#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/01/7150135.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_7150135
loop_
_publ_author_name
'Kanamori, Daisuke'
'Furukawa, Atsushi'
'Okamura, Taka-aki'
'Yamamoto, Hitoshi'
'Ueyama, Norikazu'
_publ_section_title
;
 Contribution of the intramolecular hydrogen bond to the shift of the
 pKa value and the oxidation potential of phenols and phenolate anions.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1453
_journal_page_last               1459
_journal_paper_doi               10.1039/b419361j
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C16 H23 N2 O3, C4 H12 N'
_chemical_formula_sum            'C20 H35 N3 O3'
_chemical_formula_weight         365.51
_chemical_name_systematic
;
?
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_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            4
_cell_length_a                   13.2912(6)
_cell_length_b                   13.0775(5)
_cell_length_c                   12.1094(5)
_cell_measurement_reflns_used    10935
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     2104.80(15)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9436
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(10)
_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     127
_refine_ls_number_reflns         2451
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0637P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                2171
_reflns_number_total             2451
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b419361j-ccdc.txt
_cod_data_source_block           2'ONMe4
_cod_original_sg_symbol_Hall     'C 2c -2     '
_cod_original_sg_symbol_H-M      'C m c 21     '
_cod_database_code               7150135
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'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
O1 O 0.72771(7) 0.66397(7) 0.85876(8) 0.0370(2) Uani 1 1 d . . .
O11 O 1.0000 0.54281(10) 0.97458(12) 0.0334(3) Uani 1 2 d S . .
N1 N 0.80465(8) 0.53963(8) 0.95973(9) 0.0281(3) Uani 1 1 d . . .
H1 H 0.8637 0.5153 0.9794 0.034 Uiso 1 1 calc R . .
N11 N 1.0000 0.30242(11) 0.77480(13) 0.0295(3) Uani 1 2 d S . .
C1 C 0.80537(9) 0.62052(9) 0.89151(10) 0.0254(3) Uani 1 1 d . . .
C11 C 1.0000 0.61349(12) 0.89826(15) 0.0246(4) Uani 1 2 d S . .
C12 C 0.90796(9) 0.65401(9) 0.85382(11) 0.0252(3) Uani 1 1 d . . .
C13 C 0.91059(9) 0.72639(10) 0.77009(11) 0.0284(3) Uani 1 1 d . . .
H13 H 0.8489 0.7519 0.7415 0.034 Uiso 1 1 calc R . .
C14 C 1.0000 0.76262(14) 0.72685(16) 0.0324(4) Uani 1 2 d S . .
H14 H 1.0000 0.8114 0.6687 0.039 Uiso 1 2 calc SR . .
C17 C 0.71609(9) 0.48729(10) 1.00523(11) 0.0292(3) Uani 1 1 d . . .
C18 C 0.64712(14) 0.45046(15) 0.91402(16) 0.0569(5) Uani 1 1 d . . .
H18A H 0.6844 0.4047 0.8647 0.068 Uiso 1 1 calc R . .
H18B H 0.6223 0.5093 0.8720 0.068 Uiso 1 1 calc R . .
H18C H 0.5901 0.4136 0.9464 0.068 Uiso 1 1 calc R . .
C19 C 0.66019(13) 0.55816(13) 1.08305(14) 0.0494(4) Uani 1 1 d . . .
H19A H 0.7059 0.5812 1.1415 0.059 Uiso 1 1 calc R . .
H19B H 0.6033 0.5216 1.1161 0.059 Uiso 1 1 calc R . .
H19C H 0.6353 0.6175 1.0419 0.059 Uiso 1 1 calc R . .
C20 C 0.75680(14) 0.39590(13) 1.06882(19) 0.0589(5) Uani 1 1 d . . .
H20A H 0.8014 0.4199 1.1279 0.071 Uiso 1 1 calc R . .
H20B H 0.7946 0.3515 1.0185 0.071 Uiso 1 1 calc R . .
H20C H 0.7007 0.3575 1.1010 0.071 Uiso 1 1 calc R . .
C21 C 1.0000 0.19983(17) 0.7210(2) 0.0459(5) Uani 1 2 d S . .
H21A H 1.0000 0.2082 0.6406 0.055 Uiso 1 2 calc SR . .
H21B H 0.9398 0.1619 0.7435 0.055 Uiso 0.50 1 calc PR . .
