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#$Date: 2020-06-27 02:19:37 +0300 (Sat, 27 Jun 2020) $
#$Revision: 253494 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038529.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_4038529
loop_
_publ_author_name
'Brahmachari, Goutam'
'Karmakar, Indrajit'
_publ_section_title
;
 Visible Light-Induced and Singlet Oxygen-Mediated Photochemical
 Conversion of 4-Hydroxy-alpha-benzopyrones to
 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides/carboxylates Using
 Rose Bengal as a Photosensitizer.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00726
_journal_year                    2020
_chemical_formula_moiety         'C13 H11 N O4, H2 O'
_chemical_formula_sum            'C13 H13 N O5'
_chemical_formula_weight         263.24
_chemical_name_systematic
;
 2-Hydroxy-5-methyl-3-oxo-N-(prop-2-yn-1-yl)-2,3-dihydrobenzofuran-2-carboxamide
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.923(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7637(7)
_cell_length_b                   14.5153(8)
_cell_length_c                   7.3338(4)
_cell_measurement_reflns_used    1617
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.3910
_cell_measurement_theta_min      2.2500
_cell_volume                     1225.26(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelxl97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 15.9974
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3533
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0549P)²+0.0308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1330
_reflns_number_gt                1762
_reflns_number_total             2382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00726_si_002.cif
_cod_data_source_block           gb_1470_lt_mo
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4038529
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
O1 O 0.69286(12) 0.51784(10) 0.50345(18) 0.0222(4) Uani 1 1 d . . .
O2 O 0.89469(12) 0.52021(10) 0.55803(19) 0.0239(4) Uani 1 1 d . . .
H2 H 0.8934 0.5449 0.4571 0.036 Uiso 1 1 calc R . .
O1W O 0.88795(15) 0.60799(12) 0.2349(2) 0.0259(4) Uani 1 1 d . . .
O9 O 0.73287(13) 0.53008(10) 0.91034(19) 0.0272(4) Uani 1 1 d . . .
O3 O 0.86285(13) 0.70190(10) 0.7307(2) 0.0297(4) Uani 1 1 d . . .
N10 N 0.88045(15) 0.43729(12) 0.8664(2) 0.0211(4) Uani 1 1 d . . .
H101 H 0.9287 0.4254 0.7959 0.025 Uiso 1 1 calc R . .
C9 C 0.80233(18) 0.50302(14) 0.8159(3) 0.0182(5) Uani 1 1 d . . .
C3A C 0.67452(18) 0.67630(14) 0.5278(3) 0.0193(5) Uani 1 1 d . . .
C7A C 0.62394(18) 0.59457(14) 0.4551(3) 0.0193(5) Uani 1 1 d . . .
C5 C 0.50447(18) 0.75983(15) 0.3808(3) 0.0230(5) Uani 1 1 d . . .
C2 C 0.79977(17) 0.54766(14) 0.6254(3) 0.0191(5) Uani 1 1 d . . .
C4 C 0.61505(19) 0.76010(15) 0.4892(3) 0.0214(5) Uani 1 1 d . . .
H4 H 0.6498 0.8151 0.5361 0.026 Uiso 1 1 calc R . .
C3 C 0.78688(18) 0.65440(14) 0.6396(3) 0.0197(5) Uani 1 1 d . . .
C7 C 0.51290(18) 0.59200(15) 0.3462(3) 0.0234(5) Uani 1 1 d . . .
H7 H 0.4785 0.5371 0.2981 0.028 Uiso 1 1 calc R . .
C11 C 0.8877(2) 0.38402(15) 1.0381(3) 0.0247(5) Uani 1 1 d . . .
H112 H 0.9647 0.3911 1.1155 0.030 Uiso 1 1 calc R . .
H111 H 0.8320 0.4083 1.1066 0.030 Uiso 1 1 calc R . .
C6 C 0.45578(19) 0.67555(16) 0.3126(3) 0.0249(5) Uani 1 1 d . . .
H6 H 0.3808 0.6757 0.2406 0.030 Uiso 1 1 calc R . .
C12 C 0.8644(2) 0.28629(16) 1.0016(3) 0.0296(6) Uani 1 1 d . . .
C8 C 0.4373(2) 0.84828(17) 0.3338(3) 0.0329(6) Uani 1 1 d . . .
H81 H 0.4796 0.8983 0.4018 0.049 Uiso 1 1 calc R . .
H82 H 0.3628 0.8428 0.3671 0.049 Uiso 1 1 calc R . .
H83 H 0.4267 0.8600 0.2025 0.049 Uiso 1 1 calc R . .
C13 C 0.8465(3) 0.2080(2) 0.9769(3) 0.0549(9) Uani 1 1 d . . .
H11 H 0.881(3) 0.669(3) 0.230(4) 0.080(12) Uiso 1 1 d . . .
H12 H 0.834(2) 0.5865(18) 0.147(4) 0.036(7) Uiso 1 1 d . . .
H13 H 0.824(3) 0.144(3) 0.950(4) 0.091(12) Uiso 1 1 d . . .
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'
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
C7A O1 C2 107.83(15) . . ?
C2 O2 H2 109.5 . . ?
H11 O1W H12 107(3) . . ?
C9 N10 C11 122.30(17) . . ?
C9 N10 H101 118.9 . . ?
C11 N10 H101 118.9 . . ?
O9 C9 N10 124.91(18) . . ?
