# 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_compound_5
_database_code_depnum_ccdc_archive 'CCDC 1967795'
loop_
_audit_author_name
_audit_author_address
'Christian Jandl'
;Technische Universitaet Muenchen
Germany
;
_audit_update_record             
;
2019-11-25 deposited with the CCDC.	2020-01-14 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 Cl N O2'
_chemical_formula_structural     ?
_chemical_formula_sum            'C17 H14 Cl N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         299.74
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_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                   5.3182(4)
_cell_length_b                   10.9400(7)
_cell_length_c                   23.9705(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1394.63(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9204
_cell_measurement_theta_min      2.5491
_cell_measurement_theta_max      26.9031
_cell_special_details            
;
;

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.110
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.277
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_absorpt_correction_T_min  0.7196
_exptl_absorpt_correction_T_max  0.7454

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             C. Jandl
scanspeed                           1-10 s per frame
dx                                  50 mm
2350 frames measured in 10 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
shutterless mode
;
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_monochromator  'Helios optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker Photon CMOS '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CMOS plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            37764
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2851
# number of observed reflections (> n sig(I))
_reflns_number_gt                2821
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX III Control Software (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2017)'
_computing_data_reduction        'SAINT (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL (Sheldrick, 2017), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2014)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0421P)²+0.4183P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed


_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.022(6)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration ad

_refine_ls_number_reflns         2851
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.042

