#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/61/1506157.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_1506157
loop_
_publ_author_name
'Das, Suven'
'Fröhlich, Roland'
'Pramanik, Animesh'
_publ_section_title
;
 Synthesis and fluorescent properties of a new class of heterocycles of
 isoindole fused imidazoles with phenolic subunits.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4263
_journal_page_last               4266
_journal_paper_doi               10.1021/ol061520n
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C17 H14 N2 O5'
_chemical_formula_weight         326.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.103(1)
_cell_length_b                   13.709(1)
_cell_length_c                   14.869(1)
_cell_measurement_reflns_used    2458
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1447.9(2)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12370
_diffrn_reflns_theta_full        67.79
_diffrn_reflns_theta_max         67.79
_diffrn_reflns_theta_min         5.95
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  0.8342
_exptl_absorpt_correction_T_min  0.7343
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0270
_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)+(0.0425P)²+0.2382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0725
_reflns_number_gt                2552
_reflns_number_total             2564
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061520nsi20060621_104959.cif
_cod_data_source_block           fro3514
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1506157
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 -0.02462(17) 0.22835(9) 0.64671(8) 0.0297(3) Uani 1 1 d .
H1 H -0.015(3) 0.1662(15) 0.6611(13) 0.052(5) Uiso 1 1 d .
C2 C -0.00953(19) 0.30199(9) 0.70840(9) 0.0294(3) Uani 1 1 d .
O2 O 0.02764(16) 0.29532(7) 0.78843(7) 0.0396(3) Uani 1 1 d .
N3 N -0.04838(17) 0.38582(8) 0.65902(7) 0.0286(2) Uani 1 1 d .
C4 C -0.0586(2) 0.48706(9) 0.67553(9) 0.0300(3) Uani 1 1 d .
O41 O -0.02750(18) 0.52652(7) 0.74717(6) 0.0428(3) Uani 1 1 d .
C5 C -0.1158(2) 0.52805(10) 0.58773(9) 0.0292(3) Uani 1 1 d .
C6 C -0.1568(2) 0.62457(10) 0.56766(10) 0.0363(3) Uani 1 1 d .
H6 H -0.1405 0.6741 0.6107 0.044 Uiso 1 1 calc R
C7 C -0.2225(2) 0.64570(10) 0.48207(10) 0.0392(3) Uani 1 1 d .
H7 H -0.2531 0.7103 0.4668 0.047 Uiso 1 1 calc R
C8 C -0.2436(2) 0.57177(11) 0.41847(10) 0.0370(3) Uani 1 1 d .
H8 H -0.2893 0.5876 0.3609 0.044 Uiso 1 1 calc R
C9 C -0.1990(2) 0.47546(10) 0.43783(9) 0.0310(3) Uani 1 1 d .
H9 H -0.2120 0.4266 0.3939 0.037 Uiso 1 1 calc R
C10 C -0.13454(18) 0.45297(9) 0.52377(9) 0.0271(3) Uani 1 1 d .
C11 C -0.08671(18) 0.36203(9) 0.56858(9) 0.0268(3) Uani 1 1 d .
C12 C -0.07090(18) 0.26402(9) 0.56045(9) 0.0264(3) Uani 1 1 d .
C13 C -0.08005(17) 0.20000(9) 0.48168(9) 0.0273(3) Uani 1 1 d .
C14 C -0.02737(19) 0.23655(10) 0.39702(9) 0.0292(3) Uani 1 1 d .
H14 H 0.0081 0.3023 0.3910 0.035 Uiso 1 1 calc R
C15 C -0.02757(19) 0.17611(10) 0.32241(9) 0.0328(3) Uani 1 1 d .
O151 O 0.02281(17) 0.20544(8) 0.23692(7) 0.0439(3) Uani 1 1 d .
C152 C 0.0422(3) 0.30743(12) 0.22163(11) 0.0473(4) Uani 1 1 d .
