# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
# 
#######################################################################

data_cvd484
_audit_block_doi                 10.5517/ccdc.csd.cc1q3ht4
_database_code_depnum_ccdc_archive 'CCDC 1582296'
_audit_update_record             
;
2017-10-26 deposited with the CCDC.
2017-12-28 downloaded from the CCDC.
;
_audit_creation_date             2017-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H14 Cl2 Ga N O'
_chemical_formula_sum            'C8 H14 Cl2 Ga N O'
_chemical_formula_weight         280.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6310(4)
_cell_length_b                   9.5059(4)
_cell_length_c                   12.4590(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.923(3)
_cell_angle_gamma                90
_cell_volume                     1137.97(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2145
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      76.2970
_cell_measurement_theta_min      4.6730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.053
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4035
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         5.624
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean 10.4372
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   27.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3552   38.0000   30.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega   96.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega  108.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   87.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
  5 omega   49.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   33.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3552 -125.0000   60.0000 65

#__ type_ start__ end____ width___ exp.time_
 13 omega   46.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
 14 omega -106.00  -70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3552 -140.0000   15.0000 36

#__ type_ start__ end____ width___ exp.time_
 15 omega -119.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3552  -99.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
 16 omega -124.00  -99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3552  -99.0000   30.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1923
_reflns_number_total             2156
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0239
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0592
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C5(H5A,H5B,H5C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ga1 Ga 0.49403(3) 0.72815(3) 0.65747(2) 0.01590(9) Uani 1 1 d . . . . .
Cl1 Cl 0.50110(5) 0.51681(5) 0.72262(4) 0.02168(12) Uani 1 1 d . . . . .
Cl2 Cl 0.45202(6) 0.87511(6) 0.78407(4) 0.02462(13) Uani 1 1 d . . . . .
O1 O 0.66571(15) 0.77594(16) 0.61107(11) 0.0212(3) Uani 1 1 d . . . . .
N1 N 0.37730(18) 0.74741(18) 0.52683(13) 0.0157(3) Uani 1 1 d . . . . .
C4 C 0.4305(2) 0.8006(2) 0.44043(16) 0.0172(4) Uani 1 1 d . . . . .
C2 C 0.6777(2) 0.8295(2) 0.51462(16) 0.0175(4) Uani 1 1 d . . . . .
C3 C 0.5716(2) 0.8445(2) 0.43714(16) 0.0185(4) Uani 1 1 d . . . . .
H3 H 0.5948 0.8899 0.3728 0.022 Uiso 1 1 calc R . . . .
C7 C 0.2315(2) 0.6942(2) 0.52249(17) 0.0184(4) Uani 1 1 d . . . . .
H7 H 0.1748 0.7485 0.4664 0.022 Uiso 1 1 calc R . . . .
C6 C 0.2282(2) 0.5387(2) 0.49082(17) 0.0221(4) Uani 1 1 d . . . . .
H6A H 0.2684 0.5273 0.4212 0.033 Uiso 1 1 calc GR . . . .
H6B H 0.1317 0.5053 0.4854 0.033 Uiso 1 1 calc GR . . . .
H6C H 0.2825 0.4839 0.5456 0.033 Uiso 1 1 calc GR . . . .
C8 C 0.1699(2) 0.7170(2) 0.63083(18) 0.0235(5) Uani 1 1 d . . . . .
H8A H 0.2219 0.6610 0.6861 0.035 Uiso 1 1 calc GR . . . .
H8B H 0.0721 0.6879 0.6258 0.035 Uiso 1 1 calc GR . . . .
H8C H 0.1763 0.8169 0.6501 0.035 Uiso 1 1 calc GR . . . .
C5 C 0.3406(2) 0.8183(2) 0.33735(16) 0.0218(4) Uani 1 1 d . . . . .
H5A H 0.3022 0.7268 0.3143 0.033 Uiso 1 1 calc GR . . . .
H5B H 0.3968 0.8562 0.2814 0.033 Uiso 1 1 calc GR . . . .
H5C H 0.2643 0.8834 0.3494 0.033 Uiso 1 1 calc GR . . . .
C1 C 0.8230(2) 0.8726(2) 0.49468(17) 0.0230(5) Uani 1 1 d . . . . .
H1A H 0.8630 0.9260 0.5566 0.034 Uiso 1 1 calc GR . . . .
H1B H 0.8216 0.9314 0.4300 0.034 Uiso 1 1 calc GR . . . .
H1C H 0.8795 0.7886 0.4843 0.034 Uiso 1 1 calc GR . . . .


_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
Ga1 Cl1 2.1661(6) . ?
Ga1 Cl2 2.1657(6) . ?
Ga1 O1 1.8453(15) . ?
Ga1 N1 1.9226(17) . ?
O1 C2 1.318(2) . ?
N1 C4 1.324(3) . ?
N1 C7 1.490(3) . ?
C4 C3 1.425(3) . ?
C4 C5 1.508(3) . ?
C2 C3 1.364(3) . ?
C2 C1 1.494(3) . ?
C3 H3 0.9500 . ?
C7 H7 1.0000 . ?
C7 C6 1.529(3) . ?
C7 C8 1.526(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
Cl2 Ga1 Cl1 109.15(2) . . ?
O1 Ga1 Cl1 109.87(5) . . ?
O1 Ga1 Cl2 106.58(5) . . ?
O1 Ga1 N1 101.30(7) . . ?
N1 Ga1 Cl1 114.03(5) . . ?
N1 Ga1 Cl2 115.31(5) . . ?
C2 O1 Ga1 121.16(13) . . ?
C4 N1 Ga1 119.24(14) . . ?
C4 N1 C7 121.09(17) . . ?
C7 N1 Ga1 119.56(13) . . ?
N1 C4 C3 123.93(18) . . ?
N1 C4 C5 120.23(19) . . ?
C3 C4 C5 115.84(18) . . ?
O1 C2 C3 125.26(19) . . ?
O1 C2 C1 113.53(17) . . ?
C3 C2 C1 121.20(18) . . ?
C4 C3 H3 115.9 . . ?
C2 C3 C4 128.23(19) . . ?
C2 C3 H3 115.9 . . ?
N1 C7 H7 108.5 . . ?
N1 C7 C6 109.89(17) . . ?
N1 C7 C8 109.96(17) . . ?
C6 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C8 C7 C6 111.31(18) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
Ga1 O1 C2 C3 -5.7(3) . . . . ?
Ga1 O1 C2 C1 175.22(13) . . . . ?
Ga1 N1 C4 C3 0.5(3) . . . . ?
Ga1 N1 C4 C5 -179.29(15) . . . . ?
Ga1 N1 C7 C6 -87.13(19) . . . . ?
Ga1 N1 C7 C8 35.7(2) . . . . ?
Cl1 Ga1 O1 C2 130.44(15) . . . . ?
Cl2 Ga1 O1 C2 -111.43(15) . . . . ?
O1 C2 C3 C4 -3.5(4) . . . . ?
N1 Ga1 O1 C2 9.53(17) . . . . ?
N1 C4 C3 C2 6.4(4) . . . . ?
