# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_Ga_Dpaa_ga
_database_code_depnum_ccdc_archive 'CCDC 1530703'
_audit_update_record             
;
2017-10-31 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.750 0.250 -0.016 118 43 ' '
2 0.250 0.750 -0.064 119 43 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
 	C19 H17 Ga N3 O9, 3(H2 O) +[0.5H2O identified by squeeze] 
;

_chemical_formula_sum            'C19 H23 Ga N3 O12'
_chemical_formula_weight         555.12

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'
Ga Ga 0.2610 1.5380 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.7850(12)
_cell_length_b                   30.2224(18)
_cell_length_c                   7.2085(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4528.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1261
_cell_measurement_theta_min      3.5026
_cell_measurement_theta_max      27.0532

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             2280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    1.182
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.99474
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CCP4 7.0.027: AIMLESS, version 0.5.31 : 12/12/16
Scaling & analysis of unmerged intensities, absorption correction using 
spherical harmonics
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Diamond beam line I19'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            12211
_diffrn_reflns_av_unetI/netI     0.2288
_diffrn_reflns_av_R_equivalents  0.2109
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.152
_diffrn_reflns_theta_max         24.835
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4251
_reflns_number_gt                2286
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'GDA 8.44; generic data acquisition software'
_computing_cell_refinement       
;
DIALS 2theta refinement, DIALS 1.4.2-g92ff257-release   
;
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.4.2-g92ff257-release
pointless (Evans, P., 2006)
XIA2 0.5.170-g7abc92b-dials-1.4 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0889P)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_number_reflns         4251
_refine_ls_number_parameters     342
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1604
_refine_ls_R_factor_gt           0.0999
_refine_ls_wR_factor_ref         0.2888
_refine_ls_wR_factor_gt          0.2359
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.969
_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
C1 C 0.6836(4) 0.6659(3) 0.8611(13) 0.043(2) Uani 1 1 d . . . . .
C2 C 0.6315(4) 0.7012(3) 0.8458(11) 0.0380(19) Uani 1 1 d . . . . .
C3 C 0.6462(5) 0.7462(3) 0.8474(13) 0.046(2) Uani 1 1 d . . . . .
H3 H 0.689164 0.756841 0.854612 0.055 Uiso 1 1 calc R U . . .
C4 C 0.5935(5) 0.7745(3) 0.8376(14) 0.051(2) Uani 1 1 d . . . . .
H4 H 0.600139 0.805553 0.839097 0.061 Uiso 1 1 calc R U . . .
C5 C 0.5329(5) 0.7583(3) 0.8258(13) 0.048(2) Uani 1 1 d . . . . .
H5 H 0.497202 0.777849 0.819474 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5233(4) 0.7120(3) 0.8232(12) 0.043(2) Uani 1 1 d . . . . .
C7 C 0.4565(5) 0.6924(3) 0.8022(19) 0.065(3) Uani 1 1 d . . . . .
H7A H 0.426679 0.707132 0.889522 0.078 Uiso 1 1 calc R U . . .
H7B H 0.440693 0.697647 0.674556 0.078 Uiso 1 1 calc R U . . .
C8 C 0.4383(4) 0.6320(3) 1.0361(14) 0.052(2) Uani 1 1 d . . . . .
H8 H 0.424683 0.600390 1.023738 0.063 Uiso 1 1 calc R U . . .
C9 C 0.4966(4) 0.6303(3) 1.1591(13) 0.039(2) Uani 1 1 d . . . . .
C10 C 0.4140(5) 0.6219(3) 0.7099(14) 0.047(2) Uani 1 1 d . . . . .
H10A H 0.418249 0.634117 0.583033 0.056 Uiso 1 1 calc R U . . .
H10B H 0.368709 0.625363 0.750059 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4326(4) 0.5735(3) 0.7112(13) 0.046(2) Uani 1 1 d . . . . .
C12 C 0.3913(5) 0.5407(4) 0.6574(14) 0.053(2) Uani 1 1 d . . . . .
H12 H 0.349008 0.547863 0.617713 0.063 Uiso 1 1 calc R U . . .
C13 C 0.4113(5) 0.4973(4) 0.6608(14) 0.057(3) Uani 1 1 d . . . . .
H13 H 0.382470 0.474488 0.624167 0.069 Uiso 1 1 calc R U . . .
C14 C 0.4721(4) 0.4867(3) 0.7165(12) 0.042(2) Uani 1 1 d . . . . .
H14 H 0.486783 0.456979 0.717671 0.051 Uiso 1 1 calc R U . . .
C15 C 0.5124(4) 0.5221(3) 0.7726(13) 0.041(2) Uani 1 1 d . . . . .
C16 C 0.5805(4) 0.5160(3) 0.8339(12) 0.041(2) Uani 1 1 d . . . . .
C17 C 0.3796(5) 0.6553(4) 1.1195(15) 0.063(3) Uani 1 1 d . . . . .
