#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/88/2228830.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_2228830
loop_
_publ_author_name
'Kettmann, Viktor'
'Světlík, Jan'
_publ_section_title
;
 Methyl
 5'-(2-hydroxyphenyl)-4',5',6',7'-tetrahydrospiro[2H-1-benzopyran-2,7'-1,2,4-triazolo[1,5-a]pyrimidine]-3-carboxylate
;
_journal_coeditor_code           NK2069
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o92
_journal_paper_doi               10.1107/S160053681005052X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H18 N4 O4'
_chemical_formula_moiety         'C21 H18 N4 O4'
_chemical_formula_sum            'C21 H18 N4 O4'
_chemical_formula_weight         390.39
_chemical_melting_point          511
_chemical_name_systematic
;
Methyl
5'-(2-hydroxyphenyl)-4',5',6',7'-tetrahydrospiro[2H-1-benzopyran-2,7'-
1,2,4-triazolo[1,5-a]pyrimidine]-3-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.337(6)
_cell_length_b                   14.824(5)
_cell_length_c                   13.932(5)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      7
_cell_volume                     3955(2)
_computing_cell_refinement       'XSCANS (Siemens, 1994)'
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'XSCANS (Siemens, 1994)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω/2θ
_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  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            12311
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         1.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         10237
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0530
_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)+(0.0583P)²+0.3383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                5854
_reflns_number_total             10237
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nk2069.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228830
_cod_database_fobs_code          2228830
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_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
N N1 0.89134(6) 0.49569(8) 0.23684(9) 0.0380(3) Uani d . 1 . .
N N2 0.87417(6) 0.41939(8) 0.28645(9) 0.0413(3) Uani d . 1 . .
C C1 0.81119(8) 0.43874(10) 0.30354(11) 0.0423(4) Uani d . 1 . .
H H1 0.7857 0.3993 0.3369 0.051 Uiso calc R 1 . .
N N3 0.78455(6) 0.52028(8) 0.26983(10) 0.0413(3) Uani d . 1 . .
C C2 0.83683(7) 0.55417(10) 0.22834(10) 0.0362(3) Uani d . 1 . .
N N4 0.84032(6) 0.63458(8) 0.18381(10) 0.0430(3) Uani d . 1 . .
H H4 0.8037 0.6669 0.1671 0.052 Uiso calc R 1 . .
C C3 0.90931(8) 0.66378(10) 0.16555(11) 0.0394(3) Uani d . 1 . .
H H3 0.9373 0.6789 0.2275 0.047 Uiso calc R 1 . .
C C4 0.94364(8) 0.58371(10) 0.12003(11) 0.0403(3) Uani d . 1 . .
H H4A 0.9154 0.5672 0.0596 0.048 Uiso calc R 1 . .
H H4B 0.9892 0.6018 0.1054 0.048 Uiso calc R 1 . .
C C5 0.95183(8) 0.50135(10) 0.18751(11) 0.0402(3) Uani d . 1 . .
O O1 1.00884(5) 0.51615(8) 0.26455(8) 0.0508(3) Uani d D 1 . .
C C6 1.07550(9) 0.49704(15) 0.24576(13) 0.0616(5) Uani d D 1 . .
C C7 1.12993(10) 0.5448(2) 0.29503(16) 0.0905(8) Uani d D 1 . .
H H7 1.1217 0.5906 0.3378 0.109 Uiso calc R 1 . .
C C8 1.19812(12) 0.5235(3) 0.27976(19) 0.1107(10) Uani d D 1 . .
H H8 1.2356 0.5557 0.3121 0.133 Uiso calc R 1 . .
C C9 1.20987(12) 0.4559(3) 0.2179(2) 0.1105(10) Uani d D 1 . .
H H9 1.2555 0.4421 0.2091 0.133 Uiso calc R 1 . .
C C10 1.15617(11) 0.4082(2) 0.16873(17) 0.0901(8) Uani d D 1 . .
H H10 1.1654 0.3626 0.1265 0.108 Uiso calc R 1 . .
C C11 1.08687(10) 0.42749(15) 0.18141(14) 0.0654(5) Uani d D 1 . .
C C12 1.02669(10) 0.38182(13) 0.13138(13) 0.0586(5) Uani d D 1 . .
H H12 1.0326 0.3292 0.0971 0.070 Uiso calc R 1 . .
C C13 0.96249(9) 0.41406(11) 0.13359(12) 0.0492(4) Uani d D 1 . .
C C14 0.89967(11) 0.37507(14) 0.07541(14) 0.0644(5) Uani d D 1 . .
O O2 0.84434(8) 0.41265(11) 0.05622(11) 0.0803(4) Uani d D 1 . .
O O3 0.91120(9) 0.28860(11) 0.04917(13) 0.0974(5) Uani d D 1 . .
C C15 0.85174(15) 0.2483(2) -0.0140(2) 0.1287(12) Uani d D 1 . .
H H15A 0.8114 0.2478 0.0193 0.193 Uiso calc R 1 . .
H H15B 0.8632 0.1876 -0.0300 0.193 Uiso calc R 1 . .
H H15C 0.8419 0.2832 -0.0723 0.193 Uiso calc R 1 . .
