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_1568129
_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         'C44 H44 N2'
_chemical_formula_sum            'C44 H44 N2'
_chemical_formula_weight         600.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2c5h68
_audit_creation_date             2020-08-22
_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                109.684(8)
_cell_angle_beta                 98.078(7)
_cell_angle_gamma                93.683(7)
_cell_formula_units_Z            2
_cell_length_a                   7.4324(5)
_cell_length_b                   14.6018(14)
_cell_length_c                   16.6369(14)
_cell_measurement_reflns_used    4454
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.7470
_cell_measurement_theta_min      2.2950
_cell_volume                     1671.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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   -115.00  65.00   1.00   12.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00   12.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00   12.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0015587000
_diffrn_orient_matrix_UB_12      -0.0387861000
_diffrn_orient_matrix_UB_13      0.0166414000
_diffrn_orient_matrix_UB_21      0.0063598000
_diffrn_orient_matrix_UB_22      0.0342744000
_diffrn_orient_matrix_UB_23      0.0425723000
_diffrn_orient_matrix_UB_31      -0.0968667000
_diffrn_orient_matrix_UB_32      -0.0046076000
_diffrn_orient_matrix_UB_33      -0.0048891000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.609
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6813
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1649
_refine_ls_R_factor_gt           0.0887
_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^)+(0.1204P)^2^+0.2588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3416
_reflns_number_total             6813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05608a2.cif
_cod_data_source_block           r20200810a
_cod_depositor_comments
'Adding full bibliography for 1568129--1568130.cif.'
_cod_database_code               1568129
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H42 of C42, H41 of C41, H40 of C40, H43 of C43, H24 of
  C24, H25 of C25, H26 of C26, H28 of C28, H32 of C32, H5 of C5, H4 of C4, H3
  of C3, H2 of C2, H18 of C18, H19 of C19
 At 1.5 times of:
  All C(H,H,H) groups, H10 of C10
2. Restrained distances
 C10-H10
 0.95 with sigma of 0.01
3.a Riding coordinates:
 C10(H10)
3.b Ternary CH refined with riding coordinates:
 C32(H32)
3.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C33(H33A,
 H33B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C24(H24), C25(H25),
 C26(H26), C28(H28), C40(H40), C41(H41), C42(H42), C43(H43)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C34(H34A,H34B,H34C), C38(H38A,H38B,
 H38C)
;
_shelx_res_checksum              42105
_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 1.721
_oxdiff_exptl_absorpt_empirical_full_min 0.661