#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:30:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180302 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151614.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_7151614
loop_
_publ_author_name
'Olsen, Jacob'
'Seiler, Paul'
'Wagner, Björn'
'Fischer, Holger'
'Tschopp, Thomas'
'Obst-Sander, Ulrike'
'Banner, David W.'
'Kansy, Manfred'
'Müller, Klaus'
'Diederich, François'
_publ_section_title
;
 A fluorine scan of the phenylamidinium needle of tricyclic thrombin
 inhibitors: effects of fluorine substitution on pKa and binding
 affinity and evidence for intermolecular C-F...CN interactions.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1339
_journal_page_last               1352
_journal_paper_doi               10.1039/b402515f
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C23 H19 F2 N3 O2'
_chemical_formula_sum            'C23 H19 F2 N3 O2'
_chemical_formula_weight         407.41
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.22(1)
_cell_angle_beta                 106.92(1)
_cell_angle_gamma                90.85(1)
_cell_formula_units_Z            2
_cell_length_a                   7.673(1)
_cell_length_b                   11.394(2)
_cell_length_c                   11.894(2)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      24.40
_cell_measurement_theta_min      18.60
_cell_volume                     985.5(3)
_computing_cell_refinement       'CAD4 VMS-software (Nonius, 1989)'
_computing_data_collection       'CAD4 VMS-software (Nonius, 1989)'
_computing_data_reduction        'MOLEN VMS-software (Nonius, 1990)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,1994)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'NONIUS CAD4'
_diffrn_measurement_method       θ/θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4111
_diffrn_reflns_theta_full        74.90
_diffrn_reflns_theta_max         74.90
_diffrn_reflns_theta_min         3.92
_diffrn_standards_decay_%        0.200
_diffrn_standards_interval_time  '167 min.'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  0.8616
_exptl_absorpt_correction_T_min  0.8345
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0050(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    'H-atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0569P)²+0.2816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                3272
_reflns_number_total             3904
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b402515f.txt
_cod_data_source_block           olsen3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151614
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7394(2) 0.36009(17) 0.96883(16) 0.0610(5) Uani 1 d . . .
N2 N 0.74261(18) 0.35181(13) 0.85262(13) 0.0553(4) Uani 1 d . . .
C3 C 0.6798(2) 0.24175(15) 0.78805(15) 0.0530(4) Uani 1 d . . .
C4 C 0.6164(2) 0.16642(15) 0.86572(15) 0.0524(4) Uani 1 d . . .
H4A H 0.6811 0.0919 0.8726 0.063(5) Uiso 1 calc R . .
C5 C 0.6575(2) 0.24508(16) 0.98676(15) 0.0573(4) Uani 1 d . . .
H5A H 0.7401 0.2081 1.0516 0.075(6) Uiso 1 calc R . .
O6 O 0.7903(2) 0.44793(14) 1.04118(13) 0.0840(5) Uani 1 d . . .
O7 O 0.67845(18) 0.21599(12) 0.68626(12) 0.0672(4) Uani 1 d . . .
C8 C 0.7985(2) 0.44880(18) 0.79999(19) 0.0668(5) Uani 1 d . . .
H8A H 0.8692 0.4176 0.7473 0.090(7) Uiso 1 calc R . .
H8B H 0.8784 0.5059 0.8632 0.090(7) Uiso 1 calc R . .
C9 C 0.6402(2) 0.51236(15) 0.73025(16) 0.0565(4) Uani 1 d . . .
C10 C 0.4659(2) 0.49831(17) 0.74034(18) 0.0624(5) Uani 1 d . . .
H10A H 0.4438 0.4492 0.7932 0.069(6) Uiso 1 calc R . .
C11 C 0.3249(3) 0.5563(2) 0.6730(2) 0.0789(6) Uani 1 d . . .
H11A H 0.2064 0.5472 0.6796 0.095(8) Uiso 1 calc R . .
