#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/79/4027946.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_4027946
loop_
_publ_author_name
'Jan Vávra'
'Lukáš Severa'
'Ivana Císařová'
'Blanka Klepetářová'
'David Šaman'
'Dušan Koval'
'Václav Kašička'
'Filip Teplý'
_publ_section_title
;
 Search for Conglomerate in Set of [7]Helquat Salts: Multigram Resolution
 of Helicene-Viologen Hybrid by Preferential Crystallization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1329
_journal_page_last               1342
_journal_paper_doi               10.1021/jo301615k
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C30 H26 N2, 2(I)'
_chemical_formula_sum            'C30 H26 I2 N2'
_chemical_formula_weight         668.33
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.3229(4)
_cell_length_b                   18.3554(5)
_cell_length_c                   22.9405(6)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.67
_cell_volume                     5189.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            42564
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.445
_exptl_absorpt_correction_T_max  0.6813
_exptl_absorpt_correction_T_min  0.3657
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_description       prism
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_refine_diff_density_max         2.221
_refine_diff_density_min         -1.593
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0261P)²+12.3709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0788
_reflns_number_gt                4905
_reflns_number_total             5967
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo301615k_2_I.cif
_cod_data_source_block           jv_1916_acoet
_cod_database_code               4027946
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'
'-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
C11 C 0.0930(2) 0.22750(18) 0.32661(13) 0.0221(6) Uani 1 1 d .
H11 H 0.0889 0.2030 0.3630 0.027 Uiso 1 1 calc R
C12 C 0.0460(3) 0.1972(2) 0.27845(15) 0.0285(7) Uani 1 1 d .
H12 H 0.0105 0.1514 0.2814 0.034 Uiso 1 1 calc R
C13 C 0.0499(3) 0.2335(2) 0.22430(15) 0.0327(8) Uani 1 1 d .
H13 H 0.0194 0.2110 0.1908 0.039 Uiso 1 1 calc R
C14 C 0.0970(3) 0.3006(2) 0.21953(14) 0.0316(8) Uani 1 1 d .
H14 H 0.0960 0.3253 0.1831 0.038 Uiso 1 1 calc R
C15 C 0.1473(3) 0.33371(19) 0.26839(14) 0.0262(7) Uani 1 1 d .
C16 C 0.1938(3) 0.4036(2) 0.26671(16) 0.0336(8) Uani 1 1 d .
H16 H 0.1979 0.4292 0.2308 0.040 Uiso 1 1 calc R
C17 C 0.2325(3) 0.43461(19) 0.31583(16) 0.0328(8) Uani 1 1 d .
H17 H 0.2572 0.4836 0.3149 0.039 Uiso 1 1 calc R
N18 N 0.2365(2) 0.39659(15) 0.36682(12) 0.0258(6) Uani 1 1 d .
C19 C 0.2757(3) 0.43347(19) 0.42070(16) 0.0324(8) Uani 1 1 d .
H19A H 0.2657 0.4868 0.4170 0.039 Uiso 1 1 calc R
H19B H 0.3540 0.4236 0.4261 0.039 Uiso 1 1 calc R
C21 C 0.8917(2) 0.19669(17) 0.42140(13) 0.0184(6) Uani 1 1 d .
H21 H 0.8772 0.1710 0.3863 0.022 Uiso 1 1 calc R
C22 C 0.9307(2) 0.15976(18) 0.46879(13) 0.0232(7) Uani 1 1 d .
H22 H 0.9423 0.1087 0.4665 0.028 Uiso 1 1 calc R
C23 C 0.9538(3) 0.19721(19) 0.52127(14) 0.0280(7) Uani 1 1 d .
H23 H 0.9786 0.1709 0.5543 0.034 Uiso 1 1 calc R
C24 C 0.9405(3) 0.27107(19) 0.52462(14) 0.0283(7) Uani 1 1 d .
H24 H 0.9578 0.2959 0.5597 0.034 Uiso 1 1 calc R
C25 C 0.9012(2) 0.31057(17) 0.47628(13) 0.0217(6) Uani 1 1 d .
C26 C 0.8902(3) 0.38714(19) 0.47762(14) 0.0291(7) Uani 1 1 d .
H26 H 0.9033 0.4130 0.5128 0.035 Uiso 1 1 calc R
C27 C 0.8611(3) 0.42355(18) 0.42895(15) 0.0290(7) Uani 1 1 d .
H27 H 0.8600 0.4753 0.4292 0.035 Uiso 1 1 calc R
N28 N 0.8332(2) 0.38705(14) 0.37933(11) 0.0203(5) Uani 1 1 d .
C29 C 0.8067(3) 0.42955(17) 0.32632(14) 0.0256(7) Uani 1 1 d .
H29A H 0.8368 0.4794 0.3295 0.031 Uiso 1 1 calc R
H29B H 0.7270 0.4332 0.3217 0.031 Uiso 1 1 calc R
C110 C 0.2131(3) 0.40582(18) 0.47284(15) 0.0297(7) Uani 1 1 d .
