#------------------------------------------------------------------------------
#$Date: 2019-11-24 23:30:39 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/70/4517040.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_4517040
loop_
_publ_author_name
'Braga, Dario'
'd’Agostino, Simone'
'Grepioni, Fabrizia'
_publ_section_title
;
 Co-Crystals and Salts Obtained from Dinitrogen Bases and
 1,2,3,4-Cyclobutane Tetracarboxylic Acid and the Use of the Latter As a
 Template for Solid-State Photocyclization Reactions
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4880
_journal_paper_doi               10.1021/cg300716q
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.893(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0584(4)
_cell_length_b                   10.8433(6)
_cell_length_c                   18.2878(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1394.58(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.869
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14623
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0393P)²+0.2428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                2043
_reflns_number_total             3300
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-2-3abc-4-5-6.CIF
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4517040
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.04797(17) 0.54852(9) 0.17352(5) 0.0605(3) Uani 1 1 d .
H1O H 0.013(3) 0.5216(19) 0.2280(11) 0.113(7) Uiso 1 1 d .
O2 O 0.04511(17) 0.36289(10) 0.14120(5) 0.0665(3) Uani 1 1 d .
O3 O 0.20303(16) 0.73983(9) 0.09269(6) 0.0576(3) Uani 1 1 d .
H3O H 0.293(3) 0.7464(18) 0.1389(13) 0.113(7) Uiso 1 1 d .
O4 O 0.36611(16) 0.57177(11) 0.06975(6) 0.0709(4) Uani 1 1 d .
C1 C 0.2245(2) 0.63392(13) 0.05992(7) 0.0438(3) Uani 1 1 d .
C2 C 0.05176(19) 0.59479(12) 0.01137(6) 0.0399(3) Uani 1 1 d .
H2 H -0.0189 0.6662 -0.0094 0.048 Uiso 1 1 calc R
C3 C -0.08282(19) 0.50161(12) 0.04764(6) 0.0399(3) Uani 1 1 d .
H3 H -0.2145 0.5312 0.0434 0.048 Uiso 1 1 calc R
C4 C -0.0208(2) 0.46300(13) 0.12558(7) 0.0429(3) Uani 1 1 d .
N1 N 0.08368(17) 0.48575(12) 0.30581(6) 0.0490(3) Uani 1 1 d .
N2 N 0.60352(17) 0.25898(11) 0.77630(6) 0.0492(3) Uani 1 1 d .
C5 C 0.1623(2) 0.37687(15) 0.32287(8) 0.0556(4) Uani 1 1 d .
H5 H 0.1649 0.3178 0.2861 0.067 Uiso 1 1 calc R
C6 C 0.2402(2) 0.34734(14) 0.39246(7) 0.0513(4) Uani 1 1 d .
H6 H 0.2946 0.2702 0.4019 0.062 Uiso 1 1 calc R
C7 C 0.23649(18) 0.43391(13) 0.44811(7) 0.0416(3) Uani 1 1 d .
C8 C 0.15633(19) 0.54724(14) 0.42970(7) 0.0464(3) Uani 1 1 d .
H8 H 0.1526 0.6084 0.4652 0.056 Uiso 1 1 calc R
C9 C 0.0821(2) 0.56957(14) 0.35890(7) 0.0489(4) Uani 1 1 d .
H9 H 0.0286 0.6464 0.3477 0.059 Uiso 1 1 calc R
C10 C 0.31085(19) 0.41236(14) 0.52466(7) 0.0462(3) Uani 1 1 d .
H10 H 0.3083 0.4794 0.5563 0.055 Uiso 1 1 calc R
C11 C 0.38041(19) 0.30917(14) 0.55352(7) 0.0470(4) Uani 1 1 d .
H11 H 0.3842 0.2411 0.5227 0.056 Uiso 1 1 calc R
C12 C 0.4292(2) 0.37962(16) 0.68484(8) 0.0629(5) Uani 1 1 d .
H12 H 0.3623 0.4519 0.6733 0.076 Uiso 1 1 calc R
C13 C 0.45268(18) 0.29294(13) 0.63078(7) 0.0427(3) Uani 1 1 d .
C14 C 0.5520(2) 0.18843(14) 0.65260(7) 0.0527(4) Uani 1 1 d .
H14 H 0.5683 0.1258 0.6190 0.063 Uiso 1 1 calc R
C15 C 0.5051(2) 0.35876(16) 0.75591(8) 0.0639(4) Uani 1 1 d .
H15 H 0.4860 0.4180 0.7913 0.077 Uiso 1 1 calc R
C16 C 0.6273(2) 0.17646(14) 0.72432(8) 0.0551(4) Uani 1 1 d .
H16 H 0.6990 0.1065 0.7370 0.066 Uiso 1 1 calc R
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
O4 C1 O3 123.25(13) . .
O4 C1 C2 123.31(13) . .
O3 C1 C2 113.39(12) . .
C1 C2 C3 116.75(11) . 3_565
C1 C2 C3 114.85(10) . .
C3 C2 C3 89.23(10) 3_565 .
C4 C3 C2 115.30(11) . 3_565
C4 C3 C2 116.01(11) . .
C2 C3 C2 90.77(10) 3_565 .
O2 C4 O1 123.91(12) . .
O2 C4 C3 123.14(12) . .
O1 C4 C3 112.94(12) . .
C5 N1 C9 117.67(12) . .
C15 N2 C16 116.45(12) . .
N1 C5 C6 123.20(14) . .
C5 C6 C7 119.26(14) . .
C8 C7 C6 117.14(12) . .
C8 C7 C10 118.57(12) . .
C6 C7 C10 124.29(13) . .
C9 C8 C7 120.04(13) . .
N1 C9 C8 122.69(14) . .
C11 C10 C7 127.45(14) . .
C10 C11 C13 125.07(14) . .
C15 C12 C13 120.02(15) . .
C14 C13 C12 116.22(12) . .
C14 C13 C11 120.28(13) . .
C12 C13 C11 123.50(13) . .
C13 C14 C16 119.99(14) . .
N2 C15 C12 123.49(14) . .
N2 C16 C14 123.78(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.3015(16) .
O2 C4 1.2057(16) .
O3 C1 1.3101(17) .
O4 C1 1.2062(16) .
C1 C2 1.5068(18) .
C2 C3 1.5315(18) 3_565
C2 C3 1.5718(19) .
C3 C4 1.5140(17) .
C3 C2 1.5315(18) 3_565
N1 C5 1.3303(19) .
N1 C9 1.3307(17) .
N2 C15 1.3221(19) .
N2 C16 1.3266(18) .
C5 C6 1.3803(19) .
C6 C7 1.3863(19) .
C7 C8 1.3825(19) .
C7 C10 1.4714(17) .
C8 C9 1.3761(18) .
C10 C11 1.3142(19) .
C11 C13 1.4712(18) .
C12 C15 1.381(2) .
C12 C13 1.384(2) .
C13 C14 1.3737(19) .
C14 C16 1.3788(19) .