H17A H 0.393514 0.679435 1.203481 0.075 Uiso 1 1 calc R U . . .
H17B H 0.352722 0.668229 1.019944 0.075 Uiso 1 1 calc R U . . .
C18 C 0.3421(5) 0.6209(4) 1.226(2) 0.073(3) Uani 1 1 d . . . . .
H18A H 0.334093 0.595594 1.141692 0.088 Uiso 1 1 calc R U . . .
H18B H 0.369705 0.609953 1.327962 0.088 Uiso 1 1 calc R U . . .
C19 C 0.2808(6) 0.6340(5) 1.306(2) 0.096(5) Uani 1 1 d . . . . .
N1 N 0.5724(3) 0.6852(2) 0.8316(10) 0.0393(16) Uani 1 1 d . . . . .
N2 N 0.4574(4) 0.6457(3) 0.8389(11) 0.0472(19) Uani 1 1 d . . . . .
N3 N 0.4928(3) 0.5650(2) 0.7674(10) 0.0396(16) Uani 1 1 d . . . . .
O1 O 0.6620(3) 0.6262(2) 0.8595(8) 0.0409(14) Uani 1 1 d . . . . .
O2 O 0.7410(3) 0.6767(2) 0.8769(9) 0.0484(16) Uani 1 1 d . . . . .
O3 O 0.5505(3) 0.61728(18) 1.0936(8) 0.0398(13) Uani 1 1 d . . . . .
O4 O 0.4891(3) 0.6363(2) 1.3292(8) 0.0438(15) Uani 1 1 d . . . . .
O5 O 0.6103(3) 0.55262(19) 0.8680(9) 0.0434(15) Uani 1 1 d . . . . .
O6 O 0.6038(3) 0.4793(2) 0.8485(9) 0.0522(17) Uani 1 1 d . . . . .
O7 O 0.2656(6) 0.6726(4) 1.326(3) 0.183(9) Uani 1 1 d . . . . .
O8 O 0.2399(4) 0.6022(4) 1.3641(17) 0.110(4) Uani 1 1 d D . . . .
Ga1 Ga 0.56832(4) 0.61273(3) 0.82979(12) 0.0363(4) Uani 1 1 d . . . . .
O1W O 0.5774(2) 0.61343(17) 0.5602(7) 0.0311(12) Uani 1 1 d D . . . .
H1A H 0.6135(18) 0.604(2) 0.524(9) 0.047 Uiso 1 1 d D U . . .
H1B H 0.557(3) 0.625(3) 0.469(7) 0.047 Uiso 1 1 d D U . . .
O2W O 0.2693(4) 0.5248(3) 1.2706(18) 0.093(3) Uani 1 1 d D . . . .
H2A H 0.257(6) 0.5515(16) 1.28(2) 0.140 Uiso 1 1 d D U . . .
H2B H 0.308(3) 0.525(5) 1.23(2) 0.140 Uiso 1 1 d D U . . .
O3W O 0.6902(3) 0.6034(2) 0.4171(9) 0.0506(16) Uani 1 1 d D . . . .
H3A H 0.716(4) 0.625(2) 0.429(12) 0.076 Uiso 1 1 d D U . . .
H3B H 0.699(5) 0.591(3) 0.314(8) 0.076 Uiso 1 1 d D U . . .
O4W O 0.7174(3) 0.5535(2) 0.1083(9) 0.0447(15) Uani 1 1 d D . . . .
H4A H 0.689(3) 0.554(3) 0.026(9) 0.067 Uiso 1 1 d D U . . .
H4B H 0.752(2) 0.565(3) 0.067(11) 0.067 Uiso 1 1 d D 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
C1 O2 1.243(10) . ?
C1 O1 1.281(11) . ?
C1 C2 1.524(12) . ?
C2 N1 1.325(11) . ?
C2 C3 1.395(12) . ?
C3 C4 1.390(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.354(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.413(13) . ?
C5 H5 0.9500 . ?
C6 N1 1.303(11) . ?
C6 C7 1.518(13) . ?
C7 N2 1.435(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.502(13) . ?
C8 C17 1.532(14) . ?
C8 N2 1.533(12) . ?
C8 H8 1.0000 . ?
C9 O4 1.250(10) . ?
C9 O3 1.278(10) . ?
C10 N2 1.482(12) . ?
C10 C11 1.513(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N3 1.340(11) . ?
C11 C12 1.367(14) . ?
C12 C13 1.377(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.364(14) . ?
C13 H13 0.9500 . ?
C14 C15 1.416(12) . ?
C14 H14 0.9500 . ?
C15 N3 1.360(11) . ?
C15 C16 1.495(12) . ?
C16 O6 1.214(11) . ?
C16 O5 1.292(10) . ?
C17 C18 1.511(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.452(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O7 1.216(18) . ?
C19 O8 1.352(17) . ?
N1 Ga1 2.191(7) . ?
N3 Ga1 2.180(7) . ?
