Constructing bridged multifunctional calixarenes by intramolecular indole coupling
Bolshchikov, Boris; Volkov, Sergey; Sokolova, Daria; Gorbunov, Alexander; Serebryannikova, Alina; Gloriozov, Igor; Cheshkov, Dmitry; Bezzubov, Stanislav; Chung, Wen-Sheng; Kovalev, Vladimir; Vatsouro, Ivan; Organic Chemistry Frontiers 6 (2019) 3327–; doi:10.1039/C9QO00859D

data_1555094
_publ_section_title
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 Constructing bridged multifunctional calixarenes by intramolecular indole
 coupling
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_journal_issue                   19
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3327
_journal_paper_doi               10.1039/C9QO00859D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C76 H68 N8 O8'
_chemical_formula_sum            'C76 H68 N8 O8'
_chemical_formula_weight         1222.19
_chemical_melting_point_gt       573
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2018-09-06 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.5570(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.104(3)
_cell_length_b                   23.487(2)
_cell_length_c                   26.090(4)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.476
_cell_measurement_theta_min      2.201
_cell_volume                     15719(3)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            63317
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.175
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0743 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.8306.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.033
_exptl_crystal_description       nugget
_exptl_crystal_F_000             5155
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMSO, ethanol'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     762
_refine_ls_number_reflns         15461
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.2181
_refine_ls_R_factor_gt           0.1640
_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^)+(0.0857P)^2^+249.6758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3643
_refine_ls_wR_factor_ref         0.3949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9096
_reflns_number_total             15461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00859d2.cif
_cod_data_source_block           z_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_chemical_melting_point' was changed to
'_chemical_melting_point_gt' since the value was specified as 'more
than' ('>') a certain temperature.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        15720(3)
_cod_database_code               1555094
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
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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
2. Restrained distances
 N8AB-C1R
 1.35 with sigma of 0.02
 C2N-C2M
 1.38 with sigma of 0.02
 C2E-N4AA
 1.36 with sigma of 0.02
 C1Z-C24
 1.38 with sigma of 0.02
 C24-C1Z
 1.38 with sigma of 0.02
3. Restrained planarity
 C1X, C1Y, C1Z, C24, C25, C29
 with sigma of 0.1
 C1C, C1J, C1I, C1H, C1G, C1F, C1E, C1D, N6BB
 with sigma of 0.1
 C32, C39, N6BA, C38, C37, C36, C35, C34, C33
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(N6BB) = Uanis(N6BA)
Uanis(C34) = Uanis(C1H)
Uanis(C1G) = Uanis(C35)
Uanis(N0AA) = Uanis(N1A)
Uanis(N8AB) = Uanis(N8AA)
Uanis(O8AA) = Uanis(O8AB)
Uanis(C2E) = Uanis(C1T)
Uanis(C2I) = Uanis(C2O) = Uanis(C2N) = Uanis(C2M) = Uanis(C2L) = Uanis(C2K)
Uanis(C2Q) = Uanis(C2P) = Uanis(C2U) = Uanis(C2T) = Uanis(C2S) = Uanis(C2R) =
Uanis(C3A) = Uanis(C29A) = Uanis(N1A)
Uanis(C32) = Uanis(C39) = Uanis(N6BA) = Uanis(C38) = Uanis(C37) = Uanis(C36) =
