#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:32:31 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268950 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158230.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_7158230
loop_
_publ_author_name
'Yadav, Maruti B.'
'Jeong, Yeon Tae'
_publ_section_title
;
 A one-pot ring-closure and ring-opening sequence for the cascade
 synthesis of dihydrofurofurans and functionalized furans.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7409
_journal_page_last               7419
_journal_paper_doi               10.1039/d1ob01300a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C26 H17 F N2 O3'
_chemical_formula_sum            'C26 H17 F N2 O3'
_chemical_formula_weight         424.42
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.8865(7)
_cell_length_b                   22.291(3)
_cell_length_c                   25.817(2)
_cell_measurement_reflns_used    8758
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.9
_cell_measurement_theta_min      2.414
_cell_volume                     3963.1(7)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20978
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0571P)²+0.8835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                2929
_reflns_number_total             3505
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01300a2.cif
_cod_data_source_block           d23190
_cod_depositor_comments
'Adding full bibliography for 7158230--7158231.cif.'
_cod_database_code               7158230
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3293(2) 0.56808(6) 0.52801(5) 0.0233(3) Uani 1 1 d . . .
C2 C 0.4666(2) 0.61213(6) 0.50386(5) 0.0221(3) Uani 1 1 d . . .
C3 C 0.3938(2) 0.66717(7) 0.48656(6) 0.0262(3) Uani 1 1 d . . .
H3 H 0.2596 0.6760 0.4906 0.031 Uiso 1 1 calc R . .
C4 C 0.5151(2) 0.70892(7) 0.46362(6) 0.0303(4) Uani 1 1 d . . .
H4 H 0.4650 0.7466 0.4527 0.036 Uiso 1 1 calc R . .
C5 C 0.7106(2) 0.69562(7) 0.45654(6) 0.0323(4) Uani 1 1 d . . .
H5 H 0.7937 0.7239 0.4402 0.039 Uiso 1 1 calc R . .
C6 C 0.7842(2) 0.64109(7) 0.47324(6) 0.0305(4) Uani 1 1 d . . .
H6 H 0.9177 0.6320 0.4683 0.037 Uiso 1 1 calc R . .
C7 C 0.6633(2) 0.59964(7) 0.49727(5) 0.0256(3) Uani 1 1 d . . .
H7 H 0.7149 0.5626 0.5092 0.031 Uiso 1 1 calc R . .
C8 C 0.3766(2) 0.54189(6) 0.57702(5) 0.0225(3) Uani 1 1 d . . .
C9 C 0.2502(2) 0.50382(7) 0.60212(5) 0.0231(3) Uani 1 1 d . . .
C10 C 0.5090(2) 0.50653(7) 0.65733(5) 0.0228(3) Uani 1 1 d . . .
C11 C 0.6508(2) 0.45537(6) 0.66432(5) 0.0225(3) Uani 1 1 d . . .
C12 C 0.6399(2) 0.40442(7) 0.63339(6) 0.0308(4) Uani 1 1 d . . .
H12 H 0.5361 0.4002 0.6094 0.037 Uiso 1 1 calc R . .
C13 C 0.7799(3) 0.35956(7) 0.63723(6) 0.0357(4) Uani 1 1 d . . .
H13 H 0.7731 0.3247 0.6161 0.043 Uiso 1 1 calc R . .
C14 C 0.9278(2) 0.36691(7) 0.67223(6) 0.0316(4) Uani 1 1 d . . .
C15 C 0.9412(2) 0.41606(7) 0.70417(6) 0.0317(4) Uani 1 1 d . . .
H15 H 1.0438 0.4195 0.7286 0.038 Uiso 1 1 calc R . .
C16 C 0.8015(2) 0.46053(7) 0.69989(6) 0.0273(4) Uani 1 1 d . . .
H16 H 0.8089 0.4949 0.7215 0.033 Uiso 1 1 calc R . .
C17 C 0.5309(2) 0.60063(7) 0.69322(6) 0.0227(3) Uani 1 1 d . . .
C18 C 0.5348(2) 0.63957(7) 0.73899(6) 0.0243(3) Uani 1 1 d . . .
C19 C 0.5520(2) 0.61428(8) 0.78842(6) 0.0284(4) Uani 1 1 d . . .
H19 H 0.5583 0.5719 0.7923 0.034 Uiso 1 1 calc R . .
C20 C 0.5598(2) 0.65085(8) 0.83159(6) 0.0359(4) Uani 1 1 d . . .
H20 H 0.5719 0.6335 0.8650 0.043 Uiso 1 1 calc R . .
C21 C 0.5503(3) 0.71248(9) 0.82648(7) 0.0411(5) Uani 1 1 d . . .
H21 H 0.5564 0.7374 0.8563 0.049 Uiso 1 1 calc R . .
C22 C 0.5319(3) 0.73783(8) 0.77800(7) 0.0410(4) Uani 1 1 d . . .
H22 H 0.5246 0.7802 0.7746 0.049 Uiso 1 1 calc R . .
C23 C 0.5239(2) 0.70191(7) 0.73424(6) 0.0321(4) Uani 1 1 d . . .
