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#$Date: 2023-05-06 13:47:59 +0300 (Sat, 06 May 2023) $
#$Revision: 283592 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/42/2244231.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244231
loop_
_publ_author_name
'Ismail, Ahmad Zaidi'
'Gunasekharan, Mohanapriya'
'Karunakaran, Thiruventhan'
'Mohd Faudzi, Siti Munirah'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 3-(3-hy-droxy-phen-yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one
 hemihydrate.
;
_journal_coeditor_code           YZ2023
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              287
_journal_page_last               291
_journal_paper_doi               10.1107/S2056989023001925
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          '2C13 H11 N O2, H2 O'
_chemical_formula_moiety         '2(C13 H11 N O2), H2 O'
_chemical_formula_sum            'C26 H24 N2 O5'
_chemical_formula_weight         444.47
_chemical_name_systematic
;
3-(3-Hydroxyphenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one hemihydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 105.3560(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.90960(10)
_cell_length_b                   5.58360(10)
_cell_length_c                   16.8121(2)
_cell_measurement_reflns_used    9119
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0860
_cell_measurement_theta_min      3.8270
_cell_volume                     1078.07(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
PublCif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13888
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.232
_diffrn_reflns_theta_min         3.849
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.188
_refine_ls_extinction_coef       0.0039(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0344
_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)+(0.0512P)²+0.3933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                2067
_reflns_number_total             2221
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2023sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2244231.cif.'
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               2244231
_cod_database_fobs_code          2244231
_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_min   0.872
_shelx_estimated_absorpt_t_max   0.905
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.27900(7) 0.42189(15) 0.33951(5) 0.0268(2) Uani d 1 . .
O O2 0.81284(7) 0.95369(15) 0.59533(5) 0.0215(2) Uani d 1 . .
O O3 0.000000 0.0526(2) 0.250000 0.0208(3) Uani d 1 . .
N N1 0.10566(8) 0.45548(17) 0.19188(5) 0.0186(2) Uani d 1 . .
C C1 0.17738(9) 0.7925(2) 0.15408(6) 0.0178(2) Uani d 1 . .
H H1A 0.225141 0.928386 0.153517 0.021 Uiso calc 1 . .
C C2 0.07695(9) 0.7278(2) 0.09255(6) 0.0222(3) Uani d 1 . .
H H2A 0.044033 0.812012 0.042726 0.027 Uiso calc 1 . .
C C3 0.03512(9) 0.5190(2) 0.11809(6) 0.0222(3) Uani d 1 . .
H H3 -0.032172 0.434067 0.088590 0.027 Uiso calc 1 . .
C C4 0.19382(9) 0.62052(19) 0.21594(6) 0.0159(2) Uani d 1 . .
C C5 0.28203(9) 0.59293(19) 0.29291(6) 0.0177(2) Uani d 1 . .
C C6 0.37555(9) 0.7736(2) 0.31381(6) 0.0179(2) Uani d 1 . .
H H6 0.376212 0.901776 0.276763 0.021 Uiso calc 1 . .
C C7 0.45937(9) 0.75864(19) 0.38443(6) 0.0173(2) Uani d 1 . .
H H7 0.455306 0.624717 0.418413 0.021 Uiso calc 1 . .
C C8 0.55672(9) 0.92326(19) 0.41588(6) 0.0155(2) Uani d 1 . .
C C9 0.56928(9) 1.14020(19) 0.37719(6) 0.0174(2) Uani d 1 . .
H H9 0.513693 1.186081 0.327786 0.021 Uiso calc 1 . .
C C10 0.66350(9) 1.28752(19) 0.41156(6) 0.0184(2) Uani d 1 . .
H H10 0.672229 1.433834 0.384975 0.022 Uiso calc 1 . .
C C11 0.74552(9) 1.22472(19) 0.48433(6) 0.0181(2) Uani d 1 . .
H H11 0.809769 1.326921 0.507080 0.022 Uiso calc 1 . .
C C12 0.73238(9) 1.0110(2) 0.52331(6) 0.0166(2) Uani d 1 . .
C C13 0.63891(9) 0.86102(19) 0.48899(6) 0.0161(2) Uani d 1 . .
H H13 0.630823 0.714363 0.515581 0.019 Uiso calc 1 . .
H H2O 0.7856(15) 0.832(3) 0.6202(11) 0.050(5) Uiso d 1 . .
H H1N 0.0948(13) 0.324(3) 0.2186(9) 0.034(4) Uiso d 1 . .
H H3O -0.0335(16) -0.039(4) 0.2091(11) 0.062(6) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O2 H2O . . 109.4(11) ?
H3O O3 H3O . 2 108(3) ?
