#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/72/2227299.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_2227299
loop_
_publ_author_name
'Xiao, Jie'
'Zhao, Hong'
_publ_section_title
;
 1-[Phenyl(pyridin-2-ylamino)methyl]-2-naphthol
;
_journal_coeditor_code           BX2316
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2938
_journal_paper_doi               10.1107/S1600536810042327
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H18 N2 O'
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38
_chemical_name_systematic
;
1-[Phenyl(pyridin-2-ylamino)methyl]-2-naphthol
;
_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                111.00(3)
_cell_angle_beta                 98.64(5)
_cell_angle_gamma                90.83(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5841(10)
_cell_length_b                   10.1890(15)
_cell_length_c                   11.9745(15)
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.724
_cell_volume                     851.7(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'SHELXS97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0777
_diffrn_reflns_av_sigmaI/netI    0.1088
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8701
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.2089
_refine_ls_R_factor_gt           0.0965
_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)+(0.0643P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.2175
_reflns_number_gt                1655
_reflns_number_total             3841
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bx2316.cif
_cod_data_source_block           I
_cod_original_cell_volume        851.7(2)
_cod_database_code               2227299
_cod_database_fobs_code          2227299
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.0666(3) 0.3873(3) 0.8523(2) 0.0617(8) Uani d . 1 . .
H H1A 1.1414 0.4523 0.8658 0.093 Uiso d R 1 . .
N N1 0.7935(4) 0.2729(3) 0.9263(3) 0.0566(9) Uani d . 1 . .
H H1B 0.8964 0.3093 0.9682 0.068 Uiso d R 1 . .
N N2 0.6664(4) 0.4120(3) 1.0857(3) 0.0530(8) Uani d . 1 . .
C C1 0.7861(5) 0.1892(4) 0.7972(3) 0.0485(9) Uani d . 1 . .
C C2 0.7985(5) 0.2805(4) 0.7231(3) 0.0470(9) Uani d . 1 . .
C C3 0.9439(5) 0.3761(4) 0.7531(3) 0.0520(10) Uani d . 1 . .
C C4 0.9660(6) 0.4595(4) 0.6832(4) 0.0642(11) Uani d . 1 . .
H H4 1.0659 0.5228 0.7041 0.077 Uiso calc R 1 . .
C C5 0.8400(6) 0.4467(5) 0.5847(4) 0.0700(12) Uani d . 1 . .
H H5 0.8559 0.5009 0.5384 0.084 Uiso calc R 1 . .
C C6 0.6862(6) 0.3526(4) 0.5520(3) 0.0604(11) Uani d . 1 . .
C C7 0.6633(5) 0.2706(4) 0.6231(3) 0.0545(10) Uani d . 1 . .
C C8 0.5032(6) 0.1824(4) 0.5882(4) 0.0720(13) Uani d . 1 . .
H H8 0.4822 0.1276 0.6331 0.086 Uiso calc R 1 . .
C C9 0.3793(7) 0.1749(5) 0.4913(5) 0.0960(17) Uani d . 1 . .
H H9 0.2751 0.1165 0.4718 0.115 Uiso calc R 1 . .
C C10 0.4070(8) 0.2538(6) 0.4213(5) 0.0990(19) Uani d . 1 . .
H H10 0.3222 0.2467 0.3542 0.119 Uiso calc R 1 . .
C C11 0.5562(7) 0.3408(5) 0.4499(4) 0.0817(14) Uani d . 1 . .
H H11 0.5740 0.3932 0.4024 0.098 Uiso calc R 1 . .
C C12 0.9204(5) 0.0761(4) 0.7796(3) 0.0488(9) Uani d . 1 . .
C C13 0.9214(6) -0.0125(4) 0.8453(3) 0.0650(11) Uani d . 1 . .
H H13 0.8439 0.0007 0.9010 0.078 Uiso calc R 1 . .
C C14 1.0357(7) -0.1196(5) 0.8290(4) 0.0769(13) Uani d . 1 . .
H H14 1.0342 -0.1783 0.8732 0.092 Uiso calc R 1 . .
C C15 1.1510(6) -0.1395(5) 0.7479(4) 0.0793(13) Uani d . 1 . .
H H15 1.2311 -0.2094 0.7388 0.095 Uiso calc R 1 . .
C C16 1.1481(6) -0.0558(4) 0.6801(4) 0.0739(13) Uani d . 1 . .
