#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:59:07 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257718 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/96/7059697.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_7059697
loop_
_publ_author_name
'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.'
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0166P)²+0.9379P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 1.0625(8) 0.1444(2) 0.7157(3) 0.0493(11) Uani 1 1 d D U . . .
H12 H 1.006813 0.164480 0.777318 0.059 Uiso 0.743(5) 1 calc R U P A 1
H12A H 1.003074 0.165629 0.775720 0.059 Uiso 0.257(5) 1 calc R U P A 2
C9 C 0.9600(7) 0.16167(18) 0.6116(3) 0.0328(9) Uani 1 1 d . U . . .
C10 C 1.0761(8) 0.1228(2) 0.5370(3) 0.0529(12) Uani 1 1 d D U . . .
H10 H 1.033140 0.127628 0.463565 0.063 Uiso 0.743(5) 1 calc R U P A 1
H10A H 1.034917 0.125210 0.463163 0.063 Uiso 0.257(5) 1 calc R U P A 2
C11A C 1.249(4) 0.0957(9) 0.7158(11) 0.055(3) Uani 0.743(5) 1 d D U P A 1
H11A H 1.342985 0.079156 0.778151 0.066 Uiso 0.743(5) 1 calc R U P A 1
S1A S 1.3013(7) 0.06600(18) 0.5900(2) 0.0594(8) Uani 0.743(5) 1 d D U P A 1
S1B S 1.298(3) 0.0832(7) 0.7256(10) 0.060(3) Uani 0.257(5) 1 d D U P A 2
C11B C 1.257(7) 0.0812(15) 0.5876(18) 0.066(10) Uani 0.257(5) 1 d D U P A 2
H11B H 1.358626 0.051554 0.549343 0.079 Uiso 0.257(5) 1 calc R U P A 2
O1 O 0.7113(5) 0.23018(14) 0.48258(19) 0.0468(8) Uani 1 1 d . . . . .
N2 N 0.6192(5) 0.24226(14) 0.6553(2) 0.0306(7) Uani 1 1 d . . . . .
H2 H 0.654169 0.230320 0.721132 0.037 Uiso 1 1 calc R U . . .
N1 N 0.4227(5) 0.29085(15) 0.6274(2) 0.0324(8) Uani 1 1 d . . . . .
O2 O 0.6948(6) 0.22247(18) 0.88353(18) 0.0613(9) Uani 1 1 d G . . . .
H2B H 0.832298 0.228402 0.929651 0.092 Uiso 1 1 d G U . . .
H2C H 0.554294 0.233489 0.915893 0.092 Uiso 1 1 d G U . . .
C8 C 0.7541(7) 0.21415(18) 0.5778(3) 0.0321(9) Uani 1 1 d . . . . .
C1 C 0.0975(7) 0.36860(18) 0.6888(3) 0.0319(9) Uani 1 1 d . . . . .
C7 C 0.3061(7) 0.31618(18) 0.7056(3) 0.0345(9) Uani 1 1 d . . . . .
H7 H 0.355292 0.300827 0.774777 0.041 Uiso 1 1 calc R U . . .
C2 C -0.0248(7) 0.39395(19) 0.7757(3) 0.0406(10) Uani 1 1 d . . . . .
H2A H 0.025955 0.376991 0.843823 0.049 Uiso 1 1 calc R U . . .
C6 C 0.0147(8) 0.3935(2) 0.5877(3) 0.0451(11) Uani 1 1 d . . . . .
H6 H 0.093214 0.376787 0.527888 0.054 Uiso 1 1 calc R U . . .
C3 C -0.2225(8) 0.4444(2) 0.7632(3) 0.0471(11) Uani 1 1 d . . . . .
H3 H -0.300917 0.461812 0.822461 0.057 Uiso 1 1 calc R U . . .
C5 C -0.1846(9) 0.4432(2) 0.5757(4) 0.0572(12) Uani 1 1 d . . . . .
H5 H -0.240230 0.459752 0.507824 0.069 Uiso 1 1 calc R U . . .
C4 C -0.3001(8) 0.4680(2) 0.6630(4) 0.0553(12) Uani 1 1 d . . . . .
H4 H -0.433737 0.501440 0.653982 0.066 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C12 H12 124.2 . . ?
C9 C12 H12A 122.1 . . ?
C9 C12 S1B 115.8(5) . . ?
C11A C12 H12 124.2 . . ?
C11A C12 C9 111.6(7) . . ?
S1B C12 H12A 122.1 . . ?
C12 C9 C8 128.0(3) . . ?
C10 C9 C12 111.2(4) . . ?
