Near-infrared electrochemiluminescence in water through regioselective sulfonation of diaza [4] and [6]helicene dyes.
Li, Haidong; Duwald, Romain; Pascal, Simon; Voci, Silvia; Besnard, Céline; Bosson, Johann; Bouffier, Laurent; Lacour, Jérôme; Sojic, Neso; Chemical communications (Cambridge, England) 56 (2020) 9771–9774; doi:10.1039/d0cc04156d

data_7126958
_publ_section_title
;
 Near-infrared electrochemiluminescence in water through regioselective
 sulfonation of diaza [4] and [6]helicene dyes.
;
_journal_issue                   68
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9771
_journal_page_last               9774
_journal_paper_doi               10.1039/d0cc04156d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '2(C27 H28 N2 O5 S), 5(H2 O)'
_chemical_formula_sum            'C54 H66 N4 O15 S2'
_chemical_formula_weight         1075.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-05-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-09 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                87.576(2)
_cell_angle_beta                 85.907(2)
_cell_angle_gamma                86.452(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1378(3)
_cell_length_b                   10.9386(3)
_cell_length_c                   23.3534(6)
_cell_measurement_reflns_used    17373
_cell_measurement_temperature    180.15
_cell_measurement_theta_max      73.7240
_cell_measurement_theta_min      3.7550
_cell_volume                     2576.31(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004  (Burla et al.,  2007)'
_diffrn_ambient_temperature      180.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.973
_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    -44.00  32.00   1.00    3.00    --  -37.56  37.00  30.00   76
  2  \w    -41.00  42.00   1.00    3.00    --  -37.56  37.00-120.00   83
  3  \w   -111.00  -5.00   1.00    3.00    --  -37.56 -57.00  90.00  106
  4  \w    -36.00  22.00   1.00    3.00    --  -37.56  37.00 -30.00   58
  5  \w     72.00 129.00   1.00    3.00    --   37.56 178.00 120.00   57
  6  \w     71.00 128.00   1.00    3.00    --   37.56-178.00   0.00   57
  7  \w    126.00 158.00   1.00   15.00    --  110.40  61.00  30.00   32
  8  \w     49.00  82.00   1.00   15.00    --  110.40-111.00  90.00   33
  9  \w     25.00  56.00   1.00   15.00    --  110.40 -15.00-150.00   31
 10  \w     53.00 112.00   1.00   15.00    --  110.40-111.00-120.00   59
 11  \w     64.00 115.00   1.00   15.00    --  110.40-111.00  60.00   51
 12  \w     78.00 105.00   1.00   15.00    --  110.40  61.00  30.00   27
 13  \w     59.00  85.00   1.00   15.00    --  110.40 -30.00-150.00   26
 14  \w     32.00  57.00   1.00   15.00    --  110.40 -94.00 -30.00   25
 15  \w     34.00  70.00   1.00   15.00    --  110.40 -30.00 150.00   36
 16  \w     29.00  91.00   1.00   15.00    --  110.40 -30.00  60.00   62
 17  \w     82.00 108.00   1.00   15.00    --  110.40 -94.00 -30.00   26
 18  \w     60.00  91.00   1.00   15.00    --  110.40 -30.00  90.00   31
 19  \w     60.00 173.00   1.00   15.00    --  110.40 -15.00-150.00  113
 20  \w     29.00  90.00   1.00   15.00    --  110.40 -30.00   0.00   61
 21  \w     31.00 120.00   1.00   15.00    --  110.40 -77.00  90.00   89
 22  \w     31.00 143.00   1.00   15.00    --  110.40 -77.00-120.00  112
 23  \w     -7.00  18.00   1.00    3.00    --   36.00  94.00  92.14   25
 24  \w    -43.00  -6.00   1.00    3.00    --  -37.56 -57.00 -90.00   37
 25  \w   -115.00  19.00   1.00    3.00    --  -37.56 -19.00-150.00  134
 26  \w     78.00 127.00   1.00    3.00    --   37.56 171.00-107.00   49
 27  \w      9.00  34.00   1.00    3.00    --   48.00  86.00  98.50   25
 28  \w      9.00  34.00   1.00    3.00    --   48.00  86.00-144.62   25
 29  \w     19.00  44.00   1.00    3.00    --   56.00  82.00 -12.13   25
 30  \w     20.00  45.00   1.00    3.00    --   56.00  79.00 -54.82   25
 31  \w     19.00  44.00   1.00    3.00    --   56.00  80.00 -90.77   25
 32  \w     19.00  44.00   1.00    3.00    --   56.00  82.00 164.90   25
 33  \w     28.00  77.00   1.00    3.00    --   64.00  77.00  14.32   49
 34  \w     34.00  60.00   1.00    3.00    --   68.00  76.00 112.67   26
 35  \w     32.00  58.00   1.00    3.00    --   68.00  77.00-166.99   26
 36  \w     89.00 146.00   1.00    3.00    --   68.00  76.00 -59.88   57
 37  \w     32.00  57.00   1.00    3.00    --   68.00  75.00  42.94   25
 38  \w     32.00  76.00   1.00    3.00    --   68.00  76.00 -59.88   44
 39  \w    121.00 156.00   1.00    3.00    --   72.00  77.00-152.22   35
