# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_villani-major-1_a
_database_code_depnum_ccdc_archive 'CCDC 1897062'
loop_
_audit_author_name
_audit_author_address
'Andrea Mazzanti'
;university of Bologna
Italy
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;
_audit_creation_date             02/15/2018
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'compound 1a'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 Cl N O3'
_chemical_formula_weight         321.79

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      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                   10.0517(8)
_cell_length_b                   11.1214(9)
_cell_length_c                   15.3258(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1713.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    510
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.00

_exptl_crystal_description       brick
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   0.911
_exptl_transmission_factor_max   0.943
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'bruker 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
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5581
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             3184
_reflns_number_gt                2977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_max     0.894
_reflns_Friedel_fraction_full    0.908

_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)+(0.0397P)²+0.2876P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.067(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1122 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3184
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
Cl01 Cl -0.17013(7) 0.65765(7) 0.54100(5) 0.0673(3) Uani 1 1 d . . . . .
O1 O 0.72731(17) 0.40851(19) 0.26475(13) 0.0586(5) Uani 1 1 d . . . . .
O2 O 0.6217(2) 0.57758(19) 0.23033(16) 0.0715(6) Uani 1 1 d . . . . .
N1 N 0.1257(2) 0.31808(19) 0.41484(14) 0.0472(5) Uani 1 1 d . . . . .
O3 O 0.5419(2) 0.3181(2) 0.43352(14) 0.0777(7) Uani 1 1 d . . . . .
C3 C 0.1250(2) 0.63079(19) 0.36867(14) 0.0381(5) Uani 1 1 d . . . . .
H3 H 0.1732 0.6827 0.3331 0.046 Uiso 1 1 calc R U . . .
C1 C 0.2558(2) 0.43484(19) 0.33085(13) 0.0350(5) Uani 1 1 d . . . . .
C9 C 0.3682(2) 0.47821(19) 0.27364(13) 0.0349(5) Uani 1 1 d . . . . .
H9 H 0.3802 0.5638 0.2868 0.042 Uiso 1 1 calc R U . . .
C7 C 0.0776(2) 0.4322(2) 0.42395(14) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.1557(2) 0.50763(19) 0.37098(12) 0.0325(4) Uani 1 1 d . . . . .
C4 C 0.0231(2) 0.6738(2) 0.41944(15) 0.0448(5) Uani 1 1 d . . . . .
H4 H 0.0021 0.7552 0.4184 0.054 Uiso 1 1 calc R U . . .
C6 C -0.0261(2) 0.4747(2) 0.47586(15) 0.0431(5) Uani 1 1 d . . . . .
H6 H -0.0769 0.4237 0.5106 0.052 Uiso 1 1 calc R U . . .
C8 C 0.2340(2) 0.3208(2) 0.36017(15) 0.0445(5) Uani 1 1 d . . . . .
H8 H 0.2852 0.2543 0.3453 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4997(2) 0.4157(2) 0.29862(14) 0.0386(5) Uani 1 1 d . . . . .
H10 H 0.4971 0.3329 0.2768 0.046 Uiso 1 1 calc R U . . .
C5 C -0.0488(2) 0.5957(2) 0.47261(16) 0.0439(6) Uani 1 1 d . . . . .
C11 C 0.6201(2) 0.4781(2) 0.25944(15) 0.0436(5) Uani 1 1 d . . . . .
C12 C 0.5217(2) 0.4120(2) 0.39720(16) 0.0476(6) Uani 1 1 d . . . . .
C15 C 0.3387(3) 0.4701(3) 0.17431(15) 0.0492(6) Uani 1 1 d . . . . .
H15 H 0.4205 0.4932 0.1438 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5180(4) 0.5285(3) 0.44583(18) 0.0703(9) Uani 1 1 d . . . . .
H13A H 0.4295 0.5608 0.4440 0.105 Uiso 1 1 calc R U . . .
H13B H 0.5785 0.5844 0.4193 0.105 Uiso 1 1 calc R U . . .
H13C H 0.5435 0.5152 0.5054 0.105 Uiso 1 1 calc R U . . .
C16 C 0.2322(3) 0.5604(4) 0.14832(19) 0.0768(10) Uani 1 1 d . . . . .
