#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/61/1506140.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_1506140
loop_
_publ_author_name
'Magnus, Philip'
'Padilla, Angela I.'
_publ_section_title
;
 Proposed biogenetic origin of secu'amamine A from allosecurinine: a model
 study to support the intermediacy of the putative aziridinium ion.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3569
_journal_page_last               3571
_journal_paper_doi               10.1021/ol061391a
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C15 H21 N2 O5.5'
_chemical_formula_weight         317.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 99.1970(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.9440(4)
_cell_length_b                   9.1830(2)
_cell_length_c                   15.9020(4)
_cell_measurement_reflns_used    3605
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3
_cell_volume                     3163.25(12)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6753
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.002
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0035(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.878
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      2.879
_refine_ls_R_factor_all          0.1616
_refine_ls_R_factor_gt           0.0964
_refine_ls_shift/su_max          0.343
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0330P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2159
_refine_ls_wR_factor_ref         0.2271
_reflns_number_gt                1973
_reflns_number_total             3599
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061391asi20060620_035539.cif
_cod_data_source_block           ap211
_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C15 H21 N2 O5.50'
_cod_database_code               1506140
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
N1 N 0.65976(11) -0.0690(3) 0.33622(16) 0.0475(7) Uani 1 1 d .
C2 C 0.70220(16) 0.0545(5) 0.3605(3) 0.0866(14) Uani 1 1 d .
H2A H 0.7439 0.0236 0.3496 0.104 Uiso 1 1 calc R
C3 C 0.68665(17) 0.1820(5) 0.3127(3) 0.0915(15) Uani 1 1 d .
H3A H 0.7197 0.2572 0.3262 0.110 Uiso 1 1 calc R
C4 C 0.67927(18) 0.1360(4) 0.2166(2) 0.0692(11) Uani 1 1 d .
H4A H 0.6606 0.2188 0.1817 0.083 Uiso 1 1 calc R
H4B H 0.7210 0.1203 0.2022 0.083 Uiso 1 1 calc R
C5 C 0.64168(17) 0.0039(5) 0.1907(2) 0.0764(12) Uani 1 1 d .
H5A H 0.6472 -0.0246 0.1323 0.092 Uiso 1 1 calc R
H5B H 0.5975 0.0267 0.1897 0.092 Uiso 1 1 calc R
C6 C 0.65986(16) -0.1224(4) 0.2507(2) 0.0634(10) Uani 1 1 d .
H6A H 0.6300 -0.2034 0.2380 0.076 Uiso 1 1 calc R
H6B H 0.7014 -0.1585 0.2445 0.076 Uiso 1 1 calc R
C7 C 0.68180(18) -0.1720(4) 0.4039(2) 0.0728(12) Uani 1 1 d .
H7A H 0.7224 -0.2126 0.3964 0.087 Uiso 1 1 calc R
H7B H 0.6521 -0.2530 0.4046 0.087 Uiso 1 1 calc R
C8 C 0.6871(2) -0.0835(5) 0.4847(3) 0.0891(14) Uani 1 1 d .
H8A H 0.7184 -0.1267 0.5295 0.107 Uiso 1 1 calc R
H8B H 0.6470 -0.0809 0.5056 0.107 Uiso 1 1 calc R
C9 C 0.70622(17) 0.0687(5) 0.4631(2) 0.0773(14) Uani 1 1 d .
H9A H 0.7486 0.0919 0.4914 0.093 Uiso 1 1 calc R
H9B H 0.6773 0.1432 0.4785 0.093 Uiso 1 1 calc R
O10 O 0.62787(9) 0.2345(3) 0.33521(19) 0.0827(9) Uani 1 1 d .
C11 C 0.61604(17) 0.3773(4) 0.3248(3) 0.0680(11) Uani 1 1 d .
O12 O 0.64979(12) 0.4614(3) 0.2986(2) 0.0895(10) Uani 1 1 d .
C13 C 0.55532(15) 0.4143(3) 0.3514(2) 0.0546(9) Uani 1 1 d .
C14 C 0.53792(17) 0.5592(3) 0.3494(2) 0.0600(10) Uani 1 1 d .
