#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:28:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180300 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/14/7151446.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_7151446
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            'C16 H23 N O3'
_chemical_formula_weight         277.35
_chemical_melting_point          81.5(15)
_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                100.57(2)
_cell_angle_beta                 90.17(2)
_cell_angle_gamma                95.16(2)
_cell_formula_units_Z            2
_cell_length_a                   6.179(2)
_cell_length_b                   11.071(3)
_cell_length_c                   11.130(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      12
_cell_volume                     745.3(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2888
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  9600
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.011(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0439
_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)+(0.0785P)²+0.2995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                2196
_reflns_number_total             2622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303453d.txt
_cod_data_source_block           compound4i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '80-83' was changed to '81.5(15)' -
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               7151446
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
C1 C 0.3865(3) 0.07958(15) 0.85672(14) 0.0234(4) Uani 1 1 d . . .
H1 H 0.4509 0.1144 0.9397 0.028 Uiso 1 1 calc R . .
C2 C 0.1834(3) -0.00456(16) 0.86885(15) 0.0275(4) Uani 1 1 d . . .
H2A H 0.0708 0.0457 0.9098 0.033 Uiso 1 1 calc R . .
H2B H 0.2174 -0.0636 0.9215 0.033 Uiso 1 1 calc R . .
C3 C 0.0918(3) -0.07673(15) 0.74619(15) 0.0241(4) Uani 1 1 d . . .
H3A H 0.0425 -0.0185 0.6965 0.029 Uiso 1 1 calc R . .
H3B H -0.0358 -0.1328 0.7605 0.029 Uiso 1 1 calc R . .
C4 C 0.2623(2) -0.15245(14) 0.67575(14) 0.0205(4) Uani 1 1 d . . .
H4 H 0.3132 -0.2067 0.7306 0.025 Uiso 1 1 calc R . .
C5 C 0.4576(3) -0.06245(15) 0.65725(14) 0.0234(4) Uani 1 1 d . . .
H5A H 0.5711 -0.1093 0.6126 0.028 Uiso 1 1 calc R . .
H5B H 0.4115 -0.0043 0.6065 0.028 Uiso 1 1 calc R . .
C6 C 0.5537(3) 0.01078(15) 0.77855(15) 0.0227(4) Uani 1 1 d . . .
H6A H 0.6164 -0.0465 0.8248 0.027 Uiso 1 1 calc R . .
H6B H 0.6731 0.0708 0.7616 0.027 Uiso 1 1 calc R . .
C7 C 0.1731(3) -0.23881(15) 0.55625(15) 0.0243(4) Uani 1 1 d . . .
C8 C 0.3532(3) -0.31444(18) 0.49629(17) 0.0362(5) Uani 1 1 d . . .
H8A H 0.4094 -0.3612 0.5544 0.054 Uiso 1 1 calc R . .
H8B H 0.4712 -0.2588 0.4727 0.054 Uiso 1 1 calc R . .
H8C H 0.2941 -0.3717 0.4235 0.054 Uiso 1 1 calc R . .
C9 C 0.0866(3) -0.16610(18) 0.46449(16) 0.0340(4) Uani 1 1 d . . .
H9A H 0.2031 -0.1074 0.4445 0.051 Uiso 1 1 calc R . .
H9B H -0.0342 -0.1211 0.5005 0.051 Uiso 1 1 calc R . .
H9C H 0.0355 -0.2233 0.3899 0.051 Uiso 1 1 calc R . .
C10 C -0.0119(3) -0.32990(17) 0.58622(17) 0.0314(4) Uani 1 1 d . . .
H10A H 0.0411 -0.3771 0.6448 0.047 Uiso 1 1 calc R . .
H10B H -0.0627 -0.3865 0.5112 0.047 Uiso 1 1 calc R . .
H10C H -0.1322 -0.2843 0.6218 0.047 Uiso 1 1 calc R . .
C11 C 0.4309(3) 0.29030(15) 0.82239(14) 0.0217(4) Uani 1 1 d . . .
C12 C 0.6414(3) 0.31271(15) 0.87319(15) 0.0247(4) Uani 1 1 d . . .
H12 H 0.7123 0.2474 0.8960 0.030 Uiso 1 1 calc R . .
C13 C 0.7453(3) 0.43071(16) 0.89000(15) 0.0250(4) Uani 1 1 d . . .
H13 H 0.8885 0.4466 0.9240 0.030 Uiso 1 1 calc R . .
C14 C 0.6412(3) 0.52519(15) 0.85750(14) 0.0222(4) Uani 1 1 d . . .
C15 C 0.4310(3) 0.50498(15) 0.80790(14) 0.0247(4) Uani 1 1 d . . .
H15 H 0.3594 0.5712 0.7877 0.030 Uiso 1 1 calc R . .
