#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:00:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178455 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/76/4027641.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_4027641
loop_
_publ_author_name
'Stephen Hanessian'
'Ramkrishna Reddy Vakiti'
'Stéphane Dorich'
'Shyamapada Banerjee'
'Benoît Deschênes-Simard'
_publ_section_title
;
 Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9458
_journal_page_last               9472
_journal_paper_doi               10.1021/jo301638z
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C17 H22 N4 O6'
_chemical_formula_sum            'C17 H22 N4 O6'
_chemical_formula_weight         378.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 92.706(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0802(1)
_cell_length_b                   34.2482(4)
_cell_length_c                   7.5495(1)
_cell_measurement_reflns_used    21588
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.15
_cell_measurement_theta_min      2.58
_cell_volume                     1828.59(4)
_computing_cell_refinement       'SAINT V7.60A(Bruker AXS, 2008)'
_computing_data_collection       'APEX2  (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT V7.60A(Bruker AXS, 2008)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            24164
_diffrn_reflns_theta_full        72.55
_diffrn_reflns_theta_max         72.55
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  0.9232
_exptl_absorpt_correction_T_min  0.7071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), 3271 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         6968
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0364
_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)+(0.0733P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                6673
_reflns_number_total             6968
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo301638z_si_008.cif
_cod_data_source_block           bent88
_cod_database_code               4027641
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
O11 O 0.44211(17) 0.59733(3) 0.46094(15) 0.0322(2) Uani 1 1 d . A .
H11 H 0.3606 0.5985 0.3765 0.048 Uiso 1 1 calc R . .
O12 O 0.25123(16) 0.56393(3) 0.85942(15) 0.0319(2) Uani 1 1 d . . .
H12 H 0.2437 0.5395 0.8518 0.048 Uiso 1 1 calc R . .
O13 O 0.76076(17) 0.57328(4) 0.78546(17) 0.0370(3) Uani 1 1 d . . .
H13 H 0.7990 0.5903 0.8586 0.056 Uiso 1 1 calc R . .
O14 O 0.26393(18) 0.64143(3) 0.73499(16) 0.0357(3) Uani 1 1 d . A .
H14 H 0.2633 0.6413 0.6237 0.054 Uiso 1 1 calc R . .
O15 O 0.6845(2) 0.45220(4) 0.8098(2) 0.0419(3) Uani 1 1 d . A .
O16 O 0.1027(2) 0.32215(4) 1.0101(2) 0.0486(4) Uani 1 1 d . A .
N11 N 0.4291(2) 0.49157(4) 0.8004(2) 0.0326(3) Uani 1 1 d . A .
C12 C 0.5486(11) 0.53330(18) 0.5535(5) 0.0343(5) Uani 0.415(7) 1 d PD A 1
H12B H 0.6682 0.5461 0.5186 0.041 Uiso 0.415(7) 1 calc PR A 1
N12 N 0.5017(10) 0.5027(3) 0.4213(16) 0.0574(10) Uani 0.415(7) 1 d PD A 1
N13 N 0.3368(12) 0.4967(5) 0.377(2) 0.0536(8) Uani 0.415(7) 1 d PDU A 1
N14 N 0.1921(9) 0.4829(2) 0.3373(11) 0.0657(10) Uani 0.415(7) 1 d PDU A 1
C32 C 0.5326(8) 0.53053(13) 0.5512(4) 0.0343(5) Uani 0.585(7) 1 d PD A 2
H12C H 0.6514 0.5414 0.5045 0.041 Uiso 0.585(7) 1 calc PR A 2
N32 N 0.4723(8) 0.4990(2) 0.4289(11) 0.0574(10) Uani 0.585(7) 1 d PD A 2
N33 N 0.3129(9) 0.4989(3) 0.3624(15) 0.0536(8) Uani 0.585(7) 1 d PDU A 2
N34 N 0.1796(6) 0.49875(16) 0.2674(7) 0.0657(10) Uani 0.585(7) 1 d PDU A 2
C11 C 0.5853(2) 0.51617(5) 0.7416(2) 0.0310(3) Uani 1 1 d D . .
C13 C 0.3996(2) 0.56570(5) 0.5739(2) 0.0292(3) Uani 1 1 d D . .
H13A H 0.2702 0.5554 0.5425 0.035 Uiso 1 1 calc R A 1
C14 C 0.4163(2) 0.57713(5) 0.7735(2) 0.0282(3) Uani 1 1 d . A .
