# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1941779'
loop_
_audit_author_name
_audit_author_address
'Ray J Butcher'
;Howard University
United States of America
;
_audit_update_record             
;
2019-07-19 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N4 O2, C H4 O'
_chemical_formula_sum            'C19 H20 N4 O3'
_chemical_formula_weight         352.39

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   31.955(5)
_cell_length_b                   5.0786(5)
_cell_length_c                   23.326(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.477(13)
_cell_angle_gamma                90
_cell_volume                     3445.3(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2476
_cell_measurement_theta_min      4.0910
_cell_measurement_theta_max      30.8370

_exptl_crystal_description       
;
long plate
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            10807
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.499
_diffrn_reflns_theta_max         31.398
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4849
_reflns_number_gt                2974
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Shelxt (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.1053P)²+4.0854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4849
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0924
_refine_ls_wR_factor_ref         0.2537
_refine_ls_wR_factor_gt          0.2183
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.80080(7) 0.4164(4) 0.52484(9) 0.0245(5) Uani 1 1 d . . . . .
O2 O 0.61545(8) 1.1175(4) 0.29939(10) 0.0331(6) Uani 1 1 d . . . . .
O3 O 0.60105(9) 1.3970(5) 0.38994(11) 0.0422(6) Uani 1 1 d . . . . .
H3 H 0.6139 1.3277 0.3688 0.063 Uiso 1 1 calc R U . . .
N1 N 0.82585(8) 0.0834(4) 0.48230(11) 0.0214(5) Uani 1 1 d . . . . .
H1A H 0.8477 0.0491 0.5197 0.026 Uiso 1 1 calc R U . . .
N2 N 0.69478(8) 0.6040(4) 0.35796(11) 0.0219(5) Uani 1 1 d . . . . .
N3 N 0.67035(9) 0.8284(5) 0.35670(11) 0.0244(5) Uani 1 1 d . . . . .
H3B H 0.6785 0.9269 0.3907 0.029 Uiso 1 1 calc R U . . .
N4 N 0.61925(9) 0.7142(4) 0.25733(11) 0.0247(5) Uani 1 1 d . . . . .
H4N H 0.6328 0.5595 0.2670 0.047(11) Uiso 1 1 calc R . . . .
C1 C 0.79594(10) 0.2853(5) 0.47769(13) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.75972(9) 0.3349(5) 0.41551(12) 0.0201(5) Uani 1 1 d . . . . .
C3 C 0.75741(10) 0.1873(5) 0.36555(13) 0.0214(6) Uani 1 1 d . . . . .
H3A H 0.7338 0.2225 0.3251 0.026 Uiso 1 1 calc R U . . .
C4 C 0.78943(10) -0.0184(5) 0.37210(13) 0.0208(6) Uani 1 1 d . . . . .
C5 C 0.78758(10) -0.1711(6) 0.32042(13) 0.0238(6) Uani 1 1 d . . . . .
H5A H 0.7646 -0.1370 0.2794 0.029 Uiso 1 1 calc R U . . .
C6 C 0.81907(10) -0.3691(6) 0.32941(14) 0.0249(6) Uani 1 1 d . . . . .
H6A H 0.8177 -0.4719 0.2947 0.030 Uiso 1 1 calc R U . . .
C7 C 0.85302(10) -0.4190(6) 0.38965(14) 0.0249(6) Uani 1 1 d . . . . .
H7A H 0.8745 -0.5566 0.3951 0.030 Uiso 1 1 calc R U . . .
C8 C 0.85640(10) -0.2747(5) 0.44153(14) 0.0227(6) Uani 1 1 d . . . . .
C9 C 0.82410(10) -0.0698(5) 0.43224(13) 0.0205(6) Uani 1 1 d . . . . .
C10 C 0.89313(10) -0.3321(6) 0.50581(14) 0.0266(6) Uani 1 1 d . . . . .
H10A H 0.9125 -0.4765 0.5030 0.040 Uiso 1 1 calc R U . . .
H10B H 0.8788 -0.3828 0.5341 0.040 Uiso 1 1 calc R U . . .
