#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/50/4035024.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_4035024
loop_
_publ_author_name
'Villuri, Bharath Kumar'
'Ichake, Sachin S.'
'Reddy, Sabbasani Rajasekhara'
'Kavala, Veerababurao'
'Bandi, Vijayalakshmi'
'Kuo, Chun-Wei'
'Yao, Ching-Fa'
_publ_section_title
;
 Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and
 Dibenzo[ b, f]oxepine-10-carbonitrile Derivatives.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10241
_journal_page_last               10247
_journal_paper_doi               10.1021/acs.joc.8b01443
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C15 H8 F N O'
_chemical_formula_sum            'C15 H8 F N O'
_chemical_formula_weight         237.22
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 92.452(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.7895(8)
_cell_length_b                   21.669(5)
_cell_length_c                   13.318(4)
_cell_measurement_reflns_used    1410
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.758
_cell_measurement_theta_min      2.418
_cell_volume                     1092.6(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1485
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10716
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_correction_T_min  0.9296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.047(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0564
_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)+(0.0673P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1603
_reflns_number_gt                1246
_reflns_number_total             1955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01443_si_001.cif
_cod_data_source_block           d19331
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035024
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7335(7) 0.50285(10) 0.3305(2) 0.0330(7) Uani 1 1 d .
C2 C 0.8942(7) 0.45072(12) 0.3710(2) 0.0394(8) Uani 1 1 d .
H2 H 0.9598 0.4472 0.4404 0.047 Uiso 1 1 calc R
C3 C 0.9525(7) 0.40397(12) 0.3029(3) 0.0416(8) Uani 1 1 d .
H3 H 1.0604 0.3668 0.3265 0.050 Uiso 1 1 calc R
C4 C 0.8587(7) 0.40937(11) 0.2012(2) 0.0388(8) Uani 1 1 d .
H4 H 0.9069 0.3762 0.1572 0.047 Uiso 1 1 calc R
C5 C 0.6972(7) 0.46185(11) 0.1630(2) 0.0378(8) Uani 1 1 d .
H5 H 0.6326 0.4654 0.0935 0.045 Uiso 1 1 calc R
C6 C 0.6320(7) 0.50958(11) 0.2301(2) 0.0322(7) Uani 1 1 d .
C7 C 0.4751(7) 0.57017(11) 0.2217(2) 0.0326(7) Uani 1 1 d .
C8 C 0.3209(8) 0.59561(11) 0.1320(3) 0.0364(8) Uani 1 1 d .
C9 C 0.4927(7) 0.59609(11) 0.3159(2) 0.0310(7) Uani 1 1 d .
C10 C 0.3831(7) 0.65519(11) 0.3563(2) 0.0308(7) Uani 1 1 d .
C11 C 0.2368(7) 0.70101(11) 0.2940(2) 0.0377(7) Uani 1 1 d .
H11 H 0.2041 0.6937 0.2238 0.045 Uiso 1 1 calc R
C12 C 0.1392(7) 0.75711(11) 0.3342(3) 0.0409(8) Uani 1 1 d .
H12 H 0.0409 0.7881 0.2909 0.049 Uiso 1 1 calc R
C13 C 0.1814(8) 0.76886(12) 0.4352(2) 0.0414(8) Uani 1 1 d .
H13 H 0.1129 0.8072 0.4630 0.050 Uiso 1 1 calc R
C14 C 0.3266(8) 0.72294(12) 0.4944(2) 0.0417(8) Uani 1 1 d .
C15 C 0.4277(7) 0.66655(11) 0.4587(2) 0.0381(8) Uani 1 1 d .
H15 H 0.5258 0.6360 0.5029 0.046 Uiso 1 1 calc R
F1 F 0.3729(6) 0.73329(8) 0.59478(15) 0.0719(7) Uani 1 1 d .
O1 O 0.6497(5) 0.55555(7) 0.38390(14) 0.0354(6) Uani 1 1 d .
N1 N 0.1943(7) 0.61368(11) 0.0574(2) 0.0515(8) 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 124.3(2)
C2 C1 O1 125.4(3)
C6 C1 O1 110.4(2)
C1 C2 C3 115.0(3)
C1 C2 H2 122.5
C3 C2 H2 122.5
C2 C3 C4 122.4(3)
C2 C3 H3 118.8
C4 C3 H3 118.8
C5 C4 C3 121.3(3)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 117.5(3)
C4 C5 H5 121.2
C6 C5 H5 121.2
C1 C6 C5 119.4(2)
C1 C6 C7 105.5(2)
C5 C6 C7 135.1(3)
C9 C7 C8 127.8(2)
C9 C7 C6 107.3(3)
C8 C7 C6 124.9(3)
N1 C8 C7 177.0(3)
C7 C9 O1 110.0(2)
C7 C9 C10 133.9(3)
O1 C9 C10 116.0(3)
C15 C10 C11 119.2(2)
C15 C10 C9 119.6(2)
C11 C10 C9 121.2(3)
C12 C11 C10 120.0(3)
C12 C11 H11 120.0
C10 C11 H11 120.0
C13 C12 C11 121.3(3)
C13 C12 H12 119.3
C11 C12 H12 119.3
C14 C13 C12 117.2(3)
C14 C13 H13 121.4
C12 C13 H13 121.4
F1 C14 C13 118.5(2)
F1 C14 C15 117.5(3)
C13 C14 C15 124.0(3)
C14 C15 C10 118.3(3)
C14 C15 H15 120.9
C10 C15 H15 120.9
C9 O1 C1 106.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.382(4)
C1 C6 1.384(4)
C1 O1 1.389(3)
C2 C3 1.384(4)
C2 H2 0.9500
C3 C4 1.391(4)
C3 H3 0.9500
C4 C5 1.379(4)
C4 H4 0.9500
C5 C6 1.396(4)
C5 H5 0.9500
C6 C7 1.444(3)
C7 C9 1.373(4)
C7 C8 1.419(4)
C8 N1 1.153(4)
C9 O1 1.378(3)
C9 C10 1.457(3)
C10 C15 1.389(4)
C10 C11 1.394(4)
C11 C12 1.385(4)
C11 H11 0.9500
C12 C13 1.373(4)
C12 H12 0.9500
C13 C14 1.370(4)
C13 H13 0.9500
C14 F1 1.360(4)
C14 C15 1.372(4)
C15 H15 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328832
