#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/50/2225076.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225076
loop_
_publ_author_name
'Meng, Na-Na'
'Huang, Ting-Ting'
'Li, De-Kuan'
'Zhang, Wen-Xin'
'Yu, Luo-Ting'
_publ_section_title
;
 4-[4-(3-Methoxybenzamido)phenoxy]-N-methylpicolinamide
;
_journal_coeditor_code           OM2308
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o476
_journal_paper_doi               10.1107/S1600536809055688
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H19 N3 O4'
_chemical_formula_moiety         'C21 H19 N3 O4'
_chemical_formula_sum            'C21 H19 N3 O4'
_chemical_formula_weight         377.39
_chemical_name_systematic
;
4-[4-(3-Methoxybenzamido)phenoxy]-N-methylpicolinamide
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                71.29(3)
_cell_angle_beta                 87.74(3)
_cell_angle_gamma                76.10(3)
_cell_formula_units_Z            1
_cell_length_a                   5.0915(10)
_cell_length_b                   8.3251(17)
_cell_length_c                   11.611(2)
_cell_measurement_reflns_used    1652
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.70
_cell_volume                     452.12(18)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3733
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             198
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2108
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0349
_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)+(0.0481P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                1811
_reflns_number_total             2108
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2308.cif
_cod_data_source_block           I
_cod_original_cell_volume        452.14(16)
_cod_database_code               2225076
_cod_database_fobs_code          2225076
loop_
_symmetry_equiv_pos_as_xyz
'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 -0.3679(3) 1.5504(2) 0.23318(15) 0.0212(4) Uani d . 1 . .
O O2 -0.1469(3) 0.9491(2) 0.56055(17) 0.0249(4) Uani d . 1 . .
O O3 0.4394(3) 0.1895(2) 0.81518(15) 0.0220(4) Uani d . 1 . .
O O4 1.1345(3) 0.2263(2) 1.10678(16) 0.0230(4) Uani d . 1 . .
N N1 0.3007(3) 0.9089(2) 0.60459(17) 0.0154(4) Uani d . 1 . .
H H1N 0.443(6) 0.954(4) 0.579(3) 0.031(8) Uiso d . 1 . .
N N2 1.0377(4) -0.1617(2) 1.06587(18) 0.0197(4) Uani d . 1 . .
N N3 1.3326(4) -0.0601(3) 1.20340(18) 0.0202(4) Uani d . 1 . .
H H3N 1.353(6) -0.166(4) 1.208(3) 0.025(7) Uiso d . 1 . .
C C1 0.0404(4) 1.1969(3) 0.48677(19) 0.0138(4) Uani d . 1 . .
C C2 -0.1555(4) 1.2811(3) 0.3920(2) 0.0157(4) Uani d . 1 . .
H H2 -0.2683 1.2179 0.3713 0.019 Uiso calc R 1 . .
C C3 -0.1849(4) 1.4569(3) 0.3282(2) 0.0166(5) Uani d . 1 . .
C C4 -0.0230(4) 1.5503(3) 0.3610(2) 0.0186(5) Uani d . 1 . .
H H4 -0.0441 1.6711 0.3181 0.022 Uiso calc R 1 . .
C C5 0.1675(4) 1.4670(3) 0.4559(2) 0.0196(5) Uani d . 1 . .
H H5 0.2754 1.5316 0.4784 0.024 Uiso calc R 1 . .
C C6 0.2036(4) 1.2891(3) 0.5190(2) 0.0167(5) Uani d . 1 . .
H H6 0.3377 1.2318 0.5830 0.020 Uiso calc R 1 . .
C C7 -0.4855(5) 1.4516(3) 0.1769(2) 0.0240(5) Uani d . 1 . .
H H7A -0.6035 1.3902 0.2340 0.036 Uiso calc R 1 . .
H H7B -0.3410 1.3663 0.1549 0.036 Uiso calc R 1 . .
H H7C -0.5919 1.5310 0.1034 0.036 Uiso calc R 1 . .
C C8 0.0553(4) 1.0091(3) 0.5533(2) 0.0163(4) Uani d . 1 . .
C C9 0.3486(4) 0.7259(3) 0.66625(19) 0.0145(4) Uani d . 1 . .
C C10 0.5761(4) 0.6131(3) 0.6406(2) 0.0162(4) Uani d . 1 . .
H H10 0.7046 0.6589 0.5865 0.019 Uiso calc R 1 . .
C C11 0.6152(4) 0.4336(3) 0.6942(2) 0.0190(5) Uani d . 1 . .
H H11 0.7689 0.3560 0.6763 0.023 Uiso calc R 1 . .