C4 N1 C7 C6 89.0(2) . . . . ?
C4 N1 C7 C8 -148.2(2) . . . . ?
C7 N1 C4 C3 -175.60(19) . . . . ?
C7 N1 C4 C5 4.6(3) . . . . ?
C5 C4 C3 C2 -173.8(2) . . . . ?
C1 C2 C3 C4 175.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_cvd525f
_audit_block_doi                 10.5517/ccdc.csd.cc1q3hv5
_database_code_depnum_ccdc_archive 'CCDC 1582297'
_audit_update_record             
;
2017-10-26 deposited with the CCDC.
2017-12-28 downloaded from the CCDC.
;
_audit_creation_date             2017-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H36 Cl Ga N2 O4'
_chemical_formula_sum            'C20 H36 Cl Ga N2 O4'
_chemical_formula_weight         473.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ga1 C20 H36 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6212(2)
_cell_length_b                   13.9767(3)
_cell_length_c                   17.2781(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.153(2)
_cell_angle_gamma                90
_cell_volume                     2322.96(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9006
_cell_measurement_temperature    99.8(2)
_cell_measurement_theta_max      74.0800
_cell_measurement_theta_min      4.0420
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.487
_exptl_absorpt_coefficient_mu    2.895
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.523
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 9 1 0.1545
1 -9 -1 0.1083
1 0 -11 0.0219
-6 0 -3 0.0318
6 -2 0 0.0282
0 0 11 0.0218
-5 1 7 0.0221
-6 1 -3 0.0215
6 -1 2 0.0257

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.048
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 9.0004 0.9978 -0.0222 -0.6507 -0.7712
1.0000 -9.0004 -0.9978 0.0222 0.6507 0.7712
1.0000 -0.0038 -10.9989 -0.0078 -0.6822 0.7170
-6.0000 0.0030 -2.9997 -0.9883 -0.1704 0.0040
6.0000 -2.0037 0.0004 0.9166 0.1439 0.3339
-0.0000 0.0031 10.9989 0.1650 0.6797 -0.6864
-5.0000 1.0052 6.9991 -0.6677 0.3656 -0.6649
-6.0000 1.0030 -2.9999 -0.9749 -0.2499 -0.0714
6.0000 -1.0032 2.0000 0.9599 0.1881 0.1338

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21962
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.675
_diffrn_reflns_theta_min         4.069
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4409
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -18.00   1.00    5.00    --  -42.53 -38.00 -90.00   99
  2  ω    -67.00  32.00   1.00    5.00    --  -42.53  38.00 120.00   99
  3  ω   -115.00 -14.00   1.00    5.00    --  -42.53 -57.00  30.00  101
  4  ω      2.00  99.00   1.00    5.00    --   42.53-125.00 -90.00   97
  5  ω     76.00 158.00   1.00   20.00    --  108.66  77.00   0.00   82
  6  ω     26.00 108.00   1.00   20.00    --  108.66 -94.00  60.00   82
  7  ω     33.00 141.00   1.00   20.00    --  108.66 -77.00 120.00  108
  8  ω     36.00 134.00   1.00   20.00    --  108.66 -45.00-150.00   98
  9  ω     73.00 158.00   1.00   20.00    --  108.66 125.00  90.00   85
 10  ω     80.00 158.00   1.00   20.00    --  108.66  61.00 -90.00   78
 11  ω   -119.00 -10.00   1.00    5.00    --  -42.53 -77.00 120.00  109
 12  ω   -119.00 -10.00   1.00    5.00    --  -42.53 -77.00-120.00  109
 13  ω   -115.00 -14.00   1.00    5.00    --  -42.53 -57.00 150.00  101
 14  ω     83.00 158.00   1.00   20.00    --  108.66  45.00 -30.00   75
 15  ω     80.00 158.00   1.00   20.00    --  108.66  30.00  90.00   78
 16  ω     80.00 158.00   1.00   20.00    --  108.66  61.00-120.00   78
 17  ω     35.00 122.00   1.00   20.00    --  108.66-125.00  60.00   87
 18  ω     80.00 158.00   1.00   20.00    --  108.66  30.00-150.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1572202000
_diffrn_orient_matrix_UB_12      0.0133352000
_diffrn_orient_matrix_UB_13      0.0149962000
_diffrn_orient_matrix_UB_21      -0.0025452000
_diffrn_orient_matrix_UB_22      -0.0794312000
_diffrn_orient_matrix_UB_23      0.0618232000
_diffrn_orient_matrix_UB_31      0.0304883000
_diffrn_orient_matrix_UB_32      -0.0753778000
_diffrn_orient_matrix_UB_33      -0.0623867000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3967
_reflns_number_total             4686
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.9491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0806
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C15(H15A,H15B,H15C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ga1 Ga 0.94495(2) 0.24968(2) 0.44121(2) 0.01306(8) Uani 1 1 d . . . . .
Cl1 Cl 1.06050(4) 0.25050(2) 0.55571(2) 0.01786(10) Uani 1 1 d . . . . .
O1 O 1.00355(11) 0.33068(7) 0.36185(6) 0.0183(2) Uani 1 1 d . . . . .
O3 O 0.79275(11) 0.16612(7) 0.42998(6) 0.0181(2) Uani 1 1 d . . . . .
O2 O 0.44298(12) 0.29815(8) 0.62295(6) 0.0204(2) Uani 1 1 d . . . . .
O4 O 1.39043(12) 0.32649(8) 0.30093(7) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.80871(13) 0.35027(9) 0.47999(7) 0.0157(3) Uani 1 1 d . . . . .
N2 N 1.07749(13) 0.14848(9) 0.39866(7) 0.0161(3) Uani 1 1 d . . . . .
C1 C 1.07795(18) 0.47065(12) 0.29845(10) 0.0239(3) Uani 1 1 d . . . . .
H1A H 1.1747 0.4496 0.3046 0.036 Uiso 1 1 calc GR . . . .
H1B H 1.0734 0.5404 0.3037 0.036 Uiso 1 1 calc GR . . . .
H1C H 1.0422 0.4520 0.2471 0.036 Uiso 1 1 calc GR . . . .
C2 C 0.99125(16) 0.42460(11) 0.35972(9) 0.0174(3) Uani 1 1 d . . . . .
C3 C 0.90888(16) 0.47759(11) 0.40611(10) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.9130 0.5451 0.4002 0.022 Uiso 1 1 calc R . . . .
C4 C 0.81611(15) 0.44121(11) 0.46330(9) 0.0170(3) Uani 1 1 d . . . . .
C5 C 0.72817(17) 0.51577(12) 0.50224(10) 0.0220(3) Uani 1 1 d . . . . .
H5A H 0.6337 0.4911 0.5082 0.033 Uiso 1 1 calc GR . . . .
H5B H 0.7251 0.5739 0.4705 0.033 Uiso 1 1 calc GR . . . .
H5C H 0.7687 0.5308 0.5533 0.033 Uiso 1 1 calc GR . . . .
C6 C 0.71129(16) 0.31662(11) 0.53929(9) 0.0180(3) Uani 1 1 d . . . . .
H6A H 0.7015 0.3667 0.5793 0.022 Uiso 1 1 calc R . . . .
