# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_LQC20190608_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1960932'
loop_
_audit_author_name
_audit_author_address
'Qianchi Lin'
;Sichuan university
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2020-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H21 Cl0 N O2'
_chemical_formula_weight         247.33

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'

_cell_length_a                   8.5161(5)
_cell_length_b                   10.5750(6)
_cell_length_c                   15.9557(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1436.93(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9006
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      68.44

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.597
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5185
_exptl_absorpt_correction_T_max  0.7531
_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_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 1.54184    8.517   10.598   15.944   90.021   89.997   90.004
;
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9239
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.017
_diffrn_reflns_theta_max         68.431
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2537
_reflns_number_gt                2531
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.961

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.1459P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_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)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2537
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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 .

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.023

