#------------------------------------------------------------------------------
#$Date: 2024-03-04 21:54:36 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290103 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/26/7132604.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_7132604
loop_
_publ_author_name
'Liang, Qianqian'
'Cai, Yan'
'Jiang, Wenjun'
'Pang, Mengdi'
'Fan, Liming'
'Zhang, Guoying'
_publ_section_title
;
 Palladium-catalyzed allylation and carbonylation: access to
 allylhydrazones and allyl acylhydrazones.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1638
_journal_page_last               1641
_journal_paper_doi               10.1039/d3cc05531k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C23 H22 N2'
_chemical_formula_weight         326.43
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2023-03-20 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.962(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8961(11)
_cell_length_b                   18.4187(17)
_cell_length_c                   9.4952(8)
_cell_measurement_reflns_used    1737
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.654
_cell_measurement_theta_min      2.313
_cell_volume                     1767.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_sigmaI/netI    0.1370
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8212
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1697
_refine_ls_R_factor_gt           0.0901
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0977P)²+0.1507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2449
_reflns_number_gt                1605
_reflns_number_total             3088
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3cc05531k2.cif
_cod_data_source_block           220627f
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7132604--7132610.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7132604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3476(3) 0.67451(16) 0.3456(3) 0.0378(8) Uani 1 1 d . . .
N2 N 0.4568(3) 0.66059(16) 0.3164(3) 0.0364(8) Uani 1 1 d . . .
C1 C 0.2552(4) 0.7287(2) 0.2656(4) 0.0423(11) Uani 1 1 d . . .
H1A H 0.3036 0.7689 0.2451 0.051 Uiso 1 1 calc R . .
H1B H 0.2120 0.7467 0.3313 0.051 Uiso 1 1 calc R . .
C2 C 0.1534(4) 0.7059(2) 0.1226(4) 0.0378(10) Uani 1 1 d . . .
H2 H 0.0860 0.7388 0.0744 0.045 Uiso 1 1 calc R . .
C3 C 0.1489(4) 0.6440(2) 0.0572(4) 0.0384(10) Uani 1 1 d . . .
H3 H 0.2183 0.6124 0.1060 0.046 Uiso 1 1 calc R . .
C4 C 0.0506(4) 0.6177(2) -0.0809(4) 0.0375(10) Uani 1 1 d . . .
C5 C 0.0480(4) 0.5471(2) -0.1198(5) 0.0460(11) Uani 1 1 d . . .
H5 H 0.1148 0.5167 -0.0584 0.055 Uiso 1 1 calc R . .
C6 C -0.0470(5) 0.5183(3) -0.2437(5) 0.0538(12) Uani 1 1 d . . .
H6 H -0.0459 0.4692 -0.2656 0.065 Uiso 1 1 calc R . .
C7 C -0.1435(5) 0.5617(3) -0.3352(5) 0.0612(13) Uani 1 1 d . . .
H7 H -0.2101 0.5426 -0.4203 0.073 Uiso 1 1 calc R . .
C8 C -0.1430(5) 0.6330(3) -0.3025(5) 0.0667(14) Uani 1 1 d . . .
H8 H -0.2086 0.6633 -0.3661 0.080 Uiso 1 1 calc R . .
C9 C -0.0473(4) 0.6604(2) -0.1775(5) 0.0507(11) Uani 1 1 d . . .
H9 H -0.0482 0.7097 -0.1567 0.061 Uiso 1 1 calc R . .
C10 C 0.3352(4) 0.63628(19) 0.4645(4) 0.0356(10) Uani 1 1 d . . .
C11 C 0.4403(4) 0.6009(2) 0.5680(5) 0.0462(11) Uani 1 1 d . . .
H11 H 0.5213 0.6014 0.5562 0.055 Uiso 1 1 calc R . .
C12 C 0.4300(5) 0.5652(2) 0.6877(5) 0.0513(11) Uani 1 1 d . . .
C13 C 0.3096(5) 0.5642(2) 0.7034(5) 0.0588(13) Uani 1 1 d . . .
H13 H 0.3005 0.5405 0.7855 0.071 Uiso 1 1 calc R . .
C14 C 0.2053(5) 0.5974(2) 0.5999(6) 0.0582(13) Uani 1 1 d . . .
H14 H 0.1239 0.5957 0.6107 0.070 Uiso 1 1 calc R . .
C15 C 0.2149(4) 0.6334(2) 0.4801(5) 0.0462(11) Uani 1 1 d . . .
H15 H 0.1410 0.6558 0.4094 0.055 Uiso 1 1 calc R . .
C16 C 0.5451(5) 0.5270(3) 0.7974(5) 0.0752(16) Uani 1 1 d . . .
H16A H 0.6193 0.5317 0.7668 0.113 Uiso 1 1 calc R . .
H16B H 0.5241 0.4765 0.8003 0.113 Uiso 1 1 calc R . .
H16C H 0.5667 0.5479 0.8964 0.113 Uiso 1 1 calc R . .
C17 C 0.4733(4) 0.6898(2) 0.2049(4) 0.0388(10) Uani 1 1 d . . .
H17 H 0.4091 0.7204 0.1399 0.047 Uiso 1 1 calc R . .
C18 C 0.5939(4) 0.6751(2) 0.1797(4) 0.0363(9) Uani 1 1 d . . .
C19 C 0.6936(4) 0.6362(3) 0.2781(5) 0.0594(13) Uani 1 1 d . . .
H19 H 0.6857 0.6179 0.3656 0.071 Uiso 1 1 calc R . .
