Design, synthesis, crystal structure and anti-plasmodial evaluation of tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine derivatives
Pal, Kavita; Raza, Md Kausar; Legac, Jenny; Ataur Rahman, Md.; Manzoor, Shoaib; Rosenthal, Philip J.; Hoda, Nasimul; RSC Medicinal Chemistry  (2021) –; doi:10.1039/D1MD00038A

data_7242873
_publ_section_title
;
 Design, synthesis, crystal structure and anti-plasmodial evaluation of
 tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine derivatives
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D1MD00038A
_journal_year                    2021
_chemical_formula_moiety
'0.5(C28 H31 N4 O2 S), 0.5(C28 H30 N4 O2 S), 0.25(C6 H12), 0.25(C6 H14)'
_chemical_formula_sum            'C31 H37 N4 O2 S'
_chemical_formula_weight         529.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_update_record
;
2020-06-04 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                79.88(2)
_cell_angle_beta                 76.458(13)
_cell_angle_gamma                68.561(13)
_cell_formula_units_Z            4
_cell_length_a                   10.221(5)
_cell_length_b                   13.970(9)
_cell_length_c                   21.807(13)
_cell_measurement_reflns_used    8271
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.76
_cell_measurement_theta_min      3.15
_cell_volume                     2804(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9655
_diffrn_measured_fraction_theta_max 0.9630
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.5243
_diffrn_reflns_av_unetI/netI     0.7166
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            72468
_diffrn_reflns_theta_full        31.7101
_diffrn_reflns_theta_max         31.71
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5245
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.2548
_exptl_crystal_description       block
_exptl_crystal_F_000             1132.9261
_refine_diff_density_max         2.2558
_refine_diff_density_min         -2.1205
_refine_diff_density_rms         0.4970
_refine_ls_d_res_high            0.6761
_refine_ls_d_res_low             7.0318
_refine_ls_goodness_of_fit_ref   1.0110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    120
_refine_ls_number_parameters     694
_refine_ls_number_reflns         18309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0110
_refine_ls_R_factor_all          0.5005
_refine_ls_R_factor_gt           0.1731
_refine_ls_shift/su_max          0.0030
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1743P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3161
_refine_ls_wR_factor_ref         0.4787
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              20
_reflns_limit_k_min              -20
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                3834
_reflns_number_total             18309
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1md00038a2.cif
_cod_data_source_block           F1
_cod_database_code               7242873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H02f,H02g,H7aa} of C024, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, {H01k,H01n,H01o} of C01X, {H5aa,Hd,He} of C01Y, {H02h,H02i,
  H02j} of C021, {H02c,H02d,H02e} of C022
2.a Ternary CH refined with riding coordinates:
 C00Q(H00Q), C018(H018)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00a,H00c), C00M(H00d,H00e), C00U(H00g,H00i), C00Z(H00j,H00k), C01B(H01v,
 H01w), C01G(H01z,H), C01J(H01b,H01c), C01N(H01d,H01f), C01R(H1aa,Ha),
 C01S(H01g,H01h), C01U(H3aa,Hb), C01V(H4aa,Hc), C01W(H01i,H01j), C010(H01r,
 H01s), C015(H6aa,Hf), C019(H01t,H01u), C020(H02a,H02b), C023(H02k,H02l),
 C024(H02f,H02g)
2.c Aromatic/amide H refined with riding coordinates:
 N00B(H00B), C00H(H00H), C00L(H00L), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C01A(H01A), C01D(H01x), C01E(H01E), C01F(H01y), C01I(H01), C01L(H01L),
 C01M(H01M), C01O(H0aa), C01P(H01P), C01Q(H01Q), C01T(H2aa), C013(H013),
 C016(H016)
2.d Idealised Me refined as rotating group:
 C01X(H01k,H01n,H01o), C01Y(H5aa,Hd,He), C021(H02h,H02i,H02j), C022(H02c,H02d,
 H02e)
2.e Idealised tetrahedral OH refined as rotating group:
 O004(H004), O007(H007)
;
_olex2_submission_special_instructions 'No special instructions were received'