# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1547189'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2017-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N O4, Cl'
_chemical_formula_sum            'C20 H22 Cl N O4'
_chemical_formula_weight         375.84

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                   7.5563(3)
_cell_length_b                   9.6115(5)
_cell_length_c                   23.9913(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1742.43(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2103
_cell_measurement_theta_min      3.1798
_cell_measurement_theta_max      28.8800

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             792.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.9525
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5216
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.186
_diffrn_reflns_theta_max         25.746
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3326
_reflns_number_gt                2781
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_max     0.912
_reflns_Friedel_fraction_full    0.922

_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)+(0.0419P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 948 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3326
_refine_ls_number_parameters     260
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.037
_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
H1N H 0.445(3) 0.078(4) 0.1550(14) 0.055(12) Uiso 1 1 d D . . . .
C20 C 0.6440(6) 0.7417(4) 0.01673(17) 0.0490(11) Uani 1 1 d . . . . .
H20C H 0.6867 0.7744 -0.0186 0.063(13) Uiso 1 1 calc R . . . .
H20B H 0.5448 0.7971 0.0282 0.053(12) Uiso 1 1 calc R . . . .
H20A H 0.7365 0.7490 0.0440 0.080(16) Uiso 1 1 calc R . . . .
C19 C 0.3417(5) 0.3810(4) -0.03629(14) 0.0438(9) Uani 1 1 d . . . . .
H19C H 0.3528 0.3326 -0.0711 0.084(16) Uiso 1 1 calc R . . . .
H19A H 0.2269 0.3634 -0.0207 0.093(16) Uiso 1 1 calc R . . . .
H19B H 0.3558 0.4791 -0.0424 0.080(14) Uiso 1 1 calc R . . . .
C18 C 0.0065(5) -0.0001(4) 0.41547(13) 0.0406(8) Uani 1 1 d . . . . .
H18A H -0.1179 -0.0066 0.4251 0.039(9) Uiso 1 1 calc R . . . .
H18B H 0.0749 0.0015 0.4497 0.052(10) Uiso 1 1 calc R . . . .
C3 C 0.1055(4) -0.0637(3) 0.33160(14) 0.0288(8) Uani 1 1 d . . . . .
C4 C 0.1606(4) -0.1343(3) 0.28512(14) 0.0307(8) Uani 1 1 d . . . . .
H4 H 0.1692 -0.2308 0.2851 0.038(10) Uiso 1 1 calc R . . . .
C5 C 0.2038(4) -0.0559(3) 0.23739(13) 0.0268(7) Uani 1 1 d . . . . .
C17 C 0.1928(4) 0.0898(3) 0.23874(13) 0.0248(7) Uani 1 1 d . . . . .
C1 C 0.1369(4) 0.1591(3) 0.28761(13) 0.0282(8) Uani 1 1 d . . . . .
H1 H 0.1305 0.2557 0.2892 0.028(9) Uiso 1 1 calc R . . . .
C2 C 0.0932(4) 0.0798(3) 0.33183(14) 0.0279(7) Uani 1 1 d . . . . .
C6 C 0.2621(4) -0.1300(3) 0.18564(13) 0.0324(8) Uani 1 1 d . . . . .
H6A H 0.1932 -0.2145 0.1814 0.030(9) Uiso 1 1 calc R . . . .
H6B H 0.3854 -0.1565 0.1895 0.051(11) Uiso 1 1 calc R . . . .
C7 C 0.2408(5) -0.0415(3) 0.13408(13) 0.0334(8) Uani 1 1 d . . . . .
H7A H 0.2935 -0.0880 0.1023 0.042(10) Uiso 1 1 calc R . . . .
H7B H 0.1162 -0.0270 0.1263 0.035(9) Uiso 1 1 calc R . . . .
C16 C 0.2374(4) 0.1779(3) 0.18838(13) 0.0266(7) Uani 1 1 d . . . . .
H16 H 0.1262 0.2128 0.1727 0.039(10) Uiso 1 1 calc R . . . .
C15 C 0.3533(5) 0.3028(3) 0.20207(13) 0.0317(8) Uani 1 1 d . . . . .
H15A H 0.2898 0.3633 0.2275 0.036(9) Uiso 1 1 calc R . . . .
H15B H 0.4592 0.2706 0.2210 0.037(10) Uiso 1 1 calc R . . . .
C8 C 0.3483(5) 0.1750(4) 0.09035(13) 0.0298(8) Uani 1 1 d . . . . .
H8A H 0.2347 0.1770 0.0716 0.042(10) Uiso 1 1 calc R . . . .
H8B H 0.4314 0.1269 0.0663 0.035(9) Uiso 1 1 calc R . . . .
C9 C 0.4115(4) 0.3226(3) 0.09911(13) 0.0254(7) Uani 1 1 d . . . . .
C14 C 0.4065(4) 0.3849(3) 0.15167(13) 0.0263(7) Uani 1 1 d . . . . .
C13 C 0.4563(4) 0.5235(3) 0.15641(13) 0.0315(8) Uani 1 1 d . . . . .
H13 H 0.4491 0.5665 0.1911 0.048(11) Uiso 1 1 calc R . . . .
C12 C 0.5162(4) 0.5997(4) 0.11118(13) 0.0332(8) Uani 1 1 d . . . . .
H12 H 0.5500 0.6921 0.1156 0.038(10) Uiso 1 1 calc R . . . .
C11 C 0.5253(4) 0.5365(3) 0.05923(13) 0.0303(8) Uani 1 1 d . . . . .
C10 C 0.4698(4) 0.3977(3) 0.05330(13) 0.0277(7) Uani 1 1 d . . . . .
N1 N 0.3302(3) 0.0958(3) 0.14362(11) 0.0262(6) Uani 1 1 d D . . . .
O3 O 0.4761(3) 0.3330(2) 0.00172(9) 0.0351(6) Uani 1 1 d . . . . .
O4 O 0.5903(3) 0.5992(3) 0.01167(10) 0.0428(6) Uani 1 1 d . . . . .
O2 O 0.0569(3) -0.1170(3) 0.38240(10) 0.0420(6) Uani 1 1 d . . . . .
O1 O 0.0379(3) 0.1237(3) 0.38442(9) 0.0393(6) Uani 1 1 d . . . . .
Cl1 Cl 0.20698(11) 0.49360(10) -0.16597(4) 0.0480(3) 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
C20 O4 1.434(5) . ?
C20 H20C 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20A 0.9600 . ?
C19 O3 1.441(4) . ?
C19 H19C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C18 O1 1.424(4) . ?
C18 O2 1.427(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C3 C4 1.370(4) . ?
C3 O2 1.372(4) . ?
C3 C2 1.382(4) . ?
C4 C5 1.409(4) . ?
C4 H4 0.9300 . ?
C5 C17 1.404(4) . ?
C5 C6 1.498(4) . ?
C17 C1 1.413(4) . ?
C17 C16 1.513(4) . ?
C1 C2 1.347(4) . ?
C1 H1 0.9300 . ?
C2 O1 1.395(4) . ?
C6 C7 1.510(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N1 1.500(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C16 N1 1.506(4) . ?
C16 C15 1.522(4) . ?
C16 H16 0.9800 . ?
C15 C14 1.499(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C8 N1 1.494(4) . ?
C8 C9 1.512(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.387(4) . ?
C9 C14 1.397(4) . ?
C14 C13 1.389(4) . ?
C13 C12 1.385(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.388(4) . ?
C12 H12 0.9300 . ?
C11 O4 1.381(4) . ?
C11 C10 1.406(5) . ?
C10 O3 1.386(4) . ?
N1 H1N 0.92(2) . ?

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
O4 C20 H20C 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
O4 C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
O3 C19 H19C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C18 O2 108.8(2) . . ?
O1 C18 H18A 109.9 . . ?
O2 C18 H18A 109.9 . . ?
O1 C18 H18B 109.9 . . ?
O2 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C4 C3 O2 128.3(3) . . ?
C4 C3 C2 121.2(3) . . ?
O2 C3 C2 110.6(3) . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C17 C5 C4 120.1(3) . . ?
C17 C5 C6 120.7(3) . . ?
