#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/85/1508543.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_1508543
loop_
_publ_author_name
'Markle, Todd F.'
'Tronic, Tristan A.'
'Dipasquale, Antonio G.'
'Kaminsky, Werner'
'Mayer, James M.'
_publ_section_title
;
 Effect of basic site substituents on concerted proton-electron transfer
 in hydrogen-bonded pyridyl-phenols.
;
_journal_issue                   50
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              12249
_journal_page_last               12259
_journal_paper_doi               10.1021/jp311388n
_journal_volume                  116
_journal_year                    2012
_chemical_formula_moiety         'C20 H27 N O'
_chemical_formula_sum            'C20 H27 N O'
_chemical_formula_weight         297.43
_chemical_name_common            HOArpyCH3
_chemical_name_systematic
; 
 HOArpyCH3
;
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      57
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_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                   9.6250(3)
_cell_length_b                   26.7940(4)
_cell_length_c                   6.9060(14)
_cell_measurement_reflns_used    109
_cell_measurement_temperature    130(2)
_cell_volume                     1781.0(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'maXus, Zortep'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_av_sigmaI/netI    0.0809
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1925
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   HKL-2000
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0607
_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)+(0.0730P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1520
_reflns_number_gt                976
_reflns_number_total             1925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp311388n_si_002.cif
_cod_data_source_block           HOArpyCH3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               1508543
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y-1/2, 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
O1 O -0.34977(18) 0.13876(8) 0.2500 0.0371(5) Uani 1 2 d S
H1 H -0.377(3) 0.1752(13) 0.2500 0.056 Uiso 1 2 d S
C3 C 0.0020(3) 0.08979(10) 0.2500 0.0311(7) Uani 1 2 d S
H3 H 0.0479 0.0584 0.2500 0.037 Uiso 1 2 calc SR
C2 C -0.1428(3) 0.09015(10) 0.2500 0.0270(7) Uani 1 2 d S
C1 C -0.2084(3) 0.13734(10) 0.2500 0.0286(6) Uani 1 2 d S
C6 C -0.1304(3) 0.18188(10) 0.2500 0.0281(7) Uani 1 2 d S
N1 N -0.3369(2) 0.23326(9) 0.2500 0.0365(6) Uani 1 2 d S
C7 C -0.2281(3) 0.04195(10) 0.2500 0.0326(7) Uani 1 2 d S
C13 C -0.1967(3) 0.23171(10) 0.2500 0.0297(7) Uani 1 2 d S
C14 C -0.1207(3) 0.27624(11) 0.2500 0.0331(7) Uani 1 2 d S
H14 H -0.0221 0.2748 0.2500 0.040 Uiso 1 2 calc SR
C5 C 0.0139(3) 0.17783(10) 0.2500 0.0316(7) Uani 1 2 d S
H5 H 0.0674 0.2076 0.2500 0.038 Uiso 1 2 calc SR
C15 C -0.1857(3) 0.32221(10) 0.2500 0.0343(7) Uani 1 2 d S
C4 C 0.0833(3) 0.13260(10) 0.2500 0.0284(6) Uani 1 2 d S
C9 C -0.1373(3) -0.00506(11) 0.2500 0.0410(8) Uani 1 2 d S
H9A H -0.1965 -0.0347 0.2500 0.061 Uiso 1 2 d SR
H9B H -0.0848 -0.0068 0.3714 0.061 Uiso 0.50 1 d PR
H9C H -0.0725 -0.0038 0.1406 0.061 Uiso 0.50 1 d PR
C18 C -0.1016(3) 0.36881(11) 0.2500 0.0442(8) Uani 1 2 d S
H18A H -0.0689 0.3757 0.3817 0.066 Uiso 0.50 1 calc PR
H18B H -0.1590 0.3967 0.2047 0.066 Uiso 0.50 1 calc PR
H18C H -0.0217 0.3647 0.1636 0.066 Uiso 0.50 1 calc PR
C10 C 0.2420(3) 0.13230(11) 0.2500 0.0348(7) Uani 1 2 d S
C17 C -0.3999(3) 0.27809(12) 0.2500 0.0433(8) Uani 1 2 d S
H17 H -0.4985 0.2790 0.2500 0.052 Uiso 1 2 calc SR
C8 C -0.3195(2) 0.03929(8) 0.0673(3) 0.0406(6) Uani 1 1 d .
H8A H -0.3780 0.0692 0.0599 0.061 Uiso 1 1 calc R
H8B H -0.3786 0.0095 0.0735 0.061 Uiso 1 1 calc R
H8C H -0.2601 0.0375 -0.0477 0.061 Uiso 1 1 calc R
C16 C -0.3290(3) 0.32254(12) 0.2500 0.0415(8) Uani 1 2 d S
H16 H -0.3782 0.3533 0.2500 0.050 Uiso 1 2 calc SR
C11 C 0.2973(2) 0.15892(10) 0.4297(3) 0.0639(8) Uani 1 1 d .
H11A H 0.2675 0.1939 0.4278 0.096 Uiso 1 1 calc R
H11B H 0.3991 0.1574 0.4305 0.096 Uiso 1 1 calc R
H11C H 0.2609 0.1426 0.5461 0.096 Uiso 1 1 calc R
C12 C 0.3015(3) 0.07939(13) 0.2500 0.0638(10) Uani 1 2 d S
H12A H 0.4025 0.0809 0.2665 0.096 Uiso 0.50 1 calc PR
H12B H 0.2795 0.0631 0.1268 0.096 Uiso 0.50 1 calc PR
H12C H 0.2605 0.0603 0.3567 0.096 Uiso 0.50 1 calc PR
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
C1 O1 H1 106.4(18) . .