C15 C 0.5954(2) 0.55492(5) 0.8478(2) 0.0290(3) Uani 1 1 d . A .
C16 C 0.6043(3) 0.54982(6) 1.0470(2) 0.0386(4) Uani 1 1 d . . .
H16A H 0.7247 0.5375 1.0847 0.058 Uiso 1 1 calc R A .
H16B H 0.4995 0.5332 1.0813 0.058 Uiso 1 1 calc R . .
H16C H 0.5947 0.5754 1.1040 0.058 Uiso 1 1 calc R . .
C17 C 0.4275(2) 0.62115(5) 0.8051(2) 0.0325(3) Uani 1 1 d . . .
H17A H 0.4423 0.6261 0.9342 0.039 Uiso 1 1 calc R A .
H17B H 0.5409 0.6316 0.7494 0.039 Uiso 1 1 calc R . .
C18 C 0.7636(3) 0.49011(5) 0.7675(3) 0.0372(4) Uani 1 1 d . A .
H18 H 0.8409 0.4998 0.8728 0.045 Uiso 1 1 calc R . .
C19 C 0.8907(3) 0.48586(7) 0.6129(3) 0.0497(5) Uani 1 1 d . . .
H19A H 0.9929 0.4675 0.6445 0.075 Uiso 1 1 calc R A .
H19B H 0.9446 0.5113 0.5848 0.075 Uiso 1 1 calc R . .
H19C H 0.8167 0.4760 0.5094 0.075 Uiso 1 1 calc R . .
C110 C 0.4983(3) 0.45757(5) 0.8317(2) 0.0334(4) Uani 1 1 d . . .
C111 C 0.3931(3) 0.42302(5) 0.8870(2) 0.0351(4) Uani 1 1 d . A .
C112 C 0.2076(3) 0.42597(5) 0.9356(3) 0.0393(4) Uani 1 1 d . . .
H112 H 0.1491 0.4509 0.9383 0.047 Uiso 1 1 calc R A .
C113 C 0.1057(3) 0.39308(6) 0.9805(3) 0.0411(4) Uani 1 1 d . A .
H113 H -0.0210 0.3955 1.0151 0.049 Uiso 1 1 calc R . .
C114 C 0.1905(3) 0.35648(5) 0.9745(2) 0.0384(4) Uani 1 1 d . . .
C115 C 0.3780(3) 0.35338(5) 0.9303(3) 0.0430(4) Uani 1 1 d . A .
H115 H 0.4376 0.3285 0.9311 0.052 Uiso 1 1 calc R . .
C116 C 0.4790(3) 0.38627(5) 0.8852(3) 0.0411(4) Uani 1 1 d . . .
H116 H 0.6066 0.3839 0.8529 0.049 Uiso 1 1 calc R A .
C117 C -0.0968(3) 0.32264(6) 1.0253(3) 0.0516(5) Uani 1 1 d . . .
H11A H -0.1287 0.3396 1.1241 0.077 Uiso 1 1 calc R A .
H11B H -0.1417 0.2961 1.0472 0.077 Uiso 1 1 calc R . .
H11C H -0.1576 0.3326 0.9150 0.077 Uiso 1 1 calc R . .
O21 O 0.96466(17) 0.63436(4) -0.06107(15) 0.0323(3) Uani 1 1 d . B .
H21 H 1.0515 0.6338 -0.1331 0.048 Uiso 1 1 calc R . .
O22 O 1.16390(16) 0.66277(3) 0.36113(15) 0.0321(2) Uani 1 1 d . . .
H22 H 1.1515 0.6867 0.3822 0.048 Uiso 1 1 calc R . .
O23 O 0.65644(17) 0.64728(3) 0.25737(15) 0.0326(3) Uani 1 1 d . . .
H23 H 0.6062 0.6339 0.3355 0.049 Uiso 1 1 calc R . .
O24 O 1.17103(19) 0.58783(4) 0.21468(17) 0.0387(3) Uani 1 1 d . B .
H24 H 1.1659 0.5877 0.1033 0.058 Uiso 1 1 calc R . .
O25 O 0.70799(17) 0.77074(3) 0.32128(16) 0.0352(3) Uani 1 1 d . B .
O26 O 1.2958(3) 0.89760(4) 0.6100(2) 0.0609(4) Uani 1 1 d . B .
