# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_042rxb
_database_code_depnum_ccdc_archive 'CCDC 1053047'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 F3 Ga N3 O3'
_chemical_formula_sum            'C15 H17 F3 Ga N3 O3'
_chemical_formula_weight         414.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   10.323(5)
_cell_length_b                   9.708(5)
_cell_length_c                   16.131(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 100.484(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1589.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7774
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    1.785
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9160
_exptl_absorpt_correction_T_max  0.9484
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9623
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3646
_reflns_number_gt                2743
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  
'PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).'


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
Short O-H interaction due to the effects of H-bonding within the structure.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0394P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3646
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ga1 Ga 0.29647(3) -0.08625(3) 0.157525(16) 0.01290(10) Uani 1 1 d . . .
F1 F 0.16623(16) -0.22227(15) 0.13068(9) 0.0176(3) Uani 1 1 d . . .
F3 F 0.41973(17) 0.05887(16) 0.18066(9) 0.0185(4) Uani 1 1 d . . .
F2 F 0.34251(17) -0.14945(17) 0.26903(9) 0.0220(4) Uani 1 1 d . . .
C3 C -0.0635(3) 0.2377(3) 0.14534(17) 0.0201(6) Uani 1 1 d . . .
H3 H -0.1351 0.2973 0.1406 0.024 Uiso 1 1 calc R . .
C7 C 0.1426(3) 0.1331(3) -0.06674(15) 0.0157(6) Uani 1 1 d . . .
H7 H 0.0774 0.1989 -0.0827 0.019 Uiso 1 1 calc R . .
C15 C 0.4959(3) -0.3120(3) 0.13553(16) 0.0163(6) Uani 1 1 d . . .
H15 H 0.4913 -0.3357 0.1908 0.020 Uiso 1 1 calc R . .
C9 C 0.3141(3) -0.0144(3) -0.09996(15) 0.0170(6) Uani 1 1 d . . .
H9 H 0.3654 -0.0463 -0.1377 0.020 Uiso 1 1 calc R . .
C2 C -0.0129(3) 0.1765(3) 0.22220(17) 0.0189(6) Uani 1 1 d . . .
H2 H -0.0491 0.1956 0.2697 0.023 Uiso 1 1 calc R . .
O1 O 0.1039(3) -0.5388(2) -0.07370(14) 0.0297(5) Uani 1 1 d . . .
O2 O 0.1760(2) -0.4894(2) 0.10030(14) 0.0266(5) Uani 1 1 d . . .
N1 N 0.1473(2) 0.0575(2) 0.15927(12) 0.0138(5) Uani 1 1 d . . .
C5 C 0.0984(3) 0.1188(3) 0.08466(15) 0.0134(5) Uani 1 1 d . . .
C12 C 0.5038(3) -0.2454(3) -0.02792(16) 0.0181(6) Uani 1 1 d . . .
H12 H 0.5041 -0.2226 -0.0839 0.022 Uiso 1 1 calc R . .
N3 N 0.4214(2) -0.2075(2) 0.09908(12) 0.0136(5) Uani 1 1 d . . .
C8 C 0.2185(3) 0.0860(3) -0.12350(16) 0.0181(6) Uani 1 1 d . . .
H8 H 0.2054 0.1219 -0.1778 0.022 Uiso 1 1 calc R . .
N2 N 0.2582(2) -0.0170(2) 0.03576(12) 0.0127(5) Uani 1 1 d . . .
O3 O 0.3650(3) -0.6576(3) 0.19656(13) 0.0256(5) Uani 1 1 d . . .
C4 C -0.0064(3) 0.2094(3) 0.07571(16) 0.0180(6) Uani 1 1 d . . .
H4 H -0.0382 0.2506 0.0239 0.022 Uiso 1 1 calc R . .
C1 C 0.0911(3) 0.0876(3) 0.22701(16) 0.0164(6) Uani 1 1 d . . .
H1 H 0.1244 0.0463 0.2785 0.020 Uiso 1 1 calc R . .
C14 C 0.5792(3) -0.3854(3) 0.09399(17) 0.0188(6) Uani 1 1 d . . .
H14 H 0.6306 -0.4569 0.1208 0.023 Uiso 1 1 calc R . .
C10 C 0.3307(3) -0.0656(3) -0.01849(15) 0.0132(5) Uani 1 1 d . . .
C13 C 0.5844(3) -0.3500(3) 0.01123(16) 0.0197(6) Uani 1 1 d . . .
H13 H 0.6414 -0.3960 -0.0178 0.024 Uiso 1 1 calc R . .
C6 C 0.1663(3) 0.0796(3) 0.01454(15) 0.0133(5) Uani 1 1 d . . .
C11 C 0.4232(3) -0.1758(3) 0.01751(15) 0.0141(6) Uani 1 1 d . . .
H25 H 0.225(3) -0.540(3) 0.1300(19) 0.014(8) Uiso 1 1 d . . .
H22 H 0.190(5) -0.398(5) 0.117(3) 0.066(14) Uiso 1 1 d . . .
H20 H 0.000(6) -0.509(5) -0.087(3) 0.090(17) Uiso 1 1 d . . .
H21 H 0.128(5) -0.515(5) -0.005(3) 0.090(16) Uiso 1 1 d . . .
H24 H 0.357(5) -0.752(5) 0.185(2) 0.065(14) Uiso 1 1 d . . .
H23 H 0.443(5) -0.630(5) 0.205(3) 0.063(16) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 F2 1.8780(16) . ?
Ga1 F1 1.8781(17) . ?
Ga1 F3 1.8895(17) . ?
Ga1 N2 2.045(2) . ?
Ga1 N1 2.082(2) . ?
Ga1 N3 2.093(2) . ?
C3 C4 1.388(4) . ?
C3 C2 1.389(4) . ?
C3 H3 0.9300 . ?
C7 C8 1.387(4) . ?
C7 C6 1.390(3) . ?
C7 H7 0.9300 . ?
C15 N3 1.342(4) . ?
C15 C14 1.381(4) . ?
C15 H15 0.9300 . ?
C9 C10 1.386(3) . ?
C9 C8 1.389(4) . ?
C9 H9 0.9300 . ?
C2 C1 1.368(4) . ?
C2 H2 0.9300 . ?
O1 H20 1.10(6) . ?
O1 H21 1.11(5) . ?
O2 H25 0.80(3) . ?
O2 H22 0.93(5) . ?
N1 C5 1.355(3) . ?
N1 C1 1.359(3) . ?
C5 C4 1.381(4) . ?
C5 C6 1.484(3) . ?
C12 C11 1.381(4) . ?
C12 C13 1.390(4) . ?
C12 H12 0.9300 . ?
N3 C11 1.355(3) . ?
C8 H8 0.9300 . ?
N2 C6 1.334(4) . ?
N2 C10 1.337(3) . ?
O3 H24 0.93(5) . ?
O3 H23 0.83(5) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C14 C13 1.389(4) . ?
C14 H14 0.9300 . ?
C10 C11 1.481(4) . ?
C13 H13 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
F2 Ga1 F1 92.12(7) . . ?
F2 Ga1 F3 90.60(7) . . ?
F1 Ga1 F3 176.29(7) . . ?
F2 Ga1 N2 176.54(8) . . ?
F1 Ga1 N2 90.25(8) . . ?
F3 Ga1 N2 87.15(8) . . ?
F2 Ga1 N1 105.36(7) . . ?
F1 Ga1 N1 88.53(9) . . ?
F3 Ga1 N1 88.32(9) . . ?
N2 Ga1 N1 77.21(8) . . ?
F2 Ga1 N3 100.27(8) . . ?
F1 Ga1 N3 88.53(9) . . ?
F3 Ga1 N3 93.48(9) . . ?
N2 Ga1 N3 77.26(9) . . ?
N1 Ga1 N3 154.28(8) . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C8 C7 C6 118.5(3) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
N3 C15 C14 122.4(2) . . ?
N3 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C10 C9 C8 118.0(2) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
H20 O1 H21 100(3) . . ?
H25 O2 H22 112(4) . . ?
C5 N1 C1 118.4(2) . . ?
C5 N1 Ga1 116.05(16) . . ?
C1 N1 Ga1 125.45(18) . . ?
N1 C5 C4 122.0(2) . . ?
N1 C5 C6 114.4(2) . . ?
C4 C5 C6 123.6(2) . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C15 N3 C11 119.3(2) . . ?
C15 N3 Ga1 125.38(17) . . ?
C11 N3 Ga1 115.37(17) . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C6 N2 C10 122.5(2) . . ?
C6 N2 Ga1 118.78(16) . . ?
C10 N2 Ga1 118.65(18) . . ?
H24 O3 H23 113(4) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C1 C2 122.4(2) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C15 C14 C13 118.3(3) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
N2 C10 C9 120.4(2) . . ?
N2 C10 C11 113.3(2) . . ?
C9 C10 C11 126.2(2) . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N2 C6 C7 119.9(2) . . ?
N2 C6 C5 113.4(2) . . ?
C7 C6 C5 126.6(2) . . ?
N3 C11 C12 121.4(2) . . ?
N3 C11 C10 115.0(2) . . ?
C12 C11 C10 123.6(2) . . ?

