# 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_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Cl N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         359.79
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   6.6270(3)
_cell_length_b                   7.9739(3)
_cell_length_c                   32.9949(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1743.55(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.6784
_cell_measurement_theta_max      68.2242
_cell_measurement_temperature    173

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            17563
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_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       -39
_diffrn_reflns_limit_l_max       39

_refine_special_details          
;
;

_reflns_number_total             3176
_reflns_number_gt                3030
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1107
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_number_reflns         3176
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0787P)²+0.3355P] 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_ls_shift/su_mean         0.000
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1215 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.055(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 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6663(4) 0.5571(3) 0.21155(8) 0.0298(6) Uani d . . . 1 . .
C C2 0.8325(4) 0.4553(4) 0.21824(9) 0.0387(7) Uani d . . . 1 . .
H H2 0.887 0.3916 0.1965 0.046 Uiso calc U . R 1 . .
C C3 0.9206(5) 0.4452(5) 0.25664(11) 0.0497(8) Uani d . . . 1 . .
H H3 1.0345 0.3752 0.2611 0.06 Uiso calc U . R 1 . .
C C4 0.8405(5) 0.5380(4) 0.28811(9) 0.0471(8) Uani d . . . 1 . .
H H4 0.9001 0.5321 0.3143 0.057 Uiso calc U . R 1 . .
C C5 0.6759(5) 0.6384(4) 0.28186(9) 0.0447(7) Uani d . . . 1 . .
H H5 0.621 0.7009 0.3037 0.054 Uiso calc U . R 1 . .
C C6 0.5886(5) 0.6493(4) 0.24362(9) 0.0374(6) Uani d . . . 1 . .
H H6 0.4752 0.7201 0.2394 0.045 Uiso calc U . R 1 . .
C C7 0.5730(4) 0.5625(3) 0.16895(8) 0.0293(6) Uani d . . . 1 . .
C C8 0.6588(4) 0.7139(4) 0.14529(8) 0.0298(6) Uani d . . . 1 . .
C C9 0.6941(6) 1.0084(4) 0.14453(10) 0.0449(8) Uani d . . . 1 . .
H H9A 0.8304 0.9908 0.1338 0.067 Uiso calc U . R 1 . .
H H9B 0.6957 1.1013 0.164 0.067 Uiso calc U . R 1 . .
H H9C 0.6022 1.0354 0.1222 0.067 Uiso calc U . R 1 . .
C C10 0.3405(4) 0.5828(4) 0.17055(9) 0.0332(6) Uani d . . . 1 . .
H H10A 0.2826 0.4876 0.1859 0.04 Uiso calc U . R 1 . .
H H10B 0.3078 0.687 0.1855 0.04 Uiso calc U . R 1 . .
C C11 0.2410(4) 0.5900(4) 0.12910(9) 0.0343(6) Uani d . . . 1 . .
C C12 0.2189(5) 0.7320(4) 0.10914(12) 0.0500(9) Uani d . . . 1 . .
H H12A 0.1638 0.7314 0.0826 0.06 Uiso calc U . R 1 . .
H H12B 0.2579 0.8349 0.1213 0.06 Uiso calc U . R 1 . .
C C13 0.1809(4) 0.4250(4) 0.11074(8) 0.0319(6) Uani d . . . 1 . .
C C14 -0.0885(4) 0.2938(4) 0.06911(8) 0.0301(6) Uani d . . . 1 . .
C C15 0.0013(5) 0.1393(4) 0.06156(8) 0.0375(6) Uani d . . . 1 . .
H H15 0.1364 0.1192 0.0698 0.045 Uiso calc U . R 1 . .
C C16 -0.1067(6) 0.0152(4) 0.04196(9) 0.0447(8) Uani d . . . 1 . .
H H16 -0.0459 -0.0904 0.0366 0.054 Uiso calc U . R 1 . .
C C17 -0.3035(5) 0.0453(4) 0.03024(9) 0.0425(7) Uani d . . . 1 . .
