#------------------------------------------------------------------------------
#$Date: 2023-04-04 13:15:53 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282334 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/63/7246369.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_7246369
loop_
_publ_author_name
'Barton, Benita'
'Caira, Mino R.'
'Senekal, Ulrich'
'Hosten, Eric C.'
_publ_section_title
;
 Complementary host behaviour of three anthracenyl-derived roof-shaped
 compounds in mixed pyridines
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1740
_journal_page_last               1754
_journal_paper_doi               10.1039/D3CE00080J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         '2(C20 H18 O4), C6 H7 N'
_chemical_formula_sum            'C46 H43 N O8'
_chemical_formula_weight         737.81
_chemical_name_systematic
'trans-dimethyl 9,10-dihydro-9,10- ethanoanthracene-11,12-dicarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-01-13 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.136(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2912(6)
_cell_length_b                   21.2529(13)
_cell_length_c                   15.8162(10)
_cell_measurement_reflns_used    9162
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.41
_cell_volume                     3795.4(4)
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'
_computing_structure_refinement
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            96013
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_min         0.958
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9060
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1560
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 3-methylpyridine'
_exptl_crystal_size_max          0.636
_exptl_crystal_size_mid          0.504
_exptl_crystal_size_min          0.402
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         9440
_refine_ls_number_restraints     189
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0971P)²+1.6172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8453
_reflns_number_total             9440
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00080j2.cif
_cod_data_source_block           ma047
_cod_depositor_comments
'Adding full bibliography for 7246364--7246371.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246369
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O11 O -0.04749(13) 0.26280(8) 0.56544(10) 0.0405(4) Uani 1 1 d . . . . .
O12 O 0.14769(15) 0.27546(10) 0.57373(15) 0.0622(6) Uani 1 1 d . . . . .
O13 O 0.34658(13) 0.11339(7) 0.43028(11) 0.0372(3) Uani 1 1 d . . . . .
O14 O 0.19946(15) 0.08550(8) 0.51568(12) 0.0475(4) Uani 1 1 d . . . . .
O21 O 0.45692(14) 0.23045(7) -0.03797(11) 0.0406(4) Uani 1 1 d . . . . .
O22 O 0.65251(16) 0.21593(9) -0.03469(13) 0.0529(5) Uani 1 1 d . . . . .
O23 O 0.84511(13) 0.38969(7) 0.09054(11) 0.0378(3) Uani 1 1 d . . . . .
O24 O 0.70280(15) 0.40942(8) -0.00461(11) 0.0455(4) Uani 1 1 d . . . . .
C11 C -0.02769(16) 0.20046(8) 0.41119(12) 0.0265(3) Uani 1 1 d . . . . .
H11 H -0.110010 0.203593 0.433986 0.032 Uiso 1 1 calc R U . . .
C12 C 0.06695(16) 0.19443(8) 0.48348(12) 0.0263(3) Uani 1 1 d . . . . .
H12 H 0.048625 0.155342 0.516114 0.032 Uiso 1 1 calc R U . . .
C13 C 0.19040(16) 0.18626(8) 0.44443(12) 0.0266(3) Uani 1 1 d . . . . .
H13 H 0.243459 0.220278 0.466264 0.032 Uiso 1 1 calc R U . . .
C14 C 0.18186(16) 0.19200(8) 0.34545(12) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.261227 0.189226 0.317784 0.034 Uiso 1 1 calc R U . . .
C15 C 0.06289(18) 0.24915(10) 0.54452(13) 0.0325(4) Uani 1 1 d . . . . .
C16 C -0.0637(3) 0.31141(14) 0.6274(2) 0.0605(8) Uani 1 1 d . . . . .
H16A H -0.023248 0.349762 0.608831 0.091 Uiso 1 1 calc R U . . .
H16B H -0.030571 0.297631 0.681644 0.091 Uiso 1 1 calc R U . . .
H16C H -0.148483 0.320002 0.634026 0.091 Uiso 1 1 calc R U . . .
C17 C 0.24287(17) 0.12271(9) 0.46840(13) 0.0301(4) Uani 1 1 d . . . . .
C18 C 0.4033(2) 0.05320(10) 0.44530(16) 0.0410(5) Uani 1 1 d . . . . .
H18A H 0.360352 0.020178 0.414716 0.061 Uiso 1 1 calc R U . . .
H18B H 0.402494 0.043903 0.505983 0.061 Uiso 1 1 calc R U . . .
H18C H 0.485328 0.054839 0.425345 0.061 Uiso 1 1 calc R U . . .
