#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024774.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_4024774
loop_
_publ_author_name
'Chunyong Ding'
'Shanghui Tu'
'Fuying Li'
'Yuanxiang Wang'
'Qizheng Yao'
'Wenxiang Hu'
'Hua Xie'
'Linghua Meng'
'Ao Zhang'
_publ_section_title
;
Synthesis Study on Marmycin A: Preparation of the C3'-Desmethyl Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6111
_journal_page_last               6119
_journal_paper_doi               10.1021/jo9011078
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H23 N O6'
_chemical_formula_weight         433.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.787(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.730(3)
_cell_length_b                   9.2370(13)
_cell_length_c                   25.600(4)
_cell_measurement_reflns_used    1210
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.987
_cell_measurement_theta_min      4.652
_cell_volume                     4140.7(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1449
_diffrn_reflns_av_sigmaI/netI    0.1582
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10765
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5534
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1741
_refine_ls_R_factor_gt           0.1104
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1082P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2220
_refine_ls_wR_factor_ref         0.2538
_reflns_number_gt                2438
_reflns_number_total             4113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9011078_si_004.cif
_cod_data_source_block           cd28491
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4024774
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
N1 N 0.1594(5) 0.5695(10) 0.1914(4) 0.045(2) Uani 1 1 d . . .
H1A H 0.2045 0.5491 0.1920 0.054 Uiso 1 1 calc R . .
N2 N 0.8070(4) 0.6638(9) 0.1469(3) 0.033(2) Uani 1 1 d . . .
H2A H 0.8481 0.7145 0.1595 0.040 Uiso 1 1 calc R . .
O1 O 0.2635(5) 0.9960(13) 0.3800(4) 0.086(3) Uani 1 1 d . . .
O2 O 0.2998(4) 0.6854(10) 0.2157(3) 0.054(2) Uani 1 1 d . . .
O3 O -0.0256(3) 0.6945(8) 0.1447(3) 0.0370(18) Uani 1 1 d . . .
O4 O 0.1145(3) 0.6236(8) 0.0770(3) 0.0382(18) Uani 1 1 d . . .
H4 H 0.0936 0.6411 0.0436 0.057 Uiso 1 1 calc R . .
O5 O -0.0826(4) 0.7380(8) 0.0249(3) 0.0395(18) Uani 1 1 d . . .
H5 H -0.1233 0.7629 0.0274 0.059 Uiso 1 1 calc R . .
O6 O 0.6715(5) 0.8428(13) 0.3167(4) 0.089(3) Uani 1 1 d . . .
O7 O 0.8889(4) 0.8417(10) 0.2272(3) 0.057(2) Uani 1 1 d . . .
O8 O 0.6325(4) 0.5668(10) 0.0516(3) 0.058(2) Uani 1 1 d . . .
O9 O 0.7836(4) 0.8001(8) 0.0392(3) 0.0394(18) Uani 1 1 d . . .
H9 H 0.8032 0.7916 0.0154 0.059 Uiso 1 1 calc RD . .
O11 O 0.7660(5) 0.0248(12) 0.1022(5) 0.077(3) Uani 1 1 d D . .
O12 O 0.9276(14) 0.077(4) 0.1698(12) 0.206(13) Uiso 1 1 d D . .
O10 O 0.5388(8) 0.760(3) -0.0219(9) 0.099(8) Uani 0.50 1 d PD A 1
H10 H 0.5330 0.7305 0.0065 0.138 Uiso 0.50 1 calc PR A 1
O10' O 0.6171(12) 0.670(4) -0.0597(8) 0.140(14) Uani 0.50 1 d PD A 2
H10' H 0.5762 0.6782 -0.0856 0.165 Uiso 0.50 1 calc PR A 2
C1 C 0.4036(8) 1.1361(16) 0.4006(4) 0.063(4) Uani 1 1 d . . .
H1 H 0.3589 1.1477 0.4082 0.076 Uiso 1 1 calc R . .
C2 C 0.4653(7) 1.2199(19) 0.4274(5) 0.073(4) Uani 1 1 d . . .
H2 H 0.4608 1.2875 0.4530 0.087 Uiso 1 1 calc R . .
C3 C 0.5339(7) 1.2118(17) 0.4193(5) 0.064(4) Uani 1 1 d . . .
C4 C 0.5366(7) 1.1123(15) 0.3790(5) 0.056(4) Uani 1 1 d . . .
H4A H 0.5808 1.1080 0.3705 0.068 Uiso 1 1 calc R . .
C5 C 0.4773(6) 1.0197(16) 0.3510(5) 0.055(3) Uani 1 1 d . . .
C6 C 0.4808(7) 0.9255(14) 0.3077(5) 0.052(3) Uani 1 1 d . . .
H6 H 0.5264 0.9164 0.3012 0.062 Uiso 1 1 calc R . .
