Large Aromatic Hydrocarbon Radical Cation with Global Aromaticity and State-Associated Magnetic Activity
Guo, Jing; Zhou, Cong; Xie, Sheng; Luo, Shenglian; Gopalakrishna, Tullimilli Y.; Sun, Zhe; Jouha, Jabrane; Wu, Jishan; Zeng, Zebing; Chemistry of Materials 32 (2020) 5927–5936; doi:10.1021/acs.chemmater.9b05099

data_4003632
_publ_section_title
;
 Large Aromatic Hydrocarbon Radical Cation with Global Aromaticity and
 State-Associated Magnetic Activity
;
_journal_issue                   14
_journal_name_full               'Chemistry of Materials'
_journal_page_first              5927
_journal_page_last               5936
_journal_paper_doi               10.1021/acs.chemmater.9b05099
_journal_volume                  32
_journal_year                    2020
_chemical_formula_moiety         'C72 H78 O8'
_chemical_formula_sum            'C72 H78 O8'
_chemical_formula_weight         1071.34
_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
_audit_creation_date             2017-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.2100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3015(5)
_cell_length_b                   22.8272(6)
_cell_length_c                   18.6041(5)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      44.138
_cell_measurement_theta_min      4.559
_cell_volume                     6098.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            94050
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.468
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016) was used for absorption correction. wR2(int) was 0.1375 before and 0.0699 after correction. The Ratio of minimum to maximum transmission is 0.9254. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0054(6)
_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   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     866
_refine_ls_number_reflns         10727
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0998P)^2^+4.3324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.2308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6399
_reflns_number_total             10727
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm9b05099_si_006.cif
_cod_data_source_block           mo_d8v17232_0m
_cod_depositor_comments
;Adding full bibliography for 4003630--4003634.cif.

 Adding full bibliography for 4003630--4003634.cif.
;
_cod_database_code               4003632
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Shared sites
{C67, C67'}
2. Others
 Fixed Sof: C55(0.7) H55A(0.7) H55B(0.7) C56(0.7) H56A(0.7) H56B(0.7) C57(0.7)
 H57A(0.7) H57B(0.7) C58(0.7) H58A(0.7) H58B(0.7) H58C(0.7) C55'(0.3) H55C(0.3)
 H55D(0.3) C56'(0.3) H56C(0.3) H56D(0.3) C57'(0.3) H57C(0.3) H57D(0.3)
 C58'(0.3) H58D(0.3) H58E(0.3) H58F(0.3) C63(0.6) H63A(0.6) H63B(0.6) C64(0.6)
 H64A(0.6) H64B(0.6) C65(0.6) H65A(0.6) H65B(0.6) C66(0.6) H66A(0.6) H66B(0.6)
 H66C(0.6) C63'(0.4) H63C(0.4) H63D(0.4) C64'(0.4) H64C(0.4) H64D(0.4)
 C65'(0.4) H65C(0.4) H65D(0.4) C66'(0.4) H66D(0.4) H66E(0.4) H66F(0.4) C67(0.5)