C16 C 0.3292(3) 0.38710(16) 0.78880(15) 0.0245(4) Uani 1 1 d . . .
H16 H 0.1879 0.3714 0.7523 0.029 Uiso 1 1 calc R . .
N1 N 0.7489(2) 0.65006(13) 0.88015(12) 0.0262(4) Uani 1 1 d . . .
O1 O 0.31333(18) 0.17921(10) 0.80173(10) 0.0250(3) Uani 1 1 d . . .
O2 O 0.6475(2) 0.73451(11) 0.85959(12) 0.0343(3) Uani 1 1 d . . .
O3 O 0.9383(2) 0.66542(12) 0.91877(13) 0.0389(4) Uani 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
_geom_angle_publ_flag
O1 C1 C2 105.47(13) . . ?
O1 C1 C6 111.61(13) . . ?
C2 C1 C6 111.33(14) . . ?
O1 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
C6 C1 H1 109.5 . . ?
C1 C2 C3 113.25(13) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 111.39(14) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 107.57(13) . . ?
C3 C4 C7 114.09(13) . . ?
C5 C4 C7 114.23(13) . . ?
C3 C4 H4 106.8 . . ?
C5 C4 H4 106.8 . . ?
C7 C4 H4 106.8 . . ?
C6 C5 C4 112.16(13) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C1 C6 C5 112.72(13) . . ?
C1 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C1 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C9 C7 C10 108.54(14) . . ?
C9 C7 C8 108.97(15) . . ?
C10 C7 C8 107.59(15) . . ?
C9 C7 C4 111.92(14) . . ?
C10 C7 C4 109.85(13) . . ?
C8 C7 C4 109.87(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C16 115.58(14) . . ?
O1 C11 C12 124.80(15) . . ?
C16 C11 C12 119.61(15) . . ?
C13 C12 C11 119.47(15) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.02(15) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.37(15) . . ?
C13 C14 N1 119.52(15) . . ?
C15 C14 N1 119.05(15) . . ?
C16 C15 C14 118.63(15) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C11 120.86(15) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
O2 N1 O3 123.19(15) . . ?
O2 N1 C14 118.62(14) . . ?
O3 N1 C14 118.19(14) . . ?
C11 O1 C1 119.05(13) . . ?
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
C1 O1 1.460(2) . ?
C1 C2 1.516(2) . ?
C1 C6 1.520(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.529(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.533(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.534(2) . ?
C4 C7 1.556(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.530(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.534(2) . ?
C7 C10 1.534(2) . ?
C7 C8 1.534(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O1 1.352(2) . ?
C11 C16 1.396(2) . ?
C11 C12 1.399(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 N1 1.457(2) . ?
C15 C16 1.376(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N1 O2 1.2257(19) . ?
N1 O3 1.232(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 70.72(17) . . . . ?
C6 C1 C2 C3 -50.49(19) . . . . ?
C1 C2 C3 C4 56.24(19) . . . . ?
C2 C3 C4 C5 -58.25(17) . . . . ?
C2 C3 C4 C7 173.94(13) . . . . ?
C3 C4 C5 C6 58.23(17) . . . . ?
C7 C4 C5 C6 -174.04(13) . . . . ?
O1 C1 C6 C5 -67.81(17) . . . . ?
C2 C1 C6 C5 49.75(18) . . . . ?
C4 C5 C6 C1 -55.38(18) . . . . ?
C3 C4 C7 C9 61.46(18) . . . . ?
C5 C4 C7 C9 -62.86(18) . . . . ?
C3 C4 C7 C10 -59.18(18) . . . . ?
C5 C4 C7 C10 176.50(13) . . . . ?
C3 C4 C7 C8 -177.35(14) . . . . ?
C5 C4 C7 C8 58.33(18) . . . . ?
O1 C11 C12 C13 -179.95(14) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C12 C13 C14 N1 177.55(14) . . . . ?
C13 C14 C15 C16 -1.6(2) . . . . ?
N1 C14 C15 C16 -178.88(14) . . . . ?
C14 C15 C16 C11 2.3(2) . . . . ?
O1 C11 C16 C15 178.57(14) . . . . ?
C12 C11 C16 C15 -1.7(2) . . . . ?
C13 C14 N1 O2 -174.33(14) . . . . ?
C15 C14 N1 O2 3.0(2) . . . . ?
C13 C14 N1 O3 5.9(2) . . . . ?
C15 C14 N1 O3 -176.73(14) . . . . ?
C16 C11 O1 C1 -167.24(13) . . . . ?
C12 C11 O1 C1 13.0(2) . . . . ?
C2 C1 O1 C11 154.01(13) . . . . ?
C6 C1 O1 C11 -84.96(16) . . . . ?
