#------------------------------------------------------------------------------
#$Date: 2016-02-04 23:00:40 +0200 (Thu, 04 Feb 2016) $
#$Revision: 175856 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/07/1540717.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_1540717
loop_
_publ_author_name
'Mallick, Suman'
'Chandra, Falguni'
'Koner, Apurba L.'
_publ_section_title
;
 A ratiometric fluorescent probe for detection of biogenic primary amines
 with nanomolar sensitivity.
;
_journal_issue                   3
_journal_name_full               'The Analyst'
_journal_page_first              827
_journal_page_last               831
_journal_paper_doi               10.1039/c5an01911g
_journal_volume                  141
_journal_year                    2016
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.24
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                76.992(3)
_cell_angle_beta                 76.986(3)
_cell_angle_gamma                86.369(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9160(7)
_cell_length_b                   8.3188(8)
_cell_length_c                   10.4144(9)
_cell_measurement_reflns_used    2002
_cell_measurement_temperature    218(2)
_cell_measurement_theta_max      24.987
_cell_measurement_theta_min      2.882
_cell_volume                     568.75(9)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      218(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_laue_measured_fraction_full 0.973
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         2.882
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       Needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0576P)²+0.1522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1582
_reflns_number_total             2002
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5an01911g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1540717.cif.'
_cod_database_code               1540717
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.1781(3) 0.3761(2) 0.94082(17) 0.0437(4) Uani 1 1 d . .
C2 C -0.0053(2) 0.3827(2) 0.78144(17) 0.0424(4) Uani 1 1 d . .
C3 C 0.1649(2) 0.49176(19) 0.71866(16) 0.0373(4) Uani 1 1 d . .
C4 C 0.2784(2) 0.48521(19) 0.81636(16) 0.0389(4) Uani 1 1 d . .
C5 C 0.4516(2) 0.5693(2) 0.78676(16) 0.0413(4) Uani 1 1 d . .
H5 H 0.5259 0.5634 0.8518 0.050 Uiso 1 1 calc R U
C6 C 0.5151(2) 0.66477(19) 0.65569(16) 0.0383(4) Uani 1 1 d . .
C7 C 0.3989(2) 0.67477(18) 0.55585(16) 0.0360(4) Uani 1 1 d . .
C8 C 0.2195(2) 0.58361(19) 0.59098(16) 0.0381(4) Uani 1 1 d . .
H8 H 0.1419 0.5870 0.5281 0.046 Uiso 1 1 calc R U
C9 C 0.4640(2) 0.7709(2) 0.42558(17) 0.0404(4) Uani 1 1 d . .
H9 H 0.3861 0.7783 0.3624 0.049 Uiso 1 1 calc R U
C10 C 0.6420(3) 0.8553(2) 0.38848(17) 0.0422(4) Uani 1 1 d . .
C11 C 0.7564(3) 0.8426(2) 0.48866(18) 0.0477(4) Uani 1 1 d . .
H11 H 0.8761 0.8979 0.4662 0.057 Uiso 1 1 calc R U
C12 C 0.6951(2) 0.7523(2) 0.61521(18) 0.0451(4) Uani 1 1 d . .
H12 H 0.7738 0.7475 0.6776 0.054 Uiso 1 1 calc R U
C13 C 0.8881(3) 1.0423(3) 0.2240(2) 0.0665(6) Uani 1 1 d . .
H13A H 0.9113 1.0953 0.1300 0.100 Uiso 1 1 calc R U
H13B H 0.8715 1.1246 0.2773 0.100 Uiso 1 1 calc R U
H13C H 0.9992 0.9720 0.2408 0.100 Uiso 1 1 calc R U
C14 C 0.5847(4) 0.9726(3) 0.1623(2) 0.0675(6) Uani 1 1 d . .
H14A H 0.6552 1.0367 0.0780 0.101 Uiso 1 1 calc R U
H14B H 0.5496 0.8686 0.1491 0.101 Uiso 1 1 calc R U
H14C H 0.4665 1.0312 0.1951 0.101 Uiso 1 1 calc R U
N1 N 0.7100(2) 0.9444(2) 0.25990(15) 0.0576(4) Uani 1 1 d . .
O1 O 0.00800(18) 0.31712(14) 0.91532(11) 0.0488(3) Uani 1 1 d . .
O2 O 0.2147(2) 0.33406(17) 1.05039(13) 0.0620(4) Uani 1 1 d . .
