# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1057152'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;
_audit_creation_date             2015-03-31
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H18 Cl F4 N O2'
_chemical_formula_moiety         'C15 H18 F4 N O2, Cl'
_chemical_formula_weight         355.76
_chemical_melting_point          ?
_chemical_absolute_configuration rmad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.3827(19)
_cell_length_b                   7.108(2)
_cell_length_c                   20.990(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.301(6)
_cell_angle_gamma                90.0000
_cell_volume                     796.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    844
_cell_measurement_theta_min      19.10
_cell_measurement_theta_max      47.30
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368.00
_exptl_absorpt_coefficient_mu    2.606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.214
_exptl_absorpt_correction_T_max  0.974

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            7844
_diffrn_reflns_av_R_equivalents  0.1436
_diffrn_reflns_theta_max         68.293
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          Twin
_reflns_number_total             2667
_reflns_number_gt                1704
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0966
_refine_ls_wR_factor_ref         0.2711
_refine_ls_wR_factor_gt          0.2465
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2667
_refine_ls_number_parameters     222
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1611P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.038(9)
_refine_ls_abs_structure_details 
;
 Flack x determined using 359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.7416(7) 0.4443(6) 0.9259(2) 0.0830(12) Uani 1 1 d . . . . .
F8 F 0.5256(17) 0.6947(11) 0.6644(4) 0.077(2) Uani 1 1 d . . . . .
F9 F 0.9512(19) 0.8566(13) 0.6395(5) 0.093(3) Uani 1 1 d . . . . .
F11 F 0.6905(19) 0.3659(16) 0.4920(5) 0.092(3) Uani 1 1 d . . . . .
F12 F 0.3734(15) 0.4077(15) 0.5814(4) 0.080(2) Uani 1 1 d . . . . .
O15 O 0.5873(19) -0.0674(18) 0.9385(6) 0.088(3) Uani 1 1 d . . . . .
O16 O 0.336(2) -0.2767(19) 0.8827(7) 0.091(3) Uani 1 1 d D . . . .
H16 H 0.46(4) -0.38(3) 0.888(12) 0.137 Uiso 1 1 d D U . . .
N17 N 0.228(2) 0.1933(18) 0.9441(7) 0.074(3) Uani 1 1 d D . . . .
H17A H 0.27(5) 0.15(3) 0.988(4) 0.112 Uiso 1 1 d D U . . .
H17B H 0.11(3) 0.30(2) 0.933(10) 0.112 Uiso 1 1 d D U . . .
H17C H 0.38(2) 0.24(3) 0.930(10) 0.112 Uiso 1 1 d D U . . .
C1 C 0.522(2) 0.303(2) 0.7156(9) 0.070(4) Uani 1 1 d . . . . .
C2 C 0.398(3) 0.415(2) 0.7561(8) 0.078(4) Uani 1 1 d . . . . .
H2 H 0.4264 0.5467 0.7578 0.093 Uiso 1 1 calc R U . . .
C3 C 0.228(3) 0.332(2) 0.7949(7) 0.071(4) Uani 1 1 d . . . . .
H3 H 0.1321 0.4091 0.8196 0.085 Uiso 1 1 calc R U . . .
C4 C 0.203(3) 0.138(2) 0.7964(8) 0.071(4) Uani 1 1 d . . . . .
C5 C 0.333(3) 0.029(2) 0.7567(10) 0.088(5) Uani 1 1 d . . . . .
H5 H 0.3154 -0.1044 0.7572 0.105 Uiso 1 1 calc R U . . .
C6 C 0.488(3) 0.110(2) 0.7161(10) 0.078(4) Uani 1 1 d . . . . .
H6 H 0.5714 0.0325 0.6885 0.094 Uiso 1 1 calc R U . . .
C7 C 0.697(3) 0.3812(19) 0.6689(8) 0.068(3) Uani 1 1 d . . . . .
H7 H 0.8626 0.3183 0.6803 0.081 Uiso 1 1 calc R U . . .
