# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_comp1
_database_code_depnum_ccdc_archive 'CCDC 1477242'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 B2 O4'
_chemical_formula_weight         380.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.5530(3)
_cell_length_b                   11.3416(3)
_cell_length_c                   10.3481(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.428(4)
_cell_angle_gamma                90
_cell_volume                     1069.71(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1671
_cell_measurement_theta_min      3.8943
_cell_measurement_theta_max      61.2024


_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.616
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.7539  -77.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega -104.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.7539  -77.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
  3 omega   58.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.7539 -178.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.7539 -178.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  -66.00   25.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   61.0000  120.0000 91

#__ type_ start__ end____ width___ exp.time_
  6 omega   83.00  157.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       91.4517   77.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
  7 omega  108.00  164.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       91.4517  111.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega   90.00  160.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       91.4517   30.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   19.00  110.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       91.4517 -111.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
 10 omega   69.00   97.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       91.4517   61.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega  112.00  150.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       91.4517  111.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega  105.00  137.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       91.4517   78.0000  -99.0000 32

#__ type_ start__ end____ width___ exp.time_
 13 omega   20.00   73.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       91.4517  -94.0000 -150.0000 53
;

_diffrn_detector_area_resol_mean 16.2974
_diffrn_reflns_number            3064
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.852
_diffrn_reflns_theta_max         61.289
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.835
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.835
_reflns_number_total             1625
_reflns_number_gt                1464
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.1982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1625
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.76583(14) 0.42632(12) -0.11892(13) 0.0214(3) Uani 1 1 d . . . . .
H1A H 0.8623 0.4153 -0.0500 0.026 Uiso 1 1 calc R U . . .
H1B H 0.7497 0.3582 -0.1815 0.026 Uiso 1 1 calc R U . . .
C2 C 0.77171(16) 0.53816(13) -0.19892(15) 0.0278(4) Uani 1 1 d . . . . .
H2A H 0.6792 0.5472 -0.2717 0.042 Uiso 1 1 calc R U . . .
H2B H 0.8530 0.5326 -0.2381 0.042 Uiso 1 1 calc R U . . .
H2C H 0.7867 0.6065 -0.1384 0.042 Uiso 1 1 calc R U . . .
C3 C 0.62791(15) 0.31121(13) 0.04112(14) 0.0239(3) Uani 1 1 d . . . . .
H3A H 0.7212 0.3003 0.1144 0.029 Uiso 1 1 calc R U . . .
H3B H 0.5496 0.3247 0.0841 0.029 Uiso 1 1 calc R U . . .
C4 C 0.59339(16) 0.19803(13) -0.04270(15) 0.0285(4) Uani 1 1 d . . . . .
H4A H 0.4961 0.2045 -0.1092 0.043 Uiso 1 1 calc R U . . .
H4B H 0.5947 0.1309 0.0173 0.043 Uiso 1 1 calc R U . . .
H4C H 0.6672 0.1861 -0.0899 0.043 Uiso 1 1 calc R U . . .
C5 C 0.63582(14) 0.55922(11) 0.15423(13) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.74915(14) 0.59877(11) 0.27719(13) 0.0193(3) Uani 1 1 d . . . . .
C7 C 0.89640(15) 0.59964(13) 0.27960(14) 0.0237(3) Uani 1 1 d . . . . .
H7 H 0.9230 0.5755 0.2022 0.028 Uiso 1 1 calc R U . . .
C8 C 1.00286(16) 0.63585(13) 0.39538(15) 0.0280(4) Uani 1 1 d . . . . .
H8 H 1.1031 0.6362 0.3978 0.034 Uiso 1 1 calc R U . . .
C9 C 0.96393(16) 0.67166(13) 0.50798(15) 0.0281(4) Uani 1 1 d . . . . .
H9 H 1.0376 0.6963 0.5874 0.034 Uiso 1 1 calc R U . . .
C10 C 0.81808(16) 0.67165(12) 0.50519(14) 0.0263(3) Uani 1 1 d . . . . .
H10 H 0.7920 0.6969 0.5824 0.032 Uiso 1 1 calc R U . . .
C11 C 0.71043(15) 0.63505(12) 0.39039(13) 0.0222(3) Uani 1 1 d . . . . .
H11 H 0.6105 0.6346 0.3887 0.027 Uiso 1 1 calc R U . . .
B1 B 0.64154(16) 0.42569(14) -0.04457(15) 0.0202(4) Uani 1 1 d . . . . .
O1 O 0.67567(10) 0.53511(8) 0.05060(9) 0.0212(3) Uani 1 1 d . . . . .
O2 O 0.49542(9) 0.44715(8) -0.15942(9) 0.0209(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.525(2) . ?
C1 B1 1.5966(19) . ?
C3 C4 1.529(2) . ?
C3 B1 1.600(2) . ?
C5 O1 1.2705(16) . ?
C5 O2 1.2728(16) 3_665 ?
C5 C6 1.4722(19) . ?
C6 C11 1.3921(19) . ?
C6 C7 1.3994(19) . ?
C7 C8 1.381(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.385(2) . ?
C10 C11 1.3818(19) . ?
B1 O1 1.5568(17) . ?
B1 O2 1.5577(17) . ?
O2 C5 1.2729(16) 3_665 ?

