#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/52/7215247.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_7215247
loop_
_publ_author_name
'Hutchins, Kristin M.'
'Sumrak, Joseph C.'
'Swenson, Dale C.'
'MacGillivray, Leonard R.'
_publ_section_title
;
 Head-to-tail photodimerization of a thiophene in a co-crystal and a rare
 adipic acid dimer in the presence of a heterosynthon
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              5762
_journal_paper_doi               10.1039/c4ce00481g
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C11 H9 N S, C6 H10 O4'
_chemical_formula_sum            'C17 H19 N O4 S'
_chemical_formula_weight         333.39
_chemical_name_common            'BPTE Adipic Acid'
_chemical_name_systematic
; 
1-(4-pyridyl)-2-(3-thienyl)ethylene hexanedioic acid 
;
_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                83.851(5)
_cell_angle_beta                 83.879(5)
_cell_angle_gamma                74.142(5)
_cell_formula_units_Z            2
_cell_length_a                   5.6534(6)
_cell_length_b                   8.1587(8)
_cell_length_c                   18.996(2)
_cell_measurement_reflns_used    1531
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.0
_cell_volume                     835.24(15)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD 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  0.0601
_diffrn_reflns_av_sigmaI/netI    0.1250
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3741
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.08
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1643
_refine_ls_R_factor_gt           0.0610
_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)+(0.0335P)²+0.3587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                1190
_reflns_number_total             2472
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00481g2.cif
_cod_data_source_block           mcg1394
_cod_depositor_comments
'Adding full bibliography for 7215244--7215247.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7215247
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
S1 S 0.7593(2) 0.02253(16) 0.43813(6) 0.0734(5) Uani 1 1 d .
O1 O 0.0792(5) 0.7619(4) 0.92078(16) 0.0786(10) Uani 1 1 d .
H1A H -0.0445 0.7620 0.9476 0.118 Uiso 1 1 calc R
O3 O 0.7716(5) 0.3877(4) 0.52984(15) 0.0686(9) Uani 1 1 d .
H3A H 0.8789 0.3999 0.4987 0.103 Uiso 1 1 calc R
O2 O -0.0757(5) 0.6050(4) 0.86000(16) 0.0871(11) Uani 1 1 d .
O4 O 0.8817(5) 0.5945(4) 0.57531(14) 0.0716(10) Uani 1 1 d .
C15 C 0.5336(6) 0.5926(5) 0.69713(19) 0.0531(11) Uani 1 1 d .
H15A H 0.5126 0.7114 0.6796 0.064 Uiso 1 1 calc R
H15B H 0.6856 0.5548 0.7207 0.064 Uiso 1 1 calc R
C7 C 1.1617(6) -0.0661(5) 0.2544(2) 0.0530(12) Uani 1 1 d .
H7 H 1.2676 0.0043 0.2514 0.064 Uiso 1 1 calc R
C13 C 0.2921(6) 0.6834(5) 0.8123(2) 0.0517(11) Uani 1 1 d .
H13A H 0.4429 0.6451 0.8364 0.062 Uiso 1 1 calc R
H13B H 0.2759 0.8014 0.7942 0.062 Uiso 1 1 calc R
C12 C 0.0787(7) 0.6778(5) 0.8659(2) 0.0538(12) Uani 1 1 d .
C16 C 0.5523(7) 0.4867(5) 0.6354(2) 0.0584(12) Uani 1 1 d .
H16A H 0.5780 0.3680 0.6537 0.070 Uiso 1 1 calc R
H16B H 0.3953 0.5211 0.6144 0.070 Uiso 1 1 calc R
C8 C 0.9873(7) -0.0572(5) 0.3174(2) 0.0493(11) Uani 1 1 d .
C17 C 0.7504(7) 0.4974(6) 0.5782(2) 0.0543(12) Uani 1 1 d .
C5 C 1.3646(6) -0.1748(5) 0.1393(2) 0.0474(11) Uani 1 1 d .
