#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/47/2204759.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_2204759
loop_
_publ_author_name
'Daqing Shi'
'Nan Wu'
'Qiya Zhuang'
'Yong Zhang'
_publ_section_title
;2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile
 N,N-dimethylformamide solvate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2359
_journal_page_last               o2361
_journal_paper_doi               10.1107/S1600536804029356
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C20 H14 N2 O4, C3 H7 N O'
_chemical_formula_moiety         'C20 H14 N2 O4, C3 H7 N O'
_chemical_formula_sum            'C23 H21 N3 O5'
_chemical_formula_weight         419.43
_chemical_melting_point          507.5(5)
_chemical_name_systematic
;
2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile
N,N-dimethylformamide solvate
;
_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
_cell_angle_alpha                99.799(4)
_cell_angle_beta                 95.399(4)
_cell_angle_gamma                104.785(5)
_cell_formula_units_Z            4
_cell_length_a                   12.472(3)
_cell_length_b                   13.003(3)
_cell_length_c                   13.620(3)
_cell_measurement_reflns_used    7449
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.1
_cell_volume                     2082.5(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20798
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         7573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0489
_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)+(0.0527P)²+0.4884P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                6262
_reflns_number_total             7573
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6421.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '507-508' was changed to '507.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '507-508' was changed to '507.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2204759
_cod_database_fobs_code          2204759
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_type_symbol
O1 0.14762(10) 0.48882(9) 0.36840(9) 0.0350(3) Uani d . 1 O
O2 0.05189(12) 0.37143(11) 0.66709(10) 0.0466(3) Uani d . 1 O
O3 0.12952(11) 0.54572(10) 0.67259(9) 0.0398(3) Uani d . 1 O
O4 0.37998(12) 0.08166(11) 0.60148(11) 0.0526(4) Uani d . 1 O
O5 0.22769(12) 0.61508(11) 0.20001(11) 0.0497(4) Uani d . 1 O
O6 0.37217(10) 0.44134(10) 0.15573(8) 0.0338(3) Uani d . 1 O
O7 0.58637(12) 0.21129(12) 0.02717(10) 0.0513(4) Uani d . 1 O
O8 0.49066(11) 0.27886(11) -0.07718(9) 0.0423(3) Uani d . 1 O
O9 0.25075(12) -0.11340(11) 0.26341(12) 0.0540(4) Uani d . 1 O
O10 0.12581(15) 0.23867(15) 1.03764(12) 0.0697(5) Uani d . 1 O
N1 0.11478(15) 0.39218(16) 0.21213(12) 0.0436(4) Uani d . 1 N
N2 -0.00172(17) 0.11149(16) 0.22949(16) 0.0670(6) Uani d . 1 N