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
C2 C1 B1 114.77(11) . . ?
C4 C3 B1 113.99(11) . . ?
O1 C5 O2 124.84(12) . 3_665 ?
O1 C5 C6 117.80(11) . . ?
O2 C5 C6 117.36(11) 3_665 . ?
C11 C6 C7 120.13(12) . . ?
C11 C6 C5 120.35(12) . . ?
C7 C6 C5 119.51(12) . . ?
C8 C7 C6 119.51(13) . . ?
C7 C8 C9 120.20(13) . . ?
C10 C9 C8 120.27(13) . . ?
C11 C10 C9 120.20(13) . . ?
C10 C11 C6 119.69(13) . . ?
O1 B1 O2 109.15(10) . . ?
O1 B1 C1 104.85(10) . . ?
O2 B1 C1 104.92(10) . . ?
O1 B1 C3 109.43(11) . . ?
O2 B1 C3 110.28(11) . . ?
C1 B1 C3 117.81(11) . . ?
C5 O1 B1 130.29(10) . . ?
C5 O2 B1 128.89(10) 3_665 . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.043

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_comp2
_database_code_depnum_ccdc_archive 'CCDC 1477243'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Al2 O4'
_chemical_formula_weight         356.31

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'
O O 0.0106 0.0060 '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'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4170(3)
_cell_length_b                   8.6964(8)
_cell_length_c                   9.1984(8)
_cell_angle_alpha                117.254(9)
_cell_angle_beta                 109.439(6)
_cell_angle_gamma                94.798(6)
_cell_volume                     477.25(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2192
_cell_measurement_theta_min      3.0292
_cell_measurement_theta_max      28.9957

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             188
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00  -59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5002  147.0000   58.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00  -42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5002  124.0000    5.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0783   19.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega   12.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0783 -124.0000  -73.0000 65

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0783  -57.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
  6 omega  -18.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0783   19.0000  120.0000 107

;

_diffrn_detector_area_resol_mean 16.2974
_diffrn_reflns_number            3254
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.035
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1948
_reflns_number_gt                1769
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+0.1577P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1948
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8321(2) 0.7968(2) 0.7052(2) 0.0261(4) Uani 1 1 d . . . . .
H1A H 0.9196 0.8395 0.6636 0.039 Uiso 1 1 calc R U . . .
H1B H 0.8038 0.6656 0.6488 0.039 Uiso 1 1 calc R U . . .
H1C H 0.8980 0.8536 0.8364 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3705(2) 0.8016(2) 0.7005(2) 0.0275(4) Uani 1 1 d . . . . .
H2A H 0.4204 0.8598 0.8316 0.041 Uiso 1 1 calc R U . . .
H2B H 0.3244 0.6707 0.6452 0.041 Uiso 1 1 calc R U . . .
H2C H 0.2595 0.8451 0.6555 0.041 Uiso 1 1 calc R U . . .
C3 C 0.6232(2) 1.2431(2) 0.7428(2) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.7100(2) 1.4147(2) 0.91831(19) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.8186(2) 1.4154(2) 1.0753(2) 0.0203(3) Uani 1 1 d . . . . .
H5 H 0.8373 1.3064 1.0696 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8988(2) 1.5763(2) 1.2395(2) 0.0267(4) Uani 1 1 d . . . . .
H6 H 0.9720 1.5777 1.3469 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8724(2) 1.7353(2) 1.2471(2) 0.0285(4) Uani 1 1 d . . . . .
H7 H 0.9283 1.8454 1.3598 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7648(3) 1.7345(2) 1.0909(2) 0.0276(4) Uani 1 1 d . . . . .
H8 H 0.7475 1.8440 1.0969 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6829(2) 1.5741(2) 0.9266(2) 0.0208(3) Uani 1 1 d . . . . .
H9 H 0.6082 1.5730 0.8196 0.025 Uiso 1 1 calc R U . . .
O1 O 0.65363(18) 1.10133(15) 0.73846(16) 0.0281(3) Uani 1 1 d . . . . .
O2 O 0.47796(18) 0.75360(16) 0.39628(15) 0.0270(3) Uani 1 1 d . . . . .
Al1 Al 0.58378(6) 0.85956(6) 0.63900(6) 0.01617(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 Al1 1.9460(17) . ?
C2 Al1 1.9490(17) . ?
C3 O1 1.2568(19) . ?
C3 O2 1.2644(19) 2_676 ?
C3 C4 1.480(2) . ?
C4 C9 1.388(2) . ?
C4 C5 1.397(2) . ?
C5 C6 1.385(2) . ?
C6 C7 1.385(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.385(2) . ?
O1 Al1 1.8073(13) . ?
O2 C3 1.2644(19) 2_676 ?
O2 Al1 1.8106(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C3 O2 123.09(14) . 2_676 ?
O1 C3 C4 118.77(14) . . ?
O2 C3 C4 118.14(14) 2_676 . ?
C9 C4 C5 120.28(14) . . ?
C9 C4 C3 120.02(14) . . ?
C5 C4 C3 119.70(14) . . ?
C6 C5 C4 119.52(15) . . ?
C7 C6 C5 120.04(16) . . ?
C6 C7 C8 120.42(15) . . ?
C9 C8 C7 119.88(16) . . ?
C8 C9 C4 119.86(15) . . ?
C3 O1 Al1 151.93(11) . . ?
C3 O2 Al1 148.90(11) 2_676 . ?
O1 Al1 O2 108.70(6) . . ?
O1 Al1 C1 105.84(7) . . ?
O2 Al1 C1 105.96(7) . . ?
O1 Al1 C2 106.69(7) . . ?
O2 Al1 C2 106.73(7) . . ?
C1 Al1 C2 122.40(8) . . ?

_refine_diff_density_max         0.644
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_comp4
_database_code_depnum_ccdc_archive 'CCDC 1477244'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 B N O2'
_chemical_formula_weight         283.16

