#------------------------------------------------------------------------------
#$Date: 2021-01-04 05:11:55 +0200 (Mon, 04 Jan 2021) $
#$Revision: 260424 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/54/4135404.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_4135404
loop_
_publ_author_name
'Saal, Fridolin'
'Zhang, Fangyuan'
'Holzapfel, Marco'
'Stolte, Matthias'
'Michail, Evripidis'
'Moos, Michael'
'Schmiedel, Alexander'
'Krause, Ana-Maria'
'Lambert, Christoph'
'Würthner, Frank'
'Ravat, Prince'
_publ_section_title
;
 [n]Helicene Diimides (n = 5, 6, and 7): Through-Bond versus
 Through-Space Conjugation.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              21298
_journal_page_last               21303
_journal_paper_doi               10.1021/jacs.0c11053
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C40 H34 N2 O6'
_chemical_formula_sum            'C40 H34 N2 O6'
_chemical_formula_weight         638.69
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 117.911(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.9274(17)
_cell_length_b                   10.0744(6)
_cell_length_c                   13.9318(8)
_cell_measurement_reflns_used    5043
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      7212
_cell_measurement_theta_min      4.01
_cell_volume                     3091.7(4)
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_PhotonII
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.341
_diffrn_reflns_theta_min         4.014
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0643
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0887P)²+2.6706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2188
_reflns_number_total             3047
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c11053_si_002.cif
_cod_data_source_block           757_6HDI_OMe_0m_a
_cod_depositor_comments
'Adding full bibliography for 4135403--4135404.cif.'
_cod_original_cell_volume        3091.7(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4135404
_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.
;
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
C1 C 0.59678(12) 0.8275(3) 0.5790(2) 0.0454(6) Uani 1 1 d . . . . .
C2 C 0.54995(12) 0.7555(2) 0.48544(19) 0.0417(6) Uani 1 1 d . . . . .
C3 C 0.49763(12) 0.8208(2) 0.41494(19) 0.0417(6) Uani 1 1 d . . . . .
H3 H 0.493243 0.912742 0.424794 0.050 Uiso 1 1 calc R U . . .
C4 C 0.45119(12) 0.7529(2) 0.32940(19) 0.0415(6) Uani 1 1 d . . . . .
H4 H 0.414449 0.797611 0.283509 0.050 Uiso 1 1 calc R U . . .
C5 C 0.45816(12) 0.6206(2) 0.31071(19) 0.0406(5) Uani 1 1 d . . . . .
C6 C 0.51415(12) 0.5533(2) 0.37443(19) 0.0409(6) Uani 1 1 d . . . . .
C7 C 0.52780(12) 0.4184(2) 0.3541(2) 0.0428(6) Uani 1 1 d . . . . .
C8 C 0.500000 0.3523(3) 0.250000 0.0442(8) Uani 1 2 d S T P . .
C9 C 0.500000 0.2123(3) 0.250000 0.0470(8) Uani 1 2 d S T P . .
C10 C 0.53782(14) 0.1409(3) 0.3466(2) 0.0533(7) Uani 1 1 d . . . . .
H10 H 0.536587 0.046654 0.346562 0.064 Uiso 1 1 calc R U . . .
C11 C 0.57555(14) 0.2067(3) 0.4385(2) 0.0521(7) Uani 1 1 d . . . . .
H11 H 0.604795 0.159002 0.499317 0.062 Uiso 1 1 calc R U . . .
C12 C 0.57147(13) 0.3471(2) 0.4440(2) 0.0458(6) Uani 1 1 d . . . . .
C13 C 0.61228(13) 0.4168(3) 0.5388(2) 0.0466(6) Uani 1 1 d . . . . .
H13 H 0.642844 0.368383 0.597404 0.056 Uiso 1 1 calc R U . . .
C14 C 0.60911(12) 0.5505(2) 0.5485(2) 0.0433(6) Uani 1 1 d . . . . .
C15 C 0.65606(12) 0.6203(3) 0.6443(2) 0.0475(6) Uani 1 1 d . . . . .
C16 C 0.55786(12) 0.6205(2) 0.46801(19) 0.0407(6) Uani 1 1 d . . . . .