C3 N1 C4 . . 109.61(9) ?
C3 N1 H1N . . 122.9(10) ?
C4 N1 H1N . . 127.4(10) ?
C4 C1 C2 . . 107.27(10) ?
C4 C1 H1A . . 126.4 ?
C2 C1 H1A . . 126.4 ?
C3 C2 C1 . . 107.15(9) ?
C3 C2 H2A . . 126.4 ?
C1 C2 H2A . . 126.4 ?
N1 C3 C2 . . 108.67(10) ?
N1 C3 H3 . . 125.7 ?
C2 C3 H3 . . 125.7 ?
N1 C4 C1 . . 107.30(9) ?
N1 C4 C5 . . 120.68(9) ?
C1 C4 C5 . . 132.01(10) ?
O1 C5 C4 . . 120.80(10) ?
O1 C5 C6 . . 121.48(9) ?
C4 C5 C6 . . 117.73(9) ?
C7 C6 C5 . . 120.54(10) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 127.97(10) ?
C6 C7 H7 . . 116.0 ?
C8 C7 H7 . . 116.0 ?
C13 C8 C9 . . 119.15(9) ?
C13 C8 C7 . . 117.69(9) ?
C9 C8 C7 . . 123.14(9) ?
C10 C9 C8 . . 119.53(9) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C11 . . 121.19(10) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C12 C11 C10 . . 119.33(10) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
O2 C12 C11 . . 118.55(9) ?
O2 C12 C13 . . 121.51(10) ?
C11 C12 C13 . . 119.94(9) ?
C12 C13 C8 . . 120.84(10) ?
C12 C13 H13 . . 119.6 ?
C8 C13 H13 . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 . 1.2417(13) ?
O2 C12 . 1.3683(12) ?
O2 H2O . 0.901(19) ?
O3 H3O . 0.864(18) ?
O3 H3O 2 0.864(18) ?
N1 C3 . 1.3484(13) ?
N1 C4 . 1.3749(13) ?
N1 H1N . 0.888(17) ?
C1 C4 . 1.3906(14) ?
C1 C2 . 1.4056(14) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.3804(17) ?
C2 H2A . 0.9500 ?
C3 H3 . 0.9500 ?
C4 C5 . 1.4429(14) ?
C5 C6 . 1.4748(14) ?
C6 C7 . 1.3362(14) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.4642(14) ?
C7 H7 . 0.9500 ?
C8 C13 . 1.3973(14) ?
C8 C9 . 1.4015(15) ?
C9 C10 . 1.3879(15) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3932(14) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3902(15) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.3903(15) ?
C13 H13 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2O O1 3_666 0.901(19) 1.828(19) 2.7257(11) 174.2(16) yes
N1 H1N O3 . 0.888(17) 2.041(17) 2.8722(13) 155.4(14) yes
C13 H13 O1 3_666 0.95 2.51 3.2050(13) 130.4 yes
O3 H3O O2 4_465 0.864(18) 2.320(18) 2.9430(7) 129.2(16) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 C1 C2 C3 . . . . -0.20(12) ?
C4 N1 C3 C2 . . . . 0.25(13) ?
C1 C2 C3 N1 . . . . -0.03(13) ?
C3 N1 C4 C1 . . . . -0.38(12) ?
C3 N1 C4 C5 . . . . -179.58(9) ?
C2 C1 C4 N1 . . . . 0.35(12) ?
C2 C1 C4 C5 . . . . 179.42(11) ?
N1 C4 C5 O1 . . . . -1.17(16) ?
C1 C4 C5 O1 . . . . 179.86(11) ?
N1 C4 C5 C6 . . . . 178.55(9) ?
C1 C4 C5 C6 . . . . -0.42(17) ?
O1 C5 C6 C7 . . . . -0.66(16) ?
C4 C5 C6 C7 . . . . 179.62(10) ?
C5 C6 C7 C8 . . . . -178.53(9) ?
C6 C7 C8 C13 . . . . -175.38(10) ?
C6 C7 C8 C9 . . . . 6.06(17) ?
C13 C8 C9 C10 . . . . 0.72(14) ?
C7 C8 C9 C10 . . . . 179.26(9) ?
C8 C9 C10 C11 . . . . -0.54(15) ?
C9 C10 C11 C12 . . . . -0.24(16) ?
C10 C11 C12 O2 . . . . -179.10(9) ?
C10 C11 C12 C13 . . . . 0.84(15) ?
O2 C12 C13 C8 . . . . 179.27(9) ?
C11 C12 C13 C8 . . . . -0.67(15) ?
C9 C8 C13 C12 . . . . -0.12(15) ?
C7 C8 C13 C12 . . . . -178.74(9) ?