H16A H 0.2223 0.5604 0.0860 0.115 Uiso 1 1 calc R U . . .
H16B H 0.2579 0.6392 0.1676 0.115 Uiso 1 1 calc R U . . .
H16C H 0.1492 0.5386 0.1750 0.115 Uiso 1 1 calc R U . . .
C17 C 0.3042(4) 0.3449(3) 0.1448(2) 0.0820(10) Uani 1 1 d . . . . .
H17A H 0.2210 0.3212 0.1703 0.123 Uiso 1 1 calc R U . . .
H17B H 0.3728 0.2903 0.1630 0.123 Uiso 1 1 calc R U . . .
H17C H 0.2968 0.3434 0.0824 0.123 Uiso 1 1 calc R U . . .
C14 C 0.8516(3) 0.4608(4) 0.2370(2) 0.0778(10) Uani 1 1 d . . . . .
H14A H 0.8476 0.4783 0.1758 0.117 Uiso 1 1 calc R U . . .
H14B H 0.9227 0.4051 0.2480 0.117 Uiso 1 1 calc R U . . .
H14C H 0.8674 0.5337 0.2689 0.117 Uiso 1 1 calc R U . . .
H1N H 0.103(3) 0.260(2) 0.4463(18) 0.047(7) 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
Cl01 C5 1.750(2) . ?
O1 C11 1.330(3) . ?
O1 C14 1.442(3) . ?
O2 C11 1.193(3) . ?
N1 C7 1.365(3) . ?
N1 C8 1.374(3) . ?
N1 H1N 0.84(3) . ?
O3 C12 1.200(3) . ?
C3 C4 1.372(3) . ?
C3 C2 1.405(3) . ?
C3 H3 0.9300 . ?
C1 C8 1.363(3) . ?
C1 C2 1.431(3) . ?
C1 C9 1.509(3) . ?
C9 C10 1.542(3) . ?
C9 C15 1.554(3) . ?
C9 H9 0.9800 . ?
C7 C6 1.394(3) . ?
C7 C2 1.406(3) . ?
C4 C5 1.393(4) . ?
C4 H4 0.9300 . ?
C6 C5 1.366(4) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.518(3) . ?
C10 C12 1.527(3) . ?
C10 H10 0.9800 . ?
C12 C13 1.496(4) . ?
C15 C17 1.504(4) . ?
C15 C16 1.521(4) . ?
C15 H15 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C11 O1 C14 116.7(2) . . ?
C7 N1 C8 108.8(2) . . ?
C7 N1 H1N 124.4(18) . . ?
C8 N1 H1N 125.6(18) . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C8 C1 C2 105.74(18) . . ?
C8 C1 C9 127.5(2) . . ?
C2 C1 C9 126.56(18) . . ?
C1 C9 C10 110.69(17) . . ?
C1 C9 C15 114.06(18) . . ?
C10 C9 C15 112.38(18) . . ?
C1 C9 H9 106.4 . . ?
C10 C9 H9 106.4 . . ?
C15 C9 H9 106.4 . . ?
N1 C7 C6 129.6(2) . . ?
N1 C7 C2 107.3(2) . . ?
C6 C7 C2 123.0(2) . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C1 134.1(2) . . ?
C7 C2 C1 107.65(19) . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C5 C6 C7 116.0(2) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
C1 C8 N1 110.4(2) . . ?
C1 C8 H8 124.8 . . ?
N1 C8 H8 124.8 . . ?
C11 C10 C12 106.74(19) . . ?
C11 C10 C9 112.22(18) . . ?
C12 C10 C9 112.44(19) . . ?
C11 C10 H10 108.4 . . ?
C12 C10 H10 108.4 . . ?
C9 C10 H10 108.4 . . ?
C6 C5 C4 123.3(2) . . ?
C6 C5 Cl01 118.85(19) . . ?
C4 C5 Cl01 117.81(19) . . ?
O2 C11 O1 123.5(2) . . ?
O2 C11 C10 125.7(2) . . ?
O1 C11 C10 110.8(2) . . ?
O3 C12 C13 121.8(2) . . ?
O3 C12 C10 120.4(3) . . ?
C13 C12 C10 117.8(2) . . ?
C17 C15 C16 111.7(3) . . ?
C17 C15 C9 113.1(2) . . ?
