# 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. 
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data_md408_ph_rz01
_database_code_depnum_ccdc_archive 'CCDC 1569393'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
_audit_creation_date             2017-05-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H28 Ga2 N2 O2'
_chemical_formula_sum            'C10 H28 Ga2 N2 O2'
_chemical_formula_weight         347.78
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 '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'

_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                   6.6946(3)
_cell_length_b                   10.7516(5)
_cell_length_c                   11.4183(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.446(4)
_cell_angle_gamma                90
_cell_volume                     818.15(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2639
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      31.0510
_cell_measurement_theta_min      4.1670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.285
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 0 10 0.1035
11 0 -12 0.0895
0 11 -18 0.0334
-7 17 1 0.0981
0 -11 18 0.0343
7 -17 -1 0.1103
0 -11 -18 0.1361
-11 0 -10 0.1140
-11 0 12 0.0957
7 17 -1 0.0978
-7 -17 1 0.0875
-3 13 7 0.0807

_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.068
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.394
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00   7.00   1.00   18.00    --  -19.34 -77.00-150.00  105
  2  ω    -45.00 -10.00   1.00   18.00    --  -19.34 -38.00-120.00   35
  3  ω    -98.00 -71.00   1.00   18.00    --  -19.34-179.00-120.00   27
  4  ω    -68.00 -35.00   1.00   18.00    --  -19.34-179.00-120.00   33
  5  ω    -54.00  48.00   1.00   18.00    --   20.12 -57.00  90.00  102
  6  ω    -39.00  44.00   1.00   18.00    --   20.12 -38.00-120.00   83
  7  ω     77.00 110.00   1.00   18.00    --   20.12 179.00-120.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0220495000
_diffrn_orient_matrix_UB_12      0.0267015000
_diffrn_orient_matrix_UB_13      -0.0565745000
_diffrn_orient_matrix_UB_21      -0.0954734000
_diffrn_orient_matrix_UB_22      -0.0291706000
_diffrn_orient_matrix_UB_23      -0.0048044000
_diffrn_orient_matrix_UB_31      -0.0414214000
_diffrn_orient_matrix_UB_32      0.0528035000
_diffrn_orient_matrix_UB_33      0.0259615000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1465
_reflns_number_total             1672
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1672
_refine_ls_number_restraints     101
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.2920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          
;
_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 Ga1-N11 ∼ Ga1-N1
 with sigma of 0.02
 N1-C2 ∼ N11-C12
 with sigma of 0.02
 C11-C12 ∼ C1-C2
 with sigma of 0.02
 O11-C11 ∼ O1-C1
 with sigma of 0.02
 Ga1-O1 ∼ Ga1-O11
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 ∼ O11 ∼ N1 ∼ N11 ∼ C1 ∼ C2 ∼ C11 ∼ C12: within
2A with sigma of 0.008 and sigma for terminal atoms of 0.006
4. Others
 Sof(O11)=Sof(N11)=Sof(H11)=Sof(H31B)=Sof(H31A)=Sof(H31C)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=1-FVAR(1)
 Sof(O1)=Sof(N1)=Sof(H1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2A)=Sof(H2B)=
 Sof(H3A)=Sof(H3C)=Sof(H3B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 N1(H1), N11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C11(H11A,H11B), C12(H12A,H12B)
5.c Me refined with riding coordinates:
 C3(H3A,H3C,H3B), C3(H31B,H31A,H31C)
5.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.45774(5) 0.63132(3) 0.43775(3) 0.02997(17) Uani 1 1 d D . . . .
