One-pot synthesis of porphyrin-based [5]rotaxanes.
Martinez-Bulit, Pablo; Wilson, Benjamin H.; Loeb, Stephen J.; Organic & biomolecular chemistry 18 (2020) 4395–4400; doi:10.1039/d0ob00906g

data_7157517
_publ_section_title
;
 One-pot synthesis of porphyrin-based [5]rotaxanes.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4395
_journal_page_last               4400
_journal_paper_doi               10.1039/d0ob00906g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C96 H96 N8 O16, 3(B2 F8), 4(C24 H32 O8)'
_chemical_formula_sum            'C192 H224 B6 F24 N8 O48'
_chemical_formula_weight         3932.64
_chemical_name_systematic        '[5]rotaxane'
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_Hall           '-P 4bc'
_space_group_name_H-M_alt        'P 42/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-29 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   25.0521(11)
_cell_length_b                   25.0521(11)
_cell_length_c                   15.1716(18)
_cell_measurement_reflns_used    7197
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.8500
_cell_measurement_theta_min      2.4510
_cell_volume                     9521.8(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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    193.23 288.23   1.00   75.00    --  -88.38 -59.86 110.31   95
  2  \w   -134.58 -25.58   1.00   75.00    -- -103.38  84.78  59.60  109
  3  \w    -11.09  81.91   1.00   75.00    --    4.61  59.85 -20.31   93
  4  \f     13.54 250.54   1.00   75.00 -86.12-103.38 -59.16    --   237
  5  \f     71.67 299.67   1.00   75.00 -23.88-103.38  30.17    --   228
  6  \f     91.67 240.67   1.00   75.00  -3.05   5.65  30.17    --   149
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0430431000
_diffrn_orient_matrix_UB_12      -0.0423501000
_diffrn_orient_matrix_UB_13      0.0192231000
_diffrn_orient_matrix_UB_21      0.0434462000
_diffrn_orient_matrix_UB_22      -0.0433310000
_diffrn_orient_matrix_UB_23      0.0048268000
_diffrn_orient_matrix_UB_31      0.0061988000
_diffrn_orient_matrix_UB_32      0.0102779000
_diffrn_orient_matrix_UB_33      0.0996931000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38551
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        50.412
_diffrn_reflns_theta_max         50.412
_diffrn_reflns_theta_min         2.494
_diffrn_source                   'I\mS Microfocus Source'
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       plate
_exptl_crystal_F_000             4124
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile - isopropyl ether'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.677
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     656
_refine_ls_number_reflns         4886
_refine_ls_number_restraints     611
_refine_ls_restrained_S_all      1.654
_refine_ls_R_factor_all          0.2752
_refine_ls_R_factor_gt           0.1892
_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          0.4626
_refine_ls_wR_factor_ref         0.5216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2121
_reflns_number_total             4886
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00906g2.cif
_cod_data_source_block           cu_pb029_3
_cod_depositor_comments
;Adding full bibliography for 7157517.cif.

 Adding full bibliography for 7157517.cif.
