# Electronic Supplementary Material (ESI) for ChemComm.
# 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_151015b
_database_code_depnum_ccdc_archive 'CCDC 1445774'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N O3'
_chemical_formula_weight         311.37

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'

_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'

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

_cell_length_a                   5.9975(11)
_cell_length_b                   15.485(3)
_cell_length_c                   18.460(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1714.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2752
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11285
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.716
_diffrn_reflns_theta_max         27.591
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3815
_reflns_number_gt                2740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   -2.1(18)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3815
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_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 0.7951(5) 0.66245(16) 0.88339(13) 0.0460(6) Uani 1 1 d . . . . .
C2 C 0.7475(6) 0.62117(18) 0.94796(15) 0.0603(8) Uani 1 1 d . . . . .
H2 H 0.6109 0.5943 0.9558 0.072 Uiso 1 1 calc R U . . .
C3 C 0.9111(7) 0.6216(2) 1.00013(15) 0.0682(10) Uani 1 1 d . . . . .
H3 H 0.8856 0.5958 1.0449 0.082 Uiso 1 1 calc R U . . .
C4 C 1.1118(6) 0.6603(2) 0.98596(16) 0.0694(9) Uani 1 1 d . . . . .
H4 H 1.2245 0.6609 1.0206 0.083 Uiso 1 1 calc R U . . .
C5 C 1.1426(5) 0.6977(2) 0.92017(16) 0.0611(8) Uani 1 1 d . . . . .
H5 H 1.2795 0.7235 0.9107 0.073 Uiso 1 1 calc R U . . .
C6 C 0.6812(4) 0.71133(16) 0.76694(13) 0.0430(6) Uani 1 1 d . . . . .
H6 H 0.8132 0.6867 0.7434 0.052 Uiso 1 1 calc R U . . .
C7 C 0.4836(5) 0.70289(18) 0.71812(14) 0.0469(6) Uani 1 1 d . . . . .
H7 H 0.3485 0.7268 0.7326 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4941(5) 0.66281(16) 0.65540(14) 0.0457(6) Uani 1 1 d . . . . .
H8 H 0.6309 0.6378 0.6442 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3190(5) 0.65236(16) 0.60100(13) 0.0442(6) Uani 1 1 d . . . . .
C10 C 0.1253(5) 0.70137(19) 0.59983(15) 0.0515(7) Uani 1 1 d . . . . .
H10 H 0.0993 0.7420 0.6359 0.062 Uiso 1 1 calc R U . . .
C11 C -0.0296(5) 0.6898(2) 0.54492(17) 0.0632(8) Uani 1 1 d . . . . .
H11 H -0.1568 0.7241 0.5437 0.076 Uiso 1 1 calc R U . . .
C12 C 0.0023(7) 0.6291(2) 0.49289(17) 0.0728(10) Uani 1 1 d . . . . .
H12 H -0.1038 0.6211 0.4568 0.087 Uiso 1 1 calc R U . . .
C13 C 0.1914(7) 0.5796(2) 0.49387(17) 0.0748(10) Uani 1 1 d . . . . .
H13 H 0.2130 0.5376 0.4585 0.090 Uiso 1 1 calc R U . . .
C14 C 0.3481(6) 0.59144(19) 0.54631(16) 0.0616(8) Uani 1 1 d . . . . .
