#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/01/7150133.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_7150133
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         'C11 H14 N O2, C8 H20 N, H2 O'
_chemical_formula_sum            'C19 H36 N2 O3'
_chemical_formula_weight         340.50
_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                97.147(15)
_cell_angle_beta                 92.285(15)
_cell_angle_gamma                109.753(14)
_cell_formula_units_Z            2
_cell_length_a                   10.0678(16)
_cell_length_b                   12.211(3)
_cell_length_c                   9.0829(12)
_cell_measurement_reflns_used    9
_cell_measurement_temperature    298
_cell_measurement_theta_max      13.7
_cell_measurement_theta_min      13.1
_cell_volume                     1038.7(4)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    MULTAN88
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.2334
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5729
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0.53
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.3179
_refine_ls_R_factor_gt           0.0688
_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)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.2319
_reflns_number_gt                1179
_reflns_number_total             4752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b419361j-ccdc.txt
_cod_data_source_block           1'ONEt4
_cod_original_cell_volume        1038.8(3)
_cod_original_sg_symbol_Hall     '-P 1         '
_cod_original_sg_symbol_H-M      'P -1         '
_cod_database_code               7150133
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
O11 O 0.3893(2) 0.3755(2) 0.7916(3) 0.0593(8) Uani 1 1 d . . .
O1 O -0.0119(3) 0.1119(2) 0.7047(3) 0.0829(10) Uani 1 1 d . . .
O100 O 0.3411(3) 0.5125(2) 1.0420(3) 0.0850(10) Uani 1 1 d . . .
N1 N 0.1076(3) 0.3059(3) 0.7266(3) 0.0543(9) Uani 1 1 d . . .
H1 H 0.1906 0.3583 0.7309 0.065 Uiso 1 1 calc R . .
N21 N 0.3178(4) 0.2147(3) 0.2154(4) 0.0677(10) Uani 1 1 d . . .
C11 C 0.3731(4) 0.2667(4) 0.7449(4) 0.0491(10) Uani 1 1 d . . .
C12 C 0.2390(4) 0.1748(3) 0.7057(4) 0.0473(10) Uani 1 1 d . . .
C13 C 0.2319(5) 0.0606(4) 0.6528(4) 0.0621(12) Uani 1 1 d . . .
H13 H 0.1439 0.0019 0.6279 0.075 Uiso 1 1 calc R . .
C14 C 0.3530(6) 0.0334(4) 0.6370(5) 0.0754(14) Uani 1 1 d . . .
H14 H 0.3467 -0.0431 0.6010 0.091 Uiso 1 1 calc R . .
C15 C 0.4836(5) 0.1199(5) 0.6747(5) 0.0795(14) Uani 1 1 d . . .
H15 H 0.5655 0.1016 0.6639 0.095 Uiso 1 1 calc R . .
C16 C 0.4937(5) 0.2321(4) 0.7277(4) 0.0667(12) Uani 1 1 d . . .
H16 H 0.5832 0.2884 0.7538 0.080 Uiso 1 1 calc R . .
C1 C 0.1018(4) 0.1940(4) 0.7141(4) 0.0510(10) Uani 1 1 d . . .
C17 C -0.0118(4) 0.3497(3) 0.7339(5) 0.0607(11) Uani 1 1 d . . .
C18 C -0.1115(5) 0.2982(4) 0.5929(5) 0.0901(16) Uani 1 1 d . . .
H18A H -0.0603 0.3187 0.5076 0.108 Uiso 1 1 calc R . .
H18B H -0.1873 0.3293 0.5956 0.108 Uiso 1 1 calc R . .
H18C H -0.1498 0.2142 0.5865 0.108 Uiso 1 1 calc R . .
C19 C 0.0525(5) 0.4822(4) 0.7431(6) 0.0943(16) Uani 1 1 d . . .
H19A H 0.1015 0.5012 0.6561 0.113 Uiso 1 1 calc R . .
