#------------------------------------------------------------------------------
#$Date: 2024-03-05 22:29:40 +0200 (Tue, 05 Mar 2024) $
#$Revision: 290320 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/24/2312415.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_2312415
loop_
_publ_author_name
'Safarova, Ayten S.'
'Khalilov, Ali N.'
'Akkurt, Mehmet'
'Maharramov, Abel M.'
'Bhattarai, Ajaya'
'Naghiyev, Farid N.'
'Mamedov, İbrahim G'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (2E)-1-phenyl-3-(1H-pyrrol-2-yl)propen-1-one.
;
_journal_coeditor_code           TX2080
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              191
_journal_page_last               195
_journal_paper_doi               10.1107/S2056989024000495
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C13 H11 N O'
_chemical_formula_moiety         'C13 H11 N O'
_chemical_formula_sum            'C13 H11 N O'
_chemical_formula_weight         197.23
_chemical_name_systematic
;
(2E)-1-Phenyl-3-(1H-pyrrol-2-yl)propen-1-one
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                106.519(8)
_cell_angle_beta                 91.912(9)
_cell_angle_gamma                92.326(9)
_cell_formula_units_Z            2
_cell_length_a                   5.7855(16)
_cell_length_b                   7.3347(19)
_cell_length_c                   12.424(3)
_cell_measurement_reflns_used    5813
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.90
_cell_volume                     504.5(2)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18072
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.565
_diffrn_reflns_theta_min         2.916
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0493
_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)+(0.0348P)²+0.1277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                1908
_reflns_number_total             2535
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2080.cif
_cod_data_source_block           global
_cod_database_code               2312415
_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   0.990
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.2761(2) 0.1954(2) 0.68844(12) 0.0384(3) Uani d 1 . .
H H1 0.152580 0.148144 0.636826 0.046 Uiso calc 1 . .
C C2 0.2561(3) 0.1996(2) 0.79934(13) 0.0454(4) Uani d 1 . .
H H2 0.120202 0.152611 0.822105 0.055 Uiso calc 1 . .
C C3 0.4365(3) 0.2729(2) 0.87637(13) 0.0482(4) Uani d 1 . .
H H3 0.421898 0.276227 0.951211 0.058 Uiso calc 1 . .
C C4 0.6386(3) 0.3416(2) 0.84307(13) 0.0455(4) Uani d 1 . .
H H4 0.759276 0.393419 0.895615 0.055 Uiso calc 1 . .
C C5 0.6619(2) 0.3335(2) 0.73212(12) 0.0378(3) Uani d 1 . .
H H5 0.800320 0.376468 0.709453 0.045 Uiso calc 1 . .
C C6 0.4805(2) 0.26175(18) 0.65370(11) 0.0324(3) Uani d 1 . .
C C7 0.5128(2) 0.25283(19) 0.53401(11) 0.0354(3) Uani d 1 . .
C C8 0.3085(2) 0.2513(2) 0.46122(12) 0.0383(3) Uani d 1 . .
H H8 0.168759 0.287979 0.493566 0.046 Uiso calc 1 . .
C C9 0.3176(2) 0.19850(19) 0.34947(11) 0.0357(3) Uani d 1 . .
H H9 0.455504 0.148284 0.321134 0.043 Uiso calc 1 . .
C C10 0.1436(2) 0.20911(19) 0.26803(11) 0.0335(3) Uani d 1 . .
C C11 0.1590(3) 0.1715(2) 0.15357(12) 0.0407(4) Uani d 1 . .
H H11 0.283975 0.120383 0.112231 0.049 Uiso calc 1 . .
C C12 -0.0454(3) 0.2235(2) 0.11041(13) 0.0457(4) Uani d 1 . .
H H12 -0.081206 0.214416 0.035462 0.055 Uiso calc 1 . .
C C13 -0.1829(3) 0.2901(2) 0.19837(13) 0.0436(4) Uani d 1 . .
H H13 -0.330437 0.334068 0.193755 0.052 Uiso calc 1 . .
N N1 -0.0693(2) 0.28171(17) 0.29363(10) 0.0386(3) Uani d 1 . .
H H1N -0.130(3) 0.302(2) 0.3590(14) 0.046 Uiso d 1 . .
O O1 0.70997(17) 0.25046(16) 0.49928(8) 0.0496(3) Uani 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.07(14) ?
