#------------------------------------------------------------------------------
#$Date: 2021-01-09 08:04:25 +0200 (Sat, 09 Jan 2021) $
#$Revision: 260882 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243714.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_2243714
loop_
_publ_author_name
'Holmberg, Ryne'
'Franz, Vanessa'
'Moser, Kristen M.'
'Solano, Ricardo'
'Moore, Curtis'
'Rheingold, Arnold L.'
'Smith, Gary L. N.'
_publ_section_title
;
 Crystal structure of
 2,2'-{[(2-nitrobenzyl)azanediyl]bis(propane-3,1-diyl)}bis[1H-isoindole-1,3(2H)-dione]
;
_journal_coeditor_code           ZN2003
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              83
_journal_page_last               85
_journal_paper_doi               10.1107/S2056989020016771
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C29 H26 N4 O6'
_chemical_formula_moiety         'C29 H26 N4 O6'
_chemical_formula_sum            'C29 H26 N4 O6'
_chemical_formula_weight         526.54
_chemical_name_systematic
2,2'-{[(2-Nitrobenzyl)azanediyl}bis(propane-3,1-diyl)}bis[1H-isoindole-1,3(2H)-dione]
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                94.2950(10)
_cell_angle_beta                 104.6030(10)
_cell_angle_gamma                101.0420(10)
_cell_formula_units_Z            2
_cell_length_a                   7.8576(10)
_cell_length_b                   12.3468(15)
_cell_length_c                   14.1147(17)
_cell_measurement_reflns_used    4970
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.41
_cell_volume                     1289.6(3)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX 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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11940
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0604
_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)+(0.0222P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                3422
_reflns_number_total             4518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            zn2003sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2243714
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4890(4) 0.8275(2) 0.3635(2) 0.0271(7) Uani d . 1 1 . .
C C2 0.6627(4) 0.9044(2) 0.3687(2) 0.0243(6) Uani d . 1 1 . .
C C3 0.7287(4) 1.0141(2) 0.4092(2) 0.0311(7) Uani d . 1 1 . .
H H3 0.6606 1.0541 0.4398 0.037 Uiso calc R 1 1 . .
C C4 0.9008(4) 1.0641(3) 0.4031(2) 0.0351(8) Uani d . 1 1 . .
H H4 0.9497 1.1401 0.4292 0.042 Uiso calc R 1 1 . .
C C5 1.0010(4) 1.0052(3) 0.3599(2) 0.0337(8) Uani d . 1 1 . .
H H5 1.1175 1.0414 0.3572 0.040 Uiso calc R 1 1 . .
C C6 0.9345(4) 0.8945(3) 0.3206(2) 0.0301(7) Uani d . 1 1 . .
H H6 1.0036 0.8536 0.2916 0.036 Uiso calc R 1 1 . .
C C7 0.7637(4) 0.8458(2) 0.3253(2) 0.0241(6) Uani d . 1 1 . .
C C8 0.6567(4) 0.7305(2) 0.2896(2) 0.0245(6) Uani d . 1 1 . .
C C9 0.3523(4) 0.6256(2) 0.2976(2) 0.0294(7) Uani d . 1 1 . .
H H9A 0.3190 0.6152 0.3600 0.035 Uiso calc R 1 1 . .
H H9B 0.3999 0.5606 0.2796 0.035 Uiso calc R 1 1 . .
C C10 0.1841(4) 0.6293(2) 0.2168(2) 0.0256(6) Uani d . 1 1 . .
H H10A 0.1377 0.6952 0.2335 0.031 Uiso calc R 1 1 . .
H H10B 0.2155 0.6367 0.1535 0.031 Uiso calc R 1 1 . .
C C11 0.0385(4) 0.5247(2) 0.2048(2) 0.0261(6) Uani d . 1 1 . .
H H11A -0.0070 0.5243 0.2641 0.031 Uiso calc R 1 1 . .
H H11B -0.0633 0.5259 0.1472 0.031 Uiso calc R 1 1 . .