H H16 1.2231 -0.0718 0.6226 0.089 Uiso calc R 1 . .
C C17 1.0346(5) 0.0526(4) 0.6962(3) 0.0607(11) Uani d . 1 . .
H H17 1.0355 0.1096 0.6506 0.073 Uiso calc R 1 . .
C C18 0.6481(5) 0.2977(4) 0.9857(3) 0.0476(9) Uani d . 1 . .
C C19 0.4937(5) 0.2068(4) 0.9475(4) 0.0648(12) Uani d . 1 . .
H H19 0.4829 0.1254 0.8784 0.078 Uiso calc R 1 . .
C C20 0.3584(6) 0.2405(5) 1.0143(4) 0.0775(13) Uani d . 1 . .
H H20 0.2535 0.1820 0.9890 0.093 Uiso calc R 1 . .
C C21 0.3736(6) 0.3571(5) 1.1164(4) 0.0780(13) Uani d . 1 . .
H H21 0.2824 0.3802 1.1625 0.094 Uiso calc R 1 . .
C C22 0.5309(6) 0.4390(5) 1.1480(4) 0.0689(12) Uani d . 1 . .
H H22 0.5443 0.5195 1.2181 0.083 Uiso calc R 1 . .
H H66 0.668(4) 0.142(3) 0.776(3) 0.041(9) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 H1A . . 109.5 ?
C18 N1 C1 . . 125.0(3) ?
C18 N1 H1B . . 117.5 ?
C1 N1 H1B . . 117.5 ?
C18 N2 C22 . . 117.9(3) ?
N1 C1 C2 . . 112.2(3) ?
N1 C1 C12 . . 110.8(3) ?
C2 C1 C12 . . 114.6(3) ?
N1 C1 H66 . . 102.0(18) ?
C2 C1 H66 . . 109.0(18) ?
C12 C1 H66 . . 107.4(19) ?
C3 C2 C7 . . 119.2(3) ?
C3 C2 C1 . . 119.0(3) ?
C7 C2 C1 . . 121.7(3) ?
O1 C3 C2 . . 117.8(3) ?
O1 C3 C4 . . 121.0(3) ?
C2 C3 C4 . . 121.2(4) ?
C5 C4 C3 . . 119.7(4) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 C6 . . 121.2(4) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C5 C6 C7 . . 119.0(4) ?
C5 C6 C11 . . 120.6(4) ?
C7 C6 C11 . . 120.4(4) ?
C8 C7 C6 . . 116.1(4) ?
C8 C7 C2 . . 124.3(4) ?
C6 C7 C2 . . 119.6(4) ?
C9 C8 C7 . . 122.3(5) ?
C9 C8 H8 . . 118.9 ?
C7 C8 H8 . . 118.9 ?
C8 C9 C10 . . 120.5(5) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C11 C10 C9 . . 120.4(5) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C6 . . 120.3(5) ?
C10 C11 H11 . . 119.9 ?
C6 C11 H11 . . 119.9 ?
C17 C12 C13 . . 118.2(4) ?
C17 C12 C1 . . 122.6(3) ?
C13 C12 C1 . . 119.0(3) ?
C14 C13 C12 . . 121.1(4) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C15 C14 C13 . . 120.0(4) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 119.6(4) ?
C14 C15 H15 . . 120.2 ?
C16 C15 H15 . . 120.2 ?
C15 C16 C17 . . 120.8(4) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C12 C17 C16 . . 120.2(4) ?
C12 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
N2 C18 N1 . . 115.6(3) ?
N2 C18 C19 . . 121.3(3) ?
N1 C18 C19 . . 123.1(4) ?
C20 C19 C18 . . 118.2(4) ?
C20 C19 H19 . . 120.9 ?
C18 C19 H19 . . 120.9 ?
C21 C20 C19 . . 121.5(4) ?
C21 C20 H20 . . 119.2 ?
C19 C20 H20 . . 119.2 ?
C20 C21 C22 . . 116.2(4) ?
C20 C21 H21 . . 121.9 ?
C22 C21 H21 . . 121.9 ?
N2 C22 C21 . . 124.8(4) ?
N2 C22 H22 . . 117.6 ?
C21 C22 H22 . . 117.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . 1.363(4) ?
O1 H1A . 0.8194 ?
N1 C18 . 1.378(4) ?
N1 C1 . 1.466(4) ?