O1 Ga1 2.001(6) . ?
O3 Ga1 1.942(6) . ?
O5 Ga1 2.034(6) . ?
Ga1 O1W 1.952(5) . ?
O1W H1A 0.845(15) . ?
O1W H1B 0.845(15) . ?
O2W H2A 0.850(15) . ?
O2W H2B 0.854(15) . ?
O3W H3A 0.854(15) . ?
O3W H3B 0.849(15) . ?
O4W H4A 0.845(16) . ?
O4W H4B 0.847(16) . ?

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 C1 O1 125.6(8) . . ?
O2 C1 C2 120.4(8) . . ?
O1 C1 C2 114.0(7) . . ?
N1 C2 C3 124.0(8) . . ?
N1 C2 C1 114.2(7) . . ?
C3 C2 C1 121.8(8) . . ?
C4 C3 C2 115.2(8) . . ?
C4 C3 H3 122.4 . . ?
C2 C3 H3 122.4 . . ?
C5 C4 C3 121.0(9) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.3(9) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 120.3(8) . . ?
N1 C6 C7 118.5(8) . . ?
C5 C6 C7 121.1(8) . . ?
N2 C7 C6 110.7(8) . . ?
N2 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C17 115.2(9) . . ?
C9 C8 N2 110.4(7) . . ?
C17 C8 N2 116.4(8) . . ?
C9 C8 H8 104.4 . . ?
C17 C8 H8 104.4 . . ?
N2 C8 H8 104.4 . . ?
O4 C9 O3 121.2(8) . . ?
O4 C9 C8 118.2(8) . . ?
O3 C9 C8 120.0(8) . . ?
N2 C10 C11 108.0(7) . . ?
N2 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
N2 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
N3 C11 C12 122.1(9) . . ?
N3 C11 C10 115.3(8) . . ?
C12 C11 C10 122.6(9) . . ?
C11 C12 C13 119.8(9) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.5(9) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 117.1(9) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
N3 C15 C14 122.3(8) . . ?
N3 C15 C16 114.2(7) . . ?
C14 C15 C16 123.5(8) . . ?
O6 C16 O5 125.2(9) . . ?
O6 C16 C15 121.0(8) . . ?
O5 C16 C15 113.8(7) . . ?
C18 C17 C8 107.1(9) . . ?
C18 C17 H17A 110.3 . . ?
C8 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
C8 C17 H17B 110.3 . . ?
H17A C17 H17B 108.6 . . ?
C19 C18 C17 117.7(11) . . ?
C19 C18 H18A 107.9 . . ?
C17 C18 H18A 107.9 . . ?
C19 C18 H18B 107.9 . . ?
C17 C18 H18B 107.9 . . ?
H18A C18 H18B 107.2 . . ?
O7 C19 O8 118.8(14) . . ?
O7 C19 C18 122.5(14) . . ?
O8 C19 C18 118.7(14) . . ?
C6 N1 C2 120.2(8) . . ?
C6 N1 Ga1 126.2(6) . . ?
C2 N1 Ga1 113.6(5) . . ?
C7 N2 C10 110.7(8) . . ?
C7 N2 C8 115.7(9) . . ?
C10 N2 C8 107.1(7) . . ?
C11 N3 C15 118.2(7) . . ?
C11 N3 Ga1 127.4(6) . . ?
C15 N3 Ga1 114.2(5) . . ?
C1 O1 Ga1 122.1(5) . . ?
C9 O3 Ga1 123.4(6) . . ?
C16 O5 Ga1 122.4(6) . . ?
O3 Ga1 O1W 172.8(2) . . ?
O3 Ga1 O1 93.8(2) . . ?
O1W Ga1 O1 90.6(2) . . ?
O3 Ga1 O5 90.7(2) . . ?
O1W Ga1 O5 95.9(2) . . ?
O1 Ga1 O5 75.5(2) . . ?
O3 Ga1 N3 96.4(3) . . ?
O1W Ga1 N3 82.6(2) . . ?
O1 Ga1 N3 149.1(3) . . ?
O5 Ga1 N3 75.2(2) . . ?
O3 Ga1 N1 86.0(2) . . ?
O1W Ga1 N1 89.5(2) . . ?
O1 Ga1 N1 76.1(2) . . ?
O5 Ga1 N1 151.1(2) . . ?
N3 Ga1 N1 133.7(3) . . ?
Ga1 O1W H1A 113(5) . . ?
Ga1 O1W H1B 137(5) . . ?
H1A O1W H1B 109(4) . . ?
H2A O2W H2B 108(4) . . ?
H3A O3W H3B 107(4) . . ?
H4A O4W H4B 109(4) . . ?