Uanis(C35) = Uanis(C34) = Uanis(C33)
Uiso(C31) = Uiso(N5BA) = Uiso(C2Z) = Uiso(C2Y) = Uiso(C2X) = Uiso(C2W) =
Uiso(C2V) = Uiso(C30)
Uanis(C1J) = Uanis(C1C) = Uanis(N6BB) = Uanis(C1D) = Uanis(C1E) = Uanis(C1F) =
Uanis(C1G) = Uanis(C1H) = Uanis(C1I)
Uanis(C1A) = Uanis(N5BB) = Uanis(C5) = Uanis(C4) = Uanis(C2) = Uanis(C1) =
Uanis(C3) = Uanis(C6)
Uanis(C1L) = Uanis(C1AA) = Uanis(N0AA) = Uanis(C0AA) = Uanis(C1Q) = Uanis(C1P)
= Uanis(C1O) = Uanis(C1N) = Uanis(C1M)
Uanis(C1W) = Uanis(C1X) = Uanis(C1Y) = Uanis(C1Z) = Uanis(C24) = Uanis(C25) =
Uanis(C29) = Uanis(N8AB) = Uanis(C1R)
Uanis(C1U) = Uanis(C2F)
Uanis(N4AA) = Uanis(N4AB)
Uanis(C2C) = Uanis(C0)
Uanis(C1T) = Uanis(O8AB)
Uanis(C2E) = Uanis(O8AA)
Uanis(C2H) = Uanis(C1W)
Uanis(C1U) = Uanis(C1V)
Uanis(C1S) = Uanis(C1T) = Uanis(C2D) = Uanis(C2E) = Uanis(O8AB) = Uanis(O8AA) =
Uanis(N4AB) = Uanis(N4AA)
Uanis(C51B) = Uanis(C51A)
Uanis(N4AA) = Uanis(C2F)
Uanis(C3B) = Uanis(C4B) = Uanis(C2B)
5. Others
 Sof(N8AB)=Sof(H8AB)=Sof(N8AA)=Sof(H8AA)=FVAR(1)
 Fixed Sof: O6B(0.5) N5BB(0.5) H5BB(0.5) N6BB(0.5) H6BB(0.5) C3(0.5) C1(0.5)
 H1(0.5) C2(0.5) H2(0.5) C4(0.5) H4(0.5) C5(0.5) H5(0.5) C6(0.5) C1A(0.5)
 C1C(0.5) C1D(0.5) C1E(0.5) H1E(0.5) C1F(0.5) H1F(0.5) C1G(0.5) H1G(0.5)
 C1H(0.5) H1H(0.5) C1I(0.5) C1J(0.5) C1K(0.5) H1KA(0.5) H1KB(0.5) C51B(0.5)
 H52C(0.5) H52D(0.5) H52A(0.5) H52B(0.5) H56C(0.5) H56D(0.5) H56A(0.5)
 H56B(0.5) C1L(0.5) C1M(0.5) C1N(0.5) H1N(0.5) C1O(0.5) H1O(0.5) C1P(0.5)
 H1P(0.5) C1Q(0.5) H1Q(0.5) C1R(0.5) C1S(0.5) H1SA(0.5) H1SB(0.5) C1T(0.5)
 O8AB(0.5) N4AB(0.5) H4AB(0.5) C1U(0.5) H1UA(0.5) H1UB(0.5) C1V(0.5) H1VA(0.5)
 H1VB(0.5) C1W(0.5) C1X(0.5) C1Y(0.5) H1Y(0.5) C1Z(0.5) H1Z(0.5) C24(0.5)
 H24(0.5) C25(0.5) H25(0.5) C29(0.5) N2AB(0.5) H2AB(0.5) N0AA(0.5) H0AA(0.5)
 C0AA(0.5) C1AA(0.5) C0(0.5) H0A(0.5) H0B(0.5) C2A(0.5) H2AA(0.5) H2AC(0.5)
 C2C(0.5) H2CA(0.5) H2CB(0.5) C2D(0.5) H2DA(0.5) H2DB(0.5) C2E(0.5) N4AA(0.5)
 H4AA(0.5) O8AA(0.5) C2F(0.5) H2FA(0.5) H2FB(0.5) C2G(0.5) H2GA(0.5) H2GB(0.5)
 C2H(0.5) C2I(0.5) C2J(0.5) C2K(0.5) C2L(0.5) H2L(0.5) C2M(0.5) H2M(0.5)
 C2N(0.5) H2N(0.5) C2O(0.5) H2O(0.5) C2P(0.5) H2P(0.5) C2Q(0.5) H2Q(0.5)
 C2R(0.5) H2R(0.5) C2S(0.5) H2S(0.5) C2T(0.5) C2U(0.5) N1A(0.5) H1A(0.5)
 C2V(0.5) H2V(0.5) C2W(0.5) H2W(0.5) C2X(0.5) H2X(0.5) C2Y(0.5) H2Y(0.5)
 C2Z(0.5) C30(0.5) C31(0.5) N5BA(0.5) H5BA(0.5) C32(0.5) C33(0.5) C34(0.5)
 H34(0.5) C35(0.5) H35(0.5) C36(0.5) H36(0.5) C37(0.5) H37(0.5) C38(0.5)
 N6BA(0.5) H6BD(0.5) C39(0.5) N2AA(0.5) H2AD(0.5) C51A(0.5) O6A(0.5) C3A(0.5)
 C29A(0.5)
6.a Riding coordinates:
 N2AB(H2AB)
6.b Secondary CH2 refined with riding coordinates:
 C6B(H6BA,H6BC), C12(H12A,H12B), C18(H18A,H18B), C24B(H24A,H24B), C29B(H29A,
 H29B), C31B(H31A,H31B), C32B(H32A,H32B), C1K(H1KA,H1KB), C52(H52C,H52D),
 C52(H52A,H52B), C53(H53A,H53B), C55B(H55A,H55B), C56B(H56C,H56D), C56B(H56A,
 H56B), C1S(H1SA,H1SB), C1U(H1UA,H1UB), C1V(H1VA,H1VB), C0(H0A,H0B), C2A(H2AA,
 H2AC), C2C(H2CA,H2CB), C2D(H2DA,H2DB), C2F(H2FA,H2FB), C2G(H2GA,H2GB)
6.c Aromatic/amide H refined with riding coordinates:
 N1B(H1B), N3(H3), N5BB(H5BB), N6BB(H6BB), C2B(H2B), C3B(H3B), C4B(H4B),
 C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C20(H20), C21(H21),
 C22(H22), C1(H1), C2(H2), C4(H4), C5(H5), C1E(H1E), C1F(H1F), C1G(H1G),
 C1H(H1H), C1N(H1N), C1O(H1O), C1P(H1P), C1Q(H1Q), N4AB(H4AB), C1Y(H1Y),
 C1Z(H1Z), C24(H24), C25(H25), N8AB(H8AB), N0AA(H0AA), N4AA(H4AA), N8AA(H8AA),
 C2L(H2L), C2M(H2M), C2N(H2N), C2O(H2O), C2P(H2P), C2Q(H2Q), C2R(H2R), C2S(H2S),
  N1A(H1A), C2V(H2V), C2W(H2W), C2X(H2X), C2Y(H2Y), N5BA(H5BA), C34(H34),
 C35(H35), C36(H36), C37(H37), N6BA(H6BD), N2AA(H2AD)
;
_shelx_fab_checksum              83802
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'