H14 H 0.4772 0.5582 0.5456 0.074 Uiso 1 1 calc R U . . .
C15 C 0.7227(4) 0.80610(17) 0.78490(12) 0.0415(6) Uani 1 1 d . . . . .
C16 C 0.9469(5) 0.93034(16) 0.74629(15) 0.0511(7) Uani 1 1 d . . . . .
C17 C 1.0486(8) 0.9448(2) 0.81963(19) 0.0825(11) Uani 1 1 d . . . . .
H17A H 1.1581 0.9010 0.8289 0.124 Uiso 1 1 calc R U . . .
H17B H 0.9342 0.9421 0.8560 0.124 Uiso 1 1 calc R U . . .
H17C H 1.1183 1.0006 0.8209 0.124 Uiso 1 1 calc R U . . .
C18 C 1.1209(6) 0.9361(2) 0.6868(2) 0.0767(11) Uani 1 1 d . . . . .
H18A H 1.0527 0.9235 0.6410 0.115 Uiso 1 1 calc R U . . .
H18B H 1.2375 0.8951 0.6961 0.115 Uiso 1 1 calc R U . . .
H18C H 1.1825 0.9933 0.6858 0.115 Uiso 1 1 calc R U . . .
C19 C 0.7544(7) 0.9896(2) 0.73078(19) 0.0774(10) Uani 1 1 d . . . . .
H19A H 0.6503 0.9875 0.7703 0.116 Uiso 1 1 calc R U . . .
H19B H 0.6815 0.9717 0.6870 0.116 Uiso 1 1 calc R U . . .
H19C H 0.8083 1.0476 0.7252 0.116 Uiso 1 1 calc R U . . .
N1 N 0.9858(4) 0.69948(15) 0.86784(12) 0.0501(6) Uani 1 1 d . . . . .
O1 O 0.6314(3) 0.66420(12) 0.83174(10) 0.0539(5) Uani 1 1 d . . . . .
O2 O 0.8739(3) 0.83903(11) 0.74014(9) 0.0444(4) Uani 1 1 d . . . . .
O3 O 0.6219(3) 0.84437(13) 0.83060(10) 0.0573(5) 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 N1 1.311(4) . ?
C1 O1 1.369(3) . ?
C1 C2 1.382(4) . ?
C2 C3 1.375(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.348(4) . ?
C5 H5 0.9300 . ?
C6 O1 1.433(3) . ?
C6 C7 1.495(4) . ?
C6 C15 1.525(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.315(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.462(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(4) . ?
C9 C14 1.393(4) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O3 1.195(3) . ?
C15 O2 1.329(3) . ?
C16 O2 1.484(3) . ?
C16 C17 1.501(4) . ?
C16 C19 1.503(4) . ?
C16 C18 1.517(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
N1 C1 O1 117.7(2) . . ?
N1 C1 C2 124.8(3) . . ?
O1 C1 C2 117.5(3) . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 123.7(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
O1 C6 C7 107.1(2) . . ?
O1 C6 C15 110.04(19) . . ?
C7 C6 C15 110.2(2) . . ?
O1 C6 H6 109.8 . . ?
C7 C6 H6 109.8 . . ?
C15 C6 H6 109.8 . . ?
C8 C7 C6 122.3(3) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 128.5(3) . . ?
C7 C8 H8 115.7 . . ?
C9 C8 H8 115.7 . . ?
C10 C9 C14 117.6(3) . . ?
C10 C9 C8 123.5(2) . . ?
C14 C9 C8 118.9(3) . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
O3 C15 O2 126.4(3) . . ?
O3 C15 C6 123.2(2) . . ?
O2 C15 C6 110.2(2) . . ?
O2 C16 C17 109.3(2) . . ?
O2 C16 C19 109.9(2) . . ?
C17 C16 C19 113.1(3) . . ?
O2 C16 C18 101.7(2) . . ?
C17 C16 C18 111.4(3) . . ?
C19 C16 C18 110.8(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 C5 116.2(2) . . ?
C1 O1 C6 116.2(2) . . ?
C15 O2 C16 121.29(19) . . ?

