#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/87/2008774.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2008774
loop_
_publ_author_name
'Batey, Robert A.'
'MacKay, D. Bruce'
'Lough, Alan J.'
_publ_section_title
;
 3-Butyl-5-hydroxy-4-iodohexahydropyrrolo[1,2-c][1,3]oxazin-1-one
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1362
_journal_page_last               1363
_journal_paper_doi               10.1107/S0108270199004497
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C11 H18 I N O3'
_chemical_formula_weight         339.16
_chemical_name_systematic
;
 3-Butyl-5-hydroxy-4-iodo-hexahydro-pyrolo[1,2-c][1,3]
 oxazin-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.672(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.0869(2)
_cell_length_b                   13.7875(5)
_cell_length_c                   9.4187(6)
_cell_measurement_reflns_used    17165
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      4.08
_cell_volume                     2544.95(19)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa CCD server software (Nonius, 1997)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.046
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17165
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         4.16
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_T_max  0.7046
_exptl_absorpt_correction_T_min  0.5197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Denzo-SMN; Ottwinowski & Minor, 1997)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block cut from needle'
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.848
_refine_diff_density_min         -0.658
_refine_ls_extinction_coef       0.00045(11)
_refine_ls_extinction_method     'SHELXTL/PC (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0273P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0624
_reflns_number_gt                3762
_reflns_number_total             4470
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1542.cif
_cod_data_source_block           k98135rr
_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 2.4.1 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 (12 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 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 (12
times).

'_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 (3
times).

'_geom_torsion_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 (2 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2008774
_cod_database_fobs_code          2008774
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1A 0.309270(10) 0.258929(15) -0.05132(2) 0.02274(8) Uani d . 1 . . I
N1A 0.51521(12) 0.19279(19) -0.0967(2) 0.0193(5) Uani d . 1 . . N
C1A 0.51134(16) 0.1028(2) -0.1528(3) 0.0191(6) Uani d . 1 . . C
O1A 0.44431(12) 0.36817(18) -0.2305(2) 0.0247(5) Uani d . 1 . . O
H1AA 0.4483(18) 0.422(3) -0.251(4) 0.030(11) Uiso d . 1 . . H
O2A 0.55751(11) 0.06515(15) -0.2003(2) 0.0229(5) Uani d . 1 . . O
O3A 0.45427(10) 0.05090(15) -0.1584(2) 0.0214(5) Uani d . 1 . . O
C3A 0.39438(15) 0.0904(2) -0.1119(3) 0.0194(7) Uani d . 1 . . C
H3AA 0.3976 0.0745 -0.0070 0.023 Uiso calc R 1 . . H
C4A 0.39307(14) 0.1991(2) -0.1312(3) 0.0164(6) Uani d . 1 . . C
H4AA 0.3867 0.2146 -0.2371 0.020 Uiso calc R 1 . . H
C5A 0.45893(15) 0.2437(2) -0.0496(3) 0.0173(6) Uani d . 1 . . C
H5AA 0.4634 0.2345 0.0574 0.021 Uiso calc R 1 . . H