N3 0.13395(14) 0.67670(14) 0.08311(12) 0.0461(4) Uani d . 1 N
N4 0.39254(13) 0.53437(13) 0.31202(12) 0.0346(4) Uani d . 1 N
N5 0.57986(13) 0.42745(13) 0.46251(11) 0.0392(4) Uani d . 1 N
N6 0.19487(16) 0.11396(15) 0.94561(14) 0.0584(5) Uani d . 1 N
C1 0.10962(14) 0.38592(14) 0.30882(13) 0.0324(4) Uani d . 1 C
C2 0.07248(14) 0.29731(14) 0.34877(13) 0.0321(4) Uani d . 1 C
C3 0.07391(14) 0.30022(13) 0.46097(13) 0.0315(4) Uani d . 1 C
H3 -0.0028 0.2623 0.4729 0.038 Uiso calc R 1 H
C4 0.10298(13) 0.41725(13) 0.51436(13) 0.0295(4) Uani d . 1 C
C5 0.13998(13) 0.50097(13) 0.46880(13) 0.0288(4) Uani d . 1 C
C6 0.09160(15) 0.43893(15) 0.62027(14) 0.0353(4) Uani d . 1 C
C7 0.17269(14) 0.63000(14) 0.62555(14) 0.0349(4) Uani d . 1 C
C8 0.21087(16) 0.73315(16) 0.68554(15) 0.0440(5) Uani d . 1 C
H8 0.2078 0.7441 0.7559 0.053 Uiso calc R 1 H
C9 0.25346(16) 0.81969(16) 0.64090(17) 0.0478(5) Uani d . 1 C
H9 0.2805 0.8908 0.6811 0.057 Uiso calc R 1 H
C10 0.25716(16) 0.80394(15) 0.53804(17) 0.0455(5) Uani d . 1 C
H10 0.2858 0.8645 0.5084 0.055 Uiso calc R 1 H
C11 0.21966(14) 0.70128(14) 0.47850(15) 0.0378(4) Uani d . 1 C
H11 0.2228 0.6910 0.4082 0.045 Uiso calc R 1 H
C12 0.17674(13) 0.61195(14) 0.52252(13) 0.0312(4) Uani d . 1 C
C13 0.03168(15) 0.19503(16) 0.28218(15) 0.0409(5) Uani d . 1 C
C14 0.15704(14) 0.24366(13) 0.50088(13) 0.0296(4) Uani d . 1 C
C15 0.27074(14) 0.28573(13) 0.50077(13) 0.0312(4) Uani d . 1 C
H15 0.2965 0.3514 0.4775 0.037 Uiso calc R 1 H
C16 0.34805(15) 0.23457(14) 0.53369(13) 0.0337(4) Uani d . 1 C
H16 0.4257 0.2646 0.5327 0.040 Uiso calc R 1 H
C17 0.31059(15) 0.13912(14) 0.56802(13) 0.0357(4) Uani d . 1 C
C18 0.19724(16) 0.09620(15) 0.57001(15) 0.0413(5) Uani d . 1 C
H18 0.1717 0.0312 0.5942 0.050 Uiso calc R 1 H
C19 0.12156(15) 0.14839(14) 0.53661(14) 0.0379(4) Uani d . 1 C
H19 0.0439 0.1187 0.5381 0.046 Uiso calc R 1 H
C20 0.49548(19) 0.1196(2) 0.5921(2) 0.0659(7) Uani d . 1 C
H20A 0.5029 0.1256 0.5222 0.099 Uiso calc R 1 H
H20B 0.5350 0.0682 0.6113 0.099 Uiso calc R 1 H
H20C 0.5280 0.1909 0.6363 0.099 Uiso calc R 1 H
C21 0.22539(17) 0.67052(16) 0.13514(14) 0.0411(4) Uani d . 1 C
H21 0.2951 0.7119 0.1219 0.049 Uiso calc R 1 H
C22 0.1396(2) 0.7476(3) 0.0103(2) 0.0906(10) Uani d . 1 C
H22A 0.2182 0.7843 0.0081 0.136 Uiso calc R 1 H
H22B 0.0997 0.8018 0.0304 0.136 Uiso calc R 1 H
H22C 0.1048 0.7042 -0.0565 0.136 Uiso calc R 1 H
C23 0.02261(18) 0.6230(2) 0.10248(18) 0.0570(6) Uani d . 1 C
H23A 0.0289 0.5747 0.1494 0.085 Uiso calc R 1 H
H23B -0.0231 0.5804 0.0391 0.085 Uiso calc R 1 H
H23C -0.0129 0.6777 0.1320 0.085 Uiso calc R 1 H
C24 0.42044(14) 0.45440(14) 0.25398(12) 0.0292(4) Uani d . 1 C
C25 0.48696(13) 0.39295(13) 0.27937(12) 0.0289(4) Uani d . 1 C
C26 0.50287(14) 0.29848(14) 0.20592(12) 0.0309(4) Uani d . 1 C
H26 0.5838 0.3001 0.2164 0.037 Uiso calc R 1 H
C27 0.47483(14) 0.31646(14) 0.10087(12) 0.0308(4) Uani d . 1 C
