#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:53:40 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178922 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/51/4115159.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_4115159
loop_
_publ_author_name
'Sabrina Antonello'
'Marco Crisma'
'Fernando Formaggio'
'Alessandro Moretto'
'Ferdinando Taddei'
'Claudio Toniolo'
'Flavio Maran'
_publ_section_title
;
 Insights into the Free-Energy Dependence of Intramolecular Dissociative
 Electron Transfers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11503
_journal_page_last               11513
_journal_paper_doi               10.1021/ja0263644
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C19 H23 N O5'
_chemical_formula_weight         345.38
_chemical_name_systematic
; 
 N-phtaloyl-cis-1-aminocyclohexane-4-carboxylate
 tert-butyl perester 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.019(3)
_cell_length_b                   11.515(3)
_cell_length_c                   26.124(4)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      12
_cell_volume                     3615.5(14)
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PARST96 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Philips PW1100 diffractometer'
_diffrn_measurement_method       'θ-2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0081
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2988
_diffrn_reflns_theta_full        60.11
_diffrn_reflns_theta_max         60.11
_diffrn_reflns_theta_min         5.00
_diffrn_standards_decay_%        5
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0067(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0682P)²+0.8862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2379
_reflns_number_total             2676
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0263644_s2_1.cif
_cod_data_source_block           1a
_cod_database_code               4115159
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C1 C 0.66488(15) 0.14521(16) 0.44791(7) 0.0587(5) Uani 1 1 d .
C2 C 0.68710(17) 0.14594(18) 0.49938(8) 0.0683(6) Uani 1 1 d .
H2 H 0.6462 0.1006 0.5221 0.082 Uiso 1 1 calc R
C3 C 0.77280(18) 0.21667(19) 0.51641(9) 0.0743(6) Uani 1 1 d .
H3 H 0.7905 0.2179 0.5511 0.089 Uiso 1 1 calc R
C4 C 0.83226(18) 0.28514(19) 0.48290(9) 0.0748(6) Uani 1 1 d .
H4 H 0.8886 0.3327 0.4954 0.090 Uiso 1 1 calc R
C5 C 0.80951(16) 0.28432(18) 0.43101(9) 0.0702(6) Uani 1 1 d .
H5 H 0.8495 0.3307 0.4084 0.084 Uiso 1 1 calc R
C6 C 0.72595(15) 0.21269(15) 0.41389(7) 0.0584(5) Uani 1 1 d .
C7 C 0.68173(15) 0.19179(17) 0.36179(8) 0.0615(5) Uani 1 1 d .
O1 O 0.71037(13) 0.23558(14) 0.32188(5) 0.0799(5) Uani 1 1 d .
C8 C 0.57938(16) 0.08201(16) 0.41820(7) 0.0606(5) Uani 1 1 d .
O2 O 0.50678(12) 0.01861(13) 0.43414(6) 0.0770(5) Uani 1 1 d .
N1 N 0.59708(12) 0.10982(14) 0.36694(6) 0.0608(4) Uani 1 1 d .
C9 C 0.52663(16) 0.07225(17) 0.32404(7) 0.0612(5) Uani 1 1 d .
H9 H 0.5609 0.1009 0.2924 0.073 Uiso 1 1 calc R
C10 C 0.52028(16) -0.06006(18) 0.32015(8) 0.0640(5) Uani 1 1 d .
H10A H 0.5943 -0.0911 0.3144 0.077 Uiso 1 1 calc R
H10B H 0.4928 -0.0915 0.3522 0.077 Uiso 1 1 calc R
C11 C 0.44426(18) -0.09778(18) 0.27687(8) 0.0701(6) Uani 1 1 d .
H11A H 0.4362 -0.1816 0.2779 0.084 Uiso 1 1 calc R
H11B H 0.4786 -0.0776 0.2445 0.084 Uiso 1 1 calc R
C12 C 0.32857(17) -0.04203(19) 0.27948(8) 0.0690(6) Uani 1 1 d .
H12 H 0.2894 -0.0603 0.2476 0.083 Uiso 1 1 calc R
C13 C 0.33936(18) 0.09047(18) 0.28319(9) 0.0730(6) Uani 1 1 d .
H13A H 0.3716 0.1201 0.2518 0.088 Uiso 1 1 calc R
H13B H 0.2660 0.1244 0.2870 0.088 Uiso 1 1 calc R
C14 C 0.41113(17) 0.12628(17) 0.32784(8) 0.0665(5) Uani 1 1 d .
H14A H 0.3761 0.1019 0.3595 0.080 Uiso 1 1 calc R
H14B H 0.4178 0.2102 0.3285 0.080 Uiso 1 1 calc R
C15 C 0.26136(17) -0.09086(18) 0.32338(9) 0.0694(6) Uani 1 1 d .
O3 O 0.28789(14) -0.16260(16) 0.35324(8) 0.1011(6) Uani 1 1 d .
O4 O 0.15979(13) -0.04061(16) 0.32272(7) 0.0923(6) Uani 1 1 d .
O5 O 0.08884(14) -0.08461(13) 0.36370(8) 0.1014(6) Uani 1 1 d .
C16 C 0.03863(17) 0.01389(18) 0.38928(9) 0.0732(6) Uani 1 1 d .
C17 C -0.0380(2) -0.0442(3) 0.42630(14) 0.1212(11) Uani 1 1 d .
H17A H -0.0971 -0.0817 0.4079 0.182 Uiso 1 1 calc R
H17B H -0.0687 0.0127 0.4491 0.182 Uiso 1 1 calc R
H17C H 0.0026 -0.1010 0.4457 0.182 Uiso 1 1 calc R
C18 C 0.1253(2) 0.0826(3) 0.41620(11) 0.1033(9) Uani 1 1 d .
