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_7123179
_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         'C32 H31 N3'
_chemical_formula_sum            'C32 H31 N3'
_chemical_formula_weight         457.60
_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                 90.546(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.079(2)
_cell_length_b                   13.5974(16)
_cell_length_c                   11.5541(10)
_cell_measurement_reflns_used    562
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3670
_cell_measurement_theta_min      2.7570
_cell_volume                     2526.0(5)
_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      293(2)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.868
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details
;
  1 omega  -21.00    5.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6143   28.0000 -140.0000 26

  2 omega  -69.00  -24.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6143   28.0000 -140.0000 45

  3 omega  -98.00  -31.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6143  125.0000 -120.0000 67

  4 omega -115.00  -76.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6143 -125.0000   60.0000 39

  5 omega  102.00  160.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 58

  6 omega   38.00   98.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -127.0000   86.0000 60

  7 omega   48.00   77.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 29

  8 omega   95.00  175.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 80

  9 omega   37.00   88.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   91.0000 51

 10 omega   36.00   56.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -28.0000   57.0000 20
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0526311000
_diffrn_orient_matrix_UB_12      0.0306428000
_diffrn_orient_matrix_UB_13      -0.1048137000
_diffrn_orient_matrix_UB_21      -0.0798820000
_diffrn_orient_matrix_UB_22      0.0263003000
_diffrn_orient_matrix_UB_23      -0.0679062000
_diffrn_orient_matrix_UB_31      0.0045009000
_diffrn_orient_matrix_UB_32      0.1057871000
_diffrn_orient_matrix_UB_33      0.0471399000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.1066
_diffrn_reflns_Laue_measured_fraction_full 0.868
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5905
_diffrn_reflns_point_group_measured_fraction_full 0.868
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        64.995
_diffrn_reflns_theta_max         64.995
_diffrn_reflns_theta_min         2.748
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37806
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.203
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.2768
_exptl_crystal_size_min          0.0638
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0933
_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^)+(0.1451P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2415
_refine_ls_wR_factor_ref         0.2844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2078
_reflns_number_total             3719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01201j9.cif
_cod_data_source_block           jk262
_cod_database_code               7123179
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C32 H31 N3'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.806
_reflns_odcompleteness_completeness 85.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H20(0.048) H131(0.051) H15(0.049) H81(0.052) H17(0.054) H6(0.05)
 H16(0.053) H4(0.054) H2(0.057) H5(0.052) H111(0.053) H1(0.054) H101(0.055)
 H83A(0.099) H83B(0.099) H83C(0.099) H85A(0.103) H85B(0.103) H85C(0.103)
 H72A(0.108) H72B(0.108) H72C(0.108) H84A(0.102) H84B(0.102) H84C(0.102)
 H70A(0.107) H70B(0.107) H70C(0.107) H71A(0.115) H71B(0.115) H71C(0.115)
 Fixed X: H20(0.425464) H131(0.339496) H15(0.47691) H81(0.272667)
 H17(0.691929) H6(0.40188) H16(0.620272) H4(0.641055) H2(0.679059) H5(0.540209)
 H111(0.139572) H1(0.695467) H101(0.115752) H83A(0.154145) H83B(0.059575)
 H83C(0.087889) H85A(0.137098) H85B(0.08388) H85C(0.179397) H72A(0.223307)
 H72B(0.174293) H72C(0.262618) H84A(0.015949) H84B(-0.014447) H84C(0.032286)
 H70A(0.063771) H70B(0.058351) H70C(0.107659) H71A(0.196402) H71B(0.115704)
 H71C(0.114028)
 Fixed Y: H20(0.411956) H131(0.622248) H15(0.622745) H81(0.275245)
 H17(0.54417) H6(0.230839) H16(0.625059) H4(0.29475) H2(0.38333) H5(0.217713)
 H111(0.537115) H1(0.455935) H101(0.417707) H83A(0.170621) H83B(0.181207)
 H83C(0.177856) H85A(0.417561) H85B(0.330266) H85C(0.316248) H72A(0.609337)
 H72B(0.708965) H72C(0.704368) H84A(0.338766) H84B(0.335078) H84C(0.428269)
 H70A(0.574213) H70B(0.623092) H70C(0.524618) H71A(0.776482) H71B(0.781276)
 H71C(0.727418)
 Fixed Z: H20(0.648007) H131(0.949273) H15(0.970763) H81(0.334724)
 H17(0.827732) H6(0.294448) H16(0.970313) H4(0.359754) H2(0.514956)
 H5(0.245115) H111(0.762045) H1(0.662758) H101(0.546093) H83A(0.323047)
 H83B(0.291196) H83C(0.421346) H85A(0.220572) H85B(0.171172) H85C(0.19413)
 H72A(1.107692) H72B(1.110322) H72C(1.054276) H84A(0.458371) H84B(0.329121)
 H84C(0.376138) H70A(0.903057) H70B(1.025638) H70C(1.009814) H71A(0.867605)
 H71B(0.94248) H71C(0.822514)
;
_shelx_res_checksum              11911
_olex2_submission_special_instructions 'No special instructions were received'