# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_20160229-heyun-pengxiaojiao-pxj-cl-danjing1
_database_code_depnum_ccdc_archive 'CCDC 1496241'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;
_audit_creation_date             2016-02-29
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5097)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 Cl N2 O3'
_chemical_formula_sum            'C15 H17 Cl N2 O3'
_chemical_formula_weight         308.75
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_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'
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                   7.2915(5)
_cell_length_b                   12.7983(10)
_cell_length_c                   15.9552(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1488.92(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1880
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      4.0870
_cell_measurement_theta_max      26.6620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_min  0.76780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6234
_diffrn_reflns_point_group_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_min         3.430
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.500
_reflns_Friedel_fraction_full    0.736
_reflns_Friedel_fraction_max     0.597
_reflns_number_gt                2641
_reflns_number_total             3524
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.052
_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)+(0.0384P)²+0.1578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1103
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00e,H00i)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C00D(H00D), C00F(H00F), C00H(H00H)
2.d Idealised Me refined as rotating group:
 C00B(H00a,H00b,H00c), C00K(H00j,H00k,H00l), C00L(H00m,H00n,H00o)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl01 Cl 0.65918(13) 0.17919(7) 0.41821(5) 0.0513(3) Uani 1 1 d . . . . .
O002 O 0.6976(4) 0.11735(17) 0.94577(14) 0.0471(6) Uani 1 1 d . . . . .
O003 O 0.4967(4) 0.48385(18) 0.81141(14) 0.0550(7) Uani 1 1 d . . . . .
N004 N 0.4752(4) 0.2231(2) 0.84215(15) 0.0331(6) Uani 1 1 d . . . . .
H004 H 0.387(4) 0.240(3) 0.875(2) 0.040 Uiso 1 1 d R . . . .
N005 N 0.5894(4) 0.50078(19) 0.67513(16) 0.0433(7) Uani 1 1 d . . . . .
H005 H 0.5891 0.5678 0.6718 0.052 Uiso 1 1 calc R . . . .
O006 O 0.8717(5) 0.2556(2) 0.97438(16) 0.0714(9) Uani 1 1 d . . . . .
C007 C 0.7532(4) 0.2908(2) 0.78525(18) 0.0327(6) Uani 1 1 d . . . . .
C008 C 0.6257(4) 0.3306(2) 0.63501(18) 0.0318(6) Uani 1 1 d . . . . .
C009 C 0.6293(5) 0.4338(2) 0.60787(19) 0.0382(7) Uani 1 1 d . . . . .
C00A C 0.5902(4) 0.3290(2) 0.72841(17) 0.0315(6) Uani 1 1 d . . . . .
C00B C 0.8315(5) 0.1868(2) 0.7530(2) 0.0427(8) Uani 1 1 d . . . . .
H00A H 0.7337 0.1373 0.7463 0.064 Uiso 1 1 calc GR . . . .
H00B H 0.9189 0.1603 0.7926 0.064 Uiso 1 1 calc GR . . . .
H00C H 0.8907 0.1980 0.7000 0.064 Uiso 1 1 calc GR . . . .
C00C C 0.6591(5) 0.2781(2) 0.49319(18) 0.0367(7) Uani 1 1 d . . . . .
C00D C 0.6373(4) 0.2504(2) 0.57689(19) 0.0345(7) Uani 1 1 d . . . . .
H00D H 0.6307 0.1808 0.5932 0.041 Uiso 1 1 calc R . . . .
C00E C 0.5517(5) 0.4465(2) 0.7459(2) 0.0376(7) Uani 1 1 d . . . . .
C00F C 0.6578(6) 0.4611(3) 0.5253(2) 0.0468(9) Uani 1 1 d . . . . .
H00F H 0.6666 0.5307 0.5089 0.056 Uiso 1 1 calc R . . . .
C00G C 0.6457(5) 0.2738(2) 0.86826(18) 0.0334(7) Uani 1 1 d . . . . .
H00G H 0.6143 0.3427 0.8909 0.040 Uiso 1 1 calc R . . . .
C00H C 0.6728(5) 0.3801(3) 0.4677(2) 0.0465(8) Uani 1 1 d . . . . .
H00H H 0.6923 0.3952 0.4114 0.056 Uiso 1 1 calc R . . . .
C00I C 0.4290(4) 0.2607(3) 0.75714(18) 0.0354(7) Uani 1 1 d . . . . .
H00E H 0.3166 0.3012 0.7583 0.042 Uiso 1 1 calc R . . . .
H00I H 0.4124 0.2022 0.7192 0.042 Uiso 1 1 calc R . . . .
C00J C 0.7504(5) 0.2158(3) 0.9343(2) 0.0438(8) Uani 1 1 d . . . . .
C00K C 0.9072(5) 0.3705(3) 0.7941(2) 0.0485(9) Uani 1 1 d . . . . .
