#------------------------------------------------------------------------------
#$Date: 2024-01-06 11:04:17 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288858 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/28/7062800.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_7062800
loop_
_publ_author_name
'Samyuktha, Arimalai Dinakararaja'
'Ethiraj, Kannatt Radhakrishnan'
'Shanmugam, Ponnusamy'
_publ_section_title
;
 Unusual participation of O-propargyl group during the cyclization of
 6-hydroxy-2-propargyl ethers of aryl chalcones: one-pot synthesis of
 2-acyl-3-styrylbenzofuran and 7-aryldibenzo[b,d]furan-1,7-diols
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20818
_journal_page_last               20830
_journal_paper_doi               10.1039/D3NJ03766E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C24 H16 O3'
_chemical_formula_sum            'C24 H16 O3'
_chemical_formula_weight         352.37
_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
_audit_update_record
;
2022-06-25 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                105.164(2)
_cell_angle_beta                 92.910(2)
_cell_angle_gamma                109.138(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1787(5)
_cell_length_b                   9.1920(5)
_cell_length_c                   11.2622(6)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.38
_cell_volume                     856.66(8)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            38013
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_min         2.376
_diffrn_source                   'i-mu-s-microfocus source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0465
_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)+(0.0605P)²+0.3197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3088
_reflns_number_total             4227
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj03766e2.cif
_cod_data_source_block           SA_98RE_250422_0m_a
_cod_depositor_comments
'Adding full bibliography for 7062800--7062802.cif.'
_cod_database_code               7062800
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.93069(13) 0.31243(14) 0.27708(10) 0.0515(3) Uani 1 1 d . . . . .
O2 O 0.81086(16) 0.01954(14) 0.57457(12) 0.0588(3) Uani 1 1 d . . . . .
H1 H 0.775(3) 0.024(3) 0.644(2) 0.088 Uiso 1 1 d . U . . .
O3 O 0.69277(17) 0.67468(16) 0.45184(12) 0.0645(4) Uani 1 1 d . . . . .
H1B H 0.704(3) 0.776(3) 0.465(2) 0.097 Uiso 1 1 d . U . . .
C1 C 0.40847(18) 0.18307(19) 1.01344(14) 0.0443(3) Uani 1 1 d . . . . .
C2 C 0.2608(2) 0.0697(3) 1.00242(18) 0.0657(5) Uani 1 1 d . . . . .
H2 H 0.213519 -0.005989 0.925916 0.079 Uiso 1 1 calc R U . . .
C3 C 0.1830(2) 0.0688(3) 1.1055(2) 0.0767(6) Uani 1 1 d . . . . .
H3 H 0.084026 -0.007507 1.097125 0.092 Uiso 1 1 calc R U . . .
C4 C 0.2509(2) 0.1792(3) 1.21932(19) 0.0648(5) Uani 1 1 d . . . . .
H4 H 0.196764 0.180345 1.286949 0.078 Uiso 1 1 calc R U . . .
C5 C 0.3987(2) 0.2875(2) 1.23254(17) 0.0576(4) Uani 1 1 d . . . . .
H5 H 0.447028 0.359627 1.310142 0.069 Uiso 1 1 calc R U . . .
C6 C 0.4764(2) 0.2898(2) 1.13057(15) 0.0491(4) Uani 1 1 d . . . . .
H6 H 0.576601 0.364535 1.140684 0.059 Uiso 1 1 calc R U . . .
C7 C 0.48993(17) 0.19430(18) 0.90376(13) 0.0410(3) Uani 1 1 d . . . . .
C8 C 0.58789(18) 0.34361(18) 0.89676(14) 0.0441(3) Uani 1 1 d . . . . .
H8 H 0.603267 0.435677 0.962267 0.053 Uiso 1 1 calc R U . . .
C9 C 0.66221(18) 0.35717(17) 0.79465(14) 0.0430(3) Uani 1 1 d . . . . .
H9 H 0.727296 0.458141 0.793048 0.052 Uiso 1 1 calc R U . . .
C10 C 0.64191(17) 0.22282(17) 0.69378(13) 0.0401(3) Uani 1 1 d . . . . .
C11 C 0.54265(18) 0.07392(18) 0.70035(14) 0.0458(4) Uani 1 1 d . . . . .
H11 H 0.525367 -0.017868 0.634078 0.055 Uiso 1 1 calc R U . . .
C12 C 0.46949(18) 0.06017(18) 0.80347(15) 0.0460(4) Uani 1 1 d . . . . .
H12 H 0.405365 -0.040891 0.805645 0.055 Uiso 1 1 calc R U . . .
C13 C 0.72158(17) 0.24327(17) 0.58436(13) 0.0398(3) Uani 1 1 d . . . . .
C14 C 0.72101(17) 0.36770(17) 0.53553(13) 0.0406(3) Uani 1 1 d . . . . .
H14 H 0.671040 0.437712 0.571556 0.049 Uiso 1 1 calc R U . . .