O1 O 0.4073(11) 0.5414(7) 0.5773(5) 0.0379(15) Uani 0.763(12) 1 d D U P A 1
O11 O 0.367(4) 0.527(2) 0.5574(17) 0.037(3) Uani 0.237(12) 1 d D U P A 2
N1 N 0.2333(9) 0.7622(4) 0.5221(4) 0.0339(11) Uani 0.763(12) 1 d D U P A 1
H1 H 0.0966 0.7423 0.4837 0.041 Uiso 0.763(12) 1 calc R . P A 1
N11 N 0.319(3) 0.7746(12) 0.5585(15) 0.039(2) Uani 0.237(12) 1 d D U P A 2
H11 H 0.4362 0.7960 0.6157 0.047 Uiso 0.237(12) 1 calc R . P A 2
C1 C 0.2672(13) 0.5813(7) 0.6513(7) 0.0487(16) Uani 0.763(12) 1 d D U P A 1
H1A H 0.3131 0.5587 0.7335 0.058 Uiso 0.763(12) 1 calc R . P A 1
H1B H 0.1374 0.5392 0.6297 0.058 Uiso 0.763(12) 1 calc R . P A 1
C2 C 0.2396(11) 0.7173(7) 0.6423(6) 0.0389(14) Uani 0.763(12) 1 d D U P A 1
H2A H 0.1131 0.7402 0.6752 0.047 Uiso 0.763(12) 1 calc R . P A 1
H2B H 0.3512 0.7588 0.6903 0.047 Uiso 0.763(12) 1 calc R . P A 1
C3 C 0.2568(7) 0.8947(4) 0.5146(4) 0.0607(12) Uani 1 1 d . . . . .
H3A H 0.2512 0.9195 0.4318 0.091 Uiso 0.763(12) 1 calc R . P A 1
H3C H 0.1485 0.9359 0.5518 0.091 Uiso 0.763(12) 1 calc R . P A 1
H3B H 0.3865 0.9190 0.5551 0.091 Uiso 0.763(12) 1 calc R . P A 1
H31B H 0.3593 0.9287 0.4678 0.091 Uiso 0.237(12) 1 calc R . P A 2
H31A H 0.1294 0.8870 0.4652 0.091 Uiso 0.237(12) 1 calc R . P A 2
H31C H 0.2392 0.9504 0.5807 0.091 Uiso 0.237(12) 1 calc R . P A 2
C4 C 0.2705(6) 0.6176(4) 0.2946(4) 0.0595(12) Uani 1 1 d . . . . .
H4A H 0.3374 0.5756 0.2329 0.089 Uiso 1 1 calc GR . . . .
H4B H 0.2283 0.7009 0.2678 0.089 Uiso 1 1 calc GR . . . .
H4C H 0.1527 0.5693 0.3120 0.089 Uiso 1 1 calc GR . . . .
C5 C 0.6975(6) 0.7376(4) 0.4566(3) 0.0505(10) Uani 1 1 d . . . . .
H5A H 0.7519 0.7381 0.5393 0.076 Uiso 1 1 calc GR . . . .
H5B H 0.6613 0.8225 0.4317 0.076 Uiso 1 1 calc GR . . . .
H5C H 0.7988 0.7052 0.4080 0.076 Uiso 1 1 calc GR . . . .
C11 C 0.217(4) 0.569(2) 0.6218(19) 0.036(2) Uani 0.237(12) 1 d D U P A 2
H11A H 0.2409 0.5346 0.7022 0.043 Uiso 0.237(12) 1 calc R . P A 2
H11B H 0.0880 0.5349 0.5863 0.043 Uiso 0.237(12) 1 calc R . P A 2
C12 C 0.195(4) 0.701(2) 0.631(2) 0.040(2) Uani 0.237(12) 1 d D U P A 2
H12A H 0.2285 0.7256 0.7147 0.048 Uiso 0.237(12) 1 calc R . P A 2
H12B H 0.0525 0.7231 0.6100 0.048 Uiso 0.237(12) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ga1 O1 2.079(8) 3_666 ?
Ga1 O1 1.922(5) . ?
Ga1 O11 1.912(15) . ?
Ga1 O11 2.06(3) 3_666 ?
Ga1 N1 2.333(4) . ?
Ga1 N11 2.321(11) . ?
Ga1 C4 1.968(4) . ?
Ga1 C5 1.965(4) . ?
O1 Ga1 2.079(8) 3_666 ?
O1 C1 1.388(6) . ?
O11 Ga1 2.06(3) 3_666 ?
