#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/50/2205037.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_2205037
loop_
_publ_author_name
'Fernández, Daniel'
'Vega, Daniel'
'Ellena, Javier A.'
_publ_section_title
;
 Candesartan cilexetil, an antihypertensive agent containing an
 extended double ester chain
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o309
_journal_page_last               o312
_journal_paper_doi               10.1107/S1600536805000097
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C33 H34 N6 O6'
_chemical_formula_moiety         'C33 H34 N6 O6'
_chemical_formula_sum            'C33 H34 N6 O6'
_chemical_formula_weight         610.66
_chemical_name_systematic
;
(+-)-1-[(cyclohexyloxy)carbonyloxy]ethyl
2-ethoxy-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-
7-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   constr
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 104.102(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.3545(4)
_cell_length_b                   10.8868(3)
_cell_length_c                   18.4635(5)
_cell_measurement_reflns_used    10007
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1.0
_cell_volume                     3188.32(15)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ZORTEP (Zsolnai & Pritzkow, 1995) and GRETEP (Laugier & Bochu, 2004)
;
_computing_publication_material
;
PLATON (Spek, 2003) and WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ scans with κ at 0°, and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10191
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.332
_refine_ls_extinction_coef       0.030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5575
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0877
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.01767P)²+1.1617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2531
_refine_ls_wR_factor_ref         0.2917
_reflns_number_gt                3772
_reflns_number_total             5575
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6437.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205037
_cod_database_fobs_code          2205037
loop_
_symmetry_equiv_pos_as_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_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
N1 0.0100(2) -0.1337(3) 0.31614(17) 0.0801(8) Uani d . 1 N
N2 0.0473(2) -0.1589(3) 0.38853(17) 0.0904(9) Uani d . 1 N
N3 0.0936(2) -0.2567(3) 0.39389(16) 0.0819(8) Uani d . 1 N
N4 0.08563(18) -0.2963(3) 0.32338(14) 0.0683(6) Uani d . 1 N
H4 0.1094 -0.3605 0.3106 0.102 Uiso calc R 1 H
N5 0.25720(16) 0.3236(2) 0.30014(15) 0.0666(6) Uani d . 1 N
N6 0.18918(17) 0.4970(3) 0.31724(15) 0.0689(7) Uani d . 1 N
O1 0.20737(15) 0.4449(2) 0.19794(13) 0.0732(6) Uani d . 1 O