H10C H 0.9120 -0.1746 0.5223 0.040 Uiso 1 1 calc R U . . .
C11 C 0.72899(10) 0.5542(5) 0.41034(13) 0.0211(6) Uani 1 1 d . . . . .
H11A H 0.7343 0.6614 0.4461 0.025 Uiso 1 1 calc R U . . .
C12 C 0.63379(10) 0.8986(5) 0.30349(13) 0.0234(6) Uani 1 1 d . . . . .
C13 C 0.58500(9) 0.7417(5) 0.19574(13) 0.0201(5) Uani 1 1 d . . . . .
C14 C 0.58505(11) 0.5624(7) 0.15172(15) 0.0340(7) Uani 1 1 d . . . . .
H14A H 0.6074 0.4258 0.1642 0.041 Uiso 1 1 calc R U . . .
C15 C 0.55333(12) 0.5762(8) 0.08960(15) 0.0372(8) Uani 1 1 d . . . . .
H15A H 0.5540 0.4503 0.0599 0.045 Uiso 1 1 calc R U . . .
C16 C 0.52085(11) 0.7720(6) 0.07102(15) 0.0337(7) Uani 1 1 d . . . . .
H16A H 0.4990 0.7837 0.0285 0.040 Uiso 1 1 calc R U . . .
C17 C 0.52041(14) 0.9499(7) 0.11471(19) 0.0511(11) Uani 1 1 d . . . . .
H17A H 0.4980 1.0860 0.1019 0.061 Uiso 1 1 calc R U . . .
C18 C 0.55183(13) 0.9372(6) 0.17725(17) 0.0423(9) Uani 1 1 d . . . . .
H18A H 0.5506 1.0612 0.2070 0.051 Uiso 1 1 calc R U . . .
C19 C 0.55801(14) 1.5036(10) 0.34858(19) 0.0563(11) Uani 1 1 d . . . . .
H19A H 0.5358 1.4828 0.3672 0.084 Uiso 1 1 calc R U . . .
H19B H 0.5469 1.4105 0.3082 0.084 Uiso 1 1 calc R U . . .
H19C H 0.5617 1.6910 0.3418 0.084 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
O1 C1 1.239(3) . ?
O2 C12 1.242(3) . ?
O3 C19 1.420(5) . ?
O3 H3 0.8400 . ?
N1 C1 1.375(4) . ?
N1 C9 1.385(3) . ?
N1 H1A 0.8800 . ?
N2 C11 1.282(3) . ?
N2 N3 1.375(3) . ?
N3 C12 1.353(4) . ?
N3 H3B 0.8800 . ?
N4 C12 1.356(4) . ?
N4 C13 1.407(3) . ?
N4 H4N 0.8800 . ?
C1 C2 1.455(4) . ?
C2 C3 1.362(4) . ?
C2 C11 1.457(4) . ?
C3 C4 1.426(4) . ?
C3 H3A 0.9500 . ?
C4 C9 1.406(4) . ?
C4 C5 1.414(4) . ?
C5 C6 1.376(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.397(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.380(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.418(4) . ?
C8 C10 1.501(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9500 . ?
C13 C14 1.373(4) . ?
C13 C18 1.385(4) . ?
C14 C15 1.384(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.372(5) . ?
C15 H15A 0.9500 . ?
C16 C17 1.366(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.388(5) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O3 H3 109.5 . . ?
C1 N1 C9 124.7(2) . . ?
C1 N1 H1A 117.7 . . ?
C9 N1 H1A 117.7 . . ?
C11 N2 N3 115.9(2) . . ?
C12 N3 N2 120.3(2) . . ?
C12 N3 H3B 119.8 . . ?
N2 N3 H3B 119.8 . . ?
C12 N4 C13 127.5(2) . . ?
C12 N4 H4N 116.3 . . ?
C13 N4 H4N 116.3 . . ?
O1 C1 N1 120.2(2) . . ?
O1 C1 C2 123.2(3) . . ?
N1 C1 C2 116.6(2) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 C11 123.7(2) . . ?
C1 C2 C11 116.5(2) . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C9 C4 C5 119.1(3) . . ?
