#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:19:02 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257598 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239952.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_7239952
loop_
_publ_author_name
'Largeron, Martine'
'Deschamps, Patrick'
'Hammad, Karim'
'Fleury, Maurice-Bernard'
_publ_section_title
;
 A dual biomimetic process for the selective aerobic oxidative coupling of
 primary amines using pyrogallol as a precatalyst. Isolation of the [5 +
 2] cycloaddition redox intermediates
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1894
_journal_page_last               1905
_journal_paper_doi               10.1039/C9GC03992A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C17 H17 N'
_chemical_formula_sum            'C17 H17 N'
_chemical_formula_weight         235.31
_chemical_name_common
(E)-N-(2,3-dihydro-1H-inden-2-yl)-1(p-tolyl)methanimine
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-02-04 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                103.2590(10)
_cell_angle_beta                 95.0990(10)
_cell_angle_gamma                95.6240(10)
_cell_formula_units_Z            2
_cell_length_a                   5.6742(2)
_cell_length_b                   8.7921(4)
_cell_length_c                   13.5713(5)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.8
_cell_measurement_theta_min      3.37
_cell_volume                     651.48(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP(III)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS ICMMO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21496
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        63.997
_diffrn_reflns_theta_max         63.997
_diffrn_reflns_theta_min         3.368
_diffrn_source                   'Fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  0.9524
_exptl_absorpt_correction_T_min  0.8641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0439
_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)+(0.0631P)²+0.2041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1995
_reflns_number_total             2166
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc03992a2.cif
_cod_data_source_block           24j
_cod_depositor_comments
;Adding full bibliography for 7239951--7239953.cif.

 Adding full bibliography for 7239951--7239953.cif.
;
_cod_database_code               7239952
_shelx_shelxl_version_number     2016/6
_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_min   0.889
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.7763(2) 0.30884(14) 0.64462(9) 0.0198(3) Uani 1 1 d . . . . .
H1 H 0.892630 0.253848 0.667926 0.024 Uiso 1 1 calc R U . . .
N2 N 0.72673(19) 0.29012(12) 0.54939(8) 0.0247(3) Uani 1 1 d . . . . .
C3 C 0.8528(2) 0.17918(14) 0.48290(9) 0.0219(3) Uani 1 1 d . . . . .
H3 H 0.945772 0.122907 0.524033 0.026 Uiso 1 1 calc R U . . .
C4 C 1.0205(2) 0.26094(15) 0.42226(9) 0.0253(3) Uani 1 1 d . . . . .
H4A H 0.966840 0.359034 0.413716 0.033 Uiso 1 1 calc R U . . .
H4B H 1.182258 0.282333 0.456130 0.033 Uiso 1 1 calc R U . . .
C4A C 1.0056(2) 0.14313(14) 0.32093(9) 0.0204(3) Uani 1 1 d . . . . .
C5 C 1.1535(2) 0.13928(15) 0.24440(10) 0.0280(3) Uani 1 1 d . . . . .
H5 H 1.284697 0.215076 0.252644 0.034 Uiso 1 1 calc R U . . .
C6 C 1.1029(2) 0.02092(16) 0.15547(10) 0.0272(3) Uani 1 1 d . . . . .
H6 H 1.201262 0.017184 0.103883 0.033 Uiso 1 1 calc R U . . .
C7 C 0.9071(2) -0.09167(15) 0.14303(9) 0.0246(3) Uani 1 1 d . . . . .
H7 H 0.874484 -0.170206 0.082996 0.030 Uiso 1 1 calc R U . . .
C8 C 0.7592(2) -0.08824(15) 0.21941(10) 0.0255(3) Uani 1 1 d . . . . .
H8 H 0.627356 -0.163698 0.210875 0.031 Uiso 1 1 calc R U . . .
C8A C 0.8107(2) 0.02953(14) 0.30887(9) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.6784(2) 0.05919(16) 0.40174(10) 0.0284(3) Uani 1 1 d . . . . .
H9A H 0.641437 -0.037182 0.423562 0.037 Uiso 1 1 calc R U . . .
