Controllable room temperature phosphorescence, mechanoluminescence and polymorphism of a carbazole derivative.
Zhang, Hongyan; Ma, Huili; Huang, Wenbin; Gong, Wenqi; He, Zikai; Huang, Guangxi; Li, Bing Shi; Tang, Ben Zhong; Materials horizons 8 (2021) 2816–2822; doi:10.1039/d1mh00956g

data_1564539
_publ_section_title
;
 Controllable room temperature phosphorescence, mechanoluminescence and
 polymorphism of a carbazole derivative.
;
_journal_issue                   10
_journal_name_full               'Materials horizons'
_journal_page_first              2816
_journal_page_last               2822
_journal_paper_doi               10.1039/d1mh00956g
_journal_volume                  8
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C40 H53 N O2'
_chemical_formula_sum            'C40 H53 N O2'
_chemical_formula_weight         579.83
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-23 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                111.3480(10)
_cell_angle_beta                 112.1740(10)
_cell_angle_gamma                95.3590(10)
_cell_formula_units_Z            4
_cell_length_a                   14.8060(7)
_cell_length_b                   15.4949(7)
_cell_length_c                   17.2480(8)
_cell_measurement_reflns_used    9459
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.27
_cell_volume                     3288.5(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            112219
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         2.275
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0717 before and 0.0551 after correction. The Ratio of minimum to maximum transmission is 0.9145. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 12068 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.37(19)
_refine_ls_extinction_coef       0.0034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1589
_refine_ls_number_reflns         30227
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0620P)^2^+0.5982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                26926
_reflns_number_total             30227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1mh00956g2.cif
_cod_data_source_block           cxy1198_0m
_cod_depositor_comments
'Adding full bibliography for 1564539--1564540.cif.'
_cod_database_code               1564539
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.977
_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
 C123-C122 = C130-C123
 1.39 with sigma of 0.02
 C1M-C1B
 1.38 with sigma of 0.01
 C1M-C1E
 1.4 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N4 \\sim C125 \\sim C126 \\sim C127 \\sim C128 \\sim C129 \\sim C124 \\sim C123
\\sim C122 \\sim C133 \\sim C132 \\sim C131 \\sim C130: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O7) = Uanis(O7A)
Uanis(C121) = Uanis(C1A)
Uanis(O8) = Uanis(O8A)
Uanis(N4) = Uanis(N4A)
Uanis(C124) = Uanis(C1G)
Uanis(C125) = Uanis(C1H)
Uanis(C129) = Uanis(C1I)
Uanis(C128) = Uanis(C1J)
Uanis(C127) = Uanis(C1K)
Uanis(C126) = Uanis(C1L)
Uanis(C122) = Uanis(C1B)
Uanis(C132) = Uanis(C1C)
Uanis(C133) = Uanis(C1D)
Uanis(C130) = Uanis(C1E)
Uanis(C131) = Uanis(C1F)
Uanis(C123) = Uanis(C1)
Uanis(C1M) = Uanis(C123)
4. Others
 Sof(H13C)=Sof(O7A)=Sof(C1A)=Sof(O8A)=Sof(N4A)=Sof(C1B)=Sof(C1C)=Sof(H1C)=
 Sof(C1D)=Sof(H1D)=Sof(C1E)=Sof(H1E)=Sof(C1F)=Sof(H1F)=Sof(C1G)=Sof(C1H)=
 Sof(C1I)=Sof(H1I)=Sof(C1J)=Sof(H1J)=Sof(C1K)=Sof(H1K)=Sof(C1L)=Sof(H1L)=
 Sof(C1M)=1-FVAR(1)
 Sof(O7)=Sof(O8)=Sof(N4)=Sof(C124)=Sof(C129)=Sof(H129)=Sof(C128)=Sof(H128)=
 Sof(C127)=Sof(H127)=Sof(C126)=Sof(H126)=Sof(C125)=Sof(C122)=Sof(C133)=
 Sof(H133)=Sof(C132)=Sof(H132)=Sof(C131)=Sof(H131)=Sof(C130)=Sof(H130)=
 Sof(C123)=Sof(C121)=Sof(H134)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C27(H27), C24(H24), C26(H26), C20(H20), C14(H14), C31(H31), C21(H21),
 C61(H61), C60(H60), C54(H54), C67(H67), C66(H66), C71(H71), C64(H64),
 C104(H104), C100(H100), C94(H94), C111(H111), C101(H101), C107(H107),
 C106(H106), C144(H144), C147(H147), C146(H146), C141(H141), C151(H151),
 C140(H140), C134(H134), C134(H13C)
5.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C28(H28A,H28B), C29(H29A,H29B), C38(H38A,H38B), C35(H35A,
 H35B), C15(H15W,H15X), C19(H19A,H19B), C37(H37A,H37B), C36(H36A,H36B),
 C30(H30A,H30B), C18(H18A,H18B), C76(H76A,H76B), C78(H78A,H78B), C55(H55A,H55B),
  C75(H75A,H75B), C59(H59A,H59B), C77(H77A,H77B), C62(H62A,H62B), C58(H58A,
 H58B), C69(H69A,H69B), C70(H70A,H70B), C68(H68A,H68B), C95(H95A,H95B),
 C99(H99A,H99B), C98(H98A,H98B), C115(H11A,H11B), C116(H11C,H11D), C118(H11E,
 H11F), C109(H10A,H10B), C110(H11J,H11K), C102(H10C,H10D), C117(H11U,H11V),
 C108(H10E,H10F), C158(H15A,H15B), C155(H15F,H15G), C157(H15H,H15I), C135(H13A,
 H13B), C156(H15P,H15Q), C149(H14A,H14B), C142(H14C,H14D), C148(H14E,H14F),
 C138(H13D,H13E), C150(H15R,H15S), C139(H13F,H13G)
5.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C9(H9), C12(H12), C11(H11), C13(H13), C6(H6), C7(H7), C8(H8),
 C10(H10), C46(H46), C52(H52), C63(H63), C48(H48), C47(H47), C51(H51), C50(H50),
  C53(H53), C49(H49), C103(H103), C93(H93), C86(H86), C88(H88), C89(H89),
 C90(H90), C91(H91), C92(H92), C87(H87), C143(H143), C129(H129), C128(H128),
 C127(H127), C126(H126), C133(H133), C132(H132), C131(H131), C130(H130),
 C1C(H1C), C1D(H1D), C1E(H1E), C1F(H1F), C1I(H1I), C1J(H1J), C1K(H1K), C1L(H1L)
5.d Fitted hexagon refined as free rotating group:
 C124(C129,C128,C127,C126,C125), C122(C133,C132,C131,C130,C123)
5.e Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C40(H40A,H40B,H40C), C34(H34A,H34B,H34C), C33(H33A,H33B,
 H33C), C39(H39A,H39B,H39C), C79(H79A,H79B,H79C), C80(H80A,H80B,H80C), C72(H72A,
 H72B,H72C), C74(H74A,H74B,H74C), C73(H73A,H73B,H73C), C114(H11G,H11H,H11I),
 C112(H11L,H11M,H11N), C113(H11O,H11P,H11Q), C120(H12A,H12B,H12C), C119(H11R,
 H11S,H11T), C154(H15C,H15D,H15E), C160(H16A,H16B,H16C), C159(H15J,H15K,H15L),
 C152(H15M,H15N,H15O), C153(H15T,H15U,H15V)
;
_olex2_submission_special_instructions 'No special instructions were received'