#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:36:27 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284283 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/66/7246605.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_7246605
loop_
_publ_author_name
'Devi, Arpita'
'Bharali, Mrinmoy Manash'
'Biswas, Subir'
'Bora, Tonmoy J.'
'Nath, Jayanta K.'
'Lee, Seonghwan'
'Park, Young-Bin'
'Saikia, Lakshi'
'Baruah, Manash J.'
'Bania, Kusum K.'
_publ_section_title
;
 Utilization of methanol and ethanol for 3,3′-bis(indolyl)methane
 synthesis through activation of peroxymonosulfate over a copper catalyst
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3443
_journal_page_last               3448
_journal_paper_doi               10.1039/D3GC00440F
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 N2'
_chemical_formula_sum            'C18 H16 N2'
_chemical_formula_weight         260.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-12-28 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.607(2)
_cell_length_b                   10.064(2)
_cell_length_c                   21.600(4)
_cell_measurement_reflns_used    4197
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.23
_cell_measurement_theta_min      2.26
_cell_volume                     1436.2(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1610
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            44792
_diffrn_reflns_theta_full        28.77
_diffrn_reflns_theta_max         28.77
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            BROWN
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.2277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1528
_reflns_number_gt                2145
_reflns_number_total             3681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3gc00440f2.cif
_cod_data_source_block           appp01_a
_cod_depositor_comments
'Adding full bibliography for 7246605--7246607.cif.'
_cod_original_cell_volume        1436.1(6)
_cod_database_code               7246605
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2279(4) 0.2385(3) 0.44888(11) 0.0689(7) Uani 1 1 d . . .
N2 N 0.5595(4) 0.6154(3) 0.25789(10) 0.0731(7) Uani 1 1 d . . .
C12 C 0.5407(4) 0.2615(2) 0.40876(10) 0.0483(6) Uani 1 1 d . . .
C4 C 0.7818(4) 0.6481(2) 0.33571(10) 0.0515(6) Uani 1 1 d . . .
C11 C 0.4709(4) 0.3904(3) 0.42905(10) 0.0525(6) Uani 1 1 d . . .
C3 C 0.6207(4) 0.5665(2) 0.35854(10) 0.0534(6) Uani 1 1 d . . .
C2 C 0.5948(4) 0.5179(3) 0.42522(10) 0.0550(6) Uani 1 1 d . . .
C17 C 0.3872(4) 0.1677(3) 0.42297(10) 0.0570(7) Uani 1 1 d . . .
C18 C 0.2810(5) 0.3714(3) 0.45347(12) 0.0638(7) Uani 1 1 d . . .
C13 C 0.7256(4) 0.2155(3) 0.38242(11) 0.0588(7) Uani 1 1 d . . .
C9 C 0.7397(4) 0.6787(3) 0.27222(10) 0.0566(6) Uani 1 1 d . . .
C10 C 0.4905(5) 0.5482(3) 0.30977(12) 0.0686(8) Uani 1 1 d . . .
C16 C 0.4122(6) 0.0314(3) 0.41211(13) 0.0710(8) Uani 1 1 d . . .
C5 C 0.9622(4) 0.6994(3) 0.36174(14) 0.0672(8) Uani 1 1 d . . .
C15 C 0.5919(6) -0.0100(4) 0.38644(13) 0.0753(9) Uani 1 1 d . . .
C8 C 0.8646(5) 0.7584(3) 0.23613(14) 0.0723(8) Uani 1 1 d . . .
C1 C 0.5030(7) 0.6296(4) 0.46626(14) 0.0776(10) Uani 1 1 d . . .
C14 C 0.7470(5) 0.0807(3) 0.37126(12) 0.0713(8) Uani 1 1 d . . .
C6 C 1.0870(6) 0.7790(4) 0.32547(17) 0.0855(10) Uani 1 1 d . . .
C7 C 1.0384(6) 0.8093(4) 0.26308(16) 0.0847(10) Uani 1 1 d . . .
H18 H 0.177(5) 0.444(4) 0.4729(15) 0.104(11) Uiso 1 1 d . . .
H13 H 0.835(4) 0.281(3) 0.3726(12) 0.068(8) Uiso 1 1 d . . .
H14 H 0.874(5) 0.045(3) 0.3520(14) 0.091(10) Uiso 1 1 d . . .
H2 H 0.737(4) 0.493(3) 0.4401(12) 0.064(7) Uiso 1 1 d . . .
H6 H 1.214(6) 0.809(4) 0.3433(19) 0.133(14) Uiso 1 1 d . . .
H7 H 1.138(5) 0.869(4) 0.2413(15) 0.100(11) Uiso 1 1 d . . .
H10 H 0.359(5) 0.499(3) 0.3074(15) 0.095(11) Uiso 1 1 d . . .
H1A H 0.362(5) 0.652(3) 0.4461(15) 0.087(10) Uiso 1 1 d . . .
H1B H 0.592(5) 0.706(3) 0.4634(13) 0.081(10) Uiso 1 1 d . . .
H1C H 0.469(5) 0.592(3) 0.5085(17) 0.098(10) Uiso 1 1 d . . .
H5 H 0.988(5) 0.684(3) 0.4060(16) 0.101(11) Uiso 1 1 d . . .
