# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_R20180427A1
_audit_block_doi                 10.5517/ccdc.csd.cc22c7xm
_database_code_depnum_ccdc_archive 'CCDC 1917440'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H40 N4 O4'
_chemical_formula_weight         568.70

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'

_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                   10.186(2)
_cell_length_b                   7.5771(15)
_cell_length_c                   38.191(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2947.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4867
_cell_measurement_theta_min      2.1331
_cell_measurement_theta_max      27.8864

_exptl_crystal_description       prism
_exptl_crystal_colour            transparent
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7211
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17678
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2590
_reflns_number_gt                2266
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0781P)²+0.7684P] 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     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0045(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2590
_refine_ls_number_parameters     205
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1389
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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_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 0.79235(14) 0.1019(2) 0.44316(4) 0.0357(4) Uani 1 1 d . . . . .
O2 O 0.63292(13) 0.04703(18) 0.48144(3) 0.0287(4) Uani 1 1 d . . . . .
N1 N 0.75140(18) 0.0420(3) 0.37619(4) 0.0324(5) Uani 1 1 d D . . . .
C1 C 1.0146(2) -0.0660(3) 0.36802(6) 0.0365(5) Uani 1 1 d . . . . .
H1A H 1.0574 0.0291 0.3811 0.055 Uiso 1 1 calc R U . . .
H1B H 1.0813 -0.1473 0.3590 0.055 Uiso 1 1 calc R U . . .
H1C H 0.9546 -0.1302 0.3835 0.055 Uiso 1 1 calc R U . . .
C2 C 0.9382(2) 0.0115(3) 0.33789(5) 0.0287(5) Uani 1 1 d . . . . .
C3 C 0.9976(2) 0.0355(3) 0.30493(5) 0.0350(5) Uani 1 1 d . . . . .
C4 C 0.9256(2) 0.1131(3) 0.27800(6) 0.0423(6) Uani 1 1 d . . . . .
H4 H 0.9652 0.1288 0.2557 0.051 Uiso 1 1 calc R U . . .
C5 C 0.7978(2) 0.1676(3) 0.28318(6) 0.0385(6) Uani 1 1 d . . . . .
H5 H 0.7511 0.2230 0.2647 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7374(2) 0.1418(3) 0.31521(5) 0.0308(5) Uani 1 1 d . . . . .
H6 H 0.6489 0.1776 0.3186 0.037 Uiso 1 1 calc R U . . .
C7 C 0.8072(2) 0.0630(3) 0.34257(5) 0.0280(5) Uani 1 1 d . . . . .
C8 C 1.1374(3) -0.0229(4) 0.29846(7) 0.0506(7) Uani 1 1 d . . . . .
H8A H 1.1599 -0.0033 0.2738 0.076 Uiso 1 1 calc R U . . .
H8B H 1.1459 -0.1487 0.3040 0.076 Uiso 1 1 calc R U . . .
H8C H 1.1969 0.0453 0.3134 0.076 Uiso 1 1 calc R U . . .
C9 C 0.62427(19) 0.0029(3) 0.38520(5) 0.0258(5) Uani 1 1 d . . . . .
C10 C 0.5324(2) -0.0583(3) 0.36030(5) 0.0300(5) Uani 1 1 d . . . . .
H10 H 0.5595 -0.0750 0.3367 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4051(2) -0.0941(3) 0.36943(6) 0.0345(5) Uani 1 1 d . . . . .
H11 H 0.3458 -0.1365 0.3522 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3614(2) -0.0694(3) 0.40367(5) 0.0332(5) Uani 1 1 d . . . . .
H12 H 0.2718 -0.0874 0.4096 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4512(2) -0.0180(3) 0.42882(5) 0.0268(5) Uani 1 1 d . . . . .
H13 H 0.4226 -0.0051 0.4524 0.032 Uiso 1 1 calc R U . . .
C14 C 0.58305(19) 0.0158(3) 0.42074(5) 0.0241(5) Uani 1 1 d . . . . .
C15 C 0.6746(2) 0.0580(3) 0.45050(5) 0.0244(5) Uani 1 1 d . . . . .
C16 C 0.08907(19) 0.0929(3) 0.47746(5) 0.0268(5) Uani 1 1 d . . . . .
H16A H 0.1629 0.1184 0.4935 0.032 Uiso 1 1 calc R U . . .
H16B H 0.1112 0.1422 0.4542 0.032 Uiso 1 1 calc R U . . .
N2 N -0.03234(16) 0.1783(2) 0.49083(4) 0.0252(4) Uani 1 1 d D . . . .
C17 C -0.0706(2) 0.1041(3) 0.52551(5) 0.0267(5) Uani 1 1 d . . . . .
H17A H -0.1532 0.1595 0.5335 0.032 Uiso 1 1 calc R U . . .
H17B H -0.0014 0.1301 0.5430 0.032 Uiso 1 1 calc R U . . .
H1 H 0.802(2) 0.071(3) 0.3946(5) 0.053(8) Uiso 1 1 d D . . . .
H2A H -0.018(2) 0.2959(15) 0.4936(6) 0.051(8) Uiso 1 1 d D . . . .
