# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1863144'
_audit_update_record             
;
2018-08-21 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 Cl N2 O2, C5 H9 N O2'
_chemical_formula_sum            'C18 H20 Cl N3 O4'
_chemical_formula_weight         377.82

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   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   5.7721(7)
_cell_length_b                   12.3373(15)
_cell_length_c                   24.977(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1778.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4321
_cell_measurement_theta_min      2.321
_cell_measurement_theta_max      25.253

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13863
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3213
_reflns_number_gt                2936
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0347P)²+0.1438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_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   0.00(5)
_refine_ls_number_reflns         3213
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration rmad

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 -0.52883(9) 0.79656(5) 0.242036(19) 0.04884(15) Uani 1 1 d . . .
N11 N 0.3826(3) 1.00391(11) 0.39339(6) 0.0314(3) Uani 1 1 d . . .
N12 N 0.1656(3) 0.85446(12) 0.36534(6) 0.0285(3) Uani 1 1 d . . .
O11 O 0.6168(2) 0.65373(10) 0.45176(5) 0.0334(3) Uani 1 1 d . . .
O12 O 0.2935(2) 0.66001(10) 0.40336(6) 0.0392(3) Uani 1 1 d . . .
C11 C 0.4550(3) 0.70632(14) 0.42457(6) 0.0276(4) Uani 1 1 d . . .
C12 C 0.4945(3) 0.82478(13) 0.42271(6) 0.0254(4) Uani 1 1 d . . .
C13 C 0.6852(3) 0.86939(14) 0.44854(7) 0.0282(4) Uani 1 1 d . . .
C14 C 0.7245(4) 0.97897(14) 0.44658(7) 0.0325(4) Uani 1 1 d . . .
C15 C 0.5685(3) 1.04173(15) 0.41941(7) 0.0337(4) Uani 1 1 d . . .
C16 C 0.3478(3) 0.89672(12) 0.39375(6) 0.0249(4) Uani 1 1 d . . .
C21 C 0.0077(3) 0.90231(13) 0.32991(6) 0.0263(4) Uani 1 1 d . . .
C22 C -0.1597(3) 0.83224(14) 0.30733(6) 0.0277(4) Uani 1 1 d . . .
C23 C -0.3192(3) 0.87811(15) 0.27256(7) 0.0330(4) Uani 1 1 d . . .
C24 C -0.3237(3) 0.98704(16) 0.26001(8) 0.0376(4) Uani 1 1 d . . .
C25 C -0.1559(4) 1.05265(16) 0.28203(7) 0.0387(5) Uani 1 1 d . . .
C26 C 0.0093(4) 1.01172(14) 0.31644(7) 0.0342(4) Uani 1 1 d . . .
C27 C -0.1582(4) 0.71380(16) 0.32071(9) 0.0384(4) Uani 1 1 d . . .
H11 H 0.594(4) 0.5826(19) 0.4470(9) 0.059(7) Uiso 1 1 d . . .
H12 H 0.159(3) 0.7828(15) 0.3695(6) 0.023(4) Uiso 1 1 d . . .
H13 H 0.790(3) 0.8217(14) 0.4664(7) 0.029(5) Uiso 1 1 d . . .
H14 H 0.848(4) 1.0081(16) 0.4621(8) 0.045(6) Uiso 1 1 d . . .
H15 H 0.593(3) 1.1186(16) 0.4171(7) 0.039(5) Uiso 1 1 d . . .
H24 H -0.441(4) 1.0118(14) 0.2364(8) 0.039(5) Uiso 1 1 d . . .
H25 H -0.156(3) 1.1276(15) 0.2741(7) 0.035(5) Uiso 1 1 d . . .
H26 H 0.120(3) 1.0554(15) 0.3310(7) 0.034(5) Uiso 1 1 d . . .
H271 H -0.283(5) 0.677(2) 0.3031(10) 0.075(8) Uiso 1 1 d . . .
H272 H -0.014(4) 0.6801(16) 0.3080(8) 0.050(6) Uiso 1 1 d . . .
H273 H -0.163(4) 0.6972(16) 0.3585(9) 0.045(6) Uiso 1 1 d . . .
N1 N 1.1545(2) 0.34409(11) 0.44095(5) 0.0216(3) Uani 1 1 d . . .
O1 O 0.56904(19) 0.44696(9) 0.45036(5) 0.0297(3) Uani 1 1 d . . .
O2 O 0.73243(19) 0.28850(9) 0.46997(5) 0.0285(3) Uani 1 1 d . . .
C1 C 0.7397(3) 0.38208(13) 0.45291(6) 0.0203(3) Uani 1 1 d . . .
C2 C 0.9672(3) 0.42476(12) 0.43022(6) 0.0205(3) Uani 1 1 d . . .
C3 C 0.9595(3) 0.43056(14) 0.36917(6) 0.0285(4) Uani 1 1 d . . .
C4 C 1.0013(3) 0.31345(14) 0.35283(7) 0.0310(4) Uani 1 1 d . . .
C5 C 1.1880(3) 0.27571(16) 0.39131(8) 0.0343(4) Uani 1 1 d . . .
H1 H 1.288(4) 0.3779(15) 0.4493(8) 0.035(5) Uiso 1 1 d . . .
H2 H 1.116(3) 0.2998(15) 0.4698(8) 0.035(5) Uiso 1 1 d . . .
