#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/55/2015553.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_2015553
loop_
_publ_author_name
'Lin-Hai Jing'
'Da-Bin Qin'
'Shao-Jin Gu'
'Huan-Xia Zhang'
'Gang Lei'
_publ_section_title
;
 N,N'-Bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide
;
_journal_coeditor_code           GA3018
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o561
_journal_page_last               o562
_journal_paper_doi               10.1107/S0108270106026928
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C26 H22 N2 O4'
_chemical_formula_moiety         'C26 H22 N2 O4'
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.46
_chemical_name_systematic
;
N,N'-Bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.9750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   34.7194(9)
_cell_length_b                   6.04620(10)
_cell_length_c                   10.0042(3)
_cell_measurement_reflns_used    9668
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     2095.03(9)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0109
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8696
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.213
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         2074
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0291
_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)+(0.0592P)²+0.5976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                2049
_reflns_number_total             2074
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga3018.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2015553
_cod_database_fobs_code          2015553
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
O O1 0.26715(4) 0.5097(3) 0.23758(13) 0.0243(3) Uani d . 1
O O2 0.22530(4) 0.1268(2) 0.57759(14) 0.0255(3) Uani d . 1
O O3 0.44834(4) 0.5514(3) 0.66101(14) 0.0267(3) Uani d . 1
O O4 0.49031(5) 0.1080(3) 0.33995(15) 0.0296(4) Uani d . 1
N N1 0.25272(5) 0.4794(3) 0.45421(15) 0.0177(3) Uani d . 1
H H1N 0.2615 0.4942 0.5384 0.021 Uiso calc R 1
N N2 0.46429(5) 0.4694(3) 0.45087(16) 0.0182(3) Uani d . 1
H H2N 0.4560 0.4692 0.3658 0.022 Uiso calc R 1
C C1 0.31914(5) 0.5484(3) 0.40293(18) 0.0167(4) Uani d . 1
C C2 0.34382(5) 0.3959(3) 0.35411(17) 0.0190(4) Uani d . 1
H H2 0.3342 0.2883 0.2911 0.023 Uiso calc R 1
C C3 0.38327(5) 0.3976(3) 0.39666(17) 0.0194(4) Uani d . 1
H H3 0.4000 0.2891 0.3636 0.023 Uiso calc R 1
C C4 0.39798(5) 0.5550(3) 0.48565(18) 0.0166(4) Uani d . 1
C C5 0.38814(5) 0.9061(3) 0.61120(17) 0.0190(4) Uani d . 1
H H5 0.4149 0.9134 0.6377 0.023 Uiso calc R 1
C C6 0.36402(6) 1.0679(3) 0.65184(18) 0.0212(4) Uani d . 1
H H6 0.3741 1.1852 0.7069 0.025 Uiso calc R 1