C12 C 0.3593(3) 0.6271(2) 0.5966(2) 0.0834(7) Uani 1 d . . .
C13 C 0.5282(3) 0.6452(2) 0.5857(2) 0.0814(6) Uani 1 d . . .
H13A H 0.5487 0.6956 0.5335 0.111(9) Uiso 1 calc R . .
C14 C 0.6684(3) 0.58743(18) 0.6533(2) 0.0705(5) Uani 1 d . . .
H14A H 0.7867 0.5991 0.6472 0.103(8) Uiso 1 calc R . .
F15 F 0.2189(2) 0.68030(18) 0.52778(19) 0.1350(7) Uani 1 d . . .
C16 C 0.4060(2) 0.14205(14) 0.82495(14) 0.0489(4) Uani 1 d . . .
H16A H 0.3762 0.0708 0.8570 0.055(5) Uiso 1 calc R . .
N17 N 0.34423(18) 0.24710(11) 0.88525(12) 0.0487(3) Uani 1 d . . .
C18 C 0.1648(2) 0.22777(18) 0.90441(18) 0.0645(5) Uani 1 d . . .
H18A H 0.0841 0.1757 0.8369 0.067(6) Uiso 1 calc R . .
H18B H 0.1075 0.3034 0.9125 0.080(6) Uiso 1 calc R . .
C19 C 0.1960(3) 0.1709(3) 1.0173(2) 0.0915(8) Uani 1 d . . .
H19A H 0.1519 0.0875 0.9986 0.166(15) Uiso 1 calc R . .
H19B H 0.1322 0.2124 1.0696 0.148(13) Uiso 1 calc R . .
C20 C 0.4021(3) 0.18185(19) 1.07610(18) 0.0721(5) Uani 1 d . . .
H20A H 0.4556 0.1046 1.0699 0.100(8) Uiso 1 calc R . .
H20B H 0.4313 0.2149 1.1600 0.080(6) Uiso 1 calc R . .
C21 C 0.4709(2) 0.26621(15) 1.00594(15) 0.0544(4) Uani 1 d . . .
H21A H 0.4684 0.3492 1.0418 0.063(5) Uiso 1 calc R . .
C22 C 0.3176(2) 0.12593(14) 0.69254(14) 0.0487(4) Uani 1 d . . .
C23 C 0.2114(2) 0.20964(16) 0.63399(16) 0.0556(4) Uani 1 d . . .
H23A H 0.1915 0.2800 0.6780 0.061(5) Uiso 1 calc R . .
C24 C 0.1341(2) 0.19204(18) 0.51231(17) 0.0619(5) Uani 1 d . . .
H24A H 0.0634 0.2502 0.4740 0.078(7) Uiso 1 calc R . .
C25 C 0.1616(2) 0.08758(18) 0.44675(16) 0.0605(5) Uani 1 d . . .
C26 C 0.2657(3) 0.00209(17) 0.50210(17) 0.0632(5) Uani 1 d . . .
H26A H 0.2849 -0.0687 0.4585 0.092(7) Uiso 1 calc R . .
C27 C 0.3401(3) 0.02360(15) 0.62264(16) 0.0564(4) Uani 1 d . . .
F28 F 0.44564(19) -0.05853(10) 0.67760(11) 0.0824(4) Uani 1 d . . .
C29 C 0.0775(3) 0.0713(2) 0.31993(19) 0.0775(6) Uani 1 d . . .
N30 N 0.0072(3) 0.0617(2) 0.22035(18) 0.1077(8) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
_geom_angle_publ_flag
O6 C1 N2 124.11(19) . . ?
O6 C1 C5 127.22(18) . . ?
N2 C1 C5 108.63(15) . . ?
C1 N2 C3 113.16(16) . . ?
C1 N2 C8 124.36(15) . . ?
C3 N2 C8 122.43(15) . . ?
O7 C3 N2 122.96(17) . . ?
O7 C3 C4 128.34(16) . . ?
N2 C3 C4 108.69(14) . . ?