C C12 0.4271(4) 0.3690(3) 0.7740(2) 0.0174(5) Uani d . 1 . .
C C13 0.2105(4) 0.4795(3) 0.8055(2) 0.0213(5) Uani d . 1 . .
H H13 0.0892 0.4336 0.8640 0.026 Uiso calc R 1 . .
C C14 0.1710(4) 0.6586(3) 0.7512(2) 0.0204(5) Uani d . 1 . .
H H14 0.0215 0.7356 0.7723 0.025 Uiso calc R 1 . .
C C15 0.6403(4) 0.0792(3) 0.8978(2) 0.0169(5) Uani d . 1 . .
C C16 0.6760(5) -0.0977(3) 0.9182(2) 0.0194(5) Uani d . 1 . .
H H16 0.5661 -0.1394 0.8757 0.023 Uiso calc R 1 . .
C C17 0.8763(5) -0.2126(3) 1.0024(2) 0.0210(5) Uani d . 1 . .
H H17 0.9012 -0.3341 1.0161 0.025 Uiso calc R 1 . .
C C18 0.9936(4) 0.0107(3) 1.0450(2) 0.0163(4) Uani d . 1 . .
C C19 0.8000(4) 0.1369(3) 0.9625(2) 0.0161(4) Uani d . 1 . .
H H19 0.7777 0.2578 0.9509 0.019 Uiso calc R 1 . .
C C20 1.1623(4) 0.0692(3) 1.1206(2) 0.0172(5) Uani d . 1 . .
C C21 1.4960(5) -0.0250(3) 1.2878(2) 0.0220(5) Uani d . 1 . .
H H21A 1.3916 0.0733 1.3122 0.033 Uiso calc R 1 . .
H H21B 1.6598 0.0043 1.2484 0.033 Uiso calc R 1 . .
H H21C 1.5470 -0.1288 1.3599 0.033 Uiso calc R 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 C7 . . 116.81(17) ?
C15 O3 C12 . . 119.17(17) ?
C8 N1 C9 . . 122.98(18) ?
C8 N1 H1N . . 116(2) ?
C9 N1 H1N . . 118(2) ?
C18 N2 C17 . . 116.25(18) ?
C20 N3 C21 . . 121.4(2) ?
C20 N3 H3N . . 122(2) ?
C21 N3 H3N . . 117(2) ?
C6 C1 C2 . . 120.42(19) ?
C6 C1 C8 . . 122.61(19) ?
C2 C1 C8 . . 116.91(19) ?
C3 C2 C1 . . 119.96(19) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
O1 C3 C2 . . 124.4(2) ?
O1 C3 C4 . . 115.84(19) ?
C2 C3 C4 . . 119.77(19) ?
C5 C4 C3 . . 120.0(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.8(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C1 C6 C5 . . 119.04(19) ?
C1 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 N1 . . 122.4(2) ?
O2 C8 C1 . . 120.97(19) ?
N1 C8 C1 . . 116.65(19) ?
C14 C9 C10 . . 119.6(2) ?
C14 C9 N1 . . 120.77(18) ?
C10 C9 N1 . . 119.64(19) ?
C11 C10 C9 . . 120.1(2) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C12 C11 C10 . . 119.2(2) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C13 C12 C11 . . 121.2(2) ?
C13 C12 O3 . . 118.26(19) ?
C11 C12 O3 . . 120.3(2) ?
C12 C13 C14 . . 119.4(2) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C13 C14 C9 . . 120.4(2) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
O3 C15 C16 . . 116.9(2) ?
O3 C15 C19 . . 123.2(2) ?
C16 C15 C19 . . 119.86(19) ?
C15 C16 C17 . . 118.2(2) ?
C15 C16 H16 . . 120.9 ?
C17 C16 H16 . . 120.9 ?
N2 C17 C16 . . 123.7(2) ?
N2 C17 H17 . . 118.1 ?
C16 C17 H17 . . 118.1 ?
N2 C18 C19 . . 124.8(2) ?
N2 C18 C20 . . 116.87(18) ?
C19 C18 C20 . . 118.32(19) ?
C18 C19 C15 . . 117.2(2) ?
C18 C19 H19 . . 121.4 ?
C15 C19 H19 . . 121.4 ?
O4 C20 N3 . . 124.1(2) ?
O4 C20 C18 . . 120.93(19) ?
N3 C20 C18 . . 115.0(2) ?
N3 C21 H21A . . 109.5 ?
N3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
N3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
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 . 1.369(3) ?
O1 C7 . 1.440(3) ?
O2 C8 . 1.237(3) ?
O3 C15 . 1.368(3) ?
O3 C12 . 1.402(3) ?