H6B H 0.7501 0.2588 0.5648 0.022 Uiso 1 1 calc R . . . .
C7 C 0.56787(16) 0.29314(12) 0.50436(9) 0.0192(3) Uani 1 1 d . . . . .
H7A H 0.5202 0.3534 0.4896 0.023 Uiso 1 1 calc R . . . .
H7B H 0.5794 0.2547 0.4568 0.023 Uiso 1 1 calc R . . . .
C8 C 0.47844(17) 0.23822(11) 0.56036(10) 0.0201(3) Uani 1 1 d . . . . .
H8A H 0.3928 0.2157 0.5333 0.024 Uiso 1 1 calc R . . . .
H8B H 0.5299 0.1816 0.5800 0.024 Uiso 1 1 calc R . . . .
C9 C 0.36769(18) 0.24642(11) 0.67982(10) 0.0210(3) Uani 1 1 d . . . . .
H9A H 0.4306 0.2013 0.7074 0.025 Uiso 1 1 calc R . . . .
H9B H 0.2921 0.2091 0.6545 0.025 Uiso 1 1 calc R . . . .
C10 C 0.30772(19) 0.31625(14) 0.73623(10) 0.0276(4) Uani 1 1 d . . . . .
H10A H 0.2405 0.3577 0.7092 0.041 Uiso 1 1 calc GR . . . .
H10B H 0.3826 0.3554 0.7589 0.041 Uiso 1 1 calc GR . . . .
H10C H 0.2609 0.2812 0.7773 0.041 Uiso 1 1 calc GR . . . .
C11 C 0.65534(18) 0.02725(13) 0.42201(12) 0.0281(4) Uani 1 1 d . . . . .
H11A H 0.6102 0.0442 0.4705 0.042 Uiso 1 1 calc GR . . . .
H11B H 0.6651 -0.0424 0.4188 0.042 Uiso 1 1 calc GR . . . .
H11C H 0.5986 0.0502 0.3781 0.042 Uiso 1 1 calc GR . . . .
C12 C 0.79651(17) 0.07295(11) 0.42001(9) 0.0188(3) Uani 1 1 d . . . . .
C13 C 0.91275(17) 0.02020(11) 0.40760(9) 0.0192(3) Uani 1 1 d . . . . .
H13 H 0.9019 -0.0473 0.4064 0.023 Uiso 1 1 calc R . . . .
C14 C 1.05004(17) 0.05681(11) 0.39621(9) 0.0176(3) Uani 1 1 d . . . . .
C15 C 1.15929(18) -0.01776(12) 0.37933(10) 0.0219(3) Uani 1 1 d . . . . .
H15A H 1.1783 -0.0178 0.3238 0.033 Uiso 1 1 calc GR . . . .
H15B H 1.1255 -0.0810 0.3947 0.033 Uiso 1 1 calc GR . . . .
H15C H 1.2449 -0.0028 0.4086 0.033 Uiso 1 1 calc GR . . . .
C16 C 1.21745(16) 0.18311(11) 0.37971(10) 0.0193(3) Uani 1 1 d . . . . .
H16A H 1.2878 0.1379 0.4008 0.023 Uiso 1 1 calc R . . . .
H16B H 1.2334 0.2460 0.4047 0.023 Uiso 1 1 calc R . . . .
C17 C 1.23577(17) 0.19303(12) 0.29229(10) 0.0217(3) Uani 1 1 d . . . . .
H17A H 1.2224 0.1298 0.2675 0.026 Uiso 1 1 calc R . . . .
H17B H 1.1638 0.2369 0.2710 0.026 Uiso 1 1 calc R . . . .
C18 C 1.37836(18) 0.23120(12) 0.27298(11) 0.0244(4) Uani 1 1 d . . . . .
H18A H 1.4512 0.1906 0.2974 0.029 Uiso 1 1 calc R . . . .
H18B H 1.3908 0.2301 0.2162 0.029 Uiso 1 1 calc R . . . .
C19 C 1.52746(17) 0.36285(13) 0.29267(10) 0.0236(3) Uani 1 1 d . . . . .
H19A H 1.5543 0.3600 0.2377 0.028 Uiso 1 1 calc R . . . .
H19B H 1.5943 0.3239 0.3235 0.028 Uiso 1 1 calc R . . . .
C20 C 1.53003(19) 0.46512(13) 0.32063(11) 0.0286(4) Uani 1 1 d . . . . .
H20A H 1.4665 0.5037 0.2884 0.043 Uiso 1 1 calc GR . . . .
H20B H 1.6246 0.4906 0.3170 0.043 Uiso 1 1 calc GR . . . .
H20C H 1.5007 0.4675 0.3746 0.043 Uiso 1 1 calc GR . . . .


_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
Ga1 Cl1 2.2499(4) . ?
Ga1 O1 1.8736(11) . ?
Ga1 O3 1.8800(11) . ?
Ga1 N1 2.0443(12) . ?
Ga1 N2 2.0506(13) . ?
O1 C2 1.3184(19) . ?
O3 C12 1.3142(19) . ?
O2 C8 1.415(2) . ?
O2 C9 1.4289(19) . ?
O4 C18 1.421(2) . ?
O4 C19 1.4228(19) . ?
N1 C4 1.306(2) . ?
N1 C6 1.4792(19) . ?
N2 C14 1.309(2) . ?
N2 C16 1.4740(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.505(2) . ?
C2 C3 1.358(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.438(2) . ?
C4 C5 1.509(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.530(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.516(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.503(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C12 1.502(2) . ?
C12 C13 1.360(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.434(2) . ?
C14 C15 1.513(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.531(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.515(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.509(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O1 Ga1 Cl1 119.33(4) . . ?
O1 Ga1 O3 123.03(5) . . ?
O1 Ga1 N1 91.64(5) . . ?
O1 Ga1 N2 87.48(5) . . ?
O3 Ga1 Cl1 117.64(4) . . ?
O3 Ga1 N1 87.58(5) . . ?
O3 Ga1 N2 91.33(5) . . ?
N1 Ga1 Cl1 90.98(4) . . ?
N1 Ga1 N2 177.93(5) . . ?
N2 Ga1 Cl1 91.08(4) . . ?
C2 O1 Ga1 126.44(10) . . ?
C12 O3 Ga1 127.28(10) . . ?
C8 O2 C9 111.07(12) . . ?
C18 O4 C19 111.73(12) . . ?
C4 N1 Ga1 123.98(10) . . ?
C4 N1 C6 120.04(13) . . ?
C6 N1 Ga1 115.33(9) . . ?
C14 N2 Ga1 124.08(11) . . ?
C14 N2 C16 119.94(13) . . ?
C16 N2 Ga1 115.50(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 113.25(14) . . ?
O1 C2 C3 125.41(14) . . ?
C3 C2 C1 121.33(14) . . ?
C2 C3 H3 116.9 . . ?
C2 C3 C4 126.19(15) . . ?
C4 C3 H3 116.9 . . ?
N1 C4 C3 122.24(14) . . ?
N1 C4 C5 122.70(14) . . ?
