#------------------------------------------------------------------------------
#$Date: 2020-08-07 04:16:35 +0300 (Fri, 07 Aug 2020) $
#$Revision: 255149 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/88/1558806.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_1558806
loop_
_publ_author_name
'Xie, Jianing'
'Li, Xuetong'
'Kleij, Arjan Willem'
_publ_section_title
;
 Pd-catalyzed stereoselective tandem ring-opening amination/cyclization of
 vinyl gamma-lactones: Access to caprolactam diversity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03647A
_journal_year                    2020
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-21 deposited with the CCDC.	2020-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.545(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2396(2)
_cell_length_b                   23.7102(7)
_cell_length_c                   9.2667(3)
_cell_measurement_reflns_used    7760
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3550
_cell_measurement_theta_min      2.7680
_cell_volume                     1362.00(7)
_computing_cell_refinement
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_data_collection
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_data_reduction
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_molecular_graphics
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    Sir2019
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.432
_diffrn_reflns_theta_min         2.373
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       Block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0389
_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)+(0.0567P)²+0.3991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3098
_reflns_number_total             3456
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03647a2.cif
_cod_data_source_block           JN181
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1558806
_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.
;
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_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_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 0.54713(15) 0.67425(4) 0.15786(10) 0.01519(19) Uani 1 1 d . . . . .
N1 N 0.61044(13) 0.67103(3) 0.31138(9) 0.01646(18) Uani 1 1 d . . . . .
O1 O 0.92311(12) 0.71852(3) 0.29362(8) 0.02152(17) Uani 1 1 d . . . . .
C2 C 0.34189(16) 0.69325(4) 0.10484(11) 0.0188(2) Uani 1 1 d . . . . .
H2 H 0.243445 0.704629 0.170259 0.023 Uiso 1 1 calc R U . . .
C3 C 0.28152(17) 0.69550(4) -0.04466(12) 0.0218(2) Uani 1 1 d . . . . .
H3 H 0.140977 0.708022 -0.080833 0.026 Uiso 1 1 calc R U . . .
C4 C 0.42533(18) 0.67958(4) -0.14097(11) 0.0231(2) Uani 1 1 d . . . . .
H4 H 0.383875 0.681349 -0.242744 0.028 Uiso 1 1 calc R U . . .
C5 C 0.63039(17) 0.66104(4) -0.08746(11) 0.0216(2) Uani 1 1 d . . . . .
H5 H 0.729419 0.650213 -0.153029 0.026 Uiso 1 1 calc R U . . .
C6 C 0.69147(16) 0.65825(4) 0.06122(11) 0.0177(2) Uani 1 1 d . . . . .
H6 H 0.831737 0.645421 0.097052 0.021 Uiso 1 1 calc R U . . .
C7 C 0.79904(16) 0.69578(4) 0.36937(11) 0.0167(2) Uani 1 1 d . . . . .
C8 C 0.85234(17) 0.69135(4) 0.53191(11) 0.0193(2) Uani 1 1 d . . . . .
H8A H 0.726046 0.703412 0.579857 0.023 Uiso 1 1 calc R U . . .
H8B H 0.973813 0.716944 0.564059 0.023 Uiso 1 1 calc R U . . .
C9 C 0.91362(16) 0.63087(4) 0.57790(11) 0.0187(2) Uani 1 1 d . . . . .
H9A H 1.013669 0.615852 0.511701 0.022 Uiso 1 1 calc R U . . .
H9B H 0.992093 0.631763 0.676943 0.022 Uiso 1 1 calc R U . . .
C10 C 0.72440(15) 0.59087(4) 0.57739(10) 0.01606(19) Uani 1 1 d . . . . .
C11 C 0.53144(15) 0.59947(4) 0.50198(10) 0.0173(2) Uani 1 1 d . . . . .
H11 H 0.427750 0.570659 0.510344 0.021 Uiso 1 1 calc R U . . .
C12 C 0.45469(15) 0.64857(4) 0.40517(11) 0.0185(2) Uani 1 1 d . . . . .
H12A H 0.323522 0.636626 0.342368 0.022 Uiso 1 1 calc R U . . .
H12B H 0.412435 0.679605 0.467559 0.022 Uiso 1 1 calc R U . . .
C13 C 0.76530(16) 0.54029(4) 0.67233(10) 0.0169(2) Uani 1 1 d . . . . .
C14 C 0.96556(17) 0.51300(4) 0.68437(12) 0.0228(2) Uani 1 1 d . . . . .
H14 H 1.073863 0.525958 0.628173 0.027 Uiso 1 1 calc R U . . .
C15 C 1.00878(18) 0.46729(5) 0.77710(13) 0.0270(2) Uani 1 1 d . . . . .
H15 H 1.144827 0.448937 0.782790 0.032 Uiso 1 1 calc R U . . .
C16 C 0.85280(19) 0.44847(4) 0.86141(13) 0.0259(2) Uani 1 1 d . . . . .
H16 H 0.882827 0.417753 0.926403 0.031 Uiso 1 1 calc R U . . .
