#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:08:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180289 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/03/7150375.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_7150375
loop_
_publ_author_name
'Horsley, Helen T.'
'Holmes, Andrew B.'
'Davies, John E.'
'Goodman, Jonathan M.'
'Silva, María A'
'Pascu, Sofia I.'
'Collins, Ian'
_publ_section_title
;
 Investigation of conjugate addition/intramolecular nitrone dipolar
 cycloadditions and their use in the synthesis of dendrobatid alkaloid
 precursors.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1258
_journal_page_last               1265
_journal_paper_doi               10.1039/b402307b
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C13 H17 N3 O'
_chemical_formula_sum            'C13 H17 N3 O'
_chemical_formula_weight         231.30
_chemical_name_systematic
;
?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 97.128(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5820(9)
_cell_length_b                   9.9509(6)
_cell_length_c                   7.9189(5)
_cell_measurement_reflns_used    5714
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.00
_cell_volume                     1218.37(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3327
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         4.45
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.0(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1725
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0309
_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)+(0.0219P)²+0.4026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                1648
_reflns_number_total             1725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b402307b.txt
_cod_data_source_block           ah0304
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7150375
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'
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 0.90248(8) 0.07278(13) 0.94283(17) 0.0331(3) Uani 1 1 d . . .
N1 N 0.86782(9) 0.20849(15) 0.97281(18) 0.0259(4) Uani 1 1 d . . .
N2 N 0.75815(13) 0.2104(2) 1.3599(2) 0.0488(5) Uani 1 1 d . . .
N3 N 1.02205(13) 0.2993(2) 0.4945(2) 0.0488(5) Uani 1 1 d . . .
C1 C 0.73834(13) 0.1034(2) 1.0563(2) 0.0323(5) Uani 1 1 d . . .
H1A H 0.6760 0.0871 1.0215 0.039 Uiso 1 1 calc R . .
H1B H 0.7683 0.0154 1.0605 0.039 Uiso 1 1 calc R . .
C2 C 0.77362(11) 0.19252(18) 0.9232(2) 0.0259(4) Uani 1 1 d . . .
H2 H 0.7641 0.1459 0.8106 0.031 Uiso 1 1 calc R . .
C3 C 0.72976(12) 0.3291(2) 0.9056(2) 0.0305(4) Uani 1 1 d . . .
H3A H 0.6668 0.3171 0.8732 0.037 Uiso 1 1 calc R . .
H3B H 0.7385 0.3767 1.0162 0.037 Uiso 1 1 calc R . .
C4 C 0.76685(12) 0.4124(2) 0.7715(2) 0.0317(4) Uani 1 1 d . . .
H4A H 0.7383 0.5014 0.7610 0.038 Uiso 1 1 calc R . .
H4B H 0.7565 0.3667 0.6597 0.038 Uiso 1 1 calc R . .
C5 C 0.86347(12) 0.42974(19) 0.8234(2) 0.0295(4) Uani 1 1 d . . .
H5A H 0.8723 0.4884 0.9251 0.035 Uiso 1 1 calc R . .
H5B H 0.8885 0.4762 0.7304 0.035 Uiso 1 1 calc R . .
C6 C 0.91284(11) 0.29847(18) 0.8636(2) 0.0261(4) Uani 1 1 d . . .
C7 C 0.92244(12) 0.20625(19) 0.7092(2) 0.0289(4) Uani 1 1 d . . .
H7 H 0.8639 0.1874 0.6468 0.035 Uiso 1 1 calc R . .
C8 C 0.95628(13) 0.0795(2) 0.8067(3) 0.0339(5) Uani 1 1 d . . .
H8 H 0.9486 -0.0020 0.7325 0.041 Uiso 1 1 calc R . .
C9 C 1.05008(13) 0.0956(2) 0.8841(3) 0.0414(5) Uani 1 1 d . . .
H9A H 1.0864 0.1175 0.7937 0.050 Uiso 1 1 calc R . .
H9B H 1.0713 0.0103 0.9384 0.050 Uiso 1 1 calc R . .
C10 C 1.05700(13) 0.2076(2) 1.0162(3) 0.0406(5) Uani 1 1 d . . .
H10A H 1.1184 0.2340 1.0433 0.049 Uiso 1 1 calc R . .
H10B H 1.0369 0.1735 1.1220 0.049 Uiso 1 1 calc R . .
C11 C 1.00373(12) 0.3313(2) 0.9551(2) 0.0346(5) Uani 1 1 d . . .
H11A H 1.0358 0.3831 0.8765 0.042 Uiso 1 1 calc R . .
H11B H 0.9975 0.3893 1.0543 0.042 Uiso 1 1 calc R . .
C12 C 0.74999(13) 0.1639(2) 1.2265(3) 0.0345(5) Uani 1 1 d . . .
C13 C 0.97891(13) 0.2577(2) 0.5893(3) 0.0357(5) Uani 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
C8 O1 N1 109.45(13) . . ?
C2 N1 C6 115.85(13) . . ?
C2 N1 O1 103.20(12) . . ?
C6 N1 O1 104.39(12) . . ?
C12 C1 C2 112.37(16) . . ?
N1 C2 C3 110.37(14) . . ?
N1 C2 C1 107.98(14) . . ?
C3 C2 C1 112.68(15) . . ?
C4 C3 C2 110.28(15) . . ?
C3 C4 C5 108.83(15) . . ?
C4 C5 C6 114.53(15) . . ?
N1 C6 C5 112.05(14) . . ?
N1 C6 C11 109.12(14) . . ?
C5 C6 C11 109.00(15) . . ?
N1 C6 C7 101.63(13) . . ?
C5 C6 C7 115.90(14) . . ?
C11 C6 C7 108.82(15) . . ?
C13 C7 C8 114.58(16) . . ?
C13 C7 C6 115.38(16) . . ?
C8 C7 C6 98.66(14) . . ?
O1 C8 C9 108.72(16) . . ?
O1 C8 C7 102.57(14) . . ?
C9 C8 C7 111.62(17) . . ?
C8 C9 C10 109.65(17) . . ?
C9 C10 C11 112.47(16) . . ?
C10 C11 C6 114.11(17) . . ?
N2 C12 C1 179.2(2) . . ?
N3 C13 C7 178.9(2) . . ?
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 C8 1.447(2) . ?
O1 N1 1.4844(19) . ?
N1 C2 1.480(2) . ?
N1 C6 1.481(2) . ?
N2 C12 1.145(3) . ?
N3 C13 1.145(3) . ?
C1 C12 1.467(3) . ?
C1 C2 1.531(3) . ?
C2 C3 1.520(3) . ?
C3 C4 1.517(3) . ?
C4 C5 1.520(3) . ?
C5 C6 1.529(3) . ?
C6 C11 1.544(3) . ?
C6 C7 1.550(2) . ?
C7 C13 1.465(3) . ?
C7 C8 1.537(3) . ?
C8 C9 1.522(3) . ?
C9 C10 1.523(3) . ?
C10 C11 1.530(3) . ?
