Synthesis, Structure, and Photophysical Properties of <i>m</i>-Phenylene-Embedded Cycloparaphenylene Nanorings.
Zhao, Hongyan; Cao, Lei; Huang, Shiqing; Ma, Chenxing; Chang, Yunhao; Feng, Kai; Zhao, Liang-Liang; Zhao, Peng; Yan, Xiaoyu; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00232

data_4038420
_publ_section_title
;
 Synthesis, Structure, and Photophysical Properties of
 <i>m</i>-Phenylene-Embedded Cycloparaphenylene Nanorings.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00232
_journal_year                    2020
_chemical_formula_moiety         'C57 H42 O3'
_chemical_formula_sum            'C57 H42 O3'
_chemical_formula_weight         774.90
_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             2019-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.202(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9841(11)
_cell_length_b                   25.969(3)
_cell_length_c                   16.0268(16)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.371
_cell_measurement_theta_min      2.314
_cell_volume                     4980.0(9)
_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)'
_diffrn_ambient_temperature      199.99
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.975
_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  0.0775
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            66825
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_min         2.664
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1006 before and 0.0613 after correction. The Ratio of minimum to maximum transmission is 0.8492. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.034
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         11219
_refine_ls_number_restraints     1302
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0692P)^2^+0.3814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1526
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6686
_reflns_number_total             11219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00232_si_003.cif
_cod_data_source_block           mo_zhy2019051706_0m_a_sqd
_cod_original_cell_volume        4980.0(8)
_cod_database_code               4038420
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 3.5A with sigma of 0.01 and sigma
for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00J(H00J), C00N(H00N),
 C00O(H00O), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00Z(H00Z),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C017(H017),
 C018(H018), C019(H019), C01A(H01D), C01B(H01E), C01C(H01F), C01D(H01G),
 C01E(H01H), C01F(H01I), C01G(H01J), C01H(H01K), C01I(H01L), C01J(H01M),
 C01K(H01N), C01L(H01O), C01M(H01P)
3.b Idealised Me refined as rotating group:
 C016(H01A,H01B,H01C), C01N(H01Q,H01R,H01S), C01O(H01T,H01U,H01V)
;
_shelx_res_checksum              40827
_shelx_hkl_checksum              32064
_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_void_probe_radius 1.20