_refine_diff_density_max         2.035
_refine_diff_density_min         -1.245
_refine_diff_density_rms         0.154



####################################################################### 
# 
# 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_H4Dpaa_ga
_database_code_depnum_ccdc_archive 'CCDC 1549314'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N3 O8'
_chemical_formula_sum            'C19 H19 N3 O8'
_chemical_formula_weight         417.37

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.0852(6)
_cell_length_b                   32.290(4)
_cell_length_c                   7.6786(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.108(7)
_cell_angle_gamma                90
_cell_volume                     1752.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2923
_cell_measurement_theta_min      1.25
_cell_measurement_theta_max      25.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            9845
_diffrn_reflns_av_unetI/netI     0.1118
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.261
_diffrn_reflns_theta_max         25.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3229
_reflns_number_gt                1656
_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       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0225P)²] 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         3229
_refine_ls_number_parameters     271
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   0.766
_refine_ls_restrained_S_all      0.769
_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
C1 C 0.1514(3) 0.44364(7) 0.2416(3) 0.0272(6) Uani 1 1 d . . . . .
C2 C 0.3303(3) 0.42301(7) 0.1924(3) 0.0253(6) Uani 1 1 d . . . . .
C3 C 0.4688(3) 0.44402(7) 0.1093(3) 0.0300(6) Uani 1 1 d . . . . .
H3 H 0.450899 0.472183 0.076377 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6336(3) 0.42349(8) 0.0748(3) 0.0330(6) Uani 1 1 d . . . . .
H4 H 0.730581 0.437198 0.017795 0.040 Uiso 1 1 calc R U . . .
C5 C 0.6534(3) 0.38253(7) 0.1254(3) 0.0313(6) Uani 1 1 d . . . . .
H5 H 0.765397 0.367712 0.104427 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5098(3) 0.36336(7) 0.2064(3) 0.0267(6) Uani 1 1 d . . . . .
C7 C 0.5237(3) 0.31882(7) 0.2688(4) 0.0336(7) Uani 1 1 d . . . . .
H7A H 0.449688 0.300892 0.184487 0.040 Uiso 1 1 calc R U . . .
H7B H 0.657466 0.309786 0.272322 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1983(3) 0.44451(7) 0.7411(3) 0.0269(6) Uani 1 1 d . . . . .
C9 C 0.3867(3) 0.43076(7) 0.6782(3) 0.0227(6) Uani 1 1 d . . . . .
C10 C 0.5250(3) 0.45750(7) 0.6304(3) 0.0268(6) Uani 1 1 d . . . . .
H10 H 0.506700 0.486550 0.639324 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6905(3) 0.44238(7) 0.5695(3) 0.0286(6) Uani 1 1 d . . . . .
H11 H 0.785852 0.460926 0.536869 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7163(3) 0.39992(7) 0.5564(3) 0.0262(6) Uani 1 1 d . . . . .
H12 H 0.828959 0.389203 0.513582 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5773(3) 0.37341(7) 0.6061(3) 0.0234(6) Uani 1 1 d . . . . .
C14 C 0.5845(3) 0.32705(7) 0.5831(3) 0.0261(6) Uani 1 1 d . . . . .
H14A H 0.714664 0.318664 0.559476 0.031 Uiso 1 1 calc R U . . .
H14B H 0.551995 0.313337 0.692318 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1145(3) 0.29456(7) 0.4375(3) 0.0278(6) Uani 1 1 d D . . . .
C16A C 0.3187(4) 0.28131(8) 0.4817(5) 0.0238(5) Uiso 0.838(5) 1 d D U P A 1
H16A H 0.333101 0.277241 0.611111 0.029 Uiso 0.838(5) 1 calc R U P A 1
C17A C 0.3547(4) 0.23899(8) 0.3990(5) 0.0238(5) Uiso 0.838(5) 1 d D U P A 1
H17A H 0.346796 0.241695 0.270260 0.029 Uiso 0.838(5) 1 calc R U P A 1
H17B H 0.256371 0.219106 0.430531 0.029 Uiso 0.838(5) 1 calc R U P A 1
C16B C 0.3160(16) 0.2805(4) 0.394(2) 0.0238(5) Uiso 0.162(5) 1 d D U P A 2
H16B H 0.315673 0.274698 0.266433 0.029 Uiso 0.162(5) 1 calc R U P A 2
C17B C 0.3706(17) 0.2409(4) 0.495(2) 0.0238(5) Uiso 0.162(5) 1 d D U P A 2
H17C H 0.370743 0.247046 0.621733 0.029 Uiso 0.162(5) 1 calc R U P A 2
H17D H 0.270799 0.219948 0.467834 0.029 Uiso 0.162(5) 1 calc R U P A 2
C18 C 0.5511(3) 0.22259(7) 0.4631(4) 0.0331(7) Uani 1 1 d D . . . .
H18A H 0.647348 0.243356 0.435478 0.040 Uiso 1 1 calc R U . A 1
H18B H 0.556195 0.219640 0.591673 0.040 Uiso 1 1 calc R U . A 1
C19 C 0.6016(3) 0.18215(7) 0.3859(3) 0.0263(6) Uani 1 1 d . . . . .