H15A H -0.0727 0.3404 0.2394 0.071 Uiso 1 1 calc R
H15B H 0.0658 0.3191 0.1583 0.071 Uiso 1 1 calc R
H15C H 0.1467 0.3323 0.2568 0.071 Uiso 1 1 calc R
C16 C -0.0753(2) 0.07797(11) 0.33165(10) 0.0365(3) Uani 1 1 d .
H16 H -0.0717 0.0365 0.2814 0.044 Uiso 1 1 calc R
C17 C -0.1281(2) 0.04151(10) 0.41464(10) 0.0348(3) Uani 1 1 d .
H17 H -0.1606 -0.0247 0.4202 0.042 Uiso 1 1 calc R
C18 C -0.13361(19) 0.10180(9) 0.49002(9) 0.0291(3) Uani 1 1 d .
O181 O -0.19108(15) 0.07082(7) 0.57215(7) 0.0367(2) Uani 1 1 d .
H181 H -0.2092 0.0110 0.5708 0.055 Uiso 1 1 calc R
O100 O -0.7577(2) 0.61824(9) 0.41377(9) 0.0468(3) Uani 1 1 d .
H101 H -0.681(4) 0.6425(18) 0.3751(17) 0.072(7) Uiso 1 1 d .
H102 H -0.867(6) 0.630(3) 0.390(2) 0.122(12) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 N1 C12 111.83(11)
C2 N1 H1 123.0(12)
C12 N1 H1 125.1(12)
O2 C2 N1 127.90(13)
O2 C2 N3 128.20(12)
N1 C2 N3 103.90(11)
C2 N3 C11 110.52(11)
C2 N3 C4 136.95(12)
C11 N3 C4 112.53(11)
O41 C4 N3 125.52(13)
O41 C4 C5 130.92(12)
N3 C4 C5 103.56(11)
C6 C5 C10 122.16(13)
C6 C5 C4 127.61(12)
C10 C5 C4 110.16(11)
C7 C6 C5 117.87(13)
C7 C6 H6 121.1
C5 C6 H6 121.1
C6 C7 C8 120.46(13)
C6 C7 H7 119.8
C8 C7 H7 119.8
C9 C8 C7 121.75(13)
C9 C8 H8 119.1
C7 C8 H8 119.1
C8 C9 C10 118.44(13)
C8 C9 H9 120.8
C10 C9 H9 120.8
C9 C10 C5 119.29(12)
C9 C10 C11 133.44(12)
C5 C10 C11 107.18(12)
C12 C11 N3 107.37(11)
C12 C11 C10 146.06(13)
N3 C11 C10 106.49(11)
C11 C12 N1 106.38(11)
C11 C12 C13 131.47(12)
N1 C12 C13 121.96(11)
C18 C13 C14 119.53(12)
C18 C13 C12 121.04(12)
C14 C13 C12 119.39(11)
C15 C14 C13 120.26(13)
C15 C14 H14 119.9
C13 C14 H14 119.9
O151 C15 C14 124.28(13)
O151 C15 C16 115.79(12)
C14 C15 C16 119.91(13)
C15 O151 C152 117.29(12)
O151 C152 H15A 109.5
O151 C152 H15B 109.5
H15A C152 H15B 109.5
O151 C152 H15C 109.5
H15A C152 H15C 109.5
H15B C152 H15C 109.5
C17 C16 C15 120.18(13)
C17 C16 H16 119.9
C15 C16 H16 119.9
C16 C17 C18 120.73(12)
C16 C17 H17 119.6
C18 C17 H17 119.6
O181 C18 C17 123.18(12)
O181 C18 C13 117.47(12)
C17 C18 C13 119.34(12)
C18 O181 H181 109.5
H101 O100 H102 103(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3682(17)
N1 C12 1.4114(17)
N1 H1 0.88(2)
