#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:40:45 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257407 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557341.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_1557341
loop_
_publ_author_name
'Lin, Qianchi'
'Hu, Bowen'
'Xu, Xi'
'Dong, Shunxi'
'Liu, Xiaohua'
'Feng, Xiaoming'
_publ_section_title
;
 Chiral N,N′-dioxide/Mg(OTf)2 complex-catalyzed asymmetric
 [2,3]-rearrangement of in situ generated ammonium salts
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              3068
_journal_page_last               3073
_journal_paper_doi               10.1039/C9SC06342K
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H21 Cl0 N O2'
_chemical_formula_weight         247.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-10-23 deposited with the CCDC.	2020-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5161(5)
_cell_length_b                   10.5750(6)
_cell_length_c                   15.9557(9)
_cell_measurement_reflns_used    9006
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.44
_cell_measurement_theta_min      2.77
_cell_volume                     1436.93(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9239
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.431
_diffrn_reflns_theta_min         5.017
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             536
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 1050 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0630P)²+0.1459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                2531
_reflns_number_total             2537
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc06342k2.cif
_cod_data_source_block           cu_LQC20190608_1_0m_a
_cod_depositor_comments
;Adding full bibliography for 1557341.cif.

 Adding full bibliography for 1557341.cif.
;
_cod_database_code               1557341
_shelx_shelxl_version_number     2016/6
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.40780(17) 0.16639(12) 0.27830(10) 0.0509(4) Uani 1 1 d . . . . .
N1 N 0.53087(17) 0.31395(14) 0.11835(9) 0.0389(4) Uani 1 1 d . . . . .
C1 C 0.8740(2) 0.3267(2) 0.48680(11) 0.0505(5) Uani 1 1 d . . . . .
H1 H 0.911936 0.340794 0.542006 0.061 Uiso 1 1 calc R U . . .
C2 C 0.8099(2) 0.42449(19) 0.44146(12) 0.0477(5) Uani 1 1 d . . . . .
H2 H 0.803497 0.506480 0.465557 0.057 Uiso 1 1 calc R U . . .
O2 O 0.33193(15) 0.36834(12) 0.28579(9) 0.0453(3) Uani 1 1 d . . . . .
C3 C 0.7546(2) 0.40427(17) 0.36067(11) 0.0406(4) Uani 1 1 d . . . . .
H3 H 0.710178 0.472599 0.330119 0.049 Uiso 1 1 calc R U . . .
C4 C 0.76331(17) 0.28526(16) 0.32400(10) 0.0324(3) Uani 1 1 d . . . . .
C5 C 0.8274(2) 0.18732(17) 0.37083(11) 0.0405(4) Uani 1 1 d . . . . .
H5 H 0.833398 0.104985 0.347240 0.049 Uiso 1 1 calc R U . . .
C6 C 0.8827(2) 0.2076(2) 0.45128(12) 0.0503(5) Uani 1 1 d . . . . .
H6 H 0.926685 0.139543 0.482204 0.060 Uiso 1 1 calc R U . . .
C7 C 0.71651(19) 0.25891(15) 0.23323(10) 0.0325(4) Uani 1 1 d . . . . .
H7 H 0.696896 0.165988 0.228207 0.039 Uiso 1 1 calc R U . . .
C9 C 0.8841(2) 0.42731(17) 0.15645(12) 0.0430(4) Uani 1 1 d . . . . .
H9A H 0.977280 0.434081 0.120687 0.064 Uiso 1 1 calc R U . . .
H9B H 0.902331 0.473105 0.208951 0.064 Uiso 1 1 calc R U . . .
H9C H 0.793499 0.463989 0.127409 0.064 Uiso 1 1 calc R U . . .
C8 C 0.85234(19) 0.29116(17) 0.17521(10) 0.0356(4) Uani 1 1 d . . . . .
C10 C 0.9451(2) 0.2001(2) 0.14658(12) 0.0499(5) Uani 1 1 d . . . . .
H10A H 1.033994 0.220793 0.113343 0.060 Uiso 1 1 calc R U . . .
H10B H 0.922556 0.114268 0.159306 0.060 Uiso 1 1 calc R U . . .
C11 C 0.56449(18) 0.32683(14) 0.20839(10) 0.0326(4) Uani 1 1 d . . . . .
H11 H 0.577349 0.418819 0.221172 0.039 Uiso 1 1 calc R U . . .
C12 C 0.42926(19) 0.27578(16) 0.26212(10) 0.0347(4) Uani 1 1 d . . . . .
C13 C 0.1926(2) 0.3281(2) 0.33018(14) 0.0559(5) Uani 1 1 d . . . . .