C10 C9 C8 120.7(4) . . ?
C9 C10 H10 123.0 . . ?
C9 C10 H10A 125.6 . . ?
C9 C10 S1A 114.0(3) . . ?
S1A C10 H10 123.0 . . ?
C11B C10 C9 108.8(11) . . ?
C11B C10 H10A 125.6 . . ?
C12 C11A H11A 123.0 . . ?
C12 C11A S1A 114.0(9) . . ?
S1A C11A H11A 123.0 . . ?
C10 S1A C11A 89.2(5) . . ?
C12 S1B C11B 85.6(9) . . ?
C10 C11B S1B 118.6(15) . . ?
C10 C11B H11B 120.7 . . ?
S1B C11B H11B 120.7 . . ?
N1 N2 H2 120.7 . . ?
C8 N2 H2 120.7 . . ?
C8 N2 N1 118.6(3) . . ?
C7 N1 N2 115.2(3) . . ?
H2B O2 H2C 104.5 . . ?
O1 C8 C9 120.7(3) . . ?
O1 C8 N2 122.7(3) . . ?
N2 C8 C9 116.6(3) . . ?
C2 C1 C7 119.3(3) . . ?
C2 C1 C6 118.6(3) . . ?
C6 C1 C7 122.0(3) . . ?
N1 C7 C1 121.5(3) . . ?
N1 C7 H7 119.3 . . ?
C1 C7 H7 119.3 . . ?
C1 C2 H2A 119.5 . . ?
C1 C2 C3 121.0(4) . . ?
C3 C2 H2A 119.5 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 H6 120.0 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C12 H12 0.9300 . ?
C12 H12A 0.9300 . ?
C12 C9 1.397(5) . ?
C12 C11A 1.325(11) . ?
C12 S1B 1.669(5) . ?
C9 C10 1.371(5) . ?
C9 C8 1.482(5) . ?
C10 H10 0.9300 . ?
C10 H10A 0.9300 . ?
C10 S1A 1.669(5) . ?
C10 C11B 1.325(11) . ?
C11A H11A 0.9300 . ?
C11A S1A 1.723(11) . ?
S1B C11B 1.723(11) . ?
C11B H11B 0.9300 . ?
O1 C8 1.234(4) . ?
N2 H2 0.8600 . ?
N2 N1 1.382(3) . ?
N2 C8 1.340(4) . ?
N1 C7 1.276(4) . ?
O2 H2B 0.8500 . ?
O2 H2C 0.8498 . ?
C1 C7 1.456(5) . ?
C1 C2 1.379(5) . ?
C1 C6 1.387(5) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.388(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.362(5) . ?
C4 H4 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C9 C10 S1A 0.6(5) . . . . ?
C12 C9 C10 C11B -1(2) . . . . ?
C12 C9 C8 O1 169.9(4) . . . . ?
C12 C9 C8 N2 -10.4(5) . . . . ?
C12 C11A S1A C10 2.2(14) . . . . ?
C12 S1B C11B C10 -1(3) . . . . ?
C9 C12 C11A S1A -2.3(17) . . . . ?
C9 C12 S1B C11B 0.0(18) . . . . ?
C9 C10 S1A C11A -1.5(8) . . . . ?
C9 C10 C11B S1B 1(3) . . . . ?
C10 C9 C8 O1 -10.0(5) . . . . ?
C10 C9 C8 N2 169.7(3) . . . . ?
C11A C12 C9 C10 1.1(11) . . . . ?
C11A C12 C9 C8 -178.8(11) . . . . ?
S1B C12 C9 C10 0.8(9) . . . . ?
S1B C12 C9 C8 -179.1(8) . . . . ?
O1 C8 N2 H2 -179.5 . . . . ?
N2 N1 C7 C1 179.1(3) . . . . ?
N1 N2 C8 C9 -179.2(3) . . . . ?
N1 N2 C8 O1 0.5(5) . . . . ?
C8 C9 C10 S1A -179.5(3) . . . . ?
C8 C9 C10 C11B 178.6(19) . . . . ?
C8 N2 N1 C7 -178.9(3) . . . . ?
C1 C2 C3 C4 1.4(6) . . . . ?
C1 C6 C5 C4 0.1(6) . . . . ?
C7 C1 C2 C3 179.4(3) . . . . ?
C7 C1 C6 C5 179.8(4) . . . . ?
C2 C1 C7 N1 179.3(3) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C6 C1 C7 N1 0.2(5) . . . . ?
C6 C1 C2 C3 -1.4(5) . . . . ?
C6 C5 C4 C3 -0.1(6) . . . . ?
