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_7243069
_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         'C10 H7 N2 O6, H2 O'
_chemical_formula_sum            'C10 H9 N2 O7'
_chemical_formula_weight         269.19
_chemical_name_common
4,4'-(ethane-1,2-diylbis(azanediyl))bis(3-hydroxycyclobut-3-ene-1,2-dione)
_chemical_name_systematic        Sq-12-dimer-hydrate
_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   mixed
_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                 93.465(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8489(4)
_cell_length_b                   15.6629(4)
_cell_length_c                   11.8621(3)
_cell_measurement_reflns_used    11352
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      29.8290
_cell_measurement_theta_min      3.4480
_cell_volume                     2197.44(11)
_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      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.841
_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 -16.00 23.00 0.50 10.00 -- 4.17-101.00 69.00 78 2 \w -18.00 7.00 0.50 10.00 -- -4.95-101.00 69.00 50 3 \w -23.00 29.00 0.50 10.00 -- -4.95 -99.00 30.00 104 4 \w -23.00 29.00 0.50 10.00 -- -4.95 -99.00 -90.00 104 5 \w -23.00 38.00 0.50 10.00 -- 4.17 -99.00-180.00 122 6 \w -23.00 37.00 0.50 10.00 -- 4.17 -99.00-120.00 120 7 \w -20.00 21.00 0.50 10.00 -- -4.95 -99.00-150.00 82 8 \w 17.00 42.00 0.50 10.00 -- 4.17 37.00-150.00 50 9 \w -5.00 20.00 0.50 10.00 -- -4.95 37.00-150.00 50'
_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      -0.0492948000
_diffrn_orient_matrix_UB_12      -0.0229607000
_diffrn_orient_matrix_UB_13      0.0126461000
_diffrn_orient_matrix_UB_21      -0.0335037000
_diffrn_orient_matrix_UB_22      0.0365574000
_diffrn_orient_matrix_UB_23      -0.0133133000
_diffrn_orient_matrix_UB_31      -0.0069302000
_diffrn_orient_matrix_UB_32      -0.0136351000
_diffrn_orient_matrix_UB_33      -0.0570066000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27950
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.710
_diffrn_reflns_theta_min         3.441
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019) 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    1.627
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Water/HCl'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0617P)^2^+0.8678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4422
_reflns_number_total             5740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00623a2.cif
_cod_data_source_block           sq12
_cod_depositor_comments
;
Adding full bibliography for 7243068--7243072.cif.

2024-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C20 H18 N4 O14'
_cod_original_formula_weight         538.38
_cod_original_formula_moiety         '2(C10 H7 N2 O6), 2(H2 O)'
_cod_original_formula_units_Z            4
_cod_database_code               7243069
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H10 O6 N2'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.975
_diffrn_oxdiff_digest_frames
;
0103ab17b34419d209a2a7bcf1675077cc00026d9df
;
_diffrn_oxdiff_digest_hkl
;
01b2d198b81d84ab9be174b402798460fdc3fd
;
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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 O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O00B(H00E,H00J), O00E(H00K,H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C00Z(H00C,H00D), C011(H01A,H01B), C012(H01C,H01D)
2.c Aromatic/amide H refined with riding coordinates:
 N00F(H00F), N00G(H00G), N00H(H00H), N00I(H00I)
2.d Idealised tetrahedral OH refined as rotating group:
 O004(H004), O007(H007)
;
_shelx_res_checksum              71023
_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 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.719