H13A H 0.123039 0.282566 0.291651 0.084 Uiso 1 1 calc R U . . .
H13B H 0.137749 0.402292 0.352491 0.084 Uiso 1 1 calc R U . . .
H13C H 0.222504 0.272162 0.376468 0.084 Uiso 1 1 calc R U . . .
C14 C 0.5012(3) 0.18586(19) 0.08983(13) 0.0609(6) Uani 1 1 d . . . . .
H14A H 0.493811 0.184944 0.028534 0.091 Uiso 1 1 calc R U . . .
H14B H 0.402285 0.155424 0.113919 0.091 Uiso 1 1 calc R U . . .
H14C H 0.587322 0.130715 0.107761 0.091 Uiso 1 1 calc R U . . .
C15 C 0.4061(2) 0.3998(2) 0.09179(13) 0.0516(5) Uani 1 1 d . . . . .
H15A H 0.402665 0.403019 0.030439 0.077 Uiso 1 1 calc R U . . .
H15B H 0.426870 0.484615 0.113915 0.077 Uiso 1 1 calc R U . . .
H15C H 0.305099 0.369360 0.113206 0.077 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C14 N1 C15 111.25(17) . . ?
C14 N1 C11 115.25(14) . . ?
C15 N1 C11 111.56(14) . . ?
C2 C1 C6 119.37(17) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C1 C2 C3 120.47(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C12 O2 C13 115.57(15) . . ?
C4 C3 C2 120.78(17) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 118.03(15) . . ?
C5 C4 C7 118.46(15) . . ?
C3 C4 C7 123.38(15) . . ?
C6 C5 C4 121.13(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 120.22(18) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C4 109.74(12) . . ?
C8 C7 C11 112.34(13) . . ?
C4 C7 C11 112.34(13) . . ?
C8 C7 H7 107.4 . . ?
C4 C7 H7 107.4 . . ?
C11 C7 H7 107.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C8 C9 121.49(16) . . ?
C10 C8 C7 120.00(17) . . ?
C9 C8 C7 118.39(14) . . ?
C8 C10 H10A 120.0 . . ?
C8 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
N1 C11 C7 111.94(13) . . ?
N1 C11 C12 111.54(12) . . ?
C7 C11 C12 108.95(12) . . ?
N1 C11 H11 108.1 . . ?
C7 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
O1 C12 O2 123.43(16) . . ?
O1 C12 C11 125.05(16) . . ?
O2 C12 C11 111.45(14) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
O1 C12 1.199(2) . ?
N1 C14 1.451(2) . ?
N1 C15 1.460(2) . ?
N1 C11 1.471(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.383(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
O2 C12 1.337(2) . ?
O2 C13 1.446(2) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 C7 1.528(2) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.520(2) . ?
C7 C11 1.533(2) . ?
C7 H7 1.0000 . ?
C9 C8 1.495(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 C10 1.326(3) . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 C12 1.534(2) . ?
C11 H11 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O1 1.00 2.62 3.605(2) 167.9 3_655
C14 H14B O1 0.98 2.63 3.117(3) 111.2 .
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
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C2 C3 C4 C7 -175.06(16) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C7 C4 C5 C6 175.21(16) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C5 C4 C7 C8 -92.42(17) . . . . ?
C3 C4 C7 C8 83.29(19) . . . . ?
C5 C4 C7 C11 141.84(14) . . . . ?
C3 C4 C7 C11 -42.5(2) . . . . ?
C4 C7 C8 C10 99.51(19) . . . . ?
C11 C7 C8 C10 -134.75(17) . . . . ?
C4 C7 C8 C9 -76.48(18) . . . . ?
C11 C7 C8 C9 49.27(19) . . . . ?
C14 N1 C11 C7 64.0(2) . . . . ?
C15 N1 C11 C7 -167.93(13) . . . . ?
C14 N1 C11 C12 -58.4(2) . . . . ?
C15 N1 C11 C12 69.70(17) . . . . ?
C8 C7 C11 N1 48.57(17) . . . . ?
C4 C7 C11 N1 172.88(13) . . . . ?
C8 C7 C11 C12 172.40(13) . . . . ?
C4 C7 C11 C12 -63.29(16) . . . . ?
C13 O2 C12 O1 -2.4(3) . . . . ?
C13 O2 C12 C11 174.47(15) . . . . ?
N1 C11 C12 O1 81.0(2) . . . . ?
C7 C11 C12 O1 -43.1(2) . . . . ?
N1 C11 C12 O2 -95.88(16) . . . . ?
C7 C11 C12 O2 140.05(14) . . . . ?