C7 C 0.4201(6) 0.8510(14) 0.2767(4) 0.048(3) Uani 1 1 d . . .
H7 H 0.4232 0.7947 0.2475 0.057 Uiso 1 1 calc R . .
C8 C 0.3506(6) 0.8551(15) 0.2871(4) 0.047(3) Uani 1 1 d . . .
C9 C 0.3447(6) 0.9413(12) 0.3303(4) 0.041(3) Uani 1 1 d . . .
C10 C 0.4069(6) 1.0284(14) 0.3603(4) 0.051(3) Uani 1 1 d . . .
C11 C 0.2710(5) 0.9361(13) 0.3415(4) 0.040(3) Uani 1 1 d . . .
C12 C 0.2062(6) 0.8436(14) 0.3021(4) 0.045(3) Uani 1 1 d . . .
C13 C 0.2154(6) 0.7543(13) 0.2613(4) 0.041(3) Uani 1 1 d . . .
C14 C 0.2886(6) 0.7587(15) 0.2520(5) 0.048(3) Uani 1 1 d . . .
C15 C 0.1520(6) 0.6697(12) 0.2282(4) 0.040(3) Uani 1 1 d . . .
C16 C 0.0803(5) 0.6901(13) 0.2335(4) 0.040(3) Uani 1 1 d . . .
C17 C 0.0759(6) 0.7807(12) 0.2749(4) 0.045(3) Uani 1 1 d . . .
H17 H 0.0292 0.7898 0.2799 0.054 Uiso 1 1 calc R . .
C18 C 0.1376(6) 0.8590(12) 0.3096(4) 0.040(3) Uani 1 1 d . . .
H18 H 0.1328 0.9198 0.3371 0.048 Uiso 1 1 calc R . .
C19 C 0.0121(6) 0.6124(13) 0.1952(4) 0.042(3) Uani 1 1 d . . .
H19 H -0.0240 0.5968 0.2145 0.051 Uiso 1 1 calc R . .
C20 C 0.0360(5) 0.4639(11) 0.1791(4) 0.035(2) Uani 1 1 d . . .
H20A H 0.0589 0.4047 0.2121 0.042 Uiso 1 1 calc R . .
H20B H -0.0080 0.4132 0.1537 0.042 Uiso 1 1 calc R . .
C21 C 0.0940(6) 0.4949(13) 0.1508(4) 0.040(3) Uani 1 1 d . . .
H21 H 0.1110 0.4035 0.1396 0.048 Uiso 1 1 calc R . .
C22 C 0.0569(6) 0.5853(12) 0.1009(4) 0.039(3) Uani 1 1 d . . .
H22 H 0.0164 0.5291 0.0735 0.047 Uiso 1 1 calc R . .
C23 C 0.0228(5) 0.7261(10) 0.1139(4) 0.025(2) Uani 1 1 d . . .
H23 H 0.0652 0.7855 0.1378 0.030 Uiso 1 1 calc R . .
C24 C -0.0215(6) 0.8156(12) 0.0649(4) 0.036(2) Uani 1 1 d . . .
H24A H -0.0422 0.8989 0.0778 0.044 Uiso 1 1 calc R . .
H24B H 0.0127 0.8511 0.0469 0.044 Uiso 1 1 calc R . .
C25 C 0.6022(9) 1.305(2) 0.4495(6) 0.095(5) Uani 1 1 d . . .
H25A H 0.5865 1.4038 0.4485 0.133 Uiso 1 1 calc R . .
H25B H 0.6392 1.2959 0.4316 0.133 Uiso 1 1 calc R . .
H25C H 0.6245 1.2731 0.4876 0.133 Uiso 1 1 calc R . .
C26 C 0.7631(9) 1.0115(18) 0.4097(5) 0.081(5) Uani 1 1 d . . .
H26 H 0.7176 0.9598 0.3987 0.097 Uiso 1 1 calc R . .
C27 C 0.7792(11) 1.094(2) 0.4546(6) 0.104(6) Uani 1 1 d . . .
H27 H 0.7459 1.0933 0.4743 0.125 Uiso 1 1 calc R . .
C28 C 0.8445(11) 1.182(2) 0.4737(6) 0.091(5) Uani 1 1 d . . .
C29 C 0.8942(9) 1.1717(16) 0.4453(5) 0.081(5) Uani 1 1 d . . .
H29 H 0.9386 1.2268 0.4571 0.097 Uiso 1 1 calc R . .
C30 C 0.8798(7) 1.0811(16) 0.3992(5) 0.063(4) Uani 1 1 d . . .
C31 C 0.9317(8) 1.0807(18) 0.3686(5) 0.074(4) Uani 1 1 d . . .
H31 H 0.9737 1.1424 0.3797 0.089 Uiso 1 1 calc R . .
