#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:05:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179651 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/04/4510470.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_4510470
loop_
_publ_author_name
'Prohens, Rafel'
'Portell, Anna'
'Font-Bardia, Mercè'
'Bauzá, Antonio'
'Frontera, Antonio'
_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 & Design'
_journal_page_first              2578
_journal_paper_doi               10.1021/cg500264k
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C12 H24 N4 O2, C4 O4, H2 O'
_chemical_formula_sum            'C16 H24 N4 O7'
_chemical_formula_weight         384.39
_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   mixed
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 119.13(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.737(6)
_cell_length_b                   11.931(5)
_cell_length_c                   16.323(7)
_cell_measurement_reflns_used    98
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     1826.5(16)
_computing_cell_refinement       'AUTOMAR (Claudio Klein, 2007)'
_computing_data_collection       'MARXDS (Claudio Klein, 2005)'
_computing_data_reduction        'MARSCALE (Claudio Klein, 2007)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 'image plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.892
_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  0.0637
_diffrn_reflns_av_sigmaI/netI    0.1122
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13716
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.489
_diffrn_reflns_theta_min         2.171
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5900
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.1469
_refine_ls_R_factor_gt           0.0532
_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)+(0.0409P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1345
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2531
_reflns_number_total             5900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500264k_si_012.cif
_cod_data_source_block           anpm179b1_Compound_5
_cod_depositor_comments
'Adding full bibliography for 4510466--4510471.cif.'
_cod_database_code               4510470
#BEGIN Tags that were not found in dictionaries:
_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           2012-9
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.53704(16) 0.76564(12) 0.52632(10) 0.0722(4) Uani 1 1 d . . . . .
O2 O 0.35795(15) 0.59528(11) 0.35564(10) 0.0694(4) Uani 1 1 d . . . . .
N1 N 0.54472(16) 0.46700(12) 0.20357(10) 0.0543(4) Uani 1 1 d . U . . .
H1N H 0.6026 0.5258 0.2382 0.065 Uiso 1 1 d R U . A .
N2 N 0.64537(14) 0.45401(11) 0.41407(9) 0.0448(3) Uani 1 1 d . U . . .
H2N H 0.7255 0.4179 0.4271 0.054 Uiso 1 1 d R U . . .
N3 N 0.82129(17) 0.61829(12) 0.58811(11) 0.0571(4) Uani 1 1 d . . . . .
H3N H 0.9073 0.5890 0.6038 0.069 Uiso 1 1 d R U . . .
N4 N 0.96332(19) 0.85577(13) 0.62752(11) 0.0701(5) Uani 1 1 d . U . . .
H4N H 0.9459 0.8090 0.5795 0.084 Uiso 1 1 d R U . . .
C1 C 0.5637(2) 0.68059(15) 0.49590(13) 0.0553(5) Uani 1 1 d . . . . .
C2 C 0.4803(2) 0.60627(16) 0.41679(15) 0.0610(5) Uani 1 1 d . U . . .
C3 C 0.61455(18) 0.54314(14) 0.44601(12) 0.0482(4) Uani 1 1 d . U . . .
C4 C 0.6881(2) 0.61326(14) 0.52121(12) 0.0519(4) Uani 1 1 d . . . . .
C5 C 0.8645(2) 0.68898(16) 0.67100(14) 0.0681(5) Uani 1 1 d . U . . .
H5A H 0.8851 0.6423 0.7248 0.082 Uiso 1 1 calc R U . . .
H5B H 0.7871 0.7392 0.6606 0.082 Uiso 1 1 calc R U . . .
C6 C 0.9976(3) 0.75787(18) 0.69112(16) 0.0821(7) Uani 1 1 d . U . . .
H6A H 1.0429 0.7840 0.7555 0.099 Uiso 1 1 calc R U . . .
H6B H 1.0649 0.7100 0.6842 0.099 Uiso 1 1 calc R U . . .
C8 C 1.0926(3) 0.9134(2) 0.6444(2) 0.1018(9) Uani 1 1 d . U . . .
H8A H 1.0683 0.9778 0.6042 0.153 Uiso 1 1 calc R U . . .
H8B H 1.1510 0.8637 0.6313 0.153 Uiso 1 1 calc R U . . .
H8C H 1.1440 0.9369 0.7087 0.153 Uiso 1 1 calc R U . . .
C9 C 0.8595(3) 0.93536(19) 0.63710(17) 0.0918(8) Uani 1 1 d . . . . .
H9A H 0.8408 0.9986 0.5963 0.138 Uiso 1 1 calc R U . . .
H9B H 0.9006 0.9608 0.7008 0.138 Uiso 1 1 calc R U . . .
H9C H 0.7718 0.8967 0.6202 0.138 Uiso 1 1 calc R U . . .
C10 C 0.53664(19) 0.38609(15) 0.34067(13) 0.0553(5) Uani 1 1 d . U . . .
