#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202322.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_2202322
loop_
_publ_author_name
'Winkler, Torsten'
'Herges, Rainer'
'Jones, Peter G.'
'Dix, Ina'
_publ_section_title
;
 A tetrakis(tertiary amide) derivative of norbornadiene:
 7-isopropylidenenorborna-2,5-diene-2,3,5,6-tetracarboxylic acid
 tetrakis(diethylamide)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1101
_journal_page_last               o1102
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C30 H48 N4 O4'
_chemical_formula_moiety         'C30 H48 N4 O4'
_chemical_formula_sum            'C30 H48 N4 O4'
_chemical_formula_weight         528.72
_chemical_name_systematic
;
7-isopropylidenenorborna-2,5-diene-2,3,5,6-tetracarboxylic acid
tetrakis(diethylamide)
;
_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                 106.353(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7945(12)
_cell_length_b                   25.449(3)
_cell_length_c                   11.6710(12)
_cell_measurement_reflns_used    4910
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2.2
_cell_volume                     3076.4(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       \w
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19202
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0417
_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/[\s^2^(Fo^2^)+(0.062P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                4102
_reflns_number_total             6300
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bt6290.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_database_code               2202322
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_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_type_symbol
O1 0.79816(11) 0.66733(5) 0.09104(9) 0.0359(3) Uani d . 1 O
O2 0.75937(10) 0.51322(4) 0.37644(10) 0.0362(3) Uani d . 1 O
O3 0.66659(10) 0.62720(5) 0.66299(9) 0.0366(3) Uani d . 1 O
O4 0.42995(10) 0.68820(5) 0.22351(9) 0.0326(3) Uani d . 1 O
N1 0.66646(12) 0.59666(5) 0.06782(11) 0.0297(3) Uani d . 1 N
N2 0.94430(11) 0.53210(5) 0.33016(11) 0.0271(3) Uani d . 1 N
N3 0.48350(11) 0.60232(5) 0.52538(11) 0.0271(3) Uani d . 1 N
N4 0.44752(13) 0.74008(6) 0.38489(12) 0.0389(4) Uani d . 1 N
C1 0.73255(13) 0.68912(6) 0.32409(13) 0.0232(3) Uani d . 1 C
H1 0.7278 0.7219 0.2759 0.028 Uiso calc R 1 H
C2 0.75545(13) 0.63725(6) 0.26518(13) 0.0227(3) Uani d . 1 C
C3 0.80098(12) 0.60263(6) 0.35372(12) 0.0212(3) Uani d . 1 C
C4 0.80330(13) 0.63064(6) 0.47131(12) 0.0217(3) Uani d . 1 C
H4 0.8578 0.6145 0.5469 0.026 Uiso calc R 1 H
