#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:48:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178445 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/66/4026639.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_4026639
loop_
_publ_author_name
'Wei-Ti Chuang'
'Cheng-Chih Hsieh'
'Chin-Hung Lai'
'Cheng-Hsuan Lai'
'Chun-Wei Shih'
'Kew-Yu Chen'
'Wen-Yi Hung'
'Yu-Hsiang Hsu'
'Pi-Tai Chou'
_publ_section_title
;
 Excited-State Intramolecular Proton Transfer Molecules Bearing o-Hydroxy
 Analogues of Green Fluorescent Protein Chromophore
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8189
_journal_page_last               8202
_journal_paper_doi               10.1021/jo2012384
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C15 H13 N3 O'
_chemical_formula_weight         251.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 98.678(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.454(2)
_cell_length_b                   13.7918(12)
_cell_length_c                   6.6660(6)
_cell_measurement_reflns_used    225
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      14.19
_cell_measurement_theta_min      3.41
_cell_volume                     2495.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1283
_diffrn_reflns_av_sigmaI/netI    0.1311
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6448
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.234
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.2360
_refine_ls_R_factor_gt           0.1095
_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)+(0.1314P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2136
_refine_ls_wR_factor_ref         0.2988
_reflns_number_gt                902
_reflns_number_total             2193
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2012384_si_007.cif
_cod_data_source_block           ic12698
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' 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_database_code               4026639
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.19210(19) 0.6406(3) 0.0884(6) 0.0810(17) Uani 1 1 d .
N1 N 0.1149(3) 0.6340(4) -0.2153(8) 0.083(2) Uani 1 1 d .
H1 H 0.1310 0.6492 -0.0951 0.100 Uiso 1 1 calc R
N2 N 0.2753(3) 0.6052(3) -0.2635(7) 0.0719(18) Uani 1 1 d .
N3 N 0.2751(3) 0.6319(3) 0.0688(7) 0.0713(19) Uani 1 1 d .
C1 C 0.0651(4) 0.6347(5) -0.2672(11) 0.091(3) Uani 1 1 d .
H1A H 0.0418 0.6499 -0.1799 0.109 Uiso 1 1 calc R
C2 C 0.0545(3) 0.6094(5) -0.4678(10) 0.082(2) Uani 1 1 d .
H2 H 0.0225 0.6050 -0.5446 0.098 Uiso 1 1 calc R
C3 C 0.0985(3) 0.5915(4) -0.5396(11) 0.076(2) Uani 1 1 d .
H3 H 0.1021 0.5727 -0.6737 0.092 Uiso 1 1 calc R
C4 C 0.1362(4) 0.6060(4) -0.3797(10) 0.073(2) Uani 1 1 d .
C5 C 0.1872(4) 0.5989(4) -0.3825(10) 0.076(2) Uani 1 1 d .
H5 H 0.1961 0.5848 -0.5118 0.091 Uiso 1 1 calc R
C6 C 0.2265(3) 0.6090(4) -0.2287(10) 0.071(2) Uani 1 1 d .
C7 C 0.2262(4) 0.6278(4) -0.0114(10) 0.078(2) Uani 1 1 d .
C8 C 0.3028(3) 0.6183(4) -0.0886(10) 0.074(2) Uani 1 1 d .
C9 C 0.3564(4) 0.6241(4) -0.0606(9) 0.072(2) Uani 1 1 d .
C10 C 0.3796(3) 0.6792(4) -0.1940(9) 0.069(2) Uani 1 1 d .
H10 H 0.3603 0.7146 -0.2997 0.083 Uiso 1 1 calc R
C11 C 0.4303(3) 0.6830(5) -0.1740(9) 0.073(2) Uani 1 1 d .
H11 H 0.4455 0.7209 -0.2661 0.088 Uiso 1 1 calc R
C12 C 0.4594(3) 0.6321(4) -0.0211(10) 0.081(2) Uani 1 1 d .
H12 H 0.4944 0.6346 -0.0062 0.097 Uiso 1 1 calc R
C13 C 0.4357(4) 0.5775(5) 0.1089(10) 0.090(3) Uani 1 1 d .
H13 H 0.4551 0.5423 0.2144 0.109 Uiso 1 1 calc R
C14 C 0.3857(4) 0.5719(5) 0.0927(10) 0.086(3) Uani 1 1 d .
H14 H 0.3709 0.5330 0.1845 0.103 Uiso 1 1 calc R
C15 C 0.2928(3) 0.6498(4) 0.2829(8) 0.076(2) Uani 1 1 d .
H15A H 0.2683 0.6877 0.3417 0.115 Uiso 1 1 calc R
H15B H 0.3239 0.6860 0.2963 0.115 Uiso 1 1 calc R
H15C H 0.2983 0.5878 0.3546 0.115 Uiso 1 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'
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
C1 N1 C4 109.4(7)
C8 N2 C6 106.7(6)
C7 N3 C8 108.3(6)
C7 N3 C15 123.6(5)
C8 N3 C15 128.2(7)
N1 C1 C2 107.7(8)
C1 C2 C3 108.3(8)
C4 C3 C2 107.4(7)
N1 C4 C3 107.2(8)
N1 C4 C5 125.1(8)
C3 C4 C5 127.6(7)
C6 C5 C4 130.7(6)
C5 C6 N2 122.4(6)
C5 C6 C7 128.9(8)
N2 C6 C7 108.6(8)
O1 C7 N3 124.0(6)
O1 C7 C6 132.1(9)
N3 C7 C6 103.9(7)
N2 C8 N3 112.5(7)
N2 C8 C9 124.0(6)
N3 C8 C9 123.4(7)
C10 C9 C14 118.6(8)
C10 C9 C8 119.8(7)
C14 C9 C8 121.5(7)
C11 C10 C9 120.6(7)
C10 C11 C12 120.8(7)
C13 C12 C11 117.5(8)
C14 C13 C12 123.1(8)
C13 C14 C9 119.3(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.240(8)
N1 C1 1.360(9)
N1 C4 1.373(8)
N2 C8 1.302(8)
N2 C6 1.393(9)
N3 C7 1.370(9)
N3 C8 1.398(8)
N3 C15 1.458(7)
C1 C2 1.370(9)
C2 C3 1.388(9)
C3 C4 1.384(9)
C4 C5 1.407(10)
C5 C6 1.379(9)
C6 C7 1.473(9)
C8 C9 1.459(10)
C9 C10 1.394(9)
C9 C14 1.400(10)
C10 C11 1.380(9)
C11 C12 1.387(9)
C12 C13 1.383(10)
C13 C14 1.362(10)
