#------------------------------------------------------------------------------
#$Date: 2022-11-08 21:41:24 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567720.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_1567720
loop_
_publ_author_name
Vinaya
'Basavaraju, Yeriyur B.'
'Nagma Banu, Holalagudu A.'
'Kalluraya, Balakrishna'
'Yathirajan, Hemmige S.'
'Balerao, Rishik'
'Butcher, Ray J.'
_publ_section_title
;
 3-(3-Nitrophenyl)-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one
;
_journal_coeditor_code           BT4126
_journal_issue                   10
_journal_name_full               IUCrData
_journal_page_first              x220957
_journal_paper_doi               10.1107/S2414314622009579
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C18 H13 N O4'
_chemical_formula_moiety         'C18 H13 N O4'
_chemical_formula_sum            'C18 H13 N O4'
_chemical_formula_weight         307.29
_chemical_name_systematic
;
3-(3-Nitrophenyl)-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                94.433(7)
_cell_angle_beta                 97.953(8)
_cell_angle_gamma                97.019(7)
_cell_formula_units_Z            2
_cell_length_a                   7.6534(16)
_cell_length_b                   8.6079(15)
_cell_length_c                   11.369(2)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.85
_cell_measurement_theta_min      2.71
_cell_volume                     732.8(2)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            47166
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.395
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7293
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0459
_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)+(0.0642P)²+0.1082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                2700
_reflns_number_total             3638
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4126.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1567720.cif.'
_cod_original_cell_volume        732.8(3)
_cod_database_code               1567720
_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.
;
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
O O1 0.8224(2) -0.53179(13) 0.40582(11) 0.0732(4) Uani d 1 . .
O O2 0.78869(16) -0.48667(12) 0.22192(10) 0.0557(3) Uani d 1 . .
O O3 0.38666(16) 0.19330(12) 0.03294(9) 0.0557(3) Uani d 1 . .
O O4 0.12863(14) 0.82184(10) 0.22678(8) 0.0419(3) Uani d 1 . .
N N1 0.79204(16) -0.44535(13) 0.32710(11) 0.0436(3) Uani d 1 . .
C C1 0.63484(18) -0.05300(15) 0.30785(12) 0.0358(3) Uani d 1 . .
C C2 0.67213(17) -0.20372(14) 0.27518(11) 0.0342(3) Uani d 1 . .
H H2A 0.639784 -0.249615 0.195197 0.041 Uiso calc 1 . .
C C3 0.75705(18) -0.28509(15) 0.36138(12) 0.0362(3) Uani d 1 . .
C C4 0.8101(2) -0.22355(17) 0.47820(12) 0.0446(3) Uani d 1 . .
H H4A 0.868961 -0.282414 0.535011 0.054 Uiso calc 1 . .
C C5 0.7751(2) -0.07331(18) 0.51018(13) 0.0518(4) Uani d 1 . .
H H5A 0.811026 -0.027252 0.589874 0.062 Uiso calc 1 . .
C C6 0.6882(2) 0.00972(17) 0.42650(13) 0.0469(4) Uani d 1 . .
H H6A 0.663892 0.112233 0.450078 0.056 Uiso calc 1 . .
C C7 0.54529(18) 0.03375(15) 0.21647(12) 0.0378(3) Uani d 1 . .
H H7A 0.524932 -0.013883 0.136707 0.045 Uiso calc 1 . .
C C8 0.49007(19) 0.17290(15) 0.23512(12) 0.0402(3) Uani d 1 . .
H H8A 0.505167 0.222444 0.314155 0.048 Uiso calc 1 . .
C C9 0.40553(19) 0.25253(15) 0.13558(12) 0.0386(3) Uani d 1 . .
C C10 0.34071(18) 0.40617(14) 0.16303(11) 0.0345(3) Uani d 1 . .
C C11 0.32576(18) 0.46816(15) 0.27815(11) 0.0366(3) Uani d 1 . .
H H11A 0.365827 0.414762 0.344742 0.044 Uiso calc 1 . .
C C12 0.25357(19) 0.60589(15) 0.29624(11) 0.0382(3) Uani d 1 . .
H H12A 0.242477 0.645757 0.374749 0.046 Uiso calc 1 . .
C C13 0.19719(17) 0.68610(14) 0.19960(11) 0.0343(3) Uani d 1 . .
C C14 0.2132(2) 0.62771(16) 0.08447(12) 0.0418(3) Uani d 1 . .
H H14A 0.176033 0.682647 0.018101 0.050 Uiso calc 1 . .
C C15 0.2840(2) 0.48861(16) 0.06802(12) 0.0418(3) Uani d 1 . .
H H15A 0.293985 0.448410 -0.010617 0.050 Uiso calc 1 . .
C C16 0.0652(2) 0.90385(15) 0.12751(12) 0.0412(3) Uani d 1 . .
H H16A -0.037244 0.838377 0.076985 0.049 Uiso calc 1 . .
H H16B 0.160640 0.926181 0.078194 0.049 Uiso calc 1 . .
C C17 0.01114(18) 1.05106(15) 0.17380(12) 0.0397(3) Uani d 1 . .
C C18 -0.0334(2) 1.17155(17) 0.20482(14) 0.0466(4) Uani d 1 . .
H H18A -0.067(2) 1.266(2) 0.2248(15) 0.057(5) 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 0.0033 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
C13 O4 C16 . . 116.23(10) y
O2 N1 O1 . . 122.80(12) ?
O2 N1 C3 . . 118.79(11) ?
O1 N1 C3 . . 118.40(12) ?
C2 C1 C6 . . 118.12(12) ?
C2 C1 C7 . . 118.90(11) ?
C6 C1 C7 . . 122.97(12) ?
