#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:28:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180300 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/14/7151452.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_7151452
loop_
_publ_author_name
'Spiniello, Marisa'
'White, Jonathan M.'
_publ_section_title
;
 Low-temperature X-ray structural studies of the ester and ether
 derivatives of cis- and trans-4-tert-butyl cyclohexanol and
 2-adamantanol: application of the variable oxygen probe to determine
 the relative ?-donor ability of C?H and C?C bonds
;
_journal_issue                   17
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              3094
_journal_paper_doi               10.1039/b303453d
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C17 H19 N O4'
_chemical_formula_weight         301.33
_chemical_melting_point          69.0(10)
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.30(2)
_cell_angle_beta                 76.86(2)
_cell_angle_gamma                88.83(3)
_cell_formula_units_Z            2
_cell_length_a                   7.539(3)
_cell_length_b                   8.479(2)
_cell_length_c                   12.043(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      12
_cell_volume                     724.6(4)
_computing_data_collection       'CAD-4 Software 5.0 (Enraf-Nonius, 1989)'
_computing_data_reduction        'PROCESS_DATA (Gable et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130.0(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       θ2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4014
_diffrn_reflns_theta_full        73.20
_diffrn_reflns_theta_max         73.20
_diffrn_reflns_theta_min         3.90
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  9600
_exptl_absorpt_coefficient_mu    0.809
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0173(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0402
_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)+(0.0578P)²+0.2867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                2635
_reflns_number_total             2761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303453d.txt
_cod_data_source_block           compound6c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '68-70' was changed to '69.0(10)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151452
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30953(12) 0.08925(10) 0.18764(8) 0.0234(2) Uani 1 1 d . . .
C14 C 0.21602(16) 0.57349(15) -0.08941(11) 0.0223(3) Uani 1 1 d . . .
O3 O 0.27102(16) 0.82751(12) -0.06239(9) 0.0374(3) Uani 1 1 d . . .
O2 O 0.35333(18) 0.32809(12) 0.22850(9) 0.0429(3) Uani 1 1 d . . .
O4 O 0.16115(16) 0.81940(13) -0.21348(9) 0.0408(3) Uani 1 1 d . . .
C2 C 0.36240(17) -0.00098(14) 0.29665(11) 0.0207(3) Uani 1 1 d . . .
H2 H 0.4427 0.0706 0.3205 0.025 Uiso 1 1 calc R . .
N N 0.21650(15) 0.75318(13) -0.12446(9) 0.0263(3) Uani 1 1 d . . .
C12 C 0.26038(16) 0.32898(15) 0.05055(11) 0.0212(3) Uani 1 1 d . . .
C7 C 0.52876(17) -0.24008(15) 0.38320(11) 0.0240(3) Uani 1 1 d . . .
H7A H 0.5992 -0.3353 0.3681 0.029 Uiso 1 1 calc R . .
H7B H 0.6085 -0.1666 0.4044 0.029 Uiso 1 1 calc R . .
C10 C 0.24134(19) -0.40879(16) 0.44764(12) 0.0293(3) Uani 1 1 d . . .
H10A H 0.1339 -0.4477 0.5135 0.035 Uiso 1 1 calc R . .
H10B H 0.3094 -0.5051 0.4324 0.035 Uiso 1 1 calc R . .
C5 C 0.17722(19) -0.31698(16) 0.33572(13) 0.0293(3) Uani 1 1 d . . .
H5 H 0.0976 -0.3918 0.3142 0.035 Uiso 1 1 calc R . .
C11 C 0.31200(18) 0.25105(15) 0.16563(11) 0.0238(3) Uani 1 1 d . . .
C1 C 0.46475(17) -0.14847(15) 0.27105(11) 0.0228(3) Uani 1 1 d . . .
H1 H 0.5738 -0.1110 0.2045 0.027 Uiso 1 1 calc R . .
C13 C 0.26464(16) 0.49866(15) 0.01576(11) 0.0219(3) Uani 1 1 d . . .
H13 H 0.2999 0.5618 0.0626 0.026 Uiso 1 1 calc R . .
C9 C 0.25948(19) -0.14603(17) 0.50405(11) 0.0282(3) Uani 1 1 d . . .
H9A H 0.3389 -0.0721 0.5251 0.034 Uiso 1 1 calc R . .
H9B H 0.1525 -0.1807 0.5709 0.034 Uiso 1 1 calc R . .
