# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_7d
_database_code_depnum_ccdc_archive 'CCDC 1526459'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
_audit_creation_date             2017-01-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Br N2 O4'
_chemical_formula_sum            'C21 H17 Br N2 O4'
_chemical_formula_weight         441.27
_chemical_absolute_configuration unk
_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'
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'
Br Br -0.2901 2.4595 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.610(5)
_cell_length_b                   5.974(5)
_cell_length_c                   12.888(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.487(5)
_cell_angle_gamma                90
_cell_volume                     931.0(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8036
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.239
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6005
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1315 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.8058.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10915
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.117
_diffrn_reflns_theta_max         25.117
_diffrn_reflns_theta_min         2.670
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                3042
_reflns_number_total             3246
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.253
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.076(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0191P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0551
_refine_ls_wR_factor_ref         0.0560
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br -0.51914(2) 0.22942(8) -0.90626(2) 0.03374(12) Uani 1 1 d . . . . .
O2 O -0.71034(17) 0.1617(3) -0.45939(16) 0.0157(5) Uani 1 1 d . . . . .
O3 O -0.76385(16) -0.2706(6) -0.14348(15) 0.0240(5) Uani 1 1 d . . . . .
O4 O -1.13344(17) 0.2491(5) -0.36133(16) 0.0297(5) Uani 1 1 d . . . . .
N5 N -0.8264(2) -0.1650(5) 0.0511(2) 0.0222(7) Uani 1 1 d . . . . .
O6 O -0.97210(17) 0.1772(3) -0.39514(16) 0.0198(5) Uani 1 1 d . . . . .
N7 N -0.8945(2) 0.1530(5) -0.0310(2) 0.0239(7) Uani 1 1 d . . . . .
C8 C -0.7315(2) 0.2207(8) -0.3641(2) 0.0161(6) Uani 1 1 d . . . . .
C9 C -0.6289(2) 0.3168(6) -0.5917(3) 0.0156(7) Uani 1 1 d . . . . .
C10 C -0.6622(2) 0.3436(5) -0.4925(2) 0.0160(7) Uani 1 1 d . . . . .
C11 C -0.9001(2) -0.0140(5) -0.3891(2) 0.0175(7) Uani 1 1 d . . . . .
H11 H -0.893872 -0.048365 -0.463030 0.021 Uiso 1 1 calc R . . . .
C12 C -0.7844(2) 0.0424(5) -0.3137(2) 0.0164(7) Uani 1 1 d . . . . .
H12 H -0.737893 -0.095459 -0.306259 0.020 Uiso 1 1 calc R . . . .
C13 C -0.5711(2) 0.4868(6) -0.6261(2) 0.0189(7) Uani 1 1 d . . . . .
H13 H -0.554672 0.621384 -0.585431 0.023 Uiso 1 1 calc R . . . .
C14 C -0.7868(3) 0.1125(5) -0.2005(2) 0.0179(7) Uani 1 1 d . . . . .
H14A H -0.719128 0.199545 -0.166033 0.021 Uiso 1 1 calc R . . . .
H14B H -0.851205 0.211522 -0.206669 0.021 Uiso 1 1 calc R . . . .
C15 C -0.6543(2) 0.5132(6) -0.4215(2) 0.0191(7) Uani 1 1 d . . . . .
H15 H -0.624666 0.657922 -0.426130 0.023 Uiso 1 1 calc R . . . .
C16 C -0.8795(3) -0.0600(7) 0.1155(3) 0.0253(8) Uani 1 1 d . . . . .
H16 H -0.885940 -0.110968 0.183288 0.030 Uiso 1 1 calc R . . . .
C17 C -0.6529(3) 0.1183(6) -0.6523(3) 0.0187(7) Uani 1 1 d . . . . .
H17 H -0.692232 0.001008 -0.629811 0.022 Uiso 1 1 calc R . . . .
C18 C -0.5371(3) 0.4625(6) -0.7186(3) 0.0219(7) Uani 1 1 d . . . . .
H18 H -0.497476 0.578568 -0.741595 0.026 Uiso 1 1 calc R . . . .
C19 C -0.6190(3) 0.0943(6) -0.7449(2) 0.0212(7) Uani 1 1 d . . . . .
H19 H -0.634728 -0.039736 -0.786154 0.025 Uiso 1 1 calc R . . . .
C20 C -0.9597(2) -0.2002(5) -0.3529(2) 0.0198(7) Uani 1 1 d . . . . .