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
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .
C17 H17B O3 0.96 2.45 3.001(5) 116.0 .
C19 H19A O3 0.96 2.49 3.014(4) 114.6 .

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.040

_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_151207a
_database_code_depnum_ccdc_archive 'CCDC 1445775'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 Cl2 N O3'
_chemical_formula_weight         352.20

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                   5.8604(13)
_cell_length_b                   8.2421(17)
_cell_length_c                   17.962(4)
_cell_angle_alpha                100.255(5)
_cell_angle_beta                 93.590(5)
_cell_angle_gamma                97.437(5)
_cell_volume                     843.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2070
_cell_measurement_theta_min      2.314
_cell_measurement_theta_max      30.012

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.398
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4820
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.156
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3085
_reflns_number_gt                2183
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.1672P)²+0.1546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3085
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.2620
_refine_ls_wR_factor_gt          0.2266
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.7203(7) 0.2075(4) 0.6684(2) 0.0383(9) Uani 1 1 d . . . . .
C2 C 0.9142(8) 0.3251(5) 0.6885(2) 0.0480(10) Uani 1 1 d . . . . .
H2 H 0.9490 0.3820 0.7383 0.058 Uiso 1 1 calc R U . . .
C3 C 1.0528(8) 0.3551(5) 0.6333(3) 0.0512(11) Uani 1 1 d . . . . .
H3 H 1.1858 0.4327 0.6454 0.061 Uiso 1 1 calc R U . . .
C4 C 0.9974(8) 0.2699(5) 0.5578(3) 0.0519(11) Uani 1 1 d . . . . .
C5 C 0.7979(8) 0.1573(6) 0.5453(2) 0.0567(12) Uani 1 1 d . . . . .
H5 H 0.7553 0.1007 0.4958 0.068 Uiso 1 1 calc R U . . .
C6 C 1.1509(10) 0.2966(8) 0.4949(3) 0.0774(16) Uani 1 1 d . . . . .
H6A H 1.3010 0.2689 0.5073 0.116 Uiso 1 1 calc R U . . .
H6B H 1.1649 0.4111 0.4894 0.116 Uiso 1 1 calc R U . . .
H6C H 1.0838 0.2266 0.4481 0.116 Uiso 1 1 calc R U . . .
C7 C 0.3813(7) 0.0603(5) 0.7052(2) 0.0404(9) Uani 1 1 d . . . . .
H7 H 0.2972 0.0836 0.6603 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4349(7) -0.1188(5) 0.6884(2) 0.0441(10) Uani 1 1 d . . . . .
C9 C 0.6962(10) -0.3058(6) 0.7035(3) 0.0695(14) Uani 1 1 d . . . . .
H9A H 0.6005 -0.3718 0.7317 0.104 Uiso 1 1 calc R U . . .
H9B H 0.8556 -0.3041 0.7200 0.104 Uiso 1 1 calc R U . . .
H9C H 0.6690 -0.3531 0.6504 0.104 Uiso 1 1 calc R U . . .
C10 C 0.2312(7) 0.0737(5) 0.7694(2) 0.0437(9) Uani 1 1 d . . . . .
H10 H 0.0895 0.0051 0.7619 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2817(7) 0.1748(5) 0.8363(2) 0.0429(9) Uani 1 1 d . . . . .
H11 H 0.4232 0.2435 0.8430 0.051 Uiso 1 1 calc R U . . .
C12 C 0.1399(7) 0.1899(5) 0.9002(2) 0.0400(9) Uani 1 1 d . . . . .
C13 C 0.2268(7) 0.3011(5) 0.9675(2) 0.0408(9) Uani 1 1 d . . . . .
H13 H 0.3731 0.3622 0.9702 0.049 Uiso 1 1 calc R U . . .
C14 C 0.1003(7) 0.3217(5) 1.0295(2) 0.0375(8) Uani 1 1 d . . . . .
C15 C -0.1211(7) 0.2309(5) 1.0268(2) 0.0417(9) Uani 1 1 d . . . . .
C16 C -0.2107(7) 0.1216(5) 0.9609(2) 0.0506(11) Uani 1 1 d . . . . .
H16 H -0.3571 0.0610 0.9585 0.061 Uiso 1 1 calc R U . . .
C17 C -0.0828(7) 0.1018(5) 0.8980(2) 0.0438(9) Uani 1 1 d . . . . .
H17 H -0.1459 0.0289 0.8538 0.053 Uiso 1 1 calc R U . . .
Cl1 Cl -0.2809(2) 0.25291(16) 1.10483(7) 0.0645(5) Uani 1 1 d . . . . .
Cl2 Cl 0.2137(2) 0.46441(14) 1.11077(6) 0.0564(4) Uani 1 1 d . . . . .
N1 N 0.6597(6) 0.1229(4) 0.59911(19) 0.0499(9) Uani 1 1 d . . . . .
O1 O 0.5820(5) 0.1807(3) 0.72606(14) 0.0447(7) Uani 1 1 d . . . . .
O2 O 0.6405(5) -0.1362(3) 0.71645(17) 0.0503(8) Uani 1 1 d . . . . .
O3 O 0.2949(6) -0.2324(4) 0.6542(2) 0.0715(10) 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 N1 1.317(5) . ?
C1 C2 1.378(6) . ?
C1 O1 1.385(4) . ?
C2 C3 1.357(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(7) . ?
C4 C6 1.517(6) . ?
C5 N1 1.344(5) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 O1 1.421(5) . ?
C7 C10 1.490(6) . ?
C7 C8 1.530(6) . ?
C7 H7 0.9800 . ?
C8 O3 1.209(5) . ?
C8 O2 1.312(5) . ?
C9 O2 1.458(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.326(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.456(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.402(5) . ?
C12 C17 1.404(6) . ?
C13 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.405(6) . ?
C14 Cl2 1.738(4) . ?
C15 C16 1.381(6) . ?
C15 Cl1 1.730(4) . ?
C16 C17 1.391(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

