Distinctive reactivity of <i>N</i>-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions.
Tambe, Shrikant D.; Min, Kwan Hong; Iqbal, Naeem; Cho, Eun Jin; Beilstein journal of organic chemistry 16 (2020) 1335–1342; doi:10.3762/bjoc.16.114

data_4038503
_publ_section_title
;
 Distinctive reactivity of <i>N</i>-benzylidene-[1,1'-biphenyl]-2-amines
 under photoredox conditions.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1335
_journal_page_last               1342
_journal_paper_doi               10.3762/bjoc.16.114
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C38 H32 N2'
_chemical_formula_sum            'C38 H32 N2'
_chemical_formula_weight         516.69
_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     dual
_audit_creation_date             2019-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                101.392(3)
_cell_angle_beta                 102.647(3)
_cell_angle_gamma                100.795(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5001(3)
_cell_length_b                   10.1630(3)
_cell_length_c                   15.8945(6)
_cell_measurement_reflns_used    7858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.5290
_cell_measurement_theta_min      4.6110
_cell_volume                     1424.60(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.963
_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    -10.00  15.00   0.50    1.56    --    0.00  49.00 -97.00   50
  2  \w    -88.00  25.00   0.50    1.56    --    0.00 -49.00 115.00  226
  3  \w     95.00 194.00   0.50    3.86    --  105.20  49.00 -97.00  198
  4  \w     47.00 129.00   0.50    3.86    --  105.20 -49.00 115.00  164
  5  \w    -88.00  26.00   0.50    1.56    --    0.00 -38.00 -90.00  228
  6  \w    -16.00   9.00   0.50    1.56    --    0.00  57.00-180.00   50
  7  \w    -44.00   3.00   0.50    1.56    --    0.00 -57.00  30.00   94
  8  \w    -86.00 -60.00   0.50    1.56    --    0.00 -57.00  30.00   52
  9  \w     78.00 186.00   0.50    3.86    --  105.20  30.00-120.00  216
 10  \w     59.00 105.00   0.50    3.86    --  105.20 -61.00  60.00   92
 11  \w     99.00 135.00   0.50    3.86    --  105.20 -82.00 120.00   72
 12  \w     65.00 125.00   0.50    3.86    --  105.20 -82.00-180.00  120
 13  \w     18.00 119.00   0.50    3.86    --  105.20 -82.00 -60.00  202
 14  \w    104.00 129.00   0.50    3.86    --  105.20  30.00 150.00   50
 15  \w    151.00 188.00   0.50    3.86    --  105.20  30.00 150.00   74
 16  \w     19.00 140.00   0.50    3.86    --  105.20 -82.00  60.00  242
 17  \w     16.00  46.00   0.50    3.86    --  105.20 -77.00-120.00   60
 18  \w    110.00 191.00   0.50    3.86    --  105.20  45.00 -60.00  162
 19  \w     26.00 132.00   0.50    3.86    --  105.20 -30.00 -60.00  212
 20  \w     58.00  83.00   0.50    3.86    --  105.20 -77.00-120.00   50
 21  \w     86.00 112.00   0.50    3.86    --  105.20 -82.00   0.00   52
 22  \w     30.00  56.00   0.50    3.86    --  105.20 -82.00 120.00   52
 23  \w     79.00 104.00   0.50    3.86    --  105.20 -82.00-120.00   50
 24  \w     19.00 131.00   0.50    3.86    --  105.20 -61.00 -60.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0796757000
_diffrn_orient_matrix_UB_12      -0.0679575000
_diffrn_orient_matrix_UB_13      0.0608335000
_diffrn_orient_matrix_UB_21      0.1106400000
_diffrn_orient_matrix_UB_22      -0.0927721000
_diffrn_orient_matrix_UB_23      0.0091506000
_diffrn_orient_matrix_UB_31      0.1036101000
_diffrn_orient_matrix_UB_32      0.1102765000
_diffrn_orient_matrix_UB_33      0.0820631000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16105
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.573
_diffrn_reflns_theta_min         4.573
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             546
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1192P)^2^+0.1830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4956
_reflns_number_total             5958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-114-S2.cif
_cod_data_source_block           snu_ksh_1
_cod_depositor_comments
;
          Adding full bibliography for 4038503.cif.

2025-09-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11 H10 N O'
_cod_original_formula_weight         172.20
_cod_original_formula_moiety         '0.33(C38 H32 N2)'
_cod_original_formula_units_Z            6
_cod_database_code               4038503
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N001(H001)
2.b Ternary CH refined with riding coordinates:
 C006(H006), C007(H007)
2.c Aromatic/amide H refined with riding coordinates:
 N002(H002), C008(H008), C00B(H00B), 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), C014(H014)
;
_shelx_res_checksum              79577
_shelx_hkl_checksum              73228
_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 3.227
_oxdiff_exptl_absorpt_empirical_full_min 0.302