#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:09:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180290 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/04/7150428.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_7150428
loop_
_publ_author_name
'Neumann, Helfried'
'Strübing, Dirk'
'Lalk, Michael'
'Klaus, Stefan'
'Hübner, Sandra'
'Spannenberg, Anke'
'Lindequist, Ulrike'
'Beller, Matthias'
_publ_section_title
;
 Synthesis and antimicrobial activity of N-analogous corollosporines.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1365
_journal_page_last               1375
_journal_paper_doi               10.1039/b517101f
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C17 H24 N2 O3'
_chemical_formula_weight         304.38
_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                96.61(3)
_cell_angle_beta                 97.73(3)
_cell_angle_gamma                99.99(3)
_cell_formula_units_Z            2
_cell_length_a                   8.917(2)
_cell_length_b                   8.949(2)
_cell_length_c                   10.953(2)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      4
_cell_volume                     844.3(3)
_computing_cell_refinement       STOE-CELL
_computing_data_collection       STOE-EXPOSE
_computing_data_reduction        STOE-INTEGRATE
_computing_molecular_graphics    XP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  STOE-IPDSI
_diffrn_measurement_method       'laser scanned imaging plate'
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4524
_diffrn_reflns_theta_full        24.26
_diffrn_reflns_theta_max         24.26
_diffrn_reflns_theta_min         1.90
_diffrn_standards_interval_time  360
_diffrn_standards_number         50-200
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      0.857
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0522
_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)+(0.0846P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                1344
_reflns_number_total             2510
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b517101f.txt
_cod_data_source_block           ks231
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150428
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C16A C 0.3947(10) -0.3221(6) 0.6269(6) 0.126(3) Uiso 0.70 1 d PD A 1
H16A H 0.2963 -0.2929 0.6026 0.151 Uiso 0.70 1 calc PR A 1
H16B H 0.4482 -0.3241 0.5554 0.151 Uiso 0.70 1 calc PR A 1
C17A C 0.3674(9) -0.4796(8) 0.6655(8) 0.145(3) Uiso 0.70 1 d PD A 1
H17A H 0.3075 -0.5517 0.5973 0.218 Uiso 0.70 1 calc PR A 1
H17B H 0.3126 -0.4783 0.7352 0.218 Uiso 0.70 1 calc PR A 1
H17C H 0.4646 -0.5092 0.6886 0.218 Uiso 0.70 1 calc PR A 1
C16B C 0.3598(12) -0.3323(16) 0.6656(19) 0.148(9) Uiso 0.30 1 d PD A 2
H16C H 0.3126 -0.3937 0.7227 0.178 Uiso 0.30 1 calc PR A 2
H16D H 0.2815 -0.2944 0.6141 0.178 Uiso 0.30 1 calc PR A 2
C17B C 0.4555(19) -0.417(2) 0.5894(14) 0.129(5) Uiso 0.30 1 d PD A 2
H17D H 0.3905 -0.5056 0.5390 0.193 Uiso 0.30 1 calc PR A 2
H17E H 0.5338 -0.4489 0.6440 0.193 Uiso 0.30 1 calc PR A 2
H17F H 0.5031 -0.3509 0.5368 0.193 Uiso 0.30 1 calc PR A 2
C1 C 0.8345(3) 0.3224(3) 0.7967(2) 0.0561(8) Uani 1 1 d . . .
C2 C 0.9796(3) 0.2587(3) 0.8274(2) 0.0529(7) Uani 1 1 d . . .
C3 C 1.0764(3) 0.2112(3) 0.7486(3) 0.0581(8) Uani 1 1 d . . .
C4 C 1.1976(4) 0.1475(4) 0.8009(3) 0.0708(9) Uani 1 1 d . . .
H4 H 1.2641 0.1127 0.7505 0.085 Uiso 1 1 calc R . .
C5 C 1.2208(4) 0.1351(4) 0.9264(3) 0.0743(10) Uani 1 1 d . . .
H5 H 1.3009 0.0895 0.9582 0.089 Uiso 1 1 calc R . .
C6 C 1.1283(4) 0.1884(4) 1.0053(3) 0.0675(9) Uani 1 1 d . . .
H6 H 1.1455 0.1821 1.0900 0.081 Uiso 1 1 calc R . .
C7 C 1.0088(3) 0.2518(3) 0.9534(2) 0.0550(8) Uani 1 1 d . . .
C8 C 0.8952(4) 0.3225(3) 1.0141(3) 0.0611(8) Uani 1 1 d . . .
C9 C 1.1123(4) 0.1727(4) 0.5255(3) 0.0723(9) Uani 1 1 d . . .
C10 C 1.0624(5) 0.2258(5) 0.4044(3) 0.0932(12) Uani 1 1 d . . .
H10A H 0.9954 0.2974 0.4170 0.140 Uiso 1 1 calc R . .
H10B H 1.0084 0.1394 0.3452 0.140 Uiso 1 1 calc R . .
H10C H 1.1513 0.2746 0.3734 0.140 Uiso 1 1 calc R . .
C11 C 0.6657(4) 0.4290(4) 0.9446(3) 0.0793(10) Uani 1 1 d . . .
