#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:29:37 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268674 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/30/7243071.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243071
loop_
_publ_author_name
'Singh, Abhishek'
'Singh, Reman Kumar'
'Patwari, G. Naresh'
_publ_section_title
;
 Hierarchy of π-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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -35.00   0.50    0.10    --  -47.70 -42.00  25.00  170
  2  ω     35.00 120.00   0.50    0.10    --   47.70  42.00 177.00  170
  3  ω    -24.00  60.00   0.50    0.10    --   47.70 -42.00  25.00  168
  4  ω    -75.00 -14.00   0.50    0.40    --  -86.25  42.00 177.00  122
  5  ω   -158.00 -74.00   0.50    0.40    --  -86.25 -42.00  25.00  168
  6  ω     36.00  73.00   0.50    0.40    --  107.75 -42.00  25.00   74
  7  ω     95.00 178.00   0.50    0.40    --  107.75  42.00 177.00  166
  8  ω    -60.00  25.00   0.50    0.10    --  -47.70  42.00 177.00  170
  9  ω   -121.00 -35.00   0.50    0.10    --  -47.70 -37.00 -90.00  172
 10  ω   -119.00 -73.00   0.50    0.10    --  -47.70-125.00 -90.00   92
 11  ω   -119.00 -33.00   0.50    0.10    --  -47.70 -57.00-120.00  172
 12  ω     34.00  95.00   0.50    0.10    --   47.70-125.00  30.00  122
 13  ω   -158.00 -73.00   0.50    0.40    --  -86.25 -45.00 -30.00  170
 14  ω    -86.00 -13.00   0.50    0.40    --  -86.25 125.00-150.00  146
 15  ω   -159.00 -63.00   0.50    0.40    --  -86.25 -77.00 -60.00  192
 16  ω   -159.00 -68.00   0.50    0.40    --  -86.25 -66.00 -94.51  182
 17  ω   -158.00 -73.00   0.50    0.40    --  -86.25 -45.00 -60.00  170
 18  ω   -159.00 -70.00   0.50    0.40    --  -86.25 -61.00 -60.00  178
 19  ω   -159.00 -65.00   0.50    0.40    --  -86.25 -74.00-111.44  188
 20  ω   -159.00 -64.00   0.50    0.40    --  -86.25 -75.00 -54.08  190
 21  ω     95.00 178.00   0.50    0.40    --  107.75  30.00 150.00  166
 22  ω     89.00 178.00   0.50    0.40    --  107.75  67.00 -86.55  178
 23  ω     94.00 178.00   0.50    0.40    --  107.75  15.00 120.00  168
 24  ω     85.00 178.00   0.50    0.40    --  107.75  77.00-150.00  186
 25  ω     36.00  76.00   0.50    0.40    --  107.75 -45.00-120.00   80
 26  ω     33.00  66.00   0.50    0.40    --  107.75 -30.00-180.00   66
 27  ω     36.00  76.00   0.50    0.40    --  107.75 -45.00-150.00   80
 28  ω     35.00 106.00   0.50    0.40    --  107.75 -94.00  60.00  142
 29  ω     33.00  66.00   0.50    0.40    --  107.75 -30.00 150.00   66
 30  ω    102.00 149.00   0.50    0.40    --  107.75  30.00 -30.00   94
 31  ω     87.00 133.00   0.50    0.40    --  107.75  77.00 -60.00   92
 32  ω    125.00 177.00   0.50    0.40    --  107.75  77.00-120.00  104
 33  ω     93.00 121.00   0.50    0.40    --  107.75  77.00 -90.00   56
 34  ω    145.00 170.00   0.50    0.40    --  107.75  77.00 -90.00   50
 35  ω     36.00  62.00   0.50    0.40    --  107.75 -30.00-120.00   52
 36  ω     86.00 117.00   0.50    0.40    --  107.75  77.00-120.00   62
 37  ω     47.00  73.00   0.50    0.40    --  107.75 -94.00-120.00   52
 38  ω     91.00 147.00   0.50    0.40    --  107.75  61.00-150.00  112
 39  ω    134.00 175.00   0.50    0.40    --  107.75  77.00-180.00   82
 40  ω     40.00  76.00   0.50    0.40    --  107.75 -45.00 -60.00   72
 41  ω    101.00 126.00   0.50    0.40    --  107.75  45.00 -90.00   50
 42  ω    148.00 173.00   0.50    0.40    --  107.75  45.00 -90.00   50
 43  ω     39.00  64.00   0.50    0.40    --  107.75 -45.00  60.00   50
 44  ω     35.00  62.00   0.50    0.40    --  107.75 -30.00 -90.00   54
 45  ω     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       'ω 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/[σ²(Fo²)+(0.0456P)²+1.0395P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.46479(8) 0.81817(8) 0.49816(6) 0.0216(2) Uani 1 1 d . . . . .