C C16 0.90575(8) 0.74627(10) 0.09945(11) 0.0411(4) Uani d . 1 . .
C C17 0.96473(9) 0.80048(10) 0.10207(12) 0.0447(4) Uani d . 1 . .
C C18 0.96418(10) 0.87454(12) 0.04036(13) 0.0570(5) Uani d . 1 . .
H H18 1.0034 0.9113 0.0431 0.068 Uiso calc R 1 . .
C C19 0.90558(11) 0.89336(13) -0.02473(14) 0.0644(5) Uani d . 1 . .
H H19 0.9059 0.9420 -0.0668 0.077 Uiso calc R 1 . .
C C20 0.84611(10) 0.84041(13) -0.02812(14) 0.0625(5) Uani d . 1 . .
H H20 0.8065 0.8536 -0.0716 0.075 Uiso calc R 1 . .
C C21 0.84671(9) 0.76719(12) 0.03459(13) 0.0533(4) Uani d . 1 . .
H H21 0.8069 0.7317 0.0331 0.064 Uiso calc R 1 . .
O O4 1.02225(6) 0.77752(8) 0.16686(9) 0.0573(3) Uani d . 1 . .
H H4C 1.0519 0.8172 0.1678 0.086 Uiso calc R 1 . .
N N5 0.60625(7) 0.76363(8) 0.24160(10) 0.0455(3) Uani d . 1 A .
N N6 0.61876(7) 0.83878(9) 0.18647(11) 0.0535(4) Uani d . 1 . .
C C22 0.67762(9) 0.81715(12) 0.15613(14) 0.0556(5) Uani d . 1 . .
H H22 0.6994 0.8551 0.1164 0.067 Uiso calc R 1 . .
N N7 0.70520(7) 0.73559(9) 0.18622(12) 0.0558(4) Uani d . 1 . .
C C23 0.65830(8) 0.70369(11) 0.23847(13) 0.0465(4) Uani d . 1 . .
N N8 0.65829(7) 0.62390(9) 0.28501(11) 0.0540(4) Uani d . 1 . .
H H8A 0.6955 0.5916 0.2964 0.065 Uiso calc R 1 . .
C C24 0.59260(8) 0.59469(10) 0.31523(12) 0.0430(4) Uani d . 1 . .
H H24 0.5601 0.5791 0.2573 0.052 Uiso calc R 1 . .
C C25 0.56262(9) 0.67436(10) 0.36544(13) 0.0490(4) Uani d . 1 A .
H H25A 0.5947 0.6914 0.4223 0.059 Uiso calc R 1 . .
H H25B 0.5188 0.6569 0.3865 0.059 Uiso calc R 1 . .
C C26 0.55051(10) 0.75491(12) 0.29647(15) 0.0603(5) Uani d . 1 . .
O O5 0.48981(18) 0.7585(2) 0.2439(3) 0.0514(8) Uani d PD 0.4752(18) A 1
C C27 0.4300(3) 0.7844(4) 0.2838(5) 0.0515(14) Uani d PD 0.4752(18) A 1
C C28 0.3677(2) 0.7475(4) 0.2439(4) 0.0598(12) Uani d PD 0.4752(18) A 1
H H28 0.3655 0.7049 0.1946 0.072 Uiso calc PR 0.4752(18) A 1
C C29 0.3078(6) 0.7763(12) 0.2797(15) 0.068(3) Uani d PD 0.4752(18) A 1
H H29 0.2648 0.7520 0.2542 0.081 Uiso calc PR 0.4752(18) A 1
C C30 0.31096(19) 0.8398(3) 0.3519(3) 0.0635(12) Uani d PD 0.4752(18) A 1
H H30 0.2703 0.8587 0.3746 0.076 Uiso calc PR 0.4752(18) A 1
C C31 0.37280(18) 0.8745(3) 0.3897(3) 0.0590(10) Uani d PD 0.4752(18) A 1
H H31 0.3743 0.9181 0.4379 0.071 Uiso calc PR 0.4752(18) A 1
C C32 0.4350(4) 0.8469(7) 0.3585(6) 0.0531(18) Uani d PD 0.4752(18) A 1
C C33 0.50333(18) 0.8820(3) 0.3960(3) 0.0523(9) Uani d PD 0.4752(18) A 1
H H33 0.5073 0.9313 0.4377 0.063 Uiso calc PR 0.4752(18) A 1
C C34 0.5608(2) 0.8434(3) 0.3703(4) 0.0513(10) Uani d PD 0.4752(18) A 1
C C35 0.6308(7) 0.8748(16) 0.409(3) 0.075(7) Uani d PD 0.4752(18) A 1
O O6 0.68391(16) 0.8315(2) 0.4169(2) 0.0679(8) Uani d PD 0.4752(18) A 1
O O7 0.63054(16) 0.9545(2) 0.4629(2) 0.0733(9) Uani d PD 0.4752(18) A 1
C C36 0.6950(2) 0.9830(4) 0.5187(4) 0.0913(17) Uani d PD 0.4752(18) A 1
H H36A 0.7315 0.9823 0.4785 0.137 Uiso calc PR 0.4752(18) A 1