O11 C11 1.377(15) . ?
N1 H1 1.0000 . ?
N1 C2 1.452(7) . ?
N1 C3 1.436(5) . ?
N11 H11 1.0000 . ?
N11 C3 1.432(15) . ?
N11 C12 1.460(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.476(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H31B 0.9800 . ?
C3 H31A 0.9800 . ?
C3 H31C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.434(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ga1 O1 74.4(3) . 3_666 ?
O1 Ga1 N1 77.9(3) . . ?
O1 Ga1 N1 151.06(17) 3_666 . ?
O1 Ga1 C4 120.2(2) . . ?
O1 Ga1 C5 114.1(2) . . ?
O11 Ga1 O11 73.5(11) . 3_666 ?
O11 Ga1 N11 78.0(9) . . ?
O11 Ga1 N11 142.2(8) 3_666 . ?
O11 Ga1 C4 109.2(8) . . ?
O11 Ga1 C5 125.1(8) . . ?
C4 Ga1 O1 96.4(2) . 3_666 ?
C4 Ga1 O11 106.0(7) . 3_666 ?
C4 Ga1 N1 90.2(2) . . ?
C4 Ga1 N11 106.5(6) . . ?
C5 Ga1 O1 99.9(2) . 3_666 ?
C5 Ga1 O11 91.1(6) . 3_666 ?
C5 Ga1 N1 98.94(18) . . ?
C5 Ga1 N11 85.3(5) . . ?
C5 Ga1 C4 125.69(17) . . ?
Ga1 O1 Ga1 105.6(3) . 3_666 ?
C1 O1 Ga1 130.6(4) . 3_666 ?
C1 O1 Ga1 122.1(5) . . ?
Ga1 O11 Ga1 106.5(11) . 3_666 ?
C11 O11 Ga1 119.0(16) . . ?
C11 O11 Ga1 134.5(12) . 3_666 ?
Ga1 N1 H1 106.7 . . ?
C2 N1 Ga1 103.1(4) . . ?
C2 N1 H1 106.7 . . ?
C3 N1 Ga1 119.7(3) . . ?
C3 N1 H1 106.7 . . ?
C3 N1 C2 113.2(5) . . ?
Ga1 N11 H11 101.8 . . ?
C3 N11 Ga1 120.6(8) . . ?
C3 N11 H11 101.8 . . ?
C3 N11 C12 121.6(16) . . ?
C12 N11 Ga1 105.2(14) . . ?
C12 N11 H11 101.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 C2 110.6(6) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
N1 C2 C1 112.8(5) . . ?
N1 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3C 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N11 C3 H31B 109.5 . . ?
N11 C3 H31A 109.5 . . ?
N11 C3 H31C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3C C3 H3B 109.5 . . ?
H31B C3 H31A 109.5 . . ?
H31B C3 H31C 109.5 . . ?
H31A C3 H31C 109.5 . . ?
Ga1 C4 H4A 109.5 . . ?
Ga1 C4 H4B 109.5 . . ?
Ga1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Ga1 C5 H5A 109.5 . . ?
Ga1 C5 H5B 109.5 . . ?
Ga1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O11 C11 H11A 108.0 . . ?
O11 C11 H11B 108.0 . . ?
O11 C11 C12 117.1(18) . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 H11A 108.0 . . ?
C12 C11 H11B 108.0 . . ?
N11 C12 H12A 108.5 . . ?
N11 C12 H12B 108.5 . . ?
C11 C12 N11 115.0(18) . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?

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 C1 C2 -26.2(7) . . . . ?
Ga1 O1 C1 C2 171.2(5) 3_666 . . . ?
Ga1 O11 C11 C12 151(2) 3_666 . . . ?
Ga1 O11 C11 C12 -25(3) . . . . ?
Ga1 N1 C2 C1 -34.7(6) . . . . ?
Ga1 N11 C12 C11 9(3) . . . . ?
O1 C1 C2 N1 41.4(7) . . . . ?
O11 C11 C12 N11 8(3) . . . . ?
