#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025128.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025128
loop_
_publ_author_name
'Patrick J. Gross'
'Caroline E. Hartmann'
'Martin Nieger'
'Stefan Bräse'
_publ_contact_author
;
        Martin Nieger
        Laboratory of Inorganic Chemistry
        Department of Chemistry
        Universitity of Helsinki
        P.O. Box 55
        FIN-00014 University of Helsinki
        Finland
;
_publ_contact_author_email       martin.nieger@helsinki.fi
_publ_contact_author_fax         '++358 9 191 50198'
_publ_contact_author_phone       '++358 9 191 50223'
_publ_section_title
;
 Synthesis of Methoxyfumimycin with 1,2-Addition to Ketimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              229
_journal_page_last               232
_journal_paper_doi               10.1021/jo902026s
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C25 H24 N O5 P'
_chemical_formula_sum            'C25 H24 N O5 P'
_chemical_formula_weight         449.42
_chemical_name_systematic
; 
 (E)-N-(5-hydroxy-6-methoxy-3-methyl-2-oxo-4-(prop-1-enyl)-2,3-dihydro-
 benzofuran-3-yl)-P,P-diphenylphosphinic amide
;
_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                99.86(1)
_cell_angle_beta                 105.95(1)
_cell_angle_gamma                103.28(1)
_cell_formula_units_Z            4
_cell_length_a                   10.199(1)
_cell_length_b                   13.332(1)
_cell_length_c                   17.800(1)
_cell_measurement_reflns_used    173
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     2192.7(4)
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22725
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         9958
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0469
_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)+(0.0472P)²+1.7050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                7695
_reflns_number_total             9958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902026s_si_001_2.cif
_cod_data_source_block           sb093_hy_compound_18
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:
data name '_publ_contact_autor' replaced with '_publ_contact_author'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 4998 2017-03-02 13:24:31Z antanas 
;
_cod_original_cell_volume        2192.7(3)
_cod_database_code               4025128
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44997(15) 0.71310(10) 0.04468(8) 0.0236(3) Uani 1 1 d . . .
C2 C 0.3457(2) 0.67966(15) 0.07728(12) 0.0214(4) Uani 1 1 d . . .
O2 O 0.29112(15) 0.58711(11) 0.06886(9) 0.0273(3) Uani 1 1 d . . .
C3 C 0.31342(19) 0.77619(15) 0.12194(11) 0.0186(4) Uani 1 1 d . . .
C31 C 0.1649(2) 0.77610(17) 0.07269(13) 0.0250(4) Uani 1 1 d . . .
H31A H 0.0950 0.7097 0.0689 0.038 Uiso 1 1 calc R . .
H31B H 0.1638 0.7819 0.0184 0.038 Uiso 1 1 calc R . .
H31C H 0.1407 0.8367 0.0991 0.038 Uiso 1 1 calc R . .
N3 N 0.31454(16) 0.76462(13) 0.20188(10) 0.0188(3) Uani 1 1 d D . .
H3 H 0.2336(19) 0.7495(17) 0.2090(14) 0.023 Uiso 1 1 d D . .
P3 P 0.46182(5) 0.77546(4) 0.27381(3) 0.01587(11) Uani 1 1 d . . .
O3 O 0.57579(14) 0.75689(11) 0.24135(8) 0.0205(3) Uani 1 1 d . . .
C8 C 0.5157(2) 0.90527(15) 0.34150(11) 0.0181(4) Uani 1 1 d . . .
C9 C 0.4152(2) 0.94207(16) 0.36906(12) 0.0221(4) Uani 1 1 d . . .
H9 H 0.3204 0.8972 0.3544 0.027 Uiso 1 1 calc R . .
C10 C 0.4542(2) 1.04406(16) 0.41774(13) 0.0248(4) Uani 1 1 d . . .
H10 H 0.3865 1.0690 0.4370 0.030 Uiso 1 1 calc R . .
C11 C 0.5921(2) 1.10968(16) 0.43832(13) 0.0269(5) Uani 1 1 d . . .
H11 H 0.6183 1.1798 0.4714 0.032 Uiso 1 1 calc R . .
C12 C 0.6913(2) 1.07386(17) 0.41114(13) 0.0280(5) Uani 1 1 d . . .
H12 H 0.7856 1.1195 0.4254 0.034 Uiso 1 1 calc R . .
C13 C 0.6540(2) 0.97117(16) 0.36296(13) 0.0232(4) Uani 1 1 d . . .
