#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:34:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178397 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/19/4021928.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_4021928
loop_
_publ_author_name
'Glen Baghdasarian'
'K. A. Woerpel'
_publ_section_title
;
 Electrostatic Effects on the Reactions of Cyclohexanone Oxocarbenium Ions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6851
_journal_page_last               6858
_journal_paper_doi               10.1021/jo060968z
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C25 H32 N2 O5'
_chemical_formula_weight         440.53
_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                87.037(4)
_cell_angle_beta                 84.042(3)
_cell_angle_gamma                86.669(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0052(15)
_cell_length_b                   11.777(2)
_cell_length_c                   12.237(2)
_cell_measurement_temperature    163(2)
_cell_volume                     1144.3(4)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10976
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0383
_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)+(0.0465P)²+0.3785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                3434
_reflns_number_total             4592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060968zsi20060510_123426.cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' 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_database_code               4021928
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 0.10110(12) 0.21993(8) 0.20336(8) 0.0226(2) Uani 1 1 d
O2 O -0.25229(13) 0.04614(9) -0.08907(9) 0.0259(3) Uani 1 1 d
O3 O -0.51919(14) 0.09986(9) -0.12112(9) 0.0309(3) Uani 1 1 d
O4 O -0.86050(15) -0.05946(10) -0.58024(10) 0.0365(3) Uani 1 1 d
O5 O -0.69591(17) -0.20541(12) -0.61902(12) 0.0519(4) Uani 1 1 d
N1 N -0.37505(17) -0.05139(11) -0.20625(11) 0.0235(3) Uani 1 1 d
N2 N -0.74238(16) -0.12598(11) -0.56132(11) 0.0275(3) Uani 1 1 d
C1 C 0.06398(18) 0.30606(12) 0.11818(12) 0.0206(3) Uani 1 1 d
C2 C 0.03674(19) 0.42384(13) 0.16705(14) 0.0234(3) Uani 1 1 d
C3 C 0.18979(19) 0.45922(13) 0.21910(13) 0.0237(3) Uani 1 1 d
C4 C 0.34911(19) 0.45770(12) 0.13802(13) 0.0220(3) Uani 1 1 d
C5 C 0.37660(19) 0.34195(12) 0.08507(13) 0.0220(3) Uani 1 1 d
C6 C 0.22214(19) 0.30353(13) 0.03674(12) 0.0221(3) Uani 1 1 d
C7 C -0.0919(2) 0.27690(13) 0.06467(14) 0.0247(3) Uani 1 1 d
C8 C -0.0857(2) 0.16083(13) 0.01284(14) 0.0262(3) Uani 1 1 d
C9 C -0.2590(2) 0.14275(14) -0.01935(15) 0.0297(4) Uani 1 1 d
C10 C -0.39473(19) 0.03780(12) -0.13727(12) 0.0229(3) Uani 1 1 d
C11 C -0.47554(18) -0.07017(12) -0.28983(12) 0.0210(3) Uani 1 1 d
C12 C -0.4283(2) -0.16197(13) -0.35682(13) 0.0245(3) Uani 1 1 d