H9B H 0.531270 0.102238 0.388052 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6573(2) 0.41412(14) 0.71988(9) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.4527(2) 0.47808(15) 0.69208(9) 0.0229(3) Uani 1 1 d . . . . .
H11 H 0.388868 0.454972 0.624044 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3447(2) 0.57530(15) 0.76487(10) 0.0234(3) Uani 1 1 d . . . . .
H12 H 0.206881 0.615162 0.745185 0.028 Uiso 1 1 calc R U . . .
C13 C 0.4382(2) 0.61520(14) 0.86784(9) 0.0203(3) Uani 1 1 d . . . . .
C14 C 0.3258(2) 0.72953(16) 0.94451(10) 0.0271(3) Uani 1 1 d . . . . .
H14A H 0.398268 0.733620 1.011886 0.069(4) Uiso 1 1 calc R U . . .
H14B H 0.158159 0.695673 0.939389 0.069(4) Uiso 1 1 calc R U . . .
H14C H 0.349266 0.832237 0.931176 0.069(4) Uiso 1 1 calc R U . . .
C15 C 0.6395(2) 0.54951(14) 0.89500(9) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.703511 0.572854 0.963008 0.025 Uiso 1 1 calc R U . . .
C16 C 0.7471(2) 0.44947(14) 0.82242(9) 0.0206(3) Uani 1 1 d . . . . .
H16 H 0.880536 0.405691 0.842583 0.025 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 0.0181 0.0091 '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 0.0311 0.0180 '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
N2 C1 C10 122.66(11) . . ?
N2 C1 H1 118.7 . . ?
C10 C1 H1 118.7 . . ?
C1 N2 C3 117.28(11) . . ?
N2 C3 C9 111.42(10) . . ?
N2 C3 C4 112.39(10) . . ?
C9 C3 C4 105.19(10) . . ?
N2 C3 H3 109.2 . . ?
C9 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C4A C4 C3 103.69(10) . . ?
C4A C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C4A C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C8A C4A C5 120.41(11) . . ?
C8A C4A C4 110.75(11) . . ?
C5 C4A C4 128.84(12) . . ?
C6 C5 C4A 119.17(12) . . ?
C6 C5 H5 120.4 . . ?
C4A C5 H5 120.4 . . ?
C7 C6 C5 120.44(12) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.53(12) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C8A 119.08(12) . . ?
C7 C8 H8 120.5 . . ?
C8A C8 H8 120.5 . . ?
C4A C8A C8 120.36(12) . . ?
C4A C8A C9 110.41(11) . . ?
C8 C8A C9 129.21(12) . . ?
C8A C9 C3 104.06(10) . . ?
C8A C9 H9A 110.9 . . ?
C3 C9 H9A 110.9 . . ?
C8A C9 H9B 110.9 . . ?
C3 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
C16 C10 C11 118.44(11) . . ?
C16 C10 C1 119.47(11) . . ?
C11 C10 C1 122.08(11) . . ?
C12 C11 C10 120.47(11) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.39(11) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C15 C13 C12 117.76(11) . . ?
C15 C13 C14 121.98(11) . . ?
C12 C13 C14 120.23(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 121.20(11) . . ?
C13 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C10 120.70(11) . . ?
C15 C16 H16 119.7 . . ?
C10 C16 H16 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
C1 N2 1.2670(16) . ?
C1 C10 1.4724(17) . ?
C1 H1 0.9300 . ?
N2 C3 1.4576(15) . ?
C3 C9 1.5409(18) . ?
C3 C4 1.5414(18) . ?
C3 H3 0.9800 . ?
C4 C4A 1.5101(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4A C8A 1.3871(18) . ?
C4A C5 1.3885(18) . ?
C5 C6 1.3877(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.3847(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.3877(18) . ?
C7 H7 0.9300 . ?
C8 C8A 1.3901(18) . ?
C8 H8 0.9300 . ?
C8A C9 1.5086(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C16 1.3920(17) . ?
C10 C11 1.3978(18) . ?
C11 C12 1.3803(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.4016(18) . ?
C12 H12 0.9300 . ?
C13 C15 1.3876(18) . ?
C13 C14 1.5047(16) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.3897(17) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
