##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'with notepad'
_journal_date_recd_electronic     2001-09-24
_journal_date_accepted     2001-11-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue     12
_journal_page_first     o1161
_journal_page_last     o1162
_journal_paper_category     EO
_publ_contact_author_name     'Dr Jian Ying Qi'
_publ_contact_author_address
;
Department of Applied Biology and Chemical Technology
The Hong Kong Polytechnic University
Hung Hom, Kowloon
Hong Kong
;
_publ_contact_author_email     bcqijy@polyu.edu.hk
_publ_contact_author_fax     '(852) 2365 4167'
_publ_contact_author_phone     '(852) 2766 5646'
_publ_section_title
;
N,N'-Bis(2-methoxyphenyl)pyridine-2,6-dicarboxamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yang, Qi Yun' .
;
Department of Chemistry
Yunnan Normal University
Kunming, Yunnan
People's Republic of China
;
    'Zhou, Zhong Yuan' .
;
Chengdu Institute of Organic Chemistry
Chinese Academy of Science
Chengdu, Sichuan
People's Republic of China
;
    'Qi, Jian Ying' .
;
Department of Chemistry
Yunnan Normal University
Kunming, Yunnan
People's Republic of China
;
data_I
_chemical_name_systematic
;
N,N'-Di-2-methoxyphenylpyridine-2,6-dicarboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H19 N3 O4'
_chemical_formula_sum     'C21 H19 N3 O4'
_chemical_formula_iupac     'C21 H19 N3 O4'
_chemical_formula_weight     377.39
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     4.7919(9)
_cell_length_b     15.775(3)
_cell_length_c     25.228(5)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1907.1(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4522
_cell_measurement_theta_min     1
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     294(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max      .24
_exptl_crystal_size_mid      .20
_exptl_crystal_size_min      .18
_exptl_crystal_density_diffrn     1.314
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu      .093
_exptl_absorpt_correction_type     empirical
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min      .978
_exptl_absorpt_correction_T_max      .984
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.3
_diffrn_reflns_number     12538
_diffrn_reflns_av_R_equivalents      .083
_diffrn_reflns_av_sigmaI/netI      .0989
_diffrn_reflns_theta_min     2.07
_diffrn_reflns_theta_max     27.53
_diffrn_reflns_theta_full     27.53
_diffrn_measured_fraction_theta_max      .996
_diffrn_measured_fraction_theta_full      .996
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -29
_diffrn_reflns_limit_l_max     32
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     2571
_reflns_number_gt     1007
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .142
_refine_ls_R_factor_gt      .041
_refine_ls_wR_factor_ref      .104
_refine_ls_goodness_of_fit_ref      .85
_refine_ls_restrained_S_all      .85
_refine_ls_number_reflns     2571
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                'calc w = 1/[σ²(Fo²)+(0.1P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max      .14
_refine_diff_density_min      -.20