H20 H -0.933946 -0.350091 -0.341214 0.024 Uiso 1 1 calc R . . . .
C21 C -0.5623(2) 0.2655(7) -0.7770(2) 0.0213(8) Uani 1 1 d . . . . .
C22 C -0.8374(3) -0.0303(5) -0.0371(2) 0.0182(7) Uani 1 1 d . . . . .
C23 C -0.7936(2) -0.0845(6) -0.1284(2) 0.0161(7) Uani 1 1 d . . . . .
C24 C -0.6988(3) 0.4339(5) -0.3381(3) 0.0179(7) Uani 1 1 d . . . . .
H24 H -0.704403 0.514966 -0.276407 0.022 Uiso 1 1 calc R . . . .
C25 C -1.0631(3) 0.1141(6) -0.3640(2) 0.0218(8) Uani 1 1 d . . . . .
C26 C -0.9215(3) 0.1326(6) 0.0637(3) 0.0260(8) Uani 1 1 d . . . . .
H26 H -0.963918 0.238459 0.089999 0.031 Uiso 1 1 calc R . . . .
C27 C -1.0538(3) -0.1262(6) -0.3393(2) 0.0232(8) Uani 1 1 d . . . . .
H27 H -1.106505 -0.213885 -0.317311 0.028 Uiso 1 1 calc R . . . .
C28 C -0.7679(3) -0.3774(6) 0.0742(3) 0.0347(10) Uani 1 1 d . . . . .
H28A H -0.766089 -0.427239 0.147133 0.052 Uiso 1 1 calc GR . . . .
H28B H -0.692086 -0.358334 0.069814 0.052 Uiso 1 1 calc GR . . . .
H28C H -0.806049 -0.489565 0.021239 0.052 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
Br1 C21 1.906(3) . ?
O2 C8 1.374(3) . ?
O2 C10 1.371(4) . ?
O3 C23 1.206(5) . ?
O4 C25 1.206(4) . ?
N5 C16 1.359(4) . ?
N5 C22 1.367(4) . ?
N5 C28 1.455(5) . ?
O6 C11 1.447(4) . ?
O6 C25 1.371(4) . ?
N7 C22 1.325(4) . ?
N7 C26 1.364(4) . ?
C8 C12 1.500(5) . ?
C8 C24 1.351(6) . ?
C9 C10 1.463(4) . ?
C9 C13 1.394(5) . ?
C9 C17 1.405(4) . ?
C10 C15 1.350(5) . ?
C11 C12 1.543(4) . ?
C11 C20 1.489(4) . ?
C12 C14 1.526(4) . ?
C13 C18 1.384(4) . ?
C14 C23 1.517(4) . ?
C15 C24 1.428(5) . ?
C16 C26 1.360(5) . ?
C17 C19 1.385(4) . ?
C18 C21 1.384(5) . ?
C19 C21 1.377(5) . ?
C20 C27 1.324(4) . ?
C22 C23 1.470(4) . ?
C25 C27 1.468(5) . ?

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
C10 O2 C8 106.9(3) . . ?
C16 N5 C22 106.6(3) . . ?
C16 N5 C28 125.9(3) . . ?
C22 N5 C28 127.5(3) . . ?
C25 O6 C11 109.3(2) . . ?
C22 N7 C26 104.9(3) . . ?
O2 C8 C12 115.4(3) . . ?
C24 C8 O2 110.0(3) . . ?
C24 C8 C12 134.7(3) . . ?
C13 C9 C10 120.3(3) . . ?
C13 C9 C17 119.2(3) . . ?
C17 C9 C10 120.5(3) . . ?
O2 C10 C9 116.6(3) . . ?
C15 C10 O2 109.7(3) . . ?
C15 C10 C9 133.7(3) . . ?
O6 C11 C12 109.2(2) . . ?
O6 C11 C20 104.0(2) . . ?
C20 C11 C12 115.9(3) . . ?
C8 C12 C11 109.9(2) . . ?
C8 C12 C14 110.6(3) . . ?
C14 C12 C11 113.0(2) . . ?
C18 C13 C9 121.0(3) . . ?
C23 C14 C12 113.1(3) . . ?
C10 C15 C24 107.0(3) . . ?
N5 C16 C26 106.4(3) . . ?
C19 C17 C9 119.7(3) . . ?
C13 C18 C21 118.6(3) . . ?
C21 C19 C17 119.7(3) . . ?