C C12 0.1262(3) 0.4048(2) 0.0910(2) 0.0237(6) Uani d . 1 1 . .
H H12A 0.1831 0.4769 0.0743 0.028 Uiso calc R 1 1 . .
H H12B 0.0056 0.3794 0.0434 0.028 Uiso calc R 1 1 . .
C C13 0.2396(4) 0.3205(2) 0.0790(2) 0.0264(7) Uani d . 1 1 . .
H H13A 0.3572 0.3417 0.1297 0.032 Uiso calc R 1 1 . .
H H13B 0.1775 0.2461 0.0883 0.032 Uiso calc R 1 1 . .
C C14 0.2694(4) 0.3165(2) -0.0232(2) 0.0264(6) Uani d . 1 1 . .
H H14A 0.1517 0.3070 -0.0728 0.032 Uiso calc R 1 1 . .
H H14B 0.3454 0.3884 -0.0285 0.032 Uiso calc R 1 1 . .
C C15 0.5367(3) 0.2414(2) -0.0430(2) 0.0221(6) Uani d . 1 1 . .
C C16 0.5587(3) 0.1320(2) -0.08339(19) 0.0206(6) Uani d . 1 1 . .
C C17 0.7090(3) 0.0994(2) -0.0999(2) 0.0252(6) Uani d . 1 1 . .
H H17 0.8233 0.1495 -0.0828 0.030 Uiso calc R 1 1 . .
C C18 0.6859(4) -0.0095(3) -0.1424(2) 0.0286(7) Uani d . 1 1 . .
H H18 0.7866 -0.0343 -0.1547 0.034 Uiso calc R 1 1 . .
C C19 0.5197(4) -0.0827(2) -0.1672(2) 0.0268(7) Uani d . 1 1 . .
H H19 0.5079 -0.1564 -0.1969 0.032 Uiso calc R 1 1 . .
C C20 0.3687(4) -0.0497(2) -0.1492(2) 0.0256(6) Uani d . 1 1 . .
H H20 0.2545 -0.0997 -0.1652 0.031 Uiso calc R 1 1 . .
C C21 0.3928(3) 0.0578(2) -0.10763(19) 0.0203(6) Uani d . 1 1 . .
C C22 0.2602(3) 0.1187(2) -0.0827(2) 0.0238(6) Uani d . 1 1 . .
C C23 -0.0218(3) 0.3273(2) 0.2100(2) 0.0238(6) Uani d . 1 1 . .
H H23A 0.0068 0.2568 0.1872 0.029 Uiso calc R 1 1 . .
H H23B -0.1465 0.3279 0.1729 0.029 Uiso calc R 1 1 . .
C C24 -0.0079(3) 0.3337(2) 0.3192(2) 0.0229(6) Uani d . 1 1 . .
C C25 -0.1560(4) 0.3386(2) 0.3552(2) 0.0284(7) Uani d . 1 1 . .
H H25 -0.2697 0.3350 0.3098 0.034 Uiso calc R 1 1 . .
C C26 -0.1421(4) 0.3485(3) 0.4551(2) 0.0325(7) Uani d . 1 1 . .
H H26 -0.2470 0.3475 0.4771 0.039 Uiso calc R 1 1 . .
C C27 0.0227(4) 0.3597(3) 0.5233(2) 0.0337(7) Uani d . 1 1 . .
H H27 0.0318 0.3680 0.5920 0.040 Uiso calc R 1 1 . .
C C28 0.1741(4) 0.3589(2) 0.4909(2) 0.0282(7) Uani d . 1 1 . .
H H28 0.2892 0.3687 0.5368 0.034 Uiso calc R 1 1 . .
C C29 0.1551(4) 0.3436(2) 0.3907(2) 0.0247(6) Uani d . 1 1 . .
N N1 0.4939(3) 0.72652(19) 0.31379(17) 0.0256(6) Uani d . 1 1 . .
N N2 0.1039(3) 0.42205(19) 0.19079(16) 0.0217(5) Uani d . 1 1 . .