C3 N1 C2 C1 -165.4(5) . . . . ?
C3 N11 C12 C11 150.8(18) . . . . ?

####################################################################### 
# 
# 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_md500_imp-ah-10
_database_code_depnum_ccdc_archive 'CCDC 1569395'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
_audit_creation_date             2017-05-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H48 Ga2 N2 O4'
_chemical_formula_sum            'C28 H48 Ga2 N2 O4'
_chemical_formula_weight         616.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.4049(7)
_cell_length_b                   8.2553(3)
_cell_length_c                   18.0932(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.559(3)
_cell_angle_gamma                90
_cell_volume                     3143.00(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8135
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      30.1980
_cell_measurement_theta_min      3.8200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.746
_exptl_absorpt_correction_T_max  0.701
_exptl_absorpt_correction_T_min  0.462
_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    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -12 -3 0.2080
-26 6 7 0.1447
-14 5 -18 0.1492
-20 1 -15 0.1051
2 -2 -25 0.2050
24 1 11 0.1533
27 -5 -7 0.1752
12 11 1 0.2486
0 11 -5 0.2259
-29 4 4 0.1393
2 -11 4 0.1858
-23 7 -3 0.1267
-23 -6 12 0.2145
5 -10 11 0.1742
-19 6 -11 0.1216
1 -8 18 0.1820
28 -4 2 0.1353
-22 4 -12 0.0954
16 -4 16 0.1232
-15 1 -19 0.1352
21 -1 15 0.1267
-15 -2 -19 0.1562
-23 1 20 0.1502
30 0 -6 0.1365
-17 -7 -11 0.1997

_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.414
_exptl_crystal_size_min          0.23
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16888
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.033
_diffrn_reflns_theta_min         3.259
_diffrn_ambient_temperature      293(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  64.00   1.00   22.50    --  -14.40  77.00  90.00  112
  2  ω    -93.00  19.00   1.00   22.50    --  -14.40 -77.00 -90.00  112
  3  ω    -88.00  15.00   1.00   22.50    --  -14.40 -57.00 -30.00  103
  4  ω    -61.00  41.00   1.00   22.50    --   14.72 -38.00  90.00  102
  5  ω    -44.00  16.00   1.00   22.50    --  -14.40  57.00 -60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062295000
_diffrn_orient_matrix_UB_12      -0.0570904000
_diffrn_orient_matrix_UB_13      -0.0297484000
_diffrn_orient_matrix_UB_21      0.0048850000
_diffrn_orient_matrix_UB_22      -0.0641848000
_diffrn_orient_matrix_UB_23      0.0264903000
_diffrn_orient_matrix_UB_31      -0.0327583000
_diffrn_orient_matrix_UB_32      0.0012759000
_diffrn_orient_matrix_UB_33      0.0020959000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2753
_reflns_number_total             3096
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0221
_refine_ls_restrained_S_all      1.063
_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)+(0.0320P)²+1.8530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0620
_refine_special_details          
;
_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.43412(2) 0.69097(2) 0.77437(2) 0.03490(8) Uani 1 1 d . . . . .
O1 O 0.46977(5) 0.72001(14) 0.68379(6) 0.0350(2) Uani 1 1 d . . . . .
O2 O 0.52721(6) 0.66502(16) 0.55626(7) 0.0477(3) Uani 1 1 d . . . . .
N1 N 0.33966(7) 0.6578(2) 0.66711(8) 0.0399(3) Uani 1 1 d . . . . .
H1 H 0.3378(9) 0.557(3) 0.6642(11) 0.048 Uiso 1 1 d R . . . .
C1 C 0.43640(7) 0.6617(2) 0.61421(9) 0.0353(3) Uani 1 1 d . . . . .
H1A H 0.4384 0.5431 0.6141 0.042 Uiso 1 1 calc R . . . .
C2 C 0.46421(8) 0.7260(2) 0.54907(9) 0.0402(4) Uani 1 1 d . . . . .
H2A H 0.4388 0.6909 0.5018 0.048 Uiso 1 1 calc R . . . .
