#------------------------------------------------------------------------------
#$Date: 2019-11-24 20:38:37 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239364 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/60/1556043.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_1556043
loop_
_publ_author_name
'Wang, Rui'
'Guan, Wei'
'Han, Zheng-Bo'
'Liang, Fushun'
'Suga, Takeo'
'Bi, Xihe'
'Nishide, Hiroyuki'
_publ_section_title
;
 Ambient-Light-Promoted Three-Component Annulation: Synthesis of
 Perfluoroalkylated Pyrimidines.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2358
_journal_page_last               2361
_journal_paper_doi               10.1021/acs.orglett.7b00894
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C11 H10 F7 N3 O2'
_chemical_formula_weight         349.22
_chemical_melting_point          '63-64 &#x00A1;&#x00E6;'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.161(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1302(11)
_cell_length_b                   7.5328(5)
_cell_length_c                   12.1195(13)
_cell_measurement_reflns_used    1945
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1414
_cell_measurement_theta_min      3.0317
_cell_volume                     1472.6(2)
_computing_cell_refinement
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_data_collection
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_data_reduction
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10254
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.206
_diffrn_reflns_theta_min         3.362
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             775
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0745
_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)+(0.1443P)²+0.0456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1815
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b00894_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1556043
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.0816(3) -0.2945(11) 0.7007(7) 0.122(2) Uani 1 1 d . . .
C2 C 0.1545(2) -0.2041(6) 0.7568(4) 0.0800(11) Uani 1 1 d . . .
C3 C 0.24069(19) -0.2384(4) 0.7037(3) 0.0614(8) Uani 1 1 d . . .
C4 C 0.30954(16) -0.1355(4) 0.7612(2) 0.0519(7) Uani 1 1 d . . .
C5 C 0.39657(17) -0.1290(4) 0.9082(2) 0.0550(7) Uani 1 1 d . . .
C6 C 0.39708(16) 0.1109(4) 0.7913(2) 0.0510(7) Uani 1 1 d . . .
C7 C 0.33875(16) 0.0263(3) 0.7232(2) 0.0495(7) Uani 1 1 d . . .
C8 C 0.4294(2) 0.2908(4) 0.7662(3) 0.0678(9) Uani 1 1 d . . .
H8A H 0.4685 0.3254 0.8220 0.102 Uiso 1 1 calc R U .
H8B H 0.3843 0.3739 0.7646 0.102 Uiso 1 1 calc R U .
H8C H 0.4562 0.2896 0.6956 0.102 Uiso 1 1 calc R U .
C9 C 0.31941(18) 0.1049(4) 0.6130(3) 0.0547(7) Uani 1 1 d . . .
C10 C 0.2244(3) 0.2689(8) 0.5044(4) 0.1077(16) Uani 1 1 d . . .
H10A H 0.1882 0.3691 0.5183 0.129 Uiso 1 1 calc R U .
H10B H 0.2736 0.3147 0.4684 0.129 Uiso 1 1 calc R U .
C11 C 0.1883(14) 0.167(2) 0.4380(14) 0.100(5) Uani 0.3 1 d . . P
N1 N 0.33632(14) -0.2149(3) 0.8517(2) 0.0566(7) Uani 1 1 d . . .
N2 N 0.42965(19) -0.2113(4) 0.9941(3) 0.0714(9) Uani 1 1 d . . .
N3 N 0.42537(13) 0.0348(3) 0.8833(2) 0.0518(6) Uani 1 1 d . . .
01 O 0.24937(14) 0.1949(3) 0.6107(2) 0.0747(7) Uani 1 1 d . . .
02 O 0.36611(15) 0.0917(3) 0.5360(2) 0.0749(7) Uani 1 1 d . . .
F1 F 0.01289(17) -0.2657(6) 0.7579(4) 0.1660(16) Uani 1 1 d . . .
F2' F 0.0656(9) -0.168(2) 0.6092(15) 0.170(6) Uani 0.5 1 d . . P
F2 F 0.0766(8) -0.289(2) 0.6037(12) 0.150(5) Uani 0.5 1 d . . P
F3 F 0.0936(9) -0.4842(16) 0.7292(13) 0.177(7) Uani 0.5 1 d . . P
F3' F 0.0901(6) -0.4331(18) 0.6638(15) 0.151(6) Uani 0.5 1 d . . P
F4 F 0.15625(15) -0.2564(6) 0.8624(3) 0.1419(13) Uani 1 1 d . . .
F5 F 0.1385(8) -0.0334(15) 0.7419(16) 0.118(5) Uani 0.5 1 d . . P
F5' F 0.1406(8) -0.0346(18) 0.7706(18) 0.138(6) Uani 0.5 1 d . . P
F6 F 0.23514(11) -0.1937(3) 0.59620(16) 0.0755(6) Uani 1 1 d . . .
