#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151092.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_7151092
loop_
_publ_author_name
'Cockroft, Scott L.'
'Perkins, Julie'
'Zonta, Cristiano'
'Adams, Harry'
'Spey, Sharon E.'
'Low, Caroline M. R.'
'Vinter, Jeremy G.'
'Lawson, Kevin R.'
'Urch, Christopher J.'
'Hunter, Christopher A.'
_publ_section_title
;
 Substituent effects on aromatic stacking interactions.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1062
_journal_page_last               1080
_journal_paper_doi               10.1039/b617576g
_journal_volume                  5
_journal_year                    2007
_chemical_formula_sum            'C20 H12 F4 N2 O2'
_chemical_formula_weight         388.32
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 95.503(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.261(4)
_cell_length_b                   9.225(4)
_cell_length_c                   32.382(11)
_cell_measurement_reflns_used    150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      3.33
_cell_volume                     3348(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'bruker smart'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            3053
_diffrn_reflns_theta_full        25.53
_diffrn_reflns_theta_max         25.53
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9870
_exptl_absorpt_correction_type   Semi-empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0461
_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)+(0.0435P)²+5.9945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2322
_reflns_number_total             3053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b617576g.txt
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7151092
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.03897(13) -0.09146(16) 0.41782(4) 0.0394(4) Uani 1 1 d . . .
F2 F 0.25030(13) 0.04244(15) 0.32967(4) 0.0381(4) Uani 1 1 d . . .
F3 F 0.12029(13) -0.23553(16) 0.62008(4) 0.0419(4) Uani 1 1 d . . .
F4 F 0.44943(13) 0.02487(16) 0.68085(4) 0.0410(4) Uani 1 1 d . . .
O1 O 0.19823(16) -0.17668(17) 0.44640(5) 0.0343(4) Uani 1 1 d . . .
O2 O 0.32384(15) 0.17258(17) 0.61541(5) 0.0330(4) Uani 1 1 d . . .
N1 N 0.18225(18) 0.0324(2) 0.40920(6) 0.0315(5) Uani 1 1 d . . .
H11 H 0.2009 0.1227 0.4084 0.038 Uiso 1 1 calc R . .
N2 N 0.31518(18) -0.0726(2) 0.60789(6) 0.0311(5) Uani 1 1 d . . .
H12 H 0.3263 -0.1453 0.5921 0.037 Uiso 1 1 calc R . .
C1 C 0.1110(2) -0.0288(2) 0.37534(7) 0.0297(5) Uani 1 1 d . . .
C2 C 0.0028(2) -0.0967(3) 0.37990(7) 0.0326(6) Uani 1 1 d . . .
C3 C -0.0641(2) -0.1642(3) 0.34791(7) 0.0347(6) Uani 1 1 d . . .
H1 H -0.1348 -0.2113 0.3523 0.042 Uiso 1 1 calc R . .
C4 C -0.0233(2) -0.1600(3) 0.30880(8) 0.0353(6) Uani 1 1 d . . .
H2 H -0.0665 -0.2068 0.2868 0.042 Uiso 1 1 calc R . .
C5 C 0.0805(2) -0.0874(3) 0.30206(7) 0.0346(6) Uani 1 1 d . . .
H3 H 0.1055 -0.0807 0.2756 0.041 Uiso 1 1 calc R . .
C6 C 0.1458(2) -0.0254(3) 0.33549(7) 0.0314(5) Uani 1 1 d . . .
C7 C 0.2220(2) -0.0472(3) 0.44286(7) 0.0316(6) Uani 1 1 d . . .
C8 C 0.2974(2) 0.0324(2) 0.47584(7) 0.0295(5) Uani 1 1 d . . .
C9 C 0.3816(2) 0.1343(3) 0.46583(7) 0.0323(6) Uani 1 1 d . . .
H4 H 0.3909 0.1543 0.4382 0.039 Uiso 1 1 calc R . .
C10 C 0.4514(2) 0.2059(3) 0.49707(7) 0.0343(6) Uani 1 1 d . . .
H5 H 0.5099 0.2706 0.4904 0.041 Uiso 1 1 calc R . .
C11 C 0.4338(2) 0.1808(3) 0.53808(7) 0.0326(6) Uani 1 1 d . . .
H6 H 0.4781 0.2324 0.5589 0.039 Uiso 1 1 calc R . .
C12 C 0.3502(2) 0.0786(2) 0.54855(7) 0.0290(5) Uani 1 1 d . . .
C13 C 0.2838(2) 0.0020(2) 0.51739(7) 0.0298(5) Uani 1 1 d . . .
H7 H 0.2306 -0.0692 0.5242 0.036 Uiso 1 1 calc R . .
C14 C 0.3294(2) 0.0639(3) 0.59323(7) 0.0298(5) Uani 1 1 d . . .
C15 C 0.2826(2) -0.0985(2) 0.64837(7) 0.0298(5) Uani 1 1 d . . .
