#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:23:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180427 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/96/7209623.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_7209623
loop_
_publ_author_name
'Briceño, Alexander'
'Leal, Dayana'
'Ortega, Gabriela'
'Delgado, Graciela Díaz de'
'Ocando, Edgar'
'Cubillan, Liz'
_publ_section_title
;
 Self-assembly, concomitant photochemical processes, and improvement of
 the yield of [2 + 2] photoreactions from supramolecular arrays via
 mechanochemical assistance
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              2795
_journal_paper_doi               10.1039/c3ce26752k
_journal_volume                  15
_journal_year                    2013
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C13 H11 Cl N, C4 H3 O4, 0.5(C4 H4 O4)'
_chemical_formula_sum            'C19 H16 Cl N O6'
_chemical_formula_weight         389.78
_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                104.06(3)
_cell_angle_beta                 97.67(3)
_cell_angle_gamma                105.15(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6870(17)
_cell_length_b                   8.9000(18)
_cell_length_c                   13.039(3)
_cell_measurement_reflns_used    730
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      1.52
_cell_volume                     922.8(4)
_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_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 0.967
_diffrn_measured_fraction_theta_max 0.775
_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  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13239
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.10
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.0957
_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)+(0.0432P)²+1.7336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.2090
_reflns_number_gt                2296
_reflns_number_total             3499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce26752k.txt
_cod_data_source_block           shelxle
_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_cell_volume        922.8(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7209623
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
N1 N -0.0918(5) 0.0570(5) 0.8449(3) 0.0582(10) Uani 1 1 d .
H1N H -0.0405 0.0697 0.7941 0.070 Uiso 1 1 calc R
Cl1 Cl -0.6801(2) -0.47327(18) 1.06801(13) 0.0864(5) Uani 1 1 d .
O1 O 0.3581(5) 0.5879(5) 0.7568(3) 0.0901(13) Uani 1 1 d .
H1OH H 0.2678 0.4829 0.7729 0.108 Uiso 1 1 d R
O2 O 0.5121(6) 0.6483(5) 0.6428(4) 0.1212(19) Uani 1 1 d .
O3 O 0.1668(5) 0.3409(4) 0.7736(3) 0.0801(12) Uani 1 1 d .
O4 O 0.0691(4) 0.0814(4) 0.6850(3) 0.0644(9) Uani 1 1 d .
O5 O -0.0738(4) 0.1992(4) 0.4312(3) 0.0678(10) Uani 1 1 d .
H5OH H -0.0781 0.0941 0.3905 0.081 Uiso 1 1 d R
O6 O 0.0055(5) 0.2811(4) 0.2931(3) 0.0781(11) Uani 1 1 d .
C1 C -0.4371(6) -0.1398(6) 1.1021(4) 0.0547(12) Uani 1 1 d .
H1 H -0.4591 -0.2309 1.0429 0.066 Uiso 1 1 calc R
C2 C -0.3309(6) -0.0052(6) 1.0991(4) 0.0559(12) Uani 1 1 d .
H2 H -0.3056 0.0856 1.1589 0.067 Uiso 1 1 calc R
C3 C -0.5239(5) -0.1603(6) 1.1890(4) 0.0505(11) Uani 1 1 d .
C4 C -0.6371(6) -0.3074(6) 1.1830(4) 0.0555(12) Uani 1 1 d .
C5 C -0.7193(6) -0.3270(7) 1.2644(4) 0.0706(15) Uani 1 1 d .
H5 H -0.7921 -0.4276 1.2585 0.085 Uiso 1 1 calc R
C6 C -0.6941(7) -0.1987(7) 1.3537(4) 0.0730(15) Uani 1 1 d .
H6 H -0.7490 -0.2118 1.4090 0.088 Uiso 1 1 calc R
C7 C -0.5865(7) -0.0491(7) 1.3616(4) 0.0664(14) Uani 1 1 d .
H7A H -0.5719 0.0395 1.4211 0.080 Uiso 1 1 calc R
C8 C -0.5008(6) -0.0314(6) 1.2812(4) 0.0583(12) Uani 1 1 d .
H8 H -0.4260 0.0688 1.2886 0.070 Uiso 1 1 calc R
C9 C -0.2498(5) 0.0133(6) 1.0098(3) 0.0494(11) Uani 1 1 d .
