#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/44/7204487.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_7204487
loop_
_publ_author_name
'Liang, Yongchao'
'Dvornikov, A. S.'
'Rentzepis, P. M.'
_publ_section_title
;
 New near infrared-sensitive photochromic fluorescing molecules
;
_journal_issue                   2
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              286
_journal_paper_doi               10.1039/b206577k
_journal_volume                  13
_journal_year                    2003
_chemical_formula_sum            'C21 H17 N3 O2'
_chemical_formula_weight         343.38
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                107.4560(10)
_cell_angle_beta                 97.5000(10)
_cell_angle_gamma                114.0340(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9150(5)
_cell_length_b                   10.6693(7)
_cell_length_c                   11.0624(7)
_cell_measurement_temperature    158(2)
_cell_volume                     877.33(9)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      158(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9579
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        '< 1.0'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular_plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0526
_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)+(0.0572P)²+0.4007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1446
_reflns_number_gt                2615
_reflns_number_total             4176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b206577k.txt
_cod_data_source_block           pmr4
_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:

'_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      P-1
_cod_database_code               7204487
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31083(19) 0.88696(17) 0.01758(14) 0.0337(4) Uani 1 1 d . . .
O2 O 0.3291(2) 0.73143(18) 0.11082(16) 0.0438(4) Uani 1 1 d . . .
N1 N 0.2490(2) 1.37003(19) 0.41855(17) 0.0292(4) Uani 1 1 d . . .
N2 N 0.1638(3) 1.2578(2) -0.0229(2) 0.0469(5) Uani 1 1 d . . .
N3 N 0.2899(3) 0.9307(3) -0.2774(2) 0.0542(6) Uani 1 1 d . . .
C1 C 0.2918(3) 1.4365(2) 0.5539(2) 0.0280(5) Uani 1 1 d . . .
C2 C 0.2706(3) 1.5545(2) 0.6344(2) 0.0359(5) Uani 1 1 d . . .
C3 C 0.3261(3) 1.5971(3) 0.7695(3) 0.0425(6) Uani 1 1 d . . .
C4 C 0.3997(3) 1.5263(3) 0.8250(3) 0.0430(6) Uani 1 1 d . . .
C5 C 0.4237(3) 1.4125(3) 0.7473(2) 0.0364(5) Uani 1 1 d . . .
C6 C 0.3687(2) 1.3654(2) 0.6087(2) 0.0278(5) Uani 1 1 d . . .
C7 C 0.3717(2) 1.2531(2) 0.5017(2) 0.0249(4) Uani 1 1 d . . .
C8 C 0.2958(2) 1.2571(2) 0.3860(2) 0.0253(4) Uani 1 1 d . . .
C9 C 0.2767(3) 1.1810(2) 0.2495(2) 0.0263(4) Uani 1 1 d . . .
C10 C 0.2575(2) 1.0434(2) 0.18055(19) 0.0247(4) Uani 1 1 d . . .
C11 C 0.2759(3) 1.0035(2) 0.0473(2) 0.0271(4) Uani 1 1 d . . .
C12 C 0.2949(3) 0.8297(2) 0.1192(2) 0.0314(5) Uani 1 1 d . . .
C13 C 0.2325(2) 0.9134(2) 0.21288(19) 0.0251(4) Uani 1 1 d . . .
C14 C 0.1319(3) 0.8522(2) 0.2824(2) 0.0295(5) Uani 1 1 d . . .
C15 C 0.0974(4) 0.7054(3) 0.2891(3) 0.0432(6) Uani 1 1 d . . .
C16 C 0.0361(3) 0.9219(3) 0.3522(2) 0.0359(5) Uani 1 1 d . . .
C17 C 0.1589(3) 1.4062(3) 0.3255(3) 0.0369(5) Uani 1 1 d . . .
C18 C 0.4602(3) 1.1636(3) 0.5148(2) 0.0336(5) Uani 1 1 d . . .
C19 C 0.2583(3) 1.0552(2) -0.0494(2) 0.0308(5) Uani 1 1 d . . .
C20 C 0.2078(3) 1.1686(3) -0.0344(2) 0.0337(5) Uani 1 1 d . . .
C21 C 0.2778(3) 0.9871(3) -0.1759(2) 0.0385(5) Uani 1 1 d . . .