C21 C 0.47208(16) 0.30187(8) 0.11144(12) 0.0266(3) Uani 1 1 d . . . . .
H21 H 0.390310 0.296886 0.087951 0.032 Uiso 1 1 calc R U . . .
C22 C 0.56829(16) 0.30399(8) 0.04048(12) 0.0264(3) Uani 1 1 d . . . . .
H22 H 0.550355 0.340693 0.003015 0.032 Uiso 1 1 calc R U . . .
C23 C 0.69076(16) 0.31515(8) 0.08119(12) 0.0271(3) Uani 1 1 d . . . . .
H23 H 0.744377 0.279908 0.064235 0.033 Uiso 1 1 calc R U . . .
C24 C 0.68041(16) 0.31532(9) 0.17984(12) 0.0292(4) Uani 1 1 d . . . . .
H24 H 0.759226 0.320210 0.208062 0.035 Uiso 1 1 calc R U . . .
C25 C 0.56714(17) 0.24513(10) -0.01365(12) 0.0313(4) Uani 1 1 d . . . . .
C26 C 0.4460(3) 0.17677(13) -0.09389(19) 0.0565(7) Uani 1 1 d . . . . .
H26A H 0.362055 0.168898 -0.105832 0.085 Uiso 1 1 calc R U . . .
H26B H 0.480764 0.139640 -0.066766 0.085 Uiso 1 1 calc R U . . .
H26C H 0.487647 0.185465 -0.146893 0.085 Uiso 1 1 calc R U . . .
C27 C 0.74416(16) 0.37660(9) 0.05007(13) 0.0299(4) Uani 1 1 d . . . . .
C28 C 0.9025(2) 0.44812(10) 0.06812(16) 0.0415(5) Uani 1 1 d . . . . .
H28A H 0.905898 0.451892 0.006418 0.062 Uiso 1 1 calc R U . . .
H28B H 0.983063 0.448591 0.091305 0.062 Uiso 1 1 calc R U . . .
H28C H 0.857468 0.483486 0.091426 0.062 Uiso 1 1 calc R U . . .
C111 C -0.01248(17) 0.14378(8) 0.35385(12) 0.0283(4) Uani 1 1 d . . . . .
C112 C 0.09987(18) 0.13964(8) 0.31765(12) 0.0295(4) Uani 1 1 d . . . . .
C113 C 0.1275(2) 0.09054(10) 0.26422(14) 0.0378(4) Uani 1 1 d . . . . .
H113 H 0.204730 0.087132 0.240968 0.045 Uiso 1 1 calc R U . . .
C114 C 0.0413(2) 0.04601(10) 0.24462(16) 0.0464(5) Uani 1 1 d . . . . .
H114 H 0.059089 0.012703 0.206646 0.056 Uiso 1 1 calc R U . . .
C115 C -0.0698(2) 0.05012(10) 0.28021(16) 0.0445(5) Uani 1 1 d . . . . .
H115 H -0.127973 0.019405 0.266716 0.053 Uiso 1 1 calc R U . . .
C116 C -0.0977(2) 0.09864(10) 0.33557(14) 0.0359(4) Uani 1 1 d . . . . .
H116 H -0.174018 0.100909 0.360559 0.043 Uiso 1 1 calc R U . . .
C121 C 0.00600(16) 0.25762(8) 0.36039(12) 0.0273(3) Uani 1 1 d . . . . .
C122 C 0.11921(16) 0.25317(9) 0.32545(13) 0.0291(4) Uani 1 1 d . . . . .
C123 C 0.16267(19) 0.30114(10) 0.27472(14) 0.0370(4) Uani 1 1 d . . . . .
H123 H 0.239484 0.298244 0.250659 0.044 Uiso 1 1 calc R U . . .
C124 C 0.0914(2) 0.35391(10) 0.25958(17) 0.0451(5) Uani 1 1 d . . . . .
H124 H 0.119500 0.386720 0.224116 0.054 Uiso 1 1 calc R U . . .
C125 C -0.0188(2) 0.35865(10) 0.29551(17) 0.0442(5) Uani 1 1 d . . . . .
H125 H -0.065618 0.395033 0.285388 0.053 Uiso 1 1 calc R U . . .
C126 C -0.06291(19) 0.31064(9) 0.34675(14) 0.0354(4) Uani 1 1 d . . . . .
H126 H -0.138944 0.314238 0.371880 0.042 Uiso 1 1 calc R U . . .
