#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/16/7151624.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_7151624
loop_
_publ_author_name
'Elangovan, Arumugasamy'
'Chiu, Hsing-Hua'
'Yang, Shu-Wen'
'Ho, Tong-Ing'
_publ_section_title
;
 Arylethynylacridines: electrochemiluminescence and photophysical
 properties.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3113
_journal_page_last               3118
_journal_paper_doi               10.1039/b410829a
_journal_volume                  2
_journal_year                    2004
_chemical_formula_sum            'C23 H18 N2'
_chemical_formula_weight         322.39
_chemical_name_common            9-[4-(N,N-Dimethylamino)phenyl]ethynyl-acridine
_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
_cell_angle_alpha                81.7260(10)
_cell_angle_beta                 72.9830(10)
_cell_angle_gamma                71.805(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2870(2)
_cell_length_b                   9.3930(2)
_cell_length_c                   10.7350(3)
_cell_measurement_reflns_used    16227
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     849.25(4)
_computing_cell_refinement       'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_data_collection       'COLLECT (Nonius BV)'
_computing_data_reduction        'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5997
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0175(166)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.023
_refine_ls_goodness_of_fit_obs   1.067
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_restrained_S_obs      1.067
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_obs          0.0483
_refine_ls_shift/esd_max         0.007
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0703P)²+0.1188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1449
_refine_ls_wR_factor_obs         0.1278
_reflns_number_observed          2855
_reflns_number_total             3827
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b410829a.txt
_cod_data_source_block           ic10594
_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:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.1188P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.1188P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        849.25(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151624
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.59394(14) 0.76747(13) 0.43201(12) 0.0558(3) Uani 1 d . .
N2 N 0.2235(2) -0.04113(14) 0.02629(13) 0.0646(4) Uani 1 d . .
C1 C 0.7001(2) 0.66305(15) 0.35291(13) 0.0508(3) Uani 1 d . .
C2 C 0.8624(2) 0.6548(2) 0.3261(2) 0.0668(4) Uani 1 d . .
H2A H 0.8915(2) 0.7205(2) 0.3643(2) 0.080 Uiso 1 calc R .
C3 C 0.9739(2) 0.5535(2) 0.2464(2) 0.0737(5) Uani 1 d . .
H3A H 1.0789(2) 0.5500(2) 0.2305(2) 0.088 Uiso 1 calc R .
C4 C 0.9338(2) 0.4526(2) 0.1865(2) 0.0691(4) Uani 1 d . .
H4A H 1.0122(2) 0.3838(2) 0.1311(2) 0.083 Uiso 1 calc R .
C5 C 0.7813(2) 0.4551(2) 0.20935(15) 0.0583(4) Uani 1 d . .
H5A H 0.7563(2) 0.3878(2) 0.16939(15) 0.070 Uiso 1 calc R .
C6 C 0.65960(15) 0.55923(14) 0.29358(12) 0.0466(3) Uani 1 d . .
C7 C 0.5001(2) 0.56488(13) 0.32277(12) 0.0453(3) Uani 1 d . .
C8 C 0.38803(15) 0.67089(14) 0.40847(12) 0.0463(3) Uani 1 d . .
C9 C 0.2249(2) 0.6826(2) 0.44663(14) 0.0558(4) Uani 1 d . .
H9A H 0.1884(2) 0.6172(2) 0.41502(14) 0.067 Uiso 1 calc R .
C10 C 0.1222(2) 0.7879(2) 0.5284(2) 0.0666(4) Uani 1 d . .
H10A H 0.0160(2) 0.7937(2) 0.5531(2) 0.080 Uiso 1 calc R .
C11 C 0.1752(2) 0.8889(2) 0.5765(2) 0.0703(4) Uani 1 d . .
H11A H 0.1030(2) 0.9615(2) 0.6318(2) 0.084 Uiso 1 calc R .
C12 C 0.3289(2) 0.8818(2) 0.54375(15) 0.0636(4) Uani 1 d . .
H12A H 0.3613(2) 0.9495(2) 0.57656(15) 0.076 Uiso 1 calc R .
C13 C 0.4419(2) 0.77174(15) 0.45939(13) 0.0503(3) Uani 1 d . .
C14 C 0.4526(2) 0.46297(15) 0.26714(13) 0.0508(3) Uani 1 d . .
C15 C 0.4128(2) 0.37623(15) 0.22257(14) 0.0513(3) Uani 1 d . .
C16 C 0.36525(14) 0.26997(14) 0.17219(13) 0.0481(3) Uani 1 d . .
C17 C 0.3622(2) 0.2802(2) 0.04252(14) 0.0538(3) Uani 1 d . .
H17A H 0.3916(2) 0.3578(2) -0.01284(14) 0.065 Uiso 1 calc R .