C32 C 0.9203(6) 0.9928(13) 0.3245(4) 0.044(3) Uani 1 1 d . . .
H32 H 0.9572 0.9833 0.3081 0.052 Uiso 1 1 calc R . .
C33 C 0.8500(7) 0.9141(14) 0.3033(4) 0.052(3) Uani 1 1 d . . .
C34 C 0.7966(6) 0.9173(14) 0.3266(4) 0.046(3) Uani 1 1 d . . .
C35 C 0.8105(7) 0.9954(15) 0.3764(5) 0.055(3) Uani 1 1 d . . .
C36 C 0.7244(6) 0.8291(15) 0.3021(4) 0.051(3) Uani 1 1 d . . .
C37 C 0.7144(6) 0.7477(11) 0.2499(4) 0.037(3) Uani 1 1 d . . .
C38 C 0.7723(6) 0.7456(13) 0.2264(4) 0.041(3) Uani 1 1 d . . .
C39 C 0.8393(6) 0.8349(14) 0.2484(4) 0.046(3) Uani 1 1 d . . .
C40 C 0.7590(6) 0.6671(13) 0.1759(5) 0.047(3) Uani 1 1 d . . .
C41 C 0.6919(6) 0.5745(13) 0.1541(5) 0.049(3) Uani 1 1 d . . .
C42 C 0.6400(7) 0.5856(12) 0.1823(5) 0.050(3) Uani 1 1 d . . .
H42 H 0.5945 0.5345 0.1672 0.060 Uiso 1 1 calc R . .
C43 C 0.6497(6) 0.6635(12) 0.2291(5) 0.044(3) Uani 1 1 d . . .
H43 H 0.6139 0.6602 0.2466 0.052 Uiso 1 1 calc R . .
C44 C 0.6760(6) 0.4897(14) 0.1015(4) 0.050(3) Uani 1 1 d . . .
H44 H 0.6472 0.4029 0.1039 0.060 Uiso 1 1 calc R . .
C45 C 0.7506(7) 0.4421(12) 0.0977(5) 0.049(3) Uani 1 1 d . . .
H45A H 0.7421 0.3854 0.0642 0.059 Uiso 1 1 calc R . .
H45B H 0.7790 0.3837 0.1299 0.059 Uiso 1 1 calc R . .
C46 C 0.7948(6) 0.5815(11) 0.0962(4) 0.037(2) Uani 1 1 d . . .
H46 H 0.8442 0.5563 0.0936 0.044 Uiso 1 1 calc R . .
C47 C 0.7477(5) 0.6660(12) 0.0444(4) 0.039(3) Uani 1 1 d . . .
H47 H 0.7446 0.6066 0.0119 0.047 Uiso 1 1 calc R . .
C48 C 0.6649(6) 0.6966(15) 0.0407(5) 0.051(3) Uani 1 1 d . A .
H48 H 0.6660 0.7683 0.0692 0.061 Uiso 1 1 calc R . .
C49 C 0.6158(6) 0.7527(19) -0.0153(5) 0.077(5) Uani 1 1 d D . .
H49A H 0.6333 0.8485 -0.0205 0.093 Uiso 0.50 1 calc PR A 1
H49B H 0.6216 0.6902 -0.0440 0.093 Uiso 0.50 1 calc PR A 1
H49C H 0.5641 0.7562 -0.0164 0.093 Uiso 0.50 1 d PR A 2
H49D H 0.6316 0.8493 -0.0198 0.093 Uiso 0.50 1 d PR A 2
C50 C 0.8587(12) 1.277(2) 0.5237(7) 0.145(9) Uani 1 1 d . . .
H50A H 0.8599 1.2192 0.5552 0.167 Uiso 1 1 calc R . .
H50B H 0.8186 1.3474 0.5160 0.167 Uiso 1 1 calc R . .
H50C H 0.9068 1.3257 0.5320 0.167 Uiso 1 1 calc R . .
H11A H 0.736(4) 0.094(7) 0.096(4) 0.09(3) Uiso 1 1 d D . .
H12A H 0.9727(19) 0.081(8) 0.186(2) 0.13(17) Uiso 1 1 d 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C15 N1 C21 123.0(9) . . ?
C15 N1 H1A 118.5 . . ?
C21 N1 H1A 118.5 . . ?
C40 N2 C46 125.3(9) . . ?
C40 N2 H2A 117.4 . . ?
C46 N2 H2A 117.4 . . ?
C23 O3 C19 113.4(6) . . ?
C22 O4 H4 109.5 . . ?
C24 O5 H5 109.5 . . ?
C48 O8 C44 116.6(8) . . ?
C47 O9 H9 109.5 . . ?
H11A O11 H11B 106(10) . . ?
C49 O10 H10 109.5 . . ?
C49 O10 H49C 11.0 . . ?
H10 O10 H49C 98.7 . . ?
