#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:57:15 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180324 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/38/7153827.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_7153827
loop_
_publ_author_name
'Han, Qingxin'
'Shi, Zhaohua'
'Tang, Xiaoliang'
'Yang, Lizi'
'Mou, Zuolin'
'Li, Jing'
'Shi, Jinmin'
'Chen, Chunyang'
'Liu, Wei'
'Yang, Huan'
'Liu, Weisheng'
_publ_section_title
;
 A colorimetric and ratiometric fluorescent probe for distinguishing
 cysteine from biothiols in water and living cells.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5023
_journal_page_last               5030
_journal_paper_doi               10.1039/c4ob00463a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C19 H20 I N O'
_chemical_formula_weight         405.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.3874(8)
_cell_length_b                   6.9055(3)
_cell_length_c                   12.3088(5)
_cell_measurement_reflns_used    5758
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.15
_cell_measurement_theta_min      2.95
_cell_volume                     1732.90(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9013
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.850
_exptl_absorpt_correction_T_max  0.7210
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0311
_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)+(0.1120P)²+0.3267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                1584
_reflns_number_total             1755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00463a2.cif
_cod_data_source_block           pnma
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 

 Adding full bibliography for 7153827.cif.
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               7153827
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
C1 C 0.3707(2) 0.2500 0.2876(4) 0.0435(10) Uani 1 2 d S
C2 C 0.4018(2) 0.2500 0.1890(4) 0.0592(13) Uani 1 2 d S
H2 H 0.3784 0.2500 0.1241 0.071 Uiso 1 2 calc SR
C3 C 0.4694(3) 0.2500 0.1904(5) 0.088(2) Uani 1 2 d S
H3 H 0.4920 0.2500 0.1247 0.106 Uiso 1 2 calc SR
C4 C 0.5042(3) 0.2500 0.2849(5) 0.0783(19) Uani 1 2 d S
H4 H 0.5498 0.2500 0.2824 0.094 Uiso 1 2 calc SR
C5 C 0.4727(2) 0.2500 0.3848(4) 0.0609(15) Uani 1 2 d S
H5 H 0.4966 0.2500 0.4492 0.073 Uiso 1 2 calc SR
C6 C 0.4044(2) 0.2500 0.3862(3) 0.0426(10) Uani 1 2 d S
C7 C 0.35733(18) 0.2500 0.4793(3) 0.0385(9) Uani 1 2 d S
C8 C 0.29234(19) 0.2500 0.4174(3) 0.0353(8) Uani 1 2 d S
C9 C 0.2285(2) 0.2500 0.4638(3) 0.0430(9) Uani 1 2 d S
H9 H 0.1931 0.2500 0.4160 0.052 Uiso 1 2 calc SR
C10 C 0.21474(19) 0.2500 0.5710(3) 0.0423(9) Uani 1 2 d S
H10 H 0.2502 0.2500 0.6185 0.051 Uiso 1 2 calc SR
C11 C 0.1502(3) 0.2500 0.6189(3) 0.0478(11) Uani 1 2 d S
C12 C 0.0921(2) 0.2500 0.5592(4) 0.0731(17) Uani 1 2 d S
H12 H 0.0944 0.2500 0.4838 0.088 Uiso 1 2 calc SR
C13 C 0.0321(3) 0.2500 0.6076(4) 0.082(2) Uani 1 2 d S
H13 H -0.0058 0.2500 0.5655 0.098 Uiso 1 2 calc SR
C14 C 0.0277(2) 0.2500 0.7200(4) 0.0619(14) Uani 1 2 d S
C15 C 0.0845(2) 0.2500 0.7818(4) 0.0518(11) Uani 1 2 d S
H15 H 0.0817 0.2500 0.8572 0.062 Uiso 1 2 calc SR
C16 C 0.1446(2) 0.2500 0.7325(4) 0.0468(10) Uani 1 2 d S
H16 H 0.1824 0.2500 0.7749 0.056 Uiso 1 2 calc SR
C17 C 0.2526(2) 0.2500 0.2286(4) 0.0536(11) Uani 1 2 d S
H17A H 0.2323 0.3754 0.2251 0.080 Uiso 0.50 1 calc PR
H17B H 0.2200 0.1542 0.2452 0.080 Uiso 0.50 1 calc PR
H17C H 0.2724 0.2204 0.1598 0.080 Uiso 0.50 1 calc PR
C18 C 0.36543(15) 0.0635(4) 0.5470(2) 0.0487(7) Uani 1 1 d .
H18A H 0.3553 -0.0469 0.5027 0.073 Uiso 1 1 calc R
H18B H 0.3362 0.0673 0.6081 0.073 Uiso 1 1 calc R
H18C H 0.4098 0.0540 0.5724 0.073 Uiso 1 1 calc R
I1 I 0.326766(16) 0.2500 0.87257(3) 0.0585(3) Uani 1 2 d S
N1 N 0.30300(19) 0.2500 0.3135(3) 0.0397(8) Uani 1 2 d S
O1 O -0.03010(18) 0.2500 0.7736(3) 0.0830(14) Uani 1 2 d S
H1 H -0.0587 0.2951 0.7343 0.125 Uiso 0.50 1 calc 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'
I I -0.4742 1.8119 '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
C2 C1 C6 122.9(4) . .
C2 C1 N1 130.6(4) . .
C6 C1 N1 106.5(4) . .
C1 C2 C3 116.8(5) . .
C1 C2 H2 121.6 . .
C3 C2 H2 121.6 . .
