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

data_1558179
_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         'C168 H96, 3(C H2 Cl2), 6(C5 H12)'
_chemical_formula_sum            'C201 H174 Cl6'
_chemical_formula_weight         2802.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                 109.884(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   46.422(4)
_cell_length_b                   7.7267(6)
_cell_length_c                   46.356(4)
_cell_measurement_reflns_used    4157
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      18.8560
_cell_measurement_theta_min      2.3450
_cell_volume                     15636(2)
_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 0.993
_diffrn_measured_fraction_theta_max 0.928
_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   -110.00  70.00   0.50  100.00    --  -20.00  45.00   0.00  360
  2  \w   -110.00  70.00   0.50  100.00    --  -20.00  45.00  70.00  360
  3  \w   -110.00  70.00   0.50  100.00    --  -20.00  45.00 140.00  360
  4  \w   -110.00  70.00   0.50  100.00    --  -20.00  45.00 210.00  360
  5  \w   -110.00  70.00   0.50  100.00    --  -20.00  45.00 280.00  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      -0.0004917000
_diffrn_orient_matrix_UB_12      -0.0911997000
_diffrn_orient_matrix_UB_13      -0.0018667000
_diffrn_orient_matrix_UB_21      -0.0162382000
_diffrn_orient_matrix_UB_22      0.0027401000
_diffrn_orient_matrix_UB_23      -0.0054138000
_diffrn_orient_matrix_UB_31      -0.0000735000
_diffrn_orient_matrix_UB_32      0.0102411000
_diffrn_orient_matrix_UB_33      -0.0152301000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.4476
_diffrn_reflns_av_unetI/netI     0.4720
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            92326
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.991
_diffrn_reflns_theta_min         1.866
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61379
_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            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             5928
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1039
_refine_ls_number_reflns         15814
_refine_ls_number_restraints     270
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.4275
_refine_ls_R_factor_gt           0.1677
_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^)+(0.1885P)^2^+69.9761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3823
_refine_ls_wR_factor_ref         0.4979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4075
_reflns_number_total             15814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02501a2.cif
_cod_data_source_block           12
_cod_original_sg_symbol_H-M      'C 1 2/m 1'
_cod_database_code               1558179
_shelx_shelxl_version_number     2018/3
_cell_oxdiff_angle_alpha         89.982(7)
_cell_oxdiff_angle_beta          109.893(6)
_cell_oxdiff_angle_gamma         89.993(7)
_cell_oxdiff_length_a            46.431(3)
_cell_oxdiff_length_b            7.7254(8)
_cell_oxdiff_length_c            46.357(3)
_cell_oxdiff_measurement_reflns_used 4161
_cell_oxdiff_volume              15636(2)
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.992
_reflns_odcompleteness_completeness 92.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C92-C93 = C93-C94 = C94-C95 = C95-C96
 1.54 with sigma of 0.01
 C92-C94 = C94-C96 = C93-C95
 2.54 with sigma of 0.02
 C85-Cl1 = C85-Cl2 = C86-Cl3 = C85-Cl4
 1.76 with sigma of 0.01
 Cl1-Cl2 = Cl3-Cl3_$1 = Cl2-Cl4
 2.85 with sigma of 0.02
 C1A-C98A
 2.54 with sigma of 0.02
 C99A-C97A
