#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202324.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2202324
loop_
_publ_author_name
'Winkler, Torsten'
'Herges, Rainer'
'Jones, Peter G.'
'Dix, Ina'
_publ_section_title
;A tetrakis(tertiary amide) derivative of quadricyclane:
 3-isopropylidene-tetracyclo[3.2.0.0^2,7^.0^4,6^]heptan-1,5,6,7-tetracarboxylic
 acid tetrakis(diethylamide)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1103
_journal_page_last               o1105
_journal_paper_doi               10.1107/S1600536803013898
_journal_volume                  59
_journal_year                    2003
_chemical_formula_sum            'C30 H48 N4 O4'
_chemical_formula_weight         528.72
_chemical_name_systematic
;
 3-Isopropylidene-tetracyclo[3.2.0.0^2,7^.0^4,6^]heptan-1,5,6,7-
 tetracarboxylic acid tetrakis(diethylamide)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.065(3)
_cell_angle_beta                 101.073(3)
_cell_angle_gamma                106.800(3)
_cell_formula_units_Z            2
_cell_length_a                   10.8375(8)
_cell_length_b                   11.6922(8)
_cell_length_c                   13.7337(10)
_cell_measurement_reflns_used    6653
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.2
_cell_volume                     1493.6(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    ' XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω-scan
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17805
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.333
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         7353
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0418
_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)+(0.0586P)²+0.0907P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                5396
_reflns_number_total             7353
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6292.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1493.59(19)
_cod_database_code               2202324
_cod_database_fobs_code          2202324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.20249(9) 0.78494(9) 0.40800(7) 0.0303(2) Uani d . 1 A . O
O2 0.38325(9) 0.38040(8) 0.24123(8) 0.0325(2) Uani d . 1 . . O
O3 0.30457(9) 0.50436(9) 0.04316(7) 0.0332(2) Uani d . 1 A . O
O4 0.44982(9) 1.01521(8) 0.34527(7) 0.0287(2) Uani d . 1 . . O
N1 0.29341(10) 0.70016(10) 0.51542(8) 0.0240(2) Uani d . 1 A . N
N2 0.18476(11) 0.40507(10) 0.23941(10) 0.0357(3) Uani d D 1 . . N
N3 0.46959(11) 0.68472(10) 0.05547(8) 0.0277(2) Uani d . 1 A . N
N4 0.27657(11) 0.87143(10) 0.19391(9) 0.0283(2) Uani d . 1 . . N