C49 O10' H10' 109.5 . . ?
C2 C1 C10 120.5(13) . . ?
C2 C1 H1 119.8 . . ?
C10 C1 H1 119.8 . . ?
C1 C2 C3 124.5(15) . . ?
C1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 C4 115.3(13) . . ?
C2 C3 C25 124.2(15) . . ?
C4 C3 C25 120.5(13) . . ?
C5 C4 C3 123.9(11) . . ?
C5 C4 H4A 118.1 . . ?
C3 C4 H4A 118.1 . . ?
C4 C5 C10 120.0(12) . . ?
C4 C5 C6 121.9(11) . . ?
C10 C5 C6 117.7(11) . . ?
C7 C6 C5 120.9(11) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.6(11) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 119.9(11) . . ?
C9 C8 C14 123.8(10) . . ?
C7 C8 C14 116.3(10) . . ?
C8 C9 C10 118.6(10) . . ?
C8 C9 C11 117.8(10) . . ?
C10 C9 C11 123.5(9) . . ?
C9 C10 C5 121.0(10) . . ?
C9 C10 C1 123.2(11) . . ?
C5 C10 C1 115.7(12) . . ?
O1 C11 C9 122.2(10) . . ?
O1 C11 C12 120.7(9) . . ?
C9 C11 C12 117.1(9) . . ?
C18 C12 C13 122.7(11) . . ?
C18 C12 C11 114.3(9) . . ?
C13 C12 C11 123.0(9) . . ?
C12 C13 C15 118.2(9) . . ?
C12 C13 C14 118.5(11) . . ?
C15 C13 C14 123.2(9) . . ?
O2 C14 C13 121.8(11) . . ?
O2 C14 C8 118.8(10) . . ?
C13 C14 C8 119.4(10) . . ?
N1 C15 C16 119.4(11) . . ?
N1 C15 C13 121.0(9) . . ?
C16 C15 C13 119.5(9) . . ?
C17 C16 C15 118.3(10) . . ?
C17 C16 C19 121.9(9) . . ?
C15 C16 C19 119.8(10) . . ?
C16 C17 C18 123.2(10) . . ?
C16 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C12 C18 C17 117.7(9) . . ?
C12 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
O3 C19 C16 111.6(9) . . ?
O3 C19 C20 108.9(8) . . ?
C16 C19 C20 109.9(9) . . ?
O3 C19 H19 108.8 . . ?
C16 C19 H19 108.8 . . ?
C20 C19 H19 108.8 . . ?
C21 C20 C19 106.4(8) . . ?
C21 C20 H20A 110.4 . . ?
C19 C20 H20A 110.5 . . ?
C21 C20 H20B 110.5 . . ?
C19 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
N1 C21 C22 111.4(9) . . ?
N1 C21 C20 107.8(7) . . ?
C22 C21 C20 108.6(8) . . ?
N1 C21 H21 109.6 . . ?
C22 C21 H21 109.6 . . ?
C20 C21 H21 109.6 . . ?
O4 C22 C21 107.9(8) . . ?
O4 C22 C23 108.2(8) . . ?
C21 C22 C23 113.3(8) . . ?
O4 C22 H22 109.1 . . ?
C21 C22 H22 109.1 . . ?
C23 C22 H22 109.1 . . ?
O3 C23 C24 107.9(7) . . ?
O3 C23 C22 109.9(7) . . ?
C24 C23 C22 116.0(7) . . ?
O3 C23 H23 107.6 . . ?
C24 C23 H23 107.6 . . ?
C22 C23 H23 107.6 . . ?
O5 C24 C23 113.0(8) . . ?
O5 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
O5 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C3 C25 H25A 109.5 . . ?
C3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C35 125.3(17) . . ?
C27 C26 H26 117.4 . . ?
C35 C26 H26 117.3 . . ?
C26 C27 C28 122.5(16) . . ?
C26 C27 H27 118.7 . . ?
C28 C27 H27 118.8 . . ?
C29 C28 C27 116.5(14) . . ?
C29 C28 C50 122.9(19) . . ?
C27 C28 C50 120.5(17) . . ?
C28 C29 C30 121.7(16) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.2 . . ?
C29 C30 C31 119.6(15) . . ?
C29 C30 C35 123.0(13) . . ?
C31 C30 C35 117.2(11) . . ?
C32 C31 C30 121.2(14) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C31 C32 C33 118.3(12) . . ?
C31 C32 H32 120.8 . . ?
C33 C32 H32 120.8 . . ?
C34 C33 C32 123.7(11) . . ?
C34 C33 C39 123.0(11) . . ?
C32 C33 C39 113.1(10) . . ?
C33 C34 C35 119.3(12) . . ?
C33 C34 C36 120.3(10) . . ?
C35 C34 C36 120.3(10) . . ?
C34 C35 C26 129.4(13) . . ?
