# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1560692'
_audit_update_record             
;
2017-07-11 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 Al N2'
_chemical_formula_weight         392.46

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'
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                   9.0644(4)
_cell_length_b                   10.8851(5)
_cell_length_c                   12.5763(6)
_cell_angle_alpha                64.3590(10)
_cell_angle_beta                 74.9900(10)
_cell_angle_gamma                86.6500(10)
_cell_volume                     1078.45(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6206
_cell_measurement_theta_min      2.866
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10669
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.866
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             5169
_reflns_number_gt                4274
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+0.4414P] 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         5169
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Al1 Al 0.26630(5) 0.73067(4) 0.19061(4) 0.02317(12) Uani 1 1 d . . . . .
N1 N 0.45466(14) 0.72123(12) 0.24225(10) 0.0237(2) Uani 1 1 d . . . . .
N2 N 0.36006(14) 0.75885(13) 0.02726(11) 0.0252(3) Uani 1 1 d . . . . .
C11 C 0.51177(16) 0.78239(14) -0.02586(12) 0.0238(3) Uani 1 1 d . . . . .
C9 C 0.44512(17) 0.69340(15) 0.36335(13) 0.0255(3) Uani 1 1 d . . . . .
C12 C 0.57367(16) 0.82429(14) -0.15993(12) 0.0234(3) Uani 1 1 d . . . . .
C10 C 0.61798(16) 0.77737(16) 0.03731(13) 0.0276(3) Uani 1 1 d . . . . .
H10 H 0.7213 0.7982 -0.0102 0.033 Uiso 1 1 calc R U . . .
C4 C 0.57676(18) 0.68836(15) 0.40482(13) 0.0283(3) Uani 1 1 d . . . . .
C20 C 0.28123(17) 0.61075(15) -0.05140(13) 0.0284(3) Uani 1 1 d . . . . .
H20 H 0.3593 0.5519 -0.0255 0.034 Uiso 1 1 calc R U . . .
C3 C 0.72197(18) 0.71262(17) 0.31971(14) 0.0321(3) Uani 1 1 d . . . . .
H3 H 0.8128 0.7089 0.3451 0.039 Uiso 1 1 calc R U . . .
C1 C 0.59539(16) 0.74576(15) 0.16222(13) 0.0247(3) Uani 1 1 d . . . . .
C17 C 0.51662(17) 0.93465(15) -0.24475(13) 0.0279(3) Uani 1 1 d . . . . .
H17 H 0.4289 0.9759 -0.2174 0.033 Uiso 1 1 calc R U . . .
C14 C 0.76907(18) 0.81388(16) -0.32721(14) 0.0297(3) Uani 1 1 d . . . . .
H14 H 0.8549 0.7710 -0.3549 0.036 Uiso 1 1 calc R U . . .
C15 C 0.71543(18) 0.92625(16) -0.41210(13) 0.0287(3) Uani 1 1 d . . . . .
C19 C 0.26438(16) 0.72957(15) -0.03454(12) 0.0243(3) Uani 1 1 d . . . . .
C21 C 0.18479(18) 0.57803(17) -0.10569(14) 0.0318(3) Uani 1 1 d . . . . .
H21 H 0.1960 0.4962 -0.1160 0.038 Uiso 1 1 calc R U . . .
C13 C 0.69945(17) 0.76344(15) -0.20310(13) 0.0267(3) Uani 1 1 d . . . . .
H13 H 0.7381 0.6866 -0.1470 0.032 Uiso 1 1 calc R U . . .
C23 C 0.05469(18) 0.78262(18) -0.12886(14) 0.0328(3) Uani 1 1 d . . . . .
H23 H -0.0220 0.8422 -0.1565 0.039 Uiso 1 1 calc R U . . .
C2 C 0.73046(17) 0.74088(17) 0.20287(14) 0.0308(3) Uani 1 1 d . . . . .
H2 H 0.8280 0.7580 0.1462 0.037 Uiso 1 1 calc R U . . .
C16 C 0.58716(18) 0.98448(15) -0.36867(13) 0.0294(3) Uani 1 1 d . . . . .
H16 H 0.5471 1.0599 -0.4250 0.035 Uiso 1 1 calc R U . . .
C22 C 0.07202(18) 0.66404(18) -0.14505(14) 0.0328(3) Uani 1 1 d . . . . .
H22 H 0.0066 0.6418 -0.1831 0.039 Uiso 1 1 calc R U . . .
C26 C 0.1465(2) 0.55429(17) 0.27457(15) 0.0359(4) Uani 1 1 d . . . . .