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1995)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SHELXTL (Siemens, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    O1  .3689(8)  .20900(18)  .25572(11)  .1129(13) Uani d . 1 . . O
    O2 1.0181(7)  -.02251(16)  .23433(10)  .0797(8) Uani d . 1 . . O
    O3 1.1365(7)  .10741(15)  .48373(10)  .0982(11) Uani d . 1 . . O
    O4 1.0396(6)  -.11966(15)  .36016(9)  .0738(8) Uani d . 1 . . O
    N1  .7888(6)  .13141(16)  .36080(11)  .0543(8) Uani d . 1 . . N
    N2  .6785(7)  .10072(17)  .25762(10)  .0636(9) Uani d . 1 . . N
    H2A  .7890  .0741  .2787  .076 Uiso calc R 1 . . H
    N3 1.1108(7)  .01954(17)  .41213(10)  .0630(9) Uani d . 1 . . N
    H3A 1.0491  .0171  .3801  .076 Uiso calc R 1 . . H
    C1 1.2034(10)  -.0912(2)  .22548(16)  .0900(15) Uani d . 1 . . C
    H1B 1.3066  -.1025  .2573  .135 Uiso calc R 1 . . H
    H1C 1.3304  -.0769  .1974  .135 Uiso calc R 1 . . H
    H1D 1.0985  -.1406  .2157  .135 Uiso calc R 1 . . H
    C2  .8516(9)  .0033(3)  .19318(16)  .0662(11) Uani d . 1 . . C
    C3  .8550(10)  -.0318(2)  .14311(18)  .0794(14) Uani d . 1 . . C
    H3B  .9765  -.0758  .1350  .095 Uiso calc R 1 . . H
    C4  .6727(12)  .0001(3)  .10503(18)  .0898(17) Uani d . 1 . . C
    H4A  .6746  -.0231  .0711  .108 Uiso calc R 1 . . H
    C5  .4911(11)  .0645(3)  .11623(16)  .0862(15) Uani d . 1 . . C
    H5A  .3690  .0846  .0905  .103 Uiso calc R 1 . . H
    C6  .4926(10)  .0994(2)  .16694(15)  .0725(12) Uani d . 1 . . C
    H6A  .3711  .1435  .1750  .087 Uiso calc R 1 . . H
    C7  .6699(9)  .0697(2)  .20503(14)  .0591(11) Uani d . 1 . . C
    C8  .5389(10)  .1658(2)  .27928(15)  .0675(12) Uani d . 1 . . C
    C9  .6133(9)  .1839(2)  .33589(14)  .0582(11) Uani d . 1 . . C
    C10  .5008(9)  .2547(2)  .35993(15)  .0725(12) Uani d . 1 . . C
    H10A  .3745  .2890  .3419  .087 Uiso calc R 1 . . H
    C11  .5789(10)  .2738(2)  .41112(15)  .0801(13) Uani d . 1 . . C
    H11A  .5092  .3219  .4278  .096 Uiso calc R 1 . . H
    C12  .7589(10)  .2216(2)  .43699(14)  .0742(13) Uani d . 1 . . C
    H12A  .8129  .2331  .4717  .089 Uiso calc R 1 . . H
    C13  .8609(9)  .1505(2)  .41071(14)  .0589(11) Uani d . 1 . . C
    C14 1.0511(9)  .0906(2)  .43950(15)  .0642(11) Uani d . 1 . . C
    C15 1.2627(8)  -.0510(2)  .43016(13)  .0539(10) Uani d . 1 . . C
    C16 1.4442(9)  -.0510(2)  .47177(14)  .0701(12) Uani d . 1 . . C
    H16A 1.4746  -.0013  .4907  .084 Uiso calc R 1 . . H
    C17 1.5841(9)  -.1246(3)  .48614(15)  .0755(12) Uani d . 1 . . C
    H17A 1.7064  -.1243  .5148  .091 Uiso calc R 1 . . H
    C18 1.5413(9)  -.1976(2)  .45809(15)  .0731(12) Uani d . 1 . . C
    H18A 1.6358  -.2468  .4676  .088 Uiso calc R 1 . . H
    C19 1.3606(9)  -.1988(2)  .41614(14)  .0665(11) Uani d . 1 . . C
    H19A 1.3315  -.2488  .3975  .080 Uiso calc R 1 . . H
    C20 1.2214(8)  -.1260(2)  .40137(13)  .0565(10) Uani d . 1 . . C
    C21  .9571(11)  -.1966(2)  .33382(14)  .0881(15) Uani d . 1 . . C
    H21B  .8291  -.1834  .3057  .132 Uiso calc R 1 . . H
    H21C  .8680  -.2337  .3588  .132 Uiso calc R 1 . . H
    H21A 1.1189  -.2240  .3194  .132 Uiso calc R 1 . . H
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C8 . 1.217(4) ?
    O2 C2 . 1.371(4) ?
