#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/49/2224927.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_2224927
loop_
_publ_author_name
'Zhu, Yanping'
'Sun, Yichong'
'Qiu, Mingqiang'
_publ_section_title
;Diethyl
 2-tert-butyl-4,11-dioxo-2,3-dihydro-cis-1H,5H,10H-2,3a,4a,10a,11a-pentaazabenzo[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate
;
_journal_coeditor_code           CV2681
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o289
_journal_paper_doi               10.1107/S1600536810000097
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C24 H31 N5 O6'
_chemical_formula_moiety         'C24 H31 N5 O6'
_chemical_formula_sum            'C24 H31 N5 O6'
_chemical_formula_weight         485.54
_chemical_name_systematic
;
Diethyl 2-tert-butyl-4,11-dioxo-2,3-dihydro-cis-
1H,5H,10H-2,3a,4a,10a,11a-
pentaazabenzo[f]indeno[2,1,7ija]azulene-11b,11c-dicarboxylate
;
_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                100.493(2)
_cell_angle_beta                 105.438(2)
_cell_angle_gamma                102.445(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7133(14)
_cell_length_b                   11.1013(15)
_cell_length_c                   11.3352(15)
_cell_measurement_reflns_used    2728
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      23.27
_cell_measurement_theta_min      2.33
_cell_volume                     1227.2(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9853
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0622
_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)+(0.1160P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1949
_reflns_number_gt                2734
_reflns_number_total             4253
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv2681.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224927
_cod_database_fobs_code          2224927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
C C1 0.2330(3) -0.0629(3) 0.5732(4) 0.0707(9) Uani d . 1 . .
C C2 0.1387(4) -0.1323(3) 0.4603(5) 0.0946(12) Uani d . 1 . .
H H2 0.1646 -0.1474 0.3881 0.114 Uiso calc R 1 . .
C C3 0.0032(5) -0.1810(4) 0.4517(7) 0.131(2) Uani d . 1 . .
H H3 -0.0605 -0.2276 0.3745 0.157 Uiso calc R 1 . .
C C4 -0.0332(6) -0.1590(6) 0.5575(10) 0.141(3) Uani d . 1 . .
H H4 -0.1225 -0.1915 0.5525 0.169 Uiso calc R 1 . .
C C5 0.0599(6) -0.0892(5) 0.6724(7) 0.1203(18) Uani d . 1 . .
H H5 0.0326 -0.0752 0.7439 0.144 Uiso calc R 1 . .
C C6 0.1936(4) -0.0398(3) 0.6825(4) 0.0825(11) Uani d . 1 . .
C C7 0.2936(5) 0.0298(3) 0.8120(4) 0.0916(12) Uani d . 1 D .
H H7A 0.2447 0.0388 0.8723 0.110 Uiso calc R 1 . .
H H7B 0.3532 -0.0220 0.8374 0.110 Uiso calc R 1 . .
C C8 0.3760(3) -0.0180(2) 0.5746(3) 0.0634(8) Uani d . 1 D .
H H8A 0.4280 -0.0669 0.6193 0.076 Uiso calc R 1 . .
H H8B 0.3772 -0.0372 0.4880 0.076 Uiso calc R 1 . .
C C9 0.4226(3) 0.2080(2) 0.5675(2) 0.0450(6) Uani d . 1 D .
C C10 0.3472(3) 0.2665(3) 0.8592(3) 0.0641(8) Uani d . 1 D .
C C11 0.4844(3) 0.1701(2) 0.7674(2) 0.0576(7) Uani d . 1 D .
C C12 0.5931(4) 0.1179(3) 0.8426(3) 0.0844(11) Uani d D 1 . .
