#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/54/1515405.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_1515405
loop_
_publ_author_name
'Johnston, Priscilla'
'Wheldale, Dylan'
'Braybrook, Carl'
'Saito, Kei'
_publ_section_title
;
 Topochemical polymerization using bis-thyminyl monomers
;
_journal_issue                   14
_journal_name_full               'Polymer Chemistry'
_journal_page_first              4375
_journal_paper_doi               10.1039/c4py00265b
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C21 H28 N4 O8'
_chemical_formula_sum            'C21 H28 N4 O8'
_chemical_formula_weight         464.47
_chemical_name_common            PropBisThyPropOate
_chemical_name_systematic
;
 Propyl-linked bis-thymine propanoate
;
_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                87.67(3)
_cell_angle_beta                 67.81(3)
_cell_angle_gamma                73.16(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6130(19)
_cell_length_b                   10.826(2)
_cell_length_c                   12.485(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1148.0(5)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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     0.71070
_diffrn_reflns_av_R_equivalents  0.1109
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27656
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9997
_exptl_absorpt_correction_T_min  0.9979
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.002
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0768
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1146P)²+1.2874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2072
_refine_ls_wR_factor_ref         0.2159
_reflns_number_gt                3301
_reflns_number_total             4010
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4py00265b2.cif
_cod_data_source_block           9PropBisThyPropOate
_cod_depositor_comments
'Adding full bibliography for 1515405--1515407.cif.'
_cod_original_cell_volume        1148.1(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1515405
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
N3 N 0.9406(3) 0.9203(2) 0.3909(2) 0.0246(5) Uani 1 1 d .
O8 O 0.8952(3) 1.0680(2) 0.26236(18) 0.0335(5) Uani 1 1 d .
O9 O 0.9878(3) 0.7761(2) 0.52028(19) 0.0353(5) Uani 1 1 d .
O27 O 1.0841(3) 0.4447(2) 0.19515(19) 0.0339(5) Uani 1 1 d .
N21 N 0.8599(3) 0.6114(2) 0.2300(2) 0.0261(6) Uani 1 1 d .
O26 O 0.6496(2) 0.7868(2) 0.24737(19) 0.0337(5) Uani 1 1 d .
N1 N 0.7320(3) 1.1119(2) 0.4526(2) 0.0307(6) Uani 1 1 d .
N19 N 0.6831(3) 0.6038(3) 0.1461(2) 0.0305(6) Uani 1 1 d .
O15 O 0.6140(3) 1.3798(2) 0.6165(2) 0.0438(6) Uani 1 1 d .
C17 C 1.0111(3) 0.7619(3) 0.2262(2) 0.0268(6) Uani 1 1 d .
H17A H 0.9512 0.8255 0.1882 0.032 Uiso 1 1 calc R
H17B H 1.1027 0.7029 0.1643 0.032 Uiso 1 1 calc R
C23 C 0.9034(4) 0.4173(3) 0.1177(2) 0.0281(7) Uani 1 1 d .
C20 C 0.7249(4) 0.6754(3) 0.2101(2) 0.0280(7) Uani 1 1 d .
C2 C 0.8579(3) 1.0364(3) 0.3625(2) 0.0264(6) Uani 1 1 d .
C22 C 0.9601(4) 0.4876(3) 0.1811(2) 0.0276(7) Uani 1 1 d .
O13 O 0.7621(3) 1.4972(2) 0.5045(2) 0.0408(6) Uani 1 1 d .
C25 C 0.9971(4) 0.2813(3) 0.0723(3) 0.0327(7) Uani 1 1 d .
H25A H 0.9415 0.2440 0.0369 0.049 Uiso 1 1 calc R
H25B H 1.0112 0.2304 0.1362 0.049 Uiso 1 1 calc R
H25C H 1.1002 0.2798 0.0138 0.049 Uiso 1 1 calc R
C18 C 0.9071(4) 0.6840(3) 0.3010(2) 0.0262(6) Uani 1 1 d .
H18A H 0.9646 0.6228 0.3419 0.031 Uiso 1 1 calc R
H18B H 0.8120 0.7431 0.3601 0.031 Uiso 1 1 calc R
C4 C 0.9065(4) 0.8789(3) 0.5037(2) 0.0267(7) Uani 1 1 d .
C28 C 0.5413(4) 0.6640(4) 0.1225(3) 0.0353(8) Uani 1 1 d .
H28A H 0.4587 0.7168 0.1929 0.042 Uiso 1 1 calc R
H28B H 0.5021 0.5954 0.1050 0.042 Uiso 1 1 calc R
C5 C 0.7718(4) 0.9643(3) 0.5931(3) 0.0308(7) Uani 1 1 d .
C16 C 1.0701(3) 0.8334(3) 0.2940(3) 0.0270(6) Uani 1 1 d .
H16A H 1.1395 0.7695 0.3250 0.032 Uiso 1 1 calc R
H16B H 1.1333 0.8848 0.2409 0.032 Uiso 1 1 calc R
C29 C 0.5703(4) 0.7500(3) 0.0211(3) 0.0331(7) Uani 1 1 d .
H29A H 0.5904 0.8278 0.0436 0.040 Uiso 1 1 calc R
H29B H 0.6643 0.7021 -0.0460 0.040 Uiso 1 1 calc R
C24 C 0.7693(4) 0.4785(3) 0.1029(2) 0.0302(7) Uani 1 1 d .