C1 0.38238(11) 0.72177(11) 0.36999(9) 0.0197(2) Uani d . 1 A . C
C2 0.52392(11) 0.82734(11) 0.40662(9) 0.0193(2) Uani d . 1 A . C
H2 0.5513 0.9128 0.4696 0.023 Uiso calc R 1 . . H
C3 0.62373(11) 0.76636(11) 0.38673(9) 0.0202(2) Uani d . 1 . . C
C4 0.53939(11) 0.64552(11) 0.28906(9) 0.0208(2) Uani d . 1 A . C
H4 0.5798 0.5823 0.2547 0.025 Uiso calc R 1 . . H
C5 0.39286(11) 0.59675(11) 0.28954(9) 0.0203(2) Uani d . 1 . . C
C6 0.43074(11) 0.67008(11) 0.21909(9) 0.0203(2) Uani d . 1 A . C
C7 0.42035(11) 0.79429(11) 0.29908(9) 0.0193(2) Uani d . 1 . . C
C8 0.75585(12) 0.80992(12) 0.44102(10) 0.0241(2) Uani d . 1 . . C
C9 0.82600(13) 0.93387(13) 0.54204(11) 0.0338(3) Uani d . 1 . . C
H9A 0.7589 0.9692 0.5633 0.041 Uiso calc R 1 . . H
H9B 0.8933 0.9979 0.5282 0.041 Uiso calc R 1 . . H
H9C 0.8716 0.9156 0.6007 0.041 Uiso calc R 1 . . H
C10 0.84586(12) 0.73922(13) 0.40492(12) 0.0321(3) Uani d . 1 . . C
H10A 0.7916 0.6585 0.3399 0.039 Uiso calc R 1 . . H
H10B 0.8870 0.7177 0.4631 0.039 Uiso calc R 1 . . H
H10C 0.9176 0.7954 0.3882 0.039 Uiso calc R 1 . . H
C11 0.28542(11) 0.73851(11) 0.43291(9) 0.0217(2) Uani d . 1 . . C
C12 0.19938(13) 0.71676(13) 0.57739(11) 0.0324(3) Uani d . 1 . . C
H12A 0.1886 0.6545 0.6126 0.039 Uiso calc R 1 A . H
H12B 0.1093 0.6946 0.5266 0.039 Uiso calc R 1 . . H
C13 0.24526(16) 0.85370(16) 0.66354(13) 0.0464(4) Uani d . 1 A . C
H13A 0.3344 0.8766 0.7142 0.056 Uiso calc R 1 . . H
H13B 0.1793 0.8576 0.7032 0.056 Uiso calc R 1 . . H
H13C 0.2517 0.9156 0.6290 0.056 Uiso calc R 1 . . H
C14 0.40144(13) 0.66079(12) 0.55725(10) 0.0282(3) Uani d . 1 . . C
H14A 0.4434 0.7140 0.6364 0.034 Uiso calc R 1 A . H
H14B 0.4726 0.6789 0.5225 0.034 Uiso calc R 1 . . H
C15 0.35012(15) 0.51725(14) 0.53655(13) 0.0396(3) Uani d . 1 A . C
H15A 0.2771 0.4980 0.5683 0.048 Uiso calc R 1 . . H
H15B 0.4248 0.4969 0.5698 0.048 Uiso calc R 1 . . H
H15C 0.3153 0.4639 0.4581 0.048 Uiso calc R 1 . . H
C16 0.31929(12) 0.45210(12) 0.25344(10) 0.0251(3) Uani d . 1 A . C
C17 0.1234(2) 0.26610(19) 0.2222(2) 0.0314(6) Uani d PD 0.756(5) A 1 C
H17A 0.0568 0.2565 0.2622 0.038 Uiso calc PR 0.756(5) A 1 H
H17B 0.1951 0.2381 0.2509 0.038 Uiso calc PR 0.756(5) A 1 H
C18 0.0537(3) 0.1813(2) 0.1035(2) 0.0570(8) Uani d PD 0.756(5) A 1 C
H18A -0.0181 0.2084 0.0756 0.068 Uiso calc PR 0.756(5) A 1 H
H18B 0.0137 0.0898 0.0932 0.068 Uiso calc PR 0.756(5) A 1 H
H18C 0.1200 0.1902 0.0642 0.068 Uiso calc PR 0.756(5) A 1 H
C17' 0.1000(6) 0.2618(6) 0.1660(6) 0.0297(17) Uani d PD 0.244(5) A 2 C
H17C 0.0082 0.2490 0.1242 0.036 Uiso calc PR 0.244(5) A 2 H
H17D 0.1455 0.2233 0.1156 0.036 Uiso calc PR 0.244(5) A 2 H