C C7 0.32411(6) 1.0615(3) 0.61225(19) 0.0213(4) Uani d . 1
H H7 0.3075 1.1735 0.6416 0.026 Uiso calc R 1
C C8 0.30945(5) 0.8947(3) 0.53204(18) 0.0197(4) Uani d . 1
H H8 0.2827 0.8941 0.5045 0.024 Uiso calc R 1
C C9 0.33338(5) 0.7222(3) 0.48894(17) 0.0158(3) Uani d . 1
C C10 0.37386(5) 0.7271(3) 0.53005(17) 0.0164(4) Uani d . 1
C C11 0.27725(5) 0.5161(3) 0.35739(18) 0.0155(4) Uani d . 1
C C12 0.21345(5) 0.4178(3) 0.42651(18) 0.0172(4) Uani d . 1
C C13 0.19931(5) 0.2342(3) 0.49328(19) 0.0199(4) Uani d . 1
C C14 0.16084(6) 0.1713(4) 0.4682(2) 0.0274(4) Uani d . 1
H H14 0.1509 0.0485 0.5141 0.033 Uiso calc R 1
C C15 0.13710(6) 0.2880(4) 0.3764(2) 0.0315(5) Uani d . 1
H H15 0.1110 0.2438 0.3592 0.038 Uiso calc R 1
C C16 0.15099(6) 0.4683(4) 0.3094(2) 0.0312(5) Uani d . 1
H H16 0.1346 0.5469 0.2460 0.037 Uiso calc R 1
C C17 0.18924(6) 0.5337(4) 0.3355(2) 0.0231(4) Uani d . 1
H H17 0.1988 0.6585 0.2905 0.028 Uiso calc R 1
C C18 0.21267(7) -0.0657(4) 0.6459(2) 0.0330(5) Uani d . 1
H H18A 0.1922 -0.0244 0.7038 0.040 Uiso calc R 1
H H18B 0.2345 -0.1289 0.7006 0.040 Uiso calc R 1
H H18C 0.2027 -0.1753 0.5801 0.040 Uiso calc R 1
C C19 0.43904(6) 0.5291(3) 0.54159(19) 0.0174(4) Uani d . 1
C C20 0.50327(5) 0.4069(3) 0.48311(18) 0.0192(4) Uani d . 1
C C21 0.51692(6) 0.2188(3) 0.42038(19) 0.0219(4) Uani d . 1
C C22 0.55549(6) 0.1559(4) 0.4444(2) 0.0305(5) Uani d . 1
H H22 0.5652 0.0307 0.4002 0.037 Uiso calc R 1
C C23 0.57946(6) 0.2768(4) 0.5329(3) 0.0347(5) Uani d . 1
H H23 0.6056 0.2333 0.5498 0.042 Uiso calc R 1
C C24 0.56585(6) 0.4602(4) 0.5971(2) 0.0332(5) Uani d . 1
H H24 0.5826 0.5413 0.6583 0.040 Uiso calc R 1
C C25 0.52750(6) 0.5263(4) 0.5718(2) 0.0251(4) Uani d . 1
H H25 0.5181 0.6528 0.6154 0.030 Uiso calc R 1
C C26 0.50263(8) -0.0825(4) 0.2699(2) 0.0354(5) Uani d . 1
H H26A 0.5224 -0.0393 0.2095 0.042 Uiso calc R 1
H H26B 0.4805 -0.1473 0.2177 0.042 Uiso calc R 1
H H26C 0.5135 -0.1916 0.3345 0.042 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_publ_flag
C13 O2 C18 118.21(17) ?
C21 O4 C26 118.27(18) ?
C11 N1 C12 123.14(15) y
C11 N1 H1N 118.4 n
C12 N1 H1N 118.4 n
C19 N2 C20 124.74(16) y
C19 N2 H2N 117.6 n
C20 N2 H2N 117.6 n
C2 C1 C9 120.78(17) ?
C2 C1 C11 114.77(17) ?
C9 C1 C11 124.45(16) ?
C1 C2 C3 120.44(17) ?
C1 C2 H2 119.8 ?
C3 C2 H2 119.8 ?
C4 C3 C2 120.74(17) ?
C4 C3 H3 119.6 ?
C2 C3 H3 119.6 ?
C3 C4 C10 120.41(17) ?
C3 C4 C19 117.95(16) ?
C10 C4 C19 121.48(16) ?
C6 C5 C10 121.21(16) ?
C6 C5 H5 119.4 ?
C10 C5 H5 119.4 ?
C5 C6 C7 120.31(17) ?
C5 C6 H6 119.8 ?
C7 C6 H6 119.8 ?
C8 C7 C6 120.20(17) ?
C8 C7 H7 119.9 ?
C6 C7 H7 119.9 ?
C7 C8 C9 121.28(17) ?
C7 C8 H8 119.4 ?
C9 C8 H8 119.4 ?
C8 C9 C1 122.65(17) ?
C8 C9 C10 118.66(16) ?
C1 C9 C10 118.66(15) ?
C5 C10 C4 123.00(16) ?
C5 C10 C9 118.33(15) ?