C17 C 0.20717(17) 0.23888(16) -0.02006(11) 0.0240(3) Uani 1 1 d . . .
H17 H 0.2043 0.1230 0.0036 0.029 Uiso 1 1 calc R . .
C4 C 0.07179(18) -0.16736(17) 0.35736(13) 0.0299(3) Uani 1 1 d . . .
H4A H -0.0389 -0.2021 0.4214 0.036 Uiso 1 1 calc R . .
H4B H 0.0335 -0.1084 0.2850 0.036 Uiso 1 1 calc R . .
C15 C 0.16208(17) 0.48719(17) -0.16110(11) 0.0259(3) Uani 1 1 d . . .
H15 H 0.1290 0.5423 -0.2322 0.031 Uiso 1 1 calc R . .
C3 C 0.19504(17) -0.05386(16) 0.39200(11) 0.0243(3) Uani 1 1 d . . .
H3 H 0.1268 0.0438 0.4071 0.029 Uiso 1 1 calc R . .
C6 C 0.3416(2) -0.26165(16) 0.23679(12) 0.0284(3) Uani 1 1 d . . .
H6A H 0.3032 -0.2027 0.1644 0.034 Uiso 1 1 calc R . .
H6B H 0.4097 -0.3574 0.2204 0.034 Uiso 1 1 calc R . .
C8 C 0.36440(17) -0.29572(16) 0.48224(11) 0.0241(3) Uani 1 1 d . . .
H8 H 0.4032 -0.3554 0.5552 0.029 Uiso 1 1 calc R . .
C16 C 0.15823(18) 0.31823(17) -0.12528(12) 0.0275(3) Uani 1 1 d . . .
H16 H 0.1222 0.2559 -0.1723 0.033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C2 116.92(9) . . ?
C13 C14 C15 123.31(12) . . ?
C13 C14 N 118.08(11) . . ?
C15 C14 N 118.58(11) . . ?
O1 C2 C3 109.08(10) . . ?
O1 C2 C1 107.73(10) . . ?
C3 C2 C1 110.24(10) . . ?
O1 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
O3 N O4 124.25(11) . . ?
O3 N C14 117.65(11) . . ?
O4 N C14 118.10(11) . . ?
C13 C12 C17 119.66(12) . . ?
C13 C12 C11 117.15(11) . . ?
C17 C12 C11 123.18(11) . . ?
C8 C7 C1 108.76(10) . . ?
C8 C7 H7A 109.9 . . ?
C1 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C1 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C8 C10 C5 110.46(10) . . ?
C8 C10 H10A 109.6 . . ?
C5 C10 H10A 109.6 . . ?
C8 C10 H10B 109.6 . . ?
C5 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C6 C5 C4 108.82(11) . . ?
C6 C5 C10 108.64(11) . . ?
C4 C5 C10 110.41(12) . . ?
C6 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
C10 C5 H5 109.6 . . ?
O2 C11 O1 124.65(12) . . ?
O2 C11 C12 123.50(11) . . ?
O1 C11 C12 111.84(11) . . ?
C2 C1 C6 110.52(11) . . ?
C2 C1 C7 108.26(10) . . ?
C6 C1 C7 110.42(10) . . ?
C2 C1 H1 109.2 . . ?
C6 C1 H1 109.2 . . ?
C7 C1 H1 109.2 . . ?
C14 C13 C12 118.28(12) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C8 C9 C3 110.38(10) . . ?
C8 C9 H9A 109.6 . . ?
C3 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C3 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C16 C17 C12 120.57(12) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C5 C4 C3 109.22(11) . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C16 C15 C14 117.78(12) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C2 C3 C4 110.45(11) . . ?
C2 C3 C9 106.61(10) . . ?
C4 C3 C9 110.38(11) . . ?
C2 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C9 C3 H3 109.8 . . ?
C5 C6 C1 109.43(11) . . ?
C5 C6 H6A 109.8 . . ?
C1 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C1 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C7 C8 C9 108.68(11) . . ?
C7 C8 C10 109.33(11) . . ?
C9 C8 C10 109.34(11) . . ?
C7 C8 H8 109.8 . . ?
C9 C8 H8 109.8 . . ?
C10 C8 H8 109.8 . . ?
C15 C16 C17 120.39(12) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
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 C11 1.3293(15) . ?