H2B H -0.0980(19) 0.160(3) 0.4747(5) 0.059(8) Uiso 1 1 d 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 C15 1.276(2) . ?
O2 C15 1.259(2) . ?
N1 C9 1.372(3) . ?
N1 C7 1.413(3) . ?
C1 C2 1.508(3) . ?
C2 C7 1.401(3) . ?
C2 C3 1.409(3) . ?
C3 C4 1.394(3) . ?
C3 C8 1.511(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.398(3) . ?
C9 C10 1.412(3) . ?
C9 C14 1.424(3) . ?
C10 C11 1.370(3) . ?
C11 C12 1.394(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.402(3) . ?
C14 C15 1.505(3) . ?
C16 N2 1.486(3) . ?
C16 C17 1.509(3) 5_556 ?
N2 C17 1.491(2) . ?
C17 C16 1.509(3) 5_556 ?

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
C9 N1 C7 129.19(17) . . ?
C7 C2 C3 119.17(19) . . ?
C7 C2 C1 120.14(18) . . ?
C3 C2 C1 120.7(2) . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 C8 119.9(2) . . ?
C2 C3 C8 120.9(2) . . ?
C5 C4 C3 121.1(2) . . ?
C4 C5 C6 120.3(2) . . ?
C5 C6 C7 119.7(2) . . ?
C6 C7 C2 120.51(19) . . ?
C6 C7 N1 121.5(2) . . ?
C2 C7 N1 117.87(18) . . ?
N1 C9 C10 121.80(18) . . ?
N1 C9 C14 120.17(17) . . ?
C10 C9 C14 117.97(18) . . ?
C11 C10 C9 121.37(19) . . ?
C10 C11 C12 121.0(2) . . ?
C13 C12 C11 118.5(2) . . ?
C12 C13 C14 122.20(19) . . ?
C13 C14 C9 118.67(18) . . ?
C13 C14 C15 117.82(18) . . ?
C9 C14 C15 123.48(18) . . ?
O2 C15 O1 122.73(18) . . ?
O2 C15 C14 119.08(18) . . ?
O1 C15 C14 118.19(17) . . ?
N2 C16 C17 110.64(16) . 5_556 ?
C16 N2 C17 111.00(15) . . ?
N2 C17 C16 109.84(16) . 5_556 ?

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
C7 C2 C3 C4 1.3(3) . . . . ?
C1 C2 C3 C4 -177.8(2) . . . . ?
C7 C2 C3 C8 -178.2(2) . . . . ?
C1 C2 C3 C8 2.7(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C8 C3 C4 C5 180.0(2) . . . . ?
C3 C4 C5 C6 -1.6(4) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C2 0.7(3) . . . . ?
C5 C6 C7 N1 176.88(19) . . . . ?
C3 C2 C7 C6 -1.9(3) . . . . ?
C1 C2 C7 C6 177.2(2) . . . . ?
C3 C2 C7 N1 -178.22(19) . . . . ?
C1 C2 C7 N1 0.9(3) . . . . ?
C9 N1 C7 C6 36.6(3) . . . . ?
C9 N1 C7 C2 -147.1(2) . . . . ?
C7 N1 C9 C10 13.2(3) . . . . ?
C7 N1 C9 C14 -169.7(2) . . . . ?
N1 C9 C10 C11 -178.9(2) . . . . ?
C14 C9 C10 C11 3.9(3) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -3.9(3) . . . . ?
C11 C12 C13 C14 2.3(3) . . . . ?
C12 C13 C14 C9 2.4(3) . . . . ?
C12 C13 C14 C15 -175.62(19) . . . . ?
N1 C9 C14 C13 177.37(18) . . . . ?
C10 C9 C14 C13 -5.4(3) . . . . ?
N1 C9 C14 C15 -4.8(3) . . . . ?
C10 C9 C14 C15 172.49(18) . . . . ?
C13 C14 C15 O2 5.9(3) . . . . ?
C9 C14 C15 O2 -171.97(18) . . . . ?
C13 C14 C15 O1 -174.82(18) . . . . ?
C9 C14 C15 O1 7.3(3) . . . . ?
C17 C16 N2 C17 57.8(2) 5_556 . . . ?
C16 N2 C17 C16 -57.3(2) . . . 5_556 ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_shelxl
_audit_block_doi                 10.5517/ccdc.csd.cc22c7zp
_database_code_depnum_ccdc_archive 'CCDC 1917442'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 N3 O2'
_chemical_formula_weight         327.42

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'

_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                   7.5360(15)
_cell_length_b                   8.1498(16)
_cell_length_c                   28.440(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.90(3)
_cell_angle_gamma                90
_cell_volume                     1740.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4083
_cell_measurement_theta_min      2.1562
_cell_measurement_theta_max      27.8465

_exptl_crystal_description       prism
_exptl_crystal_colour            transparent
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8695
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20189
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         27.902
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4152
_reflns_number_gt                3478
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0750P)²+0.4915P] 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     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4152
_refine_ls_number_parameters     236
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.37684(16) 0.55457(15) 0.15943(4) 0.0306(3) Uani 1 1 d . . . . .
O2 O 0.26024(19) 0.34645(17) 0.19645(5) 0.0432(4) Uani 1 1 d . . . . .
