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_7123185
_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         '0.5(C H Cl3), C64 H62 N6'
_chemical_formula_sum            'C64.5 H62.78 Cl1.5 N6'
_chemical_formula_weight         975.15
_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             2019-03-20
_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                78.605(4)
_cell_angle_beta                 88.459(4)
_cell_angle_gamma                72.655(5)
_cell_formula_units_Z            4
_cell_length_a                   13.4459(9)
_cell_length_b                   22.2811(11)
_cell_length_c                   23.3879(9)
_cell_measurement_reflns_used    5008
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.6490
_cell_measurement_theta_min      3.0550
_cell_volume                     6552.5(6)
_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
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_unetI/netI     0.2017
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            48897
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.863
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.84571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrysAlisPro
_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    0.988
_exptl_crystal_description       block
_exptl_crystal_F_000             2069
_exptl_crystal_size_max          0.706
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1380
_refine_ls_number_reflns         25611
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.2309
_refine_ls_R_factor_gt           0.0992
_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^)+(0.1010P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2262
_refine_ls_wR_factor_ref         0.2788
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7926
_reflns_number_total             25611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01201j9.cif
_cod_data_source_block           mjp960
_cod_original_formula_sum        'C64.50 H62.78 Cl1.50 N6'
_cod_database_code               7123185
_shelx_shelxl_version_number     2018/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C62-C65 \\sim C65-C63
 with sigma of 0.02
3. Others
 Sof(C03M)=Sof(H03M)=Sof(C03O)=Sof(H03O)=Sof(C03P)=Sof(H03P)=1-FVAR(1)
 Sof(H03B)=Sof(C3AA)=Sof(H3AA)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C2AA)=Sof(H2AA)=
 FVAR(1)
 Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(H72C)=Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(H73C)=
 Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(H74C)=1-FVAR(2)
 Sof(C77)=Sof(H77A)=Sof(H77B)=Sof(H77C)=Sof(C76)=Sof(H76A)=Sof(H76B)=Sof(H76C)=
 Sof(C78)=Sof(H78A)=Sof(H78B)=Sof(H78C)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C00N(H00N), C00O(H00O), C01A(H01A), C01C(H01C), C01Y(H01Y), C02F(H02F),
 C02Q(H02Q), C032(H032), C03B(H03B), C03S(H03S)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 N006(H006), N008(H008), N009(H009), N00B(H00B), C012(H012), C014(H014),
 C01B(H01B), C01D(H01D), C01F(H01F), C01K(H01K), C01L(H01L), C01R(H01R),
 C01T(H01T), C01U(H01U), C01V(H01V), C01W(H01W), C020(H020), C022(H022),
 C023(H023), C025(H025), C02A(H02A), C02B(H02B), C02C(H02C), C02E(H02E),
 C02G(H02G), C02H(H02H), C02I(H02I), C02J(H02J), C02L(H02L), C02P(H02P),
 C02S(H02S), C02T(H02T), C02W(H02W), C02X(H02X), C02Y(H02Y), C031(H031),
 C035(H035), C037(H037), C03A(H03A), C03H(H03H), C03M(H03M), C03O(H03O),
 C03P(H03P), C03Q(H03Q), C3AA(H3AA), C2AA(H2AA)
4.d Idealised Me refined as rotating group:
 C71(H71A,H71B,H71C), C70(H70A,H70B,H70C), C60(H60A,H60B,H60C), C58(H58A,H58B,
 H58C), C57(H57A,H57B,H57C), C56(H56A,H56B,H56C), C69(H69A,H69B,H69C), C59(H59A,
 H59B,H59C), C63(H63A,H63B,H63C), C66(H66A,H66B,H66C), C61(H61A,H61B,H61C),
 C62(H62A,H62B,H62C), C67(H67A,H67B,H67C), C55(H55A,H55B,H55C), C53(H53A,H53B,
 H53C), C52(H52A,H52B,H52C), C68(H68A,H68B,H68C), C51(H51A,H51B,H51C), C54(H54A,
 H54B,H54C), C77(H77A,H77B,H77C), C50(H50A,H50B,H50C), C76(H76A,H76B,H76C),
 C78(H78A,H78B,H78C), C65(H65A,H65B,H65C), C72(H72A,H72B,H72C), C73(H73A,H73B,
 H73C), C74(H74A,H74B,H74C)
;
_shelx_res_checksum              46729
_shelx_fab_checksum              39345
_olex2_submission_special_instructions 'No special instructions were received'