N1 N 0.4193(3) 0.38970(5) 0.6674(2) 0.0234(5) Uani 1 1 d . . . . .
H1 H 0.325(2) 0.3710(4) 0.7054(9) 0.028 Uiso 1 1 calc R U . . .
N2 N 0.3490(3) 0.38292(5) 0.2415(3) 0.0250(5) Uani 1 1 d . . . . .
N3 N 0.4541(3) 0.31368(5) 0.4405(3) 0.0279(5) Uani 1 1 d D . . . .
O1 O 0.0418(2) 0.42710(5) 0.3320(3) 0.0409(5) Uani 1 1 d . . . . .
O2 O 0.1336(2) 0.48136(5) 0.1764(2) 0.0351(4) Uani 1 1 d . . . . .
H2 H 0.034871 0.492340 0.209611 0.053 Uiso 1 1 calc R U . . .
O3 O 0.0910(2) 0.41748(5) 0.7943(2) 0.0316(4) Uani 1 1 d . . . . .
O4 O 0.1721(2) 0.48294(5) 0.7333(2) 0.0337(4) Uani 1 1 d . . . . .
O5 O -0.0135(2) 0.27121(5) 0.4657(2) 0.0401(5) Uani 1 1 d . . . . .
O6 O 0.0762(2) 0.33259(5) 0.3803(2) 0.0345(5) Uani 1 1 d . . . . .
H6 H 0.177368 0.344635 0.359937 0.052 Uiso 1 1 calc R U . . .
O7 O 0.7583(2) 0.17475(5) 0.3405(2) 0.0369(5) Uani 1 1 d . . . . .
O8 O 0.4638(2) 0.15480(5) 0.3751(3) 0.0373(5) Uani 1 1 d . . . . .
H8 H 0.504035 0.132320 0.337078 0.056 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
C1 O1 1.203(3) . ?
C1 O2 1.319(3) . ?
C1 C2 1.504(3) . ?
C2 N2 1.352(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C6 N2 1.347(3) . ?
C6 C7 1.517(3) . ?
C7 N3 1.450(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O3 1.246(3) . ?
C8 O4 1.255(3) . ?
C8 C9 1.518(3) . ?
C9 N1 1.349(3) . ?
C9 C10 1.376(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 N1 1.352(3) . ?
C13 C14 1.509(3) . ?
C14 N3 1.447(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O5 1.211(3) . ?
C15 O6 1.325(3) . ?
C15 C16A 1.524(3) . ?
C15 C16B 1.557(12) . ?
C16A N3 1.468(3) . ?
C16A C17A 1.536(4) . ?
C16A H16A 1.0000 . ?
C17A C18 1.537(3) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C16B N3 1.477(12) . ?
C16B C17B 1.530(15) . ?
C16B H16B 1.0000 . ?
C17B C18 1.446(11) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18 C19 1.488(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O7 1.212(3) . ?
C19 O8 1.314(3) . ?
N1 H1 0.96(2) . ?
O2 H2 0.8400 . ?
O6 H6 0.8400 . ?
O8 H8 0.8400 . ?

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 C1 O2 125.5(2) . . ?
O1 C1 C2 122.6(2) . . ?
O2 C1 C2 111.9(2) . . ?
N2 C2 C3 122.6(2) . . ?
N2 C2 C1 114.9(2) . . ?
C3 C2 C1 122.4(2) . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 C6 C5 122.9(2) . . ?
N2 C6 C7 114.8(2) . . ?
C5 C6 C7 122.4(2) . . ?
N3 C7 C6 112.1(2) . . ?
N3 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
N3 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O3 C8 O4 128.1(2) . . ?
O3 C8 C9 118.1(2) . . ?
O4 C8 C9 113.9(2) . . ?
N1 C9 C10 118.2(2) . . ?
N1 C9 C8 117.7(2) . . ?
C10 C9 C8 124.1(2) . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N1 C13 C12 118.7(2) . . ?
N1 C13 C14 117.6(2) . . ?
C12 C13 C14 123.6(2) . . ?
N3 C14 C13 111.05(18) . . ?
N3 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
N3 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O5 C15 O6 119.9(2) . . ?
O5 C15 C16A 119.8(2) . . ?
O6 C15 C16A 120.2(2) . . ?
O5 C15 C16B 124.5(5) . . ?
O6 C15 C16B 111.7(5) . . ?
N3 C16A C15 112.1(2) . . ?
N3 C16A C17A 114.5(3) . . ?
C15 C16A C17A 109.9(2) . . ?
N3 C16A H16A 106.6 . . ?
C15 C16A H16A 106.6 . . ?
C17A C16A H16A 106.6 . . ?
C16A C17A C18 110.3(3) . . ?
C16A C17A H17A 109.6 . . ?
C18 C17A H17A 109.6 . . ?
C16A C17A H17B 109.6 . . ?
C18 C17A H17B 109.6 . . ?
H17A C17A H17B 108.1 . . ?
N3 C16B C17B 110.3(11) . . ?