C28 0.41112(13) 0.38163(14) 0.08196(12) 0.0304(4) Uani d . 1 C
C29 0.52106(15) 0.26488(15) 0.01902(13) 0.0375(4) Uani d . 1 C
C30 0.41951(15) 0.34084(15) -0.09583(13) 0.0371(4) Uani d . 1 C
C31 0.39054(17) 0.34596(17) -0.19534(13) 0.0456(5) Uani d . 1 C
H31 0.4201 0.3086 -0.2477 0.055 Uiso calc R 1 H
C32 0.31866(17) 0.40571(18) -0.21701(14) 0.0476(5) Uani d . 1 C
H32 0.2982 0.4095 -0.2850 0.057 Uiso calc R 1 H
C33 0.27536(17) 0.46074(17) -0.14091(14) 0.0463(5) Uani d . 1 C
H33 0.2254 0.5016 -0.1570 0.056 Uiso calc R 1 H
C34 0.30501(15) 0.45607(15) -0.04158(13) 0.0386(4) Uani d . 1 C
H34 0.2761 0.4943 0.0106 0.046 Uiso calc R 1 H
C35 0.37736(14) 0.39517(14) -0.01825(12) 0.0324(4) Uani d . 1 C
C36 0.53757(14) 0.41277(13) 0.38072(13) 0.0297(4) Uani d . 1 C
C37 0.43313(14) 0.18834(14) 0.22134(12) 0.0311(4) Uani d . 1 C
C38 0.33663(15) 0.17900(14) 0.26473(13) 0.0347(4) Uani d . 1 C
H38 0.3129 0.2423 0.2849 0.042 Uiso calc R 1 H
C39 0.27275(16) 0.08010(15) 0.28001(14) 0.0383(4) Uani d . 1 C
H39 0.2069 0.0761 0.3107 0.046 Uiso calc R 1 H
C40 0.30614(16) -0.01199(15) 0.25006(14) 0.0390(4) Uani d . 1 C
C41 0.40248(18) -0.00487(16) 0.20470(16) 0.0480(5) Uani d . 1 C
H41 0.4249 -0.0686 0.1830 0.058 Uiso calc R 1 H
C42 0.46548(17) 0.09397(15) 0.19102(15) 0.0414(4) Uani d . 1 C
H42 0.5316 0.0980 0.1607 0.050 Uiso calc R 1 H
C43 0.14690(19) -0.12423(18) 0.30156(19) 0.0584(6) Uani d . 1 C
H43A 0.1599 -0.0803 0.3698 0.088 Uiso calc R 1 H
H43B 0.1132 -0.2006 0.3032 0.088 Uiso calc R 1 H
H43C 0.0962 -0.0992 0.2579 0.088 Uiso calc R 1 H
C44 0.1685(2) 0.1637(2) 1.03095(18) 0.0654(7) Uani d . 1 C
H44 0.1843 0.1386 1.0907 0.078 Uiso calc R 1 H
C45 0.2470(3) 0.0268(2) 0.9439(3) 0.1024(11) Uani d . 1 C
H45A 0.2669 0.0187 1.0129 0.154 Uiso calc R 1 H
H45B 0.3149 0.0434 0.9119 0.154 Uiso calc R 1 H
H45C 0.1947 -0.0410 0.9055 0.154 Uiso calc R 1 H
C46 0.1669(2) 0.1429(2) 0.85135(17) 0.0675(7) Uani d . 1 C
H46A 0.0996 0.0887 0.8135 0.101 Uiso calc R 1 H
H46B 0.2293 0.1454 0.8123 0.101 Uiso calc R 1 H
H46C 0.1527 0.2144 0.8639 0.101 Uiso calc R 1 H
H1A 0.1450(18) 0.4613(19) 0.2023(16) 0.052(6) Uiso d . 1 H
H1B 0.110(2) 0.330(2) 0.1674(19) 0.066(7) Uiso d . 1 H
H4A 0.3479(18) 0.5643(17) 0.2836(16) 0.045(6) Uiso d . 1 H
H4B 0.4051(17) 0.5428(16) 0.3793(17) 0.046(6) Uiso d . 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
C5 O1 C1 118.60(13) no
C7 O3 C6 121.77(14) no
C17 O4 C20 116.73(16) ?
C28 O6 C24 117.99(13) ?
C30 O8 C29 121.81(14) ?
C40 O9 C43 117.10(16) ?
C1 N1 H1A 114.1(14) ?
C1 N1 H1B 118.1(15) ?
H1A N1 H1B 125(2) ?
C21 N3 C23 122.00(17) ?
C21 N3 C22 120.99(19) ?
C23 N3 C22 116.70(18) ?
C24 N4 H4A 117.1(14) ?
C24 N4 H4B 119.6(13) ?
H4A N4 H4B 121.3(19) ?
C44 N6 C46 120.5(2) ?
C44 N6 C45 121.9(2) ?
C46 N6 C45 117.5(2) ?
N1 C1 C2 128.95(17) no
N1 C1 O1 109.53(16) no
C2 C1 O1 121.52(16) no
C1 C2 C13 118.02(17) ?
