# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_MK49B
_database_code_depnum_ccdc_archive 'CCDC 1450009'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cl2 N O4'
_chemical_formula_sum            'C16 H13 Cl2 N O4'
_chemical_formula_weight         354.17

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.7051(13)
_cell_length_b                   7.9191(7)
_cell_length_c                   26.746(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.6625(13)
_cell_angle_gamma                90
_cell_volume                     3108.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7926
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      28.3

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.437
_shelx_estimated_absorpt_T_min   0.818
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'SADABS-2014/3 (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine focused sealed X-Ray tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15967
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.776
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3856
_reflns_number_gt                3202
_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       'SMART APEX II (Bruker, 2013)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A'
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2013)'
_computing_publication_material  SHELXTL
_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)+(0.0299P)²+3.2157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3856
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.93550(12) -0.2972(2) 0.46610(6) 0.0336(4) Uani 1 1 d . . . . .
H1A H 0.9994 -0.3222 0.4760 0.050 Uiso 1 1 calc R U . . .
H1B H 0.9325 -0.2083 0.4406 0.050 Uiso 1 1 calc R U . . .
H1C H 0.9057 -0.3994 0.4524 0.050 Uiso 1 1 calc R U . . .
C2 C 0.88754(10) -0.2384(2) 0.51131(6) 0.0241(3) Uani 1 1 d . . . . .
C3 C 0.83685(11) -0.3486(2) 0.53893(6) 0.0270(3) Uani 1 1 d . . . . .
H3 H 0.8328 -0.4642 0.5295 0.032 Uiso 1 1 calc R U . . .
C4 C 0.79197(11) -0.29263(19) 0.58001(6) 0.0237(3) Uani 1 1 d . . . . .
H4 H 0.7564 -0.3690 0.5980 0.028 Uiso 1 1 calc R U . . .
C5 C 0.79925(10) -0.12488(18) 0.59476(5) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.85093(10) -0.01308(19) 0.56814(5) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.8573 0.1014 0.5784 0.026 Uiso 1 1 calc R U . . .
C7 C 0.89306(10) -0.0707(2) 0.52642(6) 0.0234(3) Uani 1 1 d . . . . .
H7 H 0.9266 0.0067 0.5077 0.028 Uiso 1 1 calc R U . . .
N1 N 0.75819(9) -0.07262(16) 0.63911(5) 0.0200(3) Uani 1 1 d . . . . .
H1N H 0.7586(12) -0.142(2) 0.6626(7) 0.027(5) Uiso 1 1 d . . . . .
C8 C 0.72510(9) 0.08125(17) 0.64936(5) 0.0172(3) Uani 1 1 d . . . . .
C9 C 0.69461(10) 0.21490(18) 0.62120(5) 0.0182(3) Uani 1 1 d . . . . .
Cl1 Cl 0.68129(3) 0.24076(5) 0.55757(2) 0.02737(10) Uani 1 1 d . . . . .
C10 C 0.66670(9) 0.34782(18) 0.65369(5) 0.0178(3) Uani 1 1 d . . . . .
O1 O 0.63525(7) 0.48701(13) 0.64399(4) 0.0226(2) Uani 1 1 d . . . . .
O2 O 0.67989(7) 0.29709(12) 0.70231(4) 0.0183(2) Uani 1 1 d . . . . .
C11 C 0.71926(10) 0.13037(17) 0.70363(5) 0.0178(3) Uani 1 1 d . . . . .
H11 H 0.6782 0.0503 0.7203 0.021 Uiso 1 1 calc R U . . .
C12 C 0.81260(10) 0.13553(18) 0.73241(5) 0.0190(3) Uani 1 1 d . . . . .
H12 H 0.8353 0.0169 0.7361 0.023 Uiso 1 1 calc R U . . .
O3 O 0.79972(7) 0.20003(13) 0.78131(4) 0.0219(2) Uani 1 1 d . . . . .
H3A H 0.8264 0.1371 0.8029 0.033 Uiso 1 1 calc R U . . .
C13 C 0.88238(10) 0.23517(18) 0.70682(5) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.95450(11) 0.1910(2) 0.68110(6) 0.0271(3) Uani 1 1 d . . . . .
H14 H 0.9741 0.0792 0.6746 0.033 Uiso 1 1 calc R U . . .
C15 C 0.99593(11) 0.3431(2) 0.66537(6) 0.0288(4) Uani 1 1 d . . . . .
