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#$Date: 2023-09-15 00:57:31 +0300 (Fri, 15 Sep 2023) $
#$Revision: 286340 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132134.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_7132134
loop_
_publ_author_name
'Horvath, Mikayla L.'
'Jumbelic, Caylee E.'
'Burynski, Rosemarie A.'
'Mistrot, M. Brody'
'Pike, Robert D.'
'Smith, Brian J.'
'Arslan, Hasan'
_publ_section_title
;
 Rapid single crystal growth via guest displacement from host-guest
 complexes.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc03406b
_journal_year                    2023
_chemical_formula_moiety         'C36 H36 N2'
_chemical_formula_sum            'C36 H36 N2'
_chemical_formula_weight         496.67
_chemical_name_systematic
(1E,1'E)-1,1'-(anthracene-9,10-diyl)bis(N-(4-(tert-butyl)phenyl)methanimine)
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-06-27 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                79.840(4)
_cell_angle_beta                 81.504(4)
_cell_angle_gamma                75.748(4)
_cell_formula_units_Z            1
_cell_length_a                   6.1032(13)
_cell_length_b                   8.943(2)
_cell_length_c                   13.218(3)
_cell_measurement_reflns_used    2421
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.65
_cell_volume                     684.2(3)
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.7 (CCDC, 2016)'
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω and ψ'
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            2604
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.124
_diffrn_reflns_theta_min         1.575
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6359
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       plate
_exptl_crystal_F_000             266
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.629
_exptl_crystal_size_mid          0.484
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0891
_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)+2.7824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1749
_reflns_number_total             2604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03406b3.cif
_cod_data_source_block           mo_Arslan011_0m_4_a
_cod_original_cell_volume        684.1(3)
_cod_database_code               7132134
_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   0.958
_shelx_estimated_absorpt_t_max   0.989
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
N1 N 0.6622(5) 0.6924(4) 0.3211(2) 0.0181(7) Uani 1 1 d . . . . .
C1 C 0.8644(6) 0.7278(4) 0.5000(3) 0.0188(8) Uani 1 1 d . . . . .
H1 H 0.868131 0.651123 0.457892 0.023 Uiso 1 1 calc R U . . .
C2 C 1.0327(6) 0.7064(4) 0.5620(3) 0.0195(8) Uani 1 1 d . . . . .
H2 H 1.153259 0.616039 0.561640 0.023 Uiso 1 1 calc R U . . .
C3 C 1.0301(6) 0.8170(4) 0.6269(3) 0.0181(8) Uani 1 1 d . . . . .
H3 H 1.148608 0.800956 0.669590 0.022 Uiso 1 1 calc R U . . .
C4 C 0.8575(6) 0.9464(4) 0.6280(3) 0.0177(8) Uani 1 1 d . . . . .
H4 H 0.855339 1.018444 0.673291 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6782(6) 0.9773(4) 0.5626(3) 0.0163(8) Uani 1 1 d . . . . .
C6 C 0.6812(6) 0.8647(4) 0.4972(3) 0.0158(8) Uani 1 1 d . . . . .
C7 C 0.5016(6) 0.8880(4) 0.4348(3) 0.0157(8) Uani 1 1 d . . . . .
C8 C 0.4882(6) 0.7728(4) 0.3693(3) 0.0156(8) Uani 1 1 d . . . . .
H8 H 0.342481 0.757835 0.362695 0.019 Uiso 1 1 calc R U . . .
C9 C 0.6311(6) 0.5789(4) 0.2644(3) 0.0157(8) Uani 1 1 d . . . . .
C10 C 0.7921(6) 0.5443(4) 0.1801(3) 0.0195(8) Uani 1 1 d . . . . .
H10 H 0.911127 0.598612 0.161843 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7797(6) 0.4305(4) 0.1224(3) 0.0176(8) Uani 1 1 d . . . . .
H11 H 0.887915 0.410973 0.064042 0.021 Uiso 1 1 calc R U . . .
C12 C 0.6128(6) 0.3457(4) 0.1486(3) 0.0153(8) Uani 1 1 d . . . . .
C13 C 0.4525(6) 0.3803(4) 0.2345(3) 0.0189(8) Uani 1 1 d . . . . .
H13 H 0.336166 0.323792 0.254159 0.023 Uiso 1 1 calc R U . . .
C14 C 0.4614(6) 0.4953(4) 0.2910(3) 0.0186(8) Uani 1 1 d . . . . .
H14 H 0.350830 0.517020 0.348286 0.022 Uiso 1 1 calc R U . . .
C15 C 0.6123(6) 0.2097(4) 0.0917(3) 0.0158(8) Uani 1 1 d . . . . .
C16 C 0.7429(7) 0.2249(5) -0.0178(3) 0.0242(9) Uani 1 1 d . . . . .
H16A H 0.728474 0.141157 -0.053496 0.036 Uiso 1 1 calc R U . . .
