#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151876.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_7151876
loop_
_publ_author_name
'Chaitanya, T. Krishna'
'Nagarajan, Rajagopal'
_publ_section_title
;
 Synthesis of functionalized ellipticinium and ellipticine derivatives
 via electrophilic cyclization
;
_journal_issue                   12
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4662
_journal_paper_doi               10.1039/c1ob05258f
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C31 H24 Cl F3 N2 O3 S'
_chemical_formula_sum            'C31 H24 Cl F3 N2 O3 S'
_chemical_formula_weight         597.03
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.23(3)
_cell_angle_beta                 99.20(3)
_cell_angle_gamma                104.73(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1010(16)
_cell_length_b                   11.081(2)
_cell_length_c                   16.926(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.49
_cell_volume                     1412.1(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Phi and omega 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  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0924
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9776
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_correction_T_min  0.9013
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1654
_refine_ls_R_factor_gt           0.0954
_refine_ls_shift/su_max          0.116
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0806P)²+1.5027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1895
_refine_ls_wR_factor_ref         0.2240
_reflns_number_gt                2714
_reflns_number_total             4948
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05258f.txt
_cod_data_source_block           rn99_
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1412.1(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151876
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S 0.7627(2) 0.11271(16) 0.16036(11) 0.0696(5) Uani 1 1 d . . .
Cl1 Cl 0.4737(3) -0.34412(17) 0.53944(13) 0.1085(8) Uani 1 1 d . . .
N1 N 0.8258(5) 0.6755(4) 1.0160(3) 0.0428(11) Uani 1 1 d . . .
N2 N 0.7683(5) 0.1729(4) 0.7571(3) 0.0449(11) Uani 1 1 d . . .
C9 C 0.6927(6) 0.5166(5) 1.0717(3) 0.0386(12) Uani 1 1 d . . .
C15 C 0.8198(6) 0.5650(4) 0.9651(3) 0.0385(12) Uani 1 1 d . . .
C2 C 0.8541(6) 0.4227(5) 0.8510(3) 0.0395(12) Uani 1 1 d . . .
C8 C 0.7336(6) 0.4591(4) 0.9966(3) 0.0368(12) Uani 1 1 d . . .
C6 C 0.7620(6) 0.3160(5) 0.8796(3) 0.0390(12) Uani 1 1 d . . .
C7 C 0.7060(6) 0.3369(5) 0.9545(3) 0.0395(12) Uani 1 1 d . . .
H7 H 0.6512 0.2680 0.9747 0.047 Uiso 1 1 calc R . .
C3 C 0.9101(7) 0.3928(5) 0.7768(3) 0.0488(14) Uani 1 1 d . . .
H3 H 0.9782 0.4593 0.7589 0.059 Uiso 1 1 calc R . .
C1 C 0.8832(6) 0.5472(5) 0.8944(3) 0.0439(13) Uani 1 1 d . . .
H1 H 0.9437 0.6166 0.8764 0.053 Uiso 1 1 calc R . .
C5 C 0.7206(6) 0.1948(5) 0.8295(3) 0.0429(13) Uani 1 1 d . . .
H5 H 0.6571 0.1255 0.8466 0.051 Uiso 1 1 calc R . .
C14 C 0.7482(6) 0.6486(4) 1.0809(3) 0.0396(12) Uani 1 1 d . . .
C19 C 0.6942(7) 0.0454(5) 0.7043(3) 0.0432(13) Uani 1 1 d . . .
C25 C 0.9362(7) 0.2456(6) 0.6555(4) 0.0584(16) Uani 1 1 d . . .
C11 C 0.5920(7) 0.5472(5) 1.1978(3) 0.0459(13) Uani 1 1 d . . .
C10 C 0.6154(6) 0.4655(5) 1.1309(3) 0.0451(13) Uani 1 1 d . . .
H10 H 0.5797 0.3772 1.1256 0.054 Uiso 1 1 calc R . .
O2 O 0.9012(6) 0.0575(4) 0.1535(3) 0.0858(14) Uani 1 1 d . . .
C4 C 0.8691(7) 0.2725(5) 0.7308(3) 0.0475(14) Uani 1 1 d . . .
C21 C 0.6791(9) -0.1737(6) 0.6741(4) 0.0669(17) Uani 1 1 d . . .
H21 H 0.7146 -0.2425 0.6874 0.080 Uiso 1 1 calc R . .
C13 C 0.7230(7) 0.7319(5) 1.1463(3) 0.0508(14) Uani 1 1 d . . .
H13 H 0.7575 0.8202 1.1515 0.061 Uiso 1 1 calc R . .
C17 C 0.8975(7) 0.8040(5) 1.0038(3) 0.0520(14) Uani 1 1 d . . .