C16 C15 C9 110.6(2) . . ?
C17 C15 H15 107.0 . . ?
C16 C15 H15 107.0 . . ?
C9 C15 H15 107.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
C8 C1 C9 C10 -38.7(3) . . . . ?
C2 C1 C9 C10 136.1(2) . . . . ?
C8 C1 C9 C15 89.2(3) . . . . ?
C2 C1 C9 C15 -96.0(3) . . . . ?
C8 N1 C7 C6 -176.5(2) . . . . ?
C8 N1 C7 C2 2.0(3) . . . . ?
C4 C3 C2 C7 1.7(3) . . . . ?
C4 C3 C2 C1 -176.9(2) . . . . ?
N1 C7 C2 C3 179.6(2) . . . . ?
C6 C7 C2 C3 -1.8(3) . . . . ?
N1 C7 C2 C1 -1.5(2) . . . . ?
C6 C7 C2 C1 177.1(2) . . . . ?
C8 C1 C2 C3 179.1(2) . . . . ?
C9 C1 C2 C3 3.4(4) . . . . ?
C8 C1 C2 C7 0.4(2) . . . . ?
C9 C1 C2 C7 -175.33(19) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
N1 C7 C6 C5 178.4(2) . . . . ?
C2 C7 C6 C5 0.1(3) . . . . ?
C2 C1 C8 N1 0.9(3) . . . . ?
C9 C1 C8 N1 176.5(2) . . . . ?
C7 N1 C8 C1 -1.8(3) . . . . ?
C1 C9 C10 C11 -165.52(18) . . . . ?
C15 C9 C10 C11 65.7(2) . . . . ?
C1 C9 C10 C12 -45.2(2) . . . . ?
C15 C9 C10 C12 -174.0(2) . . . . ?
C7 C6 C5 C4 1.8(3) . . . . ?
C7 C6 C5 Cl01 -175.96(17) . . . . ?
C3 C4 C5 C6 -1.9(4) . . . . ?
C3 C4 C5 Cl01 175.92(18) . . . . ?
C14 O1 C11 O2 3.0(4) . . . . ?
C14 O1 C11 C10 -174.6(2) . . . . ?
C12 C10 C11 O2 -106.8(3) . . . . ?
C9 C10 C11 O2 16.8(3) . . . . ?
C12 C10 C11 O1 70.7(2) . . . . ?
C9 C10 C11 O1 -165.69(19) . . . . ?
C11 C10 C12 O3 -111.4(3) . . . . ?
C9 C10 C12 O3 125.1(3) . . . . ?
C11 C10 C12 C13 68.3(3) . . . . ?
C9 C10 C12 C13 -55.2(3) . . . . ?
C1 C9 C15 C17 -57.3(3) . . . . ?
C10 C9 C15 C17 69.7(3) . . . . ?
C1 C9 C15 C16 68.9(3) . . . . ?
C10 C9 C15 C16 -164.0(2) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.027

####################################################################### 
# 
# 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_villani-minor2_a
_database_code_depnum_ccdc_archive 'CCDC 1897063'
loop_
_audit_author_name
_audit_author_address
'Andrea Mazzanti'
;university of Bologna
Italy
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;
_audit_creation_date             01/29/2018
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'compound 2b'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 Cl N O3'
_chemical_formula_weight         321.79

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      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                   9.9020(12)
_cell_length_b                   19.022(2)
_cell_length_c                   9.2904(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1749.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    603
_cell_measurement_theta_min      1.79
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   0.973
_exptl_transmission_factor_max   0.977
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'Bruker 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
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24496
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         27.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3897
_reflns_number_gt                3445
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.999

_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)+(0.0622P)²+0.2438P] 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_abs_structure_details 
;
 Flack x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3897
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
Cl01 Cl 0.64753(10) 0.50764(5) 0.79235(10) 0.0819(3) Uani 1 1 d . . . . .
O002 O 0.3535(2) 0.73230(11) -0.06445(19) 0.0665(6) Uani 1 1 d . . . . .
O1 O 0.3935(3) 0.86798(11) 0.2801(3) 0.0822(7) Uani 1 1 d . . . . .
O004 O 0.5416(2) 0.78861(13) 0.2065(3) 0.0852(8) Uani 1 1 d . . . . .