C4 C5 C6 119.2(3) . . ?
C5 C17 C1 120.5(3) . . ?
C5 C17 C16 121.8(3) . . ?
C1 C17 C16 117.7(3) . . ?
C2 C1 C17 117.4(3) . . ?
C2 C1 H1 121.3 . . ?
C17 C1 H1 121.3 . . ?
C1 C2 C3 123.0(3) . . ?
C1 C2 O1 127.9(3) . . ?
C3 C2 O1 109.0(3) . . ?
C5 C6 C7 112.3(2) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N1 C7 C6 108.8(2) . . ?
N1 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
N1 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N1 C16 C17 112.3(2) . . ?
N1 C16 C15 107.4(2) . . ?
C17 C16 C15 113.4(2) . . ?
N1 C16 H16 107.8 . . ?
C17 C16 H16 107.8 . . ?
C15 C16 H16 107.8 . . ?
C14 C15 C16 113.3(3) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
N1 C8 C9 112.9(3) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C14 120.0(3) . . ?
C10 C9 C8 118.6(3) . . ?
C14 C9 C8 121.3(3) . . ?
C13 C14 C9 118.6(3) . . ?
C13 C14 C15 120.8(3) . . ?
C9 C14 C15 120.6(3) . . ?
C12 C13 C14 122.1(3) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
O4 C11 C12 124.7(3) . . ?
O4 C11 C10 115.9(3) . . ?
C12 C11 C10 119.4(3) . . ?
O3 C10 C9 119.0(3) . . ?
O3 C10 C11 120.4(3) . . ?
C9 C10 C11 120.6(3) . . ?
C8 N1 C7 111.0(2) . . ?
C8 N1 C16 112.7(2) . . ?
C7 N1 C16 111.1(2) . . ?
C8 N1 H1N 105(2) . . ?
C7 N1 H1N 108(2) . . ?
C16 N1 H1N 109(2) . . ?
C10 O3 C19 113.4(2) . . ?
C11 O4 C20 116.6(3) . . ?
C3 O2 C18 105.7(2) . . ?
C2 O1 C18 105.7(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 C5 180.0(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C17 1.1(5) . . . . ?
C3 C4 C5 C6 -179.2(3) . . . . ?
C4 C5 C17 C1 -0.6(5) . . . . ?
C6 C5 C17 C1 179.7(3) . . . . ?
C4 C5 C17 C16 -179.8(3) . . . . ?
C6 C5 C17 C16 0.5(5) . . . . ?
C5 C17 C1 C2 -0.8(5) . . . . ?
C16 C17 C1 C2 178.4(3) . . . . ?
C17 C1 C2 C3 1.8(5) . . . . ?
C17 C1 C2 O1 178.7(3) . . . . ?
C4 C3 C2 C1 -1.3(5) . . . . ?
O2 C3 C2 C1 178.5(3) . . . . ?
C4 C3 C2 O1 -178.7(3) . . . . ?
O2 C3 C2 O1 1.1(4) . . . . ?
C17 C5 C6 C7 -20.6(4) . . . . ?
C4 C5 C6 C7 159.6(3) . . . . ?
C5 C6 C7 N1 52.3(3) . . . . ?
C5 C17 C16 N1 -12.7(4) . . . . ?
C1 C17 C16 N1 168.1(2) . . . . ?
C5 C17 C16 C15 -134.7(3) . . . . ?
C1 C17 C16 C15 46.0(4) . . . . ?
N1 C16 C15 C14 51.8(3) . . . . ?
C17 C16 C15 C14 176.5(3) . . . . ?
N1 C8 C9 C10 166.5(3) . . . . ?
N1 C8 C9 C14 -15.7(4) . . . . ?
C10 C9 C14 C13 1.7(4) . . . . ?
C8 C9 C14 C13 -176.1(3) . . . . ?
C10 C9 C14 C15 -176.6(3) . . . . ?
C8 C9 C14 C15 5.6(4) . . . . ?
C16 C15 C14 C13 157.3(3) . . . . ?
C16 C15 C14 C9 -24.5(4) . . . . ?
C9 C14 C13 C12 -2.3(5) . . . . ?
C15 C14 C13 C12 176.0(3) . . . . ?
C14 C13 C12 C11 0.7(5) . . . . ?
C13 C12 C11 O4 -176.8(3) . . . . ?
C13 C12 C11 C10 1.4(5) . . . . ?
C14 C9 C10 O3 179.1(3) . . . . ?
C8 C9 C10 O3 -3.1(4) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C8 C9 C10 C11 178.3(3) . . . . ?
O4 C11 C10 O3 -2.2(4) . . . . ?
C12 C11 C10 O3 179.4(3) . . . . ?
O4 C11 C10 C9 176.4(3) . . . . ?
C12 C11 C10 C9 -2.0(4) . . . . ?
C9 C8 N1 C7 171.1(3) . . . . ?
C9 C8 N1 C16 45.7(3) . . . . ?
C6 C7 N1 C8 167.5(3) . . . . ?
C6 C7 N1 C16 -66.3(3) . . . . ?
C17 C16 N1 C8 170.6(3) . . . . ?
C15 C16 N1 C8 -64.0(3) . . . . ?
C17 C16 N1 C7 45.3(3) . . . . ?
C15 C16 N1 C7 170.6(2) . . . . ?
C9 C10 O3 C19 108.3(3) . . . . ?
C11 C10 O3 C19 -73.0(4) . . . . ?
C12 C11 O4 C20 -3.0(5) . . . . ?
C10 C11 O4 C20 178.7(3) . . . . ?
C4 C3 O2 C18 -178.4(3) . . . . ?
C2 C3 O2 C18 1.8(4) . . . . ?
O1 C18 O2 C3 -3.9(3) . . . . ?
C1 C2 O1 C18 179.3(3) . . . . ?
C3 C2 O1 C18 -3.5(4) . . . . ?
O2 C18 O1 C2 4.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H19C O2 0.96 2.45 3.291(5) 146.2 2_554
C19 H19C Cl1 0.96 2.96 3.447(3) 112.5 .
C19 H19B O4 0.96 2.48 3.042(5) 117.1 .
C4 H4 Cl1 0.93 2.94 3.782(3) 151.6 2
C1 H1 Cl1 0.93 2.91 3.711(3) 145.0 2_565
C8 H8A O3 0.97 2.63 3.577(4) 165.3 4_455
C19 H19C O2 0.96 2.45 3.291(5) 146.2 2_554
C19 H19C Cl1 0.96 2.96 3.447(3) 112.5 .
C19 H19B O4 0.96 2.48 3.042(5) 117.1 .
C4 H4 Cl1 0.93 2.94 3.782(3) 151.6 2
C1 H1 Cl1 0.93 2.91 3.711(3) 145.0 2_565
C8 H8A O3 0.97 2.63 3.577(4) 165.3 4_455
C19 H19C O2 0.96 2.45 3.291(5) 146.2 2_554
C19 H19C Cl1 0.96 2.96 3.447(3) 112.5 .
C19 H19B O4 0.96 2.48 3.042(5) 117.1 .
C4 H4 Cl1 0.93 2.94 3.782(3) 151.6 2
C1 H1 Cl1 0.93 2.91 3.711(3) 145.0 2_565
C6 H6B Cl1 0.97 2.95 3.639(3) 129.4 4
C16 H16 O2 0.98 2.52 3.423(4) 153.5 3
C15 H15A Cl1 0.97 2.90 3.750(3) 146.5 2_565
C8 H8A O3 0.97 2.63 3.577(4) 165.3 4_455

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1547191'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2017-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '	C20 H22 N O4, C2 H4 O2, Cl'
_chemical_formula_sum            'C22 H26 Cl N O6'
_chemical_formula_weight         435.89

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   35.9919(19)
_cell_length_b                   7.4630(5)
_cell_length_c                   16.1702(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4343.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3732
_cell_measurement_theta_min      3.9550
_cell_measurement_theta_max      29.0060

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.214
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9750
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.453
_diffrn_reflns_theta_max         23.996
_diffrn_reflns_theta_full        23.996
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measured_fraction_theta_full 0.874
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_Laue_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.874
_reflns_number_total             6821
_reflns_number_gt                5503
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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)+(0.0901P)²+70.4680P] 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_number_reflns         6821
_refine_ls_number_parameters     549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.1427
_refine_ls_wR_factor_ref         0.3563
_refine_ls_wR_factor_gt          0.3547
_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
O1 O 0.54629(19) 0.8516(11) 0.2037(5) 0.056(2) Uani 1 1 d . . . . .
