#------------------------------------------------------------------------------
#$Date: 2022-05-13 00:54:51 +0300 (Fri, 13 May 2022) $
#$Revision: 275372 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/00/7130074.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_7130074
loop_
_publ_author_name
'Trifonova, Evgeniya A.'
'Ankudinov, Nikita M.'
'Chusov, Denis'
'Nelyubina, Yulia V.'
'Perekalin, Dmitry S.'
_publ_section_title
;
 Asymmetric cyclopropanation of electron-rich alkenes by the racemic diene
 rhodium catalyst: the chiral poisoning approach
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01648F
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_sum            'C18 H23 N O3'
_chemical_formula_weight         301.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2022-03-21 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.66(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1340(18)
_cell_length_b                   6.2150(12)
_cell_length_c                   14.976(3)
_cell_measurement_reflns_used    3026
_cell_measurement_temperature    120
_cell_measurement_theta_max      14.85
_cell_measurement_theta_min      2.26
_cell_volume                     814.5(3)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type
'MarExperts mardtb goniostat and Rayonix SX 165 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.745
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.1191
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8466
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        26.551
_diffrn_reflns_theta_max         31.098
_diffrn_reflns_theta_min         2.467
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5296
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1825 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         4400
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0590
_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)+(0.0790P)²+0.0622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                4250
_reflns_number_total             4400
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc01648f3.cif
_cod_data_source_block           9a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130074
_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_max   0.994
_shelx_estimated_absorpt_t_min   0.964
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O1 O -0.7241(2) -0.8120(3) -0.43780(12) 0.0269(4) Uani 1 1 d . . . . .
O2 O -0.26965(18) -0.4988(3) -0.26243(11) 0.0263(4) Uani 1 1 d . . . . .
O3 O -0.42384(16) -0.5949(2) -0.17472(10) 0.0199(3) Uani 1 1 d . . . . .
N1 N -0.7022(2) -0.4571(3) -0.47337(11) 0.0183(3) Uani 1 1 d . . . . .
C1 C -0.5522(2) -0.4342(3) -0.41081(13) 0.0178(4) Uani 1 1 d . . . . .
H1 H -0.4736 -0.5323 -0.4234 0.021 Uiso 1 1 calc R U . . .
C2 C -0.5295(2) -0.3819(3) -0.30720(12) 0.0164(3) Uani 1 1 d . . . . .
C3 C -0.4941(2) -0.2186(3) -0.37367(14) 0.0210(4) Uani 1 1 d . . . . .
H3A H -0.5642 -0.0945 -0.3923 0.025 Uiso 1 1 calc R U . . .
H3B H -0.3854 -0.1860 -0.3667 0.025 Uiso 1 1 calc R U . . .
C4 C -0.7697(2) -0.6542(3) -0.48711(14) 0.0214(4) Uani 1 1 d . . . . .
C6 C -0.9138(3) -0.4124(4) -0.60503(15) 0.0254(4) Uani 1 1 d . . . . .
H6BC H -0.9299 -0.3961 -0.6729 0.030 Uiso 0.768(13) 1 calc R U P A 2
H6BD H -1.0006 -0.3454 -0.5883 0.030 Uiso 0.768(13) 1 calc R U P A 2
H6AA H -0.9996 -0.3137 -0.6068 0.030 Uiso 0.232(13) 1 calc R U P A 1
H6AB H -0.9129 -0.4414 -0.6699 0.030 Uiso 0.232(13) 1 calc R U P A 1
C7 C -0.7634(3) -0.3104(4) -0.55053(17) 0.0313(5) Uani 1 1 d . U . . .
H7A H -0.6930 -0.2972 -0.5897 0.038 Uiso 1 1 calc R U . . .
H7B H -0.7805 -0.1659 -0.5276 0.038 Uiso 1 1 calc R U . . .
C8 C -0.3927(2) -0.4959(3) -0.24639(13) 0.0193(4) Uani 1 1 d . . . . .
C9 C -0.3047(2) -0.7151(4) -0.10484(13) 0.0204(4) Uani 1 1 d . . . . .
C10 C -0.3934(3) -0.8022(4) -0.04055(15) 0.0256(4) Uani 1 1 d . . . . .
H10A H -0.4763 -0.8951 -0.0762 0.038 Uiso 1 1 calc R U . . .
H10B H -0.4363 -0.6820 -0.0140 0.038 Uiso 1 1 calc R U . . .
H10C H -0.3244 -0.8854 0.0098 0.038 Uiso 1 1 calc R U . . .
C11 C -0.2429(3) -0.8989(4) -0.15068(17) 0.0301(5) Uani 1 1 d . . . . .
H11A H -0.1819 -0.8403 -0.1892 0.045 Uiso 1 1 calc R U . . .
H11B H -0.3282 -0.9825 -0.1899 0.045 Uiso 1 1 calc R U . . .
H11C H -0.1786 -0.9923 -0.1024 0.045 Uiso 1 1 calc R U . . .
