#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:28:05 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180300 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/14/7151442.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_7151442
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 H22 N2 O6'
_chemical_formula_weight         350.37
_chemical_melting_point          90.0(5)
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 112.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.388(5)
_cell_length_b                   7.1290(10)
_cell_length_c                   16.839(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      12
_cell_volume                     1705.9(9)
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3114
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  9600
_exptl_absorpt_coefficient_mu    0.104
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slabs
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0053(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0421
_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)+(0.0619P)²+0.3901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                2323
_reflns_number_total             2993
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303453d.txt
_cod_data_source_block           compound4e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '89.5-90.5' was changed to '90.0(5)'
- 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      P21/c
_cod_database_code               7151442
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.72333(14) 0.5798(3) 0.05189(13) 0.0252(4) Uani 1 1 d . . .
H1 H 0.7334 0.4554 0.0293 0.030 Uiso 1 1 calc R . .
C2 C 0.61885(14) 0.6181(3) 0.02241(13) 0.0272(4) Uani 1 1 d . . .
H2A H 0.5880 0.5081 0.0363 0.033 Uiso 1 1 calc R . .
H2B H 0.5921 0.6339 -0.0408 0.033 Uiso 1 1 calc R . .
C3 C 0.59658(13) 0.7923(3) 0.06375(12) 0.0238(4) Uani 1 1 d . . .
H3A H 0.5275 0.8040 0.0455 0.029 Uiso 1 1 calc R . .
H3B H 0.6196 0.9049 0.0434 0.029 Uiso 1 1 calc R . .
C4 C 0.64212(13) 0.7838(3) 0.16209(12) 0.0213(4) Uani 1 1 d . . .
H4 H 0.6178 0.6677 0.1798 0.026 Uiso 1 1 calc R . .
C5 C 0.74868(13) 0.7566(3) 0.18905(12) 0.0236(4) Uani 1 1 d . . .
H5A H 0.7753 0.8681 0.1715 0.028 Uiso 1 1 calc R . .
H5B H 0.7785 0.7466 0.2525 0.028 Uiso 1 1 calc R . .
C6 C 0.77208(14) 0.5819(3) 0.14896(12) 0.0258(4) Uani 1 1 d . . .
H6A H 0.8410 0.5757 0.1649 0.031 Uiso 1 1 calc R . .
H6B H 0.7531 0.4693 0.1727 0.031 Uiso 1 1 calc R . .
C7 C 0.61510(13) 0.9508(3) 0.20753(12) 0.0238(4) Uani 1 1 d . . .
C8 C 0.64759(15) 1.1391(3) 0.18508(14) 0.0297(5) Uani 1 1 d . . .
H8A H 0.7159 1.1364 0.2009 0.045 Uiso 1 1 calc R . .
H8B H 0.6316 1.2397 0.2167 0.045 Uiso 1 1 calc R . .
H8C H 0.6162 1.1618 0.1232 0.045 Uiso 1 1 calc R . .
C9 C 0.66088(15) 0.9241(3) 0.30551(13) 0.0308(5) Uani 1 1 d . . .
H9A H 0.7294 0.9193 0.3236 0.046 Uiso 1 1 calc R . .
H9B H 0.6386 0.8067 0.3213 0.046 Uiso 1 1 calc R . .
H9C H 0.6438 1.0294 0.3341 0.046 Uiso 1 1 calc R . .
C10 C 0.50833(14) 0.9561(3) 0.18173(14) 0.0314(5) Uani 1 1 d . . .
H10A H 0.4917 1.0624 0.2101 0.047 Uiso 1 1 calc R . .
H10B H 0.4875 0.8391 0.1994 0.047 Uiso 1 1 calc R . .
H10C H 0.4774 0.9703 0.1192 0.047 Uiso 1 1 calc R . .
C11 C 0.84148(13) 0.6946(3) 0.00463(12) 0.0227(4) Uani 1 1 d . . .
C12 C 0.86919(13) 0.8504(3) -0.04093(11) 0.0209(4) Uani 1 1 d . . .
C13 C 0.83455(12) 1.0331(3) -0.04923(11) 0.0204(4) Uani 1 1 d . . .
C14 C 0.85605(13) 1.1673(3) -0.09753(12) 0.0231(4) Uani 1 1 d . . .
H14 H 0.8308 1.2905 -0.1033 0.028 Uiso 1 1 calc R . .
C15 C 0.91591(13) 1.1152(3) -0.13733(12) 0.0224(4) Uani 1 1 d . . .
C16 C 0.95376(13) 0.9374(3) -0.13050(12) 0.0234(4) Uani 1 1 d . . .
H16 H 0.9952 0.9063 -0.1583 0.028 Uiso 1 1 calc R . .
C17 C 0.92966(13) 0.8056(3) -0.08198(12) 0.0224(4) Uani 1 1 d . . .
H17 H 0.9548 0.6824 -0.0766 0.027 Uiso 1 1 calc R . .
N1 N 0.77733(11) 1.0995(2) -0.00208(11) 0.0235(4) Uani 1 1 d . . .
N2 N 0.94115(12) 1.2581(2) -0.18833(11) 0.0289(4) Uani 1 1 d . . .
O1 O 0.76166(9) 0.73029(18) 0.01427(8) 0.0216(3) Uani 1 1 d . . .
O2 O 0.88637(10) 0.5506(2) 0.02498(10) 0.0331(4) Uani 1 1 d . . .
O3 O 0.81521(10) 1.1043(2) 0.07652(9) 0.0294(3) Uani 1 1 d . . .
