Toward electron-deficient pyrene derivatives: construction of pyrene tetracarboxylic diimide containing five-membered imide rings.
Zou, Lin; Wang, Xiao-Ye; Zhang, Xiao-Xiao; Dai, Ya-Zhong; Wu, Yun-Dong; Wang, Jie-Yu; Pei, Jian; Chemical communications (Cambridge, England) 51 (2015) 12585–12588; doi:10.1039/c5cc04860e

data_7117624
_publ_section_title
;
 Toward electron-deficient pyrene derivatives: construction of pyrene
 tetracarboxylic diimide containing five-membered imide rings.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12585
_journal_page_last               12588
_journal_paper_doi               10.1039/c5cc04860e
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C26 H20 N2 O4'
_chemical_formula_sum            'C26 H20 N2 O4'
_chemical_formula_weight         424.44
_chemical_name_common            PyrDI
_chemical_name_systematic        'pyrene-1,2:6,7-tetracarboxylic diimides'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-07
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_audit_update_record
;
2015-02-02 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                80.826(5)
_cell_angle_beta                 89.447(5)
_cell_angle_gamma                85.419(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3610(5)
_cell_length_b                   8.3907(5)
_cell_length_c                   16.3626(10)
_cell_measurement_reflns_used    2338
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      29.7400
_cell_measurement_theta_min      3.7560
_cell_volume                     994.50(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9886
_diffrn_measured_fraction_theta_max 0.8383
_diffrn_measurement_details
;
  1 omega  -20.00   56.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8167  -99.0000  150.0000 76

  2 omega  -11.00   84.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8167   57.0000   30.0000 95

  3 omega  -55.00   40.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8167  -57.0000 -120.0000 95
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0278394000
_diffrn_orient_matrix_UB_12      0.0808467000
_diffrn_orient_matrix_UB_13      0.0048480000
_diffrn_orient_matrix_UB_21      -0.0861694000
_diffrn_orient_matrix_UB_22      -0.0074604000
_diffrn_orient_matrix_UB_23      -0.0174291000
_diffrn_orient_matrix_UB_31      -0.0338315000
_diffrn_orient_matrix_UB_32      -0.0280521000
_diffrn_orient_matrix_UB_33      0.0400111000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6115
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.65
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0509
_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/[\s^2^(Fo^2^)+(0.0571P)^2^+0.6631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                3041
_reflns_number_total             3899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc04860e2.cif
_cod_data_source_block           zoulin
_cod_database_code               7117624
_chemical_oxdiff_formula         C24H18O4N2
_reflns_odcompleteness_completeness 98.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H6 of C6, H9 of C9, H22 of C22, H16 of C16, H25 of C25, H26 of C26, H12 of
  C12, H13 of C13
 At 1.5 times of:
  {H11a,H11b,H11c} of C11, {H10a,H10b,H10c} of C10, {H23a,H23b,H23c} of C23,
  {H24a,H24b,H24c} of C24
2.a Ternary CH refined with riding coordinates:
 C9(H9), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C13(H13), C16(H16), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C23(H23a,H23b,H23c), C24(H24a,H24b,
 H24c)
;