Controlling the selective synthesis of [2]- and [3]rotaxanes by intermolecular steric hindrance between the macrocyclic hosts.
Ye, Zecong; Wang, Jian; Kothapalli, Sudarshana Santhosh Kumar; Yang, Zhiyao; Chen, Lixi; Xu, Weitao; Cai, Yimin; Zhang, Tinghui; Xiao, Xin; Deng, Pengchi; Feng, Wen; Yuan, Lihua; Chemical communications (Cambridge, England) 56 (2020) 1066–1069; doi:10.1039/c9cc08253k

data_7125694
_publ_section_title
;
 Controlling the selective synthesis of [2]- and [3]rotaxanes by
 intermolecular steric hindrance between the macrocyclic hosts.
;
_journal_issue                   7
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1066
_journal_page_last               1069
_journal_paper_doi               10.1039/c9cc08253k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety
'2(F6 P), C80 H108 N8 O12, C40 H54 N2, 2(C4 H8 O2), 2(C4.5 O2)'
_chemical_formula_sum            'C137 H197 F12 N10 O20 P2'
_chemical_formula_weight         2593.97
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-12 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                100.477(3)
_cell_angle_beta                 97.247(3)
_cell_angle_gamma                114.357(4)
_cell_formula_units_Z            1
_cell_length_a                   14.0229(5)
_cell_length_b                   16.6854(7)
_cell_length_c                   17.4200(5)
_cell_measurement_reflns_used    8361
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      73.2990
_cell_measurement_theta_min      4.3620
_cell_volume                     3558.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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   -109.00 -16.00   1.00    2.00    --  -40.08 -38.00 -60.00   93
  2  \w   -110.00 -25.00   1.00    2.00    --  -40.08 -38.00  30.00   85
  3  \w    -68.00  33.00   1.00    2.00    --  -40.08  57.00-180.00  101
  4  \w      1.00  81.00   1.00    2.00    --   40.08 -99.00 -90.00   80
  5  \w     42.00 118.00   1.00    2.00    --  105.48-125.00  30.00   76
  6  \w    103.00 177.00   1.00    2.00    --  105.48 125.00-180.00   74
  7  \w     75.00 118.00   1.00    2.00    --  105.48-125.00-150.00   43
  8  \w     32.00  61.00   1.00    2.00    --  105.48 -45.00 -90.00   29
  9  \w     88.00 130.00   1.00    2.00    --  105.48 -45.00 -90.00   42
 10  \w     33.00 134.00   1.00    2.00    --  105.48 -61.00  60.00  101
 11  \w     78.00 178.00   1.00    2.00    --  105.48  30.00 150.00  100
 12  \w     42.00 153.00   1.00    2.00    --  105.48 -15.00 120.00  111
 13  \w     40.00 135.00   1.00    2.00    --  105.48 -61.00-180.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0166680000
_diffrn_orient_matrix_UB_12      0.0932282000
_diffrn_orient_matrix_UB_13      -0.0133239000
_diffrn_orient_matrix_UB_21      -0.1093681000
_diffrn_orient_matrix_UB_22      -0.0459936000
_diffrn_orient_matrix_UB_23      -0.0602720000
_diffrn_orient_matrix_UB_31      -0.0554604000
_diffrn_orient_matrix_UB_32      0.0142240000
_diffrn_orient_matrix_UB_33      0.0686121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20980
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.456
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.955
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             1387
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.014
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.00077(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     919
_refine_ls_number_reflns         12457
_refine_ls_number_restraints     384
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0745
_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^)+(0.1300P)^2^+2.2684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2131
_refine_ls_wR_factor_ref         0.2308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9806
_reflns_number_total             12457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08253k2.cif
_cod_data_source_block           s
_cod_depositor_comments
'Adding full bibliography for 7125693--7125694.cif.'
_cod_original_cell_volume        3558.0(2)
_cod_database_code               7125694
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     C4A-C2-CaCL2
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.847
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C38-C39A
 1.5 with sigma of 0.02
 C38-C39
 1.5 with sigma of 0.02
 C65-C66
 1.5 with sigma of 0.02
 C66-O8
 1.22 with sigma of 0.02
 C66-O9
 1.23 with sigma of 0.02
 O9-C67
 1.35 with sigma of 0.02
 C67-C68
 1.5 with sigma of 0.02
 C66A-O8A
 1.25 with sigma of 0.02
 C66A-O9
 1.25 with sigma of 0.02
 C65A-C66A
 1.5 with sigma of 0.02
 C67A-O9
 1.35 with sigma of 0.02
 C67A-C68A
 1.5 with sigma of 0.02
 O8-C65
 2.35 with sigma of 0.02
 O9-C65
 2.35 with sigma of 0.02
 O8A-C65A
 2.38 with sigma of 0.02
 O9-C68A
 2.45 with sigma of 0.02
3. Rigid bond restraints
 O9, C65, C66, O8, C67, C66A, C67A, C68, C65A, O8A, C68A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F3 \\sim F2A \\sim F2 \\sim F5A \\sim F1 \\sim F4A \\sim F4 \\sim F3A: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O9 \\sim C65 \\sim C66 \\sim O8 \\sim C67 \\sim C66A \\sim C67A \\sim C68 \\sim
C65A \\sim O8A \\sim C68A: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(F3A) \\sim Ueq, Uanis(P1) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim
Ueq, Uanis(F4) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F2A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C64) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C63)
\\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(C61) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C65) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(O8)
\\sim Ueq, Uanis(C68) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(O9) \\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(O8)
\\sim Ueq, Uanis(C67A) \\sim Ueq, Uanis(C68A) \\sim Ueq, Uanis(C67) \\sim Ueq,
Uanis(C66A) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C65A) \\sim Ueq, Uanis(O8A)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Fixed Sof: F4(0.5) H38A(0.5) H38(0.5) F3(0.5) F2(0.5) F1(0.5) C39A(0.5)
 H39A(0.5) H39B(0.5) H39C(0.5) C39(0.5) H39D(0.5) H39E(0.5) H39F(0.5) F3A(0.5)
 F5A(0.5) F4A(0.5) F2A(0.5) C66(0.5) C67(0.5) C68(0.5) O8(0.5) C65A(0.5)
 C66A(0.5) C67A(0.5) C68A(0.5) O8A(0.5)
6.a Ternary CH refined with riding coordinates:
 C16(H16), C2(H2A), C38(H38A), C38(H38), C33(H33)
6.b Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C13(H13A,H13B), C36(H36A,H36B), C31(H31A,H31B), C5(H5A,H5B),
 C14(H14A,H14B), C4(H4A,H4B), C37(H37A,H37B), C32(H32A,H32B), C63(H63A,H63B)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C41(H41), C24(H24), C48(H48), C9(H9), C12(H12), C52(H52),
 C26(H26), C50(H50), C29(H29), C30(H30), C21(H21), C22(H22), C45(H45), C43(H43),
  C44(H44)
6.d Idealised Me refined as rotating group:
 C56(H56A,H56B,H56C), C55(H55A,H55B,H55C), C54(H54A,H54B,H54C), C59(H59A,H59B,
 H59C), C58(H58A,H58B,H58C), C15(H15A,H15B,H15C), C60(H60A,H60B,H60C), C17(H17A,
 H17B,H17C), C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C64(H64A,H64B,H64C), C40(H40A,
 H40B,H40C), C61(H61A,H61B,H61C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C),
 C39A(H39A,H39B,H39C), C39(H39D,H39E,H39F)
;
_shelx_res_checksum              74951
_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 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.684