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_1542340
_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, 15(C8 H10)'
_chemical_formula_sum            'C388 H398'
_chemical_formula_weight         5061.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                99.349(5)
_cell_angle_beta                 97.218(6)
_cell_angle_gamma                114.704(5)
_cell_formula_units_Z            1
_cell_length_a                   19.769(3)
_cell_length_b                   20.688(2)
_cell_length_c                   21.451(3)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    150
_cell_measurement_theta_max      65.073
_cell_measurement_theta_min      2.421
_cell_volume                     7678.8(18)
_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 0.989
_diffrn_measured_fraction_theta_max 0.969
_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  0.0765
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_laue_measured_fraction_full 0.989
_diffrn_reflns_laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            116866
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.722
_diffrn_reflns_theta_min         2.138
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Bruker Microstar/FR591 generator'
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1140 before and 0.0884 after correction.
The Ratio of minimum to maximum transmission is 0.6741.
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    1.094
_exptl_crystal_description       block
_exptl_crystal_F_000             2726
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2016
_refine_ls_number_reflns         28603
_refine_ls_number_restraints     1088
_refine_ls_restrained_S_all      1.248
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.1120
_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          0.3181
_refine_ls_wR_factor_ref         0.3570
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                16877
_reflns_number_total             28603
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jw1674.cif
_cod_data_source_block           jw1674
_cod_original_cell_volume        7679.0(17)
_cod_database_code               1542340
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.918
_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
 C204-C206 = C205-C207
 1.53 with sigma of 0.01
 C212-C214 = C213-C215
 1.53 with sigma of 0.01
 C237-C239 = C236-C238
 1.53 with sigma of 0.01
 C221-C223 = C220-C222
 1.53 with sigma of 0.01
 C22F-C22G = C22E-C22H
 1.53 with sigma of 0.01
 C244-C246 = C243-C247
 1.53 with sigma of 0.01
 C254-C257 = C255-C256
 1.53 with sigma of 0.01
 C270-C277 = C271-C276
 1.53 with sigma of 0.01
 C278-C285 = C283-C284
 1.53 with sigma of 0.01
 C286-C293 = C291-C292
 1.53 with sigma of 0.01
 C17-C18A = C17-C19A = C17-C20A = C17-C18B = C17-C19B = C17-C20B
