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#$Date: 2024-12-06 22:38:35 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296694 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160236.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_7160236
loop_
_publ_author_name
'Granhøj, Jeppe'
'Pedersen, Viktor Bliksted Roug'
'Mikkelsen, Kurt V.'
'Nielsen, Mogens Brøndsted'
_publ_section_title
;
 Extended tetrathiafulvalene with a
 pentaleno[1,2-b:4,5-b']difluorene core - a donor-acceptor
 multi-redox system.
;
_journal_issue                   47
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9259
_journal_page_last               9265
_journal_paper_doi               10.1039/d4ob01755b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C48 H34 O2, C H2 Cl2  '
_chemical_formula_sum            'C49 H36 Cl2 O2'
_chemical_formula_weight         727.68
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;FinalCif V143 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-10-03 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                87.358(4)
_cell_angle_beta                 77.624(6)
_cell_angle_gamma                87.173(5)
_cell_formula_units_Z            1
_cell_length_a                   8.0184(9)
_cell_length_b                   9.0834(7)
_cell_length_c                   12.9502(12)
_cell_measurement_reflns_used    3915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7475
_cell_measurement_theta_min      2.6025
_cell_volume                     919.57(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       APEX4
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            39614
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.246
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method
'Single crystals were obtained from diffusion of methanol into a solution of the compound in dichloromethane from a bilayer system.'
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0434
_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)+(0.0489P)²+0.4923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2787
_reflns_number_total             3757
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01755b2.cif
_cod_data_source_block           mo_D8V6035_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160236--7160237.cif.'
_cod_database_code               7160236
_shelx_shelxl_version_number     2019/2
_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.
;
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
loop_
_space_group_symop_operation_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_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
O1 O 0.05723(18) 0.61743(14) 0.85580(10) 0.0347(3) Uani 1 1 d . . . . .
C1 C 0.1333(2) 0.79223(19) 0.97329(14) 0.0261(4) Uani 1 1 d . . . . .
C2 C 0.2301(2) 0.91866(18) 0.95326(13) 0.0240(4) Uani 1 1 d . . . . .
C3 C 0.2541(2) 1.0000(2) 1.03610(14) 0.0284(4) Uani 1 1 d . . . . .
H3 H 0.319624 1.085775 1.023478 0.034 Uiso 1 1 calc R U . . .
C4 C 0.1792(2) 0.9524(2) 1.13888(14) 0.0321(4) Uani 1 1 d . . . . .
H4 H 0.194010 1.006954 1.196893 0.039 Uiso 1 1 calc R U . . .
C5 C 0.0837(2) 0.8273(2) 1.15791(14) 0.0329(4) Uani 1 1 d . . . . .
H5 H 0.033762 0.797688 1.228656 0.040 Uiso 1 1 calc R U . . .
C6 C 0.0598(2) 0.7444(2) 1.07506(14) 0.0306(4) Uani 1 1 d . . . . .
H6 H -0.004752 0.657992 1.087881 0.037 Uiso 1 1 calc R U . . .
C7 C 0.1284(2) 0.72731(18) 0.87026(14) 0.0256(4) Uani 1 1 d . . . . .
C8 C 0.2311(2) 0.82539(17) 0.78764(13) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.2916(2) 0.93917(18) 0.83721(13) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.2699(2) 0.81218(17) 0.67853(13) 0.0216(3) Uani 1 1 d . . . . .
H10 H 0.226280 0.735440 0.645823 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3751(2) 0.91595(17) 0.61964(12) 0.0204(3) Uani 1 1 d . . . . .
C12 C 0.4329(2) 1.03429(17) 0.66931(13) 0.0212(3) Uani 1 1 d . . . . .
C13 C 0.4607(2) 0.87000(17) 0.41288(12) 0.0198(3) Uani 1 1 d . . . . .
C14 C 0.4501(2) 0.93393(16) 0.50688(13) 0.0206(3) Uani 1 1 d . . . . .