H13 H 0.7229 0.9462 0.3448 0.028 Uiso 1 1 calc R . .
C14 C 0.41275(19) 0.68270(14) 0.33099(12) 0.0178(4) Uani 1 1 d . . .
C15 C 0.4849(2) 0.70573(16) 0.41341(12) 0.0206(4) Uani 1 1 d . . .
H15 H 0.5540 0.7729 0.4399 0.025 Uiso 1 1 calc R . .
C16 C 0.4571(2) 0.63160(17) 0.45733(13) 0.0246(4) Uani 1 1 d . . .
H16 H 0.5069 0.6482 0.5136 0.030 Uiso 1 1 calc R . .
C17 C 0.3572(2) 0.53386(17) 0.41941(14) 0.0264(4) Uani 1 1 d . . .
H17 H 0.3382 0.4831 0.4495 0.032 Uiso 1 1 calc R . .
C18 C 0.2848(2) 0.50980(17) 0.33743(14) 0.0281(5) Uani 1 1 d . . .
H18 H 0.2161 0.4424 0.3114 0.034 Uiso 1 1 calc R . .
C19 C 0.3119(2) 0.58339(16) 0.29297(13) 0.0238(4) Uani 1 1 d . . .
H19 H 0.2620 0.5663 0.2367 0.029 Uiso 1 1 calc R . .
C3A C 0.42867(19) 0.86700(15) 0.11680(11) 0.0182(4) Uani 1 1 d . . .
C4 C 0.46233(19) 0.97795(15) 0.14495(11) 0.0186(4) Uani 1 1 d . . .
C41 C 0.3813(2) 1.02186(16) 0.19168(12) 0.0217(4) Uani 1 1 d . . .
H41 H 0.3141 0.9705 0.2039 0.026 Uiso 1 1 calc R . .
C42 C 0.3877(2) 1.12252(17) 0.21961(14) 0.0288(5) Uani 1 1 d . . .
H42 H 0.4534 1.1773 0.2094 0.035 Uiso 1 1 calc R . .
C43 C 0.2953(3) 1.15311(19) 0.26661(16) 0.0360(5) Uani 1 1 d . . .
H43A H 0.2309 1.0887 0.2706 0.054 Uiso 1 1 calc R . .
H43B H 0.2391 1.1947 0.2391 0.054 Uiso 1 1 calc R . .
H43C H 0.3554 1.1959 0.3209 0.054 Uiso 1 1 calc R . .
C5 C 0.5747(2) 1.03886(15) 0.12603(12) 0.0210(4) Uani 1 1 d . . .
O5 O 0.61549(16) 1.14727(11) 0.15255(10) 0.0305(4) Uani 1 1 d D . .
H5 H 0.690(2) 1.170(2) 0.1425(17) 0.046 Uiso 1 1 d D . .
C6 C 0.6480(2) 0.99137(16) 0.08115(12) 0.0209(4) Uani 1 1 d . . .
O6 O 0.75976(15) 1.06302(11) 0.07176(9) 0.0264(3) Uani 1 1 d . . .
C61 C 0.8516(2) 1.01950(19) 0.03745(15) 0.0321(5) Uani 1 1 d . . .
H61A H 0.8847 0.9699 0.0674 0.048 Uiso 1 1 calc R . .
H61B H 0.9338 1.0771 0.0405 0.048 Uiso 1 1 calc R . .
H61C H 0.7995 0.9816 -0.0191 0.048 Uiso 1 1 calc R . .
C7 C 0.6107(2) 0.88210(16) 0.05146(12) 0.0216(4) Uani 1 1 d . . .
H7 H 0.6583 0.8494 0.0200 0.026 Uiso 1 1 calc R . .
C7A C 0.4999(2) 0.82418(15) 0.07072(11) 0.0198(4) Uani 1 1 d . . .
O1' O 0.91473(15) 0.57811(10) 0.07365(8) 0.0211(3) Uani 1 1 d . . .
C2' C 0.8263(2) 0.62958(16) 0.09721(12) 0.0225(4) Uani 1 1 d . . .
O2' O 0.80240(18) 0.70339(12) 0.07269(9) 0.0319(4) Uani 1 1 d . . .
C3' C 0.7680(2) 0.57848(15) 0.15735(11) 0.0191(4) Uani 1 1 d . . .
C31' C 0.6072(2) 0.52749(17) 0.11657(13) 0.0259(5) Uani 1 1 d . . .
H31D H 0.5670 0.4945 0.1536 0.039 Uiso 1 1 calc R . .