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.2950(3)
_cell_length_b                   14.3120(3)
_cell_length_c                   17.2530(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.2280(10)
_cell_angle_gamma                90
_cell_volume                     3182.17(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3216
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9352
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             5498
_reflns_number_gt                5015
_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       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0848P)²+1.7754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5498
_refine_ls_number_parameters     385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1606
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.60718(14) 0.79251(13) 0.25860(11) 0.0252(4) Uani 1 1 d . . . . .
H1A H 0.5815 0.8479 0.2253 0.030 Uiso 1 1 calc R U . . .
H1B H 0.6413 0.8152 0.3129 0.030 Uiso 1 1 calc R U . . .
C2 C 0.68888(16) 0.74417(14) 0.22404(12) 0.0319(5) Uani 1 1 d . . . . .
H2A H 0.7099 0.6854 0.2527 0.048 Uiso 1 1 calc R U . . .
H2B H 0.7495 0.7850 0.2301 0.048 Uiso 1 1 calc R U . . .
H2C H 0.6597 0.7310 0.1672 0.048 Uiso 1 1 calc R U . . .
C3 C 0.41274(14) 0.78755(13) 0.28142(11) 0.0252(4) Uani 1 1 d . . . . .
H3A H 0.4383 0.8248 0.3307 0.030 Uiso 1 1 calc R U . . .
H3B H 0.3883 0.8320 0.2368 0.030 Uiso 1 1 calc R U . . .
C4 C 0.32012(15) 0.72981(13) 0.29108(12) 0.0305(4) Uani 1 1 d . . . . .
H4A H 0.2906 0.6959 0.2414 0.046 Uiso 1 1 calc R U . . .
H4B H 0.2674 0.7714 0.3032 0.046 Uiso 1 1 calc R U . . .
H4C H 0.3429 0.6851 0.3349 0.046 Uiso 1 1 calc R U . . .
C5 C 0.43963(13) 0.69148(12) 0.12086(11) 0.0228(4) Uani 1 1 d . . . . .
C6 C 0.40234(13) 0.61329(12) 0.06358(10) 0.0208(4) Uani 1 1 d . . . . .
C7 C 0.39651(14) 0.52158(12) 0.08954(11) 0.0248(4) Uani 1 1 d . . . . .
H7 H 0.4152 0.5073 0.1450 0.030 Uiso 1 1 calc R U . . .
C8 C 0.36318(15) 0.45153(13) 0.03360(12) 0.0308(4) Uani 1 1 d . . . . .
H8 H 0.3580 0.3892 0.0512 0.037 Uiso 1 1 calc R U . . .
C9 C 0.33737(14) 0.47105(14) -0.04716(11) 0.0278(4) Uani 1 1 d . . . . .
H9 H 0.3169 0.4221 -0.0849 0.033 Uiso 1 1 calc R U . . .
C10 C 0.34133(15) 0.56203(15) -0.07297(11) 0.0307(5) Uani 1 1 d . . . . .
H10 H 0.3220 0.5759 -0.1285 0.037 Uiso 1 1 calc R U . . .
C11 C 0.37353(14) 0.63322(14) -0.01770(11) 0.0268(4) Uani 1 1 d . . . . .
H11 H 0.3759 0.6958 -0.0356 0.032 Uiso 1 1 calc R U . . .
C12 C 0.56491(14) 0.56292(13) 0.32645(11) 0.0259(4) Uani 1 1 d . . . . .
H12 H 0.5527 0.5399 0.2733 0.031 Uiso 1 1 calc R U . . .
C13 C 0.59924(15) 0.50161(13) 0.38913(11) 0.0267(4) Uani 1 1 d . . . . .
H13 H 0.6097 0.4377 0.3784 0.032 Uiso 1 1 calc R U . . .
C14 C 0.61869(13) 0.53238(13) 0.46771(11) 0.0246(4) Uani 1 1 d . . . . .
C15 C 0.60037(14) 0.62660(14) 0.47907(11) 0.0266(4) Uani 1 1 d . . . . .
H15 H 0.6117 0.6511 0.5317 0.032 Uiso 1 1 calc R U . . .
C16 C 0.56582(14) 0.68426(13) 0.41414(10) 0.0252(4) Uani 1 1 d . . . . .
H16 H 0.5539 0.7483 0.4234 0.030 Uiso 1 1 calc R U . . .
C17 C 0.65734(15) 0.46716(14) 0.53664(11) 0.0297(4) Uani 1 1 d . . . . .
H17A H 0.6278 0.4049 0.5227 0.045 Uiso 1 1 calc R U . . .
H17B H 0.6363 0.4904 0.5837 0.045 Uiso 1 1 calc R U . . .
H17C H 0.7332 0.4636 0.5485 0.045 Uiso 1 1 calc R U . . .
C18 C 0.91125(14) 1.05150(12) 0.29186(11) 0.0247(4) Uani 1 1 d . . . . .
H18A H 0.9428 1.0892 0.3398 0.030 Uiso 1 1 calc R U . . .
H18B H 0.8872 1.0954 0.2467 0.030 Uiso 1 1 calc R U . . .
C19 C 0.81695(16) 1.00061(14) 0.30682(13) 0.0343(5) Uani 1 1 d . . . . .
H19A H 0.7848 0.9628 0.2599 0.051 Uiso 1 1 calc R U . . .
H19B H 0.7666 1.0464 0.3165 0.051 Uiso 1 1 calc R U . . .
H19C H 0.8388 0.9599 0.3536 0.051 Uiso 1 1 calc R U . . .
C20 C 1.10253(14) 1.03964(13) 0.26211(10) 0.0240(4) Uani 1 1 d . . . . .
H20A H 1.0809 1.0964 0.2294 0.029 Uiso 1 1 calc R U . . .
H20B H 1.1425 1.0602 0.3156 0.029 Uiso 1 1 calc R U . . .
C21 C 1.17427(14) 0.98191(13) 0.22334(11) 0.0274(4) Uani 1 1 d . . . . .
H21A H 1.1907 0.9225 0.2519 0.041 Uiso 1 1 calc R U . . .
H21B H 1.2385 1.0167 0.2261 0.041 Uiso 1 1 calc R U . . .
H21C H 1.1394 0.9696 0.1673 0.041 Uiso 1 1 calc R U . . .
C22 C 0.92879(13) 0.95019(12) 0.12874(10) 0.0227(4) Uani 1 1 d . . . . .
C23 C 0.89651(13) 0.87374(13) 0.06865(10) 0.0218(4) Uani 1 1 d . . . . .
C24 C 0.88069(14) 0.78175(13) 0.09057(10) 0.0236(4) Uani 1 1 d . . . . .
H24 H 0.8902 0.7657 0.1453 0.028 Uiso 1 1 calc R U . . .
C25 C 0.85104(14) 0.71439(13) 0.03171(11) 0.0270(4) Uani 1 1 d . . . . .