C13 C -0.5152(2) -0.18162(13) -0.44486(13) 0.0250(3) Uani 1 1 d
C14 C -0.65121(18) -0.10812(12) -0.46638(12) 0.0220(3) Uani 1 1 d
C15 C -0.70195(19) -0.01781(13) -0.40097(13) 0.0236(3) Uani 1 1 d
C16 C -0.61579(19) 0.00099(13) -0.31221(13) 0.0242(3) Uani 1 1 d
C17 C -0.0245(2) 0.20583(18) 0.29340(16) 0.0370(4) Uani 1 1 d
C18 C 0.5055(2) 0.48386(13) 0.19256(14) 0.0245(3) Uani 1 1 d
C19 C 0.4958(2) 0.59903(14) 0.24553(16) 0.0324(4) Uani 1 1 d
C20 C 0.64748(19) 0.61888(13) 0.30466(13) 0.0255(3) Uani 1 1 d
C21 C 0.6808(2) 0.55290(15) 0.39849(14) 0.0322(4) Uani 1 1 d
C22 C 0.8164(2) 0.57364(16) 0.45511(15) 0.0387(4) Uani 1 1 d
C23 C 0.9215(2) 0.65960(16) 0.41839(16) 0.0393(4) Uani 1 1 d
C24 C 0.8916(2) 0.72463(15) 0.32524(16) 0.0347(4) Uani 1 1 d
C25 C 0.7555(2) 0.70441(13) 0.26896(14) 0.0287(4) Uani 1 1 d
H1 H -0.282(2) -0.0971(16) -0.2016(15) 0.038(5) Uiso 1 1 d
H2A H -0.063(2) 0.4274(14) 0.2212(15) 0.031(5) Uiso 1 1 d
H2B H 0.013(2) 0.4805(14) 0.1061(14) 0.027(4) Uiso 1 1 d
H3A H 0.2087(19) 0.4060(14) 0.2845(13) 0.023(4) Uiso 1 1 d
H3B H 0.164(2) 0.5345(15) 0.2481(14) 0.032(5) Uiso 1 1 d
H4A H 0.331(2) 0.5193(14) 0.0787(13) 0.024(4) Uiso 1 1 d
H5A H 0.4132(19) 0.2827(13) 0.1412(13) 0.021(4) Uiso 1 1 d
H5B H 0.473(2) 0.3440(14) 0.0290(14) 0.028(4) Uiso 1 1 d
H6A H 0.197(2) 0.3560(14) -0.0296(14) 0.026(4) Uiso 1 1 d
H6B H 0.2435(19) 0.2254(14) 0.0110(13) 0.024(4) Uiso 1 1 d
H7A H -0.111(2) 0.3373(15) 0.0077(15) 0.031(5) Uiso 1 1 d
H7B H -0.192(2) 0.2827(14) 0.1204(14) 0.031(5) Uiso 1 1 d
H8A H -0.004(2) 0.1583(15) -0.0519(16) 0.038(5) Uiso 1 1 d
H8B H -0.052(2) 0.0981(15) 0.0661(14) 0.030(4) Uiso 1 1 d
H9A H -0.338(2) 0.1256(14) 0.0512(15) 0.033(5) Uiso 1 1 d
H9B H -0.298(2) 0.2088(16) -0.0591(15) 0.038(5) Uiso 1 1 d
H12 H -0.331(2) -0.2106(14) -0.3433(14) 0.029(4) Uiso 1 1 d
H13 H -0.481(2) -0.2406(15) -0.4900(14) 0.030(5) Uiso 1 1 d
H15 H -0.797(2) 0.0317(14) -0.4184(14) 0.029(4) Uiso 1 1 d
H16 H -0.649(2) 0.0622(14) -0.2671(14) 0.029(4) Uiso 1 1 d
H17A H -0.046(3) 0.2783(19) 0.3387(18) 0.054(6) Uiso 1 1 d
H17B H -0.134(3) 0.1907(18) 0.2706(18) 0.056(6) Uiso 1 1 d
H17C H 0.017(3) 0.1441(17) 0.3429(17) 0.048(6) Uiso 1 1 d
H18A H 0.525(2) 0.4214(14) 0.2488(14) 0.029(4) Uiso 1 1 d
H18B H 0.602(2) 0.4787(14) 0.1389(14) 0.027(4) Uiso 1 1 d
H19A H 0.397(3) 0.6020(16) 0.2998(17) 0.046(6) Uiso 1 1 d
H19B H 0.481(2) 0.6621(17) 0.1884(16) 0.042(5) Uiso 1 1 d
H21 H 0.607(2) 0.4907(15) 0.4253(14) 0.033(5) Uiso 1 1 d
H22 H 0.835(3) 0.5257(17) 0.5189(18) 0.050(6) Uiso 1 1 d
H23 H 1.015(3) 0.6758(17) 0.4585(17) 0.047(6) Uiso 1 1 d
H24 H 0.971(2) 0.7827(17) 0.2974(16) 0.042(5) Uiso 1 1 d
H25 H 0.735(2) 0.7506(15) 0.2053(15) 0.037(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
C17 O1 C1 116.75(12)
C10 O2 C9 113.01(11)
C10 N1 C11 126.21(13)
O5 N2 O4 122.84(14)
O5 N2 C14 118.54(13)
