#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/39/4123917.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_4123917
loop_
_publ_author_name
'Fujikawa, Takao'
'Segawa, Yasutomo'
'Itami, Kenichiro'
_publ_section_title
;
 Synthesis, Structures, and Properties of π-Extended Double Helicene: A
 Combination of Planar and Nonplanar π-Systems.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7763
_journal_page_last               7768
_journal_paper_doi               10.1021/jacs.5b03118
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C58 H28'
_chemical_formula_weight         724.80
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.688(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.056(8)
_cell_length_b                   39.67(3)
_cell_length_c                   7.531(5)
_cell_measurement_reflns_used    2446
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      25.2954
_cell_measurement_theta_min      3.1327
_cell_volume                     3273(4)
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_collection       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_molecular_graphics    ORTEP-III
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Saturn724 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14225
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0736
_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)+(0.0806P)²+2.5332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1861
_reflns_number_gt                1951
_reflns_number_total             2877
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b03118_si_002.cif
_cod_data_source_block           DH
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity' tag as specified in the
replacement file
'/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 3376 2015-05-07 07:48:27Z andrius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4123917
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4705(2) 0.74999(7) 0.6573(4) 0.0353(7) Uani 1 1 d .
C2 C 0.4422(3) 0.78003(8) 0.5656(5) 0.0467(9) Uani 1 1 d .
H1 H 0.4645 0.8009 0.6226 0.056 Uiso 1 1 calc R
C3 C 0.3809(3) 0.77980(8) 0.3897(5) 0.0516(10) Uani 1 1 d .
H2 H 0.3630 0.8005 0.3285 0.062 Uiso 1 1 calc R
C4 C 0.3467(3) 0.74995(7) 0.3053(5) 0.0447(8) Uani 1 1 d .
H3 H 0.3027 0.7502 0.1879 0.054 Uiso 1 1 calc R
C5 C 0.3760(3) 0.71899(7) 0.3909(4) 0.0357(8) Uani 1 1 d .
C6 C 0.4390(2) 0.71871(7) 0.5684(4) 0.0321(7) Uani 1 1 d .
C7 C 0.3463(3) 0.68703(7) 0.2992(4) 0.0336(7) Uani 1 1 d .
C8 C 0.2921(3) 0.68596(8) 0.1165(4) 0.0420(8) Uani 1 1 d .
H4 H 0.2673 0.7064 0.0566 0.050 Uiso 1 1 calc R
C9 C 0.2754(3) 0.65663(9) 0.0271(4) 0.0430(8) Uani 1 1 d .
H5 H 0.2362 0.6565 -0.0932 0.052 Uiso 1 1 calc R
C10 C 0.3151(3) 0.62614(8) 0.1095(4) 0.0355(7) Uani 1 1 d .
H6 H 0.3089 0.6057 0.0430 0.043 Uiso 1 1 calc R
C11 C 0.3631(3) 0.62610(7) 0.2873(4) 0.0318(7) Uani 1 1 d .
H13 H 0.3889 0.6054 0.3430 0.038 Uiso 1 1 calc R
C12 C 0.3751(2) 0.65608(7) 0.3899(4) 0.0297(7) Uani 1 1 d .
C13 C 0.4672(2) 0.68715(7) 0.6607(4) 0.0276(7) Uani 1 1 d .
C14 C 0.4263(2) 0.65660(7) 0.5801(4) 0.0278(7) Uani 1 1 d .
C15 C 0.4498(2) 0.62554(7) 0.6801(4) 0.0273(7) Uani 1 1 d .
C16 C 0.3808(2) 0.59436(7) 0.6501(4) 0.0273(7) Uani 1 1 d .
C17 C 0.2493(2) 0.59439(7) 0.5867(4) 0.0294(7) Uani 1 1 d .
C18 C 0.1779(3) 0.62424(7) 0.5777(4) 0.0356(7) Uani 1 1 d .
H14 H 0.2166 0.6451 0.6109 0.043 Uiso 1 1 calc R
C19 C 0.0539(3) 0.62375(8) 0.5221(4) 0.0399(8) Uani 1 1 d .
