#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/29/7152990.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_7152990
loop_
_publ_author_name
'Dudkin, Sergii'
'Iaroshenko, Viktor O.'
'Sosnovskikh, Vyacheslav Ya'
'Tolmachev, Andrey A.'
'Villinger, Alexander'
'Langer, Peter'
_publ_section_title
;
 Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5351
_journal_page_last               5361
_journal_paper_doi               10.1039/c3ob26837c
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C15 H14 F3 N3 O3'
_chemical_formula_sum            'C15 H14 F3 N3 O3'
_chemical_formula_weight         341.29
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 109.1480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.9524(3)
_cell_length_b                   6.20460(10)
_cell_length_c                   14.3442(2)
_cell_measurement_reflns_used    5832
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      59.928
_cell_measurement_theta_min      5.696
_cell_volume                     1509.37(4)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17011
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0510
_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)+(0.0626P)²+0.9729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1387
_reflns_number_gt                3462
_reflns_number_total             4381
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ob26837c.txt
_cod_data_source_block           av_sd341
_cod_original_sg_symbol_Hall     'P 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7152990
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.09734(7) 0.0124(2) 0.34928(8) 0.0184(2) Uani 1 1 d .
N2 N 0.23186(7) 0.2221(3) 0.18854(9) 0.0278(3) Uani 1 1 d .
N3 N 0.11988(7) 0.0485(2) 0.19769(8) 0.0185(2) Uani 1 1 d .
O1 O 0.33373(6) 0.32844(18) 0.33243(7) 0.0231(2) Uani 1 1 d .
O2 O 0.01155(7) -0.1268(2) 0.20860(8) 0.0299(3) Uani 1 1 d .
O3 O 0.18070(7) 0.1634(2) 0.48971(8) 0.0289(3) Uani 1 1 d .
F1 F 0.22639(8) 0.61957(19) 0.46271(10) 0.0488(3) Uani 1 1 d .
F2 F 0.32935(7) 0.7056(2) 0.42579(11) 0.0536(4) Uani 1 1 d .
F3 F 0.21733(7) 0.67715(17) 0.31189(9) 0.0446(3) Uani 1 1 d .
C1 C 0.07181(8) -0.0272(2) 0.24960(10) 0.0189(3) Uani 1 1 d .
C2 C 0.16328(8) 0.1366(2) 0.39928(10) 0.0183(3) Uani 1 1 d .
C3 C 0.20644(8) 0.2216(2) 0.34092(10) 0.0175(3) Uani 1 1 d .
C4 C 0.27999(8) 0.3505(2) 0.38627(10) 0.0201(3) Uani 1 1 d .
H4 H 0.3065 0.2925 0.4541 0.024 Uiso 1 1 calc R
C5 C 0.30047(9) 0.3623(3) 0.22980(11) 0.0242(3) Uani 1 1 d .
H5 H 0.2846 0.5167 0.2162 0.029 Uiso 1 1 calc R
C9 C 0.36247(9) 0.3047(3) 0.18349(11) 0.0263(3) Uani 1 1 d .
C10 C 0.38383(10) 0.4568(3) 0.12762(13) 0.0333(4) Uani 1 1 d .
H10 H 0.3597 0.5949 0.1186 0.040 Uiso 1 1 calc R
C11 C 0.44042(12) 0.4099(4) 0.08441(15) 0.0414(5) Uani 1 1 d .
H11 H 0.4547 0.5156 0.0454 0.050 Uiso 1 1 calc R
C12 C 0.47625(11) 0.2104(4) 0.09769(15) 0.0442(5) Uani 1 1 d .
H12 H 0.5155 0.1787 0.0685 0.053 Uiso 1 1 calc R
C13 C 0.45440(11) 0.0558(3) 0.15423(16) 0.0424(5) Uani 1 1 d .
H13 H 0.4786 -0.0823 0.1639 0.051 Uiso 1 1 calc R
C14 C 0.39690(10) 0.1047(3) 0.19653(14) 0.0350(4) Uani 1 1 d .
H14 H 0.3814 -0.0008 0.2346 0.042 Uiso 1 1 calc R
C6 C 0.18615(8) 0.1681(2) 0.24284(9) 0.0174(3) Uani 1 1 d .
C7 C 0.04742(10) -0.0746(3) 0.40317(12) 0.0290(3) Uani 1 1 d .
H7A H -0.0058 -0.0142 0.3759 0.043 Uiso 1 1 calc R
H7B H 0.0698 -0.0359 0.4731 0.043 Uiso 1 1 calc R
H7C H 0.0449 -0.2319 0.3966 0.043 Uiso 1 1 calc R
C8 C 0.26328(10) 0.5890(3) 0.39649(13) 0.0302(3) Uani 1 1 d .
C15 C 0.10187(10) -0.0247(3) 0.09560(11) 0.0313(4) Uani 1 1 d .