C18' 0.0955(6) 0.2072(6) 0.2532(6) 0.045(2) Uani d PD 0.244(5) A 2 C
H18D 0.1878 0.2200 0.2916 0.054 Uiso calc PR 0.244(5) A 2 H
H18E 0.0388 0.1136 0.2188 0.054 Uiso calc PR 0.244(5) A 2 H
H18F 0.0570 0.2530 0.3049 0.054 Uiso calc PR 0.244(5) A 2 H
C19 0.09622(13) 0.47470(13) 0.22217(12) 0.0332(3) Uani d . 1 A . C
H19A 0.0434 0.4360 0.1441 0.040 Uiso calc R 1 . . H
H19B 0.1529 0.5672 0.2422 0.040 Uiso calc R 1 . . H
C20 -0.00118(14) 0.46942(15) 0.28792(14) 0.0418(4) Uani d . 1 . . C
H20A -0.0678 0.3798 0.2599 0.050 Uiso calc R 1 A . H
H20B -0.0485 0.5280 0.2821 0.050 Uiso calc R 1 . . H
H20C 0.0497 0.4971 0.3642 0.050 Uiso calc R 1 . . H
C21 0.39500(12) 0.61257(12) 0.09818(10) 0.0239(2) Uani d . 1 . . C
C22 0.58444(13) 0.80895(12) 0.12003(11) 0.0295(3) Uani d . 1 . . C
H22A 0.5748 0.8477 0.1925 0.035 Uiso calc R 1 A . H
H22B 0.5817 0.8699 0.0845 0.035 Uiso calc R 1 . . H
C23 0.72126(14) 0.79567(15) 0.13429(13) 0.0435(4) Uani d . 1 A . C
H23A 0.7280 0.7418 0.1752 0.052 Uiso calc R 1 . . H
H23B 0.7940 0.8825 0.1741 0.052 Uiso calc R 1 . . H
H23C 0.7302 0.7542 0.0628 0.052 Uiso calc R 1 . . H
C24 0.44416(15) 0.63029(15) -0.06204(10) 0.0368(3) Uani d . 1 . . C
H24A 0.3992 0.5339 -0.0915 0.044 Uiso calc R 1 A . H
H24B 0.5320 0.6512 -0.0768 0.044 Uiso calc R 1 . . H
C25 0.35664(19) 0.6826(2) -0.11906(13) 0.0590(5) Uani d . 1 A . C
H25A 0.2680 0.6587 -0.1074 0.071 Uiso calc R 1 . . H
H25B 0.3442 0.6452 -0.1970 0.071 Uiso calc R 1 . . H
H25C 0.4006 0.7781 -0.0900 0.071 Uiso calc R 1 . . H
C26 0.38140(11) 0.90130(11) 0.28165(9) 0.0215(2) Uani d . 1 A . C
C27 0.25626(15) 0.98161(14) 0.17382(12) 0.0374(3) Uani d . 1 . . C
H27A 0.2801 1.0556 0.2443 0.045 Uiso calc R 1 . . H
H27B 0.1591 0.9553 0.1347 0.045 Uiso calc R 1 . . H
C28 0.3401(2) 1.02584(19) 0.10872(17) 0.0594(5) Uani d . 1 . . C
H28A 0.4361 1.0481 0.1453 0.071 Uiso calc R 1 . . H
H28B 0.3280 1.1030 0.1018 0.071 Uiso calc R 1 . . H
H28C 0.3112 0.9554 0.0363 0.071 Uiso calc R 1 . . H
C29 0.17208(13) 0.74177(13) 0.12725(11) 0.0316(3) Uani d . 1 . . C
H29A 0.2042 0.6758 0.1412 0.038 Uiso calc R 1 . . H
H29B 0.1583 0.7251 0.0497 0.038 Uiso calc R 1 . . H
C30 0.03673(14) 0.72489(16) 0.14871(13) 0.0438(4) Uani d . 1 . . C
H30A 0.0491 0.7394 0.2250 0.053 Uiso calc R 1 . . H
H30B -0.0290 0.6360 0.1018 0.053 Uiso calc R 1 . . H
H30C 0.0029 0.7883 0.1332 0.053 Uiso calc R 1 . . H
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_publ_flag
C11 N1 C14 124.43(10) ?
C11 N1 C12 117.64(10) ?
C14 N1 C12 117.32(10) ?
C16 N2 C19 123.72(10) ?
C16 N2 C17 116.14(12) ?
C19 N2 C17 119.28(12) ?
C16 N2 C17' 119.1(2) ?
C19 N2 C17' 105.2(3) ?
C21 N3 C22 124.09(10) ?