C005 C 0.2968(3) 0.77291(13) 0.0139(2) 0.0441(5) Uani 1 1 d . . . . .
C006 C 0.3219(2) 0.68814(13) 0.2251(2) 0.0412(5) Uani 1 1 d . . . . .
H006 H 0.4049 0.6703 0.1808 0.049 Uiso 1 1 calc R U . . .
C007 C 0.4294(2) 0.63781(12) 0.4611(2) 0.0406(5) Uani 1 1 d . . . . .
N1 N 0.3166(3) 0.70093(15) 0.6225(2) 0.0646(7) Uani 1 1 d . . . . .
C009 C 0.3412(2) 0.68442(13) 0.3864(2) 0.0427(5) Uani 1 1 d . . . . .
C00A C 0.4293(3) 0.80704(14) 0.2226(3) 0.0504(6) Uani 1 1 d . . . . .
C00B C 0.3062(2) 0.76489(13) 0.1776(2) 0.0409(5) Uani 1 1 d . . . . .
H00B H 0.2253 0.7850 0.2224 0.049 Uiso 1 1 calc R U . . .
C00C C 0.4101(3) 0.64929(13) 0.6086(3) 0.0469(6) Uani 1 1 d . . . . .
C00D C 0.2752(3) 0.72143(16) 0.4891(3) 0.0593(7) Uani 1 1 d . . . . .
H00D H 0.2107 0.7559 0.4712 0.071 Uiso 1 1 calc R U . . .
C00E C 0.5897(3) 0.54847(16) 0.5223(3) 0.0598(7) Uani 1 1 d . . . . .
H00E H 0.6513 0.5141 0.4948 0.072 Uiso 1 1 calc R U . . .
C00F C 0.4769(3) 0.61054(14) 0.7141(3) 0.0542(6) Uani 1 1 d . . . . .
H00F H 0.4622 0.6184 0.8117 0.065 Uiso 1 1 calc R U . . .
C00G C 0.5233(3) 0.58707(14) 0.4202(3) 0.0529(6) Uani 1 1 d . . . . .
H00G H 0.5410 0.5794 0.3231 0.063 Uiso 1 1 calc R U . . .
C00H C 0.5649(3) 0.56067(14) 0.6669(3) 0.0538(6) Uani 1 1 d . . . . .
C00I C 0.2168(4) 0.83303(16) -0.0410(3) 0.0658(8) Uani 1 1 d . . . . .
H00A H 0.2311 0.8378 -0.1427 0.099 Uiso 1 1 calc R U . . .
H00C H 0.2448 0.8753 0.0069 0.099 Uiso 1 1 calc R U . . .
H00H H 0.1227 0.8249 -0.0226 0.099 Uiso 1 1 calc R U . . .
C00J C 0.2044(3) 0.64118(16) 0.1707(4) 0.0673(8) Uani 1 1 d . . . . .
H00J H 0.1942 0.6508 0.0676 0.081 Uiso 1 1 calc R U . . .
C00K C 0.0712(4) 0.6578(3) 0.2399(7) 0.1142(18) Uani 1 1 d . . . . .
H00I H 0.0009 0.6318 0.1927 0.171 Uiso 1 1 calc R U . . .
H00K H 0.0533 0.7072 0.2315 0.171 Uiso 1 1 calc R U . . .
H00L H 0.0742 0.6449 0.3398 0.171 Uiso 1 1 calc R U . . .
C00L C 0.2412(5) 0.56401(19) 0.1846(7) 0.1121(17) Uani 1 1 d . . . . .
H00M H 0.2399 0.5507 0.2842 0.168 Uiso 1 1 calc R U . . .
H00N H 0.3299 0.5564 0.1459 0.168 Uiso 1 1 calc R U . . .
H00O H 0.1769 0.5361 0.1323 0.168 Uiso 1 1 calc R U . . .
C00M C 0.5047(6) 0.9132(2) 0.3217(6) 0.1169(19) Uani 1 1 d . . . . .
H00P H 0.5593 0.8897 0.3923 0.175 Uiso 1 1 calc R U . . .
H00Q H 0.4698 0.9560 0.3617 0.175 Uiso 1 1 calc R U . . .