C34 C35 C30 119.7(11) . . ?
C26 C35 C30 110.8(12) . . ?
O6 C36 C37 119.0(11) . . ?
O6 C36 C34 122.5(11) . . ?
C37 C36 C34 117.1(9) . . ?
C43 C37 C38 122.0(10) . . ?
C43 C37 C36 116.5(9) . . ?
C38 C37 C36 121.2(10) . . ?
C37 C38 C40 118.6(10) . . ?
C37 C38 C39 121.3(10) . . ?
C40 C38 C39 119.7(9) . . ?
O7 C39 C38 123.0(10) . . ?
O7 C39 C33 120.4(11) . . ?
C38 C39 C33 116.5(10) . . ?
N2 C40 C38 124.9(10) . . ?
N2 C40 C41 115.3(10) . . ?
C38 C40 C41 119.7(9) . . ?
C42 C41 C40 114.9(10) . . ?
C42 C41 C44 123.2(10) . . ?
C40 C41 C44 121.4(9) . . ?
C43 C42 C41 126.4(11) . . ?
C43 C42 H42 116.8 . . ?
C41 C42 H42 116.8 . . ?
C42 C43 C37 117.7(10) . . ?
C42 C43 H43 121.1 . . ?
C37 C43 H43 121.1 . . ?
O8 C44 C41 114.2(11) . . ?
O8 C44 C45 109.6(8) . . ?
C41 C44 C45 108.6(9) . . ?
O8 C44 H44 108.1 . . ?
C41 C44 H44 108.1 . . ?
C45 C44 H44 108.1 . . ?
C44 C45 C46 106.1(9) . . ?
C44 C45 H45A 110.5 . . ?
C46 C45 H45A 110.5 . . ?
C44 C45 H45B 110.5 . . ?
C46 C45 H45B 110.5 . . ?
H45A C45 H45B 108.7 . . ?
N2 C46 C47 111.7(8) . . ?
N2 C46 C45 109.4(8) . . ?
C47 C46 C45 107.6(9) . . ?
N2 C46 H46 109.4 . . ?
C47 C46 H46 109.4 . . ?
C45 C46 H46 109.4 . . ?
O9 C47 C46 112.2(8) . . ?
O9 C47 C48 109.2(9) . . ?
C46 C47 C48 113.9(8) . . ?
O9 C47 H47 107.1 . . ?
C46 C47 H47 107.1 . . ?
C48 C47 H47 107.1 . . ?
O8 C48 C49 108.8(10) . . ?
O8 C48 C47 108.9(10) . . ?
C49 C48 C47 112.6(8) . . ?
O8 C48 H48 108.8 . . ?
C49 C48 H48 108.8 . . ?
C47 C48 H48 108.8 . . ?
O10' C49 O10 104.3(17) . . ?
O10' C49 C48 114.6(17) . . ?
O10 C49 C48 113.1(12) . . ?
O10' C49 H49A 106.6 . . ?
O10 C49 H49A 108.9 . . ?
C48 C49 H49A 109.0 . . ?
O10' C49 H49B 5.9 . . ?
O10 C49 H49B 109.0 . . ?
C48 C49 H49B 109.0 . . ?
H49A C49 H49B 107.8 . . ?
O10' C49 H49C 108.0 . . ?
O10 C49 H49C 5.1 . . ?
C48 C49 H49C 108.1 . . ?
H49A C49 H49C 110.6 . . ?
H49B C49 H49C 112.4 . . ?
O10' C49 H49D 108.6 . . ?
O10 C49 H49D 106.8 . . ?
C48 C49 H49D 109.1 . . ?
H49A C49 H49D 2.5 . . ?
H49B C49 H49D 109.9 . . ?
H49C C49 H49D 108.4 . . ?
C28 C50 H50A 109.5 . . ?
C28 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C28 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
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
N1 C15 1.363(13) . ?
N1 C21 1.467(13) . ?
N1 H1A 0.8600 . ?
N2 C40 1.355(11) . ?
N2 C46 1.450(12) . ?
N2 H2A 0.8600 . ?
O1 C11 1.180(12) . ?
O2 C14 1.226(13) . ?
O3 C23 1.427(9) . ?
O3 C19 1.447(11) . ?
O4 C22 1.461(11) . ?
O4 H4 0.8200 . ?
O5 C24 1.430(11) . ?
O5 H5 0.8200 . ?
O6 C36 1.183(12) . ?
O7 C39 1.235(12) . ?
O8 C48 1.416(15) . ?
O8 C44 1.437(14) . ?
O9 C47 1.438(12) . ?
O9 H9 0.8200 . ?
O11 H11A 0.82(13) . ?
O11 H11B 0.82(13) . ?
O12 H12A 0.80(13) . ?
O10 C49 1.393(13) . ?
O10 H10 0.8200 . ?
