Angularly fused diaza-dinaphthopyrenes: regio-selective synthesis, crystal structures and isomer-dependent mechanochromic fluorescent properties.
Kou, Yan; Li, Guangwu; Han, Yi; Li, Mengwei; Wang, Tingting; Qu, Zhiyu; Chen, Yulan; Chemical science 14 (2023) 668–674; doi:10.1039/d2sc05608a

data_1568130
_publ_section_title
;
 Angularly fused diaza-dinaphthopyrenes: regio-selective synthesis,
 crystal structures and isomer-dependent mechanochromic fluorescent
 properties.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              668
_journal_page_last               674
_journal_paper_doi               10.1039/d2sc05608a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H22 N'
_chemical_formula_sum            'C22 H22 N'
_chemical_formula_weight         300.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2c5hgj
_audit_creation_date             2021-08-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-18 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.455(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.43800(10)
_cell_length_b                   17.7484(5)
_cell_length_c                   19.3921(6)
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      74.7530
_cell_measurement_theta_min      3.3510
_cell_volume                     1871.04(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.948
_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     31.00  73.00   0.50    2.00    --   45.75  57.00 -30.00   84
  2  \w     76.00 104.00   0.50    2.00    --   45.75  57.00 -30.00   56
  3  \w    106.00 131.00   0.50   11.97    --  101.75  96.00 -90.00   50
  4  \w     69.00  98.00   0.50   11.97    --  101.75 -45.00 150.00   58
  5  \w     39.00 109.00   0.50   11.97    --  101.75 -96.00 161.00  140
  6  \w     -8.00  78.00   0.50    2.00    --   45.75 -96.00 161.00  172
  7  \w    -32.00  26.00   0.50    2.00    --  -45.75  96.00 -90.00  116
  8  \w    -53.00 -27.00   0.50   11.97    -- -100.00  45.00 120.00   52
  9  \w    -96.00 -70.00   0.50   11.97    -- -100.00  45.00 120.00   52
 10  \w   -116.00 -27.00   0.50   11.97    -- -100.00 125.00  60.00  178
 11  \w   -105.00 -50.00   0.50   11.97    -- -100.00  96.00 -90.00  110
 12  \w    -71.00 -34.00   0.50   11.97    -- -100.00  45.00 -90.00   74
 13  \w   -159.00 -87.00   0.50   11.97    -- -100.00 -96.00 161.00  144
 14  \w   -119.00 -94.00   0.50    2.00    --  -45.75-125.00  30.00   50
 15  \w   -117.00 -76.00   0.50    2.00    --  -45.75-125.00 -60.00   82
 16  \w   -170.00 -84.00   0.50   11.97    -- -100.00 -61.00 -90.00  172
 17  \w   -167.00-110.00   0.50   11.97    -- -100.00 -45.00-150.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1595770000
_diffrn_orient_matrix_UB_12      0.0665091000
_diffrn_orient_matrix_UB_13      0.0258540000
_diffrn_orient_matrix_UB_21      -0.0869778000
_diffrn_orient_matrix_UB_22      0.0470365000
_diffrn_orient_matrix_UB_23      -0.0628132000
_diffrn_orient_matrix_UB_31      -0.2175772000
_diffrn_orient_matrix_UB_32      0.0297706000
_diffrn_orient_matrix_UB_33      0.0413156000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11255
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.780
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0814
_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/[\s^2^(Fo^2^)+(0.1275P)^2^+1.2041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2371
_refine_ls_wR_factor_ref         0.2466
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2867
_reflns_number_total             3630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05608a2.cif
_cod_data_source_block           045377_ky_160k_a
_cod_depositor_comments
'Adding full bibliography for 1568129--1568130.cif.'
_cod_database_code               1568130
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.905
_reflns_odcompleteness_completeness 99.97
_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.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              33003
_shelx_fab_checksum              25923
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.698
_oxdiff_exptl_absorpt_empirical_full_min 0.621