C17A C 0.69508(13) 0.8292(3) 0.7441(2) 0.0551(7) Uani 0.646(9) 1 d D . P A 1
H17A H 0.693810 0.924644 0.726367 0.066 Uiso 0.646(9) 1 calc R U P A 1
H17B H 0.735860 0.794383 0.762209 0.066 Uiso 0.646(9) 1 calc R U P A 1
C18A C 0.6823(3) 0.8104(7) 0.8408(5) 0.0569(15) Uani 0.646(9) 1 d D . P A 1
H18A H 0.690454 0.716998 0.865622 0.068 Uiso 0.646(9) 1 calc R U P A 1
H18B H 0.638858 0.828755 0.817243 0.068 Uiso 0.646(9) 1 calc R U P A 1
C19A C 0.7217(2) 0.9028(6) 0.9357(4) 0.0567(14) Uani 0.646(9) 1 d D . P A 1
H19A H 0.719539 0.873708 1.001698 0.068 Uiso 0.646(9) 1 calc R U P A 1
H19B H 0.764479 0.895902 0.950483 0.068 Uiso 0.646(9) 1 calc R U P A 1
C20A C 0.7012(3) 1.0482(6) 0.9116(6) 0.069(2) Uani 0.646(9) 1 d D . P A 1
H20A H 0.703875 1.077958 0.847051 0.103 Uiso 0.646(9) 1 calc R U P A 1
H20B H 0.727505 1.103590 0.973872 0.103 Uiso 0.646(9) 1 calc R U P A 1
H20C H 0.659137 1.055922 0.898675 0.103 Uiso 0.646(9) 1 calc R U P A 1
C17B C 0.69508(13) 0.8292(3) 0.7441(2) 0.0551(7) Uani 0.354(9) 1 d . . P A 2
H17C H 0.707670 0.907099 0.716242 0.066 Uiso 0.354(9) 1 calc R U P A 2
H17D H 0.730991 0.770886 0.781192 0.066 Uiso 0.354(9) 1 calc R U P A 2
C18B C 0.6760(5) 0.8784(12) 0.8298(8) 0.049(2) Uani 0.354(9) 1 d . . P A 2
H18C H 0.633669 0.911084 0.791123 0.059 Uiso 0.354(9) 1 calc R U P A 2
H18D H 0.676659 0.801862 0.874940 0.059 Uiso 0.354(9) 1 calc R U P A 2
C19B C 0.7164(5) 0.9897(15) 0.9057(10) 0.063(4) Uani 0.354(9) 1 d . . P A 2
H19C H 0.758968 0.958053 0.943842 0.076 Uiso 0.354(9) 1 calc R U P A 2
H19D H 0.715068 1.067457 0.861202 0.076 Uiso 0.354(9) 1 calc R U P A 2
C20B C 0.6972(4) 1.0324(11) 0.9889(8) 0.068(3) Uani 0.354(9) 1 d . . P A 2
H20D H 0.653817 1.053847 0.952297 0.103 Uiso 0.354(9) 1 calc R U P A 2
H20E H 0.720493 1.110911 1.027593 0.103 Uiso 0.354(9) 1 calc R U P A 2
H20F H 0.704831 0.960131 1.040811 0.103 Uiso 0.354(9) 1 calc R U P A 2
C21 C 0.35635(12) 0.6090(3) 0.1663(2) 0.0479(6) Uani 1 1 d . . . . .
H21A H 0.328682 0.543986 0.114478 0.072 Uiso 1 1 calc R U . . .
H21B H 0.364061 0.680633 0.126736 0.072 Uiso 1 1 calc R U . . .
H21C H 0.337903 0.646016 0.209028 0.072 Uiso 1 1 calc R U . . .
N1 N 0.64825(10) 0.7564(2) 0.65091(17) 0.0468(5) Uani 1 1 d . . . . .
O1 O 0.59294(9) 0.94520(18) 0.59473(16) 0.0556(5) Uani 1 1 d . . . . .
O2 O 0.70012(9) 0.5631(2) 0.71439(16) 0.0581(5) Uani 1 1 d . . . . .
O3 O 0.41232(8) 0.54562(16) 0.23731(13) 0.0430(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 C1 N1 119.5(2) . . ?
O1 C1 C2 122.9(2) . . ?
N1 C1 C2 117.6(2) . . ?
C3 C2 C16 120.0(2) . . ?
C3 C2 C1 119.3(2) . . ?
C16 C2 C1 120.7(2) . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
O3 C5 C4 123.0(2) . . ?
O3 C5 C6 116.1(2) . . ?
C4 C5 C6 120.9(2) . . ?
C16 C6 C5 116.8(2) . . ?
