#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:05:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179651 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/04/4510471.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_4510471
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         'C10 H28 N4, 2(C4 O4), 3(H2 O)'
_chemical_formula_sum            'C18 H34 N4 O11'
_chemical_formula_weight         482.49
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 102.90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.512(11)
_cell_length_b                   7.339(3)
_cell_length_c                   16.768(8)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     2220.6(19)
_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      293(2)
_diffrn_detector_area_resol_mean 'image plate'
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.774
_diffrn_measurement_device_type  'Mar345 with image plate detector'
_diffrn_measurement_method       phi-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.774
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7470
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.664
_diffrn_reflns_theta_min         2.257
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0444
_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)+(0.0545P)²+1.4593P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2274
_reflns_number_total             2430
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500264k_si_009.cif
_cod_data_source_block           anpm26_compound_2
_cod_depositor_comments
'Adding full bibliography for 4510466--4510471.cif.'
_cod_database_code               4510471
#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, -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
O1 O 0.37362(6) 0.20710(19) 0.35662(7) 0.0492(3) Uani 1 1 d . . .
O2 O 0.38501(6) 0.20288(18) 0.16628(7) 0.0470(3) Uani 1 1 d . . .
O3 O 0.20714(6) 0.25296(16) 0.11027(6) 0.0422(3) Uani 1 1 d . . .
O4 O 0.19326(6) 0.25460(17) 0.29634(7) 0.0460(3) Uani 1 1 d . . .
N1 N 0.17545(6) 0.25167(15) 0.44816(7) 0.0289(3) Uani 1 1 d . . .
H1N H 0.1849(9) 0.253(2) 0.3978(12) 0.035 Uiso 1 1 d . U .
N2 N -0.06590(7) 0.30673(19) 0.37716(9) 0.0382(3) Uani 1 1 d . . .
H2B H -0.0581(10) 0.377(3) 0.3369(12) 0.046 Uiso 1 1 d . U .
H2A H -0.1187(11) 0.287(2) 0.3735(11) 0.046 Uiso 1 1 d . U .
H2 H -0.0455(10) 0.361(3) 0.4223(12) 0.046 Uiso 1 1 d . U .
C1 C 0.32853(7) 0.2210(2) 0.28910(8) 0.0334(3) Uani 1 1 d . . .
C2 C 0.33330(7) 0.21954(19) 0.20318(9) 0.0328(3) Uani 1 1 d . . .
C3 C 0.25326(7) 0.24205(18) 0.17770(8) 0.0309(3) Uani 1 1 d . . .
C4 C 0.24761(8) 0.24281(19) 0.26288(9) 0.0325(3) Uani 1 1 d . . .
C5 C 0.09279(7) 0.2577(2) 0.43851(9) 0.0366(3) Uani 1 1 d . . .
H5A H 0.0763 0.3828 0.4288 0.044 Uiso 1 1 calc R U .
H5B H 0.0809 0.2184 0.4893 0.044 Uiso 1 1 calc R U .
C6 C 0.05052(7) 0.1403(2) 0.36965(9) 0.0367(3) Uani 1 1 d . . .
H61 H 0.0722 0.0194 0.3737 0.044 Uiso 1 1 calc R U .
H62 H 0.0545 0.1924 0.3176 0.044 Uiso 1 1 calc R U .
C7 C -0.03080(7) 0.1262(2) 0.37289(10) 0.0389(3) Uani 1 1 d . . .
H7A H -0.0574 0.0622 0.3246 0.047 Uiso 1 1 calc R U .
H7B H -0.0349 0.0550 0.4204 0.047 Uiso 1 1 calc R U .
C8 C 0.20883(7) 0.41761(19) 0.49423(8) 0.0325(3) Uani 1 1 d . . .
H8A H 0.1953 0.4216 0.5469 0.039 Uiso 1 1 calc R U .
H8B H 0.1892 0.5260 0.4639 0.039 Uiso 1 1 calc R U .
C9 C 0.20764(7) 0.08382(19) 0.49284(8) 0.0330(3) Uani 1 1 d . . .