N N3 0.3550(3) 0.22716(19) -0.04578(17) 0.0227(5) Uani d . 1 1 . .
N N4 0.3188(3) 0.3337(2) 0.36090(19) 0.0298(6) Uani d . 1 1 . .
O O1 0.3652(3) 0.84351(18) 0.39538(16) 0.0375(5) Uani d . 1 1 . .
O O2 0.6965(3) 0.65364(18) 0.24824(15) 0.0328(5) Uani d . 1 1 . .
O O3 0.6476(2) 0.32780(17) -0.01314(15) 0.0300(5) Uani d . 1 1 . .
O O4 0.1007(2) 0.08489(17) -0.09265(15) 0.0315(5) Uani d . 1 1 . .
O O5 0.4580(3) 0.4043(2) 0.40052(17) 0.0434(6) Uani d . 1 1 . .
O O6 0.3096(3) 0.25346(19) 0.30131(17) 0.0373(5) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 124.5(3) ?
O1 C1 C2 . . 129.7(3) ?
N1 C1 C2 . . 105.8(2) ?
C3 C2 C7 . . 121.3(3) ?
C3 C2 C1 . . 130.6(3) ?
C7 C2 C1 . . 108.1(2) ?
C2 C3 C4 . . 117.0(3) ?
C2 C3 H3 . . 121.5 ?
C4 C3 H3 . . 121.5 ?
C5 C4 C3 . . 121.5(3) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C6 C5 C4 . . 121.2(3) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C7 C6 C5 . . 117.3(3) ?
C7 C6 H6 . . 121.3 ?
C5 C6 H6 . . 121.3 ?
C6 C7 C2 . . 121.8(3) ?
C6 C7 C8 . . 129.9(3) ?
C2 C7 C8 . . 108.4(2) ?
O2 C8 N1 . . 125.2(3) ?
O2 C8 C7 . . 129.1(3) ?
N1 C8 C7 . . 105.7(2) ?
N1 C9 C10 . . 112.9(2) ?
N1 C9 H9A . . 109.0 ?
C10 C9 H9A . . 109.0 ?
N1 C9 H9B . . 109.0 ?
C10 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C11 C10 C9 . . 111.1(2) ?
C11 C10 H10A . . 109.4 ?
C9 C10 H10A . . 109.4 ?
C11 C10 H10B . . 109.4 ?
C9 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
N2 C11 C10 . . 112.6(2) ?
N2 C11 H11A . . 109.1 ?
C10 C11 H11A . . 109.1 ?
N2 C11 H11B . . 109.1 ?
C10 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.8 ?
N2 C12 C13 . . 113.8(2) ?
N2 C12 H12A . . 108.8 ?
C13 C12 H12A . . 108.8 ?
N2 C12 H12B . . 108.8 ?
C13 C12 H12B . . 108.8 ?
H12A C12 H12B . . 107.7 ?
C14 C13 C12 . . 109.8(2) ?
C14 C13 H13A . . 109.7 ?
C12 C13 H13A . . 109.7 ?
C14 C13 H13B . . 109.7 ?
C12 C13 H13B . . 109.7 ?
H13A C13 H13B . . 108.2 ?
N3 C14 C13 . . 113.3(2) ?
N3 C14 H14A . . 108.9 ?
C13 C14 H14A . . 108.9 ?
N3 C14 H14B . . 108.9 ?
C13 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
O3 C15 N3 . . 124.6(3) ?
O3 C15 C16 . . 129.6(2) ?
N3 C15 C16 . . 105.9(2) ?
C17 C16 C21 . . 120.9(3) ?
C17 C16 C15 . . 130.6(2) ?
C21 C16 C15 . . 108.5(2) ?
C16 C17 C18 . . 117.3(3) ?
C16 C17 H17 . . 121.3 ?
C18 C17 H17 . . 121.3 ?
C19 C18 C17 . . 121.5(3) ?
C19 C18 H18 . . 119.2 ?