H25 H 0.8394 0.6521 0.0464 0.032 Uiso 1 1 calc R U . . .
C26 C 0.83824(15) 0.73671(14) -0.04804(11) 0.0279(4) Uani 1 1 d . . . . .
H26 H 0.8183 0.6898 -0.0878 0.033 Uiso 1 1 calc R U . . .
C27 C 0.85455(15) 0.82791(14) -0.06996(11) 0.0284(4) Uani 1 1 d . . . . .
H27 H 0.8460 0.8434 -0.1247 0.034 Uiso 1 1 calc R U . . .
C28 C 0.88327(14) 0.89622(13) -0.01176(11) 0.0248(4) Uani 1 1 d . . . . .
H28 H 0.8939 0.9586 -0.0268 0.030 Uiso 1 1 calc R U . . .
C29 C 1.04877(14) 0.81762(12) 0.33238(11) 0.0244(4) Uani 1 1 d . . . . .
H29 H 1.0300 0.7944 0.2792 0.029 Uiso 1 1 calc R U . . .
C30 C 1.08608(14) 0.75563(13) 0.39443(11) 0.0245(4) Uani 1 1 d . . . . .
H30 H 1.0926 0.6912 0.3833 0.029 Uiso 1 1 calc R U . . .
C31 C 1.11395(13) 0.78737(13) 0.47282(11) 0.0246(4) Uani 1 1 d . . . . .
C32 C 1.10365(14) 0.88256(13) 0.48503(11) 0.0256(4) Uani 1 1 d . . . . .
H32 H 1.1226 0.9076 0.5376 0.031 Uiso 1 1 calc R U . . .
C33 C 1.06578(14) 0.94068(13) 0.42047(10) 0.0236(4) Uani 1 1 d . . . . .
H33 H 1.0590 1.0055 0.4301 0.028 Uiso 1 1 calc R U . . .
C34 C 1.15449(16) 0.72133(14) 0.54127(11) 0.0302(4) Uani 1 1 d . . . . .
H34A H 1.1264 0.6587 0.5267 0.045 Uiso 1 1 calc R U . . .
H34B H 1.1330 0.7431 0.5886 0.045 Uiso 1 1 calc R U . . .
H34C H 1.2304 0.7192 0.5530 0.045 Uiso 1 1 calc R U . . .
O1 O 0.47290(10) 0.66295(8) 0.19509(7) 0.0233(3) Uani 1 1 d . . . . .
O2 O 0.43778(11) 0.77264(9) 0.09894(8) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.95587(10) 0.91991(8) 0.20313(7) 0.0235(3) Uani 1 1 d . . . . .
O4 O 0.92945(10) 1.03177(9) 0.10878(8) 0.0288(3) Uani 1 1 d . . . . .
B1 B 0.50863(16) 0.72967(14) 0.26455(12) 0.0229(4) Uani 1 1 d . . . . .
B2 B 0.99988(16) 0.98563(14) 0.27199(12) 0.0228(4) Uani 1 1 d . . . . .
N1 N 0.54807(11) 0.65403(10) 0.33785(9) 0.0216(3) Uani 1 1 d . . . . .
N2 N 1.03819(11) 0.90952(10) 0.34466(9) 0.0218(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.527(3) . ?
C1 B1 1.613(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.526(3) . ?
C3 B1 1.606(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 O2 1.220(2) . ?
C5 O1 1.313(2) . ?
C5 C6 1.495(2) . ?
C6 C11 1.389(2) . ?
C6 C7 1.395(2) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 N1 1.346(2) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 C17 1.500(2) . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 N1 1.350(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.526(3) . ?
C18 B2 1.610(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.534(3) . ?
C20 B2 1.614(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O4 1.218(2) . ?
C22 O3 1.318(2) . ?
C22 C23 1.496(2) . ?
C23 C28 1.393(2) . ?
C23 C24 1.400(3) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.386(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 N2 1.345(2) . ?
C29 C30 1.385(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(3) . ?
C31 C34 1.505(2) . ?
C32 C33 1.382(3) . ?
C32 H32 0.9500 . ?
C33 N2 1.345(2) . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
O1 B1 1.514(2) . ?
O2 B1 2.847(2) . ?
O3 B2 1.515(2) . ?
B1 N1 1.649(2) . ?
B2 N2 1.644(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
C2 C1 B1 116.04(15) . . ?
C2 C1 H1A 108.3 . . ?
B1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
B1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 B1 116.00(15) . . ?
C4 C3 H3A 108.3 . . ?
B1 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
B1 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 O1 125.08(16) . . ?
O2 C5 C6 121.99(16) . . ?
O1 C5 C6 112.93(15) . . ?
C11 C6 C7 119.60(16) . . ?
C11 C6 C5 118.55(16) . . ?
C7 C6 C5 121.85(16) . . ?
C8 C7 C6 119.36(17) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 120.95(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.80(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 119.99(17) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 120.27(18) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
N1 C12 C13 122.45(17) . . ?
N1 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C14 120.66(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 116.59(17) . . ?
C13 C14 C17 121.49(17) . . ?
C15 C14 C17 121.92(17) . . ?
C16 C15 C14 120.07(17) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
N1 C16 C15 123.01(17) . . ?
N1 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 B2 115.54(15) . . ?
C19 C18 H18A 108.4 . . ?
B2 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
B2 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 B2 114.87(15) . . ?
C21 C20 H20A 108.5 . . ?