H2B H 0.4647 0.8435 0.5499 0.048 Uiso 1 1 calc R . . . .
C3 C 0.36708(8) 0.7145(2) 0.60399(9) 0.0408(4) Uani 1 1 d . . . . .
H3A H 0.3644 0.8317 0.6010 0.049 Uiso 1 1 calc R . . . .
H3B H 0.3435 0.6700 0.5575 0.049 Uiso 1 1 calc R . . . .
C4 C 0.42131(9) 0.4617(2) 0.79670(11) 0.0518(5) Uani 1 1 d . . . . .
H4A H 0.4238 0.3974 0.7532 0.078 Uiso 1 1 calc GR . . . .
H4B H 0.3802 0.4481 0.8100 0.078 Uiso 1 1 calc GR . . . .
H4C H 0.4536 0.4277 0.8378 0.078 Uiso 1 1 calc GR . . . .
C5 C 0.40343(9) 0.8987(2) 0.80581(10) 0.0479(4) Uani 1 1 d . . . . .
H5A H 0.4390 0.9652 0.8270 0.072 Uiso 1 1 calc GR . . . .
H5B H 0.3773 0.8803 0.8428 0.072 Uiso 1 1 calc GR . . . .
H5C H 0.3790 0.9525 0.7630 0.072 Uiso 1 1 calc GR . . . .
C6 C 0.27670(9) 0.7242(3) 0.67155(12) 0.0540(5) Uani 1 1 d . . . . .
H6 H 0.2805 0.8424 0.6750 0.065 Uiso 1 1 calc R . . . .
C7 C 0.25621(11) 0.6645(3) 0.74172(13) 0.0684(6) Uani 1 1 d . . . . .
H7A H 0.2540 0.5484 0.7407 0.103 Uiso 1 1 calc GR . . . .
H7B H 0.2151 0.7081 0.7445 0.103 Uiso 1 1 calc GR . . . .
H7C H 0.2864 0.6989 0.7849 0.103 Uiso 1 1 calc GR . . . .
C8 C 0.22589(11) 0.6840(5) 0.60352(15) 0.1109(14) Uani 1 1 d . . . . .
H8A H 0.2351 0.7394 0.5601 0.166 Uiso 1 1 calc GR . . . .
H8B H 0.1851 0.7179 0.6127 0.166 Uiso 1 1 calc GR . . . .
H8C H 0.2254 0.5692 0.5948 0.166 Uiso 1 1 calc GR . . . .
C9 C 0.56243(9) 0.7113(2) 0.50396(10) 0.0450(4) Uani 1 1 d . . . . .
C10 C 0.62489(10) 0.6596(3) 0.51859(13) 0.0616(6) Uani 1 1 d . . . . .
H10 H 0.6406 0.6010 0.5619 0.074 Uiso 1 1 calc R . . . .
C11 C 0.66393(12) 0.6969(3) 0.46725(18) 0.0815(9) Uani 1 1 d . . . . .
H11 H 0.7060 0.6626 0.4763 0.098 Uiso 1 1 calc R . . . .
C12 C 0.64088(16) 0.7837(3) 0.40337(18) 0.0872(10) Uani 1 1 d . . . . .
H12 H 0.6673 0.8081 0.3694 0.105 Uiso 1 1 calc R . . . .
C13 C 0.57943(15) 0.8340(3) 0.38999(15) 0.0751(7) Uani 1 1 d . . . . .
H13 H 0.5642 0.8931 0.3467 0.090 Uiso 1 1 calc R . . . .
C14 C 0.53884(11) 0.7991(2) 0.43963(11) 0.0535(5) Uani 1 1 d . . . . .
H14 H 0.4968 0.8339 0.4299 0.064 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ga1 O1 1.9452(11) . ?
Ga1 O1 2.0717(11) 2_656 ?
Ga1 C4 1.9648(18) . ?
Ga1 C5 1.9578(18) . ?
O1 Ga1 2.0717(11) 2_656 ?
O1 C1 1.4134(18) . ?
O2 C2 1.423(2) . ?
