#------------------------------------------------------------------------------
#$Date: 2017-09-29 08:02:51 +0300 (Fri, 29 Sep 2017) $
#$Revision: 201498 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/74/1547470.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_1547470
loop_
_publ_author_name
'Roy Chowdhury, Additi'
'Mondal, Amita'
'Roy, Biswajit Gopal'
'K, Jagadeesh C. Bose'
'Mukhopadhyay, Sudit'
'Banerjee, Priyabrata'
_publ_section_title
;
 Hydrazine functionalized probes for chromogenic and fluorescent
 ratiometric sensing of pH and F−: experimental and DFT studies
;
_journal_name_full               'Photochem. Photobiol. Sci.'
_journal_paper_doi               10.1039/C7PP00246G
_journal_year                    2017
_chemical_formula_sum            'C13 H6 F5 N3 O3'
_chemical_formula_weight         347.21
_chemical_name_systematic
; 
 ? 
;
_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_block_doi                 10.5517/cc132p3z
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-02 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.612(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.404(2)
_cell_length_b                   13.281(3)
_cell_length_c                   11.867(3)
_cell_measurement_reflns_used    4943
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.27
_cell_measurement_theta_min      2.33
_cell_volume                     1292.6(5)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.0875
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9515
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .16
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0751
_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)+(0.1675P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2086
_refine_ls_wR_factor_ref         0.2322
_reflns_number_gt                1867
_reflns_number_total             2166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7pp00246g2.cif
_cod_data_source_block           sensor1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1292.5(5)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1547470
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
C6 C 0.7091(3) -0.1228(2) 1.0428(2) 0.0149(6) Uani 1 1 d .
C1 C 0.7236(3) -0.2259(2) 1.0252(2) 0.0173(6) Uani 1 1 d .
C5 C 0.6342(3) -0.09539(18) 1.1324(2) 0.0161(6) Uani 1 1 d .
C4 C 0.5807(3) -0.1677(2) 1.2009(2) 0.0189(7) Uani 1 1 d .
C2 C 0.6700(3) -0.2979(2) 1.0921(2) 0.0190(7) Uani 1 1 d .
C3 C 0.5984(3) -0.2688(2) 1.1805(2) 0.0205(7) Uani 1 1 d .
F5 F 0.61033(19) 0.00154(12) 1.15722(14) 0.0243(5) Uani 1 1 d .
F4 F 0.5112(2) -0.13676(13) 1.28626(15) 0.0278(5) Uani 1 1 d .
F1 F 0.79481(19) -0.25678(11) 0.93895(13) 0.0210(5) Uani 1 1 d .
F2 F 0.6876(2) -0.39595(12) 1.06978(15) 0.0277(5) Uani 1 1 d .
F3 F 0.5468(2) -0.33866(12) 1.24727(15) 0.0296(5) Uani 1 1 d .
N1 N 0.7693(3) -0.05804(17) 0.9710(2) 0.0204(6) Uani 1 1 d .
H1 H 0.8112 -0.0823 0.9169 0.024 Uiso 1 1 calc R
N2 N 0.7634(3) 0.04426(16) 0.98466(19) 0.0160(6) Uani 1 1 d .
C7 C 0.8228(3) 0.09873(19) 0.9140(2) 0.0159(6) Uani 1 1 d .
H7 H 0.8659 0.0679 0.8569 0.019 Uiso 1 1 calc R
C10 C 0.8940(3) 0.3682(2) 0.8532(2) 0.0183(7) Uani 1 1 d .
C9 C 0.8924(3) 0.2649(2) 0.8460(2) 0.0157(6) Uani 1 1 d .
H9 H 0.9373 0.2330 0.7905 0.019 Uiso 1 1 calc R
C11 C 0.8254(3) 0.4199(2) 0.9342(2) 0.0198(7) Uani 1 1 d .
H11 H 0.8262 0.4899 0.9366 0.024 Uiso 1 1 calc R
C8 C 0.8232(3) 0.2074(2) 0.9224(2) 0.0153(6) Uani 1 1 d .
C13 C 0.7546(3) 0.2603(2) 1.0059(2) 0.0151(6) Uani 1 1 d .
C12 C 0.7568(3) 0.3651(2) 1.0102(2) 0.0206(7) Uani 1 1 d .
H12 H 0.7117 0.3984 1.0648 0.025 Uiso 1 1 calc R
N3 N 0.9697(3) 0.42544(18) 0.7748(2) 0.0196(6) Uani 1 1 d .
O3 O 0.6848(2) 0.21087(15) 1.08155(16) 0.0193(6) Uani 1 1 d .
H3 H 0.6948 0.1500 1.0737 0.029 Uiso 1 1 calc R
O2 O 0.9639(3) 0.51875(15) 0.7781(2) 0.0303(6) Uani 1 1 d .
O1 O 1.0379(3) 0.37915(16) 0.70897(18) 0.0265(6) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5RA06105A 2015
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C6 C1 117.6(2)
N1 C6 C5 126.4(2)
C1 C6 C5 116.0(2)
F1 C1 C2 118.5(2)
F1 C1 C6 118.5(2)
C2 C1 C6 123.0(3)
F5 C5 C4 116.6(2)
F5 C5 C6 122.0(2)
C4 C5 C6 121.4(2)
F4 C4 C3 120.9(2)
F4 C4 C5 118.6(2)
C3 C4 C5 120.5(3)
F2 C2 C3 120.6(3)
F2 C2 C1 119.7(3)
C3 C2 C1 119.8(3)
F3 C3 C2 120.3(2)
F3 C3 C4 120.4(3)
C2 C3 C4 119.3(3)
N2 N1 C6 121.1(2)
C7 N2 N1 116.8(2)
N2 C7 C8 120.7(2)
C9 C10 C11 122.1(2)
C9 C10 N3 118.8(2)
C11 C10 N3 119.1(2)
C10 C9 C8 120.1(2)
C12 C11 C10 118.9(3)
C9 C8 C13 117.7(2)
C9 C8 C7 119.5(2)
C13 C8 C7 122.8(2)
O3 C13 C12 117.8(2)
O3 C13 C8 121.5(2)
C12 C13 C8 120.7(2)
C11 C12 C13 120.4(2)
O1 N3 O2 123.1(2)
O1 N3 C10 118.4(2)
O2 N3 C10 118.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 N1 1.382(4)
C6 C1 1.395(4)
C6 C5 1.396(4)
C1 F1 1.357(3)
C1 C2 1.380(4)
C5 F5 1.346(3)
C5 C4 1.395(4)
C4 F4 1.340(3)
C4 C3 1.378(4)
C2 F2 1.343(3)
C2 C3 1.374(4)
C3 F3 1.351(3)
N1 N2 1.370(3)
N2 C7 1.288(4)
C7 C8 1.447(4)
C10 C9 1.375(4)
C10 C11 1.403(4)
C10 N3 1.452(3)
C9 C8 1.405(4)
C11 C12 1.380(4)
C8 C13 1.433(3)
C13 O3 1.346(3)
C13 C12 1.394(4)
N3 O1 1.229(3)
N3 O2 1.241(3)