O2 0.39722(19) 0.1300(3) 0.40182(18) 0.1052(9) Uani d . 1 O
O3 0.3194(2) 0.0446(3) 0.4735(2) 0.1201(11) Uani d D 1 O
O4 0.3784(3) -0.0886(4) 0.5681(2) 0.1517(14) Uani d D 1 O
O5 0.4529(3) 0.0857(4) 0.6080(3) 0.1549(15) Uani d . 1 O
O6 0.4206(3) -0.0626(4) 0.6866(3) 0.1622(16) Uani d D 1 O
C1 0.0350(2) -0.2202(3) 0.27666(18) 0.0636(7) Uani d . 1 C
C2 0.00973(19) -0.2339(3) 0.19436(17) 0.0606(7) Uani d . 1 C
C3 -0.0470(2) -0.3263(3) 0.16427(19) 0.0704(8) Uani d . 1 C
H5 -0.0676 -0.3778 0.1959 0.084 Uiso calc R 1 H
C4 -0.0730(2) -0.3426(3) 0.0882(2) 0.0761(9) Uani d . 1 C
H6 -0.1108 -0.4048 0.0685 0.091 Uiso calc R 1 H
C5 -0.0427(2) -0.2660(4) 0.0414(2) 0.0811(10) Uani d . 1 C
H7 -0.0601 -0.2766 -0.0100 0.097 Uiso calc R 1 H
C6 0.0133(2) -0.1739(3) 0.07056(19) 0.0747(9) Uani d . 1 C
H8 0.0332 -0.1227 0.0383 0.090 Uiso calc R 1 H
C7 0.0409(2) -0.1555(3) 0.14714(17) 0.0613(7) Uani d . 1 C
C8 0.10352(19) -0.0573(3) 0.17634(17) 0.0618(7) Uani d . 1 C
C9 0.1768(2) -0.0805(3) 0.2308(2) 0.0743(9) Uani d . 1 C
H9 0.1869 -0.1590 0.2508 0.089 Uiso calc R 1 H
C10 0.2351(2) 0.0120(3) 0.2558(2) 0.0740(9) Uani d . 1 C
H10 0.2840 -0.0059 0.2921 0.089 Uiso calc R 1 H
C11 0.22234(19) 0.1297(3) 0.22805(18) 0.0630(7) Uani d . 1 C
C12 0.1483(2) 0.1532(3) 0.17386(17) 0.0648(7) Uani d . 1 C
H11 0.1380 0.2321 0.1545 0.078 Uiso calc R 1 H
C13 0.0902(2) 0.0622(3) 0.14857(18) 0.0648(8) Uani d . 1 C
H12 0.0413 0.0805 0.1124 0.078 Uiso calc R 1 H
C14 0.2862(2) 0.2290(3) 0.2555(2) 0.0679(8) Uani d . 1 C
H13 0.3372 0.1918 0.2855 0.081 Uiso calc R 1 H
H14 0.3002 0.2679 0.2128 0.081 Uiso calc R 1 H
C15 0.2150(2) 0.4265(3) 0.26992(18) 0.0637(7) Uani d . 1 C
C16 0.2157(2) 0.4352(3) 0.38498(19) 0.0705(8) Uani d . 1 C
C17 0.2046(3) 0.4695(4) 0.4542(2) 0.0858(10) Uani d . 1 C
H15 0.1776 0.5425 0.4603 0.103 Uiso calc R 1 H
C18 0.2349(3) 0.3921(5) 0.5136(2) 0.0976(12) Uani d . 1 C
H16 0.2284 0.4134 0.5607 0.117 Uiso calc R 1 H
C19 0.2751(2) 0.2822(4) 0.5044(2) 0.0909(11) Uani d . 1 C
H17 0.2933 0.2303 0.5451 0.109 Uiso calc R 1 H
C20 0.2884(2) 0.2490(4) 0.4361(2) 0.0775(9) Uani d . 1 C
C21 0.2579(2) 0.3259(3) 0.37580(18) 0.0672(8) Uani d . 1 C
C22 0.1638(3) 0.5546(3) 0.1650(2) 0.0785(9) Uani d . 1 C
H18 0.1943 0.6271 0.1872 0.094 Uiso calc R 1 H
H19 0.1077 0.5573 0.1736 0.094 Uiso calc R 1 H
C23 0.1588(4) 0.5513(5) 0.0852(3) 0.1219(18) Uani d . 1 C
H1 0.1346 0.6266 0.0627 0.183 Uiso calc R 1 H
H2 0.1240 0.4835 0.0630 0.183 Uiso calc R 1 H
H3 0.2143 0.5415 0.0774 0.183 Uiso calc R 1 H
C24 0.3405(2) 0.1371(4) 0.4339(2) 0.0891(11) Uani d . 1 C
C25 0.3806(7) -0.0521(8) 0.4924(5) 0.147(5) Uani d PD 0.75 C
H20 0.4366 -0.0335 0.4848 0.177 Uiso calc PR 0.75 H
C251 0.3734(14) -0.071(2) 0.4842(9) 0.149(18) Uani d PD 0.25 C
