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_1575347
_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         'C20 H18 N2'
_chemical_formula_sum            'C20 H18 N2'
_chemical_formula_weight         286.36
_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             2025-01-20
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2025-03-05 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                63.3760(10)
_cell_angle_beta                 66.6870(10)
_cell_angle_gamma                81.2350(10)
_cell_formula_units_Z            4
_cell_length_a                   11.1239(2)
_cell_length_b                   12.7204(2)
_cell_length_c                   13.2024(2)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    102.0(2)
_cell_measurement_theta_max      24.81
_cell_measurement_theta_min      2.29
_cell_volume                     1533.00(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      102.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 Quest, Photon III C7'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            72285
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.052
_diffrn_reflns_theta_max         25.052
_diffrn_reflns_theta_min         1.792
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1127 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.9533.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         5412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0543P)^2^+1.2823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4584
_reflns_number_total             5412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00765h2.cif
_cod_data_source_block           kg_rc_416_1553_0m_a
_cod_depositor_comments
'Adding full bibliography for 1575346--1575352.cif.'
_cod_database_code               1575347
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H) groups
2. Shared sites
{C24A, C24B}
3. Uiso/Uaniso restraints and constraints
Uanis(C24A) = Uanis(C24B)
Uanis(C21A) = Uanis(C21B)
4. Others
 Sof(C21B)=Sof(H21B)=Sof(C24B)=Sof(H24B)=Sof(C22B)=Sof(H22A)=Sof(H22B)=
 Sof(C23B)=Sof(H23A)=Sof(H23B)=1-FVAR(1)
 Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C24A)=
 Sof(H24A)=Sof(C21A)=Sof(H21A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C14(H14), C21B(H21B), C24B(H24B), C24A(H24A), C21A(H21A)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C22B(H22A,H22B), C23B(H23A,H23B), C23A(H23C,
 H23D), C22A(H22C,H22D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C5(H5A), C6(H6), C8(H8), C13(H13), C17(H17), C18(H18),
 C19(H19), C20(H20), C26(H26), C30(H30), C33(H33), C34(H34), C35(H35), C36(H36),
  C37(H37), C38(H38), C39(H39), C40(H40)
;
_shelx_res_checksum              66037
_olex2_submission_special_instructions 'No special instructions were received'