Cyclo[2]carbazole[2]pyrrole: a preorganized calix[4]pyrrole analogue.
Lee, Areum; Yang, Ju Ho; Oh, Ju Hyun; Hay, Benjamin P.; Lee, Kyounghoon; Lynch, Vincent M.; Sessler, Jonathan L.; Kim, Sung Kuk; Chemical science 14 (2023) 1218–1226; doi:10.1039/d2sc06376j

data_1568270
_publ_section_title
;
 Cyclo[2]carbazole[2]pyrrole: a preorganized calix[4]pyrrole analogue.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              1218
_journal_page_last               1226
_journal_paper_doi               10.1039/d2sc06376j
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C60 H68 N4 O8'
_chemical_formula_sum            'C60 H68 N4 O8'
_chemical_formula_weight         973.18
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-14 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9159(3)
_cell_length_b                   21.2730(4)
_cell_length_c                   18.6760(3)
_cell_measurement_reflns_used    9703
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.22
_cell_volume                     6043.25(19)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            169247
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_min         1.489
_diffrn_source_current           18.0
_diffrn_source_power             0.9
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7114
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0850 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.9540.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_description       Block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.289
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     729
_refine_ls_number_reflns         14976
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0631
_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^)+(0.0845P)^2^+3.3588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10470
_reflns_number_total             14976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06376j2.cif
_cod_data_source_block           lar-mc1
_cod_depositor_comments
'Adding full bibliography for 1568270--1568271.cif.'
_cod_database_code               1568270
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.971
_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
 C37-C38 = C37-C39 = C37-C40 = C37-C38A = C37-C39A = C37-C40A
 1.54 with sigma of 0.01
 C7-C8 = C7-C9 = C7-C10 = C7-C8A = C7-C9A = C7-C10A
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(C30) = Uanis(C29A) = Uanis(C30A)
Uanis(C48) = Uanis(C48A) = Uanis(C49) = Uanis(C49A) = Uanis(C50) = Uanis(C50A)
Uanis(C59) = Uanis(C60) = Uanis(C60A)
4. Others
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=
 Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
 Sof(C38A)=Sof(H38D)=Sof(H38E)=Sof(H38F)=Sof(C39A)=Sof(H39D)=Sof(H39E)=
 Sof(H39F)=Sof(C40A)=Sof(H40D)=Sof(H40E)=Sof(H40F)=1-FVAR(2)
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=
 Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(2)
 Sof(C29A)=Sof(H29C)=Sof(H29D)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(3)
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(3)
 Sof(C48A)=Sof(H48D)=Sof(H48E)=Sof(H48F)=Sof(C49A)=Sof(H49D)=Sof(H49E)=
 Sof(H49F)=Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=1-FVAR(4)
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=
 Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=FVAR(4)
 Sof(H59C)=Sof(H59D)=Sof(C60A)=Sof(H60D)=Sof(H60E)=Sof(H60F)=1-FVAR(5)
 Sof(H59A)=Sof(H59B)=Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(H60C)=FVAR(5)
5.a Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B), C26(H26A,H26B), C59(H59A,H59B), C59(H59C,H59D), C29(H29A,
 H29B), C29A(H29C,H29D)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), N4(H4), N3(H3), C3(H3A), C1(H1A), C14(H14), C32(H32),
 C16(H16), C44(H44), C46(H46), C34(H34)
5.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C57(H57A,H57B,
 H57C), C19(H19A,H19B,H19C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,
 H10C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C30(H30A,
 H30B,H30C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C),
 C60(H60A,H60B,H60C), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C10A(H10D,H10E,
 H10F), C38A(H38D,H38E,H38F), C39A(H39D,H39E,H39F), C40A(H40D,H40E,H40F),
 C30A(H30D,H30E,H30F), C48A(H48D,H48E,H48F), C49A(H49D,H49E,H49F), C50A(H50D,
 H50E,H50F), C60A(H60D,H60E,H60F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              73889
_shelx_fab_checksum              28476
_olex2_submission_special_instructions 'No special instructions were received'