O2 O 0.49732(19) 0.9467(13) 0.2861(4) 0.062(2) Uani 1 1 d . . . . .
O4 O 0.2306(2) 0.734(2) -0.0022(5) 0.102(4) Uani 1 1 d . . . . .
O3 O 0.2901(2) 0.7508(14) -0.1044(5) 0.070(2) Uani 1 1 d . . . . .
N1 N 0.3987(2) 0.7479(11) -0.0120(4) 0.0323(17) Uani 1 1 d . . . . .
C17 C 0.4433(2) 0.8565(11) 0.0981(6) 0.030(2) Uani 1 1 d . . . . .
C5 C 0.4723(2) 0.7979(13) 0.0482(5) 0.035(2) Uani 1 1 d . . . . .
C4 C 0.5083(3) 0.7908(15) 0.0804(6) 0.045(3) Uani 1 1 d . . . . .
H4 H 0.5280 0.7481 0.0487 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4659(2) 0.7342(13) -0.0395(6) 0.037(2) Uani 1 1 d . . . . .
H6A H 0.4673 0.6044 -0.0409 0.045 Uiso 1 1 calc R U . . .
H6B H 0.4854 0.7808 -0.0748 0.045 Uiso 1 1 calc R U . . .
C7 C 0.4286(2) 0.7934(14) -0.0730(6) 0.041(2) Uani 1 1 d . . . . .
H7A H 0.4288 0.9217 -0.0828 0.049 Uiso 1 1 calc R U . . .
H7B H 0.4237 0.7338 -0.1252 0.049 Uiso 1 1 calc R U . . .
C1 C 0.4494(3) 0.9104(12) 0.1791(6) 0.036(2) Uani 1 1 d . . . . .
H1 H 0.4299 0.9499 0.2122 0.044 Uiso 1 1 calc R U . . .
C16 C 0.4030(3) 0.8586(12) 0.0664(6) 0.034(2) Uani 1 1 d . . . . .
H16 H 0.3959 0.9826 0.0546 0.040 Uiso 1 1 calc R U . . .
C15 C 0.3759(2) 0.7804(15) 0.1298(6) 0.040(2) Uani 1 1 d . . . . .
H15A H 0.3845 0.6626 0.1464 0.048 Uiso 1 1 calc R U . . .
H15B H 0.3757 0.8562 0.1786 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5139(2) 0.8481(13) 0.1592(6) 0.037(2) Uani 1 1 d . . . . .
C2 C 0.4848(3) 0.9039(13) 0.2087(6) 0.041(2) Uani 1 1 d . . . . .
C9 C 0.3305(3) 0.7627(16) 0.0112(6) 0.048(3) Uani 1 1 d . . . . .
C8 C 0.3617(3) 0.7759(16) -0.0503(6) 0.045(3) Uani 1 1 d . . . . .
H8B H 0.3581 0.6871 -0.0933 0.055 Uiso 1 1 calc R U . . .
H8A H 0.3612 0.8933 -0.0760 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3366(3) 0.7649(17) 0.0963(6) 0.048(3) Uani 1 1 d . . . . .
C13 C 0.3071(3) 0.761(2) 0.1488(7) 0.067(4) Uani 1 1 d . . . . .
H13 H 0.3110 0.7693 0.2056 0.081 Uiso 1 1 calc R U . . .
C12 C 0.2714(3) 0.746(2) 0.1189(8) 0.083(5) Uani 1 1 d . . . . .
H12 H 0.2515 0.7421 0.1556 0.099 Uiso 1 1 calc R U . . .
C10 C 0.2949(3) 0.750(2) -0.0197(7) 0.066(4) Uani 1 1 d . . . . .
C11 C 0.2649(3) 0.736(2) 0.0346(8) 0.076(4) Uani 1 1 d . . . . .
C18 C 0.5362(3) 0.9131(18) 0.2841(8) 0.063(3) Uani 1 1 d . . . . .
H18A H 0.5425 0.8232 0.3250 0.076 Uiso 1 1 calc R U . . .
H18B H 0.5497 1.0221 0.2971 0.076 Uiso 1 1 calc R U . . .
C20 C 0.1989(3) 0.727(3) 0.0510(9) 0.096(6) Uani 1 1 d . . . . .
H20A H 0.1969 0.8380 0.0809 0.144 Uiso 1 1 calc R U . . .
H20C H 0.2015 0.6299 0.0893 0.144 Uiso 1 1 calc R U . . .
H20B H 0.1769 0.7098 0.0184 0.144 Uiso 1 1 calc R U . . .
O7 O 0.2099(2) 0.2436(14) -0.1039(5) 0.069(3) Uani 1 1 d . . . . .
O8 O 0.2694(2) 0.251(2) -0.0015(5) 0.101(4) Uani 1 1 d . . . . .
O5 O -0.04653(18) 0.1518(11) 0.2044(5) 0.053(2) Uani 1 1 d . . . . .
O6 O 0.0024(2) 0.0557(13) 0.2858(4) 0.061(2) Uani 1 1 d . . . . .
N2 N 0.1012(2) 0.2451(10) -0.0111(5) 0.0301(17) Uani 1 1 d . . . . .
C37 C 0.0568(2) 0.1464(12) 0.0977(6) 0.034(2) Uani 1 1 d . . . . .
C27 C 0.0713(2) 0.2052(13) -0.0726(6) 0.036(2) Uani 1 1 d . . . . .
H27A H 0.0706 0.0775 -0.0836 0.043 Uiso 1 1 calc R U . . .
H27B H 0.0765 0.2667 -0.1242 0.043 Uiso 1 1 calc R U . . .
C29 C 0.1696(3) 0.2295(15) 0.0113(6) 0.045(2) Uani 1 1 d . . . . .
C34 C 0.1630(3) 0.2261(15) 0.0968(6) 0.043(2) Uani 1 1 d . . . . .
C21 C 0.0502(3) 0.0903(13) 0.1791(6) 0.040(2) Uani 1 1 d . . . . .
H21 H 0.0697 0.0495 0.2120 0.048 Uiso 1 1 calc R U . . .
C28 C 0.1385(2) 0.2195(14) -0.0504(6) 0.039(2) Uani 1 1 d . . . . .
H28A H 0.1422 0.3109 -0.0922 0.047 Uiso 1 1 calc R U . . .
H28B H 0.1392 0.1037 -0.0776 0.047 Uiso 1 1 calc R U . . .
C23 C -0.0140(2) 0.1576(12) 0.1591(6) 0.034(2) Uani 1 1 d . . . . .
C25 C 0.0281(2) 0.2017(11) 0.0480(5) 0.030(2) Uani 1 1 d . . . . .
C26 C 0.0346(3) 0.2657(15) -0.0393(6) 0.042(2) Uani 1 1 d . . . . .
H26A H 0.0149 0.2206 -0.0746 0.051 Uiso 1 1 calc R U . . .
H26B H 0.0336 0.3955 -0.0405 0.051 Uiso 1 1 calc R U . . .
C30 C 0.2054(3) 0.239(2) -0.0190(7) 0.069(4) Uani 1 1 d . . . . .
C22 C 0.0148(3) 0.0963(14) 0.2094(6) 0.041(2) Uani 1 1 d . . . . .
C31 C 0.2358(3) 0.241(2) 0.0347(8) 0.077(4) Uani 1 1 d . . . . .
C33 C 0.1934(3) 0.229(2) 0.1489(7) 0.063(4) Uani 1 1 d . . . . .
H33 H 0.1896 0.2225 0.2057 0.076 Uiso 1 1 calc R U . . .
C38 C -0.0368(3) 0.0852(19) 0.2851(8) 0.064(3) Uani 1 1 d . . . . .
H38A H -0.0436 0.1717 0.3272 0.077 Uiso 1 1 calc R U . . .
