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_4038421
_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         'C4 H10 O, C54 H36, C H2 Cl, 0.3(H2 O)'
_chemical_formula_sum            'C59 H48.6 Cl O1.3'
_chemical_formula_weight         813.83
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.848(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9728(6)
_cell_length_b                   25.9830(13)
_cell_length_c                   15.1667(9)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      24.791
_cell_measurement_theta_min      2.322
_cell_volume                     4684.5(4)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      169.97
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_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  0.1005
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            66634
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.583
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1532 before and 0.0615 after correction. The Ratio of minimum to maximum transmission is 0.8482. 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    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.194
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         10724
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.0773
_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^)+(0.1115P)^2^+4.2021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.2317
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6321
_reflns_number_total             10724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00232_si_002.cif
_cod_data_source_block           mo_zhy2019040203_0m_a
_cod_original_formula_sum        'C59 H48.60 Cl O1.30'
_cod_database_code               4038421
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.981
_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, All O(H,H) groups
2. Restrained distances
 C3A-Cl0A
 1.8 with sigma of 0.02
 H1B-C00T
 3.4 with sigma of 0.01
 H1A-C008
 4.192 with sigma of 0.01
3. Rigid bond restraints
 H1B, O1, H1A
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
4. Uiso/Uaniso restraints and constraints
O1: within 3.5A with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=1-FVAR(1)
 Sof(C3)=Sof(H3A)=Sof(H3B)=FVAR(1)
 Fixed Sof: Cl1(0.5) Cl0A(0.5) O1(0.3) H1A(0.3) H1B(0.3)
6.a Free rotating group:
 O1(H1A,H1B)
6.b Secondary CH2 refined with riding coordinates:
 C01M(H01F,H01M), C01N(H01N,H01O), C3(H3A,H3B), C3A(H3AA,H3AB)
6.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N),
 C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C011(H011), C013(H013), C015(H015), C017(H017), C018(H018),
 C019(H019), C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E),
 C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L)
6.d Idealised Me refined as rotating group:
 C01O(H01P,H01Q,H01R), C01P(H01S,H01T,H01U)
;
_shelx_res_checksum              15073
_shelx_hkl_checksum              75561
_olex2_submission_special_instructions 'No special instructions were received'