A shape-persistent alleno-acetylenic macrocycle with a modifiable periphery: synthesis, chiroptical properties and H-bond-driven self-assembly into a homochiral columnar structure
Manolis D. Tzirakis; Nicolas Marion; W. Bernd Schweizer; Francois Diederich; Chem.Commun. 49 (2013) 7605–; doi:10.1039/c3cc44101f

data_7109646
_publ_section_title
;
 A shape-persistent alleno-acetylenic macrocycle with a modifiable
 periphery: synthesis, chiroptical properties and H-bond-driven
 self-assembly into a homochiral columnar structure
;
_journal_name_full               Chem.Commun.
_journal_page_first              7605
_journal_paper_doi               10.1039/c3cc44101f
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C H2 Cl2, C100 H88 O8, 2(C3.5 H8)'
_chemical_formula_sum            'C108 H106 Cl2 O8'
_chemical_formula_weight         1602.83
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-04
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr  9 2013 14:10:59, GUI svn.r4458)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.190(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   27.930(3)
_cell_length_b                   8.9770(9)
_cell_length_c                   20.9383(15)
_cell_measurement_reflns_used    5471
_cell_measurement_temperature    100
_cell_measurement_theta_max      49.48
_cell_measurement_theta_min      3.33
_cell_volume                     4894.9(8)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9424
_diffrn_reflns_theta_full        50.08
_diffrn_reflns_theta_max         50.08
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_T_max  0.7499
_exptl_absorpt_correction_T_min  0.5764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0957 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.7686.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
'Flack H D (1983), Acta Cryst. A39, 876-881'
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.408
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         2706
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.410
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.1055
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2781
_refine_ls_wR_factor_ref         0.2893
_reflns_number_gt                2392
_reflns_number_total             2706
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44101f.txt
_cod_data_source_block           cu_d050412_0m
_cod_original_cell_volume        4894.8(8)
_cod_database_code               7109646
_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, All O(H) groups
2. Restrained distances
 C61-C60 = C62-C61 = C63-C62
 1.53 with sigma of 0.02
 C57-C56
 1.53 with sigma of 0.02
 C57-C58
 1.53 with sigma of 0.02
 C58-C59
 1.53 with sigma of 0.02
 Cl1-C55 = Cl2-C55
 1.77 with sigma of 0.02
 C60-C62 = C61-C63
 2.45 with sigma of 0.04
 C56-C58
 2.45 with sigma of 0.04
 C57-C59
 2.45 with sigma of 0.04
 Cl1-Cl2
 2.93 with sigma of 0.04
3. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) C55(0.5) H55A(0.5) H55B(0.5) C56(0.5) H56A(0.5)
 H56B(0.5) H56C(0.5) C57(0.5) H57A(0.5) H57B(0.5) C58(0.5) H58A(0.5) H58B(0.5)
 C59(0.25) H59A(0.25) H59B(0.25) C60(0.5) H60A(0.5) H60B(0.5) H60C(0.5)
 C61(0.5) H61A(0.5) H61B(0.5) C62(0.5) H62A(0.5) H62B(0.5) C63(0.25) H63A(0.25)
 H63B(0.25)
 Fixed X: C59(0)
 Fixed Z: C59(0)
4.a Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C61(H61A,
 H61B), C62(H62A,H62B), C63(H63A,H63B)
4.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C22(H22), C23(H23), C29(H29), C30(H30), C32(H32),
 C33(H33), C39(H39), C40(H40), C42(H42), C43(H43), C49(H49), C50(H50), C52(H52),
  C53(H53)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C), C56(H56A,H56B,H56C), C60(H60A,H60B,H60C)
4.d Idealised tetrahedral OH refined as rotating group:
 O24(H24), O34(H34), O44(H44), O54(H54)
;