C3 C4 C5 115.06(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
N1 C6 C7 111.96(13) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 112.06(13) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O2 C8 C7 109.67(13) . . ?
O2 C8 H8A 109.7 . . ?
O2 C8 H8B 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O2 C9 H9A 109.9 . . ?
O2 C9 H9B 109.9 . . ?
O2 C9 C10 108.91(13) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
O3 C12 C11 113.02(14) . . ?
O3 C12 C13 125.64(15) . . ?
C13 C12 C11 121.33(15) . . ?
C12 C13 H13 116.9 . . ?
C12 C13 C14 126.22(15) . . ?
C14 C13 H13 116.9 . . ?
N2 C14 C13 122.06(14) . . ?
N2 C14 C15 122.70(14) . . ?
C13 C14 C15 115.23(14) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
N2 C16 C17 111.89(13) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 C16 111.83(14) . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
O4 C18 C17 108.86(13) . . ?
O4 C18 H18A 109.9 . . ?
O4 C18 H18B 109.9 . . ?
C17 C18 H18A 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O4 C19 H19A 110.0 . . ?
O4 C19 H19B 110.0 . . ?
O4 C19 C20 108.39(14) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Ga1 O1 C2 C1 166.13(11) . . . . ?
Ga1 O1 C2 C3 -14.7(2) . . . . ?
Ga1 O3 C12 C11 173.61(11) . . . . ?
Ga1 O3 C12 C13 -7.5(2) . . . . ?
Ga1 N1 C4 C3 9.7(2) . . . . ?
Ga1 N1 C4 C5 -170.40(11) . . . . ?
Ga1 N1 C6 C7 -99.77(12) . . . . ?
Ga1 N2 C14 C13 13.8(2) . . . . ?
Ga1 N2 C14 C15 -167.76(11) . . . . ?
Ga1 N2 C16 C17 -104.92(13) . . . . ?
Cl1 Ga1 O1 C2 -70.96(13) . . . . ?
Cl1 Ga1 O3 C12 -75.62(13) . . . . ?
O1 Ga1 O3 C12 104.16(13) . . . . ?
O1 C2 C3 C4 -2.9(3) . . . . ?
O3 Ga1 O1 C2 109.27(13) . . . . ?
O3 C12 C13 C14 -6.0(3) . . . . ?
N1 Ga1 O1 C2 21.09(13) . . . . ?
N1 Ga1 O3 C12 -165.45(13) . . . . ?
N1 C6 C7 C8 167.17(13) . . . . ?
N2 Ga1 O1 C2 -160.78(13) . . . . ?
N2 Ga1 O3 C12 16.30(13) . . . . ?
N2 C16 C17 C18 178.45(13) . . . . ?
C1 C2 C3 C4 176.25(15) . . . . ?
C2 C3 C4 N1 4.6(3) . . . . ?
C2 C3 C4 C5 -175.27(16) . . . . ?
C4 N1 C6 C7 89.09(17) . . . . ?
C6 N1 C4 C3 -179.93(14) . . . . ?
C6 N1 C4 C5 -0.1(2) . . . . ?
C6 C7 C8 O2 68.11(17) . . . . ?
C8 O2 C9 C10 -168.57(14) . . . . ?
C9 O2 C8 C7 -175.51(13) . . . . ?
C11 C12 C13 C14 172.82(16) . . . . ?
C12 C13 C14 N2 1.7(3) . . . . ?
C12 C13 C14 C15 -176.87(16) . . . . ?
C14 N2 C16 C17 82.71(18) . . . . ?
C16 N2 C14 C13 -174.54(14) . . . . ?
C16 N2 C14 C15 3.9(2) . . . . ?
C16 C17 C18 O4 -65.76(18) . . . . ?
C18 O4 C19 C20 177.79(14) . . . . ?
C19 O4 C18 C17 173.23(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.517
_oxdiff_exptl_absorpt_empirical_full_min 0.800
####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc1q3hw6
_database_code_depnum_ccdc_archive 'CCDC 1582298'
_audit_update_record             
;
2017-10-26 deposited with the CCDC.
2017-12-28 downloaded from the CCDC.
;
_audit_creation_date             2017-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H26 Ga N3 O'
_chemical_formula_sum            'C12 H26 Ga N3 O'
_chemical_formula_weight         298.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ga C12H26 N3 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7637(2)
_cell_length_b                   14.6029(4)
_cell_length_c                   13.3304(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.544(3)
_cell_angle_gamma                90
_cell_volume                     1490.38(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    101.3(2)
_cell_measurement_theta_max      75.1140
_cell_measurement_theta_min      4.5050
_shelx_estimated_absorpt_T_max   0.828
_shelx_estimated_absorpt_T_min   0.696
_exptl_absorpt_coefficient_mu    2.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9173
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.110
_diffrn_reflns_theta_min         4.526
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101.3(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4409
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  35.00   1.00    1.00    --  -40.78  77.00 -60.00   27
  2  ω    -32.00  65.00   1.00    1.00    --   40.78 -38.00-150.00   97
  3  ω     82.00 109.00   1.00    4.00    --  109.91 -94.00 -60.00   27
  4  ω     74.00 138.00   1.00    4.00    --  109.91 -77.00 -30.00   64
  5  ω     63.00 119.00   1.00    4.00    --  109.91-125.00 -90.00   56
  6  ω     37.00 121.00   1.00    4.00    --  109.91 -30.00  30.00   84
  7  ω     95.00 142.00   1.00    4.00    --  109.91  30.00 -60.00   47
  8  ω     88.00 158.00   1.00    4.00    --  109.91  77.00-150.00   70
  9  ω     60.00 158.00   1.00    4.00    --  109.91  15.00  30.00   98
 10  ω     91.00 117.00   1.00    4.00    --  109.91-125.00 120.00   26
 11  ω     43.00 136.00   1.00    4.00    --  109.91 -45.00 120.00   93
 12  ω     36.00  94.00   1.00    4.00    --  109.91 -94.00 150.00   58
 13  ω     -7.00  67.00   1.00    1.00    --   40.78 -77.00  90.00   74
 14  ω    -20.00  61.00   1.00    1.00    --   40.78 -57.00 150.00   81
 15  ω    -71.00 -44.00   1.00    1.00    --  -40.78  77.00 -60.00   27
 16  ω   -111.00 -15.00   1.00    1.00    --  -40.78 -57.00-120.00   96
 17  ω     38.00 138.00   1.00    4.00    --  109.91 -61.00-120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1058013000
_diffrn_orient_matrix_UB_12      -0.0808209000
_diffrn_orient_matrix_UB_13      -0.0326202000
_diffrn_orient_matrix_UB_21      -0.1059124000
_diffrn_orient_matrix_UB_22      -0.0669731000
_diffrn_orient_matrix_UB_23      0.0551345000
_diffrn_orient_matrix_UB_31      -0.1343967000
_diffrn_orient_matrix_UB_32      -0.0106686000
_diffrn_orient_matrix_UB_33      -0.0981347000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2608
_reflns_number_total             3016
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3016
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+1.5086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0853
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C),
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ga Ga 0.19049(3) 0.22224(2) 0.40991(2) 0.01871(10) Uani 1 1 d . . . . .
