#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:58:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178414 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/35/4023570.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_4023570
loop_
_publ_author_name
'Christophe Pardin'
'William D. Lubell'
_publ_contact_author_address
;
      Université de Montréal
      Département de Chimie
      C.P. 6128, Succ. Centre-ville
      Montréal, Québec
      Canada, H3C 3J7
;
_publ_contact_author_email       william.lubell@umontreal.ca
_publ_contact_author_fax         '+1 514 343-7586'
_publ_contact_author_name        'Dr William Lubell'
_publ_contact_author_phone       '+1 514 343-7339'
_publ_section_title
;
 Cinnamoyl Inhibitors of Tissue Transglutaminase
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5766
_journal_page_last               5775
_journal_paper_doi               10.1021/jo8004843
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C15 H10 N4 O4, C2 H F3 O2'
_chemical_formula_sum            'C17 H11 F3 N4 O6'
_chemical_formula_weight         424.30
_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                96.2560(10)
_cell_angle_beta                 107.4280(10)
_cell_angle_gamma                96.4560(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7137(2)
_cell_length_b                   9.7911(2)
_cell_length_c                   12.1711(2)
_cell_measurement_reflns_used    4454
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      4.60
_cell_volume                     861.55(3)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker AXS Smart 4K/Platform'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         anode
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6422
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         3.85
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         77
_exptl_absorpt_coefficient_mu    1.287
_exptl_absorpt_correction_T_max  0.9400
_exptl_absorpt_correction_T_min  0.9300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0398
_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)+(0.0792P)²+0.1541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                2653
_reflns_number_total             3034
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo8004843-File001.cif
_cod_data_source_block           keilr2
_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.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (31
time).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (44 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023570
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
N1 N 0.46613(18) -0.00822(12) 0.73319(10) 0.0216(3) Uani 1 1 d . . .
N2 N 0.61969(18) 0.09022(12) 0.76633(10) 0.0226(3) Uani 1 1 d . . .
N3 N 0.71800(18) 0.06685(12) 0.86806(10) 0.0210(3) Uani 1 1 d . . .
O3 O 0.87442(15) 0.14219(11) 0.92493(8) 0.0265(3) Uani 1 1 d . . .
C1 C 0.4719(2) -0.09490(14) 0.81681(12) 0.0212(3) Uani 1 1 d . . .
C2 C 0.3526(2) -0.20897(14) 0.82476(13) 0.0234(3) Uani 1 1 d . . .
H2 H 0.2404 -0.2444 0.7646 0.028 Uiso 1 1 calc R . .
C3 C 0.4079(2) -0.26694(15) 0.92565(13) 0.0249(3) Uani 1 1 d . . .
H3 H 0.3305 -0.3442 0.9352 0.030 Uiso 1 1 calc R . .
C4 C 0.5748(2) -0.21611(15) 1.01511(12) 0.0245(3) Uani 1 1 d . . .
H4 H 0.6062 -0.2599 1.0828 0.029 Uiso 1 1 calc R . .
C5 C 0.6938(2) -0.10415(14) 1.00674(12) 0.0225(3) Uani 1 1 d . . .
H5 H 0.8072 -0.0695 1.0660 0.027 Uiso 1 1 calc R . .
C6 C 0.6354(2) -0.04590(14) 0.90526(12) 0.0205(3) Uani 1 1 d . . .
C11 C 0.3280(2) -0.01476(14) 0.62307(12) 0.0223(3) Uani 1 1 d . . .
O11 O 0.20016(16) -0.10807(10) 0.59524(9) 0.0288(3) Uani 1 1 d . . .
C12 C 0.3622(2) 0.09480(15) 0.55567(12) 0.0244(3) Uani 1 1 d . . .
H12 H 0.4677 0.1642 0.5872 0.029 Uiso 1 1 calc R . .
C13 C 0.2457(2) 0.09718(14) 0.45052(12) 0.0227(3) Uani 1 1 d . . .
H13 H 0.1417 0.0261 0.4220 0.027 Uiso 1 1 calc R . .
C14 C 0.2653(2) 0.20090(14) 0.37532(12) 0.0213(3) Uani 1 1 d . . .
C15 C 0.1328(2) 0.19083(15) 0.26630(12) 0.0234(3) Uani 1 1 d . . .
H15 H 0.0316 0.1175 0.2430 0.028 Uiso 1 1 calc R . .
C16 C 0.1461(2) 0.28593(15) 0.19124(12) 0.0253(3) Uani 1 1 d . . .
H16 H 0.0553 0.2791 0.1174 0.030 Uiso 1 1 calc R . .
C17 C 0.2958(2) 0.39068(15) 0.22743(13) 0.0251(4) Uani 1 1 d . . .
N17 N 0.3173(2) 0.48993(14) 0.14769(12) 0.0317(3) Uani 1 1 d . . .
C18 C 0.4304(2) 0.40460(16) 0.33472(13) 0.0273(4) Uani 1 1 d . . .
H18 H 0.5314 0.4780 0.3572 0.033 Uiso 1 1 calc R . .