H19B H 0.1180 0.5137 0.8303 0.113 Uiso 1 1 calc R . .
H19C H -0.0212 0.5155 0.7487 0.113 Uiso 1 1 calc R . .
C20 C -0.0893(5) 0.3193(4) 0.8694(5) 0.0913(16) Uani 1 1 d . . .
H20A H -0.0248 0.3523 0.9572 0.110 Uiso 1 1 calc R . .
H20B H -0.1280 0.2354 0.8643 0.110 Uiso 1 1 calc R . .
H20C H -0.1647 0.3509 0.8733 0.110 Uiso 1 1 calc R . .
C21 C 0.2033(5) 0.2215(4) 0.1130(6) 0.1031(17) Uani 1 1 d . . .
H21A H 0.2070 0.1815 0.0149 0.124 Uiso 1 1 calc R . .
H21B H 0.2199 0.3034 0.1045 0.124 Uiso 1 1 calc R . .
C22 C 0.0530(5) 0.1662(5) 0.1647(7) 0.134(2) Uani 1 1 d . . .
H22A H -0.0162 0.1733 0.0943 0.161 Uiso 1 1 calc R . .
H22B H 0.0476 0.2065 0.2608 0.161 Uiso 1 1 calc R . .
H22C H 0.0348 0.0846 0.1710 0.161 Uiso 1 1 calc R . .
C23 C 0.3155(8) 0.2609(6) 0.3704(6) 0.138(3) Uani 1 1 d . . .
H23A H 0.3967 0.2571 0.4280 0.165 Uiso 1 1 calc R . .
H23B H 0.2307 0.2119 0.4089 0.165 Uiso 1 1 calc R . .
C24 C 0.3189(7) 0.3965(6) 0.3917(6) 0.144(3) Uani 1 1 d . . .
H24A H 0.3174 0.4232 0.4954 0.173 Uiso 1 1 calc R . .
H24B H 0.2376 0.4005 0.3367 0.173 Uiso 1 1 calc R . .
H24C H 0.4037 0.4457 0.3554 0.173 Uiso 1 1 calc R . .
C25 C 0.4544(5) 0.2800(4) 0.1536(6) 0.1009(17) Uani 1 1 d . . .
H25A H 0.4620 0.3616 0.1559 0.121 Uiso 1 1 calc R . .
H25B H 0.4514 0.2467 0.0503 0.121 Uiso 1 1 calc R . .
C26 C 0.5868(6) 0.2756(6) 0.2391(9) 0.162(3) Uani 1 1 d . . .
H26A H 0.6698 0.3188 0.1947 0.194 Uiso 1 1 calc R . .
H26B H 0.5814 0.1953 0.2352 0.194 Uiso 1 1 calc R . .
H26C H 0.5918 0.3101 0.3411 0.194 Uiso 1 1 calc R . .
C27 C 0.3081(6) 0.0835(5) 0.2142(7) 0.1074(19) Uani 1 1 d . . .
H27A H 0.3840 0.0818 0.2821 0.129 Uiso 1 1 calc R . .
H27B H 0.2191 0.0404 0.2509 0.129 Uiso 1 1 calc R . .
C28 C 0.3177(7) 0.0234(5) 0.0647(7) 0.132(2) Uani 1 1 d . . .
H28A H 0.3111 -0.0561 0.0715 0.159 Uiso 1 1 calc R . .
H28B H 0.4067 0.0643 0.0285 0.159 Uiso 1 1 calc R . .
H28C H 0.2416 0.0230 -0.0027 0.159 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'
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
C1 N1 C17 127.5(3) . . ?
C1 N1 H1 116.2 . . ?
C17 N1 H1 116.2 . . ?
C23 N21 C21 114.7(5) . . ?
C23 N21 C25 111.6(4) . . ?
C21 N21 C25 105.6(3) . . ?
C23 N21 C27 105.8(4) . . ?