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
N1 C1 C2 124.4(4) . . ?
N1 C1 O1 119.3(3) . . ?
C2 C1 O1 116.3(3) . . ?
C3 C2 C1 117.9(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 115.6(4) . . ?
C5 C4 C6 122.1(4) . . ?
C3 C4 C6 122.3(4) . . ?
N1 C5 C4 125.0(4) . . ?
N1 C5 H5 117.5 . . ?
C4 C5 H5 117.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C10 108.5(3) . . ?
O1 C7 C8 113.2(3) . . ?
C10 C7 C8 107.6(3) . . ?
O1 C7 H7 109.1 . . ?
C10 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
O3 C8 O2 124.3(4) . . ?
O3 C8 C7 121.9(4) . . ?
O2 C8 C7 113.8(3) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 125.8(4) . . ?
C11 C10 H10 117.1 . . ?
C7 C10 H10 117.1 . . ?
C10 C11 C12 127.2(4) . . ?
C10 C11 H11 116.4 . . ?
C12 C11 H11 116.4 . . ?
C13 C12 C17 117.6(4) . . ?
C13 C12 C11 118.7(3) . . ?
C17 C12 C11 123.6(4) . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 Cl2 119.5(3) . . ?
C15 C14 Cl2 120.2(3) . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 Cl1 119.8(3) . . ?
C14 C15 Cl1 120.9(3) . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 121.1(4) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C1 N1 C5 116.5(4) . . ?
C1 O1 C7 116.3(3) . . ?
C8 O2 C9 115.6(4) . . ?

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
N1 C1 C2 C3 -0.4(6) . . . . ?
O1 C1 C2 C3 -179.6(4) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C2 C3 C4 C6 -178.4(4) . . . . ?
C3 C4 C5 N1 -1.2(7) . . . . ?
C6 C4 C5 N1 177.1(4) . . . . ?
O1 C7 C8 O3 -163.2(4) . . . . ?
C10 C7 C8 O3 76.8(5) . . . . ?
O1 C7 C8 O2 18.8(4) . . . . ?
C10 C7 C8 O2 -101.2(4) . . . . ?
O1 C7 C10 C11 -3.3(6) . . . . ?
C8 C7 C10 C11 119.6(4) . . . . ?
C7 C10 C11 C12 -179.5(4) . . . . ?
C10 C11 C12 C13 178.1(4) . . . . ?
C10 C11 C12 C17 -3.4(7) . . . . ?
C17 C12 C13 C14 0.9(6) . . . . ?
C11 C12 C13 C14 179.5(4) . . . . ?
C12 C13 C14 C15 -0.1(6) . . . . ?
C12 C13 C14 Cl2 -178.6(3) . . . . ?
C13 C14 C15 C16 -0.4(6) . . . . ?
Cl2 C14 C15 C16 178.2(3) . . . . ?
C13 C14 C15 Cl1 179.0(3) . . . . ?
Cl2 C14 C15 Cl1 -2.4(5) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
Cl1 C15 C16 C17 -179.4(3) . . . . ?
C15 C16 C17 C12 0.9(7) . . . . ?
C13 C12 C17 C16 -1.3(6) . . . . ?
C11 C12 C17 C16 -179.8(4) . . . . ?
C2 C1 N1 C5 -0.8(6) . . . . ?
O1 C1 N1 C5 178.4(3) . . . . ?
C4 C5 N1 C1 1.7(7) . . . . ?
N1 C1 O1 C7 0.3(5) . . . . ?
C2 C1 O1 C7 179.6(3) . . . . ?
C10 C7 O1 C1 -168.4(3) . . . . ?
C8 C7 O1 C1 72.2(4) . . . . ?
O3 C8 O2 C9 0.5(6) . . . . ?
C7 C8 O2 C9 178.4(4) . . . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.132

_shelxl_version_number           2014/6