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
C4 C3 C2 C1 -1.1(4) . . . . ?
F2 Ga1 N1 C5 179.49(18) . . . . ?
F1 Ga1 N1 C5 -88.72(19) . . . . ?
F3 Ga1 N1 C5 89.33(19) . . . . ?
N2 Ga1 N1 C5 1.87(19) . . . . ?
N3 Ga1 N1 C5 -5.2(3) . . . . ?
F2 Ga1 N1 C1 -4.7(2) . . . . ?
F1 Ga1 N1 C1 87.1(2) . . . . ?
F3 Ga1 N1 C1 -94.8(2) . . . . ?
N2 Ga1 N1 C1 177.7(2) . . . . ?
N3 Ga1 N1 C1 170.6(2) . . . . ?
C1 N1 C5 C4 -0.4(4) . . . . ?
Ga1 N1 C5 C4 175.7(2) . . . . ?
C1 N1 C5 C6 180.0(2) . . . . ?
Ga1 N1 C5 C6 -3.9(3) . . . . ?
C14 C15 N3 C11 2.7(4) . . . . ?
C14 C15 N3 Ga1 -178.1(2) . . . . ?
F2 Ga1 N3 C15 7.9(2) . . . . ?
F1 Ga1 N3 C15 -84.0(2) . . . . ?
F3 Ga1 N3 C15 99.2(2) . . . . ?
N2 Ga1 N3 C15 -174.6(2) . . . . ?
N1 Ga1 N3 C15 -167.5(2) . . . . ?
F2 Ga1 N3 C11 -172.86(19) . . . . ?
F1 Ga1 N3 C11 95.3(2) . . . . ?
F3 Ga1 N3 C11 -81.6(2) . . . . ?
N2 Ga1 N3 C11 4.66(19) . . . . ?
N1 Ga1 N3 C11 11.7(3) . . . . ?
C6 C7 C8 C9 1.3(4) . . . . ?
C10 C9 C8 C7 0.1(4) . . . . ?
F2 Ga1 N2 C6 -137.7(12) . . . . ?
F1 Ga1 N2 C6 89.2(2) . . . . ?
F3 Ga1 N2 C6 -88.2(2) . . . . ?
N1 Ga1 N2 C6 0.74(19) . . . . ?
N3 Ga1 N2 C6 177.6(2) . . . . ?
F2 Ga1 N2 C10 39.2(14) . . . . ?
F1 Ga1 N2 C10 -94.0(2) . . . . ?
F3 Ga1 N2 C10 88.6(2) . . . . ?
N1 Ga1 N2 C10 177.6(2) . . . . ?
N3 Ga1 N2 C10 -5.58(19) . . . . ?
N1 C5 C4 C3 -0.3(4) . . . . ?
C6 C5 C4 C3 179.3(3) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C5 N1 C1 C2 0.4(4) . . . . ?
Ga1 N1 C1 C2 -175.4(2) . . . . ?
C3 C2 C1 N1 0.4(4) . . . . ?
N3 C15 C14 C13 -0.6(4) . . . . ?
C6 N2 C10 C9 1.2(4) . . . . ?
Ga1 N2 C10 C9 -175.5(2) . . . . ?
C6 N2 C10 C11 -177.9(2) . . . . ?
Ga1 N2 C10 C11 5.4(3) . . . . ?
C8 C9 C10 N2 -1.3(4) . . . . ?
C8 C9 C10 C11 177.6(3) . . . . ?
C15 C14 C13 C12 -1.8(4) . . . . ?
C11 C12 C13 C14 2.1(4) . . . . ?
C10 N2 C6 C7 0.3(4) . . . . ?
Ga1 N2 C6 C7 176.99(19) . . . . ?
C10 N2 C6 C5 -179.6(2) . . . . ?
Ga1 N2 C6 C5 -2.9(3) . . . . ?
C8 C7 C6 N2 -1.5(4) . . . . ?
C8 C7 C6 C5 178.4(3) . . . . ?
N1 C5 C6 N2 4.4(3) . . . . ?
C4 C5 C6 N2 -175.2(3) . . . . ?
N1 C5 C6 C7 -175.5(3) . . . . ?
C4 C5 C6 C7 4.9(4) . . . . ?
C15 N3 C11 C12 -2.4(4) . . . . ?
Ga1 N3 C11 C12 178.3(2) . . . . ?
C15 N3 C11 C10 175.9(2) . . . . ?
Ga1 N3 C11 C10 -3.3(3) . . . . ?
C13 C12 C11 N3 0.0(4) . . . . ?
C13 C12 C11 C10 -178.2(3) . . . . ?
N2 C10 C11 N3 -1.2(3) . . . . ?
C9 C10 C11 N3 179.8(3) . . . . ?
N2 C10 C11 C12 177.1(3) . . . . ?
C9 C10 C11 C12 -1.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.102
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1053048'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_audit_creation_date             2015-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'Cl, C7 H17 N2'
_chemical_formula_sum            'C7 H17 Cl1 N2 '
_chemical_formula_weight         164.8
_chemical_absolute_configuration ?
_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'
Cl Cl 0.1484 0.1585 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3293(6)
_cell_length_b                   10.3564(7)
_cell_length_c                   10.3564(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     893.36(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    0
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8132
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.781
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Unknown
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.010329
_diffrn_orient_matrix_UB_12      0.049982
_diffrn_orient_matrix_UB_13      0.108669
_diffrn_orient_matrix_UB_21      0.020657
_diffrn_orient_matrix_UB_22      -0.086423
_diffrn_orient_matrix_UB_23      0.037787
_diffrn_orient_matrix_UB_31      0.093957
_diffrn_orient_matrix_UB_32      0.015447
_diffrn_orient_matrix_UB_33      -0.016035
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                1799
_reflns_number_total             2024
_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       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_collection       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         2024
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      0.961
_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)+(0.0385P)²+0.4058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0847
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_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
Cl1 Cl 0.22429(8) 0.76809(6) 0.28188(6) 0.01808(17) Uani 1 1 d . . . . .
N1 N 0.1782(3) 0.8580(2) 0.6632(2) 0.0123(5) Uani 1 1 d . . . . .
N2 N 0.2238(3) 0.6671(2) 0.8654(2) 0.0128(5) Uani 1 1 d . . . . .
C1 C 0.1649(3) 0.7139(3) 0.6403(3) 0.0142(6) Uani 1 1 d . . . . .
H1A H 0.0539 0.6875 0.6508 0.017 Uiso 1 1 calc R . . . .
H1B H 0.1965 0.6947 0.5522 0.017 Uiso 1 1 calc R . . . .
C2 C 0.2695(3) 0.6375(2) 0.7326(2) 0.0149(5) Uani 1 1 d . . . . .
H2A H 0.2564 0.5458 0.7165 0.018 Uiso 1 1 calc R . . . .
H2B H 0.3814 0.6594 0.7189 0.018 Uiso 1 1 calc R . . . .
C3 C 0.2470(3) 0.8051(2) 0.8915(2) 0.0156(6) Uani 1 1 d . . . . .
H3A H 0.3588 0.8277 0.8781 0.019 Uiso 1 1 calc R . . . .
H3B H 0.2202 0.8234 0.9808 0.019 Uiso 1 1 calc R . . . .
C4 C 0.1423(3) 0.8851(3) 0.8034(3) 0.0144(6) Uani 1 1 d . . . . .
H4A H 0.0304 0.8661 0.8208 0.017 Uiso 1 1 calc R . . . .
H4B H 0.1600 0.9760 0.8210 0.017 Uiso 1 1 calc R . . . .
C5 C 0.3404(3) 0.9076(3) 0.6259(3) 0.0164(6) Uani 1 1 d . . . . .
H5A H 0.3556 0.8969 0.5346 0.025 Uiso 1 1 calc GR . . . .
H5B H 0.4216 0.8601 0.6716 0.025 Uiso 1 1 calc GR . . . .
H5C H 0.3482 0.9975 0.6476 0.025 Uiso 1 1 calc GR . . . .
C6 C 0.0542(4) 0.9257(3) 0.5820(3) 0.0187(6) Uani 1 1 d . . . . .
H6A H 0.0765 0.9109 0.4923 0.028 Uiso 1 1 calc GR . . . .
H6B H 0.0575 1.0167 0.5994 0.028 Uiso 1 1 calc GR . . . .
H6C H -0.0504 0.8928 0.6026 0.028 Uiso 1 1 calc GR . . . .
C7 C 0.3189(4) 0.5908(3) 0.9561(3) 0.0199(6) Uani 1 1 d . . . . .
H7A H 0.3061 0.5007 0.9371 0.030 Uiso 1 1 calc GR . . . .
H7B H 0.2832 0.6077 1.0426 0.030 Uiso 1 1 calc GR . . . .
H7C H 0.4301 0.6140 0.9482 0.030 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
N1 C1 1.515(3) . ?
N1 C4 1.509(3) . ?
N1 C5 1.496(3) . ?
N1 C6 1.505(4) . ?
N2 C2 1.461(3) . ?
N2 C3 1.467(3) . ?
N2 C7 1.461(3) . ?
C1 C2 1.517(4) . ?
C3 C4 1.511(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 108.6(2) . . ?
C5 N1 C1 111.3(2) . . ?
C5 N1 C4 111.3(2) . . ?
C5 N1 C6 108.4(2) . . ?
C6 N1 C1 108.7(2) . . ?
C6 N1 C4 108.3(2) . . ?
C2 N2 C3 110.1(2) . . ?
C7 N2 C2 110.5(2) . . ?
C7 N2 C3 109.7(2) . . ?
C2 C1 N1 111.9(2) . . ?
N2 C2 C1 109.5(2) . . ?
N2 C3 C4 110.3(2) . . ?
N1 C4 C3 111.4(2) . . ?

