# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 1465336'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(Z)-diethyl 1-acetyl-5-benzylidene-4-(trifluoromethyl)pyrrolidine-2,2-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 F3 N O5'
_chemical_formula_weight         413.39

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.8343(4)
_cell_length_b                   10.9242(5)
_cell_length_c                   10.9439(5)
_cell_angle_alpha                103.635(2)
_cell_angle_beta                 97.925(2)
_cell_angle_gamma                91.114(2)
_cell_volume                     1015.12(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9665
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11891
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3536
_reflns_number_gt                2564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0677P)²+0.4206P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3536
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7447(2) 0.22502(17) 0.30896(16) 0.0397(4) Uani 1 1 d . . .
O1 O 0.4490(2) 0.1908(2) 0.04119(17) 0.0722(6) Uani 1 1 d . . .
O2 O 0.45896(18) 0.29193(18) 0.24411(15) 0.0576(5) Uani 1 1 d . . .
O3 O 0.9137(2) 0.31681(19) 0.1216(2) 0.0705(6) Uani 1 1 d . . .
O4 O 0.6882(2) 0.40276(17) 0.08941(16) 0.0604(5) Uani 1 1 d . . .
O5 O 0.8011(2) 0.43307(16) 0.36443(16) 0.0632(5) Uani 1 1 d . . .
F1 F 0.9527(2) -0.09810(19) 0.3042(2) 0.0968(6) Uani 1 1 d . . .
F2 F 0.9625(2) -0.09665(18) 0.1105(2) 0.0989(7) Uani 1 1 d . . .
F3 F 1.02967(19) 0.07039(18) 0.2589(2) 0.0940(6) Uani 1 1 d . . .
C1 C 0.5501(3) 0.2446(3) 0.5429(3) 0.0648(7) Uani 1 1 d . . .
H1A H 0.5287 0.2737 0.4693 0.078 Uiso 1 1 calc R . .
C2 C 0.4980(4) 0.3081(4) 0.6524(3) 0.0820(9) Uani 1 1 d . . .
H2A H 0.4417 0.3791 0.6520 0.098 Uiso 1 1 calc R . .
C3 C 0.5287(4) 0.2670(4) 0.7616(3) 0.0897(11) Uani 1 1 d . . .
H3A H 0.4944 0.3103 0.8357 0.108 Uiso 1 1 calc R . .
C4 C 0.6101(4) 0.1619(5) 0.7609(3) 0.0916(12) Uani 1 1 d . . .
H4A H 0.6315 0.1339 0.8351 0.110 Uiso 1 1 calc R . .
C5 C 0.6609(3) 0.0969(3) 0.6513(3) 0.0721(9) Uani 1 1 d . . .
H5A H 0.7140 0.0242 0.6517 0.086 Uiso 1 1 calc R . .
C6 C 0.6335(3) 0.1389(3) 0.5406(2) 0.0543(7) Uani 1 1 d . . .
C7 C 0.6880(3) 0.0651(2) 0.4257(2) 0.0502(6) Uani 1 1 d . . .
H7A H 0.6919 -0.0209 0.4208 0.060 Uiso 1 1 calc R . .
C8 C 0.7328(3) 0.1011(2) 0.3274(2) 0.0441(5) Uani 1 1 d . . .
C9 C 0.7659(3) 0.0129(2) 0.2068(2) 0.0496(6) Uani 1 1 d . . .
H9A H 0.6947 -0.0615 0.1850 0.060 Uiso 1 1 calc R . .
C10 C 0.7357(3) 0.0880(2) 0.1056(2) 0.0562(7) Uani 1 1 d . . .
H10A H 0.6527 0.0472 0.0402 0.067 Uiso 1 1 calc R . .
H10B H 0.8265 0.0944 0.0662 0.067 Uiso 1 1 calc R . .
C11 C 0.6923(3) 0.2208(2) 0.17422(19) 0.0414(5) Uani 1 1 d . . .
C12 C 0.5193(3) 0.2327(2) 0.1448(2) 0.0463(6) Uani 1 1 d . . .