H17A H 0.9927 0.8044 0.9756 0.062 Uiso 1 1 calc R . .
H17B H 0.9446 0.8634 1.0570 0.062 Uiso 1 1 calc R . .
C12 C 0.6449(7) 0.6781(5) 1.2032(3) 0.0494(14) Uani 1 1 d . . .
H12 H 0.6266 0.7323 1.2475 0.059 Uiso 1 1 calc R . .
C24 C 0.5724(8) 0.0274(5) 0.6345(3) 0.0549(15) Uani 1 1 d . . .
H24 H 0.5368 0.0962 0.6214 0.066 Uiso 1 1 calc R . .
C26 C 1.0225(8) 0.1532(6) 0.6419(4) 0.0717(19) Uani 1 1 d . . .
H26 H 1.0321 0.1018 0.6793 0.086 Uiso 1 1 calc R . .
O3 O 0.7521(7) 0.2028(4) 0.1116(3) 0.0936(15) Uani 1 1 d . . .
C20 C 0.7486(8) -0.0538(5) 0.7252(4) 0.0595(16) Uani 1 1 d . . .
H20 H 0.8314 -0.0404 0.7732 0.071 Uiso 1 1 calc R . .
C22 C 0.5588(9) -0.1915(5) 0.6044(4) 0.0617(17) Uani 1 1 d . . .
C23 C 0.5022(8) -0.0925(6) 0.5833(4) 0.0655(17) Uani 1 1 d . . .
H23 H 0.4184 -0.1062 0.5356 0.079 Uiso 1 1 calc R . .
F3 F 0.9840(8) 0.2976(5) 0.2740(3) 0.1388(19) Uani 1 1 d . . .
O1 O 0.6022(6) 0.0261(5) 0.1610(4) 0.130(2) Uani 1 1 d . . .
C18 C 0.7628(8) 0.8488(6) 0.9548(4) 0.078(2) Uani 1 1 d . . .
H18A H 0.7181 0.7917 0.9015 0.117 Uiso 1 1 calc R . .
H18B H 0.8154 0.9337 0.9488 0.117 Uiso 1 1 calc R . .
H18C H 0.6688 0.8496 0.9829 0.117 Uiso 1 1 calc R . .
F1 F 0.7198(8) 0.2712(6) 0.2829(3) 0.171(3) Uani 1 1 d . . .
F2 F 0.8525(8) 0.1428(6) 0.3179(3) 0.158(2) Uani 1 1 d . . .
C30 C 0.9207(10) 0.3189(7) 0.5986(4) 0.084(2) Uani 1 1 d . . .
H30 H 0.8620 0.3807 0.6063 0.101 Uiso 1 1 calc R . .
C28 C 1.0790(13) 0.2109(11) 0.5192(6) 0.130(4) Uani 1 1 d . . .
H28 H 1.1288 0.1998 0.4736 0.156 Uiso 1 1 calc R . .
C31 C 0.8286(13) 0.2103(9) 0.2627(5) 0.092(2) Uani 1 1 d . . .
C29 C 0.9923(14) 0.3012(10) 0.5299(5) 0.126(3) Uani 1 1 d . . .
H29 H 0.9813 0.3505 0.4913 0.152 Uiso 1 1 calc R . .
C27 C 1.0933(10) 0.1367(9) 0.5746(5) 0.103(3) Uani 1 1 d . . .
H27 H 1.1516 0.0748 0.5664 0.124 Uiso 1 1 calc R . .
C16 C 0.5143(8) 0.4964(6) 1.2644(4) 0.0703(18) Uani 1 1 d . . .
H16A H 0.4457 0.5488 1.2849 0.105 Uiso 1 1 calc R . .
H16B H 0.6063 0.4979 1.3083 0.105 Uiso 1 1 calc R . .
H16C H 0.4412 0.4099 1.2425 0.105 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
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
O1 S1 O3 115.6(4) . . ?
O1 S1 O2 115.1(3) . . ?
O3 S1 O2 114.5(3) . . ?
O1 S1 C31 103.2(4) . . ?
O3 S1 C31 102.8(4) . . ?
O2 S1 C31 103.2(3) . . ?
C15 N1 C14 109.7(4) . . ?
C15 N1 C17 125.5(4) . . ?
C14 N1 C17 124.7(4) . . ?
C5 N2 C4 120.5(4) . . ?
C5 N2 C19 117.5(4) . . ?
C4 N2 C19 121.6(4) . . ?
C14 C9 C10 119.7(4) . . ?
C14 C9 C8 107.4(4) . . ?
C10 C9 C8 132.9(5) . . ?
N1 C15 C1 129.2(5) . . ?
N1 C15 C8 108.8(4) . . ?
C1 C15 C8 122.1(4) . . ?
C1 C2 C3 123.0(5) . . ?
