Crystallographic evidence for global aromaticity in the di-anion and tetra-anion of a cyclophane hydrocarbon.
Stawski, Wojciech; Zhu, Yikun; Wei, Zheng; Petrukhina, Marina A.; Anderson, Harry L.; Chemical science 14 (2023) 14109–14114; doi:10.1039/d3sc04251k

data_1569913
_publ_section_title
;
 Crystallographic evidence for global aromaticity in the di-anion and
 tetra-anion of a cyclophane hydrocarbon.
;
_journal_issue                   48
_journal_name_full               'Chemical science'
_journal_page_first              14109
_journal_page_last               14114
_journal_paper_doi               10.1039/d3sc04251k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C56 H72 Na2 O6'
_chemical_formula_sum            'C56 H72 Na2 O6'
_chemical_formula_weight         887.11
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.8960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8122(3)
_cell_length_b                   26.5491(8)
_cell_length_c                   20.9892(7)
_cell_measurement_reflns_used    9188
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.40
_cell_measurement_theta_min      2.53
_cell_volume                     4904.3(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector
;
DECTRIS PILATUS3 X 1M(CdTe) pixel array detector
;
_diffrn_detector_area_resol_mean 30
_diffrn_detector_type            'CMOS pixel array detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Huber 4-circle diffractometer'
_diffrn_measurement_method       'phi rotation'
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_diffrn_radiation_monochromator  'Si(111) & Si(311)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.49594
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            247080
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        17.311
_diffrn_reflns_theta_max         24.924
_diffrn_reflns_theta_min         1.267
_diffrn_source                   synchrotron
_diffrn_source_current           103.0
_diffrn_source_power             103.0
_diffrn_source_type
'Insertion Device, Station 15 ID-B, APS, Argonne Nat'l Lab'
_diffrn_source_voltage           1000.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.046
_exptl_absorpt_correction_T_max  0.6984
_exptl_absorpt_correction_T_min  0.5797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016/2) was used for absorption correction.
wR2(int) was 0.1256 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.8300.
The \l/2 correction factor is not present.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         25085
_refine_ls_number_restraints     420
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+1.3371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18722
_reflns_number_total             25085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04251k2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569912--1569917.cif.
;
_cod_database_code               1569913
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.996
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
O3 \\sim C41 \\sim C42 \\sim C43 \\sim C44 \\sim C44X \\sim C41X \\sim C42X
\\sim C43X \\sim O3X: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
O1 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim O1X \\sim C33X \\sim C34X
\\sim C35X \\sim C36X: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(C36) = Uanis(C36X)
Uanis(C33) = Uanis(C33X)
3. Rigid body (RIGU) restrains
 O3, C41, C42, C43, C44, C44X, C41X, C42X, C43X, O3X, O1, C33, C34, C35, C36,
 O1X, C33X, C34X, C35X, C36X
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C44X)=Sof(H44C)=Sof(H44D)=Sof(C41X)=Sof(H41C)=Sof(H41D)=Sof(C42X)=
 Sof(H42C)=Sof(H42D)=Sof(C43X)=Sof(H43C)=Sof(H43D)=Sof(O3X)=1-FVAR(1)
 Sof(O3)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=
 Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=FVAR(1)
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(O1X)=Sof(C33X)=Sof(H33C)=Sof(H33D)=Sof(C34X)=
 Sof(H34C)=Sof(H34D)=Sof(C36X)=Sof(H36C)=Sof(H36D)=1-FVAR(2)
 Sof(O1)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C36)=
 Sof(H36A)=Sof(H36B)=Sof(C35X)=Sof(H35C)=Sof(H35D)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,
 H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B),
 C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B),
  C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,
 H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B),
 C56(H56A,H56B), C44X(H44C,H44D), C41X(H41C,H41D), C42X(H42C,H42D), C43X(H43C,
 H43D), C33X(H33C,H33D), C34X(H34C,H34D), C35X(H35C,H35D), C36X(H36C,H36D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
  C24(H24), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32)
;
_shelx_res_checksum              7916
_olex2_submission_special_instructions 'No special instructions were received'