Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H<sub>2</sub>O and Cell-Imaging Studies.
Adhikary, Saswati; Majumder, Leena; Pakrashy, Sourav; Srinath, Ravuri; Mukherjee, Kaustuv; Mandal, Chitra; Banerji, Biswadip; ACS omega 5 (2020) 14394–14407; doi:10.1021/acsomega.0c00934

data_4517765
_publ_section_title
;
 Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via
 Iodine/H<sub>2</sub>O and Cell-Imaging Studies.
;
_journal_issue                   24
_journal_name_full               'ACS omega'
_journal_page_first              14394
_journal_page_last               14407
_journal_paper_doi               10.1021/acsomega.0c00934
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C23 H20 N2'
_chemical_formula_sum            'C23 H20 N2'
_chemical_formula_weight         324.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.013(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9727(11)
_cell_length_b                   19.869(3)
_cell_length_c                   12.956(2)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    101.0
_cell_measurement_theta_max      72.47
_cell_measurement_theta_min      4.45
_cell_volume                     1794.7(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      101.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12501
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.584
_diffrn_reflns_theta_min         4.450
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1193 before and 0.0685 after correction. The Ratio of minimum to maximum transmission is 0.8092. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0353
_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/[\s^2^(Fo^2^)+(0.0475P)^2^+0.5554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.833
_reflns_number_gt                3248
_reflns_number_total             3254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c00934_si_001.cif
_cod_data_source_block           sa_i_ke_benz100k_0m_a
_cod_depositor_comments
'Adding full bibliography for 4517765--4517766.cif.'
_cod_database_code               4517765
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.909
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              30227
_shelx_hkl_checksum              72393
_olex2_submission_special_instructions 'No special instructions were received'