# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1-DMA
_database_code_depnum_ccdc_archive 'CCDC 2111529'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2021-09-23 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '1,10-phenanthrolinium pamoate DMA solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 O6, C12 H9 N2, C4 H9 N O'
_chemical_formula_sum            'C39 H33 N3 O7'
_chemical_formula_weight         655.68

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   11.035(2)
_cell_length_b                   11.907(2)
_cell_length_c                   13.273(3)
_cell_angle_alpha                81.380(2)
_cell_angle_beta                 70.064(2)
_cell_angle_gamma                71.719(2)
_cell_volume                     1555.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      29.00

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52350
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.087
_diffrn_reflns_theta_max         29.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8339
_reflns_number_gt                6055
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.6656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         8339
_refine_ls_number_parameters     461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.70490(11) 0.61078(10) -0.01698(9) 0.0211(2) Uani 1 1 d . . . . .
O2 O 0.51709(11) 0.74850(10) 0.06192(9) 0.0233(3) Uani 1 1 d . . . . .
C3 C 0.63350(15) 0.68470(14) 0.05614(12) 0.0174(3) Uani 1 1 d . . . . .
C4 C 0.69456(15) 0.69253(13) 0.13913(11) 0.0149(3) Uani 1 1 d . . . . .
C5 C 0.82087(15) 0.62093(13) 0.13640(11) 0.0149(3) Uani 1 1 d . . . . .
H5 H 0.870670 0.568201 0.079887 0.018 Uiso 1 1 calc R U . . .
C6 C 0.87762(14) 0.62455(13) 0.21619(12) 0.0149(3) Uani 1 1 d . . . . .
C7 C 1.00900(15) 0.55183(14) 0.21222(12) 0.0184(3) Uani 1 1 d . . . . .
H7 H 1.060280 0.500925 0.154526 0.022 Uiso 1 1 calc R U . . .
C8 C 1.06187(16) 0.55475(15) 0.29086(14) 0.0224(3) Uani 1 1 d . . . . .
H8 H 1.149104 0.505301 0.288263 0.027 Uiso 1 1 calc R U . . .
C9 C 0.98643(16) 0.63149(15) 0.37597(13) 0.0214(3) Uani 1 1 d . . . . .
H9 H 1.023824 0.633240 0.430251 0.026 Uiso 1 1 calc R U . . .
C10 C 0.86024(15) 0.70349(14) 0.38164(12) 0.0171(3) Uani 1 1 d . . . . .
H10 H 0.812355 0.755397 0.438993 0.021 Uiso 1 1 calc R U . . .
C11 C 0.79966(14) 0.70171(13) 0.30280(12) 0.0146(3) Uani 1 1 d . . . . .
C12 C 0.66700(14) 0.77370(13) 0.30812(11) 0.0139(3) Uani 1 1 d . . . . .
C13 C 0.61930(14) 0.77231(13) 0.22429(12) 0.0145(3) Uani 1 1 d . . . . .
O14 O 0.49738(10) 0.84725(10) 0.22388(9) 0.0182(2) Uani 1 1 d . . . . .
H14 H 0.487(3) 0.827(3) 0.161(3) 0.086(10) Uiso 1 1 d . . . . .
H28 H 0.652(3) 0.614(2) 0.909(2) 0.081(9) Uiso 1 1 d . . . . .
C15 C 0.57711(15) 0.84889(13) 0.40397(11) 0.0154(3) Uani 1 1 d . . . . .
H15A H 0.625800 0.900355 0.415645 0.018 Uiso 1 1 calc R U . . .
H15B H 0.495886 0.900743 0.387357 0.018 Uiso 1 1 calc R U . . .
C16 C 0.53423(14) 0.77500(13) 0.50686(12) 0.0144(3) Uani 1 1 d . . . . .
C17 C 0.44984(14) 0.70111(13) 0.51776(11) 0.0143(3) Uani 1 1 d . . . . .
C18 C 0.38905(15) 0.70180(13) 0.43858(12) 0.0163(3) Uani 1 1 d . . . . .
H18 H 0.405376 0.752130 0.375747 0.020 Uiso 1 1 calc R U . . .
C19 C 0.30721(15) 0.63088(14) 0.45161(12) 0.0186(3) Uani 1 1 d . . . . .
H19 H 0.267587 0.633370 0.397715 0.022 Uiso 1 1 calc R U . . .
C20 C 0.28085(15) 0.55456(14) 0.54324(13) 0.0200(3) Uani 1 1 d . . . . .
H20 H 0.224289 0.505811 0.551045 0.024 Uiso 1 1 calc R U . . .
C21 C 0.33766(15) 0.55147(13) 0.62084(12) 0.0177(3) Uani 1 1 d . . . . .
H21 H 0.320507 0.499718 0.682546 0.021 Uiso 1 1 calc R U . . .
C22 C 0.42189(14) 0.62425(13) 0.61088(11) 0.0152(3) Uani 1 1 d . . . . .
C23 C 0.48003(15) 0.62152(13) 0.69126(12) 0.0166(3) Uani 1 1 d . . . . .
H23 H 0.467953 0.566056 0.750635 0.020 Uiso 1 1 calc R U . . .
C24 C 0.55376(15) 0.69773(13) 0.68502(11) 0.0163(3) Uani 1 1 d . . . . .
C25 C 0.57760(14) 0.77721(13) 0.59305(12) 0.0155(3) Uani 1 1 d . . . . .
O26 O 0.64806(11) 0.85486(10) 0.58767(9) 0.0203(2) Uani 1 1 d . . . . .
H26 H 0.664(2) 0.843(2) 0.651(2) 0.055(7) Uiso 1 1 d . . . . .
C27 C 0.61209(15) 0.69593(14) 0.77239(12) 0.0186(3) Uani 1 1 d . . . . .
O28 O 0.60075(11) 0.61217(10) 0.84555(9) 0.0216(2) Uani 1 1 d . . . . .
O29 O 0.66784(12) 0.77282(11) 0.77128(9) 0.0258(3) Uani 1 1 d . . . . .
N30 N 0.08494(13) 0.81996(12) 0.09814(11) 0.0183(3) Uani 1 1 d . . . . .
H30 H 0.041(2) 0.872(2) 0.1546(19) 0.048(7) Uiso 1 1 d . . . . .
C31 C 0.20812(16) 0.75166(14) 0.09349(14) 0.0220(3) Uani 1 1 d . . . . .
H31 H 0.247697 0.759189 0.144540 0.026 Uiso 1 1 calc R U . . .
C32 C 0.27915(17) 0.66959(15) 0.01472(14) 0.0247(4) Uani 1 1 d . . . . .
H32 H 0.367695 0.622141 0.010402 0.030 Uiso 1 1 calc R U . . .
C33 C 0.21868(17) 0.65837(15) -0.05697(13) 0.0236(3) Uani 1 1 d . . . . .
H33 H 0.264666 0.600431 -0.109478 0.028 Uiso 1 1 calc R U . . .
C34 C 0.08947(16) 0.73177(14) -0.05341(12) 0.0201(3) Uani 1 1 d . . . . .
C35 C 0.02318(15) 0.81450(13) 0.02685(12) 0.0175(3) Uani 1 1 d . . . . .
C36 C -0.10828(15) 0.89289(14) 0.03543(13) 0.0186(3) Uani 1 1 d . . . . .
N37 N -0.16510(13) 0.97057(12) 0.11509(11) 0.0212(3) Uani 1 1 d . . . . .