O9 C9 C2 118.93(19) . . ?
N10 C9 C2 116.16(17) . . ?
C7A C3A C4 120.58(18) . . ?
C7A C3A C3 107.54(18) . . ?
C4 C3A C3 131.87(19) . . ?
O1 C7A C7 124.12(18) . . ?
O1 C7A C3A 114.19(17) . . ?
C7 C7A C3A 121.68(19) . . ?
C4 C5 C6 118.50(19) . . ?
C4 C5 C8 121.1(2) . . ?
C6 C5 C8 120.37(19) . . ?
O2 C2 O1 111.00(15) . . ?
O2 C2 C9 109.95(16) . . ?
O1 C2 C9 106.66(16) . . ?
O2 C2 C3 114.21(17) . . ?
O1 C2 C3 104.67(15) . . ?
C9 C2 C3 109.98(16) . . ?
C5 C4 C3A 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
C3A C4 H4 120.5 . . ?
O3 C3 C3A 132.3(2) . . ?
O3 C3 C2 121.96(18) . . ?
C3A C3 C2 105.74(17) . . ?
C7A C7 C6 116.4(2) . . ?
C7A C7 H7 121.8 . . ?
C6 C7 H7 121.8 . . ?
C12 C11 N10 112.32(16) . . ?
C12 C11 H112 109.1 . . ?
N10 C11 H112 109.1 . . ?
C12 C11 H111 109.1 . . ?
N10 C11 H111 109.1 . . ?
H112 C11 H111 107.9 . . ?
C7 C6 C5 123.71(19) . . ?
C7 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C13 C12 C11 178.4(2) . . ?
C5 C8 H81 109.5 . . ?
C5 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C5 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
C12 C13 H13 174(2) . . ?
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
O1 C7A 1.380(2) . ?
O1 C2 1.450(2) . ?
O2 C2 1.370(2) . ?
O2 H2 0.8200 . ?
O1W H11 0.89(4) . ?
O1W H12 0.86(3) . ?
O9 C9 1.239(2) . ?
O3 C3 1.214(2) . ?
N10 C9 1.323(3) . ?
N10 C11 1.465(2) . ?
N10 H101 0.8600 . ?
C9 C2 1.535(3) . ?
C3A C7A 1.384(3) . ?
C3A C4 1.403(3) . ?
C3A C3 1.440(3) . ?
C7A C7 1.384(3) . ?
C5 C4 1.377(3) . ?
C5 C6 1.399(3) . ?
C5 C8 1.510(3) . ?
C2 C3 1.562(3) . ?
C4 H4 0.9300 . ?
C7 C6 1.384(3) . ?
C7 H7 0.9300 . ?
C11 C12 1.459(3) . ?
C11 H112 0.9700 . ?
C11 H111 0.9700 . ?
C6 H6 0.9300 . ?
C12 C13 1.163(4) . ?
C8 H81 0.9600 . ?
C8 H82 0.9600 . ?
C8 H83 0.9600 . ?
C13 H13 0.97(4) . ?
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
C11 N10 C9 O9 4.4(3) . . . . ?
C11 N10 C9 C2 -175.58(17) . . . . ?
C2 O1 C7A C7 -177.11(18) . . . . ?
C2 O1 C7A C3A 1.9(2) . . . . ?
C4 C3A C7A O1 179.47(17) . . . . ?
C3 C3A C7A O1 -1.4(2) . . . . ?
C4 C3A C7A C7 -1.5(3) . . . . ?
C3 C3A C7A C7 177.59(18) . . . . ?
C7A O1 C2 O2 -125.14(17) . . . . ?
C7A O1 C2 C9 115.10(17) . . . . ?
C7A O1 C2 C3 -1.45(19) . . . . ?
O9 C9 C2 O2 169.62(18) . . . . ?
N10 C9 C2 O2 -10.4(3) . . . . ?
O9 C9 C2 O1 -69.9(2) . . . . ?
N10 C9 C2 O1 110.03(19) . . . . ?
O9 C9 C2 C3 43.0(3) . . . . ?
N10 C9 C2 C3 -137.01(18) . . . . ?
C6 C5 C4 C3A -0.2(3) . . . . ?
C8 C5 C4 C3A -179.44(19) . . . . ?
C7A C3A C4 C5 1.3(3) . . . . ?
C3 C3A C4 C5 -177.56(19) . . . . ?
C7A C3A C3 O3 -179.9(2) . . . . ?
C4 C3A C3 O3 -0.9(4) . . . . ?
C7A C3A C3 C2 0.4(2) . . . . ?
C4 C3A C3 C2 179.4(2) . . . . ?
O2 C2 C3 O3 -57.5(2) . . . . ?
O1 C2 C3 O3 -179.11(17) . . . . ?
C9 C2 C3 O3 66.7(2) . . . . ?
O2 C2 C3 C3A 122.26(17) . . . . ?
O1 C2 C3 C3A 0.7(2) . . . . ?
C9 C2 C3 C3A -113.58(17) . . . . ?
O1 C7A C7 C6 179.50(18) . . . . ?
C3A C7A C7 C6 0.6(3) . . . . ?
C9 N10 C11 C12 116.9(2) . . . . ?
C7A C7 C6 C5 0.5(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C8 C5 C6 C7 178.52(19) . . . . ?
N10 C11 C12 C13 175(100) . . . . ?