H9A H 0.1873 -0.0230 0.4617 0.040 Uiso 1 1 calc R U .
H9B H 0.1941 0.0786 0.5454 0.040 Uiso 1 1 calc R U .
O1W O 0.48022(7) 0.18997(17) 0.05892(7) 0.0452(3) Uani 1 1 d . . .
H1W H 0.4459(12) 0.203(3) 0.0879(13) 0.054 Uiso 1 1 d . U .
H1WA H 0.5225(12) 0.203(3) 0.0927(13) 0.054 Uiso 1 1 d . U .
O2W O 0.5000 -0.0027(2) 0.2500 0.0451(4) Uani 1 2 d S T P
H2W H 0.4643(10) 0.073(3) 0.2245(11) 0.054 Uiso 1 1 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C9 N1 C8 109.80(11) . .
C9 N1 C5 111.13(11) . .
C8 N1 C5 108.91(10) . .
C9 N1 H1N 110.0(10) . .
C8 N1 H1N 109.3(10) . .
C5 N1 H1N 107.7(11) . .
C7 N2 H2B 109.6(12) . .
C7 N2 H2A 108.0(11) . .
H2B N2 H2A 111.6(16) . .
C7 N2 H2 109.9(13) . .
H2B N2 H2 106.7(18) . .
H2A N2 H2 111.0(16) . .
O1 C1 C2 135.68(13) . .
O1 C1 C4 135.02(14) . .
C2 C1 C4 89.30(11) . .
O2 C2 C3 134.70(14) . .
O2 C2 C1 134.89(13) . .
C3 C2 C1 90.40(11) . .
O3 C3 C4 134.33(13) . .
O3 C3 C2 135.43(13) . .
C4 C3 C2 90.22(11) . .
O4 C4 C3 132.61(13) . .
O4 C4 C1 137.30(14) . .
C3 C4 C1 90.08(11) . .
N1 C5 C6 113.98(11) . .
N1 C5 H5A 108.8 . .
C6 C5 H5A 108.8 . .
N1 C5 H5B 108.8 . .
C6 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
C5 C6 C7 111.04(12) . .
C5 C6 H61 109.4 . .
C7 C6 H61 109.4 . .
C5 C6 H62 109.4 . .
C7 C6 H62 109.4 . .
H61 C6 H62 108.0 . .
N2 C7 C6 112.84(12) . .
N2 C7 H7A 109.0 . .
C6 C7 H7A 109.0 . .
N2 C7 H7B 109.0 . .
C6 C7 H7B 109.0 . .
H7A C7 H7B 107.8 . .
N1 C8 C9 111.02(11) . 7_556
N1 C8 H8A 109.4 . .
C9 C8 H8A 109.4 7_556 .
N1 C8 H8B 109.4 . .
C9 C8 H8B 109.4 7_556 .
H8A C8 H8B 108.0 . .
N1 C9 C8 110.97(11) . 7_556
N1 C9 H9A 109.4 . .
C8 C9 H9A 109.4 7_556 .
N1 C9 H9B 109.4 . .
C8 C9 H9B 109.4 7_556 .
H9A C9 H9B 108.0 . .
H1W O1W H1WA 106.5(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2517(17) .
O2 C2 1.2564(17) .
O3 C3 1.2581(17) .
O4 C4 1.2595(18) .
N1 C9 1.4948(17) .
N1 C8 1.4995(18) .
N1 C5 1.5031(18) .
N1 H1N 0.899(19) .
N2 C7 1.484(2) .
N2 H2B 0.89(2) .
N2 H2A 0.976(19) .
N2 H2 0.86(2) .
C1 C2 1.463(2) .
C1 C4 1.473(2) .
C2 C3 1.4568(19) .
C3 C4 1.455(2) .
C5 C6 1.511(2) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.522(2) .
C6 H61 0.9700 .
C6 H62 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.5127(19) 7_556
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C8 1.5127(19) 7_556
C9 H9A 0.9700 .
C9 H9B 0.9700 .
O1W H1W 0.89(2) .
O1W H1WA 0.86(2) .
O2W H2W 0.894(19) .