C38 C -0.28790(17) 1.04062(15) 0.12296(15) 0.0261(4) Uani 1 1 d . . . . .
H38 H -0.329994 1.094773 0.178856 0.031 Uiso 1 1 calc R U . . .
C39 C -0.35913(18) 1.03948(16) 0.05378(15) 0.0294(4) Uani 1 1 d . . . . .
H39 H -0.446574 1.092048 0.062651 0.035 Uiso 1 1 calc R U . . .
C40 C -0.30090(18) 0.96160(16) -0.02664(15) 0.0284(4) Uani 1 1 d . . . . .
H40 H -0.347423 0.959978 -0.074626 0.034 Uiso 1 1 calc R U . . .
C41 C -0.17140(17) 0.88366(15) -0.03807(13) 0.0223(3) Uani 1 1 d . . . . .
C42 C -0.10320(18) 0.79651(16) -0.11833(13) 0.0260(4) Uani 1 1 d . . . . .
H42 H -0.146627 0.789477 -0.166821 0.031 Uiso 1 1 calc R U . . .
C43 C 0.02126(18) 0.72459(15) -0.12604(13) 0.0248(4) Uani 1 1 d . . . . .
H43 H 0.064331 0.668439 -0.180270 0.030 Uiso 1 1 calc R U . . .
O44 O 0.95764(12) 1.07622(11) 0.72831(10) 0.0275(3) Uani 1 1 d . . . . .
C45 C 1.01554(17) 0.98459(15) 0.67673(13) 0.0221(3) Uani 1 1 d . . . . .
C46 C 1.16211(17) 0.92347(17) 0.66110(14) 0.0285(4) Uani 1 1 d . . . . .
H46A H 1.200359 0.972564 0.687541 0.043 Uiso 1 1 calc R U . . .
H46B H 1.209832 0.911398 0.584608 0.043 Uiso 1 1 calc R U . . .
H46C H 1.171552 0.846647 0.700981 0.043 Uiso 1 1 calc R U . . .
N47 N 0.94773(14) 0.94270(12) 0.63202(11) 0.0225(3) Uani 1 1 d . . . . .
C48 C 0.9989(2) 0.82988(16) 0.58043(16) 0.0330(4) Uani 1 1 d . . . . .
H48A H 1.092766 0.793705 0.577860 0.050 Uiso 1 1 calc R U . . .
H48B H 0.993244 0.843273 0.507287 0.050 Uiso 1 1 calc R U . . .
H48C H 0.944991 0.776873 0.621499 0.050 Uiso 1 1 calc R U . . .
C49 C 0.80642(17) 1.00621(15) 0.64649(14) 0.0251(4) Uani 1 1 d . . . . .
H49A H 0.750045 0.976684 0.713055 0.038 Uiso 1 1 calc R U . . .
H49B H 0.781897 0.993455 0.585636 0.038 Uiso 1 1 calc R U . . .
H49C H 0.792647 1.091036 0.650490 0.038 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 C3 1.2794(19) . ?
O2 C3 1.2536(19) . ?
C3 C4 1.501(2) . ?
C4 C5 1.379(2) . ?
C4 C13 1.434(2) . ?
C5 C6 1.414(2) . ?
C6 C7 1.424(2) . ?
C6 C11 1.433(2) . ?
C7 C8 1.367(2) . ?
C8 C9 1.412(2) . ?
C9 C10 1.371(2) . ?
C10 C11 1.427(2) . ?
C11 C12 1.429(2) . ?
C12 C13 1.388(2) . ?
C12 C15 1.526(2) . ?
C13 O14 1.3626(17) . ?
C15 C16 1.524(2) . ?
C16 C25 1.389(2) . ?
C16 C17 1.431(2) . ?
C17 C18 1.425(2) . ?
C17 C22 1.428(2) . ?
C18 C19 1.374(2) . ?
C19 C20 1.408(2) . ?
C20 C21 1.367(2) . ?
C21 C22 1.421(2) . ?
C22 C23 1.412(2) . ?
C23 C24 1.374(2) . ?
C24 C25 1.430(2) . ?
C24 C27 1.501(2) . ?
C25 O26 1.3632(18) . ?
C27 O29 1.2490(19) . ?
C27 O28 1.2877(19) . ?
N30 C31 1.333(2) . ?
N30 C35 1.3602(19) . ?
C31 C32 1.389(2) . ?
C32 C33 1.377(2) . ?
C33 C34 1.409(2) . ?
C34 C35 1.404(2) . ?
C34 C43 1.436(2) . ?
C35 C36 1.435(2) . ?
C36 N37 1.358(2) . ?
C36 C41 1.411(2) . ?
N37 C38 1.328(2) . ?
C38 C39 1.401(2) . ?
C39 C40 1.366(3) . ?
C40 C41 1.410(2) . ?
C41 C42 1.440(2) . ?
C42 C43 1.350(3) . ?
O44 C45 1.247(2) . ?
C45 N47 1.337(2) . ?
C45 C46 1.506(2) . ?
N47 C48 1.459(2) . ?
N47 C49 1.463(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C3 O1 123.61(14) . . ?
O2 C3 C4 119.47(14) . . ?
O1 C3 C4 116.91(13) . . ?
C5 C4 C13 119.49(13) . . ?
C5 C4 C3 120.64(13) . . ?
C13 C4 C3 119.84(13) . . ?
C4 C5 C6 121.19(13) . . ?
C5 C6 C7 121.07(13) . . ?
C5 C6 C11 118.78(13) . . ?
C7 C6 C11 120.15(13) . . ?
C8 C7 C6 120.48(14) . . ?
C7 C8 C9 119.83(15) . . ?
C10 C9 C8 121.19(14) . . ?
C9 C10 C11 121.05(14) . . ?
C10 C11 C12 122.25(13) . . ?
C10 C11 C6 117.29(13) . . ?
C12 C11 C6 120.46(13) . . ?
C13 C12 C11 118.40(13) . . ?
C13 C12 C15 119.90(13) . . ?
C11 C12 C15 121.69(13) . . ?
O14 C13 C12 119.17(13) . . ?
O14 C13 C4 119.39(13) . . ?
C12 C13 C4 121.43(13) . . ?
C16 C15 C12 112.99(12) . . ?
C25 C16 C17 118.01(13) . . ?
C25 C16 C15 120.35(13) . . ?
C17 C16 C15 121.64(13) . . ?
C18 C17 C22 117.35(13) . . ?
C18 C17 C16 122.25(13) . . ?
C22 C17 C16 120.39(13) . . ?
C19 C18 C17 121.06(14) . . ?
C18 C19 C20 121.33(14) . . ?
C21 C20 C19 119.20(14) . . ?
C20 C21 C22 121.21(14) . . ?
C23 C22 C21 121.23(14) . . ?
C23 C22 C17 118.93(13) . . ?
C21 C22 C17 119.84(13) . . ?
C24 C23 C22 121.09(14) . . ?
C23 C24 C25 119.46(13) . . ?
C23 C24 C27 120.54(13) . . ?
C25 C24 C27 119.98(13) . . ?
O26 C25 C16 118.72(13) . . ?
O26 C25 C24 119.65(13) . . ?
C16 C25 C24 121.59(13) . . ?
O29 C27 O28 123.73(14) . . ?
O29 C27 C24 120.07(14) . . ?
O28 C27 C24 116.21(13) . . ?
C31 N30 C35 122.61(14) . . ?
N30 C31 C32 120.63(15) . . ?
C33 C32 C31 118.69(16) . . ?
C32 C33 C34 120.79(15) . . ?
C35 C34 C33 118.05(14) . . ?
C35 C34 C43 118.51(15) . . ?
C33 C34 C43 123.42(15) . . ?
N30 C35 C34 119.17(14) . . ?
N30 C35 C36 119.41(14) . . ?
C34 C35 C36 121.42(14) . . ?
N37 C36 C41 124.01(15) . . ?
N37 C36 C35 117.69(14) . . ?
C41 C36 C35 118.30(15) . . ?
C38 N37 C36 116.70(14) . . ?
N37 C38 C39 123.95(17) . . ?
C40 C39 C38 118.99(16) . . ?
C39 C40 C41 119.68(16) . . ?
C40 C41 C36 116.65(16) . . ?
C40 C41 C42 123.80(15) . . ?
C36 C41 C42 119.54(15) . . ?
C43 C42 C41 121.29(15) . . ?
C42 C43 C34 120.92(16) . . ?
O44 C45 N47 119.55(15) . . ?
O44 C45 C46 120.60(15) . . ?
N47 C45 C46 119.81(15) . . ?
C45 N47 C48 124.77(15) . . ?
C45 N47 C49 118.30(14) . . ?
C48 N47 C49 116.49(14) . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.054