C C13 0.7589(10) 0.0161(11) 0.8247(10) 0.138(4) Uani d PDU 0.58(13) A 1
H H13A 0.7778 -0.0399 0.7594 0.166 Uiso calc PR 0.58 A 1
H H13B 0.7242 -0.0352 0.8757 0.166 Uiso calc PR 0.58 A 1
C C14 0.8840(12) 0.1122(12) 0.9046(13) 0.184(6) Uani d PDU 0.58(13) A 1
H H14A 0.9079 0.1746 0.8599 0.276 Uiso calc PR 0.58 A 1
H H14B 0.9548 0.0719 0.9253 0.276 Uiso calc PR 0.58 A 1
H H14C 0.8712 0.1533 0.9809 0.276 Uiso calc PR 0.58 A 1
C C15 0.5263(3) 0.3179(2) 0.7817(2) 0.0504(7) Uani d . 1 . .
C C16 0.6759(4) 0.3861(3) 0.8485(3) 0.0730(9) Uani d D 1 B .
C C17 0.8800(10) 0.4862(14) 0.8238(14) 0.188(5) Uani d PDU 0.56(12) B 1
H H17A 0.9208 0.4584 0.8974 0.225 Uiso calc PR 0.56 B 1
H H17B 0.9202 0.4634 0.7588 0.225 Uiso calc PR 0.56 B 1
C C18 0.8945(16) 0.6226(16) 0.856(2) 0.190(8) Uani d PDU 0.56 B 1
H H18A 0.8694 0.6505 0.7802 0.286 Uiso calc PR 0.56 B 1
H H18B 0.9865 0.6674 0.9046 0.286 Uiso calc PR 0.56 B 1
H H18C 0.8370 0.6399 0.9055 0.286 Uiso calc PR 0.56 B 1
C C19 0.4409(3) 0.4385(2) 0.6278(2) 0.0519(7) Uani d . 1 . .
H H19A 0.3984 0.4254 0.5377 0.062 Uiso calc R 1 D .
H H19B 0.5196 0.5119 0.6559 0.062 Uiso calc R 1 . .
C C20 0.4129(3) 0.4808(2) 0.8311(2) 0.0569(7) Uani d . 1 . .
H H20A 0.4942 0.5514 0.8604 0.068 Uiso calc R 1 D .
H H20B 0.3532 0.5012 0.8779 0.068 Uiso calc R 1 . .
C C21 0.2878(3) 0.5689(3) 0.6669(3) 0.0642(8) Uani d . 1 . .
C C22 0.1716(4) 0.5641(4) 0.7200(4) 0.0937(11) Uani d . 1 D .
H H22A 0.1086 0.4808 0.6865 0.141 Uiso calc R 1 . .
H H22B 0.1272 0.6267 0.6965 0.141 Uiso calc R 1 . .
H H22C 0.2053 0.5818 0.8106 0.141 Uiso calc R 1 . .
C C23 0.3910(4) 0.7005(3) 0.7234(4) 0.0996(12) Uani d . 1 D .
H H23A 0.4286 0.7134 0.8132 0.149 Uiso calc R 1 . .
H H23B 0.3472 0.7654 0.7068 0.149 Uiso calc R 1 . .
H H23C 0.4616 0.7051 0.6857 0.149 Uiso calc R 1 . .
C C24 0.2300(4) 0.5452(4) 0.5232(3) 0.0966(12) Uani d . 1 D .
H H24A 0.3019 0.5505 0.4871 0.145 Uiso calc R 1 . .
H H24B 0.1848 0.6085 0.5040 0.145 Uiso calc R 1 . .
H H24C 0.1671 0.4620 0.4885 0.145 Uiso calc R 1 . .
