#------------------------------------------------------------------------------
#$Date: 2022-02-04 22:02:23 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158426.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_7158426
loop_
_publ_author_name
'Sartucci, Jenna L.'
'Maity, Arindam'
'Mohanan, Manikandan'
'Bertke, Jeffery'
'Kertesz, Miklos'
'Gavvalapalli, Nagarjuna'
_publ_section_title
;
 Molecular tetrominoes: selective masking of the donor π-face to control
 the configuration of donor-acceptor complexes.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              375
_journal_page_last               386
_journal_paper_doi               10.1039/d1ob02293h
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C22 H14, 2(C8 Cl2 N2 O2)'
_chemical_formula_sum            'C38 H14 Cl4 N4 O4'
_chemical_formula_weight         732.33
_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     intrinsic
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-25 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                92.211(8)
_cell_angle_beta                 97.288(8)
_cell_angle_gamma                102.060(7)
_cell_formula_units_Z            1
_cell_length_a                   6.4871(13)
_cell_length_b                   7.1989(15)
_cell_length_c                   17.900(4)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.30
_cell_volume                     809.0(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_collection       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_data_reduction
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            44132
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.299
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.99019
_exptl_absorpt_correction_T_min  0.91231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     430
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0327
_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)+(0.0443P)²+0.2093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2778
_reflns_number_total             3310
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02293h3.cif
_cod_data_source_block           B19324_a
_cod_depositor_comments
'Adding full bibliography for 7158425--7158427.cif.'
_cod_original_cell_volume        809.1(3)
_cod_database_code               7158426
_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.
;
_shelx_estimated_absorpt_t_min   0.881
_shelx_estimated_absorpt_t_max   0.985
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
C1 C 0.2692(2) 0.87508(17) 0.79112(7) 0.0231(3) Uani 1 1 d . . . . .
C2 C 0.4845(2) 0.92630(18) 0.82104(8) 0.0271(3) Uani 1 1 d . . . . .
H2 H 0.586174 0.986040 0.790832 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5493(2) 0.8902(2) 0.89437(8) 0.0314(3) Uani 1 1 d . . . . .
H3 H 0.695646 0.925228 0.914681 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4011(2) 0.80269(19) 0.93856(8) 0.0310(3) Uani 1 1 d . . . . .
H4 H 0.446594 0.777644 0.989022 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1881(2) 0.75184(19) 0.90963(8) 0.0286(3) Uani 1 1 d . . . . .
H5 H 0.087604 0.692325 0.940297 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1204(2) 0.78714(18) 0.83617(8) 0.0259(3) Uani 1 1 d . . . . .
H6 H -0.026322 0.751952 0.816345 0.031 Uiso 1 1 calc R U . . .
C7 C 0.2017(2) 0.91219(18) 0.71503(8) 0.0265(3) Uani 1 1 d . . . . .
C8 C 0.1462(2) 0.94015(18) 0.65065(8) 0.0268(3) Uani 1 1 d . . . . .
C9 C 0.0734(2) 0.96966(17) 0.57417(7) 0.0251(3) Uani 1 1 d . . . . .
C10 C 0.2135(2) 1.06831(18) 0.52851(8) 0.0273(3) Uani 1 1 d . . . . .
H10 H 0.359249 1.114677 0.548056 0.033 Uiso 1 1 calc R U . . .
C11 C -0.1401(2) 0.90187(18) 0.54483(8) 0.0278(3) Uani 1 1 d . . . . .
H11 H -0.235537 0.834659 0.575584 0.033 Uiso 1 1 calc R U . . .