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_1-THF
_database_code_depnum_ccdc_archive 'CCDC 2111532'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2021-09-23 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '1,10-phenanthrolinium pamoate THF solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 O6, C12 H9 N2, C4 H8 O'
_chemical_formula_sum            'C39 H32 N2 O7'
_chemical_formula_weight         640.66

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.653(3)
_cell_length_b                   11.153(3)
_cell_length_c                   13.566(4)
_cell_angle_alpha                85.062(4)
_cell_angle_beta                 74.512(3)
_cell_angle_gamma                72.396(3)
_cell_volume                     1480.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    108(2)
_cell_measurement_reflns_used    3702
_cell_measurement_theta_min      2.256
_cell_measurement_theta_max      28.263

_exptl_crystal_description       Shard
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.964
_exptl_transmission_factor_max   0.996
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'symmetry-related measurements'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      108(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focused sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18042
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.916
_diffrn_reflns_theta_max         28.829
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7068
_reflns_number_gt                4852
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_publication_material  
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'

_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)+(0.1108P)²+1.0964P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   Difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7068
_refine_ls_number_parameters     449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.2175
_refine_ls_wR_factor_gt          0.1946
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.5931(2) 0.64862(19) 0.85616(13) 0.0299(4) Uani 1 1 d . . . . .
N1 N 0.1190(2) 0.8090(2) 0.13712(18) 0.0304(5) Uani 1 1 d . . . . .
C1 C 0.6211(2) 0.7243(2) 0.78215(17) 0.0230(5) Uani 1 1 d . . . . .
O2 O 0.68853(19) 0.79717(18) 0.78294(13) 0.0293(4) Uani 1 1 d . . . . .
N2 N -0.1338(2) 0.9697(2) 0.14058(17) 0.0311(5) Uani 1 1 d . . . . .
C2 C 0.5662(2) 0.7199(2) 0.69237(16) 0.0195(5) Uani 1 1 d . . . . .
O3 O 0.67836(17) 0.86981(16) 0.60111(13) 0.0226(4) Uani 1 1 d . . . . .
C3 C 0.5979(2) 0.7948(2) 0.60363(17) 0.0184(5) Uani 1 1 d . . . . .
O4 O 0.69745(19) 0.64397(18) -0.00187(13) 0.0300(4) Uani 1 1 d . . . . .
C4 C 0.5503(2) 0.7910(2) 0.51835(16) 0.0170(4) Uani 1 1 d . . . . .
O5 O 0.51887(18) 0.80128(18) 0.07172(13) 0.0293(4) Uani 1 1 d . . . . .
C5 C 0.4601(2) 0.7175(2) 0.52374(16) 0.0172(4) Uani 1 1 d . . . . .
O6 O 0.50127(16) 0.88016(16) 0.24523(13) 0.0224(4) Uani 1 1 d . . . . .
C6 C 0.3950(2) 0.7188(2) 0.44453(17) 0.0198(5) Uani 1 1 d . . . . .
H6 H 0.4111 0.7707 0.3860 0.024 Uiso 1 1 calc R U . . .
O7 O 0.0470(3) 0.9254(2) 0.3215(2) 0.0554(6) Uani 1 1 d . . . . .
C7 C 0.3097(2) 0.6465(2) 0.45137(18) 0.0238(5) Uani 1 1 d . . . . .
H7 H 0.2670 0.6494 0.3977 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2842(2) 0.5677(2) 0.53666(19) 0.0246(5) Uani 1 1 d . . . . .
H8 H 0.2265 0.5165 0.5394 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3425(2) 0.5653(2) 0.61512(18) 0.0227(5) Uani 1 1 d . . . . .
H9 H 0.3249 0.5123 0.6726 0.027 Uiso 1 1 calc R U . . .
C10 C 0.4295(2) 0.6414(2) 0.61167(17) 0.0190(5) Uani 1 1 d . . . . .
C11 C 0.4860(2) 0.6433(2) 0.69380(17) 0.0200(5) Uani 1 1 d . . . . .
H11 H 0.4684 0.5905 0.7515 0.024 Uiso 1 1 calc R U . . .
C12 C 0.5929(2) 0.8655(2) 0.42279(16) 0.0173(4) Uani 1 1 d . . . . .
H12A H 0.6473 0.9167 0.4372 0.021 Uiso 1 1 calc R U . . .
H12B H 0.5101 0.9242 0.4069 0.021 Uiso 1 1 calc R U . . .
C13 C 0.6313(3) 0.7223(2) 0.07011(17) 0.0229(5) Uani 1 1 d . . . . .
C14 C 0.6942(2) 0.7153(2) 0.15778(16) 0.0179(4) Uani 1 1 d . . . . .
C15 C 0.6232(2) 0.7947(2) 0.24459(16) 0.0166(4) Uani 1 1 d . . . . .
C16 C 0.6756(2) 0.7851(2) 0.32914(16) 0.0162(4) Uani 1 1 d . . . . .
C17 C 0.8084(2) 0.7011(2) 0.32461(16) 0.0160(4) Uani 1 1 d . . . . .
C18 C 0.8732(2) 0.6922(2) 0.40531(17) 0.0186(5) Uani 1 1 d . . . . .
H18 H 0.8274 0.7431 0.4643 0.022 Uiso 1 1 calc R U . . .
C19 C 1.0006(2) 0.6113(2) 0.39902(18) 0.0217(5) Uani 1 1 d . . . . .
H19 H 1.0420 0.6072 0.4537 0.026 Uiso 1 1 calc R U . . .
C20 C 1.0715(2) 0.5338(2) 0.31287(19) 0.0244(5) Uani 1 1 d . . . . .
H20 H 1.1592 0.4772 0.3102 0.029 Uiso 1 1 calc R U . . .
C21 C 1.0137(2) 0.5406(2) 0.23329(19) 0.0228(5) Uani 1 1 d . . . . .
H21 H 1.0620 0.4892 0.1749 0.027 Uiso 1 1 calc R U . . .
C22 C 0.8817(2) 0.6239(2) 0.23701(16) 0.0171(4) Uani 1 1 d . . . . .
C23 C 0.8208(2) 0.6320(2) 0.15523(16) 0.0187(5) Uani 1 1 d . . . . .
H23 H 0.8677 0.5793 0.0974 0.022 Uiso 1 1 calc R U . . .
C24 C 0.2420(3) 0.7336(3) 0.1376(3) 0.0378(7) Uani 1 1 d . . . . .
H24 H 0.2797 0.7403 0.1922 0.045 Uiso 1 1 calc R U . . .
C25 C 0.3174(3) 0.6463(3) 0.0625(2) 0.0374(7) Uani 1 1 d . . . . .
H25 H 0.4051 0.5933 0.0649 0.045 Uiso 1 1 calc R U . . .
C26 C 0.2601(3) 0.6382(3) -0.0178(3) 0.0400(7) Uani 1 1 d . . . . .
H26 H 0.3099 0.5795 -0.0713 0.048 Uiso 1 1 calc R U . . .
C27 C 0.1294(3) 0.7167(3) -0.0195(2) 0.0341(6) Uani 1 1 d . . . . .
C28 C 0.0634(3) 0.7110(3) -0.0986(2) 0.0378(7) Uani 1 1 d . . . . .
H28 H 0.1090 0.6526 -0.1528 0.045 Uiso 1 1 calc R U . . .
C29 C -0.0625(3) 0.7880(3) -0.0960(2) 0.0359(6) Uani 1 1 d . . . . .
H29 H -0.1055 0.7817 -0.1475 0.043 Uiso 1 1 calc R U . . .
C30 C -0.1313(3) 0.8784(2) -0.0170(2) 0.0297(6) Uani 1 1 d . . . . .
C31 C -0.2617(3) 0.9626(3) -0.0115(2) 0.0340(6) Uani 1 1 d . . . . .
H31 H -0.3064 0.9615 -0.0632 0.041 Uiso 1 1 calc R U . . .
C32 C -0.3245(3) 1.0456(3) 0.0672(2) 0.0365(6) Uani 1 1 d . . . . .
H32 H -0.4127 1.1021 0.0712 0.044 Uiso 1 1 calc R U . . .
C33 C -0.2562(3) 1.0457(3) 0.1416(2) 0.0354(6) Uani 1 1 d . . . . .
H33 H -0.3003 1.1037 0.1962 0.043 Uiso 1 1 calc R U . . .
C34 C -0.0705(3) 0.8864(2) 0.0617(2) 0.0276(5) Uani 1 1 d . . . . .
C35 C 0.0612(3) 0.8025(3) 0.0593(2) 0.0301(6) Uani 1 1 d . . . . .
C36 C -0.0923(4) 0.9883(3) 0.3573(4) 0.0614(11) Uani 1 1 d . . . . .
H36A H -0.1256 0.9646 0.4294 0.074 Uiso 1 1 calc R U . . .
H36B H -0.1446 0.9642 0.3160 0.074 Uiso 1 1 calc R U . . .
H3O H 0.694(4) 0.861(3) 0.664(3) 0.057(11) Uiso 1 1 d . . . . .
H6O H 0.488(3) 0.867(3) 0.184(3) 0.039(9) Uiso 1 1 d . . . . .
H1O H 0.633(5) 0.650(5) 0.898(4) 0.098(17) Uiso 1 1 d . . . . .
H1N H 0.045(2) 0.882(2) 0.1965(17) 0.008(5) Uiso 1 1 d . . . . .
C37 C -0.1112(3) 1.1216(3) 0.3493(3) 0.0445(7) Uani 1 1 d . . . . .
H37A H -0.1918 1.1674 0.4020 0.053 Uiso 1 1 calc R U . . .
H37B H -0.1223 1.1536 0.2808 0.053 Uiso 1 1 calc R U . . .
C38 C 0.0194(3) 1.1348(3) 0.3667(3) 0.0470(8) Uani 1 1 d . . . . .
H38A H 0.0095 1.1481 0.4400 0.056 Uiso 1 1 calc R U . . .
H38B H 0.0458 1.2055 0.3262 0.056 Uiso 1 1 calc R U . . .
C39 C 0.1239(3) 1.0078(3) 0.3296(3) 0.0437(7) Uani 1 1 d . . . . .
H39B H 0.1853 1.0179 0.2624 0.052 Uiso 1 1 calc R U . . .
H39A H 0.1796 0.9737 0.3792 0.052 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 1.287(3) . ?
O1 H1O 0.79(5) . ?
N1 C24 1.327(4) . ?
N1 C35 1.374(3) . ?
N1 H1N 1.15(2) . ?
C1 O2 1.239(3) . ?
C1 C2 1.495(3) . ?
N2 C33 1.320(4) . ?
N2 C34 1.368(3) . ?
C2 C11 1.375(3) . ?
C2 C3 1.429(3) . ?
O3 C3 1.360(3) . ?
O3 H3O 0.91(4) . ?
C3 C4 1.390(3) . ?
O4 C13 1.273(3) . ?
C4 C5 1.424(3) . ?
C4 C12 1.519(3) . ?
O5 C13 1.249(3) . ?
C5 C6 1.423(3) . ?
C5 C10 1.427(3) . ?
O6 C15 1.358(3) . ?
O6 H6O 0.90(3) . ?
C6 C7 1.368(3) . ?
C6 H6 0.9500 . ?
O7 C36 1.405(4) . ?
O7 C39 1.432(4) . ?
C7 C8 1.409(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.363(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.425(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(3) . ?