H38B H -0.0499 -0.0259 0.2962 0.077 Uiso 1 1 calc R U . . .
C32 C 0.2295(3) 0.240(3) 0.1193(8) 0.082(5) Uani 1 1 d . . . . .
H32 H 0.2493 0.2458 0.1560 0.099 Uiso 1 1 calc R U . . .
C35 C 0.1245(2) 0.2164(13) 0.1297(6) 0.037(2) Uani 1 1 d . . . . .
H35A H 0.1165 0.3355 0.1458 0.045 Uiso 1 1 calc R U . . .
H35B H 0.1243 0.1414 0.1787 0.045 Uiso 1 1 calc R U . . .
C36 C 0.0971(2) 0.1401(13) 0.0661(6) 0.037(2) Uani 1 1 d . . . . .
H36 H 0.1037 0.0151 0.0547 0.044 Uiso 1 1 calc R U . . .
C40 C 0.3015(3) 0.252(3) 0.0512(9) 0.095(6) Uani 1 1 d . . . . .
H40A H 0.3043 0.1359 0.0764 0.142 Uiso 1 1 calc R U . . .
H40C H 0.2985 0.3408 0.0935 0.142 Uiso 1 1 calc R U . . .
H40B H 0.3232 0.2786 0.0190 0.142 Uiso 1 1 calc R U . . .
C24 C -0.0087(2) 0.2059(12) 0.0800(6) 0.037(2) Uani 1 1 d . . . . .
H24 H -0.0285 0.2412 0.0470 0.045 Uiso 1 1 calc R U . . .
C39 C 0.2287(6) 0.072(3) -0.1402(12) 0.135(8) Uani 1 1 d . . . . .
H39A H 0.2143 -0.0315 -0.1254 0.203 Uiso 1 1 calc R U . . .
H39C H 0.2533 0.0606 -0.1182 0.203 Uiso 1 1 calc R U . . .
H39B H 0.2299 0.0817 -0.1993 0.203 Uiso 1 1 calc R U . . .
O10 O 0.1196(3) 0.9597(12) 0.3137(5) 0.075(3) Uani 1 1 d . . . . .
O9 O 0.1292(3) 0.7080(11) 0.3816(5) 0.067(2) Uani 1 1 d . . . . .
H9 H 0.1242 0.7689 0.4223 0.100 Uiso 1 1 d R U . . .
C42 C 0.1458(5) 0.716(2) 0.2426(9) 0.100(5) Uani 1 1 d . . . . .
H42A H 0.1319 0.7514 0.1946 0.150 Uiso 1 1 calc R U . . .
H42C H 0.1436 0.5892 0.2504 0.150 Uiso 1 1 calc R U . . .
H42B H 0.1715 0.7471 0.2350 0.150 Uiso 1 1 calc R U . . .
C41 C 0.1314(4) 0.809(2) 0.3149(7) 0.064(3) Uani 1 1 d . . . . .
O12 O 0.3803(3) 0.0421(12) 0.3133(5) 0.072(2) Uani 1 1 d . . . . .
O11 O 0.3713(3) 0.2937(12) 0.3820(5) 0.071(2) Uani 1 1 d . . . . .
H11 H 0.3812 0.2365 0.4193 0.107 Uiso 1 1 d R U . . .
C44 C 0.3693(4) 0.192(2) 0.3146(7) 0.069(4) Uani 1 1 d . . . . .
C43 C 0.3539(6) 0.290(3) 0.2429(9) 0.110(6) Uani 1 1 d . . . . .
H43C H 0.3733 0.3122 0.2035 0.164 Uiso 1 1 calc R U . . .
H43B H 0.3436 0.4018 0.2610 0.164 Uiso 1 1 calc R U . . .
H43A H 0.3348 0.2190 0.2175 0.164 Uiso 1 1 calc R U . . .
Cl2 Cl 0.09553(7) 0.6475(3) 0.03695(16) 0.0478(7) Uani 1 1 d . . . . .
Cl1 Cl 0.40483(7) 1.3500(3) 0.03679(17) 0.0480(7) Uani 1 1 d . . . . .
C19 C 0.2745(7) 0.551(3) -0.1419(15) 0.158(9) Uiso 1 1 d . . . . .
H19A H 0.2716 0.5589 -0.2008 0.237 Uiso 1 1 calc R U . . .
H19C H 0.2921 0.4585 -0.1289 0.237 Uiso 1 1 calc R U . . .
H19B H 0.2510 0.5227 -0.1171 0.237 Uiso 1 1 calc R U . . .
H1N H 0.402(2) 0.635(13) 0.014(5) 0.03(2) Uiso 1 1 d . . . . .
H2N H 0.1008(19) 0.351(11) -0.001(4) 0.003(18) 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
O1 C3 1.370(11) . ?
O1 C18 1.425(14) . ?
O2 C2 1.369(12) . ?
O2 C18 1.421(14) . ?
O4 C11 1.371(14) . ?
O4 C20 1.429(14) . ?
O3 C10 1.381(13) . ?
O3 C19 1.70(3) . ?
N1 C8 1.481(12) . ?
N1 C7 1.499(11) . ?
N1 C16 1.522(12) . ?
N1 H1N 0.95(9) . ?
C17 C1 1.387(13) . ?
C17 C5 1.390(12) . ?
C17 C16 1.538(12) . ?
C5 C4 1.399(13) . ?
C5 C6 1.513(13) . ?
C4 C3 1.359(14) . ?
C4 H4 0.9300 . ?
C6 C7 1.514(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 C2 1.362(13) . ?
C1 H1 0.9300 . ?
C16 C15 1.531(12) . ?
C16 H16 0.9800 . ?
C15 C14 1.518(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C3 C2 1.383(13) . ?
C9 C10 1.377(15) . ?
C9 C14 1.394(14) . ?
C9 C8 1.506(13) . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C14 C13 1.361(14) . ?
C13 C12 1.378(16) . ?
C13 H13 0.9300 . ?
C12 C11 1.385(17) . ?
C12 H12 0.9300 . ?
C10 C11 1.397(16) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20C 0.9600 . ?
C20 H20B 0.9600 . ?
O7 C30 1.383(13) . ?
O7 C39 1.56(2) . ?
O8 C31 1.345(13) . ?
O8 C40 1.436(13) . ?
O5 C23 1.382(11) . ?
O5 C38 1.439(14) . ?
O6 C22 1.348(12) . ?
O6 C38 1.431(13) . ?
N2 C36 1.481(12) . ?
N2 C28 1.496(11) . ?
N2 C27 1.496(11) . ?
N2 H2N 0.81(8) . ?
C37 C25 1.372(12) . ?
C37 C21 1.402(13) . ?
C37 C36 1.538(12) . ?
C27 C26 1.497(13) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C29 C30 1.380(14) . ?
C29 C34 1.403(14) . ?
C29 C28 1.499(13) . ?
C34 C33 1.382(14) . ?
C34 C35 1.485(13) . ?
C21 C22 1.365(13) . ?
C21 H21 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C23 C24 1.342(13) . ?
C23 C22 1.397(13) . ?
C25 C24 1.421(12) . ?
C25 C26 1.509(13) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C30 C31 1.399(16) . ?
C31 C32 1.387(17) . ?
C33 C32 1.385(15) . ?
C33 H33 0.9300 . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C32 H32 0.9300 . ?
C35 C36 1.536(13) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36 0.9800 . ?
C40 H40A 0.9600 . ?
C40 H40C 0.9600 . ?
C40 H40B 0.9600 . ?
C24 H24 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39C 0.9600 . ?
C39 H39B 0.9600 . ?
O10 C41 1.203(16) . ?
O9 C41 1.317(15) . ?
O9 H9 0.8200 . ?
C42 C41 1.456(18) . ?
C42 H42A 0.9600 . ?
C42 H42C 0.9600 . ?
C42 H42B 0.9600 . ?
O12 C44 1.190(16) . ?
O11 C44 1.327(15) . ?
O11 H11 0.8200 . ?
C44 C43 1.478(19) . ?
C43 H43C 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43A 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19B 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
C3 O1 C18 105.5(8) . . ?
C2 O2 C18 105.2(8) . . ?
