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#$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180387 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/56/7205615.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_7205615
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         'C9 H7 N O'
_chemical_formula_sum            'C9 H7 N O'
_chemical_formula_weight         145.16
_chemical_name_common            isoquinolinone
_chemical_name_systematic
;
Isoquinolin-3(2H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 108.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.868(2)
_cell_length_b                   6.0890(10)
_cell_length_c                   12.466(2)
_cell_measurement_temperature    293(2)
_cell_volume                     711.8(2)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2006)'
_computing_data_reduction        'DENZO HKL2000 (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, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_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  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4352
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0661
_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)+(0.1282P)²+0.0704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2018
_reflns_number_gt                950
_reflns_number_total             1258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00489h.txt
_cod_data_source_block           Isoquinolin-3(2H)-one
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7205615
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.09287(18) 0.9376(3) -0.10159(13) 0.0639(6) Uani 1 1 d . . .
H1O1 H 0.0337 1.0115 -0.0838 0.077 Uiso 0.50 1 calc PR . .
N1 N 0.08597(17) 0.7660(3) 0.06018(14) 0.0473(6) Uani 1 1 d . . .
H1N1 H 0.0244 0.8610 0.0665 0.057 Uiso 0.50 1 calc PR . .
C1 C 0.1385(2) 0.7793(4) -0.02811(17) 0.0471(6) Uani 1 1 d . . .
C2 C 0.2371(2) 0.6260(4) -0.03941(17) 0.0511(7) Uani 1 1 d . . .
H2 H 0.2728 0.6346 -0.1001 0.061 Uiso 1 1 calc R . .
C3 C 0.2829(2) 0.4578(4) 0.04061(16) 0.0442(6) Uani 1 1 d . . .
C4 C 0.3845(2) 0.2971(4) 0.03511(18) 0.0532(7) Uani 1 1 d . . .
H4 H 0.4233 0.3003 -0.0240 0.064 Uiso 1 1 calc R . .
C5 C 0.4258(3) 0.1388(4) 0.11517(19) 0.0578(7) Uani 1 1 d . . .
H5 H 0.4936 0.0361 0.1107 0.069 Uiso 1 1 calc R . .
C6 C 0.3676(3) 0.1268(4) 0.20525(19) 0.0594(7) Uani 1 1 d . . .
H6 H 0.3962 0.0154 0.2586 0.071 Uiso 1 1 calc R . .
C7 C 0.2707(2) 0.2762(4) 0.21421(19) 0.0542(7) Uani 1 1 d . . .
H7 H 0.2333 0.2684 0.2740 0.065 Uiso 1 1 calc R . .
C8 C 0.2257(2) 0.4460(4) 0.13213(16) 0.0448(6) Uani 1 1 d . . .
C9 C 0.1285(2) 0.6077(4) 0.13733(17) 0.0500(6) Uani 1 1 d . . .
H9 H 0.0914 0.6054 0.1974 0.060 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O11 0.0704(11) 0.0770(13) 0.0548(10) 0.0196(8) 0.0346(8) 0.0265(9)
N1 0.0427(10) 0.0566(12) 0.0438(10) 0.0000(8) 0.0154(8) 0.0065(8)
C1 0.0457(12) 0.0575(14) 0.0405(11) 0.0040(9) 0.0168(9) 0.0041(10)
C2 0.0485(12) 0.0654(15) 0.0433(12) 0.0010(10) 0.0201(10) 0.0078(10)
C3 0.0423(11) 0.0507(13) 0.0380(10) -0.0056(9) 0.0100(8) -0.0009(9)
C4 0.0569(13) 0.0608(15) 0.0434(12) -0.0064(10) 0.0176(10) 0.0078(10)
C5 0.0596(14) 0.0543(15) 0.0562(14) -0.0055(11) 0.0134(11) 0.0126(11)
C6 0.0639(15) 0.0564(16) 0.0536(14) 0.0094(11) 0.0123(11) 0.0069(11)
C7 0.0566(13) 0.0623(15) 0.0438(12) 0.0054(10) 0.0160(10) -0.0009(11)
C8 0.0411(11) 0.0520(13) 0.0393(11) -0.0042(9) 0.0095(8) -0.0019(9)
C9 0.0465(12) 0.0650(15) 0.0419(11) -0.0034(10) 0.0187(9) 0.0005(10)
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'
O O 0.0106 0.0060 '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'
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 O11 H1O1 109.5 . . ?
C9 N1 C1 120.95(17) . . ?
C9 N1 H1N1 119.5 . . ?
C1 N1 H1N1 119.5 . . ?
O11 C1 N1 118.45(18) . . ?
O11 C1 C2 121.59(18) . . ?
N1 C1 C2 119.96(19) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 123.1(2) . . ?
C2 C3 C8 119.12(19) . . ?
C4 C3 C8 117.8(2) . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C3 116.93(19) . . ?
C9 C8 C7 123.1(2) . . ?
C3 C8 C7 119.97(19) . . ?
N1 C9 C8 123.02(18) . . ?
N1 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
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
O11 C1 1.310(3) . ?
O11 H1O1 0.8200 . ?
N1 C9 1.334(3) . ?
N1 C1 1.357(3) . ?
N1 H1N1 0.8600 . ?
C1 C2 1.387(3) . ?
C2 C3 1.402(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.418(3) . ?
C3 C8 1.424(3) . ?
C4 C5 1.356(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.350(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.424(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9300 . ?