C5 0.66173(13) 0.64309(6) 0.46530(12) 0.0220(3) Uani d . 1 C
C6 0.62009(13) 0.67880(6) 0.37921(12) 0.0223(3) Uani d . 1 C
C7 0.84278(13) 0.68522(6) 0.43928(12) 0.0224(3) Uani d . 1 C
C8 0.93647(14) 0.71763(6) 0.49500(13) 0.0272(4) Uani d . 1 C
C9 1.03525(15) 0.70210(7) 0.60898(15) 0.0352(4) Uani d . 1 C
H9A 1.0206 0.7221 0.6757 0.042 Uiso calc R 1 H
H9B 1.1220 0.7096 0.6023 0.042 Uiso calc R 1 H
H9C 1.0275 0.6644 0.6232 0.042 Uiso calc R 1 H
C10 0.94805(17) 0.77257(7) 0.45172(16) 0.0369(4) Uani d . 1 C
H10A 0.8897 0.7768 0.3711 0.044 Uiso calc R 1 H
H10B 1.0371 0.7789 0.4502 0.044 Uiso calc R 1 H
H10C 0.9249 0.7978 0.5057 0.044 Uiso calc R 1 H
C11 0.74030(14) 0.63450(6) 0.13440(13) 0.0258(3) Uani d . 1 C
C12 0.57984(15) 0.56158(7) 0.10810(14) 0.0333(4) Uani d . 1 C
H12A 0.6051 0.5613 0.1965 0.040 Uiso calc R 1 H
H12B 0.5899 0.5254 0.0808 0.040 Uiso calc R 1 H
C13 0.43891(15) 0.57763(8) 0.06197(16) 0.0403(4) Uani d . 1 C
H13A 0.4268 0.6122 0.0942 0.048 Uiso calc R 1 H
H13B 0.3849 0.5517 0.0874 0.048 Uiso calc R 1 H
H13C 0.4141 0.5793 -0.0254 0.048 Uiso calc R 1 H
C14 0.66111(16) 0.59381(8) -0.05969(14) 0.0372(4) Uani d . 1 C
H14A 0.6589 0.6299 -0.0917 0.045 Uiso calc R 1 H
H14B 0.5802 0.5760 -0.1038 0.045 Uiso calc R 1 H
C15 0.77390(17) 0.56487(8) -0.08165(14) 0.0420(4) Uani d . 1 C
H15A 0.8533 0.5849 -0.0476 0.050 Uiso calc R 1 H
H15B 0.7603 0.5607 -0.1678 0.050 Uiso calc R 1 H
H15C 0.7815 0.5302 -0.0439 0.050 Uiso calc R 1 H
C16 0.83304(13) 0.54597(6) 0.35305(12) 0.0228(3) Uani d . 1 C
C17 0.97370(16) 0.47609(7) 0.32691(15) 0.0367(4) Uani d . 1 C
H17A 0.9509 0.4582 0.3935 0.044 Uiso calc R 1 H
H17B 1.0677 0.4718 0.3394 0.044 Uiso calc R 1 H
C18 0.9026(2) 0.44980(8) 0.21083(17) 0.0545(5) Uani d . 1 C
H18A 0.8093 0.4527 0.1993 0.065 Uiso calc R 1 H
H18B 0.9271 0.4126 0.2136 0.065 Uiso calc R 1 H
H18C 0.9252 0.4671 0.1444 0.065 Uiso calc R 1 H
C19 1.04566(14) 0.56986(7) 0.32538(15) 0.0354(4) Uani d . 1 C
H19A 1.1274 0.5593 0.3841 0.042 Uiso calc R 1 H
H19B 1.0217 0.6049 0.3491 0.042 Uiso calc R 1 H
C20 1.06780(17) 0.57395(9) 0.20379(16) 0.0494(5) Uani d . 1 C
H20A 1.0864 0.5390 0.1775 0.059 Uiso calc R 1 H
H20B 1.1411 0.5973 0.2081 0.059 Uiso calc R 1 H
H20C 0.9903 0.5882 0.1468 0.059 Uiso calc R 1 H
C21 0.60349(14) 0.62291(6) 0.55785(13) 0.0234(3) Uani d . 1 C
C22 0.42408(16) 0.59024(7) 0.62121(14) 0.0340(4) Uani d . 1 C
H22A 0.4898 0.5748 0.6898 0.041 Uiso calc R 1 H
H22B 0.3547 0.5640 0.5922 0.041 Uiso calc R 1 H
C23 0.3686(2) 0.63881(9) 0.6614(2) 0.0629(6) Uani d . 1 C
H23A 0.4372 0.6648 0.6905 0.076 Uiso calc R 1 H