C21 N3 C24 118.60(11) ?
C22 N3 C24 117.00(10) ?
C26 N4 C29 125.44(10) ?
C26 N4 C27 116.83(11) ?
C29 N4 C27 117.15(10) ?
C11 C1 C7 125.11(9) y
C11 C1 C2 121.06(10) y
C7 C1 C2 59.99(7) y
C11 C1 C5 131.89(9) y
C7 C1 C5 90.50(8) y
C2 C1 C5 103.96(9) y
C3 C2 C7 110.12(9) y
C3 C2 C1 110.08(9) y
C7 C2 C1 59.96(7) y
C3 C2 H2 120.6 ?
C7 C2 H2 120.6 ?
C1 C2 H2 120.6 ?
C8 C3 C4 129.07(11) y
C8 C3 C2 129.53(11) y
C4 C3 C2 101.39(9) y
C3 C4 C5 110.66(9) y
C3 C4 C6 109.84(9) y
C5 C4 C6 59.99(7) y
C3 C4 H4 120.5 ?
C5 C4 H4 120.5 ?
C6 C4 H4 120.5 ?
C16 C5 C4 118.08(9) y
C16 C5 C6 127.69(10) y
C4 C5 C6 60.05(7) y
C16 C5 C1 134.13(9) y
C4 C5 C1 103.19(9) y
C6 C5 C1 89.13(8) y
C21 C6 C5 126.55(10) y
C21 C6 C4 120.54(9) y
C5 C6 C4 59.97(7) y
C21 C6 C7 131.46(9) y
C5 C6 C7 90.85(8) y
C4 C6 C7 104.05(9) y
C26 C7 C1 130.13(9) y
C26 C7 C2 118.76(10) y
C1 C7 C2 60.06(7) y
C26 C7 C6 131.97(10) y
C1 C7 C6 89.52(8) y
C2 C7 C6 103.48(8) y
C3 C8 C9 122.46(11) ?
C3 C8 C10 122.65(12) ?
C9 C8 C10 114.88(11) ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C8 C10 H10A 109.5 ?
C8 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C8 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
O1 C11 N1 122.59(10) ?
O1 C11 C1 120.01(10) ?
N1 C11 C1 117.40(10) ?
N1 C12 C13 113.58(11) ?
N1 C12 H12A 108.8 ?
C13 C12 H12A 108.9 ?
N1 C12 H12B 108.8 ?
C13 C12 H12B 108.9 ?
H12A C12 H12B 107.7 ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
N1 C14 C15 112.55(11) ?
N1 C14 H14A 109.1 ?
C15 C14 H14A 109.1 ?
N1 C14 H14B 109.1 ?
C15 C14 H14B 109.1 ?
H14A C14 H14B 107.8 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
O2 C16 N2 121.50(11) ?
O2 C16 C5 119.45(10) ?
N2 C16 C5 118.99(10) ?
N2 C17 C18 110.20(19) ?
N2 C17 H17A 109.6 ?
C18 C17 H17A 109.6 ?
N2 C17 H17B 109.6 ?
C18 C17 H17B 109.6 ?
H17A C17 H17B 108.1 ?
C18' C17' N2 98.9(5) ?
C18' C17' H17C 112.0 ?
N2 C17' H17C 112.0 ?
C18' C17' H17D 112.0 ?
N2 C17' H17D 112.0 ?
H17C C17' H17D 109.7 ?
C17' C18' H18D 109.5 ?
C17' C18' H18E 109.5 ?
H18D C18' H18E 109.5 ?
C17' C18' H18F 109.5 ?
H18D C18' H18F 109.5 ?
H18E C18' H18F 109.5 ?
N2 C19 C20 112.70(12) ?
N2 C19 H19A 109.1 ?
C20 C19 H19A 109.1 ?
N2 C19 H19B 109.1 ?
C20 C19 H19B 109.1 ?
H19A C19 H19B 107.8 ?