C6A 0.47265(16) 0.3497(2) -0.0811(3) 0.0203(7) Uani d . 1 . . C
H6AA 0.4535 0.3946 -0.0168 0.024 Uiso calc R 1 . . H
C7A 0.55064(16) 0.3539(2) -0.0477(3) 0.0215(7) Uani d . 1 . . C
H7AA 0.5667 0.4107 -0.0952 0.026 Uiso calc R 1 . . H
H7AB 0.5695 0.3576 0.0585 0.026 Uiso calc R 1 . . H
C8A 0.57130(16) 0.2591(2) -0.1105(3) 0.0213(7) Uani d . 1 . . C
H8AA 0.5741 0.2670 -0.2135 0.026 Uiso calc R 1 . . H
H8AB 0.6157 0.2354 -0.0538 0.026 Uiso calc R 1 . . H
C9A 0.33396(16) 0.0381(2) -0.2041(3) 0.0225(7) Uani d . 1 . . C
H9AA 0.3345 0.0478 -0.3080 0.027 Uiso calc R 1 . . H
H9AB 0.2915 0.0677 -0.1869 0.027 Uiso calc R 1 . . H
C10A 0.33272(16) -0.0704(2) -0.1735(3) 0.0226(7) Uani d . 1 . . C
H10C 0.3340 -0.0805 -0.0689 0.027 Uiso calc R 1 . . H
H10D 0.3739 -0.1009 -0.1955 0.027 Uiso calc R 1 . . H
C11A 0.26911(18) -0.1194(3) -0.2641(4) 0.0329(8) Uani d . 1 . . C
H11C 0.2281 -0.0853 -0.2477 0.039 Uiso calc R 1 . . H
H11D 0.2697 -0.1131 -0.3685 0.039 Uiso calc R 1 . . H
C12A 0.26394(18) -0.2253(3) -0.2282(4) 0.0316(8) Uani d . 1 . . C
H12D 0.2230 -0.2530 -0.2910 0.047 Uiso calc R 1 . . H
H12E 0.2611 -0.2320 -0.1261 0.047 Uiso calc R 1 . . H
H12F 0.3044 -0.2596 -0.2442 0.047 Uiso calc R 1 . . H
I1B 0.141834(11) 0.366340(16) 0.05835(2) 0.02811(8) Uani d . 1 . . I
N1B -0.03683(13) 0.1961(2) 0.0841(3) 0.0239(6) Uani d . 1 . . N
C1B -0.01299(16) 0.1097(3) 0.1356(3) 0.0255(7) Uani d . 1 . . C
O1B -0.00675(12) 0.37183(18) 0.2535(2) 0.0301(5) Uani d . 1 . . O
H1BA 0.011(2) 0.435(4) 0.263(5) 0.073(15) Uiso d . 1 . . H
O2B -0.04642(11) 0.05076(17) 0.1860(2) 0.0308(5) Uani d . 1 . . O
O3B 0.05169(11) 0.08622(16) 0.1292(2) 0.0250(5) Uani d . 1 . . O
C3B 0.09636(16) 0.1537(2) 0.0751(3) 0.0233(7) Uani d . 1 . . C
H3BA 0.0875 0.1494 -0.0334 0.028 Uiso calc R 1 . . H
C4B 0.07820(16) 0.2549(2) 0.1192(3) 0.0218(7) Uani d . 1 . . C
H4BA 0.0833 0.2565 0.2272 0.026 Uiso calc R 1 . . H
C5B 0.00478(16) 0.2762(2) 0.0481(3) 0.0242(7) Uani d . 1 . . C
H5BA -0.0004 0.2796 -0.0598 0.029 Uiso calc R 1 . . H
C6B -0.02871(16) 0.3653(2) 0.1000(3) 0.0239(7) Uani d . 1 . . C
H6BA -0.0193 0.4261 0.0499 0.029 Uiso calc R 1 . . H
C7B -0.10378(17) 0.3369(3) 0.0603(4) 0.0314(8) Uani d . 1 . . C
H7BA -0.1227 0.3453 -0.0452 0.038 Uiso calc R 1 . . H
H7BB -0.1308 0.3764 0.1150 0.038 Uiso calc R 1 . . H
C8B -0.10396(17) 0.2304(3) 0.1033(4) 0.0317(8) Uani d . 1 . . C
H8BA -0.1082 0.2232 0.2056 0.038 Uiso calc R 1 . . H
H8BB -0.1416 0.1948 0.0390 0.038 Uiso calc R 1 . . H
C9B 0.16791(16) 0.1200(2) 0.1394(3) 0.0256(7) Uani d . 1 . . C
H9BA 0.1755 0.1218 0.2468 0.031 Uiso calc R 1 . . H
H9BB 0.2005 0.1659 0.1104 0.031 Uiso calc R 1 . . H
C10B 0.18332(18) 0.0174(3) 0.0923(3) 0.0321(8) Uani d . 1 . . C
H10A 0.1520 -0.0291 0.1240 0.038 Uiso calc R 1 . . H
H10B 0.1748 0.0149 -0.0152 0.038 Uiso calc R 1 . . H
C11B 0.25641(18) -0.0128(3) 0.1557(4) 0.0374(9) Uani d . 1 . . C
H11A 0.2874 0.0378 0.1327 0.045 Uiso calc R 1 . . H
H11B 0.2660 -0.0736 0.1080 0.045 Uiso calc R 1 . . H
C12B 0.27223(18) -0.0285(3) 0.3195(4) 0.0379(9) Uani d . 1 . . C
H12A 0.3202 -0.0471 0.3527 0.057 Uiso calc R 1 . . H
H12B 0.2430 -0.0802 0.3433 0.057 Uiso calc R 1 . . H
H12C 0.2637 0.0316 0.3680 0.057 Uiso calc R 1 . . H
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'
I I -0.4742 1.8119 '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_publ_flag
C1A N1A C8A 121.0(2) ?