H00R H 0.5587 0.9238 0.2387 0.175 Uiso 1 1 calc R U . . .
H1N H 0.276(4) 0.7112(19) 0.698(5) 0.082(11) 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
Cl01 C00H 1.745(3) . ?
O002 C005 1.201(3) . ?
O1 C00A 1.325(3) . ?
O1 C00M 1.449(5) . ?
O004 C00A 1.175(4) . ?
C005 C00I 1.481(4) . ?
C005 C00B 1.532(3) . ?
C006 C009 1.513(3) . ?
C006 C00B 1.533(3) . ?
C006 C00J 1.551(4) . ?
C006 H006 0.9800 . ?
C007 C00G 1.393(3) . ?
C007 C00C 1.401(3) . ?
C007 C009 1.425(3) . ?
N1 C00C 1.356(4) . ?
N1 C00D 1.362(4) . ?
N1 H1N 0.83(4) . ?
C009 C00D 1.354(4) . ?
C00A C00B 1.518(4) . ?
C00B H00B 0.9800 . ?
C00C C00F 1.394(4) . ?
C00D H00D 0.9300 . ?
C00E C00G 1.368(4) . ?
C00E C00H 1.385(4) . ?
C00E H00E 0.9300 . ?
C00F C00H 1.360(4) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00I H00A 0.9600 . ?
C00I H00C 0.9600 . ?
C00I H00H 0.9600 . ?
C00J C00K 1.501(6) . ?
C00J C00L 1.518(5) . ?
C00J H00J 0.9800 . ?
C00K H00I 0.9600 . ?
C00K H00K 0.9600 . ?
C00K H00L 0.9600 . ?
C00L H00M 0.9600 . ?
C00L H00N 0.9600 . ?
C00L H00O 0.9600 . ?
C00M H00P 0.9600 . ?
C00M H00Q 0.9600 . ?
C00M H00R 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
C00A O1 C00M 115.1(3) . . ?
O002 C005 C00I 122.6(2) . . ?
O002 C005 C00B 120.6(2) . . ?
C00I C005 C00B 116.8(2) . . ?
C009 C006 C00B 110.02(19) . . ?
C009 C006 C00J 113.0(2) . . ?
C00B C006 C00J 112.3(2) . . ?
C009 C006 H006 107.1 . . ?
C00B C006 H006 107.1 . . ?
C00J C006 H006 107.1 . . ?
C00G C007 C00C 117.8(2) . . ?
C00G C007 C009 135.0(2) . . ?
C00C C007 C009 107.2(2) . . ?
C00C N1 C00D 109.1(2) . . ?
C00C N1 H1N 125(3) . . ?
C00D N1 H1N 124(3) . . ?
C00D C009 C007 106.1(2) . . ?
C00D C009 C006 127.8(2) . . ?
C007 C009 C006 126.1(2) . . ?
O004 C00A O1 124.4(3) . . ?
O004 C00A C00B 124.6(2) . . ?
O1 C00A C00B 111.0(2) . . ?
C00A C00B C005 105.6(2) . . ?
C00A C00B C006 110.0(2) . . ?
C005 C00B C006 112.76(19) . . ?
C00A C00B H00B 109.4 . . ?
C005 C00B H00B 109.4 . . ?
C006 C00B H00B 109.4 . . ?
N1 C00C C00F 129.8(2) . . ?
N1 C00C C007 107.4(2) . . ?
C00F C00C C007 122.7(2) . . ?
C009 C00D N1 110.3(2) . . ?
C009 C00D H00D 124.9 . . ?
N1 C00D H00D 124.9 . . ?
C00G C00E C00H 119.8(3) . . ?
C00G C00E H00E 120.1 . . ?
C00H C00E H00E 120.1 . . ?
C00H C00F C00C 116.5(2) . . ?
C00H C00F H00F 121.8 . . ?
C00C C00F H00F 121.8 . . ?
C00E C00G C007 120.2(2) . . ?
C00E C00G H00G 119.9 . . ?
C007 C00G H00G 119.9 . . ?
C00F C00H C00E 122.9(3) . . ?
C00F C00H Cl01 119.2(2) . . ?
C00E C00H Cl01 117.9(2) . . ?
C005 C00I H00A 109.5 . . ?
C005 C00I H00C 109.5 . . ?