C21 N21 C27 110.7(3) . . ?
C25 N21 C27 108.4(4) . . ?
O11 C11 C16 120.0(4) . . ?
O11 C11 C12 124.6(4) . . ?
C16 C11 C12 115.4(4) . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 C1 116.2(4) . . ?
C11 C12 C1 123.2(3) . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.7(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 122.8(4) . . ?
C15 C16 H16 118.6 . . ?
C11 C16 H16 118.6 . . ?
O1 C1 N1 121.6(4) . . ?
O1 C1 C12 122.2(4) . . ?
N1 C1 C12 116.1(3) . . ?
N1 C17 C20 111.0(3) . . ?
N1 C17 C19 106.0(3) . . ?
C20 C17 C19 109.7(4) . . ?
N1 C17 C18 109.4(3) . . ?
C20 C17 C18 110.6(4) . . ?
C19 C17 C18 110.0(4) . . ?
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 . . ?
N21 C21 C22 113.4(4) . . ?
N21 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
N21 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N21 C23 C24 112.4(4) . . ?
N21 C23 H23A 109.1 . . ?
C24 C23 H23A 109.1 . . ?
N21 C23 H23B 109.1 . . ?
C24 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N21 C25 C26 113.6(4) . . ?
N21 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
N21 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 N21 113.6(4) . . ?
C28 C27 H27A 108.8 . . ?
N21 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
N21 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
O11 C11 1.295(4) . ?
O1 C1 1.232(4) . ?
N1 C1 1.338(4) . ?
N1 C17 1.472(5) . ?
N1 H1 0.8600 . ?
N21 C23 1.454(6) . ?
N21 C21 1.484(5) . ?
N21 C25 1.508(5) . ?
N21 C27 1.570(6) . ?
C11 C16 1.423(5) . ?
C11 C12 1.431(5) . ?
C12 C13 1.394(5) . ?
C12 C1 1.481(5) . ?
C13 C14 1.376(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C20 1.502(6) . ?
C17 C19 1.515(5) . ?
C17 C18 1.521(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.552(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.632(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.535(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.485(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
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
O11 C11 C12 C13 178.4(3) . . . . ?
C16 C11 C12 C13 -0.9(5) . . . . ?
O11 C11 C12 C1 0.1(6) . . . . ?
C16 C11 C12 C1 -179.1(3) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C1 C12 C13 C14 178.4(4) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C14 C15 C16 C11 -1.0(7) . . . . ?
O11 C11 C16 C15 -177.9(4) . . . . ?
C12 C11 C16 C15 1.4(6) . . . . ?
C17 N1 C1 O1 1.2(6) . . . . ?
C17 N1 C1 C12 178.6(3) . . . . ?
C13 C12 C1 O1 14.3(5) . . . . ?
C11 C12 C1 O1 -167.4(4) . . . . ?
C13 C12 C1 N1 -163.2(3) . . . . ?
C11 C12 C1 N1 15.2(5) . . . . ?
C1 N1 C17 C20 62.5(5) . . . . ?
C1 N1 C17 C19 -178.4(4) . . . . ?
C1 N1 C17 C18 -59.9(5) . . . . ?
C23 N21 C21 C22 -52.6(6) . . . . ?
C25 N21 C21 C22 -175.9(5) . . . . ?
C27 N21 C21 C22 67.0(6) . . . . ?
C21 N21 C23 C24 -55.6(6) . . . . ?
C25 N21 C23 C24 64.4(6) . . . . ?
C27 N21 C23 C24 -177.8(5) . . . . ?
C23 N21 C25 C26 58.8(6) . . . . ?
C21 N21 C25 C26 -176.0(5) . . . . ?
C27 N21 C25 C26 -57.4(6) . . . . ?
C23 N21 C27 C28 -176.6(5) . . . . ?
C21 N21 C27 C28 58.6(6) . . . . ?
C25 N21 C27 C28 -56.8(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653334