H21 H 1.009(3) 0.4940(13) 0.4466(6) 0.026(4) Uiso 1 1 d . . .
H31 H 1.087(3) 0.4760(13) 0.3573(7) 0.022(4) Uiso 1 1 d . . .
H32 H 0.809(4) 0.4617(15) 0.3573(7) 0.036(5) Uiso 1 1 d . . .
H41 H 1.056(3) 0.3062(13) 0.3165(7) 0.031(5) Uiso 1 1 d . . .
H42 H 0.865(3) 0.2706(14) 0.3591(7) 0.029(5) Uiso 1 1 d . . .
H51 H 1.353(4) 0.2953(17) 0.3777(8) 0.048(6) Uiso 1 1 d . . .
H52 H 1.182(3) 0.1992(17) 0.4010(7) 0.040(5) 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
Cl1 C23 1.7488(18) . ?
N11 C16 1.338(2) . ?
N11 C15 1.339(2) . ?
N12 C16 1.372(2) . ?
N12 C21 1.401(2) . ?
N12 H12 0.892(18) . ?
O11 C11 1.324(2) . ?
O11 H11 0.90(2) . ?
O12 C11 1.215(2) . ?
C11 C12 1.480(2) . ?
C12 C13 1.390(2) . ?
C12 C16 1.424(2) . ?
C13 C14 1.372(2) . ?
C13 H13 0.953(18) . ?
C14 C15 1.368(3) . ?
C14 H14 0.89(2) . ?
C15 H15 0.96(2) . ?
C21 C26 1.391(2) . ?
C21 C22 1.414(2) . ?
C22 C23 1.386(2) . ?
C22 C27 1.499(3) . ?
C23 C24 1.380(3) . ?
C24 C25 1.377(3) . ?
C24 H24 0.95(2) . ?
C25 C26 1.380(3) . ?
C25 H25 0.946(18) . ?
C26 H26 0.91(2) . ?
C27 H271 0.96(3) . ?
C27 H272 0.98(2) . ?
C27 H273 0.97(2) . ?
N1 C2 1.4933(19) . ?
N1 C5 1.512(2) . ?
N1 H1 0.90(2) . ?
N1 H2 0.932(19) . ?
O1 C1 1.2709(19) . ?
O2 C1 1.2313(19) . ?
C1 C2 1.524(2) . ?
C2 C3 1.527(2) . ?
C2 H21 0.977(17) . ?
C3 C4 1.521(3) . ?
C3 H31 0.970(18) . ?
C3 H32 0.99(2) . ?
C4 C5 1.517(3) . ?
C4 H41 0.963(18) . ?
C4 H42 0.961(19) . ?
C5 H51 1.04(2) . ?
C5 H52 0.98(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
C16 N11 C15 117.50(15) . . ?
C16 N12 C21 131.71(14) . . ?
C16 N12 H12 110.5(11) . . ?
C21 N12 H12 117.6(11) . . ?
C11 O11 H11 107.8(15) . . ?
O12 C11 O11 122.29(15) . . ?
O12 C11 C12 124.67(15) . . ?
O11 C11 C12 113.04(15) . . ?
C13 C12 C16 117.39(15) . . ?
C13 C12 C11 119.89(15) . . ?
C16 C12 C11 122.68(15) . . ?
C14 C13 C12 120.30(18) . . ?
C14 C13 H13 121.4(11) . . ?
C12 C13 H13 118.2(11) . . ?
C15 C14 C13 117.85(19) . . ?
C15 C14 H14 121.1(13) . . ?
C13 C14 H14 121.1(13) . . ?
N11 C15 C14 124.84(17) . . ?
N11 C15 H15 115.6(11) . . ?
C14 C15 H15 119.5(12) . . ?
N11 C16 N12 119.18(15) . . ?
N11 C16 C12 122.02(15) . . ?
N12 C16 C12 118.80(14) . . ?
C26 C21 N12 123.87(16) . . ?
C26 C21 C22 120.11(16) . . ?
N12 C21 C22 116.03(14) . . ?
C23 C22 C21 117.00(15) . . ?
C23 C22 C27 122.77(16) . . ?
C21 C22 C27 120.23(16) . . ?
C24 C23 C22 123.53(17) . . ?
C24 C23 Cl1 116.62(15) . . ?
C22 C23 Cl1 119.85(14) . . ?
C25 C24 C23 117.94(18) . . ?
C25 C24 H24 124.1(11) . . ?
C23 C24 H24 117.9(11) . . ?
C24 C25 C26 121.32(19) . . ?
C24 C25 H25 119.2(12) . . ?
C26 C25 H25 119.4(12) . . ?
C25 C26 C21 120.07(18) . . ?
C25 C26 H26 121.1(12) . . ?
C21 C26 H26 118.9(12) . . ?
C22 C27 H271 110.7(15) . . ?
C22 C27 H272 110.2(12) . . ?
H271 C27 H272 106.8(18) . . ?
C22 C27 H273 115.1(12) . . ?
H271 C27 H273 109(2) . . ?
H272 C27 H273 104.6(17) . . ?
C2 N1 C5 108.50(13) . . ?
C2 N1 H1 110.6(12) . . ?
C5 N1 H1 109.9(13) . . ?
C2 N1 H2 110.8(11) . . ?
C5 N1 H2 109.8(11) . . ?
H1 N1 H2 107.3(16) . . ?
O2 C1 O1 125.54(15) . . ?
O2 C1 C2 118.82(13) . . ?
O1 C1 C2 115.57(13) . . ?
N1 C2 C1 109.06(12) . . ?
N1 C2 C3 103.38(13) . . ?
C1 C2 C3 111.24(13) . . ?
N1 C2 H21 109.1(11) . . ?
C1 C2 H21 111.1(11) . . ?
C3 C2 H21 112.6(10) . . ?
C4 C3 C2 102.65(13) . . ?
C4 C3 H31 110.3(10) . . ?
C2 C3 H31 108.1(10) . . ?
C4 C3 H32 115.2(11) . . ?
C2 C3 H32 110.0(11) . . ?
H31 C3 H32 110.2(14) . . ?
C5 C4 C3 103.54(14) . . ?
C5 C4 H41 109.7(11) . . ?
C3 C4 H41 113.1(10) . . ?
C5 C4 H42 108.0(10) . . ?
C3 C4 H42 110.4(10) . . ?
H41 C4 H42 111.7(15) . . ?
N1 C5 C4 104.91(13) . . ?
N1 C5 H51 104.8(11) . . ?
C4 C5 H51 111.9(11) . . ?
N1 C5 H52 109.4(11) . . ?
C4 C5 H52 115.4(12) . . ?
H51 C5 H52 109.7(17) . . ?