H00A C00I H00C 109.5 . . ?
C005 C00I H00H 109.5 . . ?
H00A C00I H00H 109.5 . . ?
H00C C00I H00H 109.5 . . ?
C00K C00J C00L 112.2(4) . . ?
C00K C00J C006 113.5(3) . . ?
C00L C00J C006 110.5(3) . . ?
C00K C00J H00J 106.8 . . ?
C00L C00J H00J 106.8 . . ?
C006 C00J H00J 106.8 . . ?
C00J C00K H00I 109.5 . . ?
C00J C00K H00K 109.5 . . ?
H00I C00K H00K 109.5 . . ?
C00J C00K H00L 109.5 . . ?
H00I C00K H00L 109.5 . . ?
H00K C00K H00L 109.5 . . ?
C00J C00L H00M 109.5 . . ?
C00J C00L H00N 109.5 . . ?
H00M C00L H00N 109.5 . . ?
C00J C00L H00O 109.5 . . ?
H00M C00L H00O 109.5 . . ?
H00N C00L H00O 109.5 . . ?
O1 C00M H00P 109.5 . . ?
O1 C00M H00Q 109.5 . . ?
H00P C00M H00Q 109.5 . . ?
O1 C00M H00R 109.5 . . ?
H00P C00M H00R 109.5 . . ?
H00Q C00M H00R 109.5 . . ?

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
C00G C007 C009 C00D -179.6(3) . . . . ?
C00C C007 C009 C00D 0.5(3) . . . . ?
C00G C007 C009 C006 3.2(4) . . . . ?
C00C C007 C009 C006 -176.7(2) . . . . ?
C00B C006 C009 C00D 42.1(4) . . . . ?
C00J C006 C009 C00D -84.3(4) . . . . ?
C00B C006 C009 C007 -141.4(2) . . . . ?
C00J C006 C009 C007 92.3(3) . . . . ?
C00M O1 C00A O004 1.1(5) . . . . ?
C00M O1 C00A C00B -177.8(3) . . . . ?
O004 C00A C00B C005 -76.0(4) . . . . ?
O1 C00A C00B C005 102.9(3) . . . . ?
O004 C00A C00B C006 46.0(4) . . . . ?
O1 C00A C00B C006 -135.1(2) . . . . ?
O002 C005 C00B C00A 89.6(3) . . . . ?
C00I C005 C00B C00A -89.6(3) . . . . ?
O002 C005 C00B C006 -30.7(3) . . . . ?
C00I C005 C00B C006 150.2(2) . . . . ?
C009 C006 C00B C00A 58.0(3) . . . . ?
C00J C006 C00B C00A -175.2(2) . . . . ?
C009 C006 C00B C005 175.7(2) . . . . ?
C00J C006 C00B C005 -57.5(3) . . . . ?
C00D N1 C00C C00F -177.3(3) . . . . ?
C00D N1 C00C C007 0.9(4) . . . . ?
C00G C007 C00C N1 179.2(2) . . . . ?
C009 C007 C00C N1 -0.9(3) . . . . ?
C00G C007 C00C C00F -2.4(4) . . . . ?
C009 C007 C00C C00F 177.5(2) . . . . ?
C007 C009 C00D N1 0.1(3) . . . . ?
C006 C009 C00D N1 177.2(3) . . . . ?
C00C N1 C00D C009 -0.6(4) . . . . ?
N1 C00C C00F C00H 178.9(3) . . . . ?
C007 C00C C00F C00H 0.8(4) . . . . ?
C00H C00E C00G C007 -1.0(4) . . . . ?
C00C C007 C00G C00E 2.4(4) . . . . ?
C009 C007 C00G C00E -177.4(3) . . . . ?
C00C C00F C00H C00E 0.7(4) . . . . ?
C00C C00F C00H Cl01 -177.5(2) . . . . ?
C00G C00E C00H C00F -0.6(5) . . . . ?
C00G C00E C00H Cl01 177.6(2) . . . . ?
C009 C006 C00J C00K 57.1(4) . . . . ?
C00B C006 C00J C00K -68.1(3) . . . . ?
C009 C006 C00J C00L -69.9(4) . . . . ?
C00B C006 C00J C00L 164.9(3) . . . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.035