B2 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
B2 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 O3 124.84(16) . . ?
O4 C22 C23 121.73(16) . . ?
O3 C22 C23 113.42(15) . . ?
C28 C23 C24 119.72(16) . . ?
C28 C23 C22 117.78(16) . . ?
C24 C23 C22 122.50(15) . . ?
C25 C24 C23 119.41(16) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 120.82(18) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 119.90(17) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 119.90(17) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C23 120.24(17) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?
N2 C29 C30 122.41(17) . . ?
N2 C29 H29 118.8 . . ?
C30 C29 H29 118.8 . . ?
C29 C30 C31 120.18(17) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 117.11(17) . . ?
C30 C31 C34 121.15(17) . . ?
C32 C31 C34 121.73(17) . . ?
C33 C32 C31 119.83(17) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
N2 C33 C32 122.86(17) . . ?
N2 C33 H33 118.6 . . ?
C32 C33 H33 118.6 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C5 O1 B1 122.73(14) . . ?
C5 O2 B1 60.44(11) . . ?
C22 O3 B2 121.31(14) . . ?
O1 B1 C3 111.11(15) . . ?
O1 B1 C1 113.76(15) . . ?
C3 B1 C1 114.67(15) . . ?
O1 B1 N1 99.89(13) . . ?
C3 B1 N1 108.45(14) . . ?
C1 B1 N1 107.73(14) . . ?
O1 B1 O2 51.69(8) . . ?
C3 B1 O2 89.36(11) . . ?
C1 B1 O2 83.64(11) . . ?
N1 B1 O2 151.13(12) . . ?
O3 B2 C18 111.63(15) . . ?
O3 B2 C20 112.84(15) . . ?
C18 B2 C20 115.09(15) . . ?
O3 B2 N2 100.04(13) . . ?
C18 B2 N2 109.34(14) . . ?
C20 B2 N2 106.64(14) . . ?
C12 N1 C16 117.22(16) . . ?
C12 N1 B1 123.85(14) . . ?
C16 N1 B1 118.92(14) . . ?
C33 N2 C29 117.61(15) . . ?
C33 N2 B2 118.77(14) . . ?
C29 N2 B2 123.53(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C5 C6 C11 5.8(3) . . . . ?
O1 C5 C6 C11 -174.50(15) . . . . ?
O2 C5 C6 C7 -174.60(17) . . . . ?
O1 C5 C6 C7 5.1(2) . . . . ?
C11 C6 C7 C8 0.8(3) . . . . ?
C5 C6 C7 C8 -178.79(16) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C8 C9 C10 -2.2(3) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C6 0.3(3) . . . . ?
C7 C6 C11 C10 -1.5(3) . . . . ?
C5 C6 C11 C10 178.13(16) . . . . ?
N1 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C12 C13 C14 C17 -179.19(17) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C17 C14 C15 C16 179.39(17) . . . . ?
C14 C15 C16 N1 0.0(3) . . . . ?
O4 C22 C23 C28 10.3(3) . . . . ?
O3 C22 C23 C28 -169.45(15) . . . . ?
O4 C22 C23 C24 -170.45(17) . . . . ?
O3 C22 C23 C24 9.8(2) . . . . ?
C28 C23 C24 C25 -0.6(3) . . . . ?
C22 C23 C24 C25 -179.85(16) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C26 C27 C28 C23 0.4(3) . . . . ?
C24 C23 C28 C27 0.0(3) . . . . ?
C22 C23 C28 C27 179.27(16) . . . . ?
N2 C29 C30 C31 0.2(3) . . . . ?
C29 C30 C31 C32 -0.7(3) . . . . ?
C29 C30 C31 C34 179.88(17) . . . . ?
C30 C31 C32 C33 0.8(3) . . . . ?
C34 C31 C32 C33 -179.80(17) . . . . ?
C31 C32 C33 N2 -0.3(3) . . . . ?
O2 C5 O1 B1 3.3(3) . . . . ?
C6 C5 O1 B1 -176.33(15) . . . . ?
O1 C5 O2 B1 -1.71(14) . . . . ?
C6 C5 O2 B1 177.9(2) . . . . ?
O4 C22 O3 B2 -5.2(3) . . . . ?
C23 C22 O3 B2 174.58(14) . . . . ?
C5 O1 B1 C3 69.8(2) . . . . ?
C5 O1 B1 C1 -61.4(2) . . . . ?
C5 O1 B1 N1 -175.85(14) . . . . ?
C5 O1 B1 O2 -1.49(12) . . . . ?
C4 C3 B1 O1 51.9(2) . . . . ?
C4 C3 B1 C1 -177.38(16) . . . . ?
C4 C3 B1 N1 -56.9(2) . . . . ?
C4 C3 B1 O2 99.91(15) . . . . ?
C2 C1 B1 O1 -37.0(2) . . . . ?
C2 C1 B1 C3 -166.45(16) . . . . ?
C2 C1 B1 N1 72.72(19) . . . . ?
C2 C1 B1 O2 -80.09(15) . . . . ?
C22 O3 B2 C18 74.2(2) . . . . ?
C22 O3 B2 C20 -57.2(2) . . . . ?
C22 O3 B2 N2 -170.17(14) . . . . ?
C19 C18 B2 O3 53.6(2) . . . . ?
C19 C18 B2 C20 -176.09(16) . . . . ?
C19 C18 B2 N2 -56.1(2) . . . . ?
C21 C20 B2 O3 -35.8(2) . . . . ?
C21 C20 B2 C18 -165.55(15) . . . . ?
C21 C20 B2 N2 73.01(18) . . . . ?
C13 C12 N1 C16 -0.2(3) . . . . ?
C13 C12 N1 B1 179.13(16) . . . . ?
C15 C16 N1 C12 0.4(3) . . . . ?
C15 C16 N1 B1 -178.96(16) . . . . ?
O1 B1 N1 C12 14.8(2) . . . . ?
C3 B1 N1 C12 131.12(17) . . . . ?
C1 B1 N1 C12 -104.22(19) . . . . ?
O2 B1 N1 C12 5.6(4) . . . . ?
O1 B1 N1 C16 -165.86(15) . . . . ?
C3 B1 N1 C16 -49.5(2) . . . . ?
C1 B1 N1 C16 75.12(19) . . . . ?
O2 B1 N1 C16 -175.1(2) . . . . ?
C32 C33 N2 C29 -0.2(3) . . . . ?
C32 C33 N2 B2 -176.82(16) . . . . ?
C30 C29 N2 C33 0.3(3) . . . . ?
C30 C29 N2 B2 176.73(16) . . . . ?
O3 B2 N2 C33 -168.20(14) . . . . ?
C18 B2 N2 C33 -50.9(2) . . . . ?
C20 B2 N2 C33 74.13(19) . . . . ?
O3 B2 N2 C29 15.4(2) . . . . ?
C18 B2 N2 C29 132.70(17) . . . . ?
C20 B2 N2 C29 -102.28(18) . . . . ?

