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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/85/1508544.cif $
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#
# 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_1508544
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         'C21 H32 N2 O'
_chemical_formula_sum            'C21 H32 N2 O'
_chemical_formula_weight         328.49
_chemical_name_common            HOArpyNMe2
_chemical_name_systematic
;
 HOArpyNMe2
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      12
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.2190(32)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   18.83960(140)
_cell_length_b                   6.95260(59)
_cell_length_c                   14.93540(150)
_cell_measurement_reflns_used    304
_cell_measurement_temperature    130(2)
_cell_volume                     1868.6(3)
_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    SIR-2004
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0673
_diffrn_reflns_av_sigmaI/netI    0.0994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2958
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   HKL-2000
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0698
_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)+(0.1062P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1965
_reflns_number_gt                956
_reflns_number_total             1796
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp311388n_si_002.cif
_cod_data_source_block           HOArpyNMe2
_cod_original_cell_volume        1868.621(285)
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               1508544
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C1 C 0.81871(19) 0.0000 0.2637(3) 0.0309(9) Uani 1 2 d S
C2 C 0.79146(19) 0.0000 0.3428(3) 0.0304(9) Uani 1 2 d S
C3 C 0.71586(19) 0.0000 0.3266(3) 0.0323(9) Uani 1 2 d S
H3 H 0.6973 0.0000 0.3792 0.039 Uiso 1 2 calc SR
C4 C 0.66405(19) 0.0000 0.2362(3) 0.0287(9) Uani 1 2 d S
C5 C 0.6925(2) 0.0000 0.1616(3) 0.0299(9) Uani 1 2 d S
H5 H 0.6588 0.0000 0.1000 0.036 Uiso 1 2 calc SR
C6 C 0.76912(19) 0.0000 0.1720(3) 0.0286(9) Uani 1 2 d S
C7 C 0.8471(2) 0.0000 0.4423(3) 0.0341(10) Uani 1 2 d S
C8 C 0.89518(15) 0.1810(5) 0.4575(2) 0.0494(9) Uani 1 1 d .
H8A H 0.9311 0.1776 0.5203 0.074 Uiso 1 1 calc R
H8B H 0.8635 0.2949 0.4518 0.074 Uiso 1 1 calc R
H8C H 0.9218 0.1866 0.4103 0.074 Uiso 1 1 calc R
C9 C 0.8092(2) 0.0000 0.5200(3) 0.0355(10) Uani 1 2 d S
H9A H 0.8449 0.0407 0.5791 0.053 Uiso 0.50 1 calc PR
H9B H 0.7915 -0.1299 0.5271 0.053 Uiso 1 1 calc R
H9C H 0.7670 0.0892 0.5034 0.053 Uiso 1 1 calc R
C10 C 0.5804(2) 0.0000 0.2248(3) 0.0321(10) Uani 1 2 d S
C11 C 0.55993(15) 0.1798(5) 0.2703(2) 0.0509(9) Uani 1 1 d .
H11A H 0.5880 0.1818 0.3371 0.076 Uiso 1 1 calc R
H11B H 0.5066 0.1785 0.2635 0.076 Uiso 1 1 calc R
H11C H 0.5721 0.2945 0.2397 0.076 Uiso 1 1 calc R
C12 C 0.5346(2) 0.0000 0.1209(3) 0.0480(12) Uani 1 2 d S
H12A H 0.5436 0.1198 0.0915 0.072 Uiso 0.50 1 calc PR
H12B H 0.4816 -0.0101 0.1158 0.072 Uiso 0.50 1 calc PR
H12C H 0.5493 -0.1097 0.0892 0.072 Uiso 0.50 1 calc PR
C13 C 0.79642(19) 0.0000 0.0878(3) 0.0293(9) Uani 1 2 d S
C14 C 0.7485(2) 0.0000 -0.0035(3) 0.0295(9) Uani 1 2 d S
H14 H 0.6963 0.0000 -0.0135 0.035 Uiso 1 2 calc SR
C15 C 0.7765(2) 0.0000 -0.0809(3) 0.0292(9) Uani 1 2 d S
C16 C 0.8547(2) 0.0000 -0.0607(3) 0.0392(11) Uani 1 2 d S
H16 H 0.8771 0.0000 -0.1099 0.047 Uiso 1 2 calc SR
C17 C 0.8975(2) 0.0000 0.0308(3) 0.0417(11) Uani 1 2 d S
H17 H 0.9499 0.0000 0.0429 0.050 Uiso 1 2 calc SR
C18 C 0.6509(2) 0.0000 -0.1886(3) 0.0405(11) Uani 1 2 d S
H18A H 0.6365 -0.1043 -0.1534 0.061 Uiso 0.50 1 calc PR
H18B H 0.6271 -0.0191 -0.2558 0.061 Uiso 0.50 1 calc PR
H18C H 0.6350 0.1235 -0.1693 0.061 Uiso 0.50 1 calc PR
C19 C 0.7611(2) 0.0000 -0.2487(3) 0.0372(10) Uani 1 2 d S
H19A H 0.7214 0.0294 -0.3063 0.056 Uiso 0.50 1 calc PR
H19B H 0.7820 -0.1269 -0.2543 0.056 Uiso 0.50 1 calc PR
H19C H 0.8002 0.0975 -0.2387 0.056 Uiso 0.50 1 calc PR
N1 N 0.87097(16) 0.0000 0.1049(2) 0.0375(9) Uani 1 2 d S
N2 N 0.73100(16) 0.0000 -0.1698(2) 0.0351(9) Uani 1 2 d S
O1 O 0.89341(14) 0.0000 0.2785(2) 0.0405(8) Uani 1 2 d S
H1 H 0.901(3) 0.037(10) 0.220(4) 0.061 Uiso 0.50 1 d P
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
O1 C1 C6 121.0(3) . .
