#------------------------------------------------------------------------------
#$Date: 2019-11-24 23:08:14 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/70/4517006.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_4517006
loop_
_publ_author_name
'Udagawa, Akihiro'
'Johnston, Priscilla'
'Uekusa, Hidehiro'
'Koshima, Hideko'
'Saito, Kei'
'Asahi, Toru'
_publ_section_title
;
 Solid-State Photochemical Reaction of Multisubstituted Thymine
 Derivatives
;
_journal_issue                   11
_journal_name_full               'ACS Sustainable Chemistry & Engineering'
_journal_page_first              6107
_journal_paper_doi               10.1021/acssuschemeng.6b01529
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C46 H54 N8 O16'
_chemical_formula_sum            'C46 H54 N8 O16'
_chemical_formula_weight         974.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-01
_audit_creation_method           'by CrystalStructure 4.2'
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.704(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.0679(5)
_cell_length_b                   13.2125(5)
_cell_length_c                   16.1614(7)
_cell_measurement_reflns_used    12727
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.35
_cell_volume                     2263.63(17)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24593
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_min         4.170
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1028.00
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.51
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0867P)²+2.2063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3289
_reflns_number_total             4150
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            sc6b01529_si_005.cif
_cod_data_source_block           global
_cod_database_code               4517006
_shelxl_version_number           2014/6
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.89998(19) 0.04506(16) 1.14520(12) 0.0455(5) Uani 1 1 d . .
O2 O 0.70018(19) -0.26199(14) 1.08004(13) 0.0448(5) Uani 1 1 d . .
O3 O 0.77863(17) 0.05471(15) 0.85082(12) 0.0426(5) Uani 1 1 d . .
O4 O 0.54582(19) -0.10474(13) 1.27954(12) 0.0415(5) Uani 1 1 d . .
O5 O 0.6694(2) -0.61821(16) 1.03348(14) 0.0554(6) Uani 1 1 d . .
O6 O 1.0008(2) 0.39815(18) 0.90358(17) 0.0646(7) Uani 1 1 d . .
O7 O 0.8526(3) -0.6472(2) 1.13124(17) 0.0751(8) Uani 1 1 d . .
O8 O 0.7969(2) 0.43844(17) 0.85325(16) 0.0611(6) Uani 1 1 d . .
N9 N 0.6008(2) -0.35838(16) 1.15822(15) 0.0386(5) Uani 1 1 d . .
N10 N 0.62478(18) -0.18381(14) 1.18069(13) 0.0296(5) Uani 1 1 d . .
N11 N 0.84148(18) 0.04711(15) 0.99833(13) 0.0307(5) Uani 1 1 d . .
N12 N 0.9396(2) 0.15707(16) 0.92412(14) 0.0357(5) Uani 1 1 d . .
C13 C 0.5853(2) -0.04383(16) 1.07330(15) 0.0271(5) Uani 1 1 d . .
C14 C 0.5637(2) -0.18392(19) 1.24553(16) 0.0322(6) Uani 1 1 d . .
C15 C 0.8485(2) 0.08465(19) 0.91940(17) 0.0333(6) Uani 1 1 d . .
C16 C 1.0089(2) 0.15773(19) 1.07805(17) 0.0335(6) Uani 1 1 d . .
C17 C 0.6271(2) -0.01577(17) 1.00268(15) 0.0273(5) Uani 1 1 d . .
C18 C 1.0163(2) 0.19150(19) 1.00210(17) 0.0339(6) Uani 1 1 d . .
H18 H 1.0775 0.2418 1.0016 0.041 Uiso 1 1 calc R U
C19 C 0.7573(2) -0.04050(18) 0.99602(17) 0.0318(6) Uani 1 1 d . .
H19A H 0.7988 -0.0866 1.0441 0.038 Uiso 1 1 calc R U
H19B H 0.7480 -0.0777 0.9414 0.038 Uiso 1 1 calc R U
C20 C 0.6463(2) -0.26824(19) 1.13609(17) 0.0348(6) Uani 1 1 d . .
C21 C 0.5408(2) 0.02761(17) 0.93104(16) 0.0286(5) Uani 1 1 d . .
H21 H 0.5692 0.0469 0.8832 0.034 Uiso 1 1 calc R U
C22 C 0.5257(2) -0.28240(19) 1.26830(17) 0.0336(6) Uani 1 1 d . .
C23 C 0.6714(2) -0.08641(18) 1.15667(16) 0.0313(5) Uani 1 1 d . .