C1 C2 C3 124.07(15) ?
C13 C2 C3 117.90(16) ?
C4 C3 C2 108.09(14) ?
C4 C3 C14 110.94(13) ?
C2 C3 C14 111.55(14) ?
C4 C3 H3 108.7 ?
C2 C3 H3 108.7 ?
C14 C3 H3 108.7 ?
C5 C4 C6 119.35(16) ?
C5 C4 C3 123.15(16) ?
C6 C4 C3 117.49(15) ?
C4 C5 O1 123.53(15) ?
C4 C5 C12 122.62(16) ?
O1 C5 C12 113.85(15) ?
O2 C6 O3 116.93(17) no
O2 C6 C4 125.24(17) no
O3 C6 C4 117.83(16) no
O3 C7 C8 116.94(17) ?
O3 C7 C12 121.31(16) ?
C8 C7 C12 121.74(18) ?
C9 C8 C7 118.58(19) ?
C9 C8 H8 120.7 ?
C7 C8 H8 120.7 ?
C8 C9 C10 120.76(18) ?
C8 C9 H9 119.6 ?
C10 C9 H9 119.6 ?
C11 C10 C9 120.63(19) ?
C11 C10 H10 119.7 ?
C9 C10 H10 119.7 ?
C10 C11 C12 119.55(19) ?
C10 C11 H11 120.2 ?
C12 C11 H11 120.2 ?
C7 C12 C11 118.74(16) ?
C7 C12 C5 116.82(16) ?
C11 C12 C5 124.39(17) ?
N2 C13 C2 179.0(2) no
C15 C14 C19 118.11(16) ?
C15 C14 C3 120.28(15) ?
C19 C14 C3 121.60(15) ?
C14 C15 C16 121.68(16) ?
C14 C15 H15 119.2 ?
C16 C15 H15 119.2 ?
C17 C16 C15 119.17(16) ?
C17 C16 H16 120.4 ?
C15 C16 H16 120.4 ?
O4 C17 C18 116.03(16) ?
O4 C17 C16 123.80(17) ?
C18 C17 C16 120.17(16) ?
C19 C18 C17 119.72(17) ?
C19 C18 H18 120.1 ?
C17 C18 H18 120.1 ?
C18 C19 C14 121.15(17) ?
C18 C19 H19 119.4 ?
C14 C19 H19 119.4 ?
O4 C20 H20A 109.5 ?
O4 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
O4 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
O5 C21 N3 125.00(19) ?
O5 C21 H21 117.5 ?
N3 C21 H21 117.5 ?
N3 C22 H22A 109.5 ?
N3 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
N3 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
N3 C23 H23A 109.5 ?
N3 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
N3 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
N4 C24 C25 129.25(15) ?
N4 C24 O6 109.66(14) ?
C25 C24 O6 121.07(15) ?
C24 C25 C36 118.55(15) ?
C24 C25 C26 122.83(14) ?
C36 C25 C26 118.47(15) ?
C27 C26 C25 107.48(14) ?
C27 C26 C37 112.15(13) ?
C25 C26 C37 112.56(14) ?
C27 C26 H26 108.2 ?
C25 C26 H26 108.2 ?
C37 C26 H26 108.2 ?
C28 C27 C29 118.98(16) ?
C28 C27 C26 121.84(15) ?
C29 C27 C26 119.14(16) ?
C27 C28 O6 123.11(15) ?
C27 C28 C35 123.04(16) ?
O6 C28 C35 113.84(15) ?
O7 C29 O8 116.28(16) ?
O7 C29 C27 125.54(17) ?
O8 C29 C27 118.17(16) ?
O8 C30 C31 117.29(17) ?
O8 C30 C35 121.41(16) ?
C31 C30 C35 121.29(19) ?
C32 C31 C30 118.98(19) ?
C32 C31 H31 120.5 ?
C30 C31 H31 120.5 ?
C31 C32 C33 120.87(17) ?
C31 C32 H32 119.6 ?
C33 C32 H32 119.6 ?
C34 C33 C32 120.0(2) ?
C34 C33 H33 120.0 ?
C32 C33 H33 120.0 ?
C33 C34 C35 119.88(19) ?
C33 C34 H34 120.1 ?
C35 C34 H34 120.1 ?
C30 C35 C34 118.95(16) ?
C30 C35 C28 116.34(17) ?
C34 C35 C28 124.69(16) ?