H2 H 0.221(3) 1.605(3) 0.592(2) 0.044(7) Uiso 1 1 d . . .
H3 H 0.312(3) 1.678(3) 0.826(3) 0.050(7) Uiso 1 1 d . . .
H4 H 0.431(3) 1.559(3) 0.922(3) 0.051(7) Uiso 1 1 d . . .
H5 H 0.476(3) 1.362(3) 0.785(2) 0.045(7) Uiso 1 1 d . . .
H9 H 0.281(3) 1.239(2) 0.198(2) 0.029(6) Uiso 1 1 d . . .
H15A H -0.024(5) 0.634(4) 0.237(3) 0.085(10) Uiso 1 1 d . . .
H15B H 0.116(4) 0.716(3) 0.385(3) 0.075(10) Uiso 1 1 d . . .
H15C H 0.166(3) 0.662(3) 0.249(3) 0.053(8) Uiso 1 1 d . . .
H16A H 0.089(4) 0.966(4) 0.454(3) 0.083(10) Uiso 1 1 d . . .
H16B H -0.076(4) 0.847(3) 0.335(3) 0.050(7) Uiso 1 1 d . . .
H16C H 0.023(3) 0.999(3) 0.322(3) 0.050(7) Uiso 1 1 d . . .
H17A H 0.116(4) 1.473(4) 0.373(3) 0.086(10) Uiso 1 1 d . . .
H17B H 0.223(4) 1.444(3) 0.269(3) 0.071(9) Uiso 1 1 d . . .
H17C H 0.063(4) 1.319(4) 0.264(3) 0.079(10) Uiso 1 1 d . . .
H18A H 0.548(4) 1.213(3) 0.602(3) 0.058(8) Uiso 1 1 d . . .
H18B H 0.381(4) 1.059(3) 0.509(3) 0.060(8) Uiso 1 1 d . . .
H18C H 0.521(4) 1.149(3) 0.445(3) 0.064(8) 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 0.0033 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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 109.81(15) . . ?
C1 N1 C8 108.68(17) . . ?
C1 N1 C17 125.00(18) . . ?
C8 N1 C17 126.21(18) . . ?
N1 C1 C2 130.3(2) . . ?
N1 C1 C6 107.97(17) . . ?
C2 C1 C6 121.7(2) . . ?
C3 C2 C1 117.1(2) . . ?
C2 C3 C4 121.8(2) . . ?
C5 C4 C3 121.5(2) . . ?
C4 C5 C6 118.6(2) . . ?
C5 C6 C1 119.30(19) . . ?
C5 C6 C7 133.3(2) . . ?
C1 C6 C7 107.45(18) . . ?
C8 C7 C6 106.81(17) . . ?
C8 C7 C18 127.56(19) . . ?
C6 C7 C18 125.22(19) . . ?
C7 C8 N1 109.08(17) . . ?
C7 C8 C9 132.23(18) . . ?
N1 C8 C9 118.28(18) . . ?
C10 C9 C8 132.3(2) . . ?
C9 C10 C11 121.12(19) . . ?
C9 C10 C13 134.16(19) . . ?
C11 C10 C13 104.51(16) . . ?
O1 C11 C19 116.97(18) . . ?
O1 C11 C10 110.00(17) . . ?
C19 C11 C10 132.96(19) . . ?
O2 C12 O1 118.07(19) . . ?
O2 C12 C13 135.4(2) . . ?
O1 C12 C13 106.54(16) . . ?
C14 C13 C10 129.63(18) . . ?
C14 C13 C12 122.23(19) . . ?
C10 C13 C12 105.64(17) . . ?
C13 C14 C16 122.2(2) . . ?
C13 C14 C15 123.6(2) . . ?
C16 C14 C15 114.1(2) . . ?
C11 C19 C20 122.36(19) . . ?
C11 C19 C21 119.9(2) . . ?
C20 C19 C21 117.5(2) . . ?
N2 C20 C19 178.7(2) . . ?
N3 C21 C19 178.6(3) . . ?
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
O1 C11 1.359(2) . ?
O1 C12 1.429(3) . ?
O2 C12 1.187(2) . ?
N1 C1 1.373(3) . ?
