Building Giant Carbocycles by Reversible C-C Bond Formation
Daniel Beaudoin; Olivier Levasseur-Grenon; Thierry Maris; James D. Wuest; Angew. Chem. Int. Ed. 55 (2016) 894–898; doi:

data_1542339
_publ_section_title
;
 Building Giant Carbocycles by Reversible C-C Bond Formation
;
_journal_name_full               'Angew. Chem. Int. Ed.'
_journal_page_first              894
_journal_page_last               898
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         'C268 H248, 9(C8 H10)'
_chemical_formula_sum            'C340 H338'
_chemical_formula_weight         4424.08
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.4036(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   40.4249(14)
_cell_length_b                   19.5832(7)
_cell_length_c                   34.5941(12)
_cell_measurement_reflns_used    9728
_cell_measurement_temperature    150
_cell_measurement_theta_max      66.489
_cell_measurement_theta_min      2.257
_cell_volume                     26525.6(16)
_computing_cell_refinement
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker Platinum 135 CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Microstar X8'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            504181
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.853
_diffrn_reflns_theta_min         2.257
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Bruker Microstar/FR591 generator'
_exptl_absorpt_coefficient_mu    0.464
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.6385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0721 after correction.
The Ratio of minimum to maximum transmission is 0.8475.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light Colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_description       block
_exptl_crystal_F_000             9512
_exptl_crystal_recrystallization_method 'Crystallized in p-Xylene'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1607
_refine_ls_number_reflns         25395
_refine_ls_number_restraints     360
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1048P)^2^+43.5399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1890
_refine_ls_wR_factor_ref         0.2036
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                20412
_reflns_number_total             25395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jw1644.cif
_cod_data_source_block           jw1644
_cod_database_code               1542339
_cod_database_fobs_code          1542339
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.946
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C172-C174
 1.55 with sigma of 0.001
 C159-C160 = C163-C166 = C1F-C1H = C1A-C1C
 1.55 with sigma of 0.001
 C14-C15 = C14-C16 = C14-C17 = C14-C15B = C14-C16B = C14-C17B
 1.55 with sigma of 0.001
 C64-C65 = C64-C66 = C64-C67 = C64-C65B = C64-C66B = C64-C67B
 1.55 with sigma of 0.001
 C81-C82 = C81-C83 = C81-C84 = C81-C82B = C81-C83B = C81-C84B
 1.55 with sigma of 0.001
 C171-C174 \\sim C173-C174 \\sim C170-C167 \\sim C168-C167
 with sigma of 0.02
 C159-C161 \\sim C159-C165 \\sim C166-C164 \\sim C166-C162
 with sigma of 0.02
 C1H-C1E \\sim C1H-C1G \\sim C1A-C1B \\sim C1A-C1D
 with sigma of 0.02
 C14-C15 \\sim C14-C16 \\sim C14-C17 \\sim C14-C15B \\sim C14-C16B \\sim
C14-C17B
 with sigma of 0.02
 C64-C65 \\sim C64-C66 \\sim C64-C67 \\sim C64-C65B \\sim C64-C66B \\sim
C64-C67B
 with sigma of 0.02
 C81-C82 \\sim C81-C83 \\sim C81-C84 \\sim C81-C82B \\sim C81-C83B \\sim
C81-C84B
 with sigma of 0.02
3. Restrained planarity
 C167, C168, C169, C170, C171, C172, C173, C174
 with sigma of 0.1
 C1A, C1B, C1C, C1D, C1E, C1F, C1G, C1H
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C167 \\sim C168 \\sim C169 \\sim C170 \\sim C171 \\sim C172 \\sim C173 \\sim
C174: within 1.7A with sigma of 0.001 and sigma for terminal atoms of 0.001
C159 \\sim C160 \\sim C161 \\sim C162 \\sim C163 \\sim C164 \\sim C165 \\sim
C166 \\sim C1A \\sim C1B \\sim C1C \\sim C1D \\sim C1E \\sim C1F \\sim C1G
