Hierarchy of π-stacking determines the conformational preferences of bis-squaramates
Singh, Abhishek; Singh, Reman Kumar; Patwari, G. Naresh; CrystEngComm 23 (2021) 5331–5336; doi:10.1039/D1CE00623A

data_7243068
_publ_section_title
;
 Hierarchy of \p-stacking determines the conformational preferences of
 bis-squaramates
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              5331
_journal_page_last               5336
_journal_paper_doi               10.1039/D1CE00623A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C7 H8 N O3'
_chemical_formula_sum            'C14 H16 N2 O6'
_chemical_formula_weight         154.14
_chemical_name_common
4,4'-(butane-1,4-diylbis(azanediyl))bis(3-methoxycyclobut-3-ene-1,2-dione)
_chemical_name_systematic        Sq-1,4-dimer
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-02-26 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.535(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4828(16)
_cell_length_b                   12.528(2)
_cell_length_c                   6.6496(11)
_cell_measurement_reflns_used    1215
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.5550
_cell_measurement_theta_min      2.8890
_cell_volume                     706.0(2)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00  69.50   0.50    8.00    --  -20.00   0.00  36.00  359
  2  \w    -70.00 -36.00   0.50    8.00    --  -20.00 -72.00 -36.00   68
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0477730000
_diffrn_orient_matrix_UB_12      0.0424282000
_diffrn_orient_matrix_UB_13      -0.0385813000
_diffrn_orient_matrix_UB_21      0.0099960000
_diffrn_orient_matrix_UB_22      -0.0186373000
_diffrn_orient_matrix_UB_23      -0.0993259000
_diffrn_orient_matrix_UB_31      -0.0680032000
_diffrn_orient_matrix_UB_32      -0.0325303000
_diffrn_orient_matrix_UB_33      0.0066367000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2742
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.958
_diffrn_reflns_theta_max         24.957
_diffrn_reflns_theta_min         2.902
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/ACN/CHCl3'
_exptl_crystal_size_max          0.0411
_exptl_crystal_size_mid          0.0321
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0954
_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^)+(0.1908P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2552
_refine_ls_wR_factor_ref         0.2825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                865
_reflns_number_total             1223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00623a2.cif
_cod_data_source_block           gnp-ab-1-4-dimer_mo
_cod_depositor_comments
'Adding full bibliography for 7243068--7243072.cif.'
_cod_database_code               7243068
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 88.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              14818
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.996
_oxdiff_exptl_absorpt_empirical_full_min 0.739