Experimental and Theoretical Study of Aromaticity Effects in the Solid State Architecture on Squaric Acid Derivatives
Prohens, Rafel; Portell, Anna; Font-Bardia, Mercè; Bauzá, Antonio; Frontera, Antonio; Crystal Growth & Design 14 (2014) 2578–; doi:10.1021/cg500264k

data_4510468
_publ_section_title
;
 Experimental and Theoretical Study of Aromaticity Effects in the Solid
 State Architecture on Squaric Acid Derivatives
;
_journal_issue                   5
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              2578
_journal_paper_doi               10.1021/cg500264k
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C8 H10 N O3, C4 H12 N'
_chemical_formula_sum            'C12 H22 N2 O3'
_chemical_formula_weight         242.31
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 104.25(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.041(4)
_cell_length_b                   12.717(5)
_cell_length_c                   16.156(7)
_cell_measurement_reflns_used    340
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     1402.1(12)
_computing_cell_refinement       AUTOMAR
_computing_data_collection       MARXDS
_computing_data_reduction        MARSCALE
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      105(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.811
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.811
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12749
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.342
_diffrn_reflns_theta_min         2.063
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0753P)^2^+0.1868P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.1815
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3050
_reflns_number_total             4065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg500264k_si_010.cif
_cod_data_source_block           anpm112a1_Compound_3
_cod_depositor_comments
'Adding full bibliography for 4510466--4510471.cif.'
_cod_database_code               4510468
_shelxl_version_number           2012-9
_shelx_res_checksum              27958
_shelx_hkl_checksum              67104