 1.53 with sigma of 0.01
 C38-C39A = C38-C40A = C38-C41A = C38-C39B = C38-C40B = C38-C41B
 1.53 with sigma of 0.01
 C42-C43A = C42-C44A = C42-C45A = C42-C43B = C42-C44B = C42-C45B
 1.53 with sigma of 0.01
 C84-C85A = C84-C86A = C84-C87A = C84-C85B = C84-C86B = C84-C87B
 1.53 with sigma of 0.01
 C109-C110 = C109-C111 = C109-C112 = C109-C11A = C109-C11B = C109-C11C
 1.53 with sigma of 0.01
 C203-C206 \\sim C205-C206 \\sim C204-C207 \\sim C200-C207
 with sigma of 0.01
 C211-C214 \\sim C213-C214 \\sim C212-C215 \\sim C208-C215
 with sigma of 0.01
 C216-C223 \\sim C220-C223 \\sim C219-C222 \\sim C221-C222
 with sigma of 0.01
 C250-C256 \\sim C254-C256 \\sim C255-C257 \\sim C253-C257
 with sigma of 0.01
 C22A-C22G \\sim C22E-C22G \\sim C22F-C22H \\sim C22D-C22H
 with sigma of 0.01
 C275-C277 \\sim C271-C277 \\sim C270-C276 \\sim C272-C276
 with sigma of 0.01
 C279-C285 \\sim C283-C285 \\sim C278-C284 \\sim C282-C284
 with sigma of 0.01
 C287-C293 \\sim C291-C293 \\sim C286-C292 \\sim C290-C292
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C200 \\sim C201 \\sim C202 \\sim C203 \\sim C204 \\sim C205 \\sim C206 \\sim
C207 \\sim C208 \\sim C209 \\sim C210 \\sim C211 \\sim C212 \\sim C213 \\sim
C214 \\sim C215: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
C216 \\sim C217 \\sim C218 \\sim C219 \\sim C220 \\sim C221 \\sim C222 \\sim
C223 \\sim C22A \\sim C22B \\sim C22C \\sim C22D \\sim C22E \\sim C22F \\sim
C22G \\sim C22H: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
C240 \\sim C241 \\sim C242 \\sim C243 \\sim C244 \\sim C245 \\sim C246 \\sim
C247 \\sim C250 \\sim C251 \\sim C252 \\sim C253 \\sim C254 \\sim C255 \\sim
C256 \\sim C257: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
C270 \\sim C271 \\sim C272 \\sim C273 \\sim C274 \\sim C275 \\sim C276 \\sim
C277 \\sim C278 \\sim C279 \\sim C280 \\sim C281 \\sim C282 \\sim C283 \\sim
C284 \\sim C285 \\sim C286 \\sim C287 \\sim C288 \\sim C289 \\sim C290 \\sim
C291 \\sim C292 \\sim C293: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.01
C17 \\sim C18A \\sim C19A \\sim C20A \\sim C18B \\sim C19B \\sim C20B: within
1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
C38 \\sim C39A \\sim C40A \\sim C41A \\sim C39B \\sim C40B \\sim C41B: within
1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
C42 \\sim C43A \\sim C44A \\sim C45A \\sim C43B \\sim C44B \\sim C45B: within
1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
C109 \\sim C110 \\sim C111 \\sim C112 \\sim C11A \\sim C11B \\sim C11C: within
1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C18A) = Uanis(C18B)
Uanis(C19A) = Uanis(C19B)
Uanis(C20A) = Uanis(C20B)
Uanis(C39A) = Uanis(C39B)
Uanis(C40A) = Uanis(C40B)
Uanis(C41A) = Uanis(C41B)
Uanis(C45A) = Uanis(C45B)
Uanis(C43A) = Uanis(C43B)
Uanis(C44A) = Uanis(C44B)
