#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/01/8000199.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_8000199
loop_
_publ_author_name
'Fang, Xinxiu'
'Wang, Yan'
'Wang, Dan'
'Zhao, Guiyan'
'Zhang, Wenwen'
'Ren, Aimin'
'Wang, Haiyu'
'Xu, Jingwei'
'Gao, Bing-Rong'
'Yang, Wei'
_publ_section_title
;
 Synthesized Blue Fluorescent Protein Analogue with Tunable Colors from
 Excited-State Intramolecular Proton Transfer through an
 N--H···N Hydrogen Bond
;
_journal_issue                   1
_journal_name_full               'The Journal of Physical Chemistry Letters'
_journal_page_first              92
_journal_paper_doi               10.1021/jz402280w
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C14 H12 N4 O'
_chemical_formula_weight         252.28
_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-97
_cell_angle_alpha                99.619(2)
_cell_angle_beta                 109.189(2)
_cell_angle_gamma                109.599(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5326(11)
_cell_length_b                   9.6002(13)
_cell_length_c                   10.1649(14)
_cell_measurement_reflns_used    1058
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      2.23
_cell_volume                     621.42(15)
_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      190(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX 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  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3355
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0505
_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)+(0.0597P)²+0.1342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1298
_reflns_number_gt                1858
_reflns_number_total             2383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jz402280w_si_002.cif
_cod_data_source_block           w122
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8000199
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
N1 N 0.3326(2) 0.63668(19) 0.66199(18) 0.0485(4) Uani 1 1 d .
H1A H 0.2871 0.6630 0.5828 0.058 Uiso 1 1 calc R
N2 N 0.5359(3) 0.5829(2) 0.83969(18) 0.0518(4) Uani 1 1 d .
N3 N 0.7464(2) 0.80719(19) 0.37741(17) 0.0463(4) Uani 1 1 d .
N4 N 0.4905(2) 0.73305(19) 0.45507(17) 0.0466(4) Uani 1 1 d .
O1 O 0.9969(2) 0.75651(18) 0.54071(17) 0.0622(4) Uani 1 1 d .
C1 C 0.2325(3) 0.5991(3) 0.7484(2) 0.0574(6) Uani 1 1 d .
H1 H 0.1004 0.5961 0.7358 0.069 Uiso 1 1 calc R
C2 C 0.3590(3) 0.5666(3) 0.8567(2) 0.0561(6) Uani 1 1 d .
H2 H 0.3282 0.5365 0.9338 0.067 Uiso 1 1 calc R
C3 C 0.5156(3) 0.6264(2) 0.7197(2) 0.0435(4) Uani 1 1 d .
C4 C 0.6712(3) 0.6641(2) 0.6638(2) 0.0460(5) Uani 1 1 d .
H4A H 0.7938 0.6527 0.7142 0.055 Uiso 1 1 calc R
C5 C 0.6600(3) 0.7139(2) 0.5466(2) 0.0441(5) Uani 1 1 d .
C6 C 0.8270(3) 0.7587(2) 0.4951(2) 0.0466(5) Uani 1 1 d .
C7 C 0.5459(3) 0.7863(2) 0.3589(2) 0.0442(5) Uani 1 1 d .
C8 C 0.8462(3) 0.8426(3) 0.2787(2) 0.0587(6) Uani 1 1 d .
H8A H 0.8920 0.9536 0.2884 0.088 Uiso 1 1 calc R
H8B H 0.7476 0.7810 0.1774 0.088 Uiso 1 1 calc R
H8C H 0.9661 0.8169 0.3039 0.088 Uiso 1 1 calc R
C9 C 0.4102(3) 0.8205(2) 0.2395(2) 0.0443(5) Uani 1 1 d .
C10 C 0.4805(3) 0.9578(3) 0.2063(2) 0.0577(6) Uani 1 1 d .
H10 H 0.6205 1.0317 0.2595 0.069 Uiso 1 1 calc R
C11 C 0.3458(4) 0.9865(3) 0.0957(3) 0.0628(6) Uani 1 1 d .
H11 H 0.3929 1.0810 0.0738 0.075 Uiso 1 1 calc R
C12 C 0.1438(4) 0.8785(3) 0.0170(2) 0.0594(6) Uani 1 1 d .
H12 H 0.0529 0.8982 -0.0602 0.071 Uiso 1 1 calc R
C13 C 0.0725(3) 0.7423(3) 0.0494(2) 0.0583(6) Uani 1 1 d .
H13 H -0.0673 0.6684 -0.0048 0.070 Uiso 1 1 calc R
C14 C 0.2055(3) 0.7140(3) 0.1611(2) 0.0522(5) Uani 1 1 d .
H14 H 0.1563 0.6207 0.1845 0.063 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
C3 N1 C1 107.44(16)
C3 N1 H1A 126.3
C1 N1 H1A 126.3
C3 N2 C2 104.80(16)
C6 N3 C7 107.64(15)
C6 N3 C8 122.89(16)
C7 N3 C8 128.43(16)
C7 N4 C5 105.68(15)
N1 C1 C2 106.05(18)
N1 C1 H1 127.0
C2 C1 H1 127.0
C1 C2 N2 110.73(18)
C1 C2 H2 124.6
N2 C2 H2 124.6
N2 C3 N1 110.97(17)
N2 C3 C4 124.24(17)
N1 C3 C4 124.73(17)
C5 C4 C3 126.10(17)
C5 C4 H4A 116.9
C3 C4 H4A 116.9
C4 C5 N4 125.73(17)
C4 C5 C6 124.99(17)
N4 C5 C6 109.28(15)
O1 C6 N3 125.94(19)
O1 C6 C5 130.72(18)
N3 C6 C5 103.34(15)
N4 C7 N3 114.01(16)
N4 C7 C9 123.44(17)
N3 C7 C9 122.54(17)
N3 C8 H8A 109.5
N3 C8 H8B 109.5
H8A C8 H8B 109.5
N3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C14 119.48(18)
C10 C9 C7 121.81(18)
C14 C9 C7 118.69(17)
C11 C10 C9 119.7(2)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 120.3(2)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 120.46(19)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C14 119.5(2)
C12 C13 H13 120.2
C14 C13 H13 120.2
C13 C14 C9 120.6(2)
C13 C14 H14 119.7
C9 C14 H14 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.354(2)
N1 C1 1.352(3)
N1 H1A 0.8800
N2 C3 1.332(2)
N2 C2 1.360(3)
N3 C6 1.384(2)
N3 C7 1.398(2)
N3 C8 1.458(2)
N4 C7 1.297(2)
N4 C5 1.401(2)
O1 C6 1.219(2)
C1 C2 1.358(3)
C1 H1 0.9500
C2 H2 0.9500
C3 C4 1.432(3)
C4 C5 1.344(3)
C4 H4A 0.9500
C5 C6 1.479(3)
C7 C9 1.473(3)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.389(3)
C9 C14 1.386(3)
C10 C11 1.382(3)
C10 H10 0.9500
C11 C12 1.376(3)
C11 H11 0.9500
C12 C13 1.377(3)
C12 H12 0.9500
C13 C14 1.381(3)
C13 H13 0.9500
C14 H14 0.9500
