Well-defined zinc(ii) catalysts for sustainable synthesis of bis(indolyl)methanes via the activation of aromatic and aliphatic alcohols
Chauhan, Rahul; Kukreti, Prashant; Sharma, Keshav; Singh, Ovender; Ghosh, Kaushik; Catalysis Science & Technology 15 (2025) 6693–6702; doi:10.1039/D5CY00765H

data_1575348
_publ_section_title
;
 Well-defined zinc(ii) catalysts for sustainable synthesis of
 bis(indolyl)methanes via the activation of aromatic and aliphatic
 alcohols
;
_journal_issue                   22
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              6693
_journal_page_last               6702
_journal_paper_doi               10.1039/D5CY00765H
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         '7(C H Cl3), 4(C25 H23 N3)'
_chemical_formula_sum            'C107 H99 Cl21 N12'
_chemical_formula_weight         2297.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-01-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-05 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.4049(2)
_cell_length_b                   18.5983(3)
_cell_length_c                   20.5244(3)
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.23
_cell_measurement_theta_min      2.21
_cell_volume                     5392.01(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0660
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            167309
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         1.442
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1288 before and 0.0668 after correction. The Ratio of minimum to maximum transmission is 0.9369. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       plate
_exptl_crystal_F_000             2364
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.019
_refine_diff_density_max         1.422
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 8189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.486(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1269
_refine_ls_number_reflns         22082
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+6.6024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                19304
_reflns_number_total             22082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00765h2.cif
_cod_data_source_block           kg_rc_371_1382_0m_a
_cod_depositor_comments
'Adding full bibliography for 1575346--1575352.cif.'
_cod_database_code               1575348
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.867
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C9(H9), C34(H34), C59(H59), C84(H84), C101(H101), C102(H102), C103(H103),
 C104(H104), C105(H105), C106(H106), C107(H107)
1.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N4(H4A), N5(H5A), N7(H7A), N8(H8), N10(H10), N11(H11A),
 C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C12(H12), C14(H14),
 C15(H15), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29),
  C30(H30), C31(H31), C33(H33), C36(H36), C40(H40), C41(H41), C43(H43),
 C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C53(H53), C54(H54), C55(H55),
  C56(H56), C58(H58), C61(H61), C65(H65), C66(H66), C68(H68), C69(H69),
 C70(H70), C71(H71), C72(H72), C73(H73), C77(H77), C78(H78), C79(H79), C80(H80),
  C82(H82), C86(H86), C87(H87), C89(H89), C90(H90), C94(H94), C96(H96),
 C97(H97), C98(H98), C99(H99)
1.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C25(H25A,H25B,H25C), C49(H49A,H49B,H49C), C50(H50A,H50B,
 H50C), C74(H74A,H74B,H74C), C75(H75A,H75B,H75C), C95(H95A,H95B,H95C),
 C100(H10A,H10B,H10C)
;
_shelx_res_checksum              85919
_olex2_submission_special_instructions 'No special instructions were received'