C3 C4 C5 104.64(14) . . ?
C3 C4 C16 112.54(14) . . ?
C5 C4 C16 104.69(13) . . ?
C1 C5 C21 109.42(15) . . ?
C1 C5 C4 104.78(14) . . ?
C21 C5 C4 105.22(13) . . ?
N2 C8 C9 113.32(14) . . ?
C10 C9 C14 118.41(18) . . ?
C10 C9 C8 122.13(17) . . ?
C14 C9 C8 119.46(17) . . ?
C11 C10 C9 120.03(19) . . ?
C12 C11 C10 119.2(2) . . ?
C13 C12 F15 118.5(2) . . ?
C13 C12 C11 122.7(2) . . ?
F15 C12 C11 118.8(2) . . ?
C12 C13 C14 117.8(2) . . ?
C13 C14 C9 121.79(19) . . ?
N17 C16 C22 112.17(13) . . ?
N17 C16 C4 102.10(12) . . ?
C22 C16 C4 115.29(13) . . ?
C21 N17 C16 105.36(12) . . ?
C21 N17 C18 103.53(13) . . ?
C16 N17 C18 113.85(13) . . ?
N17 C18 C19 107.72(17) . . ?
C18 C19 C20 105.51(17) . . ?
C19 C20 C21 103.67(17) . . ?
N17 C21 C5 103.54(13) . . ?
N17 C21 C20 106.16(15) . . ?
C5 C21 C20 117.49(16) . . ?
C23 C22 C27 116.41(16) . . ?
C23 C22 C16 123.19(14) . . ?
C27 C22 C16 120.40(15) . . ?
C24 C23 C22 121.44(16) . . ?
C23 C24 C25 119.59(18) . . ?
C26 C25 C24 120.56(17) . . ?
C26 C25 C29 121.18(19) . . ?
C24 C25 C29 118.3(2) . . ?
C27 C26 C25 117.80(17) . . ?
F28 C27 C26 118.32(16) . . ?
F28 C27 C22 117.46(16) . . ?
C26 C27 C22 124.21(18) . . ?
N30 C29 C25 177.6(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O6 1.213(2) . ?
C1 N2 1.381(2) . ?
C1 C5 1.511(3) . ?
N2 C3 1.385(2) . ?
N2 C8 1.454(2) . ?
C3 O7 1.206(2) . ?
C3 C4 1.509(3) . ?
C4 C5 1.542(2) . ?
C4 C16 1.554(2) . ?
C5 C21 1.531(2) . ?
C8 C9 1.510(3) . ?
C9 C10 1.386(2) . ?
C9 C14 1.387(3) . ?
C10 C11 1.377(3) . ?
C11 C12 1.365(3) . ?
C12 C13 1.355(3) . ?
C12 F15 1.353(3) . ?
C13 C14 1.374(3) . ?
C16 N17 1.4734(19) . ?
C16 C22 1.509(2) . ?
N17 C21 1.468(2) . ?
N17 C18 1.477(2) . ?
C18 C19 1.521(3) . ?
C19 C20 1.528(3) . ?
C20 C21 1.531(3) . ?
C22 C23 1.385(2) . ?
C22 C27 1.388(2) . ?
C23 C24 1.382(3) . ?
C24 C25 1.392(3) . ?
C25 C26 1.378(3) . ?
C25 C29 1.444(3) . ?
C26 C27 1.368(3) . ?
C27 F28 1.352(2) . ?
C29 N30 1.140(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C1 N2 C3 179.13(17) . . . . ?
C5 C1 N2 C3 -2.82(19) . . . . ?
O6 C1 N2 C8 -3.2(3) . . . . ?
C5 C1 N2 C8 174.80(15) . . . . ?
C1 N2 C3 O7 -177.20(15) . . . . ?
C8 N2 C3 O7 5.1(2) . . . . ?
C1 N2 C3 C4 3.25(18) . . . . ?