 2.54 with sigma of 0.02
 C97-C98 = C98-C99 = C99-C100 = C100-C101
 1.54 with sigma of 0.01
 C97-C99 = C98-C100 = C99-C101
 2.54 with sigma of 0.02
 C1B-C99A
 2.54 with sigma of 0.02
 C89A-C87A
 2.54 with sigma of 0.02
 C88A-C90A
 2.54 with sigma of 0.02
 C87-C88 = C88-C89 = C89-C90 = C90-C91
 1.54 with sigma of 0.01
 C87-C89 = C89-C91 = C88-C90
 2.54 with sigma of 0.02
 C91A-C89A
 2.54 with sigma of 0.02
 C99A-C1A = C1B-C1A = C99A-C98A = C98A-C97A = C88A-C87A = C89A-C88A = C90A-
 C89A = C91A-C90A
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C97) \\sim Ueq, Uanis(C98) \\sim Ueq, Uanis(C99) \\sim Ueq, Uanis(C100)
\\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(C86) \\sim Ueq:
with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C87) \\sim Ueq, Uanis(C88) \\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(C90)
\\sim Ueq, Uanis(C91) \\sim Ueq, Uanis(C92) \\sim Ueq, Uanis(C93) \\sim Ueq,
Uanis(C94) \\sim Ueq, Uanis(C95) \\sim Ueq, Uanis(C96) \\sim Ueq: with sigma of
0.02 and sigma for terminal atoms of 0.02
Uanis(C90A) \\sim Ueq, Uanis(C98A) \\sim Ueq, Uanis(C97A) \\sim Ueq,
Uanis(C91A) \\sim Ueq, Uanis(C99A) \\sim Ueq, Uanis(C88A) \\sim Ueq,
Uanis(C87A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C100, C97, C99, C98, C101, C97A, C98A, C99A, C1A, C1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C89, C90, C91, C88, C87, C89A, C90A, C91A, C88A, C87A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H85C)=Sof(H85D)=Sof(Cl4)=1-FVAR(1)
 Sof(Cl1)=Sof(H85A)=Sof(H85B)=FVAR(1)
 Sof(C97A)=Sof(H97D)=Sof(H97E)=Sof(H97F)=Sof(C98A)=Sof(H98C)=Sof(H98D)=
 Sof(C99A)=Sof(H99C)=Sof(H99D)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1B)=Sof(H1BA)=
 Sof(H1BB)=Sof(H1BC)=1-FVAR(2)
 Sof(C100)=Sof(H10A)=Sof(H10B)=Sof(C97)=Sof(H97A)=Sof(H97B)=Sof(H97C)=Sof(C99)=
 Sof(H99A)=Sof(H99B)=Sof(C98)=Sof(H98A)=Sof(H98B)=Sof(C101)=Sof(H10C)=Sof(H10D)=
 Sof(H10E)=FVAR(2)
 Sof(C89A)=Sof(H89C)=Sof(H89D)=Sof(C90A)=Sof(H90C)=Sof(H90D)=Sof(C91A)=
 Sof(H91D)=Sof(H91E)=Sof(H91F)=Sof(C88A)=Sof(H88C)=Sof(H88D)=Sof(C87A)=
 Sof(H87D)=Sof(H87E)=Sof(H87F)=1-FVAR(3)
 Sof(C89)=Sof(H89A)=Sof(H89B)=Sof(C90)=Sof(H90A)=Sof(H90B)=Sof(C91)=Sof(H91A)=
 Sof(H91B)=Sof(H91C)=Sof(C88)=Sof(H88A)=Sof(H88B)=Sof(C87)=Sof(H87A)=Sof(H87B)=
 Sof(H87C)=FVAR(3)
 Fixed Sof: C86(0.5) H86A(0.5) H86B(0.5)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C15(H15), C16(H16), C23(H23), C24(H24), C31(H31), C32(H32),
 C51(H51), C52(H52), C71(H71), C72(H72)
6.b Secondary CH2 refined with riding coordinates:
 C85(H85A,H85B), C85(H85C,H85D), C86(H86A,H86B), C89(H89A,H89B), C90(H90A,
 H90B), C88(H88A,H88B), C93(H93A,H93B), C94(H94A,H94B), C95(H95A,H95B),
 C100(H10A,H10B), C99(H99A,H99B), C98(H98A,H98B), C98A(H98C,H98D), C99A(H99C,
 H99D), C1A(H1AA,H1AB), C89A(H89C,H89D), C90A(H90C,H90D), C88A(H88C,H88D)
6.c Me refined with riding coordinates:
 C91(H91A,H91B,H91C), C87(H87A,H87B,H87C), C96(H96A,H96B,H96C), C92(H92A,H92B,
 H92C), C97(H97A,H97B,H97C), C101(H10C,H10D,H10E), C97A(H97D,H97E,H97F),
 C1B(H1BA,H1BB,H1BC), C91A(H91D,H91E,H91F), C87A(H87D,H87E,H87F)
6.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C11(H11), C12(H12), C18(H18), C19(H19), C26(H26), C29(H29),
 C34(H34), C35(H35), C36(H36), C37(H37), C40(H40), C41(H41), C42(H42), C43(H43),
  C46(H46), C49(H49), C54(H54), C55(H55), C56(H56), C57(H57), C60(H60),
 C61(H61), C62(H62), C63(H63), C66(H66), C69(H69), C74(H74), C75(H75), C76(H76),
  C77(H77), C80(H80), C81(H81), C82(H82), C83(H83)
;
_shelx_res_checksum              75207
_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 1.492
_oxdiff_exptl_absorpt_empirical_full_min 0.627