H26A H 0.0654 0.5582 0.2348 0.054 Uiso 1 1 calc R U . . .
H26B H 0.1007 0.5351 0.3602 0.054 Uiso 1 1 calc R U . . .
H26C H 0.2138 0.4818 0.2704 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5612(2) 0.66274(17) 0.52730(14) 0.0356(4) Uani 1 1 d . . . . .
H5 H 0.6501 0.6591 0.5550 0.043 Uiso 1 1 calc R U . . .
C25 C 0.1537(2) 0.88804(17) 0.19711(17) 0.0361(4) Uani 1 1 d . . . . .
H25A H 0.2259 0.9601 0.1837 0.054 Uiso 1 1 calc R U . . .
H25B H 0.0808 0.8599 0.2774 0.054 Uiso 1 1 calc R U . . .
H25C H 0.0982 0.9226 0.1335 0.054 Uiso 1 1 calc R U . . .
C8 C 0.30114(19) 0.67099(17) 0.44713(14) 0.0321(3) Uani 1 1 d . . . . .
H8 H 0.2109 0.6725 0.4216 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2898(2) 0.64681(18) 0.56616(15) 0.0388(4) Uani 1 1 d . . . . .
H7 H 0.1915 0.6324 0.6215 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4197(2) 0.64315(18) 0.60657(15) 0.0408(4) Uani 1 1 d . . . . .
H6 H 0.4103 0.6272 0.6886 0.049 Uiso 1 1 calc R U . . .
C18 C 0.7949(2) 0.9838(2) -0.54690(15) 0.0427(4) Uani 1 1 d . . . . .
H18A H 0.7609 0.9298 -0.5825 0.064 Uiso 1 1 calc R U . . .
H18B H 0.9058 0.9801 -0.5579 0.064 Uiso 1 1 calc R U . . .
H18C H 0.7694 1.0788 -0.5877 0.064 Uiso 1 1 calc R U . . .
C24 C 0.14942(17) 0.81449(16) -0.07215(14) 0.0290(3) Uani 1 1 d . . . . .
H24 H 0.1355 0.8946 -0.0591 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Al1 N2 1.9020(13) . ?
Al1 N1 1.9605(13) . ?
Al1 C25 1.9638(16) . ?
Al1 C26 1.9685(16) . ?
N1 C1 1.3615(18) . ?
N1 C9 1.3979(18) . ?
N2 C11 1.3491(18) . ?
N2 C19 1.4330(18) . ?
C11 C10 1.383(2) . ?
C11 C12 1.4967(18) . ?
C9 C8 1.406(2) . ?
C9 C4 1.410(2) . ?
C12 C13 1.391(2) . ?
C12 C17 1.397(2) . ?
C10 C1 1.4150(19) . ?
C4 C5 1.411(2) . ?
C4 C3 1.419(2) . ?
C20 C21 1.383(2) . ?
C20 C19 1.392(2) . ?
C3 C2 1.346(2) . ?
C1 C2 1.434(2) . ?
C17 C16 1.387(2) . ?
C14 C13 1.387(2) . ?
C14 C15 1.393(2) . ?
C15 C16 1.392(2) . ?
C15 C18 1.512(2) . ?
C19 C24 1.389(2) . ?
C21 C22 1.384(2) . ?
C23 C22 1.385(2) . ?
C23 C24 1.390(2) . ?
C5 C6 1.367(3) . ?
C8 C7 1.380(2) . ?
C7 C6 1.391(3) . ?

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 Al1 N1 97.35(5) . . ?
N2 Al1 C25 111.92(7) . . ?
N1 Al1 C25 110.47(7) . . ?
N2 Al1 C26 107.70(6) . . ?
N1 Al1 C26 112.20(7) . . ?
C25 Al1 C26 115.68(8) . . ?
C1 N1 C9 118.71(12) . . ?
C1 N1 Al1 121.76(10) . . ?
C9 N1 Al1 119.48(10) . . ?
C11 N2 C19 118.23(11) . . ?
C11 N2 Al1 124.73(10) . . ?
C19 N2 Al1 116.14(9) . . ?
N2 C11 C10 122.75(13) . . ?
N2 C11 C12 121.12(12) . . ?
C10 C11 C12 116.03(12) . . ?
N1 C9 C8 119.87(14) . . ?
N1 C9 C4 121.88(13) . . ?
C8 C9 C4 118.24(13) . . ?
C13 C12 C17 118.40(13) . . ?