C11 O4 C20 117.3(10) . . ?
C10 O3 C19 113.0(12) . . ?
C8 N1 C7 109.7(7) . . ?
C8 N1 C16 111.4(7) . . ?
C7 N1 C16 110.5(7) . . ?
C8 N1 H1N 116(5) . . ?
C7 N1 H1N 113(5) . . ?
C16 N1 H1N 96(5) . . ?
C1 C17 C5 121.4(8) . . ?
C1 C17 C16 117.4(7) . . ?
C5 C17 C16 121.1(8) . . ?
C17 C5 C4 119.5(9) . . ?
C17 C5 C6 121.9(8) . . ?
C4 C5 C6 118.6(8) . . ?
C3 C4 C5 118.3(8) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C5 C6 C7 112.2(8) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N1 C7 C6 109.6(8) . . ?
N1 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C2 C1 C17 118.0(8) . . ?
C2 C1 H1 121.0 . . ?
C17 C1 H1 121.0 . . ?
N1 C16 C17 111.7(7) . . ?
N1 C16 C15 106.6(7) . . ?
C17 C16 C15 112.0(7) . . ?
N1 C16 H16 108.8 . . ?
C17 C16 H16 108.8 . . ?
C15 C16 H16 108.8 . . ?
C14 C15 C16 112.6(8) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C4 C3 O1 128.6(9) . . ?
C4 C3 C2 121.7(9) . . ?
O1 C3 C2 109.6(9) . . ?
C1 C2 O2 128.4(9) . . ?
C1 C2 C3 121.1(9) . . ?
O2 C2 C3 110.5(9) . . ?
C10 C9 C14 120.5(9) . . ?
C10 C9 C8 117.4(9) . . ?
C14 C9 C8 122.1(9) . . ?
N1 C8 C9 112.7(8) . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
H8B C8 H8A 107.8 . . ?
C13 C14 C9 119.4(9) . . ?
C13 C14 C15 120.4(9) . . ?
C9 C14 C15 120.1(8) . . ?
C14 C13 C12 120.8(11) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C12 C11 120.4(10) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O3 C10 C9 118.5(10) . . ?
O3 C10 C11 121.8(10) . . ?
C9 C10 C11 119.7(11) . . ?
O4 C11 C12 125.4(11) . . ?
O4 C11 C10 115.1(11) . . ?
C12 C11 C10 119.0(10) . . ?
O2 C18 O1 109.2(9) . . ?
O2 C18 H18A 109.8 . . ?
O1 C18 H18A 109.8 . . ?
O2 C18 H18B 109.8 . . ?
O1 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
C30 O7 C39 113.7(12) . . ?
C31 O8 C40 117.7(10) . . ?
C23 O5 C38 106.7(7) . . ?
C22 O6 C38 106.6(8) . . ?
C36 N2 C28 112.4(7) . . ?
C36 N2 C27 112.5(7) . . ?
C28 N2 C27 109.8(7) . . ?
C36 N2 H2N 110(5) . . ?
C28 N2 H2N 103(5) . . ?
C27 N2 H2N 109(5) . . ?
C25 C37 C21 120.9(8) . . ?
C25 C37 C36 121.6(8) . . ?
C21 C37 C36 117.5(8) . . ?
N2 C27 C26 109.7(7) . . ?
N2 C27 H27A 109.7 . . ?
C26 C27 H27A 109.7 . . ?
N2 C27 H27B 109.7 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C30 C29 C34 120.6(9) . . ?
C30 C29 C28 117.6(9) . . ?
C34 C29 C28 121.9(9) . . ?
C33 C34 C29 117.8(9) . . ?
C33 C34 C35 121.4(9) . . ?
C29 C34 C35 120.8(8) . . ?
C22 C21 C37 119.0(8) . . ?
C22 C21 H21 120.5 . . ?
C37 C21 H21 120.5 . . ?
N2 C28 C29 112.3(8) . . ?
N2 C28 H28A 109.1 . . ?
C29 C28 H28A 109.1 . . ?
N2 C28 H28B 109.1 . . ?
C29 C28 H28B 109.1 . . ?
H28A C28 H28B 107.9 . . ?
C24 C23 O5 129.5(8) . . ?
C24 C23 C22 122.4(8) . . ?
O5 C23 C22 108.1(8) . . ?
C37 C25 C24 119.6(8) . . ?
C37 C25 C26 121.7(8) . . ?
C24 C25 C26 118.6(8) . . ?
C27 C26 C25 112.3(8) . . ?
C27 C26 H26A 109.2 . . ?
C25 C26 H26A 109.2 . . ?
C27 C26 H26B 109.2 . . ?
C25 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C29 C30 O7 117.7(9) . . ?
C29 C30 C31 120.8(10) . . ?
O7 C30 C31 121.5(9) . . ?
O6 C22 C21 129.1(9) . . ?
O6 C22 C23 111.2(8) . . ?
C21 C22 C23 119.7(9) . . ?
O8 C31 C32 125.3(10) . . ?
O8 C31 C30 115.8(11) . . ?
C32 C31 C30 118.9(10) . . ?
C34 C33 C32 122.2(10) . . ?
C34 C33 H33 118.9 . . ?
C32 C33 H33 118.9 . . ?
O6 C38 O5 107.4(9) . . ?
O6 C38 H38A 110.2 . . ?
O5 C38 H38A 110.2 . . ?
O6 C38 H38B 110.2 . . ?
O5 C38 H38B 110.2 . . ?
H38A C38 H38B 108.5 . . ?
C31 C32 C33 119.7(10) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C34 C35 C36 112.1(8) . . ?
C34 C35 H35A 109.2 . . ?
C36 C35 H35A 109.2 . . ?
C34 C35 H35B 109.2 . . ?
C36 C35 H35B 109.2 . . ?
H35A C35 H35B 107.9 . . ?
N2 C36 C35 107.7(7) . . ?
N2 C36 C37 111.1(7) . . ?
C35 C36 C37 111.8(7) . . ?
N2 C36 H36 108.7 . . ?
C35 C36 H36 108.7 . . ?
C37 C36 H36 108.7 . . ?
O8 C40 H40A 109.5 . . ?
O8 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
O8 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40C C40 H40B 109.5 . . ?
C23 C24 C25 118.4(8) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
O7 C39 H39A 109.5 . . ?
O7 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
O7 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39C C39 H39B 109.5 . . ?
C41 O9 H9 110.6 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42C C42 H42B 109.5 . . ?
O10 C41 O9 121.9(12) . . ?
O10 C41 C42 123.8(13) . . ?
O9 C41 C42 114.0(13) . . ?
C44 O11 H11 109.4 . . ?
O12 C44 O11 122.1(12) . . ?
O12 C44 C43 125.1(14) . . ?
O11 C44 C43 112.7(14) . . ?
C44 C43 H43C 109.5 . . ?
C44 C43 H43B 109.5 . . ?
H43C C43 H43B 109.5 . . ?
C44 C43 H43A 109.5 . . ?
H43C C43 H43A 109.5 . . ?
H43B C43 H43A 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19C C19 H19B 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
C1 C17 C5 C4 0.8(14) . . . . ?
C16 C17 C5 C4 -177.3(9) . . . . ?
C1 C17 C5 C6 178.4(8) . . . . ?
C16 C17 C5 C6 0.2(13) . . . . ?
C17 C5 C4 C3 -2.3(15) . . . . ?
C6 C5 C4 C3 -179.9(9) . . . . ?
C17 C5 C6 C7 17.3(13) . . . . ?
C4 C5 C6 C7 -165.2(9) . . . . ?
C8 N1 C7 C6 -170.1(8) . . . . ?
C16 N1 C7 C6 66.7(10) . . . . ?
C5 C6 C7 N1 -49.8(11) . . . . ?
C5 C17 C1 C2 -0.2(14) . . . . ?
C16 C17 C1 C2 178.0(8) . . . . ?
C8 N1 C16 C17 -170.0(7) . . . . ?
C7 N1 C16 C17 -47.7(9) . . . . ?
C8 N1 C16 C15 67.4(9) . . . . ?
C7 N1 C16 C15 -170.3(8) . . . . ?
C1 C17 C16 N1 -163.4(8) . . . . ?