C C13' 0.8049(12) 0.0858(17) 0.867(2) 0.169(8) Uani d PDU 0.42(13) C 2
H H13C 0.8264 0.1281 0.9558 0.203 Uiso calc PR 0.42 C 2
H H13D 0.8837 0.1142 0.8419 0.203 Uiso calc PR 0.42 C 2
C C14' 0.7753(15) -0.0522(15) 0.8527(12) 0.165(6) Uani d PDU 0.42(13) C 2
H H14D 0.7121 -0.0780 0.8957 0.248 Uiso calc PR 0.42 C 2
H H14E 0.8571 -0.0735 0.8885 0.248 Uiso calc PR 0.42 C 2
H H14F 0.7374 -0.0957 0.7645 0.248 Uiso calc PR 0.42 C 2
C C17' 0.8558(11) 0.5710(11) 0.8799(13) 0.095(3) Uani d PDU 0.44(12) B 2
H H17C 0.9176 0.5259 0.8575 0.113 Uiso calc PR 0.44 B 2
H H17D 0.8793 0.5963 0.9713 0.113 Uiso calc PR 0.44 B 2
C C18' 0.8578(12) 0.6842(12) 0.8253(13) 0.127(5) Uani d PDU 0.44(12) B 2
H H18D 0.8380 0.6571 0.7353 0.190 Uiso calc PR 0.44 B 2
H H18E 0.9454 0.7444 0.8619 0.190 Uiso calc PR 0.44 B 2
H H18F 0.7913 0.7236 0.8435 0.190 Uiso calc PR 0.44 B 2
N N1 0.4438(2) 0.11805(18) 0.63279(19) 0.0510(6) Uani d . 1 . .
N N2 0.3746(3) 0.1548(2) 0.8183(2) 0.0725(8) Uani d . 1 . .
N N3 0.4818(2) 0.32668(18) 0.65159(18) 0.0479(5) Uani d . 1 D .
N N4 0.4467(2) 0.3659(2) 0.85387(19) 0.0550(6) Uani d . 1 D .
N N5 0.3465(2) 0.46257(18) 0.69526(18) 0.0503(6) Uani d . 1 D .
O O1 0.36756(19) 0.18819(16) 0.45526(17) 0.0599(5) Uani d . 1 . .
O O2 0.2539(3) 0.2773(2) 0.8978(2) 0.0899(8) Uani d . 1 . .
O O3 0.5872(17) 0.0875(14) 0.9359(8) 0.135(5) Uani d PDU 0.58(13) D 1
O O4 0.6596(7) 0.0723(8) 0.7670(7) 0.098(3) Uani d PDU 0.58(13) A 1
O O5 0.7302(5) 0.3777(6) 0.9524(3) 0.0774(14) Uani d PD 0.56(12) B 1
O O6 0.7316(6) 0.4306(9) 0.7765(6) 0.136(3) Uani d PDU 0.56 B 1
O O3' 0.624(2) 0.1280(19) 0.9535(9) 0.124(6) Uani d PDU 0.42(13) D 2
O O4' 0.6965(9) 0.1227(10) 0.7948(10) 0.086(3) Uani d PDU 0.42(13) C 2
O O5' 0.7607(13) 0.3412(14) 0.893(2) 0.259(8) Uani d PDU 0.44(12) B 2
O O6' 0.7172(6) 0.4933(5) 0.8223(8) 0.091(3) Uani d PD 0.44(12) B 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.5(3) ?
C2 C1 C8 . . 117.4(3) ?
C6 C1 C8 . . 123.1(3) ?
C1 C2 C3 . . 120.9(5) ?
C1 C2 H2 . . 119.5 ?
C3 C2 H2 . . 119.5 ?
C4 C3 C2 . . 119.0(6) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C5 . . 121.2(5) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C4 C5 C6 . . 120.6(5) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C5 C6 C1 . . 118.8(5) ?
C5 C6 C7 . . 118.7(4) ?
C1 C6 C7 . . 122.4(3) ?
N2 C7 C6 . . 114.3(3) ?
N2 C7 H7A . . 108.7 ?
C6 C7 H7A . . 108.7 ?
N2 C7 H7B . . 108.7 ?
C6 C7 H7B . . 108.7 ?
H7A C7 H7B . . 107.6 ?
N1 C8 C1 . . 116.0(2) ?
N1 C8 H8A . . 108.3 ?
C1 C8 H8A . . 108.3 ?
N1 C8 H8B . . 108.3 ?
C1 C8 H8B . . 108.3 ?
H8A C8 H8B . . 107.4 ?
O1 C9 N1 . . 126.4(2) ?
