#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/37/1503774.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_1503774
loop_
_publ_author_name
'Jones, Raymond C. F.'
'Yau, Sze Chak'
'Iley, James N.'
'Smith, Janet E.'
'Dickson, James'
'Elsegood, Mark R. J.'
'McKee, Vickie'
'Coles, Simon J.'
_publ_section_title
;
 Synthesis of the pyoverdin chromophore by a biomimetic oxidative
 cyclization.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1519
_journal_page_last               1522
_journal_paper_doi               10.1021/ol802804c
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C13 H19 N2 O2, C F3 O3 S'
_chemical_formula_sum            'C14 H19 F3 N2 O5 S'
_chemical_formula_weight         384.37
_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                103.85(3)
_cell_angle_beta                 99.40(3)
_cell_angle_gamma                92.57(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2689(15)
_cell_length_b                   7.8204(16)
_cell_length_c                   15.025(3)
_cell_measurement_reflns_used    4127
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     815.0(3)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.872
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans to fill Ewald Sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_sigmaI/netI    0.1342
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7049
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.001(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                1782
_reflns_number_total             3230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802804c_si_003.cif
_cod_data_source_block           15a
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1503774
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
C14 C 0.6629(6) 0.4193(5) 0.3845(3) 0.0339(9) Uani 1 1 d .
O3 O 0.6112(4) 0.4829(4) 0.22310(19) 0.0463(8) Uani 1 1 d .
O4 O 0.7678(4) 0.7144(3) 0.3546(2) 0.0446(8) Uani 1 1 d .
O5 O 0.9286(4) 0.4582(4) 0.2978(2) 0.0489(8) Uani 1 1 d .
F1 F 0.6481(4) 0.2454(3) 0.35258(18) 0.0580(8) Uani 1 1 d .
F2 F 0.4938(3) 0.4656(4) 0.39672(19) 0.0645(8) Uani 1 1 d .
F3 F 0.7740(3) 0.4562(3) 0.46747(16) 0.0542(7) Uani 1 1 d .
S1 S 0.75336(13) 0.53149(12) 0.30550(7) 0.0304(3) Uani 1 1 d .
C1 C 0.2140(5) -0.4819(4) 0.0560(3) 0.0276(9) Uani 1 1 d .
C2 C 0.3075(5) -0.4010(5) -0.0050(3) 0.0273(9) Uani 1 1 d .
H2 H 0.3200 -0.4704 -0.0645 0.033 Uiso 1 1 calc R
C3 C 0.3744(5) -0.2343(4) 0.0210(2) 0.0261(9) Uani 1 1 d .
H3 H 0.4388 -0.1912 -0.0205 0.031 Uiso 1 1 calc R
C4 C 0.3577(5) -0.1066(4) 0.1106(3) 0.0240(8) Uani 1 1 d .
C5 C 0.6952(5) -0.0540(5) 0.1631(3) 0.0360(10) Uani 1 1 d .
H5A H 0.7041 -0.0876 0.2223 0.054 Uiso 1 1 calc R
H5B H 0.7984 0.0343 0.1675 0.054 Uiso 1 1 calc R
H5C H 0.7025 -0.1587 0.1131 0.054 Uiso 1 1 calc R
C6 C 0.3245(5) -0.2009(4) 0.1854(2) 0.0232(8) Uani 1 1 d .
H6 H 0.4455 -0.2456 0.2084 0.028 Uiso 1 1 calc R
C7 C 0.1781(5) -0.3623(4) 0.1447(2) 0.0277(9) Uani 1 1 d .
H7A H 0.1767 -0.4317 0.1918 0.033 Uiso 1 1 calc R
H7B H 0.0526 -0.3193 0.1328 0.033 Uiso 1 1 calc R
C8 C 0.1990(5) 0.0076(4) 0.0932(2) 0.0241(8) Uani 1 1 d .
H8A H 0.0789 -0.0672 0.0723 0.029 Uiso 1 1 calc R
H8B H 0.2190 0.0658 0.0434 0.029 Uiso 1 1 calc R
C9 C 0.1903(5) 0.1471(4) 0.1820(2) 0.0258(9) Uani 1 1 d .