H7 H 0.0084 0.6441 0.5156 0.048 Uiso 1 1 calc R
C20 C -0.0034(3) 0.59367(8) 0.4760(5) 0.0531(10) Uani 1 1 d .
H8 H -0.0885 0.5933 0.4351 0.064 Uiso 1 1 calc R
C21 C 0.0617(3) 0.56418(8) 0.4890(5) 0.0457(9) Uani 1 1 d .
H9 H 0.0203 0.5436 0.4591 0.055 Uiso 1 1 calc R
C22 C 0.1882(2) 0.56355(7) 0.5452(4) 0.0313(7) Uani 1 1 d .
C23 C 0.2548(3) 0.53201(7) 0.5674(4) 0.0300(7) Uani 1 1 d .
C24 C 0.2026(3) 0.50132(7) 0.5079(4) 0.0344(7) Uani 1 1 d .
H10 H 0.1229 0.5010 0.4427 0.041 Uiso 1 1 calc R
C25 C 0.2652(3) 0.47126(7) 0.5423(4) 0.0371(8) Uani 1 1 d .
H11 H 0.2283 0.4507 0.4989 0.044 Uiso 1 1 calc R
C26 C 0.3804(3) 0.47079(7) 0.6388(4) 0.0292(7) Uani 1 1 d .
H12 H 0.4207 0.4499 0.6646 0.035 Uiso 1 1 calc R
C27 C 0.4386(2) 0.50072(7) 0.6992(3) 0.0280(7) Uani 1 1 d .
C28 C 0.3765(2) 0.53201(6) 0.6593(3) 0.0262(6) Uani 1 1 d .
C29 C 0.4387(2) 0.56374(6) 0.7044(3) 0.0245(6) 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'
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
C2 C1 C6 119.1(3) . .
C2 C1 C1 121.1(2) . 2_656
C6 C1 C1 119.81(17) . 2_656
C1 C2 C3 120.7(3) . .
C1 C2 H1 119.7 . .
C3 C2 H1 119.7 . .
C4 C3 C2 120.7(3) . .
C4 C3 H2 119.7 . .
C2 C3 H2 119.7 . .
C3 C4 C5 120.6(3) . .
C3 C4 H3 119.7 . .
C5 C4 H3 119.7 . .
C4 C5 C6 119.5(3) . .
C4 C5 C7 121.2(3) . .
C6 C5 C7 119.3(3) . .
C5 C6 C1 119.4(3) . .
C5 C6 C13 120.4(3) . .
C1 C6 C13 120.2(3) . .
C12 C7 C8 118.5(3) . .
C12 C7 C5 120.1(3) . .
C8 C7 C5 121.4(3) . .
C9 C8 C7 121.4(3) . .
C9 C8 H4 119.3 . .
C7 C8 H4 119.3 . .
C8 C9 C10 120.7(3) . .
C8 C9 H5 119.7 . .
C10 C9 H5 119.7 . .
C11 C10 C9 119.3(3) . .
C11 C10 H6 120.3 . .
C9 C10 H6 120.3 . .
C10 C11 C12 121.9(3) . .
C10 C11 H13 119.1 . .
C12 C11 H13 119.1 . .
C11 C12 C7 117.7(3) . .
C11 C12 C14 122.7(2) . .
C7 C12 C14 119.3(3) . .
C14 C13 C13 119.81(16) . 2_656
C14 C13 C6 120.2(3) . .
C13 C13 C6 119.88(17) 2_656 .
C13 C14 C15 119.0(3) . .
C13 C14 C12 119.6(2) . .
C15 C14 C12 120.9(2) . .
C15 C15 C14 116.90(17) 2_656 .
C15 C15 C16 117.09(17) 2_656 .
C14 C15 C16 126.0(2) . .
C29 C16 C15 118.7(2) . .
C29 C16 C17 119.1(2) . .
C15 C16 C17 121.7(2) . .
C22 C17 C18 117.8(3) . .
C22 C17 C16 119.6(2) . .
C18 C17 C16 122.4(3) . .
C19 C18 C17 121.7(3) . .
C19 C18 H14 119.1 . .
C17 C18 H14 119.1 . .
C20 C19 C18 119.7(3) . .
C20 C19 H7 120.1 . .
C18 C19 H7 120.1 . .