C19 C 0.4145(2) 0.30950(15) 0.40813(12) 0.0255(4) Uani 1 1 d . . .
H19 H 0.5058 0.3176 0.4820 0.031 Uiso 1 1 calc R . .
O18 O 0.4450(2) 0.58687(12) 0.18497(11) 0.0433(3) Uani 1 1 d . . .
O19 O 0.20745(19) 0.46973(12) 0.04891(10) 0.0393(3) Uani 1 1 d . . .
O21 O 0.94122(17) 0.32555(11) 0.79791(9) 0.0309(3) Uani 1 1 d . . .
H21 H 0.9262 0.2649 0.8394 0.046 Uiso 1 1 calc R . .
O22 O 1.09062(17) 0.17400(11) 0.72274(9) 0.0318(3) Uani 1 1 d . . .
C20 C 1.0265(2) 0.27954(15) 0.72723(12) 0.0244(3) Uani 1 1 d . . .
C21 C 1.0349(2) 0.38422(15) 0.64224(13) 0.0260(4) Uani 1 1 d . . .
F21 F 1.11248(16) 0.51033(9) 0.69997(9) 0.0424(3) Uani 1 1 d . . .
F22 F 1.13066(15) 0.34778(10) 0.57333(8) 0.0387(3) Uani 1 1 d . . .
F23 F 0.86648(15) 0.39461(11) 0.57521(9) 0.0429(3) 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 0.0181 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'
F F 0.0727 0.0534 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . . 111.09(12) y
N2 N1 C11 . . . 120.52(11) y
C1 N1 C11 . . . 128.36(13) y
N3 N2 N1 . . . 105.46(11) y
O3 N3 N2 . . . 121.71(11) y
O3 N3 C6 . . . 125.65(12) y
N2 N3 C6 . . . 112.64(12) y
C6 C1 N1 . . . 105.37(12) y
C6 C1 C2 . . . 121.09(13) y
N1 C1 C2 . . . 133.53(14) y
C3 C2 C1 . . . 115.71(14) y
C3 C2 H2 . . . 122.1 ?
C1 C2 H2 . . . 122.1 ?
C2 C3 C4 . . . 122.68(14) y
C2 C3 H3 . . . 118.7 ?
C4 C3 H3 . . . 118.7 ?
C5 C4 C3 . . . 121.62(13) y
C5 C4 H4 . . . 119.2 ?
C3 C4 H4 . . . 119.2 ?
C4 C5 C6 . . . 115.08(14) y
C4 C5 H5 . . . 122.5 ?
C6 C5 H5 . . . 122.5 ?
C1 C6 C5 . . . 123.81(13) y
C1 C6 N3 . . . 105.43(12) y
C5 C6 N3 . . . 130.76(14) y
O11 C11 N1 . . . 117.91(13) y
O11 C11 C12 . . . 127.42(13) y
N1 C11 C12 . . . 114.66(13) y
C13 C12 C11 . . . 120.08(14) y
C13 C12 H12 . . . 120 ?
C11 C12 H12 . . . 120 ?
C12 C13 C14 . . . 125.00(14) y
C12 C13 H13 . . . 117.5 ?
C14 C13 H13 . . . 117.5 ?
C15 C14 C19 . . . 118.58(13) y
C15 C14 C13 . . . 119.11(13) y
C19 C14 C13 . . . 122.31(13) y
C16 C15 C14 . . . 121.32(14) y
C16 C15 H15 . . . 119.3 ?
C14 C15 H15 . . . 119.3 ?
C17 C16 C15 . . . 117.89(14) y
C17 C16 H16 . . . 121.1 ?
C15 C16 H16 . . . 121.1 ?
C16 C17 C18 . . . 122.74(14) y
C16 C17 N17 . . . 119.08(14) y
C18 C17 N17 . . . 118.16(15) y
O19 N17 O18 . . . 124.49(13) y
O19 N17 C17 . . . 118.00(14) y
O18 N17 C17 . . . 117.51(14) y
C19 C18 C17 . . . 118.53(15) y
C19 C18 H18 . . . 120.7 ?
C17 C18 H18 . . . 120.7 ?
C18 C19 C14 . . . 120.94(14) y
C18 C19 H19 . . . 119.5 ?
C14 C19 H19 . . . 119.5 ?
C20 O21 H21 . . . 109.5 ?
O22 C20 O21 . . . 128.84(14) y
O22 C20 C21 . . . 121.87(14) y
O21 C20 C21 . . . 109.29(13) y
F22 C21 F21 . . . 107.61(12) y
F22 C21 F23 . . . 107.90(12) y
F21 C21 F23 . . . 107.40(13) y
F22 C21 C20 . . . 112.09(13) y
F21 C21 C20 . . . 110.89(12) y
F23 C21 C20 . . . 110.76(13) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . . 1.3664(17) y
N1 C1 . . 1.3885(17) y
N1 C11 . . 1.4304(19) y
N2 N3 . . 1.3034(17) y
N3 O3 . . 1.2912(16) y
N3 C6 . . 1.3976(18) y
C1 C6 . . 1.385(2) y
C1 C2 . . 1.396(2) y
C2 C3 . . 1.380(2) y
C2 H2 . . 0.95 ?
