#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/64/1506409.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_1506409
loop_
_publ_author_name
'Otsuki, Joe'
'Suwa, Kazuya'
'Narutaki, Koichi'
'Sinha, Chittaranjan'
'Yoshikawa, Isao'
'Araki, Koji'
_publ_section_title
;
 Photochromism of 2-(phenylazo)imidazoles.
;
_journal_issue                   35
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              8064
_journal_page_last               8069
_journal_paper_doi               10.1021/jp0531917
_journal_volume                  109
_journal_year                    2005
_chemical_formula_moiety         'C10 H10 N4'
_chemical_formula_sum            'C10 H10 N4'
_chemical_formula_weight         186.22
_chemical_name_systematic
; 
1-N-methyl-2-(phenylazo)imidazole
;
_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                 114.56(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6700(10)
_cell_length_b                   11.506(2)
_cell_length_c                   12.975(2)
_cell_measurement_reflns_used    7914
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.22
_cell_measurement_theta_min      5.37
_cell_volume                     905.7(4)
_computing_cell_refinement       Scalepack
_computing_data_collection       'MacScience Xpress'
_computing_data_reduction        'Denzo and Scalepack'
_computing_molecular_graphics    maXus
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.907
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'MacScience DIP-Labo'
_diffrn_measurement_method       IP
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7914
_diffrn_reflns_theta_full        73.22
_diffrn_reflns_theta_max         73.22
_diffrn_reflns_theta_min         5.37
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.9202
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0598
_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)+(0.1306P)²+0.4746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1828
_refine_ls_wR_factor_ref         0.1990
_reflns_number_gt                1510
_reflns_number_total             1654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp0531917si20050717_114203.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_cell_volume        905.7(3)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1506409
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
N1 N 0.1151(3) 0.90156(15) 0.12146(15) 0.0242(5) Uani 1 1 d .
N2 N 0.1053(3) 0.82583(15) 0.04922(14) 0.0232(5) Uani 1 1 d .
C3 C 0.2982(3) 0.97813(17) 0.15060(17) 0.0217(5) Uani 1 1 d .
C4 C 0.2949(4) 1.07565(18) 0.21387(18) 0.0245(5) Uani 1 1 d .
H1 H 0.1749 1.0876 0.2341 0.029 Uiso 1 1 calc R
C15 C -0.0670(3) 0.74743(17) 0.02326(17) 0.0218(5) Uani 1 1 d .
C6 C 0.4765(4) 0.95938(17) 0.12299(17) 0.0239(5) Uani 1 1 d .
H2 H 0.4799 0.8928 0.0805 0.029 Uiso 1 1 calc R
N3 N -0.0975(3) 0.66664(14) -0.05917(14) 0.0228(5) Uani 1 1 d .
C8 C -0.2719(3) 0.60027(18) -0.06730(18) 0.0258(5) Uani 1 1 d .
H3 H -0.3345 0.5370 -0.1175 0.031 Uiso 1 1 calc R
N4 N -0.2114(3) 0.73472(15) 0.06876(15) 0.0254(5) Uani 1 1 d .
C10 C 0.6431(4) 1.13647(19) 0.21960(18) 0.0277(5) Uani 1 1 d .
H4 H 0.7611 1.1907 0.2427 0.033 Uiso 1 1 calc R
C11 C 0.4669(4) 1.15513(18) 0.24729(18) 0.0269(5) Uani 1 1 d .
H5 H 0.4635 1.2223 0.2892 0.032 Uiso 1 1 calc R
C12 C 0.6484(4) 1.03830(19) 0.15779(18) 0.0265(5) Uani 1 1 d .
H6 H 0.7706 1.0256 0.1395 0.032 Uiso 1 1 calc R
C13 C 0.0265(4) 0.65580(19) -0.12910(18) 0.0272(5) Uani 1 1 d .
H7 H 0.0735 0.5750 -0.1282 0.041 Uiso 1 1 calc R
H8 H 0.1564 0.7063 -0.0988 0.041 Uiso 1 1 calc R
H9 H -0.0675 0.6789 -0.2071 0.041 Uiso 1 1 calc R
C14 C -0.3387(4) 0.64293(18) 0.01141(18) 0.0271(5) Uani 1 1 d .
H10 H -0.4584 0.6127 0.0246 0.033 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
N1 0.0255(10) 0.0237(9) 0.0240(9) -0.0014(7) 0.0112(8) -0.0007(7)
N2 0.0252(10) 0.0238(9) 0.0201(9) 0.0000(6) 0.0089(7) -0.0007(7)
C3 0.0232(11) 0.0221(10) 0.0200(10) 0.0017(7) 0.0091(8) -0.0009(7)
C4 0.0239(11) 0.0244(10) 0.0260(11) 0.0010(8) 0.0113(9) 0.0018(8)
C15 0.0235(11) 0.0236(10) 0.0185(10) -0.0003(7) 0.0090(8) -0.0013(8)
C6 0.0285(11) 0.0247(10) 0.0202(11) -0.0004(7) 0.0119(9) 0.0000(8)
N3 0.0252(9) 0.0226(9) 0.0221(9) -0.0005(6) 0.0112(8) -0.0012(7)
C8 0.0264(11) 0.0246(10) 0.0251(11) 0.0003(8) 0.0094(9) -0.0031(8)
N4 0.0250(10) 0.0273(9) 0.0256(10) -0.0019(7) 0.0121(8) -0.0026(7)
C10 0.0300(12) 0.0285(11) 0.0246(11) 0.0027(8) 0.0113(9) -0.0057(9)
C11 0.0335(12) 0.0224(10) 0.0232(11) -0.0006(7) 0.0102(9) -0.0014(8)
C12 0.0260(11) 0.0329(11) 0.0226(11) 0.0021(8) 0.0121(9) -0.0022(8)
C13 0.0287(12) 0.0291(11) 0.0273(12) -0.0032(8) 0.0153(10) -0.0011(8)
C14 0.0265(11) 0.0294(11) 0.0266(11) 0.0003(8) 0.0122(9) -0.0062(8)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 C3 113.47(18)
N1 N2 C15 114.28(18)
C6 C3 C4 119.96(19)
C6 C3 N1 124.43(18)
C4 C3 N1 115.58(18)
C11 C4 C3 120.0(2)
N4 C15 N3 111.87(17)
N4 C15 N2 130.01(18)
N3 C15 N2 118.10(18)
C12 C6 C3 119.64(19)
C8 N3 C15 106.71(17)
C8 N3 C13 126.13(18)
C15 N3 C13 127.12(17)
N3 C8 C14 105.97(19)
C15 N4 C14 104.11(17)
C11 C10 C12 120.2(2)
C10 C11 C4 119.9(2)
C6 C12 C10 120.3(2)
C8 C14 N4 111.34(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.261(2)
N1 C3 1.424(3)
N2 C15 1.388(3)
C3 C6 1.394(3)
C3 C4 1.396(3)
C4 C11 1.388(3)
C15 N4 1.331(3)
C15 N3 1.367(3)
C6 C12 1.383(3)
N3 C8 1.358(3)
N3 C13 1.465(3)
C8 C14 1.364(3)
N4 C14 1.365(3)
C10 C11 1.381(3)
C10 C12 1.394(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4402144