C9 C4 C3 118.5(2) . . ?
C5 C4 C3 122.4(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 H7A 118.9 . . ?
C6 C7 H7A 118.9 . . ?
C7 C8 C9 117.9(3) . . ?
C7 C8 C10 121.2(3) . . ?
C9 C8 C10 120.9(3) . . ?
N1 C9 C4 118.5(3) . . ?
N1 C9 C8 120.7(2) . . ?
C4 C9 C8 120.8(3) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C2 120.6(3) . . ?
N2 C11 H11A 119.7 . . ?
C2 C11 H11A 119.7 . . ?
O2 C12 N3 120.5(3) . . ?
O2 C12 N4 124.2(3) . . ?
N3 C12 N4 115.3(2) . . ?
C14 C13 C18 118.7(3) . . ?
C14 C13 N4 117.2(3) . . ?
C18 C13 N4 124.1(3) . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14A 119.2 . . ?
C15 C14 H14A 119.2 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16A 120.5 . . ?
C15 C16 H16A 120.5 . . ?
C16 C17 C18 121.8(3) . . ?
C16 C17 H17A 119.1 . . ?
C18 C17 H17A 119.1 . . ?
C13 C18 C17 119.2(3) . . ?
C13 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 N3 C12 179.7(2) . . . . ?
C9 N1 C1 O1 -178.2(2) . . . . ?
C9 N1 C1 C2 1.1(4) . . . . ?
O1 C1 C2 C3 178.1(2) . . . . ?
N1 C1 C2 C3 -1.2(4) . . . . ?
O1 C1 C2 C11 1.2(4) . . . . ?
N1 C1 C2 C11 -178.1(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C11 C2 C3 C4 177.2(2) . . . . ?
C2 C3 C4 C9 0.4(4) . . . . ?
C2 C3 C4 C5 -179.4(2) . . . . ?
C9 C4 C5 C6 0.8(4) . . . . ?
C3 C4 C5 C6 -179.4(2) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C6 C7 C8 C10 179.9(3) . . . . ?
C1 N1 C9 C4 -0.2(4) . . . . ?
C1 N1 C9 C8 -179.8(2) . . . . ?
C5 C4 C9 N1 179.2(2) . . . . ?
C3 C4 C9 N1 -0.6(4) . . . . ?
C5 C4 C9 C8 -1.1(4) . . . . ?
C3 C4 C9 C8 179.1(2) . . . . ?
C7 C8 C9 N1 -179.5(2) . . . . ?
C10 C8 C9 N1 0.3(4) . . . . ?
C7 C8 C9 C4 0.8(4) . . . . ?
C10 C8 C9 C4 -179.3(2) . . . . ?
N3 N2 C11 C2 -174.6(2) . . . . ?
C3 C2 C11 N2 6.6(4) . . . . ?
C1 C2 C11 N2 -176.6(2) . . . . ?
N2 N3 C12 O2 -170.4(3) . . . . ?
N2 N3 C12 N4 10.5(4) . . . . ?
C13 N4 C12 O2 6.9(5) . . . . ?
C13 N4 C12 N3 -174.0(3) . . . . ?
C12 N4 C13 C14 161.1(3) . . . . ?
C12 N4 C13 C18 -18.6(5) . . . . ?
C18 C13 C14 C15 1.1(5) . . . . ?
N4 C13 C14 C15 -178.7(3) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C14 C13 C18 C17 -1.5(5) . . . . ?
N4 C13 C18 C17 178.3(3) . . . . ?
C16 C17 C18 C13 1.1(6) . . . . ?

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
O3 H3 O2 0.84 1.96 2.737(3) 154.3 .
N1 H1A O3 0.88 2.08 2.929(3) 161.0 7_666
N3 H3B O1 0.88 1.97 2.838(3) 169.2 7_666
N4 H4N O2 0.88 2.50 3.203(3) 137.0 1_545
C11 H11A O1 0.95 2.64 3.408(3) 138.7 7_666
C18 H18A O2 0.95 2.31 2.879(4) 118.1 .

