Synthesis and crystal structure of pH-sensitive fluorescent pyrene-based double aza- and diaza[4]helicenes
Tonkoglazova, Daria; Oryabinskaya, Lyubov M.; Shcherbatykh, Aleksandr; Gulevskaya, Anna V.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00204C

data_7158567
_publ_section_title
;
 Synthesis and crystal structure of pH-sensitive fluorescent pyrene-based
 double aza- and diaza[4]helicenes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00204C
_journal_year                    2022
_chemical_formula_moiety         'C28 H15 I N2'
_chemical_formula_sum            'C28 H15 I N2'
_chemical_formula_weight         506.32
_chemical_melting_point          541.5(5)
_chemical_name_systematic        8-Iodo-7-phenylpyreno[1,2-f]quinoxaline
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-28 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.4740(8)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   47.1826(3)
_cell_length_b                   6.90335(5)
_cell_length_c                   24.9480(2)
_cell_measurement_reflns_used    25554
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.4010
_cell_measurement_theta_min      2.3120
_cell_volume                     7902.35(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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    -80.00   9.00   0.50    0.50    --  -47.44  98.00 -13.00  178
  2  \w    -18.00  19.00   0.50    0.50    --   47.44 -98.00-120.00   74
  3  \w     23.00  61.00   0.50    0.50    --   47.44 -98.00-120.00   76
  4  \w   -161.00-107.00   0.50    2.00    -- -106.00 -98.00-120.00  108
  5  \w   -104.00 -53.00   0.50    2.00    -- -106.00  98.00 -13.00  102
  6  \w     69.00 103.00   0.50    2.00    --  113.25 -98.00-120.00   68
  7  \w    -26.00  27.00   0.50    0.50    --  -47.44  19.00 -90.00  106
  8  \w     74.00  99.00   0.50    0.50    --   47.44 125.00-180.00   50
  9  \w    -17.00  24.00   0.50    0.50    --   47.44 -19.00  90.00   82
 10  \w     76.00 119.00   0.50    0.50    --   47.44 125.00 -90.00   86
 11  \w   -173.00 -89.00   0.50    2.00    -- -106.00 -61.00 -90.00  168
 12  \w    -94.00 -55.00   0.50    2.00    -- -106.00  77.00   0.00   78
 13  \w    -71.00 -39.00   0.50    2.00    -- -106.00  61.00  90.00   64
 14  \w   -157.00-131.00   0.50    2.00    -- -106.00 -15.00 120.00   52
 15  \w    -71.00 -33.00   0.50    2.00    -- -106.00  61.00 -30.00   76
 16  \w    -66.00 -33.00   0.50    2.00    -- -106.00  61.00   0.00   66
 17  \w   -119.00 -94.00   0.50    2.00    -- -106.00 -15.00 120.00   50
 18  \w     42.00  67.00   0.50    2.00    --  113.25 -61.00 -90.00   50
 19  \w    134.00 170.00   0.50    2.00    --  113.25  30.00 -90.00   72
 20  \w    106.00 132.00   0.50    2.00    --  113.25  30.00 -90.00   52
 21  \w     43.00  71.00   0.50    2.00    --  113.25 -61.00 120.00   56
 22  \w     75.00 101.00   0.50    2.00    --  113.25 -94.00 -90.00   52
 23  \w    145.00 170.00   0.50    2.00    --  113.25  45.00-120.00   50
 24  \w     48.00  74.00   0.50    2.00    --  113.25 -77.00-120.00   52
 25  \w    109.00 135.00   0.50    2.00    --  113.25  45.00-120.00   52
 26  \w     43.00  68.00   0.50    2.00    --  113.25 -61.00  60.00   50
 27  \w     42.00  68.00   0.50    2.00    --  113.25 -61.00  30.00   52
 28  \w     57.00  84.00   0.50    2.00    --  113.25-125.00  90.00   54
 29  \w    102.00 178.00   0.50    2.00    --  113.25  98.00 -13.00  152
 30  \w     17.00  67.00   0.50    0.50    --   47.44 -98.00-120.00  100
 31  \w     -7.00  21.00   0.50    0.50    --   47.44 -19.00 -90.00   56
 32  \w    -27.00  -2.00   0.50    0.50    --   47.44 -19.00-180.00   50
 33  \w     74.00  99.00   0.50    0.50    --   47.44 125.00 150.00   50
 34  \w    -24.00  17.00   0.50    0.50    --   47.44 -19.00-120.00   82
 35  \w   -177.00-139.00   0.50    2.00    -- -106.00 -61.00 150.00   76
 36  \w   -157.00-131.00   0.50    2.00    -- -106.00 -85.00 -55.68   52
 37  \w   -104.00 -79.00   0.50    2.00    -- -106.00 -85.00 -55.68   50
 38  \w   -109.00 -83.00   0.50    2.00    -- -106.00 -77.00 -54.05   52
 39  \w   -102.00 -63.00   0.50    2.00    -- -106.00  77.00 120.00   78
 40  \w   -126.00-100.00   0.50    2.00    -- -106.00 -45.00-180.00   52
 41  \w   -107.00 -80.00   0.50    2.00    -- -106.00 107.00-155.02   54
 42  \w   -170.00-144.00   0.50    2.00    -- -106.00 -45.00-180.00   52
 43  \w   -115.00-109.50   0.50    2.00    -- -106.00 129.00 -30.70   11
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0011648000
_diffrn_orient_matrix_UB_12      0.0810256000
_diffrn_orient_matrix_UB_13      0.0580126000
_diffrn_orient_matrix_UB_21      -0.0114944000
_diffrn_orient_matrix_UB_22      -0.1943676000
_diffrn_orient_matrix_UB_23      0.0167000000
_diffrn_orient_matrix_UB_31      0.0315233000
_diffrn_orient_matrix_UB_32      -0.0738517000
_diffrn_orient_matrix_UB_33      0.0197064000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            37110
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.989
_diffrn_reflns_theta_min         3.644
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_description       prism
_exptl_crystal_F_000             4000
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.937
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         7488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0218
_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^)+(0.0317P)^2^+10.6833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7110
_reflns_number_total             7488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00204c2.cif
_cod_data_source_block           19381_sp-67a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '541-542' was changed to
'541.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        7902.37(11)
_cod_database_code               7158567
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H15 I N2'
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C1'(H1'),
  C2'(H2'), C10'(H10'), C11'(H11'), C13'(H13'), C14'(H14'), C15'(H15'),
 C17'(H17'), C18'(H18'), C20'(H20'), C24'(H24'), C25'(H25'), C26'(H26'),
 C27'(H27'), C28'(H28')
;
_shelx_res_checksum              4158
_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 1.940
_oxdiff_exptl_absorpt_empirical_full_min 0.607