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
C12 H12 O1 0.95 2.31 2.706(2) 104.2 .
C29 H29 O3 0.95 2.30 2.700(2) 104.6 .
C1 H1A O2 0.99 2.74 3.113(2) 102.7 .
C3 H3B O2 0.99 2.75 3.253(2) 111.8 .
C18 H18B O4 0.99 2.73 3.239(2) 112.2 .
C20 H20A O4 0.99 2.68 3.052(2) 102.5 .
C13 H13 O2 0.95 2.50 3.328(2) 145.5 2_645
C17 H17C O4 0.98 2.56 3.525(2) 167.7 4_576
C30 H30 O4 0.95 2.31 3.210(2) 158.1 2_745
C34 H34C O2 0.98 2.68 3.653(2) 173.4 4_676

_refine_diff_density_max         0.612
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.056

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_comp5
_database_code_depnum_ccdc_archive 'CCDC 1477245'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Al N O2'
_chemical_formula_weight         271.28

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'
O O 0.0106 0.0060 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2140(5)
_cell_length_b                   10.3400(6)
_cell_length_c                   10.9050(7)
_cell_angle_alpha                81.727(3)
_cell_angle_beta                 77.086(2)
_cell_angle_gamma                71.565(3)
_cell_volume                     749.81(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    451(2)
_cell_measurement_reflns_used    1656
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      451(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4823
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.720
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             2741
_reflns_number_gt                2456
_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       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0835P)²+0.6157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2741
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1620
_refine_ls_wR_factor_gt          0.1573
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6842(4) 0.2064(3) 0.3712(2) 0.0323(6) Uani 1 1 d . . . . .
H1A H 0.7262 0.1732 0.2887 0.048 Uiso 1 1 calc R U . . .
H1B H 0.7209 0.1319 0.4332 0.048 Uiso 1 1 calc R U . . .
H1C H 0.7475 0.2742 0.3753 0.048 Uiso 1 1 calc R U . . .
C2 C 0.2270(4) 0.1873(3) 0.3702(2) 0.0314(6) Uani 1 1 d . . . . .
H2A H 0.0974 0.2491 0.3648 0.047 Uiso 1 1 calc R U . . .
H2B H 0.2153 0.1173 0.4370 0.047 Uiso 1 1 calc R U . . .
H2C H 0.2856 0.1462 0.2917 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3336(3) 0.5060(2) 0.2553(2) 0.0226(5) Uani 1 1 d . . . . .
C4 C 0.2681(3) 0.6542(2) 0.2146(2) 0.0211(5) Uani 1 1 d . . . . .
C5 C 0.1771(3) 0.7517(2) 0.3027(2) 0.0251(5) Uani 1 1 d . . . . .
H5 H 0.1564 0.7242 0.3884 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1178(4) 0.8890(3) 0.2630(3) 0.0329(6) Uani 1 1 d . . . . .
H6 H 0.0581 0.9538 0.3219 0.039 Uiso 1 1 calc R U . . .
C7 C 0.1474(4) 0.9301(3) 0.1351(3) 0.0388(7) Uani 1 1 d . . . . .
H7 H 0.1068 1.0225 0.1083 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2374(4) 0.8337(3) 0.0470(3) 0.0362(6) Uani 1 1 d . . . . .
H8 H 0.2568 0.8617 -0.0386 0.043 Uiso 1 1 calc R U . . .
C9 C 0.2982(4) 0.6960(3) 0.0862(2) 0.0267(5) Uani 1 1 d . . . . .
H9 H 0.3591 0.6316 0.0270 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2445(4) 0.4140(2) 0.6500(2) 0.0281(5) Uani 1 1 d . . . . .
H10 H 0.2146 0.4957 0.5998 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2026(4) 0.4186(3) 0.7789(2) 0.0333(6) Uani 1 1 d . . . . .