C2 C1 H1 . . 120.0 ?
C6 C1 H1 . . 120.0 ?
C3 C2 C1 . . 120.16(14) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 120.20(14) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C5 C4 C3 . . 119.93(14) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.48(13) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 119.12(13) ?
C5 C6 C7 . . 119.03(12) ?
C1 C6 C7 . . 121.83(12) ?
O1 C7 C8 . . 121.73(13) ?
O1 C7 C6 . . 119.52(13) ?
C8 C7 C6 . . 118.74(12) ?
C9 C8 C7 . . 121.56(13) ?
C9 C8 H8 . . 119.2 ?
C7 C8 H8 . . 119.2 ?
C8 C9 C10 . . 128.38(13) ?
C8 C9 H9 . . 115.8 ?
C10 C9 H9 . . 115.8 ?
N1 C10 C11 . . 106.72(12) ?
N1 C10 C9 . . 124.28(12) ?
C11 C10 C9 . . 128.65(13) ?
C10 C11 C12 . . 108.08(13) ?
C10 C11 H11 . . 126.0 ?
C12 C11 H11 . . 126.0 ?
C13 C12 C11 . . 107.23(13) ?
C13 C12 H12 . . 126.4 ?
C11 C12 H12 . . 126.4 ?
N1 C13 C12 . . 108.61(14) ?
N1 C13 H13 . . 125.7 ?
C12 C13 H13 . . 125.7 ?
C13 N1 C10 . . 109.35(12) ?
C13 N1 H1N . . 125.1(10) ?
C10 N1 H1N . . 124.9(10) ?
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
C1 C2 . 1.378(2) ?
C1 C6 . 1.3886(19) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.375(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.377(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.374(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.3867(19) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.4882(19) ?
C7 O1 . 1.2318(16) ?
C7 C8 . 1.462(2) ?
C8 C9 . 1.3346(19) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.4237(19) ?
C9 H9 . 0.9300 ?
C10 N1 . 1.3728(18) ?
C10 C11 . 1.3761(19) ?
C11 C12 . 1.394(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.361(2) ?
C12 H12 . 0.9300 ?
C13 N1 . 1.3526(18) ?
C13 H13 . 0.9300 ?
N1 H1N . 0.871(16) ?
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
N1 H1N O1 1_455 0.872(17) 2.119(17) 2.9561(18) 160.7(14) yes
C2 H2 Cg1 2_556 0.93 2.82 3.450(2) 126 yes
C5 H5 Cg1 2_666 0.93 2.91 3.5233(19) 124 yes
C9 H9 Cg2 2_656 0.93 3.00 3.6207(18) 126 yes
C13 H13 Cg2 2_566 0.93 2.95 3.593(2) 127 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
C6 C1 C2 C3 . . . . 1.3(2) ?
C1 C2 C3 C4 . . . . -0.4(2) ?
C2 C3 C4 C5 . . . . -1.2(2) ?
C3 C4 C5 C6 . . . . 1.9(2) ?
C4 C5 C6 C1 . . . . -1.0(2) ?
C4 C5 C6 C7 . . . . -179.23(12) ?
C2 C1 C6 C5 . . . . -0.7(2) ?
C2 C1 C6 C7 . . . . 177.54(13) ?
C5 C6 C7 O1 . . . . 22.6(2) ?
C1 C6 C7 O1 . . . . -155.56(14) ?
C5 C6 C7 C8 . . . . -156.04(13) ?
C1 C6 C7 C8 . . . . 25.76(19) ?
O1 C7 C8 C9 . . . . 17.6(2) ?
C6 C7 C8 C9 . . . . -163.76(13) ?
C7 C8 C9 C10 . . . . -172.34(13) ?
C8 C9 C10 N1 . . . . 1.1(2) ?
C8 C9 C10 C11 . . . . 173.37(14) ?
N1 C10 C11 C12 . . . . 0.50(16) ?
C9 C10 C11 C12 . . . . -172.82(13) ?
C10 C11 C12 C13 . . . . -0.54(17) ?
C11 C12 C13 N1 . . . . 0.37(17) ?
C12 C13 N1 C10 . . . . -0.06(16) ?
C11 C10 N1 C13 . . . . -0.27(15) ?
C9 C10 N1 C13 . . . . 173.41(13) ?