H11A H 0.2401 0.4295 0.5088 0.036 Uiso 1 1 calc R
H11B H 0.1351 0.4177 0.4684 0.036 Uiso 1 1 calc R
C111 C 0.2277(2) 0.32434(18) 0.47709(14) 0.0230(6) Uani 1 1 d .
C112 C 0.2390(3) 0.28768(19) 0.53024(13) 0.0267(7) Uani 1 1 d .
C128 C 0.2344(2) 0.28701(16) 0.42409(13) 0.0196(6) Uani 1 1 d .
C129 C 0.2049(2) 0.32659(16) 0.37018(13) 0.0201(6) Uani 1 1 d .
C130 C 0.1478(2) 0.29540(17) 0.32278(13) 0.0205(6) Uani 1 1 d .
C131 C 0.2241(3) 0.3297(2) 0.58608(15) 0.0391(9) Uani 1 1 d .
H13A H 0.2904 0.3571 0.5948 0.059 Uiso 1 1 calc R
H13B H 0.2089 0.2958 0.6180 0.059 Uiso 1 1 calc R
H13C H 0.1631 0.3636 0.5818 0.059 Uiso 1 1 calc R
C210 C 0.8557(3) 0.39089(18) 0.27429(14) 0.0250(7) Uani 1 1 d .
H21A H 0.8409 0.4188 0.2382 0.030 Uiso 1 1 calc R
H21B H 0.9353 0.3868 0.2791 0.030 Uiso 1 1 calc R
C211 C 0.8056(2) 0.31604(17) 0.27013(13) 0.0195(6) Uani 1 1 d .
C212 C 0.7778(2) 0.28326(17) 0.21715(13) 0.0217(6) Uani 1 1 d .
C228 C 0.7819(2) 0.28196(15) 0.32338(12) 0.0168(6) Uani 1 1 d .
C229 C 0.8295(2) 0.31373(16) 0.37669(12) 0.0164(6) Uani 1 1 d .
C230 C 0.8728(2) 0.27296(16) 0.42397(12) 0.0171(6) Uani 1 1 d .
C231 C 0.8105(3) 0.3181(2) 0.16032(14) 0.0311(8) Uani 1 1 d .
H23A H 0.7490 0.3453 0.1443 0.047 Uiso 1 1 calc R
H23B H 0.8325 0.2802 0.1326 0.047 Uiso 1 1 calc R
H23C H 0.8714 0.3514 0.1671 0.047 Uiso 1 1 calc R
I1 I 0.958373(19) 0.059861(13) 0.139038(10) 0.03342(7) Uani 1 1 d .
I2 I 0.54071(2) 0.516982(14) 0.375283(13) 0.04528(9) Uani 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'
I I -0.4742 1.8119 '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
C12 C11 C130 120.6(3) . .
C12 C11 H11 119.7 . .
C130 C11 H11 119.7 . .
C11 C12 C13 120.3(3) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C14 C13 C12 120.8(3) . .
C14 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
C13 C14 C15 120.6(3) . .
C13 C14 H14 119.7 . .
C15 C14 H14 119.7 . .
C16 C15 C14 123.2(3) . .
C16 C15 C130 118.1(3) . .
C14 C15 C130 118.7(3) . .
C17 C16 C15 120.4(3) . .
C17 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
C16 C17 N18 120.9(3) . .
C16 C17 H17 119.5 . .
N18 C17 H17 119.5 . .
C129 N18 C17 121.8(3) . .
C129 N18 C19 118.7(3) . .
C17 N18 C19 119.4(3) . .
N18 C19 C110 109.8(3) . .
N18 C19 H19A 109.7 . .
C110 C19 H19A 109.7 . .
N18 C19 H19B 109.7 . .
C110 C19 H19B 109.7 . .
H19A C19 H19B 108.2 . .
C22 C21 C230 120.9(3) . .
C22 C21 H21 119.6 . .
C230 C21 H21 119.6 . .
C21 C22 C23 120.4(3) . .
C21 C22 H22 119.8 . .
C23 C22 H22 119.8 . .
C24 C23 C22 120.3(3) . .
C24 C23 H23 119.8 . .
C22 C23 H23 119.8 . .
C23 C24 C25 120.4(3) . .
C23 C24 H24 119.8 . .
C25 C24 H24 119.8 . .
C24 C25 C26 121.8(3) . .
C24 C25 C230 119.7(3) . .
C26 C25 C230 118.4(3) . .
C27 C26 C25 120.0(3) . .
C27 C26 H26 120.0 . .
C25 C26 H26 120.0 . .
C26 C27 N28 120.9(3) . .
C26 C27 H27 119.5 . .
N28 C27 H27 119.5 . .
C229 N28 C27 122.4(3) . .
C229 N28 C29 118.8(3) . .