C5 C17 C16 N1 14.9(11) . . . . ?
C1 C17 C16 C15 -43.9(11) . . . . ?
C5 C17 C16 C15 134.3(9) . . . . ?
N1 C16 C15 C14 -52.0(11) . . . . ?
C17 C16 C15 C14 -174.5(8) . . . . ?
C5 C4 C3 O1 179.1(10) . . . . ?
C5 C4 C3 C2 3.2(15) . . . . ?
C18 O1 C3 C4 -176.4(11) . . . . ?
C18 O1 C3 C2 -0.2(12) . . . . ?
C17 C1 C2 O2 -178.7(9) . . . . ?
C17 C1 C2 C3 1.1(14) . . . . ?
C18 O2 C2 C1 179.1(11) . . . . ?
C18 O2 C2 C3 -0.8(12) . . . . ?
C4 C3 C2 C1 -2.7(16) . . . . ?
O1 C3 C2 C1 -179.2(9) . . . . ?
C4 C3 C2 O2 177.2(10) . . . . ?
O1 C3 C2 O2 0.6(12) . . . . ?
C7 N1 C8 C9 -170.4(9) . . . . ?
C16 N1 C8 C9 -47.7(12) . . . . ?
C10 C9 C8 N1 -167.1(11) . . . . ?
C14 C9 C8 N1 13.6(16) . . . . ?
C10 C9 C14 C13 -2(2) . . . . ?
C8 C9 C14 C13 176.8(12) . . . . ?
C10 C9 C14 C15 -179.5(12) . . . . ?
C8 C9 C14 C15 -0.2(18) . . . . ?
C16 C15 C14 C13 -156.3(11) . . . . ?
C16 C15 C14 C9 20.7(15) . . . . ?
C9 C14 C13 C12 3(2) . . . . ?
C15 C14 C13 C12 -179.5(14) . . . . ?
C14 C13 C12 C11 -1(3) . . . . ?
C19 O3 C10 C9 112.5(16) . . . . ?
C19 O3 C10 C11 -67.2(19) . . . . ?
C14 C9 C10 O3 179.1(12) . . . . ?
C8 C9 C10 O3 0(2) . . . . ?
C14 C9 C10 C11 -1(2) . . . . ?
C8 C9 C10 C11 179.4(13) . . . . ?
C20 O4 C11 C12 -5(3) . . . . ?
C20 O4 C11 C10 -177.3(15) . . . . ?
C13 C12 C11 O4 -174.8(17) . . . . ?
C13 C12 C11 C10 -3(3) . . . . ?
O3 C10 C11 O4 -4(2) . . . . ?
C9 C10 C11 O4 176.6(14) . . . . ?
O3 C10 C11 C12 -176.4(15) . . . . ?
C9 C10 C11 C12 4(2) . . . . ?
C2 O2 C18 O1 0.7(13) . . . . ?
C3 O1 C18 O2 -0.3(13) . . . . ?
C36 N2 C27 C26 65.4(10) . . . . ?
C28 N2 C27 C26 -168.7(8) . . . . ?
C30 C29 C34 C33 -1.3(18) . . . . ?
C28 C29 C34 C33 177.4(11) . . . . ?
C30 C29 C34 C35 -180.0(12) . . . . ?
C28 C29 C34 C35 -1.3(17) . . . . ?
C25 C37 C21 C22 -1.9(14) . . . . ?
C36 C37 C21 C22 179.2(9) . . . . ?
C36 N2 C28 C29 -45.2(11) . . . . ?
C27 N2 C28 C29 -171.1(8) . . . . ?
C30 C29 C28 N2 -169.2(11) . . . . ?
C34 C29 C28 N2 12.1(15) . . . . ?
C38 O5 C23 C24 178.2(11) . . . . ?
C38 O5 C23 C22 0.2(11) . . . . ?
C21 C37 C25 C24 1.4(13) . . . . ?
C36 C37 C25 C24 -179.8(8) . . . . ?
C21 C37 C25 C26 178.9(9) . . . . ?
C36 C37 C25 C26 -2.2(13) . . . . ?
N2 C27 C26 C25 -48.7(11) . . . . ?
C37 C25 C26 C27 19.1(13) . . . . ?
C24 C25 C26 C27 -163.3(8) . . . . ?
C34 C29 C30 O7 -179.2(12) . . . . ?
C28 C29 C30 O7 2(2) . . . . ?
C34 C29 C30 C31 1(2) . . . . ?
C28 C29 C30 C31 -177.6(14) . . . . ?
C39 O7 C30 C29 -112.5(15) . . . . ?
C39 O7 C30 C31 67(2) . . . . ?
C38 O6 C22 C21 179.8(11) . . . . ?
C38 O6 C22 C23 2.2(13) . . . . ?
C37 C21 C22 O6 -177.3(10) . . . . ?
C37 C21 C22 C23 0.1(15) . . . . ?
C24 C23 C22 O6 -179.7(9) . . . . ?
O5 C23 C22 O6 -1.6(12) . . . . ?
C24 C23 C22 C21 2.4(15) . . . . ?
O5 C23 C22 C21 -179.4(9) . . . . ?
C40 O8 C31 C32 3(3) . . . . ?
C40 O8 C31 C30 -179.1(16) . . . . ?
C29 C30 C31 O8 -179.8(15) . . . . ?
O7 C30 C31 O8 0(3) . . . . ?
C29 C30 C31 C32 -2(3) . . . . ?
O7 C30 C31 C32 178.7(16) . . . . ?
C29 C34 C33 C32 2(2) . . . . ?
C35 C34 C33 C32 -179.2(13) . . . . ?
C22 O6 C38 O5 -2.0(13) . . . . ?
C23 O5 C38 O6 1.1(13) . . . . ?
O8 C31 C32 C33 -179.6(17) . . . . ?
C30 C31 C32 C33 2(3) . . . . ?
C34 C33 C32 C31 -3(3) . . . . ?
C33 C34 C35 C36 -156.8(11) . . . . ?
C29 C34 C35 C36 21.9(14) . . . . ?
C28 N2 C36 C35 65.9(9) . . . . ?
C27 N2 C36 C35 -169.7(7) . . . . ?
C28 N2 C36 C37 -171.4(7) . . . . ?
C27 N2 C36 C37 -46.9(10) . . . . ?
C34 C35 C36 N2 -52.5(10) . . . . ?
C34 C35 C36 C37 -174.8(8) . . . . ?
C25 C37 C36 N2 15.8(12) . . . . ?
C21 C37 C36 N2 -165.3(8) . . . . ?
C25 C37 C36 C35 136.1(9) . . . . ?
C21 C37 C36 C35 -45.0(12) . . . . ?
O5 C23 C24 C25 179.3(9) . . . . ?
C22 C23 C24 C25 -2.9(14) . . . . ?
C37 C25 C24 C23 1.0(13) . . . . ?
C26 C25 C24 C23 -176.6(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 Cl1 0.93 2.88 3.803(10) 172.0 3_675
C1 H1 O12 0.93 2.52 3.443(12) 174.4 1_565
C16 H16 Cl1 0.98 2.78 3.699(9) 157.4 .
C15 H15B O12 0.97 2.59 3.556(13) 174.8 1_565
C8 H8B O12 0.97 2.42 3.308(15) 152.3 4_565
C8 H8A O11 0.97 2.46 3.412(15) 166.6 4_575
C18 H18A Cl1 0.97 2.94 3.622(12) 128.7 2_645
C20 H20B Cl2 0.96 2.98 3.774(12) 141.0 .
C21 H21 O10 0.93 2.53 3.451(13) 173.8 1_545
C28 H28A O10 0.97 2.43 3.321(14) 152.5 4_575
C28 H28B O9 0.97 2.44 3.391(13) 165.2 4_565
C38 H38A Cl2 0.97 2.89 3.600(12) 130.9 2_545
C35 H35B O10 0.97 2.57 3.542(13) 175.3 1_545
C36 H36 Cl2 0.98 2.77 3.707(10) 159.2 1_545
C24 H24 Cl2 0.93 2.89 3.814(9) 172.9 3_565
C39 H39C O8 0.96 2.43 2.99(2) 117.1 .
