#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023972.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_4023972
loop_
_publ_author_name
'Frank Surup'
'Oliver Wagner'
'Jan von Frieling'
'Michael Schleicher'
'Stefanie Oess'
'Peter Müller'
'Stephanie Grond'
_publ_section_title
;
 The Iromycins, a New Family of Pyridone Metabolites from
 Streptomyces sp. I. Structure, NOS Inhibitory Activity,
 and Biosynthesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5085
_journal_page_last               5090
_journal_paper_doi               10.1021/jo0703303
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C20 H32 N O3.5'
_chemical_formula_weight         342.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           82
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.7063(19)
_cell_length_b                   13.7063(19)
_cell_length_c                   22.371(5)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      23.0
_cell_measurement_theta_min      2.8
_cell_volume                     4202.6(12)
_computing_cell_refinement       'Siemens SAINT (V. 5.00, Siemens 1998)'
_computing_data_collection       'Siemens SMART (V. 4.202, Siemens 1996)'
_computing_data_reduction        'Siemens SAINT (V. 5.00, Siemens 1998)'
_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      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Stoe-Siemens-Huber four circle diffractometer'
_diffrn_measurement_method       'omega and phi 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  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            24444
_diffrn_reflns_theta_full        23.24
_diffrn_reflns_theta_max         23.24
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         1554
_refine_ls_number_restraints     205
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0628
_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)+(0.1288P)²+2.5435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1812
_reflns_number_gt                1414
_reflns_number_total             1554
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0703303si20070216_044415.cif
_cod_data_source_block           tapir
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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_formula_sum        'C20 H32 N O3.50'
_cod_database_code               4023972
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2398(2) 0.2483(3) 0.15549(16) 0.0493(9) Uani 1 1 d DU . .
H1O H 1.295(2) 0.222(4) 0.160(3) 0.059 Uiso 1 1 d D . .
O2 O 1.1301(2) -0.0033(2) 0.28571(17) 0.0509(9) Uani 1 1 d U . .
O3 O 0.4285(2) 0.2275(2) 0.14263(15) 0.0427(8) Uani 1 1 d DU . .
H3O H 0.458(4) 0.265(3) 0.167(2) 0.051 Uiso 1 1 d D . .
N1 N 1.0326(3) 0.1168(3) 0.25283(19) 0.0426(10) Uani 1 1 d DU . .
H1N H 0.991(3) 0.085(4) 0.274(2) 0.051 Uiso 1 1 d D . .
C1 C 1.0097(3) 0.1987(4) 0.2213(2) 0.0460(11) Uani 1 1 d U . .
C2 C 1.0797(3) 0.2422(4) 0.1878(3) 0.0470(11) Uani 1 1 d U . .
C3 C 1.1753(3) 0.2004(3) 0.1889(2) 0.0408(11) Uani 1 1 d U . .
C4 C 1.1965(3) 0.1185(3) 0.2210(2) 0.0394(10) Uani 1 1 d U . .
C5 C 1.1220(3) 0.0738(3) 0.2549(2) 0.0406(11) Uani 1 1 d U . .
C10 C 0.9048(3) 0.2298(4) 0.2273(3) 0.0517(13) Uani 1 1 d U . .
H10A H 0.9010 0.3020 0.2263 0.062 Uiso 1 1 calc R . .
H10B H 0.8790 0.2075 0.2663 0.062 Uiso 1 1 calc R . .
C11 C 0.8430(3) 0.1882(4) 0.1777(3) 0.0539(13) Uani 1 1 d U . .
H11 H 0.8440 0.1193 0.1733 0.065 Uiso 1 1 calc R . .
C12 C 0.7869(3) 0.2376(5) 0.1392(3) 0.0578(14) Uani 1 1 d U . .
C13 C 0.7766(4) 0.3462(5) 0.1384(3) 0.0653(15) Uani 1 1 d U . .
H13A H 0.8144 0.3744 0.1713 0.098 Uiso 1 1 calc R . .
H13B H 0.7077 0.3637 0.1430 0.098 Uiso 1 1 calc R . .
H13C H 0.8011 0.3717 0.1003 0.098 Uiso 1 1 calc R . .
C14 C 0.7276(4) 0.1829(6) 0.0930(3) 0.0724(17) Uani 1 1 d U . .
H14A H 0.7432 0.2081 0.0527 0.087 Uiso 1 1 calc R . .
H14B H 0.7452 0.1128 0.0942 0.087 Uiso 1 1 calc R . .
C15 C 0.6202(4) 0.1940(5) 0.1046(3) 0.0620(15) Uani 1 1 d U . .
H15 H 0.5957 0.1673 0.1409 0.074 Uiso 1 1 calc R . .
C16 C 0.5572(4) 0.2369(5) 0.0695(3) 0.0655(16) Uani 1 1 d U . .
H16 H 0.5815 0.2623 0.0329 0.079 Uiso 1 1 calc R . .
C17 C 0.4507(4) 0.2497(5) 0.0812(2) 0.0649(16) Uani 1 1 d U . .
C18 C 0.3922(5) 0.1763(9) 0.0451(3) 0.107(3) Uani 1 1 d U . .
H18A H 0.4141 0.1101 0.0549 0.160 Uiso 1 1 calc R . .
H18B H 0.4020 0.1885 0.0024 0.160 Uiso 1 1 calc R . .
H18C H 0.3228 0.1829 0.0548 0.160 Uiso 1 1 calc R . .
C19 C 0.4222(5) 0.3561(7) 0.0679(4) 0.106(3) Uani 1 1 d U . .
H19A H 0.4621 0.4000 0.0923 0.159 Uiso 1 1 calc R . .
