A Route to a Cyclobutane-Linked Double-Looped System via a Helical Macrocycle
Klajn, Jan; Stawski, Wojciech; Chmielewski, Piotr Jan; Cybińska, Joanna; Pawlicki, Miłosz; Chemical Communications  (2019) –; doi:10.1039/C9CC01201J

data_7123184
_publ_section_title
;
 A Route to a Cyclobutane-Linked Double-Looped System via a Helical
 Macrocycle
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01201J
_journal_year                    2019
_chemical_formula_moiety         'C64 H62 N6'
_chemical_formula_sum            'C64 H62 N6'
_chemical_formula_weight         915.19
_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     dual
_audit_creation_date             2019-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-20 deposited with the CCDC.    2019-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.330(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   38.165(5)
_cell_length_b                   10.5770(13)
_cell_length_c                   12.7648(12)
_cell_measurement_reflns_used    1135
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.0463
_cell_measurement_theta_min      2.3296
_cell_volume                     5121.4(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -70.00   31.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6143   37.0000 -120.0000 101

  2 omega -100.00  -62.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6143  134.0000  -18.0000 38

  3 omega  -31.00   70.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6143  -51.0000  -35.0000 101

  4 omega   60.00  126.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -134.0000   18.0000 66

  5 omega  113.00  147.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 34

  6 omega  105.00  171.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 66

  7 omega   43.00   77.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 34

  8 omega   85.00  178.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 93

  9 omega   80.00  163.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000    0.0000 83

 10 omega   35.00  108.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 73

 11 omega   95.00  126.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -134.0000  -86.0000 31

 12 omega   76.00  150.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000  120.0000 74

 13 omega   96.00  130.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -92.0000   87.0000 34

 14 omega  102.00  128.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  133.0000  -93.0000 26

 15 omega  138.00  167.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  133.0000  -93.0000 29

 16 omega   41.00   67.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -92.0000   87.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0197196000
_diffrn_orient_matrix_UB_12      -0.0879240000
_diffrn_orient_matrix_UB_13      -0.0696598000
_diffrn_orient_matrix_UB_21      -0.0150263000
_diffrn_orient_matrix_UB_22      -0.1162508000
_diffrn_orient_matrix_UB_23      0.0526855000
_diffrn_orient_matrix_UB_31      -0.0321502000
_diffrn_orient_matrix_UB_32      0.0002300000
_diffrn_orient_matrix_UB_33      -0.0843067000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.1045
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12187
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        60.000
_diffrn_reflns_theta_max         64.989
_diffrn_reflns_theta_min         2.330
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       plate
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.2675
_exptl_crystal_size_mid          0.2377
_exptl_crystal_size_min          0.0735
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0892
_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^)+(0.1384P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2327
_refine_ls_wR_factor_ref         0.2674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2603
_reflns_number_total             4348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01201j9.cif
_cod_data_source_block           mjp_1_test
_cod_original_cell_volume        5121.3(10)
_cod_database_code               7123184
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C87)=Sof(H87A)=Sof(H87B)=Sof(H87C)=Sof(C88)=Sof(H88A)=Sof(H88B)=Sof(H88C)=
 Sof(C84)=Sof(H84A)=Sof(H84B)=Sof(H84C)=1-FVAR(1)
 Sof(C89)=Sof(H89A)=Sof(H89B)=Sof(H89C)=Sof(C86)=Sof(H86A)=Sof(H86B)=Sof(H86C)=
 Sof(C85)=Sof(H85A)=Sof(H85B)=Sof(H85C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N20(H20), C111(H111), C15(H15), C2(H2), C131(H131), C81(H81), C6(H6),
 C100(H100), C1(H1), C16(H16), C4(H4), C17(H17), C5(H5)
3.b Idealised Me refined as rotating group:
 C73(H73A,H73B,H73C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C), C87(H87A,H87B,
 H87C), C88(H88A,H88B,H88C), C84(H84A,H84B,H84C), C89(H89A,H89B,H89C), C86(H86A,
 H86B,H86C), C85(H85A,H85B,H85C)
;
_shelx_res_checksum              62795
_shelx_fab_checksum              34420
_olex2_submission_special_instructions 'No special instructions were received'