#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/53/1515317.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_1515317
loop_
_publ_author_name
'Johnston, Priscilla'
'Izgorodina, Ekaterina I.'
'Saito, Kei'
_publ_section_title
;
 The interplay between hydrogen bonding and π-π stacking interactions in
 the crystal packing of N1-thyminyl derivatives, and implications for the
 photo-chemical [2π + 2π]-cycloaddition of thyminyl compounds.
;
_journal_issue                   12
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              1938
_journal_page_last               1951
_journal_paper_doi               10.1039/c2pp25228g
_journal_volume                  11
_journal_year                    2012
_chemical_formula_moiety         'C20 H26 N4 O8, 2(H2 O)'
_chemical_formula_sum            'C20 H30 N4 O10'
_chemical_formula_weight         486.48
_chemical_name_common            ButBisThyPropOic_Compound9
_chemical_name_systematic
;
ButBisThyPropOic
;
_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                96.93(3)
_cell_angle_beta                 111.13(3)
_cell_angle_gamma                101.53(3)
_cell_formula_units_Z            1
_cell_length_a                   7.6000(15)
_cell_length_b                   8.9000(18)
_cell_length_c                   9.4500(19)
_cell_measurement_temperature    173(2)
_cell_volume                     571.1(3)
_computing_cell_refinement       XDS
_computing_data_collection       'Blu Ice'
_computing_data_reduction        XDS
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'φ goniostat with quantum 210r detector'
_diffrn_measurement_method       'f scan'
_diffrn_radiation_monochromator  'silicon double crystal'
_diffrn_radiation_source         'MX1 Beamline, Australian Synchrotron'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7078
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_correction_T_min  0.9921
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             258
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1856
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0502
_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)+(0.0602P)²+0.2804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                1687
_reflns_number_total             1856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2pp25228g.txt
_cod_data_source_block           ButBisThyPropOic_Cmpd9
_cod_original_cell_volume        571.1(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1515317
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
N1 N 0.2393(2) 0.34296(18) 0.40716(18) 0.0195(4) Uani 1 1 d .
C2 C 0.2544(2) 0.3328(2) 0.5548(2) 0.0189(4) Uani 1 1 d .
N3 N 0.2572(2) 0.46853(17) 0.64615(17) 0.0174(4) Uani 1 1 d .
C4 C 0.2465(2) 0.6097(2) 0.5975(2) 0.0182(4) Uani 1 1 d .
C5 C 0.2289(2) 0.6109(2) 0.4404(2) 0.0189(4) Uani 1 1 d .
C6 C 0.2242(2) 0.4777(2) 0.3531(2) 0.0199(4) Uani 1 1 d .
H6 H 0.2098 0.4772 0.2489 0.024 Uiso 1 1 calc R
O7 O 0.2647(2) 0.21251(15) 0.60311(16) 0.0272(4) Uani 1 1 d .
O8 O 0.25065(19) 0.72356(14) 0.68798(15) 0.0242(4) Uani 1 1 d .
C9 C 0.2142(3) 0.7590(2) 0.3818(2) 0.0246(4) Uani 1 1 d .
H9A H 0.1860 0.7387 0.2705 0.037 Uiso 1 1 calc R
H9B H 0.3382 0.8396 0.4375 0.037 Uiso 1 1 calc R
H9C H 0.1088 0.7957 0.3990 0.037 Uiso 1 1 calc R
C10 C 0.2400(3) 0.2011(2) 0.3080(2) 0.0261(5) Uani 1 1 d .
H10A H 0.3344 0.1495 0.3724 0.031 Uiso 1 1 calc R
H10B H 0.2850 0.2331 0.2274 0.031 Uiso 1 1 calc R
C11 C 0.0407(3) 0.0839(2) 0.2296(2) 0.0242(4) Uani 1 1 d .
H11A H 0.0585 -0.0201 0.1971 0.029 Uiso 1 1 calc R
H11B H -0.0198 0.0744 0.3061 0.029 Uiso 1 1 calc R
C12 C -0.0971(3) 0.1270(2) 0.0899(2) 0.0232(4) Uani 1 1 d .
O13 O -0.0575(2) 0.24318(15) 0.04132(16) 0.0293(4) Uani 1 1 d .
O14 O -0.2655(2) 0.01775(16) 0.02364(17) 0.0302(4) Uani 1 1 d .
C15 C 0.2774(2) 0.4622(2) 0.8062(2) 0.0198(4) Uani 1 1 d .
H15A H 0.2122 0.3552 0.8089 0.024 Uiso 1 1 calc R
H15B H 0.2113 0.5359 0.8400 0.024 Uiso 1 1 calc R
C16 C 0.4910(2) 0.5049(2) 0.9180(2) 0.0212(4) Uani 1 1 d .
H16A H 0.5578 0.4323 0.8837 0.025 Uiso 1 1 calc R
H16B H 0.5559 0.6127 0.9171 0.025 Uiso 1 1 calc R
O1W O -0.50888(19) 0.02331(15) -0.25123(16) 0.0264(4) Uani 1 1 d D
H2W H -0.584(3) 0.095(2) -0.282(3) 0.058(8) Uiso 1 1 d D
H3W H -0.608(3) -0.0687(17) -0.267(3) 0.057(8) Uiso 1 1 d D
H14 H -0.339(5) 0.050(3) -0.068(4) 0.059(8) Uiso 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'
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
C6 N1 C2 121.90(15) .
C6 N1 C10 121.06(15) .
C2 N1 C10 117.03(15) .
O7 C2 N1 122.38(16) .
O7 C2 N3 121.87(17) .
N1 C2 N3 115.76(15) .
C2 N3 C4 124.50(15) .
C2 N3 C15 117.04(14) .
C4 N3 C15 118.44(15) .
O8 C4 N3 119.35(16) .
O8 C4 C5 124.12(16) .
N3 C4 C5 116.53(15) .
C6 C5 C4 118.09(17) .
C6 C5 C9 123.28(17) .
C4 C5 C9 118.63(16) .
C5 C6 N1 123.20(17) .
N1 C10 C11 113.09(15) .
C12 C11 C10 113.97(16) .
O13 C12 O14 124.19(19) .
O13 C12 C11 124.68(18) .
O14 C12 C11 111.09(16) .
N3 C15 C16 111.62(14) .
C16 C16 C15 110.90(18) 2_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.368(2) .
N1 C2 1.374(2) .
N1 C10 1.481(2) .
C2 O7 1.219(2) .
C2 N3 1.390(2) .
N3 C4 1.397(2) .
N3 C15 1.474(2) .
C4 O8 1.232(2) .
C4 C5 1.444(3) .
C5 C6 1.347(3) .
C5 C9 1.499(2) .
C10 C11 1.518(3) .
C11 C12 1.507(3) .
C12 O13 1.209(2) .
C12 O14 1.324(2) .
C15 C16 1.522(2) .
C16 C16 1.520(3) 2_667