C211 C 0.50638(16) 0.24797(9) 0.16939(12) 0.0280(3) Uani 1 1 d . . . . .
C212 C 0.61881(16) 0.25524(9) 0.20572(12) 0.0287(4) Uani 1 1 d . . . . .
C213 C 0.66120(19) 0.21109(10) 0.26299(14) 0.0360(4) Uani 1 1 d . . . . .
H213 H 0.737300 0.215921 0.287909 0.043 Uiso 1 1 calc R U . . .
C214 C 0.5905(2) 0.15966(10) 0.28334(16) 0.0421(5) Uani 1 1 d . . . . .
H214 H 0.617839 0.129627 0.323368 0.050 Uiso 1 1 calc R U . . .
C215 C 0.4806(2) 0.15193(10) 0.24571(16) 0.0406(5) Uani 1 1 d . . . . .
H215 H 0.433922 0.116194 0.259412 0.049 Uiso 1 1 calc R U . . .
C216 C 0.43755(18) 0.19622(9) 0.18762(13) 0.0333(4) Uani 1 1 d . . . . .
H216 H 0.362503 0.190667 0.161391 0.040 Uiso 1 1 calc R U . . .
C221 C 0.48565(17) 0.36204(9) 0.16267(12) 0.0299(4) Uani 1 1 d . . . . .
C222 C 0.59768(18) 0.36899(9) 0.20019(12) 0.0305(4) Uani 1 1 d . . . . .
C223 C 0.6235(2) 0.42124(10) 0.24955(14) 0.0389(4) Uani 1 1 d . . . . .
H223 H 0.699546 0.426023 0.274523 0.047 Uiso 1 1 calc R U . . .
C224 C 0.5360(3) 0.46659(11) 0.26190(17) 0.0494(6) Uani 1 1 d . . . . .
H224 H 0.552173 0.502383 0.296001 0.059 Uiso 1 1 calc R U . . .
C225 C 0.4258(2) 0.45968(11) 0.22472(17) 0.0490(6) Uani 1 1 d . . . . .
H225 H 0.366999 0.490960 0.233518 0.059 Uiso 1 1 calc R U . . .
C226 C 0.3996(2) 0.40762(10) 0.17459(14) 0.0377(4) Uani 1 1 d . . . . .
H226 H 0.323825 0.403424 0.148948 0.045 Uiso 1 1 calc R U . . .
C31 C 0.2912(5) 0.5221(2) 0.4579(3) 0.0589(17) Uani 0.569(7) 1 d DG U P A 1
C32 C 0.3455(5) 0.5098(2) 0.5351(3) 0.096(2) Uani 0.569(7) 1 d DG U P A 1
H32 H 0.405328 0.537202 0.555844 0.115 Uiso 0.569(7) 1 calc R U P A 1
N3 N 0.3121(6) 0.4574(3) 0.5820(3) 0.106(2) Uani 0.569(7) 1 d DG U P A 1
C33 C 0.2245(5) 0.4174(2) 0.5517(3) 0.0716(17) Uani 0.569(7) 1 d DG U P A 1
H33 H 0.201674 0.381574 0.583714 0.086 Uiso 0.569(7) 1 calc R U P A 1
C34 C 0.1702(5) 0.4297(3) 0.4744(4) 0.126(4) Uani 0.569(7) 1 d DG U P A 1
H34 H 0.110352 0.402263 0.453691 0.151 Uiso 0.569(7) 1 calc R U P A 1
C35 C 0.2036(6) 0.4820(3) 0.4275(3) 0.117(4) Uani 0.569(7) 1 d DG U P A 1
H35 H 0.166517 0.490422 0.374744 0.140 Uiso 0.569(7) 1 calc R U P A 1
C36 C 0.3361(5) 0.5754(2) 0.4049(3) 0.087(2) Uani 0.569(7) 1 d D U P A 1
H36A H 0.289307 0.578107 0.352730 0.131 Uiso 0.569(7) 1 calc R U P A 1
H36B H 0.328965 0.614847 0.436458 0.131 Uiso 0.569(7) 1 calc R U P A 1
H36C H 0.419412 0.568000 0.390721 0.131 Uiso 0.569(7) 1 calc R U P A 1
C41 C 0.2753(7) 0.5284(2) 0.4514(4) 0.082(3) Uani 0.431(7) 1 d DG U P A 2
C42 C 0.2621(8) 0.5416(3) 0.5369(4) 0.092(3) Uani 0.431(7) 1 d DG U P A 2
H42 H 0.284445 0.581553 0.558503 0.111 Uiso 0.431(7) 1 calc R U P A 2
N4 N 0.2160(8) 0.4962(4) 0.5909(3) 0.116(3) Uani 0.431(7) 1 d DG U P A 2