O002 O 0.34496(9) 0.61729(8) 0.66874(7) 0.0233(2) Uani 1 1 d . . . . .
O003 O 0.27386(9) 0.40517(8) 0.46418(8) 0.0278(2) Uani 1 1 d . . . . .
N004 N 0.37041(10) 0.61622(9) 0.29624(8) 0.0201(2) Uani 1 1 d . . . . .
H004 H 0.339908 0.546871 0.255733 0.024 Uiso 1 1 calc R . . . .
C005 C 0.36856(11) 0.61433(11) 0.40303(9) 0.0179(2) Uani 1 1 d . . . . .
C006 C 0.40625(11) 0.70056(11) 0.49350(9) 0.0177(2) Uani 1 1 d . . . . .
C007 C 0.35681(11) 0.61344(11) 0.57116(9) 0.0186(2) Uani 1 1 d . . . . .
C008 C 0.42125(12) 0.72926(11) 0.24203(9) 0.0215(3) Uani 1 1 d . . . . .
H00A H 0.390914 0.811518 0.273120 0.026 Uiso 1 1 calc R . . . .
H00B H 0.380180 0.727301 0.161546 0.026 Uiso 1 1 calc R . . . .
C009 C 0.32044(11) 0.51533(11) 0.47629(9) 0.0195(3) Uani 1 1 d . . . . .
C00A C 0.52182(13) 0.86478(13) 0.60973(9) 0.0253(3) Uani 1 1 d . . . . .
H00C H 0.573518 0.946371 0.605564 0.038 Uiso 1 1 calc GR . . . .
H00D H 0.584129 0.797919 0.649918 0.038 Uiso 1 1 calc GR . . . .
H00E H 0.446321 0.881510 0.649037 0.038 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 1 0.0367
1 1 -1 0.0397
1 -1 0 0.1088
-1 1 0 0.1088
0 0 1 0.0292
0 0 -1 0.0042
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C006 O001 C00A 114.71(9) . . ?
C005 N004 C008 122.61(10) . . ?
N004 C005 C006 136.44(11) . . ?
N004 C005 C009 133.01(10) . . ?
C006 C005 C009 90.54(9) . . ?
O001 C006 C005 129.87(10) . . ?
O001 C006 C007 136.19(10) . . ?
C005 C006 C007 93.93(9) . . ?
O002 C007 C006 136.92(11) . . ?
O002 C007 C009 135.61(10) . . ?
C006 C007 C009 87.43(9) . . ?
N004 C008 C008 111.96(8) . 2_655 ?
O003 C009 C005 135.33(11) . . ?
O003 C009 C007 136.67(11) . . ?
C005 C009 C007 88.01(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C006 1.3235(14) . ?
O001 C00A 1.4518(13) . ?
O002 C007 1.2278(14) . ?
O003 C009 1.2078(14) . ?
N004 C005 1.3155(15) . ?
N004 C008 1.4658(14) . ?
C005 C006 1.4051(15) . ?
C005 C009 1.4895(15) . ?
C006 C007 1.4555(15) . ?
C007 C009 1.5205(16) . ?
C008 C008 1.525(2) 2_655 ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -1.0000 1.0000 -0.0791 0.0507 0.2187
1.0000 1.0000 -1.0000 0.0791 -0.0507 -0.2187
1.0000 -1.0000 0.0000 0.1686 -0.1063 0.0932
-1.0000 1.0000 -0.0000 -0.1686 0.1063 -0.0932
0.0000 -0.0000 1.0000 0.0581 0.1006 0.0539
-0.0000 0.0000 -1.0000 -0.0581 -0.1006 -0.0539