H21C H 1.0602 0.1619 0.7435 0.055 Uiso 0.50 1 calc PR . .
C22 C 1.0000 0.28741(18) 0.89683(17) 0.0421(5) Uani 1 2 d S . .
H22A H 1.0000 0.3542 0.9336 0.051 Uiso 1 2 calc SR . .
H22B H 1.0602 0.2491 0.9185 0.051 Uiso 0.50 1 calc PR . .
H22C H 0.9398 0.2491 0.9185 0.051 Uiso 0.50 1 calc PR . .
C23 C 0.90792(11) 0.36003(14) 0.74125(15) 0.0465(4) Uani 1 1 d . . .
H23A H 0.9080 0.4274 0.7768 0.056 Uiso 1 1 calc R . .
H23B H 0.8479 0.3219 0.7641 0.056 Uiso 1 1 calc R . .
H23C H 0.9074 0.3686 0.6609 0.056 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 0.0033 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'
O O 0.0106 0.0060 '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'
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
C1 N1 C17 127.14(11) . . ?
C1 N1 H1 116.4 . . ?
C17 N1 H1 116.4 . . ?
C22 N11 C21 108.34(17) . . ?
C22 N11 C23 109.64(11) . 2_755 ?
C21 N11 C23 109.56(11) . 2_755 ?
C22 N11 C23 109.64(11) . . ?
C21 N11 C23 109.56(11) . . ?
C23 N11 C23 110.07(17) 2_755 . ?
O1 C1 N1 123.42(12) . . ?
O1 C1 C12 121.53(11) . . ?
N1 C1 C12 115.02(10) . . ?
O11 C11 C12 121.69(7) . . ?
O11 C11 C12 121.69(7) . 2_755 ?
C12 C11 C12 116.62(15) . 2_755 ?
C13 C12 C11 120.23(11) . . ?
C13 C12 C1 116.33(10) . . ?
C11 C12 C1 123.42(11) . . ?
C14 C13 C12 122.16(11) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C13 118.56(16) . 2_755 ?
C13 C14 H14 120.7 . . ?
C13 C14 H14 120.7 2_755 . ?
N1 C17 C18 111.09(12) . . ?
N1 C17 C19 109.93(11) . . ?
C18 C17 C19 110.56(13) . . ?
N1 C17 C20 105.72(11) . . ?
C18 C17 C20 109.55(15) . . ?
C19 C17 C20 109.87(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N11 C21 H21A 109.5 . . ?
N11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N11 C22 H22A 109.5 . . ?
N11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N11 C23 H23A 109.5 . . ?
N11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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 C1 1.2433(15) . ?
O11 C11 1.307(2) . ?
N1 C1 1.3421(16) . ?
N1 C17 1.4690(15) . ?
N1 H1 0.8800 . ?
N11 C22 1.491(3) . ?
N11 C21 1.492(3) . ?
N11 C23 1.4934(16) 2_755 ?
N11 C23 1.4934(16) . ?
C1 C12 1.5032(17) . ?
C11 C12 1.4377(14) . ?
C11 C12 1.4377(14) 2_755 ?
C12 C13 1.3875(18) . ?
C13 C14 1.3823(15) . ?
C13 H13 0.9500 . ?
C14 C13 1.3823(15) 2_755 ?
C14 H14 0.9500 . ?
C17 C18 1.514(2) . ?
C17 C19 1.516(2) . ?
C17 C20 1.521(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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
C17 N1 C1 O1 1.4(2) . . . . ?
C17 N1 C1 C12 -176.83(11) . . . . ?
O11 C11 C12 C13 -177.71(14) . . . . ?
C12 C11 C12 C13 1.8(2) 2_755 . . . ?
O11 C11 C12 C1 0.9(2) . . . . ?
C12 C11 C12 C1 -179.63(8) 2_755 . . . ?
O1 C1 C12 C13 -8.22(18) . . . . ?
N1 C1 C12 C13 170.07(11) . . . . ?
O1 C1 C12 C11 173.12(13) . . . . ?
N1 C1 C12 C11 -8.59(18) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C1 C12 C13 C14 -179.10(14) . . . . ?
C12 C13 C14 C13 -1.0(3) . . . 2_755 ?
C1 N1 C17 C18 56.43(17) . . . . ?
C1 N1 C17 C19 -66.27(18) . . . . ?
C1 N1 C17 C20 175.20(14) . . . . ?