H23A H 0.7568 -0.0964 1.1500 0.038 Uiso 1 1 calc R U
H23B H 0.6783 -0.0369 1.2038 0.038 Uiso 1 1 calc R U
C24 C 0.5450(3) -0.3635(2) 1.22402(18) 0.0391(6) Uani 1 1 d . .
H24 H 0.5189 -0.4278 1.2388 0.047 Uiso 1 1 calc R U
C25 C 0.9525(3) 0.1976(2) 0.84199(18) 0.0416(6) Uani 1 1 d . .
H25A H 0.9369 0.1426 0.7986 0.050 Uiso 1 1 calc R U
H25B H 1.0398 0.2221 0.8510 0.050 Uiso 1 1 calc R U
C26 C 0.7636(3) -0.5950(2) 1.10390(18) 0.0429(7) Uani 1 1 d . .
C27 C 1.0944(3) 0.1935(2) 1.16277(19) 0.0435(7) Uani 1 1 d . .
H27A H 1.0725 0.1589 1.2101 0.052 Uiso 1 1 calc R U
H27B H 1.1821 0.1783 1.1655 0.052 Uiso 1 1 calc R U
H27C H 1.0845 0.2667 1.1680 0.052 Uiso 1 1 calc R U
C28 C 0.6130(3) -0.4502(2) 1.10919(19) 0.0436(7) Uani 1 1 d . .
H28A H 0.5979 -0.4328 1.0475 0.052 Uiso 1 1 calc R U
H28B H 0.5487 -0.5005 1.1135 0.052 Uiso 1 1 calc R U
C29 C 0.4651(3) -0.2863(2) 1.3406(2) 0.0468(7) Uani 1 1 d . .
H29A H 0.4611 -0.2179 1.3631 0.056 Uiso 1 1 calc R U
H29B H 0.3796 -0.3138 1.3189 0.056 Uiso 1 1 calc R U
H29C H 0.5152 -0.3298 1.3870 0.056 Uiso 1 1 calc R U
C30 C 0.8960(3) 0.3784(2) 0.8599(2) 0.0491(7) Uani 1 1 d . .
C31 C 0.8608(3) 0.2838(2) 0.80780(19) 0.0456(7) Uani 1 1 d . .
H31A H 0.8584 0.2980 0.7472 0.055 Uiso 1 1 calc R U
H31B H 0.7752 0.2626 0.8082 0.055 Uiso 1 1 calc R U
C32 C 0.7428(3) -0.4957(2) 1.14382(19) 0.0456(7) Uani 1 1 d . .
H32A H 0.7598 -0.5058 1.2068 0.055 Uiso 1 1 calc R U
H32B H 0.8053 -0.4462 1.1352 0.055 Uiso 1 1 calc R U
C33 C 0.6832(4) -0.7140(3) 0.9928(2) 0.0616(9) Uani 1 1 d . .
H33A H 0.6103 -0.7245 0.9422 0.074 Uiso 1 1 calc R U
H33B H 0.7605 -0.7127 0.9748 0.074 Uiso 1 1 calc R U
H33C H 0.6880 -0.7692 1.0341 0.074 Uiso 1 1 calc R U
C34 C 0.8249(4) 0.5321(3) 0.9024(3) 0.0815(13) Uani 1 1 d . .
H34A H 0.7472 0.5714 0.8939 0.098 Uiso 1 1 calc R U
H34B H 0.8602 0.5163 0.9639 0.098 Uiso 1 1 calc R U
H34C H 0.8862 0.5716 0.8826 0.098 Uiso 1 1 calc R U
C35 C 0.9153(2) 0.08096(19) 1.07941(17) 0.0333(6) 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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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
C26 O5 C33 115.3(2) .
C30 O8 C34 114.8(3) .
C24 N9 C20 121.4(2) .
C24 N9 C28 120.3(2) .
C20 N9 C28 118.3(2) .
C20 N10 C14 125.5(2) .
C20 N10 C23 116.0(2) .
C14 N10 C23 118.5(2) .
C15 N11 C35 124.8(2) .
C15 N11 C19 117.2(2) .
C35 N11 C19 117.8(2) .
C15 N12 C18 121.9(2) .
C15 N12 C25 117.5(2) .
C18 N12 C25 120.6(2) .
C21 C13 C17 118.6(2) 3_657
C21 C13 C23 117.8(2) 3_657
C17 C13 C23 123.6(2) .
O4 C14 N10 120.7(2) .
O4 C14 C22 123.9(2) .