H11 H 0.1468 0.5025 0.8138 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2426(4) 0.2996(3) 0.8569(2) 0.0296(6) Uani 1 1 d . . . . .
C13 C 0.3279(4) 0.1779(3) 0.7982(2) 0.0322(6) Uani 1 1 d . . . . .
H13 H 0.3587 0.0951 0.8467 0.039 Uiso 1 1 calc R U . . .
C14 C 0.3668(4) 0.1798(2) 0.6682(2) 0.0289(5) Uani 1 1 d . . . . .
H14 H 0.4226 0.0972 0.6310 0.035 Uiso 1 1 calc R U . . .
C15 C 0.1964(5) 0.3005(3) 0.9984(2) 0.0411(7) Uani 1 1 d . . . . .
H15A H 0.2166 0.3804 1.0219 0.062 Uiso 1 1 calc R U . . .
H15B H 0.2827 0.2201 1.0345 0.062 Uiso 1 1 calc R U . . .
H15C H 0.0604 0.3017 1.0293 0.062 Uiso 1 1 calc R U . . .
O1 O 0.3054(2) 0.47308(16) 0.37735(14) 0.0257(4) Uani 1 1 d . . . . .
O2 O 0.4129(3) 0.41750(17) 0.18008(16) 0.0313(4) Uani 1 1 d . . . . .
Al1 Al 0.39524(10) 0.28781(7) 0.40486(6) 0.0205(2) Uani 1 1 d . . . . .
N1 N 0.3271(3) 0.29634(19) 0.59364(17) 0.0222(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 Al1 1.956(3) . ?
C2 Al1 1.952(2) . ?
C3 O2 1.230(3) . ?
C3 O1 1.312(3) . ?
C3 C4 1.486(3) . ?
C4 C9 1.395(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.381(3) . ?
C6 C7 1.388(4) . ?
C7 C8 1.387(4) . ?
C8 C9 1.384(4) . ?
C10 N1 1.344(3) . ?
C10 C11 1.374(3) . ?
C11 C12 1.380(4) . ?
C12 C13 1.392(4) . ?
C12 C15 1.505(3) . ?
C12 C9 3.519(3) 2_666 ?
C13 C14 1.380(3) . ?
C14 N1 1.341(3) . ?
O1 Al1 1.8210(17) . ?
O2 Al1 2.6164(18) . ?
Al1 N1 2.015(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C3 O1 120.9(2) . . ?
O2 C3 C4 122.7(2) . . ?
O1 C3 C4 116.46(19) . . ?
C9 C4 C5 119.7(2) . . ?
C9 C4 C3 119.2(2) . . ?
C5 C4 C3 121.1(2) . . ?
C6 C5 C4 120.2(2) . . ?
C5 C6 C7 119.9(2) . . ?
C8 C7 C6 120.2(2) . . ?
C9 C8 C7 120.2(2) . . ?
C8 C9 C4 119.8(2) . . ?
N1 C10 C11 122.7(2) . . ?
C10 C11 C12 120.5(2) . . ?
C11 C12 C13 116.6(2) . . ?
C11 C12 C15 122.0(3) . . ?
C13 C12 C15 121.4(2) . . ?
C11 C12 C9 98.41(16) . 2_666 ?
C13 C12 C9 92.71(16) . 2_666 ?
C15 C12 C9 79.48(15) . 2_666 ?
C14 C13 C12 120.2(2) . . ?
N1 C14 C13 122.4(2) . . ?
C3 O1 Al1 108.81(14) . . ?
C3 O2 Al1 73.94(13) . . ?
O1 Al1 C2 115.60(10) . . ?
O1 Al1 C1 116.15(10) . . ?
C2 Al1 C1 119.06(12) . . ?
O1 Al1 N1 92.31(8) . . ?
C2 Al1 N1 104.36(9) . . ?
C1 Al1 N1 103.49(10) . . ?
O1 Al1 O2 56.39(6) . . ?
C2 Al1 O2 92.58(9) . . ?
C1 Al1 O2 90.45(9) . . ?
N1 Al1 O2 148.64(7) . . ?
C14 N1 C10 117.5(2) . . ?
C14 N1 Al1 119.20(16) . . ?
C10 N1 Al1 123.30(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 C9 -0.5(3) . . . . ?
O1 C3 C4 C9 178.50(19) . . . . ?
O2 C3 C4 C5 179.5(2) . . . . ?
O1 C3 C4 C5 -1.5(3) . . . . ?
C9 C4 C5 C6 -0.2(3) . . . . ?
C3 C4 C5 C6 179.8(2) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
C5 C4 C9 C8 -0.2(3) . . . . ?
C3 C4 C9 C8 179.8(2) . . . . ?
N1 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C10 C11 C12 C15 -179.3(2) . . . . ?
C10 C11 C12 C9 97.9(2) . . . 2_666 ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C15 C12 C13 C14 179.3(2) . . . . ?
C9 C12 C13 C14 -101.4(2) 2_666 . . . ?
C12 C13 C14 N1 0.6(4) . . . . ?
O2 C3 O1 Al1 -1.2(3) . . . . ?
C4 C3 O1 Al1 179.76(15) . . . . ?
O1 C3 O2 Al1 0.83(18) . . . . ?
C4 C3 O2 Al1 179.8(2) . . . . ?
C3 O1 Al1 C2 -74.43(17) . . . . ?
C3 O1 Al1 C1 72.19(17) . . . . ?
C3 O1 Al1 N1 178.44(15) . . . . ?
C3 O1 Al1 O2 0.59(13) . . . . ?
C13 C14 N1 C10 -0.7(4) . . . . ?
C13 C14 N1 Al1 178.70(18) . . . . ?
C11 C10 N1 C14 0.7(4) . . . . ?
C11 C10 N1 Al1 -178.62(19) . . . . ?