\\sim C1H: within 1.7A with sigma of 0.001 and sigma for terminal atoms of 0.001
Uanis(C167) = Uanis(C174)
Uanis(C168) = Uanis(C171)
Uanis(C169) = Uanis(C172)
Uanis(C170) = Uanis(C173)
Uanis(C15) = Uanis(C15B)
Uanis(C16) = Uanis(C16B)
Uanis(C17) = Uanis(C17B)
Uanis(C65) = Uanis(C65B)
Uanis(C66) = Uanis(C66B)
Uanis(C67) = Uanis(C67B)
Uanis(C82) = Uanis(C82B)
Uanis(C83) = Uanis(C83B)
Uanis(C84) = Uanis(C84B)
Uanis(C159) = Uanis(C1A)
Uanis(C160) = Uanis(C1B)
Uanis(C161) = Uanis(C1C)
Uanis(C162) = Uanis(C1D)
Uanis(C163) = Uanis(C1E)
Uanis(C164) = Uanis(C1F)
Uanis(C165) = Uanis(C1G)
Uanis(C166) = Uanis(C1H)
5. Others
 Sof(C15B)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C16B)=Sof(H16D)=Sof(H16E)=
 Sof(H16F)=Sof(C17B)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(1)
 Sof(C65B)=Sof(H65D)=Sof(H65E)=Sof(H65F)=Sof(C66B)=Sof(H66D)=Sof(H66E)=
 Sof(H66F)=Sof(C67B)=Sof(H67D)=Sof(H67E)=Sof(H67F)=1-FVAR(2)
 Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=
 Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(H67C)=FVAR(2)
 Sof(C82B)=Sof(H82D)=Sof(H82E)=Sof(H82F)=Sof(C83B)=Sof(H83D)=Sof(H83E)=
 Sof(H83F)=Sof(C84B)=Sof(H84D)=Sof(H84E)=Sof(H84F)=1-FVAR(3)
 Sof(C82)=Sof(H82A)=Sof(H82B)=Sof(H82C)=Sof(C83)=Sof(H83A)=Sof(H83B)=Sof(H83C)=
 Sof(C84)=Sof(H84A)=Sof(H84B)=Sof(H84C)=FVAR(3)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1B)=Sof(H1B)=Sof(C1C)=Sof(C1D)=
 Sof(H1D)=Sof(C1E)=Sof(H1E)=Sof(C1F)=Sof(C1G)=Sof(H1G)=Sof(C1H)=Sof(H1HA)=
 Sof(H1HB)=Sof(H1HC)=1-FVAR(4)
 Sof(C159)=Sof(H15P)=Sof(H15Q)=Sof(H15R)=Sof(C160)=Sof(C161)=Sof(H161)=
 Sof(C162)=Sof(H162)=Sof(C163)=Sof(C164)=Sof(H164)=Sof(C165)=Sof(H165)=
 Sof(C166)=Sof(H16G)=Sof(H16H)=Sof(H16I)=FVAR(4)
 Fixed Sof: C167(0.5) H16J(0.5) H16K(0.5) H16L(0.5) C168(0.5) H168(0.5)
 C169(0.5) C170(0.5) H170(0.5) C171(0.5) H171(0.5) C172(0.5) C173(0.5)
 H173(0.5) C174(0.5) H17G(0.5) H17H(0.5) H17I(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C23(H23), C24(H24),
 C27(H27), C28(H28), C30(H30), C34(H34), C36(H36), C37(H37), C38(H38), C39(H39),
  C42(H42), C43(H43), C44(H44), C45(H45), C49(H49), C51(H51), C52(H52),
 C55(H55), C56(H56), C58(H58), C70(H70), C72(H72), C73(H73), C76(H76), C77(H77),
  C79(H79), C90(H90), C91(H91), C94(H94), C95(H95), C97(H97), C101(H101),
 C103(H103), C104(H104), C105(H105), C106(H106), C109(H109), C110(H110),
 C111(H111), C112(H112), C116(H116), C118(H118), C119(H119), C122(H122),
 C123(H123), C125(H125), C136(H136), C137(H137), C139(H139), C140(H140),
 C145(H145), C146(H146), C148(H148), C149(H149), C153(H153), C154(H154),
 C156(H156), C157(H157), C161(H161), C162(H162), C164(H164), C165(H165),
 C1B(H1B), C1D(H1D), C1E(H1E), C1G(H1G), C168(H168), C170(H170), C171(H171),
 C173(H173)
6.b Fitted hexagon refined as free rotating group:
 C160(C161,C162,C163,C164,C165), C1B(C1C,C1D,C1E,C1F,C1G), C168(C169,C170,C171,
 C172,C173)
6.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15B(H15D,H15E,
 H15F), C16B(H16D,H16E,H16F), C17B(H17D,H17E,H17F), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C61(H61A,H61B,H61C), C62(H62A,H62B,
 H62C), C63(H63A,H63B,H63C), C65(H65A,H65B,H65C), C66(H66A,H66B,H66C), C67(H67A,
 H67B,H67C), C65B(H65D,H65E,H65F), C66B(H66D,H66E,H66F), C67B(H67D,H67E,H67F),
 C82(H82A,H82B,H82C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C82B(H82D,H82E,
 H82F), C83B(H83D,H83E,H83F), C84B(H84D,H84E,H84F), C86(H86A,H86B,H86C),
 C87(H87A,H87B,H87C), C88(H88A,H88B,H88C), C128(H12A,H12B,H12C), C129(H12D,H12E,
 H12F), C130(H13A,H13B,H13C), C132(H13D,H13E,H13F), C133(H13G,H13H,H13I),
 C134(H13J,H13K,H13L), C141(H14A,H14B,H14C), C142(H14D,H14E,H14F), C143(H14G,
 H14H,H14I), C150(H15G,H15H,H15I), C151(H15J,H15K,H15L), C158(H15M,H15N,H15O),
 C159(H15P,H15Q,H15R), C166(H16G,H16H,H16I), C1A(H1AA,H1AB,H1AC), C1H(H1HA,H1HB,
 H1HC), C167(H16J,H16K,H16L), C174(H17G,H17H,H17I)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Mounted on a Cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'