H31E H 0.5896 0.4730 0.0674 0.039 Uiso 1 1 calc R . .
H31F H 0.5621 0.5822 0.1026 0.039 Uiso 1 1 calc R . .
N3' N 0.79478(16) 0.66348(12) 0.22872(10) 0.0180(3) Uani 1 1 d D . .
H3' H 0.726(2) 0.6902(16) 0.2295(14) 0.022 Uiso 1 1 d D . .
P3' P 0.95623(5) 0.73209(4) 0.28970(3) 0.01578(11) Uani 1 1 d . . .
O3' O 1.07013(14) 0.71261(10) 0.25734(8) 0.0209(3) Uani 1 1 d . . .
C8' C 0.97174(19) 0.69791(14) 0.38469(11) 0.0176(4) Uani 1 1 d . . .
C9' C 0.8658(2) 0.70278(16) 0.41974(12) 0.0221(4) Uani 1 1 d . . .
H9' H 0.7866 0.7247 0.3937 0.027 Uiso 1 1 calc R . .
C10' C 0.8760(2) 0.67571(16) 0.49240(13) 0.0267(5) Uani 1 1 d . . .
H10' H 0.8043 0.6800 0.5164 0.032 Uiso 1 1 calc R . .
C11' C 0.9898(3) 0.64250(17) 0.53010(13) 0.0302(5) Uani 1 1 d . . .
H11' H 0.9964 0.6237 0.5799 0.036 Uiso 1 1 calc R . .
C12' C 1.0942(2) 0.63669(17) 0.49515(14) 0.0313(5) Uani 1 1 d . . .
H12' H 1.1723 0.6134 0.5209 0.038 Uiso 1 1 calc R . .
C13' C 1.0856(2) 0.66460(16) 0.42286(13) 0.0241(4) Uani 1 1 d . . .
H13' H 1.1581 0.6609 0.3994 0.029 Uiso 1 1 calc R . .
C14' C 0.96015(19) 0.87019(15) 0.31027(11) 0.0176(4) Uani 1 1 d . . .
C15' C 1.0381(2) 0.93687(15) 0.38690(12) 0.0220(4) Uani 1 1 d . . .
H15' H 1.0817 0.9081 0.4291 0.026 Uiso 1 1 calc R . .
C16' C 1.0522(2) 1.04530(16) 0.40175(13) 0.0240(4) Uani 1 1 d . . .
H16' H 1.1051 1.0905 0.4540 0.029 Uiso 1 1 calc R . .
C17' C 0.9892(2) 1.08728(15) 0.34031(13) 0.0230(4) Uani 1 1 d . . .
H17' H 0.9987 1.1614 0.3504 0.028 Uiso 1 1 calc R . .
C18' C 0.9122(2) 1.02161(16) 0.26405(13) 0.0240(4) Uani 1 1 d . . .
H18' H 0.8694 1.0508 0.2219 0.029 Uiso 1 1 calc R . .
C19' C 0.8974(2) 0.91306(15) 0.24895(12) 0.0216(4) Uani 1 1 d . . .
H19' H 0.8444 0.8682 0.1966 0.026 Uiso 1 1 calc R . .
C3A' C 0.84881(19) 0.49656(14) 0.16819(11) 0.0175(4) Uani 1 1 d . . .
C4' C 0.84874(19) 0.41875(15) 0.21259(11) 0.0190(4) Uani 1 1 d . . .
C41' C 0.7627(2) 0.39450(18) 0.26522(13) 0.0277(5) Uani 1 1 d . . .
H41' H 0.7583 0.3284 0.2791 0.033 Uiso 1 1 calc R . .
C42' C 0.6925(2) 0.45062(18) 0.29507(14) 0.0305(5) Uani 1 1 d . . .
H42' H 0.6981 0.5190 0.2851 0.037 Uiso 1 1 calc R . .
C43' C 0.6026(2) 0.4132(2) 0.34480(15) 0.0359(6) Uani 1 1 d . . .
H43D H 0.6096 0.3431 0.3519 0.054 Uiso 1 1 calc R . .
H43E H 0.5030 0.4081 0.3172 0.054 Uiso 1 1 calc R . .
H43F H 0.6366 0.4640 0.3977 0.054 Uiso 1 1 calc R . .
C5' C 0.9358(2) 0.35390(15) 0.20238(12) 0.0208(4) Uani 1 1 d . . .
O5' O 0.94451(17) 0.27757(12) 0.24564(10) 0.0300(3) Uani 1 1 d D . .