C8 N2 C3 C4 -174.42(14) . . . . ?
O7 C3 C4 C5 178.23(17) . . . . ?
N2 C3 C4 C5 -2.25(17) . . . . ?
O7 C3 C4 C16 -68.7(2) . . . . ?
N2 C3 C4 C16 110.84(14) . . . . ?
O6 C1 C5 C21 66.8(2) . . . . ?
N2 C1 C5 C21 -111.20(15) . . . . ?
O6 C1 C5 C4 179.17(18) . . . . ?
N2 C1 C5 C4 1.20(18) . . . . ?
C3 C4 C5 C1 0.63(16) . . . . ?
C16 C4 C5 C1 -117.94(14) . . . . ?
C3 C4 C5 C21 115.98(14) . . . . ?
C16 C4 C5 C21 -2.58(18) . . . . ?
C1 N2 C8 C9 -97.79(19) . . . . ?
C3 N2 C8 C9 79.6(2) . . . . ?
N2 C8 C9 C10 14.8(2) . . . . ?
N2 C8 C9 C14 -165.12(17) . . . . ?
C14 C9 C10 C11 1.3(3) . . . . ?
C8 C9 C10 C11 -178.64(18) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 -1.4(4) . . . . ?
C10 C11 C12 F15 177.7(2) . . . . ?
F15 C12 C13 C14 -177.9(2) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C10 C9 C14 C13 -1.5(3) . . . . ?
C8 C9 C14 C13 178.43(19) . . . . ?
C3 C4 C16 N17 -85.93(15) . . . . ?
C5 C4 C16 N17 27.13(16) . . . . ?
C3 C4 C16 C22 35.95(18) . . . . ?
C5 C4 C16 C22 149.01(14) . . . . ?
C22 C16 N17 C21 -167.19(13) . . . . ?
C4 C16 N17 C21 -43.20(16) . . . . ?
C22 C16 N17 C18 80.06(17) . . . . ?
C4 C16 N17 C18 -155.95(14) . . . . ?
C21 N17 C18 C19 -30.3(2) . . . . ?
C16 N17 C18 C19 83.56(19) . . . . ?
N17 C18 C19 C20 11.5(2) . . . . ?
C18 C19 C20 C21 11.0(2) . . . . ?
C16 N17 C21 C5 42.00(16) . . . . ?
C18 N17 C21 C5 161.83(14) . . . . ?
C16 N17 C21 C20 -82.34(16) . . . . ?
C18 N17 C21 C20 37.49(17) . . . . ?
C1 C5 C21 N17 88.98(16) . . . . ?
C4 C5 C21 N17 -23.12(17) . . . . ?
C1 C5 C21 C20 -154.40(16) . . . . ?
C4 C5 C21 C20 93.50(18) . . . . ?
C19 C20 C21 N17 -30.2(2) . . . . ?
C19 C20 C21 C5 -145.39(18) . . . . ?
N17 C16 C22 C23 8.6(2) . . . . ?
C4 C16 C22 C23 -107.71(17) . . . . ?
N17 C16 C22 C27 -171.43(14) . . . . ?
C4 C16 C22 C27 72.28(19) . . . . ?
C27 C22 C23 C24 -0.6(2) . . . . ?
C16 C22 C23 C24 179.36(15) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C23 C24 C25 C29 179.39(16) . . . . ?
C24 C25 C26 C27 0.0(3) . . . . ?
C29 C25 C26 C27 -179.66(17) . . . . ?
C25 C26 C27 F28 -178.63(16) . . . . ?
C25 C26 C27 C22 -0.1(3) . . . . ?
C23 C22 C27 F28 178.94(15) . . . . ?
C16 C22 C27 F28 -1.1(2) . . . . ?
C23 C22 C27 C26 0.4(3) . . . . ?
C16 C22 C27 C26 -179.64(16) . . . . ?
C26 C25 C29 N30 164(5) . . . . ?
C24 C25 C29 N30 -15(5) . . . . ?
