Inherently chiral heterocyclic resorcinarenes using Diels-Alder reaction
Iwanek, Waldemar; Stefańska, Karolina; Szumna, Agnieszka; Wierzbicki, Michał; RSC Adv.  (2016) –; doi:10.1039/C5RA26106F

data_7224033
_publ_section_title
;
 Inherently chiral heterocyclic resorcinarenes using Diels-Alder reaction
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA26106F
_journal_year                    2016
_chemical_formula_moiety         'C84 H96 O8'
_chemical_formula_sum            'C84 H96 O8'
_chemical_formula_weight         1233.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-08 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                101.233(4)
_cell_angle_beta                 109.150(4)
_cell_angle_gamma                90.535(4)
_cell_formula_units_Z            2
_cell_length_a                   16.2545(7)
_cell_length_b                   16.3681(9)
_cell_length_c                   19.4099(7)
_cell_measurement_reflns_used    10718
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      70.0810
_cell_measurement_theta_min      3.8720
_cell_volume                     4769.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.895
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -13.00   16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   60.0000 29

  2 omega   -9.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -87.0000   53.0000 33

  3 omega   36.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  150.0000 33

  4 omega   59.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 45

  5 omega   66.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 50

  6 omega   72.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 44

  7 omega  107.00  134.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 27

  8 omega   81.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 33

  9 omega  118.00  145.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -180.0000 27

 10 omega   85.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   37.0000 -150.0000 83

 11 omega  105.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 71

 12 omega  104.00  171.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 67

 13 omega  100.00  140.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 40

 14 omega  123.00  150.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   30.0000 27

 15 omega  144.00  174.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  150.0000 30

 16 omega  128.00  160.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   87.0000  170.0000 32

 17 omega  106.00  151.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 45

 18 omega   86.00  167.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -60.0000 81

 19 omega   86.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 90

 20 omega   58.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 26

 21 omega   61.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 58

 22 omega   39.00   67.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000  150.0000 28

 23 omega   29.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   37.0000  120.0000 96

 24 omega   43.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -60.0000 61

 25 omega   46.00  120.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -180.0000 74

 26 omega   41.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 30

 27 omega   36.00   82.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 46

 28 omega   37.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000 -180.0000 39

 29 omega   37.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -180.0000 64

 30 omega   30.00   75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -120.0000 45

 31 omega   33.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -120.0000 77

 32 omega   26.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000    0.0000 35

 33 omega   36.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 67

 34 omega   31.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   37.0000   30.0000 84

 35 omega  -10.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 79

 36 omega  -18.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -37.0000 -180.0000 92

 37 omega  -26.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 30

 38 omega  -66.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   60.0000 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0210648000
_diffrn_orient_matrix_UB_12      0.0813443000
_diffrn_orient_matrix_UB_13      -0.0287246000
_diffrn_orient_matrix_UB_21      0.0693306000
_diffrn_orient_matrix_UB_22      0.0496014000
_diffrn_orient_matrix_UB_23      0.0715116000
_diffrn_orient_matrix_UB_31      0.0698495000
_diffrn_orient_matrix_UB_32      -0.0137372000
_diffrn_orient_matrix_UB_33      -0.0380028000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.895
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36541
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.429
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    0.859
_exptl_crystal_F_000             1328
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_refine_diff_density_max         0.916
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     889
_refine_ls_number_reflns         16771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0996
_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          0.2922
_refine_ls_wR_factor_ref         0.3162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11852
_reflns_number_total             16771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra26106f2.cif
_cod_data_source_block           ks5
_cod_database_code               7224033
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C60 H40 N4 O12'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H80C)=Sof(H80D)=Sof(C81B)=Sof(H81B)=Sof(C82B)=Sof(H82D)=Sof(H82E)=
 Sof(H82F)=Sof(C83B)=Sof(H83D)=Sof(H83E)=Sof(H83F)=1-FVAR(1)
 Sof(H80A)=Sof(H80B)=Sof(C81A)=Sof(H81A)=Sof(C82A)=Sof(H82A)=Sof(H82B)=
 Sof(H82C)=Sof(C83A)=Sof(H83A)=Sof(H83B)=Sof(H83C)=FVAR(1)
 Sof(H20A)=Sof(H20B)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(H23C)=1-FVAR(2)
 Sof(H20C)=Sof(H20D)=Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C23B)=Sof(H23D)=Sof(H23E)=Sof(H23F)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C19(H19), C21A(H21A), C21B(H21B), C49(H49), C51A(H51A), C79(H79), C81A(H81A),
 C81B(H81B), C109(H109), C111(H111)
3.b Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C2AA(H2AA,H2AB), C20(H20A,H20B), C20(H20C,H20D), C40(H40A,
 H40B), C41(H41A,H41B), C50(H50A,H50B), C70(H70A,H70B), C71(H71A,H71B),
 C80(H80A,H80B), C80(H80C,H80D), C100(H10A,H10B), C101(H10C,H10D), C110(H11A,
 H11B)
3.c Me refined with riding coordinates:
 C22A(H22A,H22B,H22C), C23A(H23A,H23B,H23C), C22B(H22D,H22E,H22F), C23B(H23D,
 H23E,H23F), C52A(H52A,H52B,H52C), C53A(H53A,H53B,H53C), C82A(H82A,H82B,H82C),
 C83A(H83A,H83B,H83C), C82B(H82D,H82E,H82F), C83B(H83D,H83E,H83F), C112(H11C,
 H11D,H11E), C113(H11F,H11G,H11H)
3.d Aromatic/amide H refined with riding coordinates:
 C8AA(H8AA), C1CA(H1CA), C3AA(H3AA), C16(H16), C17(H17), C18(H18), C32(H32),
 C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C62(H62), C74(H74), C75(H75),
  C76(H76), C77(H77), C78(H78), C92(H92), C104(H104), C105(H105), C106(H106),
 C107(H107), C108(H108)
3.e Tetrahedral OH refined with riding coordinates:
 O7(H7), O37(H37), O67(H67), O97(H97)
3.f Idealised Me refined as rotating group:
 C3BA(H3BA,H3BB,H3BC), C42(H42A,H42B,H42C), C72(H72A,H72B,H72C), C102(H10E,
 H10F,H10G)
;
_shelx_res_checksum              77372
_olex2_submission_special_instructions 'No special instructions were received'