O1 C2 1.4776(15) . ?
C14 C13 1.3910(18) . ?
C14 C15 1.3924(19) . ?
C14 N 1.4740(17) . ?
O3 N 1.2305(16) . ?
O2 C11 1.2098(17) . ?
O4 N 1.2358(15) . ?
C2 C3 1.4882(18) . ?
C2 C1 1.5175(17) . ?
C2 H2 1.0000 . ?
C12 C13 1.3915(18) . ?
C12 C17 1.4018(18) . ?
C12 C11 1.5095(18) . ?
C7 C8 1.4989(18) . ?
C7 C1 1.5521(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 C8 1.5389(18) . ?
C10 C5 1.5508(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C5 C6 1.498(2) . ?
C5 C4 1.530(2) . ?
C5 H5 1.0000 . ?
C1 C6 1.5377(19) . ?
C1 H1 1.0000 . ?
C13 H13 0.9500 . ?
C9 C8 1.5294(19) . ?
C9 C3 1.5540(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C17 C16 1.4016(19) . ?
C17 H17 0.9500 . ?
C4 C3 1.5427(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C3 H3 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8 1.0000 . ?
C16 H16 0.9500 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 C2 C3 96.03(13) . . . . ?
C11 O1 C2 C1 -144.31(11) . . . . ?
C13 C14 N O3 4.47(17) . . . . ?
C15 C14 N O3 -177.36(11) . . . . ?
C13 C14 N O4 -175.03(11) . . . . ?
C15 C14 N O4 3.15(17) . . . . ?
C8 C10 C5 C6 60.11(15) . . . . ?
C8 C10 C5 C4 -59.15(14) . . . . ?
C2 O1 C11 O2 -0.37(19) . . . . ?
C2 O1 C11 C12 178.47(9) . . . . ?
C13 C12 C11 O2 1.16(19) . . . . ?
C17 C12 C11 O2 -177.95(13) . . . . ?
C13 C12 C11 O1 -177.69(10) . . . . ?
C17 C12 C11 O1 3.19(17) . . . . ?
O1 C2 C1 C6 -61.49(12) . . . . ?
C3 C2 C1 C6 57.44(13) . . . . ?
O1 C2 C1 C7 177.47(9) . . . . ?
C3 C2 C1 C7 -63.60(13) . . . . ?
C8 C7 C1 C2 61.23(13) . . . . ?
C8 C7 C1 C6 -59.88(13) . . . . ?
C15 C14 C13 C12 0.48(18) . . . . ?
N C14 C13 C12 178.56(10) . . . . ?
C17 C12 C13 C14 -0.26(18) . . . . ?
C11 C12 C13 C14 -179.41(10) . . . . ?
C13 C12 C17 C16 -0.02(18) . . . . ?
C11 C12 C17 C16 179.07(11) . . . . ?
C6 C5 C4 C3 -60.75(14) . . . . ?
C10 C5 C4 C3 58.41(14) . . . . ?
C13 C14 C15 C16 -0.40(19) . . . . ?
N C14 C15 C16 -178.47(11) . . . . ?
O1 C2 C3 C4 60.62(13) . . . . ?
C1 C2 C3 C4 -57.48(13) . . . . ?
O1 C2 C3 C9 -179.44(9) . . . . ?
C1 C2 C3 C9 62.46(13) . . . . ?
C5 C4 C3 C2 59.33(14) . . . . ?
C5 C4 C3 C9 -58.32(14) . . . . ?
C8 C9 C3 C2 -61.05(14) . . . . ?
C8 C9 C3 C4 58.94(14) . . . . ?
C4 C5 C6 C1 60.80(14) . . . . ?
C10 C5 C6 C1 -59.46(13) . . . . ?
C2 C1 C6 C5 -59.36(14) . . . . ?
C7 C1 C6 C5 60.40(13) . . . . ?
C1 C7 C8 C9 -60.05(13) . . . . ?
C1 C7 C8 C10 59.23(13) . . . . ?
C3 C9 C8 C7 60.95(14) . . . . ?
C3 C9 C8 C10 -58.33(14) . . . . ?
C5 C10 C8 C7 -60.43(14) . . . . ?
C5 C10 C8 C9 58.45(14) . . . . ?
C14 C15 C16 C17 0.09(19) . . . . ?
C12 C17 C16 C15 0.11(19) . . . . ?