C19 C20 H20A 109.5 ?
C19 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C19 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
O3 C21 N3 123.29(11) ?
O3 C21 C6 120.55(11) ?
N3 C21 C6 116.14(10) ?
N3 C22 C23 113.38(11) ?
N3 C22 H22A 108.9 ?
C23 C22 H22A 108.9 ?
N3 C22 H22B 108.9 ?
C23 C22 H22B 108.9 ?
H22A C22 H22B 107.7 ?
C22 C23 H23A 109.5 ?
C22 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C22 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
N3 C24 C25 112.33(12) ?
N3 C24 H24A 109.1 ?
C25 C24 H24A 109.1 ?
N3 C24 H24B 109.1 ?
C25 C24 H24B 109.1 ?
H24A C24 H24B 107.9 ?
C24 C25 H25A 109.5 ?
C24 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
C24 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
O4 C26 N4 121.23(10) ?
O4 C26 C7 118.83(10) ?
N4 C26 C7 119.86(10) ?
N4 C27 C28 112.51(12) ?
N4 C27 H27A 109.1 ?
C28 C27 H27A 109.1 ?
N4 C27 H27B 109.1 ?
C28 C27 H27B 109.1 ?
H27A C27 H27B 107.8 ?
C27 C28 H28A 109.5 ?
C27 C28 H28B 109.5 ?
H28A C28 H28B 109.5 ?
C27 C28 H28C 109.5 ?
H28A C28 H28C 109.5 ?
H28B C28 H28C 109.5 ?
N4 C29 C30 113.30(11) ?
N4 C29 H29A 108.9 ?
C30 C29 H29A 108.9 ?
N4 C29 H29B 108.9 ?
C30 C29 H29B 108.9 ?
H29A C29 H29B 107.7 ?
C29 C30 H30A 109.5 ?
C29 C30 H30B 109.5 ?
H30A C30 H30B 109.5 ?
C29 C30 H30C 109.5 ?
H30A C30 H30C 109.5 ?
H30B C30 H30C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . 1.2267(14) ?
O2 C16 . 1.2248(14) ?
O3 C21 . 1.2274(15) ?
O4 C26 . 1.2277(14) ?
N1 C11 . 1.3451(15) ?
N1 C14 . 1.4624(15) ?
N1 C12 . 1.4629(15) ?
N2 C16 . 1.3508(16) ?
N2 C19 . 1.4593(17) ?
N2 C17 . 1.484(2) ?
N2 C17' . 1.522(6) ?
N3 C21 . 1.3493(15) ?
N3 C22 . 1.4611(16) ?
N3 C24 . 1.4636(16) ?
N4 C26 . 1.3544(15) ?
N4 C29 . 1.4565(17) ?
N4 C27 . 1.4686(16) ?
C1 C11 . 1.4987(15) ?
C1 C7 . 1.5259(15) y
C1 C2 . 1.5274(15) y
C1 C5 . 1.5683(16) y
C2 C3 . 1.4782(15) y
C2 C7 . 1.5264(15) y
C2 H2 . 1.0000 ?
C3 C8 . 1.3363(16) y
C3 C4 . 1.4749(16) y
C4 C5 . 1.5264(15) y
C4 C6 . 1.5276(15) y
C4 H4 . 1.0000 ?
C5 C16 . 1.5042(16) ?
C5 C6 . 1.5267(15) y
C6 C21 . 1.4941(16) ?
C6 C7 . 1.5584(15) ?
C7 C26 . 1.5044(15) ?
C8 C9 . 1.4992(18) ?
C8 C10 . 1.5050(17) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C12 C13 . 1.512(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 C15 . 1.5149(19) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C17 C18 . 1.500(3) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C17' C18' . 1.532(9) ?
C17' H17C . 0.9900 ?
C17' H17D . 0.9900 ?
C18' H18D . 0.9800 ?
C18' H18E . 0.9800 ?
C18' H18F . 0.9800 ?