H5' H 1.001(3) 0.245(2) 0.2356(17) 0.045 Uiso 1 1 d D . .
C6' C 1.0175(2) 0.36390(15) 0.15117(12) 0.0204(4) Uani 1 1 d . . .
O6' O 1.09883(16) 0.29461(12) 0.15163(9) 0.0290(3) Uani 1 1 d . . .
C61' C 1.1998(3) 0.3098(2) 0.10955(16) 0.0400(6) Uani 1 1 d . . .
H61D H 1.1492 0.2965 0.0517 0.060 Uiso 1 1 calc R . .
H61E H 1.2569 0.2603 0.1181 0.060 Uiso 1 1 calc R . .
H61F H 1.2626 0.3831 0.1299 0.060 Uiso 1 1 calc R . .
C7' C 1.0143(2) 0.43784(15) 0.10600(12) 0.0195(4) Uani 1 1 d . . .
H7' H 1.0678 0.4450 0.0701 0.023 Uiso 1 1 calc R . .
C7A' C 0.9279(2) 0.50075(14) 0.11668(11) 0.0176(4) Uani 1 1 d . . .
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'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C7A 107.49(14) . . ?
O2 C2 O1 121.37(18) . . ?
O2 C2 C3 128.26(19) . . ?
O1 C2 C3 110.36(16) . . ?
N3 C3 C3A 117.60(15) . . ?
N3 C3 C31 109.64(16) . . ?
C3A C3 C31 111.62(17) . . ?
N3 C3 C2 109.44(16) . . ?
C3A C3 C2 100.65(15) . . ?
C31 C3 C2 107.08(15) . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C3 N3 P3 122.32(13) . . ?
C3 N3 H3 116.2(16) . . ?
P3 N3 H3 121.5(16) . . ?
O3 P3 N3 112.08(8) . . ?
O3 P3 C8 111.85(8) . . ?
N3 P3 C8 107.79(9) . . ?
O3 P3 C14 113.06(8) . . ?
N3 P3 C14 106.06(9) . . ?
C8 P3 C14 105.55(9) . . ?
C13 C8 C9 119.91(17) . . ?
C13 C8 P3 120.41(14) . . ?
C9 C8 P3 119.58(14) . . ?
C10 C9 C8 119.81(18) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.98(18) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.42(18) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.22(19) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 119.65(18) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C19 118.91(19) . . ?
C15 C14 P3 119.72(14) . . ?
C19 C14 P3 121.12(16) . . ?
C16 C15 C14 120.67(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.48(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 119.99(19) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C7A C3A C4 120.32(17) . . ?
C7A C3A C3 107.74(16) . . ?
C4 C3A C3 131.77(17) . . ?
C5 C4 C3A 115.94(17) . . ?
C5 C4 C41 124.77(17) . . ?
C3A C4 C41 119.28(17) . . ?
C42 C41 C4 129.8(2) . . ?
C42 C41 H41 115.1 . . ?
C4 C41 H41 115.1 . . ?
C41 C42 C43 122.6(2) . . ?
C41 C42 H42 118.7 . . ?
C43 C42 H42 118.7 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O5 C5 C4 119.42(17) . . ?
O5 C5 C6 118.86(17) . . ?
C4 C5 C6 121.71(17) . . ?
C5 O5 H5 107(2) . . ?
O6 C6 C7 124.44(18) . . ?
O6 C6 C5 113.77(17) . . ?
C7 C6 C5 121.77(18) . . ?
C6 O6 C61 116.62(16) . . ?
O6 C61 H61A 109.5 . . ?
O6 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
O6 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C7A C7 C6 115.33(18) . . ?
C7A C7 H7 122.3 . . ?
C6 C7 H7 122.3 . . ?
C3A C7A C7 124.83(18) . . ?
C3A C7A O1 113.36(17) . . ?
C7 C7A O1 121.81(17) . . ?
C2' O1' C7A' 107.91(15) . . ?
O2' C2' O1' 121.82(19) . . ?
O2' C2' C3' 127.90(18) . . ?
O1' C2' C3' 110.28(17) . . ?
N3' C3' C3A' 117.13(16) . . ?
N3' C3' C31' 109.70(15) . . ?
C3A' C3' C31' 112.61(16) . . ?
N3' C3' C2' 107.80(15) . . ?
C3A' C3' C2' 101.12(15) . . ?
C31' C3' C2' 107.65(17) . . ?
C3' C31' H31D 109.5 . . ?
C3' C31' H31E 109.5 . . ?
H31D C31' H31E 109.5 . . ?