O1 O 0.1428(2) 0.13323(11) 0.50559(13) 0.0249(3) Uani 1 1 d . . . . .
N3 N 0.4471(2) 0.22781(13) 0.45803(14) 0.0196(4) Uani 1 1 d . . . . .
N1 N 0.1633(3) 0.17481(13) 0.27814(14) 0.0227(4) Uani 1 1 d . . . . .
N2 N 0.0512(3) 0.31925(13) 0.43719(15) 0.0227(4) Uani 1 1 d . . . . .
C3 C 0.4383(3) 0.10008(16) 0.57230(17) 0.0233(5) Uani 1 1 d . . . . .
H3 H 0.5103 0.0587 0.6155 0.028 Uiso 1 1 calc R . . . .
C4 C 0.5274(3) 0.16902(16) 0.52468(17) 0.0217(4) Uani 1 1 d . . . . .
C5 C 0.7221(3) 0.17269(18) 0.56021(19) 0.0284(5) Uani 1 1 d . . . . .
H5A H 0.7810 0.1858 0.5022 0.043 Uiso 1 1 calc GR . . . .
H5B H 0.7625 0.1136 0.5902 0.043 Uiso 1 1 calc GR . . . .
H5C H 0.7493 0.2211 0.6113 0.043 Uiso 1 1 calc GR . . . .
C10 C -0.0077(3) 0.17182(16) 0.21498(17) 0.0245(5) Uani 1 1 d . . . . .
H10A H 0.0055 0.1634 0.1437 0.037 Uiso 1 1 calc GR . . . .
H10B H -0.0694 0.2294 0.2221 0.037 Uiso 1 1 calc GR . . . .
H10C H -0.0748 0.1207 0.2364 0.037 Uiso 1 1 calc GR . . . .
C8 C 0.4491(3) 0.38660(17) 0.3935(2) 0.0308(5) Uani 1 1 d . . . . .
H8A H 0.3499 0.3777 0.3385 0.046 Uiso 1 1 calc GR . . . .
H8B H 0.5255 0.4346 0.3743 0.046 Uiso 1 1 calc GR . . . .
H8C H 0.4060 0.4048 0.4557 0.046 Uiso 1 1 calc GR . . . .
C11 C 0.0012(3) 0.39399(16) 0.36677(19) 0.0271(5) Uani 1 1 d . . . . .
H11A H -0.1149 0.4163 0.3747 0.041 Uiso 1 1 calc GR . . . .
H11B H -0.0016 0.3723 0.2969 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.0862 0.4438 0.3811 0.041 Uiso 1 1 calc GR . . . .
C1 C 0.1909(3) 0.01457(17) 0.62616(19) 0.0292(5) Uani 1 1 d . . . . .
H1A H 0.1187 0.0439 0.6707 0.044 Uiso 1 1 calc GR . . . .
H1B H 0.2878 -0.0180 0.6676 0.044 Uiso 1 1 calc GR . . . .
H1C H 0.1197 -0.0289 0.5811 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.2583(3) 0.09078(17) 0.26690(19) 0.0282(5) Uani 1 1 d . . . . .
H9A H 0.1912 0.0384 0.2854 0.042 Uiso 1 1 calc GR . . . .
H9B H 0.3720 0.0928 0.3116 0.042 Uiso 1 1 calc GR . . . .
H9C H 0.2759 0.0844 0.1961 0.042 Uiso 1 1 calc GR . . . .
C7 C 0.5990(3) 0.26043(18) 0.3137(2) 0.0299(5) Uani 1 1 d . . . . .
H7A H 0.6678 0.2043 0.3279 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.6678 0.3063 0.2840 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.4920 0.2470 0.2658 0.045 Uiso 1 1 calc GR . . . .
C6 C 0.5513(3) 0.29747(16) 0.41243(18) 0.0241(5) Uani 1 1 d . . . . .
H6 H 0.6613 0.3097 0.4612 0.029 Uiso 1 1 calc R . . . .
C2 C 0.2624(3) 0.08637(16) 0.56342(17) 0.0230(5) Uani 1 1 d . . . . .
C12 C 0.0650(3) 0.34932(18) 0.54176(19) 0.0288(5) Uani 1 1 d . . . . .
H12A H 0.1550 0.3968 0.5557 0.043 Uiso 1 1 calc GR . . . .
H12B H 0.0967 0.2972 0.5874 0.043 Uiso 1 1 calc GR . . . .
H12C H -0.0475 0.3743 0.5529 0.043 Uiso 1 1 calc GR . . . .


_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
Ga O1 1.9000(16) . ?
Ga N3 1.9907(19) . ?
Ga N1 1.8673(19) . ?
Ga N2 1.8545(19) . ?
O1 C2 1.299(3) . ?
N3 C4 1.316(3) . ?
N3 C6 1.490(3) . ?
N1 C10 1.450(3) . ?
N1 C9 1.452(3) . ?
N2 C11 1.450(3) . ?
N2 C12 1.448(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.429(3) . ?
C3 C2 1.366(3) . ?
C4 C5 1.508(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C6 1.523(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.503(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C6 1.524(3) . ?
C6 H6 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
O1 Ga N3 96.18(7) . . ?
N1 Ga O1 111.93(8) . . ?
N1 Ga N3 105.62(8) . . ?
N2 Ga O1 101.89(8) . . ?
N2 Ga N3 119.38(8) . . ?
N2 Ga N1 119.29(9) . . ?
C2 O1 Ga 124.00(15) . . ?
C4 N3 Ga 121.87(15) . . ?
C4 N3 C6 119.47(19) . . ?
C6 N3 Ga 118.57(14) . . ?
C10 N1 Ga 120.47(15) . . ?
C10 N1 C9 110.28(19) . . ?
C9 N1 Ga 115.49(16) . . ?
C11 N2 Ga 123.39(15) . . ?
C12 N2 Ga 117.89(16) . . ?
C12 N2 C11 111.35(19) . . ?
C4 C3 H3 116.0 . . ?
C2 C3 H3 116.0 . . ?
C2 C3 C4 128.0(2) . . ?
N3 C4 C3 123.3(2) . . ?
N3 C4 C5 121.8(2) . . ?
C3 C4 C5 114.8(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
N3 C6 C8 110.34(19) . . ?
N3 C6 C7 109.62(19) . . ?
N3 C6 H6 108.7 . . ?
C8 C6 C7 110.8(2) . . ?
C8 C6 H6 108.7 . . ?
C7 C6 H6 108.7 . . ?
O1 C2 C3 125.5(2) . . ?
O1 C2 C1 113.8(2) . . ?
C3 C2 C1 120.6(2) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
Ga O1 C2 C3 7.2(3) . . . . ?
Ga O1 C2 C1 -175.02(15) . . . . ?
Ga N3 C4 C3 -3.6(3) . . . . ?
Ga N3 C4 C5 179.33(16) . . . . ?
Ga N3 C6 C8 37.8(2) . . . . ?
Ga N3 C6 C7 -84.5(2) . . . . ?
O1 Ga N1 C10 84.12(18) . . . . ?
O1 Ga N1 C9 -52.42(18) . . . . ?
