#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:36:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180087 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/33/7053386.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_7053386
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 H11 Cl N, 0.5(C10 H4 O8)'
_chemical_formula_sum            'C18 H13 Cl N O4'
_chemical_formula_weight         342.74
_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                66.39(3)
_cell_angle_beta                 73.94(3)
_cell_angle_gamma                79.39(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4116(15)
_cell_length_b                   9.874(2)
_cell_length_c                   12.082(2)
_cell_measurement_reflns_used    1320
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.4978
_cell_volume                     775.9(3)
_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 0.977
_diffrn_measured_fraction_theta_max 0.783
_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  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0911
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8867
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.09
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1380
_refine_ls_R_factor_gt           0.0780
_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)+(0.0441P)²+0.4522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1759
_reflns_number_gt                1763
_reflns_number_total             2956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b9nj00608g.txt
_cod_data_source_block           shelxle3
_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               7053386
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
Cl1 Cl 0.10868(17) 0.93492(14) 0.89177(12) 0.0770(4) Uani 1 1 d .
O1 O 1.2363(4) 0.3082(3) 0.0805(2) 0.0606(8) Uani 1 1 d .
O2 O 1.2158(4) 0.1217(3) 0.2607(2) 0.0628(8) Uani 1 1 d .
N1 N 1.0128(5) 0.4464(4) 0.2274(3) 0.0559(9) Uani 1 1 d .
H1N H 1.0940 0.3981 0.1810 0.068(14) Uiso 1 1 d R
C17 C 1.3868(5) -0.0796(4) 0.1161(3) 0.0427(9) Uani 1 1 d .
O4 O 1.2586(4) -0.3096(3) 0.2437(3) 0.0724(10) Uani 1 1 d .
O3 O 1.1998(5) -0.1415(3) 0.3285(2) 0.0739(10) Uani 1 1 d .
H3O H 1.2121 -0.0223 0.3033 0.110(18) Uiso 1 1 d R
C19 C 1.5030(5) -0.1489(4) 0.0393(3) 0.0456(10) Uani 1 1 d .
H19A H 1.5050 -0.2515 0.0667 0.055 Uiso 1 1 calc R
C2 C 0.6455(6) 0.6792(5) 0.4395(4) 0.0599(12) Uani 1 1 d .
H2A H 0.5947 0.7725 0.3951 0.072 Uiso 1 1 calc R
C10 C 0.7754(6) 0.5946(4) 0.3685(4) 0.0498(10) Uani 1 1 d .
C14 C 0.8133(6) 0.6550(5) 0.2398(4) 0.0572(11) Uani 1 1 d .
H14A H 0.7573 0.7481 0.2000 0.069 Uiso 1 1 calc R
C3 C 0.4709(6) 0.7073(5) 0.6394(4) 0.0552(11) Uani 1 1 d .
C11 C 0.8641(6) 0.4552(4) 0.4229(4) 0.0518(10) Uani 1 1 d .
H11A H 0.8436 0.4108 0.5088 0.062 Uiso 1 1 calc R
C12 C 0.9804(6) 0.3838(4) 0.3513(4) 0.0542(11) Uani 1 1 d .
H12A H 1.0381 0.2905 0.3886 0.065 Uiso 1 1 calc R
C16 C 1.3830(5) 0.0761(4) 0.0759(3) 0.0419(9) Uani 1 1 d .
C1 C 0.5968(6) 0.6313(5) 0.5614(4) 0.0595(11) Uani 1 1 d .
H1A H 0.6489 0.5374 0.6033 0.071 Uiso 1 1 calc R
C15 C 1.2691(6) 0.1746(5) 0.1440(4) 0.0528(11) Uani 1 1 d .
C18 C 1.2744(6) -0.1860(5) 0.2364(4) 0.0547(11) Uani 1 1 d .
C8 C 0.3718(6) 0.8435(5) 0.5918(4) 0.0629(12) Uani 1 1 d .
H8A H 0.3815 0.8885 0.5066 0.075 Uiso 1 1 calc R
C7 C 0.2589(6) 0.9133(5) 0.6688(4) 0.0605(12) Uani 1 1 d .
H7A H 0.1927 1.0043 0.6360 0.073 Uiso 1 1 calc R
C6 C 0.2457(6) 0.8463(5) 0.7943(4) 0.0571(11) Uani 1 1 d .
C13 C 0.9311(6) 0.5799(5) 0.1712(4) 0.0585(12) Uani 1 1 d .
