Design of a Primary-Amide-Functionalized Highly Efficient and Recyclable Hydrogen-Bond-Donating Heterogeneous Catalyst for the Friedel‒Crafts Alkylation of Indoles with β-Nitrostyrenes
Markad, Datta; Mandal, Sanjay K.; ACS Catalysis 9 (2019) 3165–; doi:10.1021/acscatal.8b04962

data_4514749
_publ_section_title
;
 Design of a Primary-Amide-Functionalized Highly Efficient and Recyclable
 Hydrogen-Bond-Donating Heterogeneous Catalyst for the Friedel--Crafts
 Alkylation of Indoles with \b-Nitrostyrenes
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              3165
_journal_paper_doi               10.1021/acscatal.8b04962
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C44 H40 N6 O10 Zn2'
_chemical_formula_sum            'C44 H40 N6 O10 Zn2'
_chemical_formula_weight         943.56
_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             2018-07-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                82.784(3)
_cell_angle_beta                 81.615(3)
_cell_angle_gamma                88.403(3)
_cell_formula_units_Z            1
_cell_length_a                   8.7707(9)
_cell_length_b                   11.7137(12)
_cell_length_c                   13.5892(12)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.002
_cell_measurement_theta_min      2.35
_cell_volume                     1370.2(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX-II'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34423
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.075
_diffrn_reflns_theta_max         25.075
_diffrn_reflns_theta_min         2.347
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/4 (Bruker,2014/4)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       needle
_exptl_crystal_F_000             486
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.072
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0958P)^2^+2.4569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.1911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4038
_reflns_number_total             4856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04962_si_002.cif
_cod_data_source_block           1
_cod_database_code               4514749
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.897
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C11(H11), C16(H16), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_shelx_res_checksum              75885
_shelx_hkl_checksum              75127
_shelx_fab_checksum              11437
_olex2_submission_special_instructions 'No special instructions were received'