Uanis(C110) = Uanis(C11A)
Uanis(C111) = Uanis(C11B)
4. Others
 Sof(C18B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C19B)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19A)=Sof(H19A)=Sof(H19B)=
 Sof(H19C)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
 Sof(C39B)=Sof(H39D)=Sof(H39E)=Sof(H39F)=Sof(C40B)=Sof(H40D)=Sof(H40E)=
 Sof(H40F)=Sof(C41B)=Sof(H41D)=Sof(H41E)=Sof(H41F)=1-FVAR(2)
 Sof(C39A)=Sof(H39A)=Sof(H39B)=Sof(H39C)=Sof(C40A)=Sof(H40A)=Sof(H40B)=
 Sof(H40C)=Sof(C41A)=Sof(H41A)=Sof(H41B)=Sof(H41C)=FVAR(2)
 Sof(C85B)=Sof(H85D)=Sof(H85E)=Sof(H85F)=Sof(C86B)=Sof(H86D)=Sof(H86E)=
 Sof(H86F)=Sof(C87B)=Sof(H87D)=Sof(H87E)=Sof(H87F)=1-FVAR(3)
 Sof(C85A)=Sof(H85A)=Sof(H85B)=Sof(H85C)=Sof(C86A)=Sof(H86A)=Sof(H86B)=
 Sof(H86C)=Sof(C87A)=Sof(H87A)=Sof(H87B)=Sof(H87C)=FVAR(3)
 Sof(C22A)=Sof(H22J)=Sof(C22B)=Sof(H22K)=Sof(C22C)=Sof(H22L)=Sof(C22D)=
 Sof(H22M)=Sof(C22E)=Sof(C22F)=Sof(C22G)=Sof(H22N)=Sof(H22O)=Sof(H22P)=
 Sof(C22H)=Sof(H22Q)=Sof(H22R)=Sof(H22S)=1-FVAR(4)
 Sof(C216)=Sof(H216)=Sof(C217)=Sof(H217)=Sof(C218)=Sof(H218)=Sof(C219)=
 Sof(H219)=Sof(C220)=Sof(C221)=Sof(C222)=Sof(H22D)=Sof(H22E)=Sof(H22F)=
 Sof(C223)=Sof(H22G)=Sof(H22H)=Sof(H22I)=FVAR(4)
 Sof(C250)=Sof(H250)=Sof(C251)=Sof(H251)=Sof(C252)=Sof(H252)=Sof(C253)=
 Sof(H253)=Sof(C254)=Sof(C255)=Sof(C256)=Sof(H25A)=Sof(H25B)=Sof(H25C)=
 Sof(C257)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(5)
 Sof(C240)=Sof(H240)=Sof(C241)=Sof(H241)=Sof(C242)=Sof(H242)=Sof(C243)=
 Sof(C244)=Sof(C245)=Sof(H245)=Sof(C246)=Sof(H24D)=Sof(H24E)=Sof(H24F)=
 Sof(C247)=Sof(H24G)=Sof(H24H)=Sof(H24I)=FVAR(5)
 Sof(C43A)=Sof(H43A)=Sof(H43B)=Sof(H43C)=Sof(C44A)=Sof(H44A)=Sof(H44B)=
 Sof(H44C)=Sof(C45A)=Sof(H45A)=Sof(H45B)=Sof(H45C)=1-FVAR(6)
 Sof(C43B)=Sof(H43D)=Sof(H43E)=Sof(H43F)=Sof(C44B)=Sof(H44D)=Sof(H44E)=
 Sof(H44F)=Sof(C45B)=Sof(H45D)=Sof(H45E)=Sof(H45F)=FVAR(6)
 Sof(C11A)=Sof(H11J)=Sof(H11K)=Sof(H11L)=Sof(C11B)=Sof(H11M)=Sof(H11N)=
 Sof(H11O)=Sof(C11C)=Sof(H11P)=Sof(H11Q)=Sof(H11R)=1-FVAR(7)
 Sof(C110)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C111)=Sof(H11D)=Sof(H11E)=
 Sof(H11F)=Sof(C112)=Sof(H11G)=Sof(H11H)=Sof(H11I)=FVAR(7)
 Fixed Sof: C270(0.5) C271(0.5) C272(0.5) H272(0.5) C273(0.5) H273(0.5)
 C274(0.5) H274(0.5) C275(0.5) H275(0.5) C276(0.5) H27A(0.5) H27B(0.5)
 H27C(0.5) C277(0.5) H27D(0.5) H27E(0.5) H27F(0.5) C278(0.5) C279(0.5)
 H279(0.5) C280(0.5) H280(0.5) C281(0.5) H281(0.5) C282(0.5) H282(0.5)
 C283(0.5) C284(0.5) H28A(0.5) H28B(0.5) H28C(0.5) C285(0.5) H28D(0.5)
 H28E(0.5) H28F(0.5) C286(0.5) C287(0.5) H287(0.5) C288(0.5) H288(0.5)
 C289(0.5) H289(0.5) C290(0.5) H290(0.5) C291(0.5) C292(0.5) H29A(0.5)
 H29B(0.5) H29C(0.5) C293(0.5) H29D(0.5) H29E(0.5) H29F(0.5)
5.a Free rotating group:
 C200(C201,C202,C203,C204,C205), C208(C209,C210,C211,C212,C213), C216(C217,