H9A H 0.3000 0.2350 0.1960 0.031 Uiso 1 1 calc R
H9B H 0.0761 0.2096 0.1725 0.031 Uiso 1 1 calc R
C10 C 0.1883(5) 0.0674(4) 0.2633(2) 0.0231(8) Uani 1 1 d .
C11 C 0.0995(5) 0.0943(5) 0.4158(3) 0.0324(9) Uani 1 1 d .
H11A H -0.0165 0.0158 0.4062 0.039 Uiso 1 1 calc R
H11B H 0.0976 0.1966 0.4692 0.039 Uiso 1 1 calc R
C12 C 0.2678(5) -0.0041(5) 0.4353(3) 0.0343(10) Uani 1 1 d .
H12A H 0.2585 -0.0551 0.4888 0.041 Uiso 1 1 calc R
H12B H 0.3823 0.0786 0.4518 0.041 Uiso 1 1 calc R
C13 C 0.2813(5) -0.1504(5) 0.3509(2) 0.0296(9) Uani 1 1 d .
H13A H 0.4025 -0.2019 0.3611 0.036 Uiso 1 1 calc R
H13B H 0.1799 -0.2450 0.3418 0.036 Uiso 1 1 calc R
N1 N 0.2659(4) -0.0818(4) 0.2661(2) 0.0237(7) Uani 1 1 d .
N2 N 0.1113(4) 0.1549(4) 0.3318(2) 0.0286(8) Uani 1 1 d .
O1 O 0.1541(3) -0.6382(3) 0.03313(18) 0.0340(7) Uani 1 1 d .
O2 O 0.5213(3) 0.0186(3) 0.14325(17) 0.0292(6) Uani 1 1 d .
H2A H 0.062(4) 0.250(4) 0.323(2) 0.003(8) Uiso 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
F1 C14 F2 107.0(3)
F1 C14 F3 106.6(3)
F2 C14 F3 108.3(3)
F1 C14 S1 112.0(3)
F2 C14 S1 111.0(3)
F3 C14 S1 111.6(3)
O5 S1 O4 114.83(19)
O5 S1 O3 116.02(19)
O4 S1 O3 114.65(18)
O5 S1 C14 102.45(17)
O4 S1 C14 103.15(17)
O3 S1 C14 103.11(18)
O1 C1 C2 121.9(3)
O1 C1 C7 120.5(3)
C2 C1 C7 117.4(3)
C3 C2 C1 121.4(3)
C2 C3 C4 125.4(3)
O2 C4 C3 110.6(3)
O2 C4 C8 103.8(2)
C3 C4 C8 109.6(3)
O2 C4 C6 110.8(3)
C3 C4 C6 112.0(3)
C8 C4 C6 109.8(3)
N1 C6 C4 112.5(3)
N1 C6 C7 109.7(3)
C4 C6 C7 111.2(3)
C1 C7 C6 113.9(3)
C4 C8 C9 110.0(3)
C10 C9 C8 111.7(3)
N2 C10 N1 122.2(3)
N2 C10 C9 116.9(3)
N1 C10 C9 120.9(3)
N2 C11 C12 107.7(3)
C11 C12 C13 110.4(3)
N1 C13 C12 110.7(3)
C10 N1 C6 124.2(3)
C10 N1 C13 120.7(3)
C6 N1 C13 114.8(3)
C10 N2 C11 123.2(3)
C5 O2 C4 116.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C14 F1 1.322(4)
C14 F2 1.325(4)
C14 F3 1.329(4)
C14 S1 1.820(4)
O3 S1 1.438(3)
O4 S1 1.434(3)
O5 S1 1.431(3)
C1 O1 1.226(4)
C1 C2 1.464(5)
C1 C7 1.503(5)
C2 C3 1.314(5)
C3 C4 1.499(5)
C4 O2 1.445(4)
C4 C8 1.517(5)
C4 C6 1.529(4)
C5 O2 1.425(4)
C6 N1 1.478(4)
C6 C7 1.548(5)
C8 C9 1.520(5)
C9 C10 1.499(4)
C10 N2 1.314(4)
C10 N1 1.326(4)
C11 N2 1.464(5)
C11 C12 1.500(5)
C12 C13 1.510(5)
C13 N1 1.485(4)
