Highly emissive phenylene-expanded [5]radialene.
Yu, Jie; Tang, Chunlin; Gu, Xinggui; Zheng, Xiaoyan; Yu, Zhen-Qiang; He, Zikai; Li, Xin-Gui; Tang, Ben Zhong; Chemical communications (Cambridge, England) 56 (2020) 3911–3914; doi:10.1039/d0cc00122h

data_7126076
_publ_section_title
;
 Highly emissive phenylene-expanded [5]radialene.
;
_journal_issue                   27
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3911
_journal_page_last               3914
_journal_paper_doi               10.1039/d0cc00122h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '2(C6 H5 Cl), C100 H70'
_chemical_formula_sum            'C112 H80 Cl2'
_chemical_formula_weight         1496.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc249ry5
_audit_creation_date             2018-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-06 deposited with the CCDC.	2020-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.253(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.9806(9)
_cell_length_b                   24.2530(8)
_cell_length_c                   26.5964(8)
_cell_measurement_reflns_used    9774
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      74.614
_cell_measurement_theta_min      3.645
_cell_volume                     16624.5(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1790
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            216484
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         2.475
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.088
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1629 before and 0.1000 after correction. The Ratio of minimum to maximum transmission is 0.5854. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             6288
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.899
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.00022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2120
_refine_ls_number_reflns         29528
_refine_ls_number_restraints     198
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0945
_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^)+(0.1276P)^2^+25.0814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2318
_refine_ls_wR_factor_ref         0.2680
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18676
_reflns_number_total             29528
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc00122h2.cif
_cod_data_source_block           cu_1218_3_0m
_cod_depositor_comments          'Adding full bibliography for 7126076.cif.'
_cod_database_code               7126076
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.881
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Cl2 \\sim C10 \\sim C11 \\sim C12 \\sim C15 \\sim C18 \\sim C21: within 1.7A
with sigma of 0.004 and sigma for terminal atoms of 0.008
Cl5 \\sim C25 \\sim C26 \\sim C30 \\sim C27 \\sim C29 \\sim C28: within 1.7A
with sigma of 0.004 and sigma for terminal atoms of 0.008
C23 \\sim Cl4 \\sim C19 \\sim C20 \\sim C24 \\sim C21 \\sim C22: within 1.7A
with sigma of 0.004 and sigma for terminal atoms of 0.008
Cl3 \\sim C13 \\sim C14 \\sim C18 \\sim C15 \\sim C17 \\sim C16: within 1.7A
with sigma of 0.004 and sigma for terminal atoms of 0.008
Cl6 \\sim C31 \\sim C32 \\sim C36 \\sim C33 \\sim C35 \\sim C34: within 1.7A
with sigma of 0.004 and sigma for terminal atoms of 0.008
Cl2 \\sim C7 \\sim C8 \\sim C12 \\sim C9 \\sim C11 \\sim C10: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
3. Others
 Fixed Sof: Cl2(0.8) Cl6(0.2) C9(0.8) H9(0.8) C10(0.8) H10(0.8) C11(0.8)
 H11(0.8) C12(0.8) H12(0.8) C7(0.8) C8(0.8) H8(0.8) C31(0.2) C32(0.2) H32(0.2)
 C33(0.2) H33(0.2) C34(0.2) H34(0.2) C35(0.2) H35(0.2) C36(0.2) H36(0.2)
 Cl4(0.7) Cl5(0.3) C19(0.7) C20(0.7) H20(0.7) C21(0.7) H21(0.7) C22(0.7)
 H22(0.7) C23(0.7) H23(0.7) C24(0.7) H24(0.7) C27(0.3) H27(0.3) C28(0.3)
 H28(0.3) C29(0.3) H29(0.3) C30(0.3) H30(0.3) C25(0.3) C26(0.3) H26(0.3)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6(H6), C5(H5), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C8(H8), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C27(H27), C28(H28), C29(H29), C30(H30), C26(H26), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50),
  C52(H52), C53(H53), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62),
 C64(H64), C65(H65), C66(H66), C67(H67), C68(H68), C70(H70), C71(H71), C76(H76),
  C77(H77), C78(H78), C79(H79), C80(H80), C82(H82), C83(H83), C84(H84),
 C85(H85), C86(H86), C88(H88), C89(H89), C94(H94), C95(H95), C96(H96), C97(H97),
  C98(H98), C100(H100), C101(H101), C102(H102), C103(H103), C104(H104),
 C106(H106), C107(H107), C112(H112), C113(H113), C114(H114), C115(H115),
 C116(H116), C118(H118), C119(H119), C120(H120), C121(H121), C122(H122),
 C124(H124), C125(H125), C127(H127), C128(H128), C129(H129), C130(H130),
 C131(H131), C132(H132), C133(H133), C134(H134), C135(H135), C136(H136),
 C140(H140), C141(H141), C142(H142), C143(H143), C144(H144), C146(H146),
 C147(H147), C148(H148), C149(H149), C150(H150), C152(H152), C153(H153),
 C158(H158), C159(H159), C160(H160), C161(H161), C162(H162), C164(H164),
 C165(H165), C166(H166), C167(H167), C168(H168), C170(H170), C171(H171),
 C176(H176), C177(H177), C178(H178), C179(H179), C180(H180), C182(H182),
 C183(H183), C184(H184), C185(H185), C186(H186), C188(H188), C189(H189),
 C194(H194), C195(H195), C196(H196), C197(H197), C198(H198), C200(H200),
 C201(H201), C202(H202), C203(H203), C204(H204), C206(H206), C207(H207),
 C212(H212), C213(H213), C214(H214), C215(H215), C216(H216), C218(H218),
 C219(H219), C220(H220), C221(H221), C222(H222), C224(H224), C225(H225),
 C227(H227), C228(H228), C229(H229), C230(H230), C231(H231), C232(H232),
 C233(H233), C234(H234), C235(H235), C236(H236)
4.b Fitted hexagon refined as free rotating group:
 C3(C2,C1,C6,C5,C4), C9(C10,C11,C12,C7,C8), C31(C32,C33,C34,C35,C36), C19(C20,
 C21,C22,C23,C24), C27(C28,C29,C30,C25,C26)
;
_shelx_res_checksum              75
_shelx_hkl_checksum              95911
_olex2_submission_special_instructions 'No special instructions were received'