C16 C6 C7 118.3(2) . . ?
C5 C6 C7 124.8(2) . . ?
C12 C7 C8 117.7(2) . . ?
C12 C7 C6 117.0(2) . . ?
C8 C7 C6 125.3(2) . . ?
C9 C8 C7 117.46(15) . 2_655 ?
C9 C8 C7 117.46(15) . . ?
C7 C8 C7 125.1(3) 2_655 . ?
C8 C9 C10 120.34(17) . 2_655 ?
C8 C9 C10 120.34(17) . . ?
C10 C9 C10 119.3(3) 2_655 . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C13 119.6(2) . . ?
C7 C12 C11 120.2(3) . . ?
C13 C12 C11 120.3(3) . . ?
C14 C13 C12 122.2(2) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C16 118.8(2) . . ?
C13 C14 C15 120.2(2) . . ?
C16 C14 C15 120.9(2) . . ?
O2 C15 N1 120.9(3) . . ?
O2 C15 C14 122.3(3) . . ?
N1 C15 C14 116.9(2) . . ?
C2 C16 C6 120.6(2) . . ?
C2 C16 C14 119.0(2) . . ?
C6 C16 C14 120.3(2) . . ?
N1 C17A C18A 107.9(3) . . ?
N1 C17A H17A 110.1 . . ?
C18A C17A H17A 110.1 . . ?
N1 C17A H17B 110.1 . . ?
C18A C17A H17B 110.1 . . ?
H17A C17A H17B 108.4 . . ?
C17A C18A C19A 111.6(5) . . ?
C17A C18A H18A 109.3 . . ?
C19A C18A H18A 109.3 . . ?
C17A C18A H18B 109.3 . . ?
C19A C18A H18B 109.3 . . ?
H18A C18A H18B 108.0 . . ?
C20A C19A C18A 112.1(5) . . ?
C20A C19A H19A 109.2 . . ?
C18A C19A H19A 109.2 . . ?
C20A C19A H19B 109.2 . . ?
C18A C19A H19B 109.2 . . ?
H19A C19A H19B 107.9 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
N1 C17B C18B 115.7(5) . . ?
N1 C17B H17C 108.4 . . ?
C18B C17B H17C 108.4 . . ?
N1 C17B H17D 108.4 . . ?
C18B C17B H17D 108.4 . . ?
H17C C17B H17D 107.4 . . ?
C19B C18B C17B 114.8(8) . . ?
C19B C18B H18C 108.6 . . ?
C17B C18B H18C 108.6 . . ?
C19B C18B H18D 108.6 . . ?
C17B C18B H18D 108.6 . . ?
H18C C18B H18D 107.5 . . ?
C20B C19B C18B 113.1(9) . . ?
C20B C19B H19C 109.0 . . ?
C18B C19B H19C 109.0 . . ?
C20B C19B H19D 109.0 . . ?
C18B C19B H19D 109.0 . . ?
H19C C19B H19D 107.8 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 N1 C1 124.5(2) . . ?
C15 N1 C17B 118.1(2) . . ?
C1 N1 C17B 117.3(2) . . ?
C15 N1 C17A 118.1(2) . . ?
C1 N1 C17A 117.3(2) . . ?
C5 O3 C21 118.66(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
C1 O1 1.217(3) . ?
C1 N1 1.400(3) . ?
C1 C2 1.471(3) . ?
C2 C3 1.378(3) . ?
C2 C16 1.411(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 O3 1.352(3) . ?
C5 C6 1.427(3) . ?
C6 C16 1.420(3) . ?
C6 C7 1.460(3) . ?
C7 C12 1.412(4) . ?
C7 C8 1.445(3) . ?
C8 C9 1.410(5) . ?
C9 C10 1.425(3) 2_655 ?
C9 C10 1.425(3) . ?
C10 C11 1.355(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.423(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.419(4) . ?
C13 C14 1.360(4) . ?
C13 H13 0.9500 . ?
C14 C16 1.430(3) . ?
C14 C15 1.477(4) . ?
C15 O2 1.220(3) . ?
C15 N1 1.394(3) . ?
C17A N1 1.472(3) . ?
C17A C18A 1.534(6) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C18A C19A 1.538(8) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C19A C20A 1.536(7) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C17B N1 1.472(3) . ?
C17B C18B 1.558(10) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18B C19B 1.547(15) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19B C20B 1.509(14) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21 O3 1.429(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