C27 C20 C11 110.1(3) . . ?
C18 C21 Br1 119.5(3) . . ?
C19 C21 Br1 118.6(3) . . ?
C19 C21 C18 121.8(3) . . ?
N5 C22 C23 124.3(3) . . ?
N7 C22 N5 111.5(3) . . ?
N7 C22 C23 124.2(3) . . ?
O3 C23 C14 122.8(3) . . ?
O3 C23 C22 122.5(3) . . ?
C22 C23 C14 114.8(3) . . ?
C8 C24 C15 106.4(3) . . ?
O4 C25 O6 120.5(3) . . ?
O4 C25 C27 131.4(3) . . ?
O6 C25 C27 108.1(3) . . ?
C16 C26 N7 110.7(3) . . ?
C20 C27 C25 108.5(3) . . ?

_shelx_SHELXL_version_number     2016/4

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_5x
_database_code_depnum_ccdc_archive 'CCDC 1526458'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
_audit_creation_date             2017-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N2 O3 S'
_chemical_formula_sum            'C16 H16 N2 O3 S'
_chemical_formula_weight         316.37
_chemical_absolute_configuration unk
_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'
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'
S S 0.1246 0.1234 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.683(5)
_cell_length_b                   10.196(5)
_cell_length_c                   19.340(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1515.0(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7538
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1448 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.8807.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12101
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.045
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_min         2.106
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2502
_reflns_number_total             2671
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         1.460
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 
;
 Flack x determined using 994 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2671
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.060
_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)+(0.1173P)²+3.3665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1796
_refine_ls_wR_factor_ref         0.1839
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C10
 1.32 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15), C2(H2), C16(H16), C11(H11), C12(H12), C10(H10)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S1 S 0.8232(2) 0.67703(17) 0.37718(9) 0.0356(5) Uani 1 1 d . . . . .
O1 O 0.5030(5) 0.7111(4) 0.25429(19) 0.0155(8) Uani 1 1 d . . . . .
O3 O 0.6365(5) 1.0179(4) 0.4521(2) 0.0221(10) Uani 1 1 d . . . . .
N1 N 0.9369(6) 1.1698(4) 0.4126(2) 0.0156(9) Uani 1 1 d . . . . .
N2 N 0.9426(6) 1.0562(4) 0.3150(2) 0.0170(10) Uani 1 1 d . . . . .
C6 C 0.5054(7) 0.8096(5) 0.3695(3) 0.0153(11) Uani 1 1 d . . . . .
H6 H 0.423451 0.847670 0.404325 0.018 Uiso 1 1 calc R . . . .
O2 O 0.5153(6) 0.7669(5) 0.1422(2) 0.0291(11) Uani 1 1 d . . . . .
C9 C 0.6225(7) 0.7160(5) 0.4082(3) 0.0157(11) Uani 1 1 d D . . . .
C8 C 0.6971(7) 1.0077(5) 0.3942(3) 0.0157(11) Uani 1 1 d . . . . .
C14 C 0.8846(8) 1.2209(6) 0.4807(3) 0.0209(13) Uani 1 1 d . . . . .
H14A H 0.893819 1.151000 0.515298 0.031 Uiso 1 1 calc GR . . . .
H14B H 0.764102 1.252084 0.478533 0.031 Uiso 1 1 calc GR . . . .
H14C H 0.961256 1.293748 0.493713 0.031 Uiso 1 1 calc GR . . . .
C3 C 0.2888(7) 0.8525(5) 0.2174(3) 0.0211(12) Uani 1 1 d . . . . .
H3 H 0.221005 0.906073 0.187528 0.025 Uiso 1 1 calc R . . . .
C4 C 0.4443(7) 0.7772(5) 0.1975(3) 0.0181(12) Uani 1 1 d . . . . .
C15 C 1.0800(7) 1.2093(5) 0.3771(3) 0.0165(11) Uani 1 1 d . . . . .
H15 H 1.162458 1.273643 0.390851 0.020 Uiso 1 1 calc R . . . .
C5 C 0.3922(7) 0.7422(5) 0.3139(3) 0.0135(11) Uani 1 1 d . . . . .
C2 C 0.2597(7) 0.8332(5) 0.2833(3) 0.0208(13) Uani 1 1 d . . . . .
H2 H 0.166689 0.871729 0.308420 0.025 Uiso 1 1 calc R . . . .
