#------------------------------------------------------------------------------
#$Date: 2021-10-20 00:02:59 +0200 (Wed 20 de Oct de 2021) $
#$Revision: 270026 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/91/7129143.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_7129143
loop_
_publ_author_name
'Berntsen, Linn Neerbye'
'Nordbø Solvi, Thomas'
'Sørnes, Kristian'
'Wragg, David S.'
'Sandtorv, Alexander Harald H.'
_publ_section_title
;
 Cu-catalyzed C(sp2)-N-bond coupling of boronic acids and cyclic imides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC04356K
_journal_year                    2021
_chemical_formula_moiety         'C20 H15 F N2 O2'
_chemical_formula_sum            'C20 H15 F N2 O2'
_chemical_formula_weight         334.34
_chemical_name_systematic        (E,E)-1,3-distyryl-5-fluorouracil
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-27 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   33.8915(10)
_cell_length_b                   33.8915(10)
_cell_length_c                   7.0535(13)
_cell_measurement_reflns_used    1455
_cell_measurement_temperature    99.9
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.40
_cell_volume                     7016.4(13)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.9
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5543
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_min         2.082
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 31204 reflections, Rint = 0.0562
 (21115 with I > 3sig(I), Rint = 0.0420)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       needle
_exptl_crystal_F_000             3132
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5543
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0537
_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)+(0.0410P)²+4.9561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                4523
_reflns_number_total             5543
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04356k2.cif
_cod_data_source_block           LNB381_twin
_cod_original_cell_volume        7016.4(14)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               7129143
_shelx_shelxl_version_number     2018/3
_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_max   0.982
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.34163
 0.26796 0.39041
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C6(H6), C5(H5), C13(H13), C12(H12), C11(H11), C14(H14),
 C00J(H00J), C19(H19), C18(H18), C4(H4), C8(H8), C9(H9), C10(H10)
;
_olex2_date_sample_data_collection 2021-04-16
_olex2_date_sample_submission    2021-04-16
_olex2_submission_original_sample_id LNB381
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.02236(9) 0.32037(9) 0.5801(4) 0.0237(7) Uani 1 1 d . . . . .
O1 O 0.05297(10) 0.26365(11) 0.6900(5) 0.0197(8) Uani 1 1 d . . . . .
O2 O 0.19727(10) 0.36854(11) 0.4896(5) 0.0226(8) Uani 1 1 d . . . . .
N1 N 0.12543(12) 0.31391(12) 0.5825(5) 0.0130(9) Uani 1 1 d . . . . .
N2 N 0.14091(12) 0.38585(12) 0.4682(6) 0.0141(9) Uani 1 1 d . . . . .
C2 C 0.07894(15) 0.30017(15) 0.6173(7) 0.0148(10) Uani 1 1 d . . . . .
C15 C 0.20396(15) 0.51277(15) 0.3740(6) 0.0131(10) Uani 1 1 d . . . . .
C16 C 0.24424(15) 0.52291(15) 0.2790(6) 0.0131(10) Uani 1 1 d . . . . .
H16 H 0.251042 0.499313 0.256380 0.016 Uiso 1 1 calc R . . . .
C7 C 0.18884(16) 0.24869(15) 0.6730(6) 0.0152(10) Uani 1 1 d . . . . .
C3 C 0.15731(14) 0.35661(14) 0.5119(7) 0.0150(10) Uani 1 1 d . . . . .
C17 C 0.27424(15) 0.56658(14) 0.2176(6) 0.0158(11) Uani 1 1 d . . . . .
H17 H 0.301521 0.572871 0.154314 0.019 Uiso 1 1 calc R . . . .
C1 C 0.06677(14) 0.33317(16) 0.5580(7) 0.0150(10) Uani 1 1 d . . . . .
C6 C 0.17932(15) 0.28504(15) 0.6192(7) 0.0153(10) Uani 1 1 d . . . . .
H6 H 0.203905 0.312968 0.574190 0.018 Uiso 1 1 calc R . . . .
C5 C 0.13846(16) 0.28115(15) 0.6299(6) 0.0157(11) Uani 1 1 d . . . . .
H5 H 0.114709 0.252735 0.675221 0.019 Uiso 1 1 calc R . . . .
C13 C 0.17395(15) 0.43030(15) 0.4068(7) 0.0150(10) Uani 1 1 d . . . . .