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl Uani 0.46211(12) 0.45836(5) 0.51035(2) 1.000 0.0365(2) d . . .
O1 O Uani 0.9137(3) 0.38333(13) 0.76994(6) 1.000 0.0251(4) d . . .
O2 O Uani 0.7192(3) 0.04619(12) 0.70010(6) 1.000 0.0222(4) d . . .
N1 N Uani 0.6465(3) 0.35232(14) 0.84371(7) 1.000 0.0198(4) d . . .
C1 C Uani 0.7486(3) 0.32064(17) 0.79304(8) 1.000 0.0198(5) d . . .
C2 C Uani 0.6568(4) 0.20826(16) 0.76724(8) 1.000 0.0184(5) d . . .
C3 C Uani 0.4675(4) 0.14418(16) 0.79096(8) 1.000 0.0202(5) d . . .
C4 C Uani 0.3559(4) 0.18239(17) 0.84219(8) 1.000 0.0209(5) d . . .
C5 C Uani 0.1570(4) 0.11786(19) 0.86698(9) 1.000 0.0274(6) d . . .
C6 C Uani 0.0552(4) 0.1552(2) 0.91692(9) 1.000 0.0308(6) d . . .
C7 C Uani 0.1531(4) 0.2581(2) 0.94332(8) 1.000 0.0294(6) d . . .
C8 C Uani 0.3478(4) 0.32437(18) 0.92012(8) 1.000 0.0250(5) d . . .
C9 C Uani 0.4517(4) 0.28789(16) 0.86896(7) 1.000 0.0199(5) d . . .
C10 C Uani 0.7423(4) 0.4625(2) 0.87146(9) 1.000 0.0284(6) d . . .
C11 C Uani 0.7782(3) 0.16981(16) 0.71316(8) 1.000 0.0188(5) d . . .
C12 C Uani 0.6949(3) 0.24690(16) 0.66352(8) 1.000 0.0191(5) d . . .
C13 C Uani 0.8333(4) 0.2407(2) 0.61463(9) 1.000 0.0307(6) d . . .
C14 C Uani 0.7621(5) 0.3051(2) 0.56726(9) 1.000 0.0330(6) d . . .
C15 C Uani 0.5501(4) 0.37561(18) 0.56954(8) 1.000 0.0255(5) d . . .
C16 C Uani 0.4084(4) 0.3844(2) 0.61711(9) 1.000 0.0300(6) d . . .
C17 C Uani 0.4817(4) 0.31927(19) 0.66456(8) 1.000 0.0251(5) d . . .
H2 H Uiso 0.835(6) 0.000(3) 0.7159(13) 1.000 0.047(8) d . . .
H3 H Uiso 0.40765 0.07226 0.77316 1.000 0.0240 c RU . .
H5 H Uiso 0.09160 0.04732 0.84900 1.000 0.0330 c RU . .
H6 H Uiso -0.08027 0.11129 0.93321 1.000 0.0370 c RU . .
H7 H Uiso 0.08452 0.28320 0.97807 1.000 0.0350 c RU . .
H8 H Uiso 0.41126 0.39452 0.93876 1.000 0.0300 c RU . .
H10A H Uiso 0.88503 0.49506 0.85031 1.000 0.0430 c RU . .
H10B H Uiso 0.79702 0.44177 0.90934 1.000 0.0430 c RU . .
H10C H Uiso 0.60884 0.52410 0.87325 1.000 0.0430 c RU . .
H11 H Uiso 0.96472 0.17733 0.71721 1.000 0.0230 c RU . .
H13 H Uiso 0.98011 0.19131 0.61349 1.000 0.0370 c RU . .
H14 H Uiso 0.85860 0.30019 0.53399 1.000 0.0400 c RU . .
H16 H Uiso 0.26198 0.43414 0.61782 1.000 0.0360 c RU . .
H17 H Uiso 0.38450 0.32474 0.69772 1.000 0.0300 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C15 1.747(2) . . yes
O1 C1 1.244(2) . . yes
O2 C11 1.423(2) . . yes
N1 C1 1.375(2) . . yes
N1 C9 1.392(3) . . yes
N1 C10 1.468(3) . . yes
O2 H2 0.88(3) . . no
C1 C2 1.460(3) . . no
C2 C3 1.352(3) . . no
C2 C11 1.508(3) . . no
C3 C4 1.427(3) . . no
C4 C9 1.415(3) . . no
C4 C5 1.404(3) . . no
C5 C6 1.376(3) . . no
C6 C7 1.392(3) . . no
C7 C8 1.381(3) . . no
C8 C9 1.403(3) . . no
C11 C12 1.524(3) . . no
C12 C17 1.383(3) . . no
C12 C13 1.386(3) . . no
C13 C14 1.389(3) . . no
C14 C15 1.367(3) . . no
C15 C16 1.370(3) . . no
C16 C17 1.398(3) . . no
C3 H3 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C10 H10A 0.9800 . . no
C10 H10B 0.9800 . . no
C10 H10C 0.9800 . . no
C11 H11 1.0000 . . no
C13 H13 0.9500 . . no
C14 H14 0.9500 . . no
C16 H16 0.9500 . . no
C17 H17 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 123.41(15) . . . yes
C1 N1 C10 118.05(16) . . . yes
C9 N1 C10 118.50(16) . . . yes
C11 O2 H2 107(2) . . . no
O1 C1 C2 120.77(17) . . . yes
N1 C1 C2 117.02(16) . . . yes
O1 C1 N1 122.21(17) . . . yes
C1 C2 C3 120.49(17) . . . no
C1 C2 C11 117.11(16) . . . no
C3 C2 C11 122.39(16) . . . no
C2 C3 C4 121.32(17) . . . no
C3 C4 C5 122.04(18) . . . no
C5 C4 C9 119.30(18) . . . no
C3 C4 C9 118.65(18) . . . no
C4 C5 C6 121.03(19) . . . no
C5 C6 C7 119.2(2) . . . no
C6 C7 C8 121.45(19) . . . no
C7 C8 C9 119.87(18) . . . no
N1 C9 C4 118.94(16) . . . yes
C4 C9 C8 119.11(18) . . . no
N1 C9 C8 121.96(17) . . . yes
O2 C11 C12 106.86(15) . . . yes
C2 C11 C12 113.10(14) . . . no
O2 C11 C2 111.09(15) . . . yes
C11 C12 C17 122.75(16) . . . no
C13 C12 C17 118.60(18) . . . no
C11 C12 C13 118.61(16) . . . no
C12 C13 C14 121.5(2) . . . no
C13 C14 C15 118.6(2) . . . no
Cl1 C15 C14 118.74(16) . . . yes
Cl1 C15 C16 119.49(16) . . . yes
C14 C15 C16 121.76(19) . . . no
C15 C16 C17 119.22(19) . . . no
C12 C17 C16 120.39(18) . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C6 C7 H7 119.00 . . . no
C8 C7 H7 119.00 . . . no
C7 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
N1 C10 H10A 109.00 . . . no
N1 C10 H10B 109.00 . . . no
N1 C10 H10C 109.00 . . . no
H10A C10 H10B 109.00 . . . no
H10A C10 H10C 110.00 . . . no
H10B C10 H10C 109.00 . . . no
O2 C11 H11 109.00 . . . no
C2 C11 H11 109.00 . . . no
C12 C11 H11 109.00 . . . no
C12 C13 H13 119.00 . . . no
C14 C13 H13 119.00 . . . no
C13 C14 H14 121.00 . . . no
C15 C14 H14 121.00 . . . no
C15 C16 H16 120.00 . . . no
C17 C16 H16 120.00 . . . no
C12 C17 H17 120.00 . . . no
C16 C17 H17 120.00 . . . no