N10 C14 C22 115.4(2) .
O3 C15 N12 122.6(2) .
O3 C15 N11 121.9(2) .
N12 C15 N11 115.5(2) .
C18 C16 C35 118.7(2) .
C18 C16 C27 123.1(2) .
C35 C16 C27 118.1(2) .
C21 C17 C13 118.6(2) .
C21 C17 C19 118.0(2) .
C13 C17 C19 123.1(2) .
C16 C18 N12 123.2(2) .
C16 C18 H18 118.4 .
N12 C18 H18 118.4 .
N11 C19 C17 115.83(19) .
N11 C19 H19A 108.3 .
C17 C19 H19A 108.3 .
N11 C19 H19B 108.3 .
C17 C19 H19B 108.3 .
H19A C19 H19B 107.4 .
O2 C20 N9 122.9(2) .
O2 C20 N10 121.6(2) .
N9 C20 N10 115.5(2) .
C13 C21 C17 122.8(2) 3_657
C13 C21 H21 118.6 3_657
C17 C21 H21 118.6 .
C24 C22 C14 118.7(2) .
C24 C22 C29 124.2(2) .
C14 C22 C29 117.0(2) .
N10 C23 C13 112.24(19) .
N10 C23 H23A 109.2 .
C13 C23 H23A 109.2 .
N10 C23 H23B 109.2 .
C13 C23 H23B 109.2 .
H23A C23 H23B 107.9 .
C22 C24 N9 123.3(2) .
C22 C24 H24 118.3 .
N9 C24 H24 118.3 .
N12 C25 C31 111.8(2) .
N12 C25 H25A 109.3 .
C31 C25 H25A 109.3 .
N12 C25 H25B 109.3 .
C31 C25 H25B 109.3 .
H25A C25 H25B 107.9 .
O7 C26 O5 123.1(3) .
O7 C26 C32 124.2(3) .
O5 C26 C32 112.7(2) .
C16 C27 H27A 109.5 .
C16 C27 H27B 109.5 .
H27A C27 H27B 109.5 .
C16 C27 H27C 109.5 .
H27A C27 H27C 109.5 .
H27B C27 H27C 109.5 .
N9 C28 C32 110.6(2) .
N9 C28 H28A 109.5 .
C32 C28 H28A 109.5 .
N9 C28 H28B 109.5 .
C32 C28 H28B 109.5 .
H28A C28 H28B 108.1 .
C22 C29 H29A 109.5 .
C22 C29 H29B 109.5 .
H29A C29 H29B 109.5 .
C22 C29 H29C 109.5 .
H29A C29 H29C 109.5 .
H29B C29 H29C 109.5 .
O6 C30 O8 123.5(3) .
O6 C30 C31 124.3(3) .
O8 C30 C31 112.1(3) .
C30 C31 C25 112.5(2) .
C30 C31 H31A 109.1 .
C25 C31 H31A 109.1 .
C30 C31 H31B 109.1 .
C25 C31 H31B 109.1 .
H31A C31 H31B 107.8 .
C28 C32 C26 115.7(2) .
C28 C32 H32A 108.4 .
C26 C32 H32A 108.4 .
C28 C32 H32B 108.4 .
C26 C32 H32B 108.4 .
H32A C32 H32B 107.4 .
O5 C33 H33A 109.5 .
O5 C33 H33B 109.5 .
H33A C33 H33B 109.5 .
O5 C33 H33C 109.5 .
H33A C33 H33C 109.5 .
H33B C33 H33C 109.5 .
O8 C34 H34A 109.5 .
O8 C34 H34B 109.5 .
H34A C34 H34B 109.5 .
O8 C34 H34C 109.5 .
H34A C34 H34C 109.5 .
H34B C34 H34C 109.5 .
O1 C35 N11 120.0(2) .
O1 C35 C16 124.2(2) .
N11 C35 C16 115.7(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C35 1.220(3) .
O2 C20 1.222(3) .
O3 C15 1.221(3) .
O4 C14 1.224(3) .
O5 C26 1.339(4) .
O5 C33 1.454(4) .
O6 C30 1.200(4) .
O7 C26 1.179(4) .
O8 C30 1.333(4) .
O8 C34 1.455(4) .
N9 C24 1.376(3) .
N9 C20 1.380(3) .
N9 C28 1.477(3) .
N10 C20 1.385(3) .
N10 C14 1.401(3) .
N10 C23 1.479(3) .
N11 C15 1.392(3) .
N11 C35 1.403(3) .
N11 C19 1.480(3) .