C13 C 0.2931(3) 0.3064(4) 0.2228(3) 0.0807(10) Uani 1 1 d . . .
H13A H 0.2686 0.3526 0.1577 0.097 Uiso 1 1 calc R . .
H13B H 0.2397 0.2240 0.1938 0.097 Uiso 1 1 calc R . .
C14 C 0.2451(4) 0.3724(5) 0.3377(4) 0.1334(19) Uani 1 1 d . . .
H14A H 0.1366 0.3814 0.3237 0.200 Uiso 1 1 calc R . .
H14B H 0.2970 0.4544 0.3653 0.200 Uiso 1 1 calc R . .
H14C H 0.2692 0.3262 0.4017 0.200 Uiso 1 1 calc R . .
C15 C 0.7802(3) 0.3210(2) 0.1284(2) 0.0487(6) Uani 1 1 d . . .
C16 C 0.7598(4) 0.4953(3) 0.0352(3) 0.0833(10) Uani 1 1 d . . .
H16A H 0.6812 0.5321 -0.0138 0.100 Uiso 1 1 calc R . .
H16B H 0.8274 0.4531 -0.0222 0.100 Uiso 1 1 calc R . .
C17 C 0.8489(5) 0.5974(3) 0.1351(4) 0.0968(12) Uani 1 1 d . . .
H17A H 0.8946 0.6559 0.0959 0.145 Uiso 1 1 calc R . .
H17B H 0.9277 0.5615 0.1831 0.145 Uiso 1 1 calc R . .
H17C H 0.7819 0.6408 0.1908 0.145 Uiso 1 1 calc R . .
C18 C 0.8144(3) 0.3323(2) 0.3921(2) 0.0475(6) Uani 1 1 d . . .
C19 C 0.9116(3) 0.3178(3) 0.5116(2) 0.0615(7) Uani 1 1 d . . .
H19A H 0.9527 0.3992 0.5611 0.092 Uiso 1 1 calc R . .
H19B H 0.9939 0.2647 0.4897 0.092 Uiso 1 1 calc R . .
H19C H 0.8501 0.2802 0.5603 0.092 Uiso 1 1 calc R . .
C20 C 0.9268(4) -0.0276(3) 0.2203(3) 0.0671(8) 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
N1 C18 1.376(3) . ?
N1 C8 1.420(3) . ?
N1 C11 1.473(3) . ?
O1 C12 1.196(3) . ?
O2 C12 1.313(3) . ?
O2 C13 1.469(3) . ?
O3 C15 1.192(3) . ?
O4 C15 1.324(3) . ?
O4 C16 1.462(3) . ?
O5 C18 1.213(3) . ?
F1 C20 1.331(3) . ?
F2 C20 1.340(3) . ?
F3 C20 1.339(3) . ?
C1 C6 1.379(4) . ?
C1 C2 1.379(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.368(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.366(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.387(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.472(4) . ?
C7 C8 1.333(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.508(3) . ?
C9 C20 1.495(4) . ?
C9 C10 1.525(4) . ?
C9 H9A 0.9800 . ?
C10 C11 1.550(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.532(3) . ?
C11 C15 1.545(3) . ?
C13 C14 1.418(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C17 1.488(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.505(3) . ?
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
C18 N1 C8 128.58(19) . . ?
C18 N1 C11 121.85(18) . . ?
C8 N1 C11 108.83(17) . . ?
C12 O2 C13 116.1(2) . . ?
C15 O4 C16 115.9(2) . . ?
C6 C1 C2 121.1(3) . . ?
C6 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C1 C6 C5 117.9(3) . . ?
C1 C6 C7 123.6(2) . . ?
C5 C6 C7 118.5(3) . . ?
C8 C7 C6 130.7(2) . . ?
C8 C7 H7A 114.6 . . ?
C6 C7 H7A 114.6 . . ?
C7 C8 N1 128.1(2) . . ?
C7 C8 C9 125.1(2) . . ?
N1 C8 C9 106.56(18) . . ?
C20 C9 C8 111.5(2) . . ?