 C218,C219,C220,C221), C232(C233,C234,C235,C236,C237)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15),
 C27(H27), C29(H29), C30(H30), C33(H33), C34(H34), C36(H36), C47(H47), C48(H48),
  C51(H51), C53(H53), C54(H54), C56(H56), C60(H60), C61(H61), C62(H62),
 C63(H63), C66(H66), C67(H67), C68(H68), C69(H69), C73(H73), C75(H75), C76(H76),
  C79(H79), C80(H80), C82(H82), C94(H94), C96(H96), C97(H97), C100(H100),
 C101(H101), C103(H103), C114(H114), C115(H115), C118(H118), C122(H122),
 C127(H127), C128(H128), C129(H129), C130(H130), C133(H133), C134(H134),
 C135(H135), C136(H136), C200(H200), C201(H201), C202(H202), C203(H203),
 C208(H208), C209(H209), C210(H210), C211(H211), C216(H216), C217(H217),
 C218(H218), C219(H219), C22A(H22J), C22B(H22K), C22C(H22L), C22D(H22M),
 C224(H224), C225(H225), C226(H226), C227(H227), C232(H232), C233(H233),
 C234(H234), C235(H235), C240(H240), C241(H241), C242(H242), C245(H245),
 C250(H250), C251(H251), C252(H252), C253(H253), C272(H272), C273(H273),
 C274(H274), C275(H275), C279(H279), C280(H280), C281(H281), C282(H282),
 C287(H287), C288(H288), C289(H289), C290(H290)
5.c Fitted hexagon refined as free rotating group:
 C22A(C22B,C22C,C22D,C22E,C22F), C240(C241,C242,C243,C244,C245), C250(C251,
 C252,C253,C254,C255), C270(C271,C272,C273,C274,C275), C278(C279,C280,C281,C282,
 C283), C286(C287,C288,C289,C290,C291)
5.d Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C19A(H19A,H19B,H19C), C20A(H20A,H20B,H20C), C18B(H18D,
 H18E,H18F), C19B(H19D,H19E,H19F), C20B(H20D,H20E,H20F), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C39A(H39A,H39B,H39C), C40A(H40A,H40B,
 H40C), C41A(H41A,H41B,H41C), C39B(H39D,H39E,H39F), C40B(H40D,H40E,H40F),
 C41B(H41D,H41E,H41F), C43A(H43A,H43B,H43C), C44A(H44A,H44B,H44C), C45A(H45A,
 H45B,H45C), C43B(H43D,H43E,H43F), C44B(H44D,H44E,H44F), C45B(H45D,H45E,H45F),
 C85A(H85A,H85B,H85C), C86A(H86A,H86B,H86C), C87A(H87A,H87B,H87C), C85B(H85D,
 H85E,H85F), C86B(H86D,H86E,H86F), C87B(H87D,H87E,H87F), C89(H89A,H89B,H89C),
 C90(H90A,H90B,H90C), C91(H91A,H91B,H91C), C106(H10A,H10B,H10C), C107(H10D,H10E,
 H10F), C108(H10G,H10H,H10I), C110(H11A,H11B,H11C), C111(H11D,H11E,H11F),
 C112(H11G,H11H,H11I), C11A(H11J,H11K,H11L), C11B(H11M,H11N,H11O), C11C(H11P,
 H11Q,H11R), C206(H20G,H20H,H20I), C207(H20J,H20K,H20L), C214(H21A,H21B,H21C),
 C215(H21D,H21E,H21F), C222(H22D,H22E,H22F), C223(H22G,H22H,H22I), C22G(H22N,
 H22O,H22P), C22H(H22Q,H22R,H22S), C230(H23D,H23E,H23F), C231(H23G,H23H,H23I),
 C238(H23J,H23K,H23L), C239(H23M,H23N,H23O), C246(H24D,H24E,H24F), C247(H24G,
 H24H,H24I), C256(H25A,H25B,H25C), C257(H25D,H25E,H25F), C276(H27A,H27B,H27C),
 C277(H27D,H27E,H27F), C284(H28A,H28B,H28C), C285(H28D,H28E,H28F), C292(H29A,
 H29B,H29C), C293(H29D,H29E,H29F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_cod_database_fobs_code 1542340