O1 Ga N2 C11 -161.56(18) . . . . ?
O1 Ga N2 C12 51.06(18) . . . . ?
N3 Ga N1 C10 -172.40(17) . . . . ?
N3 Ga N1 C9 51.06(18) . . . . ?
N3 Ga N2 C11 94.28(19) . . . . ?
N3 Ga N2 C12 -53.11(19) . . . . ?
N1 Ga N2 C11 -37.8(2) . . . . ?
N1 Ga N2 C12 174.82(16) . . . . ?
N2 Ga N1 C10 -34.6(2) . . . . ?
N2 Ga N1 C9 -171.14(16) . . . . ?
C4 N3 C6 C8 -145.6(2) . . . . ?
C4 N3 C6 C7 92.1(2) . . . . ?
C4 C3 C2 O1 2.6(4) . . . . ?
C4 C3 C2 C1 -175.0(2) . . . . ?
C6 N3 C4 C3 179.9(2) . . . . ?
C6 N3 C4 C5 2.9(3) . . . . ?
C2 C3 C4 N3 -4.4(4) . . . . ?
C2 C3 C4 C5 172.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.629
####################################################################### 
# 
# 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_rod-013i
_audit_block_doi                 10.5517/ccdc.csd.cc1q3hx7
_database_code_depnum_ccdc_archive 'CCDC 1582299'
_audit_update_record             
;
2017-10-26 deposited with the CCDC.
2017-12-28 downloaded from the CCDC.
;
_audit_creation_date             2017-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H48 Ga N3 O6'
_chemical_formula_sum            'C27 H48 Ga N3 O6'
_chemical_formula_weight         580.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ga2 C50 H100 O6 N3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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'
Ga Ga -1.2850 0.7760 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.4543(4)
_cell_length_b                   8.65960(10)
_cell_length_c                   22.4511(9)
_cell_angle_alpha                90
_cell_angle_beta                 122.791(2)
_cell_angle_gamma                90
_cell_volume                     3016.12(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6085
_cell_measurement_temperature    111.1(3)
_cell_measurement_theta_max      76.2040
_cell_measurement_theta_min      5.0430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13120
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.332
_diffrn_reflns_theta_min         3.950
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      111.1(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4372
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -116.00  -80.00   1.0000    5.1850
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -99.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -84.00   1.0000    5.1850
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -99.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00   68.00   1.0000    5.1850
omega____ theta____ kappa____ phi______ frames
    -       41.2302  -57.0000 -120.0000 97

#__ type_ start__ end____ width___ exp.time_
  4 omega   17.00  111.00   1.0000    5.1850
omega____ theta____ kappa____ phi______ frames
    -       41.2302   57.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega  108.00  144.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   46.00   77.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   77.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
  8 omega   36.00   69.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   69.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
 11 omega   30.00   58.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00   69.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   92.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
 14 omega  109.00  135.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   35.00  116.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   90.0000 81

#__ type_ start__ end____ width___ exp.time_
 16 omega   92.00  138.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 17 omega   51.00  103.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  150.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0812117000
_diffrn_orient_matrix_UB_12      0.0509781000
_diffrn_orient_matrix_UB_13      -0.0038044000
_diffrn_orient_matrix_UB_21      0.0252159000
_diffrn_orient_matrix_UB_22      0.0108726000
_diffrn_orient_matrix_UB_23      0.0814470000
_diffrn_orient_matrix_UB_31      0.0227069000
_diffrn_orient_matrix_UB_32      0.1700379000
_diffrn_orient_matrix_UB_33      -0.0039773000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5425
_reflns_number_total             6196
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+1.2047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0823
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C21(H21)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C23(H23A,H23B,
 H23C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ga1 Ga 0.25251(2) 0.15444(2) 0.03846(2) 0.01816(7) Uani 1 1 d . . . . .
O1 O 0.30686(7) 0.25449(13) 0.13051(6) 0.0218(2) Uani 1 1 d . . . . .
O2 O 0.43858(9) -0.17985(15) 0.03391(7) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.24479(8) 0.34792(13) -0.01093(6) 0.0224(2) Uani 1 1 d . . . . .
O4 O 0.12209(9) 0.20380(15) 0.18322(7) 0.0298(3) Uani 1 1 d . . . . .
O5 O 0.19079(7) 0.06170(13) -0.05671(6) 0.0220(2) Uani 1 1 d . . . . .
O6 O 0.25752(10) -0.15911(15) 0.20808(7) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.37257(9) 0.12603(16) 0.05183(7) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.13549(9) 0.20744(15) 0.02577(7) 0.0192(3) Uani 1 1 d . . . . .
N3 N 0.26014(9) -0.06483(15) 0.07983(7) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.40455(12) 0.3823(2) 0.23712(10) 0.0311(4) Uani 1 1 d . . . . .
H1A H 0.3744 0.4815 0.2210 0.047 Uiso 1 1 calc GR . . . .
H1B H 0.4667 0.4005 0.2685 0.047 Uiso 1 1 calc GR . . . .
H1C H 0.3839 0.3256 0.2629 0.047 Uiso 1 1 calc GR . . . .
C2 C 0.38704(11) 0.28874(19) 0.17380(9) 0.0226(3) Uani 1 1 d . . . . .
C3 C 0.45386(11) 0.2464(2) 0.16689(9) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.5105 0.2701 0.2054 0.030 Uiso 1 1 calc R . . . .
C4 C 0.44642(11) 0.16972(19) 0.10711(9) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.53116(11) 0.1441(2) 0.11233(10) 0.0272(3) Uani 1 1 d . . . . .
H5A H 0.5367 0.0348 0.1042 0.041 Uiso 1 1 calc GR . . . .
H5B H 0.5792 0.1741 0.1596 0.041 Uiso 1 1 calc GR . . . .
H5C H 0.5323 0.2071 0.0766 0.041 Uiso 1 1 calc GR . . . .
C6 C 0.36984(11) 0.0645(2) -0.01050(9) 0.0247(3) Uani 1 1 d . . . . .
H6A H 0.4238 0.0928 -0.0073 0.030 Uiso 1 1 calc R . . . .
H6B H 0.3214 0.1132 -0.0538 0.030 Uiso 1 1 calc R . . . .
C7 C 0.35909(11) -0.1094(2) -0.01723(9) 0.0273(3) Uani 1 1 d . . . . .
H7A H 0.3135 -0.1416 -0.0093 0.033 Uiso 1 1 calc R . . . .
H7B H 0.3418 -0.1421 -0.0654 0.033 Uiso 1 1 calc R . . . .
C8 C 0.43092(15) -0.3426(2) 0.03680(13) 0.0394(5) Uani 1 1 d . . . . .
H8A H 0.4087 -0.3886 -0.0104 0.047 Uiso 1 1 calc R . . . .
H8B H 0.3903 -0.3676 0.0513 0.047 Uiso 1 1 calc R . . . .
C9 C 0.5187(2) -0.4059(3) 0.08969(15) 0.0597(7) Uani 1 1 d . . . . .
H9A H 0.5155 -0.5186 0.0914 0.090 Uiso 1 1 calc GR . . . .