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
N1 C1 C2 N2 58.2(3) . . . . ?
N2 C3 C4 N1 -58.3(3) . . . . ?
C1 N1 C4 C3 53.9(3) . . . . ?
C2 N2 C3 C4 61.3(3) . . . . ?
C3 N2 C2 C1 -60.8(3) . . . . ?
C4 N1 C1 C2 -54.1(3) . . . . ?
C5 N1 C1 C2 68.7(3) . . . . ?
C5 N1 C4 C3 -69.1(3) . . . . ?
C6 N1 C1 C2 -171.9(2) . . . . ?
C6 N1 C4 C3 171.8(2) . . . . ?
C7 N2 C2 C1 177.9(2) . . . . ?
C7 N2 C3 C4 -176.9(2) . . . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
####################################################################### 
# 
# 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_2013gws065ra
_database_code_depnum_ccdc_archive 'CCDC 1053152'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Al2 F8 O2 H4, 2(C7 H17 N2),4(H2 O)'
_chemical_formula_sum            'C14 H46 Al2 F8 N4 O6'
_chemical_formula_weight         568.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_as_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                   24.054(10)
_cell_length_b                   7.558(3)
_cell_length_c                   16.389(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.374(4)
_cell_angle_gamma                90.00
_cell_volume                     2488.3(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1813
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9873
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            5785
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2822
_reflns_number_gt                2141
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  
'PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
H-atoms on both the coordinated and solvent oxygen atoms not identified from the difference map. There presence is inferred from H-bonding distances between O...F and O...O.Short intermolceular contacts due to H-bonding interactions 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1504P)²+5.5878P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2822
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.2383
_refine_ls_wR_factor_gt          0.2189
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Al1 Al 0.06162(5) 0.26502(12) 0.24826(7) 0.0150(3) Uani 1 1 d . . .
F5 F 0.0000 0.4193(3) 0.2500 0.0164(6) Uani 1 2 d S . .
F1 F 0.0000 0.1094(3) 0.2500 0.0177(6) Uani 1 2 d S . .
F2 F 0.10973(9) 0.4418(3) 0.25162(14) 0.0200(5) Uani 1 1 d . . .
F3 F 0.11047(9) 0.0882(3) 0.25384(14) 0.0218(5) Uani 1 1 d . . .
F4 F 0.00985(10) 0.2638(3) 0.11854(14) 0.0217(5) Uani 1 1 d . . .
O1 O 0.10786(12) 0.2678(3) 0.38635(16) 0.0187(5) Uani 1 1 d . . .
O3 O 0.18209(12) 0.6429(4) 0.20601(18) 0.0260(6) Uani 1 1 d . . .
O2 O 0.23004(13) 0.0477(4) 0.82022(18) 0.0261(6) Uani 1 1 d . . .
N1 N 0.06358(13) -0.2408(3) 0.45727(19) 0.0148(6) Uani 1 1 d . . .
N2 N 0.17291(14) -0.0035(4) 0.4997(2) 0.0206(6) Uani 1 1 d . . .
C4 C 0.08006(18) -0.0725(5) 0.5155(2) 0.0207(7) Uani 1 1 d . . .
H4A H 0.0527 0.0247 0.4707 0.025 Uiso 1 1 calc R . .
H4B H 0.0676 -0.0869 0.5635 0.025 Uiso 1 1 calc R . .
C1 C 0.08961(16) -0.2283(4) 0.3922(2) 0.0166(7) Uani 1 1 d . . .
H1A H 0.0629 -0.1406 0.3399 0.020 Uiso 1 1 calc R . .
H1B H 0.0845 -0.3444 0.3608 0.020 Uiso 1 1 calc R . .
C6 C 0.09093(19) -0.3988(5) 0.5228(3) 0.0254(8) Uani 1 1 d . . .
H7A H 0.0747 -0.3998 0.5661 0.038 Uiso 1 1 calc R . .
H7B H 0.1397 -0.3933 0.5621 0.038 Uiso 1 1 calc R . .
H7C H 0.0763 -0.5067 0.4832 0.038 Uiso 1 1 calc R . .
C2 C 0.16234(17) -0.1741(5) 0.4491(2) 0.0214(7) Uani 1 1 d . . .
H2A H 0.1895 -0.2667 0.4978 0.026 Uiso 1 1 calc R . .
H2B H 0.1773 -0.1639 0.4039 0.026 Uiso 1 1 calc R . .
C3 C 0.15133(19) -0.0210(5) 0.5684(3) 0.0255(8) Uani 1 1 d . . .
H3A H 0.1580 0.0931 0.6024 0.031 Uiso 1 1 calc R . .
H3B H 0.1789 -0.1115 0.6183 0.031 Uiso 1 1 calc R . .
C5 C -0.01076(17) -0.2575(5) 0.3939(3) 0.0217(7) Uani 1 1 d . . .
H5A H -0.0228 -0.3653 0.3544 0.033 Uiso 1 1 calc R . .
H5B H -0.0295 -0.1543 0.3508 0.033 Uiso 1 1 calc R . .
H5C H -0.0285 -0.2639 0.4352 0.033 Uiso 1 1 calc R . .
C7 C 0.24401(18) 0.0488(5) 0.5533(3) 0.0277(8) Uani 1 1 d . . .
H6A H 0.2714 -0.0434 0.6008 0.041 Uiso 1 1 calc R . .
H6B H 0.2503 0.1606 0.5877 0.041 Uiso 1 1 calc R . .
H6C H 0.2573 0.0638 0.5070 0.041 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Al1 F2 1.749(2) . ?
Al1 F3 1.748(2) . ?
Al1 F4 1.777(2) . ?
Al1 O1 1.895(3) . ?
Al1 F5 1.8984(19) . ?
Al1 F1 1.9048(19) . ?
Al1 Al1 2.996(2) 2 ?
F5 Al1 1.8984(19) 2 ?
F1 Al1 1.9048(19) 2 ?
N1 C6 1.495(4) . ?
N1 C5 1.500(4) . ?
N1 C1 1.508(4) . ?
N1 C4 1.507(4) . ?
N2 C2 1.477(4) . ?
N2 C7 1.483(4) . ?
N2 C3 1.483(4) . ?
C4 C3 1.486(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C1 C2 1.518(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C6 H7A 0.9800 . ?
C6 H7B 0.9800 . ?
C6 H7C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H6A 0.9800 . ?
C7 H6B 0.9800 . ?
C7 H6C 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
F2 Al1 F3 99.71(11) . . ?
F2 Al1 F4 93.31(10) . . ?
F3 Al1 F4 93.84(10) . . ?
F2 Al1 O1 90.60(10) . . ?
F3 Al1 O1 90.57(10) . . ?
F4 Al1 O1 173.53(11) . . ?
F2 Al1 F5 92.22(10) . . ?
F3 Al1 F5 167.55(11) . . ?
F4 Al1 F5 88.97(8) . . ?
O1 Al1 F5 85.72(8) . . ?
F2 Al1 F1 168.07(11) . . ?
F3 Al1 F1 91.90(11) . . ?
F4 Al1 F1 88.61(8) . . ?
O1 Al1 F1 86.52(8) . . ?
F5 Al1 F1 76.03(10) . . ?
F2 Al1 Al1 130.08(7) . 2 ?
F3 Al1 Al1 129.97(8) . 2 ?
F4 Al1 Al1 88.46(8) . 2 ?
O1 Al1 Al1 85.07(9) . 2 ?
F5 Al1 Al1 37.89(7) . 2 ?
F1 Al1 Al1 38.14(7) . 2 ?
Al1 F5 Al1 104.22(14) 2 . ?
Al1 F1 Al1 103.73(14) . 2 ?
C6 N1 C5 108.4(3) . . ?
C6 N1 C1 111.6(3) . . ?
C5 N1 C1 108.5(3) . . ?
C6 N1 C4 111.2(3) . . ?
C5 N1 C4 107.9(3) . . ?
C1 N1 C4 109.2(2) . . ?
C2 N2 C7 110.6(3) . . ?
C2 N2 C3 108.9(3) . . ?
C7 N2 C3 110.1(3) . . ?
C3 C4 N1 114.1(3) . . ?
C3 C4 H4A 108.7 . . ?
N1 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
N1 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
N1 C1 C2 111.6(3) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
N1 C6 H7A 109.5 . . ?
N1 C6 H7B 109.5 . . ?
H7A C6 H7B 109.5 . . ?
N1 C6 H7C 109.5 . . ?
H7A C6 H7C 109.5 . . ?
H7B C6 H7C 109.5 . . ?
N2 C2 C1 111.4(3) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 110.7(3) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C7 H6A 109.5 . . ?
N2 C7 H6B 109.5 . . ?
H6A C7 H6B 109.5 . . ?
N2 C7 H6C 109.5 . . ?
H6A C7 H6C 109.5 . . ?
H6B C7 H6C 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
F2 Al1 F5 Al1 -177.91(8) . . . 2 ?
F3 Al1 F5 Al1 -14.5(4) . . . 2 ?
F4 Al1 F5 Al1 88.82(7) . . . 2 ?
O1 Al1 F5 Al1 -87.47(8) . . . 2 ?
F1 Al1 F5 Al1 0.0 . . . 2 ?
F2 Al1 F1 Al1 10.2(4) . . . 2 ?
F3 Al1 F1 Al1 176.91(8) . . . 2 ?
F4 Al1 F1 Al1 -89.29(8) . . . 2 ?
O1 Al1 F1 Al1 86.45(8) . . . 2 ?
F5 Al1 F1 Al1 0.0 . . . 2 ?
C6 N1 C4 C3 71.7(4) . . . . ?
C5 N1 C4 C3 -169.6(3) . . . . ?
C1 N1 C4 C3 -51.9(4) . . . . ?
C6 N1 C1 C2 -72.1(3) . . . . ?
C5 N1 C1 C2 168.5(3) . . . . ?
C4 N1 C1 C2 51.1(3) . . . . ?
C7 N2 C2 C1 -178.9(3) . . . . ?
C3 N2 C2 C1 59.9(4) . . . . ?
N1 C1 C2 N2 -57.4(4) . . . . ?
C2 N2 C3 C4 -58.8(4) . . . . ?
C7 N2 C3 C4 179.7(3) . . . . ?
N1 C4 C3 N2 56.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.300
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.138
_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_2013gws050rrig2
_database_code_depnum_ccdc_archive 'CCDC 1053153'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Al F3 N2 O, 2(H2 O)'
_chemical_formula_sum            'C10 H14 Al F3 N2 O3'
_chemical_formula_weight         294.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_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                   8.976(5)
_cell_length_b                   7.300(5)
_cell_length_c                   19.062(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 93.331(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1246.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2807
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9877
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8257
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2848
_reflns_number_gt                1876
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  
'PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
H-atoms on O2 and O3 not located in difference map but there presence is inferred from H-bonding interactions. H-atoms are not included in the refinement but included in formulae.
Short intermolecular contacts arise from the significant H-bonding within the structure.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0837P)²+0.2911P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2848
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1676
_refine_ls_wR_factor_gt          0.1436
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Al1 Al -0.17742(10) 0.21329(14) 0.67155(5) 0.0153(3) Uani 1 1 d . . .
F2 F -0.1152(2) 0.4414(3) 0.68873(9) 0.0187(4) Uani 1 1 d . . .
F3 F -0.3577(2) 0.2826(3) 0.64471(10) 0.0226(5) Uani 1 1 d . . .
F1 F -0.2237(2) -0.0231(3) 0.65984(9) 0.0201(4) Uani 1 1 d . . .
O1 O -0.2088(3) 0.1890(4) 0.76881(12) 0.0176(5) Uani 1 1 d . . .
O3 O 0.4812(3) 0.5338(4) 0.57135(13) 0.0326(6) Uani 1 1 d . . .
N2 N 0.0445(3) 0.1368(4) 0.68590(14) 0.0164(6) Uani 1 1 d . . .
O2 O 0.5589(3) 0.8938(4) 0.55433(13) 0.0311(6) Uani 1 1 d . . .
N1 N -0.1072(3) 0.2313(4) 0.57135(14) 0.0156(6) Uani 1 1 d . . .
C6 C 0.1274(4) 0.1588(5) 0.62915(17) 0.0173(7) Uani 1 1 d . . .
C1 C -0.1962(4) 0.2710(5) 0.51535(17) 0.0203(7) Uani 1 1 d . . .
H1 H -0.3001 0.2841 0.5210 0.024 Uiso 1 1 calc R . .
C2 C -0.1438(4) 0.2941(5) 0.44898(18) 0.0244(8) Uani 1 1 d . . .
H2 H -0.2107 0.3218 0.4100 0.029 Uiso 1 1 calc R . .
C9 C 0.2661(4) 0.0488(5) 0.75329(18) 0.0216(7) Uani 1 1 d . . .
H9 H 0.3118 0.0084 0.7968 0.026 Uiso 1 1 calc R . .
C3 C 0.0084(4) 0.2762(5) 0.44046(18) 0.0251(8) Uani 1 1 d . . .
H3 H 0.0478 0.2926 0.3957 0.030 Uiso 1 1 calc R . .
C7 C 0.2806(4) 0.1308(5) 0.63299(18) 0.0221(7) Uani 1 1 d . . .
H7 H 0.3368 0.1492 0.5929 0.027 Uiso 1 1 calc R . .
C8 C 0.3501(4) 0.0757(5) 0.69613(19) 0.0239(8) Uani 1 1 d . . .
H8 H 0.4549 0.0565 0.7000 0.029 Uiso 1 1 calc R . .
C5 C 0.0406(4) 0.2095(4) 0.56376(17) 0.0170(7) Uani 1 1 d . . .
C10 C 0.1134(4) 0.0819(5) 0.74652(17) 0.0206(7) Uani 1 1 d . . .
H10 H 0.0559 0.0649 0.7863 0.025 Uiso 1 1 calc R . .
C4 C 0.1012(4) 0.2338(5) 0.49884(18) 0.0233(8) Uani 1 1 d . . .
H4 H 0.2057 0.2213 0.4946 0.028 Uiso 1 1 calc R . .
H1A H -0.233(5) 0.296(8) 0.795(3) 0.057(15) Uiso 1 1 d . . .
H1B H -0.270(6) 0.097(8) 0.782(3) 0.067(17) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Al1 F3 1.743(2) . ?
Al1 F2 1.781(2) . ?
Al1 F1 1.786(2) . ?
Al1 O1 1.900(2) . ?
Al1 N1 2.050(3) . ?
Al1 N2 2.072(3) . ?
O1 H1A 0.96(6) . ?
O1 H1B 0.91(6) . ?
N2 C10 1.340(4) . ?
N2 C6 1.357(4) . ?
N1 C1 1.327(4) . ?
N1 C5 1.353(4) . ?
C6 C7 1.388(5) . ?
C6 C5 1.478(5) . ?
C1 C2 1.385(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(5) . ?
C2 H2 0.9500 . ?
C9 C8 1.374(5) . ?
C9 C10 1.390(5) . ?
C9 H9 0.9500 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9500 . ?
C7 C8 1.383(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C5 C4 1.392(5) . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F3 Al1 F2 93.35(11) . . ?
F3 Al1 F1 92.22(11) . . ?
F2 Al1 F1 174.13(10) . . ?
F3 Al1 O1 97.24(10) . . ?
F2 Al1 O1 88.30(11) . . ?
F1 Al1 O1 89.16(11) . . ?
F3 Al1 N1 92.19(10) . . ?
F2 Al1 N1 90.08(10) . . ?
F1 Al1 N1 91.55(10) . . ?
O1 Al1 N1 170.51(11) . . ?
F3 Al1 N2 170.36(11) . . ?
F2 Al1 N2 86.50(11) . . ?
F1 Al1 N2 88.32(11) . . ?
O1 Al1 N2 92.39(11) . . ?
N1 Al1 N2 78.18(11) . . ?
Al1 O1 H1A 119(3) . . ?
Al1 O1 H1B 117(3) . . ?
H1A O1 H1B 108(4) . . ?
C10 N2 C6 118.4(3) . . ?
C10 N2 Al1 125.9(2) . . ?
C6 N2 Al1 115.5(2) . . ?
C1 N1 C5 119.2(3) . . ?
C1 N1 Al1 124.1(2) . . ?
C5 N1 Al1 116.7(2) . . ?
N2 C6 C7 121.8(3) . . ?
N2 C6 C5 114.6(3) . . ?
C7 C6 C5 123.6(3) . . ?
N1 C1 C2 122.8(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
N1 C5 C4 121.1(3) . . ?
N1 C5 C6 114.3(3) . . ?
C4 C5 C6 124.6(3) . . ?
N2 C10 C9 122.3(3) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?

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
F3 Al1 N2 C10 -178.3(6) . . . . ?
F2 Al1 N2 C10 92.3(3) . . . . ?
F1 Al1 N2 C10 -84.9(3) . . . . ?
O1 Al1 N2 C10 4.2(3) . . . . ?
N1 Al1 N2 C10 -176.9(3) . . . . ?
F3 Al1 N2 C6 7.0(8) . . . . ?
F2 Al1 N2 C6 -82.5(2) . . . . ?
F1 Al1 N2 C6 100.3(2) . . . . ?
O1 Al1 N2 C6 -170.6(2) . . . . ?
N1 Al1 N2 C6 8.4(2) . . . . ?
F3 Al1 N1 C1 -4.3(3) . . . . ?
F2 Al1 N1 C1 -97.6(3) . . . . ?
F1 Al1 N1 C1 88.0(3) . . . . ?
O1 Al1 N1 C1 -177.8(7) . . . . ?
N2 Al1 N1 C1 175.9(3) . . . . ?
F3 Al1 N1 C5 172.4(2) . . . . ?
F2 Al1 N1 C5 79.0(2) . . . . ?
F1 Al1 N1 C5 -95.4(2) . . . . ?
O1 Al1 N1 C5 -1.1(9) . . . . ?
N2 Al1 N1 C5 -7.4(2) . . . . ?
C10 N2 C6 C7 -1.8(5) . . . . ?
Al1 N2 C6 C7 173.4(3) . . . . ?
C10 N2 C6 C5 176.8(3) . . . . ?
Al1 N2 C6 C5 -8.0(4) . . . . ?
C5 N1 C1 C2 -1.0(5) . . . . ?
Al1 N1 C1 C2 175.6(3) . . . . ?
N1 C1 C2 C3 -0.4(6) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
N2 C6 C7 C8 1.2(5) . . . . ?
C5 C6 C7 C8 -177.1(3) . . . . ?
C10 C9 C8 C7 -1.4(5) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C1 N1 C5 C4 2.0(5) . . . . ?
Al1 N1 C5 C4 -174.8(3) . . . . ?
C1 N1 C5 C6 -177.8(3) . . . . ?
Al1 N1 C5 C6 5.4(4) . . . . ?
N2 C6 C5 N1 1.8(4) . . . . ?
C7 C6 C5 N1 -179.7(3) . . . . ?
N2 C6 C5 C4 -178.0(3) . . . . ?
C7 C6 C5 C4 0.5(5) . . . . ?
C6 N2 C10 C9 0.7(5) . . . . ?
Al1 N2 C10 C9 -173.9(3) . . . . ?
C8 C9 C10 N2 0.9(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
N1 C5 C4 C3 -1.7(5) . . . . ?
C6 C5 C4 C3 178.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.101


_exptl_crystal_recrystallization_method 'Solvent evaporation'
####################################################################### 
# 
# 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_012ky
_database_code_depnum_ccdc_archive 'CCDC 1053154'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Gallium trifluoride terpyridine trihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 Al F3 N3 3(H2 O)'
_chemical_formula_sum            'C15 H17 Al F3 N3 O3'
_chemical_formula_weight         371.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   9.4806(9)
_cell_length_b                   25.104(2)
_cell_length_c                   7.0846(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.425(7)
_cell_angle_gamma                90.00
_cell_volume                     1633.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4974
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.329
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'