H H36B 0.7068 0.9426 0.5724 0.137 Uiso calc PR 0.4752(18) A 1
H H36C 0.6897 1.0430 0.5425 0.137 Uiso calc PR 0.4752(18) A 1
O O5' 0.49251(17) 0.7216(2) 0.2109(3) 0.0570(8) Uani d PD 0.5248(18) A 2
C C27' 0.42271(17) 0.7236(2) 0.2215(3) 0.0531(9) Uani d PD 0.5248(18) A 2
C C28' 0.37876(18) 0.6636(3) 0.1708(3) 0.0663(10) Uani d PD 0.5248(18) A 2
H H28' 0.3957 0.6209 0.1312 0.080 Uiso calc PR 0.5248(18) A 2
C C29' 0.3080(2) 0.6672(3) 0.1793(3) 0.0753(12) Uani d PD 0.5248(18) A 2
H H29' 0.2775 0.6261 0.1454 0.090 Uiso calc PR 0.5248(18) A 2
C C30' 0.2826(2) 0.7305(3) 0.2368(4) 0.0707(12) Uani d PD 0.5248(18) A 2
H H30' 0.2354 0.7309 0.2435 0.085 Uiso calc PR 0.5248(18) A 2
C C31' 0.3258(5) 0.7922(11) 0.2837(14) 0.065(3) Uani d PD 0.5248(18) A 2
H H31' 0.3080 0.8367 0.3206 0.079 Uiso calc PR 0.5248(18) A 2
C C32' 0.3977(3) 0.7896(4) 0.2773(4) 0.0529(12) Uani d PD 0.5248(18) A 2
C C33' 0.4482(4) 0.8512(6) 0.3314(6) 0.0536(17) Uani d PD 0.5248(18) A 2
H H33' 0.4324 0.9002 0.3638 0.064 Uiso calc PR 0.5248(18) A 2
C C34' 0.5176(2) 0.8370(2) 0.3345(3) 0.0510(9) Uani d PD 0.5248(18) A 2
C C35' 0.5655(2) 0.8960(3) 0.3948(3) 0.0578(10) Uani d PD 0.5248(18) A 2
O O6' 0.55115(14) 0.96768(19) 0.4274(2) 0.0794(9) Uani d PD 0.5248(18) A 2
O O7' 0.6326(4) 0.8630(9) 0.4186(13) 0.056(2) Uani d PD 0.5248(18) A 2
C C36' 0.6826(2) 0.9153(3) 0.4829(4) 0.0819(13) Uani d PD 0.5248(18) A 2
H H36D 0.6833 0.9762 0.4596 0.123 Uiso calc PR 0.5248(18) A 2
H H36E 0.7282 0.8891 0.4849 0.123 Uiso calc PR 0.5248(18) A 2
H H36F 0.6694 0.9152 0.5468 0.123 Uiso calc PR 0.5248(18) A 2
C C37 0.60185(8) 0.51266(10) 0.38106(12) 0.0428(4) Uani d . 1 . .
C C38 0.54356(9) 0.45826(11) 0.38742(12) 0.0469(4) Uani d . 1 . .
C C39 0.55036(10) 0.38129(12) 0.44557(13) 0.0575(5) Uani d . 1 . .
H H39 0.5119 0.3445 0.4494 0.069 Uiso calc R 1 . .
C C40 0.61396(12) 0.36000(14) 0.49714(14) 0.0676(5) Uani d . 1 . .
H H40 0.6180 0.3089 0.5362 0.081 Uiso calc R 1 . .
C C41 0.67168(11) 0.41263(14) 0.49217(15) 0.0685(5) Uani d . 1 . .
H H41 0.7147 0.3969 0.5266 0.082 Uiso calc R 1 . .
C C42 0.66511(9) 0.48984(12) 0.43498(13) 0.0561(4) Uani d . 1 . .
H H42 0.7038 0.5268 0.4329 0.067 Uiso calc R 1 . .
O O8 0.48171(6) 0.48419(8) 0.33605(9) 0.0604(3) Uani d . 1 . .
H H8B 0.4576 0.4395 0.3211 0.091 Uiso calc R 1 . .
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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
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 N1 N2 . . 109.09(11) ?
C2 N1 C5 . . 126.44(12) ?
N2 N1 C5 . . 123.44(11) ?
C1 N2 N1 . . 101.84(11) ?
N2 C1 N3 . . 116.56(13) ?
N2 C1 H1 . . 121.7 ?
N3 C1 H1 . . 121.7 ?
C2 N3 C1 . . 102.10(12) ?
N3 C2 N4 . . 128.49(13) ?
N3 C2 N1 . . 110.40(13) ?
N4 C2 N1 . . 121.10(13) ?
C2 N4 C3 . . 116.58(12) ?
C2 N4 H4 . . 121.7 ?
C3 N4 H4 . . 121.7 ?
N4 C3 C16 . . 112.15(12) ?
N4 C3 C4 . . 107.46(12) ?
C16 C3 C4 . . 110.81(12) ?
N4 C3 H3 . . 108.8 ?
C16 C3 H3 . . 108.8 ?