N5 C36 C25 178.66(19) ?
C38 C37 C42 117.88(17) ?
C38 C37 C26 121.33(15) ?
C42 C37 C26 120.78(16) ?
C37 C38 C39 122.20(17) ?
C37 C38 H38 118.9 ?
C39 C38 H38 118.9 ?
C40 C39 C38 119.13(18) ?
C40 C39 H39 120.4 ?
C38 C39 H39 120.4 ?
O9 C40 C39 124.01(18) ?
O9 C40 C41 116.25(17) ?
C39 C40 C41 119.73(17) ?
C42 C41 C40 120.41(18) ?
C42 C41 H41 119.8 ?
C40 C41 H41 119.8 ?
C41 C42 C37 120.64(18) ?
C41 C42 H42 119.7 ?
C37 C42 H42 119.7 ?
O9 C43 H43A 109.5 ?
O9 C43 H43B 109.5 ?
H43A C43 H43B 109.5 ?
O9 C43 H43C 109.5 ?
H43A C43 H43C 109.5 ?
H43B C43 H43C 109.5 ?
O10 C44 N6 125.0(2) ?
O10 C44 H44 117.5 ?
N6 C44 H44 117.5 ?
N6 C45 H45A 109.5 ?
N6 C45 H45B 109.5 ?
H45A C45 H45B 109.5 ?
N6 C45 H45C 109.5 ?
H45A C45 H45C 109.5 ?
H45B C45 H45C 109.5 ?
N6 C46 H46A 109.5 ?
N6 C46 H46B 109.5 ?
H46A C46 H46B 109.5 ?
N6 C46 H46C 109.5 ?
H46A C46 H46C 109.5 ?
H46B C46 H46C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.365(2) y
O1 C1 1.381(2) y
O2 C6 1.204(2) y
O3 C7 1.380(2) y
O3 C6 1.387(2) y
O4 C17 1.374(2) ?
O4 C20 1.424(3) ?
O5 C21 1.234(2) ?
O6 C28 1.366(2) yes
O6 C24 1.3788(19) yes
O7 C29 1.208(2) yes
O8 C30 1.376(2) yes
O8 C29 1.384(2) yes
O9 C40 1.375(2) ?
O9 C43 1.423(3) ?
O10 C44 1.219(3) ?
N1 C1 1.340(2) y
N1 H1A 0.92(2) ?
N1 H1B 0.91(3) ?
N2 C13 1.147(3) y
N3 C21 1.313(2) ?
N3 C23 1.457(3) ?
N3 C22 1.459(3) ?
N4 C24 1.336(2) yes
N4 H4A 0.86(2) ?
N4 H4B 0.90(2) ?
N5 C36 1.150(2) yes
N6 C44 1.343(3) ?
N6 C46 1.435(3) ?
N6 C45 1.441(3) ?
C1 C2 1.352(2) no
C2 C13 1.417(3) ?
C2 C3 1.520(2) no
C3 C4 1.506(2) ?
C3 C14 1.527(2) ?
C3 H3 1.0000 ?
C4 C5 1.346(2) no
C4 C6 1.449(3) ?
C5 C12 1.438(2) ?
C7 C8 1.386(3) ?
C7 C12 1.391(3) ?
C8 C9 1.381(3) ?
C8 H8 0.9500 ?
C9 C10 1.388(3) ?
C9 H9 0.9500 ?
C10 C11 1.378(3) ?
C10 H10 0.9500 ?
C11 C12 1.405(3) ?
C11 H11 0.9500 ?
C14 C15 1.384(2) ?
C14 C19 1.391(2) ?
C15 C16 1.386(2) ?
C15 H15 0.9500 ?
C16 C17 1.386(3) ?
C16 H16 0.9500 ?
C17 C18 1.386(3) ?
C18 C19 1.382(3) ?
C18 H18 0.9500 ?
C19 H19 0.9500 ?
C20 H20A 0.9800 ?
C20 H20B 0.9800 ?
C20 H20C 0.9800 ?
C21 H21 0.9500 ?
C22 H22A 0.9800 ?
C22 H22B 0.9800 ?
C22 H22C 0.9800 ?
C23 H23A 0.9800 ?
C23 H23B 0.9800 ?
C23 H23C 0.9800 ?
C24 C25 1.351(2) ?
C25 C36 1.415(2) ?