    O2 C1 . 1.418(4) ?
    O3 C14 . 1.218(4) ?
    O4 C20 . 1.360(4) ?
    O4 C21 . 1.439(4) ?
    N1 C9 . 1.337(4) ?
    N1 C13 . 1.340(4) ?
    N2 C8 . 1.342(4) ?
    N2 C7 . 1.415(4) ?
    N3 C14 . 1.348(4) ?
    N3 C15 . 1.405(4) ?
    C2 C3 . 1.379(5) ?
    C2 C7 . 1.394(5) ?
    C3 C4 . 1.392(5) ?
    C4 C5 . 1.368(6) ?
    C5 C6 . 1.393(5) ?
    C6 C7 . 1.366(5) ?
    C8 C9 . 1.499(5) ?
    C9 C10 . 1.381(4) ?
    C10 C11 . 1.378(5) ?
    C11 C12 . 1.360(5) ?
    C12 C13 . 1.391(4) ?
    C13 C14 . 1.500(5) ?
    C15 C16 . 1.363(4) ?
    C15 C20 . 1.402(4) ?
    C16 C17 . 1.390(5) ?
    C17 C18 . 1.367(4) ?
    C18 C19 . 1.368(5) ?
    C19 C20 . 1.380(5) ?
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
    C2 O2 C1 . . 118.2(3) ?
    C20 O4 C21 . . 117.9(3) ?
    C9 N1 C13 . . 117.7(3) ?
    C8 N2 C7 . . 129.2(3) ?
    C14 N3 C15 . . 127.1(3) ?
    O2 C2 C3 . . 124.5(4) ?
    O2 C2 C7 . . 115.1(4) ?
    C3 C2 C7 . . 120.3(4) ?
    C2 C3 C4 . . 118.7(4) ?
    C5 C4 C3 . . 121.7(4) ?
    C4 C5 C6 . . 118.7(5) ?
    C7 C6 C5 . . 120.9(4) ?
    C6 C7 C2 . . 119.7(4) ?
    C6 C7 N2 . . 124.0(4) ?
    C2 C7 N2 . . 116.3(4) ?
    O1 C8 N2 . . 124.3(4) ?
    O1 C8 C9 . . 121.1(4) ?
    N2 C8 C9 . . 114.6(4) ?
    N1 C9 C10 . . 122.7(3) ?
    N1 C9 C8 . . 118.6(3) ?
    C10 C9 C8 . . 118.7(4) ?
    C11 C10 C9 . . 118.8(4) ?
    C12 C11 C10 . . 119.4(4) ?
    C11 C12 C13 . . 118.8(4) ?
    N1 C13 C12 . . 122.6(4) ?
    N1 C13 C14 . . 118.0(3) ?
    C12 C13 C14 . . 119.3(3) ?
    O3 C14 N3 . . 125.4(4) ?
    O3 C14 C13 . . 120.7(3) ?
    N3 C14 C13 . . 113.9(3) ?
    C16 C15 C20 . . 119.3(4) ?
    C16 C15 N3 . . 125.5(3) ?
    C20 C15 N3 . . 115.3(3) ?
    C15 C16 C17 . . 120.6(4) ?
    C18 C17 C16 . . 119.8(4) ?
    C17 C18 C19 . . 120.4(4) ?
    C18 C19 C20 . . 120.3(4) ?
    O4 C20 C19 . . 125.2(3) ?
    O4 C20 C15 . . 115.1(3) ?
    C19 C20 C15 . . 119.6(4) ?
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
    C1 O2 C2 C3 . . . . -1.3(5) ?
    C1 O2 C2 C7 . . . . 178.5(3) ?
    O2 C2 C3 C4 . . . . 179.4(3) ?
    C7 C2 C3 C4 . . . .  -.3(5) ?
    C2 C3 C4 C5 . . . .  -.4(6) ?
    C3 C4 C5 C6 . . . .  .8(6) ?