C4 C3 H3 . . 108.8 ?
C5 C4 C3 . . 112.01(12) ?
C5 C4 H4A . . 109.2 ?
C3 C4 H4A . . 109.2 ?
C5 C4 H4B . . 109.2 ?
C3 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
N1 C5 O1 . . 103.95(12) ?
N1 C5 C13 . . 111.11(13) ?
O1 C5 C13 . . 110.71(12) ?
N1 C5 C4 . . 108.48(11) ?
O1 C5 C4 . . 109.72(13) ?
C13 C5 C4 . . 112.50(13) ?
C6 O1 C5 . . 117.69(13) ?
C7 C6 O1 . . 118.12(19) ?
C7 C6 C11 . . 121.48(19) ?
O1 C6 C11 . . 120.33(17) ?
C6 C7 C8 . . 118.7(3) ?
C6 C7 H7 . . 120.6 ?
C8 C7 H7 . . 120.6 ?
C9 C8 C7 . . 120.4(3) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C10 . . 121.3(2) ?
C8 C9 H9 . . 119.4 ?
C10 C9 H9 . . 119.4 ?
C9 C10 C11 . . 120.4(3) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C6 C11 C10 . . 117.8(2) ?
C6 C11 C12 . . 117.85(16) ?
C10 C11 C12 . . 124.4(2) ?
C13 C12 C11 . . 120.83(18) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 122.87(17) ?
C12 C13 C5 . . 120.33(16) ?
C14 C13 C5 . . 116.38(14) ?
O2 C14 O3 . . 123.40(19) ?
O2 C14 C13 . . 125.29(17) ?
O3 C14 C13 . . 111.25(18) ?
C14 O3 C15 . . 113.54(19) ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C21 C16 C17 . . 119.01(15) ?
C21 C16 C3 . . 122.38(14) ?
C17 C16 C3 . . 118.57(14) ?
O4 C17 C16 . . 117.39(14) ?
O4 C17 C18 . . 122.45(15) ?
C16 C17 C18 . . 120.16(16) ?
C19 C18 C17 . . 120.05(16) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C19 C20 . . 120.66(17) ?
C18 C19 H19 . . 119.7 ?
C20 C19 H19 . . 119.7 ?
C19 C20 C21 . . 118.98(17) ?
C19 C20 H20 . . 120.5 ?
C21 C20 H20 . . 120.5 ?
C16 C21 C20 . . 121.12(17) ?
C16 C21 H21 . . 119.4 ?
C20 C21 H21 . . 119.4 ?
C17 O4 H4C . . 109.5 ?
C23 N5 N6 . . 108.78(12) ?
C23 N5 C26 . . 125.94(14) ?
N6 N5 C26 . . 125.16(12) ?
C22 N6 N5 . . 101.97(13) ?
N6 C22 N7 . . 116.03(15) ?
N6 C22 H22 . . 122.0 ?
N7 C22 H22 . . 122.0 ?
C23 N7 C22 . . 102.52(13) ?
N7 C23 N5 . . 110.68(14) ?
N7 C23 N8 . . 128.47(14) ?
N5 C23 N8 . . 120.85(14) ?
C23 N8 C24 . . 117.21(13) ?
C23 N8 H8A . . 121.4 ?
C24 N8 H8A . . 121.4 ?
N8 C24 C37 . . 112.18(13) ?
N8 C24 C25 . . 107.67(13) ?
C37 C24 C25 . . 111.29(13) ?
N8 C24 H24 . . 108.5 ?
C37 C24 H24 . . 108.5 ?
C25 C24 H24 . . 108.5 ?
C24 C25 C26 . . 110.53(14) ?
C24 C25 H25A . . 109.5 ?
C26 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
C26 C25 H25B . . 109.5 ?
H25A C25 H25B . . 108.1 ?
O5 C26 N5 . . 112.9(2) ?
O5 C26 C34' . . 76.8(2) ?
N5 C26 C34' . . 120.6(2) ?
O5 C26 C25 . . 115.8(2) ?
N5 C26 C25 . . 110.47(13) ?
C34' C26 C25 . . 116.5(2) ?
N5 C26 O5' . . 97.70(18) ?
C34' C26 O5' . . 103.0(2) ?
C25 C26 O5' . . 104.97(18) ?
O5 C26 C34 . . 109.8(2) ?
N5 C26 C34 . . 103.2(2) ?
C25 C26 C34 . . 103.4(2) ?
O5' C26 C34 . . 135.8(2) ?
C26 O5 C27 . . 121.2(4) ?
C28 C27 C32 . . 122.6(5) ?
C28 C27 O5 . . 117.1(5) ?
C32 C27 O5 . . 120.3(5) ?
C27 C28 C29 . . 117.5(7) ?
C27 C28 H28 . . 121.3 ?
C29 C28 H28 . . 121.3 ?
C30 C29 C28 . . 121.2(9) ?
C30 C29 H29 . . 119.4 ?
C28 C29 H29 . . 119.4 ?
C31 C30 C29 . . 119.9(6) ?
C31 C30 H30 . . 120.1 ?
C29 C30 H30 . . 120.1 ?
