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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/19/4031924.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_4031924
loop_
_publ_author_name
'Ouyang, Lu'
'Qi, Chaorong'
'He, Haitao'
'Peng, Youbin'
'Xiong, Wenfang'
'Ren, Yanwei'
'Jiang, Huanfeng'
_publ_section_title
;
 Base-Promoted Formal [4 + 3] Annulation between 2-Fluorophenylacetylenes
 and Ketones: A Route to Benzoxepines.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              912
_journal_page_last               919
_journal_paper_doi               10.1021/acs.joc.5b02487
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C18 H14 O'
_chemical_formula_weight         246.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4783(13)
_cell_length_b                   8.4999(17)
_cell_length_c                   23.571(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1297.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku CCD'
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12729
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.077
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.7(14)
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                1865
_reflns_number_total             2963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02487_si_003.cif
_cod_data_source_block           qi
_cod_original_cell_volume        1297.9(4)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4031924
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'
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
C7 C 0.00412(17) 0.44683(13) 0.03323(6) 0.0486(3) Uani 1 1 d .
C8 C -0.15774(17) 0.49632(14) 0.06633(6) 0.0531(3) Uani 1 1 d .
O1 O -0.17651(14) 0.46277(12) 0.12417(4) 0.0680(3) Uani 1 1 d .
C1 C -0.00025(18) 0.49165(14) -0.02538(5) 0.0493(3) Uani 1 1 d .
C2 C -0.1697(2) 0.57877(13) -0.04778(6) 0.0547(3) Uani 1 1 d .
C6 C 0.1618(2) 0.45277(16) -0.06341(6) 0.0596(3) Uani 1 1 d .
H6A H 0.2742 0.3954 -0.0502 0.071 Uiso 1 1 calc R
C5 C 0.1559(2) 0.49779(19) -0.11874(7) 0.0699(4) Uani 1 1 d .
H5A H 0.2648 0.4718 -0.1427 0.084 Uiso 1 1 calc R
C4 C -0.0111(3) 0.58218(18) -0.14007(7) 0.0718(4) Uani 1 1 d .
H4A H -0.0136 0.6114 -0.1781 0.086 Uiso 1 1 calc R
C10 C -0.3314(2) 0.62193(16) -0.01109(7) 0.0629(4) Uani 1 1 d .
H10A H -0.4441 0.6773 -0.0251 0.075 Uiso 1 1 calc R
C11 C 0.1838(2) 0.34740(17) 0.05346(6) 0.0575(3) Uani 1 1 d .
C3 C -0.1696(3) 0.62176(16) -0.10562(7) 0.0664(4) Uani 1 1 d .
H3A H -0.2805 0.6782 -0.1203 0.080 Uiso 1 1 calc R
C12 C 0.1869(2) 0.29590(16) 0.11498(6) 0.0642(4) Uani 1 1 d .
H12A H 0.0735 0.2236 0.1214 0.077 Uiso 1 1 calc R
H12B H 0.3144 0.2395 0.1222 0.077 Uiso 1 1 calc R
C14 C -0.0146(2) 0.51049(16) 0.15906(6) 0.0585(3) Uani 1 1 d .
C9 C -0.3236(2) 0.58331(16) 0.04439(7) 0.0627(4) Uani 1 1 d .
H9A H -0.4296 0.6148 0.0684 0.075 Uiso 1 1 calc R
C13 C 0.1699(2) 0.42961(15) 0.15612(6) 0.0570(3) Uani 1 1 d .
C15 C -0.0479(3) 0.63037(19) 0.19714(7) 0.0742(4) Uani 1 1 d .
H15A H -0.1746 0.6817 0.1986 0.089 Uiso 1 1 calc R
C17 C 0.2984(3) 0.5980(2) 0.23030(7) 0.0812(5) Uani 1 1 d .
H17A H 0.4055 0.6287 0.2541 0.097 Uiso 1 1 calc R
C18 C 0.3283(2) 0.47666(18) 0.19204(6) 0.0690(4) Uani 1 1 d .
H18A H 0.4555 0.4262 0.1903 0.083 Uiso 1 1 calc R
C16 C 0.1110(3) 0.6731(2) 0.23320(7) 0.0865(5) Uani 1 1 d .
H16A H 0.0908 0.7531 0.2595 0.104 Uiso 1 1 calc R
H11A H 0.308(2) 0.4054(15) 0.0460(6) 0.055(4) Uiso 1 1 d .
H11B H 0.195(2) 0.2521(19) 0.0299(6) 0.077(4) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 C7 C1 116.82(11)
C8 C7 C11 125.35(12)
C1 C7 C11 117.83(11)
C7 C8 O1 123.92(11)
C7 C8 C9 122.46(13)
O1 C8 C9 113.60(11)
C14 O1 C8 116.79(9)
C6 C1 C2 117.17(12)
C6 C1 C7 122.15(11)
C2 C1 C7 120.68(11)
C10 C2 C3 121.76(13)
C10 C2 C1 118.76(13)
C3 C2 C1 119.48(12)
C5 C6 C1 121.28(13)
C6 C5 C4 120.90(14)
C3 C4 C5 120.11(15)
C9 C10 C2 120.29(13)
C7 C11 C12 118.22(12)
C4 C3 C2 121.06(14)
C13 C12 C11 113.54(11)
C15 C14 C13 122.50(14)
C15 C14 O1 118.90(13)
C13 C14 O1 118.50(12)
C10 C9 C8 120.95(13)
C14 C13 C18 117.75(13)
C14 C13 C12 118.29(13)
C18 C13 C12 123.95(13)
C14 C15 C16 118.63(16)
C16 C17 C18 120.19(17)
C17 C18 C13 120.55(15)
C17 C16 C15 120.33(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C7 C8 1.3731(17)
C7 C1 1.4333(18)
C7 C11 1.5152(18)
C8 O1 1.3981(17)
C8 C9 1.4030(18)
O1 C14 1.3930(17)
C1 C6 1.4194(18)
C1 C2 1.4254(18)
C2 C10 1.407(2)
C2 C3 1.412(2)
C6 C5 1.360(2)
C5 C4 1.392(2)
C4 C3 1.352(2)
C10 C9 1.349(2)
C11 C12 1.515(2)
C12 C13 1.498(2)
C14 C15 1.375(2)
C14 C13 1.3807(18)
C13 C18 1.389(2)
C15 C16 1.383(3)
C17 C16 1.373(3)
C17 C18 1.384(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094642
