# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H37 Cl N O4'
_chemical_formula_weight         366.94

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   5.3932(8)
_cell_length_b                   7.7138(11)
_cell_length_c                   49.332(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2052.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9871
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      23.00

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9445
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'

_exptl_special_details           
; 
  'Blessing, Acta Cryst. (1995) A51, 33-38'  
;

_diffrn_ambient_temperature      200(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 512x512
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33911
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_theta_min         0.83
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3482
_reflns_number_gt                2948
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1416P)²+18.7674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_number_reflns         3482
_refine_ls_number_parameters     225
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.1146
_refine_ls_wR_factor_ref         0.3183
_refine_ls_wR_factor_gt          0.3128
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.4004(2) 0.55977(13) 0.94552(2) 0.0452(3) Uani 1 1 d . . .
N1 N 0.8842(6) 0.7700(4) 0.94214(6) 0.0340(8) Uani 1 1 d . . .
H1 H 0.895(8) 0.646(5) 0.9425(8) 0.037 Uiso 1 1 d . . .
C2 C 0.8680(6) 0.8436(4) 0.97053(7) 0.0276(10) Uani 1 1 d D . .
H2A H 0.8135 0.7503 0.9830 0.033 Uiso 1 1 calc R . .
H2B H 1.0360 0.8800 0.9763 0.033 Uiso 1 1 calc RD . .
C3 C 0.6987(8) 0.9920(5) 0.97356(8) 0.0430(12) Uani 1 1 d D . .
H3 H 0.5456 0.9707 0.9626 0.052 Uiso 1 1 calc R . .
O3 O 0.6350(8) 0.9902(5) 1.00247(7) 0.0740(13) Uani 1 1 d . . .
H3A H 0.7451 1.0427 1.0113 0.111 Uiso 1 1 calc R . .
C4 C 0.8175(6) 1.1687(5) 0.96469(7) 0.0331(10) Uani 1 1 d D . .
H4 H 0.7144 1.2662 0.9719 0.040 Uiso 1 1 calc R . .
O4 O 1.0341(7) 1.1604(7) 0.97899(7) 0.109(2) Uani 1 1 d D . .
H4A H 1.1527 1.1890 0.9689 0.164 Uiso 1 1 calc RD . .
C5 C 0.8581(8) 1.1945(5) 0.93428(7) 0.0464(12) Uani 1 1 d . . .
H5 H 0.9650 1.2985 0.9311 0.056 Uiso 1 1 calc R . .
O5 O 0.6078(6) 1.2235(4) 0.92237(5) 0.0470(8) Uani 1 1 d . . .
H5A H 0.6186 1.2941 0.9095 0.071 Uiso 1 1 calc R . .
C6 C 0.9528(6) 1.0418(4) 0.91741(7) 0.0223(9) Uani 1 1 d . . .
H6 H 0.9482 1.0802 0.8981 0.027 Uiso 1 1 calc R . .
O6 O 1.2112(5) 0.9974(4) 0.92332(6) 0.0436(8) Uani 1 1 d . . .
H6A H 1.3043 1.0774 0.9178 0.065 Uiso 1 1 calc R . .
C7 C 0.8084(7) 0.8763(5) 0.91877(7) 0.0269(9) Uani 1 1 d . . .
H7 H 0.6295 0.9068 0.9211 0.032 Uiso 1 1 calc R . .
C8 C 0.8332(6) 0.7686(4) 0.89224(6) 0.0218(9) Uani 1 1 d . . .
H8A H 1.0052 0.7763 0.8853 0.026 Uiso 1 1 calc R . .
H8B H 0.7958 0.6452 0.8960 0.026 Uiso 1 1 calc R . .
C9 C 0.6540(7) 0.8384(5) 0.87115(7) 0.0324(10) Uani 1 1 d . . .
H9A H 0.4823 0.8176 0.8775 0.039 Uiso 1 1 calc R . .
H9B H 0.6774 0.9653 0.8696 0.039 Uiso 1 1 calc R . .
C10 C 0.6858(7) 0.7573(6) 0.84339(8) 0.0355(11) Uani 1 1 d . . .
H10A H 0.6834 0.6295 0.8452 0.043 Uiso 1 1 calc R . .
H10B H 0.8493 0.7911 0.8359 0.043 Uiso 1 1 calc R . .
C11 C 0.4817(7) 0.8133(5) 0.82357(7) 0.0321(10) Uani 1 1 d . . .
H11A H 0.3197 0.7760 0.8310 0.038 Uiso 1 1 calc R . .
H11B H 0.4802 0.9415 0.8227 0.038 Uiso 1 1 calc R . .
C12 C 0.5061(7) 0.7429(6) 0.79493(7) 0.0345(11) Uani 1 1 d . . .
H12A H 0.5056 0.6147 0.7955 0.041 Uiso 1 1 calc R . .
H12B H 0.6666 0.7807 0.7872 0.041 Uiso 1 1 calc R . .
C13 C 0.2944(8) 0.8055(6) 0.77654(8) 0.0400(12) Uani 1 1 d . . .
H13A H 0.1350 0.7647 0.7842 0.048 Uiso 1 1 calc R . .
H13B H 0.2917 0.9338 0.7767 0.048 Uiso 1 1 calc R . .
C14 C 0.3135(7) 0.7436(6) 0.74724(8) 0.0380(11) Uani 1 1 d . . .
H14A H 0.4739 0.7825 0.7396 0.046 Uiso 1 1 calc R . .
H14B H 0.3125 0.6152 0.7470 0.046 Uiso 1 1 calc R . .