C6 C 1.1854(6) -0.1633(5) 0.2014(2) 0.0518(11) Uani 1 1 d .
H6 H 1.0768 -0.2315 0.2037 0.062 Uiso 1 1 calc R
C4 C 1.3748(7) -0.2856(5) 0.0886(2) 0.0608(13) Uani 1 1 d .
H4 H 1.2628 -0.3518 0.0927 0.073 Uiso 1 1 calc R
C14 C 0.3180(6) 0.5776(5) 0.75029(19) 0.0508(11) Uani 1 1 d .
H14A H 0.1669 0.6137 0.7263 0.061 Uiso 1 1 calc R
H14B H 0.3404 0.4587 0.7678 0.061 Uiso 1 1 calc R
C3 C 1.5507(8) -0.2988(5) 0.0316(2) 0.0673(14) Uani 1 1 d .
H3 H 1.5511 -0.3737 -0.0020 0.081 Uiso 1 1 calc R
C9 C 0.9790(6) 0.0413(5) 0.3714(2) 0.0568(12) Uani 1 1 d .
H9 H 1.0829 0.1120 0.3718 0.068 Uiso 1 1 calc R
N1 N 1.7198(6) -0.2106(4) 0.02194(17) 0.0593(10) Uani 1 1 d .
C2 C 1.7082(7) -0.1023(5) 0.0701(2) 0.0627(13) Uani 1 1 d .
H2 H 1.8222 -0.0376 0.0645 0.075 Uiso 1 1 calc R
C1 C 1.5376(7) -0.0796(5) 0.1280(2) 0.0598(13) Uani 1 1 d .
H1 H 1.5378 -0.0004 0.1598 0.072 Uiso 1 1 calc R
C10 C 0.6689(7) -0.1180(5) 0.3955(2) 0.0590(12) Uani 1 1 d .
H10 H 0.5430 -0.1682 0.4130 0.071 Uiso 1 1 calc R
C11 C 0.8040(7) -0.1490(5) 0.3317(2) 0.0619(13) Uani 1 1 d .
H11 H 0.7786 -0.2227 0.3009 0.074 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'
S S 0.1246 0.1234 '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
C10 S1 C9 91.78(19)
C16 C15 C14 111.4(3)
C6 C7 C8 127.1(4)
C12 C13 C14 115.5(3)
O2 C12 O1 123.2(4)
O2 C12 C13 124.8(4)
O1 C12 C13 112.0(3)
C17 C16 C15 116.3(3)
C9 C8 C11 110.1(3)
C9 C8 C7 124.0(4)
C11 C8 C7 125.9(4)
O4 C17 O3 122.7(4)
O4 C17 C16 124.7(4)
O3 C17 C16 112.5(4)
C4 C5 C1 115.6(3)
C4 C5 C6 121.1(3)
C1 C5 C6 123.3(4)
C7 C6 C5 126.9(4)
C5 C4 C3 120.2(4)
C13 C14 C15 112.9(3)
N1 C3 C4 124.0(4)
C8 C9 S1 113.3(3)
C2 N1 C3 115.9(3)
N1 C2 C1 124.0(4)
C2 C1 C5 120.3(4)
C11 C10 S1 111.5(3)
C10 C11 C8 113.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.685(4)
S1 C9 1.703(4)
O1 C12 1.309(4)
O3 C17 1.324(4)
O2 C12 1.202(4)
O4 C17 1.218(4)
C15 C16 1.507(4)
C15 C14 1.521(4)
C7 C6 1.322(4)
C7 C8 1.461(5)
C13 C12 1.500(5)
C13 C14 1.506(4)
C16 C17 1.490(5)
C8 C9 1.358(5)
C8 C11 1.425(5)
C5 C4 1.377(5)
C5 C1 1.393(5)
C5 C6 1.463(5)
C4 C3 1.382(5)
C3 N1 1.332(4)
N1 C2 1.324(4)
C2 C1 1.376(5)
C10 C11 1.370(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198416