C8 C 0.743(3) 0.593(2) 0.6780(8) 0.070(4) Uani 1 1 d . . . . .
H8 H 0.8189 0.6180 0.7232 0.083 Uiso 1 1 calc R U . . .
C9 C 0.921(3) 0.660(2) 0.6314(9) 0.076(4) Uani 1 1 d . . . . .
H9 H 1.0875 0.5985 0.6433 0.091 Uiso 1 1 calc R U . . .
C10 C 0.830(3) 0.613(3) 0.5623(10) 0.088(5) Uani 1 1 d . . . . .
H10A H 0.9560 0.6538 0.5345 0.106 Uiso 1 1 calc R U . . .
H10B H 0.6717 0.6811 0.5483 0.106 Uiso 1 1 calc R U . . .
C11 C 0.788(3) 0.404(2) 0.5560(8) 0.070(4) Uani 1 1 d . . . . .
H11 H 0.9533 0.3387 0.5659 0.084 Uiso 1 1 calc R U . . .
C12 C 0.611(3) 0.331(2) 0.6011(8) 0.076(4) Uani 1 1 d . . . . .
H12 H 0.6007 0.1909 0.5973 0.091 Uiso 1 1 calc R U . . .
C13 C 0.028(3) 0.052(2) 0.8403(7) 0.070(4) Uani 1 1 d . . . . .
H13A H -0.0417 -0.0668 0.8208 0.084 Uiso 1 1 calc R U . . .
H13B H -0.1139 0.1391 0.8429 0.084 Uiso 1 1 calc R U . . .
C14 C 0.154(3) 0.010(2) 0.9092(8) 0.072(3) Uani 1 1 d . . . . .
H14 H 0.0302 -0.0564 0.9330 0.086 Uiso 1 1 calc R U . . .
C15 C 0.389(3) -0.1135(19) 0.9114(9) 0.079(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
F8 C8 1.376(18) . ?
F9 C9 1.415(18) . ?
F11 C11 1.406(19) . ?
F12 C12 1.404(18) . ?
O15 C15 1.191(19) . ?
O16 C15 1.32(2) . ?
O16 H16 0.98(3) . ?
N17 C14 1.52(2) . ?
N17 H17A 0.99(3) . ?
N17 H17B 0.98(3) . ?
N17 H17C 0.98(3) . ?
C1 C6 1.38(2) . ?
C1 C2 1.39(2) . ?
C1 C7 1.55(2) . ?
C2 C3 1.43(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.39(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.39(2) . ?
C4 C13 1.53(2) . ?
C5 C6 1.39(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.48(2) . ?
C7 C8 1.53(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.53(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.51(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.51(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.52(2) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 C14 1.55(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.53(2) . ?
C14 H14 1.0000 . ?

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
C15 O16 H16 118(10) . . ?
C14 N17 H17A 100(10) . . ?
C14 N17 H17B 115(10) . . ?
H17A N17 H17B 123(10) . . ?
C14 N17 H17C 110(10) . . ?
H17A N17 H17C 109(10) . . ?
H17B N17 H17C 99(10) . . ?
C6 C1 C2 119.1(15) . . ?
C6 C1 C7 116.9(14) . . ?
C2 C1 C7 124.0(12) . . ?
C1 C2 C3 120.3(14) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.7(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.9(15) . . ?
C3 C4 C13 118.7(14) . . ?
C5 C4 C13 122.3(14) . . ?
C4 C5 C6 121.5(15) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 120.4(16) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C12 C7 C8 112.5(13) . . ?
C12 C7 C1 112.5(13) . . ?
C8 C7 C1 112.1(12) . . ?
C12 C7 H7 106.4 . . ?
C8 C7 H7 106.4 . . ?
C1 C7 H7 106.4 . . ?
F8 C8 C7 111.8(12) . . ?
F8 C8 C9 106.6(13) . . ?
C7 C8 C9 109.4(12) . . ?
F8 C8 H8 109.7 . . ?
C7 C8 H8 109.7 . . ?
C9 C8 H8 109.7 . . ?