C4 C10 C9 118.66(15) ?
O1 C11 N1 122.94(17) ?
O1 C11 C1 120.30(16) ?
N1 C11 C1 116.59(15) ?
C17 C12 C13 119.82(18) ?
C17 C12 N1 121.70(18) ?
C13 C12 N1 118.48(17) ?
O2 C13 C14 124.66(19) ?
O2 C13 C12 115.83(17) ?
C14 C13 C12 119.50(18) ?
C15 C14 C13 120.0(2) ?
C15 C14 H14 120.0 ?
C13 C14 H14 120.0 ?
C14 C15 C16 120.77(19) ?
C14 C15 H15 119.6 ?
C16 C15 H15 119.6 ?
C15 C16 C17 119.5(2) ?
C15 C16 H16 120.3 ?
C17 C16 H16 120.3 ?
C12 C17 C16 120.4(2) ?
C12 C17 H17 119.8 ?
C16 C17 H17 119.8 ?
O2 C18 H18A 109.5 ?
O2 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O2 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
O3 C19 N2 123.01(18) ?
O3 C19 C4 122.11(17) ?
N2 C19 C4 114.82(16) ?
C25 C20 C21 120.19(18) ?
C25 C20 N2 122.31(18) ?
C21 C20 N2 117.49(17) ?
O4 C21 C22 124.9(2) ?
O4 C21 C20 115.44(17) ?
C22 C21 C20 119.7(2) ?
C23 C22 C21 119.6(2) ?
C23 C22 H22 120.2 ?
C21 C22 H22 120.2 ?
C24 C23 C22 120.8(2) ?
C24 C23 H23 119.6 ?
C22 C23 H23 119.6 ?
C23 C24 C25 119.9(2) ?
C23 C24 H24 120.1 ?
C25 C24 H24 120.1 ?
C20 C25 C24 119.8(2) ?
C20 C25 H25 120.1 ?
C24 C25 H25 120.1 ?
O4 C26 H26A 109.5 ?
O4 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
O4 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1.226(2) ?
O2 C13 1.357(2) ?
O2 C18 1.434(2) ?
O3 C19 1.223(2) ?
O4 C21 1.359(3) ?
O4 C26 1.429(3) ?
N1 C11 1.352(3) y
N1 C12 1.422(2) y
N1 H1N 0.8800 ?
N2 C19 1.354(2) y
N2 C20 1.420(2) y
N2 H2N 0.8800 ?
C1 C2 1.372(3) ?
C1 C9 1.425(3) ?
C1 C11 1.506(2) y
C2 C3 1.406(2) ?
C2 H2 0.9500 ?
C3 C4 1.377(3) ?
C3 H3 0.9500 ?
C4 C10 1.426(3) ?
C4 C19 1.503(2) y
C5 C6 1.368(3) ?
C5 C10 1.421(3) ?
C5 H5 0.9500 ?
C6 C7 1.415(3) ?
C6 H6 0.9500 ?
C7 C8 1.365(3) ?
C7 H7 0.9500 ?
C8 C9 1.419(3) ?
C8 H8 0.9500 ?
C9 C10 1.437(2) ?
C12 C17 1.386(3) ?
C12 C13 1.402(3) ?
C13 C14 1.395(3) ?
C14 C15 1.384(3) ?
C14 H14 0.9500 ?
C15 C16 1.384(4) ?
C15 H15 0.9500 ?
C16 C17 1.393(3) ?
C16 H16 0.9500 ?
C17 H17 0.9500 ?
C18 H18A 0.9800 ?
C18 H18B 0.9800 ?
C18 H18C 0.9800 ?
C20 C25 1.383(3) ?
C20 C21 1.398(3) ?
C21 C22 1.397(3) ?
C22 C23 1.381(4) ?
C22 H22 0.9500 ?
C23 C24 1.381(4) ?
C23 H23 0.9500 ?
C24 C25 1.397(3) ?
C24 H24 0.9500 ?