N21 N 0.9682(2) 0.73268(4) 0.31797(18) 0.0301(3) Uani 1 1 d . B .
N22 N 0.9201(2) 0.72952(5) -0.0561(2) 0.0396(3) Uani 1 1 d D . .
N23 N 0.8059(3) 0.74315(5) -0.1663(2) 0.0407(4) Uani 0.936(3) 1 d PD B 3
N24 N 0.7119(3) 0.75833(7) -0.2722(3) 0.0592(6) Uani 0.936(3) 1 d PD B 3
N43 N 1.057(2) 0.7242(3) -0.145(2) 0.0407(4) Uani 0.064(3) 1 d PD B 4
N44 N 1.185(3) 0.7294(8) -0.232(3) 0.0592(6) Uani 0.064(3) 1 d PD B 4
C21 C 0.8123(2) 0.70806(5) 0.2443(2) 0.0281(3) Uani 1 1 d . . .
C22 C 0.8519(2) 0.69643(4) 0.0509(2) 0.0296(3) Uani 1 1 d D B .
H22A H 0.7340 0.6855 -0.0079 0.035 Uiso 1 1 calc R . .
C23 C 1.0032(2) 0.66417(5) 0.0673(2) 0.0286(3) Uani 1 1 d . . .
H23A H 1.1300 0.6758 0.0476 0.034 Uiso 1 1 calc R B .
C24 C 0.9997(2) 0.64888(4) 0.2619(2) 0.0273(3) Uani 1 1 d . B .
C25 C 0.8177(2) 0.66738(5) 0.3346(2) 0.0278(3) Uani 1 1 d . B .
C26 C 0.8152(3) 0.66793(6) 0.5350(2) 0.0359(4) Uani 1 1 d . . .
H26A H 0.6991 0.6806 0.5711 0.054 Uiso 1 1 calc R B .
H26B H 0.9252 0.6824 0.5835 0.054 Uiso 1 1 calc R . .
H26C H 0.8197 0.6411 0.5800 0.054 Uiso 1 1 calc R . .
C27 C 1.0019(3) 0.60475(5) 0.2766(2) 0.0336(3) Uani 1 1 d . . .
H27A H 0.9889 0.5973 0.4022 0.040 Uiso 1 1 calc R B .
H27B H 0.8919 0.5940 0.2070 0.040 Uiso 1 1 calc R . .
C28 C 0.6323(2) 0.73218(5) 0.2754(2) 0.0324(3) Uani 1 1 d . B .
H28 H 0.5717 0.7213 0.3818 0.039 Uiso 1 1 calc R . .
C29 C 0.4825(3) 0.73577(6) 0.1274(3) 0.0431(4) Uani 1 1 d . . .
H29A H 0.3733 0.7499 0.1704 0.065 Uiso 1 1 calc R B .
H29B H 0.4430 0.7097 0.0876 0.065 Uiso 1 1 calc R . .
H29C H 0.5339 0.7501 0.0282 0.065 Uiso 1 1 calc R . .
C210 C 0.8965(2) 0.76595(5) 0.3533(2) 0.0303(3) Uani 1 1 d . . .
C211 C 1.0028(3) 0.79991(5) 0.4238(2) 0.0335(4) Uani 1 1 d . B .
C212 C 1.1963(3) 0.79739(6) 0.4582(3) 0.0400(4) Uani 1 1 d . . .
H212 H 1.2590 0.7733 0.4402 0.048 Uiso 1 1 calc R B .
C213 C 1.3006(3) 0.82965(6) 0.5188(3) 0.0434(4) Uani 1 1 d . B .
H213 H 1.4333 0.8276 0.5416 0.052 Uiso 1 1 calc R . .
C214 C 1.2087(3) 0.86472(6) 0.5454(3) 0.0448(5) Uani 1 1 d . . .
C215 C 1.0152(3) 0.86740(6) 0.5149(3) 0.0481(5) Uani 1 1 d . B .
H215 H 0.9528 0.8914 0.5352 0.058 Uiso 1 1 calc R . .
C216 C 0.9111(3) 0.83525(6) 0.4547(3) 0.0428(4) Uani 1 1 d . . .
H216 H 0.7780 0.8373 0.4347 0.051 Uiso 1 1 calc R B .
C217 C 1.4955(4) 0.89805(7) 0.6275(3) 0.0604(6) Uani 1 1 d . . .
