Better big or strained? Deformations of shape persistent arylene butadiynylene macrocycles
Małecki, Marcin S.; Dopieralski, Przemysław; Gulia, Nurbey; Pigulski, Bartłomiej; Lis, Tadeusz; Szafert, Sławomir; New Journal of Chemistry 47 (2023) 6086–6094; doi:10.1039/D3NJ00155E

data_7062272
_publ_section_title
;
 Better big or strained? Deformations of shape persistent arylene
 butadiynylene macrocycles
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6086
_journal_page_last               6094
_journal_paper_doi               10.1039/D3NJ00155E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C108 H108 O12, C8 H18'
_chemical_formula_sum            'C116 H126 O12'
_chemical_formula_weight         1712.16
_chemical_name_systematic
'6-cyclo-[2,6-diethynyl-4-isopropylphenyl pivalate]'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-10-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-17 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.235(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.277(2)
_cell_length_b                   14.732(2)
_cell_length_c                   39.413(3)
_cell_measurement_reflns_used    2877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0770
_cell_measurement_theta_min      3.8840
_cell_volume                     10371(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2332
_diffrn_reflns_av_unetI/netI     0.2505
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            97597
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.680
_diffrn_reflns_theta_min         2.294
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77331
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_description       block
_exptl_crystal_F_000             3672
_exptl_crystal_recrystallization_method
'evaporation of solvent from mixture od DCM and isooctane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1181
_refine_ls_number_reflns         21303
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.3711
_refine_ls_R_factor_gt           0.1547
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3642
_refine_ls_wR_factor_ref         0.4870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5300
_reflns_number_total             21303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00155e1.cif
_cod_data_source_block           255okt
_cod_depositor_comments
'Adding full bibliography for 7062272--7062273.cif.'
_cod_database_code               7062272
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1X) \\sim Ueq, Uanis(C4X) \\sim Ueq, Uanis(C2X) \\sim Ueq, Uanis(C3X)
\\sim Ueq, Uanis(C5X) \\sim Ueq, Uanis(C6X) \\sim Ueq, Uanis(C7X) \\sim Ueq,
Uanis(C8X) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: H14M(0.5) H14N(0.5) H14O(0.5) H14P(0.5) H14Q(0.5) H14R(0.5)
4.a Everything fixed:
 H13M, H13N, H13O
4.b Ternary CH refined with riding coordinates:
 C16D(H16D), C16C(H16C), C16E(H16E), C16B(H16B), C15A(H15D), C16F(H16F),
 C4X(H4X)
4.c Secondary CH2 refined with riding coordinates:
 C3X(H3XA,H3XB)
4.d Me refined with riding coordinates:
 C1X(H1XA,H1XB,H1XC), C5X(H5XA,H5XB,H5XC), C6X(H6XA,H6XB,H6XC), C7X(H7XA,H7XB,
 H7XC), C8X(H8XA,H8XB,H8XC)
4.e Aromatic/amide H refined with riding coordinates:
 C8C(H8C), C10D(H10D), C10C(H10C), C8E(H8E), C8D(H8D), C8B(H8B), C10E(H10E),
 C10B(H10B), C10A(H10A), C8F(H8F), C8A(H8A), C10F(H10F)
4.f Disordered Me refined with riding coordinates:
 C14E(H14M,H14N,H14O,H14P,H14Q,H14R)
4.g Idealised Me refined as rotating group:
 C14C(H14A,H14B,H14C), C18C(H18A,H18B,H18C), C17E(H17A,H17B,H17C), C15C(H15A,
 H15B,H15C), C13C(H13A,H13B,H13C), C13B(H13D,H13E,H13F), C15B(H15E,H15F,H15G),
 C17C(H17D,H17E,H17F), C17D(H17G,H17H,H17I), C14B(H14D,H14E,H14F), C18F(H18D,
 H18E,H18F), C17A(H17J,H17K,H17L), C17B(H17M,H17N,H17O), C02X(H02A,H02B,H02C),
 C16A(H16A,H16G,H16H), C18B(H18G,H18H,H18I), C18E(H18J,H18K,H18L), C13F(H13G,
 H13H,H13I), C14A(H14G,H14H,H14I), C13A(H13J,H13K,H13L), C18D(H18M,H18N,H18O),
 C17F(H17P,H17Q,H17R), C14D(H14J,H14K,H14L), C15D(H15H,H15I,H15J), C13E(H13P,
 H13Q,H13R), C15E(H15K,H15L,H15M), C14F(H14S,H14T,H14U), C15F(H15N,H15O,H15P)
;
_shelx_res_checksum              44559
_olex2_submission_special_instructions 'No special instructions were received'