N1 N 0.6318(2) 0.49824(18) 0.10356(5) 0.0309(4) Uani 1 1 d D . . . .
N2 N 0.15347(19) 0.73623(17) 0.20633(5) 0.0258(3) Uani 1 1 d D . . . .
N3 N 0.08755(18) 1.06322(17) 0.24102(5) 0.0258(3) Uani 1 1 d D . . . .
C1 C 0.8096(3) 0.8488(3) -0.02745(7) 0.0396(5) Uani 1 1 d . . . . .
H1A H 0.9197 0.8900 -0.0392 0.059 Uiso 1 1 calc R U . . .
H1B H 0.7382 0.9415 -0.0178 0.059 Uiso 1 1 calc R U . . .
H1C H 0.7415 0.7873 -0.0525 0.059 Uiso 1 1 calc R U . . .
C2 C 0.8546(2) 0.7376(2) 0.01428(6) 0.0270(4) Uani 1 1 d . . . . .
C3 C 1.0311(2) 0.7014(2) 0.02834(6) 0.0313(4) Uani 1 1 d . . . . .
H3A H 1.1226 0.7484 0.0117 0.038 Uiso 1 1 calc R U . . .
C4 C 1.0766(2) 0.5981(2) 0.06611(6) 0.0323(4) Uani 1 1 d . . . . .
H4 H 1.1982 0.5738 0.0749 0.039 Uiso 1 1 calc R U . . .
C5 C 0.9454(2) 0.5307(2) 0.09092(6) 0.0304(4) Uani 1 1 d . . . . .
H5 H 0.9763 0.4615 0.1172 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7669(2) 0.5644(2) 0.07735(6) 0.0251(4) Uani 1 1 d . . . . .
C7 C 0.7188(2) 0.6677(2) 0.03879(6) 0.0247(4) Uani 1 1 d . . . . .
C8 C 0.5259(2) 0.7038(2) 0.02452(7) 0.0333(4) Uani 1 1 d . . . . .
H8A H 0.4529 0.6103 0.0328 0.050 Uiso 1 1 calc R U . . .
H8B H 0.5098 0.7226 -0.0096 0.050 Uiso 1 1 calc R U . . .
H8C H 0.4895 0.8019 0.0411 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6096(2) 0.3345(2) 0.11362(5) 0.0238(4) Uani 1 1 d . . . . .
C10 C 0.7089(2) 0.2120(2) 0.09272(6) 0.0286(4) Uani 1 1 d . . . . .
H10 H 0.7966 0.2435 0.0724 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6819(2) 0.0481(2) 0.10101(6) 0.0332(4) Uani 1 1 d . . . . .
H11 H 0.7499 -0.0317 0.0861 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5560(3) -0.0021(2) 0.13105(7) 0.0350(4) Uani 1 1 d . . . . .
H12 H 0.5371 -0.1152 0.1370 0.042 Uiso 1 1 calc R U . . .
C13 C 0.4595(2) 0.1170(2) 0.15192(6) 0.0312(4) Uani 1 1 d . . . . .
H13 H 0.3744 0.0834 0.1727 0.037 Uiso 1 1 calc R U . . .
C14 C 0.4806(2) 0.2844(2) 0.14403(6) 0.0242(4) Uani 1 1 d . . . . .
C15 C 0.3638(2) 0.4021(2) 0.16850(6) 0.0255(4) Uani 1 1 d . . . . .
C16 C 0.0539(2) 0.8578(2) 0.17536(6) 0.0283(4) Uani 1 1 d . . . . .
H16A H -0.0376 0.8007 0.1543 0.034 Uiso 1 1 calc R U . . .
H16B H 0.1368 0.9139 0.1554 0.034 Uiso 1 1 calc R U . . .
C17 C -0.0353(2) 0.9840(2) 0.20516(6) 0.0287(4) Uani 1 1 d . . . . .
H17A H -0.0912 1.0695 0.1841 0.034 Uiso 1 1 calc R U . . .
H17B H -0.1311 0.9293 0.2210 0.034 Uiso 1 1 calc R U . . .
C18 C 0.1891(2) 0.9420(2) 0.27037(6) 0.0292(4) Uani 1 1 d . . . . .
H18A H 0.1073 0.8847 0.2903 0.035 Uiso 1 1 calc R U . . .
H18B H 0.2793 0.9999 0.2916 0.035 Uiso 1 1 calc R U . . .
C19 C 0.2824(2) 0.8153(2) 0.24192(6) 0.0289(4) Uani 1 1 d . . . . .
H19A H 0.3781 0.8691 0.2257 0.035 Uiso 1 1 calc R U . . .
H19B H 0.3378 0.7306 0.2634 0.035 Uiso 1 1 calc R U . . .
H1 H 0.553(2) 0.564(2) 0.1162(7) 0.041(6) Uiso 1 1 d D . . . .
H2A H 0.071(2) 0.679(2) 0.2213(6) 0.039(6) Uiso 1 1 d D . . . .
H2B H 0.221(2) 0.666(2) 0.1900(7) 0.046(6) Uiso 1 1 d D . . . .