H23B 0.3307 0.6297 0.7259 0.076 Uiso calc R 1 H
H23C 0.3017 0.6536 0.5941 0.076 Uiso calc R 1 H
C24 0.40765(15) 0.59014(7) 0.40285(14) 0.0305(4) Uani d . 1 C
H24A 0.4483 0.6075 0.3466 0.037 Uiso calc R 1 H
H24B 0.3200 0.6050 0.3891 0.037 Uiso calc R 1 H
C25 0.39613(17) 0.53208(7) 0.37571(15) 0.0400(4) Uani d . 1 C
H25A 0.4819 0.5176 0.3820 0.048 Uiso calc R 1 H
H25B 0.3400 0.5266 0.2946 0.048 Uiso calc R 1 H
H25C 0.3590 0.5143 0.4329 0.048 Uiso calc R 1 H
C26 0.49095(14) 0.70284(6) 0.32486(13) 0.0264(3) Uani d . 1 C
C27 0.52281(19) 0.76161(8) 0.50031(16) 0.0461(5) Uani d . 1 C
H27A 0.5818 0.7341 0.5451 0.055 Uiso calc R 1 H
H27B 0.4634 0.7715 0.5476 0.055 Uiso calc R 1 H
C28 0.6009(2) 0.80920(9) 0.48557(19) 0.0650(6) Uani d . 1 C
H28A 0.6586 0.7997 0.4373 0.078 Uiso calc R 1 H
H28B 0.6523 0.8214 0.5643 0.078 Uiso calc R 1 H
H28C 0.5425 0.8373 0.4456 0.078 Uiso calc R 1 H
C29 0.32216(18) 0.76484(9) 0.32497(18) 0.0557(6) Uani d . 1 C
H29A 0.3160 0.7704 0.2396 0.067 Uiso calc R 1 H
H29B 0.3172 0.7996 0.3615 0.067 Uiso calc R 1 H
C30 0.21109(19) 0.73157(12) 0.3348(2) 0.0785(9) Uani d . 1 C
H30A 0.2147 0.6974 0.2972 0.094 Uiso calc R 1 H
H30B 0.1297 0.7492 0.2945 0.094 Uiso calc R 1 H
H30C 0.2162 0.7264 0.4192 0.094 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0428(7) 0.0354(7) 0.0336(7) -0.0058(6) 0.0177(5) 0.0043(5)
O2 0.0339(6) 0.0246(7) 0.0550(8) -0.0029(5) 0.0204(6) 0.0046(5)
O3 0.0336(6) 0.0517(8) 0.0232(6) -0.0091(5) 0.0058(5) 0.0009(5)
O4 0.0290(6) 0.0393(7) 0.0265(6) 0.0062(5) 0.0028(5) 0.0009(5)
N1 0.0307(7) 0.0355(8) 0.0223(7) -0.0043(6) 0.0066(6) -0.0040(6)
N2 0.0217(6) 0.0244(7) 0.0352(7) 0.0042(5) 0.0079(6) 0.0007(6)
N3 0.0225(6) 0.0345(8) 0.0256(7) -0.0034(6) 0.0089(5) -0.0001(6)
N4 0.0368(8) 0.0437(9) 0.0327(8) 0.0201(7) 0.0041(6) -0.0038(7)
C1 0.0250(7) 0.0204(8) 0.0248(8) 0.0008(6) 0.0081(6) 0.0028(6)
C2 0.0188(7) 0.0222(8) 0.0277(8) -0.0028(6) 0.0077(6) -0.0004(6)
C3 0.0158(7) 0.0219(8) 0.0267(8) -0.0022(6) 0.0071(6) -0.0002(6)
C4 0.0183(7) 0.0218(8) 0.0239(8) 0.0015(6) 0.0043(6) 0.0012(6)
C5 0.0213(7) 0.0223(8) 0.0223(8) 0.0003(6) 0.0062(6) -0.0037(6)
C6 0.0217(7) 0.0221(8) 0.0229(8) 0.0012(6) 0.0057(6) -0.0031(6)
C7 0.0225(7) 0.0211(8) 0.0251(8) 0.0020(6) 0.0094(6) -0.0011(6)
C8 0.0270(8) 0.0264(9) 0.0307(8) -0.0017(7) 0.0123(7) -0.0056(7)
C9 0.0266(8) 0.0356(10) 0.0409(10) -0.0059(7) 0.0053(7) -0.0103(8)
C10 0.0423(10) 0.0274(10) 0.0454(10) -0.0090(8) 0.0194(8) -0.0071(8)
C11 0.0251(8) 0.0255(9) 0.0274(8) 0.0045(7) 0.0084(7) 0.0025(7)
C12 0.0357(9) 0.0326(10) 0.0293(9) -0.0077(8) 0.0055(7) -0.0038(7)
C13 0.0353(9) 0.0432(12) 0.0417(10) -0.0060(8) 0.0096(8) -0.0067(8)
