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_7243071
_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         '0.8(C12 H12 N2 O6)'
_chemical_formula_sum            'C12 H12 N2 O6'
_chemical_formula_weight         224.19
_chemical_name_common
4,4'-(ethane-1,2-diylbis(azanediyl))bis(3-methoxycyclobut-3-ene-1,2-dione)
_chemical_name_systematic        Sq-1,2-dimer
_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             2020-02-13
_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                 101.6170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            5
_cell_length_a                   9.85680(10)
_cell_length_b                   10.16330(10)
_cell_length_c                   12.28110(10)
_cell_measurement_reflns_used    9047
_cell_measurement_temperature    122.99(10)
_cell_measurement_theta_max      77.1640
_cell_measurement_theta_min      6.2890
_cell_volume                     1205.09(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      122.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_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   -120.00 -35.00   0.50    0.10    --  -47.70 -42.00  25.00  170
  2  \w     35.00 120.00   0.50    0.10    --   47.70  42.00 177.00  170
  3  \w    -24.00  60.00   0.50    0.10    --   47.70 -42.00  25.00  168
  4  \w    -75.00 -14.00   0.50    0.40    --  -86.25  42.00 177.00  122
  5  \w   -158.00 -74.00   0.50    0.40    --  -86.25 -42.00  25.00  168
  6  \w     36.00  73.00   0.50    0.40    --  107.75 -42.00  25.00   74
  7  \w     95.00 178.00   0.50    0.40    --  107.75  42.00 177.00  166
  8  \w    -60.00  25.00   0.50    0.10    --  -47.70  42.00 177.00  170
  9  \w   -121.00 -35.00   0.50    0.10    --  -47.70 -37.00 -90.00  172
 10  \w   -119.00 -73.00   0.50    0.10    --  -47.70-125.00 -90.00   92
 11  \w   -119.00 -33.00   0.50    0.10    --  -47.70 -57.00-120.00  172
 12  \w     34.00  95.00   0.50    0.10    --   47.70-125.00  30.00  122
 13  \w   -158.00 -73.00   0.50    0.40    --  -86.25 -45.00 -30.00  170
 14  \w    -86.00 -13.00   0.50    0.40    --  -86.25 125.00-150.00  146
 15  \w   -159.00 -63.00   0.50    0.40    --  -86.25 -77.00 -60.00  192
 16  \w   -159.00 -68.00   0.50    0.40    --  -86.25 -66.00 -94.51  182
 17  \w   -158.00 -73.00   0.50    0.40    --  -86.25 -45.00 -60.00  170
 18  \w   -159.00 -70.00   0.50    0.40    --  -86.25 -61.00 -60.00  178
 19  \w   -159.00 -65.00   0.50    0.40    --  -86.25 -74.00-111.44  188
 20  \w   -159.00 -64.00   0.50    0.40    --  -86.25 -75.00 -54.08  190
 21  \w     95.00 178.00   0.50    0.40    --  107.75  30.00 150.00  166
 22  \w     89.00 178.00   0.50    0.40    --  107.75  67.00 -86.55  178
 23  \w     94.00 178.00   0.50    0.40    --  107.75  15.00 120.00  168
 24  \w     85.00 178.00   0.50    0.40    --  107.75  77.00-150.00  186
 25  \w     36.00  76.00   0.50    0.40    --  107.75 -45.00-120.00   80
 26  \w     33.00  66.00   0.50    0.40    --  107.75 -30.00-180.00   66
 27  \w     36.00  76.00   0.50    0.40    --  107.75 -45.00-150.00   80
 28  \w     35.00 106.00   0.50    0.40    --  107.75 -94.00  60.00  142
 29  \w     33.00  66.00   0.50    0.40    --  107.75 -30.00 150.00   66
 30  \w    102.00 149.00   0.50    0.40    --  107.75  30.00 -30.00   94
 31  \w     87.00 133.00   0.50    0.40    --  107.75  77.00 -60.00   92
 32  \w    125.00 177.00   0.50    0.40    --  107.75  77.00-120.00  104
 33  \w     93.00 121.00   0.50    0.40    --  107.75  77.00 -90.00   56
 34  \w    145.00 170.00   0.50    0.40    --  107.75  77.00 -90.00   50
 35  \w     36.00  62.00   0.50    0.40    --  107.75 -30.00-120.00   52
 36  \w     86.00 117.00   0.50    0.40    --  107.75  77.00-120.00   62
 37  \w     47.00  73.00   0.50    0.40    --  107.75 -94.00-120.00   52
 38  \w     91.00 147.00   0.50    0.40    --  107.75  61.00-150.00  112
 39  \w    134.00 175.00   0.50    0.40    --  107.75  77.00-180.00   82
 40  \w     40.00  76.00   0.50    0.40    --  107.75 -45.00 -60.00   72
 41  \w    101.00 126.00   0.50    0.40    --  107.75  45.00 -90.00   50
 42  \w    148.00 173.00   0.50    0.40    --  107.75  45.00 -90.00   50
 43  \w     39.00  64.00   0.50    0.40    --  107.75 -45.00  60.00   50
 44  \w     35.00  62.00   0.50    0.40    --  107.75 -30.00 -90.00   54
 45  \w     55.00 106.00   0.50    0.40    --  107.75-125.00 -60.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1529140000
_diffrn_orient_matrix_UB_12      -0.0157206000
_diffrn_orient_matrix_UB_13      0.0580565000
_diffrn_orient_matrix_UB_21      -0.0281816000
_diffrn_orient_matrix_UB_22      0.0780727000
_diffrn_orient_matrix_UB_23      0.1006349000
_diffrn_orient_matrix_UB_31      -0.0358130000
_diffrn_orient_matrix_UB_32      -0.1289813000
_diffrn_orient_matrix_UB_33      0.0538620000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11091
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.539
_diffrn_reflns_theta_min         6.323
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.081
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.480
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.545
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/ACN'
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0456P)^2^+1.0395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1224
_reflns_number_total             1259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00623a2.cif
_cod_data_source_block           mx140_19
_cod_depositor_comments
'Adding full bibliography for 7243068--7243072.cif.'
_cod_database_code               7243071
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_diffrn_oxdiff_digest_frames
;
01007bb4685622e96caffd171b46951674054483bf3
;
_diffrn_oxdiff_digest_hkl
;
010fa7d80f327d745ee5650285391290c829e3
;
_reflns_odcompleteness_completeness 99.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C008(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 N004(H004)
2.c Idealised Me refined as rotating group:
 C00A(H00C,H00D,H00E)
;
_shelx_res_checksum              49272
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.492
_oxdiff_exptl_absorpt_empirical_full_min 0.729