H9B H 0.5391 -0.3627 0.1366 0.090 Uiso 1 1 calc GR . . . .
H9C H 0.5587 -0.3777 0.0756 0.090 Uiso 1 1 calc GR . . . .
C10 C 0.18016(13) 0.5045(2) -0.11308(10) 0.0318(4) Uani 1 1 d . . . . .
H10A H 0.2144 0.4544 -0.1291 0.048 Uiso 1 1 calc GR . . . .
H10B H 0.2086 0.6004 -0.0881 0.048 Uiso 1 1 calc GR . . . .
H10C H 0.1225 0.5281 -0.1541 0.048 Uiso 1 1 calc GR . . . .
C11 C 0.17252(11) 0.39801(19) -0.06378(9) 0.0233(3) Uani 1 1 d . . . . .
C12 C 0.09222(11) 0.36616(19) -0.07614(9) 0.0241(3) Uani 1 1 d . . . . .
H12 H 0.0436 0.4012 -0.1197 0.029 Uiso 1 1 calc R . . . .
C13 C 0.07588(10) 0.28515(18) -0.02925(9) 0.0216(3) Uani 1 1 d . . . . .
C14 C -0.01566(11) 0.2958(2) -0.04645(10) 0.0279(4) Uani 1 1 d . . . . .
H14A H -0.0508 0.3572 -0.0896 0.042 Uiso 1 1 calc GR . . . .
H14B H -0.0152 0.3454 -0.0070 0.042 Uiso 1 1 calc GR . . . .
H14C H -0.0401 0.1919 -0.0539 0.042 Uiso 1 1 calc GR . . . .
C15 C 0.11601(11) 0.14910(18) 0.07707(9) 0.0211(3) Uani 1 1 d . . . . .
H15A H 0.1519 0.0571 0.1014 0.025 Uiso 1 1 calc R . . . .
H15B H 0.0547 0.1178 0.0519 0.025 Uiso 1 1 calc R . . . .
C16 C 0.13382(11) 0.27303(19) 0.13161(9) 0.0241(3) Uani 1 1 d . . . . .
H16A H 0.1935 0.3120 0.1541 0.029 Uiso 1 1 calc R . . . .
H16B H 0.0936 0.3607 0.1086 0.029 Uiso 1 1 calc R . . . .
C17 C 0.13207(13) 0.3091(2) 0.23600(10) 0.0324(4) Uani 1 1 d . . . . .
H17A H 0.1079 0.2617 0.2617 0.039 Uiso 1 1 calc R . . . .
H17B H 0.0983 0.4036 0.2124 0.039 Uiso 1 1 calc R . . . .
C18 C 0.22418(15) 0.3541(3) 0.28872(12) 0.0487(6) Uani 1 1 d . . . . .
H18A H 0.2465 0.4127 0.2646 0.073 Uiso 1 1 calc GR . . . .
H18B H 0.2590 0.2609 0.3099 0.073 Uiso 1 1 calc GR . . . .
H18C H 0.2270 0.4181 0.3259 0.073 Uiso 1 1 calc GR . . . .
C19 C 0.06756(12) -0.0560(2) -0.15286(9) 0.0321(4) Uani 1 1 d . . . . .
H19A H 0.0372 0.0432 -0.1676 0.048 Uiso 1 1 calc GR . . . .
H19B H 0.0265 -0.1386 -0.1618 0.048 Uiso 1 1 calc GR . . . .
H19C H 0.0941 -0.0763 -0.1799 0.048 Uiso 1 1 calc GR . . . .
C20 C 0.13649(10) -0.0506(2) -0.07499(9) 0.0230(3) Uani 1 1 d . . . . .
C21 C 0.14020(11) -0.1624(2) -0.02992(9) 0.0238(3) Uani 1 1 d . . . . .
H21 H 0.0940 -0.2342 -0.0486 0.029 Uiso 1 1 calc R . . . .
C22 C 0.20822(10) -0.17923(19) 0.04291(9) 0.0212(3) Uani 1 1 d . . . . .
C23 C 0.21924(12) -0.33982(19) 0.07370(10) 0.0257(3) Uani 1 1 d . . . . .
H23A H 0.1692 -0.4033 0.0410 0.039 Uiso 1 1 calc GR . . . .
H23B H 0.2241 -0.3329 0.1193 0.039 Uiso 1 1 calc GR . . . .
H23C H 0.2716 -0.3871 0.0807 0.039 Uiso 1 1 calc GR . . . .
C24 C 0.33379(11) -0.09337(19) 0.15257(9) 0.0233(3) Uani 1 1 d . . . . .
H24A H 0.3837 -0.0324 0.1606 0.028 Uiso 1 1 calc R . . . .
H24B H 0.3497 -0.2039 0.1572 0.028 Uiso 1 1 calc R . . . .
C25 C 0.31663(11) -0.0526(2) 0.20976(9) 0.0256(3) Uani 1 1 d . . . . .
H25A H 0.3713 -0.0555 0.2568 0.031 Uiso 1 1 calc R . . . .
H25B H 0.2928 0.0532 0.2018 0.031 Uiso 1 1 calc R . . . .
C26 C 0.23832(14) -0.1279(2) 0.26036(10) 0.0320(4) Uani 1 1 d . . . . .
H26A H 0.2243 -0.0172 0.2593 0.038 Uiso 1 1 calc R . . . .
H26B H 0.2888 -0.1526 0.3081 0.038 Uiso 1 1 calc R . . . .
C27 C 0.1630(3) -0.2252(4) 0.24472(19) 0.0780(11) Uani 1 1 d . . . . .
H27A H 0.1111 -0.1887 0.2011 0.117 Uiso 1 1 calc GR . . . .
H27B H 0.1545 -0.2177 0.2841 0.117 Uiso 1 1 calc GR . . . .
H27C H 0.1740 -0.3330 0.2387 0.117 Uiso 1 1 calc GR . . . .


_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
Ga1 O1 1.9448(11) . ?
Ga1 O3 1.9712(11) . ?
Ga1 O5 1.9675(11) . ?
Ga1 N1 2.0831(14) . ?
Ga1 N2 2.0712(13) . ?
Ga1 N3 2.0848(14) . ?
O1 C2 1.290(2) . ?
O2 C7 1.421(2) . ?
O2 C8 1.421(2) . ?
O3 C11 1.289(2) . ?
O4 C16 1.422(2) . ?
O4 C17 1.426(2) . ?
O5 C20 1.293(2) . ?
O6 C25 1.413(2) . ?
O6 C26 1.424(2) . ?
N1 C4 1.307(2) . ?
N1 C6 1.473(2) . ?
N2 C13 1.310(2) . ?
N2 C15 1.469(2) . ?
N3 C22 1.314(2) . ?
N3 C24 1.473(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.512(2) . ?
C2 C3 1.373(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.436(2) . ?
C4 C5 1.520(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.515(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.500(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C11 1.505(2) . ?
C11 C12 1.380(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.426(2) . ?
C13 C14 1.518(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.524(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.504(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C20 1.506(2) . ?
C20 C21 1.375(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.431(2) . ?