C20 C9 C10 112.0(2) . . ?
C8 C9 C10 104.69(19) . . ?
C20 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C9 C10 C11 106.64(19) . . ?
C9 C10 H10A 110.4 . . ?
C11 C10 H10A 110.4 . . ?
C9 C10 H10B 110.4 . . ?
C11 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
N1 C11 C12 113.14(17) . . ?
N1 C11 C15 111.64(17) . . ?
C12 C11 C15 110.42(19) . . ?
N1 C11 C10 102.71(18) . . ?
C12 C11 C10 109.85(19) . . ?
C15 C11 C10 108.74(19) . . ?
O1 C12 O2 124.7(2) . . ?
O1 C12 C11 122.1(2) . . ?
O2 C12 C11 113.14(19) . . ?
C14 C13 O2 109.6(3) . . ?
C14 C13 H13A 109.8 . . ?
O2 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
O2 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 125.5(2) . . ?
O3 C15 C11 122.2(2) . . ?
O4 C15 C11 112.1(2) . . ?
O4 C16 C17 111.9(3) . . ?
O4 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
O4 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
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 . . ?
O5 C18 N1 119.4(2) . . ?
O5 C18 C19 122.6(2) . . ?
N1 C18 C19 117.9(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F1 C20 F3 106.4(3) . . ?
F1 C20 F2 106.3(2) . . ?
F3 C20 F2 106.6(2) . . ?
F1 C20 C9 112.5(2) . . ?
F3 C20 C9 112.4(2) . . ?
F2 C20 C9 112.2(3) . . ?

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 0.2(5) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
C2 C1 C6 C5 1.2(4) . . . . ?
C2 C1 C6 C7 178.0(3) . . . . ?
C4 C5 C6 C1 -2.1(4) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C1 C6 C7 C8 32.9(4) . . . . ?
C5 C6 C7 C8 -150.3(3) . . . . ?
C6 C7 C8 N1 2.3(4) . . . . ?
C6 C7 C8 C9 -171.2(2) . . . . ?
C18 N1 C8 C7 49.0(4) . . . . ?
C11 N1 C8 C7 -140.8(2) . . . . ?
C18 N1 C8 C9 -136.5(2) . . . . ?
C11 N1 C8 C9 33.7(2) . . . . ?
C7 C8 C9 C20 -85.5(3) . . . . ?
N1 C8 C9 C20 99.9(2) . . . . ?
C7 C8 C9 C10 153.3(2) . . . . ?
N1 C8 C9 C10 -21.3(2) . . . . ?
C20 C9 C10 C11 -118.5(2) . . . . ?
C8 C9 C10 C11 2.4(3) . . . . ?
C18 N1 C11 C12 -101.6(2) . . . . ?
C8 N1 C11 C12 87.5(2) . . . . ?
C18 N1 C11 C15 23.7(3) . . . . ?
C8 N1 C11 C15 -147.26(19) . . . . ?
C18 N1 C11 C10 140.1(2) . . . . ?
C8 N1 C11 C10 -30.9(2) . . . . ?
C9 C10 C11 N1 16.3(2) . . . . ?
C9 C10 C11 C12 -104.3(2) . . . . ?
C9 C10 C11 C15 134.8(2) . . . . ?
C13 O2 C12 O1 -0.2(4) . . . . ?
C13 O2 C12 C11 -179.8(2) . . . . ?
N1 C11 C12 O1 -154.5(2) . . . . ?
C15 C11 C12 O1 79.6(3) . . . . ?
C10 C11 C12 O1 -40.4(3) . . . . ?
N1 C11 C12 O2 25.1(3) . . . . ?
C15 C11 C12 O2 -100.8(2) . . . . ?
C10 C11 C12 O2 139.3(2) . . . . ?
C12 O2 C13 C14 -179.6(3) . . . . ?
C16 O4 C15 O3 -0.7(4) . . . . ?
C16 O4 C15 C11 -175.5(2) . . . . ?
N1 C11 C15 O3 66.1(3) . . . . ?
C12 C11 C15 O3 -167.2(2) . . . . ?
