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_7241322
_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         'C20 H16 N8'
_chemical_formula_sum            'C20 H16 N8'
_chemical_formula_weight         368.41
_chemical_name_common            TPCB
_chemical_name_systematic        rctt-tetrakis-(5-pyrimidyl)-cyclobutane
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-20 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.938(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6660(16)
_cell_length_b                   7.1513(7)
_cell_length_c                   17.0738(17)
_cell_measurement_reflns_used    3010
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.91
_cell_volume                     1774.3(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_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      298
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5586
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_min         3.015
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.8276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_preparation       'solvent evaporation'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1618
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0577
_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/[\s^2^(Fo^2^)+(0.0405P)^2^+1.9570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1375
_reflns_number_total             1618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01280g2.cif
_cod_data_source_block           mcg13116
_cod_database_code               7241322
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C9A, C9B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10A, C10B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Same fragment restrains
{C9A, C10A} sigma for 1-2: 0.02, 1-3: 0.04
{C9A, C10A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C9B, C10B}
4. Others
 Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=1-FVAR(1)
 Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9A(H9A), C10A(H10A), C9B(H9B), C10B(H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C8(H8)
;
_shelx_res_checksum              65125
_olex2_submission_special_instructions 'No special instructions were received'