#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/06/2200642.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2200642
loop_
_publ_author_name
'Anwar Usman'
'Ibrahim Abdul Razak'
'Hoong-Kun Fun'
'Suchada Chantrapromma'
'Yan Zhang'
'Jian-Hua Xu'
_publ_section_title
;
 4-[α-Benzoyl-α-(2-phenylethynyl)methylene]isoquinoline-1,3-dione
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1055
_journal_page_last               o1057
_journal_paper_doi               10.1107/S1600536801016956
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C25 H15 N O3'
_chemical_formula_moiety         'C25 H15 N O3'
_chemical_formula_sum            'C25 H15 N O3'
_chemical_formula_weight         377.38
_chemical_name_systematic
;
4-[α-benzoyl-α-(2-phenylethynyl)methylene]isoquinoline-1,3-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.2730(10)
_cell_angle_beta                 100.5620(10)
_cell_angle_gamma                100.7030(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5566(5)
_cell_length_b                   10.3679(7)
_cell_length_c                   12.7275(8)
_cell_measurement_reflns_used    3718
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.55
_cell_measurement_theta_min      1.68
_cell_volume                     931.28(11)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .965
_diffrn_measured_fraction_theta_max .965
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .067
_diffrn_reflns_av_sigmaI/netI    .1407
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5135
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_count none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .089
_exptl_absorpt_correction_T_max  .984
_exptl_absorpt_correction_T_min  .970
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          .34
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .18
_refine_diff_density_max         .35
_refine_diff_density_min         -.33
_refine_ls_extinction_coef       .077(10)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   .91
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .91
_refine_ls_R_factor_all          .099
_refine_ls_R_factor_gt           .074
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0735P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .195
_reflns_number_gt                1918
_reflns_number_total             3151
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6064.cif
_cod_data_source_block           I
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2200642
_cod_database_fobs_code          2200642
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 -.4918(3) -.5972(2) -.13467(17) .0542(7) Uani d . 1 . . O
O2 -.2570(4) -.1525(2) .01873(17) .0619(7) Uani d . 1 . . O
O3 -.4693(3) -.1049(2) -.36443(18) .0559(7) Uani d . 1 . . O
N1 -.3748(4) -.3734(3) -.0629(2) .0414(7) Uani d . 1 . . N
H1A -.398(4) -.377(3) -.005(3) .044(9) Uiso d . 1 . . H
C1 -.2972(4) -.3435(3) -.2645(2) .0330(7) Uani d . 1 . . C
C2 -.2354(4) -.3373(3) -.3609(2) .0418(8) Uani d . 1 . . C
H2A -.1844 -.2534 -.3713 .050 Uiso calc R 1 . . H
C3 -.2493(5) -.4540(3) -.4405(3) .0519(9) Uani d . 1 . . C
H3A -.2109 -.4474 -.5049 .062 Uiso calc R 1 . . H
C4 -.3184(5) -.5796(3) -.4270(3) .0493(8) Uani d . 1 . . C
H4A -.3274 -.6576 -.4816 .059 Uiso calc R 1 . . H
C5 -.3746(4) -.5886(3) -.3310(3) .0441(8) Uani d . 1 . . C