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
C9 H9 O2 0.93 2.55 2.837(3) 98.1 .
C10 H10 O1 0.93 2.39 2.911(3) 115.0 .
C9 H9 O2 0.93 2.49 3.298(3) 145.3 2_665

_refine_diff_density_max         0.600
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.078

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_comp6
_database_code_depnum_ccdc_archive 'CCDC 1477246'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Ga N O2'
_chemical_formula_weight         314.02

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

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

_cell_length_a                   17.1050(17)
_cell_length_b                   9.7120(7)
_cell_length_c                   11.5220(10)
_cell_angle_alpha                90
_cell_angle_beta                 129.322(4)
_cell_angle_gamma                90
_cell_volume                     1480.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1476
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.855
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3009
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3004
_reflns_number_gt                2760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.979

_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       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+20.6782P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3004
_refine_ls_number_parameters     176
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4082(8) -0.0546(10) 0.6662(11) 0.029(2) Uani 1 1 d . . . . .
H1A H 0.3490 -0.0858 0.5667 0.044 Uiso 1 1 calc R U . . .
H1B H 0.4202 -0.1169 0.7429 0.044 Uiso 1 1 calc R U . . .
H1C H 0.4675 -0.0542 0.6711 0.044 Uiso 1 1 calc R U . . .
C2 C 0.4812(10) 0.2519(13) 0.8743(13) 0.028(3) Uani 1 1 d . . . . .
H2A H 0.5431 0.2594 0.8864 0.042 Uiso 1 1 calc R U . . .
H2B H 0.4972 0.2124 0.9654 0.042 Uiso 1 1 calc R U . . .
H2C H 0.4515 0.3435 0.8567 0.042 Uiso 1 1 calc R U . . .
C3 C 0.3430(7) 0.2720(10) 0.4703(10) 0.0233(19) Uani 1 1 d . . . . .
C4 C 0.2797(7) 0.3445(9) 0.3208(10) 0.0203(18) Uani 1 1 d . . . . .
C5 C 0.1755(7) 0.3636(9) 0.2368(11) 0.0183(18) Uani 1 1 d . . . . .
H5 H 0.1432 0.3329 0.2753 0.022 Uiso 1 1 calc R U . . .
C6 C 0.1195(8) 0.4267(11) 0.0983(12) 0.027(2) Uani 1 1 d . . . . .
H6 H 0.0488 0.4394 0.0415 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1666(8) 0.4713(9) 0.0426(10) 0.025(2) Uani 1 1 d . . . . .
H7 H 0.1276 0.5151 -0.0527 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2686(7) 0.4540(10) 0.1216(10) 0.025(2) Uani 1 1 d . . . . .
H8 H 0.2999 0.4854 0.0817 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3260(8) 0.3889(9) 0.2625(11) 0.026(2) Uani 1 1 d . . . . .
H9 H 0.3965 0.3753 0.3179 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2118(7) -0.0015(10) 0.6726(11) 0.0254(19) Uani 1 1 d . . . . .
H10 H 0.2259 -0.0776 0.6366 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1336(7) -0.0130(11) 0.6781(12) 0.030(2) Uani 1 1 d . . . . .
H11 H 0.0940 -0.0945 0.6444 0.036 Uiso 1 1 calc R U . . .
C12 C 0.1139(9) 0.0959(12) 0.7333(14) 0.029(2) Uani 1 1 d . . . . .
C13 C 0.1723(7) 0.2134(10) 0.7792(11) 0.026(2) Uani 1 1 d . . . . .
H13 H 0.1598 0.2899 0.8168 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2490(7) 0.2190(9) 0.7701(10) 0.0233(19) Uani 1 1 d . . . . .
H14 H 0.2890 0.3000 0.8029 0.028 Uiso 1 1 calc R U . . .
C15 C 0.0268(9) 0.0855(13) 0.7378(15) 0.040(3) Uani 1 1 d . . . . .
H15A H -0.0320 0.1349 0.6520 0.060 Uiso 1 1 calc R U . . .
H15B H 0.0473 0.1264 0.8312 0.060 Uiso 1 1 calc R U . . .
H15C H 0.0093 -0.0116 0.7332 0.060 Uiso 1 1 calc R U . . .
O1 O 0.2950(6) 0.2306(9) 0.5167(9) 0.0247(19) Uani 1 1 d . . . . .
O2 O 0.4334(5) 0.2509(7) 0.5398(8) 0.0295(16) Uani 1 1 d . . . . .
Ga1 Ga 0.38403(9) 0.13213(8) 0.70201(10) 0.0211(2) Uani 1 1 d . . . . .
N1 N 0.2691(6) 0.1129(8) 0.7162(8) 0.0235(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 Ga1 1.961(9) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 Ga1 1.968(12) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 O2 1.227(11) . ?
C3 O1 1.296(12) . ?
C3 C4 1.506(12) . ?
C4 C9 1.393(13) . ?
C4 C5 1.400(12) . ?
C5 C6 1.379(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.406(13) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 N1 1.350(12) . ?
C10 C11 1.385(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(15) . ?
C12 C15 1.526(16) . ?
C13 C14 1.380(14) . ?
C13 H13 0.9500 . ?
C14 N1 1.355(12) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1 Ga1 1.916(8) . ?
O2 Ga1 2.745(7) . ?
Ga1 N1 2.082(8) . ?

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
Ga1 C1 H1A 109.5 . . ?
Ga1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Ga1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Ga1 C2 H2A 109.5 . . ?
Ga1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Ga1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C3 O1 123.0(9) . . ?
O2 C3 C4 121.4(9) . . ?
O1 C3 C4 115.6(8) . . ?
C9 C4 C5 119.2(9) . . ?
C9 C4 C3 118.7(8) . . ?
C5 C4 C3 122.0(9) . . ?
C6 C5 C4 120.4(9) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.7(10) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 121.6(9) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.0(9) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C4 C9 C8 120.1(9) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N1 C10 C11 122.9(9) . . ?
N1 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C12 C11 C10 119.0(10) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 118.7(10) . . ?
C11 C12 C15 119.5(11) . . ?
C13 C12 C15 121.8(10) . . ?
C14 C13 C12 119.6(9) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N1 C14 C13 122.3(9) . . ?
N1 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 O1 Ga1 110.5(6) . . ?
C3 O2 Ga1 73.2(6) . . ?
O1 Ga1 C1 110.6(4) . . ?
O1 Ga1 C2 113.3(4) . . ?
C1 Ga1 C2 127.1(5) . . ?
O1 Ga1 N1 90.5(3) . . ?
C1 Ga1 N1 105.6(4) . . ?
C2 Ga1 N1 102.1(4) . . ?
O1 Ga1 O2 53.3(3) . . ?
C1 Ga1 O2 92.8(3) . . ?
C2 Ga1 O2 90.6(4) . . ?
N1 Ga1 O2 143.5(3) . . ?
C10 N1 C14 117.4(9) . . ?
C10 N1 Ga1 122.9(7) . . ?
C14 N1 Ga1 119.7(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 C9 -0.6(13) . . . . ?
O1 C3 C4 C9 -178.6(9) . . . . ?
O2 C3 C4 C5 176.9(9) . . . . ?
O1 C3 C4 C5 -1.0(13) . . . . ?
C9 C4 C5 C6 -0.5(14) . . . . ?
C3 C4 C5 C6 -178.0(9) . . . . ?
C4 C5 C6 C7 -0.1(15) . . . . ?
C5 C6 C7 C8 0.3(15) . . . . ?
C6 C7 C8 C9 0.1(14) . . . . ?
C5 C4 C9 C8 0.9(13) . . . . ?
C3 C4 C9 C8 178.5(8) . . . . ?
C7 C8 C9 C4 -0.7(14) . . . . ?
N1 C10 C11 C12 -1.4(15) . . . . ?
C10 C11 C12 C13 0.9(16) . . . . ?
C10 C11 C12 C15 179.1(10) . . . . ?
C11 C12 C13 C14 -0.5(16) . . . . ?
C15 C12 C13 C14 -178.7(10) . . . . ?
C12 C13 C14 N1 0.6(15) . . . . ?
O2 C3 O1 Ga1 -1.1(12) . . . . ?
C4 C3 O1 Ga1 176.8(6) . . . . ?
O1 C3 O2 Ga1 0.7(8) . . . . ?
C4 C3 O2 Ga1 -177.1(9) . . . . ?
C11 C10 N1 C14 1.4(14) . . . . ?
C11 C10 N1 Ga1 -178.2(7) . . . . ?
C13 C14 N1 C10 -1.0(13) . . . . ?
C13 C14 N1 Ga1 178.6(7) . . . . ?

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
C11 H11 O2 0.95 2.66 3.551(13) 157.0 3_445
C6 H6 O2 0.95 2.70 3.294(12) 121.5 4_454

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.114

_shelxl_version_number           2014/6

