#------------------------------------------------------------------------------
#$Date: 2025-11-29 18:06:41 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303499 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/53/1575352.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1575352
loop_
_publ_author_name
'Chauhan, Rahul'
'Kukreti, Prashant'
'Sharma, Keshav'
'Singh, Ovender'
'Ghosh, Kaushik'
_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 & Technology'
_journal_page_first              6693
_journal_page_last               6702
_journal_paper_doi               10.1039/D5CY00765H
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C35 H27 Cl2 N7 Zn'
_chemical_formula_sum            'C35 H27 Cl2 N7 Zn'
_chemical_formula_weight         681.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-10-16
_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                90
_cell_angle_beta                 115.630(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.8911(4)
_cell_length_b                   16.2580(4)
_cell_length_c                   23.8268(6)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.276
_cell_measurement_theta_min      2.679
_cell_volume                     7296.4(3)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            159456
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.426
_diffrn_reflns_theta_min         1.658
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0826 before and 0.0606 after correction. The Ratio of minimum to maximum transmission is 0.9556. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic dark green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             2800
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         9157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0356
_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/[σ²(Fo²)+(0.0424P)²+7.0638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7765
_reflns_number_total             9157
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cy00765h2.cif
_cod_data_source_block           kg_rc_69_0158_0ma_a
_cod_depositor_comments
'Adding full bibliography for 1575346--1575352.cif.'
_cod_database_code               1575352
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.874
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N7(H7), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11),
 C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22),
  C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32),
 C33(H33), C34(H34), C35(H35)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.43345(2) 0.27880(2) 0.37756(2) 0.01992(6) Uani 1 1 d . . . . .
Cl1 Cl 0.50905(2) 0.37030(3) 0.37139(2) 0.03478(11) Uani 1 1 d . . . . .
Cl2 Cl 0.39021(2) 0.17922(3) 0.30380(2) 0.02472(9) Uani 1 1 d . . . . .
N1 N 0.37125(9) 0.40970(10) 0.17529(7) 0.0297(3) Uani 1 1 d . . . . .
H1 H 0.396614 0.390996 0.156644 0.036 Uiso 1 1 calc R . . . .
N2 N 0.33541(7) 0.35956(8) 0.34071(6) 0.0201(3) Uani 1 1 d . . . . .
N3 N 0.39980(7) 0.27526(8) 0.44518(6) 0.0182(3) Uani 1 1 d . . . . .
N4 N 0.30457(7) 0.35817(9) 0.38272(6) 0.0215(3) Uani 1 1 d . . . . .
N5 N 0.49670(8) 0.19325(10) 0.50435(7) 0.0261(3) Uani 1 1 d . . . . .
N6 N 0.51733(8) 0.20042(9) 0.45602(6) 0.0229(3) Uani 1 1 d . . . . .
N7 N 0.62642(8) 0.18144(10) 0.33634(7) 0.0295(3) Uani 1 1 d . . . . .
H7 H 0.617686 0.187958 0.297023 0.035 Uiso 1 1 calc R . . . .
C1 C 0.29548(9) 0.48597(10) 0.19772(8) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.32531(9) 0.47559(11) 0.15527(8) 0.0251(4) Uani 1 1 d . . . . .
C3 C 0.30755(10) 0.52621(12) 0.10336(9) 0.0303(4) Uani 1 1 d . . . . .
H3 H 0.328120 0.518543 0.075136 0.036 Uiso 1 1 calc R . . . .
C4 C 0.25879(11) 0.58792(12) 0.09482(9) 0.0327(4) Uani 1 1 d . . . . .
H4 H 0.244849 0.622822 0.059513 0.039 Uiso 1 1 calc R . . . .
C5 C 0.22949(10) 0.60020(12) 0.13689(9) 0.0312(4) Uani 1 1 d . . . . .
H5 H 0.196352 0.643510 0.129802 0.037 Uiso 1 1 calc R . . . .
C6 C 0.24776(9) 0.55060(11) 0.18862(9) 0.0261(4) Uani 1 1 d . . . . .
H6 H 0.228309 0.560170 0.217446 0.031 Uiso 1 1 calc R . . . .
C7 C 0.32550(9) 0.42218(10) 0.24421(8) 0.0231(3) Uani 1 1 d . . . . .