H5A -.4205 -.6734 -.3206 .053 Uiso calc R 1 . . H
C6 -.3632(4) -.4724(3) -.2500(2) .0348(7) Uani d . 1 . . C
C7 -.4167(4) -.4871(3) -.1472(2) .0393(7) Uani d . 1 . . C
C8 -.3000(4) -.2426(3) -.0653(2) .0377(7) Uani d . 1 . . C
C9 -.2880(3) -.2212(3) -.1776(2) .0327(7) Uani d . 1 . . C
C10 -.2815(4) -.0947(3) -.1910(2) .0343(7) Uani d . 1 . . C
C11 -.2649(4) .0218(3) -.1047(2) .0400(7) Uani d . 1 . . C
C12 -.2451(4) .1249(3) -.0370(3) .0431(8) Uani d . 1 . . C
C13 -.2161(4) .2361(3) .0581(2) .0384(7) Uani d . 1 . . C
C14 -.2562(4) .2101(3) .1548(3) .0457(8) Uani d . 1 . . C
H14A -.3022 .1213 .1570 .055 Uiso calc R 1 . . H
C15 -.2283(5) .3147(4) .2476(3) .0546(9) Uani d . 1 . . C
H15A -.2566 .2968 .3120 .065 Uiso calc R 1 . . H
C16 -.1584(5) .4462(4) .2447(3) .0601(10) Uani d . 1 . . C
H16A -.1382 .5169 .3076 .072 Uiso calc R 1 . . H
C17 -.1186(5) .4736(4) .1498(3) .0569(9) Uani d . 1 . . C
H17A -.0714 .5625 .1484 .068 Uiso calc R 1 . . H
C18 -.1483(4) .3694(3) .0563(3) .0493(8) Uani d . 1 . . C
H18A -.1229 .3884 -.0083 .059 Uiso calc R 1 . . H
C19 -.3155(4) -.0618(3) -.3040(2) .0370(7) Uani d . 1 . . C
C20 -.1625(4) .0263(3) -.3304(2) .0358(7) Uani d . 1 . . C
C21 .0167(4) .0594(3) -.2653(2) .0439(8) Uani d . 1 . . C
H21A .029(4) .011(3) -.205(3) .055(9) Uiso d . 1 . . H
C22 .1587(5) .1403(3) -.2928(3) .0549(9) Uani d . 1 . . C
H22A .2780 .1633 -.2484 .066 Uiso calc R 1 . . H
C23 .1222(5) .1872(3) -.3870(3) .0581(10) Uani d . 1 . . C
H23A .2179 .2405 -.4065 .070 Uiso calc R 1 . . H
C24 -.0544(5) .1552(3) -.4517(3) .0545(9) Uani d . 1 . . C
H24A -.0774 .1879 -.5142 .065 Uiso calc R 1 . . H
C25 -.1983(4) .0754(3) -.4250(2) .0454(8) Uani d . 1 . . C
H25A -.3176 .0543 -.4691 .055 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 '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_publ_flag
C7 N1 C8 127.2(3) ?
C7 N1 H1A 120(2) ?
C8 N1 H1A 112(2) ?
C6 C1 C2 117.4(3) ?
C6 C1 C9 119.9(2) ?
C2 C1 C9 122.7(3) ?
C3 C2 C1 120.7(3) ?
C3 C2 H2A 119.7 ?
C1 C2 H2A 119.7 ?
C4 C3 C2 121.5(3) ?
C4 C3 H3A 119.3 ?
C2 C3 H3A 119.3 ?
C3 C4 C5 118.9(3) ?
C3 C4 H4A 120.5 ?
C5 C4 H4A 120.5 ?
C4 C5 C6 120.7(3) ?
C4 C5 H5A 119.7 ?
C6 C5 H5A 119.7 ?
C5 C6 C1 120.8(3) ?
C5 C6 C7 118.7(3) ?
C1 C6 C7 120.5(3) ?
O1 C7 N1 120.2(3) ?
O1 C7 C6 122.8(3) ?
N1 C7 C6 117.0(3) ?
O2 C8 N1 119.8(3) ?
O2 C8 C9 124.1(3) ?
N1 C8 C9 116.1(3) ?
C10 C9 C1 126.3(2) ?
C10 C9 C8 117.4(3) ?
C1 C9 C8 116.2(2) ?
C9 C10 C11 124.8(2) yes
C9 C10 C19 123.9(2) yes
C11 C10 C19 110.8(2) yes
C12 C11 C10 175.2(3) yes
C11 C12 C13 170.3(3) yes
C14 C13 C18 118.9(3) ?
C14 C13 C12 119.3(3) ?
C18 C13 C12 121.7(3) ?
C15 C14 C13 120.5(3) ?
C15 C14 H14A 119.7 ?
C13 C14 H14A 119.7 ?
C14 C15 C16 119.7(3) ?
C14 C15 H15A 120.2 ?
C16 C15 H15A 120.2 ?
C17 C16 C15 120.5(3) ?
C17 C16 H16A 119.8 ?
C15 C16 H16A 119.8 ?
C16 C17 C18 120.1(3) ?
C16 C17 H17A 120.0 ?
C18 C17 H17A 120.0 ?
C17 C18 C13 120.3(3) ?
C17 C18 H18A 119.9 ?
C13 C18 H18A 119.9 ?
O3 C19 C20 123.7(2) ?
O3 C19 C10 118.2(2) ?
C20 C19 C10 118.0(2) ?
C21 C20 C25 119.5(3) ?
C21 C20 C19 121.5(2) ?
C25 C20 C19 119.0(3) ?
C22 C21 C20 120.5(3) ?
C22 C21 H21A 126.5(17) ?
C20 C21 H21A 112.7(17) ?
C21 C22 C23 119.6(3) ?
C21 C22 H22A 120.2 ?
C23 C22 H22A 120.2 ?
C24 C23 C22 120.3(3) ?
C24 C23 H23A 119.8 ?
C22 C23 H23A 119.8 ?
C23 C24 C25 120.9(3) ?
C23 C24 H24A 119.6 ?
C25 C24 H24A 119.6 ?
C24 C25 C20 119.2(3) ?