H201 0.4264 -0.0250 0.4935 0.179 Uiso calc PR 0.25 H
C26 0.3372(7) -0.1678(7) 0.4518(7) 0.182(4) Uani d PD 0.75 C
H21 0.3723 -0.2033 0.4225 0.272 Uiso calc PR 0.75 H
H22 0.2838 -0.1454 0.4197 0.272 Uiso calc PR 0.75 H
H23 0.3285 -0.2266 0.4880 0.272 Uiso calc PR 0.75 H
C261 0.3809(11) -0.1161(15) 0.4058(12) 0.187(17) Uani d PD 0.25 C
H211 0.4092 -0.1940 0.4107 0.280 Uiso calc PR 0.25 H
H221 0.4126 -0.0573 0.3850 0.280 Uiso calc PR 0.25 H
H231 0.3256 -0.1246 0.3733 0.280 Uiso calc PR 0.25 H
C27 0.4186(4) -0.0130(6) 0.6211(4) 0.144(2) Uani d . 1 C
C28 0.4578(4) 0.0093(10) 0.7539(3) 0.184(3) Uani d D 1 C
H24 0.4360 0.0935 0.7478 0.221 Uiso calc R 1 H
C29 0.5535(4) 0.0113(12) 0.7711(6) 0.266(6) Uani d D 1 C
H25 0.5760 -0.0715 0.7771 0.319 Uiso calc R 1 H
H26 0.5726 0.0516 0.7314 0.319 Uiso calc R 1 H
C30 0.5802(7) 0.0814(10) 0.8422(5) 0.222(4) Uani d D 1 C
H27 0.5534 0.1616 0.8362 0.267 Uiso calc R 1 H
H28 0.6408 0.0937 0.8540 0.267 Uiso calc R 1 H
C31 0.5564(4) 0.0134(11) 0.9058(5) 0.230(5) Uani d D 1 C
H29 0.5793 0.0549 0.9528 0.277 Uiso calc R 1 H
H30 0.5781 -0.0699 0.9094 0.277 Uiso calc R 1 H
C32 0.4600(5) 0.0123(13) 0.8880(4) 0.272(7) Uani d D 1 C
H31 0.4414 -0.0269 0.9283 0.326 Uiso calc R 1 H
H32 0.4389 0.0960 0.8831 0.326 Uiso calc R 1 H
C33 0.4259(4) -0.0564(10) 0.8162(4) 0.201(4) Uani d D 1 C
H33 0.3647 -0.0566 0.8041 0.242 Uiso calc R 1 H
H34 0.4454 -0.1408 0.8211 0.242 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
C1 N1 N2 106.0(3) ?
N3 N2 N1 110.9(3) ?
N2 N3 N4 105.8(3) ?
C1 N4 N3 109.0(2) ?
C1 N4 H4 125.5 ?
N3 N4 H4 125.5 ?
C15 N5 C21 105.97(19) ?
C15 N5 C14 123.2(2) ?
C21 N5 C14 130.5(2) ?
C15 N6 C16 103.7(2) ?
C15 O1 C22 117.7(2) ?
C24 O3 C25 115.3(4) ?
C24 O3 C251 118.4(9) ?
C27 O4 C25 114.4(5) ?
C27 O4 C251 124.1(10) ?
C27 O6 C28 118.0(4) ?
N1 C1 N4 108.4(2) ?
N1 C1 C2 126.4(3) y
N4 C1 C2 125.2(2) ?
C3 C2 C7 120.1(3) ?
C3 C2 C1 118.4(3) ?
C7 C2 C1 121.6(3) ?
C4 C3 C2 120.7(3) ?
C4 C3 H5 119.6 ?
C2 C3 H5 119.6 ?
C3 C4 C5 119.6(3) ?
C3 C4 H6 120.2 ?
C5 C4 H6 120.2 ?
C6 C5 C4 120.2(3) ?
C6 C5 H7 119.9 ?
C4 C5 H7 119.9 ?
C5 C6 C7 121.5(3) ?
C5 C6 H8 119.2 ?
C7 C6 H8 119.2 ?
C6 C7 C2 117.9(3) ?
C6 C7 C8 119.7(3) ?
C2 C7 C8 122.3(3) y
C9 C8 C13 117.7(3) ?
C9 C8 C7 122.0(3) ?
C13 C8 C7 120.3(3) ?
C10 C9 C8 120.8(3) ?
C10 C9 H9 119.6 ?
C8 C9 H9 119.6 ?
C11 C10 C9 121.5(3) ?
C11 C10 H10 119.3 ?
C9 C10 H10 119.3 ?
C10 C11 C12 117.7(3) ?
C10 C11 C14 120.9(3) ?
C12 C11 C14 121.4(3) ?
C13 C12 C11 121.3(3) ?
C13 C12 H11 119.3 ?
C11 C12 H11 119.3 ?
C12 C13 C8 121.0(3) ?
C12 C13 H12 119.5 ?
C8 C13 H12 119.5 ?
N5 C14 C11 113.7(2) y
N5 C14 H13 108.8 ?
C11 C14 H13 108.8 ?
N5 C14 H14 108.8 ?
C11 C14 H14 108.8 ?
H13 C14 H14 107.7 ?
N6 C15 O1 128.1(3) ?
N6 C15 N5 115.0(2) ?
O1 C15 N5 116.8(2) ?