H16B H 0.903820 0.216939 -0.012276 0.036 Uiso 1 1 calc R U . . .
H16C H 0.678995 0.326124 -0.056940 0.036 Uiso 1 1 calc R U . . .
C17 C 0.7262(7) 0.0570(4) 0.1555(3) 0.0243(9) Uani 1 1 d . . . . .
H17A H 0.726392 -0.031195 0.120788 0.036 Uiso 1 1 calc R U . . .
H17B H 0.641663 0.045422 0.224435 0.036 Uiso 1 1 calc R U . . .
H17C H 0.883074 0.059412 0.162099 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3685(6) 0.2042(5) 0.0796(3) 0.0239(9) Uani 1 1 d . . . . .
H18A H 0.372016 0.117542 0.042745 0.036 Uiso 1 1 calc R U . . .
H18B H 0.294445 0.302498 0.040275 0.036 Uiso 1 1 calc R U . . .
H18C H 0.283361 0.188984 0.148097 0.036 Uiso 1 1 calc R U . . .
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'
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
C8 N1 C9 119.0(3) . . ?
C2 C1 C6 121.0(4) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.9(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C7 C5 C6 120.6(3) 2_676 . ?
C7 C5 C4 121.3(3) 2_676 . ?
C6 C5 C4 118.1(3) . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 C1 122.0(3) . . ?
C5 C6 C1 118.3(3) . . ?
C5 C7 C6 119.7(3) 2_676 . ?
C5 C7 C8 117.7(3) 2_676 . ?
C6 C7 C8 122.5(3) . . ?
N1 C8 C7 123.6(3) . . ?
N1 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C14 C9 C10 118.6(3) . . ?
C14 C9 N1 124.6(3) . . ?
C10 C9 N1 116.7(3) . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 117.7(3) . . ?
C11 C12 C15 121.4(3) . . ?
C13 C12 C15 120.8(3) . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C9 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C18 C15 C17 109.4(3) . . ?
C18 C15 C12 110.8(3) . . ?
C17 C15 C12 108.2(3) . . ?
C18 C15 C16 107.5(3) . . ?
C17 C15 C16 109.1(3) . . ?
C12 C15 C16 111.9(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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
N1 C8 1.279(5) . ?
N1 C9 1.427(5) . ?
C1 C2 1.364(5) . ?
C1 C6 1.440(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.415(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.360(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.438(5) . ?
C4 H4 0.9500 . ?
C5 C7 1.417(5) 2_676 ?
C5 C6 1.433(5) . ?
C6 C7 1.421(5) . ?
C7 C8 1.482(5) . ?
C8 H8 0.9500 . ?
C9 C14 1.391(5) . ?
C9 C10 1.397(5) . ?
C10 C11 1.397(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.410(5) . ?
C12 C15 1.540(5) . ?
C13 C14 1.389(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C18 1.533(5) . ?
C15 C17 1.536(5) . ?
C15 C16 1.546(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
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 1.1(6) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 -1.7(6) . . . . ?
C3 C4 C5 C7 179.5(4) . . . 2_676 ?
C3 C4 C5 C6 1.8(5) . . . . ?
C7 C5 C6 C7 -0.3(6) 2_676 . . . ?
C4 C5 C6 C7 177.4(3) . . . . ?
C7 C5 C6 C1 -178.2(3) 2_676 . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C2 C1 C6 C7 -178.7(4) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
C5 C6 C7 C5 0.3(6) . . . 2_676 ?
C1 C6 C7 C5 178.1(4) . . . 2_676 ?
C5 C6 C7 C8 -177.0(3) . . . . ?
C1 C6 C7 C8 0.8(6) . . . . ?
C9 N1 C8 C7 176.8(3) . . . . ?
C5 C7 C8 N1 146.0(4) 2_676 . . . ?
C6 C7 C8 N1 -36.6(6) . . . . ?
C8 N1 C9 C14 -31.3(5) . . . . ?
C8 N1 C9 C10 152.7(3) . . . . ?
C14 C9 C10 C11 1.4(5) . . . . ?
N1 C9 C10 C11 177.7(3) . . . . ?
C9 C10 C11 C12 -2.0(6) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
C10 C11 C12 C15 -174.1(3) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C15 C12 C13 C14 175.3(3) . . . . ?
C12 C13 C14 C9 -0.5(6) . . . . ?
C10 C9 C14 C13 -0.2(5) . . . . ?
N1 C9 C14 C13 -176.1(3) . . . . ?
C11 C12 C15 C18 -143.5(3) . . . . ?
C13 C12 C15 C18 41.3(5) . . . . ?
C11 C12 C15 C17 96.6(4) . . . . ?
C13 C12 C15 C17 -78.5(4) . . . . ?
C11 C12 C15 C16 -23.6(5) . . . . ?
C13 C12 C15 C16 161.2(3) . . . . ?