C10 C11 C15 O3 -46.6(3) . . . . ?
N1 C11 C15 O4 -119.0(2) . . . . ?
C12 C11 C15 O4 7.8(3) . . . . ?
C10 C11 C15 O4 128.4(2) . . . . ?
C15 O4 C16 C17 -76.8(4) . . . . ?
C8 N1 C18 O5 -173.2(2) . . . . ?
C11 N1 C18 O5 17.8(3) . . . . ?
C8 N1 C18 C19 10.0(4) . . . . ?
C11 N1 C18 C19 -159.1(2) . . . . ?
C8 C9 C20 F1 65.9(3) . . . . ?
C10 C9 C20 F1 -177.2(2) . . . . ?
C8 C9 C20 F3 -54.2(3) . . . . ?
C10 C9 C20 F3 62.7(3) . . . . ?
C8 C9 C20 F2 -174.3(2) . . . . ?
C10 C9 C20 F2 -57.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DCM/Hexane
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1465337'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'diethyl 2-acetamido-2-(2-(difluoromethylene)-4-phenylbut-3-yn-1-yl)malonate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 F2 N O5'
_chemical_formula_weight         393.38

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.7953(10)
_cell_length_b                   21.8368(19)
_cell_length_c                   9.4439(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.580(2)
_cell_angle_gamma                90.00
_cell_volume                     2040.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9481
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18996
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3587
_reflns_number_gt                2389
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0549P)²+0.8494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3587
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.28156(19) 0.21173(8) 0.3527(2) 0.0310(5) Uani 1 1 d . . .
H1A H 0.2699 0.2225 0.4364 0.037 Uiso 1 1 calc R . .
O1 O 0.18822(17) 0.11636(8) 0.02903(18) 0.0427(5) Uani 1 1 d . . .
O2 O 0.06542(16) 0.18897(8) 0.08225(18) 0.0425(4) Uani 1 1 d . . .
O3 O 0.13034(16) 0.06298(7) 0.30457(17) 0.0353(4) Uani 1 1 d . . .
O4 O 0.13170(17) 0.14052(7) 0.46316(19) 0.0398(4) Uani 1 1 d . . .
O5 O 0.33773(18) 0.23955(7) 0.15744(18) 0.0410(4) Uani 1 1 d . . .
F1 F 0.60764(16) 0.18912(8) 0.50206(18) 0.0618(5) Uani 1 1 d . . .
F2 F 0.64334(16) 0.14700(9) 0.72089(17) 0.0691(5) Uani 1 1 d . . .
C1 C 0.3306(3) 0.01222(12) 0.8885(3) 0.0423(6) Uani 1 1 d . . .
H1B H 0.3491 0.0539 0.9179 0.051 Uiso 1 1 calc R . .
C2 C 0.2854(3) -0.02602(13) 0.9731(3) 0.0519(7) Uani 1 1 d . . .
H2A H 0.2712 -0.0105 1.0594 0.062 Uiso 1 1 calc R . .
C3 C 0.2609(3) -0.08646(14) 0.9331(3) 0.0576(8) Uani 1 1 d . . .
H3A H 0.2317 -0.1131 0.9933 0.069 Uiso 1 1 calc R . .
C4 C 0.2784(3) -0.10877(13) 0.8065(4) 0.0608(8) Uani 1 1 d . . .
H4A H 0.2603 -0.1506 0.7785 0.073 Uiso 1 1 calc R . .
C5 C 0.3222(3) -0.07055(12) 0.7196(3) 0.0450(7) Uani 1 1 d . . .
H5A H 0.3338 -0.0862 0.6318 0.054 Uiso 1 1 calc R . .
C6 C 0.3494(2) -0.00956(11) 0.7599(3) 0.0341(6) Uani 1 1 d . . .
C7 C 0.3945(2) 0.03064(12) 0.6693(3) 0.0362(6) Uani 1 1 d . . .
C8 C 0.4303(2) 0.06528(12) 0.5951(3) 0.0359(6) Uani 1 1 d . . .
