Structure–property relationship studies of 3-acyl-substituted furans: the serendipitous identification and characterization of a new non-classical hydrogen bond donor moiety
Rodrigues, Daniel A.; Pinheiro, Pedro de Sena M.; S. Sagrillo, Fernanda; R. Freitas, Maria Clara; A. Alves, Marina; Thota, Sreekanth; Tinoco, Luzineide W.; Magalhães, Alvicler; Sant’Anna, Carlos M. R.; Fraga, Carlos A. M.; New Journal of Chemistry 44 (2020) 10994–11005; doi:10.1039/D0NJ01598A

data_7059697
_publ_section_title
;
 Structure--property relationship studies of 3-acyl-substituted furans:
 the serendipitous identification and characterization of a new
 non-classical hydrogen bond donor moiety
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10994
_journal_page_last               11005
_journal_paper_doi               10.1039/D0NJ01598A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C12 H10 N2 O S, H2 O'
_chemical_formula_sum            'C12 H12 N2 O2 S'
_chemical_formula_weight         248.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-05 deposited with the CCDC.	2020-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.013(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8356(8)
_cell_length_b                   19.976(4)
_cell_length_c                   12.518(3)
_cell_measurement_reflns_used    1582
_cell_measurement_temperature    293
_cell_measurement_theta_max      20.72
_cell_measurement_theta_min      3.27
_cell_volume                     1204.6(4)
_computing_data_collection       'Apex3 (Bruker, 2012)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2339
_diffrn_reflns_av_unetI/netI     0.1089
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16061
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.613
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  20.72
_exptl_absorpt_correction_T_min  3.27
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0076(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0166P)^2^+0.9379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1114
_reflns_number_total             2119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01598a2.cif
_cod_data_source_block           mo_pit4_0m_a
_cod_depositor_comments
;Adding full bibliography for 7059697--7059698.cif.

 Adding full bibliography for 7059697--7059698.cif.
;
_cod_database_code               7059697
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C10-C11B \\sim C12-C11A
 with sigma of 0.001
 C10-S1A \\sim C12-S1B
 with sigma of 0.001
 C11A-S1A \\sim C11B-S1B
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
S1A \\sim S1B \\sim C11A \\sim C11B \\sim C12 \\sim C9 \\sim C10: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Others
 Sof(H12A)=Sof(H10A)=Sof(S1B)=Sof(C11B)=Sof(H11B)=1-FVAR(1)
 Sof(H12)=Sof(H10)=Sof(C11A)=Sof(H11A)=Sof(S1A)=FVAR(1)
5.a Free rotating group:
 O2(H2B,H2C)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C12(H12A), C10(H10), C10(H10A), C11A(H11A), C11B(H11B), N2(H2),
 C7(H7), C2(H2A), C6(H6), C3(H3), C5(H5), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'