Synthesis of ExnBox Cyclophanes
Jonathan C. Barnes; Michal Juríček; Nicolaas A. Vermeulen; Edward J. Dale; J. Fraser Stoddart; Journal of Organic Chemistry 78 (2013) 11962–11969; doi:10.1021/jo401993n

data_4028816
_publ_section_title
;
 Synthesis of ExnBox Cyclophanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11962
_journal_page_last               11969
_journal_paper_doi               10.1021/jo401993n
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C84 H80 N4, 4(F6 P), C2 H3 N'
_chemical_formula_sum            'C86 H83 F24 N5 P4'
_chemical_formula_weight         1766.45
_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     dual
_audit_creation_date             2013-05-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                78.589(9)
_cell_angle_beta                 89.279(9)
_cell_angle_gamma                84.548(11)
_cell_formula_units_Z            1
_cell_length_a                   7.0565(9)
_cell_length_b                   11.3492(17)
_cell_length_c                   26.647(3)
_cell_measurement_reflns_used    944
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      50.38
_cell_measurement_theta_min      3.38
_cell_volume                     2082.4(5)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXD, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.526
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_Laue_measured_fraction_full 0.526
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3991
_diffrn_reflns_point_group_measured_fraction_full 0.526
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         50.536
_diffrn_reflns_theta_min         3.384
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.735
_exptl_absorpt_correction_T_max  0.749954
_exptl_absorpt_correction_T_min  0.516682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0952 before and 0.0421 after correction.
  
For component 2:
 wR2(int) was 0.1296 before and 0.0402 after correction.
 The Ratio of minimum to maximum transmission is 0.69.
 
Final HKLF 4 output contains 9365 reflections, Rint = 0.0727
 (3767 with I > 3sig(I), Rint = 0.0628)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       needle
_exptl_crystal_F_000             910
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         3991
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0821
_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^)+(0.1420P)^2^+0.8313P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2110
_refine_ls_wR_factor_ref         0.2358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2626
_reflns_number_total             3991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo401993n_si_002.cif
_cod_data_source_block           n2687
_cod_database_code               4028816
_cod_database_fobs_code          4028816
_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. Rigid bond restraints
 C2S, N1S, C1S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2S \\sim N1S \\sim C1S: within 1.7A with sigma of 0.04 and sigma for terminal
 atoms of 0.08
4. others
 Fixed Sof: N1S(0.5) C1S(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5) H2SC(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C42(H42A,H42B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C11(H11), C16(H16), C19(H19),
 C24(H24), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34), C37(H37), 
 C38(H38),
  C40(H40), C41(H41)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C2S(H2SA,H2SB,H2SC)
;
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.760
_shelxl_version_number           2012-9