#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:46:42 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230258 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/69/7056922.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_7056922
loop_
_publ_author_name
'Prasannan, Dijo'
'Arunkumar, Chellaiah'
_publ_section_title
;
 A “turn-on-and-off” pH sensitive BODIPY fluorescent probe
 for imaging E. coli cells
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3473
_journal_paper_doi               10.1039/C7NJ04313A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_sum            'C17 H16 B F2 N3'
_chemical_formula_weight         311.14
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-01-17 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.339(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2654(11)
_cell_length_b                   10.5756(10)
_cell_length_c                   13.3074(12)
_cell_measurement_reflns_used    3205
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      2.6
_cell_volume                     1547.0(2)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14496
_diffrn_reflns_theta_full        24.80
_diffrn_reflns_theta_max         24.80
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0068(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.5962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                1786
_reflns_number_total             2655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7nj04313a2.cif
_cod_data_source_block           shelxl_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7056921--7056922.cif.'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7056922
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.5199(2) -0.0304(2) 0.8424(2) 0.0605(7) Uani 1 1 d .
H1 H 0.4805 -0.0405 0.8876 0.073 Uiso 1 1 calc R
C2 C 0.4688(2) -0.0561(2) 0.7291(2) 0.0651(7) Uani 1 1 d .
H2 H 0.3907 -0.0866 0.6855 0.078 Uiso 1 1 calc R
C3 C 0.5548(2) -0.0281(2) 0.69278(19) 0.0532(6) Uani 1 1 d .
H3 H 0.5452 -0.0351 0.6196 0.064 Uiso 1 1 calc R
C4 C 0.65968(19) 0.01278(19) 0.78585(17) 0.0429(5) Uani 1 1 d .
C5 C 0.77137(19) 0.05892(18) 0.79517(17) 0.0400(5) Uani 1 1 d .
C6 C 0.85605(19) 0.1107(2) 0.89664(17) 0.0418(5) Uani 1 1 d .
C7 C 0.9727(2) 0.1603(2) 0.92947(19) 0.0512(6) Uani 1 1 d .
H7 H 1.0131 0.1668 0.8849 0.061 Uiso 1 1 calc R
C8 C 1.0166(2) 0.1978(2) 1.0393(2) 0.0634(7) Uani 1 1 d .
H8 H 1.0914 0.2357 1.0825 0.076 Uiso 1 1 calc R
C9 C 0.9285(2) 0.1684(2) 1.0733(2) 0.0626(7) Uani 1 1 d .
H9 H 0.9358 0.1829 1.1450 0.075 Uiso 1 1 calc R
C10 C 0.79575(18) 0.05394(19) 0.69695(16) 0.0403(5) Uani 1 1 d .
C11 C 0.7767(2) -0.0556(2) 0.63331(18) 0.0488(6) Uani 1 1 d .
H11 H 0.7497 -0.1280 0.6551 0.059 Uiso 1 1 calc R
C12 C 0.7964(2) -0.0604(2) 0.53966(18) 0.0515(6) Uani 1 1 d .
H12 H 0.7854 -0.1363 0.5011 0.062 Uiso 1 1 calc R
C13 C 0.83283(18) 0.0476(2) 0.50125(17) 0.0453(5) Uani 1 1 d .
C14 C 0.8516(2) 0.1583(2) 0.56460(18) 0.0490(6) Uani 1 1 d .
H14 H 0.8753 0.2319 0.5414 0.059 Uiso 1 1 calc R
C15 C 0.83568(19) 0.1601(2) 0.66057(17) 0.0455(5) Uani 1 1 d .
H15 H 0.8520 0.2341 0.7024 0.055 Uiso 1 1 calc R
C16 C 0.8307(3) -0.0702(3) 0.3418(2) 0.0754(8) Uani 1 1 d .