C43 C 0.1833(7) 0.4376(3) 0.5594(3) 0.101(3) Uani 0.431(7) 1 d DG U P A 2
H43 H 0.151817 0.406619 0.596303 0.121 Uiso 0.431(7) 1 calc R U P A 2
C44 C 0.1965(6) 0.4245(2) 0.4739(3) 0.0582(19) Uani 0.431(7) 1 d DG U P A 2
H44 H 0.174163 0.384495 0.452291 0.070 Uiso 0.431(7) 1 calc R U P A 2
C45 C 0.2426(6) 0.4699(3) 0.4198(3) 0.0499(15) Uani 0.431(7) 1 d DG U P A 2
H45 H 0.251650 0.460900 0.361383 0.060 Uiso 0.431(7) 1 calc R U P A 2
C46 C 0.3361(5) 0.5754(2) 0.4049(3) 0.128(4) Uani 0.431(7) 1 d D U P A 2
H46A H 0.341633 0.562527 0.345493 0.193 Uiso 0.431(7) 1 calc R U P A 2
H46B H 0.292753 0.615208 0.408728 0.193 Uiso 0.431(7) 1 calc R U P A 2
H46C H 0.415919 0.580820 0.428211 0.193 Uiso 0.431(7) 1 calc R U P A 2
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
C15 O11 C16 116.78(18) . . ?
C17 O13 C18 116.43(17) . . ?
C25 O21 C26 115.92(18) . . ?
C27 O23 C28 116.36(17) . . ?
C121 C11 C111 107.00(15) . . ?
C121 C11 C12 106.40(14) . . ?
C111 C11 C12 107.03(14) . . ?
C121 C11 H11 112.0 . . ?
C111 C11 H11 112.0 . . ?
C12 C11 H11 112.0 . . ?
C15 C12 C13 111.88(15) . . ?
C15 C12 C11 112.40(15) . . ?
C13 C12 C11 109.48(14) . . ?
C15 C12 H12 107.6 . . ?
C13 C12 H12 107.6 . . ?
C11 C12 H12 107.6 . . ?
C17 C13 C12 110.68(15) . . ?
C17 C13 C14 109.85(15) . . ?
C12 C13 C14 109.75(14) . . ?
C17 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?
C112 C14 C122 106.61(15) . . ?
C112 C14 C13 105.57(15) . . ?
C122 C14 C13 107.59(15) . . ?
C112 C14 H14 112.2 . . ?
C122 C14 H14 112.2 . . ?
C13 C14 H14 112.2 . . ?
O12 C15 O11 123.57(19) . . ?
O12 C15 C12 125.35(19) . . ?
O11 C15 C12 111.00(16) . . ?
O11 C16 H16A 109.5 . . ?
O11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O14 C17 O13 123.16(18) . . ?
O14 C17 C13 125.68(19) . . ?
O13 C17 C13 111.16(16) . . ?
O13 C18 H18A 109.5 . . ?
O13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C211 C21 C221 106.72(15) . . ?
C211 C21 C22 106.17(14) . . ?
C221 C21 C22 106.77(14) . . ?
C211 C21 H21 112.3 . . ?
C221 C21 H21 112.3 . . ?
C22 C21 H21 112.3 . . ?
C25 C22 C23 111.66(14) . . ?
C25 C22 C21 112.11(15) . . ?
C23 C22 C21 109.17(15) . . ?
C25 C22 H22 107.9 . . ?
C23 C22 H22 107.9 . . ?
C21 C22 H22 107.9 . . ?
C27 C23 C22 110.65(15) . . ?
C27 C23 C24 110.57(16) . . ?
C22 C23 C24 110.34(14) . . ?
C27 C23 H23 108.4 . . ?
C22 C23 H23 108.4 . . ?
C24 C23 H23 108.4 . . ?
C222 C24 C212 107.17(15) . . ?
C222 C24 C23 105.19(15) . . ?
C212 C24 C23 107.68(15) . . ?
C222 C24 H24 112.1 . . ?
C212 C24 H24 112.1 . . ?
C23 C24 H24 112.1 . . ?
O22 C25 O21 123.31(19) . . ?
O22 C25 C22 125.47(19) . . ?
O21 C25 C22 111.19(16) . . ?
O21 C26 H26A 109.5 . . ?
