# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_sengoku-p-Cl-ph-181021a
_database_code_depnum_ccdc_archive 'CCDC 1878739'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C17 H16 Cl N O4'
_chemical_formula_moiety         'C17 H16 Cl N O4'
_chemical_formula_weight         333.77
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.7177(5)
_cell_length_b                   7.7029(6)
_cell_length_c                   35.315(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1555.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3784
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.00
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.974

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            14382
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.307
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3534
_reflns_number_gt                3262
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.987

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1235
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3534
_refine_ls_number_parameters     220
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0734P)²+0.0480P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.17884(16) 0.53504(12) 0.20159(2) 0.0457(2) Uani 1 1 d . . . . .
O1 O 0.4805(3) 0.7322(3) 0.56740(5) 0.0292(4) Uani 1 1 d . . . . .
O2 O 0.9798(3) 0.5172(3) 0.49502(6) 0.0293(4) Uani 1 1 d . . . . .
O3 O 0.7007(4) 0.6501(3) 0.37596(6) 0.0363(5) Uani 1 1 d . . . . .
O4 O 0.0046(4) 0.3184(3) 0.41003(7) 0.0493(6) Uani 1 1 d . . . . .
N1 N 0.3501(4) 0.5103(3) 0.36680(6) 0.0292(5) Uani 1 1 d . . . . .
C1 C 0.6487(4) 0.6238(3) 0.58219(7) 0.0226(5) Uani 1 1 d . . . . .
C2 C 0.6613(5) 0.5928(3) 0.62118(7) 0.0278(5) Uani 1 1 d . . . . .
H2 H 0.549188 0.642830 0.637761 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8387(5) 0.4886(4) 0.63550(7) 0.0305(6) Uani 1 1 d . . . . .
H3 H 0.848158 0.467426 0.661958 0.037 Uiso 1 1 calc R U . . .
C4 C 1.0033(5) 0.4149(4) 0.61109(8) 0.0299(6) Uani 1 1 d . . . . .
H4 H 1.126585 0.345593 0.620915 0.036 Uiso 1 1 calc R U . . .
C5 C 0.9856(4) 0.4436(3) 0.57226(8) 0.0260(5) Uani 1 1 d . . . . .
H5 H 1.096785 0.392141 0.555721 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8082(4) 0.5460(3) 0.55725(7) 0.0222(5) Uani 1 1 d . . . . .
C7 C 0.7765(4) 0.5720(3) 0.51514(7) 0.0236(5) Uani 1 1 d . . . . .
H7 H 0.748723 0.698011 0.510005 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5630(4) 0.4668(4) 0.50128(7) 0.0250(5) Uani 1 1 d . . . . .
H8A H 0.590136 0.341597 0.505909 0.030 Uiso 1 1 calc R U . . .
H8B H 0.422267 0.502186 0.515653 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5245(4) 0.4960(3) 0.46099(7) 0.0261(5) Uani 1 1 d . . . . .
C10 C 0.5115(5) 0.5281(4) 0.42805(8) 0.0275(5) Uani 1 1 d . . . . .
C11 C 0.5297(5) 0.5696(4) 0.38813(7) 0.0274(5) Uani 1 1 d . . . . .
C12 C 0.3195(5) 0.5247(4) 0.32728(7) 0.0278(5) Uani 1 1 d . . . . .
C13 C 0.1186(6) 0.4492(5) 0.31239(9) 0.0390(7) Uani 1 1 d . . . . .
H13 H 0.010250 0.394468 0.328914 0.047 Uiso 1 1 calc R U . . .
C14 C 0.0742(6) 0.4525(5) 0.27391(9) 0.0387(7) Uani 1 1 d . . . . .
H14 H -0.063002 0.399753 0.264015 0.046 Uiso 1 1 calc R U . . .
C15 C 0.2312(5) 0.5333(4) 0.25004(8) 0.0325(6) Uani 1 1 d . . . . .
C16 C 0.4299(6) 0.6117(5) 0.26432(9) 0.0416(7) Uani 1 1 d . . . . .
H16 H 0.535555 0.668681 0.247689 0.050 Uiso 1 1 calc R U . . .
C17 C 0.4756(6) 0.6074(4) 0.30305(8) 0.0374(7) Uani 1 1 d . . . . .
H17 H 0.612675 0.660606 0.312868 0.045 Uiso 1 1 calc R U . . .
H1 H 0.213(8) 0.470(7) 0.3855(14) 0.081(16) Uiso 1 1 d . . . . .
H6 H 0.380(9) 0.772(7) 0.5884(11) 0.067(13) Uiso 1 1 d . . . . .
H9 H 0.991(7) 0.569(6) 0.4771(12) 0.055(13) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b30 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b30'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b30'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Cl1 C15 1.737(3) . ?
O1 C1 1.376(3) . ?
O1 H6 0.99(5) . ?
O2 C7 1.426(3) . ?
O2 H9 0.75(4) . ?
O3 C11 1.235(3) . ?
N1 C11 1.353(3) . ?
N1 C12 1.411(3) . ?
N1 H1 1.07(5) . ?
C1 C2 1.399(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.512(3) . ?
C7 C8 1.545(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.457(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.191(4) . ?
C10 C11 1.449(3) . ?
C12 C13 1.391(4) . ?
C12 C17 1.391(4) . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(4) . ?
C16 C17 1.393(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
C1 O1 H6 108(3) . . ?
C7 O2 H9 110(3) . . ?
C11 N1 C12 128.2(2) . . ?
C11 N1 H1 108(3) . . ?
C12 N1 H1 123(3) . . ?
O1 C1 C2 120.9(2) . . ?
O1 C1 C6 118.4(2) . . ?
C2 C1 C6 120.7(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 122.6(2) . . ?
C1 C6 C7 118.9(2) . . ?
O2 C7 C6 110.7(2) . . ?
O2 C7 C8 109.3(2) . . ?
C6 C7 C8 109.7(2) . . ?
O2 C7 H7 109.0 . . ?
C6 C7 H7 109.0 . . ?
C8 C7 H7 109.0 . . ?
C9 C8 C7 110.3(2) . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 174.1(3) . . ?
C9 C10 C11 172.2(3) . . ?
O3 C11 N1 125.2(2) . . ?
O3 C11 C10 120.4(2) . . ?
N1 C11 C10 114.4(2) . . ?
C13 C12 C17 119.3(3) . . ?
C13 C12 N1 116.3(2) . . ?
C17 C12 N1 124.4(2) . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 Cl1 119.5(2) . . ?
C16 C15 Cl1 119.9(2) . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.6(3) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?

