#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:42:59 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278402 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/06/7130632.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7130632
loop_
_publ_author_name
'Balakrishna, Bugga'
'Mossin, Susanne'
'Kramer, Søren'
_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         'C26 H20 N2'
_chemical_formula_sum            'C26 H20 N2'
_chemical_formula_weight         360.44
_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             2021-10-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-05-06 deposited with the CCDC.	2022-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.488(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.8743(10)
_cell_length_b                   5.4117(2)
_cell_length_c                   16.0179(7)
_cell_measurement_reflns_used    7329
_cell_measurement_temperature    119.97(11)
_cell_measurement_theta_max      29.3760
_cell_measurement_theta_min      4.1030
_cell_volume                     1890.34(14)
_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      119.97(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3073
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  43.00   1.00    3.02    --   10.87 -77.00-120.00   71
  2  ω    -13.00  78.00   1.00    3.02    --   10.87  37.00  90.00   91
  3  ω    -10.00  83.00   1.00    3.02    --   10.87  37.00 -30.00   93
  4  ω    -42.00  14.00   1.00    3.02    --   10.87 -77.00 150.00   56
  5  ω    -13.00  81.00   1.00    3.02    --   10.87  57.00-180.00   94
  6  ω    -58.00  39.00   1.00    3.02    --   10.87 -57.00  30.00   97
  7  ω    -66.00 -40.00   1.00    3.02    --  -11.58 122.00 -88.50   26
  8  ω     17.00  42.00   1.00    3.02    --  -11.58  19.00  30.00   25
  9  ω    -84.00 -56.00   1.00    3.02    --  -11.58 150.00  47.74   28
 10  ω    -50.00  -5.00   1.00    3.02    --  -11.58  19.00  30.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0310484000
_diffrn_orient_matrix_UB_12      -0.0236667000
_diffrn_orient_matrix_UB_13      -0.0137843000
_diffrn_orient_matrix_UB_21      0.0076215000
_diffrn_orient_matrix_UB_22      0.0045813000
_diffrn_orient_matrix_UB_23      -0.0421931000
_diffrn_orient_matrix_UB_31      0.0059766000
_diffrn_orient_matrix_UB_32      -0.1288770000
_diffrn_orient_matrix_UB_33      0.0010368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13668
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         3.278
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0446
_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/[σ²(Fo²)+(0.0421P)²+1.9589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1609
_reflns_number_total             1807
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc04204e2.cif
_cod_data_source_block           bb-296
_cod_depositor_comments
'Adding full bibliography for 7130632--7130634.cif.'
_cod_database_code               7130632
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H20 N2'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C006(H006), C007(H007), C008(H008), C009(H009), C00A(H00A),
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.269
_oxdiff_exptl_absorpt_empirical_full_min 0.610
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.52780(5) 0.1873(2) 0.77441(7) 0.0194(3) Uani 1 1 d . . . . .
C002 C 0.57421(6) 0.2784(2) 0.74034(9) 0.0185(3) Uani 1 1 d . . . . .
C003 C 0.57167(6) 0.4116(3) 0.65850(9) 0.0193(3) Uani 1 1 d . . . . .
C004 C 0.63485(6) 0.2574(3) 0.78884(9) 0.0193(3) Uani 1 1 d . . . . .
C005 C 0.67911(7) 0.4388(3) 0.78130(9) 0.0230(3) Uani 1 1 d . . . . .
H005 H 0.671131 0.571244 0.743087 0.028 Uiso 1 1 calc R U . . .
C006 C 0.53647(7) 0.6242(3) 0.64534(9) 0.0242(4) Uani 1 1 d . . . . .
H006 H 0.512301 0.681737 0.688112 0.029 Uiso 1 1 calc R U . . .
C007 C 0.64778(7) 0.0617(3) 0.84435(9) 0.0235(3) Uani 1 1 d . . . . .
H007 H 0.618275 -0.065012 0.849683 0.028 Uiso 1 1 calc R U . . .
C008 C 0.60690(7) 0.3301(3) 0.59496(9) 0.0246(4) Uani 1 1 d . . . . .
H008 H 0.631947 0.187435 0.603331 0.030 Uiso 1 1 calc R U . . .
C009 C 0.73494(7) 0.4283(3) 0.82908(10) 0.0268(4) Uani 1 1 d . . . . .
H009 H 0.764782 0.553609 0.823623 0.032 Uiso 1 1 calc R U . . .
C00A C 0.57018(7) 0.6679(3) 0.50741(9) 0.0281(4) Uani 1 1 d . . . . .
H00A H 0.569328 0.754213 0.455685 0.034 Uiso 1 1 calc R U . . .
C00B C 0.74697(7) 0.2354(3) 0.88453(10) 0.0287(4) Uani 1 1 d . . . . .
H00B H 0.784898 0.228521 0.917662 0.034 Uiso 1 1 calc R U . . .
C00C C 0.53627(7) 0.7528(3) 0.57059(10) 0.0283(4) Uani 1 1 d . . . . .