C C18 -0.3926(5) 0.1982(4) 0.03585(9) 0.0383(7) Uani d . . . 1 . .
H H18 -0.5262 0.2184 0.0266 0.046 Uiso calc U . R 1 . .
C C19 -0.2840(5) 0.3234(4) 0.05531(8) 0.0346(6) Uani d . . . 1 . .
H H19 -0.3436 0.4305 0.0593 0.042 Uiso calc U . R 1 . .
Cl Cl1 -0.44684(18) -0.11667(12) 0.00880(3) 0.0675(3) Uani d . . . 1 . .
N N1 0.0059(4) 0.4264(3) 0.09028(7) 0.0324(5) Uani d . . . 1 . .
H H1 -0.0588 0.5228 0.09 0.039 Uiso calc U . R 1 . .
O O1 0.6301(3) 0.4158(2) 0.14824(6) 0.0322(4) Uani d . . . 1 . .
H H1A 0.5276 0.3711 0.1378 0.048 Uiso calc U . R 1 . .
O O2 0.7438(3) 0.7048(3) 0.11306(6) 0.0377(5) Uani d . . . 1 . .
O O3 0.6256(3) 0.8568(2) 0.16466(6) 0.0391(5) Uani d . . . 1 . .
O O4 0.2884(3) 0.3006(3) 0.11489(7) 0.0442(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.386(4) ?
C1 C6 . 1.388(4) ?
C1 C7 . 1.536(4) ?
C2 C3 . 1.397(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.381(5) ?
C3 H3 . 0.95 ?
C4 C5 . 1.369(5) ?
C4 H4 . 0.95 ?
C5 C6 . 1.391(4) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 O1 . 1.407(3) ?
C7 C8 . 1.546(4) ?
C7 C10 . 1.550(4) ?
C8 O2 . 1.206(3) ?
C8 O3 . 1.324(4) ?
C9 O3 . 1.452(4) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 C11 . 1.519(4) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.318(5) ?
C11 C13 . 1.502(4) ?
C12 H12A . 0.95 ?
C12 H12B . 0.95 ?
C13 O4 . 1.229(4) ?
C13 N1 . 1.342(4) ?
C14 C15 . 1.390(4) ?
C14 C19 . 1.393(4) ?
C14 N1 . 1.414(4) ?
C15 C16 . 1.382(4) ?
C15 H15 . 0.95 ?
C16 C17 . 1.381(5) ?
C16 H16 . 0.95 ?
C17 C18 . 1.368(5) ?
C17 Cl1 . 1.752(3) ?
C18 C19 . 1.388(4) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
N1 H1 . 0.88 ?
O1 H1A . 0.84 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 118.9(3) ?
C2 C1 C7 . . 118.8(2) ?
C6 C1 C7 . . 122.2(2) ?
C1 C2 C3 . . 120.7(3) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.3(3) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C5 C4 C3 . . 120.4(3) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.3(3) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C1 C6 C5 . . 120.3(3) ?
C1 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
O1 C7 C1 . . 108.2(2) ?
O1 C7 C8 . . 107.8(2) ?
C1 C7 C8 . . 109.6(2) ?
O1 C7 C10 . . 111.8(2) ?
C1 C7 C10 . . 111.8(2) ?
C8 C7 C10 . . 107.5(2) ?
O2 C8 O3 . . 123.7(3) ?
O2 C8 C7 . . 124.7(3) ?
O3 C8 C7 . . 111.5(2) ?
O3 C9 H9A . . 109.5 ?
O3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C7 . . 113.9(2) ?
C11 C10 H10A . . 108.8 ?
C7 C10 H10A . . 108.8 ?
C11 C10 H10B . . 108.8 ?
C7 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
C12 C11 C13 . . 121.4(3) ?
C12 C11 C10 . . 122.0(3) ?
C13 C11 C10 . . 116.4(2) ?
C11 C12 H12A . . 120.0 ?
C11 C12 H12B . . 120.0 ?
H12A C12 H12B . . 120.0 ?
O4 C13 N1 . . 124.3(3) ?
O4 C13 C11 . . 120.6(2) ?
