#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:30:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180302 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151615.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_7151615
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                93.680(1)
_cell_angle_beta                 94.130(1)
_cell_angle_gamma                115.220(1)
_cell_formula_units_Z            2
_cell_length_a                   9.4926(2)
_cell_length_b                   10.3004(3)
_cell_length_c                   10.9831(3)
_cell_measurement_reflns_used    4273
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      1.87
_cell_volume                     963.64(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Kappa CCD'
_computing_data_reduction        'Denzo + Scalepak (Otwinowski & Minor, 1997)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8020
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.059(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    'H-atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0656P)²+0.1529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                3458
_reflns_number_total             4404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b402515f.txt
_cod_data_source_block           olsen7
_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               7151615
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 0.55094(17) 0.49647(16) 0.28585(14) 0.0441(3) Uani 1 d . . .
N2 N 0.53867(13) 0.39606(12) 0.36816(10) 0.0386(3) Uani 1 d . . .
C3 C 0.39128(16) 0.32973(14) 0.40580(11) 0.0362(3) Uani 1 d . . .
C4 C 0.28336(16) 0.37654(14) 0.33149(12) 0.0359(3) Uani 1 d . . .
H4A H 0.2237 0.4104 0.3851 0.041(4) Uiso 1 calc R . .
C5 C 0.39321(17) 0.49887(15) 0.26242(13) 0.0401(3) Uani 1 d . . .
H5A H 0.3971 0.5934 0.2918 0.050(5) Uiso 1 calc R . .
O6 O 0.66969(13) 0.56698(14) 0.24192(13) 0.0646(4) Uani 1 d . . .
O7 O 0.35890(12) 0.24896(12) 0.48535(9) 0.0477(3) Uani 1 d . . .
C8 C 0.66795(17) 0.36058(17) 0.40802(14) 0.0444(3) Uani 1 d . . .
H8A H 0.6633 0.3415 0.4943 0.059(5) Uiso 1 calc R . .
H8B H 0.7679 0.4435 0.4019 0.052(5) Uiso 1 calc R . .
C9 C 0.66103(15) 0.23086(16) 0.33167(13) 0.0405(3) Uani 1 d . . .
C10 C 0.6767(2) 0.2341(2) 0.20692(15) 0.0547(4) Uani 1 d . . .
H10A H 0.6967 0.3197 0.1709 0.075(6) Uiso 1 calc R . .
C11 C 0.6633(2) 0.1139(2) 0.13538(17) 0.0651(5) Uani 1 d . . .
H11A H 0.6733 0.1165 0.0509 0.079(7) Uiso 1 calc R . .
C12 C 0.6352(2) -0.0092(2) 0.18938(19) 0.0619(5) Uani 1 d . . .
C13 C 0.62320(19) -0.01663(19) 0.31271(19) 0.0578(4) Uani 1 d . . .
H13A H 0.6070 -0.1018 0.3483 0.070(6) Uiso 1 calc R . .
C14 C 0.63551(17) 0.10466(18) 0.38319(15) 0.0471(4) Uani 1 d . . .
H14A H 0.6264 0.1013 0.4677 0.059(5) Uiso 1 calc R . .
F15 F 0.61762(18) -0.12905(16) 0.11861(15) 0.0988(5) Uani 1 d . . .
C16 C 0.17185(15) 0.25819(14) 0.22770(12) 0.0348(3) Uani 1 d . . .
H16A H 0.0725 0.2677 0.2151 0.043(4) Uiso 1 calc R . .
N17 N 0.25438(14) 0.29702(12) 0.11781(10) 0.0374(3) Uani 1 d . . .
C18 C 0.1459(2) 0.25423(18) 0.00385(13) 0.0494(4) Uani 1 d . . .
H18A H 0.0565 0.1613 0.0086 0.053(5) Uiso 1 calc R . .
H18B H 0.1996 0.2452 -0.0669 0.070(6) Uiso 1 calc R . .
C19 C 0.0904(2) 0.3730(2) -0.00899(15) 0.0550(4) Uani 1 d . . .
H19A H 0.0938 0.3993 -0.0933 0.063(5) Uiso 1 calc R . .
H19B H -0.0171 0.3405 0.0122 0.076(6) Uiso 1 calc R . .
C20 C 0.2034(2) 0.50114(18) 0.08023(15) 0.0510(4) Uani 1 d . . .
H20A H 0.1502 0.5190 0.1481 0.072(6) Uiso 1 calc R . .
H20B H 0.2488 0.5887 0.0384 0.070(6) Uiso 1 calc R . .
C21 C 0.33020(18) 0.45554(15) 0.12689(13) 0.0405(3) Uani 1 d . . .
H21A H 0.4177 0.4891 0.0752 0.043(4) Uiso 1 calc R . .
C22 C 0.13502(14) 0.10523(14) 0.25249(11) 0.0338(3) Uani 1 d . . .