C3 C2 C1 . . 118.80(12) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C4 C3 C2 . . 123.22(12) ?
C4 C3 N1 . . 118.22(11) ?
C2 C3 N1 . . 118.56(11) ?
C3 C4 C5 . . 117.94(12) ?
C3 C4 H4A . . 121.0 ?
C5 C4 H4A . . 121.0 ?
C6 C5 C4 . . 120.11(13) ?
C6 C5 H5A . . 119.9 ?
C4 C5 H5A . . 119.9 ?
C5 C6 C1 . . 121.80(13) ?
C5 C6 H6A . . 119.1 ?
C1 C6 H6A . . 119.1 ?
C8 C7 C1 . . 125.96(12) ?
C8 C7 H7A . . 117.0 ?
C1 C7 H7A . . 117.0 ?
C7 C8 C9 . . 121.55(12) ?
C7 C8 H8A . . 119.2 ?
C9 C8 H8A . . 119.2 ?
O3 C9 C8 . . 120.87(12) ?
O3 C9 C10 . . 120.22(12) ?
C8 C9 C10 . . 118.90(11) ?
C15 C10 C11 . . 118.06(11) ?
C15 C10 C9 . . 117.85(11) ?
C11 C10 C9 . . 124.01(11) ?
C12 C11 C10 . . 120.89(11) ?
C12 C11 H11A . . 119.6 ?
C10 C11 H11A . . 119.6 ?
C11 C12 C13 . . 119.98(12) ?
C11 C12 H12A . . 120.0 ?
C13 C12 H12A . . 120.0 ?
O4 C13 C12 . . 115.58(11) ?
O4 C13 C14 . . 124.35(11) ?
C12 C13 C14 . . 120.07(11) ?
C15 C14 C13 . . 119.11(12) ?
C15 C14 H14A . . 120.4 ?
C13 C14 H14A . . 120.4 ?
C14 C15 C10 . . 121.89(12) ?
C14 C15 H15A . . 119.1 ?
C10 C15 H15A . . 119.1 ?
O4 C16 C17 . . 108.45(11) ?
O4 C16 H16A . . 110.0 ?
C17 C16 H16A . . 110.0 ?
O4 C16 H16B . . 110.0 ?
C17 C16 H16B . . 110.0 ?
H16A C16 H16B . . 108.4 ?
C18 C17 C16 . . 176.40(14) ?
C17 C18 H18A . . 177.0(11) ?
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 N1 . 1.2232(15) y
O2 N1 . 1.2168(16) y
O3 C9 . 1.2189(16) y
O4 C13 . 1.3693(14) ?
O4 C16 . 1.4362(15) ?
N1 C3 . 1.4706(17) y
C1 C2 . 1.3957(17) ?
C1 C6 . 1.3996(19) ?
C1 C7 . 1.4680(18) ?
C2 C3 . 1.3838(17) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.3780(19) ?
C4 C5 . 1.384(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.380(2) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 C8 . 1.3295(17) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.4815(18) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.4940(17) ?
C10 C15 . 1.3866(17) ?
C10 C11 . 1.3997(18) ?
C11 C12 . 1.3809(17) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.3888(17) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.3924(18) ?
C14 C15 . 1.3835(18) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9500 ?
C16 C17 . 1.4627(18) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.1746(19) ?
C18 H18A . 0.901(18) ?
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
C18 H18A O2 1_475 0.901(18) 2.519(18) 3.3927(18) 163.6(15) 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 . . . . 1.0(2) ?
C7 C1 C2 C3 . . . . 179.80(12) ?
C1 C2 C3 C4 . . . . -1.3(2) ?
C1 C2 C3 N1 . . . . 178.51(11) ?
O2 N1 C3 C4 . . . . -161.56(14) ?
O1 N1 C3 C4 . . . . 18.8(2) ?
O2 N1 C3 C2 . . . . 18.64(19) ?
O1 N1 C3 C2 . . . . -160.96(13) ?
C2 C3 C4 C5 . . . . 0.5(2) ?
N1 C3 C4 C5 . . . . -179.33(13) ?
C3 C4 C5 C6 . . . . 0.6(2) ?
C4 C5 C6 C1 . . . . -0.7(3) ?
C2 C1 C6 C5 . . . . -0.1(2) ?
C7 C1 C6 C5 . . . . -178.78(15) ?
C2 C1 C7 C8 . . . . 175.05(13) ?
C6 C1 C7 C8 . . . . -6.3(2) ?
C1 C7 C8 C9 . . . . 178.18(13) ?
C7 C8 C9 O3 . . . . -1.1(2) ?
C7 C8 C9 C10 . . . . 177.91(13) ?
O3 C9 C10 C15 . . . . -9.4(2) ?
C8 C9 C10 C15 . . . . 171.57(13) ?
O3 C9 C10 C11 . . . . 167.42(14) ?
C8 C9 C10 C11 . . . . -11.6(2) ?
C15 C10 C11 C12 . . . . 1.2(2) ?
C9 C10 C11 C12 . . . . -175.62(13) ?
C10 C11 C12 C13 . . . . -1.0(2) ?
C16 O4 C13 C12 . . . . -178.35(11) ?
C16 O4 C13 C14 . . . . 2.0(2) ?
C11 C12 C13 O4 . . . . -179.60(12) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
O4 C13 C14 C15 . . . . -179.70(13) ?
C12 C13 C14 C15 . . . . 0.7(2) ?
C13 C14 C15 C10 . . . . -0.5(2) ?
C11 C10 C15 C14 . . . . -0.4(2) ?
C9 C10 C15 C14 . . . . 176.58(13) ?
C13 O4 C16 C17 . . . . -175.40(11) ?