C9 C 0.4653(2) 0.10854(11) 0.5026(3) 0.0333(6) Uani 1 1 d . . .
C10 C 0.5655(3) 0.14637(13) 0.5710(3) 0.0464(7) Uani 1 1 d . . .
C11 C 0.3824(2) 0.11255(11) 0.3311(2) 0.0312(5) Uani 1 1 d . . .
H11A H 0.3588 0.0707 0.2884 0.037 Uiso 1 1 calc R . .
H11B H 0.4368 0.1322 0.2807 0.037 Uiso 1 1 calc R . .
C12 C 0.2511(2) 0.14980(10) 0.2940(2) 0.0290(5) Uani 1 1 d . . .
C13 C 0.1682(2) 0.14987(11) 0.1180(3) 0.0329(5) Uani 1 1 d . . .
C14 C -0.0174(3) 0.19580(14) -0.0812(3) 0.0578(8) Uani 1 1 d . . .
H14A H -0.0641 0.1569 -0.1245 0.069 Uiso 1 1 calc R . .
H14B H 0.0393 0.2073 -0.1374 0.069 Uiso 1 1 calc R . .
C15 C -0.1173(3) 0.24467(14) -0.0966(4) 0.0830(12) Uani 1 1 d . . .
H15A H -0.1755 0.2506 -0.2061 0.124 Uiso 1 1 calc R . .
H15B H -0.0698 0.2829 -0.0536 0.124 Uiso 1 1 calc R . .
H15C H -0.1727 0.2328 -0.0405 0.124 Uiso 1 1 calc R . .
C16 C 0.1633(2) 0.11858(11) 0.3663(2) 0.0300(5) Uani 1 1 d . . .
C17 C 0.0594(2) 0.02303(11) 0.3701(3) 0.0398(6) Uani 1 1 d . . .
H17A H -0.0336 0.0382 0.3440 0.048 Uiso 1 1 calc R . .
H17B H 0.1072 0.0215 0.4840 0.048 Uiso 1 1 calc R . .
C18 C 0.0560(3) -0.03931(13) 0.3022(4) 0.0587(8) Uani 1 1 d . . .
H18A H 0.0090 -0.0678 0.3439 0.088 Uiso 1 1 calc R . .
H18B H 0.1486 -0.0537 0.3287 0.088 Uiso 1 1 calc R . .
H18C H 0.0081 -0.0372 0.1896 0.088 Uiso 1 1 calc R . .
C19 C 0.3277(2) 0.25293(11) 0.2792(3) 0.0342(6) Uani 1 1 d . . .
C20 C 0.3632(3) 0.31494(11) 0.3496(3) 0.0496(7) Uani 1 1 d . . .
H20A H 0.3953 0.3405 0.2858 0.074 Uiso 1 1 calc R . .
H20B H 0.4346 0.3113 0.4537 0.074 Uiso 1 1 calc R . .
H20C H 0.2831 0.3338 0.3557 0.074 Uiso 1 1 calc R . .


_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
N1 C19 1.348(3) . ?
N1 C12 1.449(3) . ?
N1 H1A 0.8800 . ?
O1 C13 1.197(3) . ?
O2 C13 1.332(3) . ?
O2 C14 1.449(3) . ?
O3 C16 1.332(3) . ?
O3 C17 1.453(3) . ?
O4 C16 1.196(3) . ?
O5 C19 1.232(3) . ?
F1 C10 1.318(3) . ?
F2 C10 1.326(3) . ?
C1 C2 1.373(3) . ?
C1 C6 1.393(3) . ?
C1 H1B 0.9500 . ?
C2 C3 1.369(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.373(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.440(3) . ?
C7 C8 1.195(3) . ?
C8 C9 1.436(3) . ?
C9 C10 1.308(3) . ?
C9 C11 1.507(3) . ?
C11 C12 1.548(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.532(3) . ?
C12 C13 1.541(3) . ?
C14 C15 1.483(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C18 1.499(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.489(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N1 C12 120.02(18) . . ?
C19 N1 H1A 120.0 . . ?