H15A H 0.0945 0.1006 0.0519 0.047 Uiso 1 1 calc R
H15B H 0.0535 -0.1109 0.0765 0.047 Uiso 1 1 calc R
H15C H 0.1456 -0.1126 0.0901 0.047 Uiso 1 1 calc R
H2 H 0.2116(13) 0.223(4) 0.1197(18) 0.044(6) 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
C1 N1 C2 124.78(11)
C1 N1 C7 115.50(12)
C2 N1 C7 119.61(12)
C6 N2 C5 120.36(12)
C6 N2 H2 120.9(14)
C5 N2 H2 114.0(14)
C6 N3 C1 121.57(11)
C6 N3 C15 120.85(11)
C1 N3 C15 117.24(12)
C5 O1 C4 114.87(11)
O2 C1 N1 122.30(12)
O2 C1 N3 121.41(13)
N1 C1 N3 116.27(12)
O3 C2 N1 119.39(12)
O3 C2 C3 124.65(13)
N1 C2 C3 115.95(11)
C6 C3 C2 120.19(12)
C6 C3 C4 118.29(12)
C2 C3 C4 121.17(12)
O1 C4 C3 111.73(11)
O1 C4 C8 109.52(12)
C3 C4 C8 112.73(12)
O1 C4 H4 107.5
C3 C4 H4 107.5
C8 C4 H4 107.5
O1 C5 N2 110.19(12)
O1 C5 C9 107.59(12)
N2 C5 C9 108.92(13)
O1 C5 H5 110.0
N2 C5 H5 110.0
C9 C5 H5 110.0
C14 C9 C10 120.16(15)
C14 C9 C5 121.12(15)
C10 C9 C5 118.73(16)
C9 C10 C11 120.27(18)
C9 C10 H10 119.9
C11 C10 H10 119.9
C12 C11 C10 120.31(18)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 119.40(16)
C11 C12 H12 120.3
C13 C12 H12 120.3
C14 C13 C12 119.63(19)
C14 C13 H13 120.2
C12 C13 H13 120.2
C9 C14 C13 120.22(17)
C9 C14 H14 119.9
C13 C14 H14 119.9
N2 C6 N3 117.43(12)
N2 C6 C3 121.70(12)
N3 C6 C3 120.81(12)
N1 C7 H7A 109.5
N1 C7 H7B 109.5
H7A C7 H7B 109.5
N1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
F2 C8 F1 107.20(14)
F2 C8 F3 106.48(15)
F1 C8 F3 106.51(14)
F2 C8 C4 111.94(14)
F1 C8 C4 111.36(14)
F3 C8 C4 112.99(13)
N3 C15 H15A 109.5
N3 C15 H15B 109.5
H15A C15 H15B 109.5
N3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3729(17)
N1 C2 1.3973(18)
N1 C7 1.4652(17)
N2 C6 1.3459(17)
N2 C5 1.465(2)
N2 H2 0.93(2)
N3 C6 1.3711(17)
N3 C1 1.3934(17)
N3 C15 1.4643(18)
O1 C5 1.4111(18)
O1 C4 1.4263(17)
O2 C1 1.2168(18)
O3 C2 1.2418(16)
F1 C8 1.3377(19)
F2 C8 1.334(2)
F3 C8 1.340(2)
C2 C3 1.4160(18)
C3 C6 1.3733(18)
C3 C4 1.4976(19)
C4 C8 1.527(2)
C4 H4 1.0000
C5 C9 1.514(2)
C5 H5 1.0000
C9 C14 1.372(3)
C9 C10 1.372(2)
C10 C11 1.384(2)
C10 H10 0.9500
C11 C12 1.379(3)
C11 H11 0.9500
C12 C13 1.393(3)
C12 H12 0.9500
C13 C14 1.392(3)
C13 H13 0.9500
C14 H14 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
C2 N1 C1 O2 -175.94(14)
C7 N1 C1 O2 0.4(2)
C2 N1 C1 N3 5.6(2)
C7 N1 C1 N3 -178.03(13)
C6 N3 C1 O2 177.38(14)
C15 N3 C1 O2 -9.2(2)
C6 N3 C1 N1 -4.2(2)
C15 N3 C1 N1 169.19(13)
C1 N1 C2 O3 179.42(13)
C7 N1 C2 O3 3.2(2)
C1 N1 C2 C3 -1.3(2)
C7 N1 C2 C3 -177.53(13)
O3 C2 C3 C6 174.59(14)
N1 C2 C3 C6 -4.62(19)
O3 C2 C3 C4 1.5(2)
N1 C2 C3 C4 -177.72(12)
C5 O1 C4 C3 50.11(16)
C5 O1 C4 C8 -75.52(15)
C6 C3 C4 O1 -22.82(18)
C2 C3 C4 O1 150.41(13)
C6 C3 C4 C8 101.02(15)
C2 C3 C4 C8 -85.75(17)
C4 O1 C5 N2 -54.23(17)
C4 O1 C5 C9 -172.84(12)
C6 N2 C5 O1 32.2(2)
C6 N2 C5 C9 149.98(14)
O1 C5 C9 C14 56.48(19)
N2 C5 C9 C14 -62.95(19)
O1 C5 C9 C10 -123.64(16)
N2 C5 C9 C10 116.94(16)
C14 C9 C10 C11 -0.3(3)
C5 C9 C10 C11 179.85(16)
C9 C10 C11 C12 -0.5(3)
C10 C11 C12 C13 0.6(3)
C11 C12 C13 C14 -0.1(3)
C10 C9 C14 C13 0.8(3)
C5 C9 C14 C13 -179.30(16)
C12 C13 C14 C9 -0.7(3)
C5 N2 C6 N3 175.68(13)
C5 N2 C6 C3 -7.2(2)
C1 N3 C6 N2 175.67(13)
C15 N3 C6 N2 2.5(2)
C1 N3 C6 C3 -1.5(2)
C15 N3 C6 C3 -174.62(14)
C2 C3 C6 N2 -170.99(14)
C4 C3 C6 N2 2.3(2)
C2 C3 C6 N3 6.1(2)
C4 C3 C6 N3 179.35(13)
O1 C4 C8 F2 -47.41(18)
C3 C4 C8 F2 -172.47(13)
O1 C4 C8 F1 -167.40(13)
C3 C4 C8 F1 67.55(17)
O1 C4 C8 F3 72.78(16)
C3 C4 C8 F3 -52.27(17)
