# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1436586'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2017-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Cl N O'
_chemical_formula_weight         78.48

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5682(10)
_cell_length_b                   9.6574(10)
_cell_length_c                   14.7650(15)
_cell_angle_alpha                88.829(2)
_cell_angle_beta                 86.829(2)
_cell_angle_gamma                76.122(2)
_cell_volume                     1322.5(2)
_cell_formula_units_Z            17
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             663
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7977
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         28.29
_reflns_number_total             5892
_reflns_number_gt                4153
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) 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     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5892
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1771
_refine_ls_R_factor_gt           0.1424
_refine_ls_wR_factor_ref         0.3979
_refine_ls_wR_factor_gt          0.3505
_refine_ls_goodness_of_fit_ref   2.407
_refine_ls_restrained_S_all      2.407
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.005

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.14470(19) 0.21648(19) 0.24907(12) 0.0525(5) Uiso 1 1 d . . .
Cl2 Cl 0.1701(2) 0.4321(2) -0.25476(13) 0.0567(6) Uiso 1 1 d . . .
O1 O 0.4646(4) 0.4222(4) -0.3349(3) 0.0367(10) Uiso 1 1 d . . .
O5 O 0.4753(4) 0.2983(4) 0.2238(3) 0.0367(10) Uiso 1 1 d . . .
O4 O 0.4344(4) 0.0990(4) 0.1630(3) 0.0386(10) Uiso 1 1 d . . .
O2 O 0.5065(5) 0.2030(5) -0.2682(3) 0.0387(10) Uiso 1 1 d . . .
O3 O 0.8080(5) 0.1837(5) 0.1192(3) 0.0425(11) Uiso 1 1 d . . .
N2 N 0.5664(5) 0.0755(5) 0.2822(3) 0.0308(11) Uiso 1 1 d . . .
C7 C 0.3697(6) 0.3833(6) -0.3959(4) 0.0316(13) Uiso 1 1 d . . .
N1 N 0.5889(5) 0.3896(5) -0.2128(3) 0.0339(11) Uiso 1 1 d . . .
C9 C 0.3376(6) 0.1788(6) 0.1051(4) 0.0276(12) Uiso 1 1 d . . .
C10 C 0.7072(6) 0.1797(6) -0.1190(4) 0.0293(12) Uiso 1 1 d . . .
O6 O 0.8827(5) 0.1961(5) 0.5631(3) 0.0485(12) Uiso 1 1 d . . .
C12 C 0.4930(6) 0.1693(6) 0.2256(4) 0.0301(12) Uiso 1 1 d . . .
C13 C 0.7156(6) 0.2194(6) 0.3474(4) 0.0308(12) Uiso 1 1 d . . .
C14 C 0.7600(6) 0.2236(6) 0.0337(4) 0.0309(12) Uiso 1 1 d . . .
C15 C 0.8051(6) 0.1600(6) 0.4955(4) 0.0315(12) Uiso 1 1 d . . .
C16 C 0.2267(6) 0.3907(6) -0.3661(4) 0.0318(13) Uiso 1 1 d . . .
C17 C 0.7399(6) 0.0450(6) 0.5027(4) 0.0338(13) Uiso 1 1 d . . .
C18 C 0.6470(6) 0.1080(6) 0.3536(4) 0.0282(12) Uiso 1 1 d . . .
C19 C 0.7615(6) 0.1299(6) -0.0361(4) 0.0282(12) Uiso 1 1 d . . .
C20 C 0.4168(6) 0.3575(6) -0.4838(4) 0.0342(13) Uiso 1 1 d . . .
C21 C 0.1955(6) 0.2351(6) 0.1352(4) 0.0329(13) Uiso 1 1 d . . .
C22 C 0.7943(6) 0.2441(6) 0.4194(4) 0.0324(13) Uiso 1 1 d . . .
C23 C 0.6501(6) 0.3281(6) -0.1317(4) 0.0297(12) Uiso 1 1 d . . .
C24 C 0.6621(6) 0.0195(6) 0.4295(4) 0.0344(13) Uiso 1 1 d . . .
C25 C 0.5201(6) 0.3247(6) -0.2702(4) 0.0294(12) Uiso 1 1 d . . .
C26 C 0.3780(7) 0.1896(6) 0.0162(4) 0.0378(14) Uiso 1 1 d . . .
C27 C 0.1306(7) 0.3670(7) -0.4270(4) 0.0418(15) Uiso 1 1 d . . .
C28 C 0.6548(6) 0.4216(6) -0.0620(4) 0.0352(13) Uiso 1 1 d . . .
C29 C 0.3190(7) 0.3378(7) -0.5461(4) 0.0412(15) Uiso 1 1 d . . .
C30 C 0.2754(7) 0.2579(7) -0.0447(4) 0.0411(15) Uiso 1 1 d . . .
C31 C 0.0928(7) 0.3041(7) 0.0753(4) 0.0413(15) Uiso 1 1 d . . .
C32 C 0.1356(7) 0.3147(7) -0.0155(4) 0.0431(16) Uiso 1 1 d . . .
C33 C 0.7078(7) 0.3698(6) 0.0206(4) 0.0371(14) Uiso 1 1 d . . .
C34 C 0.1761(7) 0.3413(7) -0.5181(5) 0.0429(15) Uiso 1 1 d . . .
C35 C 0.8655(8) 0.0343(8) 0.1365(5) 0.0479(17) Uiso 1 1 d . . .
C36 C 0.9033(8) 0.1048(8) 0.6426(5) 0.0519(18) Uiso 1 1 d . . .

