#------------------------------------------------------------------------------
#$Date: 2025-08-20 20:34:49 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301835 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/43/4134391.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_4134391
loop_
_publ_author_name
'Cong, Xuefeng'
'Zhan, Gu'
'Mo, Zhenbo'
'Nishiura, Masayoshi'
'Hou, Zhaomin'
_publ_section_title
;
 Diastereodivergent [3 + 2] Annulation of Aromatic Aldimines with Alkenes
 via C-H Activation by Half-Sandwich Rare-Earth Catalysts.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5531
_journal_page_last               5537
_journal_paper_doi               10.1021/jacs.0c01171
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C19 H22 I N'
_chemical_formula_sum            'C19 H22 I N'
_chemical_formula_weight         391.27
_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
_audit_creation_date             2018-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                92.455(4)
_cell_angle_beta                 108.753(4)
_cell_angle_gamma                115.373(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8516(12)
_cell_length_b                   9.0513(12)
_cell_length_c                   13.0251(18)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.63
_cell_volume                     872.7(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            13149
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.548
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.829
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0340
_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/[σ²(Fo²)+(0.0439P)²+0.7521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2846
_reflns_number_total             3084
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c01171_si_002.cif
_cod_data_source_block           cong01_0m_a
_cod_depositor_comments
'Adding full bibliography for 4134390--4134391.cif.'
_cod_database_code               4134391
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G),
 C00K(H00Q), C00L(H00R)
2.d Idealised Me refined as rotating group:
 C00H(H00H,H00I,H00J), C00I(H00K,H00L,H00M), C00J(H00N,H00O,H00P)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
I001 I 0.68401(3) 0.88245(3) 0.96133(2) 0.05891(13) Uani 1 1 d . . . . .
N1 N 0.5812(3) 0.8372(3) 0.3859(2) 0.0361(5) Uani 1 1 d . . . . .
C003 C 0.4633(3) 0.7277(3) 0.4377(2) 0.0271(5) Uani 1 1 d . . . . .
H003 H 0.438741 0.612649 0.414519 0.033 Uiso 1 1 calc R . . . .
C004 C 0.5415(4) 0.7743(3) 0.5637(2) 0.0283(6) Uani 1 1 d . . . . .
C005 C 0.7178(4) 0.8286(4) 0.6370(3) 0.0337(6) Uani 1 1 d . . . . .
H005 H 0.807982 0.844772 0.610124 0.040 Uiso 1 1 calc R . . . .
C006 C 0.1350(3) 0.6165(4) 0.2987(2) 0.0322(6) Uani 1 1 d . . . . .
C007 C 0.7586(4) 0.8588(4) 0.7506(3) 0.0368(6) Uani 1 1 d . . . . .
H007 H 0.875824 0.893814 0.800348 0.044 Uiso 1 1 calc R . . . .
C008 C 0.6230(4) 0.8361(4) 0.7891(2) 0.0361(6) Uani 1 1 d . . . . .
C009 C 0.6404(4) 0.7625(4) 0.3128(3) 0.0353(6) Uani 1 1 d . . . . .
C00A C 0.4080(4) 0.7525(3) 0.6046(2) 0.0320(6) Uani 1 1 d . . . . .
C00B C 0.2789(4) 0.7315(4) 0.4081(3) 0.0356(6) Uani 1 1 d . . . . .
C00C C 0.4472(4) 0.7831(4) 0.7178(3) 0.0373(6) Uani 1 1 d . . . . .
H00C H 0.357509 0.768199 0.744874 0.045 Uiso 1 1 calc R . . . .
C00D C 0.2282(4) 0.6932(4) 0.5101(3) 0.0384(7) Uani 1 1 d . . . . .
H00A H 0.165767 0.753501 0.522996 0.046 Uiso 1 1 calc R . . . .
H00D H 0.151835 0.574356 0.500707 0.046 Uiso 1 1 calc R . . . .
C00E C 0.0635(4) 0.4454(4) 0.2805(3) 0.0432(7) Uani 1 1 d . . . . .
H00E H 0.104015 0.396777 0.337449 0.052 Uiso 1 1 calc R . . . .