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
O12 C11 C12 C13 179.87(16) . . . . ?
O11 C11 C12 C13 -0.7(2) . . . . ?
O12 C11 C12 C16 -2.2(3) . . . . ?
O11 C11 C12 C16 177.27(14) . . . . ?
C16 C12 C13 C14 1.3(2) . . . . ?
C11 C12 C13 C14 179.36(16) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C16 N11 C15 C14 -0.4(3) . . . . ?
C13 C14 C15 N11 -1.7(3) . . . . ?
C15 N11 C16 N12 -176.84(15) . . . . ?
C15 N11 C16 C12 3.1(2) . . . . ?
C21 N12 C16 N11 6.5(3) . . . . ?
C21 N12 C16 C12 -173.44(16) . . . . ?
C13 C12 C16 N11 -3.5(2) . . . . ?
C11 C12 C16 N11 178.48(15) . . . . ?
C13 C12 C16 N12 176.38(15) . . . . ?
C11 C12 C16 N12 -1.6(2) . . . . ?
C16 N12 C21 C26 -0.2(3) . . . . ?
C16 N12 C21 C22 179.57(16) . . . . ?
C26 C21 C22 C23 -0.8(2) . . . . ?
N12 C21 C22 C23 179.37(15) . . . . ?
C26 C21 C22 C27 178.48(17) . . . . ?
N12 C21 C22 C27 -1.3(2) . . . . ?
C21 C22 C23 C24 -1.0(3) . . . . ?
C27 C22 C23 C24 179.67(18) . . . . ?
C21 C22 C23 Cl1 178.91(12) . . . . ?
C27 C22 C23 Cl1 -0.4(2) . . . . ?
C22 C23 C24 C25 2.1(3) . . . . ?
Cl1 C23 C24 C25 -177.86(15) . . . . ?
C23 C24 C25 C26 -1.3(3) . . . . ?
C24 C25 C26 C21 -0.5(3) . . . . ?
N12 C21 C26 C25 -178.62(17) . . . . ?
C22 C21 C26 C25 1.6(3) . . . . ?
C5 N1 C2 C1 97.61(15) . . . . ?
C5 N1 C2 C3 -20.82(18) . . . . ?
O2 C1 C2 N1 -8.2(2) . . . . ?
O1 C1 C2 N1 174.52(13) . . . . ?
O2 C1 C2 C3 105.18(17) . . . . ?
O1 C1 C2 C3 -72.10(18) . . . . ?
N1 C2 C3 C4 37.75(17) . . . . ?
C1 C2 C3 C4 -79.15(16) . . . . ?
C2 C3 C4 C5 -40.72(18) . . . . ?
C2 N1 C5 C4 -4.28(19) . . . . ?
C3 C4 C5 N1 27.83(19) . . . . ?

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
O11 H11 O1 0.90(2) 1.68(2) 2.5661(17) 169(2) .
N12 H12 O12 0.892(18) 1.901(18) 2.6836(19) 145.5(15) .
N1 H1 O1 0.90(2) 1.83(2) 2.7190(18) 167.4(18) 1_655
N1 H2 O2 0.932(19) 1.976(19) 2.7980(17) 146.1(16) 4_556

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.031
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 1863146'
_audit_update_record             
;
2018-08-21 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F3 N2 O2, C5 H9 N O2'
_chemical_formula_sum            'C18 H18 F3 N3 O4'
_chemical_formula_weight         397.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   11.8073(17)
_cell_length_b                   5.8122(8)
_cell_length_c                   13.3488(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.844(2)
_cell_angle_gamma                90.00
_cell_volume                     907.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4280
_cell_measurement_theta_min      2.161
_cell_measurement_theta_max      30.384

_exptl_crystal_description       pprism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(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 SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10012
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         29.00
_reflns_number_total             2624
_reflns_number_gt                2403
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0738P)²+0.6031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2624
_refine_ls_number_parameters     275
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration syn