C7 C 0.6093(7) 0.9254(5) 0.3389(3) 0.0161(11) Uani 1 1 d . . . . .
H7A H 0.698948 0.890838 0.306965 0.019 Uiso 1 1 calc R . . . .
H7B H 0.529575 0.981726 0.311786 0.019 Uiso 1 1 calc R . . . .
C16 C 1.0810(7) 1.1372(6) 0.3174(3) 0.0200(12) Uani 1 1 d . . . . .
H16 H 1.167464 1.143370 0.282422 0.024 Uiso 1 1 calc R . . . .
C11 C 0.7290(9) 0.5629(6) 0.4878(3) 0.0312(15) Uani 1 1 d . . . . .
H11 H 0.736936 0.504419 0.525894 0.037 Uiso 1 1 calc R . . . .
C13 C 0.8572(7) 1.0771(5) 0.3731(3) 0.0152(11) Uani 1 1 d . . . . .
C1 C 0.3078(8) 0.6145(5) 0.3392(3) 0.0188(12) Uani 1 1 d . . . . .
H1A H 0.235472 0.577627 0.302220 0.028 Uiso 1 1 calc GR . . . .
H1B H 0.235263 0.632749 0.379697 0.028 Uiso 1 1 calc GR . . . .
H1C H 0.398859 0.551450 0.351654 0.028 Uiso 1 1 calc GR . . . .
C12 C 0.8583(9) 0.5716(6) 0.4420(3) 0.0272(14) Uani 1 1 d . . . . .
H12 H 0.962256 0.521684 0.445865 0.033 Uiso 1 1 calc R . . . .
C10 C 0.5710(6) 0.6470(4) 0.4780(2) 0.0040(9) Uiso 1 1 d D . . . .
H10 H 0.469687 0.656036 0.505778 0.005 Uiso 1 1 calc R . . . .


_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
S1 C9 1.701(6) . ?
S1 C12 1.673(6) . ?
O1 C4 1.366(7) . ?
O1 C5 1.468(6) . ?
O3 C8 1.216(7) . ?
N1 C14 1.473(7) . ?
N1 C15 1.357(7) . ?
N1 C13 1.362(7) . ?
N2 C16 1.347(8) . ?
N2 C13 1.319(7) . ?
C6 C9 1.511(7) . ?
C6 C5 1.544(7) . ?
C6 C7 1.543(7) . ?
O2 C4 1.204(7) . ?
C9 C10 1.573(6) . ?
C8 C7 1.518(7) . ?
C8 C13 1.477(8) . ?
C3 C4 1.472(8) . ?
C3 C2 1.308(9) . ?
C15 C16 1.369(8) . ?
C5 C2 1.499(8) . ?
C5 C1 1.535(7) . ?
C11 C12 1.334(10) . ?
C11 C10 1.498(8) . ?

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
C12 S1 C9 91.8(3) . . ?
C4 O1 C5 109.5(4) . . ?
C15 N1 C14 124.6(5) . . ?
C15 N1 C13 106.7(4) . . ?
C13 N1 C14 128.7(5) . . ?
C13 N2 C16 105.3(5) . . ?
C9 C6 C5 113.5(4) . . ?
C9 C6 C7 111.4(4) . . ?
C7 C6 C5 111.4(4) . . ?
C6 C9 S1 120.8(4) . . ?
C6 C9 C10 123.9(4) . . ?
C10 C9 S1 115.3(4) . . ?
O3 C8 C7 121.7(5) . . ?
O3 C8 C13 122.2(5) . . ?
C13 C8 C7 116.1(4) . . ?
C2 C3 C4 108.3(5) . . ?
O1 C4 C3 108.4(5) . . ?
O2 C4 O1 121.4(5) . . ?
O2 C4 C3 130.2(5) . . ?
N1 C15 C16 105.8(5) . . ?
O1 C5 C6 108.5(4) . . ?
O1 C5 C2 102.5(4) . . ?
O1 C5 C1 108.1(4) . . ?
C2 C5 C6 112.5(4) . . ?
C2 C5 C1 111.3(4) . . ?
C1 C5 C6 113.2(4) . . ?
C3 C2 C5 111.3(5) . . ?
C8 C7 C6 112.5(4) . . ?
N2 C16 C15 110.7(5) . . ?
C12 C11 C10 118.8(6) . . ?
N1 C13 C8 123.5(5) . . ?
N2 C13 N1 111.5(5) . . ?
N2 C13 C8 125.0(5) . . ?