H16A H 0.8800 -0.1364 0.3898 0.113 Uiso 1 1 calc R
H16B H 0.8535 -0.0563 0.2823 0.113 Uiso 1 1 calc R
H16C H 0.7466 -0.0942 0.3105 0.113 Uiso 1 1 calc R
C17 C 0.8749(3) 0.1590(3) 0.3607(2) 0.0845(9) Uani 1 1 d .
H17A H 0.8156 0.2225 0.3528 0.127 Uiso 1 1 calc R
H17B H 0.8717 0.1412 0.2887 0.127 Uiso 1 1 calc R
H17C H 0.9546 0.1891 0.4106 0.127 Uiso 1 1 calc R
B1 B 0.7226(3) 0.0528(3) 0.9973(2) 0.0524(7) Uani 1 1 d .
N1 N 0.63475(16) 0.01127(17) 0.87834(14) 0.0472(5) Uani 1 1 d .
N2 N 0.83111(16) 0.11618(17) 0.98945(14) 0.0474(5) Uani 1 1 d .
N3 N 0.84890(18) 0.0449(2) 0.40597(15) 0.0593(6) Uani 1 1 d .
F1 F 0.66569(14) 0.13626(15) 1.03931(13) 0.0822(5) Uani 1 1 d .
F2 F 0.76179(14) -0.05115(14) 1.06791(11) 0.0763(5) 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
N1 C1 C2 110.5(2)
N1 C1 H1 124.8
C2 C1 H1 124.8
C3 C2 C1 107.1(2)
C3 C2 H2 126.4
C1 C2 H2 126.4
C2 C3 C4 107.6(2)
C2 C3 H3 126.2
C4 C3 H3 126.2
N1 C4 C3 107.59(18)
N1 C4 C5 120.84(19)
C3 C4 C5 131.40(19)
C6 C5 C4 119.84(18)
C6 C5 C10 121.13(18)
C4 C5 C10 119.01(19)
C7 C6 C5 131.80(19)
C7 C6 N2 107.60(18)
C5 C6 N2 120.58(18)
C8 C7 C6 107.8(2)
C8 C7 H7 126.1
C6 C7 H7 126.1
C7 C8 C9 106.8(2)
C7 C8 H8 126.6
C9 C8 H8 126.6
N2 C9 C8 111.0(2)
N2 C9 H9 124.5
C8 C9 H9 124.5
C11 C10 C15 116.67(18)
C11 C10 C5 121.78(18)
C15 C10 C5 121.52(18)
C12 C11 C10 122.3(2)
C12 C11 H11 118.9
C10 C11 H11 118.9
C11 C12 C13 120.9(2)
C11 C12 H12 119.5
C13 C12 H12 119.5
N3 C13 C14 121.5(2)
N3 C13 C12 121.4(2)
C14 C13 C12 117.07(18)
C15 C14 C13 121.1(2)
C15 C14 H14 119.4
C13 C14 H14 119.4
C14 C15 C10 121.9(2)
C14 C15 H15 119.1
C10 C15 H15 119.1
N3 C16 H16A 109.5
N3 C16 H16B 109.5
H16A C16 H16B 109.5
N3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
N3 C17 H17A 109.5
N3 C17 H17B 109.5
H17A C17 H17B 109.5
N3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
F2 B1 F1 108.41(19)
F2 B1 N1 110.3(2)
F1 B1 N1 110.5(2)
F2 B1 N2 110.0(2)
F1 B1 N2 110.9(2)
N1 B1 N2 106.80(17)
C1 N1 C4 107.17(19)
C1 N1 B1 127.39(18)
C4 N1 B1 125.43(18)
C9 N2 C6 106.80(18)
C9 N2 B1 127.11(19)
C6 N2 B1 125.29(18)
C13 N3 C17 121.2(2)
C13 N3 C16 121.2(2)
C17 N3 C16 117.43(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.345(3)