C3' C31' H31F 109.5 . . ?
H31D C31' H31F 109.5 . . ?
H31E C31' H31F 109.5 . . ?
C3' N3' P3' 122.99(12) . . ?
C3' N3' H3' 116.1(15) . . ?
P3' N3' H3' 118.1(15) . . ?
O3' P3' N3' 113.04(8) . . ?
O3' P3' C8' 112.55(9) . . ?
N3' P3' C8' 106.17(9) . . ?
O3' P3' C14' 112.96(8) . . ?
N3' P3' C14' 106.94(9) . . ?
C8' P3' C14' 104.54(9) . . ?
C13' C8' C9' 119.3(2) . . ?
C13' C8' P3' 121.06(15) . . ?
C9' C8' P3' 119.65(15) . . ?
C10' C9' C8' 120.1(2) . . ?
C10' C9' H9' 119.9 . . ?
C8' C9' H9' 119.9 . . ?
C11' C10' C9' 120.3(2) . . ?
C11' C10' H10' 119.9 . . ?
C9' C10' H10' 119.9 . . ?
C10' C11' C12' 119.7(2) . . ?
C10' C11' H11' 120.2 . . ?
C12' C11' H11' 120.2 . . ?
C11' C12' C13' 120.4(2) . . ?
C11' C12' H12' 119.8 . . ?
C13' C12' H12' 119.8 . . ?
C8' C13' C12' 120.2(2) . . ?
C8' C13' H13' 119.9 . . ?
C12' C13' H13' 119.9 . . ?
C19' C14' C15' 119.45(18) . . ?
C19' C14' P3' 120.69(14) . . ?
C15' C14' P3' 119.60(16) . . ?
C16' C15' C14' 120.24(19) . . ?
C16' C15' H15' 119.9 . . ?
C14' C15' H15' 119.9 . . ?
C17' C16' C15' 119.90(18) . . ?
C17' C16' H16' 120.1 . . ?
C15' C16' H16' 120.1 . . ?
C16' C17' C18' 120.15(18) . . ?
C16' C17' H17' 119.9 . . ?
C18' C17' H17' 119.9 . . ?
C17' C18' C19' 120.2(2) . . ?
C17' C18' H18' 119.9 . . ?
C19' C18' H18' 119.9 . . ?
C14' C19' C18' 120.08(18) . . ?
C14' C19' H19' 120.0 . . ?
C18' C19' H19' 120.0 . . ?
C7A' C3A' C4' 118.88(17) . . ?
C7A' C3A' C3' 106.96(17) . . ?
C4' C3A' C3' 133.95(17) . . ?
C5' C4' C3A' 115.78(17) . . ?
C5' C4' C41' 116.52(19) . . ?
C3A' C4' C41' 127.63(18) . . ?
C42' C41' C4' 129.1(2) . . ?
C42' C41' H41' 115.5 . . ?
C4' C41' H41' 115.5 . . ?
C41' C42' C43' 123.4(2) . . ?
C41' C42' H42' 118.3 . . ?
C43' C42' H42' 118.3 . . ?
C42' C43' H43D 109.5 . . ?
C42' C43' H43E 109.5 . . ?
H43D C43' H43E 109.5 . . ?
C42' C43' H43F 109.5 . . ?
H43D C43' H43F 109.5 . . ?
H43E C43' H43F 109.5 . . ?
O5' C5' C6' 117.86(18) . . ?
O5' C5' C4' 119.21(18) . . ?
C6' C5' C4' 122.91(19) . . ?
C5' O5' H5' 111(2) . . ?
C7' C6' O6' 124.95(18) . . ?
C7' C6' C5' 121.30(18) . . ?
O6' C6' C5' 113.74(18) . . ?
C6' O6' C61' 116.94(17) . . ?
O6' C61' H61D 109.5 . . ?
O6' C61' H61E 109.5 . . ?
H61D C61' H61E 109.5 . . ?
O6' C61' H61F 109.5 . . ?
H61D C61' H61F 109.5 . . ?
H61E C61' H61F 109.5 . . ?
C6' C7' C7A' 114.95(17) . . ?
C6' C7' H7' 122.5 . . ?
C7A' C7' H7' 122.5 . . ?
C7' C7A' C3A' 126.10(19) . . ?
C7' C7A' O1' 120.36(17) . . ?
C3A' C7A' O1' 113.54(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.370(2) . ?
O1 C7A 1.399(2) . ?
C2 O2 1.196(2) . ?
C2 C3 1.544(3) . ?