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4214(2) 0.9038(6) 0.2568(2) 0.0268(6) Uani 1 1 d . . .
H11 H 0.486(4) 0.926(10) 0.230(4) 0.051(14) Uiso 1 1 d . . .
N2 N 0.2560(2) 0.6813(6) 0.2256(2) 0.0280(6) Uani 1 1 d . . .
O1 O 0.5844(2) 0.4429(5) 0.0827(2) 0.0350(6) Uani 1 1 d . . .
H1 H 0.671(5) 0.464(15) 0.078(5) 0.09(2) Uiso 1 1 d . . .
O2 O 0.5949(2) 0.7849(5) 0.1583(2) 0.0360(6) Uani 1 1 d . . .
C11 C 0.4211(2) 0.5721(6) 0.1479(2) 0.0214(6) Uani 1 1 d . . .
C12 C 0.3643(2) 0.7189(6) 0.2102(2) 0.0217(6) Uani 1 1 d . . .
C13 C 0.2034(3) 0.4959(7) 0.1837(3) 0.0301(7) Uani 1 1 d . . .
H13 H 0.1266 0.4704 0.1948 0.036 Uiso 1 1 calc R . .
C14 C 0.2518(3) 0.3380(7) 0.1255(2) 0.0278(6) Uani 1 1 d . . .
H14 H 0.2110 0.2056 0.0991 0.033 Uiso 1 1 calc R . .
C15 C 0.3627(3) 0.3801(6) 0.1069(2) 0.0242(6) Uani 1 1 d . . .
H15 H 0.3987 0.2769 0.0660 0.029 Uiso 1 1 calc R . .
C16 C 0.5411(3) 0.6136(6) 0.1306(2) 0.0250(6) Uani 1 1 d . . .
C21 C 0.3917(3) 1.0498(6) 0.3314(2) 0.0248(6) Uani 1 1 d . . .
C22 C 0.3022(3) 1.0085(7) 0.3883(2) 0.0287(7) Uani 1 1 d . . .
H22 H 0.2553 0.8760 0.3758 0.034 Uiso 1 1 calc R . .
C23 C 0.2833(3) 1.1639(7) 0.4630(3) 0.0330(8) Uani 1 1 d . A .
C24 C 0.3481(3) 1.3628(7) 0.4818(3) 0.0344(8) Uani 1 1 d . . .
H24 H 0.3316 1.4702 0.5314 0.041 Uiso 1 1 calc R . .
C25 C 0.4372(3) 1.4005(6) 0.4267(3) 0.0340(8) Uani 1 1 d . . .
H25 H 0.4835 1.5339 0.4393 0.041 Uiso 1 1 calc R . .
C26 C 0.4595(3) 1.2460(6) 0.3534(2) 0.0277(7) Uani 1 1 d . . .
H26 H 0.5221 1.2732 0.3171 0.033 Uiso 1 1 calc R . .
C27 C 0.1889(3) 1.1172(6) 0.5253(3) 0.0494(11) Uani 1 1 d D . .
F1 F 0.1344(5) 0.9174(8) 0.5048(5) 0.0417(12) Uiso 0.49 1 d PD A 1
F2 F 0.1070(5) 1.2833(11) 0.5031(5) 0.0504(15) Uiso 0.49 1 d PD A 1
F3 F 0.2234(6) 1.1297(14) 0.6245(3) 0.0399(15) Uiso 0.49 1 d PD A 1
F4 F 0.1686(7) 0.8834(8) 0.5328(6) 0.0421(18) Uiso 0.34 1 d PD A 2
F5 F 0.2172(9) 1.1875(16) 0.6214(5) 0.055(3) Uiso 0.34 1 d PD A 2
F6 F 0.0853(6) 1.2078(15) 0.4950(7) 0.060(3) Uiso 0.34 1 d PD A 2
F7 F 0.1124(14) 0.967(3) 0.4818(14) 0.074(5) Uiso 0.17 1 d PD A 3
F8 F 0.1321(16) 1.313(2) 0.5392(15) 0.074(5) Uiso 0.17 1 d PD A 3
F9 F 0.2310(16) 1.039(3) 0.6174(8) 0.074(5) Uiso 0.17 1 d PD A 3
N3 N 0.9037(2) -0.0787(5) 0.1079(2) 0.0237(5) Uani 1 1 d . . .
H31 H 0.866(3) -0.212(8) 0.091(3) 0.024(7) Uiso 1 1 d . . .
H32 H 0.948(3) -0.044(8) 0.054(3) 0.024(7) Uiso 1 1 d . . .
O3 O 0.7959(2) 0.5026(4) 0.0705(2) 0.0296(5) Uani 1 1 d . . .
O4 O 0.9577(2) 0.3305(5) 0.0443(2) 0.0308(5) Uani 1 1 d . . .
C30 C 0.8187(2) 0.1106(5) 0.1151(2) 0.0187(5) Uani 1 1 d . . .
H30A H 0.7419 0.0676 0.0787 0.022 Uiso 1 1 calc R . .
C31 C 0.8150(3) 0.1326(6) 0.2289(2) 0.0265(6) Uani 1 1 d . . .
H31A H 0.7906 0.2888 0.2465 0.032 Uiso 1 1 calc R . .
H31B H 0.7624 0.0180 0.2523 0.032 Uiso 1 1 calc R . .
C32 C 0.9381(3) 0.0861(8) 0.2741(3) 0.0347(8) Uani 1 1 d . . .
H32A H 0.9865 0.2236 0.2692 0.042 Uiso 1 1 calc R . .
