#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:49:05 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179457 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/54/4335419.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_4335419
loop_
_publ_author_name
'Wei-Hua Ding'
'Wei, Cao'
'Xiang-Jun Zheng'
'De-Cai Fang'
'Wing-Tak Wong'
'Lin-Pei Jin'
_publ_section_title
;
 A Highly Selective Fluorescent Chemosensor for AlIII Ion and Fluorescent
 Species Formed in the Solution
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7320
_journal_page_last               7322
_journal_paper_doi               10.1021/ic401028u
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.288(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7918(19)
_cell_length_b                   5.9020(13)
_cell_length_c                   12.126(3)
_cell_measurement_reflns_used    1104
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.85
_cell_volume                     629.2(2)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3225
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.8(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         1249
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0387
_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)+(0.0596P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                1070
_reflns_number_total             1249
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic401028u_si_002.cif
_cod_data_source_block           1
_cod_database_code               4335419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
C1 C 0.0963(3) 1.0348(4) 0.29316(19) 0.0365(6) Uani 1 1 d .
C2 C 0.0542(3) 1.2334(5) 0.3524(2) 0.0406(7) Uani 1 1 d .
H2 H -0.0136 1.3357 0.3207 0.049 Uiso 1 1 calc R
C3 C 0.1109(3) 1.2749(5) 0.4532(2) 0.0397(6) Uani 1 1 d .
H3 H 0.0836 1.4085 0.4886 0.048 Uiso 1 1 calc R
C4 C 0.2113(2) 1.1226(5) 0.50821(19) 0.0342(6) Uani 1 1 d .
C5 C 0.2601(3) 1.1676(5) 0.6163(2) 0.0435(7) Uani 1 1 d .
H5 H 0.2300 1.3003 0.6513 0.052 Uiso 1 1 calc R
C6 C 0.3521(3) 1.0166(5) 0.6705(2) 0.0470(8) Uani 1 1 d .
H6 H 0.3833 1.0462 0.7425 0.056 Uiso 1 1 calc R
C7 C 0.3985(3) 0.8206(5) 0.6185(2) 0.0445(7) Uani 1 1 d .
H7 H 0.4611 0.7189 0.6557 0.053 Uiso 1 1 calc R
C8 C 0.3530(3) 0.7746(5) 0.51241(19) 0.0381(6) Uani 1 1 d .
H8 H 0.3855 0.6421 0.4784 0.046 Uiso 1 1 calc R
C9 C 0.2580(3) 0.9250(4) 0.45465(18) 0.0313(6) Uani 1 1 d .
C10 C 0.2033(3) 0.8833(4) 0.34252(18) 0.0328(6) Uani 1 1 d .
C11 C 0.2554(3) 0.6968(5) 0.28348(18) 0.0340(6) Uani 1 1 d .
H11 H 0.3237 0.5992 0.3179 0.041 Uiso 1 1 calc R
C12 C 0.2622(3) 0.4676(4) 0.1187(2) 0.0345(6) Uani 1 1 d .
C13 C 0.2033(3) 0.4513(5) 0.0118(2) 0.0393(6) Uani 1 1 d .
C14 C 0.2445(3) 0.2659(6) -0.0491(2) 0.0474(7) Uani 1 1 d .
H14 H 0.2065 0.2453 -0.1201 0.057 Uiso 1 1 calc R
C15 C 0.3428(3) 0.1114(6) -0.0036(2) 0.0518(8) Uani 1 1 d .
H15 H 0.3720 -0.0157 -0.0436 0.062 Uiso 1 1 calc R
C16 C 0.3979(3) 0.1446(6) 0.1011(2) 0.0476(7) Uani 1 1 d .
H16 H 0.4656 0.0393 0.1304 0.057 Uiso 1 1 calc R
N1 N 0.2133(2) 0.6512(4) 0.18172(16) 0.0386(5) Uani 1 1 d .
H1 H 0.147(4) 0.770(6) 0.153(2) 0.061(9) Uiso 1 1 d .
N2 N 0.3582(2) 0.3221(4) 0.16256(16) 0.0421(6) Uani 1 1 d .
O1 O 0.0391(2) 0.9955(3) 0.19808(15) 0.0508(6) Uani 1 1 d .
O2 O 0.1108(2) 0.6191(4) -0.02143(16) 0.0573(6) Uani 1 1 d .
H2A H 0.070(4) 0.572(8) -0.080(3) 0.095(14) Uiso 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
O1 C1 C2 120.2(2)
O1 C1 C10 121.4(2)
C2 C1 C10 118.5(2)
C3 C2 C1 120.9(2)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 122.6(3)
C2 C3 H3 118.7
C4 C3 H3 118.7
C9 C4 C5 120.2(2)
C9 C4 C3 119.5(2)
C5 C4 C3 120.3(3)
C6 C5 C4 120.2(3)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C7 120.1(2)
C5 C6 H6 120.0
C7 C6 H6 120.0
C8 C7 C6 120.6(2)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 C9 120.8(3)
C7 C8 H8 119.6
C9 C8 H8 119.6
C4 C9 C8 118.1(2)
C4 C9 C10 118.5(2)
C8 C9 C10 123.4(2)
C11 C10 C1 119.8(2)
C11 C10 C9 120.3(2)
C1 C10 C9 119.9(2)
N1 C11 C10 123.6(2)
N1 C11 H11 118.2
C10 C11 H11 118.2
N2 C12 N1 119.0(2)
N2 C12 C13 124.4(2)
N1 C12 C13 116.6(2)
O2 C13 C14 126.1(2)
O2 C13 C12 116.7(2)
C14 C13 C12 117.2(2)
C13 C14 C15 118.8(2)
C13 C14 H14 120.6
C15 C14 H14 120.6
C14 C15 C16 119.8(3)
C14 C15 H15 120.1
C16 C15 H15 120.1
N2 C16 C15 122.5(3)
N2 C16 H16 118.7
C15 C16 H16 118.7
C11 N1 C12 126.0(2)
C11 N1 H1 110.4(17)
C12 N1 H1 123.5(16)
C12 N2 C16 117.2(2)
C13 O2 H2A 105(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.277(3)
C1 C2 1.425(3)
C1 C10 1.427(3)
C2 C3 1.340(3)
C2 H2 0.9300
C3 C4 1.423(4)
C3 H3 0.9300
C4 C9 1.398(4)
C4 C5 1.403(3)
C5 C6 1.369(4)
C5 H5 0.9300
C6 C7 1.380(4)
C6 H6 0.9300
C7 C8 1.373(3)
C7 H7 0.9300
C8 C9 1.404(3)
C8 H8 0.9300
C9 C10 1.461(3)
C10 C11 1.392(3)
C11 N1 1.314(3)
C11 H11 0.9300
C12 N2 1.314(3)
C12 N1 1.395(3)
C12 C13 1.397(3)
C13 O2 1.342(3)
C13 C14 1.370(4)
C14 C15 1.371(4)
C14 H14 0.9300
C15 C16 1.371(4)
C15 H15 0.9300
C16 N2 1.333(4)
C16 H16 0.9300
N1 H1 0.97(3)
O2 H2A 0.84(4)