H15 H 0.621(5) -0.099(4) 0.3782(14) 0.086(10) Uiso 1 1 d . . .
H16 H 0.290(6) -0.026(4) 0.4250(17) 0.115(13) Uiso 1 1 d . . .
H2D H 0.495(7) 0.615(4) 0.219(2) 0.144(15) Uiso 1 1 d . . .
H1D H 0.113(6) 0.200(4) 0.4637(16) 0.114(13) Uiso 1 1 d . . .
H8 H 0.835(6) 0.780(4) 0.1903(19) 0.127(13) Uiso 1 1 d . . .
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'
N N 0.0061 0.0033 '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
C17 N1 C18 109.1(3) . . ?
C17 N1 H1D 123(2) . . ?
C18 N1 H1D 127(2) . . ?
C10 N2 C9 109.2(2) . . ?
C10 N2 H2D 125(3) . . ?
C9 N2 H2D 126(3) . . ?
C13 C12 C17 118.9(2) . . ?
C13 C12 C11 133.0(2) . . ?
C17 C12 C11 108.0(2) . . ?
C5 C4 C9 117.7(2) . . ?
C5 C4 C3 134.5(2) . . ?
C9 C4 C3 107.8(2) . . ?
C18 C11 C12 106.0(2) . . ?
C18 C11 C2 129.2(3) . . ?
C12 C11 C2 124.7(2) . . ?
C10 C3 C4 106.4(2) . . ?
C10 C3 C2 127.4(2) . . ?
C4 C3 C2 126.1(2) . . ?
C11 C2 C3 112.29(19) . . ?
C11 C2 C1 111.7(3) . . ?
C3 C2 C1 110.5(2) . . ?
C11 C2 H2 105.7(15) . . ?
C3 C2 H2 105.8(14) . . ?
C1 C2 H2 110.6(15) . . ?
N1 C17 C16 130.9(3) . . ?
N1 C17 C12 106.7(2) . . ?
C16 C17 C12 122.4(3) . . ?
C11 C18 N1 110.2(3) . . ?
C11 C18 H18 129.0(19) . . ?
N1 C18 H18 120.8(19) . . ?
C14 C13 C12 118.0(3) . . ?
C14 C13 H13 122.6(16) . . ?
C12 C13 H13 119.5(16) . . ?
N2 C9 C8 130.7(3) . . ?
N2 C9 C4 106.4(2) . . ?
C8 C9 C4 122.9(3) . . ?
C3 C10 N2 110.2(3) . . ?
C3 C10 H10 130.6(19) . . ?
N2 C10 H10 119.2(19) . . ?
C15 C16 C17 117.3(3) . . ?
C15 C16 H16 128(2) . . ?
C17 C16 H16 115(2) . . ?
C6 C5 C4 119.2(3) . . ?
C6 C5 H5 122(2) . . ?
C4 C5 H5 118(2) . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 H15 123(2) . . ?
C14 C15 H15 116(2) . . ?
C7 C8 C9 118.2(3) . . ?
C7 C8 H8 119(2) . . ?
C9 C8 H8 123(2) . . ?
C2 C1 H1A 104.8(18) . . ?
C2 C1 H1B 107.6(19) . . ?
H1A C1 H1B 110(3) . . ?
C2 C1 H1C 109.2(19) . . ?
H1A C1 H1C 105(3) . . ?
H1B C1 H1C 119(2) . . ?
C13 C14 C15 121.6(3) . . ?
C13 C14 H14 120(2) . . ?
C15 C14 H14 118(2) . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 118(3) . . ?
C7 C6 H6 120(3) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 124.6(19) . . ?
C6 C7 H7 114.9(19) . . ?
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
N1 C17 1.383(4) . ?
N1 C18 1.389(4) . ?
N1 H1D 0.91(4) . ?
N2 C10 1.387(3) . ?
N2 C9 1.391(3) . ?
N2 H2D 0.95(4) . ?
C12 C13 1.420(3) . ?
C12 C17 1.425(3) . ?
C12 C11 1.441(3) . ?
C4 C5 1.421(4) . ?
C4 C9 1.433(3) . ?
C4 C3 1.436(3) . ?
C11 C18 1.375(4) . ?
C11 C2 1.530(4) . ?
C3 C10 1.376(4) . ?
C3 C2 1.530(3) . ?
C2 C1 1.549(4) . ?
C2 H2 1.02(3) . ?
C17 C16 1.400(4) . ?
C18 H18 1.08(4) . ?
C13 C14 1.383(4) . ?
C13 H13 1.00(3) . ?
C9 C8 1.393(4) . ?
C10 H10 1.01(3) . ?
C16 C15 1.370(5) . ?
C16 H16 1.04(4) . ?
C5 C6 1.394(5) . ?
C5 H5 0.98(3) . ?
C15 C14 1.416(5) . ?
C15 H15 0.93(3) . ?
C8 C7 1.391(5) . ?
C8 H8 1.03(4) . ?
C1 H1A 1.05(3) . ?
C1 H1B 0.97(3) . ?
C1 H1C 1.01(4) . ?
C14 H14 1.00(3) . ?
C6 C7 1.419(5) . ?
C6 H6 0.98(4) . ?
C7 H7 1.01(4) . ?