C1A N1A C5A 125.0(3) y
C8A N1A C5A 112.4(2) ?
O2A C1A O3A 117.8(3) y
O2A C1A N1A 123.4(3) ?
O3A C1A N1A 118.9(3) y
C1A O3A C3A 122.5(2) ?
O3A C3A C4A 109.0(2) ?
O3A C3A C9A 104.9(2) ?
C4A C3A C9A 114.4(2) ?
C5A C4A C3A 110.7(2) ?
C5A C4A I1A 109.33(18) ?
C3A C4A I1A 109.43(18) ?
N1A C5A C4A 107.2(2) ?
N1A C5A C6A 102.3(2) ?
C4A C5A C6A 117.8(2) ?
O1A C6A C5A 108.3(2) ?
O1A C6A C7A 111.5(2) ?
C5A C6A C7A 102.5(2) ?
C8A C7A C6A 103.9(2) ?
N1A C8A C7A 102.6(2) ?
C3A C9A C10A 113.8(3) ?
C9A C10A C11A 112.0(3) ?
C12A C11A C10A 113.2(3) ?
C1B N1B C5B 125.3(3) ?
C1B N1B C8B 120.4(3) ?
C5B N1B C8B 111.6(3) ?
O2B C1B N1B 123.6(3) ?
O2B C1B O3B 118.4(3) ?
N1B C1B O3B 118.0(3) ?
C1B O3B C3B 122.2(3) ?
O3B C3B C9B 105.6(2) ?
O3B C3B C4B 106.6(2) ?
C9B C3B C4B 116.0(3) ?
C5B C4B C3B 109.0(3) ?
C5B C4B I1B 108.8(2) ?
C3B C4B I1B 112.9(2) ?
N1B C5B C4B 107.6(2) ?
N1B C5B C6B 102.5(2) ?
C4B C5B C6B 118.0(3) ?
O1B C6B C7B 109.7(3) ?
O1B C6B C5B 108.4(2) ?
C7B C6B C5B 101.3(3) ?
C6B C7B C8B 104.0(3) ?
N1B C8B C7B 102.7(3) ?
C3B C9B C10B 113.8(3) ?
C11B C10B C9B 112.2(3) ?
C10B C11B C12B 114.1(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1A C4A . 2.153(3) y
N1A C1A . 1.344(4) y
N1A C8A . 1.479(4) y
N1A C5A . 1.479(4) y
C1A O2A . 1.230(4) ?
C1A O3A . 1.343(4) y
O1A C6A . 1.421(3) y
O3A C3A . 1.473(3) ?
C3A C4A . 1.508(4) ?
C3A C9A . 1.511(4) ?
C4A C5A . 1.508(4) ?
C5A C6A . 1.528(4) ?
C6A C7A . 1.530(4) ?
C7A C8A . 1.530(4) ?
C9A C10A . 1.525(4) ?
C10A C11A . 1.530(4) ?
C11A C12A . 1.506(5) ?
I1B C4B . 2.155(3) y
N1B C1B . 1.335(4) y
N1B C5B . 1.469(4) y
N1B C8B . 1.477(4) y
C1B O2B . 1.215(4) ?
C1B O3B . 1.353(4) y
O1B C6B . 1.418(4) y
O3B C3B . 1.460(4) ?
C3B C9B . 1.505(4) ?
C3B C4B . 1.523(4) ?
C4B C5B . 1.509(4) ?