Cl1 Cl -0.11163(14) 0.39409(10) 0.59803(5) 0.0270(2) Uani 0.6021(19) 1 d D U P A
1
Cl2 Cl 0.3627(2) 0.57842(17) 0.57929(7) 0.0261(4) Uani 0.6021(19) 1 d D U P A 1
O1 O 0.6487(10) 0.5978(12) 0.7207(8) 0.0229(12) Uani 0.6021(19) 1 d D U P A 1
O2 O -0.1440(6) 0.2478(6) 0.74696(18) 0.0302(7) Uani 0.6021(19) 1 d D U P A 1
N1 N 0.7168(8) 0.4474(9) 0.9060(3) 0.0345(10) Uani 0.6021(19) 1 d D U P A 1
N2 N 0.1088(6) 0.2162(4) 0.92975(18) 0.0367(7) Uani 0.6021(19) 1 d D U P A 1
C12 C 0.0912(8) 0.4095(7) 0.6683(2) 0.0184(8) Uani 0.6021(19) 1 d D U P A 1
C13 C 0.2948(10) 0.4909(11) 0.6606(3) 0.0170(10) Uani 0.6021(19) 1 d D U P A 1
C14 C 0.4691(9) 0.5084(14) 0.7236(4) 0.0191(11) Uani 0.6021(19) 1 d D U P A 1
C15 C 0.4132(10) 0.4252(13) 0.7952(3) 0.0199(10) Uani 0.6021(19) 1 d D U P A 1
C16 C 0.2110(8) 0.3428(8) 0.8029(2) 0.0199(9) Uani 0.6021(19) 1 d D U P A 1
C17 C 0.0355(6) 0.3273(6) 0.73943(19) 0.0186(8) Uani 0.6021(19) 1 d D U P A 1
C18 C 0.5823(8) 0.4366(9) 0.8556(3) 0.0272(12) Uani 0.6021(19) 1 d D U P A 1
C19 C 0.1537(5) 0.2707(4) 0.8726(2) 0.0246(6) Uani 0.6021(19) 1 d D U P A 1
Cl1B Cl 0.1836(2) 0.25221(17) 0.90976(9) 0.0264(3) Uani 0.3979(19) 1 d D U P A 2
Cl2B Cl 0.6531(3) 0.4423(2) 0.88081(10) 0.0286(6) Uani 0.3979(19) 1 d D U P A 2
O1B O 0.6599(15) 0.5609(19) 0.7263(12) 0.0225(17) Uani 0.3979(19) 1 d D U P A 2
O2B O -0.1202(9) 0.2283(9) 0.7736(3) 0.0295(11) Uani 0.3979(19) 1 d D U P A 2
N1B N 0.3774(15) 0.6071(13) 0.5535(4) 0.0289(15) Uani 0.3979(19) 1 d D U P A 2
N2B N -0.2300(7) 0.3302(6) 0.58933(19) 0.0343(8) Uani 0.3979(19) 1 d D U P A 2
C12B C 0.2405(12) 0.3356(13) 0.8261(3) 0.0186(13) Uani 0.3979(19) 1 d D U P A 2
C13B C 0.4400(15) 0.4174(19) 0.8140(5) 0.0173(15) Uani 0.3979(19) 1 d D U P A 2
C14B C 0.4819(13) 0.495(2) 0.7410(6) 0.0187(17) Uani 0.3979(19) 1 d D U P A 2
C15B C 0.2969(16) 0.4726(18) 0.6807(5) 0.0194(15) Uani 0.3979(19) 1 d D U P A 2
C16B C 0.0989(11) 0.3832(10) 0.6915(3) 0.0175(13) Uani 0.3979(19) 1 d D U P A 2
C17B C 0.0594(9) 0.3083(9) 0.7655(3) 0.0190(11) Uani 0.3979(19) 1 d D U P A 2
C18B C 0.3418(10) 0.5502(10) 0.6110(3) 0.0235(14) Uani 0.3979(19) 1 d D U P A 2
C19B C -0.0803(6) 0.3577(6) 0.6341(3) 0.0242(8) Uani 0.3979(19) 1 d D 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0050
0.00 0.00 1.00 0.0180
0.00 1.00 0.00 0.1160
0.00 -1.00 0.00 0.1160
1.00 0.00 0.00 0.0850
-1.00 0.00 0.00 0.1090
2.00 2.00 -1.00 0.0890
-2.00 -2.00 1.00 0.0780
-1.00 2.00 1.00 0.1430
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
C2 C1 C6 119.55(12) . . ?
