#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/01/8000198.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_8000198
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 H12.8 N4 O1.4'
_chemical_formula_weight         259.48
_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                 108.314(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.761(2)
_cell_length_b                   16.167(5)
_cell_length_c                   9.689(3)
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.66
_cell_measurement_theta_min      2.52
_cell_volume                     1302.8(6)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8496
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.2717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1330
_reflns_number_gt                2014
_reflns_number_total             2543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jz402280w_si_003.cif
_cod_data_source_block           w154
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        1302.9(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C14 H12.80 N4 O1.40'
_cod_database_code               8000198
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
C1 C 0.5657(2) -0.08890(11) 0.2334(2) 0.0465(5) Uani 1 1 d .
C2 C 0.4153(3) -0.12628(14) 0.1961(3) 0.0640(6) Uani 1 1 d .
H2 H 0.3653 -0.1342 0.2667 0.077 Uiso 1 1 calc R
C3 C 0.3394(3) -0.15173(15) 0.0550(3) 0.0745(7) Uani 1 1 d .
H3 H 0.2390 -0.1769 0.0314 0.089 Uiso 1 1 calc R
C4 C 0.4116(3) -0.14000(14) -0.0506(3) 0.0688(7) Uani 1 1 d .
H4 H 0.3598 -0.1571 -0.1454 0.083 Uiso 1 1 calc R
C5 C 0.5608(3) -0.10294(13) -0.0162(2) 0.0587(6) Uani 1 1 d .
H5 H 0.6093 -0.0950 -0.0878 0.070 Uiso 1 1 calc R
C6 C 0.6378(2) -0.07770(11) 0.1247(2) 0.0504(5) Uani 1 1 d .
H6 H 0.7386 -0.0530 0.1476 0.060 Uiso 1 1 calc R
C7 C 0.6505(2) -0.05590(11) 0.3786(2) 0.0450(4) Uani 1 1 d .
C8 C 0.7433(2) -0.04501(12) 0.6218(2) 0.0494(5) Uani 1 1 d .
C9 C 0.8040(2) 0.02113(11) 0.5480(2) 0.0427(4) Uani 1 1 d .
C10 C 0.5671(3) -0.16671(13) 0.5342(3) 0.0668(6) Uani 1 1 d .
H10A H 0.6260 -0.1886 0.6279 0.100 Uiso 1 1 calc R
H10B H 0.5666 -0.2064 0.4603 0.100 Uiso 1 1 calc R
H10C H 0.4586 -0.1553 0.5311 0.100 Uiso 1 1 calc R
C11 C 0.9017(2) 0.08261(11) 0.61658(19) 0.0413(4) Uani 1 1 d .
H11 H 0.9322 0.0827 0.7176 0.050 Uiso 1 1 calc R
C12 C 0.9639(2) 0.14820(10) 0.54977(18) 0.0367(4) Uani 1 1 d .
C13 C 1.0874(2) 0.26148(11) 0.53922(19) 0.0440(4) Uani 1 1 d .
H13 H 1.1448 0.3105 0.5646 0.053 Uiso 1 1 calc R
C14 C 0.9571(2) 0.15979(11) 0.40783(18) 0.0412(4) Uani 1 1 d .
H14 H 0.9082 0.1252 0.3298 0.049 Uiso 1 1 calc R
N1 N 0.6433(2) -0.09040(9) 0.50864(18) 0.0500(4) Uani 1 1 d .
N2 N 0.74147(19) 0.00961(9) 0.39779(17) 0.0456(4) Uani 1 1 d .
N3 N 1.04815(18) 0.21368(9) 0.63210(15) 0.0420(4) Uani 1 1 d .
N4 N 1.03532(18) 0.23146(9) 0.40328(15) 0.0432(4) Uani 1 1 d .
H4A H 1.0582 0.2545 0.3203 0.052 Uiso 1 1 d R
O1 O 0.7722(2) -0.06049(9) 0.75120(16) 0.0671(5) Uani 1 1 d .
O1W O 1.0169(8) 0.0310(4) 0.9741(6) 0.129(2) Uani 0.40 1 d P
H1A H 0.9137 0.0261 0.9170 0.194 Uiso 0.40 1 d PR
H1B H 1.0290 0.0133 1.0655 0.194 Uiso 0.40 1 d PR
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
C2 C1 C6 118.39(19) .
C2 C1 C7 124.04(18) .
C6 C1 C7 117.47(17) .
C3 C2 C1 120.6(2) .
C3 C2 H2 119.7 .
C1 C2 H2 119.7 .
C4 C3 C2 120.3(2) .
C4 C3 H3 119.9 .
C2 C3 H3 119.9 .
C3 C4 C5 120.2(2) .
C3 C4 H4 119.9 .
C5 C4 H4 119.9 .
C4 C5 C6 119.9(2) .
C4 C5 H5 120.0 .
C6 C5 H5 120.0 .
C5 C6 C1 120.6(2) .
C5 C6 H6 119.7 .
C1 C6 H6 119.7 .
N2 C7 N1 113.24(17) .
N2 C7 C1 122.30(17) .
N1 C7 C1 124.46(17) .
O1 C8 N1 125.50(18) .
O1 C8 C9 130.88(19) .
N1 C8 C9 103.61(16) .
C11 C9 N2 126.46(16) .
C11 C9 C8 124.55(17) .
N2 C9 C8 108.99(16) .
N1 C10 H10A 109.5 .
N1 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
N1 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C9 C11 C12 126.61(17) .
C9 C11 H11 116.7 .
C12 C11 H11 116.7 .
C14 C12 N3 108.63(15) .
C14 C12 C11 130.57(16) .
N3 C12 C11 120.80(15) .
N3 C13 N4 112.26(16) .
N3 C13 H13 123.9 .
N4 C13 H13 123.9 .
N4 C14 C12 106.68(15) .
N4 C14 H14 126.7 .
C12 C14 H14 126.7 .
C8 N1 C7 107.89(15) .
C8 N1 C10 121.61(17) .
C7 N1 C10 129.99(18) .
C7 N2 C9 106.20(15) .
C13 N3 C12 105.16(14) .
C13 N4 C14 107.28(14) .
C13 N4 H4A 125.7 .
C14 N4 H4A 126.8 .
O1W O1W H1A 81.4 3_757
O1W O1W H1B 45.1 3_757
H1A O1W H1B 111.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.390(3) .
C1 C6 1.400(3) .
C1 C7 1.469(3) .
C2 C3 1.381(3) .
C2 H2 0.9300 .
C3 C4 1.375(3) .
C3 H3 0.9300 .
C4 C5 1.380(3) .
C4 H4 0.9300 .
C5 C6 1.381(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 N2 1.303(2) .
C7 N1 1.397(2) .
C8 O1 1.224(2) .
C8 N1 1.380(3) .
C8 C9 1.476(3) .
C9 C11 1.343(3) .
C9 N2 1.397(2) .
C10 N1 1.460(2) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C12 1.436(2) .
C11 H11 0.9300 .
C12 C14 1.371(2) .
C12 N3 1.390(2) .
C13 N3 1.312(2) .
C13 N4 1.342(2) .
C13 H13 0.9300 .
C14 N4 1.354(2) .
C14 H14 0.9300 .
N4 H4A 0.9629 .
O1W O1W 1.199(10) 3_757
O1W H1A 0.9029 .
O1W H1B 0.9047 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1A O1 0.90 2.20 2.922(6) 137.0 .
O1W H1B O1 0.90 2.20 2.763(6) 120.1 3_757