N12 C15 1.376(3) .
N12 C18 1.379(3) .
N12 C25 1.476(3) .
C13 C21 1.394(3) 3_657
C13 C17 1.399(3) .
C13 C23 1.517(3) .
C14 C22 1.447(3) .
C16 C18 1.331(4) .
C16 C35 1.454(3) .
C16 C27 1.499(4) .
C17 C21 1.395(3) .
C17 C19 1.511(3) .
C18 H18 0.9500 .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C21 C13 1.394(3) 3_657
C21 H21 0.9500 .
C22 C24 1.340(4) .
C22 C29 1.507(4) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 H24 0.9500 .
C25 C31 1.520(4) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 C32 1.509(4) .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 C32 1.508(4) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 C31 1.496(4) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
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_4
C20 N10 C14 O4 -177.8(2) . .
C23 N10 C14 O4 2.3(3) . .
C20 N10 C14 C22 2.5(3) . .
C23 N10 C14 C22 -177.4(2) . .
C18 N12 C15 O3 178.8(2) . .
C25 N12 C15 O3 -1.0(4) . .
C18 N12 C15 N11 -1.5(3) . .
C25 N12 C15 N11 178.7(2) . .
C35 N11 C15 O3 -177.3(2) . .
C19 N11 C15 O3 7.9(3) . .
C35 N11 C15 N12 3.0(3) . .
C19 N11 C15 N12 -171.8(2) . .
C21 C13 C17 C21 0.2(4) 3_657 .
C23 C13 C17 C21 -176.6(2) . .
C21 C13 C17 C19 -172.8(2) 3_657 .
C23 C13 C17 C19 10.3(3) . .
C35 C16 C18 N12 -0.2(4) . .
C27 C16 C18 N12 178.5(2) . .
C15 N12 C18 C16 0.2(4) . .
C25 N12 C18 C16 -180.0(2) . .
C15 N11 C19 C17 -96.8(3) . .
C35 N11 C19 C17 88.0(3) . .
C21 C17 C19 N11 73.3(3) . .
C13 C17 C19 N11 -113.6(3) . .
C24 N9 C20 O2 177.3(3) . .
C28 N9 C20 O2 -2.8(4) . .
C24 N9 C20 N10 -3.8(4) . .
C28 N9 C20 N10 176.0(2) . .
C14 N10 C20 O2 179.8(2) . .
C23 N10 C20 O2 -0.3(3) . .
C14 N10 C20 N9 1.0(4) . .
C23 N10 C20 N9 -179.1(2) . .
C13 C17 C21 C13 -0.3(4) . 3_657
C19 C17 C21 C13 173.2(2) . 3_657
O4 C14 C22 C24 177.0(3) . .
N10 C14 C22 C24 -3.4(3) . .
O4 C14 C22 C29 -2.4(4) . .
N10 C14 C22 C29 177.3(2) . .
C20 N10 C23 C13 78.1(3) . .
C14 N10 C23 C13 -102.0(2) . .
C21 C13 C23 N10 56.8(3) 3_657 .
C17 C13 C23 N10 -126.4(2) . .
C14 C22 C24 N9 0.8(4) . .
C29 C22 C24 N9 -179.9(3) . .
C20 N9 C24 C22 3.1(4) . .
C28 N9 C24 C22 -176.8(3) . .
C15 N12 C25 C31 84.9(3) . .
C18 N12 C25 C31 -94.8(3) . .
C33 O5 C26 O7 0.8(5) . .
C33 O5 C26 C32 -179.1(3) . .
C24 N9 C28 C32 -97.6(3) . .
C20 N9 C28 C32 82.6(3) . .
C34 O8 C30 O6 0.8(5) . .
C34 O8 C30 C31 -179.9(3) . .
O6 C30 C31 C25 23.7(4) . .
O8 C30 C31 C25 -155.6(3) . .
N12 C25 C31 C30 71.7(3) . .
N9 C28 C32 C26 175.1(2) . .
O7 C26 C32 C28 -169.1(3) . .
O5 C26 C32 C28 10.8(4) . .
C15 N11 C35 O1 178.1(2) . .
C19 N11 C35 O1 -7.2(3) . .
C15 N11 C35 C16 -2.9(3) . .
C19 N11 C35 C16 171.8(2) . .
C18 C16 C35 O1 -179.7(2) . .
C27 C16 C35 O1 1.6(4) . .
C18 C16 C35 N11 1.4(3) . .
C27 C16 C35 N11 -177.4(2) . .