O4 C20 . 1.239(3) ?
N1 C8 . 1.360(3) ?
N1 C9 . 1.424(3) ?
N1 H1N . 0.89(3) ?
N2 C18 . 1.340(3) ?
N2 C17 . 1.346(3) ?
N3 C20 . 1.337(3) ?
N3 C21 . 1.450(3) ?
N3 H3N . 0.85(3) ?
C1 C6 . 1.391(3) ?
C1 C2 . 1.397(3) ?
C1 C8 . 1.491(3) ?
C2 C3 . 1.386(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.397(3) ?
C4 C5 . 1.380(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.396(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C9 C14 . 1.387(3) ?
C9 C10 . 1.394(3) ?
C10 C11 . 1.389(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.387(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.376(3) ?
C13 C14 . 1.387(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C16 . 1.382(3) ?
C15 C19 . 1.387(3) ?
C16 C17 . 1.386(3) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 C19 . 1.387(3) ?
C18 C20 . 1.510(3) ?
C19 H19 . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
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
N1 H1N O2 1_655 0.89(3) 2.08(3) 2.918(2) 155(3)
N3 H3N O1 1_736 0.85(3) 2.38(3) 3.148(3) 151(2)
N3 H3N N2 . 0.85(3) 2.33(3) 2.681(3) 105(2)
C7 H7B O4 1_464 0.98 2.55 3.475(3) 158.0
C14 H14 O2 . 0.95 2.56 2.887(3) 100.2
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
C6 C1 C2 C3 . . . . 1.0(3) ?
C8 C1 C2 C3 . . . . 178.42(18) ?
C7 O1 C3 C2 . . . . -16.6(3) ?
C7 O1 C3 C4 . . . . 164.13(19) ?
C1 C2 C3 O1 . . . . 179.13(19) ?
C1 C2 C3 C4 . . . . -1.6(3) ?
O1 C3 C4 C5 . . . . -180.0(2) ?
C2 C3 C4 C5 . . . . 0.7(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
C2 C1 C6 C5 . . . . 0.5(3) ?
C8 C1 C6 C5 . . . . -176.77(19) ?
C4 C5 C6 C1 . . . . -1.4(3) ?
C9 N1 C8 O2 . . . . 2.7(3) ?
C9 N1 C8 C1 . . . . -177.13(19) ?
C6 C1 C8 O2 . . . . 149.6(2) ?
C2 C1 C8 O2 . . . . -27.7(3) ?
C6 C1 C8 N1 . . . . -30.6(3) ?
C2 C1 C8 N1 . . . . 152.10(19) ?
C8 N1 C9 C14 . . . . -46.8(3) ?
C8 N1 C9 C10 . . . . 133.0(2) ?
C14 C9 C10 C11 . . . . 4.1(3) ?
N1 C9 C10 C11 . . . . -175.67(19) ?
C9 C10 C11 C12 . . . . -0.7(3) ?
C10 C11 C12 C13 . . . . -3.2(3) ?
C10 C11 C12 O3 . . . . 170.56(18) ?
C15 O3 C12 C13 . . . . -113.2(2) ?
C15 O3 C12 C11 . . . . 72.9(3) ?
C11 C12 C13 C14 . . . . 3.7(3) ?
O3 C12 C13 C14 . . . . -170.2(2) ?
C12 C13 C14 C9 . . . . -0.3(3) ?
C10 C9 C14 C13 . . . . -3.6(3) ?
N1 C9 C14 C13 . . . . 176.2(2) ?
C12 O3 C15 C16 . . . . -168.06(19) ?
C12 O3 C15 C19 . . . . 13.8(3) ?
O3 C15 C16 C17 . . . . -179.4(2) ?
C19 C15 C16 C17 . . . . -1.1(3) ?
C18 N2 C17 C16 . . . . 0.8(3) ?
C15 C16 C17 N2 . . . . 0.3(4) ?
C17 N2 C18 C19 . . . . -1.2(3) ?
C17 N2 C18 C20 . . . . 176.7(2) ?
N2 C18 C19 C15 . . . . 0.3(3) ?
C20 C18 C19 C15 . . . . -177.45(19) ?
O3 C15 C19 C18 . . . . 178.95(19) ?
C16 C15 C19 C18 . . . . 0.8(3) ?
C21 N3 C20 O4 . . . . 1.9(3) ?
C21 N3 C20 C18 . . . . -176.19(19) ?
N2 C18 C20 O4 . . . . 179.9(2) ?
C19 C18 C20 O4 . . . . -2.2(3) ?
N2 C18 C20 N3 . . . . -2.0(3) ?
C19 C18 C20 N3 . . . . 175.94(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744220