C14 0.0397(9) 0.0470(11) 0.0230(8) 0.0021(8) 0.0058(7) -0.0034(8)
C15 0.0508(11) 0.0492(12) 0.0268(9) 0.0068(9) 0.0121(8) -0.0031(8)
C16 0.0215(7) 0.0227(8) 0.0230(8) -0.0001(6) 0.0044(6) 0.0002(6)
C17 0.0372(9) 0.0304(10) 0.0435(10) 0.0130(8) 0.0132(8) 0.0033(8)
C18 0.0782(14) 0.0325(11) 0.0533(12) 0.0103(10) 0.0191(11) -0.0068(9)
C19 0.0210(8) 0.0401(11) 0.0453(10) -0.0015(7) 0.0097(7) 0.0030(8)
C20 0.0284(9) 0.0698(15) 0.0486(11) -0.0012(9) 0.0086(8) 0.0136(10)
C21 0.0241(7) 0.0234(9) 0.0232(8) 0.0010(6) 0.0074(6) -0.0004(6)
C22 0.0313(9) 0.0416(11) 0.0335(9) -0.0060(8) 0.0166(7) 0.0001(8)
C23 0.0735(14) 0.0609(15) 0.0751(15) 0.0150(12) 0.0548(13) 0.0072(12)
C24 0.0246(8) 0.0354(10) 0.0289(8) -0.0019(7) 0.0032(7) 0.0004(7)
C25 0.0381(9) 0.0399(11) 0.0363(10) 0.0001(8) 0.0012(8) -0.0028(8)
C26 0.0256(8) 0.0280(9) 0.0256(8) 0.0055(7) 0.0073(7) 0.0035(7)
C27 0.0558(11) 0.0452(12) 0.0338(10) 0.0227(10) 0.0070(9) -0.0084(8)
C28 0.0782(15) 0.0553(15) 0.0560(13) 0.0038(13) 0.0102(12) -0.0177(11)
C29 0.0505(12) 0.0653(15) 0.0458(12) 0.0386(11) 0.0044(9) -0.0044(10)
C30 0.0384(11) 0.147(3) 0.0545(14) 0.0421(14) 0.0200(10) 0.0244(14)
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 C12 125.33(12) ?
C11 N1 C14 117.74(13) ?
C12 N1 C14 116.58(13) ?
C16 N2 C17 118.16(13) ?
C16 N2 C19 123.40(13) ?
C17 N2 C19 117.84(12) ?
C21 N3 C24 125.76(12) ?
C21 N3 C22 117.24(12) ?
C24 N3 C22 117.00(12) ?
C26 N4 C27 123.96(13) ?
C26 N4 C29 117.57(14) ?
C27 N4 C29 118.12(14) ?
C7 C1 C2 98.86(11) ?
C7 C1 C6 97.53(11) ?
C2 C1 C6 106.45(12) ?
C7 C1 H1 117.0 ?
C2 C1 H1 117.0 ?
C6 C1 H1 117.0 ?
C3 C2 C11 131.97(14) y
C3 C2 C1 106.81(12) y
C11 C2 C1 120.83(13) y
C2 C3 C16 132.06(13) y
C2 C3 C4 107.02(13) y
C16 C3 C4 120.62(12) y
C7 C4 C3 97.95(11) ?
C7 C4 C5 98.22(11) ?
C3 C4 C5 106.68(11) ?
C7 C4 H4 117.0 ?
C3 C4 H4 117.0 ?
C5 C4 H4 117.0 ?
C6 C5 C21 131.34(13) ?
C6 C5 C4 107.05(12) ?
C21 C5 C4 120.82(12) ?
C5 C6 C26 132.52(13) ?
C5 C6 C1 106.91(12) ?
C26 C6 C1 120.16(12) ?
C8 C7 C1 133.59(14) ?
C8 C7 C4 132.21(14) ?
C1 C7 C4 94.16(11) ?
C7 C8 C10 122.55(15) ?
C7 C8 C9 121.55(15) ?
C10 C8 C9 115.85(14) ?
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 122.19(14) ?
O1 C11 C2 117.77(14) ?
N1 C11 C2 120.03(13) ?
N1 C12 C13 112.89(14) ?
N1 C12 H12A 109.0 ?
C13 C12 H12A 109.0 ?
N1 C12 H12B 109.0 ?
C13 C12 H12B 109.0 ?
H12A C12 H12B 107.8 ?
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 113.08(13) ?
N1 C14 H14A 109.0 ?
C15 C14 H14A 109.0 ?
N1 C14 H14B 109.0 ?
C15 C14 H14B 109.0 ?
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 122.14(14) ?
O2 C16 C3 119.29(13) ?