H00C H 0.512739 0.899732 0.562806 0.034 Uiso 1 1 calc R U . . .
C00D C 0.60538(7) 0.4572(3) 0.51950(9) 0.0291(4) Uani 1 1 d . . . . .
H00D H 0.628703 0.398809 0.475937 0.035 Uiso 1 1 calc R U . . .
C00E C 0.70346(7) 0.0522(3) 0.89153(10) 0.0283(4) Uani 1 1 d . . . . .
H00E H 0.711950 -0.081448 0.929124 0.034 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C002 N001 N001 116.40(13) . 2_656 ?
N001 C002 C003 125.48(13) . . ?
N001 C002 C004 116.72(13) . . ?
C004 C002 C003 117.75(12) . . ?
C006 C003 C002 120.96(12) . . ?
C006 C003 C008 118.79(13) . . ?
C008 C003 C002 120.20(13) . . ?
C005 C004 C002 119.94(13) . . ?
C005 C004 C007 118.85(14) . . ?
C007 C004 C002 121.18(13) . . ?
C004 C005 H005 119.6 . . ?
C004 C005 C009 120.73(14) . . ?
C009 C005 H005 119.6 . . ?
C003 C006 H006 119.6 . . ?
C00C C006 C003 120.73(14) . . ?
C00C C006 H006 119.6 . . ?
C004 C007 H007 119.9 . . ?
C00E C007 C004 120.10(14) . . ?
C00E C007 H007 119.9 . . ?
C003 C008 H008 120.0 . . ?
C00D C008 C003 120.09(14) . . ?
C00D C008 H008 120.0 . . ?
C005 C009 H009 120.0 . . ?
C00B C009 C005 119.94(14) . . ?
C00B C009 H009 120.0 . . ?
C00C C00A H00A 120.1 . . ?
C00C C00A C00D 119.87(14) . . ?
C00D C00A H00A 120.1 . . ?
C009 C00B H00B 120.2 . . ?
C009 C00B C00E 119.68(14) . . ?
C00E C00B H00B 120.2 . . ?
C006 C00C H00C 120.0 . . ?
C00A C00C C006 120.09(15) . . ?
C00A C00C H00C 120.0 . . ?
C008 C00D H00D 119.8 . . ?
C00A C00D C008 120.40(14) . . ?
C00A C00D H00D 119.8 . . ?
C007 C00E C00B 120.69(15) . . ?
C007 C00E H00E 119.7 . . ?
C00B C00E H00E 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 N001 1.393(2) 2_656 ?
N001 C002 1.2877(18) . ?
C002 C003 1.4932(19) . ?
C002 C004 1.488(2) . ?
C003 C006 1.391(2) . ?
C003 C008 1.395(2) . ?
C004 C005 1.391(2) . ?
C004 C007 1.397(2) . ?
C005 H005 0.9500 . ?
C005 C009 1.391(2) . ?
C006 H006 0.9500 . ?
C006 C00C 1.385(2) . ?
C007 H007 0.9500 . ?
C007 C00E 1.383(2) . ?
C008 H008 0.9500 . ?
C008 C00D 1.389(2) . ?
C009 H009 0.9500 . ?
C009 C00B 1.383(2) . ?
C00A H00A 0.9500 . ?
C00A C00C 1.380(2) . ?
C00A C00D 1.381(2) . ?
C00B H00B 0.9500 . ?
C00B C00E 1.385(2) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N001 N001 C002 C003 8.39(18) 2_656 . . . ?
N001 N001 C002 C004 -174.35(9) 2_656 . . . ?
N001 C002 C003 C006 58.7(2) . . . . ?
N001 C002 C003 C008 -124.12(16) . . . . ?
N001 C002 C004 C005 -148.51(13) . . . . ?
N001 C002 C004 C007 29.45(19) . . . . ?
C002 C003 C006 C00C 177.29(13) . . . . ?
C002 C003 C008 C00D -178.72(13) . . . . ?
C002 C004 C005 C009 176.95(13) . . . . ?
C002 C004 C007 C00E -177.09(13) . . . . ?
C003 C002 C004 C005 28.96(19) . . . . ?
C003 C002 C004 C007 -153.08(13) . . . . ?
C003 C006 C00C C00A 1.4(2) . . . . ?
C003 C008 C00D C00A 1.5(2) . . . . ?
C004 C002 C003 C006 -118.56(15) . . . . ?
C004 C002 C003 C008 58.65(18) . . . . ?
C004 C005 C009 C00B 0.3(2) . . . . ?
C004 C007 C00E C00B 0.0(2) . . . . ?
C005 C004 C007 C00E 0.9(2) . . . . ?
C005 C009 C00B C00E 0.6(2) . . . . ?
C006 C003 C008 C00D -1.5(2) . . . . ?
C007 C004 C005 C009 -1.1(2) . . . . ?
C008 C003 C006 C00C 0.0(2) . . . . ?
C009 C00B C00E C007 -0.8(2) . . . . ?
C00C C00A C00D C008 0.0(2) . . . . ?
C00D C00A C00C C006 -1.4(2) . . . . ?