C2 C1 C7 120.10(12) . . ?
C6 C1 C7 120.35(13) . . ?
C3 C2 C1 120.02(13) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.10(14) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.36(13) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.28(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.69(13) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C1 178.69(15) . . ?
C7 C8 C9 178.11(15) . . ?
C11 C9 C10 119.50(13) . . ?
C11 C9 C8 119.75(12) . . ?
C10 C9 C8 120.74(13) . . ?
C11 C10 C9 120.02(13) 2_576 . ?
C11 C10 H10 120.0 2_576 . ?
C9 C10 H10 120.0 . . ?
C10 C11 C9 120.47(13) 2_576 . ?
C10 C11 H11 119.8 2_576 . ?
C9 C11 H11 119.8 . . ?
C13 C12 C17 121.4(3) . . ?
C13 C12 Cl1 122.4(3) . . ?
C17 C12 Cl1 116.2(3) . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 Cl2 122.1(4) . . ?
C14 C13 Cl2 116.3(4) . . ?
O1 C14 C13 122.8(7) . . ?
O1 C14 C15 119.9(8) . . ?
C13 C14 C15 117.0(3) . . ?
C16 C15 C18 121.2(5) . . ?
C16 C15 C14 121.5(4) . . ?
C18 C15 C14 117.3(5) . . ?
C15 C16 C19 122.0(4) . . ?
C15 C16 C17 121.2(4) . . ?
C19 C16 C17 116.8(4) . . ?
O2 C17 C12 122.7(3) . . ?
O2 C17 C16 120.0(3) . . ?
C12 C17 C16 117.3(3) . . ?
N1 C18 C15 178.2(8) . . ?
N2 C19 C16 178.6(4) . . ?
C13B C12B C17B 121.4(5) . . ?
C13B C12B Cl1B 122.9(5) . . ?
C17B C12B Cl1B 115.7(5) . . ?
C12B C13B C14B 121.2(6) . . ?
C12B C13B Cl2B 122.8(6) . . ?
C14B C13B Cl2B 116.0(6) . . ?
O1B C14B C13B 123.4(11) . . ?
O1B C14B C15B 119.2(11) . . ?
C13B C14B C15B 117.0(5) . . ?
C16B C15B C18B 122.4(6) . . ?
C16B C15B C14B 121.8(6) . . ?
C18B C15B C14B 115.8(7) . . ?
C15B C16B C19B 122.7(5) . . ?
C15B C16B C17B 120.4(5) . . ?
C19B C16B C17B 116.9(5) . . ?
O2B C17B C12B 123.0(5) . . ?
O2B C17B C16B 119.0(5) . . ?
C12B C17B C16B 118.0(4) . . ?
N1B C18B C15B 177.7(10) . . ?
N2B C19B C16B 176.8(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
C1 C2 1.398(2) . ?
C1 C6 1.4016(19) . ?
C1 C7 1.4296(19) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.200(2) . ?
C8 C9 1.4293(19) . ?
C9 C11 1.395(2) . ?
C9 C10 1.4008(19) . ?
C10 C11 1.379(2) 2_576 ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
Cl1 C12 1.684(4) . ?
Cl2 C13 1.682(5) . ?
O1 C14 1.216(5) . ?
O2 C17 1.212(4) . ?
N1 C18 1.161(5) . ?
N2 C19 1.159(4) . ?
C12 C13 1.355(7) . ?
C12 C17 1.478(4) . ?
C13 C14 1.474(6) . ?
C14 C15 1.490(6) . ?
C15 C16 1.348(7) . ?
C15 C18 1.426(5) . ?
C16 C19 1.433(5) . ?
C16 C17 1.486(4) . ?
Cl1B C12B 1.691(6) . ?
Cl2B C13B 1.684(8) . ?
O1B C14B 1.219(6) . ?
O2B C17B 1.216(5) . ?
N1B C18B 1.155(6) . ?
N2B C19B 1.155(6) . ?