N3 C16B C15 109.8(8) . . ?
C17B C16B C15 109.8(10) . . ?
N3 C16B H16B 109.0 . . ?
C17B C16B H16B 109.0 . . ?
C15 C16B H16B 109.0 . . ?
C18 C17B C16B 116.6(11) . . ?
C18 C17B H17C 108.1 . . ?
C16B C17B H17C 108.1 . . ?
C18 C17B H17D 108.1 . . ?
C16B C17B H17D 108.1 . . ?
H17C C17B H17D 107.3 . . ?
C17B C18 C19 131.9(7) . . ?
C19 C18 C17A 114.4(2) . . ?
C19 C18 H18A 108.7 . . ?
C17A C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17A C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
O7 C19 O8 122.8(2) . . ?
O7 C19 C18 122.6(2) . . ?
O8 C19 C18 114.6(2) . . ?
C9 N1 C13 123.6(2) . . ?
C9 N1 H1 118.2 . . ?
C13 N1 H1 118.2 . . ?
C6 N2 C2 117.4(2) . . ?
C14 N3 C7 114.41(19) . . ?
C14 N3 C16A 116.2(2) . . ?
C7 N3 C16A 123.2(2) . . ?
C14 N3 C16B 140.7(7) . . ?
C7 N3 C16B 97.3(7) . . ?
C1 O2 H2 109.5 . . ?
C15 O6 H6 109.5 . . ?
C19 O8 H8 109.5 . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_Ga_Dpaa
_database_code_depnum_ccdc_archive 'CCDC 1530704'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;

_vrf_PLAT417_Ga_Dpaa             
;
RESPONSE: These hydrogen atoms are for two water molecules. These atom 
positions were determined from the difference Fourier map and their
positions refined subject to sensible angle restraints. The two molecules
are approximately orthogonal so it is not the case that these two 
atoms clash into each other. 
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C16 H14 Ga N3 O7, 3(H2 O)
;

_chemical_formula_sum            'C16 H20 Ga N3 O10'
_chemical_formula_weight         484.07

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'
Ga Ga 0.2610 1.5380 '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                   7.06810(10)
_cell_length_b                   8.21920(10)
_cell_length_c                   15.9952(2)
_cell_angle_alpha                93.6180(10)
_cell_angle_beta                 93.7920(10)
_cell_angle_gamma                91.9130(10)
_cell_volume                     924.69(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11243
_cell_measurement_theta_min      1.23143
_cell_measurement_theta_max      35.90614

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    1.425
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CCP4 7.0.027: AIMLESS, version 0.5.31 : 12/12/16
Scaling & analysis of unmerged intensities, absorption correction 
using spherical harmonics
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            20701
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.239
_diffrn_reflns_theta_max         36.179
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8614
_reflns_number_gt                7301
_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       'GDA 8.44; generic data acquisition software'
_computing_cell_refinement       
;
DIALS 2theta refinement, DIALS 1.4.2-g92ff257-release   
;
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.4.2-g92ff257-release
pointless (Evans, P., 2006)
XIA2 0.5.170-g7abc92b-dials-1.4 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0431P)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_number_reflns         8614
_refine_ls_number_parameters     304
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
C16 C 0.2172(2) 0.23251(17) 0.07459(9) 0.0196(2) Uani 1 1 d . . . . .
C15 C 0.24688(19) 0.40463(17) 0.05080(9) 0.0166(2) Uani 1 1 d . . . . .
C14 C 0.2432(2) 0.44797(19) -0.03159(9) 0.0210(3) Uani 1 1 d D . . . .
H14 H 0.2263(3) 0.3685(13) -0.0766(7) 0.025 Uiso 1 1 calc DR U . . .
C13 C 0.2655(2) 0.6128(2) -0.04572(10) 0.0228(3) Uani 1 1 d D . . . .
H13 H 0.2600(2) 0.6474(6) -0.1014(9) 0.027 Uiso 1 1 calc DR U . . .
C12 C 0.2957(2) 0.72577(19) 0.02250(10) 0.0217(3) Uani 1 1 d D . . . .
H12 H 0.3115(3) 0.8364(19) 0.01429(17) 0.026 Uiso 1 1 calc DR U . . .
C11 C 0.30208(19) 0.67148(16) 0.10361(9) 0.0168(2) Uani 1 1 d . . . . .
C10 C 0.3490(2) 0.78239(16) 0.18054(9) 0.0182(2) Uani 1 1 d . . . . .
H10A H 0.488415 0.794682 0.191583 0.022 Uiso 1 1 calc R U . . .
H10B H 0.298828 0.891566 0.172006 0.022 Uiso 1 1 calc R U . . .
C8 C 0.05948(19) 0.74590(16) 0.25366(10) 0.0198(3) Uani 1 1 d . . . . .
H8A H 0.025651 0.813420 0.206171 0.024 Uiso 1 1 calc R U . . .