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
C9 N1 C1 O1 176.17(18) . . . . no
C9 N1 C1 C2 -4.5(3) . . . . no
C10 N1 C1 O1 -1.5(3) . . . . no
C10 N1 C1 C2 177.81(17) . . . . no
C1 N1 C9 C4 1.6(3) . . . . no
C1 N1 C9 C8 -178.48(18) . . . . no
C10 N1 C9 C4 179.22(17) . . . . no
C10 N1 C9 C8 -0.8(3) . . . . no
O1 C1 C2 C3 -176.26(18) . . . . no
O1 C1 C2 C11 2.5(3) . . . . no
N1 C1 C2 C3 4.4(3) . . . . no
N1 C1 C2 C11 -176.86(16) . . . . no
C1 C2 C3 C4 -1.4(3) . . . . no
C11 C2 C3 C4 179.93(18) . . . . no
C1 C2 C11 O2 165.21(16) . . . . no
C1 C2 C11 C12 -74.6(2) . . . . no
C3 C2 C11 O2 -16.1(3) . . . . no
C3 C2 C11 C12 104.1(2) . . . . no
C2 C3 C4 C5 179.1(2) . . . . no
C2 C3 C4 C9 -1.7(3) . . . . no
C3 C4 C5 C6 178.8(2) . . . . no
C9 C4 C5 C6 -0.4(3) . . . . no
C3 C4 C9 N1 1.7(3) . . . . no
C3 C4 C9 C8 -178.30(18) . . . . no
C5 C4 C9 N1 -179.10(18) . . . . no
C5 C4 C9 C8 1.0(3) . . . . no
C4 C5 C6 C7 -0.5(3) . . . . no
C5 C6 C7 C8 0.9(3) . . . . no
C6 C7 C8 C9 -0.3(3) . . . . no
C7 C8 C9 N1 179.42(19) . . . . no
C7 C8 C9 C4 -0.6(3) . . . . no
O2 C11 C12 C13 -72.4(2) . . . . no
O2 C11 C12 C17 105.2(2) . . . . no
C2 C11 C12 C13 165.08(17) . . . . no
C2 C11 C12 C17 -17.4(2) . . . . no
C11 C12 C13 C14 177.58(19) . . . . no
C17 C12 C13 C14 -0.1(3) . . . . no
C11 C12 C17 C16 -177.45(18) . . . . no
C13 C12 C17 C16 0.1(3) . . . . no
C12 C13 C14 C15 -0.1(3) . . . . no
C13 C14 C15 Cl1 179.17(17) . . . . no
C13 C14 C15 C16 0.3(3) . . . . no
Cl1 C15 C16 C17 -179.14(16) . . . . no
C14 C15 C16 C17 -0.2(3) . . . . no
C15 C16 C17 C12 0.1(3) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O2 H2 O1 0.88(3) 1.88(3) 2.739(2) 164(3) 4_746 yes
C3 H3 O2 0.9500 2.4300 2.772(2) 101.00 . yes
C10 H10A O1 0.9800 2.2900 2.739(3) 107.00 . yes
C10 H10A O2 0.9800 2.4900 3.462(3) 171.00 4_756 yes
C10 H10C O2 0.9800 2.4900 3.131(3) 123.00 4_656 yes

# Loop Mechanism for Extra Tables(s)