C21 C20 C19 120.2(3) . .
C21 C20 H8 119.9 . .
C19 C20 H8 119.9 . .
C20 C21 C22 121.9(3) . .
C20 C21 H9 119.0 . .
C22 C21 H9 119.0 . .
C21 C22 C17 118.5(3) . .
C21 C22 C23 121.3(3) . .
C17 C22 C23 120.2(3) . .
C24 C23 C28 118.5(3) . .
C24 C23 C22 122.3(3) . .
C28 C23 C22 119.1(2) . .
C25 C24 C23 121.1(3) . .
C25 C24 H10 119.4 . .
C23 C24 H10 119.4 . .
C26 C25 C24 120.8(3) . .
C26 C25 H11 119.6 . .
C24 C25 H11 119.6 . .
C25 C26 C27 120.8(3) . .
C25 C26 H12 119.6 . .
C27 C26 H12 119.6 . .
C26 C27 C28 118.8(2) . .
C26 C27 C27 121.57(16) . 2_656
C28 C27 C27 119.61(15) . 2_656
C23 C28 C27 119.7(2) . .
C23 C28 C29 119.9(2) . .
C27 C28 C29 120.3(2) . .
C16 C29 C29 120.16(15) . 2_656
C16 C29 C28 119.8(2) . .
C29 C29 C28 119.94(15) 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.392(4) .
C1 C6 1.431(4) .
C1 C1 1.460(6) 2_656
C2 C3 1.405(5) .
C2 H1 0.9500 .
C3 C4 1.373(4) .
C3 H2 0.9500 .
C4 C5 1.405(4) .
C4 H3 0.9500 .
C5 C6 1.422(4) .
C5 C7 1.460(4) .
C6 C13 1.446(4) .
C7 C12 1.421(4) .
C7 C8 1.426(4) .
C8 C9 1.345(5) .
C8 H4 0.9500 .
C9 C10 1.403(4) .
C9 H5 0.9500 .
C10 C11 1.372(4) .
C10 H6 0.9500 .
C11 C12 1.415(4) .
C11 H13 0.9500 .
C12 C14 1.468(4) .
C13 C14 1.403(4) .
C13 C13 1.440(5) 2_656
C14 C15 1.450(4) .
C15 C15 1.424(5) 2_656
C15 C16 1.455(4) .
C16 C29 1.408(4) .
C16 C17 1.469(4) .
C17 C22 1.412(4) .
C17 C18 1.419(4) .
C18 C19 1.379(4) .
C18 H14 0.9500 .
C19 C20 1.374(4) .
C19 H7 0.9500 .
C20 C21 1.371(4) .
C20 H8 0.9500 .
C21 C22 1.406(4) .
C21 H9 0.9500 .
C22 C23 1.450(4) .
C23 C24 1.395(4) .
C23 C28 1.429(4) .
C24 C25 1.386(4) .
C24 H10 0.9500 .
C25 C26 1.380(4) .
C25 H11 0.9500 .
C26 C27 1.397(4) .
C26 H12 0.9500 .
C27 C28 1.431(4) .
C27 C27 1.467(5) 2_656
C28 C29 1.453(4) .
C29 C29 1.435(5) 2_656
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 1.4(5) . .
C1 C1 C2 C3 -177.4(3) 2_656 .
C1 C2 C3 C4 0.7(5) . .
C2 C3 C4 C5 -2.3(5) . .
C3 C4 C5 C6 1.6(5) . .
C3 C4 C5 C7 -176.5(3) . .
C4 C5 C6 C1 0.5(4) . .
C7 C5 C6 C1 178.7(3) . .
C4 C5 C6 C13 178.4(3) . .
C7 C5 C6 C13 -3.4(4) . .
C2 C1 C6 C5 -2.0(4) . .
C1 C1 C6 C5 176.8(3) 2_656 .
C2 C1 C6 C13 -179.9(3) . .
C1 C1 C6 C13 -1.1(5) 2_656 .
C4 C5 C7 C12 -178.9(3) . .
C6 C5 C7 C12 2.9(4) . .
C4 C5 C7 C8 3.3(5) . .
C6 C5 C7 C8 -174.9(3) . .
C12 C7 C8 C9 -4.2(5) . .
