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_7123183
_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 O2'
_chemical_formula_sum            'C32 H31 N3 O2'
_chemical_formula_weight         489.60
_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             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                83.194(3)
_cell_angle_beta                 81.408(3)
_cell_angle_gamma                88.438(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4790(4)
_cell_length_b                   11.2211(4)
_cell_length_c                   12.2882(5)
_cell_measurement_reflns_used    4920
_cell_measurement_temperature    94.97(12)
_cell_measurement_theta_max      29.0550
_cell_measurement_theta_min      3.5440
_cell_volume                     1283.20(9)
_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      94.97(12)
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details
;
  1 omega  -86.00   13.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6889  -37.0000 -120.0000 99

  2 omega  -88.00   21.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6889  -77.0000   60.0000 109

  3 omega  -44.00   64.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6889   77.0000 -180.0000 108

  4 omega  -63.00   39.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5170  -57.0000  -60.0000 102

  5 omega  -25.00   51.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5170  -99.0000   30.0000 76

  6 omega -100.00  -71.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6889 -178.0000 -180.0000 29
;
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0212429000
_diffrn_orient_matrix_UB_12      0.0118692000
_diffrn_orient_matrix_UB_13      -0.0580475000
_diffrn_orient_matrix_UB_21      -0.0129598000
_diffrn_orient_matrix_UB_22      0.0621440000
_diffrn_orient_matrix_UB_23      0.0031288000
_diffrn_orient_matrix_UB_31      0.0714737000
_diffrn_orient_matrix_UB_32      0.0070844000
_diffrn_orient_matrix_UB_33      0.0086556000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19517
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.360
_diffrn_reflns_theta_min         2.826
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.979
_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    1.267
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.7625
_exptl_crystal_size_mid          0.2167
_exptl_crystal_size_min          0.1994
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         6223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0568P)^2^+0.4609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4916
_reflns_number_total             6223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01201j9.cif
_cod_data_source_block           mjp_carb_1
_cod_database_code               7123183
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.89
_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:
 N003(H003), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00N(H00N), C00O(H00O), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00W(H00W)
2.b Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00H), C00X(H00I,H00J,H00K), C00Y(H00L,H00M,H00P), C00Z(H00Q,
 H00V,H00X), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F)
;
_shelx_res_checksum              23286
_olex2_submission_special_instructions 'No special instructions were received'