C8 C 0.37148(10) 0.37804(11) 0.22798(9) 0.0270(4) Uani 1 1 d . . . . .
H8 H 0.399097 0.332376 0.250377 0.032 Uiso 1 1 calc R . . . .
C9 C 0.30619(9) 0.41060(10) 0.29449(8) 0.0223(3) Uani 1 1 d . . . . .
H9 H 0.268341 0.443400 0.294039 0.027 Uiso 1 1 calc R . . . .
C10 C 0.33912(9) 0.31405(10) 0.43681(8) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.31259(10) 0.31108(12) 0.48134(8) 0.0288(4) Uani 1 1 d . . . . .
H11 H 0.269322 0.337640 0.474488 0.035 Uiso 1 1 calc R . . . .
C12 C 0.35103(10) 0.26844(12) 0.53557(9) 0.0305(4) Uani 1 1 d . . . . .
H12 H 0.334727 0.266997 0.567110 0.037 Uiso 1 1 calc R . . . .
C13 C 0.41261(10) 0.22792(11) 0.54484(8) 0.0262(4) Uani 1 1 d . . . . .
H13 H 0.438705 0.197821 0.581988 0.031 Uiso 1 1 calc R . . . .
C14 C 0.43547(9) 0.23245(10) 0.49800(8) 0.0215(3) Uani 1 1 d . . . . .
C15 C 0.23026(9) 0.37618(10) 0.36190(8) 0.0203(3) Uani 1 1 d . . . . .
C16 C 0.18067(10) 0.31834(11) 0.32634(8) 0.0263(4) Uani 1 1 d . . . . .
H16 H 0.195559 0.268599 0.314695 0.032 Uiso 1 1 calc R . . . .
C17 C 0.10896(10) 0.33366(13) 0.30783(9) 0.0324(4) Uani 1 1 d . . . . .
H17 H 0.074537 0.294587 0.283013 0.039 Uiso 1 1 calc R . . . .
C18 C 0.08768(10) 0.40569(13) 0.32550(9) 0.0318(4) Uani 1 1 d . . . . .
H18 H 0.038612 0.415791 0.313029 0.038 Uiso 1 1 calc R . . . .
C19 C 0.13700(10) 0.46274(13) 0.36095(9) 0.0331(4) Uani 1 1 d . . . . .
H19 H 0.121854 0.511965 0.373040 0.040 Uiso 1 1 calc R . . . .
C20 C 0.20923(10) 0.44898(11) 0.37938(9) 0.0266(4) Uani 1 1 d . . . . .
H20 H 0.243406 0.488745 0.403462 0.032 Uiso 1 1 calc R . . . .
C21 C 0.53367(9) 0.14210(11) 0.55822(8) 0.0238(3) Uani 1 1 d . . . . .
C22 C 0.59238(10) 0.17259(12) 0.60852(8) 0.0287(4) Uani 1 1 d . . . . .
H22 H 0.610743 0.225448 0.606633 0.034 Uiso 1 1 calc R . . . .
C23 C 0.62398(11) 0.12484(14) 0.66170(9) 0.0371(5) Uani 1 1 d . . . . .
H23 H 0.664316 0.144961 0.696609 0.044 Uiso 1 1 calc R . . . .
C24 C 0.59693(11) 0.04790(14) 0.66407(10) 0.0387(5) Uani 1 1 d . . . . .
H24 H 0.618374 0.015914 0.700948 0.046 Uiso 1 1 calc R . . . .
C25 C 0.53932(11) 0.01729(12) 0.61361(10) 0.0359(5) Uani 1 1 d . . . . .
H25 H 0.521543 -0.035969 0.615336 0.043 Uiso 1 1 calc R . . . .
C26 C 0.50718(10) 0.06475(12) 0.55998(9) 0.0293(4) Uani 1 1 d . . . . .
H26 H 0.467354 0.044134 0.524858 0.035 Uiso 1 1 calc R . . . .
C27 C 0.57873(9) 0.17068(11) 0.46632(8) 0.0248(4) Uani 1 1 d . . . . .
H27 H 0.606031 0.146720 0.505946 0.030 Uiso 1 1 calc R . . . .
C28 C 0.60892(9) 0.17109(11) 0.42227(8) 0.0243(3) Uani 1 1 d . . . . .