C25 C26 1.514(2) ?
C26 C27 1.512(2) ?
C26 C37 1.534(2) ?
C26 H26 1.0000 ?
C27 C28 1.340(2) ?
C27 C29 1.445(2) ?
C28 C35 1.443(2) ?
C30 C31 1.387(3) ?
C30 C35 1.390(3) ?
C31 C32 1.370(3) ?
C31 H31 0.9500 ?
C32 C33 1.389(3) ?
C32 H32 0.9500 ?
C33 C34 1.384(3) ?
C33 H33 0.9500 ?
C34 C35 1.392(3) ?
C34 H34 0.9500 ?
C37 C38 1.377(2) ?
C37 C42 1.397(2) ?
C38 C39 1.390(3) ?
C38 H38 0.9500 ?
C39 C40 1.376(3) ?
C39 H39 0.9500 ?
C40 C41 1.392(3) ?
C41 C42 1.378(3) ?
C41 H41 0.9500 ?
C42 H42 0.9500 ?
C43 H43A 0.9800 ?
C43 H43B 0.9800 ?
C43 H43C 0.9800 ?
C44 H44 0.9500 ?
C45 H45A 0.9800 ?
C45 H45B 0.9800 ?
C45 H45C 0.9800 ?
C46 H46A 0.9800 ?
C46 H46B 0.9800 ?
C46 H46C 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
N1 H1A O5 . 0.92(2) 2.01(2) 2.921(2) 171(2)
N1 H1B O10 1_554 0.91(3) 2.01(3) 2.870(3) 157(2)
N4 H4A O5 . 0.86(2) 2.10(2) 2.952(2) 172(2)
N4 H4B N5 2_666 0.90(2) 2.11(2) 2.998(2) 173(2)
C22 H22A O7 2_665 0.98 2.52 3.423(3) 154
C46 H46A N2 2_556 0.98 2.52 3.355(3) 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
C5 O1 C1 N1 174.41(14) no
C5 O1 C1 C2 -4.5(2) y
N1 C1 C2 C13 -0.5(3) no
O1 C1 C2 C13 178.10(15) no
N1 C1 C2 C3 178.17(17) no
O1 C1 C2 C3 -3.2(3) y
C1 C2 C3 C4 10.0(2) y
C13 C2 C3 C4 -171.30(15) ?
C1 C2 C3 C14 -112.24(18) ?
C13 C2 C3 C14 66.5(2) ?
C2 C3 C4 C5 -10.6(2) ?
C14 C3 C4 C5 111.97(18) ?
C2 C3 C4 C6 170.34(14) ?
C14 C3 C4 C6 -67.06(19) ?
C6 C4 C5 O1 -176.32(14) ?
C3 C4 C5 O1 4.7(3) ?
C6 C4 C5 C12 4.6(2) ?
C3 C4 C5 C12 -174.42(14) ?
C1 O1 C5 C4 3.8(2) y
C1 O1 C5 C12 -177.05(13) no
C7 O3 C6 O2 -177.57(15) ?
C7 O3 C6 C4 2.6(2) ?
C5 C4 C6 O2 174.31(17) ?
C3 C4 C6 O2 -6.6(3) ?
C5 C4 C6 O3 -5.9(2) ?
C3 C4 C6 O3 173.20(13) ?
C6 O3 C7 C8 -178.33(15) ?
C6 O3 C7 C12 2.1(2) ?
O3 C7 C8 C9 -179.27(16) ?
C12 C7 C8 C9 0.3(3) ?
C7 C8 C9 C10 0.5(3) ?
C8 C9 C10 C11 -0.8(3) ?
C9 C10 C11 C12 0.4(3) ?
O3 C7 C12 C11 178.79(15) ?
C8 C7 C12 C11 -0.7(3) ?
O3 C7 C12 C5 -3.5(2) ?
C8 C7 C12 C5 176.97(15) ?
C10 C11 C12 C7 0.4(3) ?
C10 C11 C12 C5 -177.11(16) ?
C4 C5 C12 C7 0.1(2) ?
O1 C5 C12 C7 -179.10(14) ?
C4 C5 C12 C11 177.62(16) ?
O1 C5 C12 C11 -1.5(2) ?
C1 C2 C13 N2 -18E1(10) no
C3 C2 C13 N2 3(12) no
C4 C3 C14 C15 -55.3(2) ?