C5B C6B . 1.532(4) ?
C6B C7B . 1.523(5) ?
C7B C8B . 1.523(5) ?
C9B C10B . 1.534(5) ?
C10B C11B . 1.517(5) ?
C11B C12B . 1.520(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1A H1A O2A 2_654 0.77(4) 2.02(4) 2.791(3) 170(4)
O1B H1B O2B 2 0.94(5) 1.77(5) 2.699(3) 170(4)
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_publ_flag
C8A N1A C1A O2A 10.3(4) ?
C5A N1A C1A O2A 174.7(3) ?
C8A N1A C1A O3A -169.5(2) ?
C5A N1A C1A O3A -5.0(4) ?
O2A C1A O3A C3A -176.7(2) ?
N1A C1A O3A C3A 3.0(4) ?
C1A O3A C3A C4A 27.5(3) ?
C1A O3A C3A C9A 150.5(2) ?
O3A C3A C4A C5A -56.0(3) ?
C9A C3A C4A C5A -173.1(2) ?
O3A C3A C4A I1A -176.54(16) ?
C9A C3A C4A I1A 66.3(3) ?
C1A N1A C5A C4A -23.8(4) ?
C8A N1A C5A C4A 141.9(2) ?
C1A N1A C5A C6A -148.4(3) ?
C8A N1A C5A C6A 17.3(3) ?
C3A C4A C5A N1A 53.3(3) ?
I1A C4A C5A N1A 173.92(17) ?
C3A C4A C5A C6A 167.9(2) ?
I1A C4A C5A C6A -71.5(3) ?
N1A C5A C6A O1A 83.0(3) ?
C4A C5A C6A O1A -34.2(3) ?
N1A C5A C6A C7A -34.9(3) ?
C4A C5A C6A C7A -152.2(2) ?
O1A C6A C7A C8A -74.9(3) ?
C5A C6A C7A C8A 40.7(3) ?
C1A N1A C8A C7A 173.9(2) ?
C5A N1A C8A C7A 7.7(3) ?
C6A C7A C8A N1A -29.6(3) ?
O3A C3A C9A C10A 65.7(3) ?
C4A C3A C9A C10A -174.8(2) ?
C3A C9A C10A C11A 177.4(3) ?
C9A C10A C11A C12A -175.8(3) y
C5B N1B C1B O2B 167.8(3) ?
C8B N1B C1B O2B 8.0(5) ?
C5B N1B C1B O3B -13.1(4) ?
C8B N1B C1B O3B -173.0(3) ?
O2B C1B O3B C3B -177.9(3) ?
N1B C1B O3B C3B 3.1(4) ?
C1B O3B C3B C9B 157.7(3) ?
C1B O3B C3B C4B 33.8(3) ?
O3B C3B C4B C5B -61.6(3) ?
C9B C3B C4B C5B -178.8(2) ?
O3B C3B C4B I1B 177.29(17) ?
C9B C3B C4B I1B 60.1(3) ?
C1B N1B C5B C4B -16.3(4) ?
C8B N1B C5B C4B 145.1(3) ?
C1B N1B C5B C6B -141.3(3) ?
C8B N1B C5B C6B 20.0(3) ?
C3B C4B C5B N1B 53.0(3) ?
I1B C4B C5B N1B 176.59(18) ?
C3B C4B C5B C6B 168.3(3) ?
I1B C4B C5B C6B -68.2(3) ?
N1B C5B C6B O1B 78.1(3) ?
C4B C5B C6B O1B -39.8(4) ?
N1B C5B C6B C7B -37.3(3) ?
C4B C5B C6B C7B -155.2(3) ?
O1B C6B C7B C8B -72.6(3) ?
C5B C6B C7B C8B 41.8(3) ?
C1B N1B C8B C7B 168.2(3) ?
C5B N1B C8B C7B 5.8(3) ?
C6B C7B C8B N1B -29.7(3) ?
O3B C3B C9B C10B 61.8(3) ?
C4B C3B C9B C10B 179.6(3) ?
C3B C9B C10B C11B 178.3(3) ?
C9B C10B C11B C12B 68.8(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21105758