C13 C12 C11 120.64(13) . . ?
C17 C12 C11 120.64(13) . . ?
C11 C10 C1 129.50(13) . . ?
C9 C4 C5 119.79(15) . . ?
C9 C4 C3 118.14(13) . . ?
C5 C4 C3 122.05(15) . . ?
C21 C20 C19 120.26(14) . . ?
C2 C3 C4 119.73(14) . . ?
N1 C1 C10 123.36(13) . . ?
N1 C1 C2 120.13(13) . . ?
C10 C1 C2 116.51(13) . . ?
C16 C17 C12 120.48(14) . . ?
C13 C14 C15 121.25(14) . . ?
C16 C15 C14 117.84(13) . . ?
C16 C15 C18 121.09(15) . . ?
C14 C15 C18 121.07(15) . . ?
C24 C19 C20 119.39(14) . . ?
C24 C19 N2 120.83(13) . . ?
C20 C19 N2 119.69(13) . . ?
C22 C21 C20 120.24(15) . . ?
C14 C13 C12 120.66(14) . . ?
C22 C23 C24 120.07(15) . . ?
C3 C2 C1 121.38(14) . . ?
C17 C16 C15 121.32(14) . . ?
C21 C22 C23 119.86(14) . . ?
C6 C5 C4 120.83(16) . . ?
C7 C8 C9 120.54(16) . . ?
C8 C7 C6 121.11(16) . . ?
C5 C6 C7 119.47(15) . . ?
C19 C24 C23 120.15(14) . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1586865'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 F3 N2'
_chemical_formula_weight         390.39

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'

_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                   13.1627(5)
_cell_length_b                   7.2645(3)
_cell_length_c                   20.2474(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.6510(10)
_cell_angle_gamma                90
_cell_volume                     1854.88(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8625
_cell_measurement_theta_min      2.994
_cell_measurement_theta_max      28.302

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17402
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.994
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4596
_reflns_number_gt                3667
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.7125P] 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         4596
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
N2 N 0.70199(9) 0.84584(18) 0.15878(5) 0.0312(3) Uani 1 1 d . . . . .
H2 H 0.6581 0.8819 0.1818 0.037 Uiso 1 1 calc R U . . .
N1 N 0.50841(9) 0.71076(16) 0.14736(6) 0.0291(3) Uani 1 1 d . . . . .
C1 C 0.49161(11) 0.71682(19) 0.07932(7) 0.0287(3) Uani 1 1 d . . . . .
C22 C 0.99342(11) 0.6380(2) 0.27920(7) 0.0343(3) Uani 1 1 d . . . . .
C4 C 0.34267(11) 0.5419(2) 0.13081(8) 0.0336(3) Uani 1 1 d . . . . .
C12 C 0.73967(11) 0.95652(19) 0.05338(7) 0.0287(3) Uani 1 1 d . . . . .
C20 C 0.86867(11) 0.6829(2) 0.16691(7) 0.0302(3) Uani 1 1 d . . . . .
H20 H 0.8497 0.6644 0.1185 0.036 Uiso 1 1 calc R U . . .
C19 C 0.80084(11) 0.77717(19) 0.19680(6) 0.0274(3) Uani 1 1 d . . . . .
C21 C 0.96357(11) 0.6169(2) 0.20862(8) 0.0328(3) Uani 1 1 d . . . . .
C9 C 0.43558(11) 0.62517(19) 0.17348(7) 0.0298(3) Uani 1 1 d . . . . .
C23 C 0.92474(12) 0.7295(2) 0.30780(7) 0.0344(3) Uani 1 1 d . . . . .
C11 C 0.66790(11) 0.86129(19) 0.08701(6) 0.0280(3) Uani 1 1 d . . . . .
C8 C 0.45523(12) 0.6203(2) 0.24568(8) 0.0360(3) Uani 1 1 d . . . . .
H8 H 0.5172 0.6767 0.2746 0.043 Uiso 1 1 calc R U . . .
C10 C 0.56889(11) 0.8072(2) 0.05118(7) 0.0295(3) Uani 1 1 d . . . . .
H10 H 0.5478 0.8304 0.0030 0.035 Uiso 1 1 calc R U . . .
C24 C 0.83000(11) 0.8008(2) 0.26844(7) 0.0316(3) Uani 1 1 d . . . . .
H24 H 0.7848 0.8654 0.2896 0.038 Uiso 1 1 calc R U . . .
C3 C 0.32652(12) 0.5522(2) 0.05850(8) 0.0365(3) Uani 1 1 d . . . . .
