#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:28:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180300 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/14/7151445.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_7151445
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 Cl N O4'
_chemical_formula_weight         339.81
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 107.5550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9757(3)
_cell_length_b                   36.6182(8)
_cell_length_c                   7.0342(2)
_cell_measurement_reflns_used    25460
_cell_measurement_temperature    130.0(2)
_cell_volume                     1713.12(10)
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130.0(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10738
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.34
_exptl_absorpt_coefficient_mu    0.242
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.0407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                1991
_reflns_number_total             2860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303453d.txt
_cod_data_source_block           compound4h
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7151445
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.1205(3) -0.12455(6) 0.5856(3) 0.0300(5) Uani 1 1 d . . .
H1 H -0.0012 -0.1167 0.4765 0.036 Uiso 1 1 calc R . .
C2 C 0.2394(3) -0.15216(6) 0.5072(3) 0.0327(6) Uani 1 1 d . . .
H2A H 0.2887 -0.1404 0.4040 0.039 Uiso 1 1 calc R . .
H2B H 0.1496 -0.1725 0.4434 0.039 Uiso 1 1 calc R . .
C3 C 0.4177(3) -0.16739(6) 0.6708(3) 0.0291(5) Uani 1 1 d . . .
H3A H 0.5160 -0.1476 0.7234 0.035 Uiso 1 1 calc R . .
H3B H 0.4850 -0.1864 0.6136 0.035 Uiso 1 1 calc R . .
C4 C 0.3529(3) -0.18393(6) 0.8424(3) 0.0267(5) Uani 1 1 d . . .
H4 H 0.2529 -0.2034 0.7815 0.032 Uiso 1 1 calc R . .
C5 C 0.2388(3) -0.15516(6) 0.9230(3) 0.0311(5) Uani 1 1 d . . .
H5A H 0.3318 -0.1350 0.9840 0.037 Uiso 1 1 calc R . .
H5B H 0.1906 -0.1663 1.0285 0.037 Uiso 1 1 calc R . .
C6 C 0.0593(3) -0.13958(6) 0.7602(3) 0.0325(6) Uani 1 1 d . . .
H6A H -0.0424 -0.1590 0.7118 0.039 Uiso 1 1 calc R . .
H6B H -0.0031 -0.1198 0.8174 0.039 Uiso 1 1 calc R . .
C7 C 0.5263(3) -0.20321(6) 1.0053(3) 0.0321(6) Uani 1 1 d . . .
C8 C 0.6818(4) -0.17579(7) 1.1244(4) 0.0525(7) Uani 1 1 d . . .
H8A H 0.6151 -0.1575 1.1845 0.079 Uiso 1 1 calc R . .
H8B H 0.7459 -0.1636 1.0353 0.079 Uiso 1 1 calc R . .
H8C H 0.7841 -0.1886 1.2297 0.079 Uiso 1 1 calc R . .
C9 C 0.6314(4) -0.23113(7) 0.9103(3) 0.0447(7) Uani 1 1 d . . .
H9A H 0.5323 -0.2486 0.8321 0.067 Uiso 1 1 calc R . .
H9B H 0.7334 -0.2442 1.0150 0.067 Uiso 1 1 calc R . .
H9C H 0.6959 -0.2186 0.8228 0.067 Uiso 1 1 calc R . .
C10 C 0.4366(4) -0.22384(7) 1.1491(4) 0.0513(7) Uani 1 1 d . . .
H10A H 0.3669 -0.2066 1.2116 0.077 Uiso 1 1 calc R . .
H10B H 0.5448 -0.2359 1.2523 0.077 Uiso 1 1 calc R . .
H10C H 0.3411 -0.2422 1.0749 0.077 Uiso 1 1 calc R . .
C11 C 0.1780(3) -0.06046(6) 0.6520(3) 0.0248(5) Uani 1 1 d . . .
C12 C 0.3361(3) -0.03180(6) 0.7033(3) 0.0226(5) Uani 1 1 d . . .
C13 C 0.2788(3) 0.00446(6) 0.7147(3) 0.0231(5) Uani 1 1 d . . .
H13 H 0.1420 0.0104 0.6974 0.028 Uiso 1 1 calc R . .
C14 C 0.4220(3) 0.03158(6) 0.7510(3) 0.0225(5) Uani 1 1 d . . .
C15 C 0.6244(3) 0.02350(6) 0.7836(3) 0.0244(5) Uani 1 1 d . . .
C16 C 0.6816(3) -0.01239(6) 0.7762(3) 0.0278(5) Uani 1 1 d . . .
H16 H 0.8196 -0.0182 0.8006 0.033 Uiso 1 1 calc R . .
C17 C 0.5387(3) -0.04007(6) 0.7334(3) 0.0265(5) Uani 1 1 d . . .
H17 H 0.5788 -0.0646 0.7245 0.032 Uiso 1 1 calc R . .
N1 N 0.3542(3) 0.06959(5) 0.7486(3) 0.0275(4) Uani 1 1 d . . .
O1 O 0.2572(2) -0.09358(4) 0.6530(2) 0.0284(4) Uani 1 1 d . . .
O2 O -0.0009(2) -0.05414(4) 0.6107(2) 0.0301(4) Uani 1 1 d . . .
O3 O 0.2371(2) 0.07688(4) 0.8439(2) 0.0340(4) Uani 1 1 d . . .