C11 C12 S1 114.8(5) . . ?
C11 C10 C9 99.2(4) . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5q
_database_code_depnum_ccdc_archive 'CCDC 1526457'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
_audit_creation_date             2017-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 Cl N2 O3'
_chemical_formula_sum            'C18 H17 Cl N2 O3'
_chemical_formula_weight         344.79
_chemical_absolute_configuration unk
_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'
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'
Cl Cl 0.1484 0.1585 '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                   10.8555(4)
_cell_length_b                   12.1442(5)
_cell_length_c                   12.5528(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1654.85(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1349 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.8536.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25291
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_min         2.480
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3734
_reflns_number_total             4126
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.235
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1481 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.053
_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)+(0.0380P)²+0.3878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0789
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C16(H16), C11(H11), C15(H15), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.25746(5) 0.66521(5) 0.40678(5) 0.02803(14) Uani 1 1 d . . . . .
O1 O 0.46754(14) 0.56213(11) 0.59468(12) 0.0196(3) Uani 1 1 d . . . . .
O2 O 0.13215(13) 0.28155(12) 0.52129(12) 0.0175(3) Uani 1 1 d . . . . .
O3 O 0.11054(15) 0.10543(13) 0.56898(13) 0.0263(4) Uani 1 1 d . . . . .
N2 N 0.63983(16) 0.48983(14) 0.75710(13) 0.0151(4) Uani 1 1 d . . . . .
N1 N 0.52844(15) 0.33598(15) 0.76765(14) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.54188(18) 0.43151(16) 0.71783(15) 0.0136(4) Uani 1 1 d . . . . .
C6 C 0.36604(18) 0.38627(16) 0.59561(17) 0.0154(4) Uani 1 1 d . . . . .
H6A H 0.317265 0.360425 0.657387 0.018 Uiso 1 1 calc R . . . .
H6B H 0.409447 0.321951 0.564967 0.018 Uiso 1 1 calc R . . . .
C2 C 0.6905(2) 0.42707(18) 0.83488(17) 0.0195(4) Uani 1 1 d . . . . .
H2 H 0.760521 0.444735 0.876989 0.023 Uiso 1 1 calc R . . . .
C1 C 0.6848(2) 0.59764(17) 0.72130(18) 0.0194(4) Uani 1 1 d . . . . .
H1A H 0.703205 0.594561 0.644936 0.029 Uiso 1 1 calc GR . . . .
H1B H 0.759701 0.616807 0.760708 0.029 Uiso 1 1 calc GR . . . .
H1C H 0.621433 0.653526 0.734370 0.029 Uiso 1 1 calc GR . . . .
C13 C 0.19114(19) 0.51833(17) 0.56069(17) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.45995(19) 0.47047(17) 0.63286(16) 0.0141(4) Uani 1 1 d . . . . .
C12 C 0.1738(2) 0.62319(18) 0.51834(19) 0.0209(5) Uani 1 1 d . . . . .
C3 C 0.62083(19) 0.33293(19) 0.84080(16) 0.0200(4) Uani 1 1 d . . . . .
H3 H 0.635090 0.274064 0.889097 0.024 Uiso 1 1 calc R . . . .
C17 C 0.16419(19) 0.17342(19) 0.51711(17) 0.0192(4) Uani 1 1 d . . . . .
C7 C 0.27969(18) 0.43482(16) 0.51229(16) 0.0147(4) Uani 1 1 d . . . . .
H7 H 0.332219 0.475652 0.460112 0.018 Uiso 1 1 calc R . . . .
C8 C 0.1220(2) 0.4916(2) 0.65043(17) 0.0228(5) Uani 1 1 d . . . . .
H8 H 0.131130 0.420684 0.681327 0.027 Uiso 1 1 calc R . . . .
C16 C 0.2678(2) 0.16211(19) 0.44297(17) 0.0213(4) Uani 1 1 d . . . . .
H16 H 0.308941 0.095305 0.426117 0.026 Uiso 1 1 calc R . . . .
C18 C 0.1267(2) 0.39543(19) 0.36378(18) 0.0223(5) Uani 1 1 d . . . . .
H18A H 0.081606 0.336598 0.327296 0.033 Uiso 1 1 calc GR . . . .
H18B H 0.177203 0.435669 0.312058 0.033 Uiso 1 1 calc GR . . . .
H18C H 0.068094 0.446142 0.397190 0.033 Uiso 1 1 calc GR . . . .
