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

data_1558177
_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         'C84 H48, 2(C H Cl3), 2(C5 H12)'
_chemical_formula_sum            'C96 H74 Cl6'
_chemical_formula_weight         1440.25
_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             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                 97.9869(19)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   13.9419(3)
_cell_length_b                   18.9963(3)
_cell_length_c                   14.6207(3)
_cell_measurement_reflns_used    23233
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.1010
_cell_measurement_theta_min      2.5650
_cell_volume                     3834.65(13)
_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 0.999
_diffrn_measured_fraction_theta_max 0.922
_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   30.00    --  -15.00  45.00   0.00  360
  2  \w   -105.00  75.00   0.50   30.00    --  -15.00  45.00  90.00  360
  3  \w   -105.00  75.00   0.50   30.00    --  -15.00  45.00 180.00  360
  4  \w   -105.00  75.00   0.50   30.00    --  -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      0.0001556000
_diffrn_orient_matrix_UB_12      0.0189918000
_diffrn_orient_matrix_UB_13      -0.0417476000
_diffrn_orient_matrix_UB_21      -0.0310232000
_diffrn_orient_matrix_UB_22      -0.0255920000
_diffrn_orient_matrix_UB_23      -0.0238563000
_diffrn_orient_matrix_UB_31      -0.0409478000
_diffrn_orient_matrix_UB_32      0.0194584000
_diffrn_orient_matrix_UB_33      0.0093735000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            69561
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.613
_diffrn_reflns_theta_min         2.174
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91692
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.364
_refine_diff_density_min         -0.965
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         10893
_refine_ls_number_restraints     200
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0732
_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^)+(0.1400P)^2^+4.4484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2204
_refine_ls_wR_factor_ref         0.2390
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8234
_reflns_number_total             10893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02501a2.cif
_cod_data_source_block           2
_cod_original_cell_volume        3834.64(13)
_cod_original_sg_symbol_H-M      'P 1 21/c 1'
_cod_database_code               1558177
_shelx_shelxl_version_number     2018/3
_cell_oxdiff_angle_alpha         90.0015(12)
_cell_oxdiff_angle_beta          97.9891(12)
_cell_oxdiff_angle_gamma         90.0035(11)
_cell_oxdiff_length_a            13.9422(2)
_cell_oxdiff_length_b            18.9958(3)
_cell_oxdiff_length_c            14.6209(2)
_cell_oxdiff_measurement_reflns_used 23233
_cell_oxdiff_volume              3834.64(9)
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.973
_reflns_odcompleteness_completeness 92.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.54
_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
 C44-C45 = C45-C46 = C46-C47 = C47-C48
 1.54 with sigma of 0.01
 C44-C46 = C46-C48 = C45-C47
 2.54 with sigma of 0.01
 C49-C50 = C50-C51 = C51-C52 = C52-C53
 1.54 with sigma of 0.01
 C49-C51 = C51-C53 = C50-C52
 2.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49 \\sim C50 \\sim C51 \\sim
C52 \\sim C53: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C47)
\\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C50) \\sim Ueq,
Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq: with sigma of
0.02 and sigma for terminal atoms of 0.02
4. Others
 Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C50)=
 Sof(H50A)=Sof(H50B)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=Sof(H53B)=
 Sof(H53C)=1-FVAR(1)
 Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(C46)=
 Sof(H46A)=Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=
 Sof(H48C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C21(H21), C22(H22), C35(H35), C36(H36), C43(H43)
5.b Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C51(H51A,H51B), C50(H50A,
 H50B), C52(H52A,H52B)
5.c Me refined with riding coordinates:
 C44(H44A,H44B,H44C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C53(H53A,H53B,
 H53C)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17),
 C24(H24), C25(H25), C26(H26), C27(H27), C32(H32), C33(H33), C38(H38), C39(H39),
  C40(H40), C41(H41)
;
_shelx_res_checksum              98767
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.148
_oxdiff_exptl_absorpt_empirical_full_min 0.888