H3 H 0.156(2) 1.139(2) 0.2274(7) 0.037(6) Uiso 1 1 d 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 C15 1.275(2) . ?
O2 C15 1.2460(19) . ?
N1 C9 1.378(2) . ?
N1 C6 1.418(2) . ?
N1 H1 0.900(9) . ?
N2 C16 1.486(2) . ?
N2 C19 1.489(2) . ?
N2 H2A 0.912(9) . ?
N2 H2B 0.919(9) . ?
N3 C18 1.466(2) . ?
N3 C17 1.467(2) . ?
N3 H3 0.911(9) . ?
C1 C2 1.509(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.387(3) . ?
C2 C7 1.407(2) . ?
C3 C4 1.384(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.377(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(2) . ?
C7 C8 1.504(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.409(2) . ?
C9 C14 1.415(2) . ?
C10 C11 1.375(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.511(2) . ?
C16 C17 1.525(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.521(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 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
C9 N1 C6 125.66(14) . . ?
C9 N1 H1 113.7(14) . . ?
C6 N1 H1 120.7(14) . . ?
C16 N2 C19 112.45(13) . . ?
C16 N2 H2A 106.9(13) . . ?
C19 N2 H2A 109.6(13) . . ?
C16 N2 H2B 113.0(14) . . ?
C19 N2 H2B 104.7(14) . . ?
H2A N2 H2B 110.2(13) . . ?
C18 N3 C17 111.52(14) . . ?
C18 N3 H3 114.2(13) . . ?
C17 N3 H3 110.4(13) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 119.41(16) . . ?
C3 C2 C1 120.02(15) . . ?
C7 C2 C1 120.57(16) . . ?
C4 C3 C2 121.39(16) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C5 C4 C3 119.91(17) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.84(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.82(15) . . ?
C5 C6 N1 119.86(16) . . ?
C7 C6 N1 119.28(15) . . ?
C6 C7 C2 118.63(15) . . ?
C6 C7 C8 120.43(15) . . ?
C2 C7 C8 120.94(15) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 121.34(15) . . ?
N1 C9 C14 120.56(14) . . ?
C10 C9 C14 118.06(15) . . ?
C11 C10 C9 121.64(16) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.64(16) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 118.04(17) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C14 123.30(16) . . ?
C12 C13 H13 118.3 . . ?
C14 C13 H13 118.3 . . ?
C13 C14 C9 118.31(15) . . ?
C13 C14 C15 117.92(14) . . ?
C9 C14 C15 123.77(15) . . ?
O2 C15 O1 123.19(15) . . ?
O2 C15 C14 118.95(15) . . ?
O1 C15 C14 117.86(14) . . ?
N2 C16 C17 110.15(13) . . ?
N2 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N2 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N3 C17 C16 113.65(14) . . ?
N3 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
N3 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
N3 C18 C19 113.42(14) . . ?
N3 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
N3 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
N2 C19 C18 110.53(13) . . ?
N2 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?

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
C7 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 -179.18(17) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 N1 -178.50(16) . . . . ?
C9 N1 C6 C5 -54.7(2) . . . . ?
C9 N1 C6 C7 127.27(18) . . . . ?
C5 C6 C7 C2 -0.4(2) . . . . ?
N1 C6 C7 C2 177.53(15) . . . . ?
C5 C6 C7 C8 -179.80(16) . . . . ?
N1 C6 C7 C8 -1.8(2) . . . . ?
C3 C2 C7 C6 0.8(2) . . . . ?
C1 C2 C7 C6 179.79(16) . . . . ?
C3 C2 C7 C8 -179.85(16) . . . . ?
C1 C2 C7 C8 -0.9(2) . . . . ?
C6 N1 C9 C10 -8.7(3) . . . . ?
C6 N1 C9 C14 173.74(16) . . . . ?
N1 C9 C10 C11 -177.15(17) . . . . ?
C14 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C9 -1.0(3) . . . . ?
C12 C13 C14 C15 178.90(17) . . . . ?
N1 C9 C14 C13 178.06(16) . . . . ?
C10 C9 C14 C13 0.4(2) . . . . ?
N1 C9 C14 C15 -1.9(2) . . . . ?
C10 C9 C14 C15 -179.51(15) . . . . ?
C13 C14 C15 O2 3.6(2) . . . . ?
C9 C14 C15 O2 -176.50(16) . . . . ?
C13 C14 C15 O1 -176.55(16) . . . . ?
C9 C14 C15 O1 3.4(2) . . . . ?
C19 N2 C16 C17 -54.16(18) . . . . ?
C18 N3 C17 C16 -52.48(18) . . . . ?
N2 C16 C17 N3 53.32(19) . . . . ?
C17 N3 C18 C19 52.35(18) . . . . ?
C16 N2 C19 C18 54.36(18) . . . . ?
N3 C18 C19 N2 -53.30(19) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_shelxl_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc22c80r
_database_code_depnum_ccdc_archive 'CCDC 1917443'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-07-26 downloaded from the CCDC.