H21A H 1.5392 0.8764 0.7040 0.091 Uiso 1 1 calc R B .
H21B H 1.5379 0.9229 0.6802 0.091 Uiso 1 1 calc R . .
H21C H 1.5478 0.8951 0.5103 0.091 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C13 O11 H11 109.5 ?
C14 O12 H12 109.5 ?
C15 O13 H13 109.5 ?
C17 O14 H14 109.5 ?
C110 O15 C18 107.06(13) y
C114 O16 C117 118.00(16) y
C110 N11 C11 106.78(15) y
N12 C12 C13 116.4(6) y
N12 C12 C11 112.0(7) y
C13 C12 C11 105.5(3) y
N12 C12 H12B 107.5 ?
C13 C12 H12B 107.5 ?
C11 C12 H12B 107.5 ?
N13 N12 C12 119.2(4) y
N14 N13 N12 165.7(15) y
N32 C32 C13 118.8(4) y
N32 C32 C11 113.6(5) y
C13 C32 C11 105.47(19) y
N32 C32 H12C 106.0 ?
C13 C32 H12C 106.0 ?
C11 C32 H12C 106.0 ?
N33 N32 C32 119.9(4) y
N34 N33 N32 166.2(12) y
N11 C11 C12 113.4(4) y
N11 C11 C32 108.0(3) y
N11 C11 C15 110.53(14) y
C12 C11 C15 98.7(2) y
C32 C11 C15 102.2(2) y
N11 C11 C18 104.52(13) y
C12 C11 C18 115.7(2) y
C32 C11 C18 117.32(19) y
C15 C11 C18 114.21(14) y
O11 C13 C32 112.4(2) y
O11 C13 C12 108.9(3) y
O11 C13 C14 112.40(12) y
C32 C13 C14 106.55(16) y
C12 C13 C14 104.86(19) y
O11 C13 H13A 110.2 ?
C32 C13 H13A 104.8 ?
C12 C13 H13A 110.2 ?
C14 C13 H13A 110.2 ?
O12 C14 C17 106.12(13) y
O12 C14 C13 109.40(12) y
C17 C14 C13 113.62(13) y
O12 C14 C15 110.42(13) y
C17 C14 C15 112.91(13) y
C13 C14 C15 104.40(12) y
O13 C15 C16 112.46(14) y
O13 C15 C11 103.02(13) y
C16 C15 C11 114.46(14) y
O13 C15 C14 109.38(13) y
C16 C15 C14 114.14(14) y
C11 C15 C14 102.39(12) y
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
O14 C17 C14 112.68(14) y
O14 C17 H17A 109.1 ?
C14 C17 H17A 109.1 ?
O14 C17 H17B 109.1 ?
C14 C17 H17B 109.1 ?
H17A C17 H17B 107.8 ?
O15 C18 C19 109.39(16) y
O15 C18 C11 102.82(14) y
C19 C18 C11 117.92(16) y
O15 C18 H18 108.8 ?
C19 C18 H18 108.8 ?
C11 C18 H18 108.8 ?
C18 C19 H19A 109.5 ?
C18 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C18 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
N11 C110 O15 117.98(16) y
N11 C110 C111 126.13(17) y
O15 C110 C111 115.88(15) y
C112 C111 C116 119.16(18) y
C112 C111 C110 121.11(16) y
C116 C111 C110 119.70(18) y
C111 C112 C113 121.08(18) y
C111 C112 H112 119.5 ?
C113 C112 H112 119.5 ?
C112 C113 C114 119.51(19) y
C112 C113 H113 120.2 ?
C114 C113 H113 120.2 ?
O16 C114 C115 115.57(17) y
O16 C114 C113 124.69(19) y
C115 C114 C113 119.74(17) y
C116 C115 C114 120.49(17) y
C116 C115 H115 119.8 ?
C114 C115 H115 119.8 ?
C115 C116 C111 119.97(19) y
C115 C116 H116 120.0 ?
C111 C116 H116 120.0 ?
O16 C117 H11A 109.5 ?
O16 C117 H11B 109.5 ?
H11A C117 H11B 109.5 ?
O16 C117 H11C 109.5 ?
H11A C117 H11C 109.5 ?
H11B C117 H11C 109.5 ?
C23 O21 H21 109.5 ?
C24 O22 H22 109.5 ?
C25 O23 H23 109.5 ?
