A new family of 1,4-diaryl-1,3-butadiynes based on the “proton sponge”: synthesis, electronic and chemical properties
Filatova, Ekaterina A.; Tsybulin, Semyon V.; Rybin, Dmitry A.; Ozeryanskii, Valery A.; Gulevskaya, Anna V.; Pozharskii, Alexander F.; Borodkin, Gennady S.; New Journal of Chemistry 46 (2022) 1829–1838; doi:10.1039/D1NJ05350G

data_7061130
_publ_section_title
;
 A new family of 1,4-diaryl-1,3-butadiynes based on the &#x201C;proton
 sponge&#x201D;: synthesis, electronic and chemical properties
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1829
_journal_page_last               1838
_journal_paper_doi               10.1039/D1NJ05350G
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C30 H30 N4'
_chemical_formula_sum            'C30 H30 N4'
_chemical_formula_weight         446.58
_chemical_melting_point          503.1(10)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-08 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.9490(2)
_cell_length_b                   15.4462(2)
_cell_length_c                   19.0718(2)
_cell_measurement_reflns_used    10843
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.3920
_cell_measurement_theta_min      4.6040
_cell_volume                     4698.37(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -109.00 -59.00   0.50    1.90    --  -47.44-150.00   7.00  100
  2  \w     45.00 111.00   0.50    1.90    --   47.44  64.00-176.00  132
  3  \w    -61.00 -33.00   0.50    8.50    -- -106.00  57.00  16.00   56
  4  \w   -158.00 -85.00   0.50    8.50    -- -106.00-123.00 169.00  146
  5  \w   -177.00-125.00   0.50    8.50    -- -106.00 -57.00-124.00  104
  6  \w     47.00  73.00   0.50    8.50    --  113.25 -64.00  46.00   52
  7  \w    -24.00  28.00   0.50    1.90    --  -47.44  19.00   0.00  104
  8  \w     76.00 102.00   0.50    1.90    --   47.44 125.00  30.00   52
  9  \w   -160.00-134.00   0.50    8.50    -- -106.00 -30.00 -30.00   52
 10  \w    -71.00 -46.00   0.50    8.50    -- -106.00  61.00 120.00   50
 11  \w    105.00 178.00   0.50    8.50    --  113.25  45.00 -30.00  146
 12  \w     48.00  84.00   0.50    8.50    --  113.25 -77.00-180.00   72
 13  \w     44.00  69.00   0.50    8.50    --  113.25 -61.00 120.00   50
 14  \w     42.00  67.00   0.50    8.50    --  113.25 -61.00-120.00   50
 15  \w     46.00 111.00   0.50    8.50    --  113.25-125.00  90.00  130
 16  \w     42.00  70.00   0.50    8.50    --  113.25 -61.00  90.00   56
 17  \w     44.00  69.00   0.50    8.50    --  113.25 -61.00   0.00   50
;
_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      -0.0384736000
_diffrn_orient_matrix_UB_12      0.0310306000
_diffrn_orient_matrix_UB_13      0.0697192000
_diffrn_orient_matrix_UB_21      0.0532163000
_diffrn_orient_matrix_UB_22      -0.0668091000
_diffrn_orient_matrix_UB_23      0.0401830000
_diffrn_orient_matrix_UB_31      0.0707617000
_diffrn_orient_matrix_UB_32      0.0672293000
_diffrn_orient_matrix_UB_33      0.0076208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19614
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.989
_diffrn_reflns_theta_min         4.611
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear grayish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   grayish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether/dichloromethane'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.169
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0618P)^2^+3.0741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4010
_reflns_number_total             4446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05350g2.cif
_cod_data_source_block           19381_sp-57
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '229-231 deg.C' was changed
to '503.1(10)' -- it was converted from degrees Celsius (C) to
kelvins (K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7061130.cif.
;
_cod_original_cell_volume        4698.36(10)
_cod_database_code               7061130
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 N4'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              45991
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.765