Synthesis of Cycloiptycenes from Carbon Nanobelt
Shudo, Hiroki; Kuwayama, Motonobu; Segawa, Yasutomo; Itami, Kenichiro; Chemical Science  (2020) –; doi:10.1039/D0SC02501A

data_1558178
_publ_section_title
;
 Synthesis of Cycloiptycenes from Carbon Nanobelt
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02501A
_journal_year                    2020
_chemical_formula_moiety         '0.5(C96 H72 O12), 6(C4 H8 O2), 0.5(C4 O2)'
_chemical_formula_sum            'C74 H84 O19'
_chemical_formula_weight         1277.41
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-19 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                120.0
_cell_formula_units_Z            6
_cell_length_a                   31.0383(8)
_cell_length_b                   31.0383(8)
_cell_length_c                   11.8708(4)
_cell_measurement_reflns_used    9468
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      22.8020
_cell_measurement_theta_min      2.2600
_cell_volume                     9903.9(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -105.00  75.00   0.50   25.00    --  -15.00  45.00   0.00  360
  2  \w   -105.00  75.00   0.50   25.00    --  -15.00  45.00  90.00  360
  3  \w   -105.00  75.00   0.50   25.00    --  -15.00  45.00 180.00  360
  4  \w   -105.00  75.00   0.50   25.00    --  -15.00  45.00 270.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0081980333
_diffrn_orient_matrix_UB_12      0.0058746667
_diffrn_orient_matrix_UB_13      0.0566138667
_diffrn_orient_matrix_UB_21      -0.0197739667
_diffrn_orient_matrix_UB_22      0.0045990667
_diffrn_orient_matrix_UB_23      0.0115965667
_diffrn_orient_matrix_UB_31      -0.0153981333
_diffrn_orient_matrix_UB_32      -0.0252986667
_diffrn_orient_matrix_UB_33      0.0152376333
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            45408
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.062
_diffrn_reflns_theta_min         1.875
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             4080
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.212
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.510
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5068
_refine_ls_number_restraints     119
_refine_ls_restrained_S_all      1.568
_refine_ls_R_factor_all          0.2302
_refine_ls_R_factor_gt           0.1465
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4100
_refine_ls_wR_factor_ref         0.4520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2467
_reflns_number_total             5068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02501a2.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               1558178
_shelx_shelxl_version_number     2018/3
_cell_oxdiff_angle_alpha         90.015(2)
_cell_oxdiff_angle_beta          89.998(3)
_cell_oxdiff_angle_gamma         119.907(3)
_cell_oxdiff_length_a            31.0312(10)
_cell_oxdiff_length_b            31.0228(9)
_cell_oxdiff_length_c            11.8682(4)
_cell_oxdiff_measurement_reflns_used 9486
_cell_oxdiff_volume              9903.9(5)
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.991
_reflns_odcompleteness_completeness 94.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.00
_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
2. Restrained distances
 C17-C18 = C19-C20 = C21-C22 = C23-C24
 1.53 with sigma of 0.01
 O3-C17 = O3-C20 = O4-C18 = O4-C19 = O7-C25
 1.43 with sigma of 0.01
 O5-C21 = O5-C24 = O6-C22 = O6-C23
 1.43 with sigma of 0.01
 C17-C20 = C18-C19 = C21-C24 = C22-C23
 2.34 with sigma of 0.02
 O3-C18 = O3-C19 = O4-C17 = O4-C20
 2.43 with sigma of 0.02
 O5-C22 = O5-C23 = O6-C21 = O6-C24
 2.43 with sigma of 0.02
 C17-C19 = C18-C20 = C21-C23 = C22-C24
 2.8 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim O5 \\sim O6 \\sim O7: within
2A with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24)
\\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O6) \\sim Ueq,
Uanis(O7) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C25(0.66667)
5.a Ternary CH refined with riding coordinates:
 C7(H), C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,
 H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C13(H13)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,HA), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              43278
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.822