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.091



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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1941780'
loop_
_audit_author_name
_audit_author_address
'Ray J Butcher'
;Howard University
United States of America
;
_audit_update_record             
;
2019-07-19 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 Cl2 Cu N4 O4'
_chemical_formula_sum            'C19 H22 Cl2 Cu N4 O4'
_chemical_formula_weight         504.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.3965(18)
_cell_length_b                   9.957(2)
_cell_length_c                   13.900(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.053(4)
_cell_angle_gamma                90
_cell_volume                     1023.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4723
_cell_measurement_theta_min      2.346
_cell_measurement_theta_max      25.123

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             518
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.363
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_T_max  0.768
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4229
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.516
_diffrn_reflns_theta_max         27.899
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             4229
_reflns_number_gt                3905
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.767
_reflns_Friedel_fraction_full    0.866

_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       'Bruker Apex 3'
_computing_cell_refinement       'Bruker Apex 3'
_computing_data_reduction        'Bruker Apex 3'
_computing_structure_solution    'Shelxt (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'Shelxtl (Sheldrick, 2008)'
_computing_publication_material  'Shelxtl (Sheldrick, 2008)'
_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)+(0.0478P)²] 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_abs_structure_details 
;
 Flack x determined using 1557 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.035(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4229
_refine_ls_number_parameters     285
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
Cu Cu 0.71956(7) 0.64491(5) 0.50762(4) 0.01375(15) Uani 1 1 d . . . . .
Cl1 Cl 0.75128(16) 0.86109(10) 0.54767(8) 0.0172(2) Uani 1 1 d . . . . .
Cl2 Cl 0.73559(18) 0.20821(11) 0.24068(8) 0.0198(3) Uani 1 1 d . . . . .
O1 O 0.8900(5) 0.5829(3) 0.6064(2) 0.0173(7) Uani 1 1 d . . . . .
O2 O 0.5875(5) 0.6844(3) 0.3855(2) 0.0172(7) Uani 1 1 d . . . . .
O1W O 0.4723(5) 0.5692(4) 0.5895(3) 0.0239(8) Uani 1 1 d D . . . .
H1W1 H 0.415(9) 0.503(5) 0.572(5) 0.05(2) Uiso 1 1 d D . . . .
H1W2 H 0.413(8) 0.603(6) 0.632(4) 0.04(2) Uiso 1 1 d D . . . .
N1 N 0.9943(6) 0.4436(4) 0.7212(3) 0.0151(8) Uani 1 1 d . . . . .
H1A H 1.030781 0.515552 0.752802 0.06(2) Uiso 1 1 calc R . . . .
N2 N 0.7170(5) 0.4629(4) 0.4506(3) 0.0137(8) Uani 1 1 d . . . . .
N3 N 0.6357(6) 0.4626(4) 0.3608(3) 0.0152(8) Uani 1 1 d . . . . .
H3B H 0.629764 0.390476 0.324360 0.08(3) Uiso 1 1 calc R . . . .
N4 N 0.4763(6) 0.5825(4) 0.2480(3) 0.0158(8) Uani 1 1 d . . . . .
H4A H 0.442044 0.503565 0.225830 0.033(18) Uiso 1 1 calc R . . . .
O1S O 0.3813(6) 0.3359(4) 0.1560(3) 0.0287(9) Uani 1 1 d . . . . .
H1S H 0.472272 0.291889 0.174603 0.043 Uiso 1 1 calc R U . . .
C1 C 0.9115(7) 0.4625(4) 0.6343(3) 0.0143(9) Uani 1 1 d . . . . .
C1S C 0.2164(9) 0.2654(6) 0.1841(5) 0.0323(14) Uani 1 1 d . . . . .
H1S1 H 0.221500 0.247055 0.253376 0.048 Uiso 1 1 calc R U . . .
H1S2 H 0.206658 0.180428 0.148759 0.048 Uiso 1 1 calc R U . . .
H1S3 H 0.110743 0.321444 0.168968 0.048 Uiso 1 1 calc R U . . .