H8B H 0.039060 0.811636 0.306085 0.024 Uiso 1 1 calc R U . . .
C9 C -0.07488(19) 0.59828(17) 0.24762(9) 0.0171(2) Uani 1 1 d . . . . .
C7 C 0.3663(2) 0.77369(17) 0.33227(9) 0.0191(2) Uani 1 1 d . . . . .
H7A H 0.329857 0.886448 0.347474 0.023 Uiso 1 1 calc R U . . .
H7B H 0.504743 0.774859 0.326078 0.023 Uiso 1 1 calc R U . . .
C6 C 0.31670(19) 0.66417(17) 0.39914(9) 0.0186(2) Uani 1 1 d . . . . .
C5 C 0.3131(2) 0.7157(2) 0.48380(10) 0.0236(3) Uani 1 1 d D . . . .
H5 H 0.3401(5) 0.8288(19) 0.5022(3) 0.028 Uiso 1 1 calc DR U . . .
C4 C 0.2705(2) 0.6028(2) 0.54108(10) 0.0249(3) Uani 1 1 d D . . . .
H4 H 0.2645(2) 0.6360(6) 0.5979(9) 0.030 Uiso 1 1 calc DR U . . .
C3 C 0.2364(2) 0.4395(2) 0.51384(9) 0.0229(3) Uani 1 1 d D . . . .
H3 H 0.2112(5) 0.3627(14) 0.5506(7) 0.028 Uiso 1 1 calc DR U . . .
C2 C 0.24226(19) 0.39804(17) 0.42848(9) 0.0180(2) Uani 1 1 d . . . . .
C1 C 0.2081(2) 0.22783(17) 0.38915(9) 0.0201(3) Uani 1 1 d . . . . .
N3 N 0.27423(16) 0.51319(13) 0.11660(7) 0.01542(19) Uani 1 1 d . . . . .
N2 N 0.26346(16) 0.71232(14) 0.25296(8) 0.0164(2) Uani 1 1 d . . . . .
N1 N 0.27849(16) 0.50754(14) 0.37295(7) 0.0162(2) Uani 1 1 d . . . . .
O5 O 0.20206(15) 0.21800(12) 0.15324(6) 0.02004(19) Uani 1 1 d . . . . .
O6 O 0.20713(19) 0.11849(14) 0.02090(8) 0.0295(3) Uani 1 1 d . . . . .
O3 O -0.01440(14) 0.45408(12) 0.23767(6) 0.01701(18) Uani 1 1 d . . . . .
O4 O -0.24677(14) 0.62491(14) 0.25127(8) 0.0260(2) Uani 1 1 d . . . . .
O1 O 0.20473(15) 0.21414(12) 0.30958(7) 0.01974(19) Uani 1 1 d . . . . .
O2 O 0.18525(18) 0.11248(14) 0.43464(7) 0.0279(2) Uani 1 1 d . . . . .
Ga1 Ga 0.25012(2) 0.40888(2) 0.23906(2) 0.01428(5) Uani 1 1 d . . . . .
O1W O 0.51767(14) 0.37981(13) 0.24589(7) 0.0200(2) Uani 1 1 d D . . . .
O2W O 0.1706(2) 0.04274(16) 0.59990(8) 0.0323(3) Uani 1 1 d D . . . .
O3W O 0.64257(17) 0.09730(15) 0.26649(9) 0.0278(2) Uani 1 1 d D . . . .
O4W O 0.86426(19) 0.01859(16) 0.14066(8) 0.0298(3) Uani 1 1 d D . . . .
H1A H 0.567(3) 0.291(2) 0.2506(15) 0.047(2) Uiso 1 1 d D U . . .
H1B H 0.594(3) 0.456(2) 0.2481(15) 0.047(2) Uiso 1 1 d D U . . .
H2A H 0.189(3) 0.064(3) 0.5511(11) 0.047(2) Uiso 1 1 d D U . . .
H2B H 0.058(3) -0.004(3) 0.5978(14) 0.047(2) Uiso 1 1 d D U . . .
H3A H 0.722(3) 0.091(3) 0.2276(12) 0.047(2) Uiso 1 1 d D U . . .
H3B H 0.711(3) 0.067(3) 0.3066(11) 0.047(2) Uiso 1 1 d D U . . .
H4A H 0.969(3) 0.068(3) 0.1470(14) 0.047(2) Uiso 1 1 d D U . . .
H4B H 0.860(3) -0.017(3) 0.0896(11) 0.047(2) Uiso 1 1 d D 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
C16 O6 1.2275(17) . ?
C16 O5 1.2822(18) . ?
C16 C15 1.500(2) . ?
C15 N3 1.3358(17) . ?
C15 C14 1.386(2) . ?
C14 C13 1.393(2) . ?
C14 H14 0.940(15) . ?
C13 C12 1.388(2) . ?
C13 H13 0.950(16) . ?
C12 C11 1.397(2) . ?
C12 H12 0.931(16) . ?
