#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:13:19 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236428 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/66/7236688.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_7236688
loop_
_publ_author_name
'Zhu, Yingzhong'
'Du, Wei'
'Zhang, Mingzhu'
'Xu, Ying'
'Song, Leilei'
'Zhang, Qiong'
'Tian, Xiaohe'
'Zhou, Hongping'
'Wu, Jieying'
'Tian, Yupeng'
_publ_section_title
;
 A series of water-soluble A--π--A′ typological indolium
 derivatives with two-photon properties for rapidly detecting
 HSO3−/SO32−in living cells
;
_journal_issue                   21
_journal_name_full               'Journal of Materials Chemistry B'
_journal_page_first              3862
_journal_paper_doi               10.1039/C7TB00726D
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C18 H19 I N2'
_chemical_formula_weight         390.25
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-12-17 deposited with the CCDC.
2017-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2991(12)
_cell_length_b                   18.472(3)
_cell_length_c                   12.541(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1690.9(5)
_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_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5902
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  0.7037
_exptl_absorpt_correction_T_min  0.6010
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.236
_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   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1509
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0188
_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)+(0.0165P)²+0.6418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0418
_refine_ls_wR_factor_ref         0.0430
_reflns_number_gt                1422
_reflns_number_total             1509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7tb00726d2.cif
_cod_data_source_block           2
_cod_database_code               7236688
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, 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
I1 I 0.0000 0.317152(13) 0.05301(6) 0.05497(10) Uani 1 2 d S
C16 C 0.0000 0.1939(4) 0.4406(8) 0.055(3) Uani 1 2 d S
H16A H 0.1220 0.1748 0.4357 0.082 Uiso 0.50 1 calc PR
H16B H -0.0417 0.2076 0.3708 0.082 Uiso 0.50 1 calc PR
H16C H -0.0803 0.1577 0.4694 0.082 Uiso 0.50 1 calc PR
C8 C 0.0000 0.2569(5) 0.6137(6) 0.0400(16) Uani 1 2 d S
C7 C 0.0000 0.1901(3) 0.6723(8) 0.043(2) Uani 1 2 d S
H7 H 0.0000 0.1473 0.6332 0.052 Uiso 1 2 calc SR
N2 N 0.0000 0.2570(3) 0.5098(4) 0.0386(15) Uani 1 2 d S
C9 C 0.0000 0.3353(4) 0.6551(6) 0.0411(17) Uani 1 2 d S
C6 C 0.0000 0.1846(2) 0.7784(4) 0.0481(10) Uani 1 2 d S
H6 H 0.0000 0.2271 0.8182 0.058 Uiso 1 2 calc SR
C10 C 0.0000 0.37654(17) 0.5524(10) 0.0431(7) Uani 1 2 d S
C3 C 0.0000 0.1156(2) 0.9458(4) 0.0582(12) Uani 1 2 d S
H3 H 0.0000 0.1591 0.9830 0.070 Uiso 1 2 calc SR
C5 C 0.0000 0.1150(2) 0.8366(3) 0.0465(10) Uani 1 2 d S
C13 C 0.0000 0.3508(3) 0.3627(4) 0.0537(11) Uani 1 2 d S
H13 H 0.0000 0.3178 0.3068 0.064 Uiso 1 2 calc SR
C17 C 0.1735(4) 0.35076(17) 0.7207(2) 0.0553(8) Uani 1 1 d .
H17A H 0.1847 0.4020 0.7320 0.083 Uiso 1 1 calc R
H17B H 0.2789 0.3334 0.6827 0.083 Uiso 1 1 calc R
H17C H 0.1651 0.3265 0.7882 0.083 Uiso 1 1 calc R
C12 C 0.0000 0.4498(2) 0.5331(5) 0.0575(18) Uani 1 2 d S
H12 H 0.0000 0.4828 0.5891 0.069 Uiso 1 2 calc SR
C4 C 0.0000 0.0477(3) 0.7870(5) 0.0639(15) Uani 1 2 d S
H4 H 0.0000 0.0440 0.7131 0.077 Uiso 1 2 calc SR
N1 N 0.0000 -0.0137(2) 0.9566(4) 0.0695(11) Uani 1 2 d S
C2 C 0.0000 -0.0143(3) 0.8508(6) 0.0720(17) Uani 1 2 d S
H2 H 0.0000 -0.0591 0.8168 0.086 Uiso 1 2 calc SR
C1 C 0.0000 0.0506(3) 0.9997(5) 0.0716(15) Uani 1 2 d S
H1 H 0.0000 0.0527 1.0738 0.086 Uiso 1 2 calc SR
C15 C 0.0000 0.4238(3) 0.3447(4) 0.0682(14) Uani 1 2 d S
H15 H 0.0000 0.4407 0.2749 0.082 Uiso 1 2 calc SR
C14 C 0.0000 0.4733(3) 0.4279(5) 0.0719(15) Uani 1 2 d S
H14 H 0.0000 0.5226 0.4131 0.086 Uiso 1 2 calc SR
C11 C 0.0000 0.3286(4) 0.4669(7) 0.0413(19) Uani 1 2 d S
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'
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
N2 C16 H16A 109.5 . .
N2 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
N2 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N2 C8 C7 120.8(9) . .
N2 C8 C9 109.7(8) . .
C7 C8 C9 129.5(8) . .
C6 C7 C8 125.1(7) . .
C6 C7 H7 117.5 . .
C8 C7 H7 117.5 . .