H13 H 0.199494 0.433744 0.337285 0.018 Uiso 1 1 calc R . . . .
C12 C 0.23409(16) 0.25932(16) 0.6907(7) 0.0180(11) Uani 1 1 d . . . . .
H12 H 0.257806 0.289416 0.663881 0.022 Uiso 1 1 calc R . . . .
C11 C 0.24510(17) 0.22691(16) 0.7467(7) 0.0187(11) Uani 1 1 d . . . . .
H11 H 0.276133 0.234935 0.759495 0.022 Uiso 1 1 calc R . . . .
C14 C 0.17097(15) 0.46706(15) 0.4413(6) 0.0140(10) Uani 1 1 d . . . . .
H14 H 0.145865 0.463607 0.514203 0.017 Uiso 1 1 calc R . . . .
C00J C 0.26454(15) 0.60123(15) 0.2484(7) 0.0163(11) Uani 1 1 d . . . . .
H00J H 0.284931 0.631181 0.204421 0.020 Uiso 1 1 calc R . . . .
C19 C 0.19508(15) 0.54841(14) 0.4051(7) 0.0155(11) Uani 1 1 d . . . . .
H19 H 0.168045 0.542452 0.469591 0.019 Uiso 1 1 calc R . . . .
C18 C 0.22506(15) 0.59216(15) 0.3433(7) 0.0182(11) Uani 1 1 d . . . . .
H18 H 0.218589 0.615982 0.365878 0.022 Uiso 1 1 calc R . . . .
C4 C 0.09580(15) 0.37344(16) 0.4879(7) 0.0160(10) Uani 1 1 d . . . . .
H4 H 0.085636 0.393843 0.451114 0.019 Uiso 1 1 calc R . . . .
C8 C 0.15497(16) 0.20426(16) 0.7101(7) 0.0180(11) Uani 1 1 d . . . . .
H8 H 0.123904 0.196178 0.698043 0.022 Uiso 1 1 calc R . . . .
C9 C 0.16571(16) 0.17158(15) 0.7644(7) 0.0196(11) Uani 1 1 d . . . . .
H9 H 0.142045 0.141293 0.788488 0.023 Uiso 1 1 calc R . . . .
C10 C 0.21093(16) 0.18280(16) 0.7841(7) 0.0187(11) Uani 1 1 d . . . . .
H10 H 0.218319 0.160416 0.822785 0.022 Uiso 1 1 calc R . . . .
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
C2 N1 C5 115.4(4) . . ?
C3 N1 C2 123.9(4) . . ?
C3 N1 C5 120.7(4) . . ?
C3 N2 C13 116.0(4) . . ?
C4 N2 C3 122.6(4) . . ?
C4 N2 C13 121.4(4) . . ?
O1 C2 N1 121.7(4) . . ?
O1 C2 C1 124.9(4) . . ?
N1 C2 C1 113.4(4) . . ?
C16 C15 C14 123.4(4) . . ?
C19 C15 C16 117.8(4) . . ?
C19 C15 C14 118.8(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C12 C7 C6 118.7(4) . . ?
C8 C7 C6 123.3(4) . . ?
C8 C7 C12 118.0(4) . . ?
O2 C3 N1 123.2(4) . . ?
O2 C3 N2 120.7(4) . . ?
N2 C3 N1 116.1(4) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C00J 120.0(4) . . ?
C00J C17 H17 120.0 . . ?
F1 C1 C2 115.1(4) . . ?
C4 C1 F1 120.8(4) . . ?
C4 C1 C2 124.1(4) . . ?
C7 C6 H6 118.0 . . ?
C5 C6 C7 123.9(4) . . ?
C5 C6 H6 118.0 . . ?
N1 C5 H5 115.7 . . ?
C6 C5 N1 128.6(4) . . ?
C6 C5 H5 115.7 . . ?
N2 C13 H13 118.3 . . ?
C14 C13 N2 123.5(4) . . ?
C14 C13 H13 118.3 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.3(5) . . ?
C11 C12 H12 119.4 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C15 C14 H14 118.0 . . ?
C13 C14 C15 124.0(4) . . ?
C13 C14 H14 118.0 . . ?
C17 C00J H00J 120.0 . . ?
C17 C00J C18 120.0(4) . . ?