C29 C 0.68387(9) 0.16011(11) 0.43963(8) 0.0249(3) Uani 1 1 d . . . . .
C30 C 0.69259(10) 0.16815(11) 0.38434(9) 0.0269(4) Uani 1 1 d . . . . .
C31 C 0.57657(10) 0.18297(12) 0.35874(8) 0.0275(4) Uani 1 1 d . . . . .
H31 H 0.527116 0.190996 0.334377 0.033 Uiso 1 1 calc R . . . .
C32 C 0.74372(10) 0.14600(12) 0.49538(9) 0.0317(4) Uani 1 1 d . . . . .
H32 H 0.739474 0.140720 0.533336 0.038 Uiso 1 1 calc R . . . .
C33 C 0.80942(10) 0.13980(13) 0.49461(10) 0.0375(5) Uani 1 1 d . . . . .
H33 H 0.850353 0.129658 0.532380 0.045 Uiso 1 1 calc R . . . .
C34 C 0.81653(11) 0.14819(14) 0.43926(11) 0.0401(5) Uani 1 1 d . . . . .
H34 H 0.862363 0.143787 0.440283 0.048 Uiso 1 1 calc R . . . .
C35 C 0.75895(11) 0.16266(13) 0.38327(10) 0.0360(5) Uani 1 1 d . . . . .
H35 H 0.763969 0.168631 0.345707 0.043 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Zn1 Cl2 118.871(19) . . ?
Cl1 Zn1 N2 97.80(4) . . ?
Cl1 Zn1 N6 96.35(4) . . ?
Cl2 Zn1 N6 98.13(4) . . ?
N2 Zn1 Cl2 97.07(4) . . ?
N2 Zn1 N6 150.91(5) . . ?
N3 Zn1 Cl1 125.12(4) . . ?
N3 Zn1 Cl2 116.01(4) . . ?
N3 Zn1 N2 75.95(5) . . ?
N3 Zn1 N6 75.11(5) . . ?
C8 N1 C2 109.80(14) . . ?
N4 N2 Zn1 109.31(9) . . ?
C9 N2 Zn1 135.41(11) . . ?
C9 N2 N4 114.92(13) . . ?
C10 N3 Zn1 119.83(11) . . ?
C14 N3 Zn1 121.19(11) . . ?
C14 N3 C10 118.94(14) . . ?
N2 N4 C15 120.61(13) . . ?
C10 N4 N2 117.35(13) . . ?
C10 N4 C15 118.62(13) . . ?
N6 N5 C21 122.97(13) . . ?
C14 N5 N6 118.26(13) . . ?
C14 N5 C21 118.62(14) . . ?
N5 N6 Zn1 108.40(10) . . ?
C27 N6 Zn1 134.65(12) . . ?
C27 N6 N5 116.55(14) . . ?
C31 N7 C30 109.92(15) . . ?
C2 C1 C7 106.48(14) . . ?
C6 C1 C2 119.05(15) . . ?
C6 C1 C7 134.46(16) . . ?
N1 C2 C1 107.62(15) . . ?
N1 C2 C3 130.04(16) . . ?
C3 C2 C1 122.34(16) . . ?
C4 C3 C2 117.10(16) . . ?
C3 C4 C5 121.50(17) . . ?
C6 C5 C4 121.29(17) . . ?
C5 C6 C1 118.68(16) . . ?
C8 C7 C1 106.35(15) . . ?
C8 C7 C9 130.34(16) . . ?
C9 C7 C1 123.28(15) . . ?
N1 C8 C7 109.74(15) . . ?
N2 C9 C7 126.38(15) . . ?
N3 C10 N4 117.40(14) . . ?
N3 C10 C11 121.86(15) . . ?
N4 C10 C11 120.73(15) . . ?
C12 C11 C10 117.97(16) . . ?
C13 C12 C11 121.12(16) . . ?
C12 C13 C14 117.84(16) . . ?
N3 C14 N5 117.00(14) . . ?
N3 C14 C13 122.24(15) . . ?
N5 C14 C13 120.76(15) . . ?
C16 C15 N4 118.84(15) . . ?
C16 C15 C20 120.86(16) . . ?
C20 C15 N4 120.26(16) . . ?
C15 C16 C17 119.43(17) . . ?
