Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes.
Cera, Gianpiero; Balestri, Davide; Bazzoni, Margherita; Marchiò, Luciano; Secchi, Andrea; Arduini, Arturo; Organic & biomolecular chemistry 18 (2020) 6241–6246; doi:10.1039/d0ob01319f

data_7157608
_publ_section_title
;
 Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6241
_journal_page_last               6246
_journal_paper_doi               10.1039/d0ob01319f
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C90 H111 N3 O15 S3, 3(H2 O)'
_chemical_formula_sum            'C90 H117 N3 O18 S3'
_chemical_formula_weight         1625.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-12 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                74.481(2)
_cell_angle_beta                 69.188(2)
_cell_angle_gamma                67.602(2)
_cell_formula_units_Z            2
_cell_length_a                   15.5420(6)
_cell_length_b                   16.5195(6)
_cell_length_c                   20.2175(7)
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      69.16
_cell_measurement_theta_min      2.93
_cell_volume                     4433.3(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 PhotonII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_unetI/netI     0.1253
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36476
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.199
_diffrn_reflns_theta_min         3.208
_diffrn_source                   microfocus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.311
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0933 before and 0.0719 after correction. The Ratio of minimum to maximum transmission is 0.7933. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             1740
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1073
_refine_ls_number_reflns         16505
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.0698
_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^)+(0.0674P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7234
_reflns_number_total             16505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01319f2.cif
_cod_data_source_block           cu_jf11bis_0m_db_ok
_cod_depositor_comments          'Adding full bibliography for 7157608.cif.'
_cod_database_code               7157608
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.914
_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 O(H,H) groups
2. Restrained distances
 N1S2-H1S2
 0.9 with sigma of 0.02
 N1S1-H1S1
 0.9 with sigma of 0.02
 O1W3-H1WA = O1W3-H1WB
 0.9 with sigma of 0.02
 O1W2-H1WF = O1W2-H1WE
 0.9 with sigma of 0.02
 O2E2-C8E = O2E2-C8E2 = C8E2-C9E2 = C8E-C9E
 1.4 with sigma of 0.02
 H1WA-H1WB
 1.4 with sigma of 0.04
 H1WF-H1WE
 1.4 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C8E2 \\sim C9E2: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
C8E \\sim C9E: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C9E) \\sim Ueq, Uanis(C8E) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(C8E2) \\sim Ueq, Uanis(C9E2) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
4. Others
 Sof(C8E)=Sof(H8EG)=Sof(H8EH)=Sof(C9E)=Sof(H9EJ)=Sof(H9EK)=Sof(H9EL)=1-FVAR(1)
 Sof(C9E2)=Sof(H9EG)=Sof(H9EH)=Sof(H9EI)=Sof(C8E2)=Sof(H8EE)=Sof(H8EF)=FVAR(1)
 Fixed X: H1WA(0.544089) H1WB(0.523141) H1WC(0.49032) H1WD(0.576009) H1WE(-
 0.27562) H1WF(-0.264491)
 Fixed Y: H1WA(0.34962) H1WB(0.44218) H1WC(0.339449) H1WD(0.259749)
 H1WE(0.473459) H1WF(0.38377)
 Fixed Z: H1WA(0.21152) H1WB(0.21877) H1WC(-0.087191) H1WD(-0.099431) H1WE(-
 0.01476) H1WF(0.002429)
5.a Riding coordinates:
 N1S3(H1S3)
5.b Secondary CH2 refined with riding coordinates:
 C4ME(H4MA,H4MB), C6ME(H6MA,H6MB), C1ME(H1MA,H1MB), C6E1(H6EA,H6EB), C3ME(H3MA,
 H3MB), C5ME(H5MA,H5MB), C2ME(H2MA,H2MB), C6E2(H6EC,H6ED), C6E3(H6EE,H6EF),
 C7E1(H7EA,H7EB), C7E2(H7EC,H7ED), C7E3(H7EE,H7EF), C8E1(H8EA,H8EB), C8E3(H8EC,
 H8ED), C8E2(H8EE,H8EF), C8E(H8EG,H8EH)
5.c Aromatic/amide H refined with riding coordinates:
 C1M3(H1M3), C5E2(H5E2), C5M1(H5M1), C5M3(H5M3), C5M2(H5M2), C5E3(H5E3),
 C5E1(H5E1), C1M1(H1M1), C1E1(H1E1), C1E2(H1E2), C1M2(H1M2), C1E3(H1E3),
 C1S3(H1SA), C1S1(H1SB), C5S3(H5S3), C2S1(H2S1), C4S2(H4S2), C2S3(H2S3),
 C4S1(H4S1), C5S2(H5S2), C5S1(H5S1), C2S2(H2S2), C1S2(H1SC), C4S3(H4S3)
5.d Idealised Me refined as rotating group:
 C1MT(H1MC,H1MD,H1ME), C2MT(H2MC,H2MD,H2ME), C3MT(H3MC,H3MD,H3ME), C8M2(H8MA,
 H8MB,H8MC), C8M1(H8MD,H8ME,H8MF), C7M2(H7MA,H7MB,H7MC), C7M3(H7MD,H7ME,H7MF),
 C6S1(H6SA,H6SB,H6SC), C6S2(H6SD,H6SE,H6SF), C9M1(H9MA,H9MB,H9MC), C9E1(H9EA,
 H9EB,H9EC), C9M2(H9MD,H9ME,H9MF), C8M3(H8MG,H8MH,H8MI), C7M1(H7MG,H7MH,H7MI),
 C9M3(H9MG,H9MH,H9MI), C6S3(H6SG,H6SH,H6SI), C9E3(H9ED,H9EE,H9EF), C9E2(H9EG,
 H9EH,H9EI), C9E(H9EJ,H9EK,H9EL)
;
_shelx_res_checksum              88394
_shelx_hkl_checksum              84029
_olex2_exptl_crystal_mounting_method Cryoloop
_olex2_submission_special_instructions 'No special instructions were received'