O2 C9 1.368(2) . ?
N1 H1 0.83(2) . ?
N1 C3 1.454(2) . ?
N1 C6 1.471(2) . ?
C1 H1A 0.9800 . ?
C1 C2 1.511(2) . ?
C1 C3 1.525(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6 0.9800 . ?
C6 C7 1.500(3) . ?
C6 C8 1.523(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.382(3) . ?
C9 C14 1.385(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.358(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9300 . ?

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 O1 77.11(5) . 2_656 ?
O1 Ga1 C4 112.52(7) . . ?
O1 Ga1 C5 109.95(7) . . ?
C4 Ga1 O1 101.71(7) . 2_656 ?
C5 Ga1 O1 98.98(6) . 2_656 ?
C5 Ga1 C4 135.81(9) . . ?
Ga1 O1 Ga1 101.21(5) . 2_656 ?
C1 O1 Ga1 126.29(9) . 2_656 ?
C1 O1 Ga1 119.75(9) . . ?
C9 O2 C2 118.10(14) . . ?
C3 N1 H1 107.1(14) . . ?
C3 N1 C6 115.39(15) . . ?
C6 N1 H1 110.0(14) . . ?
O1 C1 H1A 109.1 . . ?
O1 C1 C2 111.59(13) . . ?
O1 C1 C3 109.40(13) . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 C3 108.57(13) . . ?
C3 C1 H1A 109.1 . . ?
O2 C2 C1 107.84(13) . . ?
O2 C2 H2A 110.1 . . ?
O2 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.5 . . ?
N1 C3 C1 109.67(14) . . ?
N1 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C1 C3 H3A 109.7 . . ?
C1 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
Ga1 C4 H4A 109.5 . . ?
Ga1 C4 H4B 109.5 . . ?
Ga1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Ga1 C5 H5A 109.5 . . ?
Ga1 C5 H5B 109.5 . . ?
Ga1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6 107.9 . . ?
N1 C6 C7 109.68(17) . . ?
N1 C6 C8 113.60(19) . . ?
C7 C6 H6 107.9 . . ?
C7 C6 C8 109.6(2) . . ?
C8 C6 H6 107.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C10 114.68(19) . . ?
O2 C9 C14 124.41(18) . . ?
C10 C9 C14 120.89(19) . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.8(3) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 C13 118.5(2) . . ?
C9 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ga1 O1 C1 C2 167.91(10) . . . . ?
Ga1 O1 C1 C2 -57.85(17) 2_656 . . . ?
Ga1 O1 C1 C3 -178.01(10) 2_656 . . . ?
Ga1 O1 C1 C3 47.75(16) . . . . ?
O1 C1 C2 O2 63.91(18) . . . . ?
O1 C1 C3 N1 -56.45(18) . . . . ?
O2 C9 C10 C11 178.14(18) . . . . ?
O2 C9 C14 C13 -178.12(18) . . . . ?
C2 O2 C9 C10 174.21(16) . . . . ?
C2 O2 C9 C14 -7.5(3) . . . . ?
C2 C1 C3 N1 -178.45(14) . . . . ?
C3 N1 C6 C7 -176.21(18) . . . . ?
C3 N1 C6 C8 60.7(3) . . . . ?
C3 C1 C2 O2 -175.44(14) . . . . ?
C6 N1 C3 C1 169.56(16) . . . . ?
C9 O2 C2 C1 -178.40(14) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C9 0.1(3) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?