_diffrn_reflns_number            6803
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.1081
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3669
_reflns_number_gt                2163
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  
'PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0541P)²+2.2543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3669
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.1718
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.209(4) 0.3734(15) 0.266(5) 0.017(10) Uiso 1 1 d . . .
H10 H 0.149(4) 0.8035(15) 0.417(5) 0.013(9) Uiso 1 1 d . . .
H5 H -0.210(4) 0.4789(15) 0.182(5) 0.019(10) Uiso 1 1 d . . .
H9 H -0.104(4) 0.7982(16) 0.393(6) 0.028(11) Uiso 1 1 d . . .
H2 H -0.012(5) 0.4208(16) 0.225(6) 0.027(11) Uiso 1 1 d . . .
H3 H 0.437(5) 0.4203(17) 0.316(6) 0.041(13) Uiso 1 1 d . . .
H6 H -0.391(4) 0.5436(15) 0.160(6) 0.024(11) Uiso 1 1 d . . .
H11 H 0.284(4) 0.7230(15) 0.402(6) 0.026(11) Uiso 1 1 d . . .
H4 H 0.429(5) 0.5165(16) 0.328(6) 0.032(12) Uiso 1 1 d . . .
H12 H 0.411(5) 0.3001(19) 0.371(8) 0.047(15) Uiso 1 1 d . . .
H15 H -0.644(6) 0.618(2) 0.009(8) 0.066(18) Uiso 1 1 d . . .
H14 H -0.650(7) 0.613(2) -0.193(9) 0.08(2) Uiso 1 1 d . . .
H13 H 0.482(6) 0.324(2) 0.555(9) 0.07(2) Uiso 1 1 d . . .
H8 H -0.225(5) 0.7160(19) 0.314(7) 0.050(14) Uiso 1 1 d . . .
H7 H -0.322(5) 0.6353(19) 0.223(7) 0.047(14) Uiso 1 1 d . . .
H16 H -0.418(5) 0.775(2) 0.423(7) 0.035(14) Uiso 1 1 d . . .
H17 H -0.460(8) 0.829(3) 0.409(10) 0.12(3) Uiso 1 1 d . . .
Al1 Al 0.20748(12) 0.60319(5) 0.32746(17) 0.0200(3) Uani 1 1 d . . .
F2 F 0.1729(2) 0.61126(8) 0.0729(3) 0.0219(5) Uani 1 1 d . . .
F1 F 0.2300(2) 0.59460(9) 0.5799(3) 0.0264(6) Uani 1 1 d . . .
F3 F 0.3897(2) 0.61945(9) 0.3561(3) 0.0290(6) Uani 1 1 d . . .
N1 N 0.2169(3) 0.52189(13) 0.2965(4) 0.0196(7) Uani 1 1 d . . .
N2 N -0.0023(3) 0.58168(13) 0.2851(4) 0.0192(7) Uani 1 1 d . . .
O1 O -0.5870(3) 0.61882(13) -0.0785(5) 0.0327(8) Uani 1 1 d . . .
N3 N 0.1083(3) 0.67528(13) 0.3464(5) 0.0217(7) Uani 1 1 d . . .
O2 O -0.3895(3) 0.80435(14) 0.3852(4) 0.0301(7) Uani 1 1 d . . .
C6 C -0.0387(4) 0.53037(15) 0.2533(5) 0.0202(8) Uani 1 1 d . . .
C5 C 0.0884(4) 0.49533(15) 0.2661(5) 0.0199(8) Uani 1 1 d . . .
C11 C -0.0384(4) 0.67378(15) 0.3228(5) 0.0212(8) Uani 1 1 d . . .
C10 C -0.1021(4) 0.61989(16) 0.2800(6) 0.0214(9) Uani 1 1 d . . .
C4 C 0.0820(4) 0.44023(17) 0.2525(6) 0.0247(9) Uani 1 1 d . . .
C14 C 0.1024(5) 0.76959(17) 0.3978(6) 0.0291(10) Uani 1 1 d . . .
C8 C -0.2888(4) 0.55432(18) 0.1988(6) 0.0266(10) Uani 1 1 d . . .
C1 C 0.3406(4) 0.49412(17) 0.3134(6) 0.0242(9) Uani 1 1 d . . .
C12 C -0.1189(5) 0.71889(17) 0.3377(6) 0.0259(9) Uani 1 1 d . . .
C3 C 0.2110(5) 0.41203(17) 0.2716(6) 0.0273(9) Uani 1 1 d . . .
C2 C 0.3426(5) 0.43897(17) 0.3034(6) 0.0270(9) Uani 1 1 d . . .
C13 C -0.0462(5) 0.76728(18) 0.3755(6) 0.0299(10) Uani 1 1 d . . .
C7 C -0.1837(4) 0.51464(17) 0.2079(6) 0.0242(9) Uani 1 1 d . . .
C9 C -0.2496(4) 0.60675(18) 0.2356(6) 0.0262(9) Uani 1 1 d . . .
C15 C 0.1762(5) 0.72275(16) 0.3825(6) 0.0270(9) Uani 1 1 d . . .
O3 O 0.4251(4) 0.29983(13) 0.5101(5) 0.0313(7) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Al1 F3 1.737(2) . ?
Al1 F1 1.761(2) . ?
Al1 F2 1.762(2) . ?
Al1 N2 2.010(3) . ?
Al1 N1 2.057(3) . ?
Al1 N3 2.059(3) . ?
N1 C1 1.344(5) . ?
N1 C5 1.358(5) . ?
N2 C6 1.338(5) . ?
N2 C10 1.341(5) . ?
O1 H15 0.92(6) . ?
O1 H14 0.89(6) . ?
N3 C15 1.348(5) . ?
N3 C11 1.360(5) . ?
O2 H16 0.85(5) . ?
O2 H17 0.96(7) . ?
C6 C7 1.389(5) . ?
C6 C5 1.476(5) . ?
C5 C4 1.387(5) . ?
C11 C12 1.384(5) . ?
C11 C10 1.482(5) . ?
C10 C9 1.394(5) . ?
C4 C3 1.391(6) . ?
C4 H2 0.99(4) . ?
C14 C13 1.379(6) . ?
C14 C15 1.386(6) . ?
C14 H10 0.95(4) . ?
C8 C9 1.375(6) . ?
C8 C7 1.399(6) . ?
C8 H6 0.97(4) . ?
C1 C2 1.387(6) . ?
C1 H4 0.99(4) . ?
C12 C13 1.390(6) . ?
C12 H8 0.98(5) . ?
C3 C2 1.387(6) . ?
C3 H1 0.97(4) . ?
C2 H3 1.00(4) . ?
C13 H9 0.98(4) . ?
C7 H5 0.94(4) . ?
C9 H7 0.98(5) . ?
C15 H11 1.00(4) . ?
O3 H12 0.96(5) . ?
O3 H13 0.82(6) . ?

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
F3 Al1 F1 92.55(12) . . ?
F3 Al1 F2 91.08(11) . . ?
F1 Al1 F2 176.34(13) . . ?
F3 Al1 N2 177.26(14) . . ?
F1 Al1 N2 89.07(12) . . ?
F2 Al1 N2 87.31(12) . . ?
F3 Al1 N1 100.22(12) . . ?
F1 Al1 N1 89.39(12) . . ?
F2 Al1 N1 90.39(11) . . ?
N2 Al1 N1 77.58(13) . . ?
F3 Al1 N3 104.05(13) . . ?
F1 Al1 N3 89.04(12) . . ?
F2 Al1 N3 89.65(12) . . ?
N2 Al1 N3 78.17(13) . . ?
N1 Al1 N3 155.73(13) . . ?
C1 N1 C5 119.2(3) . . ?
C1 N1 Al1 124.4(3) . . ?
C5 N1 Al1 116.3(2) . . ?
C6 N2 C10 122.3(3) . . ?
C6 N2 Al1 119.2(3) . . ?
C10 N2 Al1 118.5(3) . . ?
H15 O1 H14 104(5) . . ?
C15 N3 C11 118.2(3) . . ?
C15 N3 Al1 125.8(3) . . ?
C11 N3 Al1 115.9(3) . . ?
H16 O2 H17 103(5) . . ?
N2 C6 C7 120.7(4) . . ?
N2 C6 C5 113.0(3) . . ?
C7 C6 C5 126.2(4) . . ?
N1 C5 C4 121.5(4) . . ?
N1 C5 C6 113.8(3) . . ?
C4 C5 C6 124.7(4) . . ?
N3 C11 C12 122.3(4) . . ?
N3 C11 C10 113.7(3) . . ?
C12 C11 C10 123.9(4) . . ?
N2 C10 C9 119.8(4) . . ?
N2 C10 C11 113.5(3) . . ?
C9 C10 C11 126.6(4) . . ?
C5 C4 C3 118.6(4) . . ?
C5 C4 H2 122(2) . . ?
C3 C4 H2 120(2) . . ?
C13 C14 C15 118.4(4) . . ?
C13 C14 H10 119(2) . . ?
C15 C14 H10 123(2) . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H6 121(2) . . ?
C7 C8 H6 118(2) . . ?
N1 C1 C2 122.4(4) . . ?
N1 C1 H4 114(2) . . ?
C2 C1 H4 123(2) . . ?
C11 C12 C13 118.2(4) . . ?
C11 C12 H8 119(3) . . ?
C13 C12 H8 122(3) . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H1 120(2) . . ?
C4 C3 H1 120(2) . . ?
C1 C2 C3 118.2(4) . . ?
C1 C2 H3 119(3) . . ?
C3 C2 H3 123(3) . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H9 123(2) . . ?
C12 C13 H9 117(2) . . ?
C6 C7 C8 117.4(4) . . ?
C6 C7 H5 121(2) . . ?
C8 C7 H5 121(2) . . ?
C8 C9 C10 118.6(4) . . ?
C8 C9 H7 122(3) . . ?
C10 C9 H7 119(3) . . ?
N3 C15 C14 122.6(4) . . ?
N3 C15 H11 117(2) . . ?
C14 C15 H11 120(2) . . ?
H12 O3 H13 108(5) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.089
_exptl_crystal_recrystallization_method 'Solvent evaporation'
####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1053155'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H22 F4 Ga2 N6, P2 F12, H8 O4'
_chemical_formula_sum            'C30 H30 F16 Ga2 N6 O4 P2'
_chemical_formula_weight         1043.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  ' -P 1 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.774(2)
_cell_length_b                   10.460(2)
_cell_length_c                   10.646(2)
_cell_angle_alpha                78.064(12)
_cell_angle_beta                 62.736(8)
_cell_angle_gamma                85.448(14)
_cell_volume                     946.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3327
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    1.633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17446
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3925
_reflns_number_gt                3366
_reflns_threshold_expression     >2σ(I)