C17 C 0.65307(18) 0.47475(4) 0.85021(12) 0.0238(2) Uani 1 1 d . . . . .
H17 H 0.545426 0.461551 0.906642 0.029 Uiso 1 1 calc R U . . .
C18 C 0.60924(17) 0.52030(4) 0.75694(12) 0.0203(2) Uani 1 1 d . . . . .
H00A H 0.471973 0.538045 0.750552 0.024 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 0.0033 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'
O O 0.0106 0.0060 '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
C2 C1 C6 119.80(9) . . ?
C2 C1 N1 120.34(8) . . ?
C6 C1 N1 119.86(8) . . ?
C7 N1 C1 119.58(8) . . ?
C7 N1 C12 121.21(8) . . ?
C1 N1 C12 118.56(8) . . ?
C1 C2 C3 119.74(9) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.47(9) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.53(10) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.43(9) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.03(9) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 N1 122.27(9) . . ?
O1 C7 C8 121.33(9) . . ?
N1 C7 C8 116.34(8) . . ?
C7 C8 C9 111.26(8) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 114.56(8) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C13 120.93(9) . . ?
C11 C10 C9 124.17(9) . . ?
C13 C10 C9 114.88(8) . . ?
C10 C11 C12 129.21(9) . . ?
C10 C11 H11 115.4 . . ?
C12 C11 H11 115.4 . . ?
N1 C12 C11 116.21(8) . . ?
N1 C12 H12A 108.2 . . ?
C11 C12 H12A 108.2 . . ?
N1 C12 H12B 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C18 118.04(9) . . ?
C14 C13 C10 120.63(9) . . ?
C18 C13 C10 121.26(9) . . ?
C15 C14 C13 121.20(10) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.93(10) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 119.66(10) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.45(10) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.71(10) . . ?
C17 C18 H00A 119.6 . . ?
C13 C18 H00A 119.6 . . ?
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 C2 1.3932(13) . ?
C1 C6 1.3932(13) . ?
C1 N1 1.4345(12) . ?
N1 C7 1.3690(12) . ?
N1 C12 1.4751(12) . ?
O1 C7 1.2274(12) . ?
C2 C3 1.3946(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3881(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3898(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3886(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5087(13) . ?
C8 C9 1.5319(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5140(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3370(14) . ?
C10 C13 1.4921(13) . ?
C11 C12 1.5138(13) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.4002(14) . ?
C13 C18 1.4006(13) . ?
C14 C15 1.3903(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.3893(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3866(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3909(14) . ?
C17 H17 0.9500 . ?
C18 H00A 0.9500 . ?
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
C2 C1 N1 C7 -128.28(10) . . . . ?
C6 C1 N1 C7 51.80(12) . . . . ?
C2 C1 N1 C12 42.61(12) . . . . ?
C6 C1 N1 C12 -137.32(9) . . . . ?
C6 C1 C2 C3 0.73(14) . . . . ?
N1 C1 C2 C3 -179.20(9) . . . . ?
C1 C2 C3 C4 -0.76(15) . . . . ?
C2 C3 C4 C5 0.31(16) . . . . ?
C3 C4 C5 C6 0.18(15) . . . . ?
C4 C5 C6 C1 -0.20(15) . . . . ?
C2 C1 C6 C5 -0.26(14) . . . . ?
N1 C1 C6 C5 179.67(8) . . . . ?
C1 N1 C7 O1 -3.73(14) . . . . ?
C12 N1 C7 O1 -174.37(9) . . . . ?
C1 N1 C7 C8 179.02(8) . . . . ?
C12 N1 C7 C8 8.38(13) . . . . ?
O1 C7 C8 C9 -106.64(10) . . . . ?
N1 C7 C8 C9 70.63(11) . . . . ?
C7 C8 C9 C10 -76.82(10) . . . . ?
C8 C9 C10 C11 20.94(13) . . . . ?
C8 C9 C10 C13 -157.45(8) . . . . ?
C13 C10 C11 C12 177.38(9) . . . . ?
C9 C10 C11 C12 -0.92(16) . . . . ?
C7 N1 C12 C11 -64.41(12) . . . . ?
C1 N1 C12 C11 124.86(9) . . . . ?
C10 C11 C12 N1 40.24(14) . . . . ?
C11 C10 C13 C14 143.38(10) . . . . ?
C9 C10 C13 C14 -38.17(13) . . . . ?
C11 C10 C13 C18 -39.64(14) . . . . ?
C9 C10 C13 C18 138.82(10) . . . . ?
C18 C13 C14 C15 0.19(16) . . . . ?
C10 C13 C14 C15 177.27(10) . . . . ?
C13 C14 C15 C16 -0.94(18) . . . . ?
C14 C15 C16 C17 1.33(18) . . . . ?
C15 C16 C17 C18 -1.00(17) . . . . ?
C16 C17 C18 C13 0.26(17) . . . . ?
C14 C13 C18 C17 0.14(15) . . . . ?
C10 C13 C18 C17 -176.91(9) . . . . ?