C18 C00J H00J 120.0 . . ?
C15 C19 H19 119.5 . . ?
C18 C19 C15 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C00J C18 H18 120.0 . . ?
C19 C18 C00J 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
N2 C4 H4 120.2 . . ?
C1 C4 N2 119.7(4) . . ?
C1 C4 H4 120.2 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
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 C1 1.351(5) . ?
O1 C2 1.217(5) . ?
O2 C3 1.214(5) . ?
N1 C2 1.423(6) . ?
N1 C3 1.395(5) . ?
N1 C5 1.425(6) . ?
N2 C3 1.391(6) . ?
N2 C13 1.423(5) . ?
N2 C4 1.375(6) . ?
C2 C1 1.434(6) . ?
C15 C16 1.400(6) . ?
C15 C14 1.464(6) . ?
C15 C19 1.400(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(6) . ?
C7 C6 1.471(6) . ?
C7 C12 1.395(6) . ?
C7 C8 1.388(6) . ?
C17 H17 0.9500 . ?
C17 C00J 1.386(6) . ?
C1 C4 1.316(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.326(6) . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.322(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.382(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(6) . ?
C14 H14 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C18 1.386(7) . ?
C19 H19 0.9500 . ?
C19 C18 1.384(6) . ?
C18 H18 0.9500 . ?
C4 H4 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.381(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(6) . ?
C10 H10 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C4 N2 179.5(4) . . . . ?
O1 C2 C1 F1 -2.9(7) . . . . ?
O1 C2 C1 C4 176.6(5) . . . . ?
N1 C2 C1 F1 176.9(4) . . . . ?
N1 C2 C1 C4 -3.6(7) . . . . ?
N2 C13 C14 C15 -178.1(4) . . . . ?
C2 N1 C3 O2 177.1(5) . . . . ?
C2 N1 C3 N2 -2.4(6) . . . . ?
C2 N1 C5 C6 -177.4(5) . . . . ?
C2 C1 C4 N2 0.0(8) . . . . ?
C15 C16 C17 C00J -0.5(7) . . . . ?
C15 C19 C18 C00J 0.2(7) . . . . ?
C16 C15 C14 C13 -5.5(7) . . . . ?
C16 C15 C19 C18 0.2(6) . . . . ?
C16 C17 C00J C18 1.0(7) . . . . ?
C7 C6 C5 N1 179.8(5) . . . . ?
C7 C12 C11 C10 0.8(7) . . . . ?
C7 C8 C9 C10 0.4(7) . . . . ?
C3 N1 C2 O1 -175.4(4) . . . . ?
C3 N1 C2 C1 4.9(6) . . . . ?
C3 N1 C5 C6 1.0(7) . . . . ?
C3 N2 C13 C14 -147.8(5) . . . . ?
C3 N2 C4 C1 2.9(7) . . . . ?
C17 C00J C18 C19 -0.8(7) . . . . ?
C6 C7 C12 C11 177.9(4) . . . . ?
C6 C7 C8 C9 -178.5(4) . . . . ?
C5 N1 C2 O1 3.0(6) . . . . ?
C5 N1 C2 C1 -176.8(4) . . . . ?
C5 N1 C3 O2 -1.2(7) . . . . ?
C5 N1 C3 N2 179.3(4) . . . . ?
C13 N2 C3 O2 -3.1(7) . . . . ?
C13 N2 C3 N1 176.4(4) . . . . ?
C13 N2 C4 C1 -175.1(4) . . . . ?
C12 C7 C6 C5 -167.8(5) . . . . ?
C12 C7 C8 C9 0.5(7) . . . . ?
C12 C11 C10 C9 0.1(7) . . . . ?
C14 C15 C16 C17 179.8(4) . . . . ?
C14 C15 C19 C18 -179.6(4) . . . . ?
C19 C15 C16 C17 -0.1(6) . . . . ?
C19 C15 C14 C13 174.4(4) . . . . ?
C4 N2 C3 O2 178.8(5) . . . . ?
C4 N2 C3 N1 -1.7(7) . . . . ?
C4 N2 C13 C14 30.4(7) . . . . ?
C8 C7 C6 C5 11.1(8) . . . . ?
C8 C7 C12 C11 -1.1(7) . . . . ?
C8 C9 C10 C11 -0.7(8) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.34163
2 0.26796
3 0.39041