O1 C9 N3 . . 125.6(2) ?
N1 C9 N3 . . 107.9(2) ?
O2 C10 N2 . . 125.9(3) ?
O2 C10 N4 . . 125.6(3) ?
N2 C10 N4 . . 108.5(2) ?
N2 C11 N1 . . 113.7(2) ?
N2 C11 C12 . . 108.8(2) ?
N1 C11 C12 . . 113.5(2) ?
N2 C11 C15 . . 102.01(19) ?
N1 C11 C15 . . 102.94(17) ?
C12 C11 C15 . . 115.4(3) ?
O3 C12 O3' . . 24.2(17) ?
O3 C12 O4 . . 124.6(9) ?
O3' C12 O4 . . 124.5(10) ?
O3 C12 O4' . . 126.2(9) ?
O3' C12 O4' . . 114.3(12) ?
O4 C12 O4' . . 25.0(6) ?
O3 C12 C11 . . 121.6(8) ?
O3' C12 C11 . . 125.3(10) ?
O4 C12 C11 . . 109.8(4) ?
O4' C12 C11 . . 111.9(5) ?
O4 C13 C14 . . 111.9(9) ?
O4 C13 H13A . . 109.2 ?
C14 C13 H13A . . 109.2 ?
O4 C13 H13B . . 109.2 ?
C14 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
N4 C15 N3 . . 111.76(19) ?
N4 C15 C16 . . 109.9(2) ?
N3 C15 C16 . . 112.5(2) ?
N4 C15 C11 . . 104.0(2) ?
N3 C15 C11 . . 102.7(2) ?
C16 C15 C11 . . 115.6(2) ?
O5' C16 O5 . . 44.5(12) ?
O5' C16 O6 . . 95.8(12) ?
O5 C16 O6 . . 126.7(5) ?
O5' C16 O6' . . 115.4(9) ?
O5 C16 O6' . . 116.8(5) ?
O6 C16 O6' . . 39.5(5) ?
O5' C16 C15 . . 127.3(8) ?
O5 C16 C15 . . 120.3(4) ?
O6 C16 C15 . . 112.1(4) ?
O6' C16 C15 . . 114.4(4) ?
C18 C17 O6 . . 102.7(10) ?
C18 C17 H17A . . 111.2 ?
O6 C17 H17A . . 111.2 ?
C18 C17 H17B . . 111.2 ?
O6 C17 H17B . . 111.2 ?
H17A C17 H17B . . 109.1 ?
N3 C19 N5 . . 109.90(18) ?
N3 C19 H19A . . 109.7 ?
N5 C19 H19A . . 109.7 ?
N3 C19 H19B . . 109.7 ?
N5 C19 H19B . . 109.7 ?
H19A C19 H19B . . 108.2 ?
N4 C20 N5 . . 110.0(2) ?
N4 C20 H20A . . 109.7 ?
N5 C20 H20A . . 109.7 ?
N4 C20 H20B . . 109.7 ?
N5 C20 H20B . . 109.7 ?
H20A C20 H20B . . 108.2 ?
N5 C21 C22 . . 107.9(2) ?
N5 C21 C24 . . 108.7(2) ?
C22 C21 C24 . . 107.6(3) ?
N5 C21 C23 . . 112.8(2) ?
C22 C21 C23 . . 109.6(3) ?
C24 C21 C23 . . 110.1(3) ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C21 C23 H23A . . 109.5 ?
C21 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C21 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C21 C24 H24A . . 109.5 ?
C21 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C21 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
O4' C13' C14' . . 113.2(14) ?
O4' C13' H13C . . 108.9 ?
C14' C13' H13C . . 108.9 ?
O4' C13' H13D . . 108.9 ?
C14' C13' H13D . . 108.9 ?
H13C C13' H13D . . 107.8 ?
C13' C14' H14D . . 109.5 ?
C13' C14' H14E . . 109.5 ?
H14D C14' H14E . . 109.5 ?
C13' C14' H14F . . 109.5 ?