_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 C21 1.742(6) . ?
Cl2 C16 1.726(6) . ?
O1 C25 1.364(7) . ?
O1 C7 1.431(7) . ?
O5 C12 1.216(7) . ?
O4 C12 1.377(7) . ?
O4 C9 1.379(7) . ?
O2 C25 1.212(7) . ?
O3 C14 1.383(7) . ?
O3 C35 1.439(8) . ?
N2 C12 1.320(7) . ?
N2 C18 1.423(7) . ?
C7 C20 1.358(8) . ?
C7 C16 1.400(8) . ?
N1 C25 1.352(7) . ?
N1 C23 1.417(7) . ?
C9 C26 1.356(8) . ?
C9 C21 1.390(8) . ?
C10 C19 1.388(8) . ?
C10 C23 1.419(8) . ?
O6 C15 1.375(7) . ?
O6 C36 1.446(9) . ?
C13 C18 1.387(8) . ?
C13 C22 1.393(8) . ?
C14 C19 1.383(8) . ?
C14 C33 1.393(8) . ?
C15 C22 1.368(8) . ?
C15 C17 1.398(8) . ?
C16 C27 1.381(8) . ?
C17 C24 1.403(8) . ?
C18 C24 1.388(8) . ?
C20 C29 1.395(9) . ?
C21 C31 1.397(9) . ?
C23 C28 1.393(8) . ?
C26 C30 1.404(9) . ?
C27 C34 1.400(9) . ?
C28 C33 1.384(8) . ?
C29 C34 1.398(9) . ?
C30 C32 1.368(9) . ?
C31 C32 1.389(9) . ?

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
C25 O1 C7 117.3(4) . . ?
C12 O4 C9 118.5(4) . . ?
C14 O3 C35 117.7(5) . . ?
C12 N2 C18 125.3(5) . . ?
C20 C7 C16 122.1(5) . . ?
C20 C7 O1 118.4(5) . . ?
C16 C7 O1 119.0(5) . . ?
C25 N1 C23 125.0(5) . . ?
C26 C9 O4 119.5(5) . . ?
C26 C9 C21 120.0(5) . . ?
O4 C9 C21 120.2(5) . . ?
C19 C10 C23 119.4(5) . . ?
C15 O6 C36 117.5(5) . . ?
O5 C12 N2 129.1(5) . . ?
O5 C12 O4 121.7(5) . . ?
N2 C12 O4 109.3(5) . . ?
C18 C13 C22 119.2(5) . . ?
O3 C14 C19 124.7(5) . . ?
O3 C14 C33 115.1(5) . . ?
C19 C14 C33 120.2(5) . . ?
C22 C15 O6 116.0(5) . . ?
C22 C15 C17 121.0(5) . . ?
O6 C15 C17 123.0(5) . . ?
C27 C16 C7 119.4(5) . . ?
C27 C16 Cl2 120.3(5) . . ?
C7 C16 Cl2 120.3(4) . . ?
C15 C17 C24 117.8(6) . . ?
C13 C18 C24 119.8(5) . . ?
C13 C18 N2 122.2(5) . . ?
C24 C18 N2 117.9(5) . . ?
C14 C19 C10 120.5(5) . . ?
C7 C20 C29 118.6(6) . . ?
C9 C21 C31 120.9(5) . . ?
C9 C21 Cl1 119.3(4) . . ?
C31 C21 Cl1 119.7(5) . . ?
C15 C22 C13 120.9(6) . . ?
C28 C23 N1 116.8(5) . . ?
C28 C23 C10 119.3(5) . . ?
N1 C23 C10 123.9(5) . . ?
C18 C24 C17 121.1(6) . . ?
O2 C25 N1 128.8(5) . . ?
O2 C25 O1 123.7(5) . . ?
N1 C25 O1 107.5(5) . . ?
C9 C26 C30 119.6(6) . . ?
C16 C27 C34 119.6(6) . . ?
C33 C28 C23 120.4(6) . . ?
C20 C29 C34 120.7(6) . . ?
C32 C30 C26 120.9(6) . . ?
C32 C31 C21 118.5(6) . . ?
C30 C32 C31 120.1(6) . . ?
C28 C33 C14 120.1(6) . . ?
C29 C34 C27 119.5(6) . . ?