H00J H 0.9590 0.3847 0.7399 0.073 Uiso 1 1 calc GR . . . .
H00K H 1.0005 0.3431 0.8304 0.073 Uiso 1 1 calc GR . . . .
H00L H 0.8592 0.4340 0.8175 0.073 Uiso 1 1 calc GR . . . .
C00L C 0.7855(7) 0.0628(3) 1.0139(3) 0.0666(12) Uani 1 1 d . . . . .
H00M H 0.9132 0.0535 1.0013 0.100 Uiso 1 1 calc GR . . . .
H00N H 0.7287 -0.0043 1.0213 0.100 Uiso 1 1 calc GR . . . .
H00O H 0.7731 0.1028 1.0645 0.100 Uiso 1 1 calc GR . . . .


_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
Cl01 C00C 1.741(3) . ?
O002 C00J 1.330(4) . ?
O002 C00L 1.442(4) . ?
O003 C00E 1.217(4) . ?
N004 H004 0.86(3) . ?
N004 C00G 1.463(4) . ?
N004 C00I 1.478(4) . ?
N005 H005 0.8600 . ?
N005 C009 1.404(4) . ?
N005 C00E 1.354(4) . ?
O006 C00J 1.204(4) . ?
C007 C00A 1.573(4) . ?
C007 C00B 1.537(4) . ?
C007 C00G 1.554(4) . ?
C007 C00K 1.524(4) . ?
C008 C009 1.390(4) . ?
C008 C00A 1.513(4) . ?
C008 C00D 1.385(4) . ?
C009 C00F 1.379(4) . ?
C00A C00E 1.555(4) . ?
C00A C00I 1.535(4) . ?
C00B H00A 0.9600 . ?
C00B H00B 0.9600 . ?
C00B H00C 0.9600 . ?
C00C C00D 1.390(4) . ?
C00C C00H 1.371(5) . ?
C00D H00D 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00H 1.390(5) . ?
C00G H00G 0.9800 . ?
C00G C00J 1.498(4) . ?
C00H H00H 0.9300 . ?
C00I H00E 0.9700 . ?
C00I H00I 0.9700 . ?
C00K H00J 0.9600 . ?
C00K H00K 0.9600 . ?
C00K H00L 0.9600 . ?
C00L H00M 0.9600 . ?
C00L H00N 0.9600 . ?
C00L H00O 0.9600 . ?

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
C00J O002 C00L 115.7(3) . . ?
C00G N004 H004 111(2) . . ?
C00G N004 C00I 108.1(2) . . ?
C00I N004 H004 108(2) . . ?
C009 N005 H005 124.3 . . ?
C00E N005 H005 124.3 . . ?
C00E N005 C009 111.5(3) . . ?
C00B C007 C00A 110.9(2) . . ?
C00B C007 C00G 110.6(2) . . ?
C00G C007 C00A 98.9(2) . . ?
C00K C007 C00A 113.7(3) . . ?
C00K C007 C00B 109.7(3) . . ?
C00K C007 C00G 112.7(2) . . ?
C009 C008 C00A 108.8(3) . . ?
C00D C008 C009 119.6(3) . . ?
C00D C008 C00A 131.3(3) . . ?
C008 C009 N005 109.8(3) . . ?
C00F C009 N005 127.3(3) . . ?
C00F C009 C008 122.8(3) . . ?
C008 C00A C007 116.3(2) . . ?
C008 C00A C00E 101.2(2) . . ?
C008 C00A C00I 115.7(3) . . ?
C00E C00A C007 109.5(2) . . ?
C00I C00A C007 103.3(2) . . ?
C00I C00A C00E 111.0(3) . . ?
C007 C00B H00A 109.5 . . ?
C007 C00B H00B 109.5 . . ?
C007 C00B H00C 109.5 . . ?
H00A C00B H00B 109.5 . . ?
H00A C00B H00C 109.5 . . ?
H00B C00B H00C 109.5 . . ?
C00D C00C Cl01 118.4(2) . . ?
C00H C00C Cl01 119.2(2) . . ?
C00H C00C C00D 122.3(3) . . ?
C008 C00D C00C 117.5(3) . . ?
C008 C00D H00D 121.3 . . ?
C00C C00D H00D 121.3 . . ?
O003 C00E N005 125.6(3) . . ?
O003 C00E C00A 126.4(3) . . ?
N005 C00E C00A 108.1(3) . . ?
C009 C00F H00F 121.5 . . ?
C009 C00F C00H 117.0(3) . . ?
C00H C00F H00F 121.5 . . ?
N004 C00G C007 104.3(2) . . ?
N004 C00G H00G 107.8 . . ?
N004 C00G C00J 114.4(3) . . ?
C007 C00G H00G 107.8 . . ?
C00J C00G C007 114.3(3) . . ?