H23 H 0.5110 0.7197 0.7010 0.039 Uiso 1 1 calc R . .
C24 C 0.5586(2) 0.61048(7) 0.64211(6) 0.0225(3) Uani 1 1 d . . .
C25 C 0.5961(2) 0.66695(7) 0.61838(6) 0.0265(3) Uani 1 1 d . . .
C26 C 0.5494(2) 0.55165(6) 0.61235(5) 0.0212(3) Uani 1 1 d . . .
H26 H 0.6748 0.5427 0.5944 0.025 Uiso 1 1 calc R . .
F1 F 1.06870(16) 0.32431(5) 0.67515(4) 0.0498(3) Uani 1 1 d . . .
N1 N 0.07367(18) 0.48584(6) 0.58848(5) 0.0289(3) Uani 1 1 d . . .
H1D H 0.0356 0.4939 0.5541 0.035 Uiso 1 1 d R . .
H1E H 0.0139 0.4539 0.6075 0.035 Uiso 1 1 d R . .
N2 N 0.6258(2) 0.71210(6) 0.59836(5) 0.0401(4) Uani 1 1 d . . .
O1 O 0.17421(15) 0.55596(5) 0.50509(4) 0.0338(3) Uani 1 1 d . . .
O2 O 0.31611(14) 0.48263(5) 0.64824(4) 0.0262(3) Uani 1 1 d . . .
O3 O 0.50019(16) 0.54072(4) 0.70402(4) 0.0264(3) 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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C8 121.63(13) . . ?
O1 C1 C2 118.92(12) . . ?
C8 C1 C2 119.45(12) . . ?
C7 C2 C3 119.02(14) . . ?
C7 C2 C1 122.22(13) . . ?
C3 C2 C1 118.75(13) . . ?
C4 C3 C2 120.66(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.84(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.00(15) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.20(15) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.27(14) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C1 121.59(13) . . ?
C9 C8 C26 107.54(12) . . ?
C1 C8 C26 130.72(13) . . ?
N1 C9 O2 115.67(13) . . ?
N1 C9 C8 129.76(14) . . ?
O2 C9 C8 114.55(13) . . ?
O3 C10 O2 107.09(11) . . ?
O3 C10 C11 109.21(11) . . ?
O2 C10 C11 109.50(12) . . ?
O3 C10 C26 106.95(11) . . ?
O2 C10 C26 106.25(11) . . ?
C11 C10 C26 117.36(12) . . ?
C12 C11 C16 119.14(14) . . ?
C12 C11 C10 120.83(13) . . ?
C16 C11 C10 119.91(13) . . ?
C11 C12 C13 120.56(15) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 118.37(15) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
F1 C14 C13 118.88(15) . . ?
F1 C14 C15 118.39(14) . . ?
C13 C14 C15 122.72(15) . . ?
C14 C15 C16 118.42(15) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C11 120.77(14) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C24 C17 O3 112.10(13) . . ?
C24 C17 C18 133.48(14) . . ?
O3 C17 C18 114.36(12) . . ?
C23 C18 C19 119.01(14) . . ?
C23 C18 C17 121.14(14) . . ?
C19 C18 C17 119.85(14) . . ?
C20 C19 C18 120.06(16) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.51(16) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.90(16) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.44(17) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.07(16) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C17 C24 C25 126.13(14) . . ?
C17 C24 C26 110.32(13) . . ?
C25 C24 C26 123.53(12) . . ?
N2 C25 C24 178.77(16) . . ?
C8 C26 C24 117.41(12) . . ?
C8 C26 C10 102.42(11) . . ?
C24 C26 C10 100.79(11) . . ?
C8 C26 H26 111.7 . . ?
C24 C26 H26 111.7 . . ?
C10 C26 H26 111.7 . . ?
C9 N1 H1D 116.6 . . ?
C9 N1 H1E 118.8 . . ?
H1D N1 H1E 120.3 . . ?
C9 O2 C10 108.65(11) . . ?
C17 O3 C10 109.83(11) . . ?
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
C1 O1 1.2507(18) . ?
C1 C8 1.431(2) . ?
C1 C2 1.499(2) . ?
C2 C7 1.393(2) . ?
C2 C3 1.399(2) . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.377(2) . ?
C8 C26 1.515(2) . ?
C9 N1 1.3278(19) . ?
C9 O2 1.3590(17) . ?
C10 O3 1.4276(17) . ?
C10 O2 1.4500(17) . ?
C10 C11 1.512(2) . ?
C10 C26 1.5612(19) . ?
C11 C12 1.390(2) . ?
C11 C16 1.391(2) . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(2) . ?
C13 H13 0.9500 . ?
C14 F1 1.3599(18) . ?
C14 C15 1.374(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C24 1.351(2) . ?
C17 O3 1.3805(17) . ?
C17 C18 1.466(2) . ?
C18 C23 1.397(2) . ?
C18 C19 1.400(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.424(2) . ?
C24 C26 1.521(2) . ?
C25 N2 1.1497(19) . ?
C26 H26 1.0000 . ?
N1 H1D 0.9424 . ?
N1 H1E 0.9583 . ?