O3 O -0.13763(19) 0.34488(17) 0.73870(14) 0.0597(4) Uani 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
O2 C1 O1 119.84(15)
O2 C1 C4 132.66(17)
O1 C1 C4 107.49(14)
O3 C2 O1 120.40(15)
O3 C2 C3 132.24(16)
O1 C2 C3 107.36(14)
C8 C3 C4 122.15(15)
C8 C3 C2 130.39(15)
C4 C3 C2 107.44(14)
C5 C4 C3 121.47(15)
C5 C4 C1 130.74(15)
C3 C4 C1 107.78(14)
C4 C5 C6 118.45(15)
C4 C5 H5 120.8
C6 C5 H5 120.8
C5 C6 C12 122.26(15)
C5 C6 C7 120.61(15)
C12 C6 C7 117.12(15)
C9 C7 C8 121.05(15)
C9 C7 C6 119.94(15)
C8 C7 C6 119.01(15)
C3 C8 C7 118.30(15)
C3 C8 H8 120.9
C7 C8 H8 120.9
C10 C9 C7 121.69(16)
C10 C9 H9 119.2
C7 C9 H9 119.2
N1 C10 C9 121.95(17)
N1 C10 C11 120.46(16)
C9 C10 C11 117.57(16)
C12 C11 C10 121.67(16)
C12 C11 H11 119.2
C10 C11 H11 119.2
C11 C12 C6 122.01(16)
C11 C12 H12 119.0
C6 C12 H12 119.0
N1 C13 H13A 109.5
N1 C13 H13B 109.5
H13A C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N1 C14 H14A 109.5
N1 C14 H14B 109.5
H14A C14 H14B 109.5
N1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C10 N1 C13 121.82(17)
C10 N1 C14 120.45(16)
C13 N1 C14 116.45(16)
C2 O1 C1 109.92(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.195(2)
C1 O1 1.403(2)
C1 C4 1.460(2)
C2 O3 1.191(2)
C2 O1 1.400(2)
C2 C3 1.468(2)
C3 C8 1.359(2)
C3 C4 1.408(2)
C4 C5 1.365(2)
C5 C6 1.405(2)
C5 H5 0.9300
C6 C12 1.414(2)
C6 C7 1.436(2)
C7 C9 1.402(2)
C7 C8 1.428(2)
C8 H8 0.9300
C9 C10 1.390(2)
C9 H9 0.9300
C10 N1 1.370(2)
C10 C11 1.427(3)
C11 C12 1.351(2)
C11 H11 0.9300
C12 H12 0.9300
C13 N1 1.450(2)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 N1 1.450(3)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
O3 C2 C3 C8 0.7(3)
O1 C2 C3 C8 179.79(16)
O3 C2 C3 C4 -177.74(19)
O1 C2 C3 C4 1.38(17)
C8 C3 C4 C5 -1.1(2)
C2 C3 C4 C5 177.49(15)
C8 C3 C4 C1 -179.91(15)
C2 C3 C4 C1 -1.34(17)
O2 C1 C4 C5 2.5(3)
O1 C1 C4 C5 -177.85(16)
O2 C1 C4 C3 -178.78(19)
O1 C1 C4 C3 0.83(17)
C3 C4 C5 C6 0.5(2)
C1 C4 C5 C6 179.01(16)
C4 C5 C6 C12 -178.30(15)
C4 C5 C6 C7 0.6(2)
C5 C6 C7 C9 179.86(14)
C12 C6 C7 C9 -1.2(2)
C5 C6 C7 C8 -1.2(2)
C12 C6 C7 C8 177.81(14)
C4 C3 C8 C7 0.5(2)
C2 C3 C8 C7 -177.71(15)
C9 C7 C8 C3 179.54(14)
C6 C7 C8 C3 0.6(2)
C8 C7 C9 C10 -177.56(15)
C6 C7 C9 C10 1.4(2)
C7 C9 C10 N1 177.49(15)
C7 C9 C10 C11 -0.7(2)
N1 C10 C11 C12 -178.34(17)
C9 C10 C11 C12 -0.1(3)
C10 C11 C12 C6 0.3(3)
C5 C6 C12 C11 179.32(16)
C7 C6 C12 C11 0.4(2)
C9 C10 N1 C13 175.31(17)
C11 C10 N1 C13 -6.5(3)
C9 C10 N1 C14 8.7(3)
C11 C10 N1 C14 -173.17(17)
O3 C2 O1 C1 178.38(16)
C3 C2 O1 C1 -0.87(17)
O2 C1 O1 C2 179.72(16)
C4 C1 O1 C2 0.05(17)