H14A H 0.5640 0.6313 0.3313 0.072 Uiso 1 1 calc R
C15 C 0.48215(17) 0.5994(4) 0.3740(2) 0.0578(9) Uani 1 1 d .
H15A H 0.4697 0.6986 0.3725 0.069 Uiso 1 1 calc R
C16 C 0.44583(14) 0.4938(3) 0.40017(19) 0.0459(8) Uani 1 1 d .
C17 C 0.46169(14) 0.3490(3) 0.4022(2) 0.0542(9) Uani 1 1 d .
H17A H 0.4356 0.2775 0.4209 0.065 Uiso 1 1 calc R
C18 C 0.51685(14) 0.3100(3) 0.3763(2) 0.0579(10) Uani 1 1 d .
H18A H 0.5282 0.2102 0.3757 0.070 Uiso 1 1 calc R
N19 N 0.38756(14) 0.5359(4) 0.42742(18) 0.0598(9) Uani 1 1 d .
O20 O 0.35560(11) 0.4414(3) 0.45223(18) 0.0750(8) Uani 1 1 d .
O21 O 0.37360(14) 0.6656(3) 0.42517(18) 0.0908(10) Uani 1 1 d .
O1W O 0.53112(15) -0.0601(3) 0.3390(3) 0.0601(8) Uani 1 1 d U
O2W O 0.4806(2) -0.0340(6) 0.4877(3) 0.0703(15) Uani 0.50 1 d PU
H2W H 0.4790 -0.0445 0.4349 0.105 Uiso 0.50 1 calc PR
H1WA H 0.575(2) -0.060(4) 0.339(2) 0.102(14) Uiso 1 1 d .
H1WB H 0.517(2) -0.064(5) 0.299(3) 0.11(3) 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'
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
C6 N1 C7 115.1(3) .
C6 N1 C2 114.2(3) .
C7 N1 C2 100.6(3) .
C3 C2 N1 114.1(3) .
C3 C2 C9 116.4(4) .
N1 C2 C9 104.7(3) .
C3 C2 H2A 107.0 .
N1 C2 H2A 107.0 .
C9 C2 H2A 107.0 .
C2 C3 O10 106.7(3) .
C2 C3 C4 106.3(4) .
O10 C3 C4 111.5(3) .
C2 C3 H3A 110.7 .
O10 C3 H3A 110.7 .
C4 C3 H3A 110.7 .
C5 C4 C3 117.1(3) .
C5 C4 H4A 108.0 .
C3 C4 H4A 108.0 .
C5 C4 H4B 108.0 .
C3 C4 H4B 108.0 .
H4A C4 H4B 107.3 .
C4 C5 C6 111.8(3) .
C4 C5 H5A 109.3 .
C6 C5 H5A 109.3 .
C4 C5 H5B 109.3 .
C6 C5 H5B 109.3 .
H5A C5 H5B 107.9 .
N1 C6 C5 107.0(3) .
N1 C6 H6A 110.3 .
C5 C6 H6A 110.3 .
N1 C6 H6B 110.3 .
C5 C6 H6B 110.3 .
H6A C6 H6B 108.6 .
N1 C7 C8 104.5(3) .
N1 C7 H7A 110.9 .
C8 C7 H7A 110.8 .
N1 C7 H7B 110.9 .
C8 C7 H7B 110.9 .
H7A C7 H7B 108.9 .
C7 C8 C9 106.9(3) .
C7 C8 H8A 110.3 .
C9 C8 H8A 110.3 .
C7 C8 H8B 110.3 .
C9 C8 H8B 110.3 .
H8A C8 H8B 108.6 .
C8 C9 C2 100.4(3) .
C8 C9 H9A 111.7 .
C2 C9 H9A 111.7 .
C8 C9 H9B 111.7 .
C2 C9 H9B 111.7 .
H9A C9 H9B 109.5 .
C11 O10 C3 116.7(3) .
O12 C11 O10 123.9(3) .
O12 C11 C13 125.6(3) .
O10 C11 C13 110.5(3) .
C18 C13 C14 119.8(3) .
C18 C13 C11 122.5(3) .
C14 C13 C11 117.8(3) .
C13 C14 C15 120.0(3) .
C13 C14 H14A 120.0 .