H15 H 1.0481 0.3533 0.6464 0.035 Uiso 1 1 calc R U . . .
C16 C 0.94580(10) 0.4685(2) 0.68297(6) 0.0231(3) Uani 1 1 d . . . . .
Cl2 Cl 0.95653(3) 0.68242(5) 0.68117(2) 0.03749(12) Uani 1 1 d . . . . .
O4 O 0.87503(7) 0.40899(13) 0.70825(4) 0.0208(2) 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
C1 C2 1.512(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.389(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 N1 1.4264(18) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1 C8 1.3468(18) . ?
N1 H1N 0.835(19) . ?
C8 C9 1.359(2) . ?
C8 C11 1.5105(19) . ?
C9 C10 1.441(2) . ?
C9 Cl1 1.7128(14) . ?
C10 O1 1.2168(17) . ?
C10 O2 1.3631(16) . ?
O2 C11 1.4411(17) . ?
C11 C12 1.531(2) . ?
C11 H11 1.0000 . ?
C12 O3 1.4280(16) . ?
C12 C13 1.495(2) . ?
C12 H12 1.0000 . ?
O3 H3A 0.8400 . ?
C13 C14 1.347(2) . ?
C13 O4 1.3814(17) . ?
C14 C15 1.425(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.340(2) . ?
C15 H15 0.9500 . ?
C16 O4 1.3609(17) . ?
C16 Cl2 1.7023(17) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.95(14) . . ?
C7 C2 C1 120.39(15) . . ?
C3 C2 C1 121.66(15) . . ?
C4 C3 C2 121.17(15) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.86(14) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.88(13) . . ?
C4 C5 N1 119.01(13) . . ?
C6 C5 N1 120.98(13) . . ?
C7 C6 C5 119.25(14) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C2 121.84(14) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
C8 N1 C5 127.56(12) . . ?
C8 N1 H1N 115.5(12) . . ?
C5 N1 H1N 116.8(12) . . ?
N1 C8 C9 134.64(13) . . ?
N1 C8 C11 118.17(12) . . ?
C9 C8 C11 107.17(12) . . ?
C8 C9 C10 109.34(12) . . ?
C8 C9 Cl1 131.06(11) . . ?
C10 C9 Cl1 119.53(11) . . ?
O1 C10 O2 119.96(13) . . ?
O1 C10 C9 130.69(13) . . ?
O2 C10 C9 109.35(12) . . ?
C10 O2 C11 109.02(10) . . ?
O2 C11 C8 105.06(11) . . ?
O2 C11 C12 109.50(11) . . ?
C8 C11 C12 112.69(11) . . ?
O2 C11 H11 109.8 . . ?
C8 C11 H11 109.8 . . ?
C12 C11 H11 109.8 . . ?
O3 C12 C13 111.45(12) . . ?
O3 C12 C11 107.63(11) . . ?
C13 C12 C11 113.81(11) . . ?
O3 C12 H12 107.9 . . ?
C13 C12 H12 107.9 . . ?
C11 C12 H12 107.9 . . ?
C12 O3 H3A 109.5 . . ?
C14 C13 O4 109.79(13) . . ?
C14 C13 C12 133.07(14) . . ?
O4 C13 C12 117.14(12) . . ?
C13 C14 C15 107.26(14) . . ?
C13 C14 H14 126.4 . . ?
C15 C14 H14 126.4 . . ?
C16 C15 C14 105.52(14) . . ?
C16 C15 H15 127.2 . . ?
C14 C15 H15 127.2 . . ?
C15 C16 O4 111.90(14) . . ?
C15 C16 Cl2 132.35(13) . . ?
O4 C16 Cl2 115.72(11) . . ?
C16 O4 C13 105.53(11) . . ?

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
C7 C2 C3 C4 0.8(2) . . . . ?
C1 C2 C3 C4 -179.08(16) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C5 N1 -175.51(14) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
N1 C5 C6 C7 177.20(14) . . . . ?
C5 C6 C7 C2 -2.1(2) . . . . ?
C3 C2 C7 C6 1.0(2) . . . . ?
C1 C2 C7 C6 -179.09(15) . . . . ?
C4 C5 N1 C8 -150.92(15) . . . . ?
C6 C5 N1 C8 33.2(2) . . . . ?
C5 N1 C8 C9 22.5(3) . . . . ?
C5 N1 C8 C11 -156.15(14) . . . . ?