_diffrn_measured_fraction_theta_max 0.898
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.898
_refine_diff_density_max         2.035
_refine_diff_density_min         -1.484
_refine_diff_density_rms         0.172
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1436585'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2017-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7.50 H7 Cl0.50 N0.50 O1.50'
_chemical_formula_weight         145.86

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.407
_cell_length_b                   7.782
_cell_length_c                   16.311
_cell_angle_alpha                96.51
_cell_angle_beta                 95.82
_cell_angle_gamma                90.74
_cell_volume                     678.2
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.714
_exptl_crystal_F_000             152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4161
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.527
_diffrn_reflns_theta_max         28.245
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3028
_reflns_number_gt                2568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3028
_refine_ls_number_parameters     81
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.1170
_refine_ls_wR_factor_ref         0.3514
_refine_ls_wR_factor_gt          0.3289
_refine_ls_goodness_of_fit_ref   2.536
_refine_ls_restrained_S_all      2.536
_refine_ls_shift/su_max          1.008
_refine_ls_shift/su_mean         0.243

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 0.7217(2) 0.33174(14) -0.42923(7) 0.0400(5) Uiso 1 1 d . . . . .
O1 O 0.6740(6) 0.7281(4) -0.04686(18) 0.0316(7) Uiso 1 1 d . . . . .
C11 C 0.9436(7) 1.0349(5) 0.3309(2) 0.0246(9) Uiso 1 1 d . . . . .
O3 O 0.4179(6) 0.8212(4) 0.0499(2) 0.0383(8) Uiso 1 1 d . . . . .
O2 O 0.9627(6) 1.0904(4) 0.41347(19) 0.0329(8) Uiso 1 1 d . . . . .
C6 C 0.7474(8) 0.4974(5) -0.1869(3) 0.0288(9) Uiso 1 1 d . . . . .
C3 C 0.4340(8) 0.5306(5) -0.3317(3) 0.0296(9) Uiso 1 1 d . . . . .
C8 C 0.8644(7) 0.9125(5) 0.1615(2) 0.0233(8) Uiso 1 1 d . . . . .
C9 C 1.0780(8) 1.0117(5) 0.1938(3) 0.0274(9) Uiso 1 1 d . . . . .
C1 C 0.8047(8) 0.4173(5) -0.2629(3) 0.0288(9) Uiso 1 1 d . . . . .
C4 C 0.3813(8) 0.6111(5) -0.2551(3) 0.0295(9) Uiso 1 1 d . . . . .
N1 N 0.8430(7) 0.8430(4) 0.0766(2) 0.0286(8) Uiso 1 1 d . . . . .
C19 C 0.6284(8) 0.8017(5) 0.0298(3) 0.0279(9) Uiso 1 1 d . . . . .
C13 C 0.6908(8) 0.8744(5) 0.2155(2) 0.0255(9) Uiso 1 1 d . . . . .
C5 C 0.5326(7) 0.5945(5) -0.1829(2) 0.0240(8) Uiso 1 1 d . . . . .
C10 C 1.1176(7) 1.0741(5) 0.2775(3) 0.0254(9) Uiso 1 1 d . . . . .
C7 C 0.4547(9) 0.6746(6) -0.1018(3) 0.0336(10) Uiso 1 1 d . . . . .
C14 C 1.1912(9) 1.1660(6) 0.4515(3) 0.0349(10) Uiso 1 1 d . . . . .
C12 C 0.7302(8) 0.9373(5) 0.2986(2) 0.0257(9) Uiso 1 1 d . . . . .
C2 C 0.6468(8) 0.4341(5) -0.3341(3) 0.0259(9) Uiso 1 1 d . . . . .

