Straighforward Metal-Free Synthesis of an Azacalix[6]arene Forming a Host-Guest Complex with Fullerene C60
Canard, Gabriel; Jacquemin, Denis; SIRI, Olivier; Azarias, Cloé; Chen, Zhongrui; New J. Chem. 41 (2017) 5284–5290; doi:10.1039/C7NJ00697G

data_7056227
_publ_section_title
;
 Straighforward Metal-Free Synthesis of an Azacalix[6]arene Forming a
 Host-Guest Complex with Fullerene C60
;
_journal_issue                   13
_journal_name_full               'New J. Chem.'
_journal_page_first              5284
_journal_page_last               5290
_journal_paper_doi               10.1039/C7NJ00697G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         '9(C2 H6 O S), 2(C83.5 H125 N18 O12)'
_chemical_formula_sum            'C185 H304 N36 O33 S9'
_chemical_formula_weight         3849.16
_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     direct
_audit_creation_date             2017-05-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-05-02 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.387(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8072(5)
_cell_length_b                   41.1391(12)
_cell_length_c                   34.898(2)
_cell_measurement_reflns_used    5495
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      55.1720
_cell_measurement_theta_min      3.7850
_cell_volume                     21164.4(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega -129.00   54.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5600    0.0000 -180.0000 183

  2 omega   82.00  118.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5600  178.0000    0.0000 36

  3 omega   34.00   61.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       95.1618  -45.0000 -150.0000 27

  4 omega   48.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       95.1618  -94.0000 -150.0000 61

  5 omega   16.00   48.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       95.1618  -30.0000 -120.0000 32

  6 omega   66.00   91.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       95.1618  -30.0000 -120.0000 25

  7 omega   65.00   98.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       95.1618  -45.0000  -60.0000 33

  8 omega   11.00  130.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       95.1618  -77.0000   60.0000 119

  9 omega   59.00  178.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       95.1618   77.0000  -60.0000 119

 10 omega  118.00  148.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       95.1618   30.0000   30.0000 30

