#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/03/1520329.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_1520329
loop_
_publ_author_name
'Murphy, Patrick J.'
'Horton, Peter N.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C12H18F3N3O3
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1048
_journal_year                    2009
_chemical_formula_sum            'C12 H18 F3 N3 O3'
_chemical_formula_weight         309.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                95.866(3)
_cell_angle_beta                 107.215(4)
_cell_angle_gamma                114.500(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9832(6)
_cell_length_b                   8.8773(7)
_cell_length_c                   12.1929(10)
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     725.49(11)
_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_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12761
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9849
_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    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut Blade'
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0792
_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)+(0.0001P)²+0.8965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                2183
_reflns_number_total             3301
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-1048.cif
_cod_data_source_block           2009src1065
_cod_depositor_comments
;
Citation :
Murphy, Patrick J. and Horton, Peter N. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/1048)

More at:
http://ecrystals.chem.soton.ac.uk/1048/
;
_cod_original_cell_volume        725.49(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1520329
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.4244(4) 0.2482(3) 0.5322(2) 0.0305(6) Uani 1 1 d . . .
C2 C 0.6691(4) 0.3793(4) 0.4599(3) 0.0399(7) Uani 1 1 d . . .
H2A H 0.7117 0.4982 0.4522 0.048 Uiso 1 1 calc R . .
H2B H 0.7032 0.3178 0.4048 0.048 Uiso 1 1 calc R . .
C3 C 0.7655(4) 0.3769(4) 0.5891(3) 0.0347(7) Uani 1 1 d . . .
H3 H 0.8549 0.4969 0.6398 0.042 Uiso 1 1 calc R . .
C4 C 0.8778(5) 0.2735(5) 0.6039(3) 0.0494(9) Uani 1 1 d . . .
H4A H 1.0028 0.3353 0.5908 0.059 Uiso 1 1 calc R . .
H4B H 0.7968 0.1616 0.5438 0.059 Uiso 1 1 calc R . .
C5 C 0.9250(5) 0.2444(5) 0.7283(3) 0.0527(9) Uani 1 1 d . . .
H5A H 0.9961 0.1751 0.7363 0.063 Uiso 1 1 calc R . .
H5B H 1.0123 0.3560 0.7884 0.063 Uiso 1 1 calc R . .
C6 C 0.7341(5) 0.1520(4) 0.7504(3) 0.0466(8) Uani 1 1 d . . .
H6A H 0.7674 0.1354 0.8317 0.056 Uiso 1 1 calc R . .
H6B H 0.6518 0.0373 0.6935 0.056 Uiso 1 1 calc R . .
C7 C 0.6139(4) 0.2501(4) 0.7370(3) 0.0348(7) Uani 1 1 d . . .
H7 H 0.4788 0.1718 0.7343 0.042 Uiso 1 1 calc R . .
C8 C 0.7074(4) 0.4085(4) 0.8405(3) 0.0362(7) Uani 1 1 d . . .
H8A H 0.7408 0.3752 0.9159 0.043 Uiso 1 1 calc R . .
H8B H 0.8331 0.4935 0.8372 0.043 Uiso 1 1 calc R . .
C9 C 0.5787(5) 0.4930(4) 0.8424(3) 0.0409(7) Uani 1 1 d . . .
C10 C 0.6677(5) 0.6527(5) 0.9402(3) 0.0524(9) Uani 1 1 d . . .
H10A H 0.5684 0.6918 0.9363 0.079 Uiso 1 1 calc R . .
H10B H 0.7824 0.7423 0.9310 0.079 Uiso 1 1 calc R . .
H10C H 0.7103 0.6281 1.0173 0.079 Uiso 1 1 calc R . .
N1 N 0.5920(3) 0.2964(3) 0.6237(2) 0.0324(6) Uani 1 1 d . . .
N2 N 0.4575(4) 0.2911(3) 0.4366(2) 0.0401(6) Uani 1 1 d . . .
H2 H 0.3635 0.2691 0.3680 0.048 Uiso 1 1 calc R . .
N3 N 0.2431(3) 0.1646(3) 0.5322(2) 0.0349(6) Uani 1 1 d . . .
H3A H 0.2265 0.1364 0.5967 0.042 Uiso 1 1 calc R . .
H3B H 0.1392 0.1372 0.4676 0.042 Uiso 1 1 calc R . .
O1 O 0.4109(3) 0.4335(3) 0.7697(2) 0.0555(7) Uani 1 1 d . . .
C11 C -0.0525(4) 0.1369(4) 0.2489(3) 0.0333(7) Uani 1 1 d D . .
O11 O 0.1134(3) 0.2274(3) 0.24774(19) 0.0446(6) Uani 1 1 d . A .
O12 O -0.0974(3) 0.0638(3) 0.32452(19) 0.0482(6) Uani 1 1 d . A .