N2 C16 C3 118.53(13) ?
N2 C17 C18 113.27(14) ?
N2 C17 H17A 108.9 ?
C18 C17 H17A 108.9 ?
N2 C17 H17B 108.9 ?
C18 C17 H17B 108.9 ?
H17A C17 H17B 107.7 ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
N2 C19 C20 113.45(14) ?
N2 C19 H19A 108.9 ?
C20 C19 H19A 108.9 ?
N2 C19 H19B 108.9 ?
C20 C19 H19B 108.9 ?
H19A C19 H19B 107.7 ?
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 122.24(13) ?
O3 C21 C5 117.77(13) ?
N3 C21 C5 119.95(13) ?
N3 C22 C23 111.27(15) ?
N3 C22 H22A 109.4 ?
C23 C22 H22A 109.4 ?
N3 C22 H22B 109.4 ?
C23 C22 H22B 109.4 ?
H22A C22 H22B 108.0 ?
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 113.70(13) ?
N3 C24 H24A 108.8 ?
C25 C24 H24A 108.8 ?
N3 C24 H24B 108.8 ?
C25 C24 H24B 108.8 ?
H24A C24 H24B 107.7 ?
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 122.84(14) ?
O4 C26 C6 117.71(13) ?
N4 C26 C6 119.41(13) ?
N4 C27 C28 112.11(15) ?
N4 C27 H27A 109.2 ?
C28 C27 H27A 109.2 ?
N4 C27 H27B 109.2 ?
C28 C27 H27B 109.2 ?
H27A C27 H27B 107.9 ?
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 111.62(18) ?
N4 C29 H29A 109.3 ?
C30 C29 H29A 109.3 ?
N4 C29 H29B 109.3 ?
C30 C29 H29B 109.3 ?
H29A C29 H29B 108.0 ?
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_distance
O1 C11 1.2339(18)
O2 C16 1.2345(17)
O3 C21 1.2292(16)
O4 C26 1.2382(17)
N1 C11 1.348(2)
N1 C12 1.463(2)
N1 C14 1.475(2)
N2 C16 1.3488(18)
N2 C17 1.463(2)
N2 C19 1.469(2)
N3 C21 1.3487(19)
N3 C24 1.4670(19)
N3 C22 1.4701(19)
N4 C26 1.339(2)
N4 C27 1.469(2)
N4 C29 1.478(2)
C1 C7 1.527(2)
C1 C2 1.540(2)
C1 C6 1.548(2)
C1 H1 1.0000
C2 C3 1.342(2)
C2 C11 1.490(2)
C3 C16 1.483(2)
C3 C4 1.541(2)
C4 C7 1.530(2)
C4 C5 1.5428(19)
C4 H4 1.0000
C5 C6 1.335(2)
C5 C21 1.486(2)
C6 C26 1.491(2)
C7 C8 1.325(2)
C8 C10 1.504(2)
C8 C9 1.505(2)
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 1.520(2)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C15 1.505(2)
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C17 C18 1.512(3)
C17 H17A 0.9900
C17 H17B 0.9900
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 C20 1.507(2)
C19 H19A 0.9900
C19 H19B 0.9900
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C22 C23 1.505(3)
C22 H22A 0.9900
C22 H22B 0.9900
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C24 C25 1.509(2)
C24 H24A 0.9900
C24 H24B 0.9900
C25 H25A 0.9800
C25 H25B 0.9800
C25 H25C 0.9800
C27 C28 1.513(3)
C27 H27A 0.9900
C27 H27B 0.9900
C28 H28A 0.9800
C28 H28B 0.9800
C28 H28C 0.9800
C29 C30 1.498(3)
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
C27 H27B O1 4_576 0.99 2.52 3.423(2) 151
C22 H22B O2 3_666 0.99 2.40 3.299(2) 151
C15 H15B O3 1_554 0.98 2.58 3.286(2) 129
C9 H9A O4 4_676 0.98 2.61 3.425(2) 141
C10 H10C O4 4_676 0.98 2.55 3.383(2) 143
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
C7 C1 C2 C3 33.25(13) ?
C6 C1 C2 C3 -67.37(14) ?
C7 C1 C2 C11 -140.34(13) ?
C6 C1 C2 C11 119.04(14) ?
C11 C2 C3 C16 -11.7(3) ?
