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_7243072
_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         'C15 H18 N2 O6'
_chemical_formula_sum            'C15 H18 N2 O6'
_chemical_formula_weight         322.31
_chemical_name_common
4,4'-(propane-1,3-diylbis(methylazanediyl))bis(3-methoxycyclobut-3-ene-1,2-dione)
_chemical_name_systematic        Sq-1,3-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
_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                84.028(6)
_cell_angle_beta                 86.103(6)
_cell_angle_gamma                89.868(5)
_cell_formula_units_Z            4
_cell_length_a                   8.4804(5)
_cell_length_b                   13.0556(8)
_cell_length_c                   13.3103(10)
_cell_measurement_reflns_used    3137
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.4320
_cell_measurement_theta_min      2.7650
_cell_volume                     1462.27(17)
_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_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  25.00   0.50    8.00    --  -20.00   0.00-108.00  270
  2  \w   -110.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  258
  3  \w    -69.00  19.00   0.50    8.00    --  -20.00 -72.00  36.00  176
  4  \w    -49.50  -3.00   0.50    8.00    --  -20.00  72.00-180.00   93
  5  \w    -39.00  -9.00   0.50    8.00    --  -20.00 -72.00 -36.00   60
  6  \w    -59.00 -43.00   0.50    8.00    --  -20.00  72.00  36.00   32
;
_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_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.1189
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12356
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.568
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87357
_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    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/ACN'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         5140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0795
_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^)+(0.0822P)^2^+0.5787P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.2220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2861
_reflns_number_total             5140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00623a2.cif
_cod_data_source_block           gnp-1-2-n-methyldimer_mo
_cod_depositor_comments
;
Adding full bibliography for 7243068--7243072.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H36 N4 O12'
_cod_original_formula_weight         644.63
_cod_original_formula_moiety         '2(C15 H18 N2 O6)'
_cod_original_formula_units_Z            2
_cod_database_code               7243072
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.976
_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:
 C00K(H00A,H00B), C00N(H00C,H00D), C00O(H00H,H00I), C00Q(H00J,H00K), C00X(H00L,
 H00M), C012(H01A,H01B)
2.b Idealised Me refined as rotating group:
 C00Y(H00E,H00F,H00G), C011(H01L,H01M,H01N), C015(H01O,H01P,H01Q), C016(H01C,
 H01D,H01E), C017(H01F,H01G,H01H), C018(H01R,H01S,H01T), C019(H01I,H01J,H01K),
 C01A(H01U,H01V,H01W)
;
_shelx_res_checksum              27453
_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
;