__computing_data_collection      
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Images generated using CrystalMaker: a crystal and molecular 
structures program for Mac and Windows. CrystalMaker Software Ltd, 
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0652P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3925
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ga1 Ga 0.09619(3) 0.39951(3) -0.09032(3) 0.02374(12) Uani 1 1 d . . .
F1 F 0.0901(2) 0.4890(2) 0.0491(2) 0.0413(5) Uani 1 1 d . . .
F2 F 0.27162(19) 0.30289(17) -0.11601(17) 0.0310(4) Uani 1 1 d . . .
N1 N -0.0373(3) 0.2313(2) 0.0366(3) 0.0296(5) Uani 1 1 d . . .
N2 N 0.0500(3) 0.3301(2) -0.2313(2) 0.0262(5) Uani 1 1 d . . .
N3 N 0.2302(3) 0.5244(2) -0.2878(2) 0.0246(5) Uani 1 1 d . . .
C1 C -0.0587(4) 0.1777(3) 0.1707(3) 0.0360(7) Uani 1 1 d . . .
H1 H -0.0125 0.2182 0.2143 0.043 Uiso 1 1 calc R . .
C2 C -0.1466(4) 0.0648(3) 0.2466(4) 0.0428(8) Uani 1 1 d . . .
H2 H -0.1605 0.0282 0.3412 0.051 Uiso 1 1 calc R . .
C3 C -0.2135(4) 0.0061(3) 0.1837(4) 0.0414(8) Uani 1 1 d . . .
H3 H -0.2754 -0.0706 0.2354 0.050 Uiso 1 1 calc R . .
C4 C -0.1907(4) 0.0591(3) 0.0450(4) 0.0370(7) Uani 1 1 d . . .
H4 H -0.2360 0.0195 0.0000 0.044 Uiso 1 1 calc R . .
C5 C -0.1000(3) 0.1714(3) -0.0266(3) 0.0303(6) Uani 1 1 d . . .
C6 C -0.0539(3) 0.2322(3) -0.1808(3) 0.0284(6) Uani 1 1 d . . .
C7 C -0.1013(4) 0.1918(3) -0.2708(4) 0.0335(7) Uani 1 1 d . . .
H7 H -0.1761 0.1238 -0.2351 0.040 Uiso 1 1 calc R . .
C8 C -0.0371(4) 0.2528(3) -0.4134(3) 0.0346(7) Uani 1 1 d . . .
H8 H -0.0672 0.2254 -0.4770 0.042 Uiso 1 1 calc R . .
C9 C 0.0705(4) 0.3532(3) -0.4657(3) 0.0307(6) Uani 1 1 d . . .
H9 H 0.1154 0.3945 -0.5644 0.037 Uiso 1 1 calc R . .
C10 C 0.1107(3) 0.3918(3) -0.3694(3) 0.0268(6) Uani 1 1 d . . .
C11 C 0.2213(3) 0.4985(3) -0.4031(3) 0.0261(6) Uani 1 1 d . . .
C12 C 0.3107(3) 0.5665(3) -0.5413(3) 0.0307(6) Uani 1 1 d . . .
H12 H 0.3040 0.5464 -0.6214 0.037 Uiso 1 1 calc R . .
C13 C 0.4100(4) 0.6645(3) -0.5606(3) 0.0347(7) Uani 1 1 d . . .
H13 H 0.4714 0.7130 -0.6542 0.042 Uiso 1 1 calc R . .
C14 C 0.4189(3) 0.6912(3) -0.4426(3) 0.0328(7) Uani 1 1 d . . .
H14 H 0.4858 0.7584 -0.4538 0.039 Uiso 1 1 calc R . .
C15 C 0.3284(3) 0.6179(3) -0.3076(3) 0.0302(6) Uani 1 1 d . . .
H15 H 0.3362 0.6344 -0.2266 0.036 Uiso 1 1 calc R . .
P1 P -0.33704(10) -0.09366(8) -0.31165(9) 0.0354(2) Uani 1 1 d . . .
F3 F -0.3027(2) -0.14683(19) -0.4537(2) 0.0401(5) Uani 1 1 d . . .
F4 F -0.4855(2) -0.1884(2) -0.2208(2) 0.0455(5) Uani 1 1 d . . .
F5 F -0.2340(2) -0.2075(2) -0.2744(2) 0.0508(5) Uani 1 1 d . . .
F6 F -0.3713(3) -0.0430(2) -0.1679(2) 0.0642(7) Uani 1 1 d . . .
F7 F -0.1882(3) -0.0006(2) -0.4026(2) 0.0612(7) Uani 1 1 d . . .
F8 F -0.4398(3) 0.0181(2) -0.3492(3) 0.0746(8) Uani 1 1 d . . .
O1 O 0.2896(3) 0.4893(3) 0.1626(2) 0.0434(6) Uani 1 1 d . . .
H1A H 0.2272 0.4889 0.1275 0.065 Uiso 1 1 d R . .
H1B H 0.3614 0.5459 0.1208 0.065 Uiso 1 1 d R . .
O2 O 0.5058(3) 0.3098(3) -0.0585(3) 0.0779(11) Uani 1 1 d . . .
H2A H 0.4201 0.3072 -0.0666 0.117 Uiso 1 1 d R . .
H2B H 0.4961 0.2401 -0.0067 0.117 Uiso 1 1 d R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 F2 1.8564(17) . ?
Ga1 F1 1.889(2) . ?
Ga1 F1 2.003(2) 2_565 ?
Ga1 N2 2.026(2) . ?
Ga1 N1 2.095(3) . ?
Ga1 N3 2.110(2) . ?
F1 Ga1 2.003(2) 2_565 ?
N1 C1 1.345(4) . ?
N1 C5 1.355(4) . ?
N2 C10 1.342(4) . ?
N2 C6 1.344(4) . ?
N3 C15 1.342(4) . ?
N3 C11 1.352(4) . ?
C1 C2 1.384(5) . ?
C2 C3 1.373(5) . ?
C3 C4 1.385(5) . ?
C4 C5 1.386(4) . ?
C5 C6 1.496(4) . ?
C6 C7 1.384(4) . ?
C7 C8 1.377(5) . ?
C8 C9 1.384(5) . ?
C9 C10 1.391(4) . ?
C10 C11 1.488(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.383(4) . ?
C14 C15 1.387(4) . ?
P1 F8 1.589(2) . ?
P1 F7 1.595(2) . ?
P1 F3 1.600(2) . ?
P1 F5 1.603(2) . ?
P1 F4 1.603(2) . ?
P1 F6 1.604(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 Ga1 F1 98.39(8) . . ?
F2 Ga1 F1 174.58(7) . 2_565 ?
F1 Ga1 F1 76.19(9) . 2_565 ?
F2 Ga1 N2 97.02(8) . . ?
F1 Ga1 N2 164.58(9) . . ?
F1 Ga1 N2 88.40(9) 2_565 . ?
F2 Ga1 N1 88.84(9) . . ?
F1 Ga1 N1 102.47(9) . . ?
F1 Ga1 N1 92.37(9) 2_565 . ?
N2 Ga1 N1 77.26(10) . . ?
F2 Ga1 N3 88.19(8) . . ?
F1 Ga1 N3 103.67(9) . . ?
F1 Ga1 N3 93.03(9) 2_565 . ?
N2 Ga1 N3 77.34(9) . . ?
N1 Ga1 N3 153.85(10) . . ?
Ga1 F1 Ga1 103.81(9) . 2_565 ?
C1 N1 C5 119.1(3) . . ?
C1 N1 Ga1 125.0(2) . . ?
C5 N1 Ga1 115.82(19) . . ?
C10 N2 C6 121.4(3) . . ?
C10 N2 Ga1 119.3(2) . . ?
C6 N2 Ga1 118.88(19) . . ?
C15 N3 C11 119.2(2) . . ?
C15 N3 Ga1 125.56(19) . . ?
C11 N3 Ga1 115.07(19) . . ?
N1 C1 C2 121.5(3) . . ?
C3 C2 C1 119.3(3) . . ?
C2 C3 C4 119.9(3) . . ?
C3 C4 C5 118.3(3) . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 113.9(3) . . ?
C4 C5 C6 124.1(3) . . ?
N2 C6 C7 120.6(3) . . ?
N2 C6 C5 113.0(3) . . ?
C7 C6 C5 126.2(3) . . ?
C8 C7 C6 118.3(3) . . ?
C7 C8 C9 121.1(3) . . ?
C8 C9 C10 118.0(3) . . ?
N2 C10 C9 120.5(3) . . ?
N2 C10 C11 113.1(2) . . ?
C9 C10 C11 126.4(3) . . ?
N3 C11 C12 121.6(3) . . ?
N3 C11 C10 114.8(2) . . ?
C12 C11 C10 123.6(3) . . ?
C11 C12 C13 118.8(3) . . ?
C14 C13 C12 119.6(3) . . ?
C13 C14 C15 118.7(3) . . ?
N3 C15 C14 122.1(3) . . ?
F8 P1 F7 90.30(15) . . ?
F8 P1 F3 89.84(14) . . ?
F7 P1 F3 89.50(11) . . ?
F8 P1 F5 179.39(15) . . ?
F7 P1 F5 90.05(14) . . ?
F3 P1 F5 89.66(12) . . ?
F8 P1 F4 90.19(13) . . ?
F7 P1 F4 179.41(14) . . ?
F3 P1 F4 90.18(11) . . ?
F5 P1 F4 89.46(12) . . ?
F8 P1 F6 91.01(16) . . ?
F7 P1 F6 91.04(12) . . ?
F3 P1 F6 178.99(13) . . ?
F5 P1 F6 89.48(14) . . ?
F4 P1 F6 89.27(12) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.983
_refine_diff_density_rms         0.113
_exptl_crystal_recrystallization_method 'Solvent evaporation'
####################################################################### 
# 
# 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_2014gws062kx
_database_code_depnum_ccdc_archive 'CCDC 1053156'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H35 Cl2 Ga N3, Cl4 Ga,C H2 Cl2'
_chemical_formula_sum            'C28 H37 Cl8 Ga2 N3'
_chemical_formula_weight         838.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.674(3)
_cell_length_b                   12.642(4)
_cell_length_c                   13.756(5)
_cell_angle_alpha                89.137(17)
_cell_angle_beta                 78.682(16)
_cell_angle_gamma                65.276(15)
_cell_volume                     1803.1(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3355
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    2.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9018
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            16476
_diffrn_reflns_av_R_equivalents  0.1406
_diffrn_reflns_av_sigmaI/netI    0.1971
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7870
_reflns_number_gt                4228
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  
'PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0744P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7870
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0862
_refine_ls_wR_factor_ref         0.2111
_refine_ls_wR_factor_gt          0.1924
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_restrained_S_all      0.877
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ga1 Ga 0.07513(7) 0.23666(7) 0.03321(5) 0.0284(2) Uani 1 1 d . . .
Ga2 Ga 0.20992(7) 0.64448(7) 0.30708(6) 0.0337(2) Uani 1 1 d . . .
Cl1 Cl 0.19840(16) 0.11906(16) 0.12677(12) 0.0340(4) Uani 1 1 d . . .
Cl2 Cl 0.15890(17) 0.34131(16) -0.05351(13) 0.0357(4) Uani 1 1 d . . .
Cl3 Cl 0.40257(17) 0.50718(17) 0.30562(14) 0.0386(5) Uani 1 1 d . . .
Cl4 Cl 0.21811(18) 0.81450(17) 0.30570(14) 0.0422(5) Uani 1 1 d . . .
Cl5 Cl 0.07556(18) 0.64057(19) 0.43999(14) 0.0444(5) Uani 1 1 d . . .
Cl6 Cl 0.1501(2) 0.61141(18) 0.17447(14) 0.0456(5) Uani 1 1 d . . .
N2 N -0.0956(5) 0.2377(5) 0.0304(4) 0.0255(13) Uani 1 1 d . . .
N3 N -0.0469(5) 0.3636(5) 0.1449(4) 0.0275(13) Uani 1 1 d . . .
N1 N 0.1210(5) 0.1113(5) -0.0828(4) 0.0309(14) Uani 1 1 d . . .
C11 C -0.1727(6) 0.3913(6) 0.1562(5) 0.0278(15) Uani 1 1 d . . .
C23 C -0.5433(7) 0.2513(7) 0.1217(5) 0.041(2) Uani 1 1 d . . .
H5A H -0.6296 0.2593 0.1183 0.062 Uiso 1 1 calc R . .
H5B H -0.5508 0.3150 0.1659 0.062 Uiso 1 1 calc R . .
H5C H -0.4960 0.1762 0.1477 0.062 Uiso 1 1 calc R . .
C6 C -0.1057(6) 0.1644(6) -0.0345(5) 0.0289(15) Uani 1 1 d . . .
C14 C -0.0931(6) 0.5129(6) 0.2696(5) 0.0294(16) Uani 1 1 d . . .
H7 H -0.0623 0.5522 0.3089 0.035 Uiso 1 1 calc R . .
C10 C -0.2028(6) 0.3168(6) 0.0919(5) 0.0284(15) Uani 1 1 d . . .
C8 C -0.3360(6) 0.2461(6) 0.0237(5) 0.0263(15) Uani 1 1 d . . .
C4 C 0.0368(6) 0.0201(6) -0.1838(5) 0.0310(16) Uani 1 1 d . . .
H10 H -0.0342 0.0065 -0.1943 0.037 Uiso 1 1 calc R . .
C5 C 0.0218(6) 0.0944(6) -0.1029(5) 0.0268(15) Uani 1 1 d . . .
C12 C -0.2635(6) 0.4809(6) 0.2246(5) 0.0311(17) Uani 1 1 d . . .
H12 H -0.3524 0.4983 0.2332 0.037 Uiso 1 1 calc R . .
C20 C -0.4706(6) 0.2563(6) 0.0177(5) 0.0303(17) Uani 1 1 d . . .
C7 C -0.2227(6) 0.1645(6) -0.0398(5) 0.0277(15) Uani 1 1 d . . .
H14 H -0.2271 0.1111 -0.0851 0.033 Uiso 1 1 calc R . .
C3 C 0.1575(7) -0.0340(6) -0.2493(5) 0.0313(16) Uani 1 1 d . . .
C17 C 0.0662(7) -0.1372(7) -0.3486(5) 0.040(2) Uani 1 1 d . . .
H16A H 0.0565 -0.1830 -0.2920 0.061 Uiso 1 1 calc R . .
H16B H 0.0846 -0.1838 -0.4107 0.061 Uiso 1 1 calc R . .
H16C H -0.0138 -0.0662 -0.3444 0.061 Uiso 1 1 calc R . .
C26 C -0.3752(8) 0.5975(7) 0.4452(5) 0.045(2) Uani 1 1 d . . .
H17A H -0.4165 0.5506 0.4248 0.068 Uiso 1 1 calc R . .
H17B H -0.4381 0.6606 0.4941 0.068 Uiso 1 1 calc R . .
H17C H -0.3028 0.5479 0.4749 0.068 Uiso 1 1 calc R . .
C24 C -0.3256(7) 0.6500(6) 0.3539(5) 0.0331(17) Uani 1 1 d . . .
C15 C -0.0067(7) 0.4223(6) 0.2008(5) 0.0322(17) Uani 1 1 d . . .
H19 H 0.0830 0.4011 0.1928 0.039 Uiso 1 1 calc R . .
C9 C -0.3214(7) 0.3213(6) 0.0890(5) 0.0339(17) Uani 1 1 d . . .
H20 H -0.3957 0.3768 0.1325 0.041 Uiso 1 1 calc R . .
C16 C 0.1779(7) -0.1036(6) -0.3463(5) 0.0337(18) Uani 1 1 d . . .
C27 C -0.2647(7) 0.7274(7) 0.3860(6) 0.043(2) Uani 1 1 d . . .
H22A H -0.2033 0.6842 0.4274 0.065 Uiso 1 1 calc R . .
H22B H -0.3326 0.7981 0.4241 0.065 Uiso 1 1 calc R . .
H22C H -0.2196 0.7491 0.3269 0.065 Uiso 1 1 calc R . .
C19 C 0.3041(7) -0.2157(7) -0.3615(6) 0.046(2) Uani 1 1 d . . .
H23A H 0.3775 -0.1952 -0.3701 0.070 Uiso 1 1 calc R . .
H23B H 0.3120 -0.2622 -0.4209 0.070 Uiso 1 1 calc R . .
H23C H 0.3033 -0.2613 -0.3033 0.070 Uiso 1 1 calc R . .
C13 C -0.2234(6) 0.5459(6) 0.2812(5) 0.0298(16) Uani 1 1 d . . .
C2 C 0.2590(7) -0.0153(6) -0.2249(5) 0.0355(18) Uani 1 1 d . . .
H25 H 0.3433 -0.0528 -0.2651 0.043 Uiso 1 1 calc R . .
C21 C -0.4636(7) 0.1602(6) -0.0534(5) 0.0363(18) Uani 1 1 d . . .
H26A H -0.4201 0.0838 -0.0283 0.055 Uiso 1 1 calc R . .
H26B H -0.4152 0.1629 -0.1195 0.055 Uiso 1 1 calc R . .
H26C H -0.5511 0.1728 -0.0579 0.055 Uiso 1 1 calc R . .
C18 C 0.1824(9) -0.0226(7) -0.4297(5) 0.048(2) Uani 1 1 d . . .
H27A H 0.1010 0.0480 -0.4184 0.071 Uiso 1 1 calc R . .
H27B H 0.1950 -0.0631 -0.4938 0.071 Uiso 1 1 calc R . .
H27C H 0.2539 -0.0011 -0.4303 0.071 Uiso 1 1 calc R . .
C1 C 0.2373(7) 0.0570(6) -0.1429(5) 0.0367(19) Uani 1 1 d . . .
H28 H 0.3075 0.0689 -0.1284 0.044 Uiso 1 1 calc R . .
C25 C -0.4365(7) 0.7249(7) 0.3040(5) 0.0395(19) Uani 1 1 d . . .
H29A H -0.4025 0.7542 0.2440 0.059 Uiso 1 1 calc R . .
H29B H -0.4994 0.7909 0.3502 0.059 Uiso 1 1 calc R . .
H29C H -0.4784 0.6774 0.2858 0.059 Uiso 1 1 calc R . .
C22 C -0.5426(7) 0.3761(6) -0.0216(6) 0.0410(19) Uani 1 1 d . . .
H31A H -0.4919 0.3823 -0.0854 0.061 Uiso 1 1 calc R . .
H31B H -0.5548 0.4384 0.0263 0.061 Uiso 1 1 calc R . .
H31C H -0.6269 0.3837 -0.0306 0.061 Uiso 1 1 calc R . .
Cl7 Cl 0.2373(2) 0.3102(2) 0.35369(15) 0.0561(6) Uani 1 1 d . . .
C28 C 0.2321(8) 0.1759(7) 0.3742(6) 0.049(2) Uani 1 1 d . . .
H98A H 0.1858 0.1602 0.3272 0.059 Uiso 1 1 calc R . .
H98B H 0.1837 0.1788 0.4425 0.059 Uiso 1 1 calc R . .
Cl8 Cl 0.3899(3) 0.0604(2) 0.3583(2) 0.0827(9) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N2 1.995(5) . ?
Ga1 N3 2.066(5) . ?
Ga1 N1 2.092(5) . ?
Ga1 Cl2 2.169(2) . ?
Ga1 Cl1 2.195(2) . ?
Ga2 Cl5 2.178(2) . ?
Ga2 Cl6 2.1811(19) . ?
Ga2 Cl3 2.188(2) . ?
Ga2 Cl4 2.191(2) . ?
N2 C6 1.352(7) . ?
N2 C10 1.358(8) . ?
N3 C11 1.336(8) . ?
N3 C15 1.346(7) . ?
N1 C5 1.340(7) . ?
N1 C1 1.340(8) . ?
C11 C12 1.388(9) . ?
C11 C10 1.489(8) . ?
C23 C20 1.529(10) . ?
C23 H5A 0.9800 . ?
C23 H5B 0.9800 . ?
C23 H5C 0.9800 . ?
C6 C7 1.381(9) . ?
C6 C5 1.503(9) . ?
C14 C13 1.374(9) . ?
C14 C15 1.385(9) . ?
C14 H7 0.9500 . ?
C10 C9 1.370(9) . ?
C8 C9 1.401(8) . ?
C8 C7 1.417(9) . ?
C8 C20 1.541(9) . ?
C4 C5 1.403(8) . ?
C4 C3 1.407(9) . ?
C4 H10 0.9500 . ?
C12 C13 1.409(8) . ?
C12 H12 0.9500 . ?
C20 C21 1.536(8) . ?
C20 C22 1.543(10) . ?
C7 H14 0.9500 . ?
C3 C2 1.403(9) . ?
C3 C16 1.531(8) . ?
C17 C16 1.537(9) . ?
C17 H16A 0.9800 . ?
C17 H16B 0.9800 . ?
C17 H16C 0.9800 . ?
C26 C24 1.537(11) . ?
C26 H17A 0.9800 . ?
C26 H17B 0.9800 . ?
C26 H17C 0.9800 . ?
C24 C25 1.533(10) . ?
C24 C27 1.540(9) . ?
C24 C13 1.553(9) . ?
C15 H19 0.9500 . ?
C9 H20 0.9500 . ?
C16 C18 1.534(11) . ?
C16 C19 1.538(10) . ?
C27 H22A 0.9800 . ?
C27 H22B 0.9800 . ?
C27 H22C 0.9800 . ?
C19 H23A 0.9800 . ?
C19 H23B 0.9800 . ?
C19 H23C 0.9800 . ?
C2 C1 1.377(8) . ?
C2 H25 0.9500 . ?
C21 H26A 0.9800 . ?
C21 H26B 0.9800 . ?
C21 H26C 0.9800 . ?
C18 H27A 0.9800 . ?
C18 H27B 0.9800 . ?
C18 H27C 0.9800 . ?
C1 H28 0.9500 . ?
C25 H29A 0.9800 . ?
C25 H29B 0.9800 . ?
C25 H29C 0.9800 . ?
C22 H31A 0.9800 . ?
C22 H31B 0.9800 . ?
C22 H31C 0.9800 . ?
Cl7 C28 1.741(8) . ?
C28 Cl8 1.782(9) . ?
C28 H98A 0.9900 . ?
C28 H98B 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
N2 Ga1 N3 77.9(2) . . ?
N2 Ga1 N1 77.3(2) . . ?
N3 Ga1 N1 155.1(2) . . ?
N2 Ga1 Cl2 125.68(18) . . ?
N3 Ga1 Cl2 97.76(17) . . ?
N1 Ga1 Cl2 95.78(17) . . ?
N2 Ga1 Cl1 120.20(18) . . ?
N3 Ga1 Cl1 96.80(16) . . ?
N1 Ga1 Cl1 96.56(18) . . ?
Cl2 Ga1 Cl1 114.10(8) . . ?
Cl5 Ga2 Cl6 110.07(8) . . ?
Cl5 Ga2 Cl3 109.89(9) . . ?
Cl6 Ga2 Cl3 107.67(8) . . ?
Cl5 Ga2 Cl4 109.64(8) . . ?
Cl6 Ga2 Cl4 110.40(9) . . ?
Cl3 Ga2 Cl4 109.14(8) . . ?
C6 N2 C10 120.2(5) . . ?
C6 N2 Ga1 120.7(4) . . ?
C10 N2 Ga1 119.0(4) . . ?
C11 N3 C15 119.9(6) . . ?
C11 N3 Ga1 116.4(4) . . ?
C15 N3 Ga1 123.6(5) . . ?
C5 N1 C1 118.9(5) . . ?
C5 N1 Ga1 115.9(4) . . ?
C1 N1 Ga1 124.9(4) . . ?
N3 C11 C12 120.9(6) . . ?
N3 C11 C10 114.1(5) . . ?
C12 C11 C10 125.0(6) . . ?
C20 C23 H5A 109.5 . . ?
C20 C23 H5B 109.5 . . ?
H5A C23 H5B 109.5 . . ?
C20 C23 H5C 109.5 . . ?
H5A C23 H5C 109.5 . . ?
H5B C23 H5C 109.5 . . ?
N2 C6 C7 122.2(6) . . ?
N2 C6 C5 111.3(5) . . ?
C7 C6 C5 126.3(5) . . ?
C13 C14 C15 120.1(6) . . ?
C13 C14 H7 120.0 . . ?
C15 C14 H7 120.0 . . ?
N2 C10 C9 119.9(6) . . ?
N2 C10 C11 112.4(6) . . ?
C9 C10 C11 127.7(6) . . ?
C9 C8 C7 117.3(6) . . ?
C9 C8 C20 121.1(6) . . ?
C7 C8 C20 121.6(5) . . ?
C5 C4 C3 119.5(6) . . ?
C5 C4 H10 120.2 . . ?
C3 C4 H10 120.2 . . ?
N1 C5 C4 122.0(6) . . ?
N1 C5 C6 114.6(5) . . ?
C4 C5 C6 123.4(5) . . ?
C11 C12 C13 119.9(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C23 C20 C21 110.0(6) . . ?
C23 C20 C8 109.3(5) . . ?
C21 C20 C8 112.3(5) . . ?
C23 C20 C22 109.4(6) . . ?
C21 C20 C22 108.7(6) . . ?
C8 C20 C22 107.1(5) . . ?
C6 C7 C8 118.6(5) . . ?
C6 C7 H14 120.7 . . ?
C8 C7 H14 120.7 . . ?
C2 C3 C4 116.6(6) . . ?
C2 C3 C16 120.5(6) . . ?
C4 C3 C16 122.8(6) . . ?
C16 C17 H16A 109.5 . . ?
C16 C17 H16B 109.5 . . ?
H16A C17 H16B 109.5 . . ?
C16 C17 H16C 109.5 . . ?
H16A C17 H16C 109.5 . . ?
H16B C17 H16C 109.5 . . ?
C24 C26 H17A 109.5 . . ?
C24 C26 H17B 109.5 . . ?
H17A C26 H17B 109.5 . . ?
C24 C26 H17C 109.5 . . ?
H17A C26 H17C 109.5 . . ?
H17B C26 H17C 109.5 . . ?
C25 C24 C26 110.5(6) . . ?
C25 C24 C27 108.7(6) . . ?
C26 C24 C27 109.8(6) . . ?
C25 C24 C13 110.2(5) . . ?
C26 C24 C13 106.9(6) . . ?
C27 C24 C13 110.7(6) . . ?
N3 C15 C14 121.5(6) . . ?
N3 C15 H19 119.2 . . ?
C14 C15 H19 119.2 . . ?
C10 C9 C8 121.7(6) . . ?
C10 C9 H20 119.1 . . ?
C8 C9 H20 119.1 . . ?
C3 C16 C18 106.2(6) . . ?
C3 C16 C17 112.2(5) . . ?
C18 C16 C17 108.1(6) . . ?
C3 C16 C19 110.6(6) . . ?
C18 C16 C19 111.1(6) . . ?
C17 C16 C19 108.6(6) . . ?
C24 C27 H22A 109.5 . . ?
C24 C27 H22B 109.5 . . ?
H22A C27 H22B 109.5 . . ?
C24 C27 H22C 109.5 . . ?
H22A C27 H22C 109.5 . . ?
H22B C27 H22C 109.5 . . ?
C16 C19 H23A 109.5 . . ?
C16 C19 H23B 109.5 . . ?
H23A C19 H23B 109.5 . . ?
C16 C19 H23C 109.5 . . ?
H23A C19 H23C 109.5 . . ?
H23B C19 H23C 109.5 . . ?
C14 C13 C12 117.5(6) . . ?
C14 C13 C24 122.6(6) . . ?
C12 C13 C24 119.8(6) . . ?
C1 C2 C3 120.4(6) . . ?
C1 C2 H25 119.8 . . ?
C3 C2 H25 119.8 . . ?
C20 C21 H26A 109.5 . . ?
C20 C21 H26B 109.5 . . ?
H26A C21 H26B 109.5 . . ?
C20 C21 H26C 109.5 . . ?
H26A C21 H26C 109.5 . . ?
H26B C21 H26C 109.5 . . ?
C16 C18 H27A 109.5 . . ?
C16 C18 H27B 109.5 . . ?
H27A C18 H27B 109.5 . . ?
C16 C18 H27C 109.5 . . ?
H27A C18 H27C 109.5 . . ?
H27B C18 H27C 109.5 . . ?
N1 C1 C2 122.5(6) . . ?
N1 C1 H28 118.7 . . ?
C2 C1 H28 118.7 . . ?
C24 C25 H29A 109.5 . . ?
C24 C25 H29B 109.5 . . ?
H29A C25 H29B 109.5 . . ?
C24 C25 H29C 109.5 . . ?
H29A C25 H29C 109.5 . . ?
H29B C25 H29C 109.5 . . ?
C20 C22 H31A 109.5 . . ?
C20 C22 H31B 109.5 . . ?
H31A C22 H31B 109.5 . . ?
C20 C22 H31C 109.5 . . ?
H31A C22 H31C 109.5 . . ?
H31B C22 H31C 109.5 . . ?
Cl7 C28 Cl8 111.6(4) . . ?
Cl7 C28 H98A 109.3 . . ?
Cl8 C28 H98A 109.3 . . ?
Cl7 C28 H98B 109.3 . . ?
Cl8 C28 H98B 109.3 . . ?
H98A C28 H98B 108.0 . . ?

