#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/21/7122179.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_7122179
loop_
_publ_author_name
'Li, Ting'
'Wang, Huiyan'
'Qian, Pengcheng'
'Yang, Yuhan'
'Li, Bo'
'Zhang, Liming'
_publ_section_title
;
 Au(i)-Catalyzed expeditious access to naphtho[2,3-c]furan-1(3-H)-ones
 from readily available propargylic ynoates.
;
_journal_issue                   74
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10447
_journal_page_last               10450
_journal_paper_doi               10.1039/c8cc06056h
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C19 H13 F O2'
_chemical_formula_weight         292.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-14 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.40(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.508(15)
_cell_length_b                   12.35(2)
_cell_length_c                   14.70(3)
_cell_measurement_reflns_used    975
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.5
_cell_volume                     1363(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5101
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.890
_diffrn_reflns_theta_min         2.154
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0573
_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)+(0.0981P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1753
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1918
_reflns_number_total             2748
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc06056h2.cif
_cod_data_source_block           l06052018_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7122179.cif.
;
_cod_original_cell_volume        1363(5)
_cod_database_code               7122179
_shelx_shelxl_version_number     2014/7
_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   0.975
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.0572(3) 0.6945(2) 0.70696(16) 0.0244(5) Uani 1 1 d . .
C2 C 0.1258(3) 0.62900(18) 0.63241(16) 0.0214(5) Uani 1 1 d . .
C3 C 0.1292(3) 0.65185(18) 0.54238(16) 0.0220(5) Uani 1 1 d . .
C4 C 0.2033(3) 0.57098(18) 0.48550(16) 0.0214(5) Uani 1 1 d . .
C5 C 0.2139(3) 0.5855(2) 0.39187(16) 0.0258(6) Uani 1 1 d . .
H5 H 0.1717 0.6509 0.3651 0.031 Uiso 1 1 calc R U
C6 C 0.2842(3) 0.5072(2) 0.33814(17) 0.0278(6) Uani 1 1 d . .
H6 H 0.2905 0.5188 0.2744 0.033 Uiso 1 1 calc R U
C7 C 0.3474(3) 0.4094(2) 0.37615(17) 0.0273(6) Uani 1 1 d . .
H7 H 0.3950 0.3545 0.3385 0.033 Uiso 1 1 calc R U
C8 C 0.3395(3) 0.39524(18) 0.46488(16) 0.0231(5) Uani 1 1 d . .
C9 C 0.2686(3) 0.47142(18) 0.52463(16) 0.0212(5) Uani 1 1 d . .
C10 C 0.2615(3) 0.45205(19) 0.61783(16) 0.0205(5) Uani 1 1 d . .
H10 H 0.3044 0.3863 0.6438 0.025 Uiso 1 1 calc R U
C11 C 0.1907(2) 0.53115(18) 0.66983(16) 0.0200(5) Uani 1 1 d . .
C12 C 0.1668(3) 0.53354(19) 0.76937(16) 0.0217(5) Uani 1 1 d . .
H12 H 0.0842 0.4742 0.7873 0.026 Uiso 1 1 calc R U
C13 C 0.3423(3) 0.52337(19) 0.82297(16) 0.0223(5) Uani 1 1 d . .
C14 C 0.3964(3) 0.4220(2) 0.85386(17) 0.0280(6) Uani 1 1 d . .
H14 H 0.3198 0.3613 0.8460 0.034 Uiso 1 1 calc R U
C15 C 0.5638(3) 0.4093(2) 0.89650(17) 0.0316(6) Uani 1 1 d . .
H15 H 0.6000 0.3398 0.9176 0.038 Uiso 1 1 calc R U
C16 C 0.6770(3) 0.4966(2) 0.90829(17) 0.0309(6) Uani 1 1 d . .
H16 H 0.7914 0.4871 0.9362 0.037 Uiso 1 1 calc R U
C17 C 0.6223(3) 0.5984(2) 0.87903(17) 0.0296(6) Uani 1 1 d . .
H17 H 0.6984 0.6590 0.8882 0.036 Uiso 1 1 calc R U
C18 C 0.4562(3) 0.6119(2) 0.83618(17) 0.0267(6) Uani 1 1 d . .
H18 H 0.4201 0.6817 0.8158 0.032 Uiso 1 1 calc R U
C19 C 0.0574(3) 0.7555(2) 0.50258(18) 0.0290(6) Uani 1 1 d . .
H19C H 0.0033 0.7986 0.5506 0.044 Uiso 1 1 calc R U
H19B H -0.0328 0.7389 0.4553 0.044 Uiso 1 1 calc R U
H19A H 0.1547 0.7966 0.4759 0.044 Uiso 1 1 calc R U
F1 F 0.40230(17) 0.30114(11) 0.50185(10) 0.0310(4) Uani 1 1 d . .
O1 O 0.0835(2) 0.63792(14) 0.78500(11) 0.0263(4) Uani 1 1 d . .
