#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180387 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/56/7205616.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_7205616
loop_
_publ_author_name
'Cao, Deng-Ke'
'Sreevidya, Thekku V.'
'Botoshansky, Mark'
'Golden, Gilad'
'Benedict, Jason B.'
'Kaftory, Menahem'
_publ_section_title
;
 Formation of different photodimers of isoquinolinone by irradiation of
 solid molecular compounds
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3181
_journal_paper_doi               10.1039/c0ce00489h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C18 H14 N2 O2, 2(C2 H4 O2)'
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.42
_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_method           SHELXL-97
_cell_angle_alpha                97.37(3)
_cell_angle_beta                 95.76(3)
_cell_angle_gamma                101.14(3)
_cell_formula_units_Z            1
_cell_length_a                   7.102(6)
_cell_length_b                   7.909(6)
_cell_length_c                   9.350(5)
_cell_measurement_temperature    293(2)
_cell_volume                     506.8(6)
_computing_cell_refinement       'Denzo SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction        'Denzo SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 95
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       'phi scan & omega scan'
_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  0.053
_diffrn_reflns_av_sigmaI/netI    0.0813
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5330
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         26.54
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.10
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.817
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0951P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                1032
_reflns_number_total             1905
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00489h.txt
_cod_data_source_block           pyridacetate
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7205616
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.4245(2) 0.3927(2) 0.34442(18) 0.0523(5) Uani 1 1 d . . .
O2 O 0.8230(3) 0.7558(3) -0.1122(2) 0.0766(7) Uani 1 1 d . . .
C2 C -0.0801(3) 0.4427(3) 0.3317(2) 0.0377(6) Uani 1 1 d . . .
H2 H -0.1205 0.3834 0.2316 0.045 Uiso 1 1 calc R . .
C1 C -0.2577(3) 0.4742(3) 0.3985(2) 0.0371(6) Uani 1 1 d . . .
C3 C 0.0520(3) 0.6173(3) 0.3286(2) 0.0382(6) Uani 1 1 d . . .
O3 O 0.5239(3) 0.7700(3) -0.0747(2) 0.0762(7) Uani 1 1 d . . .
H3 H 0.488(4) 0.694(4) -0.175(3) 0.091 Uiso 1 1 d . . .
N1 N -0.2251(3) 0.5928(2) 0.5176(2) 0.0393(5) Uani 1 1 d . . .
H1 H -0.331(4) 0.619(3) 0.588(2) 0.047 Uiso 1 1 d . . .
C9 C -0.0268(3) 0.6787(3) 0.5793(2) 0.0365(6) Uani 1 1 d . . .
H9 H -0.0327 0.7828 0.6465 0.044 Uiso 1 1 calc R . .
C8 C 0.0810(3) 0.7379(3) 0.4559(2) 0.0383(6) Uani 1 1 d . . .
C7 C 0.2025(3) 0.8984(3) 0.4641(3) 0.0453(6) Uani 1 1 d . . .
H7 H 0.2225 0.9786 0.5489 0.054 Uiso 1 1 d R . .
C5 C 0.2663(4) 0.8212(3) 0.2205(3) 0.0534(7) Uani 1 1 d . . .
H5 H 0.3285 0.8498 0.1413 0.064 Uiso 1 1 calc R . .
C4 C 0.1447(3) 0.6596(3) 0.2113(3) 0.0463(6) Uani 1 1 d . . .
H4 H 0.1256 0.5799 0.1263 0.056 Uiso 1 1 calc R . .
C6 C 0.2958(4) 0.9396(3) 0.3458(3) 0.0514(7) Uani 1 1 d . . .
H6 H 0.3785 1.0476 0.3513 0.062 Uiso 1 1 calc R . .
C10 C 0.7135(4) 0.7997(4) -0.0332(3) 0.0584(7) Uani 1 1 d . . .
C11 C 0.7717(5) 0.9000(5) 0.1159(3) 0.0833(11) Uani 1 1 d . . .
H11A H 0.6942 0.9861 0.1312 0.100 Uiso 1 1 calc R . .
