#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/69/1506928.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_1506928
loop_
_publ_author_name
'Chamberland, Stephen'
'Woerpel, K. A.'
_publ_section_title
;
 Using nucleophilic substitution reactions to understand how a remote
 alkyl or alkoxy substituent influences the conformation of eight-membered
 ring oxocarbenium ions.
;
_journal_issue                   25
_journal_name_full               'Organic letters'
_journal_page_first              4739
_journal_page_last               4741
_journal_paper_doi               10.1021/ol047998d
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C18 H24 N O3'
_chemical_formula_weight         302.38
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                94.2720(10)
_cell_angle_beta                 94.6620(10)
_cell_angle_gamma                95.6630(10)
_cell_formula_units_Z            2
_cell_length_a                   5.2748(3)
_cell_length_b                   10.1002(6)
_cell_length_c                   15.4153(9)
_cell_measurement_temperature    173(2)
_cell_volume                     811.74(8)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8683
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular needle'
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0536
_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)+(0.1026P)²+0.1307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1522
_reflns_number_gt                3211
_reflns_number_total             3814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol047998dsi20041026_080507.cif
_cod_data_source_block           kaw37
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506928
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
O1 O -0.34108(17) 0.22650(9) 0.78726(6) 0.0214(2) Uani 1 1 d
O2 O 0.18253(18) 0.40891(10) 0.92033(6) 0.0244(2) Uani 1 1 d
O3 O -0.2780(2) 0.20151(10) 0.51135(6) 0.0267(2) Uani 1 1 d
N1 N -0.2472(2) 0.40624(12) 0.92289(8) 0.0239(3) Uani 1 1 d
C1 C -0.0767(2) 0.27193(13) 0.80690(8) 0.0199(3) Uani 1 1 d
C2 C 0.0294(3) 0.34114(13) 0.73037(9) 0.0226(3) Uani 1 1 d
C3 C 0.0147(3) 0.25355(14) 0.64417(9) 0.0235(3) Uani 1 1 d
C4 C -0.2566(3) 0.19838(13) 0.60523(8) 0.0226(3) Uani 1 1 d
C5 C -0.3313(3) 0.05163(14) 0.61942(9) 0.0261(3) Uani 1 1 d
C6 C -0.2715(3) 0.00977(13) 0.71164(9) 0.0245(3) Uani 1 1 d
C7 C -0.3969(3) 0.08362(13) 0.78304(9) 0.0239(3) Uani 1 1 d
C8 C -0.0382(2) 0.36891(13) 0.88931(8) 0.0201(3) Uani 1 1 d
C9 C -0.3319(3) 0.32715(15) 0.48403(9) 0.0283(3) Uani 1 1 d
C10 C -0.3401(3) 0.32243(13) 0.38585(9) 0.0239(3) Uani 1 1 d
C11 C -0.5218(3) 0.38458(14) 0.33819(9) 0.0263(3) Uani 1 1 d
C12 C -0.5272(3) 0.38223(14) 0.24774(10) 0.0281(3) Uani 1 1 d
C13 C -0.3497(3) 0.31737(14) 0.20389(9) 0.0283(3) Uani 1 1 d
C14 C -0.1684(3) 0.25416(16) 0.25078(10) 0.0295(3) Uani 1 1 d
C15 C -0.1628(3) 0.25647(15) 0.34129(9) 0.0279(3) Uani 1 1 d
C16 C 0.0213(3) 0.13310(15) 1.03303(10) 0.0302(3) Uani 1 1 d
C17 C 0.2005(3) 0.08874(16) 0.97942(10) 0.0303(3) Uani 1 1 d
C18 C 0.1786(3) -0.04388(16) 0.94660(10) 0.0308(3) Uani 1 1 d
H1 H -0.401(4) 0.3774(18) 0.9007(12) 0.029(4) Uiso 1 1 d
H2 H -0.233(4) 0.467(2) 0.9689(15) 0.042(5) Uiso 1 1 d
H1A H 0.020(3) 0.1996(16) 0.8200(11) 0.021(4) Uiso 1 1 d
H2A H -0.067(3) 0.4177(17) 0.7210(11) 0.026(4) Uiso 1 1 d
H2B H 0.207(4) 0.3753(18) 0.7485(12) 0.030(4) Uiso 1 1 d
H3A H 0.128(3) 0.1801(18) 0.6507(12) 0.028(4) Uiso 1 1 d
H3B H 0.096(4) 0.3107(19) 0.6040(13) 0.037(5) Uiso 1 1 d
H4A H -0.380(3) 0.2555(15) 0.6318(10) 0.016(3) Uiso 1 1 d
H5A H -0.513(4) 0.0281(17) 0.6035(12) 0.029(4) Uiso 1 1 d
H5B H -0.243(4) -0.0004(19) 0.5781(14) 0.039(5) Uiso 1 1 d
H6A H -0.079(3) 0.0183(15) 0.7268(10) 0.019(4) Uiso 1 1 d
H6B H -0.327(3) -0.0877(17) 0.7126(11) 0.026(4) Uiso 1 1 d
H7A H -0.589(3) 0.0678(15) 0.7731(11) 0.020(4) Uiso 1 1 d
H7B H -0.344(4) 0.0514(19) 0.8400(13) 0.037(5) Uiso 1 1 d
H9A H -0.510(3) 0.3489(18) 0.5021(12) 0.031(4) Uiso 1 1 d
H9B H -0.197(4) 0.402(2) 0.5097(13) 0.038(5) Uiso 1 1 d
H11 H -0.648(4) 0.432(2) 0.3716(14) 0.046(6) Uiso 1 1 d
H12 H -0.657(3) 0.4251(17) 0.2157(12) 0.027(4) Uiso 1 1 d
H13 H -0.352(4) 0.3172(19) 0.1408(14) 0.039(5) Uiso 1 1 d
H14 H -0.043(4) 0.2075(19) 0.2210(13) 0.037(5) Uiso 1 1 d
H15 H -0.031(3) 0.2119(17) 0.3757(12) 0.028(4) Uiso 1 1 d
H16 H 0.041(4) 0.224(2) 1.0554(13) 0.038(5) Uiso 1 1 d
H17 H 0.347(4) 0.1486(18) 0.9681(12) 0.034(5) Uiso 1 1 d
H18 H 0.306(4) -0.0762(19) 0.9086(13) 0.038(5) 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
C1 O1 C7 113.90(10) . .