C2 O2 1.2224(17)
C2 N3 1.3913(17)
N3 C11 1.4103(17)
N3 C4 1.4113(17)
C4 O41 1.2149(17)
C4 C5 1.4783(18)
C5 C6 1.3874(19)
C5 C10 1.4077(18)
C6 C7 1.386(2)
C6 H6 0.9400
C7 C8 1.394(2)
C7 H7 0.9400
C8 C9 1.388(2)
C8 H8 0.9400
C9 C10 1.392(2)
C9 H9 0.9400
C10 C11 1.4537(18)
C11 C12 1.3538(18)
C12 C13 1.4650(18)
C13 C18 1.4045(18)
C13 C14 1.4055(19)
C14 C15 1.3847(19)
C14 H14 0.9400
C15 O151 1.3804(17)
C15 C16 1.394(2)
O151 C152 1.423(2)
C152 H15A 0.9700
C152 H15B 0.9700
C152 H15C 0.9700
C16 C17 1.383(2)
C16 H16 0.9400
C17 C18 1.3931(19)
C17 H17 0.9400
C18 O181 1.3559(17)
O181 H181 0.8300
O100 H101 0.86(3)
O100 H102 0.87(4)
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
C12 N1 C2 O2 179.60(14)
C12 N1 C2 N3 0.25(14)
O2 C2 N3 C11 -179.23(14)
N1 C2 N3 C11 0.12(14)
O2 C2 N3 C4 1.1(3)
N1 C2 N3 C4 -179.57(16)
C2 N3 C4 O41 1.4(3)
C11 N3 C4 O41 -178.24(14)
C2 N3 C4 C5 -177.93(15)
C11 N3 C4 C5 2.38(15)
O41 C4 C5 C6 -3.3(3)
N3 C4 C5 C6 176.03(14)
O41 C4 C5 C10 179.85(16)
N3 C4 C5 C10 -0.82(16)
C10 C5 C6 C7 1.6(2)
C4 C5 C6 C7 -174.89(14)
C5 C6 C7 C8 -0.9(2)
C6 C7 C8 C9 -0.5(2)
C7 C8 C9 C10 1.1(2)
C8 C9 C10 C5 -0.3(2)
C8 C9 C10 C11 175.67(14)
C6 C5 C10 C9 -1.0(2)
C4 C5 C10 C9 176.03(12)
C6 C5 C10 C11 -177.98(13)
C4 C5 C10 C11 -0.93(16)
C2 N3 C11 C12 -0.46(15)
C4 N3 C11 C12 179.32(12)
C2 N3 C11 C10 177.22(11)
C4 N3 C11 C10 -3.01(15)
C9 C10 C11 C12 2.0(3)
C5 C10 C11 C12 178.3(2)
C9 C10 C11 N3 -174.03(14)
C5 C10 C11 N3 2.33(14)
N3 C11 C12 N1 0.58(14)
C10 C11 C12 N1 -175.42(19)
N3 C11 C12 C13 -174.40(12)
C10 C11 C12 C13 9.6(3)
C2 N1 C12 C11 -0.54(15)
C2 N1 C12 C13 175.03(12)
C11 C12 C13 C18 -154.53(14)
N1 C12 C13 C18 31.15(18)
C11 C12 C13 C14 28.0(2)
N1 C12 C13 C14 -146.37(12)
C18 C13 C14 C15 -0.24(19)
C12 C13 C14 C15 177.32(12)
C13 C14 C15 O151 -179.67(13)
C13 C14 C15 C16 -1.7(2)
C14 C15 O151 C152 -12.1(2)
C16 C15 O151 C152 169.89(14)
O151 C15 C16 C17 -179.91(13)
C14 C15 C16 C17 2.0(2)
C15 C16 C17 C18 -0.2(2)
C16 C17 C18 O181 177.40(13)
C16 C17 C18 C13 -1.7(2)
C14 C13 C18 O181 -177.22(12)
C12 C13 C18 O181 5.26(18)
C14 C13 C18 C17 1.94(19)
C12 C13 C18 C17 -175.58(12)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21151956 ChemSpider