C27 N28 C29 118.8(3) . .
N28 C29 C210 108.2(2) . .
N28 C29 H29A 110.1 . .
C210 C29 H29A 110.1 . .
N28 C29 H29B 110.1 . .
C210 C29 H29B 110.1 . .
H29A C29 H29B 108.4 . .
C111 C110 C19 108.8(3) . .
C111 C110 H11A 109.9 . .
C19 C110 H11A 109.9 . .
C111 C110 H11B 109.9 . .
C19 C110 H11B 109.9 . .
H11A C110 H11B 108.3 . .
C128 C111 C112 121.1(3) . .
C128 C111 C110 115.9(3) . .
C112 C111 C110 123.0(3) . .
C111 C112 C112 119.41(19) . 4
C111 C112 C131 118.8(3) . .
C112 C112 C131 121.7(2) 4 .
C111 C128 C128 119.20(18) . 4
C111 C128 C129 118.1(3) . .
C128 C128 C129 122.64(17) 4 .
N18 C129 C130 119.1(3) . .
N18 C129 C128 116.4(3) . .
C130 C129 C128 124.4(3) . .
C129 C130 C11 122.9(3) . .
C129 C130 C15 118.2(3) . .
C11 C130 C15 118.9(3) . .
C112 C131 H13A 109.5 . .
C112 C131 H13B 109.5 . .
H13A C131 H13B 109.5 . .
C112 C131 H13C 109.5 . .
H13A C131 H13C 109.5 . .
H13B C131 H13C 109.5 . .
C211 C210 C29 108.3(3) . .
C211 C210 H21A 110.0 . .
C29 C210 H21A 110.0 . .
C211 C210 H21B 110.0 . .
C29 C210 H21B 110.0 . .
H21A C210 H21B 108.4 . .
C212 C211 C228 120.9(3) . .
C212 C211 C210 123.2(3) . .
C228 C211 C210 115.8(3) . .
C211 C212 C212 119.69(18) . 4_655
C211 C212 C231 120.2(3) . .
C212 C212 C231 120.07(19) 4_655 .
C211 C228 C228 119.09(17) . 4_655
C211 C228 C229 117.5(3) . .
C228 C228 C229 123.33(16) 4_655 .
N28 C229 C230 118.6(3) . .
N28 C229 C228 116.4(3) . .
C230 C229 C228 125.0(3) . .
C21 C230 C229 123.3(3) . .
C21 C230 C25 118.1(3) . .
C229 C230 C25 118.6(3) . .
C212 C231 H23A 109.5 . .
C212 C231 H23B 109.5 . .
H23A C231 H23B 109.5 . .
C212 C231 H23C 109.5 . .
H23A C231 H23C 109.5 . .
H23B C231 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 C12 1.366(4) .
C11 C130 1.421(4) .
C11 H11 0.9500 .
C12 C13 1.411(5) .
C12 H12 0.9500 .
C13 C14 1.366(5) .
C13 H13 0.9500 .
C14 C15 1.418(5) .
C14 H14 0.9500 .
C15 C16 1.405(5) .
C15 C130 1.432(4) .
C16 C17 1.349(5) .
C16 H16 0.9500 .
C17 N18 1.363(4) .
C17 H17 0.9500 .
N18 C129 1.345(4) .
N18 C19 1.490(4) .
C19 C110 1.511(5) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C21 C22 1.368(4) .
C21 C230 1.420(4) .
C21 H21 0.9500 .
C22 C23 1.415(4) .
C22 H22 0.9500 .
C23 C24 1.368(5) .
C23 H23 0.9500 .
C24 C25 1.410(5) .
C24 H24 0.9500 .
C25 C26 1.412(5) .
C25 C230 1.428(4) .
C26 C27 1.350(5) .
C26 H26 0.9500 .
C27 N28 1.365(4) .
C27 H27 0.9500 .
N28 C229 1.348(4) .
N28 C29 1.481(4) .
C29 C210 1.514(4) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C110 C111 1.510(5) .
C110 H11A 0.9900 .
C110 H11B 0.9900 .
C111 C128 1.398(4) .
C111 C112 1.400(5) .
C112 C112 1.409(7) 4
C112 C131 1.507(5) .
C128 C128 1.411(6) 4
C128 C129 1.480(4) .
C129 C130 1.416(4) .
C131 H13A 0.9800 .
C131 H13B 0.9800 .
C131 H13C 0.9800 .
C210 C211 1.509(4) .
C210 H21A 0.9900 .
C210 H21B 0.9900 .
C211 C212 1.399(4) .
C211 C228 1.403(4) .
C212 C212 1.399(6) 4_655
C212 C231 1.507(4) .
C228 C228 1.413(6) 4_655
C228 C229 1.476(4) .
C229 C230 1.421(4) .
C231 H23A 0.9800 .
C231 H23B 0.9800 .
C231 H23C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139092551
