#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/37/1503717.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_1503717
loop_
_publ_author_name
'Cummings, Christopher G.'
'Ross, Nathan T.'
'Katt, William P.'
'Hamilton, Andrew D.'
_publ_section_title
;
 Synthesis and biological evaluation of a 5-6-5 imidazole-phenyl-thiazole
 based alpha-helix mimetic.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              25
_journal_page_last               28
_journal_paper_doi               10.1021/ol8022962
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C17 H16 F3 N3 O2 S'
_chemical_formula_weight         383.39
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.21(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.159(2)
_cell_length_b                   15.012(3)
_cell_length_c                   11.545(2)
_cell_measurement_temperature    173(2)
_cell_volume                     1720.0(7)
_computing_cell_refinement       Denzo
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Denzo
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7216
_diffrn_reflns_theta_full        29.02
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9543
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1492
_reflns_number_gt                2854
_reflns_number_total             4532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8022962_si_003.cif
_cod_data_source_block           cc01
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1720.0(6)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1503717
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
S1 S 0.21829(6) 0.16849(4) 0.31231(5) 0.03511(18) Uani 1 1 d .
N1 N -0.07403(17) 0.13422(12) -0.51317(17) 0.0291(4) Uani 1 1 d .
H1 H -0.138(3) 0.096(2) -0.587(3) 0.063(8) Uiso 1 1 d .
N2 N 0.04058(16) 0.19047(10) -0.32179(16) 0.0248(4) Uani 1 1 d .
N3 N 0.27817(16) 0.32928(11) 0.28516(16) 0.0270(4) Uani 1 1 d .
C1 C -0.0336(2) 0.21777(14) -0.5301(2) 0.0325(5) Uani 1 1 d .
H1A H -0.0529 0.2451 -0.6110 0.039 Uiso 1 1 calc R
C2 C 0.0379(2) 0.25351(14) -0.4115(2) 0.0306(5) Uani 1 1 d .
H2A H 0.0789 0.3107 -0.3924 0.037 Uiso 1 1 calc R
C3 C -0.02898(19) 0.11803(13) -0.3872(2) 0.0254(4) Uani 1 1 d .
C4 C -0.0522(2) 0.03505(13) -0.3312(2) 0.0320(5) Uani 1 1 d .
H4A H -0.1055 -0.0064 -0.4017 0.048 Uiso 1 1 calc R
H4B H -0.1010 0.0489 -0.2813 0.048 Uiso 1 1 calc R
H4C H 0.0346 0.0077 -0.2737 0.048 Uiso 1 1 calc R
C5 C 0.09493(18) 0.20698(13) -0.18406(19) 0.0237(4) Uani 1 1 d .
C6 C 0.07207(19) 0.28921(12) -0.1447(2) 0.0246(4) Uani 1 1 d .
H6A H 0.0247 0.3332 -0.2086 0.029 Uiso 1 1 calc R
C7 C 0.11673(19) 0.30937(12) -0.0138(2) 0.0234(4) Uani 1 1 d .
C8 C 0.18699(18) 0.24263(13) 0.07906(19) 0.0238(4) Uani 1 1 d .
C9 C 0.2121(2) 0.16091(13) 0.0372(2) 0.0280(5) Uani 1 1 d .
H9A H 0.2612 0.1168 0.1003 0.034 Uiso 1 1 calc R
C10 C 0.16748(19) 0.14186(13) -0.0937(2) 0.0273(5) Uani 1 1 d .
H10A H 0.1860 0.0860 -0.1207 0.033 Uiso 1 1 calc R
C11 C 0.0826(2) 0.39915(14) 0.0211(2) 0.0298(5) Uani 1 1 d .
H11A H 0.0346 0.4346 -0.0582 0.045 Uiso 1 1 calc R
H11B H 0.1657 0.4299 0.0802 0.045 Uiso 1 1 calc R
H11C H 0.0252 0.3914 0.0641 0.045 Uiso 1 1 calc R
C12 C 0.23058(19) 0.25577(13) 0.21984(19) 0.0254(4) Uani 1 1 d .