C27 O24 H24 109.5 ?
C210 O25 C28 106.27(12) y
C214 O26 C217 118.41(19) y
C210 N21 C21 106.86(14) y
N43 N22 N23 101.5(9) y
N43 N22 C22 118.3(5) y
N23 N22 C22 116.07(16) y
N24 N23 N22 173.7(2) y
N44 N43 N22 162.5(16) y
N21 C21 C28 104.16(13) y
N21 C21 C25 110.20(13) y
C28 C21 C25 114.64(13) y
N21 C21 C22 109.63(13) y
C28 C21 C22 117.82(13) y
C25 C21 C22 100.42(12) y
N22 C22 C23 110.39(13) y
N22 C22 C21 113.19(13) y
C23 C22 C21 105.33(13) y
N22 C22 H22A 109.3 ?
C23 C22 H22A 109.3 ?
C21 C22 H22A 109.3 ?
O21 C23 C22 110.43(13) y
O21 C23 C24 112.86(13) y
C22 C23 C24 105.94(13) y
O21 C23 H23A 109.2 ?
C22 C23 H23A 109.2 ?
C24 C23 H23A 109.2 ?
O22 C24 C27 106.68(13) y
O22 C24 C25 110.13(12) y
C27 C24 C25 112.66(14) y
O22 C24 C23 109.39(13) y
C27 C24 C23 113.80(13) y
C25 C24 C23 104.19(12) y
O23 C25 C26 111.44(13) y
O23 C25 C21 104.49(12) y
C26 C25 C21 115.25(13) y
O23 C25 C24 108.52(12) y
C26 C25 C24 113.95(14) y
C21 C25 C24 102.37(12) y
C25 C26 H26A 109.5 ?
C25 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
C25 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
O24 C27 C24 112.73(15) y
O24 C27 H27A 109.0 ?
C24 C27 H27A 109.0 ?
O24 C27 H27B 109.0 ?
C24 C27 H27B 109.0 ?
H27A C27 H27B 107.8 ?
O25 C28 C29 109.83(15) y
O25 C28 C21 102.90(13) y
C29 C28 C21 119.15(14) y
O25 C28 H28 108.2 ?
C29 C28 H28 108.2 ?
C21 C28 H28 108.2 ?
C28 C29 H29A 109.5 ?
C28 C29 H29B 109.5 ?
H29A C29 H29B 109.5 ?
C28 C29 H29C 109.5 ?
H29A C29 H29C 109.5 ?
H29B C29 H29C 109.5 ?
N21 C210 O25 117.86(15) y
N21 C210 C211 125.30(16) y
O25 C210 C211 116.84(14) y
C212 C211 C216 119.03(17) y
C212 C211 C210 120.20(16) y
C216 C211 C210 120.77(17) y
C211 C212 C213 121.07(18) y
C211 C212 H212 119.5 ?
C213 C212 H212 119.5 ?
C214 C213 C212 119.3(2) y
C214 C213 H213 120.3 ?
C212 C213 H213 120.3 ?
O26 C214 C215 115.66(19) y
O26 C214 C213 124.1(2) y
C215 C214 C213 120.15(18) y
C214 C215 C216 120.55(19) y
C214 C215 H215 119.7 ?
C216 C215 H215 119.7 ?
C215 C216 C211 119.8(2) y
C215 C216 H216 120.1 ?
C211 C216 H216 120.1 ?
O26 C217 H21A 109.5 ?
O26 C217 H21B 109.5 ?
H21A C217 H21B 109.5 ?
O26 C217 H21C 109.5 ?
H21A C217 H21C 109.5 ?
H21B C217 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C13 1.4196(19) y
O11 H11 0.8400 ?
O12 C14 1.4361(19) y
O12 H12 0.8400 ?
O13 C15 1.4281(19) y
O13 H13 0.8400 ?
O14 C17 1.431(2) y
O14 H14 0.8400 ?
O15 C110 1.349(2) y
O15 C18 1.455(2) y
O16 C114 1.363(2) y
O16 C117 1.423(3) y
N11 C110 1.281(2) y
N11 C11 1.475(2) y
C12 N12 1.474(4) y
C12 C13 1.544(4) y
C12 C11 1.547(4) y
C12 H12b 1.0000 ?
N12 N13 1.216(4) y
N13 N14 1.155(5) y
C32 N32 1.471(3) y
C32 C13 1.543(3) y
C32 C11 1.548(3) y
C32 H12c 1.0000 ?