;
_audit_creation_date             2018-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 Cl N O2, C4 H11 N2'
_chemical_formula_sum            'C18 H22 Cl N3 O2'
_chemical_formula_weight         347.83
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.827(2)
_cell_length_b                   7.5021(15)
_cell_length_c                   21.322(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.39(3)
_cell_angle_gamma                90
_cell_volume                     1717.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4921
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.0349
_cell_measurement_theta_min      1.9262
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19754
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.914
_diffrn_reflns_theta_min         1.926
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn 70  CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3545
_reflns_number_total             4097
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'crystalclear(Rigaku, 2008)'
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.3156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1 = N3-H3A = N2-H2A = N2-H2B
 0.9 with sigma of 0.01
 H2A-H2B
 1.5 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.13506(3) 0.53048(5) 0.16257(2) 0.03089(12) Uani 1 1 d . . . . .
O1 O 0.54007(8) 0.74154(14) 0.41094(4) 0.0316(2) Uani 1 1 d . . . . .
O2 O 0.69415(10) 0.88761(14) 0.46745(4) 0.0362(2) Uani 1 1 d . . . . .
N1 N 0.55322(9) 0.69132(15) 0.28945(5) 0.0240(2) Uani 1 1 d D . . . .
H1 H 0.5153(13) 0.695(2) 0.3243(5) 0.029 Uiso 1 1 d DR . . . .
C1 C 0.47928(11) 0.69577(15) 0.23095(5) 0.0197(2) Uani 1 1 d . . . . .
C2 C 0.51578(11) 0.77805(17) 0.17750(6) 0.0238(3) Uani 1 1 d . . . . .
H2 H 0.594271 0.836109 0.180240 0.029 Uiso 1 1 calc R . . . .
C3 C 0.43839(12) 0.77549(18) 0.12067(6) 0.0274(3) Uani 1 1 d . . . . .
H3 H 0.465567 0.828998 0.084449 0.033 Uiso 1 1 calc R . . . .
C4 C 0.32200(12) 0.69642(18) 0.11553(6) 0.0258(3) Uani 1 1 d . . . . .
H4 H 0.269327 0.693012 0.076311 0.031 Uiso 1 1 calc R . . . .
C5 C 0.28518(11) 0.62239(16) 0.16973(6) 0.0220(3) Uani 1 1 d . . . . .
C6 C 0.35982(11) 0.61739(16) 0.22780(5) 0.0203(2) Uani 1 1 d . . . . .
C7 C 0.31820(12) 0.53600(19) 0.28594(6) 0.0284(3) Uani 1 1 d . . . . .
H7A H 0.237713 0.476844 0.274662 0.043 Uiso 1 1 calc GR . . . .
H7B H 0.309745 0.629616 0.317155 0.043 Uiso 1 1 calc GR . . . .
H7C H 0.380004 0.448431 0.303923 0.043 Uiso 1 1 calc GR . . . .
C8 C 0.67933(11) 0.72810(16) 0.30367(5) 0.0199(2) Uani 1 1 d . . . . .
C9 C 0.76366(12) 0.69453(17) 0.26022(6) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.734383 0.645085 0.220035 0.030 Uiso 1 1 calc R . . . .
C10 C 0.88882(12) 0.73273(19) 0.27536(7) 0.0312(3) Uani 1 1 d . . . . .
H10 H 0.944385 0.710249 0.245224 0.037 Uiso 1 1 calc R . . . .
C11 C 0.93435(12) 0.80310(19) 0.33363(7) 0.0320(3) Uani 1 1 d . . . . .
H11 H 1.019934 0.833205 0.343141 0.038 Uiso 1 1 calc R . . . .
C12 C 0.85348(12) 0.82893(17) 0.37779(6) 0.0268(3) Uani 1 1 d . . . . .
H12 H 0.885154 0.874173 0.418290 0.032 Uiso 1 1 calc R . . . .
C13 C 0.72650(11) 0.79069(16) 0.36484(5) 0.0205(2) Uani 1 1 d . . . . .
C14 C 0.64785(11) 0.81006(16) 0.41799(5) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.86560(10) 0.71330(15) -0.01135(5) 0.0263(2) Uani 1 1 d D . . . .
H2A H 0.8490(13) 0.6004(13) 0.0009(7) 0.032 Uiso 1 1 d DR . . . .
H2B H 0.9308(11) 0.7131(18) -0.0351(6) 0.032 Uiso 1 1 d DR . . . .
N3 N 0.68078(11) 0.90849(17) 0.04787(6) 0.0372(3) Uani 1 1 d D . . . .
H3A H 0.6924(17) 1.0232(14) 0.0383(8) 0.045 Uiso 1 1 d DR . . . .
C15 C 0.90179(13) 0.8157(2) 0.04823(6) 0.0318(3) Uani 1 1 d . . . . .
H15A H 0.931074 0.935953 0.037945 0.038 Uiso 1 1 calc R . . . .
H15B H 0.970847 0.753920 0.074503 0.038 Uiso 1 1 calc R . . . .
C16 C 0.79082(14) 0.8322(2) 0.08486(7) 0.0359(3) Uani 1 1 d . . . . .
H16A H 0.769626 0.712456 0.099837 0.043 Uiso 1 1 calc R . . . .
H16B H 0.814596 0.907701 0.122557 0.043 Uiso 1 1 calc R . . . .
C17 C 0.64776(13) 0.8088(2) -0.01049(7) 0.0339(3) Uani 1 1 d . . . . .