N1 C8 1.394(2) . ?
N1 C17 1.459(3) . ?
N2 C20 1.149(3) . ?
N3 C21 1.147(3) . ?
C1 C2 1.407(3) . ?
C1 C6 1.416(3) . ?
C2 C3 1.378(4) . ?
C3 C4 1.399(4) . ?
C4 C5 1.375(3) . ?
C5 C6 1.408(3) . ?
C6 C7 1.422(3) . ?
C7 C8 1.388(3) . ?
C7 C18 1.490(3) . ?
C8 C9 1.433(3) . ?
C9 C10 1.362(3) . ?
C10 C11 1.457(3) . ?
C10 C13 1.472(3) . ?
C11 C19 1.361(3) . ?
C12 C13 1.477(3) . ?
C13 C14 1.351(3) . ?
C14 C16 1.491(3) . ?
C14 C15 1.495(3) . ?
C19 C20 1.427(3) . ?
C19 C21 1.440(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -179.9(2) . . . . ?
C17 N1 C1 C2 -3.7(3) . . . . ?
C8 N1 C1 C6 0.5(2) . . . . ?
C17 N1 C1 C6 176.7(2) . . . . ?
N1 C1 C2 C3 179.6(2) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -179.3(2) . . . . ?
N1 C1 C6 C5 -179.55(18) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
N1 C1 C6 C7 0.1(2) . . . . ?
C2 C1 C6 C7 -179.50(18) . . . . ?
C5 C6 C7 C8 178.9(2) . . . . ?
C1 C6 C7 C8 -0.7(2) . . . . ?
C5 C6 C7 C18 -8.0(4) . . . . ?
C1 C6 C7 C18 172.3(2) . . . . ?
C6 C7 C8 N1 1.1(2) . . . . ?
C18 C7 C8 N1 -171.8(2) . . . . ?
C6 C7 C8 C9 173.4(2) . . . . ?
C18 C7 C8 C9 0.6(4) . . . . ?
C1 N1 C8 C7 -1.0(2) . . . . ?
C17 N1 C8 C7 -177.1(2) . . . . ?
C1 N1 C8 C9 -174.60(17) . . . . ?
C17 N1 C8 C9 9.3(3) . . . . ?
C7 C8 C9 C10 32.1(4) . . . . ?
N1 C8 C9 C10 -156.1(2) . . . . ?
C8 C9 C10 C11 -167.2(2) . . . . ?
C8 C9 C10 C13 6.8(4) . . . . ?
C12 O1 C11 C19 -169.68(18) . . . . ?
C12 O1 C11 C10 7.8(2) . . . . ?
C9 C10 C11 O1 158.85(18) . . . . ?
C13 C10 C11 O1 -16.7(2) . . . . ?
C9 C10 C11 C19 -24.2(3) . . . . ?
C13 C10 C11 C19 160.3(2) . . . . ?
C11 O1 C12 O2 -176.62(19) . . . . ?
C11 O1 C12 C13 4.4(2) . . . . ?
C9 C10 C13 C14 41.9(4) . . . . ?
C11 C10 C13 C14 -143.4(2) . . . . ?
C9 C10 C13 C12 -156.1(2) . . . . ?
C11 C10 C13 C12 18.6(2) . . . . ?
O2 C12 C13 C14 -29.6(4) . . . . ?
O1 C12 C13 C14 149.14(19) . . . . ?
O2 C12 C13 C10 166.8(3) . . . . ?
O1 C12 C13 C10 -14.5(2) . . . . ?
C10 C13 C14 C16 -6.2(3) . . . . ?
C12 C13 C14 C16 -165.5(2) . . . . ?
C10 C13 C14 C15 169.7(2) . . . . ?
C12 C13 C14 C15 10.3(3) . . . . ?
O1 C11 C19 C20 174.73(18) . . . . ?
C10 C11 C19 C20 -2.0(4) . . . . ?
O1 C11 C19 C21 -0.4(3) . . . . ?
C10 C11 C19 C21 -177.1(2) . . . . ?
C11 C19 C20 N2 -81(10) . . . . ?
C21 C19 C20 N2 94(10) . . . . ?
C11 C19 C21 N3 82(12) . . . . ?
C20 C19 C21 N3 -94(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21190197