O10 H49C 0.4448 . ?
O10' C49 1.376(17) . ?
O10' H10' 0.8201 . ?
C1 C2 1.357(19) . ?
C1 C10 1.451(17) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(19) . ?
C3 C25 1.505(19) . ?
C4 C5 1.383(17) . ?
C4 H4A 0.9300 . ?
C5 C10 1.423(14) . ?
C5 C6 1.429(17) . ?
C6 C7 1.325(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.420(14) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(15) . ?
C8 C14 1.486(17) . ?
C9 C10 1.399(16) . ?
C9 C11 1.509(13) . ?
C11 C12 1.534(16) . ?
C12 C18 1.371(13) . ?
C12 C13 1.389(14) . ?
C13 C15 1.423(15) . ?
C13 C14 1.472(13) . ?
C15 C16 1.409(13) . ?
C16 C17 1.376(14) . ?
C16 C19 1.490(15) . ?
C17 C18 1.386(15) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.544(15) . ?
C19 H19 0.9800 . ?
C20 C21 1.533(13) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.476(15) . ?
C21 H21 0.9800 . ?
C22 C23 1.537(14) . ?
C22 H22 0.9800 . ?
C23 C24 1.486(13) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.32(2) . ?
C26 C35 1.441(17) . ?
C26 H26 0.9300 . ?
C27 C28 1.40(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.37(2) . ?
C28 C50 1.50(2) . ?
C29 C30 1.393(17) . ?
C29 H29 0.9300 . ?
C30 C31 1.449(17) . ?
C30 C35 1.453(19) . ?
C31 C32 1.345(16) . ?
C31 H31 0.9300 . ?
C32 C33 1.431(16) . ?
C32 H32 0.9300 . ?
C33 C34 1.335(14) . ?
C33 C39 1.533(15) . ?
C34 C35 1.405(16) . ?
C34 C36 1.511(17) . ?
C36 C37 1.486(15) . ?
C37 C43 1.377(14) . ?
C37 C38 1.416(13) . ?
C38 C40 1.425(16) . ?
C38 C39 1.438(15) . ?
C40 C41 1.457(15) . ?
C41 C42 1.403(14) . ?
C41 C44 1.495(15) . ?
C42 C43 1.355(15) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 C45 1.500(15) . ?
C44 H44 0.9800 . ?
C45 C46 1.538(14) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.521(15) . ?
C46 H46 0.9800 . ?
C47 C48 1.547(13) . ?
C47 H47 0.9800 . ?
C48 C49 1.494(16) . ?
C48 H48 0.9800 . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C49 H49C 0.9600 . ?
C49 H49D 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
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
O11 H11B O10' 0.82(2) 2.6(2) 3.08(2) 118(19) 4_645
O11 H11B O9 0.82(2) 2.2(2) 2.719(12) 124(22) 1_545
O11 H11A O4 0.82(2) 2.17(7) 2.828(11) 137(9) 3_545
O10' H10' O12 0.82 2.33 2.78(3) 115.3 4_655
O10 H10 O10 0.82 1.55 2.13(3) 124.5 2_655
O9 H9 O5 0.82 2.12 2.719(9) 129.6 1_655
O5 H5 O9 0.82 1.90 2.719(9) 172.8 1_455
O4 H4 O5 0.82 1.91 2.677(9) 154.6 2
N2 H2A O3 0.86 2.53 3.168(9) 131.4 1_655
N2 H2A O7 0.86 2.01 2.654(11) 131.4 .
N1 H1A O2 0.86 2.09 2.699(12) 127.2 .
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
C10 C1 C2 C3 0(2) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C1 C2 C3 C25 -179.5(13) . . . . ?
C2 C3 C4 C5 -4.2(18) . . . . ?
C25 C3 C4 C5 177.5(13) . . . . ?
C3 C4 C5 C10 3.7(18) . . . . ?
C3 C4 C5 C6 176.2(11) . . . . ?
C4 C5 C6 C7 -171.5(11) . . . . ?
C10 C5 C6 C7 1.2(18) . . . . ?
C5 C6 C7 C8 -3.6(19) . . . . ?
C6 C7 C8 C9 1.2(17) . . . . ?
C6 C7 C8 C14 -175.8(11) . . . . ?
C7 C8 C9 C10 3.6(15) . . . . ?
C14 C8 C9 C10 -179.6(10) . . . . ?
C7 C8 C9 C11 -177.0(10) . . . . ?
C14 C8 C9 C11 -0.2(15) . . . . ?
C8 C9 C10 C5 -6.0(16) . . . . ?
C11 C9 C10 C5 174.6(10) . . . . ?
C8 C9 C10 C1 171.4(10) . . . . ?
C11 C9 C10 C1 -7.9(17) . . . . ?
C4 C5 C10 C9 176.5(11) . . . . ?