C9 O3 C4 112.96(10) . .
O1 C1 C2 110.58(10) . .
O1 C1 C8 110.35(10) . .
C2 C1 C8 109.58(11) . .
C1 C2 C3 115.33(11) . .
C2 C3 C4 115.60(11) . .
O3 C4 C5 104.08(10) . .
O3 C4 C3 110.48(11) . .
C5 C4 C3 114.46(11) . .
C6 C5 C4 116.51(11) . .
C7 C6 C5 115.36(12) . .
O1 C7 C6 113.81(11) . .
O2 C8 N1 123.83(12) . .
O2 C8 C1 118.93(11) . .
N1 C8 C1 117.24(11) . .
O3 C9 C10 109.12(11) . .
C11 C10 C15 118.79(13) . .
C11 C10 C9 120.74(12) . .
C15 C10 C9 120.47(12) . .
C10 C11 C12 120.85(13) . .
C13 C12 C11 120.13(13) . .
C12 C13 C14 119.52(13) . .
C13 C14 C15 120.40(14) . .
C14 C15 C10 120.30(13) . .
C18 C16 C17 119.63(14) 2_557 .
C18 C17 C16 119.90(15) . .
C17 C18 C16 120.47(14) . 2_557
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.4251(15) .
O1 C7 1.4396(16) .
O2 C8 1.2389(16) .
O3 C9 1.4143(17) .
O3 C4 1.4454(15) .
N1 C8 1.3310(18) .
C1 C2 1.5319(19) .
C1 C8 1.5323(17) .
C2 C3 1.5326(18) .
C3 C4 1.5399(19) .
C4 C5 1.5320(19) .
C5 C6 1.5304(19) .
C6 C7 1.5162(19) .
C9 C10 1.5078(19) .
C10 C11 1.388(2) .
C10 C15 1.397(2) .
C11 C12 1.391(2) .
C12 C13 1.386(2) .
C13 C14 1.386(2) .
C14 C15 1.392(2) .
C16 C18 1.390(2) 2_557
C16 C17 1.390(2) .
C17 C18 1.387(2) .
C18 C16 1.390(2) 2_557
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C7 O1 C1 C2 116.13(12) . .
C7 O1 C1 C8 -122.47(11) . .
O1 C1 C2 C3 -60.79(15) . .
C8 C1 C2 C3 177.36(11) . .
C1 C2 C3 C4 61.53(16) . .
C9 O3 C4 C5 152.93(12) . .
C9 O3 C4 C3 -83.75(14) . .
C2 C3 C4 O3 140.58(12) . .
C2 C3 C4 C5 -102.35(14) . .
O3 C4 C5 C6 166.99(12) . .
C3 C4 C5 C6 46.31(17) . .
C4 C5 C6 C7 59.27(17) . .
C1 O1 C7 C6 -62.46(15) . .
C5 C6 C7 O1 -55.77(16) . .
O1 C1 C8 O2 173.58(11) . .
C2 C1 C8 O2 -64.43(15) . .
O1 C1 C8 N1 -7.07(16) . .
C2 C1 C8 N1 114.92(13) . .
C4 O3 C9 C10 177.73(11) . .
O3 C9 C10 C11 140.36(14) . .
O3 C9 C10 C15 -40.33(19) . .
C15 C10 C11 C12 -0.4(2) . .
C9 C10 C11 C12 178.94(13) . .
C10 C11 C12 C13 0.0(2) . .
C11 C12 C13 C14 0.5(2) . .
C12 C13 C14 C15 -0.5(2) . .
C13 C14 C15 C10 0.1(2) . .
C11 C10 C15 C14 0.4(2) . .
C9 C10 C15 C14 -178.96(14) . .
C18 C16 C17 C18 0.1(2) 2_557 .
C16 C17 C18 C16 -0.1(2) . 2_557