O21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O24 C27 O23 123.55(18) . . ?
O24 C27 C23 125.20(18) . . ?
O23 C27 C23 111.24(16) . . ?
O23 C28 H28A 109.5 . . ?
O23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C116 C111 C112 120.08(18) . . ?
C116 C111 C11 126.39(18) . . ?
C112 C111 C11 113.53(16) . . ?
C113 C112 C111 120.40(18) . . ?
C113 C112 C14 126.57(19) . . ?
C111 C112 C14 113.01(16) . . ?
C112 C113 C114 119.5(2) . . ?
C112 C113 H113 120.3 . . ?
C114 C113 H113 120.3 . . ?
C115 C114 C113 120.1(2) . . ?
C115 C114 H114 119.9 . . ?
C113 C114 H114 119.9 . . ?
C114 C115 C116 120.8(2) . . ?
C114 C115 H115 119.6 . . ?
C116 C115 H115 119.6 . . ?
C111 C116 C115 119.1(2) . . ?
C111 C116 H116 120.5 . . ?
C115 C116 H116 120.5 . . ?
C126 C121 C122 120.48(18) . . ?
C126 C121 C11 126.62(17) . . ?
C122 C121 C11 112.89(16) . . ?
C123 C122 C121 120.27(18) . . ?
C123 C122 C14 125.90(18) . . ?
C121 C122 C14 113.78(16) . . ?
C122 C123 C124 118.9(2) . . ?
C122 C123 H123 120.6 . . ?
C124 C123 H123 120.6 . . ?
C125 C124 C123 120.6(2) . . ?
C125 C124 H124 119.7 . . ?
C123 C124 H124 119.7 . . ?
C124 C125 C126 120.78(19) . . ?
C124 C125 H125 119.6 . . ?
C126 C125 H125 119.6 . . ?
C121 C126 C125 118.9(2) . . ?
C121 C126 H126 120.5 . . ?
C125 C126 H126 120.5 . . ?
C216 C211 C212 120.88(18) . . ?
C216 C211 C21 125.88(17) . . ?
C212 C211 C21 113.23(16) . . ?
C213 C212 C211 120.25(18) . . ?
C213 C212 C24 126.12(17) . . ?
C211 C212 C24 113.54(16) . . ?
C212 C213 C214 119.0(2) . . ?
C212 C213 H213 120.5 . . ?
C214 C213 H213 120.5 . . ?
C215 C214 C213 120.5(2) . . ?
C215 C214 H214 119.7 . . ?
C213 C214 H214 119.7 . . ?
C214 C215 C216 120.75(19) . . ?
C214 C215 H215 119.6 . . ?
C216 C215 H215 119.6 . . ?
C211 C216 C215 118.57(19) . . ?
C211 C216 H216 120.7 . . ?
C215 C216 H216 120.7 . . ?
C226 C221 C222 120.04(18) . . ?
C226 C221 C21 126.18(18) . . ?
C222 C221 C21 113.77(16) . . ?
C223 C222 C221 120.64(19) . . ?
C223 C222 C24 126.54(19) . . ?
C221 C222 C24 112.82(16) . . ?
C222 C223 C224 119.0(2) . . ?
C222 C223 H223 120.5 . . ?
C224 C223 H223 120.5 . . ?
C225 C224 C223 120.3(2) . . ?
C225 C224 H224 119.9 . . ?
C223 C224 H224 119.9 . . ?
C224 C225 C226 121.1(2) . . ?
C224 C225 H225 119.5 . . ?
C226 C225 H225 119.5 . . ?
C221 C226 C225 119.0(2) . . ?
C221 C226 H226 120.5 . . ?
C225 C226 H226 120.5 . . ?
C32 C31 C35 120.0 . . ?
C32 C31 C36 119.0(4) . . ?
C35 C31 C36 120.8(4) . . ?
C31 C32 N3 120.0 . . ?
C31 C32 H32 120.0 . . ?
N3 C32 H32 120.0 . . ?
C33 N3 C32 120.0 . . ?
N3 C33 C34 120.0 . . ?
N3 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C31 120.0 . . ?
C34 C35 H35 120.0 . . ?
C31 C35 H35 120.0 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C42 C41 C45 120.0 . . ?
C42 C41 C46 114.7(4) . . ?
C45 C41 C46 124.9(4) . . ?
N4 C42 C41 120.0 . . ?
N4 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C43 N4 C42 120.0 . . ?
N4 C43 C44 120.0 . . ?
N4 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C43 C44 C45 120.0 . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 C41 120.0 . . ?