C23 C 0.22422(15) 0.03850(14) 0.20814(13) 0.0367(3) Uani 1 d . . .
H23A H 0.3044 0.0860 0.1592 0.043(4) Uiso 1 calc R . .
C24 C 0.19275(15) -0.09789(15) 0.23728(13) 0.0372(3) Uani 1 d . . .
C25 C 0.07604(15) -0.17286(15) 0.30977(12) 0.0372(3) Uani 1 d . . .
C26 C -0.01569(16) -0.10693(16) 0.35090(13) 0.0431(3) Uani 1 d . . .
H26A H -0.0975 -0.1557 0.3981 0.047(4) Uiso 1 calc R . .
C27 C 0.01411(16) 0.03021(16) 0.32197(13) 0.0411(3) Uani 1 d . . .
H27A H -0.0484 0.0739 0.3497 0.047(4) Uiso 1 calc R . .
C28 C 0.05655(16) -0.31282(17) 0.33910(13) 0.0428(3) Uani 1 d . . .
N29 N 0.04784(16) -0.42330(16) 0.36139(14) 0.0548(4) Uani 1 d . . .
F30 F 0.27671(10) -0.16476(9) 0.19384(10) 0.0542(3) 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 0.0033 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
_geom_angle_publ_flag
O6 C1 N2 123.97(15) . . ?
O6 C1 C5 127.57(14) . . ?
N2 C1 C5 108.46(12) . . ?
C3 N2 C1 113.19(12) . . ?
C3 N2 C8 123.27(12) . . ?
C1 N2 C8 123.52(12) . . ?
O7 C3 N2 123.96(13) . . ?
O7 C3 C4 127.77(13) . . ?
N2 C3 C4 108.27(11) . . ?
C3 C4 C5 104.63(11) . . ?
C3 C4 C16 113.24(11) . . ?
C5 C4 C16 104.53(10) . . ?
C1 C5 C21 110.60(12) . . ?
C1 C5 C4 104.50(11) . . ?
C21 C5 C4 105.81(11) . . ?
N2 C8 C9 111.86(11) . . ?
C14 C9 C10 118.39(16) . . ?
C14 C9 C8 120.93(14) . . ?
C10 C9 C8 120.66(14) . . ?
C11 C10 C9 121.02(17) . . ?
C12 C11 C10 118.72(17) . . ?
F15 C12 C11 118.90(19) . . ?
F15 C12 C13 118.66(19) . . ?
C11 C12 C13 122.44(18) . . ?
C12 C13 C14 118.15(17) . . ?
C13 C14 C9 121.25(15) . . ?
N17 C16 C22 111.74(11) . . ?
N17 C16 C4 103.90(10) . . ?
C22 C16 C4 114.66(11) . . ?
C21 N17 C16 106.39(10) . . ?
C21 N17 C18 104.07(11) . . ?
C16 N17 C18 112.48(11) . . ?
N17 C18 C19 106.79(12) . . ?
C20 C19 C18 105.62(12) . . ?
C19 C20 C21 104.18(12) . . ?
N17 C21 C5 103.24(11) . . ?
N17 C21 C20 106.19(12) . . ?
C5 C21 C20 116.43(13) . . ?
C23 C22 C27 119.21(13) . . ?
C23 C22 C16 120.11(11) . . ?
C27 C22 C16 120.67(12) . . ?
C24 C23 C22 118.69(12) . . ?
F30 C24 C23 119.45(12) . . ?
F30 C24 C25 117.51(12) . . ?
C23 C24 C25 123.04(13) . . ?
C24 C25 C26 117.90(13) . . ?
C24 C25 C28 118.74(13) . . ?
C26 C25 C28 123.35(13) . . ?
C27 C26 C25 119.75(13) . . ?
C26 C27 C22 121.36(13) . . ?
N29 C28 C25 176.86(16) . . ?
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 1.2069(19) . ?
C1 N2 1.3903(19) . ?
C1 C5 1.512(2) . ?
N2 C3 1.3785(18) . ?
N2 C8 1.4686(18) . ?
C3 O7 1.2099(17) . ?
C3 C4 1.5163(19) . ?
C4 C5 1.539(2) . ?
C4 C16 1.5665(18) . ?
C5 C21 1.5270(19) . ?
C8 C9 1.505(2) . ?
C9 C14 1.384(2) . ?
C9 C10 1.390(2) . ?
C10 C11 1.376(3) . ?
C11 C12 1.365(3) . ?
C12 F15 1.356(2) . ?
C12 C13 1.372(3) . ?
C13 C14 1.383(2) . ?
C16 N17 1.4702(17) . ?
C16 C22 1.5093(19) . ?
N17 C21 1.4702(18) . ?
N17 C18 1.4758(18) . ?
C18 C19 1.535(2) . ?
C19 C20 1.526(2) . ?
C20 C21 1.534(2) . ?