C12 C -0.1794(3) -0.5612(5) -0.05370(16) 0.0314(5) Uani 1 1 d . . . . .
H12A H -0.2253 -0.4356 -0.0326 0.047 Uiso 1 1 calc R U . . .
H12B H -0.1210 -0.5143 -0.0958 0.047 Uiso 1 1 calc R U . . .
H12C H -0.1110 -0.6343 0.0003 0.047 Uiso 1 1 calc R U . . .
C13 C -0.6634(2) -0.3427(3) -0.27082(12) 0.0158(4) Uani 1 1 d . . . . .
C14 C -0.6880(2) -0.1376(3) -0.23963(13) 0.0187(4) Uani 1 1 d . . . . .
H14 H -0.6219 -0.0227 -0.2441 0.022 Uiso 1 1 calc R U . . .
C15 C -0.8088(2) -0.0999(3) -0.20187(14) 0.0208(4) Uani 1 1 d . . . . .
H15 H -0.8226 0.0391 -0.1792 0.025 Uiso 1 1 calc R U . . .
C16 C -0.9088(2) -0.2649(3) -0.19745(14) 0.0206(4) Uani 1 1 d . . . . .
H16 H -0.9919 -0.2389 -0.1726 0.025 Uiso 1 1 calc R U . . .
C17 C -0.8865(2) -0.4687(3) -0.22958(14) 0.0202(4) Uani 1 1 d . . . . .
H17 H -0.9553 -0.5816 -0.2271 0.024 Uiso 1 1 calc R U . . .
C18 C -0.7641(2) -0.5087(3) -0.26531(13) 0.0183(4) Uani 1 1 d . . . . .
H18 H -0.7489 -0.6492 -0.2860 0.022 Uiso 1 1 calc R U . . .
C5' C -0.9328(16) -0.614(2) -0.5589(10) 0.0239(9) Uani 0.232(13) 1 d . . P A 1
H5'A H -0.9612 -0.7332 -0.6044 0.029 Uiso 0.232(13) 1 calc R U P A 1
H5'B H -1.0122 -0.5993 -0.5261 0.029 Uiso 0.232(13) 1 calc R U P A 1
C5 C -0.8981(5) -0.6532(6) -0.5767(3) 0.0239(9) Uani 0.768(13) 1 d . . P A 2
H5A H -0.9938 -0.7083 -0.5667 0.029 Uiso 0.768(13) 1 calc R U P A 2
H5B H -0.8721 -0.7417 -0.6250 0.029 Uiso 0.768(13) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0026 0.0018 '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 0.0049 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0092 0.0067 '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
C8 O3 C9 121.23(15) . . ?
C4 N1 C1 119.80(17) . . ?
C4 N1 C7 113.01(18) . . ?
C1 N1 C7 122.49(18) . . ?
N1 C1 C3 120.47(17) . . ?
N1 C1 C2 120.58(16) . . ?
C3 C1 C2 60.22(12) . . ?
N1 C1 H1 114.9 . . ?
C3 C1 H1 114.9 . . ?
C2 C1 H1 114.9 . . ?
C13 C2 C8 118.90(15) . . ?
C13 C2 C3 118.65(16) . . ?
C8 C2 C3 114.67(16) . . ?
C13 C2 C1 120.91(16) . . ?
C8 C2 C1 111.17(16) . . ?
C3 C2 C1 58.21(13) . . ?
C1 C3 C2 61.57(13) . . ?
C1 C3 H3A 117.6 . . ?
C2 C3 H3A 117.6 . . ?
C1 C3 H3B 117.6 . . ?
C2 C3 H3B 117.6 . . ?
H3A C3 H3B 114.7 . . ?
O1 C4 N1 124.64(19) . . ?
O1 C4 C5 125.6(2) . . ?
N1 C4 C5 109.5(2) . . ?
O1 C4 C5' 128.6(5) . . ?
N1 C4 C5' 104.9(5) . . ?
C5' C6 C7 108.3(5) . . ?
C7 C6 C5 104.9(2) . . ?
C7 C6 H6BC 110.8 . . ?
C5 C6 H6BC 110.8 . . ?
C7 C6 H6BD 110.8 . . ?
C5 C6 H6BD 110.8 . . ?
H6BC C6 H6BD 108.8 . . ?
C5' C6 H6AA 110.0 . . ?
C7 C6 H6AA 110.0 . . ?
C5' C6 H6AB 110.0 . . ?
C7 C6 H6AB 110.0 . . ?
H6AA C6 H6AB 108.4 . . ?
N1 C7 C6 104.34(19) . . ?
N1 C7 H7A 110.9 . . ?
C6 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O2 C8 O3 125.02(18) . . ?
O2 C8 C2 123.03(18) . . ?
O3 C8 C2 111.95(16) . . ?
O3 C9 C12 109.52(18) . . ?
O3 C9 C11 110.66(17) . . ?
C12 C9 C11 112.1(2) . . ?