O4 N2 C14 118.61(13)
O1 C1 C6 104.32(11)
O1 C1 C7 110.36(12)
C6 C1 C7 112.05(13)
O1 C1 C2 110.24(12)
C6 C1 C2 109.50(12)
C7 C1 C2 110.23(12)
C3 C2 C1 112.75(12)
C2 C3 C4 112.34(13)
C18 C4 C3 112.37(13)
C18 C4 C5 109.86(12)
C3 C4 C5 110.13(12)
C6 C5 C4 113.85(12)
C5 C6 C1 113.23(12)
C1 C7 C8 116.76(12)
C9 C8 C7 107.75(13)
O2 C9 C8 109.93(13)
O3 C10 O2 124.43(14)
O3 C10 N1 126.11(14)
O2 C10 N1 109.46(12)
N1 C11 C12 117.79(13)
N1 C11 C16 123.18(14)
C12 C11 C16 118.98(14)
C13 C12 C11 121.05(14)
C12 C13 C14 118.59(14)
C15 C14 C13 121.64(14)
C15 C14 N2 119.02(13)
C13 C14 N2 119.34(14)
C16 C15 C14 119.65(14)
C15 C16 C11 120.06(14)
C19 C18 C4 114.93(13)
C20 C19 C18 113.50(13)
C25 C20 C21 118.01(15)
C25 C20 C19 121.41(15)
C21 C20 C19 120.57(15)
C22 C21 C20 120.66(17)
C23 C22 C21 120.27(17)
C24 C23 C22 119.82(17)
C23 C24 C25 119.96(17)
C24 C25 C20 121.28(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C17 1.422(2)
O1 C1 1.4574(17)
O2 C10 1.3478(18)
O2 C9 1.4522(19)
O3 C10 1.2064(18)
O4 N2 1.2255(17)
O5 N2 1.2189(18)
N1 C10 1.3732(19)
N1 C11 1.3989(19)
N2 C14 1.4648(19)
C1 C6 1.528(2)
C1 C7 1.532(2)
C1 C2 1.534(2)
C2 C3 1.526(2)
C3 C4 1.532(2)
C4 C18 1.532(2)
C4 C5 1.534(2)
C5 C6 1.526(2)
C7 C8 1.532(2)
C8 C9 1.511(2)
C11 C12 1.401(2)
C11 C16 1.403(2)
C12 C13 1.378(2)
C13 C14 1.389(2)
C14 C15 1.381(2)
C15 C16 1.379(2)
C18 C19 1.528(2)
C19 C20 1.512(2)
C20 C25 1.389(2)
C20 C21 1.393(2)
C21 C22 1.387(3)
C22 C23 1.381(3)
C23 C24 1.374(3)
C24 C25 1.386(2)
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
C17 O1 C1 C6 178.15(14)
C17 O1 C1 C7 -61.32(17)
C17 O1 C1 C2 60.68(17)
O1 C1 C2 C3 59.41(17)
C6 C1 C2 C3 -54.80(16)
C7 C1 C2 C3 -178.51(13)
C1 C2 C3 C4 56.42(17)
C2 C3 C4 C18 -175.40(12)
C2 C3 C4 C5 -52.58(16)
C18 C4 C5 C6 175.16(13)
C3 C4 C5 C6 50.87(17)
C4 C5 C6 C1 -52.41(17)
O1 C1 C6 C5 -65.47(15)
C7 C1 C6 C5 175.14(12)
C2 C1 C6 C5 52.52(16)
O1 C1 C7 C8 -57.33(18)
C6 C1 C7 C8 58.45(18)
C2 C1 C7 C8 -179.34(14)
C1 C7 C8 C9 171.74(14)
C10 O2 C9 C8 -168.47(13)
C7 C8 C9 O2 168.11(14)
C9 O2 C10 O3 -3.4(2)
C9 O2 C10 N1 176.66(13)
C11 N1 C10 O3 17.0(2)
C11 N1 C10 O2 -163.14(13)
C10 N1 C11 C12 175.60(14)
C10 N1 C11 C16 -1.6(2)
N1 C11 C12 C13 -176.06(14)
C16 C11 C12 C13 1.3(2)
C11 C12 C13 C14 0.2(2)
C12 C13 C14 C15 -1.0(2)
C12 C13 C14 N2 178.44(13)
O5 N2 C14 C15 179.47(15)
O4 N2 C14 C15 0.5(2)
O5 N2 C14 C13 0.0(2)
O4 N2 C14 C13 -178.92(14)
C13 C14 C15 C16 0.3(2)
N2 C14 C15 C16 -179.09(14)
C14 C15 C16 C11 1.1(2)
N1 C11 C16 C15 175.26(14)
C12 C11 C16 C15 -1.9(2)
C3 C4 C18 C19 -58.78(18)
C5 C4 C18 C19 178.25(14)
C4 C18 C19 C20 176.39(14)
C18 C19 C20 C25 115.05(17)
C18 C19 C20 C21 -66.3(2)
C25 C20 C21 C22 1.0(2)
C19 C20 C21 C22 -177.68(15)
C20 C21 C22 C23 -0.6(3)
C21 C22 C23 C24 -0.1(3)
C22 C23 C24 C25 0.5(3)
C23 C24 C25 C20 -0.1(3)
C21 C20 C25 C24 -0.6(2)
C19 C20 C25 C24 178.04(15)
