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#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520411.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_1520411
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C15H15FN4O
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              635
_journal_year                    2009
_chemical_formula_sum            'C15 H15 F N4 O'
_chemical_formula_weight         286.31
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1453(2)
_cell_length_b                   7.8485(2)
_cell_length_c                   27.6153(8)
_cell_measurement_reflns_used    12464
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1331.92(7)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9041
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_correction_T_min  0.9887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0467
_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)+(0.0130P)²+0.8629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                1611
_reflns_number_total             1781
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-635.cif
_cod_data_source_block           2009src0063
_cod_depositor_comments
;
Citation :
Spencer, John and Patel, Hiren and Callear, Samantha K. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/635)

More at:
http://ecrystals.chem.soton.ac.uk/635/
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1520411
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
C2 C -0.2643(5) 0.7695(4) -0.36426(10) 0.0300(7) Uani 1 1 d . . .
H2 H -0.3513 0.8398 -0.3845 0.036 Uiso 1 1 calc R . .
C3 C -0.0651(5) 0.7161(4) -0.38136(10) 0.0268(6) Uani 1 1 d . . .
H3 H -0.0126 0.7487 -0.4124 0.032 Uiso 1 1 calc R . .
C4 C 0.0535(5) 0.6129(3) -0.35095(9) 0.0253(6) Uani 1 1 d . . .
H4 H 0.1905 0.5720 -0.3619 0.030 Uiso 1 1 calc R . .
C6 C -0.2119(5) 0.6263(3) -0.29358(9) 0.0200(6) Uani 1 1 d . . .
C8 C -0.1453(5) 0.5011(3) -0.21300(9) 0.0211(6) Uani 1 1 d . . .
H8A H -0.0130 0.4560 -0.2289 0.025 Uiso 1 1 calc R . .
H8B H -0.2211 0.4048 -0.1972 0.025 Uiso 1 1 calc R . .
C9 C -0.0802(4) 0.6325(3) -0.17477(9) 0.0187(5) Uani 1 1 d . . .
H9A H 0.0049 0.5764 -0.1488 0.022 Uiso 1 1 calc R . .
H9B H 0.0122 0.7215 -0.1897 0.022 Uiso 1 1 calc R . .
C11 C -0.4204(4) 0.7859(3) -0.19099(9) 0.0207(5) Uani 1 1 d . . .
H11A H -0.3448 0.8814 -0.2073 0.025 Uiso 1 1 calc R . .
H11B H -0.5531 0.8315 -0.1753 0.025 Uiso 1 1 calc R . .
C12 C -0.4835(5) 0.6516(3) -0.22832(9) 0.0219(6) Uani 1 1 d . . .
H12A H -0.5715 0.5614 -0.2127 0.026 Uiso 1 1 calc R . .
H12B H -0.5725 0.7044 -0.2541 0.026 Uiso 1 1 calc R . .
C13 C -0.3623(4) 0.6736(3) -0.11004(9) 0.0197(6) Uani 1 1 d . . .
C14 C -0.2159(4) 0.6079(3) -0.07086(9) 0.0193(5) Uani 1 1 d . . .
C15 C -0.0097(4) 0.6736(3) -0.06223(9) 0.0198(5) Uani 1 1 d . . .
H15 H 0.0495 0.7559 -0.0837 0.024 Uiso 1 1 calc R . .
C16 C 0.1109(4) 0.6203(4) -0.02252(9) 0.0222(6) Uani 1 1 d . . .
H16 H 0.2514 0.6659 -0.0164 0.027 Uiso 1 1 calc R . .
C17 C 0.0216(5) 0.4996(4) 0.00776(9) 0.0235(6) Uani 1 1 d . . .
C18 C -0.1822(5) 0.4312(4) 0.00043(10) 0.0264(6) Uani 1 1 d . . .
H18 H -0.2392 0.3476 0.0218 0.032 Uiso 1 1 calc R . .
C19 C -0.3018(5) 0.4875(4) -0.03892(9) 0.0225(6) Uani 1 1 d . . .
H19 H -0.4439 0.4437 -0.0443 0.027 Uiso 1 1 calc R . .
N1 N -0.3412(4) 0.7271(3) -0.32063(8) 0.0247(5) Uani 1 1 d . . .