C24 C25 H25A 120.4 ?
C20 C25 H25A 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.233(3) ?
O2 C8 . 1.207(3) ?
O3 C19 . 1.214(3) ?
N1 C7 . 1.356(4) yes
N1 C8 . 1.378(4) yes
N1 H1A . .80(3) ?
C1 C6 . 1.399(4) yes
C1 C2 . 1.401(4) ?
C1 C9 . 1.476(4) yes
C2 C3 . 1.376(4) ?
C2 H2A . .9300 ?
C3 C4 . 1.369(4) ?
C3 H3A . .93 ?
C4 C5 . 1.379(4) ?
C4 H4A . .93 ?
C5 C6 . 1.387(4) ?
C5 H5A . .93 ?
C6 C7 . 1.468(4) ?
C8 C9 . 1.508(4) yes
C9 C10 . 1.350(4) yes
C10 C11 . 1.418(4) yes
C10 C19 . 1.535(4) yes
C11 C12 . 1.186(4) yes
C12 C13 . 1.435(4) yes
C13 C14 . 1.388(4) ?
C13 C18 . 1.389(4) ?
C14 C15 . 1.377(4) ?
C14 H14A . .93 ?
C15 C16 . 1.378(5) ?
C15 H15A . .93 ?
C16 C17 . 1.371(5) ?
C16 H16A . .93 ?
C17 C18 . 1.378(4) ?
C17 H17A . .93 ?
C18 H18A . .93 ?
C19 C20 . 1.472(4) yes
C20 C21 . 1.391(4) ?
C20 C25 . 1.405(4) ?
C21 C22 . 1.380(4) ?
C21 H21A . 1.00(3) ?
C22 C23 . 1.389(4) ?
C22 H22A . .93 ?
C23 C24 . 1.373(5) ?
C23 H23A . .93 ?
C24 C25 . 1.379(4) ?
C24 H24A . .93 ?
C25 H25A . .93 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O1 2_445 .79(4) 2.14(3) 2.928(3) 170(3) yes
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
C6 C1 C2 C3 3.5(4)
C9 C1 C2 C3 -179.0(3)
C1 C2 C3 C4 -1.9(5)
C2 C3 C4 C5 -.2(5)
C3 C4 C5 C6 .7(5)
C4 C5 C6 C1 1.0(4)
C4 C5 C6 C7 -177.3(3)
C2 C1 C6 C5 -3.0(4)
C9 C1 C6 C5 179.4(2)
C2 C1 C6 C7 175.2(3)
C9 C1 C6 C7 -2.4(4)
C8 N1 C7 O1 -176.4(3)
C8 N1 C7 C6 5.5(4)
C5 C6 C7 O1 -8.9(4)
C1 C6 C7 O1 172.9(3)
C5 C6 C7 N1 169.2(3)
C1 C6 C7 N1 -9.0(4)
C7 N1 C8 O2 -174.4(3)
C7 N1 C8 C9 9.0(4)
C6 C1 C9 C10 -159.1(3)
C2 C1 C9 C10 23.5(4)
C6 C1 C9 C8 16.6(4)
C2 C1 C9 C8 -160.9(3)
O2 C8 C9 C10 -19.9(4)
N1 C8 C9 C10 156.4(3)
O2 C8 C9 C1 164.0(3)
N1 C8 C9 C1 -19.6(4)
C1 C9 C10 C11 -177.2(2)
C8 C9 C10 C11 7.2(4)
C1 C9 C10 C19 10.8(4)
C8 C9 C10 C19 -164.8(2)
C18 C13 C14 C15 -.3(5)
C12 C13 C14 C15 179.5(3)
C13 C14 C15 C16 -.6(5)
C14 C15 C16 C17 .8(5)
C15 C16 C17 C18 .0(5)
C16 C17 C18 C13 -1.0(5)
C14 C13 C18 C17 1.1(5)
C12 C13 C18 C17 -178.7(3)
C9 C10 C19 O3 65.9(4)
C11 C10 C19 O3 -107.1(3)
C9 C10 C19 C20 -117.3(3)
C11 C10 C19 C20 69.8(3)
O3 C19 C20 C21 -172.0(3)
C10 C19 C20 C21 11.4(4)
O3 C19 C20 C25 6.7(5)
C10 C19 C20 C25 -170.0(3)
C25 C20 C21 C22 .2(5)
C19 C20 C21 C22 178.9(3)
C20 C21 C22 C23 -.9(5)
C21 C22 C23 C24 1.1(5)
C22 C23 C24 C25 -.6(5)
C23 C24 C25 C20 -.1(5)
C21 C20 C25 C24 .3(5)
C19 C20 C25 C24 -178.4(3)