_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 C2 1.749(4) . ?
O1 C19 1.362(5) . ?
O1 C7 1.439(5) . ?
C11 O2 1.360(5) . ?
C11 C10 1.399(6) . ?
C11 C12 1.396(5) . ?
O3 C19 1.223(5) . ?
O2 C14 1.414(5) . ?
C6 C5 1.397(6) . ?
C6 C1 1.389(6) . ?
C3 C4 1.390(6) . ?
C3 C2 1.384(6) . ?
C8 C9 1.403(5) . ?
C8 N1 1.422(5) . ?
C8 C13 1.402(5) . ?
C9 C10 1.390(6) . ?
C1 C2 1.389(6) . ?
C4 C5 1.384(6) . ?
N1 C19 1.337(5) . ?
C13 C12 1.382(6) . ?
C5 C7 1.499(6) . ?

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
C19 O1 C7 114.5(3) . . ?
O2 C11 C10 124.4(4) . . ?
O2 C11 C12 116.4(3) . . ?
C10 C11 C12 119.2(4) . . ?
C11 O2 C14 118.4(3) . . ?
C5 C6 C1 119.7(4) . . ?
C4 C3 C2 117.8(4) . . ?
C9 C8 N1 118.4(3) . . ?
C9 C8 C13 118.8(4) . . ?
N1 C8 C13 122.6(4) . . ?
C10 C9 C8 121.2(4) . . ?
C2 C1 C6 119.5(4) . . ?
C3 C4 C5 121.8(4) . . ?
C19 N1 C8 124.9(4) . . ?
O3 C19 N1 127.4(4) . . ?
O3 C19 O1 122.6(4) . . ?
N1 C19 O1 110.0(3) . . ?
C12 C13 C8 119.8(4) . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 C7 121.7(4) . . ?
C4 C5 C7 118.9(4) . . ?
C9 C10 C11 119.5(4) . . ?
O1 C7 C5 108.7(3) . . ?
C13 C12 C11 121.4(4) . . ?
C1 C2 C3 121.7(4) . . ?
C1 C2 Cl1 118.9(3) . . ?
C3 C2 Cl1 119.4(3) . . ?

_refine_diff_density_max         1.563
_refine_diff_density_min         -1.722
_refine_diff_density_rms         0.166

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1436584'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2017-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Br N O'
_chemical_formula_weight         122.94

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6713(19)
_cell_length_b                   20.094(5)
_cell_length_c                   10.598(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.855(4)
_cell_angle_gamma                90
_cell_volume                     1627.8(7)
_cell_formula_units_Z            20
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.508
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    12.366
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11397
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.027
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3837
_reflns_number_gt                2661
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3837
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.2049
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_restrained_S_all      1.227
_refine_ls_shift/su_max          0.183
_refine_ls_shift/su_mean         0.043