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
O1 C1 C2 C3 -177.4(2) . . . . ?
C6 C1 C2 C3 2.2(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C4 C5 C6 C7 -176.7(2) . . . . ?
O1 C1 C6 C5 176.8(2) . . . . ?
C2 C1 C6 C5 -2.8(4) . . . . ?
O1 C1 C6 C7 -5.1(3) . . . . ?
C2 C1 C6 C7 175.3(2) . . . . ?
C5 C6 C7 O2 -14.7(3) . . . . ?
C1 C6 C7 O2 167.2(2) . . . . ?
C5 C6 C7 C8 105.9(3) . . . . ?
C1 C6 C7 C8 -72.1(3) . . . . ?
O2 C7 C8 C9 -60.7(3) . . . . ?
C6 C7 C8 C9 177.8(2) . . . . ?
C12 N1 C11 O3 0.7(5) . . . . ?
C12 N1 C11 C10 -178.0(3) . . . . ?
C11 N1 C12 C13 179.1(3) . . . . ?
C11 N1 C12 C17 -0.6(5) . . . . ?
C17 C12 C13 C14 1.1(5) . . . . ?
N1 C12 C13 C14 -178.6(3) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 C16 -0.6(5) . . . . ?
C13 C14 C15 Cl1 179.0(3) . . . . ?
C14 C15 C16 C17 1.1(5) . . . . ?
Cl1 C15 C16 C17 -178.6(3) . . . . ?
C13 C12 C17 C16 -0.7(5) . . . . ?
N1 C12 C17 C16 179.0(3) . . . . ?
C15 C16 C17 C12 -0.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H6 O3 . . 3_466 2.717(3) 0.99(4) 1.73(5) 177(4) no
O2 H9 O1 . . 3_566 2.930(3) 0.75(4) 2.20(4) 166(4) no
N1 H1 O4 . . . 2.901(3) 1.07(5) 1.88(5) 158(4) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