 11 omega   76.00  101.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       95.1618   30.0000   30.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0197940000
_diffrn_orient_matrix_UB_12      -0.0059019000
_diffrn_orient_matrix_UB_13      -0.0420039000
_diffrn_orient_matrix_UB_21      0.0441072000
_diffrn_orient_matrix_UB_22      -0.0328761000
_diffrn_orient_matrix_UB_23      0.0116768000
_diffrn_orient_matrix_UB_31      -0.0926420000
_diffrn_orient_matrix_UB_32      -0.0169106000
_diffrn_orient_matrix_UB_33      -0.0081971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_av_unetI/netI     0.1292
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            78025
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.271
_diffrn_reflns_theta_max         66.271
_diffrn_reflns_theta_min         3.465
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             8296
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dimethylsulfoxyde'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.308
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.286
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2422
_refine_ls_number_reflns         36284
_refine_ls_number_restraints     445
_refine_ls_restrained_S_all      1.300
_refine_ls_R_factor_all          0.2692
_refine_ls_R_factor_gt           0.1670
_refine_ls_shift/su_max          0.002
_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          0.4174
_refine_ls_wR_factor_ref         0.4808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15657
_reflns_number_total             36284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj00697g2.cif
_cod_data_source_block           4b
_cod_database_code               7056227
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C121-C122
 1.54 with sigma of 0.02
 C122-C123
 1.54 with sigma of 0.02
 C123-C124
 1.54 with sigma of 0.02
 C126-C127
 1.54 with sigma of 0.02
 C129-C130
 1.54 with sigma of 0.02
 C130-C131
 1.54 with sigma of 0.02
 C131-C132
 1.54 with sigma of 0.02
 C132-C133
 1.54 with sigma of 0.02
 C133-C134
 1.54 with sigma of 0.02
 C134-C135
 1.54 with sigma of 0.02
 C137-C138
 1.54 with sigma of 0.02
 C138-C139
 1.54 with sigma of 0.02
 C139-C140
 1.54 with sigma of 0.02
 C140-C141
 1.54 with sigma of 0.02
 C141-C142
 1.54 with sigma of 0.02
 C142-C143
 1.54 with sigma of 0.02
 C37-C38
 1.54 with sigma of 0.02
 C38-C39
 1.54 with sigma of 0.02
 C39-C40
 1.54 with sigma of 0.02
 C40-C41
 1.54 with sigma of 0.02
 C41-C42
 1.54 with sigma of 0.02
 C42-C43
 1.54 with sigma of 0.02
 C153-C154
 1.54 with sigma of 0.02
 C154-C155
 1.54 with sigma of 0.02
 C155-C156
 1.54 with sigma of 0.02
 C156-C157
 1.54 with sigma of 0.02
 C157-C158
 1.54 with sigma of 0.02
 C158-C159
 1.54 with sigma of 0.02
 C153-C155
 2.35 with sigma of 0.02
 C154-C156
 2.35 with sigma of 0.02
 C155-C157
 2.35 with sigma of 0.02
 C156-C158
 2.35 with sigma of 0.02
 C157-C159
 2.35 with sigma of 0.02
 C37-C39
 2.35 with sigma of 0.02
 C38-C40
 2.35 with sigma of 0.02
 C39-C41
 2.35 with sigma of 0.02
 C40-C42
 2.35 with sigma of 0.02
 C41-C43
 2.35 with sigma of 0.02
 C121-C123
 2.54 with sigma of 0.02
 C122-C124
 2.54 with sigma of 0.02
 C124-C126
 2.54 with sigma of 0.02
 C129-C131
 2.35 with sigma of 0.02
 C130-C132
 2.35 with sigma of 0.02
 C131-C133
 2.54 with sigma of 0.02
 C132-C134
 2.54 with sigma of 0.02
 C133-C135
 2.54 with sigma of 0.02
 C137-C139
 2.35 with sigma of 0.02
 C138-C140
 2.35 with sigma of 0.02
 C139-C141
 2.35 with sigma of 0.02
 C140-C142
 2.35 with sigma of 0.02
 C141-C143
 2.35 with sigma of 0.02
 C143-C144
 1.54 with sigma of 0.02
 C142-C144
 2.35 with sigma of 0.02
 C127-C128
 1.54 with sigma of 0.02
 C126-C128
 2.35 with sigma of 0.02
 C135-C136
 1.54 with sigma of 0.02
 C134-C136
 2.54 with sigma of 0.02
 C159-C160
 1.54 with sigma of 0.02
 C158-C160
 2.35 with sigma of 0.02
 C43-C44
 1.54 with sigma of 0.02
 C42-C44
 2.35 with sigma of 0.02
 C50-C52
 2.35 with sigma of 0.02
 C51-C52
 1.54 with sigma of 0.02
 C124-C125
 1.54 with sigma of 0.02
 C125-C126
 1.54 with sigma of 0.02
 C123-C125
 2.54 with sigma of 0.02
 C125-C127
 2.54 with sigma of 0.02
 S13-C186
 1.54 with sigma of 0.01
 C125-C128
 3.54 with sigma of 0.02
 C131-C134
 3.54 with sigma of 0.02
 C133-C136
 3.54 with sigma of 0.02
 C78-C79
 1.54 with sigma of 0.02
 C78-C77
 1.54 with sigma of 0.02
 C79-C80
 1.54 with sigma of 0.02
 C80-C81
 1.54 with sigma of 0.02
 C81-C82
 1.54 with sigma of 0.02
 C83-C84
 1.54 with sigma of 0.02
 C74-C75
 1.45 with sigma of 0.02
 C75-C76
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C137 \\sim C138 \\sim C139 \\sim C140 \\sim C141 \\sim C142 \\sim C143 \\sim
