Improved method for the preparation of nonyl acridine orange analogues and utilization in detection of cardiolipin
Dimitrijevs, Pavels; Domracheva, Ilona; Arsenyan, Pavel; New Journal of Chemistry 44 (2020) 9626–9633; doi:10.1039/D0NJ02116D

data_7059635
_publ_section_title
;
 Improved method for the preparation of nonyl acridine orange analogues
 and utilization in detection of cardiolipin
;
_journal_issue                   23
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9626
_journal_page_last               9633
_journal_paper_doi               10.1039/D0NJ02116D
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'I, C23 H34 N3 Si'
_chemical_formula_sum            'C23 H34 I N3 Si'
_chemical_formula_weight         507.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-26
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_audit_update_record
;
2020-01-06 deposited with the CCDC.	2020-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.680(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.4926(7)
_cell_length_b                   9.8565(4)
_cell_length_c                   25.4939(11)
_cell_measurement_reflns_used    13905
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      33.7730
_cell_measurement_theta_min      3.2690
_cell_volume                     4778.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     18.00  80.00   0.50   15.00    --   11.72  19.00 -83.00  124
  2  \w     31.00  60.00   0.50   15.00    --  -12.50  57.00-180.00   58
  3  \w     -9.00  33.00   0.50   15.00    --   11.72  77.00 -30.00   84
  4  \w     46.00  79.00   0.50   15.00    --   11.72 178.00 120.00   66
  5  \w    -64.00   5.00   0.50   15.00    --   11.72 -19.00 109.00  138
  6  \w    -38.00  10.00   0.50   15.00    --  -12.50 -77.00 120.00   96
  7  \w     41.00  84.00   0.50   15.00    --   11.72-178.00  30.00   86
  8  \w    -16.00   9.00   0.50   15.00    --  -12.50 -99.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0322009000
_diffrn_orient_matrix_UB_12      0.0181721000
_diffrn_orient_matrix_UB_13      -0.0175335000
_diffrn_orient_matrix_UB_21      -0.0162489000
_diffrn_orient_matrix_UB_22      0.0040241000
_diffrn_orient_matrix_UB_23      0.0222707000
_diffrn_orient_matrix_UB_31      0.0094013000
_diffrn_orient_matrix_UB_32      0.0694767000
_diffrn_orient_matrix_UB_33      0.0032944000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            27563
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.480
_diffrn_reflns_theta_min         1.640
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.404
_exptl_absorpt_correction_T_max  0.92409
_exptl_absorpt_correction_T_min  0.73780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       Block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.417
_refine_diff_density_min         -1.230
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         7979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+2.5292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.1050
_reflns_d_resolution_high        0.6442
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5892
_reflns_number_total             7979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj02116d2.cif
_cod_data_source_block           pd20
_cod_depositor_comments
;Adding full bibliography for 7059635.cif.

 Adding full bibliography for 7059635.cif.
;
_cod_database_code               7059635
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C184 H264 I8 N24 Si8 '
_chemical_oxdiff_usercomment     'from Pavel'
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.796
_diffrn_oxdiff_digest_frames
;
014074540c2121712a29d93ddea263da60000251cb1
;
_diffrn_oxdiff_digest_hkl
;
01e34d38cd9b497ec7732c4d2844f64a5a10f4
;
_reflns_odcompleteness_completeness 99.6
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.0
_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:
 C22(H22A,H22B), C21(H21A,H21B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C1(H1), C4(H4), C7(H7), C8(H8), C2(H2)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C), C19(H19A,H19B,
 H19C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_title                     ' pd20_a.res in I2/a'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            555.93
_shelx_f_squared_multiplier      1.000