N1 C13 C11 . . 115.1(2) ?
C15 C14 C19 . . 119.3(3) ?
C15 C14 N1 . . 124.2(2) ?
C19 C14 N1 . . 116.5(3) ?
C16 C15 C14 . . 119.8(3) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C17 C16 C15 . . 119.7(3) ?
C17 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C18 C17 C16 . . 121.7(3) ?
C18 C17 Cl1 . . 118.5(3) ?
C16 C17 Cl1 . . 119.8(3) ?
C17 C18 C19 . . 118.7(3) ?
C17 C18 H18 . . 120.7 ?
C19 C18 H18 . . 120.7 ?
C18 C19 C14 . . 120.8(3) ?
C18 C19 H19 . . 119.6 ?
C14 C19 H19 . . 119.6 ?
C13 N1 C14 . . 128.7(2) ?
C13 N1 H1 . . 115.7 ?
C14 N1 H1 . . 115.7 ?
C7 O1 H1A . . 109.5 ?
C8 O3 C9 . . 116.3(2) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.0(4) ?
C7 C1 C2 C3 . . . . -179.3(3) ?
C1 C2 C3 C4 . . . . 0.0(5) ?
C2 C3 C4 C5 . . . . 0.3(5) ?
C3 C4 C5 C6 . . . . -0.6(5) ?
C2 C1 C6 C5 . . . . -0.4(4) ?
C7 C1 C6 C5 . . . . 178.9(3) ?
C4 C5 C6 C1 . . . . 0.7(5) ?
C2 C1 C7 O1 . . . . 21.4(3) ?
C6 C1 C7 O1 . . . . -157.8(2) ?
C2 C1 C7 C8 . . . . -95.9(3) ?
C6 C1 C7 C8 . . . . 84.9(3) ?
C2 C1 C7 C10 . . . . 145.0(3) ?
C6 C1 C7 C10 . . . . -34.3(4) ?
O1 C7 C8 O2 . . . . 5.8(4) ?
C1 C7 C8 O2 . . . . 123.4(3) ?
C10 C7 C8 O2 . . . . -114.9(3) ?
O1 C7 C8 O3 . . . . -174.8(2) ?
C1 C7 C8 O3 . . . . -57.3(3) ?
C10 C7 C8 O3 . . . . 64.5(3) ?
O1 C7 C10 C11 . . . . -58.9(3) ?
C1 C7 C10 C11 . . . . 179.6(2) ?
C8 C7 C10 C11 . . . . 59.2(3) ?
C7 C10 C11 C12 . . . . -87.7(4) ?
C7 C10 C11 C13 . . . . 88.5(3) ?
C12 C11 C13 O4 . . . . 138.3(3) ?
C10 C11 C13 O4 . . . . -37.9(4) ?
C12 C11 C13 N1 . . . . -41.8(4) ?
C10 C11 C13 N1 . . . . 142.0(2) ?
C19 C14 C15 C16 . . . . -2.6(4) ?
N1 C14 C15 C16 . . . . 177.4(3) ?
C14 C15 C16 C17 . . . . -0.3(5) ?
C15 C16 C17 C18 . . . . 3.0(5) ?
C15 C16 C17 Cl1 . . . . -175.3(2) ?
C16 C17 C18 C19 . . . . -2.6(5) ?
Cl1 C17 C18 C19 . . . . 175.7(2) ?
C17 C18 C19 C14 . . . . -0.4(4) ?
C15 C14 C19 C18 . . . . 3.0(4) ?
N1 C14 C19 C18 . . . . -177.0(3) ?
O4 C13 N1 C14 . . . . -1.5(5) ?
C11 C13 N1 C14 . . . . 178.6(3) ?
C15 C14 N1 C13 . . . . -8.8(4) ?
C19 C14 N1 C13 . . . . 171.2(3) ?
O2 C8 O3 C9 . . . . 1.4(4) ?
C7 C8 O3 C9 . . . . -178.0(3) ?

_database_code_depnum_ccdc_archive 'CCDC 1003520'