C17 C16 N6 128.1(3) ?
C17 C16 C21 121.2(3) ?
N6 C16 C21 110.8(3) ?
C18 C17 C16 117.9(4) ?
C18 C17 H15 121.0 ?
C16 C17 H15 121.0 ?
C17 C18 C19 121.1(4) ?
C17 C18 H16 119.5 ?
C19 C18 H16 119.5 ?
C20 C19 C18 121.4(4) ?
C20 C19 H17 119.3 ?
C18 C19 H17 119.3 ?
C19 C20 C21 118.0(4) ?
C19 C20 C24 117.3(4) ?
C21 C20 C24 124.6(4) ?
C20 C21 N5 135.0(3) ?
C20 C21 C16 120.4(3) ?
N5 C21 C16 104.6(3) ?
O1 C22 C23 107.8(3) ?
O1 C22 H18 110.1 ?
C23 C22 H18 110.1 ?
O1 C22 H19 110.1 ?
C23 C22 H19 110.1 ?
H18 C22 H19 108.5 ?
C22 C23 H1 109.5 ?
C22 C23 H2 109.5 ?
H1 C23 H2 109.5 ?
C22 C23 H3 109.5 ?
H1 C23 H3 109.5 ?
H2 C23 H3 109.5 ?
O2 C24 O3 123.1(3) ?
O2 C24 C20 124.9(3) ?
O3 C24 C20 112.0(3) ?
O3 C25 O4 104.7(7) ?
O3 C25 C26 105.6(8) ?
O4 C25 C26 97.3(7) ?
O3 C25 H20 115.7 ?
O4 C25 H20 115.7 ?
C26 C25 H20 115.7 ?
O3 C251 O4 96.9(13) ?
O3 C251 C261 108.3(12) ?
O4 C251 C261 154(2) ?
O3 C251 H201 93.3 ?
O4 C251 H201 93.3 ?
C261 C251 H201 93.3 ?
C25 C26 H21 109.5 ?
C25 C26 H22 109.5 ?
H21 C26 H22 109.5 ?
C25 C26 H23 109.5 ?
H21 C26 H23 109.5 ?
H22 C26 H23 109.5 ?
C251 C261 H211 109.5 ?
C251 C261 H221 109.5 ?
H211 C261 H221 109.5 ?
C251 C261 H231 109.5 ?
H211 C261 H231 109.5 ?
H221 C261 H231 109.5 ?
O5 C27 O6 127.7(6) ?
O5 C27 O4 123.5(5) ?
O6 C27 O4 108.7(5) ?
O6 C28 C29 112.2(6) ?
O6 C28 C33 103.7(7) ?
C29 C28 C33 111.6(7) ?
O6 C28 H24 109.8 ?
C29 C28 H24 109.8 ?
C33 C28 H24 109.8 ?
C30 C29 C28 104.9(6) ?
C30 C29 H25 110.8 ?
C28 C29 H25 110.8 ?
C30 C29 H26 110.8 ?
C28 C29 H26 110.8 ?
H25 C29 H26 108.8 ?
C29 C30 C31 110.9(8) ?
C29 C30 H27 109.5 ?
C31 C30 H27 109.5 ?
C29 C30 H28 109.5 ?
C31 C30 H28 109.5 ?
H27 C30 H28 108.1 ?
C30 C31 C32 106.4(7) ?
C30 C31 H29 110.5 ?
C32 C31 H29 110.5 ?
C30 C31 H30 110.5 ?
C32 C31 H30 110.5 ?
H29 C31 H30 108.6 ?
C33 C32 C31 109.6(6) ?
C33 C32 H31 109.8 ?
C31 C32 H31 109.8 ?
C33 C32 H32 109.8 ?
C31 C32 H32 109.8 ?
H31 C32 H32 108.2 ?
C32 C33 C28 107.7(8) ?
C32 C33 H33 110.2 ?
C28 C33 H33 110.2 ?
C32 C33 H34 110.2 ?
C28 C33 H34 110.2 ?
H33 C33 H34 108.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.316(3) ?
N1 N2 1.355(4) ?
N2 N3 1.296(4) ?
N3 N4 1.348(4) ?
N4 C1 1.330(3) ?
N4 H4 0.8600 ?
N5 C15 1.362(3) ?