C18 C17 C16 120.02(18) . . ?
C19 C18 C17 120.38(17) . . ?
C18 C19 C20 120.49(18) . . ?
C15 C20 C19 118.81(17) . . ?
C22 C21 N5 119.82(17) . . ?
C26 C21 N5 119.00(17) . . ?
C26 C21 C22 121.08(17) . . ?
C21 C22 C23 118.98(19) . . ?
C24 C23 C22 120.2(2) . . ?
C25 C24 C23 120.66(18) . . ?
C24 C25 C26 119.64(19) . . ?
C21 C26 C25 119.47(19) . . ?
N6 C27 C28 124.90(16) . . ?
C27 C28 C29 123.51(16) . . ?
C31 C28 C27 129.78(16) . . ?
C31 C28 C29 106.69(15) . . ?
C30 C29 C28 106.39(15) . . ?
C32 C29 C28 134.92(17) . . ?
C32 C29 C30 118.67(16) . . ?
N7 C30 C29 107.52(15) . . ?
N7 C30 C35 129.83(17) . . ?
C35 C30 C29 122.65(17) . . ?
N7 C31 C28 109.46(16) . . ?
C33 C32 C29 119.02(18) . . ?
C32 C33 C34 121.10(19) . . ?
C35 C34 C33 121.80(18) . . ?
C34 C35 C30 116.75(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 Cl1 2.2204(5) . ?
Zn1 Cl2 2.2698(5) . ?
Zn1 N2 2.2658(14) . ?
Zn1 N3 2.0182(13) . ?
Zn1 N6 2.3142(14) . ?
N1 C2 1.378(2) . ?
N1 C8 1.355(2) . ?
N2 N4 1.4055(18) . ?
N2 C9 1.301(2) . ?
N3 C10 1.351(2) . ?
N3 C14 1.346(2) . ?
N4 C10 1.375(2) . ?
N4 C15 1.441(2) . ?
N5 N6 1.3981(19) . ?
N5 C14 1.378(2) . ?
N5 C21 1.441(2) . ?
N6 C27 1.291(2) . ?
N7 C30 1.378(2) . ?
N7 C31 1.360(2) . ?
C1 C2 1.409(2) . ?
C1 C6 1.399(2) . ?
C1 C7 1.447(2) . ?
C2 C3 1.396(2) . ?
C3 C4 1.381(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.381(2) . ?
C7 C8 1.382(2) . ?
C7 C9 1.432(2) . ?
C10 C11 1.394(2) . ?
C11 C12 1.377(2) . ?
C12 C13 1.376(2) . ?
C13 C14 1.393(2) . ?
C15 C16 1.384(2) . ?
C15 C20 1.388(2) . ?
C16 C17 1.389(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.372(3) . ?
C19 C20 1.395(3) . ?
C21 C22 1.384(3) . ?
C21 C26 1.382(3) . ?
C22 C23 1.386(3) . ?
C23 C24 1.384(3) . ?
C24 C25 1.375(3) . ?
C25 C26 1.392(3) . ?
C27 C28 1.440(2) . ?
C28 C29 1.447(2) . ?
C28 C31 1.378(2) . ?
C29 C30 1.412(2) . ?
C29 C32 1.394(3) . ?
C30 C35 1.400(3) . ?
C32 C33 1.384(3) . ?
C33 C34 1.396(3) . ?
C34 C35 1.376(3) . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.547 677.8 145.1 ?
2 0.000 0.444 0.750 23.2 0.0 ?
3 0.000 0.556 0.250 23.2 0.0 ?
4 0.147 0.506 0.492 9.2 0.0 ?
5 0.147 0.494 0.992 9.2 0.0 ?
6 0.500 0.500 -0.865 677.8 143.9 ?
7 0.353 0.006 0.008 9.2 0.0 ?
8 0.353 -0.006 0.508 9.2 0.0 ?
9 0.500 0.056 0.250 23.2 0.0 ?
10 0.500 0.944 0.750 23.2 0.0 ?
11 0.647 0.006 0.492 9.2 0.0 ?
12 0.647 -0.006 0.992 9.2 0.0 ?
13 0.853 0.494 0.508 9.2 0.0 ?
14 0.853 0.506 0.008 9.2 0.0 ?