H17A H 0.577012 0.868948 -0.036049 0.041 Uiso 1 1 calc R . . . .
H17B H 0.619777 0.688100 0.000085 0.041 Uiso 1 1 calc R . . . .
C18 C 0.75426(12) 0.79132(19) -0.04991(6) 0.0299(3) Uani 1 1 d . . . . .
H18A H 0.728455 0.714029 -0.086914 0.036 Uiso 1 1 calc R . . . .
H18B H 0.775398 0.910186 -0.065661 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.7540(13) . ?
O1 C14 1.2663(16) . ?
O2 C14 1.2515(15) . ?
N1 H1 0.895(9) . ?
N1 C1 1.3932(16) . ?
N1 C8 1.3878(15) . ?
C1 C2 1.3970(16) . ?
C1 C6 1.4146(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3820(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3843(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.3862(17) . ?
C5 C6 1.3894(17) . ?
C6 C7 1.5019(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.4047(16) . ?
C8 C13 1.4181(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3821(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3793(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.3969(17) . ?
C13 C14 1.5095(17) . ?
N2 H2A 0.911(8) . ?
N2 H2B 0.920(8) . ?
N2 C15 1.4933(17) . ?
N2 C18 1.4890(18) . ?
N3 H3A 0.897(9) . ?
N3 C16 1.459(2) . ?
N3 C17 1.4564(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5198(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5174(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 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
C1 N1 H1 118.1(10) . . ?
C8 N1 H1 110.8(10) . . ?
C8 N1 C1 128.81(10) . . ?
N1 C1 C2 123.42(11) . . ?
N1 C1 C6 116.68(10) . . ?
C2 C1 C6 119.86(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.39(11) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.23(12) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.52(12) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 Cl1 116.59(10) . . ?
C4 C5 C6 123.86(11) . . ?
C6 C5 Cl1 119.55(9) . . ?
C1 C6 C7 119.96(11) . . ?
C5 C6 C1 117.04(11) . . ?
C5 C6 C7 123.00(11) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 121.67(11) . . ?
N1 C8 C13 119.65(10) . . ?
C9 C8 C13 118.56(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.65(12) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.00(12) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.90(12) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 122.09(12) . . ?
C13 C12 H12 119.0 . . ?
C8 C13 C14 123.44(11) . . ?
C12 C13 C8 118.60(11) . . ?
C12 C13 C14 117.89(11) . . ?
O1 C14 C13 118.17(11) . . ?
O2 C14 O1 123.50(12) . . ?
O2 C14 C13 118.29(12) . . ?
H2A N2 H2B 110.4(10) . . ?
C15 N2 H2A 105.9(9) . . ?
C15 N2 H2B 109.4(9) . . ?
C18 N2 H2A 110.4(9) . . ?
C18 N2 H2B 108.7(9) . . ?
C18 N2 C15 111.88(11) . . ?
C16 N3 H3A 111.8(11) . . ?
C17 N3 H3A 108.9(11) . . ?
C17 N3 C16 110.74(11) . . ?
N2 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
N2 C15 C16 109.92(11) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
N3 C16 C15 113.50(12) . . ?
N3 C16 H16A 108.9 . . ?
N3 C16 H16B 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
N3 C17 H17A 108.9 . . ?
N3 C17 H17B 108.9 . . ?
N3 C17 C18 113.40(12) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
N2 C18 C17 110.30(11) . . ?
N2 C18 H18A 109.6 . . ?
N2 C18 H18B 109.6 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?

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
Cl1 C5 C6 C1 -179.14(9) . . . . ?
Cl1 C5 C6 C7 0.01(16) . . . . ?
N1 C1 C2 C3 179.16(12) . . . . ?
N1 C1 C6 C5 179.57(10) . . . . ?
N1 C1 C6 C7 0.40(16) . . . . ?
N1 C8 C9 C10 179.81(12) . . . . ?
N1 C8 C13 C12 -179.20(11) . . . . ?
N1 C8 C13 C14 3.84(18) . . . . ?
C1 N1 C8 C9 -31.1(2) . . . . ?
C1 N1 C8 C13 152.92(12) . . . . ?
C1 C2 C3 C4 1.84(19) . . . . ?
C2 C1 C6 C5 1.87(17) . . . . ?
C2 C1 C6 C7 -177.30(11) . . . . ?
C2 C3 C4 C5 0.99(19) . . . . ?
C3 C4 C5 Cl1 177.69(10) . . . . ?
C3 C4 C5 C6 -2.48(19) . . . . ?
C4 C5 C6 C1 1.04(18) . . . . ?
C4 C5 C6 C7 -179.81(12) . . . . ?
C6 C1 C2 C3 -3.30(18) . . . . ?
C8 N1 C1 C2 -15.0(2) . . . . ?
C8 N1 C1 C6 167.42(12) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C8 C13 C14 O1 11.39(17) . . . . ?
C8 C13 C14 O2 -170.98(11) . . . . ?
C9 C8 C13 C12 4.69(17) . . . . ?
C9 C8 C13 C14 -172.26(11) . . . . ?
C9 C10 C11 C12 2.4(2) . . . . ?
