#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/48/2234822.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_2234822
loop_
_publ_author_name
'Huang, Liangzhu'
'Li, Youqiang'
'Gao, Dongmei'
'Du, Zhenting'
_publ_section_title
;
 3,4-Bis(4-methoxyphenyl)-2,5-dihydro-1H-pyrrole-2,5-dione
;
_journal_coeditor_code           TK5079
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1328
_journal_paper_doi               10.1107/S1600536812014158
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C18 H15 N O4'
_chemical_formula_moiety         'C18 H15 N O4'
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31
_chemical_melting_point          517
_chemical_name_systematic
;
3,4-Bis(4-methoxyphenyl)-2,5-dihydro-1H-pyrrole-2,5-dione
;
_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                90.945(6)
_cell_angle_beta                 95.205(5)
_cell_angle_gamma                97.862(5)
_cell_formula_units_Z            2
_cell_length_a                   6.030(3)
_cell_length_b                   8.971(5)
_cell_length_c                   14.023(8)
_cell_measurement_reflns_used    1101
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.59
_cell_measurement_theta_min      2.68
_cell_volume                     748.0(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3943
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.2331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.114(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0505
_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)+(0.0769P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                1751
_reflns_number_total             2607
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5079.cif
_cod_data_source_block           I
_cod_database_code               2234822
_cod_database_fobs_code          2234822
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_symmetry_multiplicity
C C1 0.3834(4) 0.3007(3) 0.96603(16) 0.0422(6) Uani d . 1 1
C C2 0.4781(4) 0.3299(2) 0.87029(14) 0.0359(6) Uani d . 1 1
C C3 0.3710(4) 0.4394(2) 0.82907(15) 0.0351(5) Uani d . 1 1
C C4 0.2055(4) 0.4800(3) 0.89376(15) 0.0385(6) Uani d . 1 1
C C5 0.6460(4) 0.2446(2) 0.83558(15) 0.0374(6) Uani d . 1 1
C C6 0.6830(4) 0.2411(3) 0.73879(16) 0.0453(6) Uani d . 1 1
H H6 0.6022 0.2964 0.6961 0.054 Uiso calc R 1 1
C C7 0.8349(4) 0.1582(3) 0.70524(16) 0.0504(7) Uani d . 1 1
H H7 0.8558 0.1583 0.6403 0.060 Uiso calc R 1 1
C C8 0.9589(4) 0.0736(2) 0.76676(16) 0.0427(6) Uani d . 1 1
C C9 0.9229(4) 0.0735(3) 0.86255(17) 0.0497(7) Uani d . 1 1
H H9 1.0021 0.0164 0.9047 0.060 Uiso calc R 1 1
C C10 0.7698(4) 0.1579(3) 0.89605(16) 0.0462(6) Uani d . 1 1
H H10 0.7486 0.1571 0.9609 0.055 Uiso calc R 1 1
C C11 1.2389(5) -0.0910(3) 0.7865(2) 0.0646(8) Uani d . 1 1
H H11A 1.3177 -0.0288 0.8385 0.097 Uiso calc R 1 1
H H11B 1.3454 -0.1313 0.7500 0.097 Uiso calc R 1 1
H H11C 1.1421 -0.1721 0.8114 0.097 Uiso calc R 1 1
C C12 0.4059(4) 0.5231(2) 0.74060(14) 0.0347(5) Uani d . 1 1
C C13 0.6128(4) 0.6031(3) 0.72713(16) 0.0449(6) Uani d . 1 1
H H13 0.7322 0.6006 0.7737 0.054 Uiso calc R 1 1
C C14 0.6481(4) 0.6866(3) 0.64669(16) 0.0465(6) Uani d . 1 1
H H14 0.7886 0.7405 0.6399 0.056 Uiso calc R 1 1
C C15 0.4738(4) 0.6893(3) 0.57684(16) 0.0441(6) Uani d . 1 1
C C16 0.2652(4) 0.6106(3) 0.58874(17) 0.0537(7) Uani d . 1 1
H H16 0.1469 0.6125 0.5416 0.064 Uiso calc R 1 1
C C17 0.2309(4) 0.5294(3) 0.66974(16) 0.0458(6) Uani d . 1 1
H H17 0.0889 0.4782 0.6772 0.055 Uiso calc R 1 1
C C18 0.6974(5) 0.8516(4) 0.4787(2) 0.0779(9) Uani d . 1 1
H H18A 0.7448 0.9232 0.5307 0.117 Uiso calc R 1 1
H H18B 0.6827 0.9037 0.4198 0.117 Uiso calc R 1 1