C22 C23 1.3925(19) . ?
C22 C27 1.3939(19) . ?
C23 C24 1.3708(19) . ?
C24 F30 1.3483(16) . ?
C24 C25 1.3908(19) . ?
C25 C26 1.394(2) . ?
C25 C28 1.434(2) . ?
C26 C27 1.381(2) . ?
C28 N29 1.149(2) . ?
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 179.72(15) . . . . ?
C5 C1 N2 C3 -0.76(17) . . . . ?
O6 C1 N2 C8 -2.2(2) . . . . ?
C5 C1 N2 C8 177.36(12) . . . . ?
C1 N2 C3 O7 -172.98(13) . . . . ?
C8 N2 C3 O7 8.9(2) . . . . ?
C1 N2 C3 C4 6.80(15) . . . . ?
C8 N2 C3 C4 -171.32(12) . . . . ?
O7 C3 C4 C5 170.04(14) . . . . ?
N2 C3 C4 C5 -9.73(14) . . . . ?
O7 C3 C4 C16 -76.74(17) . . . . ?
N2 C3 C4 C16 103.49(12) . . . . ?
O6 C1 C5 C21 60.6(2) . . . . ?
N2 C1 C5 C21 -118.87(13) . . . . ?
O6 C1 C5 C4 174.09(16) . . . . ?
N2 C1 C5 C4 -5.41(15) . . . . ?
C3 C4 C5 C1 8.92(14) . . . . ?
C16 C4 C5 C1 -110.35(12) . . . . ?
C3 C4 C5 C21 125.73(12) . . . . ?
C16 C4 C5 C21 6.47(14) . . . . ?
C3 N2 C8 C9 83.49(16) . . . . ?
C1 N2 C8 C9 -94.43(16) . . . . ?
N2 C8 C9 C14 -115.09(14) . . . . ?
N2 C8 C9 C10 63.46(18) . . . . ?
C14 C9 C10 C11 1.6(2) . . . . ?
C8 C9 C10 C11 -176.97(15) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 F15 178.18(16) . . . . ?
C10 C11 C12 C13 -1.4(3) . . . . ?
F15 C12 C13 C14 -177.61(14) . . . . ?
C11 C12 C13 C14 2.0(3) . . . . ?
C12 C13 C14 C9 -0.7(2) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C8 C9 C14 C13 177.56(13) . . . . ?
C3 C4 C16 N17 -95.57(13) . . . . ?
C5 C4 C16 N17 17.71(13) . . . . ?
C3 C4 C16 C22 26.67(16) . . . . ?
C5 C4 C16 C22 139.95(12) . . . . ?
C22 C16 N17 C21 -160.93(10) . . . . ?
C4 C16 N17 C21 -36.78(13) . . . . ?
C22 C16 N17 C18 85.74(13) . . . . ?
C4 C16 N17 C18 -150.11(11) . . . . ?
C21 N17 C18 C19 -32.24(16) . . . . ?
C16 N17 C18 C19 82.50(16) . . . . ?
N17 C18 C19 C20 15.13(18) . . . . ?
C18 C19 C20 C21 7.16(18) . . . . ?
C16 N17 C21 C5 41.05(14) . . . . ?
C18 N17 C21 C5 160.03(12) . . . . ?
C16 N17 C21 C20 -81.93(13) . . . . ?
C18 N17 C21 C20 37.05(14) . . . . ?
C1 C5 C21 N17 84.29(13) . . . . ?
C4 C5 C21 N17 -28.32(14) . . . . ?
C1 C5 C21 C20 -159.81(13) . . . . ?
C4 C5 C21 C20 87.57(15) . . . . ?
C19 C20 C21 N17 -27.27(16) . . . . ?
C19 C20 C21 C5 -141.51(14) . . . . ?
N17 C16 C22 C23 24.07(16) . . . . ?
C4 C16 C22 C23 -93.82(14) . . . . ?
N17 C16 C22 C27 -157.34(12) . . . . ?
C4 C16 C22 C27 84.78(15) . . . . ?
C27 C22 C23 C24 -1.77(19) . . . . ?
C16 C22 C23 C24 176.84(11) . . . . ?
C22 C23 C24 F30 179.18(12) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
F30 C24 C25 C26 -177.40(12) . . . . ?
C23 C24 C25 C26 2.1(2) . . . . ?
F30 C24 C25 C28 2.99(19) . . . . ?
C23 C24 C25 C28 -177.50(12) . . . . ?
C24 C25 C26 C27 -1.8(2) . . . . ?
C28 C25 C26 C27 177.80(12) . . . . ?
C25 C26 C27 C22 -0.3(2) . . . . ?
C23 C22 C27 C26 2.1(2) . . . . ?
C16 C22 C27 C26 -176.53(12) . . . . ?
C24 C25 C28 N29 21(3) . . . . ?
C26 C25 C28 N29 -159(3) . . . . ?