 40  \w    105.00 131.00   1.00    3.00    --   72.00  77.00-116.65   26
 41  \w     36.00  62.00   1.00    3.00    --   72.00  77.00-152.22   26
 42  \w     36.00  62.00   1.00    3.00    --   72.00  77.00 148.10   26
 43  \w     37.00  74.00   1.00    3.00    --   72.00  77.00  63.59   37
 44  \w     36.00  73.00   1.00    3.00    --   72.00  77.00-116.65   37
 45  \w     74.00 118.00   1.00   15.00    --  110.40  77.00 150.00   44
 46  \w     74.00 141.00   1.00   15.00    --  110.40  77.00-150.00   67
 47  \w     74.00 132.00   1.00   15.00    --  110.40  77.00  90.00   58
 48  \w     74.00 101.00   1.00   15.00    --  110.40  77.00 -60.00   27
 49  \w     74.00 108.00   1.00   15.00    --  110.40  77.00-180.00   34
 50  \w     74.00 115.00   1.00   15.00    --  110.40  77.00  60.00   41
 51  \w     74.00  99.00   1.00   15.00    --  110.40  77.00-120.00   25
 52  \w    117.00 143.00   1.00   15.00    --  110.40  77.00-120.00   26
 53  \w     79.00 149.00   1.00   15.00    --  110.40  61.00 -60.00   70
 54  \w     74.00 119.00   1.00   15.00    --  110.40  77.00 120.00   45
 55  \w     77.00 140.00   1.00   15.00    --  110.40  61.00 -90.00   63
 56  \w     77.00 156.00   1.00   15.00    --  110.40  61.00 -30.00   79
 57  \w     80.00  97.00   1.00   15.00    --  110.40  61.00  90.00   17
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0844783000
_diffrn_orient_matrix_UB_12      -0.1058841000
_diffrn_orient_matrix_UB_13      0.0272851000
_diffrn_orient_matrix_UB_21      -0.0696879000
_diffrn_orient_matrix_UB_22      0.0265753000
_diffrn_orient_matrix_UB_23      0.0593471000
_diffrn_orient_matrix_UB_31      -0.1063076000
_diffrn_orient_matrix_UB_32      -0.0896445000
_diffrn_orient_matrix_UB_33      -0.0106596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            35732
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.677
_diffrn_reflns_theta_min         3.798
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.560
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.063
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     719
_refine_ls_number_reflns         10120
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0664
_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^)+(0.1017P)^2^+3.0085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1860
_refine_ls_wR_factor_ref         0.1976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8233
_reflns_number_total             10120
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9942\% 
 around [0.71 -0.71 -0.00] (reciprocal) or [0.76 -0.65 -0.01] (direct)
;
_cod_data_source_file            d0cc04156d2.cif
_cod_data_source_block           spa015
_cod_depositor_comments          'Adding full bibliography for 7126958.cif.'
_cod_original_cell_volume        2576.32(11)
_cod_database_code               7126958
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C54 H66 N4 O15 S2'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_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, All O(H,H) groups
2. Restrained distances
 S8B-O11B \\sim S8B-O11B \\sim S8B-O9B \\sim S8B-O9B \\sim S8B-O10C \\sim
S8B-O10B
 with sigma of 0.02
 O9C-O11C \\sim O11C-O10C \\sim O10C-O9C
 with sigma of 0.04
 O9B-O10B \\sim O10B-O11B \\sim O11B-O9B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O11C) = Uanis(O11B)
4. Rigid body (RIGU) restrains
 S8B, O10B, O11B, O9B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S8B, O11B, O9B, O10C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O11C)=Sof(O9C)=Sof(O10C)=1-FVAR(1)
 Sof(O10B)=Sof(O11B)=Sof(O9B)=FVAR(1)
 Fixed Sof: OW4B(0.45314) HW4A(0.45314) HW4B(0.45314) OW4A(0.54686)
 HW4C(0.54686) HW4D(0.54686)
6.a Riding coordinates:
 OW1(HW1A,HW1B), OW4B(HW4A,HW4B), OW3(HW3A,HW3B), OW4A(HW4C,HW4D)
6.b Free rotating group:
 OW5(HW5A,HW5B), OW2(HW2A,HW2B)
6.c Secondary CH2 refined with riding coordinates:
 C30(H30C,H30D), C5(H5A,H5B), C7(H7A,H7B), C31(H31C,H31D), C6(H6A,H6B),
 C7B(H7BA,H7BB), C6B(H6BA,H6BB), C31B(H31A,H31B), C5B(H5BA,H5BB), C30B(H30A,
 H30B)
6.d Aromatic/amide H refined with riding coordinates:
 C27(H27), C2(H2), C25(H25), C26(H26), C35(H35), C15(H15), C14(H14), C13(H13),
 C1(H1), C1B(H1B), C26B(H26B), C2B(H2B), C15B(H15B), C13B(H13B), C25B(H25B),
 C27B(H27B), C35B(H35B), C14B(H14B)
6.e Idealised Me refined as rotating group:
 C18(H18D,H18E,H18F), C24(H24D,H24E,H24F), C32(H32D,H32E,H32F), C18B(H18A,H18B,
 H18C), C24B(H24A,H24B,H24C), C32B(H32A,H32B,H32C)
;
_shelx_res_checksum              21082
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.747
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2