C15 C 0.3929(2) 1.04681(17) 0.77851(13) 0.0225(4) Uani 1 1 d . . . . .
H15 H 0.432881 1.125213 0.811568 0.027 Uiso 1 1 calc R U . . .
C16 C 0.3894(2) 0.73054(17) 0.39107(12) 0.0198(3) Uani 1 1 d . . . . .
C17 C 0.2120(2) 0.71807(18) 0.40330(13) 0.0222(4) Uani 1 1 d . . . . .
C18 C 0.1498(2) 0.58484(19) 0.38272(14) 0.0263(4) Uani 1 1 d . . . . .
H18 H 0.029878 0.575811 0.392337 0.032 Uiso 1 1 calc R U . . .
C19 C 0.2579(2) 0.46453(19) 0.34852(14) 0.0271(4) Uani 1 1 d . . . . .
C20 C 0.4321(2) 0.47978(18) 0.33665(14) 0.0262(4) Uani 1 1 d . . . . .
H20 H 0.507453 0.398485 0.312868 0.031 Uiso 1 1 calc R U . . .
C21 C 0.5007(2) 0.60962(17) 0.35824(13) 0.0220(4) Uani 1 1 d . . . . .
C22 C 0.0916(2) 0.8483(2) 0.43600(14) 0.0290(4) Uani 1 1 d . . . . .
H22A H 0.127773 0.933604 0.388768 0.043 Uiso 1 1 calc R U . . .
H22B H 0.093207 0.871851 0.508881 0.043 Uiso 1 1 calc R U . . .
H22C H -0.024423 0.824326 0.431636 0.043 Uiso 1 1 calc R U . . .
C23 C 0.1907(3) 0.3214(2) 0.32377(19) 0.0422(5) Uani 1 1 d . . . . .
H23A H 0.189408 0.321390 0.248278 0.063 Uiso 1 1 calc R U . . .
H23B H 0.074425 0.310384 0.365541 0.063 Uiso 1 1 calc R U . . .
H23C H 0.264685 0.239110 0.341383 0.063 Uiso 1 1 calc R U . . .
C24 C 0.6902(2) 0.61389(19) 0.35132(15) 0.0289(4) Uani 1 1 d . . . . .
H24A H 0.750595 0.549194 0.295682 0.043 Uiso 1 1 calc R U . . .
H24B H 0.716430 0.580131 0.419259 0.043 Uiso 1 1 calc R U . . .
H24C H 0.726953 0.715111 0.334521 0.043 Uiso 1 1 calc R U . . .
Cl1_1 Cl 0.4180(13) 1.4223(10) 0.9327(6) 0.0641(16) Uani 0.359(4) 1 d D U P A -1
Cl2_1 Cl 0.5857(15) 1.6055(9) 1.0493(7) 0.076(3) Uani 0.359(4) 1 d D U P A -1
C1_1 C 0.4373(10) 1.4702(8) 1.0590(5) 0.0472(19) Uani 0.359(4) 1 d D U P A -1
H1A_1 H 0.325021 1.506944 1.099380 0.057 Uiso 0.359(4) 1 calc R U P A -1
H1B_1 H 0.473821 1.381935 1.097563 0.057 Uiso 0.359(4) 1 calc R U P A -1
Cl1_2 Cl 0.4688(11) 1.3449(10) 1.0349(18) 0.179(9) Uani 0.141(4) 1 d D U P A -2
Cl2_2 Cl 0.6371(16) 1.5970(17) 1.0214(17) 0.118(7) Uani 0.141(4) 1 d D U P A -2
C1_2 C 0.4266(19) 1.5347(14) 1.052(3) 0.093(10) Uani 0.141(4) 1 d D U P A -2
H1A_2 H 0.368661 1.555727 1.125905 0.111 Uiso 0.141(4) 1 calc R U P A -2
H1B_2 H 0.357308 1.578243 1.002959 0.111 Uiso 0.141(4) 1 calc R U P A -2
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'
O O 0.0106 0.0060 '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
C6 C1 C2 121.82(16) . . ?