C13 C 0.2830(2) 0.23605(15) 0.4461(2) 0.0345(5) Uani 1 1 d .
H13A H 0.2991 0.2181 0.5308 0.041 Uiso 1 1 calc R
C14 C 0.3084(2) 0.31810(14) 0.4156(2) 0.0308(5) Uani 1 1 d .
C15 C 0.3625(2) 0.39581(17) 0.5059(2) 0.0427(6) Uani 1 1 d .
H15A H 0.3795 0.3779 0.5937 0.064 Uiso 1 1 calc R
H15B H 0.2966 0.4444 0.4754 0.064 Uiso 1 1 calc R
H15C H 0.4468 0.4160 0.5077 0.064 Uiso 1 1 calc R
C16 C -0.3009(2) -0.02185(15) -0.6998(2) 0.0331(5) Uani 1 1 d .
O2 O -0.23740(17) -0.07144(12) -0.60798(17) 0.0526(5) Uani 1 1 d .
O1 O -0.26809(17) 0.05093(11) -0.72740(17) 0.0453(4) Uani 1 1 d .
C17 C -0.4420(2) -0.05423(14) -0.7982(2) 0.0318(5) Uani 1 1 d .
F1 F -0.53780(13) 0.00518(10) -0.81607(16) 0.0615(5) Uani 1 1 d .
F2 F -0.47836(15) -0.12971(10) -0.76133(14) 0.0522(4) Uani 1 1 d .
F3 F -0.44959(14) -0.07127(9) -0.91504(12) 0.0459(4) 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 0.0033 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'
S S 0.1246 0.1234 '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
C13 S1 C12 89.32(11)
H1 N1 C3 126.4(16)
H1 N1 C1 123.4(16)
C3 N1 C1 109.78(18)
C3 N2 C2 108.68(17)
C3 N2 C5 126.90(17)
C2 N2 C5 123.98(16)
C12 N3 C14 110.84(17)
C2 C1 N1 107.45(19)
C1 C2 N2 106.71(18)
N1 C3 N2 107.38(18)
N1 C3 C4 125.36(18)
N2 C3 C4 127.26(19)
C6 C5 C10 121.02(19)
C6 C5 N2 118.00(17)
C10 C5 N2 120.98(17)
C5 C6 C7 121.62(18)
C6 C7 C8 117.95(17)
C6 C7 C11 118.50(17)
C8 C7 C11 123.49(18)
C9 C8 C7 119.39(18)
C9 C8 C12 118.71(18)
C7 C8 C12 121.86(17)
C10 C9 C8 122.02(19)
C9 C10 C5 117.95(18)
N3 C12 C8 126.12(17)
N3 C12 S1 114.14(15)
C8 C12 S1 119.74(15)
C14 C13 S1 111.08(17)
C13 C14 N3 114.61(19)
C13 C14 C15 126.7(2)
N3 C14 C15 118.69(19)
O2 C16 O1 129.7(2)
O2 C16 C17 116.1(2)
O1 C16 C17 114.3(2)
F1 C17 F3 107.14(18)
F1 C17 F2 106.10(18)
F3 C17 F2 105.69(17)
F1 C17 C16 112.34(17)
F3 C17 C16 112.13(18)
F2 C17 C16 112.95(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C13 1.707(2)
S1 C12 1.735(2)
N1 H1 1.01(3)
N1 C3 1.326(3)
N1 C1 1.377(3)
N2 C3 1.349(2)
N2 C2 1.394(3)
N2 C5 1.441(3)
N3 C12 1.305(3)
N3 C14 1.395(3)
C1 C2 1.342(3)
C3 C4 1.479(3)
C5 C6 1.379(3)
C5 C10 1.388(3)
C6 C7 1.391(3)
C7 C8 1.414(3)
C7 C11 1.505(3)
C8 C9 1.393(3)
C8 C12 1.481(3)
C9 C10 1.388(3)
C13 C14 1.346(3)
C14 C15 1.496(3)
C16 O2 1.222(3)
C16 O1 1.239(3)
C16 C17 1.540(3)
C17 F1 1.334(2)
C17 F3 1.337(2)
C17 F2 1.337(3)