C5 C7 C8 C9 173.6(3) . .
C7 C8 C9 C10 -2.4(5) . .
C8 C9 C10 C11 5.0(5) . .
C9 C10 C11 C12 -0.8(4) . .
C10 C11 C12 C7 -5.7(4) . .
C10 C11 C12 C14 -179.9(3) . .
C8 C7 C12 C11 8.0(4) . .
C5 C7 C12 C11 -169.8(3) . .
C8 C7 C12 C14 -177.5(3) . .
C5 C7 C12 C14 4.6(4) . .
C5 C6 C13 C14 -3.9(4) . .
C1 C6 C13 C14 174.0(3) . .
C5 C6 C13 C13 178.9(3) . 2_656
C1 C6 C13 C13 -3.2(5) . 2_656
C13 C13 C14 C15 0.8(5) 2_656 .
C6 C13 C14 C15 -176.4(2) . .
C13 C13 C14 C12 -171.3(3) 2_656 .
C6 C13 C14 C12 11.5(4) . .
C11 C12 C14 C13 162.3(3) . .
C7 C12 C14 C13 -11.9(4) . .
C11 C12 C14 C15 -9.6(4) . .
C7 C12 C14 C15 176.2(2) . .
C13 C14 C15 C15 -23.9(4) . 2_656
C12 C14 C15 C15 148.1(3) . 2_656
C13 C14 C15 C16 156.5(3) . .
C12 C14 C15 C16 -31.6(4) . .
C15 C15 C16 C29 -24.2(4) 2_656 .
C14 C15 C16 C29 155.4(3) . .
C15 C15 C16 C17 147.8(3) 2_656 .
C14 C15 C16 C17 -32.6(4) . .
C29 C16 C17 C22 -13.3(4) . .
C15 C16 C17 C22 174.7(3) . .
C29 C16 C17 C18 161.8(3) . .
C15 C16 C17 C18 -10.1(4) . .
C22 C17 C18 C19 -3.1(5) . .
C16 C17 C18 C19 -178.4(3) . .
C17 C18 C19 C20 0.9(5) . .
C18 C19 C20 C21 1.4(5) . .
C19 C20 C21 C22 -1.4(6) . .
C20 C21 C22 C17 -1.0(5) . .
C20 C21 C22 C23 176.7(3) . .
C18 C17 C22 C21 3.1(4) . .
C16 C17 C22 C21 178.5(3) . .
C18 C17 C22 C23 -174.6(3) . .
C16 C17 C22 C23 0.8(4) . .
C21 C22 C23 C24 10.5(5) . .
C17 C22 C23 C24 -171.9(3) . .
C21 C22 C23 C28 -167.1(3) . .
C17 C22 C23 C28 10.5(4) . .
C28 C23 C24 C25 2.3(4) . .
C22 C23 C24 C25 -175.3(3) . .
C23 C24 C25 C26 0.9(5) . .
C24 C25 C26 C27 -2.2(4) . .
C25 C26 C27 C28 0.1(4) . .
C25 C26 C27 C27 -179.6(3) . 2_656
C24 C23 C28 C27 -4.3(4) . .
C22 C23 C28 C27 173.3(2) . .
C24 C23 C28 C29 172.8(2) . .
C22 C23 C28 C29 -9.6(4) . .
C26 C27 C28 C23 3.2(4) . .
C27 C27 C28 C23 -177.2(3) 2_656 .
C26 C27 C28 C29 -173.9(2) . .
C27 C27 C28 C29 5.7(4) 2_656 .
C15 C16 C29 C29 3.1(5) . 2_656
C17 C16 C29 C29 -169.1(3) . 2_656
C15 C16 C29 C28 -173.5(2) . .
C17 C16 C29 C28 14.3(4) . .
C23 C28 C29 C16 -2.9(4) . .
C27 C28 C29 C16 174.2(2) . .
C23 C28 C29 C29 -179.5(3) . 2_656
C27 C28 C29 C29 -2.4(5) . 2_656
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-05-07T03:25:00+03:00
;
 Replaced the '&#x00C2;&#x00A5;' sequence with a backslash symbol ('\')
 in the value of the '_diffrn_measurement_method' data item.
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 122402220