C44 C45 H45 120.0 . . ?
C41 C45 H45 120.0 . . ?
C41 C46 H46A 109.5 . . ?
C41 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C41 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
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
O11 C15 1.323(2) . ?
O11 C16 1.436(3) . ?
O12 C15 1.200(3) . ?
O13 C17 1.333(2) . ?
O13 C18 1.450(2) . ?
O14 C17 1.194(3) . ?
O21 C25 1.339(2) . ?
O21 C26 1.449(3) . ?
O22 C25 1.194(3) . ?
O23 C27 1.335(2) . ?
O23 C28 1.445(2) . ?
O24 C27 1.204(3) . ?
C11 C121 1.506(2) . ?
C11 C111 1.518(2) . ?
C11 C12 1.568(2) . ?
C11 H11 1.0000 . ?
C12 C15 1.512(3) . ?
C12 C13 1.536(2) . ?
C12 H12 1.0000 . ?
C13 C17 1.522(2) . ?
C13 C14 1.573(3) . ?
C13 H13 1.0000 . ?
C14 C112 1.512(3) . ?
C14 C122 1.513(2) . ?
C14 H14 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 C211 1.517(2) . ?
C21 C221 1.521(3) . ?
C21 C22 1.564(2) . ?
C21 H21 1.0000 . ?
C22 C25 1.516(3) . ?
C22 C23 1.542(2) . ?
C22 H22 1.0000 . ?
C23 C27 1.521(3) . ?
C23 C24 1.565(3) . ?
C23 H23 1.0000 . ?
C24 C222 1.510(3) . ?
C24 C212 1.511(3) . ?
C24 H24 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C111 C116 1.389(3) . ?
C111 C112 1.396(3) . ?
C112 C113 1.379(3) . ?
C113 C114 1.392(3) . ?
C113 H113 0.9500 . ?
C114 C115 1.379(4) . ?
C114 H114 0.9500 . ?
C115 C116 1.389(3) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C121 C126 1.386(3) . ?
C121 C122 1.397(3) . ?
C122 C123 1.388(3) . ?
C123 C124 1.401(3) . ?
C123 H123 0.9500 . ?
C124 C125 1.373(4) . ?
C124 H124 0.9500 . ?
C125 C126 1.396(3) . ?
C125 H125 0.9500 . ?
C126 H126 0.9500 . ?
C211 C216 1.378(3) . ?
C211 C212 1.401(3) . ?
C212 C213 1.389(3) . ?
C213 C214 1.392(3) . ?
C213 H213 0.9500 . ?
C214 C215 1.384(3) . ?
C214 H214 0.9500 . ?
C215 C216 1.402(3) . ?
C215 H215 0.9500 . ?
C216 H216 0.9500 . ?
C221 C226 1.385(3) . ?
C221 C222 1.404(3) . ?
C222 C223 1.388(3) . ?
C223 C224 1.394(3) . ?
C223 H223 0.9500 . ?
C224 C225 1.383(4) . ?
C224 H224 0.9500 . ?
C225 C226 1.393(3) . ?
C225 H225 0.9500 . ?
C226 H226 0.9500 . ?
C31 C32 1.3900 . ?
C31 C35 1.3900 . ?
C31 C36 1.498(6) . ?
C32 N3 1.3900 . ?
C32 H32 0.9500 . ?
N3 C33 1.3900 . ?
C33 C34 1.3900 . ?
C33 H33 0.9500 . ?
C34 C35 1.3900 . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C41 C42 1.3900 . ?
C41 C45 1.3900 . ?
C41 C46 1.418(6) . ?
C42 N4 1.3900 . ?
C42 H42 0.9500 . ?
N4 C43 1.3900 . ?
C43 C44 1.3900 . ?
C43 H43 0.9500 . ?
C44 C45 1.3900 . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
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
_geom_hbond_publ_flag
C12 H12 O14 1.00 2.26 2.803(2) 113 . yes
C13 H13 O12 1.00 2.33 2.831(3) 110 . yes
C22 H22 O24 1.00 2.26 2.800(2) 113 . yes
C23 H23 O22 1.00 2.32 2.826(3) 111 . yes
C23 H23 O11 1.00 2.52 3.398(2) 146 4_665 yes
C33 H33 O12 0.95 2.34 3.158(4) 144 . yes
C114 H114 N4 0.95 2.56 3.26(4) 131 4_565 yes
C116 H116 O24 0.95 2.56 3.394(3) 147 4_466 yes
C224 H224 N3 0.95 2.61 3.41(2) 143 3_666 yes
C226 H226 O14 0.95 2.54 3.379(3) 147 4_565 yes
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
C121 C11 C12 C15 64.69(19) . . . . ?