C30 C31 C32 . . 121.7(5) ?
C30 C31 H31 . . 119.2 ?
C32 C31 H31 . . 119.2 ?
C27 C32 C31 . . 117.1(7) ?
C27 C32 C33 . . 118.5(6) ?
C31 C32 C33 . . 124.4(7) ?
C34 C33 C32 . . 119.9(5) ?
C34 C33 H33 . . 120.1 ?
C32 C33 H33 . . 120.1 ?
C33 C34 C35 . . 121.6(8) ?
C33 C34 C26 . . 118.0(4) ?
C35 C34 C26 . . 120.4(6) ?
O6 C35 O7 . . 118.0(11) ?
O6 C35 C34 . . 126.7(12) ?
O7 C35 C34 . . 113.3(9) ?
C35 O7 C36 . . 118.0(6) ?
C27' O5' C26 . . 120.7(3) ?
C28' C27' O5' . . 118.8(3) ?
C28' C27' C32' . . 120.9(4) ?
O5' C27' C32' . . 120.1(4) ?
C27' C28' C29' . . 118.9(4) ?
C27' C28' H28' . . 120.5 ?
C29' C28' H28' . . 120.5 ?
C30' C29' C28' . . 120.8(4) ?
C30' C29' H29' . . 119.6 ?
C28' C29' H29' . . 119.6 ?
C31' C30' C29' . . 120.1(6) ?
C31' C30' H30' . . 119.9 ?
C29' C30' H30' . . 119.9 ?
C30' C31' C32' . . 120.2(9) ?
C30' C31' H31' . . 119.9 ?
C32' C31' H31' . . 119.9 ?
C27' C32' C31' . . 118.9(7) ?
C27' C32' C33' . . 118.1(5) ?
C31' C32' C33' . . 123.0(7) ?
C34' C33' C32' . . 120.5(7) ?
C34' C33' H33' . . 119.8 ?
C32' C33' H33' . . 119.8 ?
C33' C34' C35' . . 118.3(5) ?
C33' C34' C26 . . 125.5(5) ?
C35' C34' C26 . . 115.1(3) ?
O6' C35' O7' . . 118.6(5) ?
O6' C35' C34' . . 126.0(4) ?
O7' C35' C34' . . 115.3(5) ?
C35' O7' C36' . . 118.8(6) ?
O7' C36' H36D . . 109.5 ?
O7' C36' H36E . . 109.5 ?
H36D C36' H36E . . 109.5 ?
O7' C36' H36F . . 109.5 ?
H36D C36' H36F . . 109.5 ?
H36E C36' H36F . . 109.5 ?
C42 C37 C38 . . 118.92(15) ?
C42 C37 C24 . . 122.97(14) ?
C38 C37 C24 . . 118.11(14) ?
O8 C38 C39 . . 122.79(15) ?
O8 C38 C37 . . 117.45(15) ?
C39 C38 C37 . . 119.76(16) ?
C40 C39 C38 . . 119.85(17) ?
C40 C39 H39 . . 120.1 ?
C38 C39 H39 . . 120.1 ?
C41 C40 C39 . . 121.29(18) ?
C41 C40 H40 . . 119.4 ?
C39 C40 H40 . . 119.4 ?
C40 C41 C42 . . 119.12(19) ?
C40 C41 H41 . . 120.4 ?
C42 C41 H41 . . 120.4 ?
C37 C42 C41 . . 121.03(18) ?
C37 C42 H42 . . 119.5 ?
C41 C42 H42 . . 119.5 ?
C38 O8 H8B . . 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
N1 C2 . 1.3573(18) ?
N1 N2 . 1.3895(17) ?
N1 C5 . 1.4385(19) ?
N2 C1 . 1.3046(19) ?
C1 N3 . 1.3713(19) ?
C1 H1 . 0.9300 ?
N3 C2 . 1.3303(18) ?
C2 N4 . 1.3498(19) ?
N4 C3 . 1.4580(19) ?
N4 H4 . 0.8600 ?
C3 C16 . 1.527(2) ?
C3 C4 . 1.539(2) ?
C3 H3 . 0.9800 ?
C4 C5 . 1.536(2) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 O1 . 1.4453(19) ?
C5 C13 . 1.524(2) ?
O1 C6 . 1.380(2) ?
C6 C7 . 1.372(3) ?
C6 C11 . 1.403(3) ?
C7 C8 . 1.401(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.360(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.361(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.405(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.440(3) ?
C12 C13 . 1.335(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.481(3) ?
C14 O2 . 1.203(2) ?
C14 O3 . 1.360(2) ?
O3 C15 . 1.474(3) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C21 . 1.390(2) ?
C16 C17 . 1.391(2) ?
C17 O4 . 1.375(2) ?
C17 C18 . 1.394(2) ?
C18 C19 . 1.378(2) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.388(3) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.392(2) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
O4 H4C . 0.8200 ?
N5 C23 . 1.3479(19) ?
N5 N6 . 1.3931(18) ?
N5 C26 . 1.411(2) ?
N6 C22 . 1.308(2) ?
C22 N7 . 1.364(2) ?
C22 H22 . 0.9300 ?
N7 C23 . 1.326(2) ?