C14 C 0.20943(18) 0.34565(17) 0.44877(16) 0.0163(4) Uani 1 1 d . . . . .
C11 C 0.0912(2) 0.6980(2) 0.5619(2) 0.0297(6) Uani 1 1 d . . . . .
H11 H 0.080513 0.768548 0.530617 0.036 Uiso 1 1 calc R . . . .
C15 C 0.2945(2) 0.26006(18) 0.40344(18) 0.0201(4) Uani 1 1 d . . . . .
H15 H 0.358302 0.274322 0.353525 0.024 Uiso 1 1 calc R . . . .
C9 C 0.0403(2) 0.5654(2) 0.69599(19) 0.0299(6) Uani 1 1 d . . . . .
H9 H -0.005179 0.545408 0.757687 0.036 Uiso 1 1 calc R . . . .
C10 C 0.0254(2) 0.6688(2) 0.6508(2) 0.0345(6) Uani 1 1 d . . . . .
H10 H -0.030797 0.719626 0.681561 0.041 Uiso 1 1 calc R . . . .


_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 C12 1.745(2) . ?
O1 C5 1.215(2) . ?
O2 C17 1.359(3) . ?
O2 C14 1.462(2) . ?
O3 C17 1.202(3) . ?
N2 C4 1.369(3) . ?
N2 C2 1.355(3) . ?
N2 C1 1.468(3) . ?
N1 C4 1.326(3) . ?
N1 C3 1.360(3) . ?
C4 C5 1.467(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.518(3) . ?
C6 C7 1.523(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.373(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C13 C12 1.393(3) . ?
C13 C7 1.524(3) . ?
C13 C8 1.392(3) . ?
C12 C11 1.388(3) . ?
C3 H3 0.9500 . ?
C17 C16 1.466(3) . ?
C7 H7 1.0000 . ?
C7 C14 1.546(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.321(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C14 1.520(3) . ?
C14 C15 1.502(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.372(4) . ?
C15 H15 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.387(4) . ?
C10 H10 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
C17 O2 C14 110.08(16) . . ?
C4 N2 C1 127.54(17) . . ?
C2 N2 C4 106.49(17) . . ?
C2 N2 C1 125.95(17) . . ?
C4 N1 C3 105.13(18) . . ?
N2 C4 C5 124.45(18) . . ?
N1 C4 N2 111.60(17) . . ?
N1 C4 C5 123.94(18) . . ?
H6A C6 H6B 108.0 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.35(16) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
N2 C2 H2 126.8 . . ?
N2 C2 C3 106.46(18) . . ?
C3 C2 H2 126.8 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C12 C13 C7 122.8(2) . . ?
C8 C13 C12 116.7(2) . . ?
C8 C13 C7 120.5(2) . . ?
O1 C5 C4 122.76(19) . . ?
O1 C5 C6 122.78(18) . . ?
C4 C5 C6 114.45(17) . . ?
C13 C12 Cl1 120.21(17) . . ?
C11 C12 Cl1 117.44(19) . . ?
C11 C12 C13 122.3(2) . . ?
N1 C3 C2 110.31(19) . . ?
N1 C3 H3 124.8 . . ?
C2 C3 H3 124.8 . . ?
O2 C17 C16 108.14(19) . . ?
O3 C17 O2 121.2(2) . . ?
O3 C17 C16 130.6(2) . . ?
C6 C7 C13 111.84(17) . . ?
C6 C7 H7 106.9 . . ?
C6 C7 C14 112.74(16) . . ?
C13 C7 H7 106.9 . . ?
C13 C7 C14 111.14(16) . . ?
C14 C7 H7 106.9 . . ?
C13 C8 H8 119.0 . . ?
C9 C8 C13 121.9(2) . . ?
C9 C8 H8 119.0 . . ?
C17 C16 H16 125.6 . . ?
C15 C16 C17 108.8(2) . . ?
C15 C16 H16 125.6 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
O2 C14 C7 109.56(16) . . ?
O2 C14 C18 108.06(16) . . ?
O2 C14 C15 102.71(16) . . ?
C18 C14 C7 112.01(17) . . ?
C15 C14 C7 112.13(16) . . ?
C15 C14 C18 111.87(18) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.2(2) . . ?
C10 C11 H11 120.4 . . ?
C16 C15 C14 110.2(2) . . ?
C16 C15 H15 124.9 . . ?
C14 C15 H15 124.9 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