C15 C 0.1053(8) 0.8092(6) 0.72922(7) 0.0418(12) Uani 1 1 d . . .
H15A H -0.0550 0.7702 0.7369 0.050 Uiso 1 1 calc R . .
H15B H 0.1062 0.9375 0.7295 0.050 Uiso 1 1 calc R . .
C16 C 0.1224(7) 0.7487(6) 0.70001(8) 0.0413(12) Uani 1 1 d . . .
H16A H 0.1113 0.6206 0.6994 0.050 Uiso 1 1 calc R . .
H16B H 0.2854 0.7827 0.6925 0.050 Uiso 1 1 calc R . .
C17 C -0.0827(9) 0.8257(6) 0.68264(8) 0.0459(13) Uani 1 1 d . . .
H17A H -0.0724 0.9537 0.6835 0.055 Uiso 1 1 calc R . .
H17B H -0.2452 0.7907 0.6902 0.055 Uiso 1 1 calc R . .
C18 C -0.0680(9) 0.7678(7) 0.65276(9) 0.0519(14) Uani 1 1 d . . .
H18A H 0.0948 0.8021 0.6452 0.062 Uiso 1 1 calc R . .
H18B H -0.0797 0.6398 0.6519 0.062 Uiso 1 1 calc R . .
C19 C -0.2702(10) 0.8455(8) 0.63580(10) 0.0599(16) Uani 1 1 d . . .
H19A H -0.4317 0.8162 0.6437 0.090 Uiso 1 1 calc R . .
H19B H -0.2601 0.7992 0.6173 0.090 Uiso 1 1 calc R . .
H19C H -0.2508 0.9718 0.6353 0.090 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 C7 1.472(5) . ?
N1 C2 1.514(4) . ?
N1 H1 0.96(4) . ?
C2 C3 1.472(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.467(5) . ?
C3 C4 1.568(5) . ?
C3 H3 1.0000 . ?
O3 H3A 0.8400 . ?
C4 O4 1.366(5) . ?
C4 C5 1.529(5) . ?
C4 H4 1.0000 . ?
O4 H4A 0.8400 . ?
C5 O5 1.489(5) . ?
C5 C6 1.530(5) . ?
C5 H5 1.0000 . ?
O5 H5A 0.8400 . ?
C6 O6 1.464(4) . ?
C6 C7 1.497(5) . ?
C6 H6 1.0000 . ?
O6 H6A 0.8400 . ?
C7 C8 1.556(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.519(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.516(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.534(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.519(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.536(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.525(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.519(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.518(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.520(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.542(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.499(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C7 N1 C2 120.0(3) . . ?
C7 N1 H1 126(2) . . ?
C2 N1 H1 111(2) . . ?
C3 C2 N1 114.9(3) . . ?
C3 C2 H2A 108.5 . . ?
N1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
N1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
O3 C3 C2 103.7(3) . . ?
O3 C3 C4 112.0(3) . . ?
C2 C3 C4 113.2(3) . . ?
O3 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C3 O3 H3A 109.5 . . ?
O4 C4 C5 113.0(3) . . ?
O4 C4 C3 99.5(3) . . ?
C5 C4 C3 116.4(3) . . ?
O4 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C4 O4 H4A 109.5 . . ?
O5 C5 C4 106.1(3) . . ?
O5 C5 C6 101.7(3) . . ?
C4 C5 C6 118.8(3) . . ?
O5 C5 H5 109.9 . . ?
C4 C5 H5 109.9 . . ?
C6 C5 H5 109.9 . . ?
C5 O5 H5A 109.5 . . ?
O6 C6 C7 106.7(3) . . ?
O6 C6 C5 112.9(3) . . ?
C7 C6 C5 117.3(3) . . ?
O6 C6 H6 106.4 . . ?
C7 C6 H6 106.4 . . ?
C5 C6 H6 106.4 . . ?
C6 O6 H6A 109.5 . . ?
N1 C7 C6 111.4(3) . . ?
N1 C7 C8 109.7(3) . . ?
C6 C7 C8 111.9(3) . . ?
N1 C7 H7 107.9 . . ?
C6 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
C9 C8 C7 109.4(3) . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 113.6(3) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 112.3(3) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 115.5(3) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C13 111.9(3) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 114.3(3) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 113.6(3) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 114.1(4) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 111.8(4) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 112.8(4) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 112.4(4) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
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 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.054
#===END
_database_code_depnum_ccdc_archive 'CCDC 970784'
