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_7243070
_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         'C14 H16 N2 O6'
_chemical_formula_sum            'C14 H16 N2 O6'
_chemical_formula_weight         308.29
_chemical_name_common
4,4'-(ethane-1,2-diylbis(methylazanediyl))bis(3-methoxycyclobut-3-ene-1,2-dione)
_chemical_name_systematic        Sq-1,2-methyldimer
_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     direct
_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
;
2020-02-25 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                79.094(4)
_cell_angle_beta                 86.345(3)
_cell_angle_gamma                79.409(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8262(3)
_cell_length_b                   9.1203(4)
_cell_length_c                   10.2647(4)
_cell_measurement_reflns_used    6752
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.0030
_cell_measurement_theta_min      2.0480
_cell_volume                     706.86(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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 plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  19.00   0.50    8.00    --  -20.00 -72.00-180.00  258
  2  \w    -99.00  25.00   0.50    8.00    --  -20.00   0.00-180.00  248
  3  \w    -69.00  10.00   0.50    8.00    --  -20.00 -72.00 -36.00  158
  4  \w    -52.50   0.00   0.50    8.00    --  -20.00  72.00 108.00  105
  5  \w    -39.00  -9.00   0.50    8.00    --  -20.00 -72.00-108.00   60
  6  \w    -63.00  70.00   0.50    8.00    --  -20.00   0.00-108.00  266
  7  \w    -81.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  200
  8  \w    -59.00   1.50   0.50    8.00    --  -20.00  72.00 -36.00  121
  9  \w    -58.50 -12.00   0.50    8.00    --  -20.00  72.00  36.00   93
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0462716000
_diffrn_orient_matrix_UB_12      0.0699961000
_diffrn_orient_matrix_UB_13      -0.0331717000
_diffrn_orient_matrix_UB_21      -0.0749390000
_diffrn_orient_matrix_UB_22      -0.0120419000
_diffrn_orient_matrix_UB_23      0.0403548000
_diffrn_orient_matrix_UB_31      0.0274217000
_diffrn_orient_matrix_UB_32      0.0377794000
_diffrn_orient_matrix_UB_33      0.0471992000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10055
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.021
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92683
_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    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/ACN mixture'
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0740P)^2^+0.4427P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2193
_reflns_number_total             2484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00623a2.cif
_cod_data_source_block           gnp-as-13_mo
_cod_depositor_comments
'Adding full bibliography for 7243068--7243072.cif.'
_cod_database_code               7243070
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H18O6N2
_reflns_odcompleteness_completeness 91.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C6(H6A,H6B,H6C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              57823
_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 2.030
_oxdiff_exptl_absorpt_empirical_full_min 0.732