Application of a tetrapyrimidyl cyclobutane synthesized in the organic solid state: a halogen-bonded supramolecular ladder
Sinnwell, Michael A.; Santana, Carlos; Bosch, Eric; MacGillivray, Len R.; Groeneman , Ryan; CrystEngComm  (2020) –; doi:10.1039/D0CE01280G

data_7241323
_publ_section_title
;
 Application of a tetrapyrimidyl cyclobutane synthesized in the organic
 solid state: a halogen-bonded supramolecular ladder
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01280G
_journal_year                    2020
_chemical_formula_moiety         '2(C6 Cl4 I2), C20 H16 N8, C7 H8'
_chemical_formula_sum            'C39 H24 Cl8 I4 N8'
_chemical_formula_weight         1395.86
_chemical_name_systematic
'rctt-1,2,3,4-tetrakis-(5-pyrimdyl)cyclobutane tetrachloro-1,4-diiodobenzne'
_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     dual
_audit_creation_date             2020-06-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-26 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                82.686(2)
_cell_angle_beta                 74.068(2)
_cell_angle_gamma                72.653(2)
_cell_formula_units_Z            1
_cell_length_a                   8.9258(5)
_cell_length_b                   9.1762(6)
_cell_length_c                   14.6465(8)
_cell_measurement_reflns_used    6944
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.33
_cell_volume                     1099.72(11)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      102(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13882
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.328
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.361
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0999 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.8710.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_description       block
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4990
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0225
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0181P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0480
_refine_ls_wR_factor_ref         0.0499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4331
_reflns_number_total             4990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01280g2.cif
_cod_data_source_block           r23219
_cod_database_code               7241323
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17-C18
 1.51 with sigma of 0.02
 C18-C19 = C18-C23 = C20-C21
 1.39 with sigma of 0.02
 C19-C20 = C21-C22 = C22-C23
 1.38 with sigma of 0.02
 C18-C20
 2.42 with sigma of 0.04
 C19-C21
 2.39 with sigma of 0.04
 C18-C22
 2.41 with sigma of 0.04
 C20-C22 = C21-C23
 2.4 with sigma of 0.04
 C17-C19 = C17-C23
 2.52 with sigma of 0.04
 C18-C19 \\sim C19-C20 \\sim C20-C21 \\sim C21-C22 \\sim C22-C23 \\sim C23-C18
 with sigma of 0.02
 C18-C22 \\sim C18-C20 \\sim C23-C21 \\sim C19-C23 \\sim C20-C22 \\sim C19-C21
 with sigma of 0.04
 C17-C23 \\sim C17-C19
 with sigma of 0.04
3. Restrained planarity
 C17, C18, C19, C20, C21, C22, C23
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C17, C18, C19, C20, C21, C22, C23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C17(0.5) H17A(0.5) H17B(0.5) H17C(0.5) C18(0.5) C19(0.5) H19(0.5)
 C20(0.5) H20(0.5) C21(0.5) H21(0.5) C22(0.5) H22(0.5) C23(0.5) H23(0.5)
7.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C8(H8), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23)
7.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              27891
_olex2_submission_special_instructions 'No special instructions were received'