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
N3 Ga1 N2 C6 -179.4(6) . . . . ?
N1 Ga1 N2 C6 1.7(5) . . . . ?
Cl2 Ga1 N2 C6 89.7(5) . . . . ?
Cl1 Ga1 N2 C6 -88.5(5) . . . . ?
N3 Ga1 N2 C10 3.4(5) . . . . ?
N1 Ga1 N2 C10 -175.5(6) . . . . ?
Cl2 Ga1 N2 C10 -87.5(5) . . . . ?
Cl1 Ga1 N2 C10 94.3(5) . . . . ?
N2 Ga1 N3 C11 -5.1(5) . . . . ?
N1 Ga1 N3 C11 -2.5(9) . . . . ?
Cl2 Ga1 N3 C11 119.9(5) . . . . ?
Cl1 Ga1 N3 C11 -124.6(5) . . . . ?
N2 Ga1 N3 C15 179.0(6) . . . . ?
N1 Ga1 N3 C15 -178.5(6) . . . . ?
Cl2 Ga1 N3 C15 -56.1(6) . . . . ?
Cl1 Ga1 N3 C15 59.4(6) . . . . ?
N2 Ga1 N1 C5 1.0(5) . . . . ?
N3 Ga1 N1 C5 -1.6(9) . . . . ?
Cl2 Ga1 N1 C5 -124.4(5) . . . . ?
Cl1 Ga1 N1 C5 120.5(5) . . . . ?
N2 Ga1 N1 C1 174.1(7) . . . . ?
N3 Ga1 N1 C1 171.5(6) . . . . ?
Cl2 Ga1 N1 C1 48.8(6) . . . . ?
Cl1 Ga1 N1 C1 -66.4(6) . . . . ?
C15 N3 C11 C12 0.5(10) . . . . ?
Ga1 N3 C11 C12 -175.7(5) . . . . ?
C15 N3 C11 C10 -178.1(6) . . . . ?
Ga1 N3 C11 C10 5.7(8) . . . . ?
C10 N2 C6 C7 -1.5(11) . . . . ?
Ga1 N2 C6 C7 -178.6(5) . . . . ?
C10 N2 C6 C5 173.4(6) . . . . ?
Ga1 N2 C6 C5 -3.8(8) . . . . ?
C6 N2 C10 C9 0.8(10) . . . . ?
Ga1 N2 C10 C9 178.0(5) . . . . ?
C6 N2 C10 C11 -178.7(6) . . . . ?
Ga1 N2 C10 C11 -1.5(8) . . . . ?
N3 C11 C10 N2 -2.9(9) . . . . ?
C12 C11 C10 N2 178.6(7) . . . . ?
N3 C11 C10 C9 177.7(7) . . . . ?
C12 C11 C10 C9 -0.8(12) . . . . ?
C1 N1 C5 C4 1.1(11) . . . . ?
Ga1 N1 C5 C4 174.7(5) . . . . ?
C1 N1 C5 C6 -176.7(7) . . . . ?
Ga1 N1 C5 C6 -3.2(8) . . . . ?
C3 C4 C5 N1 -3.4(11) . . . . ?
C3 C4 C5 C6 174.3(7) . . . . ?
N2 C6 C5 N1 4.4(9) . . . . ?
C7 C6 C5 N1 179.0(7) . . . . ?
N2 C6 C5 C4 -173.5(7) . . . . ?
C7 C6 C5 C4 1.2(12) . . . . ?
N3 C11 C12 C13 1.8(11) . . . . ?
C10 C11 C12 C13 -179.8(7) . . . . ?
C9 C8 C20 C23 -53.8(9) . . . . ?
C7 C8 C20 C23 129.4(7) . . . . ?
C9 C8 C20 C21 -176.2(7) . . . . ?
C7 C8 C20 C21 7.1(10) . . . . ?
C9 C8 C20 C22 64.6(8) . . . . ?
C7 C8 C20 C22 -112.2(7) . . . . ?
N2 C6 C7 C8 1.3(11) . . . . ?
C5 C6 C7 C8 -172.8(7) . . . . ?
C9 C8 C7 C6 -0.6(10) . . . . ?
C20 C8 C7 C6 176.3(7) . . . . ?
C5 C4 C3 C2 4.0(11) . . . . ?
C5 C4 C3 C16 -172.0(7) . . . . ?
C11 N3 C15 C14 -0.9(11) . . . . ?
Ga1 N3 C15 C14 174.9(5) . . . . ?
C13 C14 C15 N3 -0.9(11) . . . . ?
N2 C10 C9 C8 -0.1(11) . . . . ?
C11 C10 C9 C8 179.3(7) . . . . ?
C7 C8 C9 C10 0.0(11) . . . . ?
C20 C8 C9 C10 -176.9(7) . . . . ?
C2 C3 C16 C18 -74.6(9) . . . . ?
C4 C3 C16 C18 101.2(8) . . . . ?
C2 C3 C16 C17 167.4(7) . . . . ?
C4 C3 C16 C17 -16.7(10) . . . . ?
C2 C3 C16 C19 46.0(10) . . . . ?
C4 C3 C16 C19 -138.2(7) . . . . ?
C15 C14 C13 C12 3.1(11) . . . . ?
C15 C14 C13 C24 -177.4(7) . . . . ?
C11 C12 C13 C14 -3.5(11) . . . . ?
C11 C12 C13 C24 177.0(7) . . . . ?
C25 C24 C13 C14 136.0(7) . . . . ?
C26 C24 C13 C14 -103.9(8) . . . . ?
C27 C24 C13 C14 15.7(10) . . . . ?
C25 C24 C13 C12 -44.6(9) . . . . ?
C26 C24 C13 C12 75.6(8) . . . . ?
C27 C24 C13 C12 -164.9(7) . . . . ?
C4 C3 C2 C1 -2.8(11) . . . . ?
C16 C3 C2 C1 173.4(7) . . . . ?
C5 N1 C1 C2 0.2(12) . . . . ?
Ga1 N1 C1 C2 -172.7(6) . . . . ?
C3 C2 C1 N1 0.7(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         1.902
_refine_diff_density_min         -1.029
_refine_diff_density_rms         0.184
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/hexane'
_chemical_properties_physical    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_13gws038rx2
_database_code_depnum_ccdc_archive 'CCDC 1053157'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-97 + hand edit'
_audit_creation_date             2013-09-02 # yyyy-mm-dd