C8 N2 C11 112.3(8) . .
C8 N2 C16 126.6(9) . .
C11 N2 C16 121.1(8) . .
C10 C9 C17 111.4(4) . .
C10 C9 C17 111.4(4) . 4
C17 C9 C17 111.0(5) . 4
C10 C9 C8 100.9(6) . .
C17 C9 C8 110.9(4) . .
C17 C9 C8 110.9(4) 4 .
C7 C6 C5 123.9(4) . .
C7 C6 H6 118.0 . .
C5 C6 H6 118.0 . .
C12 C10 C11 119.4(10) . .
C12 C10 C9 130.8(9) . .
C11 C10 C9 109.8(3) . .
C5 C3 C1 118.9(4) . .
C5 C3 H3 120.5 . .
C1 C3 H3 120.5 . .
C3 C5 C4 117.0(4) . .
C3 C5 C6 119.1(4) . .
C4 C5 C6 123.9(4) . .
C15 C13 C11 117.0(5) . .
C15 C13 H13 121.5 . .
C11 C13 H13 121.5 . .
C9 C17 H17A 109.5 . .
C9 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C9 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C10 C12 C14 118.4(7) . .
C10 C12 H12 120.8 . .
C14 C12 H12 120.8 . .
C5 C4 C2 118.6(6) . .
C5 C4 H4 120.7 . .
C2 C4 H4 120.7 . .
C1 N1 C2 115.0(4) . .
N1 C2 C4 124.4(6) . .
N1 C2 H2 117.8 . .
C4 C2 H2 117.8 . .
N1 C1 C3 126.2(5) . .
N1 C1 H1 116.9 . .
C3 C1 H1 116.9 . .
C13 C15 C14 121.7(5) . .
C13 C15 H15 119.1 . .
C14 C15 H15 119.1 . .
C15 C14 C12 120.5(5) . .
C15 C14 H14 119.7 . .
C12 C14 H14 119.7 . .
C13 C11 C10 123.0(7) . .
C13 C11 N2 129.6(7) . .
C10 C11 N2 107.4(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C16 N2 1.454(9) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C8 N2 1.303(5) .
C8 C7 1.437(11) .
C8 C9 1.537(10) .
C7 C6 1.335(12) .
C7 H7 0.9300 .
N2 C11 1.427(8) .
C9 C10 1.497(13) .
C9 C17 1.537(5) .
C9 C17 1.537(5) 4
C6 C5 1.478(6) .
C6 H6 0.9300 .
C10 C12 1.374(5) .
C10 C11 1.391(13) .
C3 C5 1.370(7) .
C3 C1 1.377(6) .
C3 H3 0.9300 .
C5 C4 1.390(6) .
C13 C15 1.367(7) .
C13 C11 1.369(9) .
C13 H13 0.9300 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C12 C14 1.389(9) .
C12 H12 0.9300 .
C4 C2 1.397(7) .
C4 H4 0.9300 .
N1 C1 1.305(6) .
N1 C2 1.327(8) .
C2 H2 0.9300 .
C1 H1 0.9300 .
C15 C14 1.388(8) .
C15 H15 0.9300 .
C14 H14 0.9300 .
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
N2 C8 C7 C6 180.000(2) . .
C9 C8 C7 C6 0.000(2) . .
C7 C8 N2 C11 180.000(2) . .
C9 C8 N2 C11 0.000(2) . .
C7 C8 N2 C16 0.000(3) . .
C9 C8 N2 C16 180.000(2) . .
N2 C8 C9 C10 0.000(3) . .
C7 C8 C9 C10 180.000(3) . .
N2 C8 C9 C17 -118.2(4) . .
C7 C8 C9 C17 61.8(4) . .
N2 C8 C9 C17 118.2(4) . 4
C7 C8 C9 C17 -61.8(4) . 4
C8 C7 C6 C5 180.000(2) . .
C17 C9 C10 C12 -62.3(4) . .
C17 C9 C10 C12 62.3(4) 4 .
C8 C9 C10 C12 180.000(2) . .
C17 C9 C10 C11 117.7(4) . .
C17 C9 C10 C11 -117.7(4) 4 .
C8 C9 C10 C11 0.000(2) . .
C1 C3 C5 C4 0.000(2) . .
C1 C3 C5 C6 180.000(1) . .
C7 C6 C5 C3 180.000(1) . .
C7 C6 C5 C4 0.000(2) . .
C11 C10 C12 C14 0.000(3) . .
C9 C10 C12 C14 180.000(3) . .
C3 C5 C4 C2 0.000(2) . .
C6 C5 C4 C2 180.000(1) . .
C1 N1 C2 C4 0.000(2) . .
C5 C4 C2 N1 0.000(2) . .
C2 N1 C1 C3 0.000(2) . .
C5 C3 C1 N1 0.000(2) . .
C11 C13 C15 C14 0.000(2) . .
C13 C15 C14 C12 0.000(2) . .
C10 C12 C14 C15 0.000(2) . .
C15 C13 C11 C10 0.000(3) . .
C15 C13 C11 N2 180.000(2) . .
C12 C10 C11 C13 0.000(3) . .
C9 C10 C11 C13 180.000(2) . .
C12 C10 C11 N2 180.000(3) . .
C9 C10 C11 N2 0.000(2) . .
C8 N2 C11 C13 180.000(2) . .
C16 N2 C11 C13 0.000(3) . .
C8 N2 C11 C10 0.000(2) . .
C16 N2 C11 C10 180.000(2) . .