C15 C 0.79482(17) 0.38730(17) 0.43332(13) 0.0396(3) Uani 1 1 d . . . . .
C16 C 0.86867(17) 0.28085(18) 0.38110(13) 0.0428(3) Uani 1 1 d . . . . .
C17 C 0.87666(18) 0.15912(18) 0.42745(14) 0.0466(4) Uani 1 1 d . . . . .
H17 H 0.929339 0.091534 0.392180 0.056 Uiso 1 1 calc R U . . .
C18 C 0.80221(18) 0.14243(17) 0.52934(14) 0.0434(3) Uani 1 1 d . . . . .
C19 C 0.81457(17) 0.49504(17) 0.35706(13) 0.0422(3) Uani 1 1 d . . . . .
C20 C 0.89531(18) 0.4431(2) 0.26337(15) 0.0475(4) Uani 1 1 d . . . . .
C21 C 0.7716(2) 0.62749(19) 0.35875(15) 0.0488(4) Uani 1 1 d . . . . .
C22 C 0.8079(2) 0.6996(2) 0.26531(17) 0.0583(4) Uani 1 1 d . . . . .
H22 H 0.778859 0.787263 0.264411 0.070 Uiso 1 1 calc R U . . .
C23 C 0.8869(2) 0.6428(2) 0.17307(17) 0.0639(5) Uani 1 1 d . . . . .
H23 H 0.909845 0.693791 0.111487 0.077 Uiso 1 1 calc R U . . .
C24 C 0.9327(2) 0.5129(2) 0.16951(16) 0.0599(5) Uani 1 1 d . . . . .
H24 H 0.985697 0.474907 0.107434 0.072 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'
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
C16 O1 C20 105.61(11) . . ?
C2 C1 C6 117.69(15) . . ?
C2 C1 C7 121.59(15) . . ?
C6 C1 C7 120.69(14) . . ?
C1 C2 C3 120.29(19) . . ?
C4 C3 C2 120.75(18) . . ?
C5 C4 C3 119.54(17) . . ?
C4 C5 C6 120.05(18) . . ?
C5 C6 C1 121.60(16) . . ?
C12 C7 C8 117.39(14) . . ?
C12 C7 C1 122.21(14) . . ?
C8 C7 C1 120.38(13) . . ?
C9 C8 C7 121.33(14) . . ?
C8 C9 C10 121.44(14) . . ?
C9 C10 C11 117.15(13) . . ?
C9 C10 C13 119.70(13) . . ?
C11 C10 C13 123.12(13) . . ?
C12 C11 C10 121.36(14) . . ?
C11 C12 C7 121.32(14) . . ?
C14 C13 C18 118.24(13) . . ?
C14 C13 C10 119.82(13) . . ?
C18 C13 C10 121.92(13) . . ?
C15 C14 C13 120.13(13) . . ?
C14 C15 C16 118.80(13) . . ?
C14 C15 C19 135.75(14) . . ?
C16 C15 C19 105.42(13) . . ?
C17 C16 O1 124.82(13) . . ?
C17 C16 C15 123.53(14) . . ?
O1 C16 C15 111.65(13) . . ?
C16 C17 C18 116.41(13) . . ?
O2 C18 C17 115.75(13) . . ?
O2 C18 C13 121.42(14) . . ?
C17 C18 C13 122.84(14) . . ?
C20 C19 C21 118.78(14) . . ?
C20 C19 C15 106.26(13) . . ?
C21 C19 C15 134.96(14) . . ?
C24 C20 O1 125.16(16) . . ?
C24 C20 C19 123.79(17) . . ?
O1 C20 C19 111.05(13) . . ?
O3 C21 C22 124.41(16) . . ?
O3 C21 C19 117.08(14) . . ?
C22 C21 C19 118.49(16) . . ?
C21 C22 C23 120.78(17) . . ?
C24 C23 C22 122.18(17) . . ?
C20 C24 C23 115.96(17) . . ?
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 C16 1.3850(18) . ?
O1 C20 1.386(2) . ?
O2 C18 1.3775(18) . ?
O3 C21 1.363(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.389(2) . ?
C1 C7 1.485(2) . ?
C2 C3 1.394(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.367(3) . ?
C5 C6 1.384(2) . ?
C7 C12 1.389(2) . ?
C7 C8 1.397(2) . ?
C8 C9 1.379(2) . ?
C9 C10 1.394(2) . ?
C10 C11 1.397(2) . ?
C10 C13 1.487(2) . ?
C11 C12 1.384(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.409(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.392(2) . ?
C15 C19 1.447(2) . ?
C16 C17 1.373(2) . ?
C17 C18 1.382(2) . ?
C19 C20 1.392(2) . ?
C19 C21 1.393(2) . ?
C20 C24 1.376(2) . ?
C21 C22 1.383(2) . ?
C22 C23 1.385(3) . ?
C23 C24 1.383(3) . ?