H14D C14' H14F . . 109.5 ?
H14E C14' H14F . . 109.5 ?
O6' C17' C18' . . 103.2(9) ?
O6' C17' H17C . . 111.1 ?
C18' C17' H17C . . 111.1 ?
O6' C17' H17D . . 111.1 ?
C18' C17' H17D . . 111.1 ?
H17C C17' H17D . . 109.1 ?
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 ?
C9 N1 C11 . . 111.99(19) ?
C9 N1 C8 . . 121.2(2) ?
C11 N1 C8 . . 121.5(2) ?
C10 N2 C11 . . 113.5(2) ?
C10 N2 C7 . . 124.6(3) ?
C11 N2 C7 . . 121.6(2) ?
C9 N3 C19 . . 122.0(2) ?
C9 N3 C15 . . 111.98(19) ?
C19 N3 C15 . . 118.26(19) ?
C10 N4 C15 . . 110.4(2) ?
C10 N4 C20 . . 118.8(2) ?
C15 N4 C20 . . 115.72(19) ?
C19 N5 C20 . . 108.5(2) ?
C19 N5 C21 . . 114.05(19) ?
C20 N5 C21 . . 112.94(19) ?
C12 O4 C13 . . 115.0(7) ?
C16 O6 C17 . . 118.2(7) ?
C12 O4' C13' . . 114.1(9) ?
C16 O6' C17' . . 121.3(7) ?
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
C1 C2 . 1.367(5) ?
C1 C6 . 1.410(5) ?
C1 C8 . 1.500(4) ?
C2 C3 . 1.406(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.354(8) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(8) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.385(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.514(5) ?
C7 N2 . 1.448(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N1 . 1.468(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O1 . 1.207(3) ?
C9 N1 . 1.369(3) ?
C9 N3 . 1.381(3) ?
C10 O2 . 1.212(3) ?
C10 N2 . 1.363(4) ?
C10 N4 . 1.382(4) ?
C11 N2 . 1.434(3) ?
C11 N1 . 1.439(3) ?
C11 C12 . 1.536(4) ?
C11 C15 . 1.571(4) ?
C12 O3 . 1.180(7) ?
C12 O3' . 1.189(9) ?
C12 O4 . 1.350(6) ?
C12 O4' . 1.352(7) ?
C13 O4 . 1.418(7) ?
C13 C14 . 1.463(12) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 N4 . 1.445(3) ?
C15 N3 . 1.452(3) ?
C15 C16 . 1.529(4) ?
C16 O5' . 1.170(9) ?
C16 O5 . 1.197(4) ?
C16 O6 . 1.243(6) ?
C16 O6' . 1.293(6) ?
C17 C18 . 1.455(17) ?
C17 O6 . 1.483(10) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 N3 . 1.449(3) ?
C19 N5 . 1.460(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 N4 . 1.447(3) ?
C20 N5 . 1.469(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 N5 . 1.498(3) ?
C21 C22 . 1.516(4) ?
C21 C24 . 1.530(4) ?
C21 C23 . 1.534(5) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
C13' O4' . 1.418(8) ?
C13' C14' . 1.465(14) ?
C13' H13C . 0.9700 ?
C13' H13D . 0.9700 ?
C14' H14D . 0.9600 ?
C14' H14E . 0.9600 ?
C14' H14F . 0.9600 ?
C17' O6' . 1.450(10) ?
C17' C18' . 1.497(17) ?
C17' H17C . 0.9700 ?
C17' H17D . 0.9700 ?
C18' H18D . 0.9600 ?
C18' H18E . 0.9600 ?
C18' H18F . 0.9600 ?
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
C22 H22C O5 2_667 0.96 2.52 3.474(5) 174.3
C13 H13A O1 2_656 0.97 2.54 3.288(11) 133.5
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.1(4) ?
C8 C1 C2 C3 . . . . 178.2(3) ?
C1 C2 C3 C4 . . . . -0.4(6) ?
C2 C3 C4 C5 . . . . 0.5(7) ?
