#------------------------------------------------------------------------------
#$Date: 2019-10-28 09:23:29 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/05/2240524.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_2240524
loop_
_publ_author_name
'Alshawi, Jasim'
'Yousif, Muoayed'
'Timco, Gregore'
'Vitorica Yrezabal, Inigo J.'
'Winpenny, Richard'
'Al-Jeboori, Mohamad J.'
_publ_section_title
;
 Crystal structure of diethyl
 3,3'-{2,2'-(1E)-[1,4-phenylenebis(azan-1-yl-1-ylidene)]bis(methan-1-yl-1-ylidene)bis(1H-pyrrole-2,1-diyl)}dipropanoate
;
_journal_coeditor_code           HB7371
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o259
_journal_page_last               o260
_journal_paper_doi               10.1107/S2056989015005113
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C26 H30 N4 O4'
_chemical_formula_moiety         'C26 H30 N4 O4'
_chemical_formula_sum            'C26 H30 N4 O4'
_chemical_formula_weight         462.54
_chemical_name_systematic
'Diethyl 3,3'-{2,2'-(1E)-[1,4-phenylenebis(azan-1-yl-1-ylidene)]bis(methan-1-yl-1-ylidene)bis(1H-pyrrole-2,1-diyl)}dipropanoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.395(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6153(10)
_cell_length_b                   8.1227(4)
_cell_length_c                   13.9404(8)
_cell_measurement_reflns_used    1750
_cell_measurement_temperature    150.04(11)
_cell_measurement_theta_max      27.5070
_cell_measurement_theta_min      3.7650
_cell_volume                     2440.4(2)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150.04(11)
_diffrn_detector_area_resol_mean 10.3705
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type
'Agilent SuperNova (Single source at offset, Atlas)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6592
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.509
_diffrn_reflns_theta_min         2.931
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0338P)²+0.0686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1382
_reflns_number_gt                1697
_reflns_number_total             2900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7371sup1.cf
_cod_data_source_block           I
_cod_depositor_comments
;

2019-10-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C13 H15 N2 O2'
_cod_original_formula_weight         231.27
_cod_original_formula_moiety         'C13 H15 N2 O2'
_cod_original_formula_iupac          'C13 H15 N2 O2'
_cod_original_formula_units_Z            8
_cod_database_code               2240524
_cod_database_fobs_code          2240524
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
O O14 0.34059(6) 0.02364(17) 0.24674(10) 0.0286(4) Uani d 1
N N1 0.45878(7) 0.29578(19) 0.01458(12) 0.0225(4) Uani d 1
O O17 0.41066(7) 0.2126(2) 0.29870(11) 0.0385(4) Uani d 1
N N7 0.34834(7) 0.5212(2) 0.01854(13) 0.0231(4) Uani d 1
C C13 0.38269(9) 0.1407(2) 0.23355(16) 0.0240(5) Uani d 1
C C6 0.37626(9) 0.4878(2) -0.05699(16) 0.0233(5) Uani d 1
H H6 0.3615 0.5387 -0.1140 0.028 Uiso calc 1
C C5 0.42829(9) 0.3787(2) -0.06151(16) 0.0227(5) Uani d 1
C C8 0.29823(9) 0.6351(2) 0.00733(15) 0.0213(5) Uani d 1
C C9 0.29548(9) 0.7593(2) 0.07499(16) 0.0242(5) Uani d 1
H H9 0.3258 0.7654 0.1260 0.029 Uiso calc 1
C C2 0.50726(9) 0.2115(3) -0.01898(17) 0.0285(5) Uani d 1
H H2 0.5353 0.1466 0.0181 0.034 Uiso calc 1
C C11 0.44300(9) 0.2904(3) 0.11490(15) 0.0248(5) Uani d 1
H H11A 0.4308 0.3996 0.1345 0.030 Uiso calc 1
H H11B 0.4794 0.2581 0.1556 0.030 Uiso calc 1