C10 C11 C12 C13 -1.8(2) . . . . ?
C11 C12 C13 C8 -1.80(19) . . . . ?
C11 C12 C13 C14 175.32(12) . . . . ?
C12 C13 C14 O1 -165.58(11) . . . . ?
C12 C13 C14 O2 12.04(17) . . . . ?
C13 C8 C9 C10 -4.17(19) . . . . ?
N2 C15 C16 N3 -54.51(16) . . . . ?
N3 C17 C18 N2 54.48(16) . . . . ?
C15 N2 C18 C17 -54.11(15) . . . . ?
C16 N3 C17 C18 -54.29(16) . . . . ?
C17 N3 C16 C15 54.46(16) . . . . ?
C18 N2 C15 C16 54.02(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_R20180426D1
_audit_block_doi                 10.5517/ccdc.csd.cc22c7yn
_database_code_depnum_ccdc_archive 'CCDC 1917441'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H34 Cl2 N4 O4'
_chemical_formula_weight         609.53

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                   10.303(2)
_cell_length_b                   7.6173(15)
_cell_length_c                   38.517(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3022.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3961
_cell_measurement_theta_min      2.0461
_cell_measurement_theta_max      27.5204

_exptl_crystal_description       prism
_exptl_crystal_colour            transparent
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7462
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13183
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.115
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.018
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2604
_reflns_number_gt                2235
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0704P)²+2.6772P] 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         2604
_refine_ls_number_parameters     200
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1634
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
Cl1 Cl 0.34332(9) 0.99670(16) 0.70274(2) 0.0599(4) Uani 1 1 d . . . . .
O1 O 0.7068(2) 0.9038(3) 0.55737(5) 0.0358(5) Uani 1 1 d . . . . .
O2 O 0.86676(19) 0.9549(2) 0.51891(4) 0.0280(5) Uani 1 1 d . . . . .
N1 N 0.7510(3) 0.9578(3) 0.62448(6) 0.0315(6) Uani 1 1 d D . . . .
H1 H 0.702(3) 0.931(4) 0.6062(5) 0.038 Uiso 1 1 d D U . . .
C1 C 0.4855(3) 1.0554(4) 0.63269(8) 0.0384(8) Uani 1 1 d . . . . .
H1A H 0.5427 1.1280 0.6183 0.058 Uiso 1 1 calc R U . . .
H1B H 0.4155 1.1282 0.6421 0.058 Uiso 1 1 calc R U . . .
H1C H 0.4484 0.9612 0.6185 0.058 Uiso 1 1 calc R U . . .
C2 C 0.5633(3) 0.9758(4) 0.66242(7) 0.0284(7) Uani 1 1 d . . . . .
C3 C 0.5075(3) 0.9416(4) 0.69515(7) 0.0352(7) Uani 1 1 d . . . . .
C4 C 0.5763(4) 0.8643(4) 0.72246(7) 0.0429(8) Uani 1 1 d . . . . .
H4 H 0.5356 0.8436 0.7442 0.052 Uiso 1 1 calc R U . . .
C5 C 0.7060(3) 0.8183(4) 0.71716(7) 0.0394(8) Uani 1 1 d . . . . .
H5 H 0.7537 0.7647 0.7354 0.047 Uiso 1 1 calc R U . . .
C6 C 0.7667(3) 0.8503(4) 0.68515(7) 0.0300(7) Uani 1 1 d . . . . .
H6 H 0.8550 0.8187 0.6818 0.036 Uiso 1 1 calc R U . . .
C7 C 0.6956(3) 0.9301(4) 0.65780(7) 0.0281(7) Uani 1 1 d . . . . .
C8 C 0.8787(3) 0.9942(3) 0.61551(7) 0.0249(6) Uani 1 1 d . . . . .
C9 C 0.9722(3) 1.0506(4) 0.64034(7) 0.0305(7) Uani 1 1 d . . . . .
H9 H 0.9466 1.0661 0.6638 0.037 Uiso 1 1 calc R U . . .
C10 C 1.0996(3) 1.0833(4) 0.63095(7) 0.0331(7) Uani 1 1 d . . . . .
H10 H 1.1599 1.1202 0.6481 0.040 Uiso 1 1 calc R U . . .
C11 C 1.1414(3) 1.0628(4) 0.59640(8) 0.0343(7) Uani 1 1 d . . . . .
H11 H 1.2296 1.0810 0.5902 0.041 Uiso 1 1 calc R U . . .
C12 C 1.0503(3) 1.0152(3) 0.57152(7) 0.0256(6) Uani 1 1 d . . . . .
H12 H 1.0777 1.0037 0.5481 0.031 Uiso 1 1 calc R U . . .
C13 C 0.9184(3) 0.9830(3) 0.57966(6) 0.0229(6) Uani 1 1 d . . . . .
C14 C 0.8254(3) 0.9443(3) 0.54984(7) 0.0236(6) Uani 1 1 d . . . . .
C15 C 1.0718(3) 0.6037(3) 0.52532(6) 0.0253(6) Uani 1 1 d . . . . .
H15A H 1.0036 0.6309 0.5426 0.030 Uiso 1 1 calc R U . . .