C2 C 0.8584(6) 0.3424(4) 0.5815(3) 0.0134(9) Uani 1 1 d . . . . .
C3 C 0.8948(7) 0.2189(4) 0.6191(3) 0.0155(10) Uani 1 1 d . . . . .
H3A H 0.864048 0.141293 0.582614 0.019 Uiso 1 1 calc R U . . .
C4 C 0.9775(7) 0.2027(5) 0.7115(3) 0.0141(9) Uani 1 1 d . . . . .
C5 C 1.0137(7) 0.0747(5) 0.7518(4) 0.0187(10) Uani 1 1 d . . . . .
H5A H 0.984180 -0.004492 0.716722 0.022 Uiso 1 1 calc R U . . .
C6 C 1.0918(7) 0.0660(4) 0.8417(4) 0.0206(11) Uani 1 1 d . . . . .
H6A H 1.118702 -0.019429 0.868842 0.025 Uiso 1 1 calc R U . . .
C7 C 1.1319(7) 0.1834(5) 0.8939(4) 0.0189(10) Uani 1 1 d . . . . .
H7A H 1.184432 0.174824 0.956458 0.023 Uiso 1 1 calc R U . . .
C8 C 1.0986(7) 0.3106(5) 0.8584(4) 0.0156(9) Uani 1 1 d . . . . .
C9 C 1.1350(8) 0.4339(5) 0.9181(4) 0.0214(11) Uani 1 1 d . . . . .
H9A H 1.191815 0.407635 0.979543 0.032 Uiso 1 1 calc R U . . .
H9B H 1.020859 0.480307 0.930200 0.032 Uiso 1 1 calc R U . . .
H9C H 1.216212 0.494023 0.883569 0.032 Uiso 1 1 calc R U . . .
C10 C 1.0259(7) 0.3192(4) 0.7642(4) 0.0156(10) Uani 1 1 d . . . . .
C11 C 0.7723(6) 0.3525(5) 0.4863(3) 0.0150(9) Uani 1 1 d . . . . .
H11A H 0.756979 0.272811 0.449417 0.018 Uiso 1 1 calc R U . . .
C12 C 0.5655(7) 0.5824(5) 0.3331(4) 0.0155(9) Uani 1 1 d . . . . .
C13 C 0.4312(7) 0.6945(5) 0.1900(3) 0.0164(9) Uani 1 1 d . . . . .
C14 C 0.4576(7) 0.8276(5) 0.2187(4) 0.0179(10) Uani 1 1 d . . . . .
H14A H 0.500982 0.847784 0.281781 0.021 Uiso 1 1 calc R U . . .
C15 C 0.4192(8) 0.9308(5) 0.1531(4) 0.0220(11) Uani 1 1 d . . . . .
H15A H 0.435513 1.021487 0.172602 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3584(7) 0.9037(5) 0.0610(4) 0.0217(11) Uani 1 1 d . . . . .
H16A H 0.336017 0.974762 0.016709 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3301(8) 0.7705(5) 0.0335(4) 0.0232(11) Uani 1 1 d . . . . .
H17A H 0.285567 0.750801 -0.029434 0.028 Uiso 1 1 calc R U . . .
C18 C 0.3665(7) 0.6670(5) 0.0973(3) 0.0181(10) Uani 1 1 d . . . . .
H18A H 0.347353 0.576584 0.077836 0.022 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
Cu O1 1.947(3) . ?
Cu N2 1.978(4) . ?
Cu O2 1.982(3) . ?
Cu Cl1 2.2346(12) . ?
Cu O1W 2.299(4) . ?
O1 C1 1.269(6) . ?
O2 C12 1.259(6) . ?
O1W H1W1 0.82(3) . ?
O1W H1W2 0.81(3) . ?
N1 C1 1.357(6) . ?
N1 C10 1.393(6) . ?
N1 H1A 0.8800 . ?
N2 C11 1.271(6) . ?
N2 N3 1.375(5) . ?
N3 C12 1.354(6) . ?
N3 H3B 0.8800 . ?
N4 C12 1.343(6) . ?
N4 C13 1.413(6) . ?
N4 H4A 0.8800 . ?