C00F C 0.0699(5) 0.6860(5) 0.2121(3) 0.0505(8) Uani 1 1 d . . . . .
H00F H 0.115311 0.801349 0.221535 0.061 Uiso 1 1 calc R . . . .
C00G C -0.0657(5) 0.3445(5) 0.1809(3) 0.0496(8) Uani 1 1 d . . . . .
H00G H -0.109928 0.229171 0.171143 0.059 Uiso 1 1 calc R . . . .
C00H C 0.7669(5) 0.7020(6) 0.3851(3) 0.0558(9) Uani 1 1 d . . . . .
H00H H 0.869155 0.795045 0.440275 0.084 Uiso 1 1 calc GR . . . .
H00I H 0.807197 0.653193 0.339638 0.084 Uiso 1 1 calc GR . . . .
H00J H 0.703851 0.619884 0.420789 0.084 Uiso 1 1 calc GR . . . .
C00I C 0.4865(5) 0.6226(5) 0.2172(3) 0.0564(9) Uani 1 1 d . . . . .
H00K H 0.417420 0.532819 0.245912 0.085 Uiso 1 1 calc GR . . . .
H00L H 0.534580 0.582364 0.172766 0.085 Uiso 1 1 calc GR . . . .
H00M H 0.410141 0.664171 0.172415 0.085 Uiso 1 1 calc GR . . . .
C00J C 0.7486(5) 0.9072(5) 0.2670(3) 0.0550(9) Uani 1 1 d . . . . .
H00N H 0.669822 0.944762 0.220106 0.082 Uiso 1 1 calc GR . . . .
H00O H 0.801516 0.869859 0.224756 0.082 Uiso 1 1 calc GR . . . .
H00P H 0.842325 0.997796 0.327413 0.082 Uiso 1 1 calc GR . . . .
C00K C -0.1299(5) 0.4105(5) 0.0963(3) 0.0570(10) Uani 1 1 d . . . . .
H00Q H -0.217622 0.340772 0.028999 0.068 Uiso 1 1 calc R . . . .
C00L C -0.0651(6) 0.5804(6) 0.1102(3) 0.0648(11) Uani 1 1 d . . . . .
H00R H -0.109926 0.626062 0.052743 0.078 Uiso 1 1 calc R . . . .
H00B H 0.309(5) 0.856(5) 0.408(3) 0.043(9) Uiso 1 1 d . . . . .
H1 H 0.545(5) 0.909(5) 0.351(3) 0.052 Uiso 1 1 d R . . . .
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'
I I -0.4742 1.8119 '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
C003 N1 C009 118.9(2) . . ?
C003 N1 H1 116(2) . . ?
C009 N1 H1 108(2) . . ?
N1 C003 H003 108.7 . . ?
N1 C003 C004 114.0(2) . . ?
N1 C003 C00B 114.1(2) . . ?
C004 C003 H003 108.7 . . ?
C004 C003 C00B 102.4(2) . . ?
C00B C003 H003 108.7 . . ?
C005 C004 C003 129.3(3) . . ?
C005 C004 C00A 119.8(3) . . ?
C00A C004 C003 110.9(2) . . ?
C004 C005 H005 120.2 . . ?
C004 C005 C007 119.7(3) . . ?
C007 C005 H005 120.2 . . ?
C00E C006 C00B 123.0(3) . . ?
C00E C006 C00F 117.8(3) . . ?
C00F C006 C00B 119.2(3) . . ?
C005 C007 H007 120.3 . . ?
C008 C007 C005 119.4(3) . . ?
C008 C007 H007 120.3 . . ?
C007 C008 I001 119.6(2) . . ?
C00C C008 I001 118.5(2) . . ?
C00C C008 C007 121.9(3) . . ?
N1 C009 C00H 107.8(3) . . ?
N1 C009 C00I 114.1(3) . . ?
N1 C009 C00J 105.2(3) . . ?
C00H C009 C00J 108.8(3) . . ?
C00I C009 C00H 111.1(3) . . ?
C00I C009 C00J 109.5(3) . . ?