C15 C14 H14A 120.0 .
C16 C15 C14 118.7(3) .
C16 C15 H15A 120.7 .
C14 C15 H15A 120.7 .
C15 C16 C17 122.6(3) .
C15 C16 N19 118.9(3) .
C17 C16 N19 118.6(3) .
C16 C17 C18 118.2(3) .
C16 C17 H17A 120.9 .
C18 C17 H17A 120.9 .
C13 C18 C17 120.7(3) .
C13 C18 H18A 119.6 .
C17 C18 H18A 119.6 .
O20 N19 O21 123.0(3) .
O20 N19 C16 118.8(3) .
O21 N19 C16 118.2(3) .
H1WA O1W H1WB 108(5) .
O2W O2W H2W 109.5 5_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.446(4) .
N1 C7 1.456(4) .
N1 C2 1.479(4) .
C2 C3 1.407(5) .
C2 C9 1.626(6) .
C2 H2A 1.0000 .
C3 O10 1.474(4) .
C3 C4 1.568(6) .
C3 H3A 1.0000 .
C4 C5 1.488(5) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.515(5) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.510(5) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.514(5) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
O10 C11 1.341(4) .
C11 O12 1.191(4) .
C11 C13 1.500(5) .
C13 C18 1.376(4) .
C13 C14 1.384(4) .
C14 C15 1.393(5) .
C14 H14A 0.9500 .
C15 C16 1.363(4) .
C15 H15A 0.9500 .
C16 C17 1.373(4) .
C16 N19 1.466(4) .
C17 C18 1.387(4) .
C17 H17A 0.9500 .
C18 H18A 0.9500 .
N19 O20 1.220(3) .
N19 O21 1.228(3) .
O1W H1WA 0.97(5) .
O1W H1WB 0.66(4) .
O2W O2W 1.079(8) 5_656
O2W H2W 0.8400 .
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
O2W H2W O1W 0.84 2.05 2.779(6) 144.2 .
O1W H1WA N1 0.97(5) 1.86(5) 2.831(4) 177(4) .
O1W H1WB O1W 0.66(4) 2.28(4) 2.939(9) 176(6) 2_655
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
C6 N1 C2 C3 64.7(4)
C7 N1 C2 C3 -171.5(4)
C6 N1 C2 C9 -166.9(3)
C7 N1 C2 C9 -43.0(3)
N1 C2 C3 O10 67.0(5)
C9 C2 C3 O10 -55.2(4)
N1 C2 C3 C4 -52.1(4)
C9 C2 C3 C4 -174.4(3)
C2 C3 C4 C5 47.2(4)
O10 C3 C4 C5 -68.7(4)
C3 C4 C5 C6 -48.0(5)
C7 N1 C6 C5 -174.5(3)
C2 N1 C6 C5 -58.8(3)
C4 C5 C6 N1 50.7(4)
C6 N1 C7 C8 170.9(3)
C2 N1 C7 C8 47.7(4)
N1 C7 C8 C9 -33.9(4)
C7 C8 C9 C2 6.5(4)
C3 C2 C9 C8 149.3(3)
N1 C2 C9 C8 22.3(3)
C2 C3 O10 C11 155.0(4)
C4 C3 O10 C11 -89.3(4)
C3 O10 C11 O12 0.3(6)
C3 O10 C11 C13 -179.2(3)
O12 C11 C13 C18 176.0(4)
O10 C11 C13 C18 -4.5(5)
O12 C11 C13 C14 -3.2(6)
O10 C11 C13 C14 176.2(3)
C18 C13 C14 C15 1.1(5)
C11 C13 C14 C15 -179.6(3)
C13 C14 C15 C16 0.4(5)
C14 C15 C16 C17 -0.9(5)
C14 C15 C16 N19 179.0(3)
C15 C16 C17 C18 -0.1(5)
N19 C16 C17 C18 180.0(3)
C14 C13 C18 C17 -2.2(5)
C11 C13 C18 C17 178.6(3)
C16 C17 C18 C13 1.7(5)
C15 C16 N19 O20 -178.8(3)
C17 C16 N19 O20 1.1(4)
C15 C16 N19 O21 0.3(4)
C17 C16 N19 O21 -179.8(3)