C00J C00G H00G 107.8 . . ?
C00C C00H C00F 120.6(3) . . ?
C00C C00H H00H 119.7 . . ?
C00F C00H H00H 119.7 . . ?
N004 C00I C00A 106.5(2) . . ?
N004 C00I H00E 110.4 . . ?
N004 C00I H00I 110.4 . . ?
C00A C00I H00E 110.4 . . ?
C00A C00I H00I 110.4 . . ?
H00E C00I H00I 108.6 . . ?
O002 C00J C00G 114.7(3) . . ?
O006 C00J O002 122.7(3) . . ?
O006 C00J C00G 122.6(3) . . ?
C007 C00K H00J 109.5 . . ?
C007 C00K H00K 109.5 . . ?
C007 C00K H00L 109.5 . . ?
H00J C00K H00K 109.5 . . ?
H00J C00K H00L 109.5 . . ?
H00K C00K H00L 109.5 . . ?
O002 C00L H00M 109.5 . . ?
O002 C00L H00N 109.5 . . ?
O002 C00L H00O 109.5 . . ?
H00M C00L H00N 109.5 . . ?
H00M C00L H00O 109.5 . . ?
H00N C00L H00O 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
Cl01 C00C C00D C008 -175.9(2) . . . . ?
Cl01 C00C C00H C00F 174.6(3) . . . . ?
N004 C00G C00J O002 14.6(4) . . . . ?
N004 C00G C00J O006 -164.8(3) . . . . ?
N005 C009 C00F C00H -172.2(4) . . . . ?
C007 C00A C00E O003 -64.9(4) . . . . ?
C007 C00A C00E N005 115.3(3) . . . . ?
C007 C00A C00I N004 21.5(3) . . . . ?
C007 C00G C00J O002 -105.6(3) . . . . ?
C007 C00G C00J O006 75.0(4) . . . . ?
C008 C009 C00F C00H 3.7(6) . . . . ?
C008 C00A C00E O003 171.8(3) . . . . ?
C008 C00A C00E N005 -8.0(3) . . . . ?
C008 C00A C00I N004 149.7(3) . . . . ?
C009 N005 C00E O003 -173.0(4) . . . . ?
C009 N005 C00E C00A 6.8(4) . . . . ?
C009 C008 C00A C007 -112.0(3) . . . . ?
C009 C008 C00A C00E 6.5(3) . . . . ?
C009 C008 C00A C00I 126.6(3) . . . . ?
C009 C008 C00D C00C 2.4(5) . . . . ?
C009 C00F C00H C00C 0.1(6) . . . . ?
C00A C007 C00G N004 42.4(3) . . . . ?
C00A C007 C00G C00J 168.1(3) . . . . ?
C00A C008 C009 N005 -3.0(4) . . . . ?
C00A C008 C009 C00F -179.6(3) . . . . ?
C00A C008 C00D C00C 175.5(3) . . . . ?
C00B C007 C00A C008 -49.9(4) . . . . ?
C00B C007 C00A C00E -163.8(2) . . . . ?
C00B C007 C00A C00I 77.9(3) . . . . ?
C00B C007 C00G N004 -73.9(3) . . . . ?
C00B C007 C00G C00J 51.8(3) . . . . ?
C00D C008 C009 N005 171.5(3) . . . . ?
C00D C008 C009 C00F -5.0(5) . . . . ?
C00D C008 C00A C007 74.3(4) . . . . ?
C00D C008 C00A C00E -167.2(3) . . . . ?
C00D C008 C00A C00I -47.1(4) . . . . ?
C00D C00C C00H C00F -2.6(6) . . . . ?
C00E N005 C009 C008 -2.5(4) . . . . ?
C00E N005 C009 C00F 173.8(4) . . . . ?
C00E C00A C00I N004 -95.8(3) . . . . ?
C00G N004 C00I C00A 5.6(3) . . . . ?
C00G C007 C00A C008 -166.0(2) . . . . ?
C00G C007 C00A C00E 80.1(3) . . . . ?
C00G C007 C00A C00I -38.2(3) . . . . ?
C00H C00C C00D C008 1.3(5) . . . . ?
C00I N004 C00G C007 -31.0(3) . . . . ?
C00I N004 C00G C00J -156.7(3) . . . . ?
C00I C00A C00E O003 48.5(5) . . . . ?
C00I C00A C00E N005 -131.3(3) . . . . ?
C00K C007 C00A C008 74.3(3) . . . . ?
C00K C007 C00A C00E -39.6(3) . . . . ?
C00K C007 C00A C00I -157.9(3) . . . . ?
C00K C007 C00G N004 162.9(3) . . . . ?
C00K C007 C00G C00J -71.4(3) . . . . ?
C00L O002 C00J O006 4.5(5) . . . . ?
C00L O002 C00J C00G -174.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