N1 C8 C9 C10 179.75(15) . . . . ?
C11 C8 C9 C10 -1.51(16) . . . . ?
N1 C8 C9 Cl1 2.8(3) . . . . ?
C11 C8 C9 Cl1 -178.43(11) . . . . ?
C8 C9 C10 O1 -179.59(15) . . . . ?
Cl1 C9 C10 O1 -2.3(2) . . . . ?
C8 C9 C10 O2 0.07(16) . . . . ?
Cl1 C9 C10 O2 177.40(9) . . . . ?
O1 C10 O2 C11 -178.81(13) . . . . ?
C9 C10 O2 C11 1.49(15) . . . . ?
C10 O2 C11 C8 -2.32(14) . . . . ?
C10 O2 C11 C12 118.96(12) . . . . ?
N1 C8 C11 O2 -178.68(12) . . . . ?
C9 C8 C11 O2 2.34(15) . . . . ?
N1 C8 C11 C12 62.17(16) . . . . ?
C9 C8 C11 C12 -116.82(13) . . . . ?
O2 C11 C12 O3 57.48(14) . . . . ?
C8 C11 C12 O3 174.02(11) . . . . ?
O2 C11 C12 C13 -66.55(14) . . . . ?
C8 C11 C12 C13 49.99(16) . . . . ?
O3 C12 C13 C14 133.26(17) . . . . ?
C11 C12 C13 C14 -104.79(19) . . . . ?
O3 C12 C13 O4 -47.11(16) . . . . ?
C11 C12 C13 O4 74.83(15) . . . . ?
O4 C13 C14 C15 0.28(17) . . . . ?
C12 C13 C14 C15 179.93(15) . . . . ?
C13 C14 C15 C16 0.22(18) . . . . ?
C14 C15 C16 O4 -0.65(18) . . . . ?
C14 C15 C16 Cl2 176.96(13) . . . . ?
C15 C16 O4 C13 0.82(16) . . . . ?
Cl2 C16 O4 C13 -177.23(10) . . . . ?
C14 C13 O4 C16 -0.66(16) . . . . ?
C12 C13 O4 C16 179.63(12) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_boukv2
_database_code_depnum_ccdc_archive 'CCDC 1469893'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-05-04 downloaded from the CCDC.
;
_audit_creation_date             2016-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 Cl2 N O4'
_chemical_formula_sum            'C16 H13 Cl2 N O4'
_chemical_formula_weight         354.17
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   12.8328(2)
_cell_length_b                   26.5383(4)
_cell_length_c                   9.25770(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3152.81(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.13
_cell_measurement_theta_min      3.83
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.886
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1667 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.6038.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            122420
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.178
_diffrn_reflns_theta_min         3.826
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3100
_reflns_number_total             3102
_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 (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.067
_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)+(0.0408P)²+2.3690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0806
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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 Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.56389(3) 0.37752(2) 0.57255(4) 0.01824(11) Uani 1 1 d . . . . .
Cl2 Cl 0.63049(3) 0.71109(2) 0.65179(6) 0.04389(15) Uani 1 1 d . . . . .
O1 O 0.58381(8) 0.45642(4) 0.82027(11) 0.0218(2) Uani 1 1 d . . . . .
O2 O 0.63253(7) 0.51699(4) 0.66491(10) 0.0168(2) Uani 1 1 d . . . . .
O3 O 0.83880(8) 0.50878(4) 0.54458(11) 0.0156(2) Uani 1 1 d . . . . .
O4 O 0.69248(8) 0.62390(4) 0.56006(12) 0.0204(2) Uani 1 1 d . . . . .
N1 N 0.64305(9) 0.45910(4) 0.31228(13) 0.0163(2) Uani 1 1 d . . . . .
C1 C 0.59615(16) 0.26306(6) 0.0606(2) 0.0391(5) Uani 1 1 d . . . . .
H1A H 0.5401 0.2455 0.1119 0.059 Uiso 1 1 calc GR . . . .
H1B H 0.6610 0.2438 0.0694 0.059 Uiso 1 1 calc GR . . . .
H1C H 0.5777 0.2664 -0.0417 0.059 Uiso 1 1 calc GR . . . .
C2 C 0.61114(12) 0.31477(6) 0.12556(18) 0.0242(3) Uani 1 1 d . . . . .
C3 C 0.54672(13) 0.35439(6) 0.08414(18) 0.0274(4) Uani 1 1 d . . . . .