C3 C4 C5 C6 . . . . 0.0(6) ?
C4 C5 C6 C1 . . . . -0.5(5) ?
C4 C5 C6 C7 . . . . -176.6(3) ?
C2 C1 C6 C5 . . . . 0.5(4) ?
C8 C1 C6 C5 . . . . -177.6(3) ?
C2 C1 C6 C7 . . . . 176.5(3) ?
C8 C1 C6 C7 . . . . -1.7(4) ?
C5 C6 C7 N2 . . . . -128.4(3) ?
C1 C6 C7 N2 . . . . 55.6(4) ?
C2 C1 C8 N1 . . . . 129.5(3) ?
C6 C1 C8 N1 . . . . -52.3(3) ?
N2 C11 C12 O3 . . . . -8.9(10) ?
N1 C11 C12 O3 . . . . -136.5(9) ?
C15 C11 C12 O3 . . . . 105.0(10) ?
N2 C11 C12 O3' . . . . -37.6(14) ?
N1 C11 C12 O3' . . . . -165.2(14) ?
C15 C11 C12 O3' . . . . 76.3(14) ?
N2 C11 C12 O4 . . . . 149.7(5) ?
N1 C11 C12 O4 . . . . 22.0(5) ?
C15 C11 C12 O4 . . . . -96.4(5) ?
N2 C11 C12 O4' . . . . 176.4(6) ?
N1 C11 C12 O4' . . . . 48.7(6) ?
C15 C11 C12 O4' . . . . -69.7(6) ?
N2 C11 C15 N4 . . . . 7.6(3) ?
N1 C11 C15 N4 . . . . 125.7(2) ?
C12 C11 C15 N4 . . . . -110.1(3) ?
N2 C11 C15 N3 . . . . -109.0(2) ?
N1 C11 C15 N3 . . . . 9.1(2) ?
C12 C11 C15 N3 . . . . 133.2(2) ?
N2 C11 C15 C16 . . . . 128.1(2) ?
N1 C11 C15 C16 . . . . -113.8(2) ?
C12 C11 C15 C16 . . . . 10.4(3) ?
N4 C15 C16 O5' . . . . 115.1(16) ?
N3 C15 C16 O5' . . . . -119.8(16) ?
C11 C15 C16 O5' . . . . -2.3(16) ?
N4 C15 C16 O5 . . . . 61.5(4) ?
N3 C15 C16 O5 . . . . -173.3(4) ?
C11 C15 C16 O5 . . . . -55.8(5) ?
N4 C15 C16 O6 . . . . -128.4(6) ?
N3 C15 C16 O6 . . . . -3.2(6) ?
C11 C15 C16 O6 . . . . 114.3(6) ?
N4 C15 C16 O6' . . . . -85.3(5) ?
N3 C15 C16 O6' . . . . 39.9(5) ?
C11 C15 C16 O6' . . . . 157.4(5) ?
O1 C9 N1 C11 . . . . -167.1(2) ?
N3 C9 N1 C11 . . . . 16.2(3) ?
O1 C9 N1 C8 . . . . -12.6(4) ?
N3 C9 N1 C8 . . . . 170.6(2) ?
N2 C11 N1 C9 . . . . 93.9(2) ?
C12 C11 N1 C9 . . . . -141.1(3) ?
C15 C11 N1 C9 . . . . -15.6(3) ?
N2 C11 N1 C8 . . . . -60.5(3) ?
C12 C11 N1 C8 . . . . 64.5(3) ?
C15 C11 N1 C8 . . . . -170.0(2) ?
C1 C8 N1 C9 . . . . -80.3(3) ?
C1 C8 N1 C11 . . . . 71.8(3) ?
O2 C10 N2 C11 . . . . 174.7(3) ?
N4 C10 N2 C11 . . . . -7.6(3) ?
O2 C10 N2 C7 . . . . 1.4(5) ?
N4 C10 N2 C7 . . . . 179.1(3) ?
N1 C11 N2 C10 . . . . -110.4(3) ?