N1 H1B . 0.8596 ?
N2 C18 . 1.325(4) ?
N2 C22 . 1.335(5) ?
C1 C2 . 1.508(5) ?
C1 C12 . 1.528(5) ?
C1 H66 . 0.97(3) ?
C2 C3 . 1.376(5) ?
C2 C7 . 1.427(5) ?
C3 C4 . 1.415(5) ?
C4 C5 . 1.367(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.413(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.416(5) ?
C6 C11 . 1.418(5) ?
C7 C8 . 1.415(5) ?
C8 C9 . 1.357(6) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.388(7) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.349(7) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C17 . 1.378(5) ?
C12 C13 . 1.393(5) ?
C13 C14 . 1.381(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.366(6) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.371(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.386(5) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 C19 . 1.394(5) ?
C19 C20 . 1.368(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.354(6) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.368(6) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A N2 2_767 0.82 1.87 2.677(4) 170.3
N1 H1B O1 . 0.86 2.35 2.767(4) 110.2
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C18 N1 C1 C2 . . . . 102.8(4) ?
C18 N1 C1 C12 . . . . -127.8(4) ?
N1 C1 C2 C3 . . . . 56.8(4) ?
C12 C1 C2 C3 . . . . -70.6(4) ?
N1 C1 C2 C7 . . . . -122.9(4) ?
C12 C1 C2 C7 . . . . 109.6(4) ?
C7 C2 C3 O1 . . . . 177.1(3) ?
C1 C2 C3 O1 . . . . -2.7(5) ?
C7 C2 C3 C4 . . . . -3.2(5) ?
C1 C2 C3 C4 . . . . 177.1(3) ?
O1 C3 C4 C5 . . . . -179.5(3) ?
C2 C3 C4 C5 . . . . 0.8(6) ?
C3 C4 C5 C6 . . . . 0.8(6) ?
C4 C5 C6 C7 . . . . 0.1(6) ?
C4 C5 C6 C11 . . . . 179.8(4) ?
C5 C6 C7 C8 . . . . 177.7(4) ?
C11 C6 C7 C8 . . . . -2.0(5) ?
C5 C6 C7 C2 . . . . -2.4(5) ?
C11 C6 C7 C2 . . . . 177.9(4) ?
C3 C2 C7 C8 . . . . -176.2(4) ?
C1 C2 C7 C8 . . . . 3.6(6) ?
C3 C2 C7 C6 . . . . 4.0(5) ?
C1 C2 C7 C6 . . . . -176.3(3) ?
C6 C7 C8 C9 . . . . 0.8(6) ?
C2 C7 C8 C9 . . . . -179.1(4) ?
C7 C8 C9 C10 . . . . 0.7(7) ?
C8 C9 C10 C11 . . . . -1.1(8) ?
C9 C10 C11 C6 . . . . -0.1(8) ?
C5 C6 C11 C10 . . . . -178.0(5) ?
C7 C6 C11 C10 . . . . 1.7(6) ?
N1 C1 C12 C17 . . . . -132.7(4) ?
C2 C1 C12 C17 . . . . -4.6(5) ?
N1 C1 C12 C13 . . . . 51.0(4) ?
C2 C1 C12 C13 . . . . 179.1(3) ?
C17 C12 C13 C14 . . . . 1.1(6) ?
C1 C12 C13 C14 . . . . 177.5(4) ?
C12 C13 C14 C15 . . . . 0.4(7) ?
C13 C14 C15 C16 . . . . -2.3(7) ?
C14 C15 C16 C17 . . . . 2.6(7) ?
C13 C12 C17 C16 . . . . -0.7(6) ?
C1 C12 C17 C16 . . . . -177.0(3) ?
C15 C16 C17 C12 . . . . -1.1(6) ?
C22 N2 C18 N1 . . . . -178.6(3) ?
C22 N2 C18 C19 . . . . -1.1(5) ?
C1 N1 C18 N2 . . . . -156.4(3) ?
C1 N1 C18 C19 . . . . 26.2(6) ?
N2 C18 C19 C20 . . . . 1.7(6) ?
N1 C18 C19 C20 . . . . 179.0(4) ?
C18 C19 C20 C21 . . . . -1.4(7) ?
C19 C20 C21 C22 . . . . 0.4(7) ?
C18 N2 C22 C21 . . . . 0.1(6) ?
C20 C21 C22 N2 . . . . 0.3(7) ?