C11 H11 0.9500 . ?
C12 C16 1.522(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.500(3) . ?
C14 C23 1.380(3) . ?
C14 C15 1.429(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.430(3) . ?
C17 C18 1.424(3) . ?
C17 C22 1.427(3) . ?
C18 C19 1.369(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.411(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.365(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.423(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.411(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.405(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.408(4) . ?
C26 H26 0.9500 . ?
C27 C35 1.389(4) . ?
C27 C28 1.445(4) . ?
C28 C29 1.349(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.423(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.409(4) . ?
C30 C34 1.410(4) . ?
C31 C32 1.363(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.394(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.425(4) . ?
C36 C37 1.437(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.523(4) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.539(5) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39B 0.9900 . ?
C39 H39A 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 O1 H1O 110(4) . . ?
C24 N1 C35 120.3(3) . . ?
C24 N1 H1N 129.2(11) . . ?
C35 N1 H1N 110.4(11) . . ?
O2 C1 O1 123.7(2) . . ?
O2 C1 C2 120.8(2) . . ?
O1 C1 C2 115.5(2) . . ?
C33 N2 C34 118.0(2) . . ?
C11 C2 C3 119.3(2) . . ?
C11 C2 C1 120.6(2) . . ?
C3 C2 C1 120.1(2) . . ?
C3 O3 H3O 104(2) . . ?
O3 C3 C4 118.9(2) . . ?
O3 C3 C2 119.72(19) . . ?
C4 C3 C2 121.4(2) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 C12 120.07(19) . . ?
C5 C4 C12 121.44(18) . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 C10 117.6(2) . . ?
C4 C5 C10 120.2(2) . . ?
C15 O6 H6O 103(2) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C36 O7 C39 108.8(3) . . ?
C6 C7 C8 121.1(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 C5 119.1(2) . . ?
C9 C10 C5 119.8(2) . . ?
C2 C11 C10 121.3(2) . . ?
C2 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C4 C12 C16 114.24(18) . . ?
C4 C12 H12A 108.7 . . ?
C16 C12 H12A 108.7 . . ?
C4 C12 H12B 108.7 . . ?
C16 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
O5 C13 O4 124.0(2) . . ?
O5 C13 C14 119.6(2) . . ?
O4 C13 C14 116.4(2) . . ?
C23 C14 C15 119.62(19) . . ?
C23 C14 C13 120.3(2) . . ?
C15 C14 C13 120.1(2) . . ?
O6 C15 C16 119.1(2) . . ?
O6 C15 C14 119.58(19) . . ?
C16 C15 C14 121.3(2) . . ?
C15 C16 C17 118.5(2) . . ?
C15 C16 C12 119.72(19) . . ?
C17 C16 C12 121.73(18) . . ?
C18 C17 C22 117.6(2) . . ?
C18 C17 C16 122.0(2) . . ?
C22 C17 C16 120.39(19) . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 121.2(2) . . ?
C23 C22 C17 118.9(2) . . ?
C21 C22 C17 120.0(2) . . ?
C14 C23 C22 121.1(2) . . ?
C14 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
N1 C24 C25 123.0(3) . . ?
N1 C24 H24 118.5 . . ?
C25 C24 H24 118.5 . . ?
C24 C25 C26 117.6(3) . . ?
C24 C25 H25 121.2 . . ?
C26 C25 H25 121.2 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C35 C27 C26 117.9(3) . . ?
C35 C27 C28 119.0(3) . . ?
C26 C27 C28 123.1(3) . . ?
C29 C28 C27 120.6(3) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.7(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C34 116.6(3) . . ?
C31 C30 C29 123.1(3) . . ?
C34 C30 C29 120.3(3) . . ?
C32 C31 C30 120.7(3) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 118.4(3) . . ?
C31 C32 H32 120.8 . . ?
C33 C32 H32 120.8 . . ?
N2 C33 C32 123.8(3) . . ?
N2 C33 H33 118.1 . . ?
C32 C33 H33 118.1 . . ?
N2 C34 C30 122.5(2) . . ?
N2 C34 C35 119.1(2) . . ?
C30 C34 C35 118.4(2) . . ?
N1 C35 C27 120.8(2) . . ?
N1 C35 C34 118.2(2) . . ?
C27 C35 C34 121.0(2) . . ?
O7 C36 C37 108.9(3) . . ?
O7 C36 H36A 109.9 . . ?
C37 C36 H36A 109.9 . . ?
O7 C36 H36B 109.9 . . ?
C37 C36 H36B 109.9 . . ?
H36A C36 H36B 108.3 . . ?
C36 C37 C38 103.3(3) . . ?
C36 C37 H37A 111.1 . . ?
C38 C37 H37A 111.1 . . ?
C36 C37 H37B 111.1 . . ?
C38 C37 H37B 111.1 . . ?
H37A C37 H37B 109.1 . . ?
C37 C38 C39 102.9(3) . . ?
C37 C38 H38A 111.2 . . ?
C39 C38 H38A 111.2 . . ?
C37 C38 H38B 111.2 . . ?
C39 C38 H38B 111.2 . . ?
H38A C38 H38B 109.1 . . ?
O7 C39 C38 106.3(3) . . ?
O7 C39 H39B 110.5 . . ?
C38 C39 H39B 110.5 . . ?
O7 C39 H39A 110.5 . . ?
C38 C39 H39A 110.5 . . ?
H39B C39 H39A 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C11 -176.9(2) . . . . ?
O1 C1 C2 C11 3.0(3) . . . . ?
O2 C1 C2 C3 3.7(3) . . . . ?
O1 C1 C2 C3 -176.4(2) . . . . ?
C11 C2 C3 O3 -179.2(2) . . . . ?
C1 C2 C3 O3 0.2(3) . . . . ?
C11 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 C4 178.8(2) . . . . ?
O3 C3 C4 C5 -176.6(2) . . . . ?
C2 C3 C4 C5 4.7(3) . . . . ?
O3 C3 C4 C12 2.5(3) . . . . ?
C2 C3 C4 C12 -176.2(2) . . . . ?
C3 C4 C5 C6 173.1(2) . . . . ?
C12 C4 C5 C6 -6.0(3) . . . . ?
C3 C4 C5 C10 -5.4(3) . . . . ?
C12 C4 C5 C10 175.51(19) . . . . ?
C4 C5 C6 C7 179.5(2) . . . . ?
C10 C5 C6 C7 -2.0(3) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 1.6(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C11 177.5(2) . . . . ?
C8 C9 C10 C5 -2.3(4) . . . . ?
C6 C5 C10 C11 -176.5(2) . . . . ?
C4 C5 C10 C11 2.1(3) . . . . ?
C6 C5 C10 C9 3.3(3) . . . . ?
C4 C5 C10 C9 -178.1(2) . . . . ?
C3 C2 C11 C10 -2.9(3) . . . . ?
C1 C2 C11 C10 177.7(2) . . . . ?
C9 C10 C11 C2 -177.7(2) . . . . ?
C5 C10 C11 C2 2.1(3) . . . . ?
C3 C4 C12 C16 116.6(2) . . . . ?
C5 C4 C12 C16 -64.4(3) . . . . ?
O5 C13 C14 C23 -177.4(2) . . . . ?
O4 C13 C14 C23 3.5(3) . . . . ?
O5 C13 C14 C15 2.7(3) . . . . ?
O4 C13 C14 C15 -176.4(2) . . . . ?
C23 C14 C15 O6 177.29(19) . . . . ?
C13 C14 C15 O6 -2.8(3) . . . . ?
C23 C14 C15 C16 -3.6(3) . . . . ?
C13 C14 C15 C16 176.3(2) . . . . ?
O6 C15 C16 C17 -175.61(19) . . . . ?
C14 C15 C16 C17 5.3(3) . . . . ?
O6 C15 C16 C12 2.9(3) . . . . ?
C14 C15 C16 C12 -176.17(19) . . . . ?
C4 C12 C16 C15 115.9(2) . . . . ?
C4 C12 C16 C17 -65.6(3) . . . . ?
C15 C16 C17 C18 175.6(2) . . . . ?
C12 C16 C17 C18 -2.9(3) . . . . ?
C15 C16 C17 C22 -3.5(3) . . . . ?
C12 C16 C17 C22 178.01(19) . . . . ?
C22 C17 C18 C19 -0.7(3) . . . . ?
C16 C17 C18 C19 -179.8(2) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 1.1(4) . . . . ?
C19 C20 C21 C22 -0.8(4) . . . . ?
C20 C21 C22 C23 179.9(2) . . . . ?
C20 C21 C22 C17 -0.2(3) . . . . ?
C18 C17 C22 C23 -179.10(19) . . . . ?
C16 C17 C22 C23 0.0(3) . . . . ?
C18 C17 C22 C21 1.0(3) . . . . ?
C16 C17 C22 C21 -179.9(2) . . . . ?
C15 C14 C23 C22 0.0(3) . . . . ?
C13 C14 C23 C22 -179.9(2) . . . . ?
C21 C22 C23 C14 -178.3(2) . . . . ?
C17 C22 C23 C14 1.8(3) . . . . ?
C35 N1 C24 C25 -0.2(4) . . . . ?
N1 C24 C25 C26 0.2(4) . . . . ?
C24 C25 C26 C27 -0.6(4) . . . . ?
C25 C26 C27 C35 1.0(4) . . . . ?
C25 C26 C27 C28 -178.5(3) . . . . ?
C35 C27 C28 C29 0.1(4) . . . . ?
C26 C27 C28 C29 179.6(3) . . . . ?
C27 C28 C29 C30 1.7(4) . . . . ?
C28 C29 C30 C31 178.9(3) . . . . ?
C28 C29 C30 C34 -1.9(4) . . . . ?
C34 C30 C31 C32 -0.7(4) . . . . ?
C29 C30 C31 C32 178.5(3) . . . . ?
C30 C31 C32 C33 0.4(4) . . . . ?
C34 N2 C33 C32 0.1(4) . . . . ?
C31 C32 C33 N2 -0.1(4) . . . . ?
C33 N2 C34 C30 -0.5(4) . . . . ?
C33 N2 C34 C35 -179.4(2) . . . . ?
C31 C30 C34 N2 0.8(4) . . . . ?
C29 C30 C34 N2 -178.5(2) . . . . ?
C31 C30 C34 C35 179.7(2) . . . . ?
C29 C30 C34 C35 0.4(4) . . . . ?
C24 N1 C35 C27 0.6(4) . . . . ?
C24 N1 C35 C34 -179.3(2) . . . . ?
C26 C27 C35 N1 -1.0(4) . . . . ?
C28 C27 C35 N1 178.6(2) . . . . ?
C26 C27 C35 C34 178.9(2) . . . . ?
C28 C27 C35 C34 -1.5(4) . . . . ?
N2 C34 C35 N1 0.1(3) . . . . ?
C30 C34 C35 N1 -178.8(2) . . . . ?
N2 C34 C35 C27 -179.8(2) . . . . ?
C30 C34 C35 C27 1.3(4) . . . . ?
C39 O7 C36 C37 23.4(4) . . . . ?
O7 C36 C37 C38 -32.0(4) . . . . ?
C36 C37 C38 C39 27.6(4) . . . . ?
C36 O7 C39 C38 -4.3(4) . . . . ?
C37 C38 C39 O7 -14.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O2 0.91(4) 1.69(4) 2.549(2) 156(3) .
O6 H6O O5 0.90(3) 1.66(3) 2.524(2) 159(3) .
O1 H1O O4 0.79(5) 1.67(5) 2.458(2) 171(6) 1_556
N1 H1N O7 1.15(2) 1.81(2) 2.732(4) 133.8(17) .