C18 C 0.3168(2) 0.1784(2) -0.00587(13) 0.0540(3) Uani 1 d . .
H18A H 0.3158(2) 0.1888(2) -0.09311(13) 0.065 Uiso 1 calc R .
C19 C 0.27193(15) 0.05932(14) 0.07372(13) 0.0478(3) Uani 1 d . .
C20 C 0.2765(2) 0.0488(2) 0.20443(14) 0.0544(3) Uani 1 d . .
H20A H 0.2484(2) -0.0293(2) 0.25998(14) 0.065 Uiso 1 calc R .
C21 C 0.3216(2) 0.1516(2) 0.25183(14) 0.0543(3) Uani 1 d . .
H21A H 0.3230(2) 0.1420(2) 0.33894(14) 0.065 Uiso 1 calc R .
C22 C 0.2250(2) -0.0320(2) -0.1091(2) 0.0722(5) Uani 1 d . .
H22A H 0.1879(2) -0.1107(2) -0.1246(2) 0.108 Uiso 1 calc R .
H22B H 0.3303(2) -0.0428(2) -0.1626(2) 0.108 Uiso 1 calc R .
H22C H 0.1579(2) 0.0636(2) -0.1303(2) 0.108 Uiso 1 calc R .
C23 C 0.2039(2) -0.1769(2) 0.1013(2) 0.0783(5) Uani 1 d . .
H23A H 0.1700(2) -0.2333(2) 0.0533(2) 0.117 Uiso 1 calc R .
H23B H 0.1264(2) -0.1521(2) 0.1827(2) 0.117 Uiso 1 calc R .
H23C H 0.3021(2) -0.2360(2) 0.1178(2) 0.117 Uiso 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'
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 N1 C13 117.99(11) . . ?
C19 N2 C22 120.94(13) . . ?
C19 N2 C23 120.85(13) . . ?
C22 N2 C23 116.78(13) . . ?
N1 C1 C2 118.47(13) . . ?
N1 C1 C6 123.54(12) . . ?
C2 C1 C6 117.99(13) . . ?
C3 C2 C1 121.11(14) . . ?
C2 C3 C4 120.87(14) . . ?
C5 C4 C3 120.42(15) . . ?
C4 C5 C6 120.74(14) . . ?
C7 C6 C5 123.18(12) . . ?
C7 C6 C1 117.95(12) . . ?
C5 C6 C1 118.87(12) . . ?
C6 C7 C8 119.11(11) . . ?
C6 C7 C14 120.48(12) . . ?
C8 C7 C14 120.41(12) . . ?
C7 C8 C9 123.29(12) . . ?
C7 C8 C13 118.01(12) . . ?
C9 C8 C13 118.70(12) . . ?
C10 C9 C8 120.73(14) . . ?
C9 C10 C11 120.46(14) . . ?
C12 C11 C10 121.07(14) . . ?
C11 C12 C13 120.60(14) . . ?
N1 C13 C12 118.22(12) . . ?
N1 C13 C8 123.36(12) . . ?
C12 C13 C8 118.42(13) . . ?
C15 C14 C7 178.88(14) . . ?
C14 C15 C16 178.54(14) . . ?
C17 C16 C21 117.57(12) . . ?
C17 C16 C15 121.56(12) . . ?
C21 C16 C15 120.87(12) . . ?
C18 C17 C16 121.62(13) . . ?
C17 C18 C19 121.22(12) . . ?
N2 C19 C18 121.41(12) . . ?
N2 C19 C20 121.66(12) . . ?
C18 C19 C20 116.93(12) . . ?
C21 C20 C19 121.30(13) . . ?
C20 C21 C16 121.35(12) . . ?
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
N1 C1 1.342(2) . ?
N1 C13 1.345(2) . ?
N2 C19 1.374(2) . ?
N2 C22 1.440(2) . ?
N2 C23 1.440(2) . ?
C1 C2 1.428(2) . ?
C1 C6 1.430(2) . ?
C2 C3 1.345(2) . ?
C3 C4 1.409(2) . ?
C4 C5 1.357(2) . ?
C5 C6 1.421(2) . ?
C6 C7 1.407(2) . ?
C7 C8 1.406(2) . ?
C7 C14 1.432(2) . ?
C8 C9 1.421(2) . ?
C8 C13 1.432(2) . ?
C9 C10 1.352(2) . ?
C10 C11 1.411(2) . ?
C11 C12 1.348(2) . ?
C12 C13 1.424(2) . ?
C14 C15 1.197(2) . ?
C15 C16 1.433(2) . ?
C16 C17 1.390(2) . ?
C16 C21 1.391(2) . ?
C17 C18 1.372(2) . ?
C18 C19 1.401(2) . ?
C19 C20 1.404(2) . ?
C20 C21 1.374(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9636276