C1 C2 C3 C16 175.70(14) ?
C11 C2 C3 C4 174.84(14) ?
C1 C2 C3 C4 2.25(14) ?
C2 C3 C4 C7 -36.81(13) ?
C16 C3 C4 C7 148.84(12) ?
C2 C3 C4 C5 64.29(14) ?
C16 C3 C4 C5 -110.06(14) ?
C7 C4 C5 C6 33.85(14) ?
C3 C4 C5 C6 -67.05(15) ?
C7 C4 C5 C21 -137.05(13) ?
C3 C4 C5 C21 122.05(14) ?
C21 C5 C6 C26 -16.1(3) ?
C4 C5 C6 C26 174.27(15) ?
C21 C5 C6 C1 171.43(14) ?
C4 C5 C6 C1 1.84(15) ?
C7 C1 C6 C5 -36.90(14) ?
C2 C1 C6 C5 64.70(14) ?
C7 C1 C6 C26 149.55(13) ?
C2 C1 C6 C26 -108.85(15) ?
C2 C1 C7 C8 128.98(17) ?
C6 C1 C7 C8 -122.97(17) ?
C2 C1 C7 C4 -53.26(11) ?
C6 C1 C7 C4 54.78(12) ?
C3 C4 C7 C8 -127.96(16) ?
C5 C4 C7 C8 123.80(16) ?
C3 C4 C7 C1 54.23(11) ?
C5 C4 C7 C1 -54.01(11) ?
C1 C7 C8 C10 3.7(3) ?
C4 C7 C8 C10 -173.26(14) ?
C1 C7 C8 C9 -178.73(14) ?
C4 C7 C8 C9 4.3(2) ?
C12 N1 C11 O1 -170.13(14) ?
C14 N1 C11 O1 2.8(2) ?
C12 N1 C11 C2 10.6(2) ?
C14 N1 C11 C2 -176.41(13) ?
C3 C2 C11 O1 -120.22(18) y
C1 C2 C11 O1 51.52(19) y
C3 C2 C11 N1 59.1(2) y
C1 C2 C11 N1 -129.20(15) y
C11 N1 C12 C13 102.11(17) ?
C14 N1 C12 C13 -70.93(18) ?
C11 N1 C14 C15 82.23(19) ?
C12 N1 C14 C15 -104.18(17) ?
C17 N2 C16 O2 3.4(2) ?
C19 N2 C16 O2 -167.55(14) ?
C17 N2 C16 C3 -178.59(12) ?
C19 N2 C16 C3 10.5(2) ?
C2 C3 C16 O2 -104.94(19) y
C4 C3 C16 O2 67.78(18) y
C2 C3 C16 N2 77.0(2) y
C4 C3 C16 N2 -110.30(15) y
C16 N2 C17 C18 79.40(19) ?
C19 N2 C17 C18 -109.16(17) ?
C16 N2 C19 C20 -115.96(17) ?
C17 N2 C19 C20 73.08(18) ?
C24 N3 C21 O3 -172.46(14) ?
C22 N3 C21 O3 6.5(2) ?
C24 N3 C21 C5 9.8(2) ?
C22 N3 C21 C5 -171.26(13) ?
C6 C5 C21 O3 -122.55(18) y
C4 C5 C21 O3 45.8(2) y
C6 C5 C21 N3 55.3(2) y
C4 C5 C21 N3 -136.28(15) y
C21 N3 C22 C23 80.44(19) ?
C24 N3 C22 C23 -100.47(18) ?
C21 N3 C24 C25 107.24(18) ?
C22 N3 C24 C25 -71.75(18) ?
C27 N4 C26 O4 -174.17(16) ?
C29 N4 C26 O4 -1.1(2) ?
C27 N4 C26 C6 3.7(2) ?
C29 N4 C26 C6 176.80(16) ?
C5 C6 C26 O4 -105.61(19) y
C1 C6 C26 O4 66.01(19) y
C5 C6 C26 N4 76.4(2) y
C1 C6 C26 N4 -111.95(16) y
C26 N4 C27 C28 90.6(2) ?
C29 N4 C27 C28 -82.5(2) ?
C26 N4 C29 C30 81.3(2) ?
C27 N4 C29 C30 -105.2(2) ?