C2 C3 C14 C15 65.2(2) ?
C4 C3 C14 C19 125.70(18) ?
C2 C3 C14 C19 -113.73(18) ?
C19 C14 C15 C16 0.9(3) ?
C3 C14 C15 C16 -178.05(15) ?
C14 C15 C16 C17 -0.3(3) ?
C20 O4 C17 C18 174.91(19) ?
C20 O4 C17 C16 -5.1(3) ?
C15 C16 C17 O4 179.47(16) ?
C15 C16 C17 C18 -0.5(3) ?
O4 C17 C18 C19 -179.31(17) ?
C16 C17 C18 C19 0.7(3) ?
C17 C18 C19 C14 0.0(3) ?
C15 C14 C19 C18 -0.8(3) ?
C3 C14 C19 C18 178.20(17) ?
C23 N3 C21 O5 4.5(3) ?
C22 N3 C21 O5 177.9(2) ?
C28 O6 C24 N4 165.17(14) ?
C28 O6 C24 C25 -13.4(2) yes
N4 C24 C25 C36 -0.6(3) ?
O6 C24 C25 C36 177.66(15) ?
N4 C24 C25 C26 174.77(17) ?
O6 C24 C25 C26 -7.0(3) yes
C24 C25 C26 C27 22.7(2) yes
C36 C25 C26 C27 -161.97(15) ?
C24 C25 C26 C37 -101.31(19) ?
C36 C25 C26 C37 74.05(19) ?
C25 C26 C27 C28 -21.0(2) ?
C37 C26 C27 C28 103.18(18) ?
C25 C26 C27 C29 156.82(15) ?
C37 C26 C27 C29 -78.95(19) ?
C29 C27 C28 O6 -173.98(15) ?
C26 C27 C28 O6 3.9(3) ?
C29 C27 C28 C35 6.0(3) ?
C26 C27 C28 C35 -176.11(15) ?
C24 O6 C28 C27 15.1(2) yes
C24 O6 C28 C35 -164.92(14) ?
C30 O8 C29 O7 -178.05(16) ?
C30 O8 C29 C27 0.7(2) ?
C28 C27 C29 O7 174.00(18) ?
C26 C27 C29 O7 -3.9(3) ?
C28 C27 C29 O8 -4.6(2) ?
C26 C27 C29 O8 177.42(15) ?
C29 O8 C30 C31 -177.34(16) ?
C29 O8 C30 C35 2.0(3) ?
O8 C30 C31 C32 179.14(16) ?
C35 C30 C31 C32 -0.2(3) ?
C30 C31 C32 C33 0.2(3) ?
C31 C32 C33 C34 0.3(3) ?
C32 C33 C34 C35 -0.7(3) ?
O8 C30 C35 C34 -179.52(15) ?
C31 C30 C35 C34 -0.2(3) ?
O8 C30 C35 C28 -0.8(2) ?
C31 C30 C35 C28 178.47(16) ?
C33 C34 C35 C30 0.7(3) ?
C33 C34 C35 C28 -177.92(17) ?
C27 C28 C35 C30 -3.3(2) ?
O6 C28 C35 C30 176.69(14) ?
C27 C28 C35 C34 175.31(17) ?
O6 C28 C35 C34 -4.7(2) ?
C24 C25 C36 N5 -17E1(10) ?
C26 C25 C36 N5 11(9) ?
C27 C26 C37 C38 -96.25(19) ?
C25 C26 C37 C38 25.1(2) ?
C27 C26 C37 C42 83.3(2) ?
C25 C26 C37 C42 -155.32(16) ?
C42 C37 C38 C39 0.9(3) ?
C26 C37 C38 C39 -179.52(15) ?
C37 C38 C39 C40 -0.6(3) ?
C43 O9 C40 C39 6.4(3) ?
C43 O9 C40 C41 -174.67(18) ?
C38 C39 C40 O9 178.57(16) ?
C38 C39 C40 C41 -0.3(3) ?
O9 C40 C41 C42 -177.99(18) ?
C39 C40 C41 C42 1.0(3) ?
C40 C41 C42 C37 -0.7(3) ?
C38 C37 C42 C41 -0.2(3) ?
C26 C37 C42 C41 -179.80(17) ?
C46 N6 C44 O10 -4.0(4) ?
C45 N6 C44 O10 179.0(3) ?