C11 C 0.5618(3) 0.3777(2) 0.2552(2) 0.0454(5) Uani 0.6 1 d . U P A 1
H11A H 0.6585 0.3512 0.2780 0.055 Uiso 0.6 1 calc R U P A 1
H11B H 0.4986 0.3200 0.2141 0.055 Uiso 0.6 1 calc R U P A 1
C12 C 0.5676(6) 0.4598(3) 0.1268(3) 0.0768(11) Uani 0.6 1 d . . P A 1
H12A H 0.5505 0.5316 0.0966 0.115 Uiso 0.6 1 calc R U P A 1
H12B H 0.5037 0.4055 0.0832 0.115 Uiso 0.6 1 calc R U P A 1
H12C H 0.6643 0.4374 0.1476 0.115 Uiso 0.6 1 calc R U P A 1
C13 C 0.3872(3) 0.5150(3) 0.1568(3) 0.0681(9) Uani 0.6 1 d . U P A 1
H13A H 0.3804 0.5804 0.1205 0.102 Uiso 0.6 1 calc R U P A 1
H13B H 0.3643 0.5348 0.2050 0.102 Uiso 0.6 1 calc R U P A 1
H13C H 0.3216 0.4591 0.1167 0.102 Uiso 0.6 1 calc R U P A 1
C11' C 0.4688(4) 0.4410(3) 0.2485(3) 0.0429(7) Uani 0.4 1 d . U P A 2
H11C H 0.3902 0.3935 0.2064 0.052 Uiso 0.4 1 calc R U P A 2
H11D H 0.4272 0.5103 0.2551 0.052 Uiso 0.4 1 calc R U P A 2
C12' C 0.4731(6) 0.4839(5) 0.1062(3) 0.0600(14) Uani 0.4 1 d . . P A 2
H12D H 0.5411 0.5010 0.0858 0.090 Uiso 0.4 1 calc R U P A 2
H12E H 0.4074 0.5452 0.0908 0.090 Uiso 0.4 1 calc R U P A 2
H12F H 0.4217 0.4172 0.0753 0.090 Uiso 0.4 1 calc R U P A 2
C13' C 0.6482(7) 0.3602(5) 0.2217(5) 0.092(2) Uani 0.4 1 d . . P A 2
H13D H 0.7056 0.3730 0.1923 0.137 Uiso 0.4 1 calc R U P A 2
H13E H 0.5914 0.2941 0.1957 0.137 Uiso 0.4 1 calc R U P A 2
H13F H 0.7090 0.3502 0.2879 0.137 Uiso 0.4 1 calc R U P A 2
O3 O 0.34302(12) 0.33882(9) 0.72263(8) 0.0508(3) Uani 1 1 d . . . . .
O4 O 0.06576(13) 0.49419(10) 0.65342(8) 0.0562(3) Uani 1 1 d . . . . .
O5 O -0.11140(11) 0.32377(9) 0.47984(8) 0.0510(3) Uani 1 1 d . . . . .
O6 O 0.17228(13) 0.17403(9) 0.54967(8) 0.0521(3) Uani 1 1 d . . . . .
C14 C 0.09346(18) 0.40555(13) 0.62475(12) 0.0443(4) Uani 1 1 d . . . . .
C15 C 0.21859(16) 0.33548(12) 0.65633(10) 0.0378(3) Uani 1 1 d . . . . .
C16 C 0.14197(15) 0.26218(12) 0.57959(10) 0.0345(3) Uani 1 1 d . . . . .
C17 C 0.01398(17) 0.33139(12) 0.54758(11) 0.0417(4) Uani 1 1 d . . . . .
O1W O 0.75322(18) 0.17459(16) 0.54471(14) 0.0975(6) Uani 1 1 d D . . . .
H1W H 0.771(3) 0.183(2) 0.4960(13) 0.117 Uiso 1 1 d D U . . .
H1WA H 0.6678(17) 0.201(2) 0.5316(17) 0.117 Uiso 1 1 d D U . . .