C1 C2 1.379(3)
C1 H1 0.9300
C2 C3 1.374(3)
C2 H2 0.9300
C3 C4 1.401(3)
C3 H3 0.9300
C4 N1 1.394(2)
C4 C5 1.407(3)
C5 C6 1.399(3)
C5 C10 1.465(3)
C6 C7 1.399(3)
C6 N2 1.399(2)
C7 C8 1.373(3)
C7 H7 0.9300
C8 C9 1.380(3)
C8 H8 0.9300
C9 N2 1.340(3)
C9 H9 0.9300
C10 C11 1.392(3)
C10 C15 1.394(3)
C11 C12 1.372(3)
C11 H11 0.9300
C12 C13 1.403(3)
C12 H12 0.9300
C13 N3 1.367(3)
C13 C14 1.401(3)
C14 C15 1.375(3)
C14 H14 0.9300
C15 H15 0.9300
C16 N3 1.446(3)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 N3 1.446(3)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
B1 F2 1.386(3)
B1 F1 1.388(3)
B1 N1 1.532(3)
B1 N2 1.534(3)
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
C1 H1 F1 0.93 2.60 3.477(3) 158.6 3_657
C2 H2 N3 0.93 2.67 3.495(3) 147.8 3_656
C12 H12 F1 0.93 2.59 3.471(3) 157.7 2_646
C16 H16B F2 0.96 2.56 3.362(3) 140.9 1_554
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
N1 C1 C2 C3 -0.6(3)
C1 C2 C3 C4 1.0(3)
C2 C3 C4 N1 -1.1(3)
C2 C3 C4 C5 -176.2(2)
N1 C4 C5 C6 -3.7(3)
C3 C4 C5 C6 170.9(2)
N1 C4 C5 C10 177.51(18)
C3 C4 C5 C10 -7.9(3)
C4 C5 C6 C7 178.6(2)
C10 C5 C6 C7 -2.6(4)
C4 C5 C6 N2 0.5(3)
C10 C5 C6 N2 179.28(18)
C5 C6 C7 C8 -179.6(2)
N2 C6 C7 C8 -1.3(3)
C6 C7 C8 C9 1.3(3)
C7 C8 C9 N2 -0.9(3)
C6 C5 C10 C11 132.6(2)
C4 C5 C10 C11 -48.6(3)
C6 C5 C10 C15 -49.4(3)
C4 C5 C10 C15 129.4(2)
C15 C10 C11 C12 0.3(3)
C5 C10 C11 C12 178.4(2)
C10 C11 C12 C13 -2.3(3)
C11 C12 C13 N3 -177.9(2)
C11 C12 C13 C14 1.9(3)
N3 C13 C14 C15 -179.8(2)
C12 C13 C14 C15 0.5(3)
C13 C14 C15 C10 -2.5(3)
C11 C10 C15 C14 2.1(3)
C5 C10 C15 C14 -175.9(2)
C2 C1 N1 C4 -0.1(3)
C2 C1 N1 B1 178.6(2)
C3 C4 N1 C1 0.7(2)
C5 C4 N1 C1 176.4(2)
C3 C4 N1 B1 -178.0(2)
C5 C4 N1 B1 -2.3(3)
F2 B1 N1 C1 71.5(3)
F1 B1 N1 C1 -48.3(3)
N2 B1 N1 C1 -168.9(2)
F2 B1 N1 C4 -110.0(2)
F1 B1 N1 C4 130.2(2)
N2 B1 N1 C4 9.5(3)
C8 C9 N2 C6 0.1(3)
C8 C9 N2 B1 170.2(2)
C7 C6 N2 C9 0.7(2)
C5 C6 N2 C9 179.2(2)
C7 C6 N2 B1 -169.6(2)
C5 C6 N2 B1 8.9(3)
F2 B1 N2 C9 -61.5(3)
F1 B1 N2 C9 58.4(3)
N1 B1 N2 C9 178.8(2)
F2 B1 N2 C6 106.8(2)
F1 B1 N2 C6 -133.3(2)
N1 B1 N2 C6 -12.9(3)
C14 C13 N3 C17 -5.9(3)
C12 C13 N3 C17 173.9(2)
C14 C13 N3 C16 179.3(2)
C12 C13 N3 C16 -1.0(3)