_refine_diff_density_max         1.007
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-4





#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_1-DMF
_database_code_depnum_ccdc_archive 'CCDC 2111530'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2021-09-23 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            '1,10-phenanthrolinium pamoate DMF solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 O6, C12 H9 N2, C3 H7 N O'
_chemical_formula_sum            'C38 H31 N3 O7'
_chemical_formula_weight         641.66

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.6989(18)
_cell_length_b                   11.630(2)
_cell_length_c                   13.421(2)
_cell_angle_alpha                82.162(5)
_cell_angle_beta                 72.106(5)
_cell_angle_gamma                72.058(5)
_cell_volume                     1510.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.6344
_exptl_transmission_factor_max   0.7208
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'symmetry-related measurements'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53114
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         28.355
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7485
_reflns_number_gt                5803
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.6159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         7485
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1480
_refine_ls_wR_factor_gt          0.1335
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.81966(13) 0.70830(11) 0.22509(9) 0.0342(3) Uani 1 1 d . . . . .
O2 O 0.89956(12) 0.86441(11) 0.14875(8) 0.0308(3) Uani 1 1 d . . . . .
C3 C 0.88204(15) 0.78398(14) 0.22301(11) 0.0242(3) Uani 1 1 d . . . . .
C4 C 0.94014(14) 0.78415(13) 0.31147(10) 0.0207(3) Uani 1 1 d . . . . .
C5 C 1.01552(15) 0.86194(13) 0.30771(11) 0.0219(3) Uani 1 1 d . . . . .
H5 H 1.029404 0.916783 0.248809 0.026 Uiso 1 1 calc R U . . .
C6 C 1.07295(14) 0.86237(13) 0.38935(11) 0.0206(3) Uani 1 1 d . . . . .
C7 C 1.15453(15) 0.94058(14) 0.38400(12) 0.0247(3) Uani 1 1 d . . . . .
H7 H 1.171143 0.993684 0.324164 0.030 Uiso 1 1 calc R U . . .
C8 C 1.20927(16) 0.94049(15) 0.46347(12) 0.0269(3) Uani 1 1 d . . . . .
H8 H 1.262038 0.994215 0.459642 0.032 Uiso 1 1 calc R U . . .
C9 C 1.18665(15) 0.85946(14) 0.55181(12) 0.0252(3) Uani 1 1 d . . . . .
H9 H 1.226954 0.857694 0.606177 0.030 Uiso 1 1 calc R U . . .
C10 C 1.10782(14) 0.78382(13) 0.56008(11) 0.0210(3) Uani 1 1 d . . . . .
H10 H 1.094449 0.730326 0.620031 0.025 Uiso 1 1 calc R U . . .
C11 C 1.04522(13) 0.78384(12) 0.48014(10) 0.0181(3) Uani 1 1 d . . . . .
C12 C 0.95876(14) 0.70916(12) 0.48831(10) 0.0181(3) Uani 1 1 d . . . . .
C13 C 0.91358(14) 0.70546(12) 0.40254(11) 0.0195(3) Uani 1 1 d . . . . .
O14 O 0.83848(11) 0.62826(10) 0.40624(8) 0.0252(2) Uani 1 1 d . . . . .
H14 H 0.822(3) 0.641(2) 0.339(2) 0.066(7) Uiso 1 1 d . . . . .
C15 C 0.91200(14) 0.63723(12) 0.58967(10) 0.0195(3) Uani 1 1 d . . . . .
H15A H 0.857432 0.587930 0.578092 0.023 Uiso 1 1 calc R U . . .
H15B H 0.993591 0.581099 0.607504 0.023 Uiso 1 1 calc R U . . .
C16 C 0.82660(14) 0.71684(12) 0.68177(10) 0.0178(3) Uani 1 1 d . . . . .
C17 C 0.69460(14) 0.79753(12) 0.68373(10) 0.0172(3) Uani 1 1 d . . . . .
C18 C 0.63099(15) 0.80217(13) 0.60354(11) 0.0207(3) Uani 1 1 d . . . . .
H18 H 0.676384 0.748876 0.547528 0.025 Uiso 1 1 calc R U . . .
C19 C 0.50557(15) 0.88211(14) 0.60582(12) 0.0249(3) Uani 1 1 d . . . . .
H19 H 0.466058 0.883896 0.550975 0.030 Uiso 1 1 calc R U . . .
C20 C 0.43418(15) 0.96182(14) 0.68834(13) 0.0271(3) Uani 1 1 d . . . . .
H20 H 0.347921 1.017492 0.688383 0.033 Uiso 1 1 calc R U . . .
C21 C 0.48983(15) 0.95855(14) 0.76834(12) 0.0240(3) Uani 1 1 d . . . . .
H21 H 0.440993 1.011275 0.824432 0.029 Uiso 1 1 calc R U . . .
C22 C 0.62024(14) 0.87687(12) 0.76835(10) 0.0186(3) Uani 1 1 d . . . . .
C23 C 0.67928(15) 0.87262(13) 0.85009(10) 0.0202(3) Uani 1 1 d . . . . .
H23 H 0.631626 0.925968 0.905869 0.024 Uiso 1 1 calc R U . . .
C24 C 0.80422(15) 0.79286(13) 0.85047(10) 0.0199(3) Uani 1 1 d . . . . .
C25 C 0.87710(14) 0.71234(12) 0.76630(10) 0.0190(3) Uani 1 1 d . . . . .
O26 O 0.99894(11) 0.63066(10) 0.76835(8) 0.0250(2) Uani 1 1 d . . . . .
H26 H 1.011(2) 0.649(2) 0.831(2) 0.062(7) Uiso 1 1 d . . . . .
H30 H 0.580(2) 0.348(2) 0.1720(18) 0.048(6) Uiso 1 1 d . . . . .
C27 C 0.86567(16) 0.79069(14) 0.93751(11) 0.0233(3) Uani 1 1 d . . . . .
O28 O 0.97881(12) 0.71777(11) 0.93757(9) 0.0330(3) Uani 1 1 d . . . . .
O29 O 0.79619(12) 0.86739(10) 1.00850(8) 0.0309(3) Uani 1 1 d . . . . .
N30 N 0.61666(13) 0.29923(12) 0.11780(11) 0.0248(3) Uani 1 1 d . . . . .
C31 C 0.73944(16) 0.22330(15) 0.11529(14) 0.0307(3) Uani 1 1 d . . . . .
H31 H 0.781502 0.224487 0.167874 0.037 Uiso 1 1 calc R U . . .
C32 C 0.80583(18) 0.14247(15) 0.03578(15) 0.0358(4) Uani 1 1 d . . . . .
H32 H 0.893425 0.088034 0.033568 0.043 Uiso 1 1 calc R U . . .
C33 C 0.74388(18) 0.14184(15) -0.03959(14) 0.0339(4) Uani 1 1 d . . . . .
H33 H 0.788691 0.086111 -0.093823 0.041 Uiso 1 1 calc R U . . .
C34 C 0.61466(17) 0.22281(14) -0.03752(12) 0.0282(3) Uani 1 1 d . . . . .
C35 C 0.5440(2) 0.22690(16) -0.11381(13) 0.0356(4) Uani 1 1 d . . . . .
H35 H 0.585623 0.173243 -0.169745 0.043 Uiso 1 1 calc R U . . .
C36 C 0.4193(2) 0.30580(16) -0.10732(13) 0.0359(4) Uani 1 1 d . . . . .
H36 H 0.374200 0.306198 -0.158311 0.043 Uiso 1 1 calc R U . . .
C37 C 0.35406(17) 0.38912(15) -0.02443(12) 0.0290(3) Uani 1 1 d . . . . .
C38 C 0.22376(19) 0.47277(17) -0.01366(14) 0.0369(4) Uani 1 1 d . . . . .
H38 H 0.175387 0.477634 -0.063485 0.044 Uiso 1 1 calc R U . . .
C39 C 0.16776(18) 0.54676(17) 0.06913(15) 0.0383(4) Uani 1 1 d . . . . .
H39 H 0.079963 0.603391 0.077666 0.046 Uiso 1 1 calc R U . . .
C40 C 0.24170(17) 0.53795(15) 0.14137(14) 0.0330(4) Uani 1 1 d . . . . .
H40 H 0.201176 0.589773 0.198636 0.040 Uiso 1 1 calc R U . . .
N41 N 0.36480(13) 0.46152(11) 0.13438(10) 0.0265(3) Uani 1 1 d . . . . .
C42 C 0.41949(16) 0.38793(13) 0.05253(12) 0.0240(3) Uani 1 1 d . . . . .
C43 C 0.55138(15) 0.30294(13) 0.04456(11) 0.0232(3) Uani 1 1 d . . . . .
O44 O 0.62864(14) 0.39454(12) 0.28293(11) 0.0448(3) Uani 1 1 d . . . . .
C45 C 0.61803(18) 0.48442(15) 0.32642(13) 0.0330(4) Uani 1 1 d . . . . .
H45 H 0.700623 0.497265 0.328595 0.040 Uiso 1 1 calc R U . . .
N46 N 0.50172(14) 0.56595(13) 0.37099(11) 0.0323(3) Uani 1 1 d . . . . .
C47 C 0.5008(2) 0.67126(18) 0.41832(17) 0.0464(5) Uani 1 1 d . . . . .
H47A H 0.594391 0.666261 0.417065 0.070 Uiso 1 1 calc R U . . .
H47B H 0.443086 0.673985 0.491016 0.070 Uiso 1 1 calc R U . . .
H47C H 0.464297 0.744662 0.378846 0.070 Uiso 1 1 calc R U . . .
C48 C 0.3703(2) 0.5553(2) 0.37032(18) 0.0493(5) Uani 1 1 d . . . . .
H48A H 0.384875 0.487535 0.328015 0.074 Uiso 1 1 calc R U . . .
H48B H 0.320161 0.630345 0.340249 0.074 Uiso 1 1 calc R U . . .
H48C H 0.317138 0.540952 0.442241 0.074 Uiso 1 1 calc R U . . .
H1 H 0.850(4) 0.860(3) 0.084(3) 0.118(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2508(19) . ?
O2 C3 1.2816(19) . ?
O2 H1 1.17(4) . ?
C3 C4 1.5002(19) . ?
C4 C5 1.372(2) . ?
C4 C13 1.433(2) . ?
C5 C6 1.413(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.424(2) . ?
C6 C11 1.4311(19) . ?
C7 C8 1.365(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.418(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.368(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4286(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.4243(19) . ?
C12 C13 1.3888(19) . ?
C12 C15 1.5264(19) . ?
C13 O14 1.3645(17) . ?
O14 H14 0.96(3) . ?
C15 C16 1.5221(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C25 1.3875(19) . ?
C16 C17 1.4294(19) . ?
C17 C18 1.4269(19) . ?
C17 C22 1.4327(19) . ?
C18 C19 1.371(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.412(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.370(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.426(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.4131(19) . ?
C23 C24 1.373(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.435(2) . ?
