De novo fabrication of higher arene ring incorporated contorted calix[2]phyrin(2.2.1.1.1) and its F− bound complex
Pradhan, Sourav Ranjan; Prasad, Chetan Kumar; Das, Mainak; Srinivasan, A.; Dalton Transactions 53 (2024) 15258–15263; doi:10.1039/D4DT01903B

data_7717153
_publ_section_title
;
 De novo fabrication of higher arene ring incorporated contorted
 calix[2]phyrin(2.2.1.1.1) and its F&#x2212; bound complex
;
_journal_issue                   36
_journal_name_full               'Dalton Transactions'
_journal_page_first              15258
_journal_page_last               15263
_journal_paper_doi               10.1039/D4DT01903B
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'F, H2 O, C45 H40 N2, C16 H36 N'
_chemical_formula_sum            'C61 H78 F N3 O'
_chemical_formula_weight         888.26
_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             2024-03-30
_audit_creation_method
;
Olex2 1.5-ac5-021
(compiled 2022.02.15 svn.rf212a0ae for Rigaku Oxford Diffraction, GUI svn.r6439)
;
_audit_update_record
;
2024-04-22 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.367(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0491(11)
_cell_length_b                   21.1710(12)
_cell_length_c                   18.6212(16)
_cell_measurement_reflns_used    7690
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.8800
_cell_measurement_theta_min      3.8900
_cell_volume                     5314.1(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.959
_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   -105.00 -35.00   0.50    7.00    --  -38.50 -37.00 -43.00  140
  2  \w    -42.00  28.00   0.50    7.00    --  -38.50  37.00 112.00  140
  3  \w     45.00 115.00   0.50    7.00    --   48.06  37.00 112.00  140
  4  \w    -18.00  51.00   0.50    7.00    --   48.06 -37.00 -43.00  138
  5  \w    100.00 169.00   0.50   28.00    --  102.63  37.00 112.00  138
  6  \w     36.00 106.00   0.50   28.00    --  102.63 -37.00 -43.00  140
  7  \w    -50.00  24.00   0.50    7.00    --  -38.50  57.00-180.00  148
  8  \w    -50.00  24.00   0.50    7.00    --  -38.50  57.00-120.00  148
  9  \w   -104.00 -46.00   0.50    7.00    --  -38.50 -19.00  60.00  116
 10  \w     48.00 111.00   0.50    7.00    --   48.06  37.00-150.00  126
 11  \w     43.00 105.00   0.50   28.00    --  102.63 -45.00  30.00  124
 12  \w     99.00 163.00   0.50   28.00    --  102.63  45.00-180.00  128
 13  \w     96.00 152.00   0.50   28.00    --  102.63  15.00-180.00  112
 14  \w    102.00 155.00   0.50   28.00    --  102.63  30.00   0.00  106
 15  \w     74.00 118.00   0.50   28.00    --  102.63-125.00-150.00   88
 16  \w     40.00 114.00   0.50   28.00    --  102.63 -61.00-180.00  148
 17  \w     99.00 166.00   0.50   28.00    --  102.63  45.00-120.00  134
 18  \w     40.00 107.00   0.50   28.00    --  102.63 -45.00-150.00  134
 19  \w     47.00 108.00   0.50   28.00    --  102.63 -61.00  30.00  122
 20  \w    114.00 146.00   0.50   28.00    --  102.63  45.00-150.00   64
 21  \w     37.00  78.00   0.50   28.00    --  102.63 -30.00 150.00   82
 22  \w     41.00 115.00   0.50   28.00    --  102.63-125.00 -30.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0583574000
_diffrn_orient_matrix_UB_12      -0.0283779000
_diffrn_orient_matrix_UB_13      0.0758374000
_diffrn_orient_matrix_UB_21      0.0837222000
_diffrn_orient_matrix_UB_22      -0.0196389000
_diffrn_orient_matrix_UB_23      -0.0338871000
_diffrn_orient_matrix_UB_31      0.0514240000
_diffrn_orient_matrix_UB_32      0.0640872000
_diffrn_orient_matrix_UB_33      0.0230461000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35027
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.780
_diffrn_reflns_theta_min         3.888
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       block
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.680
_refine_diff_density_min         -1.239
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         10615
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1621
_refine_ls_R_factor_gt           0.1199
_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^)+(0.0418P)^2^+22.2663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2604
_refine_ls_wR_factor_ref         0.2854
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7027
_reflns_number_total             10615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01903b2.cif
_cod_data_source_block           assncalpyrf
_cod_database_code               7717153
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C100 H100 N100 F100 '
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.904
_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, All O(H,H) groups
2. Restrained distances
 C59-C61
 2.5 with sigma of 0.02
 C64-C61
 3 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C61) = Uanis(C58) = Uanis(C59) = Uanis(C64) = Uanis(C60) = Uanis(C62) =
Uanis(C63)
4. Others
 Fixed Sof: H58C(0.5) H58D(0.5) H58A(0.5) H58B(0.5) C64(0.5) H64A(0.5)
 H64B(0.5) C59(0.5) H59A(0.5) H59B(0.5) C63(0.5) H63A(0.5) H63B(0.5) C60(0.5)
 H60A(0.5) H60B(0.5) C62(0.5) H62A(0.5) H62B(0.5) H62C(0.5) C61(0.5) H61A(0.5)
 H61B(0.5) H61C(0.5)
5.a Free rotating group:
 O1(H1A,H1B)
5.b Ternary CH refined with riding coordinates:
 C18(H18), C8(H8)
5.c Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C53(H53A,H53B), C49(H49A,H49B), C57(H57A,H57B), C48(H48A,
 H48B), C58(H58C,H58D), C58(H58A,H58B), C37(H37A,H37B), C55(H55A,H55B),
 C56(H56A,H56B), C47(H47A,H47B), C52(H52A,H52B), C51(H51A,H51B), C64(H64A,H64B),
  C59(H59A,H59B), C63(H63A,H63B), C60(H60A,H60B)
5.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C27(H27), C26(H26), C29(H29), C28(H28), C20(H20), C23(H23),
 C22(H22), C4(H4), C3(H3), C10(H10), C6(H6), C16(H16), C21(H21), C45(H45),
 C41(H41), C5(H5), C11(H11), C43(H43), C15(H15), C42(H42), C44(H44), C35(H35),
 C31(H31), C34(H34), C33(H33), C32(H32)
5.e Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C54(H54A,H54B,H54C), C46(H46A,H46B,H46C), C36(H36A,H36B,
 H36C), C50(H50A,H50B,H50C), C62(H62A,H62B,H62C), C61(H61A,H61B,H61C)
;
_shelx_res_checksum              35008
_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 2.847
_oxdiff_exptl_absorpt_empirical_full_min 0.352