C6 C5 C10 C9 3.7(17) . . . . ?
C4 C5 C10 C1 -1.1(16) . . . . ?
C6 C5 C10 C1 -173.9(11) . . . . ?
C2 C1 C10 C9 -178.3(11) . . . . ?
C2 C1 C10 C5 -0.7(17) . . . . ?
C8 C9 C11 O1 173.6(12) . . . . ?
C10 C9 C11 O1 -7.0(18) . . . . ?
C8 C9 C11 C12 -3.8(14) . . . . ?
C10 C9 C11 C12 175.6(10) . . . . ?
O1 C11 C12 C18 11.1(17) . . . . ?
C9 C11 C12 C18 -171.5(9) . . . . ?
O1 C11 C12 C13 -170.4(12) . . . . ?
C9 C11 C12 C13 7.1(16) . . . . ?
C18 C12 C13 C15 -3.5(16) . . . . ?
C11 C12 C13 C15 178.1(10) . . . . ?
C18 C12 C13 C14 172.6(10) . . . . ?
C11 C12 C13 C14 -5.8(16) . . . . ?
C12 C13 C14 O2 -178.2(11) . . . . ?
C15 C13 C14 O2 -2.2(17) . . . . ?
C12 C13 C14 C8 1.4(15) . . . . ?
C15 C13 C14 C8 177.4(10) . . . . ?
C9 C8 C14 O2 -178.8(10) . . . . ?
C7 C8 C14 O2 -1.9(15) . . . . ?
C9 C8 C14 C13 1.6(16) . . . . ?
C7 C8 C14 C13 178.5(10) . . . . ?
C21 N1 C15 C16 8.9(14) . . . . ?
C21 N1 C15 C13 -170.9(10) . . . . ?
C12 C13 C15 N1 -173.4(9) . . . . ?
C14 C13 C15 N1 10.6(16) . . . . ?
C12 C13 C15 C16 6.7(15) . . . . ?
C14 C13 C15 C16 -169.2(10) . . . . ?
N1 C15 C16 C17 173.3(9) . . . . ?
C13 C15 C16 C17 -6.8(15) . . . . ?
N1 C15 C16 C19 -5.7(14) . . . . ?
C13 C15 C16 C19 174.1(9) . . . . ?
C15 C16 C17 C18 3.7(16) . . . . ?
C19 C16 C17 C18 -177.2(10) . . . . ?
C13 C12 C18 C17 0.4(16) . . . . ?
C11 C12 C18 C17 178.9(10) . . . . ?
C16 C17 C18 C12 -0.4(17) . . . . ?
C23 O3 C19 C16 58.6(10) . . . . ?
C23 O3 C19 C20 -62.9(10) . . . . ?
C17 C16 C19 O3 92.3(11) . . . . ?
C15 C16 C19 O3 -88.7(12) . . . . ?
C17 C16 C19 C20 -146.8(10) . . . . ?
C15 C16 C19 C20 32.2(12) . . . . ?
O3 C19 C20 C21 63.2(10) . . . . ?
C16 C19 C20 C21 -59.3(9) . . . . ?
C15 N1 C21 C22 81.3(11) . . . . ?
C15 N1 C21 C20 -37.8(13) . . . . ?
C19 C20 C21 N1 60.9(10) . . . . ?
C19 C20 C21 C22 -60.0(10) . . . . ?
N1 C21 C22 O4 56.9(11) . . . . ?
C20 C21 C22 O4 175.5(8) . . . . ?
N1 C21 C22 C23 -62.9(10) . . . . ?
C20 C21 C22 C23 55.7(11) . . . . ?
C19 O3 C23 C24 -177.5(9) . . . . ?
C19 O3 C23 C22 55.1(10) . . . . ?
O4 C22 C23 O3 -171.6(7) . . . . ?
C21 C22 C23 O3 -52.0(10) . . . . ?
O4 C22 C23 C24 65.7(10) . . . . ?
C21 C22 C23 C24 -174.7(8) . . . . ?
O3 C23 C24 O5 -67.7(9) . . . . ?
C22 C23 C24 O5 56.0(10) . . . . ?
C35 C26 C27 C28 3(3) . . . . ?
C26 C27 C28 C29 -4(3) . . . . ?
C26 C27 C28 C50 177.8(16) . . . . ?
C27 C28 C29 C30 1(2) . . . . ?
C50 C28 C29 C30 179.4(15) . . . . ?
C28 C29 C30 C31 176.4(13) . . . . ?
C28 C29 C30 C35 3(2) . . . . ?
C29 C30 C31 C32 178.8(12) . . . . ?
C35 C30 C31 C32 -7.0(18) . . . . ?
C30 C31 C32 C33 8.7(18) . . . . ?
C31 C32 C33 C34 -3.5(18) . . . . ?
C31 C32 C33 C39 171.9(11) . . . . ?