H24 H 0.7327 0.4332 0.0607 0.036 Uiso 1 1 calc R
O33 O 0.3468(3) 0.7228(3) -0.0040(3) 0.0514(7) Uani 1 1 d .
C6 C 0.6909(4) 1.0745(3) 0.5643(3) 0.0331(7) Uani 1 1 d .
H6 H 0.6011 1.1293 0.6237 0.040 Uiso 1 1 calc R
C12 C 0.6895(4) 1.4058(3) 0.5220(3) 0.0323(7) Uani 1 1 d .
C11 C 0.7114(4) 1.3433(3) 0.4093(3) 0.0365(8) Uani 1 1 d .
H11A H 0.8254 1.3092 0.3622 0.044 Uiso 1 1 calc R
H11B H 0.6644 1.4099 0.3660 0.044 Uiso 1 1 calc R
O31 O 0.4054(4) 0.9077(3) -0.0494(3) 0.0604(9) Uani 1 1 d .
C30 C 0.4306(4) 0.7901(3) -0.0125(3) 0.0342(7) Uani 1 1 d .
C7 C 0.7279(5) 0.9237(4) 0.7156(3) 0.0440(9) Uani 1 1 d .
H7A H 0.6350 0.9899 0.7675 0.066 Uiso 1 1 calc R
H7B H 0.8157 0.9139 0.7402 0.066 Uiso 1 1 calc R
H7C H 0.7045 0.8411 0.7187 0.066 Uiso 1 1 calc R
C10 C 0.6385(4) 1.2345(3) 0.4244(3) 0.0379(8) Uani 1 1 d .
H10A H 0.5326 1.2621 0.4872 0.045 Uiso 1 1 calc R
H10B H 0.6251 1.2181 0.3520 0.045 Uiso 1 1 calc R
C14 C 0.7569(5) 1.5583(4) 0.6081(3) 0.0521(10) Uani 1 1 d .
H14A H 0.6505 1.6155 0.6503 0.078 Uiso 1 1 calc R
H14B H 0.8317 1.6090 0.5859 0.078 Uiso 1 1 calc R
H14C H 0.7850 1.4915 0.6580 0.078 Uiso 1 1 calc R
C32 C 0.2675(8) 0.9528(5) -0.0836(6) 0.099(2) Uani 1 1 d .
H32A H 0.2729 0.8872 -0.1380 0.148 Uiso 1 1 calc R
H32B H 0.2684 1.0341 -0.1208 0.148 Uiso 1 1 calc R
H32C H 0.1703 0.9667 -0.0144 0.148 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 0.0033 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
C2 N3 C4 124.9(2)
C2 N3 C16 116.8(2)
C4 N3 C16 118.3(2)
C20 N21 C22 125.2(3)
C20 N21 C18 116.9(2)
C22 N21 C18 117.8(2)
C2 N1 C6 121.6(3)
C2 N1 C10 117.2(3)
C6 N1 C10 121.3(3)
C20 N19 C24 122.6(3)
C20 N19 C28 118.4(3)
C24 N19 C28 119.0(3)
C18 C17 C16 113.3(2)
C24 C23 C22 118.4(3)
C24 C23 C25 123.3(3)
C22 C23 C25 118.2(3)
O26 C20 N19 122.7(3)
O26 C20 N21 122.2(3)
N19 C20 N21 115.1(3)
O8 C2 N1 122.3(3)
O8 C2 N3 121.8(3)
N1 C2 N3 115.9(3)
O27 C22 N21 120.1(3)
O27 C22 C23 124.5(3)
N21 C22 C23 115.4(3)
C12 O13 C14 115.9(3)
N21 C18 C17 111.0(2)
O9 C4 N3 120.1(3)
O9 C4 C5 124.5(3)
N3 C4 C5 115.4(3)
N19 C28 C29 112.7(2)
C6 C5 C4 119.2(3)
C6 C5 C7 123.1(3)
C4 C5 C7 117.7(3)
N3 C16 C17 112.4(2)
C30 C29 C28 110.4(3)
C23 C24 N19 122.8(3)
C5 C6 N1 123.0(3)
O15 C12 O13 123.6(3)
O15 C12 C11 125.0(3)
O13 C12 C11 111.4(3)
C12 C11 C10 113.4(3)
C30 O31 C32 115.7(3)
O33 C30 O31 123.3(3)
O33 C30 C29 123.2(3)
O31 C30 C29 113.5(3)
N1 C10 C11 113.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 C2 1.391(4)
N3 C4 1.406(4)
N3 C16 1.475(4)
O8 C2 1.228(4)
O9 C4 1.222(4)
O27 C22 1.224(4)
N21 C20 1.391(4)
N21 C22 1.404(4)
N21 C18 1.475(4)
O26 C20 1.216(4)
N1 C2 1.369(4)
N1 C6 1.377(4)
N1 C10 1.484(4)
N19 C20 1.369(4)
N19 C24 1.374(4)
N19 C28 1.464(4)
O15 C12 1.201(4)
C17 C18 1.517(4)
C17 C16 1.518(4)
C23 C24 1.345(5)
C23 C22 1.455(4)
C23 C25 1.488(4)
O13 C12 1.335(4)
O13 C14 1.454(5)
C4 C5 1.441(4)
C28 C29 1.528(4)
C5 C6 1.340(5)
C5 C7 1.508(4)
C29 C30 1.497(4)
O33 C30 1.209(4)
C12 C11 1.500(5)
C11 C10 1.509(5)
O31 C30 1.322(4)
O31 C32 1.488(5)
