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#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/03/1520399.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_1520399
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C10H6FN3O
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              705
_journal_year                    2009
_chemical_formula_sum            'C10 H6 F N3 O'
_chemical_formula_weight         203.18
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.219(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1049(2)
_cell_length_b                   6.1023(2)
_cell_length_c                   17.6777(5)
_cell_measurement_reflns_used    20507
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     873.66(4)
_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_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18331
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9718
_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    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1992
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+0.3947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                1732
_reflns_number_total             1992
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-705.cif
_cod_data_source_block           2009src0464p21n
_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/705)

More at:
http://ecrystals.chem.soton.ac.uk/705/
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1520399
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.46683(16) 0.2430(2) 0.29382(8) 0.0223(3) Uani 1 1 d . . .
C2 C 0.52866(16) 0.4506(2) 0.28216(8) 0.0233(3) Uani 1 1 d . . .
H2 H 0.4666 0.5565 0.2538 0.028 Uiso 1 1 calc R . .
C3 C 0.68449(15) 0.5001(2) 0.31313(7) 0.0199(3) Uani 1 1 d . . .
H3 H 0.7298 0.6419 0.3062 0.024 Uiso 1 1 calc R . .
C4 C 0.77475(15) 0.3424(2) 0.35438(7) 0.0170(3) Uani 1 1 d . . .
C5 C 0.70772(16) 0.1342(2) 0.36502(7) 0.0201(3) Uani 1 1 d . . .
H5 H 0.7690 0.0271 0.3932 0.024 Uiso 1 1 calc R . .
C6 C 0.55181(16) 0.0833(2) 0.33462(7) 0.0220(3) Uani 1 1 d . . .
H6 H 0.5050 -0.0576 0.3417 0.026 Uiso 1 1 calc R . .
C7 C 0.93902(15) 0.3934(2) 0.38628(7) 0.0160(3) Uani 1 1 d . . .
C9 C 1.13884(15) 0.6167(2) 0.42251(7) 0.0172(3) Uani 1 1 d . . .
C10 C 1.17973(15) 0.4036(2) 0.44022(7) 0.0171(3) Uani 1 1 d . . .
C13 C 1.32221(15) 0.3235(2) 0.47980(7) 0.0184(3) Uani 1 1 d . . .
N11 N 1.04983(12) 0.26385(18) 0.41574(6) 0.0177(2) Uani 1 1 d . . .
N12 N 1.21154(14) 0.81027(19) 0.43043(7) 0.0228(3) Uani 1 1 d D . .
N14 N 1.43622(14) 0.25444(19) 0.51281(7) 0.0241(3) Uani 1 1 d . . .
O8 O 0.98481(10) 0.61249(14) 0.38784(5) 0.0179(2) Uani 1 1 d . . .
F1 F 0.31517(10) 0.19319(16) 0.26324(5) 0.0337(2) Uani 1 1 d . . .
H12A H 1.1511(19) 0.929(3) 0.4228(9) 0.030(4) Uiso 1 1 d D . .
H12B H 1.311(2) 0.814(3) 0.4520(10) 0.042(5) Uiso 1 1 d 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
F1 C1 C6 118.41(12) . .
F1 C1 C2 118.29(12) . .
C6 C1 C2 123.30(12) . .
C1 C2 C3 118.03(13) . .
C1 C2 H2 121.0 . .
C3 C2 H2 121.0 . .
C2 C3 C4 120.37(12) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C3 C4 C5 119.86(11) . .
C3 C4 C7 120.44(12) . .
C5 C4 C7 119.69(11) . .
C6 C5 C4 120.26(12) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C1 C6 C5 118.18(12) . .
C1 C6 H6 120.9 . .
C5 C6 H6 120.9 . .
N11 C7 O8 113.62(10) . .
N11 C7 C4 129.46(12) . .
O8 C7 C4 116.89(10) . .
N12 C9 O8 117.24(11) . .
N12 C9 C10 135.79(12) . .
O8 C9 C10 106.97(10) . .
C9 C10 N11 109.37(11) . .
C9 C10 C13 128.66(12) . .
N11 C10 C13 121.90(11) . .
N14 C13 C10 178.42(14) . .
C7 N11 C10 104.64(11) . .
C9 N12 H12A 118.3(11) . .
C9 N12 H12B 117.6(13) . .
H12A N12 H12B 122.8(18) . .
C9 O8 C7 105.38(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1 1.3579(15) .
C1 C6 1.380(2) .
C1 C2 1.381(2) .
C2 C3 1.3901(18) .
C2 H2 0.9500 .
C3 C4 1.3966(18) .
C3 H3 0.9500 .
C4 C5 1.3975(18) .
C4 C7 1.4592(17) .
C5 C6 1.3891(18) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 N11 1.2909(16) .
C7 O8 1.3875(15) .
C9 N12 1.3253(17) .
C9 O8 1.3695(15) .
C9 C10 1.3746(18) .
C10 N11 1.4100(16) .
C10 C13 1.4141(17) .
C13 N14 1.1534(17) .
N12 H12A 0.882(14) .
N12 H12B 0.879(15) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N12 H12A N11 0.882(14) 2.204(15) 3.0692(16) 166.8(15) 1_565
N12 H12B N14 0.879(15) 2.157(16) 3.0151(16) 164.9(18) 3_866