C111 C11 C12 C15 178.82(15) . . . . ?
C121 C11 C12 C13 -60.29(18) . . . . ?
C111 C11 C12 C13 53.84(18) . . . . ?
C15 C12 C13 C17 117.73(17) . . . . ?
C11 C12 C13 C17 -116.99(16) . . . . ?
C15 C12 C13 C14 -120.86(17) . . . . ?
C11 C12 C13 C14 4.42(19) . . . . ?
C17 C13 C14 C112 61.39(18) . . . . ?
C12 C13 C14 C112 -60.52(18) . . . . ?
C17 C13 C14 C122 174.94(15) . . . . ?
C12 C13 C14 C122 53.03(19) . . . . ?
C16 O11 C15 O12 -0.8(4) . . . . ?
C16 O11 C15 C12 176.1(2) . . . . ?
C13 C12 C15 O12 -14.7(3) . . . . ?
C11 C12 C15 O12 -138.4(2) . . . . ?
C13 C12 C15 O11 168.41(17) . . . . ?
C11 C12 C15 O11 44.7(2) . . . . ?
C18 O13 C17 O14 3.3(3) . . . . ?
C18 O13 C17 C13 -177.49(17) . . . . ?
C12 C13 C17 O14 -4.9(3) . . . . ?
C14 C13 C17 O14 -126.3(2) . . . . ?
C12 C13 C17 O13 175.87(15) . . . . ?
C14 C13 C17 O13 54.5(2) . . . . ?
C211 C21 C22 C25 64.37(19) . . . . ?
C221 C21 C22 C25 177.96(15) . . . . ?
C211 C21 C22 C23 -59.89(18) . . . . ?
C221 C21 C22 C23 53.70(18) . . . . ?
C25 C22 C23 C27 117.28(17) . . . . ?
C21 C22 C23 C27 -118.19(16) . . . . ?
C25 C22 C23 C24 -120.03(17) . . . . ?
C21 C22 C23 C24 4.50(19) . . . . ?
C27 C23 C24 C222 61.87(18) . . . . ?
C22 C23 C24 C222 -60.86(18) . . . . ?
C27 C23 C24 C212 175.93(14) . . . . ?
C22 C23 C24 C212 53.19(19) . . . . ?
C26 O21 C25 O22 -1.2(3) . . . . ?
C26 O21 C25 C22 176.81(19) . . . . ?
C23 C22 C25 O22 -11.6(3) . . . . ?
C21 C22 C25 O22 -134.5(2) . . . . ?
C23 C22 C25 O21 170.40(16) . . . . ?
C21 C22 C25 O21 47.5(2) . . . . ?
C28 O23 C27 O24 2.6(3) . . . . ?
C28 O23 C27 C23 -178.20(17) . . . . ?
C22 C23 C27 O24 -6.5(3) . . . . ?
C24 C23 C27 O24 -129.1(2) . . . . ?
C22 C23 C27 O23 174.32(15) . . . . ?
C24 C23 C27 O23 51.8(2) . . . . ?
C121 C11 C111 C116 -125.6(2) . . . . ?
C12 C11 C111 C116 120.6(2) . . . . ?
C121 C11 C111 C112 53.97(19) . . . . ?
C12 C11 C111 C112 -59.76(19) . . . . ?
C116 C111 C112 C113 -0.6(3) . . . . ?
C11 C111 C112 C113 179.76(17) . . . . ?
C116 C111 C112 C14 -179.11(17) . . . . ?
C11 C111 C112 C14 1.3(2) . . . . ?
C122 C14 C112 C113 126.5(2) . . . . ?
C13 C14 C112 C113 -119.2(2) . . . . ?
C122 C14 C112 C111 -55.1(2) . . . . ?
C13 C14 C112 C111 59.16(19) . . . . ?
C111 C112 C113 C114 1.9(3) . . . . ?
C14 C112 C113 C114 -179.85(19) . . . . ?
C112 C113 C114 C115 -1.7(3) . . . . ?
C113 C114 C115 C116 0.3(3) . . . . ?
C112 C111 C116 C115 -0.8(3) . . . . ?
C11 C111 C116 C115 178.79(18) . . . . ?
C114 C115 C116 C111 0.9(3) . . . . ?
C111 C11 C121 C126 125.2(2) . . . . ?
