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_7123182
_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         'C34 H33 N O2'
_chemical_formula_sum            'C34 H33 N O2'
_chemical_formula_weight         487.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 108.033(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4682(13)
_cell_length_b                   5.7331(2)
_cell_length_c                   26.1392(18)
_cell_measurement_reflns_used    1745
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.7950
_cell_measurement_theta_min      2.8098
_cell_volume                     2631.7(3)
_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 10.3456
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_details
;
  1 omega  -61.00  -35.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       15.6585 -178.0000  120.0000 26

  2 omega  -35.00   71.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       15.6585  -19.0000   60.0000 106

  3 omega  -24.00   49.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       15.6585  -77.0000    0.0000 73
;
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0128670000
_diffrn_orient_matrix_UB_12      -0.0169834000
_diffrn_orient_matrix_UB_13      0.0282799000
_diffrn_orient_matrix_UB_21      -0.0261010000
_diffrn_orient_matrix_UB_22      0.0856229000
_diffrn_orient_matrix_UB_23      0.0029843000
_diffrn_orient_matrix_UB_31      -0.0280074000
_diffrn_orient_matrix_UB_32      -0.0876244000
_diffrn_orient_matrix_UB_33      -0.0025518000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.1225
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11588
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.795
_diffrn_reflns_theta_min         3.121
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.997
_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    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.2619
_exptl_crystal_size_mid          0.0957
_exptl_crystal_size_min          0.0577
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0706
_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^)+(0.0393P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3329
_reflns_number_total             5987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01201j9.cif
_cod_data_source_block           mjp_test_1
_cod_database_code               7123182
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 N21(H21), C111(H111), C131(H131), C81(H81), C3(H3), C5(H5), C15(H15), C6(H6),
 C101(H101), C19(H19), C7(H7), C18(H18), C1(H1), C17(H17), C20(H20)
2.b Idealised Me refined as rotating group:
 C84(H84A,H84B,H84C), C72(H72A,H72B,H72C), C86(H86A,H86B,H86C), C73(H73A,H73B,
 H73C), C85(H85A,H85B,H85C), C71(H71A,H71B,H71C)
;
_shelx_res_checksum              38318
_olex2_submission_special_instructions 'No special instructions were received'