N-Confused strapped calix[4]pyrrole: the missing member of calix[4]pyrrole chemistry.
Roy, Anik; Halder, Dibakar; Patra, Ashoke Kumar; Frontera, Antonio; Saha, Indrajit; Organic & biomolecular chemistry 22 (2024) 8249–8254; doi:10.1039/d4ob00799a

data_7160031
_publ_section_title
;
 N-Confused strapped calix[4]pyrrole: the missing member of
 calix[4]pyrrole chemistry.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8249
_journal_page_last               8254
_journal_paper_doi               10.1039/d4ob00799a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C54 H65 N5 O4'
_chemical_formula_sum            'C54 H65 N5 O4'
_chemical_formula_weight         848.11
_chemical_name_systematic        2
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-12-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-03-15 deposited with the CCDC.	2024-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 124.788(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.9398(15)
_cell_length_b                   11.4985(4)
_cell_length_c                   25.6469(11)
_cell_measurement_reflns_used    6972
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      20.68
_cell_measurement_theta_min      2.28
_cell_volume                     9430.9(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2085
_diffrn_reflns_av_unetI/netI     0.1468
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            91860
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.146
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0881 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.9414.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       needle
_exptl_crystal_F_000             3648
_exptl_crystal_preparation       'Layering technique'
_exptl_crystal_recrystallization_method 'Layering technique'
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         10777
_refine_ls_number_restraints     492
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.2529
_refine_ls_R_factor_gt           0.1171
_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^)+(0.1475P)^2^+18.1130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2835
_refine_ls_wR_factor_ref         0.3499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4203
_reflns_number_total             10777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00799a2.cif
_cod_data_source_block           momoc_c
_cod_depositor_comments
'Adding full bibliography for 7160030--7160031.cif.'
_cod_database_code               7160031
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C54-C53
 1.236 with sigma of 0.02
 O3-C55 = O2-C54
 1.493 with sigma of 0.02
 C18-C20 \\sim C18-C20A
 with sigma of 0.02
 C18-C21 \\sim C18-C21A
 with sigma of 0.02
 C18-C19 \\sim C18-C19A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C53 \\sim C2 \\sim C18 \\sim C55 \\sim C40 \\sim O3 \\sim C30 \\sim N5 \\sim O1
\\sim C17 \\sim C29 \\sim N3 \\sim C49 \\sim C43 \\sim C19 \\sim C33 \\sim C24
\\sim C26 \\sim C34 \\sim C27 \\sim C20 \\sim N1 \\sim C6 \\sim C16 \\sim C47
\\sim O4 \\sim C37 \\sim C22 \\sim C7 \\sim N2 \\sim C41 \\sim C12 \\sim C35
\\sim N4 \\sim C5 \\sim C15 \\sim C44 \\sim C31 \\sim C23 \\sim C10 \\sim C21
\\sim C9 \\sim C8 \\sim C48 \\sim C52 \\sim C14 \\sim C42 \\sim C28 \\sim C38
\\sim C11 \\sim C36 \\sim C50 \\sim C46 \\sim O5 \\sim C13 \\sim C25 \\sim C4
\\sim C51 \\sim C39 \\sim C32 \\sim C3 \\sim C45 \\sim C1: within 2A with sigma
of 0.002 and sigma for terminal atoms of 0.004 within 2A
C54 \\sim O2 \\sim C55 \\sim O3: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004 within 2A
C18 \\sim C20 \\sim C19 \\sim C21 \\sim C20A \\sim C19A \\sim C21A: within 2A
with sigma of 0.002 and sigma for terminal atoms of 0.004 within 2A
4. Others
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
 Fixed Sof: O3(0.66) H53A(0.66) H53B(0.66) H53C(0.34) H53D(0.34) C55(0.66)
 H55A(0.66) H55B(0.66) C54(0.34) H54A(0.34) H54B(0.34) O2(0.34)
5.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C23(H23A,H23B), C52(H52A,H52B), C24(H24A,H24B), C53(H53A,
 H53B), C53(H53C,H53D), C55(H55A,H55B), C54(H54A,H54B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C17(H17), C15(H15), C50(H50), N5(H5), C36(H36), C44(H44), C42(H42),
 C37(H37), C30(H30), C29(H29), C49(H49), C3(H3A)
5.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C33(H33A,H33B,H33C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C34(H34A,H34B,H34C), C40(H40C,H40A,H40B), C47(H47A,
 H47B,H47C), C46(H46A,H46B,H46C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C6(H6A,H6B,
 H6C), C20A(H20D,H20E,H20F), C19A(H19D,H19E,H19F), C21A(H21D,H21E,H21F)
;
_shelx_res_checksum              12134
_olex2_submission_special_instructions 'No special instructions were received'