
C3 O4 C11 C12 -173.9(2) . . . . ?
C2 N1 C13 O5 -2.7(2) . . . . ?
C2 N1 C13 C14 176.88(14) . . . . ?
C17 O6 C14 C15 0.6(2) . . . . ?
C17 O6 C14 C13 -175.63(16) . . . . ?
O5 C13 C14 C15 -5.6(3) . . . . ?
N1 C13 C14 C15 174.75(18) . . . . ?
O5 C13 C14 O6 169.78(16) . . . . ?
N1 C13 C14 O6 -9.9(2) . . . . ?
O6 C14 C15 C16 -0.3(2) . . . . ?
C13 C14 C15 C16 175.44(18) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C15 C16 C17 O6 0.5(2) . . . . ?
C14 O6 C17 C16 -0.7(2) . . . . ?