O9 H9 Cl2 0.82 2.21 2.990(9) 158.8 4_576
C42 H42A Cl2 0.96 2.97 3.820(16) 148.5 .
O11 H11 Cl1 0.82 2.18 2.978(9) 164.7 4_576
C43 H43C Cl1 0.96 2.94 3.830(17) 155.0 1_545
C19 H19B O4 0.96 2.54 3.08(3) 115.1 .
C19 H19B O7 0.96 2.56 3.32(3) 136.1 .
N1 H1N Cl1 0.95(9) 2.16(10) 3.080(9) 163(7) 1_545
N2 H2N Cl2 0.81(8) 2.30(8) 3.109(8) 175(7) .

_refine_diff_density_max         1.643
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1547190'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2017-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N O4, C H4 O, Cl'
_chemical_formula_sum            'C21 H26 Cl N O5'
_chemical_formula_weight         407.88

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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   7.2610(4)
_cell_length_b                   15.3853(8)
_cell_length_c                   36.6862(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4098.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2071
_cell_measurement_theta_min      4.1630
_cell_measurement_theta_max      26.1190

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             1728.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.218
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41438
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10277
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.295
_diffrn_reflns_theta_max         24.498
_diffrn_reflns_theta_full        24.498
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3412
_reflns_number_gt                2619
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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)+(0.1412P)²+1.1713P] 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_number_reflns         3412
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.2256
_refine_ls_wR_factor_gt          0.1810
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
H1N H 0.664(5) 0.496(2) 0.6040(8) 0.036(10) Uiso 1 1 d . . . . .
O5 O 0.9455(5) 0.6755(2) 0.87581(11) 0.0968(11) Uani 1 1 d . . . . .
H5 H 0.9333 0.6233 0.8797 0.145 Uiso 1 1 calc R U . . .
Cl1 Cl 0.35279(11) 0.48554(6) 0.60015(2) 0.0517(3) Uani 1 1 d . . . . .
O4 O 0.8093(4) 0.47691(17) 0.77019(6) 0.0584(7) Uani 1 1 d . . . . .
O3 O 0.8158(3) 0.59045(14) 0.71237(6) 0.0497(6) Uani 1 1 d . . . . .
N1 N 0.7758(4) 0.50532(16) 0.60489(6) 0.0355(6) Uani 1 1 d . . . . .
O2 O 0.8281(4) 0.30091(16) 0.45322(6) 0.0580(7) Uani 1 1 d . . . . .
C16 C 0.8685(4) 0.41926(19) 0.59788(7) 0.0352(7) Uani 1 1 d . . . . .
H16 H 0.9993 0.4253 0.6040 0.042 Uiso 1 1 calc R U . . .
O1 O 0.9255(4) 0.20468(15) 0.49758(6) 0.0571(6) Uani 1 1 d . . . . .
C9 C 0.8061(4) 0.4725(2) 0.67128(8) 0.0376(7) Uani 1 1 d . . . . .
C17 C 0.8545(4) 0.39345(19) 0.55816(7) 0.0359(7) Uani 1 1 d . . . . .
C5 C 0.7978(4) 0.4516(2) 0.53112(8) 0.0401(7) Uani 1 1 d . . . . .
C14 C 0.7930(4) 0.3841(2) 0.66336(8) 0.0379(7) Uani 1 1 d . . . . .
C6 C 0.7479(5) 0.5439(2) 0.54029(8) 0.0452(8) Uani 1 1 d . . . . .
H6A H 0.6149 0.5495 0.5409 0.054 Uiso 1 1 calc R U . . .
H6B H 0.7943 0.5821 0.5214 0.054 Uiso 1 1 calc R U . . .
C4 C 0.7864(4) 0.4251(2) 0.49451(8) 0.0447(8) Uani 1 1 d . . . . .
H4 H 0.7489 0.4635 0.4764 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8320(4) 0.3417(2) 0.48641(8) 0.0435(8) Uani 1 1 d . . . . .
C8 C 0.8194(5) 0.5402(2) 0.64194(8) 0.0432(8) Uani 1 1 d . . . . .
H8A H 0.7349 0.5872 0.6475 0.052 Uiso 1 1 calc R U . . .
H8B H 0.9431 0.5640 0.6418 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7959(5) 0.3544(2) 0.72795(8) 0.0483(8) Uani 1 1 d . . . . .
H12 H 0.7931 0.3142 0.7469 0.058 Uiso 1 1 calc R U . . .
C2 C 0.8901(4) 0.28435(19) 0.51297(8) 0.0409(7) Uani 1 1 d . . . . .
C1 C 0.9040(4) 0.30737(19) 0.54863(8) 0.0413(7) Uani 1 1 d . . . . .
H1 H 0.9444 0.2680 0.5661 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7835(4) 0.35395(19) 0.62416(7) 0.0395(7) Uani 1 1 d . . . . .
H15A H 0.6557 0.3445 0.6175 0.047 Uiso 1 1 calc R U . . .
H15B H 0.8475 0.2989 0.6219 0.047 Uiso 1 1 calc R U . . .
C7 C 0.8262(5) 0.5717(2) 0.57671(8) 0.0455(8) Uani 1 1 d . . . . .
H7A H 0.9591 0.5767 0.5750 0.055 Uiso 1 1 calc R U . . .
H7B H 0.7767 0.6280 0.5835 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7897(4) 0.3258(2) 0.69218(8) 0.0437(8) Uani 1 1 d . . . . .
H13 H 0.7833 0.2665 0.6874 0.052 Uiso 1 1 calc R U . . .
C10 C 0.8131(4) 0.5016(2) 0.70709(8) 0.0403(7) Uani 1 1 d . . . . .
C11 C 0.8062(4) 0.4421(2) 0.73573(8) 0.0444(8) Uani 1 1 d . . . . .
C20 C 0.8011(5) 0.4188(3) 0.80039(9) 0.0632(10) Uani 1 1 d . . . . .
H20A H 0.6898 0.3852 0.7991 0.095 Uiso 1 1 calc R U . . .
H20C H 0.8024 0.4514 0.8227 0.095 Uiso 1 1 calc R U . . .
H20B H 0.9055 0.3805 0.7998 0.095 Uiso 1 1 calc R U . . .
C19 C 0.9664(6) 0.6254(3) 0.73253(11) 0.0702(11) Uani 1 1 d . . . . .
H19B H 0.9552 0.6089 0.7577 0.105 Uiso 1 1 calc R U . . .
H19C H 0.9656 0.6876 0.7306 0.105 Uiso 1 1 calc R U . . .
H19A H 1.0800 0.6032 0.7229 0.105 Uiso 1 1 calc R U . . .
C18 C 0.8947(5) 0.2151(2) 0.45991(9) 0.0590(9) Uani 1 1 d . . . . .
H18B H 0.8051 0.1728 0.4516 0.071 Uiso 1 1 calc R U . . .
H18A H 1.0086 0.2057 0.4467 0.071 Uiso 1 1 calc R U . . .
C21 C 0.7847(14) 0.7076(6) 0.8558(2) 0.222(6) Uani 1 1 d . . . . .
H21C H 0.6755 0.6980 0.8699 0.332 Uiso 1 1 calc R U . . .
H21A H 0.7746 0.6773 0.8330 0.332 Uiso 1 1 calc R U . . .
H21B H 0.7987 0.7687 0.8512 0.332 Uiso 1 1 calc R U . . .


_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
O5 C21 1.466(9) . ?
O5 H5 0.8200 . ?
O4 C11 1.373(4) . ?
O4 C20 1.425(4) . ?
O3 C10 1.381(4) . ?
O3 C19 1.425(4) . ?
N1 C8 1.495(4) . ?
N1 C7 1.499(4) . ?
N1 C16 1.508(4) . ?
N1 H1N 0.82(4) . ?
O2 C3 1.370(4) . ?
O2 C18 1.427(4) . ?
C16 C17 1.514(4) . ?
C16 C15 1.523(4) . ?
C16 H16 0.9800 . ?
O1 C2 1.374(4) . ?
O1 C18 1.409(4) . ?
C9 C10 1.389(4) . ?
C9 C14 1.394(4) . ?