N32 N33 1.214(3) y
N33 N34 1.158(4) y
C11 C15 1.550(2) y
C11 C18 1.551(2) y
C13 C14 1.556(2) y
C13 H13a 1.0000 ?
C14 C17 1.528(2) y
C14 C15 1.560(2) y
C15 C16 1.512(2) y
C16 H16a 0.9800 ?
C16 H16b 0.9800 ?
C16 H16c 0.9800 ?
C17 H17a 0.9900 ?
C17 H17b 0.9900 ?
C18 C19 1.514(3) y
C18 H18 1.0000 ?
C19 H19a 0.9800 ?
C19 H19b 0.9800 ?
C19 H19c 0.9800 ?
C110 C111 1.469(3) y
C111 C112 1.384(3) y
C111 C116 1.398(2) y
C112 C113 1.388(3) y
C112 H112 0.9500 ?
C113 C114 1.392(3) y
C113 H113 0.9500 ?
C114 C115 1.388(3) y
C115 C116 1.386(3) y
C115 H115 0.9500 ?
C116 H116 0.9500 ?
C117 H11a 0.9800 ?
C117 H11b 0.9800 ?
C117 H11c 0.9800 ?
O21 C23 1.4254(19) y
O21 H21 0.8400 ?
O22 C24 1.4343(19) y
O22 H22 0.8400 ?
O23 C25 1.4334(19) y
O23 H23 0.8400 ?
O24 C27 1.429(2) y
O24 H24 0.8400 ?
O25 C210 1.355(2) y
O25 C28 1.460(2) y
O26 C214 1.363(2) y
O26 C217 1.414(3) y
N21 C210 1.281(2) y
N21 C21 1.476(2) y
N22 N43 1.219(5) y
N22 N23 1.225(2) y
N22 C22 1.4856(19) y
N23 N24 1.141(2) y
N43 N44 1.159(5) y
C21 C28 1.546(2) y
C21 C25 1.551(2) y
C21 C22 1.552(2) y
C22 C23 1.540(2) y
C22 H22a 1.0000 ?
C23 C24 1.560(2) y
C23 H23a 1.0000 ?
C24 C27 1.515(2) y
C24 C25 1.559(2) y
C25 C26 1.514(2) y
C26 H26a 0.9800 ?
C26 H26b 0.9800 ?
C26 H26c 0.9800 ?
C27 H27a 0.9900 ?
C27 H27b 0.9900 ?
C28 C29 1.509(3) y
C28 H28 1.0000 ?
C29 H29a 0.9800 ?
C29 H29b 0.9800 ?
C29 H29c 0.9800 ?
C210 C211 1.471(2) y
C211 C212 1.385(3) y
C211 C216 1.398(3) y
C212 C213 1.394(3) y
C212 H212 0.9500 ?
C213 C214 1.385(3) y
C213 H213 0.9500 ?
C214 C215 1.382(3) y
C215 C216 1.389(3) y
C215 H215 0.9500 ?
C216 H216 0.9500 ?
C217 H21a 0.9800 ?
C217 H21b 0.9800 ?
C217 H21c 0.9800 ?