C20 C 0.8060(5) 0.6233(3) 0.2511(6) 0.0723(15) Uani 1 1 d . . .
H20 H 0.8741 0.5964 0.3204 0.087 Uiso 1 1 calc R . .
C21 C 0.8191(5) 0.6490(3) 0.1262(6) 0.0629(14) Uani 1 1 d . . .
H21 H 0.8965 0.6405 0.1089 0.075 Uiso 1 1 calc R . .
C22 C 0.7211(5) 0.6869(3) 0.0265(6) 0.0692(15) Uani 1 1 d . . .
H22 H 0.7291 0.7041 -0.0617 0.083 Uiso 1 1 calc R . .
C23 C 0.6083(4) 0.7005(2) 0.0536(5) 0.0585(13) Uani 1 1 d . . .
H23 H 0.5407 0.7276 -0.0160 0.070 Uiso 1 1 calc 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'
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
N2 N1 C10 115.9(3) . . ?
N2 N1 C1 122.0(3) . . ?
C10 N1 C1 122.0(3) . . ?
C17 N2 N1 120.5(3) . . ?
N1 C1 C2 115.8(3) . . ?
N1 C1 H1A 108.3 . . ?
C2 C1 H1A 108.3 . . ?
N1 C1 H1B 108.3 . . ?
C2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C3 C2 C1 125.6(4) . . ?
C3 C2 H2 117.2 . . ?
C1 C2 H2 117.2 . . ?
C2 C3 C4 128.3(4) . . ?
C2 C3 H3 115.8 . . ?
C4 C3 H3 115.8 . . ?
C5 C4 C9 116.1(4) . . ?
C5 C4 C3 120.5(4) . . ?
C9 C4 C3 123.3(4) . . ?
C4 C5 C6 123.1(4) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C7 C6 C5 119.2(4) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 119.6(5) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 121.8(4) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
C11 C10 C15 118.7(4) . . ?
C11 C10 N1 121.4(3) . . ?
C15 C10 N1 119.9(4) . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 118.6(4) . . ?
C11 C12 C16 120.6(4) . . ?
C13 C12 C16 120.8(4) . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.9(4) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 119.1(4) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 118.9(3) . . ?
N2 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C19 C18 C23 118.1(4) . . ?
C19 C18 C17 122.2(4) . . ?
C23 C18 C17 119.8(4) . . ?
C18 C19 C20 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 120.6(5) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.6(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.9(4) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
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
N1 N2 1.343(4) . ?
N1 C10 1.379(4) . ?
N1 C1 1.420(5) . ?
N2 C17 1.259(4) . ?
C1 C2 1.457(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.291(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.431(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.351(5) . ?
C4 C9 1.366(5) . ?
C5 C6 1.351(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.347(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.348(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.351(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.364(5) . ?
C10 C15 1.375(5) . ?
C11 C12 1.354(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(6) . ?
C12 C16 1.474(6) . ?
C13 C14 1.340(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.354(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.446(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.344(5) . ?
C18 C23 1.348(5) . ?
C19 C20 1.363(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.334(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.330(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
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
C10 N1 N2 C17 176.1(3) . . . . ?
C1 N1 N2 C17 -8.0(5) . . . . ?
N2 N1 C1 C2 86.0(4) . . . . ?
C10 N1 C1 C2 -98.4(4) . . . . ?
N1 C1 C2 C3 -7.3(6) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C2 C3 C4 C5 -168.1(4) . . . . ?
C2 C3 C4 C9 9.5(6) . . . . ?
C9 C4 C5 C6 -2.0(6) . . . . ?
C3 C4 C5 C6 175.8(4) . . . . ?
C4 C5 C6 C7 0.9(6) . . . . ?
C5 C6 C7 C8 0.6(7) . . . . ?
C6 C7 C8 C9 -1.0(7) . . . . ?
C7 C8 C9 C4 -0.2(7) . . . . ?
C5 C4 C9 C8 1.6(6) . . . . ?
C3 C4 C9 C8 -176.1(4) . . . . ?
N2 N1 C10 C11 15.6(5) . . . . ?
C1 N1 C10 C11 -160.3(4) . . . . ?
N2 N1 C10 C15 -164.4(3) . . . . ?
C1 N1 C10 C15 19.7(5) . . . . ?
C15 C10 C11 C12 -2.0(6) . . . . ?
N1 C10 C11 C12 177.9(4) . . . . ?
C10 C11 C12 C13 0.6(6) . . . . ?
C10 C11 C12 C16 179.6(4) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C16 C12 C13 C14 -178.0(4) . . . . ?
C12 C13 C14 C15 -1.0(7) . . . . ?
C13 C14 C15 C10 -0.4(6) . . . . ?
C11 C10 C15 C14 1.9(6) . . . . ?
N1 C10 C15 C14 -178.1(3) . . . . ?
N1 N2 C17 C18 178.3(3) . . . . ?
N2 C17 C18 C19 -5.7(6) . . . . ?
N2 C17 C18 C23 174.0(4) . . . . ?
C23 C18 C19 C20 0.4(7) . . . . ?
C17 C18 C19 C20 -180.0(4) . . . . ?
C18 C19 C20 C21 -0.1(8) . . . . ?
C19 C20 C21 C22 -0.7(8) . . . . ?
C20 C21 C22 C23 1.2(8) . . . . ?
C19 C18 C23 C22 0.2(7) . . . . ?
C17 C18 C23 C22 -179.5(4) . . . . ?
C21 C22 C23 C18 -1.0(8) . . . . ?