N5 C21 1.395(3) ?
N5 C14 1.468(3) y
N6 C15 1.308(3) ?
N6 C16 1.393(3) ?
O1 C15 1.320(3) ?
O1 C22 1.447(3) ?
O2 C24 1.219(4) ?
O3 C24 1.338(4) ?
O3 C25 1.435(9) ?
O3 C251 1.52(2) ?
O4 C27 1.324(7) ?
O4 C25 1.462(9) ?
O4 C251 1.542(18) ?
O5 C27 1.263(7) ?
O6 C27 1.318(6) ?
O6 C28 1.470(8) ?
C1 C2 1.482(4) y
C2 C3 1.389(4) ?
C2 C7 1.402(4) ?
C3 C4 1.376(5) ?
C3 H5 0.9300 ?
C4 C5 1.377(5) ?
C4 H6 0.9300 ?
C5 C6 1.376(5) ?
C5 H7 0.9300 ?
C6 C7 1.390(4) ?
C6 H8 0.9300 ?
C7 C8 1.487(4) y
C8 C9 1.387(5) ?
C8 C13 1.397(4) ?
C9 C10 1.386(5) ?
C9 H9 0.9300 ?
C10 C11 1.377(5) ?
C10 H10 0.9300 ?
C11 C12 1.394(5) ?
C11 C14 1.503(5) y
C12 C13 1.372(4) ?
C12 H11 0.9300 ?
C13 H12 0.9300 ?
C14 H13 0.9700 ?
C14 H14 0.9700 ?
C16 C17 1.385(5) ?
C16 C21 1.406(5) ?
C17 C18 1.376(6) ?
C17 H15 0.9300 ?
C18 C19 1.395(6) ?
C18 H16 0.9300 ?
C19 C20 1.379(5) ?
C19 H17 0.9300 ?
C20 C21 1.386(5) ?
C20 C24 1.493(6) ?
C22 C23 1.455(6) ?
C22 H18 0.9700 ?
C22 H19 0.9700 ?
C23 H1 0.9600 ?
C23 H2 0.9600 ?
C23 H3 0.9600 ?
C25 C26 1.547(12) ?
C25 H20 0.9800 ?
C251 C261 1.562(10) ?
C251 H201 0.9800 ?
C26 H21 0.9600 ?
C26 H22 0.9600 ?
C26 H23 0.9600 ?
C261 H211 0.9600 ?
C261 H221 0.9600 ?
C261 H231 0.9600 ?
C28 C29 1.519(5) ?
C28 C33 1.549(10) ?
C28 H24 0.9800 ?
C29 C30 1.489(11) ?
C29 H25 0.9700 ?
C29 H26 0.9700 ?
C30 C31 1.518(8) ?
C30 H27 0.9700 ?
C30 H28 0.9700 ?
C31 C32 1.530(11) ?
C31 H29 0.9700 ?
C31 H30 0.9700 ?
C32 C33 1.505(12) ?
C32 H31 0.9700 ?
C32 H32 0.9700 ?
C33 H33 0.9700 ?
C33 H34 0.9700 ?
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
N4 H4 N6 1_545 0.86 2.01 2.835(4) 160
C14 H13 O2 . 0.97 2.24 3.061(4) 142
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
C1 N1 N2 N3 0.0(4) ?
N1 N2 N3 N4 -0.5(4) ?
N2 N3 N4 C1 0.7(3) ?
N2 N1 C1 N4 0.4(3) ?
N2 N1 C1 C2 178.7(3) ?
N3 N4 C1 N1 -0.7(3) ?
N3 N4 C1 C2 -179.0(2) ?
N1 C1 C2 C3 -105.5(3) ?
N4 C1 C2 C3 72.4(4) ?
N1 C1 C2 C7 73.7(4) y
N4 C1 C2 C7 -108.3(3) ?
C7 C2 C3 C4 0.3(5) ?
C1 C2 C3 C4 179.6(3) ?
C2 C3 C4 C5 -0.2(5) ?
C3 C4 C5 C6 0.0(6) ?
C4 C5 C6 C7 0.1(6) ?
C5 C6 C7 C2 -0.1(5) ?
C5 C6 C7 C8 178.0(3) ?
C3 C2 C7 C6 -0.1(5) ?
C1 C2 C7 C6 -179.4(3) ?