H32B H 0.9430 0.0398 0.3460 0.042 Uiso 1 1 calc R . .
C33 C 0.9736(3) -0.1087(8) 0.2102(3) 0.0375(8) Uani 1 1 d . . .
H33A H 1.0563 -0.0995 0.2049 0.045 Uiso 1 1 calc R . .
H33B H 0.9575 -0.2593 0.2398 0.045 Uiso 1 1 calc R . .
C34 C 0.8623(2) 0.3318(5) 0.0715(2) 0.0200(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.372(4) . ?
N1 C21 1.390(4) . ?
N1 H11 0.89(5) . ?
N2 C13 1.328(5) . ?
N2 C12 1.341(4) . ?
O1 C16 1.320(4) . ?
O1 H1 1.04(6) . ?
O2 C16 1.212(4) . ?
C11 C15 1.384(4) . ?
C11 C12 1.421(4) . ?
C11 C16 1.486(4) . ?
C13 C14 1.377(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 C26 1.401(4) . ?
C21 C22 1.404(4) . ?
C22 C23 1.386(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(5) . ?
C23 C27 1.504(5) . ?
C24 C25 1.381(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 F7 1.332(6) . ?
C27 F3 1.334(5) . ?
C27 F1 1.338(5) . ?
C27 F6 1.341(5) . ?
C27 F9 1.342(6) . ?
C27 F5 1.344(5) . ?
C27 F8 1.348(6) . ?
C27 F2 1.369(5) . ?
C27 F4 1.386(5) . ?
N3 C30 1.500(4) . ?
N3 C33 1.506(5) . ?
N3 H31 0.91(5) . ?
N3 H32 0.97(4) . ?
O3 C34 1.264(4) . ?
O4 C34 1.230(4) . ?
C30 C34 1.528(4) . ?
C30 C31 1.531(4) . ?
C30 H30A 1.0000 . ?
C31 C32 1.521(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.511(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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
C12 N1 C21 130.3(3) . . ?
C12 N1 H11 109(4) . . ?
C21 N1 H11 121(4) . . ?
C13 N2 C12 118.0(3) . . ?
C16 O1 H1 113(4) . . ?
C15 C11 C12 117.8(3) . . ?
C15 C11 C16 120.2(3) . . ?
C12 C11 C16 122.0(3) . . ?
N2 C12 N1 118.6(3) . . ?
N2 C12 C11 121.8(3) . . ?
N1 C12 C11 119.6(3) . . ?
N2 C13 C14 124.9(3) . . ?
N2 C13 H13 117.6 . . ?
C14 C13 H13 117.6 . . ?
C13 C14 C15 117.3(3) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C11 C15 C14 120.2(3) . . ?
C11 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
O2 C16 O1 122.9(3) . . ?
O2 C16 C11 123.9(3) . . ?
O1 C16 C11 113.2(3) . . ?
N1 C21 C26 117.0(3) . . ?
N1 C21 C22 124.5(3) . . ?
C26 C21 C22 118.5(3) . . ?
C23 C22 C21 119.0(3) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 122.2(3) . . ?
C22 C23 C27 119.0(3) . . ?
C24 C23 C27 118.8(3) . . ?
C25 C24 C23 118.5(3) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C26 C25 C24 120.5(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 121.3(3) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
F3 C27 F1 108.9(4) . . ?
F7 C27 F9 108.7(6) . . ?
F6 C27 F5 105.4(5) . . ?
F7 C27 F8 107.2(6) . . ?
F9 C27 F8 106.8(6) . . ?
F3 C27 F2 106.7(4) . . ?
F1 C27 F2 105.2(4) . . ?
F6 C27 F4 104.4(5) . . ?
F5 C27 F4 104.6(5) . . ?
F7 C27 C23 112.8(10) . . ?
F3 C27 C23 113.0(4) . . ?
F1 C27 C23 114.6(4) . . ?
F6 C27 C23 118.5(5) . . ?
F9 C27 C23 111.0(10) . . ?
F5 C27 C23 111.5(6) . . ?
F8 C27 C23 110.1(10) . . ?
F2 C27 C23 108.0(4) . . ?
F4 C27 C23 111.4(4) . . ?
C30 N3 C33 108.4(3) . . ?
C30 N3 H31 109(3) . . ?
C33 N3 H31 108(3) . . ?
C30 N3 H32 109(3) . . ?
C33 N3 H32 114(2) . . ?