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
_geom_hbond_publ_flag
O11 H11 O24 0.84 1.81 2.6285(17) 164.6 1_455 y
O11 H11 O22 0.84 2.61 3.0546(17) 114.8 1_455 y
O12 H12 N11 0.84 2.15 2.8246(19) 137.4 . y
O13 H13 O21 0.84 1.99 2.7648(17) 153.6 1_556 y
O14 H14 O22 0.84 2.2 2.9687(17) 152.4 1_455 y
O14 H14 O11 0.84 2.35 2.8982(17) 123.3 . y
O21 H21 O14 0.84 1.86 2.6883(17) 168 1_654 y
O22 H22 N21 0.84 2.08 2.7778(19) 139.7 . y
O23 H23 O11 0.84 1.98 2.7950(16) 163.7 . y
O24 H24 O12 0.84 2.13 2.8861(17) 150.3 1_654 y
O24 H24 O21 0.84 2.44 2.9531(18) 120.1 . 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
_geom_torsion_publ_flag
C13 C12 N12 N13 -23.0(17) y
C11 C12 N12 N13 98.5(15) y
C13 C32 N32 N33 -7.8(13) y
C11 C32 N32 N33 117.1(11) y
C32 N32 N33 N34 122(4) y
C110 N11 C11 C12 120.5(2) y
C110 N11 C11 C32 119.21(18) y
C110 N11 C11 C15 -129.74(15) y
C110 N11 C11 C18 -6.42(17) y
N12 C12 C11 N11 -54.0(5) y
C13 C12 C11 N11 73.5(5) y
N12 C12 C11 C32 -41(2) y
C13 C12 C11 C32 86(2) y
N12 C12 C11 C15 -171.0(5) y
C13 C12 C11 C15 -43.4(5) y
N12 C12 C11 C18 66.7(7) y
C13 C12 C11 C18 -165.7(3) y
N32 C32 C11 N11 -50.6(4) y
C13 C32 C11 N11 81.2(4) y
N32 C32 C11 C12 142(2) y
C13 C32 C11 C12 -87(2) y
N32 C32 C11 C15 -167.2(4) y
C13 C32 C11 C15 -35.4(4) y
N32 C32 C11 C18 67.1(5) y
C13 C32 C11 C18 -161.1(2) y
N32 C32 C13 O11 -94.4(6) y
C11 C32 C13 O11 136.8(3) y
N32 C32 C13 C12 -145(2) y
C11 C32 C13 C12 86(2) y
N32 C32 C13 C14 142.0(5) y
C11 C32 C13 C14 13.3(4) y
N12 C12 C13 O11 -92.7(8) y
C11 C12 C13 O11 142.5(4) y
N12 C12 C13 C32 38(2) y
C11 C12 C13 C32 -87(2) y
N12 C12 C13 C14 146.9(7) y
C11 C12 C13 C14 22.0(5) y
O11 C13 C14 O12 132.14(13) y
C32 C13 C14 O12 -104.3(3) y
C12 C13 C14 O12 -109.8(4) y
O11 C13 C14 C17 13.76(19) y
C32 C13 C14 C17 137.3(3) y
C12 C13 C14 C17 131.9(4) y
O11 C13 C14 C15 -109.67(14) y
C32 C13 C14 C15 13.9(3) y
C12 C13 C14 C15 8.4(4) y
N11 C11 C15 O13 175.40(13) y
C12 C11 C15 O13 -65.5(3) y
C32 C11 C15 O13 -69.9(3) y
C18 C11 C15 O13 57.88(17) y
N11 C11 C15 C16 52.99(18) y
C12 C11 C15 C16 172.1(3) y
C32 C11 C15 C16 167.7(3) y
C18 C11 C15 C16 -64.5(2) y
N11 C11 C15 C14 -71.06(15) y
C12 C11 C15 C14 48.0(3) y
C32 C11 C15 C14 43.7(3) y
C18 C11 C15 C14 171.43(14) y
O12 C14 C15 O13 -169.37(12) y
C17 C14 C15 O13 -50.75(17) y
C13 C14 C15 O13 73.15(15) y
O12 C14 C15 C16 -42.39(18) y
C17 C14 C15 C16 76.23(18) y
C13 C14 C15 C16 -159.88(14) y
O12 C14 C15 C11 81.86(15) y
C17 C14 C15 C11 -159.52(13) y
C13 C14 C15 C11 -35.63(15) y
O12 C14 C17 O14 -59.57(16) y
C13 C14 C17 O14 60.68(18) y
C15 C14 C17 O14 179.33(12) y
C110 O15 C18 C19 -134.33(16) y
C110 O15 C18 C11 -8.23(18) y
N11 C11 C18 O15 8.80(17) y
C12 C11 C18 O15 -116.6(4) y
C32 C11 C18 O15 -110.7(3) y
C15 C11 C18 O15 129.71(15) y
N11 C11 C18 C19 129.20(18) y
C12 C11 C18 C19 3.8(4) y
C32 C11 C18 C19 9.7(4) y