    C4 C5 C6 C7 . . . .  -.5(6) ?
    C5 C6 C7 C2 . . . .  -.2(6) ?
    C5 C6 C7 N2 . . . . -178.5(4) ?
    O2 C2 C7 C6 . . . . -179.2(3) ?
    C3 C2 C7 C6 . . . .  .6(5) ?
    O2 C2 C7 N2 . . . .  -.7(5) ?
    C3 C2 C7 N2 . . . . 179.1(3) ?
    C8 N2 C7 C6 . . . . -5.1(6) ?
    C8 N2 C7 C2 . . . . 176.6(3) ?
    C7 N2 C8 O1 . . . . 2.0(7) ?
    C7 N2 C8 C9 . . . . -176.5(3) ?
    C13 N1 C9 C10 . . . . -1.6(5) ?
    C13 N1 C9 C8 . . . . 177.5(4) ?
    O1 C8 C9 N1 . . . . 176.1(4) ?
    N2 C8 C9 N1 . . . . -5.4(5) ?
    O1 C8 C9 C10 . . . . -4.8(6) ?
    N2 C8 C9 C10 . . . . 173.8(3) ?
    N1 C9 C10 C11 . . . . 2.1(6) ?
    C8 C9 C10 C11 . . . . -177.0(4) ?
    C9 C10 C11 C12 . . . . -1.5(6) ?
    C10 C11 C12 C13 . . . .  .5(6) ?
    C9 N1 C13 C12 . . . .  .5(5) ?
    C9 N1 C13 C14 . . . . 178.3(3) ?
    C11 C12 C13 N1 . . . .  .0(6) ?
    C11 C12 C13 C14 . . . . -177.7(4) ?
    C15 N3 C14 O3 . . . . 5.1(7) ?
    C15 N3 C14 C13 . . . . -174.3(3) ?
    N1 C13 C14 O3 . . . . 175.6(4) ?
    C12 C13 C14 O3 . . . . -6.6(6) ?
    N1 C13 C14 N3 . . . . -4.9(5) ?
    C12 C13 C14 N3 . . . . 172.9(4) ?
    C14 N3 C15 C16 . . . . -20.5(6) ?
    C14 N3 C15 C20 . . . . 160.5(4) ?
    C20 C15 C16 C17 . . . .  -.9(6) ?
    N3 C15 C16 C17 . . . . -179.9(4) ?
    C15 C16 C17 C18 . . . .  .5(6) ?
    C16 C17 C18 C19 . . . .  -.4(6) ?
    C17 C18 C19 C20 . . . .  .6(6) ?
    C21 O4 C20 C19 . . . . 8.4(5) ?
    C21 O4 C20 C15 . . . . -171.2(4) ?
    C18 C19 C20 O4 . . . . 179.4(4) ?
    C18 C19 C20 C15 . . . . -1.0(6) ?
    C16 C15 C20 O4 . . . . -179.2(3) ?
    N3 C15 C20 O4 . . . .  -.1(5) ?
    C16 C15 C20 C19 . . . . 1.2(6) ?
    N3 C15 C20 C19 . . . . -179.8(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N2 H2A O2 . . 1_555  .86 2.19 2.602(4) 109.5 yes
    N2 H2A N1 . . 1_555  .86 2.26 2.700(4) 111.8 yes
    N3 H3A O4 . . 1_555  .86 2.22 2.580(4) 105.3 yes
    N3 H3A N1 . . 1_555  .86 2.25 2.678(4) 111.0 yes
    C6 H6A O1 . . 1_555  .93 2.28 2.891(5) 122.5 yes
    C11 H11A O3 . . 4_456  .93 2.57 3.260(4) 131.5 yes
    C16 H16A O3 . . 1_555  .93 2.37 2.917(4) 117.8 yes
    C21 H21B O1 . . 3_645  .96 2.49 3.124(5) 123.8 yes