C10 C -0.2874(6) -0.1072(6) 0.9121(4) 0.0552(12) Uani 1 1 d .
H10 H -0.3676 -0.2052 0.9017 0.066 Uiso 1 1 calc R
C11 C -0.2077(6) -0.0836(6) 0.8306(4) 0.0582(12) Uani 1 1 d .
H11 H -0.2342 -0.1653 0.7654 0.070 Uiso 1 1 calc R
C12 C -0.0546(6) 0.1772(7) 0.9363(4) 0.0644(13) Uani 1 1 d .
H12 H 0.0240 0.2748 0.9432 0.077 Uiso 1 1 calc R
C13 C -0.1297(6) 0.1600(6) 1.0204(4) 0.0597(13) Uani 1 1 d .
H13 H -0.1015 0.2449 1.0842 0.072 Uiso 1 1 calc R
C14 C 0.2528(6) 0.2441(6) 0.6101(4) 0.0556(12) Uani 1 1 d .
H14 H 0.2372 0.1491 0.5553 0.067 Uiso 1 1 calc R
C15 C 0.3559(6) 0.3768(6) 0.5998(4) 0.0628(13) Uani 1 1 d .
H15 H 0.3996 0.3590 0.5382 0.075 Uiso 1 1 calc R
C16 C 0.4131(7) 0.5464(7) 0.6685(5) 0.0737(15) Uani 1 1 d .
C17 C 0.1584(6) 0.2244(6) 0.6958(4) 0.0556(12) Uani 1 1 d .
C18 C 0.0006(6) 0.4786(6) 0.4485(4) 0.0549(12) Uani 1 1 d .
H18 H 0.0169 0.5597 0.4141 0.066 Uiso 1 1 calc R
C19 C -0.0220(6) 0.3111(6) 0.3827(4) 0.0543(11) Uani 1 1 d .
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
C12 N1 C11 121.2(4) .
C2 C1 C3 126.6(5) .
C1 C2 C9 125.5(4) .
C4 C3 C8 116.4(4) .
C4 C3 C1 122.1(4) .
C8 C3 C1 121.4(4) .
C5 C4 C3 122.3(5) .
C5 C4 Cl1 118.1(4) .
C3 C4 Cl1 119.6(4) .
C6 C5 C4 120.0(5) .
C5 C6 C7 119.7(5) .
C8 C7 C6 120.0(5) .
C7 C8 C3 121.5(5) .
C10 C9 C13 117.2(4) .
C10 C9 C2 123.1(4) .
C13 C9 C2 119.7(4) .
C11 C10 C9 120.8(4) .
N1 C11 C10 120.0(4) .
N1 C12 C13 121.3(5) .
C12 C13 C9 119.5(5) .
C15 C14 C17 130.0(5) .
C14 C15 C16 131.5(5) .
O2 C16 O1 120.3(5) .
O2 C16 C15 119.5(6) .
O1 C16 C15 120.2(5) .
O3 C17 O4 121.8(5) .
O3 C17 C14 122.0(4) .
O4 C17 C14 116.2(4) .
C18 C18 C19 124.9(6) 2_566
O6 C19 O5 123.7(4) .
O6 C19 C18 122.4(5) .
O5 C19 C18 113.9(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C12 1.328(6) .
N1 C11 1.339(6) .
Cl1 C4 1.748(5) .
O1 C16 1.313(6) .
O2 C16 1.221(6) .
O3 C17 1.240(5) .
O4 C17 1.269(5) .
O5 C19 1.320(5) .
O6 C19 1.203(5) .
C1 C2 1.320(6) .
C1 C3 1.464(6) .
C2 C9 1.459(6) .
C3 C4 1.394(6) .
C3 C8 1.395(6) .
C4 C5 1.376(7) .
C5 C6 1.364(7) .
C6 C7 1.383(7) .
C7 C8 1.381(6) .
C9 C10 1.386(6) .
C9 C13 1.405(6) .
C10 C11 1.372(6) .
C12 C13 1.369(6) .
C14 C15 1.330(6) .
C14 C17 1.489(6) .
C15 C16 1.470(7) .
C18 C18 1.306(9) 2_566
C18 C19 1.476(6) .