C24 C27 1.5004(19) . ?
C25 O26 1.3617(17) . ?
O26 H26 0.94(3) . ?
C27 O28 1.2459(19) . ?
C27 O29 1.2822(19) . ?
N30 C31 1.331(2) . ?
N30 C43 1.359(2) . ?
N30 H30 0.90(2) . ?
C31 C32 1.387(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.371(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.407(2) . ?
C33 H33 0.9500 . ?
C34 C43 1.405(2) . ?
C34 C35 1.436(2) . ?
C35 C36 1.351(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.437(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.411(2) . ?
C37 C42 1.411(2) . ?
C38 C39 1.367(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.404(3) . ?
C39 H39 0.9500 . ?
C40 N41 1.326(2) . ?
C40 H40 0.9500 . ?
N41 C42 1.355(2) . ?
C42 C43 1.434(2) . ?
O44 C45 1.224(2) . ?
C45 N46 1.333(2) . ?
C45 H45 0.9500 . ?
N46 C47 1.451(2) . ?
N46 C48 1.452(2) . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 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
C3 O2 H1 112.4(17) . . ?
O1 C3 O2 123.73(13) . . ?
O1 C3 C4 119.82(13) . . ?
O2 C3 C4 116.45(13) . . ?
C5 C4 C13 119.25(13) . . ?
C5 C4 C3 120.59(13) . . ?
C13 C4 C3 120.13(13) . . ?
C4 C5 C6 121.55(13) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 121.53(13) . . ?
C5 C6 C11 118.66(13) . . ?
C7 C6 C11 119.80(13) . . ?
C8 C7 C6 121.06(14) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 119.41(14) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 121.14(13) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 121.16(13) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 122.39(12) . . ?
C12 C11 C6 120.24(12) . . ?
C10 C11 C6 117.36(13) . . ?
C13 C12 C11 118.58(12) . . ?
C13 C12 C15 119.96(12) . . ?
C11 C12 C15 121.43(12) . . ?
O14 C13 C12 119.45(12) . . ?
O14 C13 C4 119.19(12) . . ?
C12 C13 C4 121.32(13) . . ?
C13 O14 H14 103.4(15) . . ?
C16 C15 C12 113.21(11) . . ?
C16 C15 H15A 108.9 . . ?
C12 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C12 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C25 C16 C17 118.50(12) . . ?
C25 C16 C15 119.82(12) . . ?
C17 C16 C15 121.68(12) . . ?
C18 C17 C16 122.21(12) . . ?
C18 C17 C22 117.35(12) . . ?
C16 C17 C22 120.43(12) . . ?
C19 C18 C17 121.23(13) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 121.07(13) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 119.72(14) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.72(13) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 121.43(13) . . ?
C23 C22 C17 118.70(12) . . ?
C21 C22 C17 119.87(12) . . ?
C24 C23 C22 121.28(13) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 119.71(12) . . ?
C23 C24 C27 120.40(13) . . ?
C25 C24 C27 119.89(13) . . ?
O26 C25 C16 119.07(12) . . ?
O26 C25 C24 119.69(12) . . ?
C16 C25 C24 121.23(12) . . ?
C25 O26 H26 101.8(15) . . ?
O28 C27 O29 123.63(13) . . ?
O28 C27 C24 120.06(13) . . ?
O29 C27 C24 116.31(13) . . ?
C31 N30 C43 123.02(14) . . ?
C31 N30 H30 114.7(14) . . ?
C43 N30 H30 122.3(14) . . ?
N30 C31 C32 119.90(16) . . ?
N30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 119.39(16) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C34 120.74(15) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C43 C34 C33 117.80(15) . . ?
C43 C34 C35 118.57(15) . . ?
C33 C34 C35 123.62(15) . . ?
C36 C35 C34 121.08(16) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C35 C36 C37 120.95(16) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
C38 C37 C42 116.84(16) . . ?
C38 C37 C36 123.25(16) . . ?
C42 C37 C36 119.90(15) . . ?
C39 C38 C37 119.38(16) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
C38 C39 C40 119.12(16) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
N41 C40 C39 123.85(17) . . ?
N41 C40 H40 118.1 . . ?
C39 C40 H40 118.1 . . ?
C40 N41 C42 116.79(14) . . ?
N41 C42 C37 124.02(14) . . ?
N41 C42 C43 117.73(14) . . ?
C37 C42 C43 118.25(14) . . ?
N30 C43 C34 119.14(14) . . ?
N30 C43 C42 119.61(13) . . ?
C34 C43 C42 121.25(14) . . ?
O44 C45 N46 126.25(17) . . ?
O44 C45 H45 116.9 . . ?
N46 C45 H45 116.9 . . ?
C45 N46 C47 121.80(15) . . ?
C45 N46 C48 121.04(15) . . ?
C47 N46 C48 117.11(15) . . ?
N46 C47 H47A 109.5 . . ?
N46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
N46 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
N46 C48 H48A 109.5 . . ?
N46 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
N46 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 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
O1 C3 C4 C5 176.28(14) . . . . ?
O2 C3 C4 C5 -4.2(2) . . . . ?
O1 C3 C4 C13 -5.7(2) . . . . ?
O2 C3 C4 C13 173.78(13) . . . . ?
C13 C4 C5 C6 3.0(2) . . . . ?
C3 C4 C5 C6 -179.02(13) . . . . ?
C4 C5 C6 C7 178.11(13) . . . . ?
C4 C5 C6 C11 -3.3(2) . . . . ?
C5 C6 C7 C8 179.83(14) . . . . ?
C11 C6 C7 C8 1.2(2) . . . . ?
C6 C7 C8 C9 1.2(2) . . . . ?
C7 C8 C9 C10 -1.8(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 -177.75(13) . . . . ?
C9 C10 C11 C6 2.5(2) . . . . ?
C5 C6 C11 C12 -1.4(2) . . . . ?
C7 C6 C11 C12 177.21(13) . . . . ?
C5 C6 C11 C10 178.29(12) . . . . ?
C7 C6 C11 C10 -3.07(19) . . . . ?
C10 C11 C12 C13 -173.42(12) . . . . ?
C6 C11 C12 C13 6.29(19) . . . . ?
C10 C11 C12 C15 8.5(2) . . . . ?
C6 C11 C12 C15 -171.78(12) . . . . ?
C11 C12 C13 O14 175.53(12) . . . . ?
C15 C12 C13 O14 -6.37(19) . . . . ?
C11 C12 C13 C4 -6.7(2) . . . . ?
C15 C12 C13 C4 171.43(12) . . . . ?
C5 C4 C13 O14 179.92(12) . . . . ?
C3 C4 C13 O14 1.92(19) . . . . ?
C5 C4 C13 C12 2.1(2) . . . . ?
C3 C4 C13 C12 -175.88(12) . . . . ?
C13 C12 C15 C16 -116.22(14) . . . . ?
C11 C12 C15 C16 61.82(17) . . . . ?
C12 C15 C16 C25 -113.86(14) . . . . ?
C12 C15 C16 C17 65.84(16) . . . . ?
C25 C16 C17 C18 -175.76(12) . . . . ?
C15 C16 C17 C18 4.5(2) . . . . ?
C25 C16 C17 C22 3.65(19) . . . . ?
C15 C16 C17 C22 -176.05(12) . . . . ?
C16 C17 C18 C19 -178.58(13) . . . . ?
C22 C17 C18 C19 2.0(2) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
C18 C19 C20 C21 -0.9(2) . . . . ?
C19 C20 C21 C22 1.1(2) . . . . ?
C20 C21 C22 C23 179.79(14) . . . . ?
C20 C21 C22 C17 0.3(2) . . . . ?
C18 C17 C22 C23 178.70(12) . . . . ?
C16 C17 C22 C23 -0.74(19) . . . . ?
C18 C17 C22 C21 -1.76(19) . . . . ?
C16 C17 C22 C21 178.80(12) . . . . ?
C21 C22 C23 C24 179.24(13) . . . . ?
C17 C22 C23 C24 -1.2(2) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C22 C23 C24 C27 179.41(12) . . . . ?
C17 C16 C25 O26 176.05(12) . . . . ?
C15 C16 C25 O26 -4.24(19) . . . . ?
C17 C16 C25 C24 -4.69(19) . . . . ?
C15 C16 C25 C24 175.02(12) . . . . ?
C23 C24 C25 O26 -177.93(12) . . . . ?
C27 C24 C25 O26 2.91(19) . . . . ?
C23 C24 C25 C16 2.8(2) . . . . ?
C27 C24 C25 C16 -176.34(12) . . . . ?
C23 C24 C27 O28 179.72(13) . . . . ?
C25 C24 C27 O28 -1.1(2) . . . . ?
C23 C24 C27 O29 -0.9(2) . . . . ?
C25 C24 C27 O29 178.24(12) . . . . ?
C43 N30 C31 C32 -0.6(2) . . . . ?
N30 C31 C32 C33 0.0(2) . . . . ?
C31 C32 C33 C34 0.6(3) . . . . ?
C32 C33 C34 C43 -0.6(2) . . . . ?
C32 C33 C34 C35 -179.92(15) . . . . ?
C43 C34 C35 C36 0.0(2) . . . . ?
C33 C34 C35 C36 179.31(15) . . . . ?
C34 C35 C36 C37 0.7(2) . . . . ?
C35 C36 C37 C38 -179.60(15) . . . . ?
C35 C36 C37 C42 -0.9(2) . . . . ?
C42 C37 C38 C39 -0.3(2) . . . . ?
C36 C37 C38 C39 178.39(15) . . . . ?
C37 C38 C39 C40 0.2(2) . . . . ?
C38 C39 C40 N41 0.3(3) . . . . ?
C39 C40 N41 C42 -0.6(2) . . . . ?
C40 N41 C42 C37 0.5(2) . . . . ?
C40 N41 C42 C43 -178.82(13) . . . . ?
C38 C37 C42 N41 -0.1(2) . . . . ?
C36 C37 C42 N41 -178.82(14) . . . . ?
C38 C37 C42 C43 179.27(13) . . . . ?
C36 C37 C42 C43 0.5(2) . . . . ?
C31 N30 C43 C34 0.5(2) . . . . ?
C31 N30 C43 C42 -179.65(13) . . . . ?
C33 C34 C43 N30 0.0(2) . . . . ?
C35 C34 C43 N30 179.42(13) . . . . ?
C33 C34 C43 C42 -179.75(13) . . . . ?
C35 C34 C43 C42 -0.4(2) . . . . ?
N41 C42 C43 N30 -0.3(2) . . . . ?
C37 C42 C43 N30 -179.68(13) . . . . ?
N41 C42 C43 C34 179.51(13) . . . . ?
C37 C42 C43 C34 0.1(2) . . . . ?
O44 C45 N46 C47 -178.43(18) . . . . ?
O44 C45 N46 C48 -1.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O14 H14 O1 0.96(3) 1.62(3) 2.5272(16) 157(2) .
O26 H26 O28 0.94(3) 1.63(3) 2.5344(16) 159(2) .
N30 H30 O44 0.90(2) 1.91(2) 2.6624(19) 140(2) .
O2 H1 O29 1.17(4) 1.28(4) 2.4506(15) 173(3) 1_554

