#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:29:37 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268674 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/30/7243070.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_7243070
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         '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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  19.00   0.50    8.00    --  -20.00 -72.00-180.00  258
  2  ω    -99.00  25.00   0.50    8.00    --  -20.00   0.00-180.00  248
  3  ω    -69.00  10.00   0.50    8.00    --  -20.00 -72.00 -36.00  158
  4  ω    -52.50   0.00   0.50    8.00    --  -20.00  72.00 108.00  105
  5  ω    -39.00  -9.00   0.50    8.00    --  -20.00 -72.00-108.00   60
  6  ω    -63.00  70.00   0.50    8.00    --  -20.00   0.00-108.00  266
  7  ω    -81.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  200
  8  ω    -59.00   1.50   0.50    8.00    --  -20.00  72.00 -36.00  121
  9  ω    -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       'ω 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/[σ²(Fo²)+(0.0740P)²+0.4427P] where P=(Fo²+2Fc²)/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 > 2σ(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
_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.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O5 O 0.60865(19) 0.55996(16) -0.14286(14) 0.0317(4) Uani 1 1 d . . . . .
O2 O 0.45977(19) 0.03455(16) 0.27468(14) 0.0326(4) Uani 1 1 d . . . . .
O1 O 0.31921(19) 0.25055(18) 0.49189(15) 0.0366(4) Uani 1 1 d . . . . .
O4 O 0.8911(2) 0.25588(18) -0.04173(16) 0.0400(4) Uani 1 1 d . . . . .
O6 O 0.67800(19) 0.68641(15) 0.12700(14) 0.0306(4) Uani 1 1 d . . . . .
O3 O 0.72851(19) 0.27098(18) 0.53765(15) 0.0358(4) Uani 1 1 d . . . . .
N1 N 0.8602(2) 0.07034(19) 0.31621(17) 0.0269(4) Uani 1 1 d . . . . .
N2 N 0.9524(2) 0.38579(18) 0.22456(16) 0.0254(4) Uani 1 1 d . . . . .
C7 C 1.0180(3) 0.1206(2) 0.3475(2) 0.0281(5) Uani 1 1 d . . . . .
H7A H 1.113646 0.032171 0.362595 0.034 Uiso 1 1 calc R . . . .
H7B H 0.996884 0.162198 0.430579 0.034 Uiso 1 1 calc R . . . .
C4 C 0.5255(3) 0.1033(2) 0.34268(19) 0.0255(5) Uani 1 1 d . . . . .
C5 C 0.4612(3) 0.2023(2) 0.4448(2) 0.0269(5) Uani 1 1 d . . . . .
C3 C 0.7054(3) 0.1215(2) 0.36564(19) 0.0238(4) Uani 1 1 d . . . . .
C8 C 1.0730(3) 0.2404(2) 0.2374(2) 0.0281(5) Uani 1 1 d . . . . .
H8A H 1.190373 0.256528 0.255312 0.034 Uiso 1 1 calc R . . . .
H8B H 1.080379 0.203240 0.152292 0.034 Uiso 1 1 calc R . . . .
C12 C 0.6999(3) 0.5132(2) -0.04646(19) 0.0250(4) Uani 1 1 d . . . . .
C13 C 0.7340(3) 0.5652(2) 0.07323(19) 0.0236(4) Uani 1 1 d . . . . .
C11 C 0.8308(3) 0.3717(2) 0.0003(2) 0.0273(5) Uani 1 1 d . . . . .
C2 C 0.6421(3) 0.2108(2) 0.4610(2) 0.0262(5) Uani 1 1 d . . . . .
C10 C 0.8543(2) 0.4345(2) 0.11965(19) 0.0229(4) Uani 1 1 d . . . . .
C9 C 0.9598(3) 0.4820(2) 0.3223(2) 0.0325(5) Uani 1 1 d . . . . .
H9A H 0.990069 0.418082 0.408585 0.049 Uiso 1 1 calc GR . . . .
H9B H 0.846198 0.546521 0.330226 0.049 Uiso 1 1 calc GR . . . .
H9C H 1.048180 0.545768 0.293660 0.049 Uiso 1 1 calc GR . . . .
C14 C 0.5574(3) 0.8042(3) 0.0480(2) 0.0411(6) Uani 1 1 d . . . . .
H14A H 0.614032 0.839921 -0.037010 0.062 Uiso 1 1 calc GR . . . .
H14B H 0.521865 0.888896 0.095668 0.062 Uiso 1 1 calc GR . . . .
H14C H 0.454821 0.763392 0.031950 0.062 Uiso 1 1 calc GR . . . .
C6 C 0.8795(3) -0.0374(3) 0.2245(2) 0.0380(5) Uani 1 1 d . . . . .
H6A H 0.901878 0.014931 0.134210 0.057 Uiso 1 1 calc GR . . . .
H6B H 0.772380 -0.079312 0.227040 0.057 Uiso 1 1 calc GR . . . .
H6C H 0.977047 -0.119847 0.251017 0.057 Uiso 1 1 calc GR . . . .
C1 C 0.6267(4) 0.3487(3) 0.6355(3) 0.0491(7) Uani 1 1 d . . . . .
H1A H 0.607270 0.458294 0.602397 0.074 Uiso 1 1 calc GR . . . .
H1B H 0.689667 0.325927 0.718504 0.074 Uiso 1 1 calc GR . . . .
H1C H 0.514513 0.314259 0.651740 0.074 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C13 O6 C14 115.00(16) . . ?
C2 O3 C1 116.72(18) . . ?
C7 N1 C6 117.36(16) . . ?