C12 C11 C121 C126 -120.7(2) . . . . ?
C111 C11 C121 C122 -54.7(2) . . . . ?
C12 C11 C121 C122 59.43(19) . . . . ?
C126 C121 C122 C123 -1.8(3) . . . . ?
C11 C121 C122 C123 178.14(18) . . . . ?
C126 C121 C122 C14 -179.25(18) . . . . ?
C11 C121 C122 C14 0.7(2) . . . . ?
C112 C14 C122 C123 -122.9(2) . . . . ?
C13 C14 C122 C123 124.2(2) . . . . ?
C112 C14 C122 C121 54.4(2) . . . . ?
C13 C14 C122 C121 -58.5(2) . . . . ?
C121 C122 C123 C124 0.2(3) . . . . ?
C14 C122 C123 C124 177.4(2) . . . . ?
C122 C123 C124 C125 1.2(4) . . . . ?
C123 C124 C125 C126 -1.0(4) . . . . ?
C122 C121 C126 C125 1.9(3) . . . . ?
C11 C121 C126 C125 -178.00(19) . . . . ?
C124 C125 C126 C121 -0.5(3) . . . . ?
C221 C21 C211 C216 125.2(2) . . . . ?
C22 C21 C211 C216 -121.2(2) . . . . ?
C221 C21 C211 C212 -54.2(2) . . . . ?
C22 C21 C211 C212 59.42(19) . . . . ?
C216 C211 C212 C213 -2.0(3) . . . . ?
C21 C211 C212 C213 177.41(18) . . . . ?
C216 C211 C212 C24 -178.89(17) . . . . ?
C21 C211 C212 C24 0.5(2) . . . . ?
C222 C24 C212 C213 -122.1(2) . . . . ?
C23 C24 C212 C213 125.2(2) . . . . ?
C222 C24 C212 C211 54.6(2) . . . . ?
C23 C24 C212 C211 -58.2(2) . . . . ?
C211 C212 C213 C214 0.2(3) . . . . ?
C24 C212 C213 C214 176.6(2) . . . . ?
C212 C213 C214 C215 1.4(3) . . . . ?
C213 C214 C215 C216 -1.2(4) . . . . ?
C212 C211 C216 C215 2.2(3) . . . . ?
C21 C211 C216 C215 -177.15(19) . . . . ?
C214 C215 C216 C211 -0.6(3) . . . . ?
C211 C21 C221 C226 -126.0(2) . . . . ?
C22 C21 C221 C226 120.8(2) . . . . ?
C211 C21 C221 C222 53.6(2) . . . . ?
C22 C21 C221 C222 -59.7(2) . . . . ?
C226 C221 C222 C223 0.1(3) . . . . ?
C21 C221 C222 C223 -179.47(17) . . . . ?
C226 C221 C222 C24 -179.47(18) . . . . ?
C21 C221 C222 C24 0.9(2) . . . . ?
C212 C24 C222 C223 125.3(2) . . . . ?
C23 C24 C222 C223 -120.2(2) . . . . ?
C212 C24 C222 C221 -55.1(2) . . . . ?
C23 C24 C222 C221 59.31(19) . . . . ?
C221 C222 C223 C224 0.5(3) . . . . ?
C24 C222 C223 C224 -180.0(2) . . . . ?
C222 C223 C224 C225 -0.6(4) . . . . ?
C223 C224 C225 C226 0.1(4) . . . . ?
C222 C221 C226 C225 -0.6(3) . . . . ?
C21 C221 C226 C225 178.9(2) . . . . ?
C224 C225 C226 C221 0.5(4) . . . . ?
C35 C31 C32 N3 0.0 . . . . ?
C36 C31 C32 N3 -174.5(5) . . . . ?
C31 C32 N3 C33 0.0 . . . . ?
C32 N3 C33 C34 0.0 . . . . ?
N3 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C31 0.0 . . . . ?
C32 C31 C35 C34 0.0 . . . . ?
C36 C31 C35 C34 174.4(5) . . . . ?
C45 C41 C42 N4 0.0 . . . . ?
C46 C41 C42 N4 -172.8(7) . . . . ?
C41 C42 N4 C43 0.0 . . . . ?
C42 N4 C43 C44 0.0 . . . . ?
N4 C43 C44 C45 0.0 . . . . ?
C43 C44 C45 C41 0.0 . . . . ?
C42 C41 C45 C44 0.0 . . . . ?
C46 C41 C45 C44 172.0(7) . . . . ?