H11A H 0.6142 0.4492 0.8672 0.119 Uiso 1 1 calc R . .
H11B H 0.6983 0.5230 1.0011 0.119 Uiso 1 1 calc R . .
H11C H 0.5962 0.3581 0.9801 0.119 Uiso 1 1 calc R . .
C12 C 0.7029(3) 0.2065(3) 0.7159(3) 0.0632(9) Uani 1 1 d D . .
H12A H 0.6152 0.2560 0.6996 0.076 Uiso 1 1 calc R . .
H12B H 0.7347 0.1778 0.6366 0.076 Uiso 1 1 calc R . .
C13 C 0.6516(4) 0.0627(3) 0.7705(3) 0.0726(9) Uani 1 1 d D . .
H13A H 0.7415 0.0213 0.7991 0.087 Uiso 1 1 calc R . .
H13B H 0.6035 0.0889 0.8424 0.087 Uiso 1 1 calc R . .
C14 C 0.5397(3) -0.0590(3) 0.6802(3) 0.0740(9) Uani 1 1 d D A .
H14A H 0.5872 -0.0829 0.6076 0.089 Uiso 1 1 calc R . .
H14B H 0.4491 -0.0177 0.6531 0.089 Uiso 1 1 calc R . .
C15 C 0.4890(5) -0.2055(4) 0.7315(4) 0.1124(15) Uani 1 1 d D . .
H15A H 0.4277 -0.1870 0.7965 0.135 Uiso 1 1 calc R A 1
H15B H 0.5783 -0.2432 0.7671 0.135 Uiso 1 1 calc R A 1
N1 N 0.7992(3) 0.3633(3) 0.9227(2) 0.0606(7) Uani 1 1 d . . .
N2 N 1.0503(3) 0.2326(3) 0.6227(2) 0.0666(8) Uani 1 1 d . . .
O1 O 0.8576(3) 0.4518(3) 0.7338(2) 0.0668(6) Uani 1 1 d . . .
O2 O 0.8891(3) 0.3451(3) 1.12614(19) 0.0751(7) Uani 1 1 d . . .
O3 O 1.1968(3) 0.0825(4) 0.5360(2) 0.0997(9) Uani 1 1 d . . .
HN2 H 0.995(4) 0.293(4) 0.613(3) 0.068(11) Uiso 1 1 d . . .
HO1 H 0.937(4) 0.528(5) 0.775(3) 0.107(15) 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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17A C16A C15 111.1(5) . . ?
C17B C16B C15 97.0(10) . . ?
O1 C1 N1 111.4(2) . . ?
O1 C1 C2 113.3(2) . . ?
N1 C1 C2 100.7(2) . . ?
O1 C1 C12 106.4(2) . . ?
N1 C1 C12 111.7(2) . . ?
C2 C1 C12 113.5(3) . . ?
C7 C2 C3 120.9(3) . . ?
C7 C2 C1 110.1(3) . . ?
C3 C2 C1 129.0(2) . . ?
C2 C3 C4 117.0(2) . . ?
C2 C3 N2 119.1(3) . . ?
C4 C3 N2 123.9(3) . . ?
C5 C4 C3 121.1(3) . . ?
C6 C5 C4 121.6(3) . . ?
C5 C6 C7 117.1(3) . . ?
C6 C7 C2 122.1(3) . . ?
C6 C7 C8 129.5(3) . . ?
C2 C7 C8 108.4(3) . . ?
O2 C8 N1 125.6(3) . . ?
O2 C8 C7 127.6(3) . . ?
N1 C8 C7 106.8(2) . . ?
O3 C9 N2 122.6(3) . . ?
O3 C9 C10 123.2(3) . . ?
N2 C9 C10 114.2(3) . . ?
C13 C12 C1 115.2(2) . . ?
C14 C13 C12 113.5(3) . . ?
C13 C14 C15 114.7(3) . . ?
C14 C15 C16B 123.7(10) . . ?
C14 C15 C16A 108.5(4) . . ?
C16B C15 C16A 21.6(8) . . ?
C8 N1 C11 123.4(3) . . ?
C8 N1 C1 113.7(2) . . ?
C11 N1 C1 122.7(2) . . ?
C9 N2 C3 128.9(3) . . ?
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
C16A C17A 1.507(2) . ?
C16A C15 1.507(2) . ?
C16B C17B 1.507(2) . ?
C16B C15 1.507(2) . ?
C1 O1 1.414(3) . ?
C1 N1 1.476(4) . ?
C1 C2 1.515(4) . ?
C1 C12 1.524(4) . ?
C2 C7 1.380(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.394(4) . ?
C3 N2 1.408(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.374(4) . ?
C6 C7 1.378(4) . ?
C7 C8 1.475(4) . ?
C8 O2 1.231(3) . ?
C8 N1 1.353(4) . ?
C9 O3 1.201(4) . ?
C9 N2 1.363(4) . ?
C9 C10 1.497(4) . ?
C11 N1 1.451(4) . ?
C12 C13 1.507(2) . ?
C13 C14 1.507(2) . ?
C14 C15 1.507(2) . ?