C3 N1 C7 122.03(17) . . ?
C3 N1 C6 120.60(17) . . ?
C10 N2 C8 120.39(17) . . ?
C10 N2 C9 121.24(17) . . ?
C9 N2 C8 117.96(17) . . ?
N1 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
N1 C7 C8 112.24(17) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O2 C4 C5 135.94(19) . . ?
O2 C4 C3 135.68(19) . . ?
C3 C4 C5 88.34(15) . . ?
O1 C5 C4 135.46(19) . . ?
O1 C5 C2 137.37(19) . . ?
C2 C5 C4 87.16(15) . . ?
N1 C3 C4 133.87(18) . . ?
N1 C3 C2 135.79(19) . . ?
C2 C3 C4 90.33(16) . . ?
N2 C8 C7 112.73(17) . . ?
N2 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O5 C12 C13 137.47(19) . . ?
O5 C12 C11 135.41(18) . . ?
C13 C12 C11 87.12(15) . . ?
O6 C13 C12 136.11(18) . . ?
O6 C13 C10 129.87(18) . . ?
C10 C13 C12 94.02(16) . . ?
O4 C11 C12 135.8(2) . . ?
O4 C11 C10 135.7(2) . . ?
C10 C11 C12 88.51(15) . . ?
O3 C2 C5 136.35(19) . . ?
O3 C2 C3 129.43(19) . . ?
C3 C2 C5 94.16(16) . . ?
N2 C10 C13 135.71(18) . . ?
N2 C10 C11 133.94(18) . . ?
C13 C10 C11 90.34(16) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
O6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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
O5 C12 1.220(2) . ?
O2 C4 1.215(2) . ?
O1 C5 1.222(3) . ?
O4 C11 1.220(3) . ?
O6 C13 1.320(2) . ?
O6 C14 1.448(3) . ?
O3 C2 1.321(2) . ?
O3 C1 1.451(3) . ?
N1 C7 1.467(3) . ?
N1 C3 1.322(3) . ?
N1 C6 1.467(3) . ?
N2 C8 1.468(3) . ?
N2 C10 1.321(3) . ?
N2 C9 1.463(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.517(3) . ?
C4 C5 1.514(3) . ?
C4 C3 1.486(3) . ?
C5 C2 1.454(3) . ?
C3 C2 1.399(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C12 C13 1.454(3) . ?
C12 C11 1.512(3) . ?
C13 C10 1.401(3) . ?
C11 C10 1.481(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C12 C13 O6 0.5(4) . . . . ?
O5 C12 C13 C10 179.7(2) . . . . ?
O5 C12 C11 O4 0.2(4) . . . . ?
O5 C12 C11 C10 -179.7(2) . . . . ?
O2 C4 C5 O1 -2.3(4) . . . . ?
O2 C4 C5 C2 177.0(2) . . . . ?
O2 C4 C3 N1 1.9(4) . . . . ?
O2 C4 C3 C2 -177.0(2) . . . . ?
O1 C5 C2 O3 2.9(4) . . . . ?
O1 C5 C2 C3 -179.9(3) . . . . ?
O4 C11 C10 N2 0.6(4) . . . . ?
O4 C11 C10 C13 179.4(3) . . . . ?
O6 C13 C10 N2 -1.2(4) . . . . ?
O6 C13 C10 C11 180.0(2) . . . . ?
N1 C7 C8 N2 69.1(2) . . . . ?
N1 C3 C2 O3 -2.2(4) . . . . ?
N1 C3 C2 C5 -179.8(2) . . . . ?
C7 N1 C3 C4 173.25(19) . . . . ?
C7 N1 C3 C2 -8.3(3) . . . . ?
C4 C5 C2 O3 -176.4(2) . . . . ?
C4 C5 C2 C3 0.84(15) . . . . ?
C4 C3 C2 O3 176.7(2) . . . . ?
C4 C3 C2 C5 -0.85(15) . . . . ?
C5 C4 C3 N1 179.8(2) . . . . ?
C5 C4 C3 C2 0.82(14) . . . . ?
C3 N1 C7 C8 -100.4(2) . . . . ?
C3 C4 C5 O1 179.9(2) . . . . ?
C3 C4 C5 C2 -0.79(14) . . . . ?
C8 N2 C10 C13 -177.0(2) . . . . ?
C8 N2 C10 C11 1.3(3) . . . . ?
C12 C13 C10 N2 179.5(2) . . . . ?
C12 C13 C10 C11 0.70(15) . . . . ?
C12 C11 C10 N2 -179.5(2) . . . . ?
C12 C11 C10 C13 -0.67(15) . . . . ?
C13 C12 C11 O4 -179.5(3) . . . . ?
C13 C12 C11 C10 0.65(14) . . . . ?
C11 C12 C13 O6 -179.9(2) . . . . ?
C11 C12 C13 C10 -0.69(15) . . . . ?
C10 N2 C8 C7 -110.9(2) . . . . ?
C9 N2 C8 C7 76.3(2) . . . . ?
C9 N2 C10 C13 -4.5(3) . . . . ?
C9 N2 C10 C11 173.8(2) . . . . ?
C14 O6 C13 C12 -3.5(3) . . . . ?
C14 O6 C13 C10 177.5(2) . . . . ?
C6 N1 C7 C8 78.2(2) . . . . ?
C6 N1 C3 C4 -5.3(3) . . . . ?
C6 N1 C3 C2 173.2(2) . . . . ?
C1 O3 C2 C5 1.4(4) . . . . ?
C1 O3 C2 C3 -175.1(2) . . . . ?