C3 C2 C7 C8 -178.2(3) ?
C1 C2 C7 C8 2.5(4) ?
C6 C7 C8 C9 -128.4(4) ?
C2 C7 C8 C9 49.6(4) y
C6 C7 C8 C13 51.0(4) ?
C2 C7 C8 C13 -131.0(3) ?
C13 C8 C9 C10 -0.9(5) ?
C7 C8 C9 C10 178.5(3) ?
C8 C9 C10 C11 0.5(6) ?
C9 C10 C11 C12 0.2(5) ?
C9 C10 C11 C14 -179.9(3) ?
C10 C11 C12 C13 -0.4(5) ?
C14 C11 C12 C13 179.7(3) ?
C11 C12 C13 C8 0.0(5) ?
C9 C8 C13 C12 0.7(5) ?
C7 C8 C13 C12 -178.7(3) ?
C15 N5 C14 C11 -89.4(3) ?
C21 N5 C14 C11 83.8(3) y
C10 C11 C14 N5 -110.8(3) ?
C12 C11 C14 N5 69.2(4) ?
C16 N6 C15 O1 -178.4(3) ?
C16 N6 C15 N5 -0.6(3) ?
C22 O1 C15 N6 -1.4(4) ?
C22 O1 C15 N5 -179.1(2) ?
C21 N5 C15 N6 1.1(3) ?
C14 N5 C15 N6 175.8(2) ?
C21 N5 C15 O1 179.1(2) ?
C14 N5 C15 O1 -6.2(3) ?
C15 N6 C16 C17 -179.9(4) ?
C15 N6 C16 C21 -0.1(3) ?
N6 C16 C17 C18 178.7(3) ?
C21 C16 C17 C18 -1.2(5) ?
C16 C17 C18 C19 -0.3(6) ?
C17 C18 C19 C20 2.1(6) ?
C18 C19 C20 C21 -2.3(6) ?
C18 C19 C20 C24 173.2(4) ?
C19 C20 C21 N5 -178.6(3) ?
C24 C20 C21 N5 6.2(6) ?
C19 C20 C21 C16 0.8(5) ?
C24 C20 C21 C16 -174.3(3) ?
C15 N5 C21 C20 178.5(4) ?
C14 N5 C21 C20 4.4(5) ?
C15 N5 C21 C16 -1.0(3) ?
C14 N5 C21 C16 -175.1(2) ?
C17 C16 C21 C20 0.9(5) ?
N6 C16 C21 C20 -178.9(3) ?
C17 C16 C21 N5 -179.5(3) ?
N6 C16 C21 N5 0.7(3) ?
C15 O1 C22 C23 -176.6(3) y
C25 O3 C24 O2 15.5(5) ?
C251 O3 C24 O2 5.1(8) ?
C25 O3 C24 C20 -162.7(5) ?
C251 O3 C24 C20 -173.1(8) ?
C19 C20 C24 O2 -134.1(4) ?
C21 C20 C24 O2 41.0(5) ?
C19 C20 C24 O3 44.1(4) ?
C21 C20 C24 O3 -140.8(3) ?
C24 O3 C25 O4 141.9(4) y
C24 O3 C25 C26 -116.0(7) ?
C27 O4 C25 O3 -77.5(7) ?
C27 O4 C25 C26 174.2(6) ?
C27 O4 C251 O3 -67.2(13) ?
C27 O4 C251 C261 131(4) ?
C28 O6 C27 O5 8.1(8) ?
O4 C27 O6 C28 -176.2(3) y
C25 O4 C27 O5 3.1(8) ?
C251 O4 C27 O5 4.4(13) ?
C25 O4 C27 O6 -172.8(5) ?
C251 O4 C27 O6 -171.5(11) ?
C27 O6 C28 C29 -76.0(8) ?
C27 O6 C28 C33 163.5(4) ?
O6 C28 C29 C30 -177.1(8) ?
C33 C28 C29 C30 -61.2(12) ?
C28 C29 C30 C31 64.9(12) ?
C29 C30 C31 C32 -66.3(11) ?
C30 C31 C32 C33 62.1(12) ?
C31 C32 C33 C28 -59.1(11) ?
O6 C28 C33 C32 -179.2(6) ?
C29 C28 C33 C32 59.8(10) ?