C12 C11 N2 C10 . . . . 122.1(3) ?
C15 C11 N2 C10 . . . . -0.3(3) ?
N1 C11 N2 C7 . . . . 63.1(3) ?
C12 C11 N2 C7 . . . . -64.4(4) ?
C15 C11 N2 C7 . . . . 173.2(3) ?
C6 C7 N2 C10 . . . . 97.0(4) ?
C6 C7 N2 C11 . . . . -75.7(4) ?
O1 C9 N3 C19 . . . . 25.1(4) ?
N1 C9 N3 C19 . . . . -158.1(2) ?
O1 C9 N3 C15 . . . . 173.8(2) ?
N1 C9 N3 C15 . . . . -9.4(3) ?
N5 C19 N3 C9 . . . . 98.0(2) ?
N5 C19 N3 C15 . . . . -48.9(3) ?
N4 C15 N3 C9 . . . . -111.2(2) ?
C16 C15 N3 C9 . . . . 124.6(2) ?
C11 C15 N3 C9 . . . . -0.3(3) ?
N4 C15 N3 C19 . . . . 38.8(3) ?
C16 C15 N3 C19 . . . . -85.3(3) ?
C11 C15 N3 C19 . . . . 149.8(2) ?
O2 C10 N4 C15 . . . . -169.4(3) ?
N2 C10 N4 C15 . . . . 12.9(3) ?
O2 C10 N4 C20 . . . . -32.3(4) ?
N2 C10 N4 C20 . . . . 150.0(2) ?
N3 C15 N4 C10 . . . . 97.5(2) ?
C16 C15 N4 C10 . . . . -136.9(2) ?
C11 C15 N4 C10 . . . . -12.6(3) ?
N3 C15 N4 C20 . . . . -41.0(3) ?
C16 C15 N4 C20 . . . . 84.6(3) ?
C11 C15 N4 C20 . . . . -151.1(2) ?
N5 C20 N4 C10 . . . . -80.5(3) ?
N5 C20 N4 C15 . . . . 54.3(3) ?
N3 C19 N5 C20 . . . . 58.7(3) ?
N3 C19 N5 C21 . . . . -174.4(2) ?
N4 C20 N5 C19 . . . . -62.2(3) ?
N4 C20 N5 C21 . . . . 170.3(2) ?
C22 C21 N5 C19 . . . . 168.0(3) ?
C24 C21 N5 C19 . . . . 51.7(3) ?
C23 C21 N5 C19 . . . . -70.7(3) ?
C22 C21 N5 C20 . . . . -67.4(3) ?
C24 C21 N5 C20 . . . . 176.2(2) ?
C23 C21 N5 C20 . . . . 53.8(3) ?
O3 C12 O4 C13 . . . . -19.6(14) ?
O3' C12 O4 C13 . . . . 9.9(17) ?
O4' C12 O4 C13 . . . . 83.1(19) ?
C11 C12 O4 C13 . . . . -177.3(7) ?
C14 C13 O4 C12 . . . . -79.4(12) ?
O5' C16 O6 C17 . . . . -38.6(14) ?
O5 C16 O6 C17 . . . . -3.6(13) ?
O6' C16 O6 C17 . . . . 85.1(10) ?
C15 C16 O6 C17 . . . . -173.0(8) ?
C18 C17 O6 C16 . . . . -101.4(14) ?
O3 C12 O4' C13' . . . . 0.4(17) ?
O3' C12 O4' C13' . . . . 24.9(17) ?
O4 C12 O4' C13' . . . . -95(2) ?
C11 C12 O4' C13' . . . . 174.9(10) ?
C14' C13' O4' C12 . . . . 74.8(19) ?
O5' C16 O6' C17' . . . . -19.1(18) ?
O5 C16 O6' C17' . . . . 30.7(11) ?
O6 C16 O6' C17' . . . . -85.5(10) ?
C15 C16 O6' C17' . . . . 178.8(8) ?
C18' C17' O6' C16 . . . . -179.2(9) ?
