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

data_1558180
_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         'C132 H84, 2(C4 H8 O), 0.5(C5 H12)'
_chemical_formula_sum            'C142.5 H106 O2'
_chemical_formula_weight         1850.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                111.731(10)
_cell_angle_beta                 95.979(8)
_cell_angle_gamma                99.110(7)
_cell_formula_units_Z            1
_cell_length_a                   11.0799(9)
_cell_length_b                   15.4092(15)
_cell_length_c                   16.833(2)
_cell_measurement_reflns_used    1628
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      24.4580
_cell_measurement_theta_min      1.8690
_cell_volume                     2594.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_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_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.772
_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    -20.00  86.00   0.50  102.09    --    4.93  37.00  60.00  212
  2  \w    -15.00  33.00   0.50  102.09    --   -4.53 -99.00 -30.00   96
  3  \w     38.00  88.00   0.50  102.09    --    4.93 179.00-120.00  100
  4  \w    -20.00  86.00   0.50  102.09    --    4.93  37.00 150.00  212
  5  \w    -88.00 -43.00   0.50  102.09    --   -4.53 179.00 150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0074405000
_diffrn_orient_matrix_UB_12      0.0032963000
_diffrn_orient_matrix_UB_13      -0.0402012000
_diffrn_orient_matrix_UB_21      0.0368311000
_diffrn_orient_matrix_UB_22      0.0468426000
_diffrn_orient_matrix_UB_23      0.0225473000
_diffrn_orient_matrix_UB_31      0.0541163000
_diffrn_orient_matrix_UB_32      -0.0191749000
_diffrn_orient_matrix_UB_33      0.0001468000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1831
_diffrn_reflns_av_unetI/netI     0.3051
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.772
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24058
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.625
_diffrn_reflns_theta_min         1.891
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
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    1.184
_exptl_crystal_description       block
_exptl_crystal_F_000             977
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.388
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         10280
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.3183
_refine_ls_R_factor_gt           0.1177
_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^)+(0.1925P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2859
_refine_ls_wR_factor_ref         0.3871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3374
_reflns_number_total             10280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02501a2.cif
_cod_data_source_block           4
_cod_original_cell_volume        2594.1(5)
_cod_original_formula_sum        'C142.50 H106 O2'
_cod_database_code               1558180
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C132 H84'
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.993
_diffrn_oxdiff_digest_frames
;
01c9afa063635abd0be0705a8aaf70d4cb000252589
;
_diffrn_oxdiff_digest_hkl
;
0123c8304af2131c969b8c9afb18d97a254aa5
;
_reflns_odcompleteness_completeness 98.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_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
 C67-C68 = C68-C69 = C69-C70
 1.54 with sigma of 0.01
 O1-C67 = O1-C70
 1.43 with sigma of 0.01
 C71-C72 = C72-C73 = C73-C74 = C74-C75
 1.54 with sigma of 0.01
 C71-C73
 2.54 with sigma of 0.01
 C74-C72
 2.54 with sigma of 0.01
 C73-C75
 2.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C67 \\sim C68 \\sim C69 \\sim C70: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C67) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C70)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C75) \\sim Ueq, Uanis(C71) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C71, C72, C73, C74, C75
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C75(0.25) H75A(0.25) H75B(0.25) H75C(0.25) C74(0.25) H74A(0.25)
 H74B(0.25) C73(0.25) H73A(0.25) H73B(0.25) C72(0.25) H72A(0.25) H72B(0.25)
 C71(0.25) H71A(0.25) H71B(0.25) H71C(0.25)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C11(H11), C14(H14), C21(H21), C24(H24)
6.b Secondary CH2 refined with riding coordinates:
 C67(H67A,H67B), C68(H68A,H68B), C69(H69A,H69B), C70(H70A,H70B), C74(H74A,
 H74B), C73(H73A,H73B), C72(H72A,H72B)
6.c Me refined with riding coordinates:
 C75(H75A,H75B,H75C), C71(H71A,H71B,H71C)
6.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C17(H17), C18(H18), C28(H28), C29(H29), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42),
  C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C50(H50), C51(H51),
 C52(H52), C53(H53), C54(H54), C56(H56), C57(H57), C58(H58), C59(H59), C60(H60),
  C62(H62), C63(H63), C64(H64), C65(H65), C66(H66)
;
_shelx_res_checksum              85340
_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 1.974
_oxdiff_exptl_absorpt_empirical_full_min 0.478