#------------------------------------------------------------------------------
#$Date: 2024-03-04 21:54:36 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290103 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/26/7132606.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_7132606
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            'C22 H20 N2'
_chemical_formula_weight         312.40
_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                 104.371(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0309(9)
_cell_length_b                   19.6236(18)
_cell_length_c                   9.0074(8)
_cell_measurement_reflns_used    1355
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.328
_cell_measurement_theta_min      2.543
_cell_volume                     1717.6(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.1191
_diffrn_reflns_av_sigmaI/netI    0.1180
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8289
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      \"i1/4\"Y
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.055
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1937
_refine_ls_R_factor_gt           0.0881
_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)+(0.0939P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2396
_reflns_number_gt                1268
_reflns_number_total             3020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3cc05531k2.cif
_cod_data_source_block           220521h
_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               7132606
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 0.3124(4) 0.16306(15) 0.6136(4) 0.0635(9) Uani 1 1 d . . .
N2 N 0.3950(4) 0.10878(15) 0.6706(4) 0.0633(9) Uani 1 1 d . . .
C1 C 0.4959(5) 0.09467(19) 0.6167(5) 0.0628(11) Uani 1 1 d . . .
H1 H 0.5144 0.1207 0.5379 0.075 Uiso 1 1 calc R . .
C2 C 0.5839(5) 0.03671(19) 0.6797(5) 0.0624(11) Uani 1 1 d . . .
C3 C 0.6965(5) 0.0248(2) 0.6263(6) 0.0875(14) Uani 1 1 d . . .
H3 H 0.7155 0.0526 0.5504 0.105 Uiso 1 1 calc R . .
C4 C 0.7827(6) -0.0283(3) 0.6844(8) 0.1128(19) Uani 1 1 d . . .
H4 H 0.8601 -0.0365 0.6477 0.135 Uiso 1 1 calc R . .
C5 C 0.7559(6) -0.0684(3) 0.7938(8) 0.1033(19) Uani 1 1 d . . .
H5 H 0.8166 -0.1034 0.8345 0.124 Uiso 1 1 calc R . .
C6 C 0.6422(6) -0.0590(2) 0.8458(6) 0.0957(17) Uani 1 1 d . . .
H6 H 0.6227 -0.0879 0.9195 0.115 Uiso 1 1 calc R . .
C7 C 0.5555(5) -0.0058(2) 0.7877(5) 0.0760(13) Uani 1 1 d . . .
H7 H 0.4767 0.0012 0.8224 0.091 Uiso 1 1 calc R . .
C8 C 0.1966(5) 0.16891(18) 0.6678(5) 0.0604(11) Uani 1 1 d . . .
C9 C 0.1137(5) 0.2277(2) 0.6362(5) 0.0767(13) Uani 1 1 d . . .
H9 H 0.1379 0.2630 0.5792 0.092 Uiso 1 1 calc R . .
C10 C -0.0005(6) 0.2329(3) 0.6884(6) 0.0895(16) Uani 1 1 d . . .
H10 H -0.0528 0.2725 0.6678 0.107 Uiso 1 1 calc R . .
C11 C -0.0419(6) 0.1832(3) 0.7688(7) 0.0990(17) Uani 1 1 d . . .
H11 H -0.1223 0.1875 0.8018 0.119 Uiso 1 1 calc R . .
C12 C 0.0389(6) 0.1253(3) 0.8012(6) 0.0935(15) Uani 1 1 d . . .
H12 H 0.0138 0.0905 0.8589 0.112 Uiso 1 1 calc R . .
C13 C 0.1540(5) 0.1187(2) 0.7498(5) 0.0752(13) Uani 1 1 d . . .
H13 H 0.2054 0.0789 0.7710 0.090 Uiso 1 1 calc R . .
C14 C 0.3328(5) 0.20116(19) 0.4824(5) 0.0713(12) Uani 1 1 d . . .
H14A H 0.2452 0.2209 0.4295 0.086 Uiso 1 1 calc R . .
H14B H 0.3591 0.1692 0.4125 0.086 Uiso 1 1 calc R . .
C15 C 0.4370(5) 0.25680(19) 0.5150(5) 0.0690(12) Uani 1 1 d . . .
H15 H 0.4336 0.2885 0.4373 0.083 Uiso 1 1 calc R . .
C16 C 0.5313(5) 0.26554(19) 0.6395(5) 0.0666(12) Uani 1 1 d . . .
H16 H 0.5316 0.2353 0.7190 0.080 Uiso 1 1 calc R . .
C17 C 0.6385(4) 0.31839(19) 0.6691(5) 0.0594(11) Uani 1 1 d . . .
C18 C 0.6609(5) 0.3613(2) 0.5587(5) 0.0781(13) Uani 1 1 d . . .
H18 H 0.6070 0.3574 0.4590 0.094 Uiso 1 1 calc R . .
C19 C 0.7600(6) 0.4092(3) 0.5921(7) 0.0969(16) Uani 1 1 d . . .
H19 H 0.7702 0.4393 0.5159 0.116 Uiso 1 1 calc R . .