N5 N -0.0144(4) 0.5673(3) -0.30681(8) 0.0224(5) Uani 1 1 d . . .
N7 N -0.2878(4) 0.5770(3) -0.24933(7) 0.0203(5) Uani 1 1 d . . .
N10 N -0.2767(3) 0.7107(3) -0.15406(7) 0.0184(5) Uani 1 1 d . . .
O20 O -0.5550(3) 0.6995(3) -0.10093(7) 0.0333(5) Uani 1 1 d . . .
F21 F 0.1388(3) 0.4463(2) 0.04670(6) 0.0350(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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 '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
N1 C2 C3 123.2(3) . .
N1 C2 H2 118.4 . .
C3 C2 H2 118.4 . .
C4 C3 C2 116.1(3) . .
C4 C3 H3 121.9 . .
C2 C3 H3 121.9 . .
N5 C4 C3 123.3(3) . .
N5 C4 H4 118.3 . .
C3 C4 H4 118.3 . .
N5 C6 N1 125.6(2) . .
N5 C6 N7 116.9(2) . .
N1 C6 N7 117.5(2) . .
N7 C8 C9 110.9(2) . .
N7 C8 H8A 109.5 . .
C9 C8 H8A 109.5 . .
N7 C8 H8B 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 108.0 . .
N10 C9 C8 109.6(2) . .
N10 C9 H9A 109.8 . .
C8 C9 H9A 109.8 . .
N10 C9 H9B 109.8 . .
C8 C9 H9B 109.8 . .
H9A C9 H9B 108.2 . .
N10 C11 C12 110.1(2) . .
N10 C11 H11A 109.6 . .
C12 C11 H11A 109.6 . .
N10 C11 H11B 109.6 . .
C12 C11 H11B 109.6 . .
H11A C11 H11B 108.2 . .
N7 C12 C11 109.7(2) . .
N7 C12 H12A 109.7 . .
C11 C12 H12A 109.7 . .
N7 C12 H12B 109.7 . .
C11 C12 H12B 109.7 . .
H12A C12 H12B 108.2 . .
O20 C13 N10 121.5(3) . .
O20 C13 C14 119.2(2) . .
N10 C13 C14 119.2(2) . .
C15 C14 C19 119.2(2) . .
C15 C14 C13 123.0(2) . .
C19 C14 C13 117.5(2) . .
C14 C15 C16 120.7(2) . .
C14 C15 H15 119.6 . .
C16 C15 H15 119.6 . .
C17 C16 C15 118.3(3) . .
C17 C16 H16 120.8 . .
C15 C16 H16 120.8 . .
F21 C17 C16 118.7(3) . .
F21 C17 C18 118.5(3) . .
C16 C17 C18 122.8(3) . .
C17 C18 C19 118.2(3) . .
C17 C18 H18 120.9 . .
C19 C18 H18 120.9 . .
C18 C19 C14 120.8(3) . .
C18 C19 H19 119.6 . .
C14 C19 H19 119.6 . .
C2 N1 C6 115.9(3) . .
C4 N5 C6 115.8(2) . .
C6 N7 C12 121.6(2) . .
C6 N7 C8 121.8(2) . .
C12 N7 C8 112.67(19) . .
C13 N10 C9 125.3(2) . .
C13 N10 C11 118.3(2) . .
C9 N10 C11 112.99(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.336(3) .
C2 C3 1.377(4) .
C2 H2 0.9500 .
C3 C4 1.376(4) .
C3 H3 0.9500 .
C4 N5 1.337(3) .
C4 H4 0.9500 .
C6 N5 1.349(4) .
C6 N1 1.348(3) .
C6 N7 1.364(3) .
C8 N7 1.459(3) .
C8 C9 1.529(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 N10 1.471(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C11 N10 1.472(3) .
C11 C12 1.525(4) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 N7 1.458(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 O20 1.227(3) .
C13 N10 1.356(3) .
C13 C14 1.499(4) .
C14 C15 1.388(4) .
C14 C19 1.396(4) .
C15 C16 1.388(4) .
C15 H15 0.9500 .
C16 C17 1.377(4) .
C16 H16 0.9500 .
C17 F21 1.360(3) .
C17 C18 1.378(4) .
C18 C19 1.384(4) .
C18 H18 0.9500 .
C19 H19 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 897797