H13A H 0.9546 0.6217 0.0851 0.070 Uiso 1 1 calc R
C4 C 0.4512(6) 0.6414(5) 0.7659(4) 0.0605(12) Uani 1 1 d .
H4A H 0.5147 0.5493 0.7995 0.073 Uiso 1 1 calc R
C5 C 0.3388(6) 0.7098(5) 0.8435(4) 0.0624(12) Uani 1 1 d .
H5A H 0.3260 0.6639 0.9289 0.075 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'
Cl Cl 0.1484 0.1585 '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
C15 O2 H3O 111.6 . .
C13 N1 C12 121.1(4) . .
C13 N1 H1N 119.6 . .
C12 N1 H1N 119.4 . .
C19 C17 C16 118.2(3) . .
C19 C17 C18 113.8(3) . .
C16 C17 C18 128.0(4) . .
C18 O3 H3O 112.9 . .
C17 C19 C16 124.7(3) . 2_855
C17 C19 H19A 117.6 . .
C16 C19 H19A 117.6 2_855 .
C1 C2 C10 124.3(4) . .
C1 C2 H2A 117.9 . .
C10 C2 H2A 117.9 . .
C14 C10 C11 116.9(4) . .
C14 C10 C2 119.2(4) . .
C11 C10 C2 123.9(4) . .
C13 C14 C10 121.0(4) . .
C13 C14 H14A 119.5 . .
C10 C14 H14A 119.5 . .
C4 C3 C8 118.4(4) . .
C4 C3 C1 118.4(4) . .
C8 C3 C1 123.2(4) . .
C12 C11 C10 120.4(4) . .
C12 C11 H11A 119.8 . .
C10 C11 H11A 119.8 . .
N1 C12 C11 120.7(4) . .
N1 C12 H12A 119.7 . .
C11 C12 H12A 119.7 . .
C19 C16 C17 117.0(3) 2_855 .
C19 C16 C15 115.5(3) 2_855 .
C17 C16 C15 127.5(3) . .
C2 C1 C3 128.1(4) . .
C2 C1 H1A 115.9 . .
C3 C1 H1A 115.9 . .
O1 C15 O2 122.7(4) . .
O1 C15 C16 117.3(3) . .
O2 C15 C16 119.9(4) . .
O4 C18 O3 121.9(4) . .
O4 C18 C17 119.2(4) . .
O3 C18 C17 118.9(4) . .
C7 C8 C3 121.1(4) . .
C7 C8 H8A 119.4 . .
C3 C8 H8A 119.4 . .
C6 C7 C8 119.1(4) . .
C6 C7 H7A 120.5 . .
C8 C7 H7A 120.5 . .
C7 C6 C5 120.7(4) . .
C7 C6 Cl1 119.5(4) . .
C5 C6 Cl1 119.7(4) . .
N1 C13 C14 120.0(4) . .
N1 C13 H13A 120.0 . .
C14 C13 H13A 120.0 . .
C5 C4 C3 120.9(4) . .
C5 C4 H4A 119.5 . .
C3 C4 H4A 119.5 . .
C6 C5 C4 119.7(4) . .
C6 C5 H5A 120.2 . .
C4 C5 H5A 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C6 1.738(4) .
O1 C15 1.250(4) .
O2 C15 1.262(4) .
O2 H3O 1.3069 .
N1 C13 1.335(5) .
N1 C12 1.339(5) .
N1 H1N 0.9086 .
C17 C19 1.386(5) .
C17 C16 1.412(5) .
C17 C18 1.529(5) .
O4 C18 1.213(5) .
O3 C18 1.303(5) .
O3 H3O 1.1065 .
C19 C16 1.393(5) 2_855
C19 H19A 0.9300 .
C2 C1 1.318(6) .
C2 C10 1.477(5) .
C2 H2A 0.9300 .
C10 C14 1.389(5) .
C10 C11 1.393(5) .
C14 C13 1.361(5) .
C14 H14A 0.9300 .
C3 C4 1.378(6) .
C3 C8 1.389(6) .
C3 C1 1.463(6) .
C11 C12 1.357(5) .
C11 H11A 0.9300 .
C12 H12A 0.9300 .
C16 C19 1.393(5) 2_855
C16 C15 1.514(5) .
C1 H1A 0.9300 .
C8 C7 1.382(5) .
C8 H8A 0.9300 .
C7 C6 1.373(6) .
C7 H7A 0.9300 .
C6 C5 1.374(6) .
C13 H13A 0.9300 .
C4 C5 1.378(5) .
C4 H4A 0.9300 .
C5 H5A 0.9300 .