C32 C33 C34 C35 -3.5(18) . . . . ?
C39 C33 C34 C35 -178.5(11) . . . . ?
C32 C33 C34 C36 -179.0(11) . . . . ?
C39 C33 C34 C36 5.9(17) . . . . ?
C33 C34 C35 C26 -178.2(13) . . . . ?
C36 C34 C35 C26 -3(2) . . . . ?
C33 C34 C35 C30 5.1(17) . . . . ?
C36 C34 C35 C30 -179.3(11) . . . . ?
C27 C26 C35 C34 -176.2(16) . . . . ?
C27 C26 C35 C30 1(2) . . . . ?
C29 C30 C35 C34 173.9(12) . . . . ?
C31 C30 C35 C34 -0.2(18) . . . . ?
C29 C30 C35 C26 -3.4(18) . . . . ?
C31 C30 C35 C26 -177.4(12) . . . . ?
C33 C34 C36 O6 -169.8(12) . . . . ?
C35 C34 C36 O6 14.7(18) . . . . ?
C33 C34 C36 C37 -3.6(16) . . . . ?
C35 C34 C36 C37 -179.0(10) . . . . ?
O6 C36 C37 C43 -15.5(17) . . . . ?
C34 C36 C37 C43 177.7(10) . . . . ?
O6 C36 C37 C38 170.8(12) . . . . ?
C34 C36 C37 C38 4.0(15) . . . . ?
C43 C37 C38 C40 7.5(15) . . . . ?
C36 C37 C38 C40 -179.2(10) . . . . ?
C43 C37 C38 C39 179.6(10) . . . . ?
C36 C37 C38 C39 -7.1(16) . . . . ?
C37 C38 C39 O7 -176.0(10) . . . . ?
C40 C38 C39 O7 -4.0(18) . . . . ?
C37 C38 C39 C33 8.7(15) . . . . ?
C40 C38 C39 C33 -179.2(10) . . . . ?
C34 C33 C39 O7 176.2(11) . . . . ?
C32 C33 C39 O7 0.6(16) . . . . ?
C34 C33 C39 C38 -8.5(16) . . . . ?
C32 C33 C39 C38 176.0(10) . . . . ?
C46 N2 C40 C38 178.4(10) . . . . ?
C46 N2 C40 C41 2.6(15) . . . . ?
C37 C38 C40 N2 175.4(9) . . . . ?
C39 C38 C40 N2 3.1(17) . . . . ?
C37 C38 C40 C41 -8.9(16) . . . . ?
C39 C38 C40 C41 178.8(10) . . . . ?
N2 C40 C41 C42 -176.1(10) . . . . ?
C38 C40 C41 C42 7.8(16) . . . . ?
N2 C40 C41 C44 -3.5(16) . . . . ?
C38 C40 C41 C44 -179.6(11) . . . . ?
C40 C41 C42 C43 -5.7(19) . . . . ?
C44 C41 C42 C43 -178.1(12) . . . . ?
C41 C42 C43 C37 4.2(19) . . . . ?
C38 C37 C43 C42 -4.9(16) . . . . ?
C36 C37 C43 C42 -178.6(10) . . . . ?
C48 O8 C44 C41 59.6(11) . . . . ?
C48 O8 C44 C45 -62.5(12) . . . . ?
C42 C41 C44 O8 83.8(13) . . . . ?
C40 C41 C44 O8 -88.2(13) . . . . ?
C42 C41 C44 C45 -153.5(11) . . . . ?
C40 C41 C44 C45 34.5(15) . . . . ?
O8 C44 C45 C46 64.4(11) . . . . ?
C41 C44 C45 C46 -61.0(12) . . . . ?
C40 N2 C46 C47 87.0(11) . . . . ?
C40 N2 C46 C45 -31.9(13) . . . . ?
C44 C45 C46 N2 60.4(11) . . . . ?
C44 C45 C46 C47 -61.1(10) . . . . ?
N2 C46 C47 O9 59.3(10) . . . . ?
C45 C46 C47 O9 179.3(7) . . . . ?
N2 C46 C47 C48 -65.4(12) . . . . ?
C45 C46 C47 C48 54.7(11) . . . . ?
C44 O8 C48 C49 174.2(9) . . . . ?
C44 O8 C48 C47 51.2(12) . . . . ?
O9 C47 C48 O8 -174.0(8) . . . . ?
C46 C47 C48 O8 -47.8(12) . . . . ?
O9 C47 C48 C49 65.3(13) . . . . ?
C46 C47 C48 C49 -168.5(11) . . . . ?
O8 C48 C49 O10' -69.2(16) . . . . ?
C47 C48 C49 O10' 51.6(19) . . . . ?
O8 C48 C49 O10 50(2) . . . . ?
C47 C48 C49 O10 170.9(17) . . . . ?