C3 N3 1.454(3) . ?
C3 C3A 1.516(3) . ?
C3 C31 1.527(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
N3 P3 1.6421(17) . ?
N3 H3 0.853(15) . ?
P3 O3 1.4828(13) . ?
P3 C8 1.7983(19) . ?
P3 C14 1.801(2) . ?
C8 C13 1.389(3) . ?
C8 C9 1.399(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 C19 1.398(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C3A C7A 1.372(3) . ?
C3A C4 1.406(3) . ?
C4 C5 1.402(3) . ?
C4 C41 1.466(3) . ?
C41 C42 1.329(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.499(3) . ?
C42 H42 0.9500 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C5 O5 1.366(2) . ?
C5 C6 1.404(3) . ?
O5 H5 0.829(17) . ?
C6 O6 1.378(2) . ?
C6 C7 1.385(3) . ?
O6 C61 1.425(2) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C7 C7A 1.376(3) . ?
C7 H7 0.9500 . ?
O1' C2' 1.362(2) . ?
O1' C7A' 1.395(2) . ?
C2' O2' 1.190(3) . ?
C2' C3' 1.542(3) . ?
C3' N3' 1.465(2) . ?
C3' C3A' 1.519(3) . ?
C3' C31' 1.530(3) . ?
C31' H31D 0.9800 . ?
C31' H31E 0.9800 . ?
C31' H31F 0.9800 . ?
N3' P3' 1.6468(16) . ?
N3' H3' 0.855(15) . ?
P3' O3' 1.4845(13) . ?
P3' C8' 1.800(2) . ?
P3' C14' 1.8034(19) . ?
C8' C13' 1.384(3) . ?
C8' C9' 1.396(3) . ?
C9' C10' 1.384(3) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.379(3) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.383(3) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.385(3) . ?
C12' H12' 0.9500 . ?
C13' H13' 0.9500 . ?
C14' C19' 1.387(3) . ?
C14' C15' 1.395(3) . ?
C15' C16' 1.390(3) . ?
C15' H15' 0.9500 . ?
C16' C17' 1.382(3) . ?
C16' H16' 0.9500 . ?
C17' C18' 1.385(3) . ?
C17' H17' 0.9500 . ?
C18' C19' 1.391(3) . ?
C18' H18' 0.9500 . ?
C19' H19' 0.9500 . ?
C3A' C7A' 1.378(3) . ?
C3A' C4' 1.408(3) . ?
C4' C5' 1.399(3) . ?
C4' C41' 1.475(3) . ?
C41' C42' 1.294(3) . ?
C41' H41' 0.9500 . ?
C42' C43' 1.503(3) . ?
C42' H42' 0.9500 . ?
C43' H43D 0.9800 . ?
C43' H43E 0.9800 . ?
C43' H43F 0.9800 . ?
C5' O5' 1.381(2) . ?
C5' C6' 1.397(3) . ?
O5' H5' 0.836(17) . ?
C6' C7' 1.375(3) . ?
C6' O6' 1.376(2) . ?
O6' C61' 1.429(3) . ?
C61' H61D 0.9800 . ?
C61' H61E 0.9800 . ?
C61' H61F 0.9800 . ?
C7' C7A' 1.376(3) . ?
C7' H7' 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O3' 0.853(15) 2.078(17) 2.909(2) 164(2) 1_455
O5 H5 O6 0.829(17) 2.12(3) 2.620(2) 119(2) .
O5 H5 O5' 0.829(17) 2.63(2) 3.210(2) 128(2) 1_565
N3' H3' O3 0.855(15) 1.984(16) 2.837(2) 175(2) .
O5' H5' O6' 0.836(17) 2.12(3) 2.597(2) 116(2) .
C7' H7' O1' 0.95 2.58 3.450(2) 151.6 2_765
C31 H31A O1' 0.98 2.26 3.229(3) 168.5 1_455
C31' H31F O1 0.98 2.51 3.480(3) 170.8 .
C41' H41' O5' 0.95 2.34 2.736(3) 104.1 .
C42 H42 O5 0.95 2.24 2.870(3) 123.3 .
C42' H42' N3' 0.95 2.45 3.317(3) 150.9 .
C43 H43B O6' 0.98 2.57 3.545(3) 173.0 1_465
C61' H61D O2' 0.98 2.40 3.212(3) 140.1 2_765
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7A O1 C2 O2 -175.06(19) . . . . ?
C7A O1 C2 C3 5.8(2) . . . . ?
O2 C2 C3 N3 50.0(3) . . . . ?