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 0.31594(7) 0.45644(3) 0.56936(6) 0.0361(2) Uani 1 1 d . . . . .
O1 O -0.2212(4) 0.79444(16) 0.3264(3) 0.0262(8) Uani 1 1 d . . . . .
C2 C 0.2121(6) 0.5401(2) 0.5291(5) 0.0264(11) Uani 1 1 d . . . . .
N2 N -0.0428(5) 0.7214(2) 0.4471(4) 0.0263(9) Uani 1 1 d . . . . .
O2 O -0.0609(5) 0.72427(18) 0.2264(3) 0.0310(8) Uani 1 1 d . . . . .
N1 N -0.2750(5) 0.8159(2) 0.4486(4) 0.0249(9) Uani 1 1 d . . . . .
C7 C 0.0559(7) 0.6365(3) 0.5936(5) 0.0309(12) Uani 1 1 d . . . . .
C9 C 0.1284(6) 0.6248(2) 0.3755(5) 0.0287(11) Uani 1 1 d . . . . .
C10 C -0.1026(6) 0.7436(2) 0.3296(5) 0.0226(10) Uani 1 1 d . . . . .
C11 C -0.2282(7) 0.8879(2) 0.4593(5) 0.0341(13) Uani 1 1 d . . . . .
C12 C 0.0499(6) 0.6606(2) 0.4698(4) 0.0213(10) Uani 1 1 d . . . . .
C13 C -0.0248(8) 0.8915(3) 0.4763(6) 0.0382(13) Uani 1 1 d . . . . .
C14 C 0.2092(6) 0.5641(3) 0.4070(5) 0.0301(12) Uani 1 1 d . . . . .
C15 C 0.1370(7) 0.5758(3) 0.6240(5) 0.0331(12) Uani 1 1 d . . . . .
C16 C -0.4612(7) 0.7946(3) 0.4537(5) 0.0318(12) Uani 1 1 d . . . . .
C17 C -0.5189(7) 0.8240(3) 0.5796(5) 0.0387(14) Uani 1 1 d . . . . .
C18 C -0.4615(7) 0.7184(3) 0.4631(6) 0.0405(14) Uani 1 1 d . . . . .
C19 C -0.2960(8) 0.9134(3) 0.5818(5) 0.0394(14) Uani 1 1 d . . . . .
C20 C -0.2939(9) 0.9311(3) 0.3465(6) 0.0473(16) Uani 1 1 d . . . . .
C21 C -0.5875(7) 0.8159(3) 0.3388(6) 0.0466(16) Uani 1 1 d . . . . .
C22 C -0.4912(8) 0.8983(3) 0.5896(6) 0.0439(15) Uani 1 1 d . . . . .


_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 C2 1.893(5) . ?
O1 C10 1.367(6) . ?
O1 N1 1.456(5) . ?
C2 C14 1.379(7) . ?
C2 C15 1.398(7) . ?
N2 C10 1.365(6) . ?
N2 C12 1.424(6) . ?
O2 C10 1.229(6) . ?
N1 C16 1.496(6) . ?
N1 C11 1.494(6) . ?
C7 C15 1.396(7) . ?
C7 C12 1.396(7) . ?
C9 C14 1.396(7) . ?
C9 C12 1.407(7) . ?
C11 C19 1.527(7) . ?
C11 C20 1.528(7) . ?
C11 C13 1.557(8) . ?
C16 C18 1.535(8) . ?
C16 C21 1.550(7) . ?
C16 C17 1.557(7) . ?
C17 C22 1.512(9) . ?
C19 C22 1.537(9) . ?

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 O1 N1 115.9(3) . . ?
C14 C2 C15 121.3(5) . . ?
C14 C2 Br1 119.7(4) . . ?
C15 C2 Br1 119.0(4) . . ?
C10 N2 C12 124.0(4) . . ?
O1 N1 C16 106.9(4) . . ?
O1 N1 C11 105.7(4) . . ?
C16 N1 C11 119.8(4) . . ?
C15 C7 C12 119.9(5) . . ?
C14 C9 C12 119.0(5) . . ?
O2 C10 N2 128.0(4) . . ?
O2 C10 O1 115.9(4) . . ?
N2 C10 O1 116.0(4) . . ?
N1 C11 C19 107.1(4) . . ?
N1 C11 C20 115.5(5) . . ?
C19 C11 C20 111.1(4) . . ?
N1 C11 C13 106.6(4) . . ?
C19 C11 C13 107.3(5) . . ?
C20 C11 C13 109.0(5) . . ?
C7 C12 C9 120.6(4) . . ?
C7 C12 N2 115.6(4) . . ?
C9 C12 N2 123.8(4) . . ?
C2 C14 C9 120.1(5) . . ?
C7 C15 C2 119.0(5) . . ?
N1 C16 C18 107.1(4) . . ?
N1 C16 C21 115.3(5) . . ?
C18 C16 C21 108.7(5) . . ?
N1 C16 C17 105.4(4) . . ?
C18 C16 C17 108.7(5) . . ?
C21 C16 C17 111.4(4) . . ?
C22 C17 C16 112.7(5) . . ?
C11 C19 C22 112.5(5) . . ?
C17 C22 C19 108.9(5) . . ?

_refine_diff_density_max         0.821
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.145