F7 F 0.2562(7) -0.4092(19) 0.7128(13) 0.069(3) Uani 0.5 1 d . . P
F7' F 0.2561(10) -0.417(2) 0.7028(17) 0.113(6) Uani 0.5 1 d . . P
C11' C 0.1331(7) 0.2286(17) 0.4871(10) 0.146(4) Uani 0.7 1 d . . P
H1 H 0.422(2) -0.327(5) 1.001(3) 0.071(10) Uiso 1 1 d . . .
H2 H 0.469(2) -0.168(5) 1.027(3) 0.066(10) 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'
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
F3' C1 F2 69.5(11)
F3' C1 F1 117.0(9)
F2 C1 F1 117.4(9)
F3' C1 F2' 108.2(15)
F2 C1 F2' 38.8(11)
F1 C1 F2' 98.2(8)
F3' C1 F3 36.5(11)
F2 C1 F3 106.0(13)
F1 C1 F3 98.3(8)
F2' C1 F3 144.5(11)
F3' C1 C2 119.5(8)
F2 C1 C2 118.8(8)
F1 C1 C2 109.8(6)
F2' C1 C2 100.4(8)
F3 C1 C2 103.1(8)
F5' C2 F5 15.3(16)
F5' C2 F4 99.7(10)
F5 C2 F4 114.8(9)
F5' C2 C1 111.3(7)
F5 C2 C1 102.9(8)
F4 C2 C1 108.1(5)
F5' C2 C3 111.6(7)
F5 C2 C3 106.2(8)
F4 C2 C3 109.3(3)
C1 C2 C3 115.6(4)
F7 C3 F6 109.7(7)
F7 C3 F7' 5.3(15)
F6 C3 F7' 104.5(9)
F7 C3 C4 108.7(7)
F6 C3 C4 111.2(2)
F7' C3 C4 111.8(8)
F7 C3 C2 107.3(5)
F6 C3 C2 107.6(3)
F7' C3 C2 109.2(8)
C4 C3 C2 112.2(3)
N1 C4 C7 124.3(2)
N1 C4 C3 112.7(2)
C7 C4 C3 122.9(3)
N2 C5 N1 117.5(3)
N2 C5 N3 117.7(3)
N1 C5 N3 124.7(3)
N3 C6 C7 121.6(2)
N3 C6 C8 116.4(2)
C7 C6 C8 122.0(3)
C4 C7 C6 115.6(3)
C4 C7 C9 125.2(2)
C6 C7 C9 118.9(2)
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
02 C9 01 124.3(3)
02 C9 C7 122.0(3)
01 C9 C7 113.6(3)
C11 C10 01 117.3(8)
C11 C10 C11' 48.7(10)
01 C10 C11' 108.1(5)
C11 C10 H10A 108.0
01 C10 H10A 108.0
C11' C10 H10A 66.1
C11 C10 H10B 108.0
01 C10 H10B 108.0
C11' C10 H10B 143.5
H10A C10 H10B 107.2
C11' C11 C10 77.5(14)
C4 N1 C5 115.9(2)
C5 N2 H1 119(2)
C5 N2 H2 121(3)
H1 N2 H2 117(3)
C6 N3 C5 117.5(2)
C9 01 C10 116.7(3)
F2 F2' C1 52.7(14)
F2' F2 C1 89(2)
F2' F2 F3' 143(3)
C1 F2 F3' 54.0(8)
F3' F3 C1 50.4(11)
F3 F3' C1 93.1(19)
F3 F3' F2 149(2)
C1 F3' F2 56.5(8)
C11 C11' C10 53.8(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 F3' 1.144(11)
C1 F2 1.179(13)
C1 F1 1.327(7)
C1 F2' 1.482(18)
C1 F3 1.483(15)
C1 C2 1.517(7)
C2 F5' 1.307(14)
C2 F5 1.324(12)
C2 F4 1.339(5)
C2 C3 1.556(6)
C3 F7 1.315(15)
C3 F6 1.348(4)
C3 F7' 1.371(19)
C3 C4 1.522(4)
C4 N1 1.321(4)
C4 C7 1.386(4)
C5 N2 1.323(4)
C5 N1 1.352(4)
C5 N3 1.353(4)
C6 N3 1.334(4)
C6 C7 1.403(4)
C6 C8 1.484(4)
C7 C9 1.493(4)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 02 1.205(4)
C9 01 1.317(4)
C10 C11 1.254(15)
C10 01 1.460(5)