C22 C23 1.517(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.521(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.496(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
O1 Ga1 O3 93.31(5) . . ?
O1 Ga1 O5 176.22(5) . . ?
O1 Ga1 N1 90.19(5) . . ?
O1 Ga1 N2 86.94(5) . . ?
O1 Ga1 N3 93.48(5) . . ?
O3 Ga1 N1 85.91(5) . . ?
O3 Ga1 N2 88.97(5) . . ?
O3 Ga1 N3 172.57(5) . . ?
O5 Ga1 O3 85.02(5) . . ?
O5 Ga1 N1 93.06(5) . . ?
O5 Ga1 N2 89.64(5) . . ?
O5 Ga1 N3 88.38(5) . . ?
N1 Ga1 N3 91.05(5) . . ?
N2 Ga1 N1 173.98(5) . . ?
N2 Ga1 N3 94.40(5) . . ?
C2 O1 Ga1 128.61(11) . . ?
C7 O2 C8 112.21(15) . . ?
C11 O3 Ga1 121.84(11) . . ?
C16 O4 C17 113.54(14) . . ?
C20 O5 Ga1 123.02(10) . . ?
C25 O6 C26 112.80(14) . . ?
C4 N1 Ga1 125.67(11) . . ?
C4 N1 C6 119.25(14) . . ?
C6 N1 Ga1 114.80(10) . . ?
C13 N2 Ga1 121.59(11) . . ?
C13 N2 C15 118.60(13) . . ?
C15 N2 Ga1 119.71(10) . . ?
C22 N3 Ga1 123.74(11) . . ?
C22 N3 C24 119.51(14) . . ?
C24 N3 Ga1 116.47(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 113.93(15) . . ?
O1 C2 C3 125.95(15) . . ?
C3 C2 C1 120.11(15) . . ?
C2 C3 H3 116.9 . . ?
C2 C3 C4 126.29(16) . . ?
C4 C3 H3 116.9 . . ?
N1 C4 C3 122.98(15) . . ?
N1 C4 C5 122.07(15) . . ?
C3 C4 C5 114.95(15) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.0 . . ?
N1 C6 H6B 109.0 . . ?
N1 C6 C7 112.93(14) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
O2 C7 C6 108.91(14) . . ?
O2 C7 H7A 109.9 . . ?
O2 C7 H7B 109.9 . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O2 C8 H8A 110.1 . . ?
O2 C8 H8B 110.1 . . ?
O2 C8 C9 107.88(18) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
O3 C11 C10 114.90(15) . . ?
O3 C11 C12 125.53(15) . . ?
C12 C11 C10 119.53(16) . . ?
C11 C12 H12 117.2 . . ?
C11 C12 C13 125.67(15) . . ?
C13 C12 H12 117.2 . . ?
N2 C13 C12 122.91(15) . . ?
N2 C13 C14 121.43(15) . . ?
C12 C13 C14 115.66(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
N2 C15 C16 110.47(13) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
O4 C16 C15 107.22(13) . . ?
O4 C16 H16A 110.3 . . ?
O4 C16 H16B 110.3 . . ?
C15 C16 H16A 110.3 . . ?
C15 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
O4 C17 H17A 108.8 . . ?
O4 C17 H17B 108.8 . . ?
O4 C17 C18 113.70(17) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
O5 C20 C19 114.47(15) . . ?
O5 C20 C21 125.08(15) . . ?
C21 C20 C19 120.41(16) . . ?
C20 C21 H21 117.4 . . ?
C20 C21 C22 125.14(15) . . ?
C22 C21 H21 117.4 . . ?
N3 C22 C21 122.21(15) . . ?
N3 C22 C23 122.13(15) . . ?
C21 C22 C23 115.60(15) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 H24A 108.7 . . ?
N3 C24 H24B 108.7 . . ?
N3 C24 C25 114.07(13) . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
O6 C25 C24 109.68(14) . . ?
O6 C25 H25A 109.7 . . ?
O6 C25 H25B 109.7 . . ?
C24 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
O6 C26 H26A 110.0 . . ?
O6 C26 H26B 110.0 . . ?
O6 C26 C27 108.32(17) . . ?
H26A C26 H26B 108.4 . . ?
C27 C26 H26A 110.0 . . ?
C27 C26 H26B 110.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
Ga1 O1 C2 C1 173.55(11) . . . . ?
Ga1 O1 C2 C3 -7.3(3) . . . . ?
Ga1 O3 C11 C10 -156.29(12) . . . . ?
Ga1 O3 C11 C12 26.1(2) . . . . ?
Ga1 O5 C20 C19 152.34(12) . . . . ?
Ga1 O5 C20 C21 -30.1(2) . . . . ?
Ga1 N1 C4 C3 -0.7(2) . . . . ?
Ga1 N1 C4 C5 179.99(12) . . . . ?
Ga1 N1 C6 C7 -80.90(15) . . . . ?
Ga1 N2 C13 C12 -13.5(2) . . . . ?
Ga1 N2 C13 C14 167.31(12) . . . . ?
Ga1 N2 C15 C16 98.27(13) . . . . ?
Ga1 N3 C22 C21 -0.7(2) . . . . ?
Ga1 N3 C22 C23 176.23(11) . . . . ?
Ga1 N3 C24 C25 89.20(15) . . . . ?
O1 C2 C3 C4 6.6(3) . . . . ?
O3 C11 C12 C13 6.5(3) . . . . ?
O5 C20 C21 C22 -5.2(3) . . . . ?
N1 C6 C7 O2 -74.86(18) . . . . ?
N2 C15 C16 O4 -174.18(13) . . . . ?
N3 C24 C25 O6 70.08(18) . . . . ?
C1 C2 C3 C4 -174.24(17) . . . . ?
C2 C3 C4 N1 -2.4(3) . . . . ?
C2 C3 C4 C5 177.01(17) . . . . ?
C4 N1 C6 C7 104.75(18) . . . . ?
C6 N1 C4 C3 173.00(15) . . . . ?
C6 N1 C4 C5 -6.3(2) . . . . ?
C7 O2 C8 C9 177.48(18) . . . . ?
C8 O2 C7 C6 172.79(15) . . . . ?
C10 C11 C12 C13 -171.01(16) . . . . ?
C11 C12 C13 N2 -12.6(3) . . . . ?
C11 C12 C13 C14 166.63(16) . . . . ?
C13 N2 C15 C16 -85.40(17) . . . . ?
C15 N2 C13 C12 170.30(15) . . . . ?
C15 N2 C13 C14 -8.9(2) . . . . ?
C16 O4 C17 C18 -73.8(2) . . . . ?
C17 O4 C16 C15 -176.74(14) . . . . ?
C19 C20 C21 C22 172.25(16) . . . . ?
C20 C21 C22 N3 21.2(3) . . . . ?
C20 C21 C22 C23 -155.89(16) . . . . ?
C22 N3 C24 C25 -96.68(17) . . . . ?
C24 N3 C22 C21 -174.39(14) . . . . ?
C24 N3 C22 C23 2.6(2) . . . . ?
C25 O6 C26 C27 168.6(2) . . . . ?
C26 O6 C25 C24 -179.97(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
