#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:29:33 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179633 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/97/4509791.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509791
loop_
_publ_author_name
'Zhang, Zuolun'
'Zhang, Yu'
'Yao, Dandan'
'Bi, Hai'
'Javed, Iqbal'
'Fan, Yan'
'Zhang, Hongyu'
'Wang, Yue'
_publ_section_title
;
 Anthracene-Arrangement-Dependent Emissions of Crystals of
 9-Anthrylpyrazole Derivatives
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5069
_journal_paper_doi               10.1021/cg9008569
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C40 H26 N4'
_chemical_formula_weight         562.65
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.00(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8701(18)
_cell_length_b                   10.946(2)
_cell_length_c                   15.512(3)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.19
_cell_volume                     1504.0(5)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 1990)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Omega scan'
_diffrn_measurement_method       10.0
_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  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13911
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;   
Higash,T(1995) Progrom for Absorption Correcttion.
Rigaku Corporation,Tokyo,Japan. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0437
_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)+(0.0500P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                2382
_reflns_number_total             3413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9008569sup1.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4509791
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.10313(15) 0.40919(11) 0.13300(8) 0.0335(3) Uani 1 1 d .
C2 C 0.15663(14) 0.51829(12) 0.09688(8) 0.0338(3) Uani 1 1 d .
C3 C 0.30963(16) 0.53478(13) 0.07479(9) 0.0427(4) Uani 1 1 d .
H3 H 0.3781 0.4711 0.0835 0.051 Uiso 1 1 calc R
C4 C 0.35679(18) 0.64189(14) 0.04126(10) 0.0509(4) Uani 1 1 d .
H4 H 0.4573 0.6506 0.0280 0.061 Uiso 1 1 calc R
C5 C 0.25556(19) 0.74074(14) 0.02613(10) 0.0520(4) Uani 1 1 d .
H5 H 0.2893 0.8133 0.0026 0.062 Uiso 1 1 calc R
C6 C 0.11023(18) 0.72909(13) 0.04606(10) 0.0465(4) Uani 1 1 d .
H6 H 0.0442 0.7940 0.0356 0.056 Uiso 1 1 calc R
C7 C 0.05545(15) 0.61916(12) 0.08290(8) 0.0354(3) Uani 1 1 d .
C8 C -0.09328(16) 0.60824(12) 0.10638(9) 0.0401(3) Uani 1 1 d .
H8 H -0.1590 0.6735 0.0964 0.048 Uiso 1 1 calc R
C9 C -0.14647(15) 0.50283(13) 0.14416(9) 0.0372(3) Uani 1 1 d .
C10 C -0.29814(17) 0.49405(15) 0.16946(11) 0.0507(4) Uani 1 1 d .
H10 H -0.3622 0.5609 0.1618 0.061 Uiso 1 1 calc R
C11 C -0.35064(18) 0.39048(17) 0.20439(12) 0.0602(5) Uani 1 1 d .
H11 H -0.4495 0.3869 0.2215 0.072 Uiso 1 1 calc R
C12 C -0.25561(19) 0.28774(16) 0.21490(12) 0.0577(4) Uani 1 1 d .
H12 H -0.2933 0.2159 0.2374 0.069 Uiso 1 1 calc R
C13 C -0.11012(18) 0.29230(14) 0.19259(10) 0.0479(4) Uani 1 1 d .
H13 H -0.0496 0.2234 0.2004 0.057 Uiso 1 1 calc R
C14 C -0.04765(15) 0.40048(12) 0.15744(8) 0.0351(3) Uani 1 1 d .
C15 C 0.20412(16) 0.30168(12) 0.14491(9) 0.0365(3) Uani 1 1 d .
C16 C 0.25002(18) 0.24131(14) 0.22152(10) 0.0480(4) Uani 1 1 d .
H16 H 0.2241 0.2606 0.2772 0.058 Uiso 1 1 calc R
C17 C 0.34078(18) 0.14830(14) 0.19718(9) 0.0476(4) Uani 1 1 d .
H17 H 0.3893 0.0915 0.2335 0.057 Uiso 1 1 calc R
C18 C 0.42446(15) 0.07602(11) 0.05465(9) 0.0353(3) Uani 1 1 d .
C19 C 0.53488(16) -0.00293(13) 0.08802(9) 0.0418(3) Uani 1 1 d .
H19 H 0.5583 -0.0052 0.1471 0.050 Uiso 1 1 calc R
C20 C 0.38986(16) 0.07836(12) -0.03298(9) 0.0411(3) Uani 1 1 d .
H20 H 0.3154 0.1310 -0.0553 0.049 Uiso 1 1 calc R
N1 N 0.34709(13) 0.15407(10) 0.11050(7) 0.0378(3) Uani 1 1 d .
N2 N 0.26291(13) 0.24872(10) 0.07676(7) 0.0381(3) Uani 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 0.0033 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
C2 C1 C14 120.42(12) . .
C2 C1 C15 120.44(12) . .
C14 C1 C15 119.13(11) . .
C1 C2 C3 123.05(12) . .
C1 C2 C7 119.42(12) . .
C3 C2 C7 117.52(12) . .
C4 C3 C2 121.11(14) . .
C3 C4 C5 121.16(14) . .
C6 C5 C4 119.67(14) . .
C5 C6 C7 121.41(14) . .
C8 C7 C6 121.60(13) . .
C8 C7 C2 119.29(12) . .
C6 C7 C2 119.11(13) . .
C9 C8 C7 121.98(13) . .
C8 C9 C10 121.29(13) . .
C8 C9 C14 119.50(12) . .
C10 C9 C14 119.20(13) . .
C11 C10 C9 121.20(15) . .
C10 C11 C12 119.98(14) . .
C13 C12 C11 120.86(15) . .
C12 C13 C14 121.48(15) . .
C1 C14 C13 123.40(13) . .
C1 C14 C9 119.35(12) . .
C13 C14 C9 117.22(12) . .
N2 C15 C16 111.00(12) . .
N2 C15 C1 120.25(12) . .
C16 C15 C1 128.75(12) . .
C17 C16 C15 105.48(13) . .
N1 C17 C16 107.26(12) . .
C20 C18 C19 119.76(12) . .
C20 C18 N1 120.08(12) . .
C19 C18 N1 120.15(12) . .
C20 C19 C18 119.73(13) 3_655 .
C18 C20 C19 120.51(12) . 3_655
C17 N1 N2 111.52(11) . .
C17 N1 C18 128.79(11) . .
N2 N1 C18 119.68(10) . .
C15 N2 N1 104.74(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.4118(18) .
C1 C14 1.4123(18) .
C1 C15 1.4846(18) .
C2 C3 1.4284(19) .
C2 C7 1.4321(18) .
C3 C4 1.358(2) .
C4 C5 1.418(2) .
C5 C6 1.347(2) .
C6 C7 1.4282(19) .
C7 C8 1.392(2) .
C8 C9 1.3879(19) .
C9 C10 1.424(2) .
C9 C14 1.4308(19) .
C10 C11 1.350(2) .
C11 C12 1.410(2) .
C12 C13 1.354(2) .
C13 C14 1.4276(19) .
C15 N2 1.3353(17) .
C15 C16 1.401(2) .
C16 C17 1.363(2) .
C17 N1 1.3502(18) .
C18 C20 1.378(2) .
C18 C19 1.3859(18) .
C18 N1 1.4190(16) .
C19 C20 1.3841(19) 3_655
C20 C19 1.3841(19) 3_655
N1 N2 1.3652(15) .
