Exploring intermolecular interactions and energetics in crystalline substituted thieno[2,3-d]pyrimidines
Deb, Pran Kishore; Menon, Anila M.; PSR, Fathima Nida; Shruti, Ipsha; Nidal, Sara; Venugopala, Katharigatta N.; Chopra, Deepak; CrystEngComm 27 (2025) 2070–2085; doi:10.1039/D5CE00071H

data_7250019
_publ_section_title
;
 Exploring intermolecular interactions and energetics in crystalline
 substituted thieno[2,3-d]pyrimidines
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2070
_journal_page_last               2085
_journal_paper_doi               10.1039/D5CE00071H
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C11 H15 N3 S'
_chemical_formula_sum            'C11 H15 N3 S'
_chemical_formula_weight         221.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-02-23 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                61.569(2)
_cell_angle_beta                 79.570(2)
_cell_angle_gamma                88.952(2)
_cell_formula_units_Z            16
_cell_length_a                   16.8994(7)
_cell_length_b                   17.1783(8)
_cell_length_c                   17.8101(8)
_cell_measurement_reflns_used    9755
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.082
_cell_measurement_theta_min      1.879
_cell_volume                     4457.8(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            310915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.082
_diffrn_reflns_theta_min         1.897
_diffrn_source_current           1.39
_diffrn_source_power             0.0695
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9421
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1139 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.9421.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.188
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1226
_refine_ls_number_reflns         26153
_refine_ls_number_restraints     110
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+2.0659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22654
_reflns_number_total             26153
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00071h2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7250012--7250019.cif.'
_cod_database_code               7250019
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.940
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C40-C41 \\sim C40-C41A
 with sigma of 0.02
 C41-C42 \\sim C41A-C42A
 with sigma of 0.02
 C85-C86 \\sim C85A-C86A
 with sigma of 0.02
 C84-C85 \\sim C84A-C85A
 with sigma of 0.02
 C40-C42 \\sim C40-C42A
 with sigma of 0.04
 C78-C84 \\sim C78-C84A
 with sigma of 0.02
 C84-C86 \\sim C84A-C86A
 with sigma of 0.04
 C78-C85 \\sim C78-C85A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C41 \\sim C42 \\sim C41A \\sim C42A: within 2A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 2A
C84 \\sim C85 \\sim C86 \\sim C84A \\sim C85A \\sim C86A: within 2A with sigma
of 0.002 and sigma for terminal atoms of 0.004 within 2A
4. Others
 Sof(C41A)=Sof(H41C)=Sof(H41D)=Sof(C42A)=Sof(H42D)=Sof(H42E)=Sof(H42F)=1-FVAR(1)
 Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=FVAR(1)
 Sof(C84A)=Sof(H84C)=Sof(H84D)=Sof(C85A)=Sof(H85C)=Sof(H85D)=Sof(C86A)=
 Sof(H86D)=Sof(H86E)=Sof(H86F)=1-FVAR(2)
 Sof(C84)=Sof(H84A)=Sof(H84B)=Sof(C85)=Sof(H85A)=Sof(H85B)=Sof(C86)=Sof(H86A)=
 Sof(H86B)=Sof(H86C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C18(H18C,H18D), C73(H73A,H73B), C7(H7A,H7B), C30(H30A,H30B),
 C51(H51A,H51B), C62(H62A,H62B), C8(H8A,H8B), C84(H84A,H84B), C74(H74A,H74B),
 C63(H63A,H63B), C19(H19A,H19B), C85(H85A,H85B), C52(H52A,H52B), C41(H41A,H41B),
  C41A(H41C,H41D), C84A(H84C,H84D), C85A(H85C,H85D)
5.b Idealised Me refined as rotating group:
 C55(H55A,H55B,H55C), C11(H11A,H11B,H11C), C54(H54A,H54B,H54C), C21(H21C,H21D,
 H21E), C33(H33A,H33B,H33C), C66(H66A,H66B,H66C), C44(H44A,H44B,H44C), C43(H43A,
 H43B,H43C), C76(H76A,H76B,H76C), C65(H65A,H65B,H65C), C10(H10A,H10B,H10C),
 C87(H87A,H87B,H87C), C88(H88A,H88B,H88C), C77(H77A,H77B,H77C), C32(H32A,H32B,
 H32C), C75(H75A,H75B,H75C), C22(H22A,H22B,H22C), C31(H31A,H31B,H31C), C9(H9A,
 H9B,H9C), C20(H20A,H20B,H20C), C53(H53A,H53B,H53C), C86(H86A,H86B,H86C),
 C64(H64A,H64B,H64C), C42(H42A,H42B,H42C), C42A(H42D,H42E,H42F), C86A(H86D,H86E,
 H86F)
;
_shelx_res_checksum              95519
_olex2_submission_original_sample_id 4
_olex2_submission_special_instructions 'No special instructions were received'