O1 C2 C3 N3 -130.89(16) . . . . ?
O2 C2 C3 C3A 174.5(2) . . . . ?
O1 C2 C3 C3A -6.4(2) . . . . ?
O2 C2 C3 C31 -68.8(3) . . . . ?
O1 C2 C3 C31 110.34(18) . . . . ?
C3A C3 N3 P3 -43.9(2) . . . . ?
C31 C3 N3 P3 -172.77(13) . . . . ?
C2 C3 N3 P3 70.06(18) . . . . ?
C3 N3 P3 O3 -21.64(17) . . . . ?
C3 N3 P3 C8 101.87(16) . . . . ?
C3 N3 P3 C14 -145.46(15) . . . . ?
O3 P3 C8 C13 -5.3(2) . . . . ?
N3 P3 C8 C13 -128.94(17) . . . . ?
C14 P3 C8 C13 118.05(18) . . . . ?
O3 P3 C8 C9 171.20(16) . . . . ?
N3 P3 C8 C9 47.55(19) . . . . ?
C14 P3 C8 C9 -65.46(18) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
P3 C8 C9 C10 -176.59(17) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C9 C8 C13 C12 -0.7(3) . . . . ?
P3 C8 C13 C12 175.83(18) . . . . ?
C11 C12 C13 C8 0.8(3) . . . . ?
O3 P3 C14 C15 88.83(16) . . . . ?
N3 P3 C14 C15 -147.96(15) . . . . ?
C8 P3 C14 C15 -33.74(17) . . . . ?
O3 P3 C14 C19 -85.38(17) . . . . ?
N3 P3 C14 C19 37.83(18) . . . . ?
C8 P3 C14 C19 152.05(16) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
P3 C14 C15 C16 -174.59(14) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C15 C14 C19 C18 0.3(3) . . . . ?
P3 C14 C19 C18 174.51(15) . . . . ?
N3 C3 C3A C7A 123.32(18) . . . . ?
C31 C3 C3A C7A -108.71(19) . . . . ?
C2 C3 C3A C7A 4.6(2) . . . . ?
N3 C3 C3A C4 -61.5(3) . . . . ?
C31 C3 C3A C4 66.5(3) . . . . ?
C2 C3 C3A C4 179.8(2) . . . . ?
C7A C3A C4 C5 -2.8(3) . . . . ?
C3 C3A C4 C5 -177.4(2) . . . . ?
C7A C3A C4 C41 177.87(18) . . . . ?
C3 C3A C4 C41 3.2(3) . . . . ?
C5 C4 C41 C42 5.5(4) . . . . ?
C3A C4 C41 C42 -175.2(2) . . . . ?
C4 C41 C42 C43 179.8(2) . . . . ?
C3A C4 C5 O5 -178.82(18) . . . . ?
C41 C4 C5 O5 0.5(3) . . . . ?
C3A C4 C5 C6 0.5(3) . . . . ?
C41 C4 C5 C6 179.80(19) . . . . ?
O5 C5 C6 O6 2.4(3) . . . . ?
C4 C5 C6 O6 -176.91(18) . . . . ?
O5 C5 C6 C7 -179.01(19) . . . . ?
C4 C5 C6 C7 1.7(3) . . . . ?
C7 C6 O6 C61 -7.7(3) . . . . ?
C5 C6 O6 C61 170.91(18) . . . . ?
O6 C6 C7 C7A 176.99(19) . . . . ?
C5 C6 C7 C7A -1.5(3) . . . . ?
C4 C3A C7A C7 3.2(3) . . . . ?
C3 C3A C7A C7 179.00(19) . . . . ?
C4 C3A C7A O1 -177.45(17) . . . . ?
C3 C3A C7A O1 -1.6(2) . . . . ?
C6 C7 C7A C3A -0.9(3) . . . . ?
C6 C7 C7A O1 179.71(18) . . . . ?
C2 O1 C7A C3A -2.7(2) . . . . ?
C2 O1 C7A C7 176.74(19) . . . . ?
C7A' O1' C2' O2' 176.12(19) . . . . ?
C7A' O1' C2' C3' -3.61(19) . . . . ?
O2' C2' C3' N3' -51.7(3) . . . . ?
O1' C2' C3' N3' 127.99(16) . . . . ?
O2' C2' C3' C3A' -175.2(2) . . . . ?
O1' C2' C3' C3A' 4.54(19) . . . . ?
O2' C2' C3' C31' 66.5(3) . . . . ?