C004 C00A C00D 110.4(3) . . ?
C00C C00A C004 121.1(3) . . ?
C00C C00A C00D 128.5(3) . . ?
C003 C00B H00B 106(2) . . ?
C006 C00B C003 113.9(2) . . ?
C006 C00B C00D 114.6(2) . . ?
C006 C00B H00B 112(2) . . ?
C00D C00B C003 104.5(2) . . ?
C00D C00B H00B 106(2) . . ?
C008 C00C C00A 118.2(3) . . ?
C008 C00C H00C 120.9 . . ?
C00A C00C H00C 120.9 . . ?
C00A C00D C00B 103.9(2) . . ?
C00A C00D H00A 111.0 . . ?
C00A C00D H00D 111.0 . . ?
C00B C00D H00A 111.0 . . ?
C00B C00D H00D 111.0 . . ?
H00A C00D H00D 109.0 . . ?
C006 C00E H00E 119.1 . . ?
C00G C00E C006 121.9(3) . . ?
C00G C00E H00E 119.1 . . ?
C006 C00F H00F 120.1 . . ?
C006 C00F C00L 119.8(3) . . ?
C00L C00F H00F 120.1 . . ?
C00E C00G H00G 119.6 . . ?
C00K C00G C00E 120.8(4) . . ?
C00K C00G H00G 119.6 . . ?
C009 C00H H00H 109.5 . . ?
C009 C00H H00I 109.5 . . ?
C009 C00H H00J 109.5 . . ?
H00H C00H H00I 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 109.5 . . ?
C009 C00I H00K 109.5 . . ?
C009 C00I H00L 109.5 . . ?
C009 C00I H00M 109.5 . . ?
H00K C00I H00L 109.5 . . ?
H00K C00I H00M 109.5 . . ?
H00L C00I H00M 109.5 . . ?
C009 C00J H00N 109.5 . . ?
C009 C00J H00O 109.5 . . ?
C009 C00J H00P 109.5 . . ?
H00N C00J H00O 109.5 . . ?
H00N C00J H00P 109.5 . . ?
H00O C00J H00P 109.5 . . ?
C00G C00K H00Q 120.1 . . ?
C00G C00K C00L 119.8(4) . . ?
C00L C00K H00Q 120.1 . . ?
C00F C00L H00R 120.1 . . ?
C00K C00L C00F 119.9(3) . . ?
C00K C00L H00R 120.1 . . ?
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
I001 C008 2.108(3) . ?
N1 C003 1.466(4) . ?
N1 C009 1.487(4) . ?
N1 H1 0.92(4) . ?
C003 H003 0.9800 . ?
C003 C004 1.519(4) . ?
C003 C00B 1.568(4) . ?
C004 C005 1.390(4) . ?
C004 C00A 1.390(4) . ?
C005 H005 0.9300 . ?
C005 C007 1.391(4) . ?
C006 C00B 1.518(4) . ?
C006 C00E 1.373(5) . ?
C006 C00F 1.398(5) . ?
C007 H007 0.9300 . ?
C007 C008 1.385(4) . ?
C008 C00C 1.381(4) . ?
C009 C00H 1.527(5) . ?
C009 C00I 1.518(5) . ?
C009 C00J 1.533(5) . ?
C00A C00C 1.388(4) . ?
C00A C00D 1.512(4) . ?
C00B C00D 1.543(4) . ?
C00B H00B 1.04(4) . ?
C00C H00C 0.9300 . ?
C00D H00A 0.9700 . ?
C00D H00D 0.9700 . ?
C00E H00E 0.9300 . ?
C00E C00G 1.369(5) . ?
C00F H00F 0.9300 . ?
C00F C00L 1.412(6) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.357(6) . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00I H00K 0.9600 . ?
C00I H00L 0.9600 . ?
C00I H00M 0.9600 . ?
C00J H00N 0.9600 . ?
C00J H00O 0.9600 . ?
C00J H00P 0.9600 . ?
C00K H00Q 0.9300 . ?
C00K C00L 1.371(6) . ?
C00L H00R 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336275