F9 C9 C10 110.6(15) . . ?
F9 C9 C8 107.7(13) . . ?
C10 C9 C8 113.2(13) . . ?
F9 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
C9 C10 C11 109.1(15) . . ?
C9 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
F11 C11 C10 107.9(14) . . ?
F11 C11 C12 109.9(13) . . ?
C10 C11 C12 112.4(13) . . ?
F11 C11 H11 108.8 . . ?
C10 C11 H11 108.8 . . ?
C12 C11 H11 108.8 . . ?
F12 C12 C7 110.5(12) . . ?
F12 C12 C11 107.8(13) . . ?
C7 C12 C11 111.8(14) . . ?
F12 C12 H12 108.9 . . ?
C7 C12 H12 108.9 . . ?
C11 C12 H12 108.9 . . ?
C4 C13 C14 114.2(13) . . ?
C4 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C4 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
N17 C14 C15 108.1(12) . . ?
N17 C14 C13 110.0(13) . . ?
C15 C14 C13 113.6(14) . . ?
N17 C14 H14 108.4 . . ?
C15 C14 H14 108.4 . . ?
C13 C14 H14 108.4 . . ?
O15 C15 O16 126.1(15) . . ?
O15 C15 C14 122.8(14) . . ?
O16 C15 C14 111.0(14) . . ?

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
C6 C1 C2 C3 -3(3) . . . . ?
C7 C1 C2 C3 176.1(14) . . . . ?
C1 C2 C3 C4 6(2) . . . . ?
C2 C3 C4 C5 -4(3) . . . . ?
C2 C3 C4 C13 177.5(13) . . . . ?
C3 C4 C5 C6 0(3) . . . . ?
C13 C4 C5 C6 178.9(17) . . . . ?
C2 C1 C6 C5 0(3) . . . . ?
C7 C1 C6 C5 -179.7(15) . . . . ?
C4 C5 C6 C1 2(3) . . . . ?
C6 C1 C7 C12 58.5(19) . . . . ?
C2 C1 C7 C12 -120.8(16) . . . . ?
C6 C1 C7 C8 -173.6(15) . . . . ?
C2 C1 C7 C8 7(2) . . . . ?
C12 C7 C8 F8 64.6(16) . . . . ?
C1 C7 C8 F8 -63.3(17) . . . . ?
C12 C7 C8 C9 -53.3(17) . . . . ?
C1 C7 C8 C9 178.8(12) . . . . ?
F8 C8 C9 F9 56.7(16) . . . . ?
C7 C8 C9 F9 177.8(13) . . . . ?
F8 C8 C9 C10 -65.8(16) . . . . ?
C7 C8 C9 C10 55.2(18) . . . . ?
F9 C9 C10 C11 -177.3(13) . . . . ?
C8 C9 C10 C11 -56.5(17) . . . . ?
C9 C10 C11 F11 176.7(12) . . . . ?
C9 C10 C11 C12 55.3(17) . . . . ?
C8 C7 C12 F12 -66.1(17) . . . . ?
C1 C7 C12 F12 61.6(16) . . . . ?
C8 C7 C12 C11 53.9(17) . . . . ?
C1 C7 C12 C11 -178.4(12) . . . . ?
F11 C11 C12 F12 -54.0(15) . . . . ?
C10 C11 C12 F12 66.3(17) . . . . ?
F11 C11 C12 C7 -175.6(12) . . . . ?
C10 C11 C12 C7 -55.3(18) . . . . ?
C3 C4 C13 C14 -88.8(18) . . . . ?
C5 C4 C13 C14 92.8(19) . . . . ?
C4 C13 C14 N17 66.9(17) . . . . ?
C4 C13 C14 C15 -54.4(18) . . . . ?
N17 C14 C15 O15 2(2) . . . . ?
C13 C14 C15 O15 124.6(18) . . . . ?
N17 C14 C15 O16 179.0(13) . . . . ?
C13 C14 C15 O16 -58.7(18) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,4-dioxane/water'
