Unidirectional complexation of pillar[4]arene[1]benzoquinoneoxime with alkyl alcohols.
Li, Kun-Ang; Wang, Zhuo; Xie, Chang-Dong; Chen, Tao; Qiang, Hui; Liu, Yahu A.; Jia, Xue-Shun; Hu, Wei-Bo; Wen, Ke; Organic & biomolecular chemistry 17 (2019) 4975–4978; doi:10.1039/c9ob00665f

data_7156805
_publ_section_title
;
 Unidirectional complexation of pillar[4]arene[1]benzoquinoneoxime with
 alkyl alcohols.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4975
_journal_page_last               4978
_journal_paper_doi               10.1039/c9ob00665f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C43 H44 N O10, C4 H10 O'
_chemical_formula_sum            'C47 H54 N O11'
_chemical_formula_weight         808.91
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-12 deposited with the CCDC.    2019-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.137(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1968(2)
_cell_length_b                   31.9446(4)
_cell_length_c                   12.4129(2)
_cell_measurement_reflns_used    29554
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1970
_cell_measurement_theta_min      4.1460
_cell_volume                     4224.34(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_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    -24.00   1.00   1.00    2.00    --    0.00  -4.00-165.00   25
  2  \w     73.00  98.00   1.00    3.00    --   95.80  -4.00-165.00   25
  3  \w    132.00 160.00   1.00    3.00    --   95.80  -4.00-165.00   28
  4  \w     18.00  44.00   1.00    3.00    --   95.80  -4.00-165.00   26
  5  \w     19.00  51.00   1.00    2.00    --    0.00  38.00  60.00   32
  6  \w    -10.00  17.00   1.00    2.00    --    0.00 -38.00 -60.00   27
  7  \w    -82.00 -52.00   1.00    2.00    --    0.00 -38.00-150.00   30
  8  \w     56.00  89.00   1.00    2.00    --    0.00  38.00 120.00   33
  9  \w     56.00  86.00   1.00    2.00    --    0.00  77.00   0.00   30
 10  \w    -23.00  12.00   1.00    2.00    --    0.00  57.00-180.00   35
 11  \w      4.00  30.00   1.00    2.00    --    0.00  57.00 -30.00   26
 12  \w    -45.00 -20.00   1.00    2.00    --    0.00 -38.00-150.00   25
 13  \w    -88.00 -57.00   1.00    2.00    --    0.00 -38.00 -60.00   31
 14  \w     25.00  68.00   1.00    2.00    --    0.00  57.00-180.00   43
 15  \w    -31.00  46.00   1.00    2.00    --    0.00  82.00 -60.00   77
 16  \w     52.00  88.00   1.00    2.00    --    0.00  82.00 -60.00   36
 17  \w    -19.00  15.00   1.00    2.00    --    0.00  38.00  60.00   34
 18  \w    -18.00  63.00   1.00    2.00    --    0.00  38.00 -90.00   81
 19  \w     59.00  87.00   1.00    2.00    --    0.00  38.00  60.00   28
 20  \w     46.00  77.00   1.00    2.00    --    0.00  57.00 -30.00   31
 21  \w    -19.00  50.00   1.00    2.00    --    0.00  38.00 120.00   69
 22  \w      5.00  31.00   1.00    2.00    --    0.00   4.00  10.00   26
 23  \w    -29.00  24.00   1.00    2.00    --    0.00  77.00   0.00   53
 24  \w    -24.00   1.00   1.00    2.00    --    0.00   4.00  10.00   25
 25  \w    151.00 182.00   1.00    3.00    --   95.80  82.00 150.00   31
 26  \w     63.00  89.00   1.00    3.00    --   95.80  82.00 150.00   26
 27  \w     65.00  93.00   1.00    3.00    --   95.80  77.00 -30.00   28
 28  \w     67.00 110.00   1.00    3.00    --   95.80  72.00-127.00   43
 29  \w    155.00 181.00   1.00    3.00    --   95.80  77.00 -90.00   26
 30  \w     65.00  90.00   1.00    3.00    --   95.80  77.00   0.00   25
 31  \w     75.00 123.00   1.00    3.00    --   95.80  45.00  30.00   48
 32  \w    127.00 185.00   1.00    3.00    --   95.80  45.00  30.00   58
 33  \w     67.00  93.00   1.00    3.00    --   95.80  71.00 -64.24   26
 34  \w    134.00 160.00   1.00    3.00    --   95.80  71.00 -64.24   26
 35  \w     77.00 125.00   1.00    3.00    --   95.80 -82.00 -30.00   48
 36  \w    137.00 162.00   1.00    3.00    --   95.80  77.00-180.00   25
 37  \w     65.00  90.00   1.00    3.00    --   95.80  77.00 -90.00   25
 38  \w     12.00 128.00   1.00    3.00    --   95.80 -82.00-120.00  116
 39  \w     65.00  90.00   1.00    3.00    --   95.80  77.00-180.00   25
 40  \w    159.00 185.00   1.00    3.00    --   95.80  82.00  60.00   26
 41  \w     64.00  94.00   1.00    3.00    --   95.80  82.00  30.00   30
 42  \w     75.00 120.00   1.00    3.00    --   95.80  45.00  90.00   45
 43  \w     64.00  89.00   1.00    3.00    --   95.80  82.00  60.00   25
 44  \w     63.00  88.00   1.00    3.00    --   95.80  82.00 -30.00   25
 45  \w    103.00 185.00   1.00    3.00    --   95.80  61.00 -30.00   82
 46  \w    125.00 181.00   1.00    3.00    --   95.80  45.00  90.00   56
 47  \w     71.00 184.00   1.00    3.00    --   95.80  61.00 -90.00  113