C12 N1 H1A 120.0 . . ?
C13 O2 C14 115.6(2) . . ?
C16 O3 C17 117.04(17) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 H1B 119.7 . . ?
C6 C1 H1B 119.7 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 120.5(2) . . ?
C1 C6 C7 120.8(2) . . ?
C8 C7 C6 178.2(3) . . ?
C7 C8 C9 176.6(2) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 C11 120.8(2) . . ?
C8 C9 C11 120.3(2) . . ?
C9 C10 F1 125.7(2) . . ?
C9 C10 F2 125.4(2) . . ?
F1 C10 F2 108.9(2) . . ?
C9 C11 C12 111.75(18) . . ?
C9 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C9 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
N1 C12 C16 109.34(17) . . ?
N1 C12 C13 110.91(18) . . ?
C16 C12 C13 106.61(17) . . ?
N1 C12 C11 110.90(18) . . ?
C16 C12 C11 109.80(18) . . ?
C13 C12 C11 109.19(17) . . ?
O1 C13 O2 125.4(2) . . ?
O1 C13 C12 124.5(2) . . ?
O2 C13 C12 109.84(19) . . ?
O2 C14 C15 107.1(3) . . ?
O2 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O2 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O3 126.3(2) . . ?
O4 C16 C12 125.4(2) . . ?
O3 C16 C12 108.36(18) . . ?
O3 C17 C18 106.8(2) . . ?
O3 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O3 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 N1 120.7(2) . . ?
O5 C19 C20 122.0(2) . . ?
N1 C19 C20 117.32(19) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 C1 C2 C3 1.2(4) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C4 C5 C6 C7 -179.7(2) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C1 C6 C7 178.9(2) . . . . ?
C5 C6 C7 C8 150(9) . . . . ?
C1 C6 C7 C8 -29(9) . . . . ?
C6 C7 C8 C9 -43(12) . . . . ?
C7 C8 C9 C10 120(4) . . . . ?
C7 C8 C9 C11 -56(4) . . . . ?
C8 C9 C10 F1 -178.7(2) . . . . ?
C11 C9 C10 F1 -2.4(4) . . . . ?
C8 C9 C10 F2 2.9(4) . . . . ?
C11 C9 C10 F2 179.2(2) . . . . ?
C10 C9 C11 C12 -96.6(3) . . . . ?
C8 C9 C11 C12 79.7(3) . . . . ?
C19 N1 C12 C16 -163.44(19) . . . . ?
C19 N1 C12 C13 -46.2(3) . . . . ?
C19 N1 C12 C11 75.3(2) . . . . ?
C9 C11 C12 N1 59.9(2) . . . . ?
C9 C11 C12 C16 -61.1(2) . . . . ?
C9 C11 C12 C13 -177.61(19) . . . . ?
C14 O2 C13 O1 -8.0(3) . . . . ?
C14 O2 C13 C12 177.1(2) . . . . ?
N1 C12 C13 O1 136.7(2) . . . . ?
C16 C12 C13 O1 -104.4(3) . . . . ?
C11 C12 C13 O1 14.2(3) . . . . ?
N1 C12 C13 O2 -48.4(2) . . . . ?
C16 C12 C13 O2 70.6(2) . . . . ?
C11 C12 C13 O2 -170.88(18) . . . . ?
C13 O2 C14 C15 -175.2(2) . . . . ?
C17 O3 C16 O4 -5.8(3) . . . . ?
C17 O3 C16 C12 173.36(18) . . . . ?
N1 C12 C16 O4 -4.2(3) . . . . ?
C13 C12 C16 O4 -124.2(2) . . . . ?
C11 C12 C16 O4 117.7(2) . . . . ?
N1 C12 C16 O3 176.64(17) . . . . ?
C13 C12 C16 O3 56.7(2) . . . . ?
C11 C12 C16 O3 -61.5(2) . . . . ?
C16 O3 C17 C18 -170.1(2) . . . . ?
C12 N1 C19 O5 3.9(3) . . . . ?
C12 N1 C19 C20 -177.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DCM/Hexane
