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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/52/7215245.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_7215245
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         'C22 H18 N2 S2'
_chemical_formula_sum            'C22 H18 N2 S2'
_chemical_formula_weight         374.50
_chemical_name_common            4p3tc
_chemical_name_systematic
; 
rctt-1,3-bis(4-pyridyl)-2,4-bis(3-thienyl) cyclobutane 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 117.334(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6886(12)
_cell_length_b                   15.1755(15)
_cell_length_c                   12.1662(12)
_cell_measurement_reflns_used    6496
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.0
_cell_volume                     1917.1(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10820
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0443
_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)+(0.0572P)²+0.5722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                2218
_reflns_number_total             3380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00481g2.cif
_cod_data_source_block           mcg149
_cod_depositor_comments
'Adding full bibliography for 7215244--7215247.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7215245
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 1.0225(2) 0.35062(16) 0.7539(2) 0.0578(6) Uani 1 1 d . . .
H1 H 0.9724 0.2999 0.7350 0.069 Uiso 1 1 calc R . .
C2 C 0.9846(3) 0.42593(19) 0.7920(3) 0.0680(7) Uani 1 1 d . . .
H2 H 0.9074 0.4240 0.7967 0.082 Uiso 1 1 calc R . .
N1 N 1.0504(2) 0.50075(14) 0.8223(2) 0.0705(6) Uani 1 1 d . . .
C3 C 1.1598(3) 0.50032(16) 0.8149(2) 0.0656(7) Uani 1 1 d . . .
H3 H 1.2091 0.5515 0.8369 0.079 Uiso 1 1 calc R . .
C4 C 1.2053(2) 0.42952(14) 0.7769(2) 0.0538(6) Uani 1 1 d . . .
H4 H 1.2828 0.4339 0.7732 0.065 Uiso 1 1 calc R . .
C5 C 1.1364(2) 0.35146(14) 0.74420(18) 0.0449(5) Uani 1 1 d . . .
C6 C 1.1851(2) 0.27415(13) 0.70163(19) 0.0441(5) Uani 1 1 d . B .
H6 H 1.2748 0.2859 0.7211 0.053 Uiso 1 1 calc R . .
C7 C 1.1776(2) 0.17981(13) 0.74492(18) 0.0445(5) Uani 1 1 d D . .
H7 H 1.0968 0.1728 0.7500 0.053 Uiso 1 1 calc R A 1
C8 C 1.2890(17) 0.147(3) 0.865(2) 0.0474(19) Uani 0.648(3) 1 d PD B 1
C9 C 1.4154(19) 0.1680(15) 0.911(2) 0.061(2) Uani 0.648(3) 1 d PD B 1
H9 H 1.4494 0.2037 0.8712 0.074 Uiso 0.648(3) 1 calc PR B 1
S1 S 1.50432(19) 0.1206(2) 1.05296(18) 0.0858(6) Uani 0.648(3) 1 d PD B 1
C10 C 1.3780(15) 0.0617(13) 1.0438(14) 0.0861(12) Uani 0.648(3) 1 d PD B 1
H10 H 1.3824 0.0188 1.1002 0.103 Uiso 0.648(3) 1 calc PR B 1
C11 C 1.2694(13) 0.086(3) 0.943(2) 0.0641(11) Uani 0.648(3) 1 d PD B 1
H11 H 1.1885 0.0643 0.9257 0.077 Uiso 0.648(3) 1 calc PR B 1
C8' C 1.273(3) 0.143(5) 0.863(4) 0.0474(19) Uani 0.352(3) 1 d PD B 2
C9' C 1.249(2) 0.084(6) 0.934(4) 0.0641(11) Uani 0.352(3) 1 d PD B 2
H9' H 1.1691 0.0593 0.9118 0.077 Uiso 0.352(3) 1 calc PR B 2
S1' S 1.3851(8) 0.0625(6) 1.0681(6) 0.0861(12) Uani 0.352(3) 1 d PD B 2
C10' C 1.4788(15) 0.1234(15) 1.0251(16) 0.0858(6) Uani 0.352(3) 1 d PD B 2
H10' H 1.5683 0.1248 1.0664 0.103 Uiso 0.352(3) 1 calc PR B 2
C11' C 1.404(4) 0.170(3) 0.922(4) 0.061(2) Uani 0.352(3) 1 d PD B 2
H11' H 1.4361 0.2148 0.8919 0.074 Uiso 0.352(3) 1 calc PR B 2
C12 C 1.3126(2) 0.02473(16) 0.6354(2) 0.0580(6) Uani 1 1 d . B .
H12 H 1.2572 -0.0153 0.6444 0.070 Uiso 1 1 calc R . .
C13 C 1.4276(3) -0.00389(19) 0.6414(2) 0.0707(7) Uani 1 1 d . . .
H13 H 1.4460 -0.0638 0.6531 0.085 Uiso 1 1 calc R . .
N2 N 1.5131(2) 0.04826(18) 0.6317(2) 0.0748(6) Uani 1 1 d . . .
C14 C 1.4808(2) 0.1318(2) 0.6103(2) 0.0687(7) Uani 1 1 d . . .