O4 O 0.4141(2) 0.09179(4) 0.6487(2) 0.0368(4) Uani 1 1 d . . .
Cl1 Cl 0.80951(8) 0.056615(16) 0.84170(8) 0.03503(19) 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'
Cl Cl 0.1484 0.1585 '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 105.08(17) . . ?
O1 C1 C6 109.45(16) . . ?
C2 C1 C6 111.76(18) . . ?
O1 C1 H1 110.1 . . ?
C2 C1 H1 110.1 . . ?
C6 C1 H1 110.1 . . ?
C1 C2 C3 112.45(18) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 111.78(17) . . ?
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 . . ?
C5 C4 C3 109.24(17) . . ?
C5 C4 C7 114.47(16) . . ?
C3 C4 C7 114.10(17) . . ?
C5 C4 H4 106.1 . . ?
C3 C4 H4 106.1 . . ?
C7 C4 H4 106.1 . . ?
C4 C5 C6 112.30(18) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C1 C6 C5 111.98(17) . . ?
C1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C9 C7 C8 108.99(19) . . ?
C9 C7 C10 107.7(2) . . ?
C8 C7 C10 108.91(18) . . ?
C9 C7 C4 110.50(17) . . ?
C8 C7 C4 111.69(19) . . ?
C10 C7 C4 109.00(18) . . ?
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 124.7(2) . . ?
O2 C11 C12 123.9(2) . . ?
O1 C11 C12 111.43(17) . . ?
C13 C12 C17 119.4(2) . . ?
C13 C12 C11 118.78(18) . . ?
C17 C12 C11 121.75(19) . . ?
C14 C13 C12 119.50(19) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.4(2) . . ?
C13 C14 N1 117.92(18) . . ?
C15 C14 N1 120.69(19) . . ?
C16 C15 C14 119.13(19) . . ?
C16 C15 Cl1 118.28(16) . . ?
C14 C15 Cl1 122.55(17) . . ?
C15 C16 C17 120.46(19) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
O4 N1 O3 124.30(18) . . ?
O4 N1 C14 118.09(17) . . ?
O3 N1 C14 117.59(17) . . ?
C11 O1 C1 118.31(16) . . ?
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 1.466(2) . ?
C1 C2 1.513(3) . ?
C1 C6 1.520(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.523(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.536(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.529(3) . ?
C4 C7 1.562(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.530(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.524(3) . ?
C7 C8 1.529(3) . ?
C7 C10 1.539(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 1.215(2) . ?
C11 O1 1.332(2) . ?
C11 C12 1.486(3) . ?
C12 C13 1.396(3) . ?
C12 C17 1.398(3) . ?
C13 C14 1.377(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 N1 1.468(3) . ?
C15 C16 1.379(3) . ?
C15 Cl1 1.728(2) . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N1 O4 1.227(2) . ?
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 65.9(2) . . . . ?
C6 C1 C2 C3 -52.7(2) . . . . ?
C1 C2 C3 C4 55.3(2) . . . . ?
C2 C3 C4 C5 -55.8(2) . . . . ?
C2 C3 C4 C7 174.62(18) . . . . ?
C3 C4 C5 C6 55.7(2) . . . . ?
C7 C4 C5 C6 -174.94(17) . . . . ?
O1 C1 C6 C5 -63.9(2) . . . . ?
C2 C1 C6 C5 52.0(2) . . . . ?
C4 C5 C6 C1 -54.6(2) . . . . ?
C5 C4 C7 C9 -179.65(19) . . . . ?
C3 C4 C7 C9 -52.8(2) . . . . ?
C5 C4 C7 C8 -58.1(2) . . . . ?
C3 C4 C7 C8 68.7(2) . . . . ?
C5 C4 C7 C10 62.2(2) . . . . ?
C3 C4 C7 C10 -170.87(19) . . . . ?
O2 C11 C12 C13 3.2(3) . . . . ?
O1 C11 C12 C13 -178.13(16) . . . . ?
O2 C11 C12 C17 -174.55(18) . . . . ?
O1 C11 C12 C17 4.1(3) . . . . ?
C17 C12 C13 C14 1.4(3) . . . . ?
C11 C12 C13 C14 -176.39(17) . . . . ?
C12 C13 C14 C15 -2.2(3) . . . . ?
C12 C13 C14 N1 175.96(17) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
N1 C14 C15 C16 -177.18(18) . . . . ?
C13 C14 C15 Cl1 -176.75(15) . . . . ?
N1 C14 C15 Cl1 5.1(3) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
Cl1 C15 C16 C17 178.95(14) . . . . ?
C15 C16 C17 C12 -2.0(3) . . . . ?
C13 C12 C17 C16 0.7(3) . . . . ?
C11 C12 C17 C16 178.38(17) . . . . ?
C13 C14 N1 O4 -130.31(19) . . . . ?
C15 C14 N1 O4 47.9(2) . . . . ?
C13 C14 N1 O3 48.2(2) . . . . ?
C15 C14 N1 O3 -133.66(18) . . . . ?
O2 C11 O1 C1 4.8(3) . . . . ?
C12 C11 O1 C1 -173.86(15) . . . . ?
C2 C1 O1 C11 152.66(16) . . . . ?
C6 C1 O1 C11 -87.2(2) . . . . ?