H3A H 0.4950 0.3488 0.0125 0.033 Uiso 1 1 calc R . . . .
C4 C 0.55658(12) 0.40194(6) 0.14559(16) 0.0219(3) Uani 1 1 d . . . . .
H4 H 0.5115 0.4285 0.1171 0.026 Uiso 1 1 calc R . . . .
C5 C 0.63279(11) 0.41006(5) 0.24868(15) 0.0157(3) Uani 1 1 d . . . . .
C6 C 0.70027(11) 0.37162(5) 0.28846(16) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.7542 0.3777 0.3565 0.023 Uiso 1 1 calc R . . . .
C7 C 0.68798(12) 0.32421(5) 0.22761(17) 0.0218(3) Uani 1 1 d . . . . .
H7 H 0.7331 0.2977 0.2564 0.026 Uiso 1 1 calc R . . . .
C8 C 0.63315(10) 0.46856(5) 0.45324(15) 0.0141(3) Uani 1 1 d . . . . .
C9 C 0.60493(10) 0.43904(5) 0.56715(14) 0.0147(3) Uani 1 1 d . . . . .
C10 C 0.60513(10) 0.46848(5) 0.69697(15) 0.0162(3) Uani 1 1 d . . . . .
C11 C 0.65204(10) 0.52107(5) 0.51172(14) 0.0146(3) Uani 1 1 d . . . . .
H11 H 0.6005 0.5448 0.4680 0.018 Uiso 1 1 calc R . . . .
C12 C 0.76255(10) 0.54204(5) 0.49023(14) 0.0138(3) Uani 1 1 d . . . . .
H12 H 0.7753 0.5483 0.3852 0.017 Uiso 1 1 calc R . . . .
C13 C 0.77357(10) 0.59033(5) 0.57268(14) 0.0148(3) Uani 1 1 d . . . . .
C14 C 0.84636(11) 0.60770(5) 0.66480(15) 0.0175(3) Uani 1 1 d . . . . .
H14 H 0.9093 0.5913 0.6917 0.021 Uiso 1 1 calc R . . . .
C15 C 0.80999(12) 0.65591(5) 0.71445(17) 0.0217(3) Uani 1 1 d . . . . .
H15 H 0.8438 0.6780 0.7802 0.026 Uiso 1 1 calc R . . . .
C16 C 0.71837(12) 0.66311(5) 0.64837(18) 0.0233(3) Uani 1 1 d . . . . .
H1 H 0.6497(14) 0.4840(7) 0.255(2) 0.023(5) Uiso 1 1 d . . . . .
H3 H 0.8656(15) 0.4927(8) 0.477(2) 0.029(5) 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 C9 1.7161(14) . ?
Cl2 C16 1.7011(15) . ?
O1 C10 1.2166(18) . ?
O2 C10 1.3672(17) . ?
O2 C11 1.4441(16) . ?
O3 C12 1.4106(15) . ?
O3 H3 0.83(2) . ?
O4 C13 1.3750(16) . ?
O4 C16 1.3643(18) . ?
N1 C5 1.4344(17) . ?
N1 C8 1.3349(18) . ?
N1 H1 0.85(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.511(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.389(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.390(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3627(19) . ?
C8 C11 1.5145(18) . ?
C9 C10 1.4335(19) . ?
C11 H11 1.0000 . ?
C11 C12 1.5364(18) . ?
C12 H12 1.0000 . ?
C12 C13 1.4982(18) . ?
C13 C14 1.346(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.437(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.339(2) . ?

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 C11 109.17(10) . . ?
C12 O3 H3 109.7(14) . . ?
C16 O4 C13 105.02(11) . . ?
C5 N1 H1 117.4(12) . . ?
C8 N1 C5 124.27(12) . . ?
C8 N1 H1 118.0(13) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.08(15) . . ?
C7 C2 C1 121.69(14) . . ?
C7 C2 C3 118.23(14) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 C2 121.27(14) . . ?
C4 C3 H3A 119.4 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.23(14) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 N1 119.31(13) . . ?
C4 C5 C6 120.63(13) . . ?
C6 C5 N1 120.05(12) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.20(13) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.37(14) . . ?
C6 C7 H7 119.3 . . ?
N1 C8 C9 132.35(13) . . ?
N1 C8 C11 120.48(12) . . ?
C9 C8 C11 107.15(12) . . ?
C8 C9 Cl1 130.62(11) . . ?
C8 C9 C10 109.58(12) . . ?