H14 H 1.5379 0.1699 0.6007 0.082 Uiso 1 1 calc R . .
C15 C 1.3679(2) 0.16704(17) 0.6012(2) 0.0580(6) Uani 1 1 d . B .
H15 H 1.3508 0.2268 0.5854 0.070 Uiso 1 1 calc R . .
C16 C 1.2800(2) 0.11314(15) 0.61569(18) 0.0452(5) Uani 1 1 d . . .
C17 C 1.15864(19) 0.14510(14) 0.61540(18) 0.0439(5) Uani 1 1 d . B .
H17 H 1.0889 0.1018 0.5795 0.053 Uiso 1 1 calc R . .
C18 C 1.1130(2) 0.23923(14) 0.56418(19) 0.0458(5) Uani 1 1 d . . .
H18 H 1.1532 0.2603 0.5140 0.055 Uiso 1 1 calc R B .
C19 C 0.9701(2) 0.25364(15) 0.50133(19) 0.0497(6) Uani 1 1 d . B .
C20 C 0.8794(2) 0.19768(17) 0.5011(2) 0.0626(7) Uani 1 1 d . . .
H20 H 0.8978 0.1426 0.5389 0.075 Uiso 1 1 calc R B .
S2 S 0.72762(7) 0.24001(6) 0.42333(9) 0.0967(3) Uani 1 1 d . B .
C21 C 0.7817(3) 0.33392(19) 0.3895(3) 0.0844(9) Uani 1 1 d . . .
H21 H 0.7295 0.3806 0.3449 0.101 Uiso 1 1 calc R B .
C22 C 0.9125(3) 0.33228(18) 0.4365(2) 0.0704(7) Uani 1 1 d . B .
H22 H 0.9595 0.3784 0.4269 0.084 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'
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
C2 C1 C5 119.3(2)
N1 C2 C1 124.6(2)
C3 N1 C2 115.6(2)
N1 C3 C4 124.3(2)
C3 C4 C5 120.2(2)
C4 C5 C1 115.9(2)
C4 C5 C6 120.46(19)
C1 C5 C6 123.6(2)
C5 C6 C7 121.30(17)
C5 C6 C18 121.79(17)
C7 C6 C18 87.92(15)
C8' C7 C8 7(2)
C8' C7 C6 123(3)
C8 C7 C6 118.2(14)
C8' C7 C17 123(4)
C8 C7 C17 120.8(18)
C6 C7 C17 88.44(15)
C9 C8 C11 110.8(3)
C9 C8 C7 127.7(15)
C11 C8 C7 121.6(14)
C8 C9 S1 111.3(5)
C10 S1 C9 92.8(9)
C11 C10 S1 110.2(13)
C10 C11 C8 114.5(8)
C9' C8' C11' 110.8(4)
C9' C8' C7 126(3)
C11' C8' C7 123(3)
C8' C9' S1' 111.4(6)
C10' S1' C9' 92.7(10)
C11' C10' S1' 109.8(14)
C10' C11' C8' 114.1(9)
C13 C12 C16 119.8(2)
N2 C13 C12 124.3(3)
C14 N2 C13 115.7(2)
N2 C14 C15 124.5(3)
C14 C15 C16 119.9(2)
C12 C16 C15 115.6(2)
C12 C16 C17 120.0(2)
C15 C16 C17 124.4(2)
C16 C17 C18 116.74(18)
C16 C17 C7 114.04(16)
C18 C17 C7 87.61(15)
C19 C18 C17 115.87(18)
C19 C18 C6 114.78(17)
C17 C18 C6 88.03(15)
C20 C19 C22 110.8(2)
C20 C19 C18 126.6(2)
C22 C19 C18 122.6(2)
C19 C20 S2 112.20(19)
C21 S2 C20 92.45(13)
C22 C21 S2 110.9(2)
C21 C22 C19 113.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.381(3)
C1 C5 1.389(3)
C2 N1 1.325(3)
N1 C3 1.323(3)
C3 C4 1.370(3)
C4 C5 1.384(3)
C5 C6 1.496(3)
C6 C7 1.542(3)
C6 C18 1.579(3)
C7 C8' 1.464(7)
C7 C8 1.525(6)
C7 C17 1.578(3)
C8 C9 1.355(10)
C8 C11 1.419(9)
C9 S1 1.711(13)
S1 C10 1.685(13)
C10 C11 1.351(18)
C8' C9' 1.355(12)
C8' C11' 1.419(11)
C9' S1' 1.710(15)
S1' C10' 1.689(13)
C10' C11' 1.352(19)
C12 C13 1.381(3)
C12 C16 1.385(3)
C13 N2 1.323(3)
N2 C14 1.315(3)
C14 C15 1.380(3)
C15 C16 1.387(3)
C16 C17 1.497(3)
C17 C18 1.552(3)
C18 C19 1.499(3)
C19 C20 1.357(3)
C19 C22 1.418(3)
C20 S2 1.707(2)
S2 C21 1.685(3)
C21 C22 1.365(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198414