H31 N3 H32 107(3) . . ?
N3 C30 C34 109.3(2) . . ?
N3 C30 C31 103.6(2) . . ?
C34 C30 C31 111.3(3) . . ?
N3 C30 H30A 110.8 . . ?
C34 C30 H30A 110.8 . . ?
C31 C30 H30A 110.8 . . ?
C32 C31 C30 102.9(2) . . ?
C32 C31 H31A 111.2 . . ?
C30 C31 H31A 111.2 . . ?
C32 C31 H31B 111.2 . . ?
C30 C31 H31B 111.2 . . ?
H31A C31 H31B 109.1 . . ?
C33 C32 C31 103.5(3) . . ?
C33 C32 H32A 111.1 . . ?
C31 C32 H32A 111.1 . . ?
C33 C32 H32B 111.1 . . ?
C31 C32 H32B 111.1 . . ?
H32A C32 H32B 109.0 . . ?
N3 C33 C32 105.4(3) . . ?
N3 C33 H33A 110.7 . . ?
C32 C33 H33A 110.7 . . ?
N3 C33 H33B 110.7 . . ?
C32 C33 H33B 110.7 . . ?
H33A C33 H33B 108.8 . . ?
O4 C34 O3 126.3(3) . . ?
O4 C34 C30 118.5(3) . . ?
O3 C34 C30 115.2(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
C13 N2 C12 N1 -177.0(3) . . . . ?
C13 N2 C12 C11 2.5(5) . . . . ?
C21 N1 C12 N2 10.2(5) . . . . ?
C21 N1 C12 C11 -169.3(3) . . . . ?
C15 C11 C12 N2 -3.1(4) . . . . ?
C16 C11 C12 N2 179.9(3) . . . . ?
C15 C11 C12 N1 176.4(3) . . . . ?
C16 C11 C12 N1 -0.6(4) . . . . ?
C12 N2 C13 C14 0.1(5) . . . . ?
N2 C13 C14 C15 -2.0(5) . . . . ?
C12 C11 C15 C14 1.1(4) . . . . ?
C16 C11 C15 C14 178.2(3) . . . . ?
C13 C14 C15 C11 1.3(5) . . . . ?
C15 C11 C16 O2 174.9(3) . . . . ?
C12 C11 C16 O2 -8.1(5) . . . . ?
C15 C11 C16 O1 -5.9(4) . . . . ?
C12 C11 C16 O1 171.1(3) . . . . ?
C12 N1 C21 C26 -170.5(3) . . . . ?
C12 N1 C21 C22 12.2(5) . . . . ?
N1 C21 C22 C23 178.0(3) . . . . ?
C26 C21 C22 C23 0.8(5) . . . . ?
C21 C22 C23 C24 1.7(5) . . . . ?
C21 C22 C23 C27 -178.8(3) . . . . ?
C22 C23 C24 C25 -2.7(5) . . . . ?
C27 C23 C24 C25 177.8(3) . . . . ?
C23 C24 C25 C26 1.2(5) . . . . ?
C24 C25 C26 C21 1.2(5) . . . . ?
N1 C21 C26 C25 -179.6(3) . . . . ?
C22 C21 C26 C25 -2.2(5) . . . . ?
C22 C23 C27 F7 -18.9(10) . . . . ?
C24 C23 C27 F7 160.6(10) . . . . ?
C22 C23 C27 F3 128.7(5) . . . . ?
C24 C23 C27 F3 -51.8(6) . . . . ?
C22 C23 C27 F1 3.3(6) . . . . ?
C24 C23 C27 F1 -177.3(4) . . . . ?
C22 C23 C27 F6 -92.8(6) . . . . ?
C24 C23 C27 F6 86.7(6) . . . . ?
C22 C23 C27 F9 103.4(10) . . . . ?
C24 C23 C27 F9 -77.1(10) . . . . ?
C22 C23 C27 F5 144.6(5) . . . . ?
C24 C23 C27 F5 -35.9(6) . . . . ?
C22 C23 C27 F8 -138.6(9) . . . . ?
C24 C23 C27 F8 40.9(10) . . . . ?
C22 C23 C27 F2 -113.6(5) . . . . ?
C24 C23 C27 F2 65.9(5) . . . . ?
C22 C23 C27 F4 28.2(5) . . . . ?
C24 C23 C27 F4 -152.3(5) . . . . ?
C33 N3 C30 C34 100.7(3) . . . . ?
C33 N3 C30 C31 -18.0(3) . . . . ?
N3 C30 C31 C32 35.8(3) . . . . ?
C34 C30 C31 C32 -81.5(3) . . . . ?
C30 C31 C32 C33 -40.3(3) . . . . ?
C30 N3 C33 C32 -6.9(4) . . . . ?
C31 C32 C33 N3 29.2(4) . . . . ?
N3 C30 C34 O4 -4.4(4) . . . . ?
C31 C30 C34 O4 109.4(3) . . . . ?
N3 C30 C34 O3 177.9(3) . . . . ?
C31 C30 C34 O3 -68.4(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
N1 H11 O2 0.89(5) 1.89(5) 2.672(4) 145(5) .
O1 H1 O3 1.04(6) 1.50(6) 2.549(3) 178(8) .
N3 H31 O3 0.91(5) 1.85(5) 2.760(4) 174(4) 1_545
N3 H32 O4 0.97(4) 1.97(4) 2.827(3) 146(4) 2_745