C17 C18 H18 . . 119.2 ?
C18 C19 C20 . . 120.9(3) ?
C18 C19 H19 . . 119.5 ?
C20 C19 H19 . . 119.5 ?
C21 C20 C19 . . 117.1(2) ?
C21 C20 H20 . . 121.5 ?
C19 C20 H20 . . 121.5 ?
C20 C21 C16 . . 122.3(2) ?
C20 C21 C22 . . 130.1(2) ?
C16 C21 C22 . . 107.5(2) ?
O4 C22 N3 . . 124.9(3) ?
O4 C22 C21 . . 128.9(3) ?
N3 C22 C21 . . 106.3(2) ?
N2 C23 C24 . . 110.2(2) ?
N2 C23 H23A . . 109.6 ?
C24 C23 H23A . . 109.6 ?
N2 C23 H23B . . 109.6 ?
C24 C23 H23B . . 109.6 ?
H23A C23 H23B . . 108.1 ?
C25 C24 C29 . . 115.5(3) ?
C25 C24 C23 . . 121.7(2) ?
C29 C24 C23 . . 122.6(2) ?
C26 C25 C24 . . 121.7(3) ?
C26 C25 H25 . . 119.1 ?
C24 C25 H25 . . 119.1 ?
C27 C26 C25 . . 120.7(3) ?
C27 C26 H26 . . 119.7 ?
C25 C26 H26 . . 119.7 ?
C28 C27 C26 . . 119.4(3) ?
C28 C27 H27 . . 120.3 ?
C26 C27 H27 . . 120.3 ?
C27 C28 C29 . . 118.7(3) ?
C27 C28 H28 . . 120.6 ?
C29 C28 H28 . . 120.6 ?
C28 C29 C24 . . 123.8(3) ?
C28 C29 N4 . . 116.1(2) ?
C24 C29 N4 . . 120.1(3) ?
C1 N1 C8 . . 112.1(2) ?
C1 N1 C9 . . 123.7(2) ?
C8 N1 C9 . . 124.0(2) ?
C12 N2 C23 . . 111.5(2) ?
C12 N2 C11 . . 110.5(2) ?
C23 N2 C11 . . 109.4(2) ?
C22 N3 C15 . . 111.8(2) ?
C22 N3 C14 . . 123.3(2) ?
C15 N3 C14 . . 124.5(2) ?
O6 N4 O5 . . 124.3(3) ?
O6 N4 C29 . . 118.0(2) ?
O5 N4 C29 . . 117.7(3) ?
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
C1 O1 . 1.212(3) ?
C1 N1 . 1.396(4) ?
C1 C2 . 1.487(4) ?
C2 C3 . 1.377(4) ?
C2 C7 . 1.388(4) ?
C3 C4 . 1.401(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.384(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.384(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.382(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.486(4) ?
C8 O2 . 1.209(3) ?
C8 N1 . 1.398(4) ?
C9 N1 . 1.464(3) ?
C9 C10 . 1.524(4) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.520(4) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 N2 . 1.474(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 N2 . 1.467(3) ?
C12 C13 . 1.520(4) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.517(4) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 N3 . 1.452(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 O3 . 1.211(3) ?
C15 N3 . 1.394(3) ?
C15 C16 . 1.485(4) ?
C16 C17 . 1.385(4) ?
C16 C21 . 1.388(4) ?
C17 C18 . 1.390(4) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.384(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.400(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.369(4) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.490(4) ?
C22 O4 . 1.211(3) ?
C22 N3 . 1.392(4) ?
C23 N2 . 1.469(3) ?
C23 C24 . 1.512(4) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C25 . 1.391(4) ?
C24 C29 . 1.394(4) ?
C25 C26 . 1.381(4) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.380(4) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.379(4) ?
C27 H27 . 0.9500 ?
C28 C29 . 1.379(4) ?
C28 H28 . 0.9500 ?
C29 N4 . 1.474(4) ?
N4 O6 . 1.229(3) ?
N4 O5 . 1.234(3) ?