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
C11 N1 C12 119.8(2)
C11' N1 C12' 119.8(3)
C11 N1 C13 112.6(2)
C12 N1 C13 101.7(3)
C11' N1 C13' 104.9(3)
C12' N1 C13' 105.6(4)
C11 N1 H1N 112.4
C11' N1 H1N 104.0
C12 N1 H1N 103.7
C12' N1 H1N 114.7
C13 N1 H1N 105.2
C13' N1 H1N 106.7
C3 N2 C10 122.11(15)
C3 N2 H2N 135.0
C10 N2 H2N 102.9
C4 N3 C5 121.48(17)
C4 N3 H3N 140.5
C5 N3 H3N 98.1
C8 N4 C6 110.61(18)
C8 N4 C9 111.35(19)
C6 N4 C9 111.20(19)
C8 N4 H4N 103.4
C6 N4 H4N 89.8
C9 N4 H4N 128.2
O1 C1 C4 135.70(19)
O1 C1 C2 134.35(18)
C4 C1 C2 89.95(16)
O1 C1 C3 177.75(17)
C2 C1 C3 47.18(11)
O2 C2 C1 138.46(19)
O2 C2 C3 134.82(19)
C1 C2 C3 86.68(16)
N2 C3 C4 135.30(17)
N2 C3 C2 133.25(17)
C4 C3 C2 91.39(15)
N2 C3 C1 178.99(15)
C4 C3 C1 45.27(11)
C2 C3 C1 46.14(11)
N3 C4 C3 133.75(17)
N3 C4 C1 134.28(17)
C3 C4 C1 91.94(16)
N3 C5 C6 110.41(19)
N3 C5 H5A 109.6
C6 C5 H5A 109.6
N3 C5 H5B 109.6
C6 C5 H5B 109.6
H5A C5 H5B 108.1
N4 C6 C5 112.50(18)
N4 C6 H6A 109.1
C5 C6 H6A 109.1
N4 C6 H6B 109.1
C5 C6 H6B 109.1
H6A C6 H6B 107.8
N4 C8 H8A 109.5
N4 C8 H8B 109.5
H8A C8 H8B 109.5
N4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N4 C9 H9A 109.5
N4 C9 H9B 109.5
H9A C9 H9B 109.5
N4 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N2 C10 C11' 113.36(19)
N2 C10 C11 110.98(16)
N1 C11 C10 119.7(2)
N1 C11 H11A 107.4
C10 C11 H11A 107.4
N1 C11 H11B 107.4
C10 C11 H11B 107.4
H11A C11 H11B 106.9
N1 C12 H12A 109.5
N1 C12 H12B 109.5
H12A C12 H12B 109.5
N1 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N1 C13 H13A 109.5
N1 C13 H13B 109.5
H13A C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N1 C11' C10 121.4(3)
N1 C11' H11C 107.0
C10 C11' H11C 107.0
N1 C11' H11D 107.0
C10 C11' H11D 107.0
H11C C11' H11D 106.7
N1 C12' H12D 109.5
N1 C12' H12E 109.5
H12D C12' H12E 109.5
N1 C12' H12F 109.5
H12D C12' H12F 109.5
H12E C12' H12F 109.5
N1 C13' H13D 109.5
N1 C13' H13E 109.5
H13D C13' H13E 109.5
N1 C13' H13F 109.5
H13D C13' H13F 109.5
H13E C13' H13F 109.5
O4 C14 C17 134.72(16)
O4 C14 C15 134.77(15)
C17 C14 C15 90.50(13)
O4 C14 C16 179.04(15)
C17 C14 C16 46.20(9)
C15 C14 C16 44.31(9)
O3 C15 C16 134.73(14)
O3 C15 C14 135.10(14)
C16 C15 C14 90.16(12)
O6 C16 C15 134.88(14)
O6 C16 C17 134.67(14)
C15 C16 C17 90.44(12)
O6 C16 C14 178.52(13)
C15 C16 C14 45.53(9)
C17 C16 C14 44.91(9)
O5 C17 C14 137.69(15)
O5 C17 C16 133.42(14)
C14 C17 C16 88.89(13)
H1W O1W H1WA 112.2(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.223(2)
O2 C2 1.209(2)
N1 C11 1.315(3)
N1 C11' 1.372(5)
N1 C12 1.392(4)
N1 C12' 1.404(5)
N1 C13 1.586(4)
N1 C13' 1.621(6)
N1 H1N 0.9252
N2 C3 1.296(2)
N2 C10 1.447(2)
N2 H2N 0.8904
N3 C4 1.312(2)
N3 C5 1.465(2)
N3 H3N 0.8997
N4 C8 1.450(3)
N4 C6 1.485(3)
N4 C9 1.529(3)
N4 H4N 0.9045
C1 C4 1.437(3)
C1 C2 1.459(3)
C1 C3 2.021(3)
C2 C3 1.485(3)
C3 C4 1.374(2)
C5 C6 1.538(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 H6A 0.9700
C6 H6B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11' 1.468(4)
C10 C11 1.547(4)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C11' H11C 0.9700
C11' H11D 0.9700
C12' H12D 0.9600
C12' H12E 0.9600
C12' H12F 0.9600
C13' H13D 0.9600
C13' H13E 0.9600
C13' H13F 0.9600
O3 C15 1.2450(18)
O4 C14 1.2496(19)
O5 C17 1.2625(19)
O6 C16 1.2672(18)
C14 C17 1.432(2)
C14 C15 1.448(2)
C14 C16 2.028(2)
C15 C16 1.417(2)
C16 C17 1.464(2)
O1W H1W 0.908(9)
O1W H1WA 0.893(9)