C9 C8 1.501(4) . ?
C17 C5 1.398(4) . ?
C17 C1 1.416(4) . ?
C5 C4 1.406(4) . ?
C5 C6 1.503(4) . ?
C14 C13 1.387(4) . ?
C14 C15 1.513(4) . ?
C6 C7 1.514(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 C3 1.359(5) . ?
C4 H4 0.9300 . ?
C3 C2 1.380(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 C11 1.381(5) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C2 C1 1.359(4) . ?
C1 H1 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 H13 0.9300 . ?
C10 C11 1.395(5) . ?
C20 H20A 0.9600 . ?
C20 H20C 0.9600 . ?
C20 H20B 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19A 0.9600 . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?
C21 H21C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 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
C21 O5 H5 109.5 . . ?
C11 O4 C20 118.0(3) . . ?
C10 O3 C19 117.2(3) . . ?
C8 N1 C7 109.3(2) . . ?
C8 N1 C16 112.1(2) . . ?
C7 N1 C16 111.8(2) . . ?
C8 N1 H1N 108(2) . . ?
C7 N1 H1N 110(2) . . ?
C16 N1 H1N 106(2) . . ?
C3 O2 C18 105.3(2) . . ?
N1 C16 C17 111.4(2) . . ?
N1 C16 C15 106.9(2) . . ?
C17 C16 C15 114.2(2) . . ?
N1 C16 H16 108.1 . . ?
C17 C16 H16 108.1 . . ?
C15 C16 H16 108.1 . . ?
C2 O1 C18 105.8(2) . . ?
C10 C9 C14 121.0(3) . . ?
C10 C9 C8 116.9(3) . . ?
C14 C9 C8 122.1(3) . . ?
C5 C17 C1 119.9(3) . . ?
C5 C17 C16 122.3(3) . . ?
C1 C17 C16 117.8(3) . . ?
C17 C5 C4 120.6(3) . . ?
C17 C5 C6 121.1(3) . . ?
C4 C5 C6 118.3(3) . . ?
C13 C14 C9 118.2(3) . . ?
C13 C14 C15 121.7(3) . . ?
C9 C14 C15 120.0(3) . . ?
C5 C6 C7 112.0(2) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C3 C4 C5 118.0(3) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C3 O2 128.5(3) . . ?
C4 C3 C2 121.6(3) . . ?
O2 C3 C2 110.0(3) . . ?
N1 C8 C9 112.9(3) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C1 C2 O1 127.9(3) . . ?
C1 C2 C3 122.4(3) . . ?
O1 C2 C3 109.7(3) . . ?
C2 C1 C17 117.6(3) . . ?
C2 C1 H1 121.2 . . ?
C17 C1 H1 121.2 . . ?
C14 C15 C16 112.4(2) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
N1 C7 C6 108.9(3) . . ?
N1 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
N1 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
O3 C10 C9 116.9(3) . . ?
O3 C10 C11 123.0(3) . . ?
C9 C10 C11 120.0(3) . . ?
O4 C11 C12 124.9(3) . . ?
O4 C11 C10 115.9(3) . . ?
C12 C11 C10 119.2(3) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
O1 C18 O2 109.1(3) . . ?
O1 C18 H18B 109.9 . . ?
O2 C18 H18B 109.9 . . ?
O1 C18 H18A 109.9 . . ?
O2 C18 H18A 109.9 . . ?
H18B C18 H18A 108.3 . . ?
O5 C21 H21C 109.5 . . ?
O5 C21 H21A 109.5 . . ?
H21C C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
H21A C21 H21B 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 N1 C16 C17 -168.8(2) . . . . ?
C7 N1 C16 C17 -45.6(3) . . . . ?
C8 N1 C16 C15 65.9(3) . . . . ?
C7 N1 C16 C15 -170.9(2) . . . . ?
N1 C16 C17 C5 12.6(4) . . . . ?
C15 C16 C17 C5 133.7(3) . . . . ?
N1 C16 C17 C1 -168.4(3) . . . . ?
C15 C16 C17 C1 -47.2(4) . . . . ?
C1 C17 C5 C4 1.0(4) . . . . ?
C16 C17 C5 C4 -179.9(3) . . . . ?
C1 C17 C5 C6 -178.8(3) . . . . ?
C16 C17 C5 C6 0.2(4) . . . . ?
C10 C9 C14 C13 -0.9(4) . . . . ?
C8 C9 C14 C13 177.1(3) . . . . ?
C10 C9 C14 C15 179.3(3) . . . . ?
C8 C9 C14 C15 -2.6(4) . . . . ?
C17 C5 C6 C7 19.3(4) . . . . ?
C4 C5 C6 C7 -160.5(3) . . . . ?
C17 C5 C4 C3 0.1(4) . . . . ?
C6 C5 C4 C3 179.9(3) . . . . ?
C5 C4 C3 O2 178.6(3) . . . . ?
C5 C4 C3 C2 -0.8(5) . . . . ?
C18 O2 C3 C4 178.2(3) . . . . ?
C18 O2 C3 C2 -2.4(3) . . . . ?
C7 N1 C8 C9 -169.4(3) . . . . ?
C16 N1 C8 C9 -44.9(4) . . . . ?
C10 C9 C8 N1 -169.3(3) . . . . ?
C14 C9 C8 N1 12.6(4) . . . . ?
C18 O1 C2 C1 -178.7(3) . . . . ?
C18 O1 C2 C3 2.4(4) . . . . ?
C4 C3 C2 C1 0.5(5) . . . . ?
O2 C3 C2 C1 -179.0(3) . . . . ?
C4 C3 C2 O1 179.5(3) . . . . ?
O2 C3 C2 O1 0.0(4) . . . . ?
O1 C2 C1 C17 -178.2(3) . . . . ?
C3 C2 C1 C17 0.6(5) . . . . ?
C5 C17 C1 C2 -1.3(4) . . . . ?
C16 C17 C1 C2 179.6(3) . . . . ?
C13 C14 C15 C16 -155.5(3) . . . . ?
C9 C14 C15 C16 24.2(4) . . . . ?
N1 C16 C15 C14 -53.9(3) . . . . ?
C17 C16 C15 C14 -177.5(2) . . . . ?
C8 N1 C7 C6 -168.9(3) . . . . ?
C16 N1 C7 C6 66.4(3) . . . . ?
C5 C6 C7 N1 -51.0(4) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C9 C14 C13 C12 1.2(5) . . . . ?
C15 C14 C13 C12 -179.1(3) . . . . ?
C19 O3 C10 C9 -123.1(3) . . . . ?
C19 O3 C10 C11 60.7(4) . . . . ?
C14 C9 C10 O3 -176.5(3) . . . . ?
C8 C9 C10 O3 5.3(4) . . . . ?
C14 C9 C10 C11 -0.3(4) . . . . ?
C8 C9 C10 C11 -178.4(3) . . . . ?
C20 O4 C11 C12 -0.1(5) . . . . ?
C20 O4 C11 C10 179.5(3) . . . . ?
C13 C12 C11 O4 178.7(3) . . . . ?
C13 C12 C11 C10 -0.9(5) . . . . ?
O3 C10 C11 O4 -2.4(4) . . . . ?
C9 C10 C11 O4 -178.4(3) . . . . ?
O3 C10 C11 C12 177.2(3) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C2 O1 C18 O2 -3.9(4) . . . . ?
C3 O2 C18 O1 3.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 Cl1 0.82 2.32 3.126(3) 167.8 6_657
C16 H16 Cl1 0.98 2.73 3.662(3) 158.5 1_655
C6 H6B O1 0.97 2.62 3.188(4) 117.6 8_765
C8 H8A O5 0.97 2.64 3.483(5) 144.8 6_557
C15 H15B O5 0.97 2.42 3.379(4) 168.2 3_746
C7 H7A O2 0.97 2.65 3.369(4) 131.4 5_766
C20 H20C Cl1 0.96 2.90 3.809(4) 158.0 6_657
C19 H19B O4 0.96 2.34 2.903(5) 117.2 .
C19 H19A O4 0.96 2.57 3.380(5) 142.0 6_657

_refine_diff_density_max         0.666
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.197