C23 N8 . 1.349(2) ?
N8 C24 . 1.4581(19) ?
N8 H8A . 0.8600 ?
C24 C37 . 1.519(2) ?
C24 C25 . 1.527(2) ?
C24 H24 . 0.9800 ?
C25 C26 . 1.530(2) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 O5 . 1.296(4) ?
C26 C34' . 1.503(4) ?
C26 O5' . 1.598(4) ?
C26 C34 . 1.663(6) ?
O5 C27 . 1.405(6) ?
C27 C28 . 1.369(6) ?
C27 C32 . 1.386(10) ?
C28 C29 . 1.390(11) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.374(12) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.341(5) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.396(8) ?
C31 H31 . 0.9300 ?
C32 C33 . 1.448(10) ?
C33 C34 . 1.341(5) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.463(13) ?
C35 O6 . 1.203(13) ?
C35 O7 . 1.398(13) ?
O7 C36 . 1.438(5) ?
C36 H36A . 0.9600 ?
C36 H36B . 0.9600 ?
C36 H36C . 0.9600 ?
O5' C27' . 1.378(4) ?
C27' C28' . 1.358(5) ?
C27' C32' . 1.379(7) ?
C28' C29' . 1.391(5) ?
C28' H28' . 0.9300 ?
C29' C30' . 1.368(6) ?
C29' H29' . 0.9300 ?
C30' C31' . 1.345(10) ?
C30' H30' . 0.9300 ?
C31' C32' . 1.406(10) ?
C31' H31' . 0.9300 ?
C32' C33' . 1.467(10) ?
C33' C34' . 1.354(8) ?
C33' H33' . 0.9300 ?
C34' C35' . 1.454(6) ?
C35' O6' . 1.202(5) ?
C35' O7' . 1.384(8) ?
O7' C36' . 1.448(8) ?
C36' H36D . 0.9600 ?
C36' H36E . 0.9600 ?
C36' H36F . 0.9600 ?
C37 C42 . 1.386(2) ?
C37 C38 . 1.399(2) ?
C38 O8 . 1.362(2) ?
C38 C39 . 1.395(2) ?
C39 C40 . 1.373(3) ?
C39 H39 . 0.9300 ?
C40 C41 . 1.371(3) ?
C40 H40 . 0.9300 ?
C41 C42 . 1.390(3) ?
C41 H41 . 0.9300 ?
C42 H42 . 0.9300 ?
O8 H8B . 0.8200 ?
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
_geom_hbond_publ_flag
N4 H4 N7 . 0.86 2.21 3.0156(19) 156.3 y
O4 H4C N2 2_755 0.82 2.12 2.9152(17) 163.4 y
N8 H8A N3 . 0.86 2.10 2.9168(19) 159.1 y
O8 H8B N6 2_645 0.82 2.09 2.8898(19) 164.1 y
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
C2 N1 N2 C1 . . . . -0.15(15) ?
C5 N1 N2 C1 . . . . -169.24(13) ?
N1 N2 C1 N3 . . . . 0.28(17) ?
N2 C1 N3 C2 . . . . -0.29(18) ?
C1 N3 C2 N4 . . . . -179.00(15) ?
C1 N3 C2 N1 . . . . 0.17(16) ?
N2 N1 C2 N3 . . . . -0.01(16) ?
C5 N1 C2 N3 . . . . 168.67(13) ?
N2 N1 C2 N4 . . . . 179.22(13) ?
C5 N1 C2 N4 . . . . -12.1(2) ?
N3 C2 N4 C3 . . . . 165.60(15) ?
N1 C2 N4 C3 . . . . -13.5(2) ?
C2 N4 C3 C16 . . . . 169.72(13) ?
C2 N4 C3 C4 . . . . 47.70(17) ?
N4 C3 C4 C5 . . . . -60.47(16) ?
C16 C3 C4 C5 . . . . 176.68(13) ?
C2 N1 C5 O1 . . . . 114.85(15) ?
N2 N1 C5 O1 . . . . -77.99(16) ?
C2 N1 C5 C13 . . . . -126.03(16) ?
N2 N1 C5 C13 . . . . 41.12(18) ?
C2 N1 C5 C4 . . . . -1.9(2) ?
N2 N1 C5 C4 . . . . 165.28(13) ?
C3 C4 C5 N1 . . . . 37.65(17) ?
C3 C4 C5 O1 . . . . -75.30(15) ?
C3 C4 C5 C13 . . . . 160.98(13) ?
N1 C5 O1 C6 . . . . 160.34(14) ?
C13 C5 O1 C6 . . . . 40.94(19) ?
C4 C5 O1 C6 . . . . -83.81(17) ?
C5 O1 C6 C7 . . . . 151.29(18) ?
C5 O1 C6 C11 . . . . -31.8(2) ?
O1 C6 C7 C8 . . . . 177.3(2) ?
C11 C6 C7 C8 . . . . 0.4(3) ?
C6 C7 C8 C9 . . . . -0.7(4) ?
C7 C8 C9 C10 . . . . 0.7(5) ?
C8 C9 C10 C11 . . . . -0.5(4) ?