C19 C20 . 1.5160(19) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
C22 C23 . 1.5175(19) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C24 C25 . 1.500(2) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C27 C28 . 1.495(2) ?
C27 H27A . 0.9900 ?
C27 H27B . 0.9900 ?
C28 H28A . 0.9800 ?
C28 H28B . 0.9800 ?
C28 H28C . 0.9800 ?
C29 C30 . 1.5212(19) ?
C29 H29A . 0.9900 ?
C29 H29B . 0.9900 ?
C30 H30A . 0.9800 ?
C30 H30B . 0.9800 ?
C30 H30C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9A O1 2_676 0.98 2.66 3.2511(16) 118.8
C2 H2 O4 2_676 1.00 2.41 3.2105(14) 136.9
C15 H15B O2 2_666 0.98 2.62 3.3651(18) 132.5
C24 H24B O2 2_665 0.99 2.55 3.3575(16) 138.1
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_publ_flag
C11 C1 C2 C3 142.47(10) ?
C7 C1 C2 C3 -102.22(10) ?
C5 C1 C2 C3 -19.88(11) ?
C11 C1 C2 C7 -115.31(11) ?
C5 C1 C2 C7 82.35(9) ?
C7 C2 C3 C8 146.13(12) ?
C1 C2 C3 C8 -149.58(11) ?
C7 C2 C3 C4 -32.58(11) ?
C1 C2 C3 C4 31.71(11) ?
C8 C3 C4 C5 149.18(12) ?
C2 C3 C4 C5 -32.10(11) ?
C8 C3 C4 C6 -146.43(12) ?
C2 C3 C4 C6 32.29(11) ?
C3 C4 C5 C16 -138.90(10) ?
C6 C4 C5 C16 119.50(11) ?
C3 C4 C5 C6 101.60(10) ?
C3 C4 C5 C1 20.41(11) ?
C6 C4 C5 C1 -81.19(9) ?
C11 C1 C5 C16 -5.5(2) ?
C7 C1 C5 C16 -146.85(13) ?
C2 C1 C5 C16 154.03(12) ?
C11 C1 C5 C4 -159.80(11) ?
C7 C1 C5 C4 58.89(9) ?
C2 C1 C5 C4 -0.23(10) ?
C11 C1 C5 C6 141.29(12) ?
C7 C1 C5 C6 -0.01(8) ?
C2 C1 C5 C6 -59.14(9) ?
C16 C5 C6 C21 3.62(18) ?
C4 C5 C6 C21 107.58(12) ?
C1 C5 C6 C21 -146.63(11) ?
C16 C5 C6 C4 -103.96(12) ?
C1 C5 C6 C4 105.79(9) ?
C16 C5 C6 C7 150.26(11) ?
C4 C5 C6 C7 -105.78(9) ?
C1 C5 C6 C7 0.01(8) ?
C3 C4 C6 C21 139.78(10) ?
C5 C4 C6 C21 -117.23(12) ?
C3 C4 C6 C5 -102.99(10) ?
C3 C4 C6 C7 -20.29(11) ?
C5 C4 C6 C7 82.70(9) ?
C11 C1 C7 C26 4.88(19) ?
C2 C1 C7 C26 -103.92(13) ?
C5 C1 C7 C26 150.20(12) ?
C11 C1 C7 C2 108.80(12) ?
C5 C1 C7 C2 -105.88(9) ?
C11 C1 C7 C6 -145.31(11) ?
C2 C1 C7 C6 105.89(8) ?
C5 C1 C7 C6 0.01(8) ?
C3 C2 C7 C26 -135.69(10) ?
C1 C2 C7 C26 122.16(11) ?
C3 C2 C7 C1 102.15(10) ?
C3 C2 C7 C6 20.66(11) ?
C1 C2 C7 C6 -81.49(9) ?
C21 C6 C7 C26 -5.4(2) ?
C5 C6 C7 C26 -149.26(12) ?