;
_cod_original_cell_volume        9521.8(14)
_cod_original_sg_symbol_H-M      'P 42/n'
_cod_database_code               7157517
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C50 H40 N2 O10 B F4'
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.724
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F4-B1
 1.402 with sigma of 0.02
 F1-B1
 1.402 with sigma of 0.02
 F2-B1
 1.402 with sigma of 0.02
 F3-B1
 1.402 with sigma of 0.02
 B2-F5
 1.402 with sigma of 0.02
 F6A-B2
 1.402 with sigma of 0.02
 B2-F8A
 1.402 with sigma of 0.02
 B2-F6B
 1.402 with sigma of 0.02
 B2-F7B
 1.402 with sigma of 0.02
 F8B-B2
 1.402 with sigma of 0.02
 F7A-B2
 1.402 with sigma of 0.02
 F7A-F8A
 2.21 with sigma of 0.02
 F8A-F6A
 2.21 with sigma of 0.02
 F6A-F7A
 2.21 with sigma of 0.02
 F5-F7A
 2.21 with sigma of 0.02
 F8A-F5
 2.21 with sigma of 0.02
 F6A-F5
 2.21 with sigma of 0.02
 F8B-F7B
 2.21 with sigma of 0.02
 F7B-F6B
 2.21 with sigma of 0.02
 F6B-F8B
 2.21 with sigma of 0.02
 F8B-F5
 2.21 with sigma of 0.02
 F6B-F5
 2.21 with sigma of 0.02
 F7B-F5
 2.21 with sigma of 0.02
 C24A-C23
 1.4 with sigma of 0.02
 C24B-C23
 1.4 with sigma of 0.02
 C24A-O4
 2.4 with sigma of 0.02
 C24B-O4
 2.4 with sigma of 0.02
 C47-O12
 1.36 with sigma of 0.02
 C47-C48
 1.395 with sigma of 0.02
 O5-C48
 1.5 with sigma of 0.02
 F7B-H27_$1
 -2.2 with sigma of 0.02
 F3-H24A
 -2.2 with sigma of 0.02
 F4-H24F
 -2.2 with sigma of 0.02
 F3-H24C
 -2.2 with sigma of 0.02
 H24B-F3
 -2.2 with sigma of 0.02
 H47A-F8B
 -2.2 with sigma of 0.02
 H47B-F8B
 -2.2 with sigma of 0.01
 H24E-F4
 -2.2 with sigma of 0.02
 C20-C21
 1.4 with sigma of 0.02
 C31-C32
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C24A \\sim C23: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(F6B) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C24A) \\sim Ueq, Uanis(C24B) \\sim Ueq: with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C21) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(F6A) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C44, O10, C43, C42, C37, C41, O9, C38, O11, C40, C36, C39, C45, C35, C46, O8,
 C34, O12, C33, O7, C32, C31, O6, C30, C25, C29, C26, O5, C28, C27, C48, C47
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, B1, F4, F3, F1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F6A, F8A, F5, B2, F7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F8B, B2, F5, F7B, F6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, N1, H1, C1, C4, C2, C5, C3, H2, C6, H3, C11, C10, H11, H7, C8, C9, H10,
 H8, C12, N2, H2A, H2B, C13, C18, C14, H18, C17, H14, C15, C16, C22, C19, H16,
 O4, O3, O2, O1, C23, C20, C24B, C24A, C21, H20A, H20B, H21A, H21B, H21C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: F3(0.5) F8A(0.5) F4(0.5) F6B(0.5) F6A(0.5) F7B(0.5) H23C(0.5)
 H23D(0.5) H23A(0.5) H23B(0.5) C24B(0.5) H24A(0.5) H24B(0.5) H24C(0.5) B1(0.5)
 F8B(0.5) F7A(0.5) C24A(0.5) H24D(0.5) H24E(0.5) H24F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C32(H32A,H32B), C12(H12A,H12B), C43(H43A,H43B), C33(H33A,H33B),
 C36(H36A,H36B), C34(H34A,H34B), C46(H46A,H46B), C31(H31A,H31B), C48(H48A,H48B),
  C47(H47A,H47B), C23(H23C,H23D), C23(H23A,H23B), C44(H44A,H44B), C35(H35A,
 H35B), C45(H45A,H45B), C20(H20A,H20B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C26(H26), C27(H27), C28(H28), C29(H29), C10(H10),
 C11(H11), C7(H7), C8(H8), C18(H18), C16(H16), C14(H14), C38(H38), C39(H39),
 C40(H40), C41(H41)
6.c Fitted hexagon refined as free rotating group:
 C30(C25,C26,C27,C28,C29), C42(C37,C38,C39,C40,C41)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24B(H24A,H24B,H24C), C24A(H24D,H24E,H24F)
;
_shelx_res_checksum              79699
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.657