O2 O -0.0114(2) 0.78277(14) 0.70792(12) 0.0331(5) Uani 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
O2 C1 O1 120.7(2)
O2 C1 C2 131.7(2)
O1 C1 C2 107.6(2)
C3 C2 C11 123.0(2)
C3 C2 C1 129.2(2)
C11 C2 C1 107.8(2)
C2 C3 C4 116.4(2)
C2 C3 C19 122.9(2)
C4 C3 C19 120.7(2)
C5 C4 C3 121.5(2)
C5 C4 C9 118.6(2)
C3 C4 C9 119.9(2)
C6 C5 C4 120.9(2)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C7 120.7(3)
C5 C6 H6 119.7
C7 C6 H6 119.7
C8 C7 C6 118.8(2)
C8 C7 H7 120.6
C6 C7 H7 120.6
C7 C8 F1 118.9(2)
C7 C8 C9 123.9(2)
F1 C8 C9 117.1(2)
C10 C9 C8 121.7(2)
C10 C9 C4 121.3(2)
C8 C9 C4 117.0(2)
C11 C10 C9 117.1(2)
C11 C10 H10 121.5
C9 C10 H10 121.5
C10 C11 C2 122.3(2)
C10 C11 C12 129.1(2)
C2 C11 C12 108.6(2)
O1 C12 C11 103.72(18)
O1 C12 C13 111.17(19)
C11 C12 C13 112.7(2)
O1 C12 H12 109.7
C11 C12 H12 109.7
C13 C12 H12 109.7
C14 C13 C18 119.1(2)
C14 C13 C12 119.0(2)
C18 C13 C12 121.7(2)
C13 C14 C15 120.0(2)
C13 C14 H14 120.0
C15 C14 H14 120.0
C16 C15 C14 120.8(2)
C16 C15 H15 119.6
C14 C15 H15 119.6
C15 C16 C17 119.5(2)
C15 C16 H16 120.3
C17 C16 H16 120.3
C16 C17 C18 120.3(2)
C16 C17 H17 119.9
C18 C17 H17 119.9
C17 C18 C13 120.4(2)
C17 C18 H18 119.8
C13 C18 H18 119.8
C3 C19 H19C 109.5
C3 C19 H19B 109.5
H19C C19 H19B 109.5
C3 C19 H19A 109.5
H19C C19 H19A 109.5
H19B C19 H19A 109.5
C1 O1 C12 112.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.207(3)
C1 O1 1.353(4)
C1 C2 1.465(4)
C2 C3 1.354(4)
C2 C11 1.410(3)
C3 C4 1.425(4)
C3 C19 1.502(4)
C4 C5 1.392(4)
C4 C9 1.439(4)
C5 C6 1.363(4)
C5 H5 0.9500
C6 C7 1.410(4)
C6 H6 0.9500
C7 C8 1.319(4)
C7 H7 0.9500
C8 F1 1.363(3)
C8 C9 1.401(4)
C9 C10 1.393(4)
C10 C11 1.357(4)
C10 H10 0.9500
C11 C12 1.479(4)
C12 O1 1.454(3)
C12 C13 1.524(4)
C12 H12 1.0000
C13 C14 1.390(4)
C13 C18 1.399(4)
C14 C15 1.399(4)
C14 H14 0.9500
C15 C16 1.382(4)
C15 H15 0.9500
C16 C17 1.387(4)
C16 H16 0.9500
C17 C18 1.393(4)
C17 H17 0.9500
C18 H18 0.9500
C19 H19C 0.9800
C19 H19B 0.9800
C19 H19A 0.9800
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
O2 C1 C2 C3 -0.1(4)
O1 C1 C2 C3 -179.8(2)
O2 C1 C2 C11 -179.4(2)
O1 C1 C2 C11 0.9(2)
C11 C2 C3 C4 -0.1(3)
C1 C2 C3 C4 -179.30(19)
C11 C2 C3 C19 179.02(18)
C1 C2 C3 C19 -0.2(3)
C2 C3 C4 C5 -179.97(19)
C19 C3 C4 C5 0.9(3)
C2 C3 C4 C9 0.2(3)
C19 C3 C4 C9 -178.91(17)
C3 C4 C5 C6 -179.62(19)
C9 C4 C5 C6 0.2(3)
C4 C5 C6 C7 0.2(3)
C5 C6 C7 C8 -0.8(3)
C6 C7 C8 F1 -179.33(17)
C6 C7 C8 C9 1.1(3)
C7 C8 C9 C10 179.3(2)
F1 C8 C9 C10 -0.3(3)
C7 C8 C9 C4 -0.8(3)
F1 C8 C9 C4 179.67(16)
C5 C4 C9 C10 -179.93(19)
C3 C4 C9 C10 -0.1(3)
C5 C4 C9 C8 0.1(3)
C3 C4 C9 C8 179.89(18)
C8 C9 C10 C11 179.87(19)
C4 C9 C10 C11 -0.1(3)
C9 C10 C11 C2 0.3(3)
C9 C10 C11 C12 -179.70(19)
C3 C2 C11 C10 -0.2(3)
C1 C2 C11 C10 179.19(19)
C3 C2 C11 C12 179.81(18)
C1 C2 C11 C12 -0.8(2)
C10 C11 C12 O1 -179.6(2)
C2 C11 C12 O1 0.5(2)
C10 C11 C12 C13 60.1(3)
C2 C11 C12 C13 -119.9(2)
O1 C12 C13 C14 148.6(2)
C11 C12 C13 C14 -95.5(3)
O1 C12 C13 C18 -36.1(3)
C11 C12 C13 C18 79.9(3)
C18 C13 C14 C15 -0.8(4)
C12 C13 C14 C15 174.7(2)
C13 C14 C15 C16 -0.1(4)
C14 C15 C16 C17 1.3(4)
C15 C16 C17 C18 -1.5(4)
C16 C17 C18 C13 0.6(4)
C14 C13 C18 C17 0.6(4)
C12 C13 C18 C17 -174.8(2)
O2 C1 O1 C12 179.67(19)
C2 C1 O1 C12 -0.6(2)
C11 C12 O1 C1 0.1(2)
C13 C12 O1 C1 121.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189019