C12 C -0.2358(17) 0.1175(16) 0.1479(10) 0.0463(10) Uani 0.441(10) 1 d PDU A 1
F11 F -0.3441(14) 0.1720(16) 0.1852(5) 0.086(3) Uani 0.441(10) 1 d PDU A 1
F12 F -0.1907(10) 0.1943(14) 0.0672(8) 0.083(3) Uani 0.441(10) 1 d PDU A 1
F13 F -0.3638(18) -0.0435(12) 0.0938(10) 0.081(4) Uani 0.441(10) 1 d PDU A 1
C212 C -0.2217(14) 0.1185(13) 0.1387(8) 0.0463(10) Uani 0.559(10) 1 d PDU A 2
F211 F -0.2359(11) 0.2600(8) 0.1443(8) 0.102(3) Uani 0.559(10) 1 d PDU A 2
F212 F -0.1949(10) 0.0877(13) 0.0386(5) 0.091(2) Uani 0.559(10) 1 d PDU A 2
F213 F -0.3920(11) -0.0103(12) 0.1200(8) 0.092(3) Uani 0.559(10) 1 d PDU A 2
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
N3 C1 N1 125.6(3) . .
N3 C1 N2 122.4(3) . .
N1 C1 N2 112.0(2) . .
N2 C2 C3 103.3(2) . .
N2 C2 H2A 111.1 . .
C3 C2 H2A 111.1 . .
N2 C2 H2B 111.1 . .
C3 C2 H2B 111.1 . .
H2A C2 H2B 109.1 . .
N1 C3 C4 109.7(2) . .
N1 C3 C2 102.5(2) . .
C4 C3 C2 114.9(3) . .
N1 C3 H3 109.8 . .
C4 C3 H3 109.8 . .
C2 C3 H3 109.8 . .
C3 C4 C5 110.5(3) . .
C3 C4 H4A 109.5 . .
C5 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
C5 C4 H4B 109.5 . .
H4A C4 H4B 108.1 . .
C6 C5 C4 110.1(3) . .
C6 C5 H5A 109.6 . .
C4 C5 H5A 109.6 . .
C6 C5 H5B 109.6 . .
C4 C5 H5B 109.6 . .
H5A C5 H5B 108.2 . .
C5 C6 C7 112.5(3) . .
C5 C6 H6A 109.1 . .
C7 C6 H6A 109.1 . .
C5 C6 H6B 109.1 . .
C7 C6 H6B 109.1 . .
H6A C6 H6B 107.8 . .
N1 C7 C8 111.1(2) . .
N1 C7 C6 108.4(2) . .
C8 C7 C6 112.6(2) . .
N1 C7 H7 108.2 . .
C8 C7 H7 108.2 . .
C6 C7 H7 108.2 . .
C9 C8 C7 114.7(2) . .
C9 C8 H8A 108.6 . .
C7 C8 H8A 108.6 . .
C9 C8 H8B 108.6 . .
C7 C8 H8B 108.6 . .
H8A C8 H8B 107.6 . .
O1 C9 C10 121.9(3) . .
O1 C9 C8 121.7(3) . .
C10 C9 C8 116.4(3) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C1 N1 C7 127.3(2) . .
C1 N1 C3 110.6(2) . .
C7 N1 C3 120.9(2) . .
C1 N2 C2 111.3(2) . .
C1 N2 H2 124.3 . .
C2 N2 H2 124.3 . .
C1 N3 H3A 120.0 . .
C1 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
O12 C11 O11 129.6(3) . .
O12 C11 C212 117.8(4) . .
O11 C11 C212 112.6(4) . .
O12 C11 C12 112.1(5) . .
O11 C11 C12 118.2(5) . .
C212 C11 C12 6.7(8) . .
F13 C12 F11 101.7(9) . .
F13 C12 F12 107.6(11) . .
F11 C12 F12 108.4(10) . .
F13 C12 C11 112.2(10) . .
F11 C12 C11 113.4(8) . .
F12 C12 C11 112.8(8) . .
F213 C212 F211 110.3(9) . .
F213 C212 F212 102.8(8) . .
F211 C212 F212 105.6(8) . .
F213 C212 C11 113.9(8) . .
F211 C212 C11 110.7(7) . .
F212 C212 C11 113.1(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N3 1.324(3) .
C1 N1 1.327(4) .
C1 N2 1.328(4) .
C2 N2 1.456(4) .
C2 C3 1.542(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 N1 1.481(3) .
C3 C4 1.517(4) .
C3 H3 1.0000 .
C4 C5 1.528(5) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.523(5) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.529(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 N1 1.463(3) .
C7 C8 1.528(4) .
C7 H7 1.0000 .
C8 C9 1.506(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 O1 1.214(4) .
C9 C10 1.502(5) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
N2 H2 0.8800 .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
C11 O12 1.234(3) .
C11 O11 1.237(3) .
C11 C212 1.535(9) .
C11 C12 1.540(11) .
C12 F13 1.311(11) .
C12 F11 1.312(12) .
C12 F12 1.305(11) .
C212 F213 1.297(9) .
C212 F211 1.305(10) .
C212 F212 1.321(10) .
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
N2 H2 O11 0.88 1.95 2.805(3) 162.4 .
N3 H3B O12 0.88 1.96 2.836(3) 177.0 .
N3 H3A O12 0.88 2.14 2.914(3) 147.1 2_556