C7 C6 C11 C10 . . . . -0.1(3) ?
O1 C6 C11 C10 . . . . -176.96(18) ?
C7 C6 C11 C12 . . . . -178.9(2) ?
O1 C6 C11 C12 . . . . 4.2(3) ?
C9 C10 C11 C6 . . . . 0.1(3) ?
C9 C10 C11 C12 . . . . 178.9(2) ?
C6 C11 C12 C13 . . . . 10.9(3) ?
C10 C11 C12 C13 . . . . -167.8(2) ?
C11 C12 C13 C14 . . . . 173.58(17) ?
C11 C12 C13 C5 . . . . 1.4(3) ?
N1 C5 C13 C12 . . . . -141.31(16) ?
O1 C5 C13 C12 . . . . -26.3(2) ?
C4 C5 C13 C12 . . . . 96.84(18) ?
N1 C5 C13 C14 . . . . 45.98(19) ?
O1 C5 C13 C14 . . . . 160.96(14) ?
C4 C5 C13 C14 . . . . -75.87(18) ?
C12 C13 C14 O2 . . . . -161.1(2) ?
C5 C13 C14 O2 . . . . 11.4(3) ?
C12 C13 C14 O3 . . . . 21.6(3) ?
C5 C13 C14 O3 . . . . -165.94(16) ?
O2 C14 O3 C15 . . . . 6.1(3) ?
C13 C14 O3 C15 . . . . -176.5(2) ?
N4 C3 C16 C21 . . . . -24.5(2) ?
C4 C3 C16 C21 . . . . 95.55(18) ?
N4 C3 C16 C17 . . . . 157.78(14) ?
C4 C3 C16 C17 . . . . -82.13(17) ?
C21 C16 C17 O4 . . . . -179.75(15) ?
C3 C16 C17 O4 . . . . -2.0(2) ?
C21 C16 C17 C18 . . . . 0.0(2) ?
C3 C16 C17 C18 . . . . 177.78(15) ?
O4 C17 C18 C19 . . . . 178.58(17) ?
C16 C17 C18 C19 . . . . -1.2(3) ?
C17 C18 C19 C20 . . . . 1.5(3) ?
C18 C19 C20 C21 . . . . -0.7(3) ?
C17 C16 C21 C20 . . . . 0.8(3) ?
C3 C16 C21 C20 . . . . -176.86(16) ?
C19 C20 C21 C16 . . . . -0.5(3) ?
C23 N5 N6 C22 . . . . -0.57(19) ?
C26 N5 N6 C22 . . . . 175.70(17) ?
N5 N6 C22 N7 . . . . -0.3(2) ?
N6 C22 N7 C23 . . . . 1.1(2) ?
C22 N7 C23 N5 . . . . -1.4(2) ?
C22 N7 C23 N8 . . . . 178.95(19) ?
N6 N5 C23 N7 . . . . 1.3(2) ?
C26 N5 C23 N7 . . . . -174.92(17) ?
N6 N5 C23 N8 . . . . -179.02(16) ?
C26 N5 C23 N8 . . . . 4.7(3) ?
N7 C23 N8 C24 . . . . -163.94(18) ?
N5 C23 N8 C24 . . . . 16.5(2) ?
C23 N8 C24 C37 . . . . -170.38(15) ?
C23 N8 C24 C25 . . . . -47.6(2) ?
N8 C24 C25 C26 . . . . 59.30(19) ?
C37 C24 C25 C26 . . . . -177.38(14) ?
C23 N5 C26 O5 . . . . -122.6(2) ?
N6 N5 C26 O5 . . . . 61.7(3) ?
C23 N5 C26 C34' . . . . 149.5(2) ?
N6 N5 C26 C34' . . . . -26.1(3) ?
C23 N5 C26 C25 . . . . 8.9(3) ?
N6 N5 C26 C25 . . . . -166.78(15) ?
C23 N5 C26 O5' . . . . -100.3(2) ?
N6 N5 C26 O5' . . . . 84.0(2) ?
C23 N5 C26 C34 . . . . 118.9(2) ?
N6 N5 C26 C34 . . . . -56.8(3) ?
C24 C25 C26 O5 . . . . 89.4(2) ?
C24 C25 C26 N5 . . . . -40.6(2) ?
C24 C25 C26 C34' . . . . 177.0(2) ?
C24 C25 C26 O5' . . . . 63.80(19) ?
C24 C25 C26 C34 . . . . -150.4(2) ?
N5 C26 O5 C27 . . . . -156.1(4) ?
C34' C26 O5 C27 . . . . -38.2(4) ?
C25 C26 O5 C27 . . . . 75.1(4) ?
O5' C26 O5 C27 . . . . 145.8(8) ?
C34 C26 O5 C27 . . . . -41.5(5) ?
C26 O5 C27 C28 . . . . -149.3(4) ?
C26 O5 C27 C32 . . . . 32.6(8) ?
C32 C27 C28 C29 . . . . 1.2(14) ?
O5 C27 C28 C29 . . . . -176.8(12) ?
C27 C28 C29 C30 . . . . 1(2) ?
C28 C29 C30 C31 . . . . -1(2) ?