O1 C1 C2 118.4(3) . .
C6 C1 C2 120.6(3) . .
C3 C2 C1 117.7(4) . .
C3 C2 C7 122.9(3) . .
C1 C2 C7 119.4(3) . .
C2 C3 C4 123.8(3) . .
C2 C3 H3 118.1 . .
C4 C3 H3 118.1 . .
C5 C4 C3 116.8(3) . .
C5 C4 C10 123.0(3) . .
C3 C4 C10 120.2(3) . .
C4 C5 C6 123.1(4) . .
C4 C5 H5 118.5 . .
C6 C5 H5 118.5 . .
C5 C6 C1 118.0(3) . .
C5 C6 C13 120.4(3) . .
C1 C6 C13 121.5(3) . .
C8 C7 C8 110.9(3) . 6
C8 C7 C9 106.0(2) . .
C8 C7 C9 106.0(2) 6 .
C8 C7 C2 110.3(2) . .
C8 C7 C2 110.3(2) 6 .
C9 C7 C2 113.2(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 . .
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 . .
C11 C10 C11 110.0(3) 6 .
C11 C10 C4 109.7(2) 6 .
C11 C10 C4 109.7(2) . .
C11 C10 C12 108.0(2) 6 .
C11 C10 C12 108.0(2) . .
C4 C10 C12 111.3(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 . .
N1 C13 C14 121.4(3) . .
N1 C13 C6 116.0(3) . .
C14 C13 C6 122.6(3) . .
C13 C14 C15 120.7(3) . .
C13 C14 H14 119.6 . .
C15 C14 H14 119.6 . .
N2 C15 C14 121.6(3) . .
N2 C15 C16 121.9(3) . .
C14 C15 C16 116.5(4) . .
C17 C16 C15 118.9(4) . .
C17 C16 H16 120.5 . .
C15 C16 H16 120.5 . .
N1 C17 C16 124.8(4) . .
N1 C17 H17 117.6 . .
C16 C17 H17 117.6 . .
N2 C18 H18A 109.5 . .
N2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
N2 C19 H19A 109.5 . .
N2 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
N2 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C17 N1 C13 117.7(3) . .
C15 N2 C18 120.8(3) . .
C15 N2 C19 120.7(3) . .
C18 N2 C19 118.5(3) . .
C1 O1 H1 106(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.358(4) .
C1 C6 1.411(5) .
C1 C2 1.421(5) .
C2 C3 1.372(5) .
C2 C7 1.545(5) .
C3 C4 1.413(5) .
C3 H3 0.9500 .
C4 C5 1.372(5) .
C4 C10 1.534(5) .
C5 C6 1.406(5) .
C5 H5 0.9500 .
C6 C13 1.492(5) .
C7 C8 1.528(4) .
C7 C8 1.528(3) 6
C7 C9 1.531(5) .
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 C11 1.526(4) 6
C10 C11 1.526(4) .
C10 C12 1.536(5) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 N1 1.351(4) .
C13 C14 1.395(5) .
C14 C15 1.407(5) .
C14 H14 0.9500 .
C15 N2 1.350(5) .
C15 C16 1.413(5) .
C16 C17 1.366(5) .
C16 H16 0.9500 .
C17 N1 1.342(5) .
C17 H17 0.9500 .
C18 N2 1.451(5) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 N2 1.451(4) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
O1 H1 0.95(6) .
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 0.95(6) 1.67(5) 2.500(4) 144(5)
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
O1 C1 C2 C3 180.0 .
C6 C1 C2 C3 0.0 .
O1 C1 C2 C7 0.0 .
C6 C1 C2 C7 180.0 .
C1 C2 C3 C4 0.0 .
C7 C2 C3 C4 180.0 .
C2 C3 C4 C5 0.0 .
C2 C3 C4 C10 180.0 .
C3 C4 C5 C6 0.0 .
C10 C4 C5 C6 180.0 .
C4 C5 C6 C1 0.0 .
C4 C5 C6 C13 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 C8 -118.6(2) .
C1 C2 C7 C8 61.4(2) .
C3 C2 C7 C8 118.6(2) 6
C1 C2 C7 C8 -61.4(2) 6
C3 C2 C7 C9 0.0 .
C1 C2 C7 C9 180.0 .
C5 C4 C10 C11 119.5(2) 6
C3 C4 C10 C11 -60.5(2) 6
C5 C4 C10 C11 -119.5(2) .
C3 C4 C10 C11 60.5(2) .
C5 C4 C10 C12 0.0 .
C3 C4 C10 C12 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 .
C13 C14 C15 N2 180.0 .
C13 C14 C15 C16 0.0 .
N2 C15 C16 C17 180.0 .
C14 C15 C16 C17 0.0 .
C15 C16 C17 N1 0.0 .
C16 C17 N1 C13 0.0 .
C14 C13 N1 C17 0.0 .
C6 C13 N1 C17 180.0 .
C14 C15 N2 C18 0.0 .
C16 C15 N2 C18 180.0 .
C14 C15 N2 C19 180.0 .
C16 C15 N2 C19 0.0 .