####################################################################### 
# 
# 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_md413_impuls_ah1
_database_code_depnum_ccdc_archive 'CCDC 1569394'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
_audit_creation_date             2017-05-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H36 Ga2 N2 O2'
_chemical_formula_sum            'C14 H36 Ga2 N2 O2'
_chemical_formula_weight         403.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 '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'

_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                   6.4969(2)
_cell_length_b                   13.5023(4)
_cell_length_c                   11.1683(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.288(3)
_cell_angle_gamma                90
_cell_volume                     975.55(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6471
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      30.3790
_cell_measurement_theta_min      3.9380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.765
_exptl_absorpt_correction_T_max  0.683
_exptl_absorpt_correction_T_min  0.183
_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    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 15 10 0.2006
-2 -12 -11 0.2258
-8 3 -7 0.3723
-7 13 3 0.4155
1 13 -11 0.0804
0 -15 -10 0.1812
-1 -10 13 0.0768
-1 -14 11 0.0714
8 9 -5 0.2716

_exptl_crystal_size_max          0.892
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.154
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.874
_diffrn_reflns_theta_min         3.530
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  61.00   1.00    2.50    --  -14.40  38.00 120.00   86
  2  ω    -43.00  29.00   1.00    2.50    --  -14.40  57.00  30.00   72
  3  ω    -77.00 -51.00   1.00    2.50    --  -14.40 133.00  34.94   26
  4  ω    -93.00 -16.00   1.00    2.50    --  -14.40 156.00 121.31   77
  5  ω    -93.00 -16.00   1.00    2.50    --  -14.40 156.00-156.31   77
  6  ω    -88.00  13.00   1.00    2.50    --  -14.40 -57.00 -30.00  101
  7  ω    -90.00  12.00   1.00    2.50    --  -14.40 -38.00  60.00  102
  8  ω    -93.00  14.00   1.00    2.50    --  -14.40 -77.00-150.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0999420000
_diffrn_orient_matrix_UB_12      0.0187863000
_diffrn_orient_matrix_UB_13      0.0183737000
_diffrn_orient_matrix_UB_21      -0.0029295000
_diffrn_orient_matrix_UB_22      -0.0233532000
_diffrn_orient_matrix_UB_23      0.0566770000
_diffrn_orient_matrix_UB_31      0.0450255000
_diffrn_orient_matrix_UB_32      -0.0431678000
_diffrn_orient_matrix_UB_33      -0.0226836000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2116
_reflns_number_total             2331
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         2331
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0206
_refine_ls_restrained_S_all      1.073
_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)+(0.0220P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0526
_refine_special_details          
;
_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 1 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.50971(2) 0.60409(2) 0.56876(2) 0.01887(7) Uani 1 1 d . . . . .
O1 O 0.59238(19) 0.54201(8) 0.42704(11) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.69736(18) 0.73113(9) 0.48286(11) 0.0165(2) Uani 1 1 d D . . . .
H1 H 0.8391(16) 0.7248(12) 0.5179(14) 0.020 Uiso 1 1 d DR . . . .
C1 C 0.7243(3) 0.58884(11) 0.35291(15) 0.0258(3) Uani 1 1 d . . . . .
H1A H 0.6958 0.5646 0.2694 0.031 Uiso 1 1 calc R . . . .
H1B H 0.8697 0.5729 0.3805 0.031 Uiso 1 1 calc R . . . .
C2 C 0.6918(3) 0.69991(12) 0.35655(14) 0.0246(3) Uani 1 1 d . . . . .
H2A H 0.8019 0.7341 0.3168 0.029 Uiso 1 1 calc R . . . .
H2B H 0.5568 0.7173 0.3134 0.029 Uiso 1 1 calc R . . . .
C3 C 0.6345(2) 0.83536(10) 0.49854(14) 0.0199(3) Uani 1 1 d . . . . .
H3 H 0.4880 0.8426 0.4634 0.024 Uiso 1 1 calc R . . . .
C4 C 0.7007(3) 0.59770(12) 0.71608(17) 0.0300(4) Uani 1 1 d . . . . .
H4A H 0.6433 0.5538 0.7745 0.045 Uiso 1 1 calc GR . . . .
H4B H 0.7193 0.6642 0.7505 0.045 Uiso 1 1 calc GR . . . .
H4C H 0.8346 0.5719 0.6965 0.045 Uiso 1 1 calc GR . . . .
C5 C 0.2378(2) 0.67017(13) 0.54451(15) 0.0255(3) Uani 1 1 d . . . . .
H5A H 0.1937 0.6737 0.4583 0.038 Uiso 1 1 calc GR . . . .
