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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/79/2227968.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_2227968
loop_
_publ_author_name
'Nishijima, Takahiro'
'Kataoka, Kotaro'
'Nagasawa, Atsushi'
'Okamoto, Akiko'
'Yonezawa, Noriyuki'
_publ_section_title
;
 1,8-Bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2904
_journal_page_last               o2905
_journal_paper_doi               10.1107/S1600536810041346
_journal_volume                  66
_journal_year                    2010
_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_melting_point_gt       580.5
_chemical_melting_point_lt       583.0
_chemical_name_common
;
1,8-Bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene
;
_chemical_name_systematic
;
[8-(4-aminobenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-aminophenyl)methanone
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.5230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2996(3)
_cell_length_b                   10.2811(2)
_cell_length_c                   15.4306(3)
_cell_measurement_reflns_used    11162
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.1
_cell_volume                     2063.90(7)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97(Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaki R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17453
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_min         5.48
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.7512
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.372
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.6125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                1690
_reflns_number_total             1892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            rz2496.cif
_cod_data_source_block           I
_cod_database_code               2227968
_cod_database_fobs_code          2227968
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'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.77436(7) -0.11857(9) 0.88398(7) 0.0426(3) Uani d . 1 . .
O O2 0.62425(7) 0.07379(8) 0.72735(6) 0.0341(3) Uani d . 1 . .
N N1 0.63099(9) 0.33681(13) 1.10437(8) 0.0405(3) Uani d . 1 . .
C C1 0.62489(9) 0.26028(13) 1.02908(8) 0.0307(3) Uani d . 1 . .
C C2 0.63071(9) 0.31736(12) 0.94876(9) 0.0311(3) Uani d . 1 . .
C C3 0.62524(9) 0.24184(12) 0.87347(8) 0.0293(3) Uani d . 1 . .
C C4 0.61301(8) 0.10665(11) 0.87440(8) 0.0268(3) Uani d . 1 . .
C C5 0.60412(9) 0.05115(13) 0.95329(9) 0.0311(3) Uani d . 1 . .
C C6 0.60986(9) 0.12582(13) 1.02970(9) 0.0333(3) Uani d . 1 . .
C C7 0.61101(8) 0.02784(12) 0.79446(8) 0.0266(3) Uani d . 1 . .
C C8 0.59675(9) -0.11834(12) 0.79669(8) 0.0278(3) Uani d . 1 . .
C C9 0.5000 -0.18296(16) 0.7500 0.0267(4) Uani d S 1 . .
C C10 0.5000 -0.32223(16) 0.7500 0.0302(4) Uani d S 1 . .
C C11 0.59352(11) -0.39011(13) 0.79714(9) 0.0355(3) Uani d . 1 . .
C C12 0.68471(11) -0.32756(13) 0.84270(9) 0.0366(3) Uani d . 1 . .
C C13 0.68596(9) -0.19016(13) 0.84184(9) 0.0328(3) Uani d . 1 . .
C C14 0.86976(11) -0.18638(16) 0.93136(11) 0.0495(4) Uani d . 1 . .
H H14A 0.9248 -0.1246 0.9574 0.059 Uiso calc R 1 . .
H H14B 0.8815 -0.2415 0.8866 0.059 Uiso calc R 1 . .
H H14C 0.8669 -0.2385 0.9818 0.059 Uiso calc R 1 . .
H H1 0.5936(11) -0.0400(16) 0.9542(10) 0.038(4) Uiso d . 1 . .
H H2 0.6079(12) 0.0862(14) 1.0838(11) 0.039(4) Uiso d . 1 . .
H H3 0.6425(15) 0.2952(19) 1.1606(14) 0.068(6) Uiso d . 1 . .
H H4 0.6672(15) 0.413(2) 1.1123(13) 0.065(5) Uiso d . 1 . .
H H5 0.6425(11) 0.4089(16) 0.9514(10) 0.038(4) Uiso d . 1 . .
H H6 0.6305(11) 0.2772(14) 0.8178(10) 0.034(3) Uiso d . 1 . .
H H7 0.5900(12) -0.4824(17) 0.7944(11) 0.047(4) Uiso d . 1 . .
H H8 0.7479(13) -0.3756(16) 0.8739(11) 0.048(4) 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C13 O1 C14 . . 118.41(11) ?
C1 N1 H3 . . 117.1(12) ?
C1 N1 H4 . . 115.9(12) ?
H3 N1 H4 . . 113.7(17) ?
N1 C1 C6 . . 121.01(12) ?
N1 C1 C2 . . 120.00(12) ?
C6 C1 C2 . . 118.97(11) ?
C3 C2 C1 . . 120.48(12) ?
C3 C2 H5 . . 122.7(8) ?
C1 C2 H5 . . 116.7(8) ?
C2 C3 C4 . . 121.05(11) ?
C2 C3 H6 . . 122.9(9) ?
C4 C3 H6 . . 116.1(9) ?
C5 C4 C3 . . 118.09(11) ?
C5 C4 C7 . . 122.03(11) ?
C3 C4 C7 . . 119.88(11) ?
C6 C5 C4 . . 121.49(12) ?
C6 C5 H1 . . 119.3(9) ?
C4 C5 H1 . . 119.2(9) ?
C5 C6 C1 . . 119.88(11) ?