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1863145'
_audit_update_record             
;
2018-08-21 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 Cl2 N O2, C5 H9 N O2'
_chemical_formula_sum            'C19 H20 Cl2 N2 O4'
_chemical_formula_weight         411.27

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           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   9.2716(9)
_cell_length_b                   5.2277(5)
_cell_length_c                   20.3473(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.235(1)
_cell_angle_gamma                90.00
_cell_volume                     963.82(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4496
_cell_measurement_theta_min      2.764
_cell_measurement_theta_max      30.048

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8770
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(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 SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9301
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4183
_reflns_number_gt                3926
_reflns_threshold_expression     I>2σ(I)
_chemical_absolute_configuration rmad

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0311P)²+0.1731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_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   0.07(4)
_refine_ls_number_reflns         4183
_refine_ls_number_parameters     304
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0650
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.046
_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 0.39299(4) 0.45637(8) 0.964059(19) 0.02910(10) Uani 1 1 d . . .
Cl2 Cl 0.03668(5) 0.99203(11) 0.76648(3) 0.04824(15) Uani 1 1 d . . .
N1 N 0.28090(15) 0.6202(3) 0.82051(7) 0.0291(3) Uani 1 1 d . . .
O1 O 0.19396(13) 0.5104(3) 0.68092(6) 0.0402(3) Uani 1 1 d . . .
O2 O 0.33638(15) 0.3100(3) 0.62204(6) 0.0377(3) Uani 1 1 d . . .
C11 C 0.43390(17) 0.6146(3) 0.82135(8) 0.0249(3) Uani 1 1 d . . .
C12 C 0.53068(19) 0.7891(4) 0.85959(8) 0.0277(4) Uani 1 1 d . . .
C13 C 0.68074(19) 0.7780(4) 0.86097(9) 0.0319(4) Uani 1 1 d . . .
C14 C 0.73576(18) 0.5961(4) 0.82373(9) 0.0328(4) Uani 1 1 d . . .
C15 C 0.64005(18) 0.4246(4) 0.78480(9) 0.0300(4) Uani 1 1 d . . .
C16 C 0.48854(17) 0.4324(4) 0.78254(7) 0.0263(3) Uani 1 1 d . . .
C17 C 0.3877(2) 0.2401(4) 0.73973(9) 0.0312(4) Uani 1 1 d . . .
C18 C 0.29544(19) 0.3657(3) 0.67800(9) 0.0298(4) Uani 1 1 d . . .
C21 C 0.22244(18) 0.7509(4) 0.86837(9) 0.0265(3) Uani 1 1 d . . .
C22 C 0.26854(17) 0.7022(3) 0.93754(9) 0.0252(3) Uani 1 1 d . . .
C23 C 0.21632(19) 0.8379(4) 0.98590(10) 0.0331(4) Uani 1 1 d . . .
C24 C 0.1084(2) 1.0212(4) 0.96648(11) 0.0396(5) Uani 1 1 d . . .
C25 C 0.05257(19) 1.0648(4) 0.89895(12) 0.0404(5) Uani 1 1 d . . .
C26 C 0.10929(17) 0.9328(4) 0.85120(9) 0.0337(4) Uani 1 1 d . . .
H1 H 0.225(2) 0.616(4) 0.7817(11) 0.036(6) Uiso 1 1 d . . .
H2 H 0.279(3) 0.410(6) 0.5846(14) 0.080(9) Uiso 1 1 d . . .
H12 H 0.490(2) 0.913(4) 0.8842(9) 0.032(5) Uiso 1 1 d . . .
H13 H 0.746(2) 0.895(4) 0.8897(9) 0.032(5) Uiso 1 1 d . . .
H14 H 0.840(2) 0.591(4) 0.8275(10) 0.041(6) Uiso 1 1 d . . .
H15 H 0.676(2) 0.299(4) 0.7623(10) 0.029(5) Uiso 1 1 d . . .
H23 H 0.257(2) 0.804(4) 1.0346(11) 0.040(6) Uiso 1 1 d . . .
H24 H 0.072(2) 1.118(4) 1.0008(10) 0.035(5) Uiso 1 1 d . . .
H25 H -0.016(3) 1.188(5) 0.8864(11) 0.052(7) Uiso 1 1 d . . .
H17 H 0.448(2) 0.096(4) 0.7260(10) 0.038(6) Uiso 1 1 d . . .
H18 H 0.317(2) 0.166(4) 0.7646(10) 0.032(5) Uiso 1 1 d . . .
N2 N 0.08698(15) -0.0018(3) 0.40543(7) 0.0234(3) Uani 1 1 d . A .
O3 O 0.04644(13) 0.4910(2) 0.41613(5) 0.0304(3) Uani 1 1 d . A .
O4 O 0.17896(15) 0.5298(2) 0.52019(6) 0.0356(3) Uani 1 1 d . A .
C30 C 0.18289(19) -0.0079(4) 0.35451(9) 0.0363(4) Uani 1 1 d D . .
H30C H 0.1824 0.1580 0.3310 0.044 Uiso 0.164(5) 1 calc PR A 2
H30D H 0.1536 -0.1462 0.3211 0.044 Uiso 0.164(5) 1 calc PR A 2
H30A H 0.1354 0.0780 0.3140 0.044 Uiso 0.836(5) 1 d PR A 1
H30B H 0.2034 -0.1811 0.3437 0.044 Uiso 0.836(5) 1 d PR A 1
C31 C 0.3238(3) 0.1280(6) 0.38693(14) 0.0475(7) Uani 0.836(5) 1 d P A 1
H31A H 0.3189 0.3119 0.3750 0.057 Uiso 0.836(5) 1 calc PR A 1
H31B H 0.4101 0.0503 0.3731 0.057 Uiso 0.836(5) 1 calc PR A 1
C35 C 0.3295(11) -0.061(3) 0.4005(4) 0.0475(7) Uani 0.164(5) 1 d PD A 2
H35A H 0.3400 -0.2455 0.4112 0.057 Uiso 0.164(5) 1 calc PR A 2
H35B H 0.4113 -0.0082 0.3790 0.057 Uiso 0.164(5) 1 calc PR A 2
C32 C 0.33203(19) 0.0904(4) 0.46227(10) 0.0405(5) Uani 1 1 d D . .
H32C H 0.3781 0.2594 0.4590 0.049 Uiso 0.164(5) 1 calc PR A 2
H32D H 0.3890 -0.0004 0.5021 0.049 Uiso 0.164(5) 1 calc PR A 2
H32A H 0.3939 0.2168 0.4885 0.049 Uiso 0.836(5) 1 d PR A 1
H32B H 0.3684 -0.0770 0.4765 0.049 Uiso 0.836(5) 1 d PR A 1
C33 C 0.17203(17) 0.1223(3) 0.46807(8) 0.0234(3) Uani 1 1 d . A .
C34 C 0.12773(18) 0.4039(3) 0.46796(8) 0.0244(4) Uani 1 1 d . . .
H21 H 0.001(2) 0.081(4) 0.3902(10) 0.030(5) Uiso 1 1 d . . .
H22 H 0.064(2) -0.172(4) 0.4117(10) 0.029(5) Uiso 1 1 d . . .
H33 H 0.1516(18) 0.039(4) 0.5063(9) 0.022(4) 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
Cl1 C22 1.7351(17) . ?
Cl2 C26 1.7404(18) . ?
N1 C21 1.390(2) . ?
N1 C11 1.415(2) . ?
N1 H1 0.85(2) . ?
O1 C18 1.219(2) . ?
O2 C18 1.307(2) . ?
O2 H2 0.98(3) . ?
C11 C12 1.395(2) . ?
C11 C16 1.399(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.94(2) . ?
C13 C14 1.379(3) . ?
C13 H13 0.96(2) . ?
C14 C15 1.386(3) . ?
C14 H14 0.95(2) . ?
C15 C16 1.396(2) . ?
C15 H15 0.90(2) . ?
C16 C17 1.516(2) . ?
C17 C18 1.512(2) . ?
C17 H17 1.01(2) . ?
C17 H18 0.99(2) . ?
C21 C26 1.404(2) . ?
C21 C22 1.405(2) . ?
C22 C23 1.381(3) . ?
C23 C24 1.381(3) . ?
C23 H23 1.00(2) . ?
C24 C25 1.381(3) . ?
C24 H24 0.98(2) . ?
C25 C26 1.383(3) . ?
C25 H25 0.91(2) . ?
N2 C33 1.497(2) . ?
N2 C30 1.502(2) . ?
N2 H21 0.90(2) . ?
N2 H22 0.93(2) . ?
O3 C34 1.2451(19) . ?
O4 C34 1.2545(19) . ?
C30 C35 1.504(10) . ?
C30 C31 1.510(3) . ?
C30 H30C 0.9900 . ?
C30 H30D 0.9900 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C31 C32 1.531(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C35 C32 1.481(9) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C32 C33 1.522(2) . ?
C32 H32C 0.9900 . ?
C32 H32D 0.9900 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9601 . ?
C33 C34 1.528(2) . ?
C33 H33 0.945(18) . ?