C10 C11' 1.517(11)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C11' 1.17(2)
N2 H1 0.88(4)
N2 H2 0.82(4)
F2' F2 0.928(17)
F2 F3' 1.32(2)
F3 F3' 0.884(19)
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
F3' C1 C2 F5' 165.0(17)
F2 C1 C2 F5' 83.5(17)
F1 C1 C2 F5' -55.8(12)
F2' C1 C2 F5' 46.9(13)
F3 C1 C2 F5' -159.7(12)
F3' C1 C2 F5 151.6(17)
F2 C1 C2 F5 70.1(16)
F1 C1 C2 F5 -69.2(11)
F2' C1 C2 F5 33.5(12)
F3 C1 C2 F5 -173.1(12)
F3' C1 C2 F4 -86.5(15)
F2 C1 C2 F4 -168.0(14)
F1 C1 C2 F4 52.7(8)
F2' C1 C2 F4 155.5(8)
F3 C1 C2 F4 -51.2(9)
F3' C1 C2 C3 36.3(16)
F2 C1 C2 C3 -45.2(15)
F1 C1 C2 C3 175.6(5)
F2' C1 C2 C3 -81.7(9)
F3 C1 C2 C3 71.6(9)
F5' C2 C3 F7 167.9(12)
F5 C2 C3 F7 -177.0(11)
F4 C2 C3 F7 58.6(8)
C1 C2 C3 F7 -63.6(9)
F5' C2 C3 F6 -74.1(10)
F5 C2 C3 F6 -59.0(9)
F4 C2 C3 F6 176.6(3)
C1 C2 C3 F6 54.4(6)
F5' C2 C3 F7' 173.1(13)
F5 C2 C3 F7' -171.8(12)
F4 C2 C3 F7' 63.8(10)
C1 C2 C3 F7' -58.4(10)
F5' C2 C3 C4 48.5(10)
F5 C2 C3 C4 63.6(9)
F4 C2 C3 C4 -60.8(4)
C1 C2 C3 C4 177.0(5)
F7 C3 C4 N1 -36.9(7)
F6 C3 C4 N1 -157.8(2)
F7' C3 C4 N1 -41.5(9)
C2 C3 C4 N1 81.6(3)
F7 C3 C4 C7 144.7(6)
F6 C3 C4 C7 23.8(4)
F7' C3 C4 C7 140.1(9)
C2 C3 C4 C7 -96.8(4)
N1 C4 C7 C6 -3.8(4)
C3 C4 C7 C6 174.5(3)
N1 C4 C7 C9 169.9(3)
C3 C4 C7 C9 -11.9(4)
N3 C6 C7 C4 3.5(4)
C8 C6 C7 C4 -175.3(3)
N3 C6 C7 C9 -170.6(2)
C8 C6 C7 C9 10.6(4)
C4 C7 C9 02 -97.7(4)
C6 C7 C9 02 75.7(4)
C4 C7 C9 01 85.1(3)
C6 C7 C9 01 -101.4(3)
01 C10 C11 C11' 90.7(11)
C7 C4 N1 C5 -0.4(4)
C3 C4 N1 C5 -178.8(3)
N2 C5 N1 C4 -174.6(3)
N3 C5 N1 C4 5.5(4)
C7 C6 N3 C5 0.9(4)
C8 C6 N3 C5 179.7(3)
N2 C5 N3 C6 174.3(3)
N1 C5 N3 C6 -5.7(4)
02 C9 01 C10 5.6(5)
C7 C9 01 C10 -177.3(3)
C11 C10 01 C9 82.0(14)
C11' C10 01 C9 134.2(7)
F3' C1 F2' F2 -2.4(17)
F1 C1 F2' F2 -124.4(14)
F3 C1 F2' F2 -7(2)
C2 C1 F2' F2 123.6(15)
C1 F2' F2 F3' 3(2)
F3' C1 F2 F2' 177.6(18)
F1 C1 F2 F2' 67.0(16)
F3 C1 F2 F2' 175.5(14)
C2 C1 F2 F2' -69.2(19)
F1 C1 F2 F3' -110.6(11)
F2' C1 F2 F3' -177.6(18)
F3 C1 F2 F3' -2.1(11)
C2 C1 F2 F3' 113.2(10)
F2 C1 F3 F3' 3.3(17)
F1 C1 F3 F3' 125.0(15)
F2' C1 F3 F3' 8(2)
C2 C1 F3 F3' -122.3(15)
C1 F3 F3' F2 -6(3)
F2 C1 F3' F3 -176.6(17)
F1 C1 F3' F3 -65.4(17)
F2' C1 F3' F3 -175.0(13)
C2 C1 F3' F3 71.1(19)
F1 C1 F3' F2 111.2(12)
F2' C1 F3' F2 1.6(12)
F3 C1 F3' F2 176.6(17)
C2 C1 F3' F2 -112.3(10)
F2' F2 F3' F3 3(6)
C1 F2 F3' F3 7(3)
F2' F2 F3' C1 -4(3)
01 C10 C11' C11 -110.9(11)