C16 C 0.1828(2) -0.1810(3) 0.65434(7) 0.0321(6) Uani 1 1 d . . .
C17 C 0.1450(2) -0.2096(3) 0.69269(8) 0.0370(6) Uani 1 1 d . . .
H8 H 0.0774 -0.2656 0.6952 0.044 Uiso 1 1 calc R . .
C18 C 0.2098(2) -0.1531(3) 0.72733(8) 0.0378(6) Uani 1 1 d . . .
H9 H 0.1853 -0.1703 0.7535 0.045 Uiso 1 1 calc R . .
C19 C 0.3114(2) -0.0707(3) 0.72340(7) 0.0358(6) Uani 1 1 d . . .
H10 H 0.3550 -0.0321 0.7467 0.043 Uiso 1 1 calc R . .
C20 C 0.3460(2) -0.0474(3) 0.68423(7) 0.0320(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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 121.8(2) . . ?
C7 N1 H11 119.1 . . ?
C1 N1 H11 119.1 . . ?
C14 N2 C15 121.95(19) . . ?
C14 N2 H12 119.0 . . ?
C15 N2 H12 119.0 . . ?
C6 C1 C2 116.0(2) . . ?
C6 C1 N1 121.6(2) . . ?
C2 C1 N1 122.4(2) . . ?
F1 C2 C3 119.1(2) . . ?
F1 C2 C1 117.6(2) . . ?
C3 C2 C1 123.2(2) . . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 H1 121.0 . . ?
C4 C3 H1 121.0 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H2 119.5 . . ?
C3 C4 H2 119.5 . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H3 120.9 . . ?
C4 C5 H3 120.9 . . ?
F2 C6 C5 119.1(2) . . ?
F2 C6 C1 117.7(2) . . ?
C5 C6 C1 123.2(2) . . ?
O1 C7 N1 122.9(2) . . ?
O1 C7 C8 121.6(2) . . ?
N1 C7 C8 115.5(2) . . ?
C9 C8 C13 119.9(2) . . ?
C9 C8 C7 121.2(2) . . ?
C13 C8 C7 118.9(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H4 120.0 . . ?
C8 C9 H4 120.0 . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H5 120.0 . . ?
C9 C10 H5 120.0 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H6 119.7 . . ?
C12 C11 H6 119.7 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 C14 122.3(2) . . ?
C11 C12 C14 117.9(2) . . ?
C12 C13 C8 119.8(2) . . ?
C12 C13 H7 120.1 . . ?
C8 C13 H7 120.1 . . ?
O2 C14 N2 122.2(2) . . ?
O2 C14 C12 120.6(2) . . ?
N2 C14 C12 117.2(2) . . ?
C16 C15 C20 115.4(2) . . ?
C16 C15 N2 120.5(2) . . ?
C20 C15 N2 124.1(2) . . ?
F3 C16 C17 119.1(2) . . ?
F3 C16 C15 117.1(2) . . ?
C17 C16 C15 123.8(2) . . ?
C16 C17 C18 118.4(2) . . ?
C16 C17 H8 120.8 . . ?
C18 C17 H8 120.8 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H9 119.7 . . ?
C19 C18 H9 119.7 . . ?
C20 C19 C18 118.5(2) . . ?
C20 C19 H10 120.7 . . ?
C18 C19 H10 120.7 . . ?
F4 C20 C19 118.2(2) . . ?
F4 C20 C15 118.5(2) . . ?
C19 C20 C15 123.3(2) . . ?
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
F1 C2 1.357(3) . ?
F2 C6 1.362(3) . ?
F3 C16 1.353(3) . ?
F4 C20 1.355(3) . ?
O1 C7 1.232(3) . ?
O2 C14 1.239(3) . ?
N1 C7 1.354(3) . ?
N1 C1 1.413(3) . ?
N1 H11 0.8600 . ?
N2 C14 1.360(3) . ?
N2 C15 1.415(3) . ?
N2 H12 0.8600 . ?
C1 C6 1.385(3) . ?
C1 C2 1.390(3) . ?
C2 C3 1.370(3) . ?
C3 C4 1.389(3) . ?
C3 H1 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H2 0.9300 . ?
C5 C6 1.373(3) . ?
C5 H3 0.9300 . ?
C7 C8 1.492(3) . ?
C8 C9 1.395(3) . ?
C8 C13 1.397(3) . ?
C9 C10 1.387(3) . ?
C9 H4 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H5 0.9300 . ?
C11 C12 1.397(3) . ?
C11 H6 0.9300 . ?
C12 C13 1.390(3) . ?
C12 C14 1.494(3) . ?
C13 H7 0.9300 . ?
C15 C16 1.386(3) . ?
C15 C20 1.386(3) . ?
C16 C17 1.376(3) . ?
C17 C18 1.381(4) . ?
C17 H8 0.9300 . ?
C18 C19 1.388(4) . ?
C18 H9 0.9300 . ?
C19 C20 1.379(3) . ?
C19 H10 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17273969
2 PubChem 16116747