 H67A(0.5) H67B(0.5) C68(0.5) H68A(0.5) H68B(0.5) C69(0.5) H69A(0.5) H69B(0.5)
 C70(0.5) H70A(0.5) H70B(0.5) H70C(0.5) C67'(0.5) H67C(0.5) H67D(0.5) C68'(0.5)
 H68C(0.5) H68D(0.5) C69'(0.5) H69C(0.5) H69D(0.5) C70'(0.5) H70D(0.5)
 H70E(0.5) H70F(0.5) O7(0.7) C71(0.7) H71A(0.7) H71B(0.7) H71C(0.7) O7'(0.3)
 C71'(0.3) H71D(0.3) H71E(0.3) H71F(0.3)
 Fixed Uiso: H2(0.079) H3(0.091) H4(0.098) H5(0.086) H29(0.087) H30(0.103)
 H31(0.102) H32(0.085) H37(0.075) H39(0.081) H41A(0.148) H41B(0.148)
 H41C(0.148) H42A(0.123) H42B(0.123) H42C(0.123) H43A(0.135) H43B(0.135)
 H43C(0.135) H46(0.074) H48(0.08) H50A(0.128) H50B(0.128) H50C(0.128)
 H51A(0.116) H51B(0.116) H51C(0.116) H52A(0.137) H52B(0.137) H52C(0.137)
 H53A(0.137) H53B(0.137) H53C(0.137) H54A(0.161) H54B(0.161) H54C(0.161)
 H55A(0.096) H55B(0.096) H56A(0.12) H56B(0.12) H57A(0.183) H57B(0.183)
 H58A(0.428) H58B(0.428) H58C(0.428) H55C(0.113) H55D(0.113) H56C(0.232)
 H56D(0.232) H57C(0.444) H57D(0.444) H58D(0.512) H58E(0.512) H58F(0.512)
 H59A(0.116) H59B(0.116) H60A(0.18) H60B(0.18) H61A(0.257) H61B(0.257)
 H62A(0.364) H62B(0.364) H62C(0.364) H63A(0.142) H63B(0.142) H64A(0.176)
 H64B(0.176) H65A(0.21) H65B(0.21) H66A(0.302) H66B(0.302) H66C(0.302)
 H63C(0.254) H63D(0.254) H64C(0.262) H64D(0.262) H65C(0.262) H65D(0.262)
 H66D(0.332) H66E(0.332) H66F(0.332) H67A(0.106) H67B(0.106) H68A(0.13)
 H68B(0.13) H69A(0.146) H69B(0.146) H70A(0.208) H70B(0.208) H70C(0.208)
 H67C(0.175) H67D(0.175) H68C(0.183) H68D(0.183) H69C(0.193) H69D(0.193)
 H70D(0.26) H70E(0.26) H70F(0.26) H72A(0.16) H72B(0.16) H72C(0.16) H71A(0.139)
 H71B(0.139) H71C(0.139) H71D(0.133) H71E(0.133) H71F(0.133)
 Fixed X: H2(0.4333) H3(0.5426) H4(0.6613) H5(0.6781) H29(0.3863) H30(0.4011)
 H31(0.5186) H32(0.6129) H37(0.894) H39(0.7096) H41A(0.5594) H41B(0.5522)
 H41C(0.5178) H42A(0.7623) H42B(0.8648) H42C(0.7925) H43A(0.8787) H43B(0.9478)
 H43C(0.8786) H46(0.2714) H48(0.1585) H50A(0.2789) H50B(0.1986) H50C(0.3026)
 H51A(0.4089) H51B(0.4692) H51C(0.3942) H52A(0.1429) H52B(0.1496) H52C(0.0742)
 H53A(0.2278) H53B(0.1391) H53C(0.1737) H54A(0.746) H54B(0.8253) H54C(0.8303)
 H55A(0.2003) H55B(0.2665) H56A(0.1614) H56B(0.1219) H57A(0.0157) H57B(0.0847)
 H58A(0.0331) H58B(-0.0496) H58C(0.0379) H55C(0.2677) H55D(0.2628) H56C(0.1213)
 H56D(0.1164) H57C(0.0287) H57D(0.0558) H58D(-0.0295) H58E(-0.08) H58F(0.0036)
 H59A(0.8302) H59B(0.7753) H60A(0.8713) H60B(0.9358) H61A(0.8996) H61B(0.973)
 H62A(0.9939) H62B(1.0396) H62C(1.071) H63A(0.2303) H63B(0.2828) H64A(0.2427)
 H64B(0.2904) H65A(0.1546) H65B(0.1076) H66A(0.1793) H66B(0.1086) H66C(0.0763)
 H63C(0.4013) H63D(0.4603) H64C(0.3555) H64D(0.3637) H65C(0.2137) H65D(0.2218)
 H66D(0.2715) H66E(0.1704) H66F(0.1931) H67A(0.6396) H67B(0.5628) H68A(0.6968)
 H68B(0.6186) H69A(0.7849) H69B(0.7036) H70A(0.8428) H70B(0.7697) H70C(0.7474)
 H67C(0.6126) H67D(0.5656) H68C(0.6278) H68D(0.6641) H69C(0.7739) H69D(0.8018)
 H70D(0.7975) H70E(0.847) H70F(0.7422) H72A(0.8217) H72B(0.8311) H72C(0.8126)