C4 C3 C2 122.1(5) . .
C4 C3 H3 118.9 . .
C2 C3 H3 118.9 . .
C3 C4 C5 121.0(5) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C4 C5 C6 118.3(5) . .
C4 C5 H5 120.9 . .
C6 C5 H5 120.9 . .
C5 C6 C1 118.8(4) . .
C5 C6 C7 130.6(4) . .
C1 C6 C7 110.6(4) . .
C6 C7 C8 100.0(3) . .
C6 C7 C18 110.2(2) . 7_565
C8 C7 C18 111.2(2) . 7_565
C6 C7 C18 110.2(2) . .
C8 C7 C18 111.2(2) . .
C18 C7 C18 113.2(3) 7_565 .
N1 C8 C9 123.3(4) . .
N1 C8 C7 110.3(3) . .
C9 C8 C7 126.4(4) . .
C10 C9 C8 125.7(4) . .
C10 C9 H9 117.2 . .
C8 C9 H9 117.2 . .
C9 C10 C11 126.1(4) . .
C9 C10 H10 116.9 . .
C11 C10 H10 116.9 . .
C12 C11 C16 117.1(4) . .
C12 C11 C10 124.1(4) . .
C16 C11 C10 118.8(4) . .
C13 C12 C11 122.3(4) . .
C13 C12 H12 118.9 . .
C11 C12 H12 118.9 . .
C12 C13 C14 119.7(5) . .
C12 C13 H13 120.2 . .
C14 C13 H13 120.2 . .
O1 C14 C15 117.5(5) . .
O1 C14 C13 123.0(5) . .
C15 C14 C13 119.6(4) . .
C16 C15 C14 120.3(4) . .
C16 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C15 C16 C11 121.0(4) . .
C15 C16 H16 119.5 . .
C11 C16 H16 119.5 . .
N1 C17 H17A 109.5 . .
N1 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N1 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C7 C18 H18A 109.5 . .
C7 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C7 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C8 N1 C1 112.7(3) . .
C8 N1 C17 125.8(4) . .
C1 N1 C17 121.5(4) . .
C14 O1 H1 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.370(6) .
C1 C6 1.394(6) .
C1 N1 1.416(6) .
C2 C3 1.380(8) .
C2 H2 0.9300 .
C3 C4 1.362(9) .
C3 H3 0.9300 .
C4 C5 1.388(7) .
C4 H4 0.9300 .
C5 C6 1.393(7) .
C5 H5 0.9300 .
C6 C7 1.495(5) .
C7 C8 1.528(6) .
C7 C18 1.543(3) 7_565
C7 C18 1.543(3) .
C8 N1 1.297(6) .
C8 C9 1.421(6) .
C9 C10 1.349(6) .
C9 H9 0.9300 .
C10 C11 1.442(6) .
C10 H10 0.9300 .
C11 C12 1.394(6) .
C11 C16 1.403(6) .
C12 C13 1.360(7) .
C12 H12 0.9300 .
C13 C14 1.387(7) .
C13 H13 0.9300 .
C14 O1 1.350(6) .
C14 C15 1.385(7) .
C15 C16 1.369(6) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 N1 1.467(5) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
O1 H1 0.8200 .
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_4
C6 C1 C2 C3 0.0 . .
N1 C1 C2 C3 180.0 . .
C1 C2 C3 C4 0.0 . .
C2 C3 C4 C5 0.0 . .
C3 C4 C5 C6 0.0 . .
C4 C5 C6 C1 0.0 . .
C4 C5 C6 C7 180.0 . .
C2 C1 C6 C5 0.0 . .
N1 C1 C6 C5 180.0 . .
C2 C1 C6 C7 180.0 . .
N1 C1 C6 C7 0.0 . .
C5 C6 C7 C8 180.0 . .
C1 C6 C7 C8 0.0 . .
C5 C6 C7 C18 62.8(2) . 7_565
C1 C6 C7 C18 -117.2(2) . 7_565
C5 C6 C7 C18 -62.8(2) . .
C1 C6 C7 C18 117.2(2) . .
C6 C7 C8 N1 0.0 . .
C18 C7 C8 N1 116.4(2) 7_565 .
C18 C7 C8 N1 -116.4(2) . .
C6 C7 C8 C9 180.0 . .
C18 C7 C8 C9 -63.6(2) 7_565 .
C18 C7 C8 C9 63.6(2) . .
N1 C8 C9 C10 180.0 . .
C7 C8 C9 C10 0.0 . .
C8 C9 C10 C11 180.0 . .
C9 C10 C11 C12 0.0 . .
C9 C10 C11 C16 180.0 . .
C16 C11 C12 C13 0.0 . .
C10 C11 C12 C13 180.0 . .
C11 C12 C13 C14 0.000(1) . .
C12 C13 C14 O1 180.0 . .
C12 C13 C14 C15 0.000(1) . .
O1 C14 C15 C16 180.000(1) . .
C13 C14 C15 C16 0.000(1) . .
C14 C15 C16 C11 0.000(1) . .
C12 C11 C16 C15 0.000(1) . .
C10 C11 C16 C15 180.0 . .
C9 C8 N1 C1 180.0 . .
C7 C8 N1 C1 0.0 . .
C9 C8 N1 C17 0.0 . .
C7 C8 N1 C17 180.0 . .
C2 C1 N1 C8 180.0 . .
C6 C1 N1 C8 0.0 . .
C2 C1 N1 C17 0.0 . .
C6 C1 N1 C17 180.0 . .