C11 N3 1.3405(17) . ?
C11 C10 1.4965(19) . ?
C10 N2 1.4808(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C8 N2 1.4776(17) . ?
C8 C9 1.5098(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O4 1.2462(17) . ?
C9 O3 1.2774(16) . ?
C7 N2 1.4713(18) . ?
C7 C6 1.492(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 N1 1.3414(18) . ?
C6 C5 1.395(2) . ?
C5 C4 1.385(2) . ?
C5 H5 0.967(16) . ?
C4 C3 1.392(2) . ?
C4 H4 0.937(15) . ?
C3 C2 1.390(2) . ?
C3 H3 0.911(16) . ?
C2 N1 1.3343(18) . ?
C2 C1 1.502(2) . ?
C1 O2 1.2437(18) . ?
C1 O1 1.2692(18) . ?
N3 Ga1 2.2017(12) . ?
N1 Ga1 2.2354(11) . ?
O5 Ga1 2.0229(10) . ?
O3 Ga1 1.9173(10) . ?
O1 Ga1 2.0441(10) . ?
Ga1 O1W 1.9109(10) . ?
O1W H1A 0.826(16) . ?
O1W H1B 0.809(16) . ?
O2W H2A 0.829(16) . ?
O2W H2B 0.871(16) . ?
O3W H3A 0.867(16) . ?
O3W H3B 0.831(16) . ?
O4W H4A 0.829(16) . ?
O4W H4B 0.848(16) . ?

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
O6 C16 O5 124.73(14) . . ?
O6 C16 C15 120.70(14) . . ?
O5 C16 C15 114.56(12) . . ?
N3 C15 C14 122.95(13) . . ?
N3 C15 C16 113.68(12) . . ?
C14 C15 C16 123.36(13) . . ?
C15 C14 C13 118.02(14) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C12 C13 C14 119.16(14) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C12 C11 119.20(14) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
N3 C11 C12 121.16(13) . . ?
N3 C11 C10 115.85(12) . . ?
C12 C11 C10 122.92(13) . . ?
N2 C10 C11 109.13(11) . . ?
N2 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
N2 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
N2 C8 C9 115.99(11) . . ?
N2 C8 H8A 108.3 . . ?
C9 C8 H8A 108.3 . . ?
N2 C8 H8B 108.3 . . ?
C9 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
O4 C9 O3 122.15(13) . . ?
O4 C9 C8 116.59(12) . . ?
O3 C9 C8 121.25(12) . . ?
N2 C7 C6 108.37(11) . . ?
N2 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
N1 C6 C5 120.79(14) . . ?
N1 C6 C7 115.27(12) . . ?
C5 C6 C7 123.92(13) . . ?
C4 C5 C6 119.19(14) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C4 C3 119.71(14) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C2 C3 C4 117.59(14) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
N1 C2 C3 122.71(14) . . ?
N1 C2 C1 113.18(12) . . ?
C3 C2 C1 124.12(14) . . ?
O2 C1 O1 124.78(14) . . ?
O2 C1 C2 119.63(14) . . ?
O1 C1 C2 115.59(12) . . ?
C15 N3 C11 119.45(12) . . ?
C15 N3 Ga1 114.25(9) . . ?
C11 N3 Ga1 126.19(9) . . ?
C7 N2 C8 110.99(11) . . ?
C7 N2 C10 110.64(11) . . ?
C8 N2 C10 111.30(11) . . ?
C2 N1 C6 119.95(12) . . ?
C2 N1 Ga1 114.45(9) . . ?
C6 N1 Ga1 125.47(10) . . ?
C16 O5 Ga1 122.08(9) . . ?
C9 O3 Ga1 122.95(9) . . ?
C1 O1 Ga1 122.55(9) . . ?
O1W Ga1 O3 175.40(4) . . ?
O1W Ga1 O5 92.32(5) . . ?
O3 Ga1 O5 92.23(4) . . ?
O1W Ga1 O1 91.66(4) . . ?
O3 Ga1 O1 90.08(4) . . ?
O5 Ga1 O1 75.92(4) . . ?
O1W Ga1 N3 89.19(5) . . ?
O3 Ga1 N3 91.36(4) . . ?
O5 Ga1 N3 74.95(4) . . ?
O1 Ga1 N3 150.87(4) . . ?
O1W Ga1 N1 88.30(5) . . ?
O3 Ga1 N1 88.09(4) . . ?
O5 Ga1 N1 149.89(4) . . ?
O1 Ga1 N1 73.97(4) . . ?
N3 Ga1 N1 135.16(4) . . ?
Ga1 O1W H1A 124.1(16) . . ?
Ga1 O1W H1B 122.6(16) . . ?
H1A O1W H1B 113.1(19) . . ?
H2A O2W H2B 106.0(18) . . ?
H3A O3W H3B 99.6(17) . . ?
H4A O4W H4B 102.3(18) . . ?

_refine_diff_density_max         1.606
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.107