_chemical_name_systematic        
; 
 aqua(2,2'-bipyridine)trifluorogallium(III) dihydrate
;

# 2,2'-bipyridyl = C10H8N2 = bipy
# 2,2'-bipyridyl  (chemspider) 
# 2,2'-bipyridine (iLab defaults & selected options) 
# 2,2'-bipyridine (chemspider systematic name) 
# 2-(2-pyridyl)pyridine  (chemspider) 



_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 F3 Ga N2 O, 2(H2 O)'
_chemical_formula_sum            'C10 H14 F3 Ga N2 O3'
_chemical_formula_weight         336.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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


loop_
_symmetry_equiv_pos_as_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                   9.056(3)
_cell_length_b                   7.371(2)
_cell_length_c                   18.904(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.462(6)
_cell_angle_gamma                90.00
_cell_volume                     1259.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5057
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      34.8

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    2.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.932 # Expt'l Tmin & Tmax 
_exptl_absorpt_correction_T_max  1.000 # scaled to Tmax=1.0
_exptl_absorpt_process_details   
;Jacobson, R.A. (1998). REQAB. Private communication to the 
 Rigaku Corporation, Tokyo, Japan. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  ?
_diffrn_radiation_collimation    'Confocal mirrors, VHF VariMax '

_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_type              'Rigaku FR-E+ Superbright'

_diffrn_measurement_device       'Four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 '
_diffrn_measurement_method       'Profile data from ω-scans'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11425
_diffrn_reflns_av_R_equivalents  0.1541
# _diffrn_reflns_av_sigmaI/netI   0.0856
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2883
_reflns_number_gt                2703
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.

 Shelxl-97 details 
 For C-H bonds H atoms were added in calculated positions with the default
 distance. For H atoms bonded to O these were identified from the Q-peaks
 in late difference maps. DFIX was applied to the O-H distance (x 8)
 with a fixed Uiso and refined coordinates.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0782P)²+0.0284P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed # geom (C-H) difmap (O-H) 
_refine_ls_hydrogen_treatment    mixed # constr (C-H) refxyz (O-H) 
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2883
_refine_ls_number_parameters     196
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ga1 Ga 0.82809(3) 0.29228(3) 0.171289(14) 0.00786(15) Uani 1 1 d . . .
F1 F 0.77314(16) 0.53764(19) 0.15767(8) 0.0128(3) Uani 1 1 d . . .
F2 F 0.63815(18) 0.21822(19) 0.14494(10) 0.0152(4) Uani 1 1 d . . .
F3 F 0.89088(15) 0.05279(18) 0.19124(8) 0.0114(3) Uani 1 1 d . . .
O1 O 0.7989(2) 0.3206(2) 0.27267(11) 0.0104(4) Uani 1 1 d D . .
H1A H 0.739(4) 0.398(5) 0.279(2) 0.050 Uiso 1 1 d D . .
H1B H 0.781(6) 0.234(4) 0.295(2) 0.050 Uiso 1 1 d D . .
N1 N 1.0505(2) 0.3699(3) 0.18376(11) 0.0101(4) Uani 1 1 d . . .
N2 N 0.8937(3) 0.2696(3) 0.06898(13) 0.0104(4) Uani 1 1 d . . .
C1 C 1.1183(3) 0.4273(3) 0.24441(15) 0.0135(5) Uani 1 1 d . . .
H1 H 1.0618 0.4470 0.2844 0.016 Uiso 1 1 calc R . .
C2 C 1.2709(3) 0.4588(3) 0.25016(14) 0.0153(6) Uani 1 1 d . . .
H2 H 1.3175 0.5014 0.2934 0.018 Uiso 1 1 calc R . .
C3 C 1.3534(3) 0.4271(4) 0.19194(16) 0.0168(5) Uani 1 1 d . . .
H3 H 1.4574 0.4452 0.1951 0.020 Uiso 1 1 calc R . .
C4 C 1.2823(3) 0.3685(4) 0.12894(16) 0.0162(5) Uani 1 1 d . . .
H4 H 1.3367 0.3462 0.0884 0.019 Uiso 1 1 calc R . .
C5 C 1.1293(3) 0.3431(3) 0.12632(14) 0.0108(5) Uani 1 1 d . . .
C6 C 1.0411(3) 0.2895(3) 0.06082(15) 0.0100(5) Uani 1 1 d . . .
C7 C 1.0987(3) 0.2643(4) -0.00466(16) 0.0162(6) Uani 1 1 d . . .
H7 H 1.2018 0.2780 -0.0098 0.019 Uiso 1 1 calc R . .
C8 C 1.0054(4) 0.2191(3) -0.06239(17) 0.0181(6) Uani 1 1 d . . .
H8 H 1.0437 0.2007 -0.1075 0.022 Uiso 1 1 calc R . .
C9 C 0.8545(4) 0.2009(3) -0.05380(16) 0.0166(6) Uani 1 1 d . . .
H9 H 0.7879 0.1713 -0.0929 0.020 Uiso 1 1 calc R . .
C10 C 0.8041(3) 0.2270(3) 0.01278(15) 0.0129(5) Uani 1 1 d . . .
H10 H 0.7013 0.2141 0.0190 0.016 Uiso 1 1 calc R . .
O2 O 0.5601(2) 0.6131(3) 0.05166(12) 0.0233(5) Uani 1 1 d D . .
H2A H 0.620(4) 0.588(6) 0.0828(19) 0.050 Uiso 1 1 d D . .
H2B1 H 0.538(11) 0.718(5) 0.061(5) 0.050 Uiso 0.50 1 d PD . .
H2B2 H 0.556(10) 0.531(9) 0.023(4) 0.050 Uiso 0.50 1 d PD . .
O3 O 0.4783(3) -0.0328(3) 0.07162(13) 0.0243(5) Uani 1 1 d D . .
H3A H 0.527(4) 0.041(5) 0.096(2) 0.050 Uiso 1 1 d D . .
H3B1 H 0.515(10) -0.132(6) 0.065(5) 0.050 Uiso 0.50 1 d PD . .
H3B2 H 0.490(12) -0.016(13) 0.0295(17) 0.050 Uiso 0.50 1 d PD . .


