Photo-induced metal-free dehydrogenative N-N homo-coupling.
Balakrishna, Bugga; Mossin, Susanne; Kramer, Søren; Chemical communications (Cambridge, England) 58 (2022) 10977–10980; doi:10.1039/d2cc04204e

data_7130634
_publ_section_title
;
 Photo-induced metal-free dehydrogenative N-N homo-coupling.
;
_journal_issue                   78
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10977
_journal_page_last               10980
_journal_paper_doi               10.1039/d2cc04204e
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C24 H20 N2'
_chemical_formula_sum            'C24 H20 N2'
_chemical_formula_weight         336.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-06
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-05-06 deposited with the CCDC.	2022-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   12.66060(10)
_cell_length_b                   35.4705(2)
_cell_length_c                   12.01470(10)
_cell_measurement_reflns_used    35159
_cell_measurement_temperature    229.99(10)
_cell_measurement_theta_max      76.4030
_cell_measurement_theta_min      3.6790
_cell_volume                     5395.54(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      229.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3073
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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   -115.00 -16.00   1.00    1.00    --  -40.81 -38.00-150.00   99
  2  \w    -87.00  -6.00   1.00    1.00    --  -40.81 125.00   0.00   81
  3  \w   -114.00 -13.00   1.00    1.00    --  -40.81 -57.00 -30.00  101
  4  \w    -69.00  32.00   1.00    1.00    --  -40.81  57.00 120.00  101
  5  \w      4.00  30.00   1.00    1.00    --   40.81  89.00 -16.06   26
  6  \w      6.00  82.00   1.00    1.00    --   40.81 -99.00-180.00   76
  7  \w      5.00  31.00   1.00    1.00    --   40.81  87.00 -39.39   26
  8  \w    104.00 178.00   1.00    3.02    --  112.00 111.00 -60.00   74
  9  \w     40.00 141.00   1.00    3.02    --  112.00 -61.00 -90.00  101
 10  \w     36.00 145.00   1.00    3.02    --  112.00 -77.00 150.00  109
 11  \w     36.00 109.00   1.00    3.02    --  112.00-111.00  30.00   73
 12  \w     36.00 109.00   1.00    3.02    --  112.00-111.00-180.00   73
 13  \w    103.00 178.00   1.00    3.02    --  112.00  77.00   0.00   75
 14  \w     85.00 178.00   1.00    3.02    --  112.00  51.00  69.76   93
 15  \w     36.00 109.00   1.00    3.02    --  112.00-111.00  60.00   73
 16  \w     36.00 109.00   1.00    3.02    --  112.00-111.00 150.00   73
 17  \w     36.00 109.00   1.00    3.02    --  112.00-111.00-120.00   73
 18  \w     36.00 109.00   1.00    3.02    --  112.00-111.00 -30.00   73
 19  \w     86.00 178.00   1.00    3.02    --  112.00  45.00 -60.00   92
 20  \w     30.00 106.00   1.00    3.02    --  112.00 -95.00-120.00   76
 21  \w    104.00 178.00   1.00    3.02    --  112.00 111.00   0.00   74
 22  \w     36.00 109.00   1.00    3.02    --  112.00-111.00  90.00   73
 23  \w     30.00 106.00   1.00    3.02    --  112.00 -95.00-150.00   76
 24  \w     40.00 141.00   1.00    3.02    --  112.00 -61.00-150.00  101
 25  \w     30.00 106.00   1.00    3.02    --  112.00 -95.00 120.00   76
 26  \w     87.00 178.00   1.00    3.02    --  112.00  43.00 117.85   91
 27  \w     36.00 109.00   1.00    3.02    --  112.00-111.00 -90.00   73
 28  \w    103.00 178.00   1.00    3.02    --  112.00  77.00  30.00   75
 29  \w    103.00 178.00   1.00    3.02    --  112.00  77.00 -90.00   75
 30  \w     36.00 109.00   1.00    3.02    --  112.00-111.00 120.00   73
 31  \w     84.00 178.00   1.00    3.02    --  112.00  30.00   0.00   94
 32  \w     61.00 146.00   1.00    3.02    --  112.00 178.00-180.00   85
 33  \w   -115.00 -16.00   1.00    1.00    --  -40.81 -38.00  90.00   99
 34  \w    -65.00  33.00   1.00    1.00    --  -40.81  38.00 -60.00   98
 35  \w    -65.00  33.00   1.00    1.00    --  -40.81  38.00  30.00   98
 36  \w      7.00  34.00   1.00    1.00    --   40.81  83.00-131.34   27
 37  \w      4.00  30.00   1.00    1.00    --   40.81  89.00  76.84   26
 38  \w      4.00  30.00   1.00    1.00    --   40.81  89.00 -92.37   26
 39  \w      8.00  42.00   1.00    1.00    --   40.81  80.00 125.87   34
 40  \w     83.00 143.00   1.00    3.02    --  112.00  61.00-150.00   60
 41  \w     83.00 178.00   1.00    3.02    --  112.00  61.00  30.00   95
 42  \w     83.00 178.00   1.00    3.02    --  112.00  61.00 150.00   95
 43  \w     84.00 178.00   1.00    3.02    --  112.00  55.00-115.40   94
 44  \w     84.00 178.00   1.00    3.02    --  112.00  30.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0946432000
_diffrn_orient_matrix_UB_12      -0.0027675000
_diffrn_orient_matrix_UB_13      0.0801043000
_diffrn_orient_matrix_UB_21      -0.0694911000
_diffrn_orient_matrix_UB_22      -0.0212015000
_diffrn_orient_matrix_UB_23      0.0847137000
_diffrn_orient_matrix_UB_31      0.0319472000
_diffrn_orient_matrix_UB_32      -0.0378032000
_diffrn_orient_matrix_UB_33      -0.0533706000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            56056
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.640
_diffrn_reflns_theta_min         3.707
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             2136
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 2394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.8594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5502
_reflns_number_total             5670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04204e2.cif
_cod_data_source_block           exp_1985_bb_598_autored
_cod_depositor_comments
'Adding full bibliography for 7130632--7130634.cif.'
_cod_database_code               7130634
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H24 N2'
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.807
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013)
;
_shelx_res_checksum              41652
_shelx_hkl_checksum              559
_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 1.380
_oxdiff_exptl_absorpt_empirical_full_min 0.699