#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/73/1507356.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_1507356
loop_
_publ_author_name
'Chao, Wenchun'
'Waldman, Jacob H.'
'Weinreb, Steven M.'
_publ_section_title
;
 Studies of intramolecular cyclizations of N-acyliminium ions derived from
 acyclic ketones: unanticipated stereochemical and structural results.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              2915
_journal_page_last               2918
_journal_paper_doi               10.1021/ol035046m
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33
_chemical_name_systematic
;
 ?
;
_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'
_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                 100.3540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3985(8)
_cell_length_b                   10.7275(9)
_cell_length_c                   13.8300(12)
_cell_measurement_temperature    98(2)
_cell_volume                     1371.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      98(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega 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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12177
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Brick
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.459
_refine_ls_shift/su_mean         0.083
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0626P)²+0.5466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                2866
_reflns_number_total             3257
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol035046msi20030704_101418.cif
_cod_data_source_block           jhw03
_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      P2(1)/c
_cod_database_code               1507356
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_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
O1 O 1.01888(10) 0.83483(8) 1.11432(6) 0.0215(2) Uani 1 1 d .
H1 H 0.9593 0.8073 1.1476 0.032 Uiso 1 1 calc R
O2 O 0.80843(9) 0.76199(8) 0.70917(6) 0.0212(2) Uani 1 1 d .
N1 N 0.91889(11) 0.90826(10) 0.81542(7) 0.0187(2) Uani 1 1 d .
C8 C 1.05212(13) 0.83702(11) 0.84720(8) 0.0182(2) Uani 1 1 d .
H8 H 1.0330 0.7483 0.8267 0.022 Uiso 1 1 calc R
C3 C 1.09605(12) 0.84040(11) 0.95959(8) 0.0178(2) Uani 1 1 d .
H3 H 1.1198 0.9290 0.9785 0.021 Uiso 1 1 calc R
C7 C 1.17441(13) 0.88588(12) 0.79794(9) 0.0218(3) Uani 1 1 d .
H7A H 1.1450 0.8804 0.7257 0.026 Uiso 1 1 calc R
H7B H 1.1931 0.9746 0.8155 0.026 Uiso 1 1 calc R
C10 C 0.80624(13) 0.86324(11) 0.75186(8) 0.0179(2) Uani 1 1 d .
C11 C 0.67156(13) 0.94119(11) 0.73498(9) 0.0188(2) Uani 1 1 d .
C2 C 0.97390(13) 0.79990(12) 1.01320(9) 0.0191(3) Uani 1 1 d .
H2 H 0.8849 0.8483 0.9856 0.023 Uiso 1 1 calc R
C4 C 1.23523(13) 0.76411(12) 0.99063(9) 0.0223(3) Uani 1 1 d .
H4A H 1.2651 0.7682 1.0629 0.027 Uiso 1 1 calc R
H4B H 1.2160 0.6757 0.9721 0.027 Uiso 1 1 calc R
C14 C 0.41608(14) 1.07897(12) 0.69829(10) 0.0247(3) Uani 1 1 d .
H14 H 0.3300 1.1272 0.6853 0.030 Uiso 1 1 calc R
C16 C 0.57810(14) 0.93107(12) 0.64469(9) 0.0218(3) Uani 1 1 d .
H16 H 0.6012 0.8763 0.5958 0.026 Uiso 1 1 calc R
C12 C 0.63418(13) 1.01851(12) 0.80762(9) 0.0217(3) Uani 1 1 d .
H12 H 0.6963 1.0246 0.8697 0.026 Uiso 1 1 calc R
C5 C 1.35767(14) 0.81300(13) 0.94183(10) 0.0250(3) Uani 1 1 d .
H5A H 1.3820 0.8994 0.9639 0.030 Uiso 1 1 calc R
H5B H 1.4449 0.7608 0.9616 0.030 Uiso 1 1 calc R
C13 C 0.50644(14) 1.08666(12) 0.78947(10) 0.0240(3) Uani 1 1 d .
H13 H 0.4808 1.1385 0.8394 0.029 Uiso 1 1 calc R
C6 C 1.31245(14) 0.81042(13) 0.83046(10) 0.0244(3) Uani 1 1 d .
H6A H 1.2961 0.7231 0.8080 0.029 Uiso 1 1 calc R
H6B H 1.3911 0.8453 0.7997 0.029 Uiso 1 1 calc R
C1 C 0.93780(15) 0.66143(13) 1.00417(10) 0.0265(3) Uani 1 1 d .
H1A H 1.0207 0.6129 1.0373 0.040 Uiso 1 1 calc R
H1B H 0.9158 0.6382 0.9346 0.040 Uiso 1 1 calc R
H1C H 0.8537 0.6442 1.0349 0.040 Uiso 1 1 calc R
C15 C 0.45173(14) 1.00062(13) 0.62602(10) 0.0248(3) Uani 1 1 d .
H15 H 0.3895 0.9948 0.5639 0.030 Uiso 1 1 calc R
H1D H 0.9193(18) 0.9855(18) 0.8358(12) 0.031(4) 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
C10 N1 C8 122.76(10)
N1 C8 C7 110.96(10)
N1 C8 C3 110.56(9)
C7 C8 C3 110.84(10)
C8 C3 C2 113.17(10)
C8 C3 C4 109.31(9)
C2 C3 C4 112.74(10)
C6 C7 C8 110.72(10)
O2 C10 N1 123.40(11)
O2 C10 C11 120.05(11)
N1 C10 C11 116.54(11)
C12 C11 C16 119.40(11)
C12 C11 C10 122.27(11)
C16 C11 C10 118.27(11)
O1 C2 C1 110.88(10)
O1 C2 C3 106.34(9)
C1 C2 C3 114.25(10)
C5 C4 C3 111.38(10)
C13 C14 C15 120.03(12)
C15 C16 C11 120.32(12)
C13 C12 C11 120.26(12)
C6 C5 C4 110.19(11)
C12 C13 C14 119.98(12)
C5 C6 C7 110.87(10)
C16 C15 C14 119.98(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.4361(14)
O2 C10 1.2382(15)
N1 C10 1.3387(16)
N1 C8 1.4653(15)
C8 C7 1.5301(17)
C8 C3 1.5352(16)
C3 C2 1.5370(16)
C3 C4 1.5373(17)
C7 C6 1.5268(17)
C10 C11 1.4999(17)
C11 C12 1.3954(17)
C11 C16 1.3959(17)
C2 C1 1.5237(18)
C4 C5 1.5276(19)
C14 C13 1.3904(19)
C14 C15 1.3922(19)
C16 C15 1.3869(18)
C12 C13 1.3895(18)
C5 C6 1.5227(18)
