#------------------------------------------------------------------------------
#$Date: 2020-11-06 17:09:52 +0200 (Fri, 06 Nov 2020) $
#$Revision: 259000 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/94/1559469.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_1559469
loop_
_publ_author_name
'Destro, Riccardo'
'Roversi, Pietro'
'Soave, Raffaella'
'Hovestad, Arjan'
'Lo Presti, Leonardo'
_publ_section_title
;
 Experimental Charge Density Analysis and Electrostatic Properties of
 Crystalline 1,3-Bis(Dimethylamino)Squaraine and Its Dihydrate from Low
 Temperature (T = 18 and 20 K) XRD Data
;
_journal_issue                   10
_journal_name_full               Crystals
_journal_page_first              894
_journal_paper_doi               10.3390/cryst10100894
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C8 H12 N2 O2'
_chemical_formula_sum            'C8 H12 N2 O2'
_chemical_formula_weight         168.20
_chemical_name_common            bis(dimethylamino)squaraine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.072(2)
_cell_length_b                   7.9873(9)
_cell_length_c                   6.8410(9)
_cell_measurement_reflns_used    90
_cell_measurement_temperature    18(1)
_cell_measurement_theta_max      15.27
_cell_measurement_theta_min      13.445
_cell_volume                     823.55(18)
_computing_cell_refinement       'In-home programs'
_computing_data_collection       'In-home programs'
_computing_data_reduction        'In-home programs'
_computing_molecular_graphics    'Diamond 3.0 (Crystal Impact GbR, 2004)'
_computing_publication_material  'VALRAY (Carnegie Mellon University, 2000)'
_diffrn_ambient_temperature      18(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Syntex P1'
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5163
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         54.394
_diffrn_reflns_theta_min         2.703
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        1.7(1)
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9789
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         5163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0488P)²+0.0980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4340
_reflns_number_total             5163
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Destro_et_al.cif
_cod_data_source_block           SQ1820
_cod_database_code               1559469
_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.
;
_shelxl_version_number           2014/4
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
C1 C 0.54013(2) 0.10316(3) 0.03600(4) 0.00500(3) Uani 1 1 d . . . . .
C2 C 0.44967(2) 0.07946(3) -0.03820(4) 0.00495(3) Uani 1 1 d . . . . .
C3 C 0.39629(2) 0.36290(3) -0.07128(5) 0.00878(4) Uani 1 1 d . . . . .
C4 C 0.30259(2) 0.12111(4) -0.17354(4) 0.00781(4) Uani 1 1 d . . . . .
N6 N 0.38514(2) 0.18221(3) -0.08824(4) 0.00584(3) Uani 1 1 d . . . . .
O5 O 0.58782(2) 0.22441(3) 0.07709(3) 0.00731(3) Uani 1 1 d . . . . .
H4A H 0.3032 -0.0119 -0.1752 0.029 Uani 1 1 d . . . . .
H4B H 0.2470 0.1644 -0.0895 0.032 Uani 1 1 d . . . . .
H4C H 0.2966 0.1698 -0.3256 0.033 Uani 1 1 d . . . . .
H3A H 0.3435 0.4142 0.0168 0.033 Uani 1 1 d . . . . .
H3B H 0.3954 0.4187 -0.2162 0.035 Uani 1 1 d . . . . .
H3C H 0.4582 0.3855 -0.0020 0.030 Uani 1 1 d . . . . .
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'
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'
H H 0.0000 0.0000 '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
O5 C1 C2 135.61(2) . 5_655 ?
O5 C1 C2 135.95(2) . . ?
C2 C1 C2 88.433(19) 5_655 . ?
N6 C2 C1 134.37(2) . 5_655 ?
N6 C2 C1 134.06(2) . . ?
C1 C2 C1 91.57(2) 5_655 . ?
N6 C3 H3A 109.60(3) . . ?
N6 C3 H3B 109.39(3) . . ?
H3A C3 H3B 110.11(3) . . ?
N6 C3 H3C 107.77(2) . . ?
H3A C3 H3C 109.57(3) . . ?
H3B C3 H3C 110.36(3) . . ?
N6 C4 H4A 109.40(2) . . ?
N6 C4 H4B 110.08(3) . . ?
H4A C4 H4B 109.53(3) . . ?
N6 C4 H4C 109.00(2) . . ?
H4A C4 H4C 109.86(3) . . ?
H4B C4 H4C 108.97(2) . . ?
C2 N6 C3 120.72(2) . . ?
C2 N6 C4 121.68(2) . . ?
C3 N6 C4 117.49(2) . . ?
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
C1 O5 1.2384(3) . ?
C1 C2 1.4668(4) 5_655 ?
C1 C2 1.4671(4) . ?
C2 N6 1.3179(3) . ?
C2 C1 1.4668(4) 5_655 ?
C3 N6 1.4576(4) . ?
C3 H3A 1.0793(3) . ?
C3 H3B 1.0873(3) . ?
C3 H3C 1.0624(3) . ?
C4 N6 1.4584(4) . ?
C4 H4A 1.0624(3) . ?
C4 H4B 1.0728(3) . ?
C4 H4C 1.1144(3) . ?