O3 C9 C10 102.14(16) . . ?
C12 C9 C10 111.42(18) . . ?
C11 C9 C10 110.58(19) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.76(17) . . ?
C14 C13 C2 119.82(16) . . ?
C18 C13 C2 121.40(17) . . ?
C15 C14 C13 120.64(18) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.17(18) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.55(18) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.59(19) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.26(19) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C6 C5' C4 103.8(7) . . ?
C6 C5' H5'A 111.0 . . ?
C4 C5' H5'A 111.0 . . ?
C6 C5' H5'B 111.0 . . ?
C4 C5' H5'B 111.0 . . ?
H5'A C5' H5'B 109.0 . . ?
C4 C5 C6 103.6(2) . . ?
C4 C5 H5A 111.0 . . ?
C6 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
C6 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
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
O1 C4 1.226(3) . ?
O2 C8 1.215(2) . ?
O3 C8 1.337(2) . ?
O3 C9 1.478(2) . ?
N1 C4 1.360(3) . ?
N1 C1 1.428(3) . ?
N1 C7 1.452(3) . ?
C1 C3 1.488(3) . ?
C1 C2 1.540(3) . ?
C1 H1 1.0000 . ?
C2 C13 1.495(3) . ?
C2 C8 1.497(3) . ?
C2 C3 1.520(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.508(4) . ?
C4 C5' 1.587(13) . ?
C6 C5' 1.465(13) . ?
C6 C7 1.520(3) . ?
C6 C5 1.551(4) . ?
C6 H6BC 0.9900 . ?
C6 H6BD 0.9900 . ?
C6 H6AA 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C12 1.520(3) . ?
C9 C11 1.523(3) . ?
C9 C10 1.524(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.398(3) . ?
C13 C18 1.400(3) . ?
C14 C15 1.397(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
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
C4 N1 C1 C3 -162.28(18) . . . . ?
C7 N1 C1 C3 43.7(3) . . . . ?
C4 N1 C1 C2 -91.1(2) . . . . ?
C7 N1 C1 C2 114.9(2) . . . . ?
N1 C1 C2 C13 -3.3(3) . . . . ?
C3 C1 C2 C13 106.6(2) . . . . ?
N1 C1 C2 C8 143.44(19) . . . . ?
C3 C1 C2 C8 -106.65(18) . . . . ?
N1 C1 C2 C3 -109.9(2) . . . . ?
N1 C1 C3 C2 110.08(19) . . . . ?
C13 C2 C3 C1 -110.49(19) . . . . ?
C8 C2 C3 C1 100.54(18) . . . . ?
C1 N1 C4 O1 13.7(3) . . . . ?
C7 N1 C4 O1 170.0(2) . . . . ?
C1 N1 C4 C5 -160.8(3) . . . . ?
C7 N1 C4 C5 -4.5(3) . . . . ?
C1 N1 C4 C5' 179.4(7) . . . . ?
C7 N1 C4 C5' -24.3(7) . . . . ?
C4 N1 C7 C6 16.8(3) . . . . ?
C1 N1 C7 C6 172.37(18) . . . . ?
C5' C6 C7 N1 -0.9(8) . . . . ?
C5 C6 C7 N1 -21.4(3) . . . . ?
C9 O3 C8 O2 2.0(3) . . . . ?
C9 O3 C8 C2 -179.11(17) . . . . ?
C13 C2 C8 O2 -165.6(2) . . . . ?
C3 C2 C8 O2 -16.8(3) . . . . ?
C1 C2 C8 O2 46.9(3) . . . . ?
C13 C2 C8 O3 15.4(3) . . . . ?
C3 C2 C8 O3 164.33(17) . . . . ?
C1 C2 C8 O3 -132.01(17) . . . . ?
C8 O3 C9 C12 63.3(2) . . . . ?
C8 O3 C9 C11 -60.7(2) . . . . ?
C8 O3 C9 C10 -178.45(18) . . . . ?
C8 C2 C13 C14 103.2(2) . . . . ?
C3 C2 C13 C14 -44.4(2) . . . . ?
C1 C2 C13 C14 -112.5(2) . . . . ?
C8 C2 C13 C18 -75.4(2) . . . . ?
C3 C2 C13 C18 136.95(19) . . . . ?
C1 C2 C13 C18 68.8(2) . . . . ?
C18 C13 C14 C15 1.3(3) . . . . ?
C2 C13 C14 C15 -177.36(17) . . . . ?
C13 C14 C15 C16 -1.9(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C2 C13 C18 C17 178.85(17) . . . . ?
C7 C6 C5' C4 -12.2(11) . . . . ?
O1 C4 C5' C6 -173.1(4) . . . . ?
N1 C4 C5' C6 22.0(10) . . . . ?
O1 C4 C5 C6 176.1(2) . . . . ?
N1 C4 C5 C6 -9.5(4) . . . . ?
C7 C6 C5 C4 18.9(4) . . . . ?