C6 C1 C7 129.50(16) . . ?
C2 C1 C7 108.68(14) . . ?
C3 C2 C1 120.21(16) . . ?
C3 C2 C9 131.20(16) . . ?
C1 C2 C9 108.59(15) . . ?
C2 C3 C4 118.09(17) . . ?
C5 C4 C3 121.29(17) . . ?
C4 C5 C6 120.98(17) . . ?
C1 C6 C5 117.61(17) . . ?
O1 C7 C8 126.80(16) . . ?
O1 C7 C1 127.78(16) . . ?
C8 C7 C1 105.43(14) . . ?
C10 C8 C9 122.37(15) . . ?
C10 C8 C7 128.76(15) . . ?
C9 C8 C7 108.85(14) . . ?
C15 C9 C8 121.11(15) . . ?
C15 C9 C2 130.45(15) . . ?
C8 C9 C2 108.44(14) . . ?
C11 C10 C8 116.98(15) . . ?
C10 C11 C12 120.85(15) . . ?
C10 C11 C14 132.97(15) . . ?
C12 C11 C14 106.17(14) . . ?
C15 C12 C11 121.66(15) . . ?
C15 C12 C13 129.15(15) . 2_676 ?
C11 C12 C13 109.16(14) . 2_676 ?
C14 C13 C16 129.07(14) . . ?
C14 C13 C12 106.70(13) . 2_676 ?
C16 C13 C12 124.20(14) . 2_676 ?
C13 C14 C14 110.85(17) . 2_676 ?
C13 C14 C11 142.09(15) . . ?
C14 C14 C11 107.05(17) 2_676 . ?
C12 C15 C9 116.95(15) . . ?
C21 C16 C17 120.00(14) . . ?
C21 C16 C13 119.24(14) . . ?
C17 C16 C13 120.76(14) . . ?
C18 C17 C16 119.05(15) . . ?
C18 C17 C22 120.52(15) . . ?
C16 C17 C22 120.42(15) . . ?
C19 C18 C17 121.90(16) . . ?
C20 C19 C18 117.94(15) . . ?
C20 C19 C23 120.15(16) . . ?
C18 C19 C23 121.91(16) . . ?
C19 C20 C21 122.44(16) . . ?
C20 C21 C16 118.65(15) . . ?
C20 C21 C24 119.25(15) . . ?
C16 C21 C24 122.02(14) . . ?
Cl2_1 C1_1 Cl1_1 110.2(5) . . ?
Cl1_2 C1_2 Cl2_2 99.9(9) . . ?
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
O1 C7 1.215(2) . ?
C1 C6 1.383(2) . ?
C1 C2 1.401(2) . ?
C1 C7 1.492(2) . ?
C2 C3 1.382(2) . ?
C2 C9 1.484(2) . ?
C3 C4 1.396(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.390(3) . ?
C7 C8 1.491(2) . ?
C8 C10 1.390(2) . ?
C8 C9 1.400(2) . ?
C9 C15 1.392(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.423(2) . ?
C11 C14 1.460(2) . ?
C12 C15 1.390(2) . ?
C12 C13 1.488(2) 2_676 ?
C13 C14 1.357(2) . ?
C13 C16 1.479(2) . ?
C14 C14 1.458(3) 2_676 ?
C16 C21 1.403(2) . ?
C16 C17 1.406(2) . ?
C17 C18 1.390(2) . ?
C17 C22 1.507(2) . ?
C18 C19 1.389(2) . ?
C19 C20 1.385(2) . ?
C19 C23 1.505(2) . ?
C20 C21 1.390(2) . ?
C21 C24 1.505(2) . ?
Cl1_1 C1_1 1.752(7) . ?
Cl2_1 C1_1 1.734(7) . ?
Cl1_2 C1_2 1.755(9) . ?
Cl2_2 C1_2 1.764(9) . ?
