#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:50:06 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223623 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/26/7232606.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_7232606
loop_
_publ_author_name
'Fornasari, Luca'
'd'Agostino, Simone'
'Braga, Dario'
_publ_section_title
;
 Supramolecular zwitterions based on a novel boronic acid--squarate
 dianion synthon
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3186
_journal_paper_doi               10.1039/C9CE00367C
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C4 O4, 2(C5 H6.8 B N O2), C10 H8.4 N2'
_chemical_formula_sum            'C24 H22 B2 N4 O8'
_chemical_formula_weight         516.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-12 deposited with the CCDC.    2019-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.765(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.3874(6)
_cell_length_b                   10.7643(4)
_cell_length_c                   8.7610(4)
_cell_measurement_reflns_used    1184
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.9070
_cell_measurement_theta_min      3.6120
_cell_volume                     1154.56(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  48.00   1.00   14.34    --  -16.52  57.00 -30.00   76
  2  ω    -25.00   1.00   1.00   14.34    --  -16.52 -99.00   0.00   26
  3  ω    -65.00 -38.00   1.00   14.34    --  -16.52-178.00 -30.00   27
  4  ω    -79.00  -4.00   1.00   14.34    --  -16.52 -57.00-150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0479032000
_diffrn_orient_matrix_UB_12      -0.0202678000
_diffrn_orient_matrix_UB_13      -0.0482640000
_diffrn_orient_matrix_UB_21      -0.0253957000
_diffrn_orient_matrix_UB_22      -0.0109993000
_diffrn_orient_matrix_UB_23      0.0660483000
_diffrn_orient_matrix_UB_31      -0.0202904000
_diffrn_orient_matrix_UB_32      0.0617817000
_diffrn_orient_matrix_UB_33      -0.0041380000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2546
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.021
_diffrn_reflns_theta_min         3.270
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0463
_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)+(0.0588P)²+0.1668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1094
_reflns_number_total             1388
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00367c2.cif
_cod_data_source_block           1a-Bpy
_cod_depositor_comments
'Adding full bibliography for 7232605--7232608.cif.'
_cod_database_code               7232606
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.978
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.4) H2A(0.1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C3(H3), C4(H4), C5(H5), C6(H6)
3.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 1.052
_oxdiff_exptl_absorpt_empirical_full_min 0.961
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
O1 O 0.92159(10) 0.64953(10) 0.13068(13) 0.0544(4) Uani 1 1 d . . . . .
O2 O 0.85568(11) 0.61185(9) 0.39845(13) 0.0549(4) Uani 1 1 d . . . . .
H2 H 0.8763 0.6032 0.3144 0.082 Uiso 1 1 calc GR . . . .
N1 N 0.69879(13) 0.5000 0.88153(18) 0.0374(4) Uani 1 2 d S T P . .
H1 H 0.6707 0.5000 0.9654 0.045 Uiso 0.8 2 calc RS T P A 1
N2 N 0.60133(14) 0.5000 1.14324(19) 0.0404(4) Uani 1 2 d S T P . .
H2A H 0.6273 0.5000 1.0577 0.049 Uiso 0.2 2 calc RS T P B 2
C7 C 0.52150(15) 0.5000 1.4247(2) 0.0314(4) Uani 1 2 d S T P . .
C1 C 0.96487(11) 0.56750(12) 0.05947(15) 0.0341(3) Uani 1 1 d . . . . .
C2 C 0.79038(15) 0.5000 0.6160(2) 0.0327(4) Uani 1 2 d S T P . .
C3 C 0.76578(13) 0.60972(13) 0.68537(16) 0.0389(4) Uani 1 1 d . . . . .
H3 H 0.7804 0.6854 0.6415 0.047 Uiso 1 1 calc R . . . .
C4 C 0.71994(13) 0.60770(14) 0.81848(17) 0.0411(4) Uani 1 1 d . . . . .
H4 H 0.7037 0.6819 0.8645 0.049 Uiso 1 1 calc R . . . .
C5 C 0.58037(14) 0.60530(15) 1.21219(17) 0.0457(4) Uani 1 1 d . . . . .
H5 H 0.5926 0.6800 1.1643 0.055 Uiso 1 1 calc R . . . .
C6 C 0.54150(13) 0.60910(14) 1.35109(16) 0.0427(4) Uani 1 1 d . . . . .
H6 H 0.5287 0.6852 1.3954 0.051 Uiso 1 1 calc R . . . .
B1 B 0.83885(18) 0.5000 0.4575(3) 0.0357(5) Uani 1 2 d S T P . .
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'
B B 0.0013 0.0007 '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
C4 N1 C4 121.71(17) 6_565 .
C5 N2 C5 117.13(16) . 6_565
C6 C7 C7 121.69(8) 6_565 5_668
C6 C7 C7 121.69(8) . 5_668
C6 C7 C6 116.61(17) . 6_565
O1 C1 C1 134.98(7) . 2_755
O1 C1 C1 135.02(7) . 6_565
C1 C1 C1 90.000(1) 6_565 2_755
C3 C2 C3 117.24(17) 6_565 .
C3 C2 B1 121.33(8) 6_565 .
C3 C2 B1 121.33(8) . .
C4 C3 C2 120.47(13) . .
N1 C4 C3 120.05(14) . .
N2 C5 C6 123.13(14) . .
C5 C6 C7 119.99(14) . .
O2 B1 O2 128.04(18) 6_565 .
O2 B1 C2 115.97(9) 6_565 .
O2 B1 C2 115.97(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2483(16) .
O2 B1 1.3393(13) .
N1 C4 1.3274(16) .
N1 C4 1.3273(16) 6_565
N2 C5 1.3284(17) .
N2 C5 1.3285(17) 6_565
C7 C7 1.497(3) 5_668
C7 C6 1.3802(17) 6_565
C7 C6 1.3802(17) .
C1 C1 1.453(3) 6_565
C1 C1 1.456(3) 2_755
C2 C3 1.3833(16) .
C2 C3 1.3833(16) 6_565
C2 B1 1.594(3) .
C3 C4 1.3729(19) .
C5 C6 1.376(2) .
B1 O2 1.3393(13) 6_565
