#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:36:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180087 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/33/7053385.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_7053385
loop_
_publ_author_name
'Linares, Maholy'
'Briceño, Alexander'
_publ_section_title
;
 Solid-state synthesis of head-to-tail photodimers from supramolecular
 assemblies directed by charge-assisted hydrogen bonds
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              587
_journal_paper_doi               10.1039/b9nj00608g
_journal_volume                  34
_journal_year                    2010
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C13 H12 N, 0.5(C10 H4 O8)'
_chemical_formula_sum            'C18 H14 N O4'
_chemical_formula_weight         308.30
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '20 August 2008'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.767(10)
_cell_angle_beta                 106.763(10)
_cell_angle_gamma                108.1770(10)
_cell_formula_units_Z            2
_cell_length_a                   7.559(4)
_cell_length_b                   10.106(6)
_cell_length_c                   11.410(7)
_cell_measurement_reflns_used    1502
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      2.00
_cell_volume                     733.8(7)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_molecular_graphics
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND
(Brandenburg, 1998)
;
_computing_publication_material
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.771
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7661
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0613
_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)+(0.0693P)²+0.3306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1642
_reflns_number_gt                2076
_reflns_number_total             2694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b9nj00608g.txt
_cod_data_source_block           shelxle2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi Scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7053385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.1316(3) 0.40051(18) 0.10206(17) 0.0569(5) Uani 1 1 d .
O2 O 0.0799(3) 0.34390(19) 0.26789(17) 0.0586(5) Uani 1 1 d .
O3 O -0.1933(3) 0.1288(2) 0.25887(19) 0.0654(6) Uani 1 1 d .
H3O3 H -0.0677 0.2181 0.2721 0.078 Uiso 1 1 d R
O4 O -0.4167(3) -0.0917(2) 0.1059(2) 0.0742(6) Uani 1 1 d .
N1 N 0.1984(3) 0.6744(2) 0.25063(19) 0.0441(5) Uani 1 1 d .
HN1 H 0.1764 0.5686 0.1975 0.053 Uiso 1 1 d R
C1 C 0.0832(4) 0.3085(3) 0.1541(2) 0.0432(6) Uani 1 1 d .
C2 C 0.0316(3) 0.1462(2) 0.0771(2) 0.0370(5) Uani 1 1 d .
C3 C -0.1162(4) 0.0186(2) 0.0752(2) 0.0382(5) Uani 1 1 d .
C4 C -0.2556(4) 0.0162(3) 0.1476(3) 0.0489(6) Uani 1 1 d .
C5 C 0.1428(4) 0.1233(2) 0.0018(2) 0.0401(5) Uani 1 1 d .
H5 H 0.2405 0.2074 0.0030 0.048 Uiso 1 1 calc R
C6 C 0.2503(4) 0.7846(3) 0.2061(2) 0.0493(6) Uani 1 1 d .
H6 H 0.2681 0.7640 0.1271 0.059 Uiso 1 1 calc R
C7 C 0.2776(4) 0.9262(3) 0.2739(3) 0.0525(6) Uani 1 1 d .
H7 H 0.3126 1.0008 0.2405 0.063 Uiso 1 1 calc R
C8 C 0.2537(4) 0.9603(3) 0.3921(2) 0.0468(6) Uani 1 1 d .
C9 C 0.2046(4) 0.8435(3) 0.4386(2) 0.0511(6) Uani 1 1 d .
H9 H 0.1910 0.8620 0.5190 0.061 Uiso 1 1 calc R
C10 C 0.1765(4) 0.7013(3) 0.3652(2) 0.0491(6) Uani 1 1 d .
H10 H 0.1421 0.6239 0.3957 0.059 Uiso 1 1 calc R
C11 C 0.2815(4) 1.1151(3) 0.4607(3) 0.0559(7) Uani 1 1 d .
H11 H 0.2996 1.1808 0.4167 0.067 Uiso 1 1 calc R
C12 C 0.2826(4) 1.1667(3) 0.5770(3) 0.0558(7) Uani 1 1 d .
H12 H 0.2631 1.0996 0.6197 0.067 Uiso 1 1 calc R
C13 C 0.3117(4) 1.3211(3) 0.6496(3) 0.0503(6) Uani 1 1 d .
C14 C 0.3284(5) 1.4330(3) 0.5981(3) 0.0622(7) Uani 1 1 d .
H14 H 0.3255 1.4134 0.5132 0.075 Uiso 1 1 calc R
C15 C 0.3496(5) 1.5743(3) 0.6723(3) 0.0699(8) Uani 1 1 d .
H15 H 0.3617 1.6485 0.6370 0.084 Uiso 1 1 calc R
C16 C 0.3526(4) 1.6041(3) 0.7974(3) 0.0646(8) Uani 1 1 d .
H16 H 0.3670 1.6983 0.8472 0.078 Uiso 1 1 calc R
C17 C 0.3342(5) 1.4936(3) 0.8482(3) 0.0653(8) Uani 1 1 d .
H17 H 0.3347 1.5127 0.9325 0.078 Uiso 1 1 calc R
C18 C 0.3151(4) 1.3546(3) 0.7751(3) 0.0595(7) Uani 1 1 d .
H18 H 0.3042 1.2815 0.8116 0.071 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
C10 N1 C6 120.8(2) . .
O1 C1 O2 123.8(2) . .
O1 C1 C2 117.3(2) . .
O2 C1 C2 118.9(2) . .
C5 C2 C3 118.0(2) . .
C5 C2 C1 115.7(2) . .
C3 C2 C1 126.3(2) . .
C5 C3 C2 118.3(2) 2 .
C5 C3 C4 114.5(2) 2 .
C2 C3 C4 127.2(2) . .
O4 C4 O3 121.3(2) . .
O4 C4 C3 120.1(2) . .
O3 C4 C3 118.5(2) . .
C2 C5 C3 123.7(2) . 2
N1 C6 C7 121.3(2) . .
C6 C7 C8 120.6(2) . .
C7 C8 C9 117.0(2) . .
C7 C8 C11 118.5(2) . .
C9 C8 C11 124.5(2) . .
C10 C9 C8 120.0(2) . .
N1 C10 C9 120.3(2) . .
C12 C11 C8 125.3(3) . .
C11 C12 C13 126.9(3) . .
C18 C13 C14 117.6(2) . .
C18 C13 C12 117.7(3) . .
C14 C13 C12 124.6(3) . .
C13 C14 C15 120.8(3) . .
C16 C15 C14 120.1(3) . .
C17 C16 C15 119.4(3) . .
C16 C17 C18 120.4(3) . .
C13 C18 C17 121.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.243(3) .
O2 C1 1.266(3) .
O3 C4 1.308(3) .
O4 C4 1.213(3) .
N1 C10 1.335(3) .
N1 C6 1.335(3) .
C1 C2 1.511(3) .
C2 C5 1.391(3) .
C2 C3 1.408(3) .
C3 C5 1.394(3) 2
C3 C4 1.514(3) .
C5 C3 1.394(3) 2
C6 C7 1.360(3) .
C7 C8 1.383(4) .
C8 C9 1.404(4) .
C8 C11 1.477(4) .
C9 C10 1.380(3) .
C11 C12 1.293(4) .
C12 C13 1.480(4) .
C13 C18 1.376(4) .
C13 C14 1.390(4) .
C14 C15 1.395(4) .
C15 C16 1.373(4) .
C16 C17 1.372(4) .
C17 C18 1.377(4) .
