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_1568271
_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         '2(C30 H33 N2 O4), C4 H10 O, 2(C16 H36 N)'
_chemical_formula_sum            'C96 H148 N6 O9'
_chemical_formula_weight         1530.20
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-14 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.2569(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4296(3)
_cell_length_b                   29.0372(5)
_cell_length_c                   18.0368(2)
_cell_measurement_reflns_used    34578
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      76.1370
_cell_measurement_theta_min      3.4570
_cell_volume                     9126.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -99.00 -31.00   0.50    8.00    --  -47.79 135.00  31.00  136
  2  \w    -99.00 -53.00   0.50    8.00    --  -47.79 135.00-148.00   92
  3  \w     35.00  60.00   0.50    8.00    --   47.79-135.00 146.00   50
  4  \w     67.00  99.00   0.50    8.00    --   47.79 135.00-148.00   64
  5  \w     70.00 119.00   0.50    8.00    --   47.79 135.00  31.00   98
  6  \w   -119.00 -32.00   0.50   31.00    -- -104.52 135.00-148.00  174
  7  \w   -119.00 -32.00   0.50   31.00    -- -104.52 135.00  31.00  174
  8  \w   -146.00-121.00   0.50   31.00    -- -104.52-135.00 146.00   50
  9  \w   -146.00-121.00   0.50   31.00    -- -104.52-135.00 -33.00   50
 10  \w     51.00  76.00   0.50   31.00    --  104.52-135.00 -33.00   50
 11  \w     84.00 123.00   0.50   31.00    --  104.52 135.00  31.00   78
 12  \w   -119.00 -82.00   0.50    8.00    --  -47.79 -57.00 -60.00   74
 13  \w    -23.00  39.00   0.50    8.00    --   47.79 -38.00 -90.00  124
 14  \w     82.00 119.00   0.50    8.00    --   47.79  57.00 -30.00   74
 15  \w     83.00 119.00   0.50    8.00    --   47.79  57.00  30.00   72
 16  \w   -172.00-100.00   0.50   31.00    -- -104.52 -77.00  60.00  144
 17  \w   -166.00-102.00   0.50   31.00    -- -104.52 -77.00   0.00  128
 18  \w   -110.00 -37.00   0.50   31.00    -- -104.52 125.00 -30.00  146
 19  \w   -177.00-100.00   0.50   31.00    -- -104.52 -77.00 -90.00  154
 20  \w     32.00 110.00   0.50   31.00    --  104.52 -77.00 -60.00  156
 21  \w     34.00  67.00   0.50   31.00    --  104.52 -61.00 -60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0004675000
_diffrn_orient_matrix_UB_12      0.0530468000
_diffrn_orient_matrix_UB_13      0.0023908000
_diffrn_orient_matrix_UB_21      -0.0006695000
_diffrn_orient_matrix_UB_22      -0.0014631000
_diffrn_orient_matrix_UB_23      0.0853482000
_diffrn_orient_matrix_UB_31      0.0884003000
_diffrn_orient_matrix_UB_32      -0.0003059000
_diffrn_orient_matrix_UB_33      0.0025323000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30978
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.479
_diffrn_reflns_theta_min         2.885
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_description       prism
_exptl_crystal_F_000             3352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.042
_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     1055
_refine_ls_number_reflns         30978
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+1.6018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                26841
_reflns_number_total             30978
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.8882\% 
around [-0.02 -0.00 1.00] (reciprocal) or [0.00 -0.00 1.00] (direct)
;
_cod_data_source_file            d2sc06376j2.cif
_cod_data_source_block           lar-1_auto
_cod_depositor_comments
'Adding full bibliography for 1568270--1568271.cif.'
_cod_database_code               1568271
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C96 H124 N8 O12'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5853(5)
 0.4147(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C75-C74
 1.52 with sigma of 0.02
 C92-C91
 1.52 with sigma of 0.02
 C74-C76
 2.5 with sigma of 0.03
 C90-C92
 2.5 with sigma of 0.03
 C76-C75
 1.52 with sigma of 0.02
 C92A-C90
 2.5 with sigma of 0.03
 C92A-C91
 1.52 with sigma of 0.02
 C75A-C74
 1.52 with sigma of 0.02
 C74-C76A
 2.5 with sigma of 0.03
 C91-C90
 1.52 with sigma of 0.02
 C76A-C75A
 1.52 with sigma of 0.02
 C91A-C92A
 1.52 with sigma of 0.02
 C92A-C91A
 1.52 with sigma of 0.02
 C91A-C90
 1.52 with sigma of 0.02
 C90-C92A
 2.55 with sigma of 0.03
 C73-C75A
 2.52 with sigma of 0.02
 C76A-C74
 2.52 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C96) \\sim Ueq, Uanis(C95) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(C93)
\\sim Ueq, Uanis(C94) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Others
 Sof(H109)=Sof(H110)=Sof(C92A)=Sof(H116)=Sof(H117)=Sof(H118)=Sof(C91A)=
 Sof(H124)=Sof(H125)=1-FVAR(1)
 Sof(H107)=Sof(H108)=Sof(C91)=Sof(H111)=Sof(H112)=Sof(C92)=Sof(H113)=Sof(H114)=
 Sof(H115)=FVAR(1)
 Sof(H71)=Sof(H72)=Sof(C76A)=Sof(H119)=Sof(H120)=Sof(H121)=Sof(C75A)=Sof(H122)=
 Sof(H123)=1-FVAR(2)
 Sof(H69)=Sof(H70)=Sof(C75)=Sof(H73)=Sof(H74)=Sof(C76)=Sof(H75)=Sof(H76)=
 Sof(H77)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C18(HE,HF), C21(HJ,HK), C48(H12,H13), C51(H17,H18), C93(H93A,H93B), C95(H95A,
 H95B), C61(H40,H41), C62(H42,H43), C63(H44,H45), C65(H49,H50), C66(H51,H52),
 C67(H53,H54), C69(H58,H59), C70(H60,H61), C71(H62,H63), C73(H67,H68), C74(H69,
 H70), C74(H71,H72), C75(H73,H74), C77(H78,H79), C78(H80,H81), C79(H82,H83),
 C81(H87,H88), C82(H89,H90), C83(H91,H92), C85(H96,H97), C86(H98,H99), C87(H100,
 H101), C89(H105,H106), C90(H107,H108), C90(H109,H110), C91(H111,H112),
 C75A(H122,H123), C91A(H124,H125)
6.b Aromatic/amide H refined with riding coordinates:
 C8(HA), C10(HB), C13(HC), C15(HD), C38(H8), C40(H9), C43(H10), C45(H11)
6.c Idealised Me refined as rotating group:
 C19(HG,HH,HI), C22(HL,HM,HN), C24(HO,HP,HQ), C25(HR,HS,HT), C26(HU,HV,HW),
 C28(HX,HY,HZ), C29(H1,H2,H3), C30(H4,H5,H6), C49(H14,H15,H16), C52(H19,H20,
 H21), C54(H22,H23,H24), C55(H25,H26,H27), C56(H28,H29,H30), C58(H31,H32,H33),
 C59(H34,H35,H36), C60(H37,H38,H39), C94(H94A,H94B,H94C), C96(H96A,H96B,H96C),
 C64(H46,H47,H48), C68(H55,H56,H57), C72(H64,H65,H66), C76(H75,H76,H77),
 C80(H84,H85,H86), C84(H93,H94,H95), C88(H102,H103,H104), C92(H113,H114,H115),
 C92A(H116,H117,H118), C76A(H119,H120,H121)
;
_shelx_res_checksum              9959
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.746
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2