C20 C 0.8443(5) 0.4144(2) 0.7331(8) 0.0947(17) Uani 1 1 d . . .
H20 H 0.9143 0.4468 0.7536 0.114 Uiso 1 1 calc R . .
C21 C 0.8262(5) 0.3717(2) 0.8457(6) 0.0863(14) Uani 1 1 d . . .
H21 H 0.8822 0.3754 0.9445 0.104 Uiso 1 1 calc R . .
C22 C 0.7247(5) 0.3233(2) 0.8125(5) 0.0706(12) Uani 1 1 d . . .
H22 H 0.7143 0.2932 0.8886 0.085 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 C8 114.7(3) . . ?
N2 N1 C14 120.7(3) . . ?
C8 N1 C14 123.2(3) . . ?
C1 N2 N1 119.8(4) . . ?
N2 C1 C2 119.2(4) . . ?
N2 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C7 119.3(4) . . ?
C3 C2 C1 118.2(4) . . ?
C7 C2 C1 122.5(4) . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 118.7(5) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 120.7(5) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C13 C8 N1 122.7(4) . . ?
C13 C8 C9 116.9(4) . . ?
N1 C8 C9 120.4(4) . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 122.6(5) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 117.8(5) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 121.7(4) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
N1 C14 C15 116.8(3) . . ?
N1 C14 H14A 108.1 . . ?
C15 C14 H14A 108.1 . . ?
N1 C14 H14B 108.1 . . ?
C15 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C16 C15 C14 126.7(4) . . ?
C16 C15 H15 116.7 . . ?
C14 C15 H15 116.7 . . ?
C15 C16 C17 126.8(4) . . ?
C15 C16 H16 116.6 . . ?
C17 C16 H16 116.6 . . ?
C18 C17 C22 117.7(4) . . ?
C18 C17 C16 123.3(4) . . ?
C22 C17 C16 118.9(4) . . ?
C19 C18 C17 121.0(5) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 121.4(5) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 119.2(5) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C21 C22 119.5(5) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C17 C22 C21 121.1(4) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 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 1.369(4) . ?
N1 C8 1.372(5) . ?
N1 C14 1.455(5) . ?
N2 C1 1.257(4) . ?
C1 C2 1.465(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.353(6) . ?
C2 C7 1.365(5) . ?
C3 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.339(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.349(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.362(5) . ?
C8 C9 1.410(5) . ?
C9 C10 1.345(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.340(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.352(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.490(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.286(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.470(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(5) . ?
C17 C22 1.367(6) . ?
C18 C19 1.347(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.344(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.362(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(6) . ?
C21 H21 0.9300 . ?
C22 H22 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
C8 N1 N2 C1 172.7(4) . . . . ?
C14 N1 N2 C1 5.3(5) . . . . ?
N1 N2 C1 C2 179.5(3) . . . . ?
N2 C1 C2 C3 -176.2(4) . . . . ?
N2 C1 C2 C7 4.7(6) . . . . ?
C7 C2 C3 C4 -2.0(7) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C3 C4 C5 C6 2.0(8) . . . . ?
C4 C5 C6 C7 -2.0(8) . . . . ?
C3 C2 C7 C6 2.1(6) . . . . ?
C1 C2 C7 C6 -178.9(4) . . . . ?
C5 C6 C7 C2 -0.1(7) . . . . ?
N2 N1 C8 C13 -11.1(5) . . . . ?
C14 N1 C8 C13 155.8(4) . . . . ?
N2 N1 C8 C9 170.6(3) . . . . ?
C14 N1 C8 C9 -22.4(6) . . . . ?
C13 C8 C9 C10 1.0(6) . . . . ?
N1 C8 C9 C10 179.3(4) . . . . ?
C8 C9 C10 C11 -1.2(8) . . . . ?
C9 C10 C11 C12 1.4(8) . . . . ?
C10 C11 C12 C13 -1.6(8) . . . . ?
C11 C12 C13 C8 1.5(7) . . . . ?
N1 C8 C13 C12 -179.5(4) . . . . ?
C9 C8 C13 C12 -1.2(6) . . . . ?
N2 N1 C14 C15 -85.3(4) . . . . ?
C8 N1 C14 C15 108.5(4) . . . . ?
N1 C14 C15 C16 16.3(6) . . . . ?
C14 C15 C16 C17 176.7(4) . . . . ?
C15 C16 C17 C18 -7.8(7) . . . . ?
C15 C16 C17 C22 175.3(4) . . . . ?
C22 C17 C18 C19 -3.5(6) . . . . ?
C16 C17 C18 C19 179.6(4) . . . . ?
C17 C18 C19 C20 3.2(7) . . . . ?
C18 C19 C20 C21 -2.2(8) . . . . ?
C19 C20 C21 C22 1.6(7) . . . . ?
C18 C17 C22 C21 2.9(6) . . . . ?
C16 C17 C22 C21 -180.0(4) . . . . ?
C20 C21 C22 C17 -2.0(6) . . . . ?