H5B H 0.2487 0.7373 0.5779 0.038 Uiso 1 1 calc GR . . . .
H5C H 0.1361 0.6323 0.5853 0.038 Uiso 1 1 calc GR . . . .
C6 C 0.6421(3) 0.85797(12) 0.63196(15) 0.0278(4) Uani 1 1 d . . . . .
H6A H 0.5560 0.8102 0.6707 0.042 Uiso 1 1 calc GR . . . .
H6B H 0.5900 0.9251 0.6434 0.042 Uiso 1 1 calc GR . . . .
H6C H 0.7851 0.8532 0.6680 0.042 Uiso 1 1 calc GR . . . .
C7 C 0.7662(3) 0.90875(12) 0.43537(18) 0.0336(4) Uani 1 1 d . . . . .
H7A H 0.9121 0.8995 0.4641 0.050 Uiso 1 1 calc GR . . . .
H7B H 0.7239 0.9765 0.4530 0.050 Uiso 1 1 calc GR . . . .
H7C H 0.7474 0.8974 0.3484 0.050 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 1.9112(11) . ?
Ga1 O1 2.0831(11) 3_666 ?
Ga1 N1 2.3589(12) . ?
Ga1 C4 1.9693(18) . ?
Ga1 C5 1.9754(16) . ?
O1 Ga1 2.0831(11) 3_666 ?
O1 C1 1.3967(18) . ?
N1 H1 0.971(9) . ?
N1 C2 1.4696(19) . ?
N1 C3 1.4804(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.516(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3 1.0000 . ?
C3 C6 1.517(2) . ?
C3 C7 1.524(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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 O1 73.60(5) . 3_666 ?
O1 Ga1 N1 151.09(4) 3_666 . ?
O1 Ga1 N1 77.70(4) . . ?
O1 Ga1 C4 117.98(7) . . ?
O1 Ga1 C5 113.62(6) . . ?
C4 Ga1 O1 96.73(6) . 3_666 ?
C4 Ga1 N1 93.56(6) . . ?
C4 Ga1 C5 128.39(7) . . ?
C5 Ga1 O1 98.52(6) . 3_666 ?
C5 Ga1 N1 96.03(6) . . ?
Ga1 O1 Ga1 106.40(5) . 3_666 ?
C1 O1 Ga1 121.81(9) . . ?
C1 O1 Ga1 131.00(9) . 3_666 ?
Ga1 N1 H1 106.1(10) . . ?
C2 N1 Ga1 102.35(8) . . ?
C2 N1 H1 107.5(10) . . ?
C2 N1 C3 113.81(12) . . ?
C3 N1 Ga1 118.98(9) . . ?
C3 N1 H1 107.4(10) . . ?
O1 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
O1 C1 C2 109.72(13) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
N1 C2 C1 108.57(13) . . ?
N1 C2 H2A 110.0 . . ?
N1 C2 H2B 110.0 . . ?
C1 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 H3 108.0 . . ?
N1 C3 C6 108.85(12) . . ?
N1 C3 C7 112.98(13) . . ?
C6 C3 H3 108.0 . . ?
C6 C3 C7 110.78(13) . . ?
C7 C3 H3 108.0 . . ?
Ga1 C4 H4A 109.5 . . ?
Ga1 C4 H4B 109.5 . . ?
Ga1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Ga1 C5 H5A 109.5 . . ?
Ga1 C5 H5B 109.5 . . ?
Ga1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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 C1 C2 -31.17(19) . . . . ?
Ga1 O1 C1 C2 160.50(11) 3_666 . . . ?
Ga1 N1 C2 C1 -41.05(13) . . . . ?
Ga1 N1 C3 C6 58.03(14) . . . . ?
Ga1 N1 C3 C7 -178.47(11) . . . . ?
O1 C1 C2 N1 49.07(18) . . . . ?
C2 N1 C3 C6 178.81(13) . . . . ?
C2 N1 C3 C7 -57.69(17) . . . . ?
C3 N1 C2 C1 -170.76(12) . . . . ?