 48  \w     65.00  91.00   1.00    3.00    --   95.80  77.00-150.00   26
 49  \w     69.00  95.00   1.00    3.00    --   95.80  67.00 119.01   26
 50  \w     71.00 124.00   1.00    3.00    --   95.80  61.00-150.00   53
 51  \w     65.00  91.00   1.00    3.00    --   95.80  77.00 -60.00   26
 52  \w     69.00 137.00   1.00    3.00    --   95.80  66.00  91.44   68
 53  \w    156.00 182.00   1.00    3.00    --   95.80  69.00-149.77   26
 54  \w     65.00  91.00   1.00    3.00    --   95.80  77.00  30.00   26
 55  \w      6.00 128.00   1.00    3.00    --   95.80 -82.00  60.00  122
 56  \w     71.00  97.00   1.00    3.00    --   95.80  61.00 -30.00   26
 57  \w     71.00 181.00   1.00    3.00    --   95.80  59.00-102.88  110
 58  \w     63.00  88.00   1.00    3.00    --   95.80  82.00 -60.00   25
 59  \w     69.00  94.00   1.00    3.00    --   95.80  65.00 154.33   25
 60  \w     75.00 118.00   1.00    3.00    --   95.80  45.00  60.00   43
 61  \w     64.00  89.00   1.00    3.00    --   95.80  82.00   0.00   25
 62  \w     65.00  90.00   1.00    3.00    --   95.80  77.00  60.00   25
 63  \w     68.00  94.00   1.00    3.00    --   95.80  72.00 -59.15   26
 64  \w    139.00 176.00   1.00    3.00    --   95.80  72.00 -59.15   37
 65  \w     65.00  91.00   1.00    3.00    --   95.80  77.00 150.00   26
 66  \w     76.00 102.00   1.00    3.00    --   95.80  45.00   0.00   26
 67  \w     29.00  75.00   1.00    3.00    --   95.80 -82.00 -90.00   46
 68  \w     69.00 182.00   1.00    3.00    --   95.80  68.00 129.05  113
 69  \w    141.00 167.00   1.00    3.00    --   95.80  82.00 120.00   26
 70  \w     68.00  93.00   1.00    3.00    --   95.80  69.00-149.77   25
 71  \w    152.00 178.00   1.00    3.00    --   95.80  69.00 156.07   26
 72  \w     75.00 175.00   1.00    3.00    --   95.80  45.00-150.00  100
 73  \w     68.00 128.00   1.00    3.00    --   95.80  69.00 156.07   60
 74  \w     63.00  88.00   1.00    3.00    --   95.80  82.00 120.00   25
 75  \w     71.00 154.00   1.00    3.00    --   95.80  61.00 120.00   83
 76  \w     44.00 127.00   1.00    3.00    --   95.80 -82.00-150.00   83
 77  \w    148.00 173.00   1.00    3.00    --   95.80  80.00  81.00   25
 78  \w     95.00 125.00   1.00    3.00    --   95.80 -82.00 -90.00   30
 79  \w    141.00 166.00   1.00    3.00    --   95.80  45.00   0.00   25
 80  \w     65.00  91.00   1.00    3.00    --   95.80  80.00  81.00   26
 81  \w     65.00  91.00   1.00    3.00    --   95.80  77.00-120.00   26
 82  \w    102.00 127.00   1.00    3.00    --   95.80  77.00 -30.00   25
 83  \w    111.00 136.00   1.00    3.00    --   95.80   4.00  10.00   25
 84  \w     45.00  70.00   1.00    3.00    --   95.80 -82.00  90.00   25
 85  \w     87.00 122.00   1.00    3.00    --   95.80 -82.00  90.00   35
 86  \w     55.00  80.00   1.00    3.00    --   95.80 -82.00 120.00   25
 87  \w     96.00 121.00   1.00    3.00    --   95.80 -82.00 120.00   25
 88  \w     10.00  35.00   1.00    3.00    --   95.80   4.00  10.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1354289000
_diffrn_orient_matrix_UB_12      -0.0004916000
_diffrn_orient_matrix_UB_13      0.1082578000
_diffrn_orient_matrix_UB_21      0.0506560000
_diffrn_orient_matrix_UB_22      0.0026797000
_diffrn_orient_matrix_UB_23      -0.0917872000
_diffrn_orient_matrix_UB_31      -0.0013850000
_diffrn_orient_matrix_UB_32      0.0481599000
_diffrn_orient_matrix_UB_33      0.0062362000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            110184
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.622
_diffrn_reflns_theta_min         4.150
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1724
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         8564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0633
_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^)+(0.0411P)^2^+5.1331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7649
_reflns_number_total             8564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00665f2.cif
_cod_data_source_block           exp_768
_cod_depositor_comments
'Adding full bibliography for 7156804--7156806.cif.'
_cod_original_cell_volume        4224.34(13)
_cod_database_code               7156805
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.77
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C11(H11), C15(H15), C18(H18), C21(H21), C24(H24),
 C26(H26), C29(H29)
2.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C43(H43A,
 H43B,H43C), C44(H44A,H44B,H44C)
2.d Idealised tetrahedral OH refined as rotating group:
 O11(H11A)
;
_shelx_res_checksum              49689
_shelx_hkl_checksum              15553
_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 7.273
_oxdiff_exptl_absorpt_empirical_full_min 0.537