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_1-DMSO
_database_code_depnum_ccdc_archive 'CCDC 2111531'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2021-09-23 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '1,10-phenanthrolinium pamoate DMSO solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 O6, C12 H9 N2, C2 H6 O S'
_chemical_formula_sum            'C37 H30 N2 O7 S'
_chemical_formula_weight         646.69

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.5540(2)
_cell_length_b                   11.3682(2)
_cell_length_c                   13.7388(2)
_cell_angle_alpha                84.1650(10)
_cell_angle_beta                 74.5500(10)
_cell_angle_gamma                72.8520(10)
_cell_volume                     1517.71(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.07

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.547
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.185
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'symmetry-related measurements'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42307
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.538
_diffrn_reflns_theta_max         28.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7684
_reflns_number_gt                5478
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+0.5931P] 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         7684
_refine_ls_number_parameters     481
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.018
_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 0.68953(14) 0.66076(12) 0.00374(9) 0.0559(3) Uani 1 1 d . . . . .
N1 N 0.86841(15) -0.03661(14) 0.13532(11) 0.0448(3) Uani 1 1 d . . . . .
H1N H 0.905(2) -0.033(2) 0.1899(19) 0.079(7) Uiso 1 1 d . . . . .
C1 C 0.74650(19) 0.04272(18) 0.13770(15) 0.0533(4) Uani 1 1 d . . . . .
H1 H 0.703614 0.097892 0.191996 0.064 Uiso 1 1 calc R U . . .
O2 O 0.51579(13) 0.81594(13) 0.07639(9) 0.0556(3) Uani 1 1 d . . . . .
N2 N 1.12042(15) -0.19278(14) 0.13846(12) 0.0498(4) Uani 1 1 d . . . . .
C2 C 0.6813(2) 0.0458(2) 0.06179(16) 0.0596(5) Uani 1 1 d . . . . .
H2 H 0.594963 0.103489 0.063048 0.071 Uiso 1 1 calc R U . . .
O3 O 0.50089(12) 0.88514(12) 0.24936(9) 0.0481(3) Uani 1 1 d . . . . .
H3O H 0.484(3) 0.878(2) 0.188(2) 0.095(8) Uiso 1 1 d . . . . .
C3 C 0.7430(2) -0.0352(2) -0.01445(15) 0.0577(5) Uani 1 1 d . . . . .
H3 H 0.698733 -0.034346 -0.066469 0.069 Uiso 1 1 calc R U . . .
O4 O 0.69317(16) 0.81217(14) 0.77999(10) 0.0625(4) Uani 1 1 d . . . . .
C4 C 0.8708(2) -0.11990(18) -0.01739(13) 0.0500(4) Uani 1 1 d . . . . .
O5 O 0.59095(15) 0.67141(14) 0.85899(9) 0.0599(4) Uani 1 1 d . . . . .
H5O H 0.638(3) 0.679(3) 0.928(2) 0.121(10) Uiso 1 1 d . . . . .
C5 C 0.9386(3) -0.2086(2) -0.09378(15) 0.0651(6) Uani 1 1 d . . . . .
H5 H 0.896253 -0.212448 -0.145888 0.078 Uiso 1 1 calc R U . . .
O6 O 0.68478(13) 0.87745(11) 0.59774(9) 0.0471(3) Uani 1 1 d . . . . .
H6O H 0.698(3) 0.870(2) 0.661(2) 0.091(8) Uiso 1 1 d . . . . .
C6 C 1.0610(3) -0.2865(2) -0.09329(16) 0.0675(6) Uani 1 1 d . . . . .
H6 H 1.104530 -0.343932 -0.145927 0.081 Uiso 1 1 calc R U . . .
C7 C 1.1286(2) -0.28614(18) -0.01602(15) 0.0553(5) Uani 1 1 d . . . . .
C8 C 1.2555(2) -0.3667(2) -0.0114(2) 0.0711(6) Uani 1 1 d . . . . .
H8 H 1.302601 -0.426466 -0.061951 0.085 Uiso 1 1 calc R U . . .
C9 C 1.3117(2) -0.3598(2) 0.0652(2) 0.0734(6) Uani 1 1 d . . . . .
H9 H 1.397964 -0.414610 0.068810 0.088 Uiso 1 1 calc R U . . .
C10 C 1.2409(2) -0.2709(2) 0.13880(18) 0.0637(5) Uani 1 1 d . . . . .
H10 H 1.281732 -0.266594 0.191688 0.076 Uiso 1 1 calc R U . . .
C11 C 1.06462(17) -0.20085(16) 0.06214(13) 0.0441(4) Uani 1 1 d . . . . .
C12 C 0.93389(17) -0.11764(16) 0.06050(12) 0.0422(4) Uani 1 1 d . . . . .
C13 C 0.62556(17) 0.73514(16) 0.07558(11) 0.0402(4) Uani 1 1 d . . . . .
C14 C 0.68974(15) 0.72271(14) 0.16272(10) 0.0341(3) Uani 1 1 d . . . . .
C15 C 0.62234(15) 0.79930(14) 0.24808(11) 0.0340(3) Uani 1 1 d . . . . .
C16 C 0.67722(15) 0.78841(13) 0.33072(10) 0.0323(3) Uani 1 1 d . . . . .
C17 C 0.80859(15) 0.70361(13) 0.32601(10) 0.0314(3) Uani 1 1 d . . . . .
C18 C 0.87791(16) 0.69273(15) 0.40389(12) 0.0384(3) Uani 1 1 d . . . . .
H18 H 0.836423 0.744159 0.460702 0.046 Uiso 1 1 calc R U . . .
C19 C 1.00267(17) 0.60979(17) 0.39824(13) 0.0464(4) Uani 1 1 d . . . . .
H19 H 1.046307 0.604052 0.451435 0.056 Uiso 1 1 calc R U . . .
C20 C 1.06777(18) 0.53285(18) 0.31549(15) 0.0536(5) Uani 1 1 d . . . . .
H20 H 1.154140 0.474749 0.313288 0.064 Uiso 1 1 calc R U . . .
C21 C 1.00683(17) 0.54157(17) 0.23807(14) 0.0463(4) Uani 1 1 d . . . . .
H21 H 1.051773 0.490043 0.181604 0.056 Uiso 1 1 calc R U . . .
C22 C 0.87708(15) 0.62676(14) 0.24098(11) 0.0341(3) Uani 1 1 d . . . . .
C23 C 0.81342(16) 0.63842(15) 0.16084(11) 0.0364(3) Uani 1 1 d . . . . .
H23 H 0.857378 0.586649 0.104423 0.044 Uiso 1 1 calc R U . . .
C24 C 0.59862(16) 0.86750(14) 0.42260(11) 0.0360(3) Uani 1 1 d . . . . .
H24A H 0.656517 0.916455 0.434309 0.043 Uiso 1 1 calc R U . . .
H24B H 0.515811 0.926057 0.407049 0.043 Uiso 1 1 calc R U . . .
C25 C 0.55487(15) 0.79650(13) 0.51973(10) 0.0326(3) Uani 1 1 d . . . . .
C26 C 0.60208(15) 0.80361(14) 0.60351(11) 0.0347(3) Uani 1 1 d . . . . .
C27 C 0.56767(16) 0.73407(15) 0.69436(11) 0.0373(3) Uani 1 1 d . . . . .
C28 C 0.62255(17) 0.74120(17) 0.78296(12) 0.0434(4) Uani 1 1 d . . . . .
C29 C 0.48661(16) 0.65844(15) 0.69880(11) 0.0399(4) Uani 1 1 d . . . . .
H29 H 0.466246 0.610224 0.758448 0.048 Uiso 1 1 calc R U . . .
C30 C 0.43238(15) 0.65013(14) 0.61702(11) 0.0363(3) Uani 1 1 d . . . . .
C31 C 0.46458(14) 0.72243(14) 0.52784(11) 0.0329(3) Uani 1 1 d . . . . .
C32 C 0.35089(17) 0.56993(16) 0.62122(13) 0.0450(4) Uani 1 1 d . . . . .
H32 H 0.331062 0.521108 0.680577 0.054 Uiso 1 1 calc R U . . .
C33 C 0.30034(18) 0.56158(17) 0.54145(14) 0.0486(4) Uani 1 1 d . . . . .
H33 H 0.248136 0.505513 0.544160 0.058 Uiso 1 1 calc R U . . .
C34 C 0.32634(17) 0.63682(17) 0.45528(13) 0.0456(4) Uani 1 1 d . . . . .
H34 H 0.288638 0.632898 0.400550 0.055 Uiso 1 1 calc R U . . .
C35 C 0.40429(15) 0.71537(15) 0.44809(11) 0.0387(3) Uani 1 1 d . . . . .
H35 H 0.418651 0.766098 0.389142 0.046 Uiso 1 1 calc R U . . .
S1 S 0.95626(8) 0.02728(7) 0.38545(5) 0.0613(3) Uani 0.845(3) 1 d . . P A 1
O7 O 0.8824(3) 0.0323(3) 0.30515(19) 0.0893(9) Uani 0.845(3) 1 d . . P A 1
C36 C 0.9842(5) 0.1738(6) 0.3843(3) 0.0724(14) Uani 0.845(3) 1 d . . P A 1
H36A H 1.034793 0.192770 0.316540 0.109 Uiso 0.845(3) 1 calc R U P A 1
H36B H 1.037464 0.172985 0.433058 0.109 Uiso 0.845(3) 1 calc R U P A 1
H36C H 0.895960 0.236546 0.402681 0.109 Uiso 0.845(3) 1 calc R U P A 1
C37 C 1.1288(3) -0.0563(3) 0.3369(3) 0.0719(8) Uani 0.845(3) 1 d . . P A 1
H37A H 1.134181 -0.142666 0.329828 0.108 Uiso 0.845(3) 1 calc R U P A 1
H37B H 1.183192 -0.051175 0.383187 0.108 Uiso 0.845(3) 1 calc R U P A 1
H37C H 1.164537 -0.021306 0.270639 0.108 Uiso 0.845(3) 1 calc R U P A 1
S2 S 0.993(2) 0.056(2) 0.3305(19) 0.380(16) Uani 0.155(3) 1 d . . P A 2
O8 O 1.1013(19) -0.0232(19) 0.2723(12) 0.132(7) Uani 0.155(3) 1 d . . P A 2
C38 C 0.851(3) 0.039(3) 0.365(3) 0.148(15) Uani 0.155(3) 1 d . . P A 2
H38A H 0.854712 -0.044227 0.348651 0.222 Uiso 0.155(3) 1 calc R U P A 2
H38B H 0.789698 0.099712 0.329910 0.222 Uiso 0.155(3) 1 calc R U P A 2
H38C H 0.816845 0.049956 0.437839 0.222 Uiso 0.155(3) 1 calc R U P A 2
C39 C 0.979(5) 0.188(4) 0.380(4) 0.17(2) Uani 0.155(3) 1 d . . P A 2
H39A H 1.067580 0.206067 0.361257 0.249 Uiso 0.155(3) 1 calc R U P A 2
H39B H 0.948272 0.181906 0.453944 0.249 Uiso 0.155(3) 1 calc R U P A 2
H39C H 0.911446 0.254950 0.354712 0.249 Uiso 0.155(3) 1 calc R U P A 2