C29 C30 C31 C32 . . . . -0.9(13) ?
C28 C27 C32 C31 . . . . -2.7(12) ?
O5 C27 C32 C31 . . . . 175.3(6) ?
C28 C27 C32 C33 . . . . -180.0(6) ?
O5 C27 C32 C33 . . . . -2.0(11) ?
C30 C31 C32 C27 . . . . 2.5(11) ?
C30 C31 C32 C33 . . . . 179.6(6) ?
C27 C32 C33 C34 . . . . -11.3(11) ?
C31 C32 C33 C34 . . . . 171.6(7) ?
C32 C33 C34 C35 . . . . -178(2) ?
C32 C33 C34 C26 . . . . -0.6(7) ?
O5 C26 C34 C33 . . . . 26.3(5) ?
N5 C26 C34 C33 . . . . 147.0(3) ?
C34' C26 C34 C33 . . . . 20.4(3) ?
C25 C26 C34 C33 . . . . -97.9(4) ?
O5' C26 C34 C33 . . . . 31.0(5) ?
O5 C26 C34 C35 . . . . -156(2) ?
N5 C26 C34 C35 . . . . -36(2) ?
C34' C26 C34 C35 . . . . -162(2) ?
C25 C26 C34 C35 . . . . 79(2) ?
O5' C26 C34 C35 . . . . -152(2) ?
C33 C34 C35 O6 . . . . 155(3) ?
C26 C34 C35 O6 . . . . -22(5) ?
C33 C34 C35 O7 . . . . -8(4) ?
C26 C34 C35 O7 . . . . 174.6(17) ?
O6 C35 O7 C36 . . . . 4(4) ?
C34 C35 O7 C36 . . . . 169.2(17) ?
O5 C26 O5' C27' . . . . -36.4(5) ?
N5 C26 O5' C27' . . . . -164.3(3) ?
C34' C26 O5' C27' . . . . -40.4(3) ?
C25 C26 O5' C27' . . . . 82.0(3) ?
C34 C26 O5' C27' . . . . -46.3(5) ?
C26 O5' C27' C28' . . . . -152.5(3) ?
C26 O5' C27' C32' . . . . 32.1(5) ?
O5' C27' C28' C29' . . . . -178.2(4) ?
C32' C27' C28' C29' . . . . -2.7(6) ?
C27' C28' C29' C30' . . . . 0.6(6) ?
C28' C29' C30' C31' . . . . 2.1(13) ?
C29' C30' C31' C32' . . . . -3(2) ?
C28' C27' C32' C31' . . . . 2.1(12) ?
O5' C27' C32' C31' . . . . 177.5(11) ?
C28' C27' C32' C33' . . . . 179.0(5) ?
O5' C27' C32' C33' . . . . -5.6(7) ?
C30' C31' C32' C27' . . . . 1(2) ?
C30' C31' C32' C33' . . . . -176.1(12) ?
C27' C32' C33' C34' . . . . -7.0(9) ?
C31' C32' C33' C34' . . . . 169.7(12) ?
C32' C33' C34' C35' . . . . -175.5(5) ?
C32' C33' C34' C26 . . . . -8.1(9) ?
O5 C26 C34' C33' . . . . 26.7(5) ?
N5 C26 C34' C33' . . . . 135.8(5) ?
C25 C26 C34' C33' . . . . -85.8(5) ?
O5' C26 C34' C33' . . . . 28.5(5) ?
C34 C26 C34' C33' . . . . -159.0(7) ?
O5 C26 C34' C35' . . . . -165.5(3) ?
N5 C26 C34' C35' . . . . -56.5(4) ?
C25 C26 C34' C35' . . . . 82.0(3) ?
O5' C26 C34' C35' . . . . -163.7(3) ?
C34 C26 C34' C35' . . . . 8.7(4) ?
C33' C34' C35' O6' . . . . -16.3(7) ?
C26 C34' C35' O6' . . . . 175.0(4) ?
C33' C34' C35' O7' . . . . 161.1(11) ?
C26 C34' C35' O7' . . . . -7.6(11) ?
O6' C35' O7' C36' . . . . 1(2) ?
C34' C35' O7' C36' . . . . -176.6(11) ?
N8 C24 C37 C42 . . . . 23.0(2) ?
C25 C24 C37 C42 . . . . -97.74(18) ?
N8 C24 C37 C38 . . . . -157.29(14) ?
C25 C24 C37 C38 . . . . 82.00(18) ?
C42 C37 C38 O8 . . . . 177.87(15) ?
C24 C37 C38 O8 . . . . -1.9(2) ?
C42 C37 C38 C39 . . . . -1.6(2) ?
C24 C37 C38 C39 . . . . 178.66(14) ?
O8 C38 C39 C40 . . . . -178.60(16) ?
C37 C38 C39 C40 . . . . 0.8(3) ?
C38 C39 C40 C41 . . . . -0.6(3) ?
C39 C40 C41 C42 . . . . 1.1(3) ?
C38 C37 C42 C41 . . . . 2.1(3) ?
C24 C37 C42 C41 . . . . -178.11(16) ?
C40 C41 C42 C37 . . . . -1.9(3) ?