C12B C13B 1.353(10) . ?
C12B C17B 1.469(5) . ?
C13B C14B 1.475(8) . ?
C14B C15B 1.486(9) . ?
C15B C16B 1.353(10) . ?
C15B C18B 1.425(6) . ?
C16B C19B 1.427(7) . ?
C16B C17B 1.480(5) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(2) . . . . ?
C7 C1 C2 C3 -179.91(13) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C2 C1 C6 C5 -0.08(19) . . . . ?
C7 C1 C6 C5 179.88(12) . . . . ?
C11 C9 C10 C11 0.1(2) . . . 2_576 ?
C8 C9 C10 C11 -179.00(12) . . . 2_576 ?
C10 C9 C11 C10 -0.1(2) . . . 2_576 ?
C8 C9 C11 C10 179.01(12) . . . 2_576 ?
C17 C12 C13 C14 -2.5(10) . . . . ?
Cl1 C12 C13 C14 178.0(6) . . . . ?
C17 C12 C13 Cl2 177.9(5) . . . . ?
Cl1 C12 C13 Cl2 -1.6(9) . . . . ?
C12 C13 C14 O1 -172.2(10) . . . . ?
Cl2 C13 C14 O1 7.4(13) . . . . ?
C12 C13 C14 C15 2.5(11) . . . . ?
Cl2 C13 C14 C15 -177.8(7) . . . . ?
O1 C14 C15 C16 172.9(10) . . . . ?
C13 C14 C15 C16 -2.0(12) . . . . ?
O1 C14 C15 C18 -7.0(13) . . . . ?
C13 C14 C15 C18 178.1(7) . . . . ?
C18 C15 C16 C19 3.0(10) . . . . ?
C14 C15 C16 C19 -176.9(7) . . . . ?
C18 C15 C16 C17 -178.7(6) . . . . ?
C14 C15 C16 C17 1.4(10) . . . . ?
C13 C12 C17 O2 -177.3(6) . . . . ?
Cl1 C12 C17 O2 2.1(6) . . . . ?
C13 C12 C17 C16 1.8(7) . . . . ?
Cl1 C12 C17 C16 -178.7(4) . . . . ?
C15 C16 C17 O2 177.9(6) . . . . ?
C19 C16 C17 O2 -3.7(7) . . . . ?
C15 C16 C17 C12 -1.2(8) . . . . ?
C19 C16 C17 C12 177.2(4) . . . . ?
C17B C12B C13B C14B 4.5(16) . . . . ?
Cl1B C12B C13B C14B -177.5(10) . . . . ?
C17B C12B C13B Cl2B -177.2(8) . . . . ?
Cl1B C12B C13B Cl2B 0.7(15) . . . . ?
C12B C13B C14B O1B -176.0(16) . . . . ?
Cl2B C13B C14B O1B 6(2) . . . . ?
C12B C13B C14B C15B -2.5(18) . . . . ?
Cl2B C13B C14B C15B 179.1(11) . . . . ?
O1B C14B C15B C16B 173.2(15) . . . . ?
C13B C14B C15B C16B -0.6(18) . . . . ?
O1B C14B C15B C18B -6.6(19) . . . . ?
C13B C14B C15B C18B 179.6(11) . . . . ?
C18B C15B C16B C19B 0.6(15) . . . . ?
C14B C15B C16B C19B -179.2(10) . . . . ?
C18B C15B C16B C17B -178.8(8) . . . . ?
C14B C15B C16B C17B 1.5(15) . . . . ?
C13B C12B C17B O2B 176.8(9) . . . . ?
Cl1B C12B C17B O2B -1.2(10) . . . . ?
C13B C12B C17B C16B -3.5(12) . . . . ?
Cl1B C12B C17B C16B 178.4(5) . . . . ?
C15B C16B C17B O2B -179.9(9) . . . . ?
C19B C16B C17B O2B 0.7(9) . . . . ?
C15B C16B C17B C12B 0.4(11) . . . . ?
C19B C16B C17B C12B -178.9(6) . . . . ?