C144: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C129 \\sim C130 \\sim C131 \\sim C132 \\sim C133 \\sim C134 \\sim C135 \\sim
C136: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C153 \\sim C154 \\sim C155 \\sim C156 \\sim C157 \\sim C158 \\sim C159 \\sim
C160: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim C44:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C49 \\sim C50 \\sim C51 \\sim C52: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
S4 \\sim O28 \\sim C175 \\sim C176: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
C121 \\sim C122 \\sim C123 \\sim C124 \\sim C125 \\sim C126 \\sim C127 \\sim
C128: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
C57 \\sim C58 \\sim C59 \\sim C60: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 4
C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81 \\sim C82 \\sim C83 \\sim C84:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
S13 \\sim O34 \\sim C186: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.1
S12 \\sim O33 \\sim C186 \\sim C187: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
C69 \\sim C70 \\sim C71 \\sim C72 \\sim C73 \\sim C74 \\sim C75 \\sim C76:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Others
 Fixed Sof: S6(0.5) S7(0.5) H17A(0.5) H17B(0.5) H17C(0.5) H17D(0.5) H17E(0.5)
 H17F(0.5) H18N(0.5) H18O(0.5) H18P(0.5) H18Q(0.5) H18R(0.5) H18S(0.5) S8(0.5)
 S9(0.5) H18W(0.5) H18X(0.5) H18Y(0.5) H18T(0.5) H18U(0.5) H18V(0.5) HF(0.5)
 HG(0.5) HH(0.5) H18Z(0.5) HI(0.5) HJ(0.5) S10(0.5) S11(0.5) H0AA(0.5) HK(0.5)
 HL(0.5) HM(0.5) HN(0.5) HO(0.5) H1AA(0.5) HP(0.5) HQ(0.5) HR(0.5) HS(0.5)
 HT(0.5) S12(0.6) S13(0.4) O33(0.6) O34(0.4) H18B(0.6) H18C(0.6) H18D(0.6)
 H18E(0.4) H18F(0.4) H18G(0.4) H18H(0.6) H18I(0.6) H18J(0.6) H18K(0.4)
 H18L(0.4) H18M(0.4) C71(0.5) H71A(0.5) H71B(0.5) C141(0.5) H14C(0.5) H14D(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,
 H41B), C42(H42A,H42B), C43(H43A,H43B), C45(H45A,H45B), C46(H46A,H46B),
 C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B),
  C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B), C56(H56A,H56B), C57(H57A,
 H57B), C58(H58A,H58B), C59(H59A,H59B), C61(H61A,H61B), C62(H62A,H62B),
 C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B), C66(H66A,H66B), C67(H67A,H67B),
  C69(H69A,H69B), C70(H70A,H70B), C71(H71A,H71B), C72(H72A,H72B), C73(H73A,
 H73B), C74(H74A,H74B), C75(H75A,H75B), C77(H77A,H77B), C78(H78A,H78B),
 C79(H79A,H79B), C80(H80A,H80B), C81(H81A,H81B), C82(H82A,H82B), C83(H83A,H83B),
  C121(H12B,H12C), C122(H12D,H12E), C123(H12F,H12G), C124(H12H,H12I), C125(H12J,
 H12K), C126(H12L,H12M), C127(H12N,H12O), C129(H12S,H12T), C130(H13A,H13B),
 C131(H13C,H13D), C132(H13E,H13F), C133(H13G,H13H), C134(H13I,H13J), C135(H13K,
 H13L), C137(H13P,H13Q), C138(H13R,H13S), C139(H13T,H13U), C140(H14A,H14B),
 C141(H14C,H14D), C142(H14E,H14F), C143(H14G,H14H), C145(H14L,H14M), C146(H14N,
 H14O), C147(H14P,H14Q), C148(H14R,H14S), C149(H14T,H14U), C150(H15A,H15B),
 C151(H15C,H15D), C153(H15H,H15I), C154(H15J,H15K), C155(H15L,H15M), C156(H15N,
 H15O), C157(H15P,H15Q), C158(H15R,H15S), C159(H15T,H15U), C161(H16D,H16E),
 C162(H16F,H16G), C163(H16H,H16I), C164(H16J,H16K), C165(H16L,H16M), C166(H16N,
 H16O), C167(H16P,H16Q)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), N5(H5), N6(H6), N7(H7), N10(H10), N11(H11), N12(H12),
 N13(H13), N16(H16), N17(H17), N18(H18), C3(H3), C6(H6A), C9(H9), C12(H12A),
 C15(H15), C18(H18A), C20(H20), C23(H23), C27(H27), C30(H30), C33(H33),
 C36(H36), N19(H19), N20(H20A), N21(H21), N22(H22), N25(H25), N26(H26),
 N27(H27A), N28(H28), N31(H31), N32(H32), N33(H33A), N34(H34), C87(H87),
 C90(H90), C93(H93), C96(H96), C98(H98), C101(H101), C104(H104), C107(H107),
 C111(H111), C114(H114), C116(H116), C119(H119)
5.c Idealised Me refined with riding coordinates:
 C169(H16U,H16V,H16W), C170(H17G,H17H,H17I), C171(H17J,H17K,H17L), C172(H17M,
 H17N,H17O), C173(H17P,H17Q,H17R), C174(H17S,H17T,H17U), C175(H17V,H17W,H17X),
 C176(H17Y,H,HA), C177(H17Z,HB,HC), C178(H2AA,HD,HE), C179(H17A,H17B,H17C),
 C179(H17D,H17E,H17F), C180(H18N,H18O,H18P), C180(H18Q,H18R,H18S), C181(H18W,
 H18X,H18Y), C181(H18T,H18U,H18V), C182(HF,HG,HH), C182(H18Z,HI,HJ), C183(H0AA,
 HK,HL), C183(HM,HN,HO), C185(H1AA,HP,HQ), C185(HR,HS,HT), C186(H18B,H18C,H18D),
  C186(H18E,H18F,H18G), C187(H18H,H18I,H18J), C187(H18K,H18L,H18M), C44(H44A,
 H44B,H44C), C52(H52A,H52B,H52C), C60(H60A,H60B,H60C), C68(H68A,H68B,H68C),
 C76(H76A,H76B,H76C), C84(H84A,H84B,H84C), C128(H12P,H12Q,H12R), C136(H13M,H13N,
 H13O), C144(H14I,H14J,H14K), C152(H15E,H15F,H15G), C160(H16A,H16B,H16C),
 C168(H16R,H16S,H16T)
;
_olex2_submission_special_instructions 'No special instructions were received'