C C12 0.39047(9) 0.1701(3) 0.12900(15) 0.0247(5) Uani d 1
H H12A 0.3521 0.2135 0.0983 0.030 Uiso calc 1
H H12B 0.3991 0.0663 0.0983 0.030 Uiso calc 1
C C15 0.33162(10) -0.0179(3) 0.34693(16) 0.0307(6) Uani d 1
H H15A 0.3205 0.0796 0.3820 0.037 Uiso calc 1
H H15B 0.3694 -0.0636 0.3782 0.037 Uiso calc 1
C C10 0.25193(9) 0.6253(2) -0.06747(16) 0.0244(5) Uani d 1
H H10 0.2528 0.5411 -0.1126 0.029 Uiso calc 1
C C4 0.45880(9) 0.3440(3) -0.14264(17) 0.0283(5) Uani d 1
H H4 0.4484 0.3843 -0.2042 0.034 Uiso calc 1
C C3 0.50810(10) 0.2377(3) -0.11602(17) 0.0318(6) Uani d 1
H H3 0.5361 0.1933 -0.1564 0.038 Uiso calc 1
C C16 0.28000(11) -0.1429(3) 0.34458(18) 0.0412(6) Uani d 1
H H16A 0.2913 -0.2375 0.3085 0.062 Uiso calc 1
H H16B 0.2427 -0.0953 0.3147 0.062 Uiso calc 1
H H16C 0.2731 -0.1756 0.4091 0.062 Uiso calc 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
C13 O14 C15 . . 115.83(16)
C5 N1 C11 . . 127.98(16)
C2 N1 C5 . . 108.38(18)
C2 N1 C11 . . 123.62(18)
C6 N7 C8 . . 116.70(18)
O14 C13 C12 . . 112.02(18)
O17 C13 O14 . . 123.3(2)
O17 C13 C12 . . 124.69(18)
N7 C6 H6 . . 117.1
N7 C6 C5 . . 125.9(2)
C5 C6 H6 . . 117.1
N1 C5 C6 . . 126.61(19)
N1 C5 C4 . . 107.45(17)
C4 C5 C6 . . 125.9(2)
C9 C8 N7 . . 118.06(19)
C9 C8 C10 . . 119.07(18)
C10 C8 N7 . . 122.86(18)
C8 C9 H9 . . 119.6
C8 C9 C10 . 7_565 120.71(19)
C10 C9 H9 7_565 . 119.6
N1 C2 H2 . . 125.4
N1 C2 C3 . . 109.23(19)
C3 C2 H2 . . 125.4
N1 C11 H11A . . 109.2
N1 C11 H11B . . 109.2
N1 C11 C12 . . 111.88(17)
H11A C11 H11B . . 107.9
C12 C11 H11A . . 109.2
C12 C11 H11B . . 109.2
C13 C12 C11 . . 111.61(17)
C13 C12 H12A . . 109.3
C13 C12 H12B . . 109.3
C11 C12 H12A . . 109.3
C11 C12 H12B . . 109.3
H12A C12 H12B . . 108.0
O14 C15 H15A . . 110.4
O14 C15 H15B . . 110.4
O14 C15 C16 . . 106.64(18)
H15A C15 H15B . . 108.6
C16 C15 H15A . . 110.4
C16 C15 H15B . . 110.4
C8 C10 H10 . . 119.9
C9 C10 C8 7_565 . 120.20(18)
C9 C10 H10 7_565 . 119.9
C5 C4 H4 . . 126.0
C5 C4 C3 . . 108.1(2)
C3 C4 H4 . . 126.0
C2 C3 C4 . . 106.86(18)
C2 C3 H3 . . 126.6
C4 C3 H3 . . 126.6
C15 C16 H16A . . 109.5
C15 C16 H16B . . 109.5
C15 C16 H16C . . 109.5
H16A C16 H16B . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O14 C13 . 1.338(2)
O14 C15 . 1.464(2)
N1 C5 . 1.381(3)
N1 C2 . 1.364(2)
N1 C11 . 1.465(3)
O17 C13 . 1.203(2)
N7 C6 . 1.282(2)
N7 C8 . 1.424(2)
C13 C12 . 1.499(3)
C6 H6 . 0.9300
C6 C5 . 1.437(3)
C5 C4 . 1.381(3)
C8 C9 . 1.386(3)
C8 C10 . 1.391(3)
C9 H9 . 0.9300
C9 C10 7_565 1.387(3)
C2 H2 . 0.9300
C2 C3 . 1.371(3)
C11 H11A . 0.9700
C11 H11B . 0.9700
C11 C12 . 1.522(3)
C12 H12A . 0.9700
C12 H12B . 0.9700
C15 H15A . 0.9700
C15 H15B . 0.9700
C15 C16 . 1.507(3)
C10 C9 7_565 1.387(3)
C10 H10 . 0.9300
C4 H4 . 0.9300
C4 C3 . 1.399(3)
C3 H3 . 0.9300
C16 H16A . 0.9600
C16 H16B . 0.9600
C16 H16C . 0.9600
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_4
_geom_torsion
O14 C13 C12 C11 . -174.17(16)
N1 C5 C4 C3 . 0.5(2)
N1 C2 C3 C4 . 0.9(2)
N1 C11 C12 C13 . 169.07(17)
O17 C13 C12 C11 . 5.8(3)
N7 C6 C5 N1 . -2.6(3)
N7 C6 C5 C4 . -179.3(2)
N7 C8 C9 C10 7_565 179.47(17)
N7 C8 C10 C9 7_565 -179.52(18)
C13 O14 C15 C16 . 176.56(17)
C6 N7 C8 C9 . -134.2(2)
C6 N7 C8 C10 . 46.7(3)
C6 C5 C4 C3 . 177.72(19)
C5 N1 C2 C3 . -0.6(2)
C5 N1 C11 C12 . 79.5(2)
C5 C4 C3 C2 . -0.8(2)
C8 N7 C6 C5 . 179.01(17)
C9 C8 C10 C9 7_565 1.3(3)
C2 N1 C5 C6 . -177.15(19)
C2 N1 C5 C4 . 0.0(2)
C2 N1 C11 C12 . -98.6(2)
C11 N1 C5 C6 . 4.5(3)
C11 N1 C5 C4 . -178.28(18)
C11 N1 C2 C3 . 177.83(18)
C15 O14 C13 O17 . -2.2(3)
C15 O14 C13 C12 . 177.75(16)
C10 C8 C9 C10 7_565 -1.4(3)