C25 H25 0.9500 ?
C26 H26A 0.9800 ?
C26 H26B 0.9800 ?
C26 H26C 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 O1 2_565 0.88 1.99 2.845(2) 164.0
N2 H2N O3 2_564 0.88 2.05 2.917(2) 168.0
C2 H2 Cg2 2_564 0.95 2.55 3.353(2) 142.0
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_publ_flag
C9 C1 C2 C3 5.1(3) ?
C11 C1 C2 C3 -175.33(16) ?
C1 C2 C3 C4 -1.4(3) ?
C2 C3 C4 C10 -3.8(3) ?
C2 C3 C4 C19 171.71(16) ?
C10 C5 C6 C7 -0.7(3) ?
C5 C6 C7 C8 -0.7(3) ?
C6 C7 C8 C9 1.4(3) ?
C7 C8 C9 C1 -178.62(17) ?
C7 C8 C9 C10 -0.8(2) ?
C2 C1 C9 C8 174.22(17) ?
C11 C1 C9 C8 -5.3(3) ?
C2 C1 C9 C10 -3.6(3) ?
C11 C1 C9 C10 176.88(15) ?
C6 C5 C10 C4 -179.93(17) ?
C6 C5 C10 C9 1.3(2) ?
C3 C4 C10 C5 -173.65(17) ?
C19 C4 C10 C5 11.0(3) ?
C3 C4 C10 C9 5.1(2) ?
C19 C4 C10 C9 -170.22(15) ?
C8 C9 C10 C5 -0.6(2) ?
C1 C9 C10 C5 177.37(16) ?
C8 C9 C10 C4 -179.39(17) ?
C1 C9 C10 C4 -1.4(2) ?
C12 N1 C11 O1 3.6(3) ?
C12 N1 C11 C1 -171.64(16) y
C2 C1 C11 O1 -56.1(2) ?
C9 C1 C11 O1 123.4(2) ?
C2 C1 C11 N1 119.28(18) y
C9 C1 C11 N1 -61.2(2) ?
C11 N1 C12 C17 -50.0(3) ?
C11 N1 C12 C13 129.65(19) ?
C18 O2 C13 C14 0.2(3) ?
C18 O2 C13 C12 -178.43(18) ?
C17 C12 C13 O2 178.11(17) ?
N1 C12 C13 O2 -1.6(3) ?
C17 C12 C13 C14 -0.6(3) ?
N1 C12 C13 C14 179.71(17) ?
O2 C13 C14 C15 -177.62(19) ?
C12 C13 C14 C15 1.0(3) ?
C13 C14 C15 C16 -0.5(3) ?
C14 C15 C16 C17 -0.4(3) ?
C13 C12 C17 C16 -0.3(3) ?
N1 C12 C17 C16 179.37(19) ?
C15 C16 C17 C12 0.8(3) ?
C20 N2 C19 O3 5.8(3) ?
C20 N2 C19 C4 -171.22(17) y
C3 C4 C19 O3 -134.0(2) ?
C10 C4 C19 O3 41.5(3) ?
C3 C4 C19 N2 43.0(2) y
C10 C4 C19 N2 -141.52(17) ?
C19 N2 C20 C25 -46.2(3) ?
C19 N2 C20 C21 134.5(2) ?
C26 O4 C21 C22 -2.6(3) ?
C26 O4 C21 C20 178.31(19) ?
C25 C20 C21 O4 177.09(18) ?
N2 C20 C21 O4 -3.6(3) ?
C25 C20 C21 C22 -2.0(3) ?
N2 C20 C21 C22 177.32(18) ?
O4 C21 C22 C23 -177.2(2) ?
C20 C21 C22 C23 1.8(3) ?
C21 C22 C23 C24 -0.5(4) ?
C22 C23 C24 C25 -0.6(4) ?
C21 C20 C25 C24 1.0(3) ?
N2 C20 C25 C24 -178.37(19) ?
C23 C24 C25 C20 0.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133438