H19B H 0.3531 0.3659 0.0774 0.159 Uiso 1 1 calc R . .
H19C H 0.4332 0.3700 0.0254 0.159 Uiso 1 1 calc R . .
C20 C 1.0611(4) 0.3296(5) 0.1489(3) 0.0659(16) Uani 1 1 d U . .
H20A H 0.9980 0.3590 0.1607 0.079 Uiso 1 1 calc R . .
H20B H 1.1126 0.3786 0.1566 0.079 Uiso 1 1 calc R . .
C21 C 1.0583(7) 0.3090(8) 0.0830(4) 0.111(3) Uani 1 1 d U . .
H21A H 1.1203 0.2776 0.0710 0.133 Uiso 1 1 calc R . .
H21B H 1.0046 0.2628 0.0745 0.133 Uiso 1 1 calc R . .
C22 C 1.0447(10) 0.3939(14) 0.0491(7) 0.219(10) Uani 1 1 d U . .
H22A H 1.0427 0.3770 0.0065 0.329 Uiso 1 1 calc R . .
H22B H 1.0988 0.4391 0.0564 0.329 Uiso 1 1 calc R . .
H22C H 0.9831 0.4250 0.0606 0.329 Uiso 1 1 calc R . .
C40 C 1.2974(3) 0.0725(4) 0.2199(3) 0.0481(12) Uani 1 1 d U . .
H40A H 1.3156 0.0577 0.1785 0.072 Uiso 1 1 calc R . .
H40B H 1.2968 0.0122 0.2434 0.072 Uiso 1 1 calc R . .
H40C H 1.3448 0.1181 0.2371 0.072 Uiso 1 1 calc R . .
O1S O 1.1211(13) 0.0476(10) -0.0009(7) 0.136(4) Uani 0.50 1 d PU A -1
H1OS H 1.0747 0.0079 -0.0038 0.204 Uiso 0.50 1 calc PR A -1
C1S C 1.1381(10) 0.0633(10) 0.0518(7) 0.074(3) Uani 0.50 1 d PU A -1
H1S1 H 1.1501 0.1339 0.0579 0.089 Uiso 0.50 1 calc PR A -1
H1S2 H 1.1975 0.0273 0.0640 0.089 Uiso 0.50 1 calc PR A -1
C2S C 1.0309(9) 0.0230(9) 0.0990(6) 0.078(3) Uani 0.50 1 d PU A -1
H2S1 H 1.0447 0.0362 0.1412 0.116 Uiso 0.50 1 calc PR A -1
H2S2 H 1.0200 -0.0471 0.0934 0.116 Uiso 0.50 1 calc PR A -1
H2S3 H 0.9724 0.0589 0.0868 0.116 Uiso 0.50 1 calc PR A -1
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'
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
C5 N1 C1 125.6(4) . . ?
C2 C1 N1 119.0(4) . . ?
C2 C1 C10 126.9(5) . . ?
N1 C1 C10 114.1(4) . . ?
C1 C2 C3 117.6(5) . . ?
C1 C2 C20 123.4(4) . . ?
C3 C2 C20 119.0(4) . . ?
O1 C3 C4 124.1(4) . . ?
O1 C3 C2 113.6(4) . . ?
C4 C3 C2 122.3(4) . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 C40 121.8(4) . . ?
C5 C4 C40 119.2(4) . . ?
O2 C5 N1 117.3(4) . . ?
O2 C5 C4 126.2(4) . . ?
N1 C5 C4 116.5(4) . . ?
C1 C10 C11 111.3(5) . . ?
C12 C11 C10 127.3(5) . . ?
C11 C12 C13 124.4(6) . . ?
C11 C12 C14 119.8(6) . . ?
C13 C12 C14 115.8(5) . . ?
C15 C14 C12 111.0(5) . . ?
C16 C15 C14 126.1(6) . . ?
C15 C16 C17 126.3(5) . . ?
O3 C17 C16 110.4(4) . . ?
O3 C17 C18 104.9(5) . . ?
C16 C17 C18 110.1(6) . . ?
O3 C17 C19 109.4(6) . . ?
C16 C17 C19 109.0(6) . . ?
C18 C17 C19 113.0(6) . . ?
C21 C20 C2 115.0(6) . . ?
C22 C21 C20 112.3(12) . . ?
O1S C1S C2S 109.8(12) . . ?
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
O1 C3 1.331(6) . ?
O2 C5 1.267(6) . ?
O3 C17 1.439(7) . ?
N1 C5 1.360(6) . ?
N1 C1 1.363(7) . ?
C1 C2 1.355(7) . ?
C1 C10 1.506(7) . ?
C2 C3 1.430(7) . ?
C2 C20 1.504(8) . ?
C3 C4 1.364(7) . ?
C4 C5 1.412(7) . ?
C4 C40 1.519(7) . ?
C10 C11 1.507(9) . ?
C11 C12 1.339(8) . ?
C12 C13 1.495(9) . ?
C12 C14 1.513(9) . ?
C14 C15 1.503(8) . ?
C15 C16 1.307(8) . ?
C16 C17 1.494(8) . ?
C17 C18 1.519(11) . ?
C17 C19 1.538(11) . ?
C20 C21 1.500(12) . ?
C21 C22 1.402(16) . ?
O1S C1S 1.220(19) . ?
C1S C2S 1.89(2) . ?
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
O1 H1O O3 0.84(2) 1.87(4) 2.619(4) 147(6) 1_655
O3 H3O O2 0.85(2) 1.87(2) 2.693(5) 165(6) 7_565
N1 H1N O2 0.86(2) 2.02(3) 2.817(5) 154(5) 2_755
O1S H1OS O1S 0.84 1.81 2.52(2) 141.7 3_665