C1 C2 C6 120.7(5) . . ?
C3 C2 C6 116.4(5) . . ?
C7 C8 C15 120.0(4) . . ?
C7 C8 C9 134.6(5) . . ?
C15 C8 C9 105.3(4) . . ?
C5 C6 C7 121.7(5) . . ?
C5 C6 C2 118.1(5) . . ?
C7 C6 C2 120.1(4) . . ?
C8 C7 C6 119.0(4) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C4 C3 C2 123.0(5) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C15 C1 C2 118.0(5) . . ?
C15 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
N2 C5 C6 122.8(5) . . ?
N2 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C9 C14 C13 121.7(5) . . ?
C9 C14 N1 108.8(4) . . ?
C13 C14 N1 129.5(5) . . ?
C24 C19 C20 121.3(5) . . ?
C24 C19 N2 119.2(5) . . ?
C20 C19 N2 119.5(5) . . ?
C30 C25 C26 118.6(6) . . ?
C30 C25 C4 119.1(6) . . ?
C26 C25 C4 122.2(6) . . ?
C12 C11 C10 118.7(5) . . ?
C12 C11 C16 120.0(5) . . ?
C10 C11 C16 121.3(5) . . ?
C11 C10 C9 119.6(5) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C3 C4 N2 118.9(5) . . ?
C3 C4 C25 121.0(5) . . ?
N2 C4 C25 120.1(5) . . ?
C22 C21 C20 119.8(6) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C12 C13 C14 117.0(5) . . ?
C12 C13 H13 121.5 . . ?
C14 C13 H13 121.5 . . ?
N1 C17 C18 112.4(4) . . ?
N1 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
N1 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C13 C12 C11 123.3(5) . . ?
C13 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C19 C24 C23 120.0(5) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C27 C26 C25 120.8(8) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C19 C20 C21 119.0(6) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C21 C22 C23 121.6(5) . . ?
C21 C22 Cl1 119.3(5) . . ?
C23 C22 Cl1 119.1(5) . . ?
C24 C23 C22 118.3(6) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C25 C30 C29 120.3(8) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C27 C28 C29 120.7(9) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.6 . . ?
F1 C31 F2 107.2(7) . . ?
F1 C31 F3 107.3(8) . . ?
F2 C31 F3 104.4(8) . . ?
F1 C31 S1 114.1(7) . . ?
F2 C31 S1 111.9(6) . . ?
F3 C31 S1 111.4(6) . . ?
C28 C29 C30 119.5(9) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C26 C27 C28 120.1(9) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
S1 O1 1.409(5) . ?
S1 O3 1.414(4) . ?
S1 O2 1.418(4) . ?
S1 C31 1.788(9) . ?
Cl1 C22 1.745(6) . ?
N1 C15 1.351(6) . ?
N1 C14 1.390(6) . ?
N1 C17 1.459(6) . ?
N2 C5 1.343(6) . ?
N2 C4 1.384(6) . ?
N2 C19 1.450(6) . ?
C9 C14 1.388(6) . ?
C9 C10 1.392(7) . ?
C9 C8 1.445(6) . ?
C15 C1 1.379(7) . ?
C15 C8 1.439(7) . ?
C2 C1 1.385(7) . ?
C2 C3 1.416(7) . ?
C2 C6 1.435(7) . ?
C8 C7 1.358(6) . ?
C6 C5 1.382(6) . ?
C6 C7 1.414(6) . ?
C7 H7 0.9300 . ?
C3 C4 1.348(7) . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?
C5 H5 0.9300 . ?
C14 C13 1.388(7) . ?
C19 C24 1.361(7) . ?
C19 C20 1.365(7) . ?
C25 C30 1.377(8) . ?
C25 C26 1.387(8) . ?
C25 C4 1.476(7) . ?
C11 C12 1.386(7) . ?
C11 C10 1.390(7) . ?
C11 C16 1.501(7) . ?
C10 H10 0.9300 . ?
C21 C22 1.355(8) . ?
C21 C20 1.373(8) . ?
C21 H21 0.9300 . ?
C13 C12 1.375(7) . ?
C13 H13 0.9300 . ?
C17 C18 1.502(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C12 H12 0.9300 . ?
C24 C23 1.374(7) . ?
C24 H24 0.9300 . ?
C26 C27 1.359(9) . ?
C26 H26 0.9300 . ?
C20 H20 0.9300 . ?
C22 C23 1.373(8) . ?
C23 H23 0.9300 . ?
F3 C31 1.340(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F1 C31 1.291(8) . ?
F2 C31 1.318(8) . ?
C30 C29 1.385(10) . ?
C30 H30 0.9300 . ?
C28 C27 1.362(13) . ?
C28 C29 1.364(13) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C27 H27 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26997445
2 PubChem 53309464