H11B H 0.9057 0.9567 0.1265 0.100 Uiso 1 1 calc R . .
H11C H 0.7525 0.8220 0.1863 0.100 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'
O O 0.0106 0.0060 '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'
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
_geom_angle_publ_flag
C1 C2 C3 108.77(17) . . ?
C1 C2 C9 110.40(18) . 2_566 ?
C3 C2 C9 111.64(18) . 2_566 ?
C1 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C9 C2 H2 108.7 2_566 . ?
O1 C1 N1 122.6(2) . . ?
O1 C1 C2 121.7(2) . . ?
N1 C1 C2 115.7(2) . . ?
C4 C3 C8 119.8(2) . . ?
C4 C3 C2 124.2(2) . . ?
C8 C3 C2 116.0(2) . . ?
C10 O3 H3 110.7(17) . . ?
C1 N1 C9 120.26(19) . . ?
C1 N1 H1 125.8(12) . . ?
C9 N1 H1 113.0(12) . . ?
N1 C9 C8 108.00(18) . . ?
N1 C9 C2 112.51(18) . 2_566 ?
C8 C9 C2 112.30(18) . 2_566 ?
N1 C9 H9 108.0 . . ?
C8 C9 H9 108.0 . . ?
C2 C9 H9 108.0 2_566 . ?
C7 C8 C3 119.9(2) . . ?
C7 C8 C9 124.2(2) . . ?
C3 C8 C9 115.9(2) . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O2 C10 O3 122.0(3) . . ?
O2 C10 C11 124.9(3) . . ?
O3 C10 C11 113.0(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.255(3) . ?
O2 C10 1.194(3) . ?
C2 C1 1.510(3) . ?
C2 C3 1.518(3) . ?
C2 C9 1.597(3) 2_566 ?
C2 H2 0.9800 . ?
C1 N1 1.331(3) . ?
C3 C4 1.379(3) . ?
C3 C8 1.397(3) . ?
O3 C10 1.330(4) . ?
O3 H3 1.03(3) . ?
N1 C9 1.464(3) . ?
N1 H1 1.08(2) . ?
C9 C8 1.521(3) . ?
C9 C2 1.597(3) 2_566 ?
C9 H9 0.9800 . ?
C8 C7 1.379(3) . ?
C7 C6 1.388(3) . ?
C7 H7 0.9300 . ?
C5 C6 1.373(3) . ?
C5 C4 1.385(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C10 C11 1.489(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C2 C1 O1 135.8(2) . . . . ?
C9 C2 C1 O1 -101.4(2) 2_566 . . . ?
C3 C2 C1 N1 -44.4(3) . . . . ?
C9 C2 C1 N1 78.4(2) 2_566 . . . ?
C1 C2 C3 C4 -136.1(2) . . . . ?
C9 C2 C3 C4 101.8(3) 2_566 . . . ?
C1 C2 C3 C8 45.3(3) . . . . ?
C9 C2 C3 C8 -76.8(2) 2_566 . . . ?
O1 C1 N1 C9 177.5(2) . . . . ?
C2 C1 N1 C9 -2.3(3) . . . . ?
C1 N1 C9 C8 47.1(3) . . . . ?
C1 N1 C9 C2 -77.4(3) . . . 2_566 ?
C4 C3 C8 C7 -0.2(3) . . . . ?
C2 C3 C8 C7 178.5(2) . . . . ?
C4 C3 C8 C9 -179.7(2) . . . . ?
C2 C3 C8 C9 -1.1(3) . . . . ?
N1 C9 C8 C7 136.5(2) . . . . ?
C2 C9 C8 C7 -98.9(3) 2_566 . . . ?
N1 C9 C8 C3 -44.0(2) . . . . ?
C2 C9 C8 C3 80.6(2) 2_566 . . . ?
C3 C8 C7 C6 -0.1(3) . . . . ?
C9 C8 C7 C6 179.4(2) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?
C8 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 C5 -178.4(2) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C8 C7 C6 C5 0.4(4) . . . . ?
