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_1555093
_publ_section_title
;
 Constructing bridged multifunctional calixarenes by intramolecular indole
 coupling
;
_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         'C72 H64 N10 O6'
_chemical_formula_sum            'C72 H64 N10 O6'
_chemical_formula_weight         1165.33
_chemical_melting_point          463.0(10)
_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'
_atom_sites_solution_hydrogens   geom
_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                 93.414(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5782(11)
_cell_length_b                   28.2895(19)
_cell_length_c                   17.3002(11)
_cell_measurement_reflns_used    8349
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.12
_cell_measurement_theta_min      2.19
_cell_volume                     8099.2(9)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       \W
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_unetI/netI     0.1069
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            69052
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.230
_diffrn_source                   'FINE-FOCUS SEALED TUBE'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0716 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.8599.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    0.956
_exptl_crystal_description       NUGGET
_exptl_crystal_F_000             2456
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.591
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       0.0058(13)
_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   1.472
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     682
_refine_ls_number_reflns         14960
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.478
_refine_ls_R_factor_all          0.2255
_refine_ls_R_factor_gt           0.1582
_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          0.4204
_refine_ls_wR_factor_ref         0.4539
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7372
_reflns_number_total             14960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00859d2.cif
_cod_data_source_block           z_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '462-464' was changed to
'463.0(10)' -- the average value was taken and precision was
estimated.

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1555093
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C54-C551 = C54-C552
 1.37 with sigma of 0.02
 C54-N51 = C54-N52 = C551-N7 = C552-N7
 1.35 with sigma of 0.02
 N51-N61 = N7-N61 = N52-N62 = N7-N62
 1.32 with sigma of 0.02
 C64-C651
 1.37 with sigma of 0.02
 C64-N81 = C64-N82 = C651-N10
 1.35 with sigma of 0.02
 N81-N91 = N10-N91 = N82-N92 = N10-N92
 1.32 with sigma of 0.02
 N82-N10
 2.15 with sigma of 0.02
 C1A-C64
 1.37 with sigma of 0.02
 C1A-N10
 1.37 with sigma of 0.02
 C57-C58
 1.39 with sigma of 0.02
 C67-C68
 1.39 with sigma of 0.02
 C68-C69
 1.39 with sigma of 0.02
 C69-C70
 1.39 with sigma of 0.02
 C70-C71
 1.39 with sigma of 0.02
 C72-C71
 1.39 with sigma of 0.02
3. Restrained planarity
 C64, C651, N10, N91, N81
 with sigma of 0.1
 C64, N10, N92, N82
 with sigma of 0.1
 C54, C551, N7, N61, N51
 with sigma of 0.1
 C54, C552, N7, N62, N52
 with sigma of 0.1
 C68, C69, C70, C71, C72, C67
 with sigma of 0.1
 C1A, C64, N10, N92, N82
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(N51) = Uanis(N52)
Uanis(N61) = Uanis(N62)
Uanis(C552) = Uanis(C551)
Uanis(N82) = Uanis(N81)
Uanis(N91) = Uanis(N92)
Uanis(C67) = Uanis(C68) = Uanis(C69) = Uanis(C70) = Uanis(C71) = Uanis(C72)
Uanis(C651) = Uanis(C64) = Uanis(N81) = Uanis(N82) = Uanis(N91) = Uanis(N92) =
Uanis(N10)
Uanis(C57) = Uanis(C62) = Uanis(C61) = Uanis(C60) = Uanis(C59) = Uanis(C58)
Uanis(C66) = Uanis(C67) = Uanis(N10)
Uanis(C1A) = Uanis(N82) = Uanis(N92)
Uanis(N51) = Uanis(C54) = Uanis(C551) = Uanis(N7) = Uanis(N61)
Uanis(C10) = Uanis(C9)
Uanis(C44) = Uanis(C45)
5. Others
 Sof(C552)=Sof(H552)=Sof(N52)=Sof(N62)=1-FVAR(1)
 Sof(C551)=Sof(H551)=Sof(N51)=Sof(N61)=FVAR(1)
 Sof(N82)=Sof(N92)=1-FVAR(2)
 Sof(N81)=Sof(N91)=FVAR(2)
 Fixed Sof: C651(0.75) H651(0.75) C1A(0.25) H1A(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B), C14(H14A,H14B), C20(H20A,H20B), C29(H29A,H29B),
 C31(H31A,H31B), C32(H32A,H32B), C49(H49A,H49B), C50(H50A,H50B), C52(H52A,H52B),
  C53(H53A,H53B), C56(H56A,H56B), C63(H63A,H63B), C66(H66A,H66B)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17),
 C18(H18), C22(H22), C23(H23), C24(H24), C35(H35), C36(H36), C37(H37), C38(H38),
  C43(H43), C44(H44), C45(H45), C46(H46), C58(H58), C59(H59), C60(H60),
 C61(H61), C62(H62), C68(H68), C69(H69), C70(H70), C71(H71), C72(H72), N1(H1),
 N2(H2), N3(H3), N4(H4A), C551(H551), C552(H552), C651(H651), C1A(H1A)
;
_shelx_fab_checksum              30957
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'