C5 C6 H2 . . 120.3(9) ?
C1 C6 H2 . . 119.7(9) ?
O2 C7 C4 . . 122.92(11) ?
O2 C7 C8 . . 118.10(10) ?
C4 C7 C8 . . 118.92(10) ?
C13 C8 C9 . . 120.11(12) ?
C13 C8 C7 . . 115.75(10) ?
C9 C8 C7 . . 123.98(11) ?
C8 C9 C8 . 2_656 124.66(15) ?
C8 C9 C10 . . 117.67(8) ?
C8 C9 C10 2_656 . 117.67(8) ?
C11 C10 C11 2_656 . 120.81(17) ?
C11 C10 C9 2_656 . 119.59(8) ?
C11 C10 C9 . . 119.59(8) ?
C12 C11 C10 . . 122.17(13) ?
C12 C11 H7 . . 121.2(9) ?
C10 C11 H7 . . 116.6(10) ?
C11 C12 C13 . . 118.78(12) ?
C11 C12 H8 . . 121.0(10) ?
C13 C12 H8 . . 120.2(10) ?
O1 C13 C8 . . 115.30(11) ?
O1 C13 C12 . . 123.02(11) ?
C8 C13 C12 . . 121.67(12) ?
O1 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 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 C13 . 1.3712(15) ?
O1 C14 . 1.4331(15) ?
O2 C7 . 1.2223(14) ?
N1 C1 . 1.3756(16) ?
N1 H3 . 0.92(2) ?
N1 H4 . 0.92(2) ?
C1 C6 . 1.3996(19) ?
C1 C2 . 1.4045(17) ?
C2 C3 . 1.3724(17) ?
C2 H5 . 0.954(16) ?
C3 C4 . 1.4017(17) ?
C3 H6 . 0.964(14) ?
C4 C5 . 1.3972(16) ?
C4 C7 . 1.4662(16) ?
C5 C6 . 1.3806(18) ?
C5 H1 . 0.950(16) ?
C6 H2 . 0.939(15) ?
C7 C8 . 1.5189(17) ?
C8 C13 . 1.3857(17) ?
C8 C9 . 1.4308(14) ?
C9 C8 2_656 1.4308(14) ?
C9 C10 . 1.432(2) ?
C10 C11 2_656 1.4132(16) ?
C10 C11 . 1.4132(16) ?
C11 C12 . 1.359(2) ?
C11 H7 . 0.950(18) ?
C12 C13 . 1.4128(19) ?
C12 H8 . 0.965(17) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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 H4 O1 7_657 0.93(2) 2.26(2) 3.1708(17) 169.1(18)
C14 H14B O2 4_646 0.96 2.57 3.5013(18) 165
N1 H3 Cg 6_556 0.92(2) 2.50(2) 3.3301(13) 149.8(18)
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
N1 C1 C2 C3 . . . . 179.66(11) ?
C6 C1 C2 C3 . . . . -2.20(18) ?
C1 C2 C3 C4 . . . . 0.48(18) ?
C2 C3 C4 C5 . . . . 1.46(17) ?
C2 C3 C4 C7 . . . . -177.87(10) ?
C3 C4 C5 C6 . . . . -1.70(17) ?
C7 C4 C5 C6 . . . . 177.61(10) ?
C4 C5 C6 C1 . . . . 0.00(18) ?
N1 C1 C6 C5 . . . . -179.93(11) ?
C2 C1 C6 C5 . . . . 1.96(18) ?
C5 C4 C7 O2 . . . . -175.91(10) ?
C3 C4 C7 O2 . . . . 3.40(17) ?
C5 C4 C7 C8 . . . . 1.21(16) ?
C3 C4 C7 C8 . . . . -179.48(10) ?
O2 C7 C8 C13 . . . . 89.52(13) ?
C4 C7 C8 C13 . . . . -87.74(13) ?
O2 C7 C8 C9 . . . . -85.85(13) ?
C4 C7 C8 C9 . . . . 96.90(12) ?
C13 C8 C9 C8 . . . 2_656 178.46(11) ?
C7 C8 C9 C8 . . . 2_656 -6.37(8) ?
C13 C8 C9 C10 . . . . -1.54(11) ?
C7 C8 C9 C10 . . . . 173.63(8) ?
C8 C9 C10 C11 . . . 2_656 -178.56(8) ?
C8 C9 C10 C11 2_656 . . 2_656 1.44(8) ?
C8 C9 C10 C11 . . . . 1.44(8) ?
C8 C9 C10 C11 2_656 . . . -178.56(8) ?
C11 C10 C11 C12 2_656 . . . 179.69(13) ?
C9 C10 C11 C12 . . . . -0.31(13) ?
C10 C11 C12 C13 . . . . -0.74(18) ?
C14 O1 C13 C8 . . . . -179.48(11) ?
C14 O1 C13 C12 . . . . -0.25(18) ?
C9 C8 C13 O1 . . . . 179.77(9) ?
C7 C8 C13 O1 . . . . 4.22(15) ?
C9 C8 C13 C12 . . . . 0.53(17) ?
C7 C8 C13 C12 . . . . -175.03(11) ?
C11 C12 C13 O1 . . . . -178.55(11) ?
C11 C12 C13 C8 . . . . 0.64(19) ?