O4 O 0.69733(10) 1.1520(2) -0.04435(10) 0.0342(4) Uani 1 1 d . . .
O5 O 0.90349(11) 1.4123(2) -0.19672(10) 0.0391(4) Uani 1 1 d . . .
O6 O 0.99891(13) 1.2138(2) -0.21819(12) 0.0470(5) 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 C6 109.95(15) . . ?
O1 C1 C2 106.05(15) . . ?
C6 C1 C2 112.08(16) . . ?
O1 C1 H1 109.6 . . ?
C6 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C1 C2 C3 113.16(16) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 111.82(16) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C5 108.54(15) . . ?
C3 C4 C7 113.83(15) . . ?
C5 C4 C7 114.05(15) . . ?
C3 C4 H4 106.6 . . ?
C5 C4 H4 106.6 . . ?
C7 C4 H4 106.6 . . ?
C6 C5 C4 112.26(16) . . ?
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 112.51(16) . . ?
C1 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C1 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C10 108.98(17) . . ?
C8 C7 C9 108.36(16) . . ?
C10 C7 C9 107.93(16) . . ?
C8 C7 C4 112.06(15) . . ?
C10 C7 C4 109.87(16) . . ?
C9 C7 C4 109.54(16) . . ?
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 . . ?
O2 C11 O1 125.71(18) . . ?
O2 C11 C12 121.91(17) . . ?
O1 C11 C12 112.26(16) . . ?
C17 C12 C13 117.87(18) . . ?
C17 C12 C11 117.29(17) . . ?
C13 C12 C11 124.73(17) . . ?
C14 C13 C12 122.66(18) . . ?
C14 C13 N1 115.12(16) . . ?
C12 C13 N1 122.10(17) . . ?
C13 C14 C15 117.13(18) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C14 C15 C16 122.99(18) . . ?
C14 C15 N2 118.01(17) . . ?
C16 C15 N2 118.99(17) . . ?
C15 C16 C17 118.15(18) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C12 121.19(18) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
O4 N1 O3 125.22(17) . . ?
O4 N1 C13 117.53(16) . . ?
O3 N1 C13 117.19(15) . . ?
O6 N2 O5 124.93(18) . . ?
O6 N2 C15 117.21(17) . . ?
O5 N2 C15 117.86(16) . . ?
C11 O1 C1 117.01(14) . . ?
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 1.479(2) . ?
C1 C6 1.515(3) . ?
C1 C2 1.514(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.532(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.537(3) . ?
C4 C7 1.555(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.524(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.530(3) . ?
C7 C10 1.530(3) . ?
C7 C9 1.537(3) . ?
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 O2 1.211(2) . ?
C11 O1 1.324(2) . ?
C11 C12 1.502(3) . ?
C12 C17 1.392(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.376(3) . ?
C13 N1 1.472(2) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C15 N2 1.477(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N1 O4 1.221(2) . ?
N1 O3 1.225(2) . ?
N2 O6 1.219(2) . ?
N2 O5 1.225(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 -69.63(19) . . . . ?
C6 C1 C2 C3 50.4(2) . . . . ?
C1 C2 C3 C4 -54.5(2) . . . . ?
C2 C3 C4 C5 56.4(2) . . . . ?
C2 C3 C4 C7 -175.43(16) . . . . ?
C3 C4 C5 C6 -56.9(2) . . . . ?
C7 C4 C5 C6 175.07(15) . . . . ?
O1 C1 C6 C5 67.5(2) . . . . ?
C2 C1 C6 C5 -50.2(2) . . . . ?
C4 C5 C6 C1 54.8(2) . . . . ?
C3 C4 C7 C8 -62.2(2) . . . . ?
C5 C4 C7 C8 63.1(2) . . . . ?
C3 C4 C7 C10 59.1(2) . . . . ?
C5 C4 C7 C10 -175.55(16) . . . . ?
C3 C4 C7 C9 177.55(15) . . . . ?
C5 C4 C7 C9 -57.2(2) . . . . ?
O2 C11 C12 C17 18.9(3) . . . . ?
O1 C11 C12 C17 -157.40(16) . . . . ?
O2 C11 C12 C13 -165.01(18) . . . . ?
O1 C11 C12 C13 18.7(3) . . . . ?
C17 C12 C13 C14 1.5(3) . . . . ?
C11 C12 C13 C14 -174.53(17) . . . . ?
C17 C12 C13 N1 -174.28(16) . . . . ?
C11 C12 C13 N1 9.7(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
N1 C13 C14 C15 174.92(16) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C13 C14 C15 N2 -179.01(16) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
N2 C15 C16 C17 179.64(16) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C13 C12 C17 C16 -0.8(3) . . . . ?
C11 C12 C17 C16 175.52(17) . . . . ?
C14 C13 N1 O4 65.2(2) . . . . ?
C12 C13 N1 O4 -118.70(19) . . . . ?
C14 C13 N1 O3 -112.05(19) . . . . ?
C12 C13 N1 O3 64.1(2) . . . . ?
C14 C15 N2 O6 175.16(18) . . . . ?
C16 C15 N2 O6 -4.0(3) . . . . ?
C14 C15 N2 O5 -4.1(3) . . . . ?
C16 C15 N2 O5 176.79(17) . . . . ?
O2 C11 O1 C1 -1.1(3) . . . . ?
C12 C11 O1 C1 175.08(14) . . . . ?
C6 C1 O1 C11 81.80(19) . . . . ?
C2 C1 O1 C11 -156.83(15) . . . . ?