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 N1 C11 122.70(14) . . ?
C21 N1 H1 114.1(14) . . ?
C11 N1 H1 115.3(14) . . ?
C18 O2 H2 110.2(16) . . ?
C12 C11 C16 119.54(15) . . ?
C12 C11 N1 121.18(16) . . ?
C16 C11 N1 119.28(15) . . ?
C13 C12 C11 120.52(17) . . ?
C13 C12 H12 121.8(12) . . ?
C11 C12 H12 117.7(12) . . ?
C14 C13 C12 120.26(17) . . ?
C14 C13 H13 120.9(11) . . ?
C12 C13 H13 118.8(11) . . ?
C13 C14 C15 119.57(16) . . ?
C13 C14 H14 117.4(14) . . ?
C15 C14 H14 122.9(14) . . ?
C14 C15 C16 121.17(18) . . ?
C14 C15 H15 120.0(12) . . ?
C16 C15 H15 118.7(13) . . ?
C15 C16 C11 118.91(16) . . ?
C15 C16 C17 119.54(17) . . ?
C11 C16 C17 121.53(14) . . ?
C18 C17 C16 111.16(15) . . ?
C18 C17 H17 110.0(11) . . ?
C16 C17 H17 110.1(11) . . ?
C18 C17 H18 106.1(11) . . ?
C16 C17 H18 111.1(12) . . ?
H17 C17 H18 108.2(17) . . ?
O1 C18 O2 123.40(16) . . ?
O1 C18 C17 122.42(16) . . ?
O2 C18 C17 114.16(16) . . ?
N1 C21 C26 122.69(16) . . ?
N1 C21 C22 122.13(16) . . ?
C26 C21 C22 115.12(16) . . ?
C23 C22 C21 122.87(17) . . ?
C23 C22 Cl1 117.98(14) . . ?
C21 C22 Cl1 119.13(13) . . ?
C22 C23 C24 119.64(18) . . ?
C22 C23 H23 120.0(13) . . ?
C24 C23 H23 120.4(13) . . ?
C25 C24 C23 119.68(19) . . ?
C25 C24 H24 120.8(12) . . ?
C23 C24 H24 119.5(12) . . ?
C24 C25 C26 119.90(18) . . ?
C24 C25 H25 119.4(15) . . ?
C26 C25 H25 120.5(15) . . ?
C25 C26 C21 122.57(17) . . ?
C25 C26 Cl2 118.83(14) . . ?
C21 C26 Cl2 118.60(15) . . ?
C33 N2 C30 108.32(13) . . ?
C33 N2 H21 110.6(13) . . ?
C30 N2 H21 112.6(12) . . ?
C33 N2 H22 113.0(12) . . ?
C30 N2 H22 105.0(12) . . ?
H21 N2 H22 107.2(18) . . ?
N2 C30 C35 99.4(4) . . ?
N2 C30 C31 105.81(15) . . ?
N2 C30 H30C 111.9 . . ?
C35 C30 H30C 111.9 . . ?
N2 C30 H30D 111.9 . . ?
C35 C30 H30D 111.9 . . ?
H30C C30 H30D 109.6 . . ?
N2 C30 H30A 110.6 . . ?
C31 C30 H30A 110.6 . . ?
N2 C30 H30B 110.6 . . ?
C31 C30 H30B 110.4 . . ?
H30A C30 H30B 108.8 . . ?
C30 C31 C32 103.42(19) . . ?
C30 C31 H31A 111.1 . . ?
C32 C31 H31A 111.1 . . ?
C30 C31 H31B 111.1 . . ?
C32 C31 H31B 111.1 . . ?
H31A C31 H31B 109.0 . . ?
C32 C35 C30 106.2(8) . . ?
C32 C35 H35A 110.5 . . ?
C30 C35 H35A 110.5 . . ?
C32 C35 H35B 110.5 . . ?
C30 C35 H35B 110.5 . . ?
H30B C35 H35B 107.7 . . ?
H35A C35 H35B 108.7 . . ?
C35 C32 C33 106.5(4) . . ?
C33 C32 C31 102.75(15) . . ?
C35 C32 H32C 110.4 . . ?
C33 C32 H32C 110.4 . . ?
C35 C32 H32D 110.4 . . ?
C33 C32 H32D 110.4 . . ?
H32C C32 H32D 108.6 . . ?
C33 C32 H32A 111.0 . . ?
C31 C32 H32A 111.5 . . ?
C33 C32 H32B 111.2 . . ?
C31 C32 H32B 111.0 . . ?
H32A C32 H32B 109.2 . . ?
N2 C33 C32 103.45(14) . . ?
N2 C33 C34 108.87(13) . . ?
C32 C33 C34 111.82(15) . . ?
N2 C33 H33 109.9(11) . . ?
C32 C33 H33 112.5(10) . . ?
C34 C33 H33 110.1(11) . . ?
O3 C34 O4 125.33(15) . . ?
O3 C34 C33 117.88(14) . . ?
O4 C34 C33 116.77(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 N1 C11 C12 -16.2(2) . . . . ?
C21 N1 C11 C16 164.52(16) . . . . ?
C16 C11 C12 C13 -2.0(2) . . . . ?
N1 C11 C12 C13 178.70(16) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C11 -1.1(2) . . . . ?
C14 C15 C16 C17 -179.56(16) . . . . ?
C12 C11 C16 C15 2.1(2) . . . . ?
N1 C11 C16 C15 -178.62(15) . . . . ?
C12 C11 C16 C17 -179.50(15) . . . . ?
N1 C11 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 C18 -107.97(18) . . . . ?
C11 C16 C17 C18 73.6(2) . . . . ?
C16 C17 C18 O1 -71.9(2) . . . . ?
C16 C17 C18 O2 106.60(18) . . . . ?
C11 N1 C21 C26 126.29(18) . . . . ?
C11 N1 C21 C22 -56.4(2) . . . . ?
N1 C21 C22 C23 177.11(16) . . . . ?
C26 C21 C22 C23 -5.4(2) . . . . ?
N1 C21 C22 Cl1 -4.6(2) . . . . ?
C26 C21 C22 Cl1 172.96(12) . . . . ?
C21 C22 C23 C24 3.5(3) . . . . ?
Cl1 C22 C23 C24 -174.86(14) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 -2.7(3) . . . . ?
C24 C25 C26 C21 0.6(3) . . . . ?
C24 C25 C26 Cl2 -179.98(15) . . . . ?
N1 C21 C26 C25 -179.20(17) . . . . ?
C22 C21 C26 C25 3.3(2) . . . . ?
N1 C21 C26 Cl2 1.4(2) . . . . ?
C22 C21 C26 Cl2 -176.11(12) . . . . ?
C33 N2 C30 C35 37.3(7) . . . . ?
C33 N2 C30 C31 -2.9(2) . . . . ?
N2 C30 C31 C32 26.2(2) . . . . ?
C35 C30 C31 C32 -59.6(6) . . . . ?
N2 C30 C35 C32 -38.8(10) . . . . ?
C31 C30 C35 C32 64.6(8) . . . . ?
C30 C35 C32 C33 27.2(11) . . . . ?
C30 C35 C32 C31 -63.0(8) . . . . ?
C30 C31 C32 C35 61.2(6) . . . . ?
C30 C31 C32 C33 -39.4(2) . . . . ?
C30 N2 C33 C32 -21.64(19) . . . . ?
C30 N2 C33 C34 97.41(16) . . . . ?
C35 C32 C33 N2 -3.5(7) . . . . ?
C31 C32 C33 N2 37.4(2) . . . . ?
C35 C32 C33 C34 -120.5(7) . . . . ?
C31 C32 C33 C34 -79.6(2) . . . . ?
N2 C33 C34 O3 -7.7(2) . . . . ?
C32 C33 C34 O3 105.96(18) . . . . ?
N2 C33 C34 O4 173.48(14) . . . . ?
C32 C33 C34 O4 -72.85(19) . . . . ?

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
N1 H1 O1 0.85(2) 2.08(2) 2.8418(19) 148.2(19) .
O2 H2 O4 0.98(3) 1.57(3) 2.5423(18) 171(3) .
N2 H21 O1 0.90(2) 2.094(19) 2.8170(18) 136.4(18) 2_546
N2 H22 O3 0.93(2) 1.78(2) 2.6932(19) 169.9(18) 1_545

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.033