_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 C13 1.274(2) . ?
N1 C1 1.330(2) . ?
N1 C12 1.350(2) . ?
C1 C2 1.387(3) . ?
O2 C13 1.246(2) . ?
N2 C10 1.320(2) . ?
N2 C11 1.355(2) . ?
C2 C3 1.359(3) . ?
O3 C15 1.3599(18) . ?
C3 C4 1.401(3) . ?
O4 C28 1.241(2) . ?
C4 C12 1.409(2) . ?
C4 C5 1.421(3) . ?
O5 C28 1.278(2) . ?
C5 C6 1.335(3) . ?
O6 C26 1.3618(19) . ?
C6 C7 1.429(3) . ?
C7 C8 1.395(3) . ?
C7 C11 1.410(3) . ?
C8 C9 1.357(3) . ?
C9 C10 1.402(3) . ?
C11 C12 1.429(2) . ?
C13 C14 1.5011(19) . ?
C14 C23 1.368(2) . ?
C14 C15 1.427(2) . ?
C15 C16 1.3854(18) . ?
C16 C17 1.426(2) . ?
C16 C24 1.524(2) . ?
C17 C18 1.4256(19) . ?
C17 C22 1.427(2) . ?
C18 C19 1.363(2) . ?
C19 C20 1.400(3) . ?
C20 C21 1.364(2) . ?
C21 C22 1.418(2) . ?
C22 C23 1.4117(19) . ?
C24 C25 1.523(2) . ?
C25 C26 1.3884(19) . ?
C25 C31 1.424(2) . ?
C26 C27 1.429(2) . ?
C27 C29 1.367(2) . ?
C27 C28 1.499(2) . ?
C29 C30 1.412(2) . ?
C30 C32 1.414(2) . ?
C30 C31 1.425(2) . ?
C31 C35 1.4253(19) . ?
C32 C33 1.363(2) . ?
C33 C34 1.403(3) . ?
C34 C35 1.362(2) . ?
S1 O7 1.499(2) . ?
S1 C37 1.767(3) . ?
S1 C36 1.773(6) . ?
S2 O8 1.35(2) . ?
S2 C38 1.51(3) . ?
S2 C39 1.66(4) . ?

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 C12 122.30(16) . . ?
N1 C1 C2 120.7(2) . . ?
C10 N2 C11 117.07(17) . . ?
C3 C2 C1 118.90(19) . . ?
C2 C3 C4 120.93(17) . . ?
C3 C4 C12 117.93(18) . . ?
C3 C4 C5 123.42(18) . . ?
C12 C4 C5 118.64(18) . . ?
C6 C5 C4 120.86(19) . . ?
C5 C6 C7 122.0(2) . . ?
C8 C7 C11 116.6(2) . . ?
C8 C7 C6 124.2(2) . . ?
C11 C7 C6 119.20(19) . . ?
C9 C8 C7 120.0(2) . . ?
C8 C9 C10 119.2(2) . . ?
N2 C10 C9 123.4(2) . . ?
N2 C11 C7 123.71(17) . . ?
N2 C11 C12 118.07(16) . . ?
C7 C11 C12 118.22(16) . . ?
N1 C12 C4 119.19(16) . . ?
N1 C12 C11 119.76(15) . . ?
C4 C12 C11 121.04(17) . . ?
O2 C13 O1 123.86(14) . . ?
O2 C13 C14 119.64(15) . . ?
O1 C13 C14 116.50(15) . . ?
C23 C14 C15 119.48(12) . . ?
C23 C14 C13 120.37(14) . . ?
C15 C14 C13 120.16(14) . . ?
O3 C15 C16 118.61(13) . . ?
O3 C15 C14 119.73(12) . . ?
C16 C15 C14 121.66(13) . . ?
C15 C16 C17 118.17(13) . . ?
C15 C16 C24 120.04(13) . . ?
C17 C16 C24 121.78(12) . . ?
C16 C17 C18 122.25(14) . . ?
C16 C17 C22 120.54(12) . . ?
C18 C17 C22 117.21(13) . . ?
C19 C18 C17 121.12(15) . . ?
C18 C19 C20 121.25(15) . . ?
C21 C20 C19 119.82(16) . . ?
C20 C21 C22 120.70(16) . . ?
C23 C22 C21 121.48(14) . . ?
C23 C22 C17 118.63(13) . . ?
C21 C22 C17 119.88(13) . . ?
C14 C23 C22 121.38(14) . . ?
C25 C24 C16 115.12(12) . . ?
C26 C25 C31 118.26(13) . . ?
C26 C25 C24 120.20(13) . . ?
C31 C25 C24 121.54(12) . . ?
O6 C26 C25 118.78(14) . . ?
O6 C26 C27 119.63(13) . . ?
C25 C26 C27 121.58(14) . . ?
C29 C27 C26 119.21(13) . . ?
C29 C27 C28 120.23(15) . . ?
C26 C27 C28 120.54(14) . . ?
O4 C28 O5 123.92(14) . . ?
O4 C28 C27 120.28(15) . . ?
O5 C28 C27 115.80(15) . . ?
C27 C29 C30 121.72(14) . . ?
C29 C30 C32 121.50(15) . . ?
C29 C30 C31 118.47(14) . . ?
C32 C30 C31 120.01(14) . . ?
C25 C31 C30 120.59(13) . . ?
C25 C31 C35 122.31(14) . . ?
C30 C31 C35 117.10(14) . . ?
C33 C32 C30 121.04(16) . . ?
C32 C33 C34 119.17(16) . . ?
C35 C34 C33 121.68(15) . . ?
C34 C35 C31 120.85(15) . . ?
O7 S1 C37 107.16(15) . . ?
O7 S1 C36 106.8(2) . . ?
C37 S1 C36 97.2(2) . . ?
O8 S2 C38 124.0(16) . . ?
O8 S2 C39 131(2) . . ?
C38 S2 C39 105(2) . . ?

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