_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 F2 1.8442(17) . ?
Ga1 F3 1.8857(14) . ?
Ga1 F1 1.8892(15) . ?
Ga1 O1 1.962(2) . ?
Ga1 N2 2.064(3) . ?
Ga1 N1 2.093(2) . ?
O1 H1A 0.802(19) . ?
O1 H1B 0.794(19) . ?
N1 C1 1.336(3) . ?
N1 C5 1.349(3) . ?
N2 C10 1.335(4) . ?
N2 C6 1.360(3) . ?
C1 C2 1.399(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.486(4) . ?
C6 C7 1.385(4) . ?
C7 C8 1.380(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
O2 H2A 0.799(19) . ?
O2 H2B1 0.82(2) . ?
O2 H2B2 0.81(2) . ?
O3 H3A 0.820(19) . ?
O3 H3B1 0.82(2) . ?
O3 H3B2 0.82(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 Ga1 F3 92.41(7) . . ?
F2 Ga1 F1 90.74(7) . . ?
F3 Ga1 F1 175.68(7) . . ?
F2 Ga1 O1 96.70(8) . . ?
F3 Ga1 O1 87.76(7) . . ?
F1 Ga1 O1 88.94(7) . . ?
F2 Ga1 N2 92.28(9) . . ?
F3 Ga1 N2 90.64(8) . . ?
F1 Ga1 N2 92.19(8) . . ?
O1 Ga1 N2 170.94(9) . . ?
F2 Ga1 N1 170.62(8) . . ?
F3 Ga1 N1 87.52(7) . . ?
F1 Ga1 N1 89.86(7) . . ?
O1 Ga1 N1 92.67(8) . . ?
N2 Ga1 N1 78.35(9) . . ?
Ga1 O1 H1A 110(3) . . ?
Ga1 O1 H1B 119(4) . . ?
H1A O1 H1B 110(5) . . ?
C1 N1 C5 119.9(2) . . ?
C1 N1 Ga1 124.92(18) . . ?
C5 N1 Ga1 114.92(16) . . ?
C10 N2 C6 119.3(3) . . ?
C10 N2 Ga1 124.7(2) . . ?
C6 N2 Ga1 115.94(19) . . ?
N1 C1 C2 121.3(2) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.6(2) . . ?
N1 C5 C6 115.2(2) . . ?
C4 C5 C6 123.2(2) . . ?
N2 C6 C7 120.8(3) . . ?
N2 C6 C5 114.6(2) . . ?
C7 C6 C5 124.6(3) . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
N2 C10 C9 122.7(3) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
H2A O2 H2B1 103(7) . . ?
H2A O2 H2B2 109(7) . . ?
H2B1 O2 H2B2 147(10) . . ?
H3A O3 H3B1 118(8) . . ?
H3A O3 H3B2 110(7) . . ?
H3B1 O3 H3B2 84(9) . . ?

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
C5 N1 C1 C2 -0.7(4) . . . . ?
Ga1 N1 C1 C2 173.33(18) . . . . ?
N1 C1 C2 C3 -1.0(4) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C1 N1 C5 C4 2.0(4) . . . . ?
Ga1 N1 C5 C4 -172.56(19) . . . . ?
C1 N1 C5 C6 -176.7(2) . . . . ?
Ga1 N1 C5 C6 8.7(3) . . . . ?
C3 C4 C5 N1 -1.6(4) . . . . ?
C3 C4 C5 C6 177.0(2) . . . . ?
C10 N2 C6 C7 -0.6(3) . . . . ?
Ga1 N2 C6 C7 175.44(18) . . . . ?
C10 N2 C6 C5 178.0(2) . . . . ?
Ga1 N2 C6 C5 -5.9(2) . . . . ?
N1 C5 C6 N2 -1.9(3) . . . . ?
C4 C5 C6 N2 179.4(2) . . . . ?
N1 C5 C6 C7 176.6(2) . . . . ?
C4 C5 C6 C7 -2.1(4) . . . . ?
N2 C6 C7 C8 0.2(4) . . . . ?
C5 C6 C7 C8 -178.2(2) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C6 N2 C10 C9 0.4(4) . . . . ?
Ga1 N2 C10 C9 -175.35(18) . . . . ?
C8 C9 C10 N2 0.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A F3 0.802(19) 1.76(2) 2.548(2) 169(5) 2_655
O1 H1B F1 0.794(19) 1.78(2) 2.571(2) 175(6) 2_645
O2 H2A F1 0.799(19) 1.956(19) 2.753(3) 177(5) .
O2 H2B1 O3 0.82(2) 1.93(2) 2.745(3) 174(10) 1_565
O2 H2B2 O2 0.81(2) 2.01(5) 2.743(4) 150(9) 3_665
O3 H3A F2 0.820(19) 1.864(19) 2.683(3) 176(5) .
O3 H3B1 O2 0.82(2) 1.94(3) 2.745(3) 168(10) 1_545
O3 H3B2 O3 0.82(2) 1.98(2) 2.802(5) 178(10) 3_655

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.166
_refine_diff_density_min         -1.637
_refine_diff_density_rms         0.150

_iucr_refine_instruction_details 
;
 Add final .res file here for Acta Cryst publications or if required.
;
_exptl_crystal_recrystallization_method 'Solvent evaporation'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1053158'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F3 Ga N2 O'
_chemical_formula_sum            'C12 H10 F3 Ga N2 O'
_chemical_formula_weight         324.94

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'
F F 0.0171 0.0103 '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'

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

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

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

_cell_length_a                   8.3906(5)
_cell_length_b                   7.1940(5)
_cell_length_c                   19.0124(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.631(3)
_cell_angle_gamma                90
_cell_volume                     1127.93(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13101
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.472
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax'
_diffrn_source                   'Rotating Anode'
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            12632
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.034
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2581
_reflns_number_gt                2362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+1.0234P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2581
_refine_ls_number_parameters     178
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0794(2) 0.4177(3) 0.23331(10) 0.0116(4) Uani 1 1 d . . . . .
H1 H 1.0303 0.4335 0.2741 0.014 Uiso 1 1 calc R U . . .
C2 C 1.2419(2) 0.4724(3) 0.23699(10) 0.0133(4) Uani 1 1 d . . . . .
H2 H 1.3012 0.5235 0.2800 0.016 Uiso 1 1 calc R U . . .
C3 C 1.3150(3) 0.4518(3) 0.17836(11) 0.0132(4) Uani 1 1 d . . . . .
H3 H 1.4256 0.4847 0.1811 0.016 Uiso 1 1 calc R U . . .
C4 C 1.2232(2) 0.3811(3) 0.11391(10) 0.0111(4) Uani 1 1 d . . . . .
C5 C 1.0624(2) 0.3293(3) 0.11501(10) 0.0093(3) Uani 1 1 d . . . . .
C6 C 1.2833(2) 0.3663(3) 0.04800(10) 0.0135(4) Uani 1 1 d . . . . .
H6 H 1.3925 0.3995 0.0471 0.016 Uiso 1 1 calc R U . . .
C7 C 1.1862(3) 0.3056(3) -0.01307(11) 0.0132(4) Uani 1 1 d . . . . .
H7 H 1.2282 0.2990 -0.0561 0.016 Uiso 1 1 calc R U . . .
C8 C 1.0205(2) 0.2510(3) -0.01336(10) 0.0104(4) Uani 1 1 d . . . . .
C9 C 0.9609(2) 0.2609(2) 0.05097(10) 0.0092(4) Uani 1 1 d . . . . .
C10 C 0.9131(3) 0.1847(3) -0.07430(10) 0.0134(4) Uani 1 1 d . . . . .
H10 H 0.9480 0.1742 -0.1189 0.016 Uiso 1 1 calc R U . . .
C11 C 0.7572(3) 0.1354(3) -0.06840(10) 0.0137(4) Uani 1 1 d . . . . .
H11 H 0.6834 0.0918 -0.1090 0.016 Uiso 1 1 calc R U . . .
C12 C 0.7084(2) 0.1503(3) -0.00157(10) 0.0120(4) Uani 1 1 d . . . . .
H12 H 0.6008 0.1162 0.0020 0.014 Uiso 1 1 calc R U . . .
F1 F 0.87657(14) -0.00536(15) 0.18029(6) 0.0117(2) Uani 1 1 d . . . . .
F2 F 0.56502(14) 0.10314(17) 0.13323(6) 0.0152(2) Uani 1 1 d . . . . .
F3 F 0.67344(14) 0.46177(15) 0.14846(6) 0.0115(2) Uani 1 1 d . . . . .
O1 O 0.7587(2) 0.2356(2) 0.26322(8) 0.0138(3) Uani 1 1 d D . . . .
Ga1 Ga 0.75946(2) 0.22026(3) 0.16038(2) 0.00816(8) Uani 1 1 d . . . . .
N1 N 0.99293(19) 0.3445(2) 0.17406(8) 0.0091(3) Uani 1 1 d . . . . .
N2 N 0.8076(2) 0.2104(2) 0.05645(8) 0.0089(3) Uani 1 1 d . . . . .
H1WA H 0.710(3) 0.318(3) 0.2814(12) 0.013 Uiso 1 1 d D U . . .
H1WB H 0.779(3) 0.147(3) 0.2906(11) 0.013 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.331(2) . ?
C1 C2 1.409(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.416(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(3) . ?
C4 C6 1.438(3) . ?
C5 N1 1.362(2) . ?
C5 C9 1.438(3) . ?
C6 C7 1.361(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.444(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.406(3) . ?
C8 C10 1.413(3) . ?
C9 N2 1.359(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.409(3) . ?
C11 H11 0.9500 . ?
C12 N2 1.325(2) . ?
C12 H12 0.9500 . ?
F1 Ga1 1.8990(11) . ?
F2 Ga1 1.8242(12) . ?
F3 Ga1 1.8790(11) . ?
O1 Ga1 1.9594(14) . ?
O1 H1WA 0.828(16) . ?
O1 H1WB 0.820(16) . ?
Ga1 N2 2.0897(16) . ?
Ga1 N1 2.1250(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.60(18) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 120.12(18) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.17(18) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 116.96(17) . . ?
C5 C4 C6 119.06(18) . . ?
C3 C4 C6 123.94(18) . . ?
N1 C5 C4 123.35(17) . . ?
N1 C5 C9 116.68(17) . . ?
C4 C5 C9 119.94(17) . . ?
C7 C6 C4 121.06(18) . . ?
C7 C6 H6 119.5 . . ?
C4 C6 H6 119.5 . . ?
C6 C7 C8 120.98(18) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C10 117.06(18) . . ?
C9 C8 C7 118.67(18) . . ?
C10 C8 C7 124.26(17) . . ?
N2 C9 C8 123.15(18) . . ?
N2 C9 C5 116.60(16) . . ?
C8 C9 C5 120.25(18) . . ?
C11 C10 C8 119.40(17) . . ?
C11 C10 H10 120.3 . . ?
C8 C10 H10 120.3 . . ?
C10 C11 C12 119.43(18) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
N2 C12 C11 122.21(19) . . ?
N2 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
Ga1 O1 H1WA 123.3(17) . . ?
Ga1 O1 H1WB 123.3(17) . . ?
H1WA O1 H1WB 111(2) . . ?
F2 Ga1 F3 95.13(5) . . ?
F2 Ga1 F1 93.69(5) . . ?
F3 Ga1 F1 170.94(5) . . ?
F2 Ga1 O1 98.11(6) . . ?
F3 Ga1 O1 89.79(5) . . ?
F1 Ga1 O1 86.92(5) . . ?
F2 Ga1 N2 92.02(6) . . ?
F3 Ga1 N2 93.11(5) . . ?
F1 Ga1 N2 88.65(5) . . ?
O1 Ga1 N2 169.17(7) . . ?
F2 Ga1 N1 170.08(6) . . ?
F3 Ga1 N1 87.18(6) . . ?
F1 Ga1 N1 84.47(6) . . ?
O1 Ga1 N1 91.54(6) . . ?
N2 Ga1 N1 78.20(6) . . ?
C1 N1 C5 118.72(17) . . ?
C1 N1 Ga1 128.04(13) . . ?
C5 N1 Ga1 112.98(12) . . ?
C12 N2 C9 118.75(16) . . ?
C12 N2 Ga1 126.65(14) . . ?
C9 N2 Ga1 114.46(13) . . ?

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
N1 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C2 C3 C4 C6 175.35(18) . . . . ?
C3 C4 C5 N1 0.2(3) . . . . ?
C6 C4 C5 N1 -177.60(17) . . . . ?
C3 C4 C5 C9 178.37(17) . . . . ?
C6 C4 C5 C9 0.6(3) . . . . ?
C5 C4 C6 C7 0.9(3) . . . . ?
C3 C4 C6 C7 -176.72(18) . . . . ?
C4 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C6 C7 C8 C10 -179.26(18) . . . . ?
C10 C8 C9 N2 -0.1(3) . . . . ?
C7 C8 C9 N2 -179.10(17) . . . . ?
C10 C8 C9 C5 -179.19(17) . . . . ?
C7 C8 C9 C5 1.8(3) . . . . ?
N1 C5 C9 N2 -2.8(2) . . . . ?
C4 C5 C9 N2 178.89(17) . . . . ?
N1 C5 C9 C8 176.37(17) . . . . ?
C4 C5 C9 C8 -1.9(3) . . . . ?
C9 C8 C10 C11 0.7(3) . . . . ?
C7 C8 C10 C11 179.64(18) . . . . ?
C8 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 N2 -0.1(3) . . . . ?
C2 C1 N1 C5 -2.6(3) . . . . ?
C2 C1 N1 Ga1 171.12(14) . . . . ?
C4 C5 N1 C1 2.3(3) . . . . ?
C9 C5 N1 C1 -175.98(16) . . . . ?
C4 C5 N1 Ga1 -172.34(14) . . . . ?
C9 C5 N1 Ga1 9.4(2) . . . . ?
C11 C12 N2 C9 0.7(3) . . . . ?
C11 C12 N2 Ga1 -174.78(14) . . . . ?
C8 C9 N2 C12 -0.6(3) . . . . ?
C5 C9 N2 C12 178.56(16) . . . . ?
C8 C9 N2 Ga1 175.37(14) . . . . ?
C5 C9 N2 Ga1 -5.5(2) . . . . ?

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Solvent evaporation'