C15 C11 C18 C19 -109.90(19) y
C11 N11 C110 O15 1.3(2) y
C11 N11 C110 C111 -177.54(16) y
C18 O15 C110 N11 4.9(2) y
C18 O15 C110 C111 -176.18(15) y
N11 C110 C111 C112 -9.5(3) y
O15 C110 C111 C112 171.64(17) y
N11 C110 C111 C116 168.30(18) y
O15 C110 C111 C116 -10.5(2) y
C116 C111 C112 C113 -0.7(3) y
C110 C111 C112 C113 177.19(18) y
C111 C112 C113 C114 -0.8(3) y
C117 O16 C114 C115 -169.12(19) y
C117 O16 C114 C113 11.1(3) y
C112 C113 C114 O16 -177.83(18) y
C112 C113 C114 C115 2.4(3) y
O16 C114 C115 C116 177.60(18) y
C113 C114 C115 C116 -2.7(3) y
C114 C115 C116 C111 1.2(3) y
C112 C111 C116 C115 0.5(3) y
C110 C111 C116 C115 -177.40(18) y
N23 N22 N43 N44 65(9) y
C22 N22 N43 N44 -167(8) y
C210 N21 C21 C28 -9.31(17) y
C210 N21 C21 C25 -132.75(14) y
C210 N21 C21 C22 117.63(14) y
N43 N22 C22 C23 15.4(13) y
N23 N22 C22 C23 136.35(16) y
N43 N22 C22 C21 133.2(13) y
N23 N22 C22 C21 -105.88(18) y
N21 C21 C22 N22 -44.32(18) y
C28 C21 C22 N22 74.49(18) y
C25 C21 C22 N22 -160.32(14) y
N21 C21 C22 C23 76.37(15) y
C28 C21 C22 C23 -164.82(13) y
C25 C21 C22 C23 -39.63(15) y
N22 C22 C23 O21 -97.30(15) y
C21 C22 C23 O21 140.19(13) y
N22 C22 C23 C24 140.18(14) y
C21 C22 C23 C24 17.67(15) y
O21 C23 C24 O22 132.62(13) y
C22 C23 C24 O22 -106.42(14) y
O21 C23 C24 C27 13.4(2) y
C22 C23 C24 C27 134.38(14) y
O21 C23 C24 C25 -109.66(14) y
C22 C23 C24 C25 11.31(15) y
N21 C21 C25 O23 177.64(12) y
C28 C21 C25 O23 60.54(16) y
C22 C21 C25 O23 -66.79(14) y
N21 C21 C25 C26 55.01(19) y
C28 C21 C25 C26 -62.09(19) y
C22 C21 C25 C26 170.58(14) y
N21 C21 C25 C24 -69.25(14) y
C28 C21 C25 C24 173.65(13) y
C22 C21 C25 C24 46.33(14) y
O22 C24 C25 O23 -168.67(12) y
C27 C24 C25 O23 -49.70(17) y
C23 C24 C25 O23 74.11(15) y
O22 C24 C25 C26 -43.88(18) y
C27 C24 C25 C26 75.09(17) y
C23 C24 C25 C26 -161.09(14) y
O22 C24 C25 C21 81.23(14) y
C27 C24 C25 C21 -159.80(13) y
C23 C24 C25 C21 -35.98(14) y
O22 C24 C27 O24 -57.38(17) y
C25 C24 C27 O24 -178.34(12) y
C23 C24 C27 O24 63.34(18) y
C210 O25 C28 C29 -140.73(15) y
C210 O25 C28 C21 -12.87(15) y
N21 C21 C28 O25 13.37(15) y
C25 C21 C28 O25 133.88(13) y
C22 C21 C28 O25 -108.29(15) y
N21 C21 C28 C29 135.11(16) y
C25 C21 C28 C29 -104.38(18) y
C22 C21 C28 C29 13.5(2) y
C21 N21 C210 O25 1.13(19) y
C21 N21 C210 C211 -177.86(15) y
C28 O25 C210 N21 8.16(19) y
C28 O25 C210 C211 -172.76(14) y
N21 C210 C211 C212 -0.3(3) y
O25 C210 C211 C212 -179.34(16) y
N21 C210 C211 C216 178.77(17) y
O25 C210 C211 C216 -0.2(2) y
C216 C211 C212 C213 -1.5(3) y
C210 C211 C212 C213 177.62(17) y
C211 C212 C213 C214 0.2(3) y
C217 O26 C214 C215 -173.8(2) y
C217 O26 C214 C213 9.4(3) y
C212 C213 C214 O26 177.7(2) y
C212 C213 C214 C215 1.1(3) y
O26 C214 C215 C216 -177.8(2) y
C213 C214 C215 C216 -1.0(3) y
C214 C215 C216 C211 -0.4(3) y
C212 C211 C216 C215 1.6(3) y
C210 C211 C216 C215 -177.54(18) y