C4 C6 C7 C26 151.55(11) ?
C21 C6 C7 C1 143.87(12) ?
C5 C6 C7 C1 -0.02(8) ?
C4 C6 C7 C1 -59.20(9) ?
C21 C6 C7 C2 -157.15(11) ?
C5 C6 C7 C2 58.97(9) ?
C4 C6 C7 C2 -0.22(10) ?
C4 C3 C8 C9 -177.87(11) ?
C2 C3 C8 C9 3.75(19) ?
C4 C3 C8 C10 2.77(19) ?
C2 C3 C8 C10 -175.61(11) ?
C14 N1 C11 O1 -171.47(11) ?
C12 N1 C11 O1 -0.67(17) ?
C14 N1 C11 C1 8.96(17) ?
C12 N1 C11 C1 179.76(10) ?
C7 C1 C11 O1 20.21(17) y
C2 C1 C11 O1 93.33(13) y
C5 C1 C11 O1 -109.96(14) y
C7 C1 C11 N1 -160.21(11) y
C2 C1 C11 N1 -87.08(13) y
C5 C1 C11 N1 69.63(16) y
C11 N1 C12 C13 -81.84(15) ?
C14 N1 C12 C13 89.63(14) ?
C11 N1 C14 C15 -113.37(13) ?
C12 N1 C14 C15 75.81(14) ?
C19 N2 C16 O2 -161.87(12) ?
C17 N2 C16 O2 7.4(2) ?
C17' N2 C16 O2 -24.9(4) ?
C19 N2 C16 C5 20.79(19) ?
C17 N2 C16 C5 -169.94(14) ?
C17' N2 C16 C5 157.8(4) ?
C4 C5 C16 O2 11.32(16) y
C6 C5 C16 O2 83.68(15) y
C1 C5 C16 O2 -140.05(13) y
C4 C5 C16 N2 -171.29(11) y
C6 C5 C16 N2 -98.92(14) y
C1 C5 C16 N2 37.35(19) y
C16 N2 C17 C18 -99.26(19) ?
C19 N2 C17 C18 70.5(2) ?
C17' N2 C17 C18 4.2(5) ?
C16 N2 C17' C18' 98.6(4) ?
C19 N2 C17' C18' -117.4(4) ?
C17 N2 C17' C18' 6.7(3) ?
C16 N2 C19 C20 -136.44(14) ?
C17 N2 C19 C20 54.61(19) ?
C17' N2 C19 C20 81.7(3) ?
C22 N3 C21 O3 -175.04(11) ?
C24 N3 C21 O3 -1.60(18) ?
C22 N3 C21 C6 3.30(17) ?
C24 N3 C21 C6 176.74(10) ?
C5 C6 C21 O3 16.84(17) y
C4 C6 C21 O3 90.22(13) y
C7 C6 C21 O3 -115.97(14) y
C5 C6 C21 N3 -161.55(11) y
C4 C6 C21 N3 -88.17(13) y
C7 C6 C21 N3 65.64(16) y
C21 N3 C22 C23 98.31(14) ?
C24 N3 C22 C23 -75.22(14) ?
C21 N3 C24 C25 99.69(15) ?
C22 N3 C24 C25 -86.41(16) ?
C29 N4 C26 O4 -166.04(11) ?
C27 N4 C26 O4 4.97(17) ?
C29 N4 C26 C7 17.24(17) ?
C27 N4 C26 C7 -171.75(10) ?
C1 C7 C26 O4 86.00(15) y
C2 C7 C26 O4 12.39(15) y
C6 C7 C26 O4 -135.97(12) y
C1 C7 C26 N4 -97.21(14) y
C2 C7 C26 N4 -170.82(10) y
C6 C7 C26 N4 40.83(17) y
C26 N4 C27 C28 86.32(16) ?
C29 N4 C27 C28 -101.91(15) ?
C26 N4 C29 C30 104.11(14) ?
C27 N4 C29 C30 -66.87(15) ?