O1S C1S 1.467(7) . ?
O1S H1S 0.8400 . ?
C1 C2 1.453(6) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
C2 C3 1.361(6) . ?
C2 C11 1.461(6) . ?
C3 C4 1.421(7) . ?
C3 H3A 0.9500 . ?
C4 C10 1.414(6) . ?
C4 C5 1.416(6) . ?
C5 C6 1.371(7) . ?
C5 H5A 0.9500 . ?
C6 C7 1.404(7) . ?
C6 H6A 0.9500 . ?
C7 C8 1.380(7) . ?
C7 H7A 0.9500 . ?
C8 C10 1.409(7) . ?
C8 C9 1.504(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9500 . ?
C13 C18 1.393(7) . ?
C13 C14 1.396(6) . ?
C14 C15 1.399(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.376(7) . ?
C15 H15A 0.9500 . ?
C16 C17 1.395(7) . ?
C16 H16A 0.9500 . ?
C17 C18 1.383(7) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?

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
O1 Cu N2 89.61(15) . . ?
O1 Cu O2 165.73(14) . . ?
N2 Cu O2 80.66(15) . . ?
O1 Cu Cl1 93.80(10) . . ?
N2 Cu Cl1 169.28(12) . . ?
O2 Cu Cl1 94.02(9) . . ?
O1 Cu O1W 93.28(15) . . ?
N2 Cu O1W 84.04(15) . . ?
O2 Cu O1W 96.04(15) . . ?
Cl1 Cu O1W 105.87(10) . . ?
C1 O1 Cu 126.2(3) . . ?
C12 O2 Cu 113.1(3) . . ?
Cu O1W H1W1 122(4) . . ?
Cu O1W H1W2 131(4) . . ?
H1W1 O1W H1W2 106(4) . . ?
C1 N1 C10 125.0(4) . . ?
C1 N1 H1A 117.5 . . ?
C10 N1 H1A 117.5 . . ?
C11 N2 N3 119.0(4) . . ?
C11 N2 Cu 129.5(3) . . ?
N3 N2 Cu 111.5(3) . . ?
C12 N3 N2 114.6(4) . . ?
C12 N3 H3B 122.7 . . ?
N2 N3 H3B 122.7 . . ?
C12 N4 C13 127.6(4) . . ?
C12 N4 H4A 116.2 . . ?
C13 N4 H4A 116.2 . . ?
C1S O1S H1S 109.5 . . ?
O1 C1 N1 117.0(4) . . ?
O1 C1 C2 126.3(4) . . ?
N1 C1 C2 116.7(4) . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 C11 119.4(4) . . ?
C1 C2 C11 120.7(4) . . ?
C2 C3 C4 121.9(4) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C10 C4 C5 119.3(4) . . ?
C10 C4 C3 118.4(4) . . ?
C5 C4 C3 122.3(4) . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C8 C7 C6 123.0(5) . . ?
C8 C7 H7A 118.5 . . ?
C6 C7 H7A 118.5 . . ?
C7 C8 C10 116.8(5) . . ?
C7 C8 C9 121.5(5) . . ?
C10 C8 C9 121.7(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C8 120.7(4) . . ?
N1 C10 C4 117.9(4) . . ?
C8 C10 C4 121.3(4) . . ?
N2 C11 C2 123.0(4) . . ?
N2 C11 H11A 118.5 . . ?
C2 C11 H11A 118.5 . . ?
O2 C12 N4 124.4(4) . . ?
O2 C12 N3 120.1(4) . . ?
N4 C12 N3 115.5(4) . . ?
C18 C13 C14 119.7(4) . . ?
C18 C13 N4 116.5(4) . . ?
C14 C13 N4 123.8(5) . . ?
C13 C14 C15 119.0(5) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C16 C15 C14 121.4(5) . . ?
C16 C15 H15A 119.3 . . ?
C14 C15 H15A 119.3 . . ?
C15 C16 C17 119.0(5) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C17 C18 C13 120.4(4) . . ?
C17 C18 H18A 119.8 . . ?
C13 C18 H18A 119.8 . . ?