C3 C4 . . 1.410(2) y
C3 H3 . . 0.95 ?
C4 C5 . . 1.382(2) y
C4 H4 . . 0.95 ?
C5 C6 . . 1.390(2) y
C5 H5 . . 0.95 ?
C11 O11 . . 1.2050(18) y
C11 C12 . . 1.467(2) y
C12 C13 . . 1.330(2) y
C12 H12 . . 0.95 ?
C13 C14 . . 1.4639(19) y
C13 H13 . . 0.95 ?
C14 C15 . . 1.397(2) y
C14 C19 . . 1.404(2) y
C15 C16 . . 1.390(2) y
C15 H15 . . 0.95 ?
C16 C17 . . 1.382(2) y
C16 H16 . . 0.95 ?
C17 C18 . . 1.385(2) y
C17 N17 . . 1.4764(18) y
N17 O19 . . 1.2260(19) y
N17 O18 . . 1.2268(19) y
C18 C19 . . 1.379(2) y
C18 H18 . . 0.95 ?
C19 H19 . . 0.95 ?
O21 C20 . . 1.3024(18) y
O21 H21 . . 0.84 ?
O22 C20 . . 1.1977(19) y
C20 C21 . . 1.543(2) y
C21 F22 . . 1.3199(18) y
C21 F21 . . 1.3302(17) y
C21 F23 . . 1.333(2) y
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
O21 H21 O3 0.84 1.76 2.5986(14) 174.7 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 N3 . . . . -0.54(15) ?
C11 N1 N2 N3 . . . . -178.80(12) ?
N1 N2 N3 O3 . . . . 179.95(11) ?
N1 N2 N3 C6 . . . . 0.21(15) ?
N2 N1 C1 C6 . . . . 0.66(16) ?
C11 N1 C1 C6 . . . . 178.74(13) ?
N2 N1 C1 C2 . . . . -179.78(15) ?
C11 N1 C1 C2 . . . . -1.7(3) ?
C6 C1 C2 C3 . . . . 0.6(2) ?
N1 C1 C2 C3 . . . . -178.91(15) ?
C1 C2 C3 C4 . . . . -0.6(2) ?
C2 C3 C4 C5 . . . . 0.0(2) ?
C3 C4 C5 C6 . . . . 0.7(2) ?
N1 C1 C6 C5 . . . . 179.71(13) ?
C2 C1 C6 C5 . . . . 0.1(2) ?
N1 C1 C6 N3 . . . . -0.50(15) ?
C2 C1 C6 N3 . . . . 179.87(13) ?
C4 C5 C6 C1 . . . . -0.7(2) ?
C4 C5 C6 N3 . . . . 179.54(14) ?
O3 N3 C6 C1 . . . . -179.54(13) ?
N2 N3 C6 C1 . . . . 0.19(16) ?
O3 N3 C6 C5 . . . . 0.2(2) ?
N2 N3 C6 C5 . . . . 179.97(14) ?
N2 N1 C11 O11 . . . . 176.06(12) ?
C1 N1 C11 O11 . . . . -1.9(2) ?
N2 N1 C11 C12 . . . . -3.07(19) ?
C1 N1 C11 C12 . . . . 179.01(13) ?
O11 C11 C12 C13 . . . . -0.8(3) ?
N1 C11 C12 C13 . . . . 178.21(14) ?
C11 C12 C13 C14 . . . . -179.95(13) ?
C12 C13 C14 C15 . . . . 179.75(15) ?
C12 C13 C14 C19 . . . . 0.7(2) ?
C19 C14 C15 C16 . . . . -0.3(2) ?
C13 C14 C15 C16 . . . . -179.40(13) ?
C14 C15 C16 C17 . . . . 0.5(2) ?
C15 C16 C17 C18 . . . . -0.5(2) ?
C15 C16 C17 N17 . . . . 177.64(13) ?
C16 C17 N17 O19 . . . . -4.8(2) ?
C18 C17 N17 O19 . . . . 173.37(14) ?
C16 C17 N17 O18 . . . . 175.51(14) ?
C18 C17 N17 O18 . . . . -6.3(2) ?
C16 C17 C18 C19 . . . . 0.3(2) ?
N17 C17 C18 C19 . . . . -177.85(13) ?
C17 C18 C19 C14 . . . . -0.1(2) ?
C15 C14 C19 C18 . . . . 0.1(2) ?
C13 C14 C19 C18 . . . . 179.17(14) ?
O22 C20 C21 F22 . . . . -4.7(2) ?
O21 C20 C21 F22 . . . . 175.76(12) ?
O22 C20 C21 F21 . . . . -125.01(16) ?
O21 C20 C21 F21 . . . . 55.47(17) ?
O22 C20 C21 F23 . . . . 115.85(16) ?
O21 C20 C21 F23 . . . . -63.68(16) ?