H18A H 0.1666 0.0327 0.4387 0.155 Uiso 1 1 calc R
H18B H 0.0905 0.1431 0.4358 0.155 Uiso 1 1 calc R
H18C H 0.1748 0.1165 0.3915 0.155 Uiso 1 1 calc R
C19 C -0.0227(3) 0.0876(3) 0.35065(12) 0.1297(13) Uani 1 1 d .
H19A H 0.0274 0.1100 0.3238 0.195 Uiso 1 1 calc R
H19B H -0.0512 0.1559 0.3672 0.195 Uiso 1 1 calc R
H19C H -0.0832 0.0439 0.3364 0.195 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 C6 121.38(18)
C2 C1 C8 130.77(18)
C6 C1 C8 107.85(17)
C1 C2 C3 117.6(2)
C4 C3 C2 121.2(2)
C3 C4 C5 121.1(2)
C6 C5 C4 117.9(2)
C5 C6 C1 120.89(19)
C5 C6 C7 131.21(18)
C1 C6 C7 107.89(17)
O1 C7 N1 125.00(19)
O1 C7 C6 128.54(18)
N1 C7 C6 106.46(16)
O2 C8 N1 125.37(18)
O2 C8 C1 128.06(19)
N1 C8 C1 106.57(15)
C8 N1 C7 111.08(16)
C8 N1 C9 125.26(15)
C7 N1 C9 123.11(15)
N1 C9 C14 110.78(15)
N1 C9 C10 111.89(16)
C14 C9 C10 111.44(16)
C11 C10 C9 111.40(16)
C10 C11 C12 113.16(16)
C15 C12 C11 111.26(18)
C15 C12 C13 111.54(17)
C11 C12 C13 110.04(18)
C14 C13 C12 111.66(17)
C13 C14 C9 111.03(16)
O3 C15 O4 123.5(2)
O3 C15 C12 128.1(2)
O4 C15 C12 108.30(19)
C15 O4 O5 111.71(18)
C16 O5 O4 108.07(16)
O5 C16 C18 110.1(2)
O5 C16 C17 101.82(19)
C18 C16 C17 111.4(2)
O5 C16 C19 109.6(2)
C18 C16 C19 111.0(2)
C17 C16 C19 112.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.371(3)
C1 C6 1.390(3)
C1 C8 1.479(3)
C2 C3 1.386(3)
C3 C4 1.378(3)
C4 C5 1.383(3)
C5 C6 1.374(3)
C6 C7 1.481(3)
C7 O1 1.208(2)
C7 N1 1.394(2)
C8 O2 1.212(2)
C8 N1 1.393(2)
N1 C9 1.470(2)
C9 C14 1.525(3)
C9 C10 1.529(3)
C10 C11 1.517(3)
C11 C12 1.533(3)
C12 C15 1.511(3)
C12 C13 1.534(3)
C13 C14 1.508(3)
C15 O3 1.180(3)
C15 O4 1.351(3)
O4 O5 1.459(2)
O5 C16 1.448(3)
C16 C18 1.485(3)
C16 C17 1.494(4)
C16 C19 1.511(4)
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
C6 C1 C2 C3 0.1(3)
C8 C1 C2 C3 -178.84(19)
C1 C2 C3 C4 1.0(3)
C2 C3 C4 C5 -1.0(3)
C3 C4 C5 C6 -0.2(3)
C4 C5 C6 C1 1.3(3)
C4 C5 C6 C7 -179.99(19)
C2 C1 C6 C5 -1.3(3)
C8 C1 C6 C5 177.86(17)
C2 C1 C6 C7 179.77(17)
C8 C1 C6 C7 -1.1(2)
C5 C6 C7 O1 -0.6(4)
C1 C6 C7 O1 178.21(19)
C5 C6 C7 N1 179.81(19)
C1 C6 C7 N1 -1.4(2)
C2 C1 C8 O2 2.7(3)
C6 C1 C8 O2 -176.38(19)
C2 C1 C8 N1 -177.79(19)
C6 C1 C8 N1 3.2(2)
O2 C8 N1 C7 175.40(18)
C1 C8 N1 C7 -4.2(2)
O2 C8 N1 C9 3.8(3)
C1 C8 N1 C9 -175.81(16)
O1 C7 N1 C8 -176.10(19)
C6 C7 N1 C8 3.5(2)
O1 C7 N1 C9 -4.3(3)
C6 C7 N1 C9 175.36(15)
C8 N1 C9 C14 65.8(2)
C7 N1 C9 C14 -104.8(2)
C8 N1 C9 C10 -59.2(2)
C7 N1 C9 C10 130.13(18)
N1 C9 C10 C11 178.08(15)
C14 C9 C10 C11 53.4(2)
C9 C10 C11 C12 -52.7(2)
C10 C11 C12 C15 -70.9(2)
C10 C11 C12 C13 53.2(2)
C15 C12 C13 C14 68.6(2)
C11 C12 C13 C14 -55.4(2)
C12 C13 C14 C9 57.5(2)
N1 C9 C14 C13 178.55(16)
C10 C9 C14 C13 -56.2(2)
C11 C12 C15 O3 -0.3(3)
C13 C12 C15 O3 -123.6(2)
C11 C12 C15 O4 -178.41(16)
C13 C12 C15 O4 58.3(2)
O3 C15 O4 O5 0.9(3)
C12 C15 O4 O5 179.15(15)
C15 O4 O5 C16 132.03(19)
O4 O5 C16 C18 -66.6(2)
O4 O5 C16 C17 175.1(2)
O4 O5 C16 C19 55.8(3)