H H18C 0.8070 0.7840 0.4750 0.117 Uiso calc R 1 1
N N1 0.2275(3) 0.3981(2) 0.97460(12) 0.0434(5) Uani d . 1 1
H H1 0.1543 0.4062 1.0239 0.052 Uiso calc R 1 1
O O1 0.0729(3) 0.57097(18) 0.88000(11) 0.0482(5) Uani d . 1 1
O O2 0.4269(3) 0.2105(2) 1.02547(12) 0.0629(6) Uani d . 1 1
O O3 1.1072(3) -0.00307(19) 0.72612(12) 0.0586(5) Uani d . 1 1
O O4 0.4878(3) 0.7688(2) 0.49458(12) 0.0668(6) Uani d . 1 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
O2 C1 N1 124.0(2)
O2 C1 C2 129.2(2)
N1 C1 C2 106.80(19)
C3 C2 C5 131.08(19)
C3 C2 C1 106.54(19)
C5 C2 C1 122.34(19)
C2 C3 C12 131.28(19)
C2 C3 C4 108.34(18)
C12 C3 C4 120.22(18)
O1 C4 N1 124.7(2)
O1 C4 C3 127.6(2)
N1 C4 C3 107.73(19)
C10 C5 C6 116.7(2)
C10 C5 C2 122.1(2)
C6 C5 C2 121.1(2)
C7 C6 C5 121.6(2)
C7 C6 H6 119.2
C5 C6 H6 119.2
C6 C7 C8 121.0(2)
C6 C7 H7 119.5
C8 C7 H7 119.5
O3 C8 C9 125.3(2)
O3 C8 C7 116.1(2)
C9 C8 C7 118.5(2)
C8 C9 C10 120.2(2)
C8 C9 H9 119.9
C10 C9 H9 119.9
C9 C10 C5 122.0(2)
C9 C10 H10 119.0
C5 C10 H10 119.0
O3 C11 H11A 109.5
O3 C11 H11B 109.5
H11A C11 H11B 109.5
O3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C17 117.5(2)
C13 C12 C3 120.88(19)
C17 C12 C3 121.5(2)
C14 C13 C12 122.1(2)
C14 C13 H13 118.9
C12 C13 H13 118.9
C15 C14 C13 119.4(2)
C15 C14 H14 120.3
C13 C14 H14 120.3
O4 C15 C14 124.7(2)
O4 C15 C16 115.7(2)
C14 C15 C16 119.6(2)
C17 C16 C15 120.6(2)
C17 C16 H16 119.7
C15 C16 H16 119.7
C16 C17 C12 120.8(2)
C16 C17 H17 119.6
C12 C17 H17 119.6
O4 C18 H18A 109.5
O4 C18 H18B 109.5
H18A C18 H18B 109.5
O4 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C4 N1 C1 110.48(18)
C4 N1 H1 124.8
C1 N1 H1 124.8
C8 O3 C11 118.18(19)
C15 O4 C18 118.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.208(2)
C1 N1 1.380(3)
C1 C2 1.519(3)
C2 C3 1.357(3)
C2 C5 1.462(3)
C3 C12 1.477(3)
C3 C4 1.485(3)
C4 O1 1.224(3)
C4 N1 1.367(3)
C5 C10 1.395(3)
C5 C6 1.396(3)
C6 C7 1.366(3)
C6 H6 0.9300
C7 C8 1.393(3)
C7 H7 0.9300
C8 O3 1.358(3)
C8 C9 1.380(3)
C9 C10 1.380(3)
C9 H9 0.9300
C10 H10 0.9300
C11 O3 1.429(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C13 1.382(3)
C12 C17 1.390(3)
C13 C14 1.381(3)
C13 H13 0.9300
C14 C15 1.373(3)
C14 H14 0.9300
C15 O4 1.369(3)
C15 C16 1.381(3)
C16 C17 1.375(3)
C16 H16 0.9300
C17 H17 0.9300
C18 O4 1.413(3)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
N1 H1 0.8600
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
_geom_hbond_publ_flag
N1 H1 O1 2_567 0.86 2.03 2.882(3) 168 yes
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
O2 C1 C2 C3 178.3(2)
N1 C1 C2 C3 -0.8(2)
O2 C1 C2 C5 0.4(4)
N1 C1 C2 C5 -178.69(19)
C5 C2 C3 C12 -8.5(4)
C1 C2 C3 C12 173.9(2)
C5 C2 C3 C4 176.3(2)
C1 C2 C3 C4 -1.4(2)
C2 C3 C4 O1 -177.7(2)
C12 C3 C4 O1 6.5(3)
C2 C3 C4 N1 3.1(2)
C12 C3 C4 N1 -172.74(19)
C3 C2 C5 C10 166.7(2)
C1 C2 C5 C10 -16.0(3)
C3 C2 C5 C6 -16.1(4)
C1 C2 C5 C6 161.3(2)
C10 C5 C6 C7 -0.7(4)
C2 C5 C6 C7 -178.1(2)
C5 C6 C7 C8 0.1(4)
C6 C7 C8 O3 -179.2(2)
C6 C7 C8 C9 0.9(4)
O3 C8 C9 C10 179.0(2)
C7 C8 C9 C10 -1.1(4)
C8 C9 C10 C5 0.4(4)
C6 C5 C10 C9 0.5(3)
C2 C5 C10 C9 177.8(2)
C2 C3 C12 C13 -56.6(3)
C4 C3 C12 C13 118.2(2)
C2 C3 C12 C17 126.1(3)
C4 C3 C12 C17 -59.2(3)
C17 C12 C13 C14 -0.2(3)
C3 C12 C13 C14 -177.7(2)
C12 C13 C14 C15 -0.9(4)
C13 C14 C15 O4 179.4(2)
C13 C14 C15 C16 1.0(4)
O4 C15 C16 C17 -178.6(2)
C14 C15 C16 C17 -0.1(4)
C15 C16 C17 C12 -1.0(4)
C13 C12 C17 C16 1.1(4)
C3 C12 C17 C16 178.6(2)
O1 C4 N1 C1 177.1(2)
C3 C4 N1 C1 -3.6(3)
O2 C1 N1 C4 -176.4(2)
C2 C1 N1 C4 2.8(2)
C9 C8 O3 C11 -0.3(3)
C7 C8 O3 C11 179.8(2)
C14 C15 O4 C18 1.5(4)
C16 C15 O4 C18 179.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9122020