C4 C3 C2 123.9(3) . .
C4 C3 H3 118.1 . .
C2 C3 H3 118.1 . .
C3 C2 C1 116.9(2) . .
C3 C2 C7 122.0(2) . .
C1 C2 C7 121.0(2) . .
O1 C1 C6 120.6(2) . .
O1 C1 C2 118.1(2) . .
C6 C1 C2 121.3(2) . .
C5 C6 C1 117.7(2) . .
C5 C6 C13 120.0(2) . .
C1 C6 C13 122.3(2) . .
C17 N1 C13 118.5(2) . .
C2 C7 C9 112.8(2) . .
C2 C7 C8 110.22(15) . .
C9 C7 C8 106.72(15) . .
C2 C7 C8 110.22(15) . 6_556
C9 C7 C8 106.72(15) . 6_556
C8 C7 C8 110.0(2) . 6_556
N1 C13 C14 119.8(2) . .
N1 C13 C6 117.3(2) . .
C14 C13 C6 122.9(3) . .
C15 C14 C13 121.6(3) . .
C15 C14 H14 119.2 . .
C13 C14 H14 119.2 . .
C4 C5 C6 123.3(3) . .
C4 C5 H5 118.3 . .
C6 C5 H5 118.3 . .
C16 C15 C14 117.3(3) . .
C16 C15 C18 122.6(3) . .
C14 C15 C18 120.2(3) . .
C5 C4 C3 116.9(2) . .
C5 C4 C10 119.2(2) . .
C3 C4 C10 124.0(3) . .
C7 C9 H9A 109.6 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 105.2 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 113.6 . .
H9B C9 H9C 109.5 . .
C15 C18 H18A 109.5 . .
C15 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C15 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C11 C10 C11 108.7(3) 6_556 .
C11 C10 C4 110.26(16) 6_556 .
C11 C10 C4 110.26(16) . .
C11 C10 C12 107.61(18) 6_556 .
C11 C10 C12 107.61(18) . .
C4 C10 C12 112.3(2) . .
N1 C17 C16 123.4(3) . .
N1 C17 H17 118.3 . .
C16 C17 H17 118.3 . .
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 . .
C17 C16 C15 119.4(3) . .
C17 C16 H16 120.3 . .
C15 C16 H16 120.3 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.361(3) .
O1 H1 1.01(3) .
C3 C4 1.389(4) .
C3 C2 1.394(3) .
C3 H3 0.9500 .
C2 C1 1.413(3) .
C2 C7 1.530(4) .
C1 C6 1.410(4) .
C6 C5 1.393(4) .
C6 C13 1.480(3) .
N1 C17 1.345(3) .
N1 C13 1.350(3) .
C7 C9 1.533(4) .
C7 C8 1.540(2) .
C7 C8 1.540(2) 6_556
C13 C14 1.400(4) .
C14 C15 1.381(4) .
C14 H14 0.9500 .
C5 C4 1.384(3) .
C5 H5 0.9500 .
C15 C16 1.379(4) .
C15 C18 1.488(4) .
C4 C10 1.527(4) .
C9 H9A 0.9765 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C10 C11 1.527(3) 6_556
C10 C11 1.527(3) .
C10 C12 1.529(4) .
C17 C16 1.373(4) .
C17 H17 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C16 H16 0.9500 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 1.01(3) 1.60(3) 2.535(3) 151(3)
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_4
C4 C3 C2 C1 0.0 .
C4 C3 C2 C7 180.0 .
C3 C2 C1 O1 180.0 .
C7 C2 C1 O1 0.0 .
C3 C2 C1 C6 0.0 .
C7 C2 C1 C6 180.0 .
O1 C1 C6 C5 180.0 .
C2 C1 C6 C5 0.0 .
O1 C1 C6 C13 0.0 .
C2 C1 C6 C13 180.0 .
C3 C2 C7 C9 0.0 .
C1 C2 C7 C9 180.0 .
C3 C2 C7 C8 -119.18(15) .
C1 C2 C7 C8 60.82(15) .
C3 C2 C7 C8 119.18(15) 6_556
C1 C2 C7 C8 -60.82(15) 6_556
C17 N1 C13 C14 0.0 .
C17 N1 C13 C6 180.0 .
C5 C6 C13 N1 180.0 .
C1 C6 C13 N1 0.0 .
C5 C6 C13 C14 0.0 .
C1 C6 C13 C14 180.0 .
N1 C13 C14 C15 0.0 .
C6 C13 C14 C15 180.0 .
C1 C6 C5 C4 0.0 .
C13 C6 C5 C4 180.0 .
C13 C14 C15 C16 0.0 .
C13 C14 C15 C18 180.0 .
C6 C5 C4 C3 0.0 .
C6 C5 C4 C10 180.0 .
C2 C3 C4 C5 0.0 .
C2 C3 C4 C10 180.0 .
C5 C4 C10 C11 -60.02(18) 6_556
C3 C4 C10 C11 119.98(18) 6_556
C5 C4 C10 C11 60.02(18) .
C3 C4 C10 C11 -119.98(18) .
C5 C4 C10 C12 180.0 .
C3 C4 C10 C12 0.0 .
C13 N1 C17 C16 0.0 .
N1 C17 C16 C15 0.0 .
C14 C15 C16 C17 0.0 .
C18 C15 C16 C17 180.0 .
