# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_103-5570-4610_l
_database_code_depnum_ccdc_archive 'CCDC 1541266'
_audit_update_record             
;
2017-03-30 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;
_audit_creation_method           'Olex2 1.2'

_audit_creation_date             2017-03-24
_chemical_formula_sum            'C10 H8 Cl N O2'
_chemical_formula_weight         209.620
_refine_ls_R_factor_all          0.058
_cell_length_a                   3.8516(2)
_cell_length_b                   11.2844(4)
_cell_length_c                   21.4208(8)
_cell_angle_alpha                90.000
_cell_angle_beta                 89.074(3)
_cell_angle_gamma                90.000
_cell_volume                     930.9(1)
_cell_formula_units_Z            4
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  -P_2ybc

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Cl ? 1.200
O ? 1.200
C ? 1.200
H ? 1.200
N ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
Cl1 Cl 0.0714(2) 0.5965(0) 0.1295(0) 1.000 4 e ? d Uani 0.0188(3)
O1 O 0.4094(5) 0.8142(2) 0.0961(1) 1.000 4 e ? d Uani 0.0182(5)
O2 O 0.0249(6) 0.6699(2) 0.4414(1) 1.000 4 e ? d Uani 0.0238(5)
C3 C 0.4622(7) 0.8940(2) 0.2014(1) 1.000 4 e ? d Uani 0.0165(6)
H3 H 0.5650 0.9638 0.1872 1.000 4 e ? calc Uiso 0.02000
N4 N 0.0300(7) 0.6604(2) 0.3759(1) 1.000 4 e ? d Uani 0.0210(6)
C5 C 0.3633(7) 0.8072(2) 0.1592(1) 1.000 4 e ? d Uani 0.0146(5)
C6 C 0.2031(7) 0.7039(2) 0.1822(1) 1.000 4 e ? d Uani 0.0159(6)
C7 C 0.1455(7) 0.6868(2) 0.2451(1) 1.000 4 e ? d Uani 0.0164(6)
H7 H 0.0375 0.6180 0.2593 1.000 4 e ? calc Uiso 0.02000
C8 C 0.1927(7) 0.7555(2) 0.3554(1) 1.000 4 e ? d Uani 0.0167(6)
C9 C 0.5785(8) 0.9187(2) 0.0728(1) 1.000 4 e ? d Uani 0.0197(6)
H9A H 0.6064 0.9130 0.0283 1.000 4 e ? calc Uiso 0.03000
H9B H 0.8023 0.9262 0.0915 1.000 4 e ? calc Uiso 0.03000
H9C H 0.4401 0.9870 0.0831 1.000 4 e ? calc Uiso 0.03000
C10 C 0.4066(7) 0.8761(2) 0.2650(1) 1.000 4 e ? d Uani 0.0165(6)
H10 H 0.4757 0.9341 0.2930 1.000 4 e ? calc Uiso 0.02000
C11 C 0.2497(7) 0.7733(2) 0.2877(1) 1.000 4 e ? d Uani 0.0154(6)
C12 C 0.2972(7) 0.8296(3) 0.4057(1) 1.000 4 e ? d Uani 0.0193(6)
H12 H 0.4156 0.9014 0.4035 1.000 4 e ? calc Uiso 0.02300
C13 C 0.1846(8) 0.7716(3) 0.4572(1) 1.000 4 e ? d Uani 0.0212(6)
H13 H 0.2131 0.7980 0.4979 1.000 4 e ? calc Uiso 0.02500



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C6 . . 1.738(3) no
O1 C5 . . 1.361(3) no
O1 C9 . . 1.433(3) no
O2 N4 . . 1.407(3) no
O2 C13 . . 1.347(4) no
C3 C5 . . 1.391(4) no
C3 C10 . . 1.391(4) no
N4 C8 . . 1.315(4) no
C5 C6 . . 1.405(4) no
C6 C7 . . 1.377(4) no
C7 C11 . . 1.398(4) no
C8 C11 . . 1.476(4) no
C8 C12 . . 1.428(4) no
C10 C11 . . 1.393(4) no
C12 C13 . . 1.349(4) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O1 C9 . . . 116.3(2) no
C13 O2 N4 . . . 108.4(2) no
C5 C3 C10 . . . 119.7(2) no
C8 N4 O2 . . . 105.7(2) no
O1 C5 C3 . . . 124.9(2) no
O1 C5 C6 . . . 116.4(2) no
C3 C5 C6 . . . 118.7(2) no
C5 C6 Cl1 . . . 118.8(2) no
C7 C6 Cl1 . . . 119.6(2) no
C7 C6 C5 . . . 121.5(2) no
C6 C7 C11 . . . 119.8(3) no
N4 C8 C11 . . . 120.2(2) no
N4 C8 C12 . . . 111.3(2) no
C12 C8 C11 . . . 128.5(3) no
C3 C10 C11 . . . 121.5(2) no
C7 C11 C8 . . . 120.4(2) no
C10 C11 C7 . . . 118.8(2) no
C10 C11 C8 . . . 120.9(2) no
C13 C12 C8 . . . 104.0(3) no
O2 C13 C12 . . . 110.6(2) no