H15B H 1.1539 0.6581 0.5332 0.030 Uiso 1 1 calc R U . . .
N2 N 1.0340(2) 0.6781(3) 0.49051(6) 0.0243(5) Uani 1 1 d D . . . .
H2A H 1.021(2) 0.7952(15) 0.4925(7) 0.029 Uiso 1 1 d D U . . .
H2B H 1.102(2) 0.655(3) 0.4758(6) 0.029 Uiso 1 1 d D U . . .
C16 C 0.9111(3) 0.5946(4) 0.47742(7) 0.0257(6) Uani 1 1 d . . . . .
H16A H 0.8890 0.6433 0.4543 0.031 Uiso 1 1 calc R U . . .
H16B H 0.8388 0.6216 0.4935 0.031 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
Cl1 C3 1.767(3) . ?
O1 C14 1.293(3) . ?
O2 C14 1.268(3) . ?
N1 C8 1.388(4) . ?
N1 C7 1.421(4) . ?
N1 H1 0.892(10) . ?
C1 C2 1.523(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.410(4) . ?
C2 C7 1.418(4) . ?
C3 C4 1.399(4) . ?
C4 C5 1.396(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.420(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.423(4) . ?
C8 C13 1.443(4) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.407(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.525(4) . ?
C15 N2 1.507(3) . ?
C15 C16 1.525(4) 5_766 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
N2 C16 1.504(4) . ?
N2 H2A 0.905(10) . ?
N2 H2B 0.916(9) . ?
C16 C15 1.525(4) 5_766 ?
C16 H16A 0.9900 . ?
C16 H16B 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
C8 N1 C7 129.4(2) . . ?
C8 N1 H1 113(2) . . ?
C7 N1 H1 117(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.3(3) . . ?
C3 C2 C1 122.1(3) . . ?
C7 C2 C1 120.6(2) . . ?
C4 C3 C2 122.9(3) . . ?
C4 C3 Cl1 117.4(2) . . ?
C2 C3 Cl1 119.6(2) . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 120.5(3) . . ?
C2 C7 N1 117.6(2) . . ?
C6 C7 N1 121.8(3) . . ?
N1 C8 C9 122.3(2) . . ?
N1 C8 C13 119.7(2) . . ?
C9 C8 C13 118.0(3) . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 122.7(3) . . ?
C11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C12 C13 C8 118.3(2) . . ?
C12 C13 C14 118.0(2) . . ?
C8 C13 C14 123.7(2) . . ?
O2 C14 O1 122.9(2) . . ?
O2 C14 C13 119.0(2) . . ?
O1 C14 C13 118.1(2) . . ?
N2 C15 C16 110.0(2) . 5_766 ?
N2 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 5_766 . ?
N2 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 5_766 . ?
H15A C15 H15B 108.2 . . ?
C16 N2 C15 110.9(2) . . ?
C16 N2 H2A 108.8(18) . . ?
C15 N2 H2A 109.4(17) . . ?
C16 N2 H2B 110.7(18) . . ?
C15 N2 H2B 106.5(18) . . ?
H2A N2 H2B 110.6(15) . . ?
N2 C16 C15 110.1(2) . 5_766 ?
N2 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 5_766 . ?
N2 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 5_766 . ?
H16A C16 H16B 108.1 . . ?

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
C7 C2 C3 C4 -0.6(5) . . . . ?
C1 C2 C3 C4 178.2(3) . . . . ?
C7 C2 C3 Cl1 179.6(2) . . . . ?
C1 C2 C3 Cl1 -1.5(4) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
Cl1 C3 C4 C5 179.6(2) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C3 C2 C7 C6 1.1(4) . . . . ?
C1 C2 C7 C6 -177.8(3) . . . . ?
C3 C2 C7 N1 177.6(3) . . . . ?
C1 C2 C7 N1 -1.3(4) . . . . ?
C5 C6 C7 C2 -0.8(4) . . . . ?
C5 C6 C7 N1 -177.1(3) . . . . ?
C8 N1 C7 C2 151.0(3) . . . . ?
C8 N1 C7 C6 -32.6(4) . . . . ?
C7 N1 C8 C9 -15.2(5) . . . . ?
C7 N1 C8 C13 167.7(3) . . . . ?
N1 C8 C9 C10 178.9(3) . . . . ?
C13 C8 C9 C10 -4.0(4) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 2.4(4) . . . . ?
C10 C11 C12 C13 -1.4(4) . . . . ?
C11 C12 C13 C8 -2.3(4) . . . . ?
C11 C12 C13 C14 175.7(3) . . . . ?
N1 C8 C13 C12 -177.9(2) . . . . ?
C9 C8 C13 C12 4.9(4) . . . . ?
N1 C8 C13 C14 4.2(4) . . . . ?
C9 C8 C13 C14 -173.0(2) . . . . ?
C12 C13 C14 O2 -5.1(4) . . . . ?
C8 C13 C14 O2 172.8(2) . . . . ?
C12 C13 C14 O1 175.6(2) . . . . ?
C8 C13 C14 O1 -6.5(4) . . . . ?
C16 C15 N2 C16 57.9(3) 5_766 . . . ?
C15 N2 C16 C15 -58.0(3) . . . 5_766 ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.063