 H71A(0.4775) H71B(0.4392) H71C(0.5287) H71D(0.2383) H71E(0.235) H71F(0.245)
 Fixed Y: H2(0.0511) H3(0.0172) H4(0.0775) H5(0.1691) H29(0.5218) H30(0.6107)
 H31(0.6745) H32(0.6533) H37(0.6514) H39(0.7224) H41A(0.6275) H41B(0.6939)
 H41C(0.6456) H42A(0.5647) H42B(0.5667) H42C(0.5233) H43A(0.7463) H43B(0.7227)
 H43C(0.7735) H46(0.0317) H48(0.0435) H50A(0.1648) H50B(0.1212) H50C(0.1039)
 H51A(0.1484) H51B(0.094) H51C(0.0881) H52A(-0.0291) H52B(-0.0534) H52C(-
 0.0063) H53A(0.1805) H53B(0.184) H53C(0.2399) H54A(0.2803) H54B(0.2332)
 H54C(0.2896) H55A(0.331) H55B(0.3847) H56A(0.4078) H56B(0.4225) H57A(0.372)
 H57B(0.3192) H58A(0.3464) H58B(0.3243) H58C(0.2844) H55C(0.3694) H55D(0.409)
 H56C(0.3341) H56D(0.3712) H57C(0.3898) H57D(0.4467) H58D(0.3445) H58E(0.4052)
 H58F(0.3976) H59A(0.2764) H59B(0.3146) H60A(0.3908) H60B(0.3363) H61A(0.387)
 H61B(0.3382) H62A(0.4521) H62B(0.4337) H62C(0.4035) H63A(0.355) H63B(0.3675)
 H64A(0.2526) H64B(0.2665) H65A(0.3159) H65B(0.2947) H66A(0.2149) H66B(0.2021)
 H66C(0.2371) H63C(0.3374) H63D(0.2972) H64C(0.2227) H64D(0.2438) H65C(0.2705)
 H65D(0.282) H66D(0.1696) H66E(0.1808) H66F(0.1898) H67A(0.5026) H67B(0.4539)
 H68A(0.3901) H68B(0.4196) H69A(0.4723) H69B(0.5093) H70A(0.4572) H70B(0.5019)
 H70C(0.4347) H67C(0.5014) H67D(0.44) H68C(0.431) H68D(0.4947) H69C(0.4047)
 H69D(0.4683) H70D(0.3742) H70E(0.4344) H70F(0.4261) H72A(0.5152) H72B(0.566)
 H72C(0.5018) H71A(0.3474) H71B(0.375) H71C(0.401) H71D(0.4799) H71E(0.4293)
 H71F(0.4145)
 Fixed Z: H2(0.4569) H3(0.4097) H4(0.4049) H5(0.4566) H29(0.8332) H30(0.8925)
 H31(0.8921) H32(0.8251) H37(0.8296) H39(0.6442) H41A(0.5825) H41B(0.6015)
 H41C(0.6454) H42A(0.8861) H42B(0.8861) H42C(0.8316) H43A(0.6796) H43B(0.7577)
 H43C(0.757) H46(0.6212) H48(0.3946) H50A(0.3706) H50B(0.3277) H50C(0.3431)
 H51A(0.6581) H51B(0.6533) H51C(0.6928) H52A(0.5595) H52B(0.4828) H52C(0.4807)
 H53A(0.5881) H53B(0.5139) H53C(0.5648) H54A(0.4649) H54B(0.4917) H54C(0.5412)
 H55A(0.4637) H55B(0.4975) H56A(0.5693) H56B(0.4814) H57A(0.522) H57B(0.5452)
 H58A(0.3921) H58B(0.4164) H58C(0.4293) H55C(0.4876) H55D(0.5553) H56C(0.4706)
 H56D(0.5377) H57C(0.3864) H57D(0.4387) H58D(0.4756) H58E(0.4548) H58F(0.5319)
 H59A(0.684) H59B(0.7246) H60A(0.7385) H60B(0.7656) H61A(0.6265) H61B(0.663)
 H62A(0.726) H62B(0.6659) H62C(0.7465) H63A(0.6928) H63B(0.7803) H64A(0.7192)
 H64B(0.8067) H65A(0.8028) H65B(0.7179) H66A(0.8356) H66B(0.7532) H66C(0.8121)
 H63C(0.8331) H63D(0.7989) H64C(0.7743) H64D(0.856) H65C(0.7271) H65D(0.813)
 H66D(0.7973) H66E(0.7401) H66F(0.8282) H67A(0.4768) H67B(0.4662) H68A(0.4426)
 H68B(0.3721) H69A(0.4656) H69B(0.4103) H70A(0.3769) H70B(0.3259) H70C(0.3196)
 H67C(0.4898) H67D(0.4652) H68C(0.3842) H68D(0.4016) H69C(0.47) H69D(0.4577)
 H70D(0.3709) H70E(0.3713) H70F(0.3203) H72A(0.7027) H72B(0.6492) H72C(0.6178)
 H71A(0.8659) H71B(0.9262) H71C(0.9155) H71D(0.7424) H71E(0.7983) H71F(0.7192)
;
_shelx_res_checksum              16463
_shelx_hkl_checksum              7609
_olex2_submission_special_instructions 'No special instructions were received'