2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2-b]pyrrole (AAPP) AIEgens: tunable RIR and TICT characteristics and their multifunctional applications
Li, Kai; Liu, Yuanyuan; Li, Yuanyuan; Feng, Qi; Hou, Hongwei; Tang, Ben Zhong; Chem. Sci.  (2017) –; doi:10.1039/C7SC03076B

data_1546920
_publ_section_title
;
 2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2-b]pyrrole
 (AAPP) AIEgens: tunable RIR and TICT characteristics and their
 multifunctional applications
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC03076B
_journal_year                    2017
_chemical_formula_moiety         'C19 H14 F3 N O2'
_chemical_formula_sum            'C19 H14 F3 N O2'
_chemical_formula_weight         345.31
_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     direct
_audit_creation_date             2017-07-11
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.06.29 svn.r3433 for OlexSys, GUI svn.r5356)
;
_audit_update_record
;
2017-07-11 deposited with the CCDC.
2017-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                63.176(4)
_cell_angle_beta                 88.118(4)
_cell_angle_gamma                81.174(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1875(3)
_cell_length_b                   12.1177(5)
_cell_length_c                   12.2490(5)
_cell_measurement_reflns_used    5625
_cell_measurement_temperature    285.00(10)
_cell_measurement_theta_max      72.3970
_cell_measurement_theta_min      6.9800
_cell_volume                     809.19(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      285.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -9.00  96.00   0.50    0.50    --   45.70  19.00  60.00  210
  2  \w    102.00 131.00   0.50    0.50    --   45.70  19.00  60.00   58
  3  \w     96.00 131.00   0.50    0.50    --   45.70  82.00  90.00   70
  4  \w    144.00 170.00   0.50    0.50    --   99.80  82.00   0.00   52
  5  \w    109.00 183.00   0.50    0.50    --   99.80  15.00 120.00  148
  6  \w     93.00 119.00   0.50    0.50    --   99.80 -82.00-120.00   52
  7  \w     95.00 128.00   0.50    0.50    --   99.80 -61.00 -90.00   66
  8  \w     74.00 100.00   0.50    0.50    --   99.80 -82.00-150.00   52
  9  \w     77.00 103.00   0.50    0.50    --   99.80 -82.00 -30.00   52
 10  \w     70.00 122.00   0.50    0.50    --   99.80 -82.00   0.00  104
 11  \w     84.00 117.00   0.50    0.50    --   99.80 -82.00 150.00   66
 12  \w     28.00 124.00   0.50    0.50    --   99.80 -61.00  90.00  192
 13  \w     89.00 184.00   0.50    0.50    --   99.80  15.00-150.00  190
 14  \w     87.00 134.00   0.50    0.50    --   99.80  82.00-150.00   94
 15  \w     10.00  85.00   0.50    0.50    --   99.80  15.00-150.00  150
 16  \w     15.00 121.00   0.50    0.50    --   99.80 -61.00 -30.00  212
 17  \w     22.00  59.00   0.50    0.50    --   45.70 -82.00  60.00   74
 18  \w     10.00 143.50   0.50    0.50    --   99.80 -82.00  90.00  267
 19  \w     22.00  72.00   0.50    0.50    --   99.80  15.00 120.00  100
 20  \w     12.00 109.00   0.50    0.50    --   99.80 -82.00 -90.00  194
 21  \w     13.00  73.00   0.50    0.50    --   99.80 -82.00-180.00  120
 22  \w     22.00  89.00   0.50    0.50    --   99.80 -61.00 -90.00  134
 23  \w    -34.00  42.00   0.50    0.50    --   45.70 -82.00 120.00  152
 24  \w    -43.00  83.00   0.50    0.50    --   45.70 -57.00-180.00  252
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0557158000
_diffrn_orient_matrix_UB_12      -0.0045750000
_diffrn_orient_matrix_UB_13      -0.1215440000
_diffrn_orient_matrix_UB_21      0.1704965000
_diffrn_orient_matrix_UB_22      0.0874618000
_diffrn_orient_matrix_UB_23      -0.0223639000
_diffrn_orient_matrix_UB_31      0.1772563000
_diffrn_orient_matrix_UB_32      -0.1145761000
_diffrn_orient_matrix_UB_33      0.0679983000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7514
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        64.996
_diffrn_reflns_theta_max         64.996
_diffrn_reflns_theta_min         4.048
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       Block
_exptl_crystal_F_000             356
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1170P)^2^+0.2870P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.1786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2546
_reflns_number_total             2722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03076b2.cif
_cod_data_source_block           hy
_cod_database_code               1546920
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     st
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-C0AA
 1.5 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C14(H14), C16(H16), C20(H20),
 C2AA(H2AA)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              12228
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.785