O1' C2' C3' C31' -113.74(17) . . . . ?
C3A' C3' N3' P3' 47.2(2) . . . . ?
C31' C3' N3' P3' 177.17(15) . . . . ?
C2' C3' N3' P3' -65.9(2) . . . . ?
C3' N3' P3' O3' 10.26(19) . . . . ?
C3' N3' P3' C8' -113.61(16) . . . . ?
C3' N3' P3' C14' 135.19(16) . . . . ?
O3' P3' C8' C13' 4.15(18) . . . . ?
N3' P3' C8' C13' 128.32(15) . . . . ?
C14' P3' C8' C13' -118.81(16) . . . . ?
O3' P3' C8' C9' -174.44(14) . . . . ?
N3' P3' C8' C9' -50.27(16) . . . . ?
C14' P3' C8' C9' 62.60(16) . . . . ?
C13' C8' C9' C10' 0.8(3) . . . . ?
P3' C8' C9' C10' 179.40(15) . . . . ?
C8' C9' C10' C11' -0.8(3) . . . . ?
C9' C10' C11' C12' 0.2(3) . . . . ?
C10' C11' C12' C13' 0.4(3) . . . . ?
C9' C8' C13' C12' -0.2(3) . . . . ?
P3' C8' C13' C12' -178.75(15) . . . . ?
C11' C12' C13' C8' -0.4(3) . . . . ?
O3' P3' C14' C19' 82.55(17) . . . . ?
N3' P3' C14' C19' -42.44(18) . . . . ?
C8' P3' C14' C19' -154.75(15) . . . . ?
O3' P3' C14' C15' -91.56(17) . . . . ?
N3' P3' C14' C15' 143.46(15) . . . . ?
C8' P3' C14' C15' 31.14(17) . . . . ?
C19' C14' C15' C16' 0.3(3) . . . . ?
P3' C14' C15' C16' 174.49(15) . . . . ?
C14' C15' C16' C17' -0.2(3) . . . . ?
C15' C16' C17' C18' -0.1(3) . . . . ?
C16' C17' C18' C19' 0.2(3) . . . . ?
C15' C14' C19' C18' -0.1(3) . . . . ?
P3' C14' C19' C18' -174.23(15) . . . . ?
C17' C18' C19' C14' -0.2(3) . . . . ?
N3' C3' C3A' C7A' -120.53(18) . . . . ?
C31' C3' C3A' C7A' 110.88(18) . . . . ?
C2' C3' C3A' C7A' -3.73(18) . . . . ?
N3' C3' C3A' C4' 65.0(3) . . . . ?
C31' C3' C3A' C4' -63.6(3) . . . . ?
C2' C3' C3A' C4' -178.25(19) . . . . ?
C7A' C3A' C4' C5' 2.5(2) . . . . ?
C3' C3A' C4' C5' 176.50(18) . . . . ?
C7A' C3A' C4' C41' -174.30(18) . . . . ?
C3' C3A' C4' C41' -0.3(3) . . . . ?
C5' C4' C41' C42' 167.7(2) . . . . ?
C3A' C4' C41' C42' -15.5(4) . . . . ?
C4' C41' C42' C43' 176.7(2) . . . . ?
C3A' C4' C5' O5' 178.22(16) . . . . ?
C41' C4' C5' O5' -4.6(3) . . . . ?
C3A' C4' C5' C6' -0.5(3) . . . . ?
C41' C4' C5' C6' 176.66(18) . . . . ?
O5' C5' C6' C7' 179.86(17) . . . . ?
C4' C5' C6' C7' -1.4(3) . . . . ?
O5' C5' C6' O6' -0.6(2) . . . . ?
C4' C5' C6' O6' 178.17(17) . . . . ?
C7' C6' O6' C61' 8.0(3) . . . . ?
C5' C6' O6' C61' -171.60(19) . . . . ?
O6' C6' C7' C7A' -178.36(17) . . . . ?
C5' C6' C7' C7A' 1.2(3) . . . . ?
C6' C7' C7A' C3A' 1.0(3) . . . . ?
C6' C7' C7A' O1' -179.41(16) . . . . ?
C4' C3A' C7A' C7' -2.9(3) . . . . ?
C3' C3A' C7A' C7' -178.42(17) . . . . ?
C4' C3A' C7A' O1' 177.46(15) . . . . ?
C3' C3A' C7A' O1' 2.0(2) . . . . ?
C2' O1' C7A' C7' -178.59(16) . . . . ?
C2' O1' C7A' C3A' 1.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091372