C10 C9 Cl1 119.64(10) . . ?
O1 C10 O2 120.60(12) . . ?
O1 C10 C9 130.01(13) . . ?
O2 C10 C9 109.37(11) . . ?
O2 C11 C8 104.74(10) . . ?
O2 C11 H11 109.3 . . ?
O2 C11 C12 108.32(11) . . ?
C8 C11 H11 109.3 . . ?
C8 C11 C12 115.77(11) . . ?
C12 C11 H11 109.3 . . ?
O3 C12 C11 111.56(10) . . ?
O3 C12 H12 109.7 . . ?
O3 C12 C13 106.74(10) . . ?
C11 C12 H12 109.7 . . ?
C13 C12 C11 109.33(11) . . ?
C13 C12 H12 109.7 . . ?
O4 C13 C12 116.08(11) . . ?
C14 C13 O4 110.91(12) . . ?
C14 C13 C12 132.94(12) . . ?
C13 C14 H14 126.8 . . ?
C13 C14 C15 106.39(13) . . ?
C15 C14 H14 126.8 . . ?
C14 C15 H15 127.3 . . ?
C16 C15 C14 105.42(13) . . ?
C16 C15 H15 127.3 . . ?
O4 C16 Cl2 114.87(11) . . ?
C15 C16 Cl2 132.87(12) . . ?
C15 C16 O4 112.25(13) . . ?

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
N1 H1 O3 0.85(2) 2.06(2) 2.8168(16) 147.3(17) 8_755
O3 H3 O1 0.83(2) 1.86(2) 2.6887(14) 176(2) 8_755

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
Cl1 C9 C10 O1 3.5(2) . . . . ?
Cl1 C9 C10 O2 -175.17(9) . . . . ?
O2 C11 C12 O3 63.62(13) . . . . ?
O2 C11 C12 C13 -54.21(13) . . . . ?
O3 C12 C13 O4 -165.90(11) . . . . ?
O3 C12 C13 C14 10.6(2) . . . . ?
O4 C13 C14 C15 -0.31(16) . . . . ?
N1 C5 C6 C7 178.90(13) . . . . ?
N1 C8 C9 Cl1 -3.8(2) . . . . ?
N1 C8 C9 C10 -178.97(14) . . . . ?
N1 C8 C11 O2 179.01(12) . . . . ?
N1 C8 C11 C12 -61.79(16) . . . . ?
C1 C2 C3 C4 177.89(17) . . . . ?
C1 C2 C7 C6 -179.00(16) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
C3 C4 C5 N1 -179.97(14) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C4 C5 C6 C7 -2.4(2) . . . . ?
C5 N1 C8 C9 -5.7(2) . . . . ?
C5 N1 C8 C11 176.13(12) . . . . ?
C5 C6 C7 C2 1.4(2) . . . . ?
C7 C2 C3 C4 -1.7(3) . . . . ?
C8 N1 C5 C4 120.05(16) . . . . ?
C8 N1 C5 C6 -61.28(19) . . . . ?
C8 C9 C10 O1 179.26(15) . . . . ?
C8 C9 C10 O2 0.63(16) . . . . ?
C8 C11 C12 O3 -53.61(15) . . . . ?
C8 C11 C12 C13 -171.43(11) . . . . ?
C9 C8 C11 O2 0.44(14) . . . . ?
C9 C8 C11 C12 119.64(13) . . . . ?
C10 O2 C11 C8 -0.06(13) . . . . ?
C10 O2 C11 C12 -124.16(11) . . . . ?
C11 O2 C10 O1 -179.11(12) . . . . ?
C11 O2 C10 C9 -0.33(14) . . . . ?
C11 C8 C9 Cl1 174.54(11) . . . . ?
C11 C8 C9 C10 -0.65(15) . . . . ?
C11 C12 C13 O4 -45.10(15) . . . . ?
C11 C12 C13 C14 131.41(16) . . . . ?
C12 C13 C14 C15 -176.95(14) . . . . ?
C13 O4 C16 Cl2 179.35(10) . . . . ?
C13 O4 C16 C15 0.02(17) . . . . ?
C13 C14 C15 C16 0.31(17) . . . . ?
C14 C15 C16 Cl2 -179.38(13) . . . . ?
C14 C15 C16 O4 -0.20(18) . . . . ?
C16 O4 C13 C12 177.45(12) . . . . ?
C16 O4 C13 C14 0.19(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