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
C11 N2 N3 C12 173.7(4) . . . . ?
Cu N2 N3 C12 -3.9(5) . . . . ?
Cu O1 C1 N1 -160.8(3) . . . . ?
Cu O1 C1 C2 20.2(7) . . . . ?
C10 N1 C1 O1 178.6(4) . . . . ?
C10 N1 C1 C2 -2.3(7) . . . . ?
O1 C1 C2 C3 178.1(4) . . . . ?
N1 C1 C2 C3 -0.9(7) . . . . ?
O1 C1 C2 C11 0.5(7) . . . . ?
N1 C1 C2 C11 -178.5(4) . . . . ?
C1 C2 C3 C4 2.7(7) . . . . ?
C11 C2 C3 C4 -179.7(4) . . . . ?
C2 C3 C4 C10 -1.3(7) . . . . ?
C2 C3 C4 C5 179.2(5) . . . . ?
C10 C4 C5 C6 1.3(8) . . . . ?
C3 C4 C5 C6 -179.2(5) . . . . ?
C4 C5 C6 C7 1.2(8) . . . . ?
C5 C6 C7 C8 -0.9(8) . . . . ?
C6 C7 C8 C10 -1.9(8) . . . . ?
C6 C7 C8 C9 177.0(5) . . . . ?
C1 N1 C10 C8 -174.3(5) . . . . ?
C1 N1 C10 C4 3.7(7) . . . . ?
C7 C8 C10 N1 -177.6(4) . . . . ?
C9 C8 C10 N1 3.5(7) . . . . ?
C7 C8 C10 C4 4.5(8) . . . . ?
C9 C8 C10 C4 -174.5(4) . . . . ?
C5 C4 C10 N1 177.8(4) . . . . ?
C3 C4 C10 N1 -1.8(7) . . . . ?
C5 C4 C10 C8 -4.2(8) . . . . ?
C3 C4 C10 C8 176.2(4) . . . . ?
N3 N2 C11 C2 -179.3(4) . . . . ?
Cu N2 C11 C2 -2.1(7) . . . . ?
C3 C2 C11 N2 172.4(5) . . . . ?
C1 C2 C11 N2 -10.0(7) . . . . ?
Cu O2 C12 N4 178.3(4) . . . . ?
Cu O2 C12 N3 -2.5(6) . . . . ?
C13 N4 C12 O2 17.1(8) . . . . ?
C13 N4 C12 N3 -162.1(5) . . . . ?
N2 N3 C12 O2 4.4(7) . . . . ?
N2 N3 C12 N4 -176.3(4) . . . . ?
C12 N4 C13 C18 169.1(5) . . . . ?
C12 N4 C13 C14 -7.1(8) . . . . ?
C18 C13 C14 C15 -0.3(8) . . . . ?
N4 C13 C14 C15 175.8(5) . . . . ?
C13 C14 C15 C16 -0.8(8) . . . . ?
C14 C15 C16 C17 1.7(8) . . . . ?
C15 C16 C17 C18 -1.4(8) . . . . ?
C16 C17 C18 C13 0.3(8) . . . . ?
C14 C13 C18 C17 0.6(8) . . . . ?
N4 C13 C18 C17 -175.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1W1 Cl1 0.82(3) 2.49(4) 3.248(4) 154(6) 2_646 yes
O1W H1W2 Cl2 0.81(3) 2.35(3) 3.160(4) 175(6) 2_656 yes
N1 H1A Cl2 0.88 2.58 3.343(4) 145.2 2_756 yes
N3 H3B Cl2 0.88 2.30 3.130(4) 157.2 . yes
N4 H4A O1S 0.88 1.98 2.851(5) 170.7 . yes
O1S H1S Cl2 0.84 2.29 3.124(4) 169.1 . yes
C11 H11A Cl2 0.95 2.97 3.709(5) 135.3 . yes
C14 H14A O2 0.95 2.26 2.873(6) 121.6 . yes
C18 H18A O1S 0.95 2.64 3.397(6) 136.9 . yes

_refine_diff_density_max         1.417
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.089