H3 H 0.2650 0.4991 0.0278 0.044 Uiso 1 1 calc R U . . .
C7 C 0.38522(14) 0.5345(2) 0.27425(9) 0.0437(4) Uani 1 1 d . . . . .
H7 H 0.3992 0.5313 0.3230 0.052 Uiso 1 1 calc R U . . .
C13 C 0.73330(12) 0.9264(2) -0.01596(7) 0.0318(3) Uani 1 1 d . . . . .
H13 H 0.6834 0.8403 -0.0421 0.038 Uiso 1 1 calc R U . . .
C2 C 0.39909(11) 0.6379(2) 0.03316(7) 0.0340(3) Uani 1 1 d . . . . .
H2A H 0.3882 0.6453 -0.0152 0.041 Uiso 1 1 calc R U . . .
C16 C 0.87923(12) 1.1776(2) 0.05851(8) 0.0366(3) Uani 1 1 d . . . . .
H16 H 0.9292 1.2637 0.0845 0.044 Uiso 1 1 calc R U . . .
C17 C 0.81329(12) 1.0852(2) 0.08975(7) 0.0336(3) Uani 1 1 d . . . . .
H17 H 0.8183 1.1098 0.1367 0.040 Uiso 1 1 calc R U . . .
C14 C 0.79895(12) 1.0207(2) -0.04684(7) 0.0354(3) Uani 1 1 d . . . . .
H14 H 0.7928 0.9989 -0.0941 0.043 Uiso 1 1 calc R U . . .
C18 C 0.94532(15) 1.2472(2) -0.04442(10) 0.0471(4) Uani 1 1 d . . . . .
H18A H 0.9777 1.3527 -0.0160 0.071 Uiso 1 1 calc R U . . .
H18B H 0.9037 1.2906 -0.0900 0.071 Uiso 1 1 calc R U . . .
H18C H 1.0011 1.1637 -0.0495 0.071 Uiso 1 1 calc R U . . .
C6 C 0.29298(14) 0.4511(2) 0.23227(10) 0.0470(4) Uani 1 1 d . . . . .
H6 H 0.2450 0.3920 0.2526 0.056 Uiso 1 1 calc R U . . .
C5 C 0.27208(13) 0.4549(2) 0.16214(10) 0.0430(4) Uani 1 1 d . . . . .
H5 H 0.2094 0.3983 0.1341 0.052 Uiso 1 1 calc R U . . .
C15 C 0.87376(12) 1.1467(2) -0.01026(8) 0.0347(3) Uani 1 1 d . . . . .
F1 F 1.02991(8) 0.52600(15) 0.17990(5) 0.0476(3) Uani 1 1 d . . . . .
F2 F 1.08700(7) 0.57384(14) 0.31848(5) 0.0492(3) Uani 1 1 d . . . . .
F3 F 0.95362(9) 0.75179(15) 0.37678(4) 0.0516(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
N2 C11 1.3971(16) . ?
N2 C19 1.4002(17) . ?
N1 C1 1.3318(17) . ?
N1 C9 1.3697(18) . ?
C1 C2 1.4259(19) . ?
C1 C10 1.457(2) . ?
C22 F2 1.3438(16) . ?
C22 C23 1.376(2) . ?
C22 C21 1.378(2) . ?
C4 C5 1.416(2) . ?
C4 C9 1.415(2) . ?
C4 C3 1.420(2) . ?
C12 C17 1.395(2) . ?
C12 C13 1.3996(18) . ?
C12 C11 1.4844(19) . ?
C20 C21 1.3781(19) . ?
C20 C19 1.3937(19) . ?
C19 C24 1.4005(18) . ?
C21 F1 1.3517(17) . ?
C9 C8 1.410(2) . ?
C23 F3 1.3481(15) . ?
C23 C24 1.374(2) . ?
C11 C10 1.3555(19) . ?
C8 C7 1.371(2) . ?
C3 C2 1.358(2) . ?
C7 C6 1.404(3) . ?
C13 C14 1.384(2) . ?
C16 C17 1.385(2) . ?
C16 C15 1.392(2) . ?
C14 C15 1.392(2) . ?
C18 C15 1.508(2) . ?
C6 C5 1.367(3) . ?

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
C11 N2 C19 124.85(11) . . ?
C1 N1 C9 119.16(12) . . ?
N1 C1 C2 121.48(13) . . ?
N1 C1 C10 119.47(12) . . ?
C2 C1 C10 119.05(12) . . ?
F2 C22 C23 121.32(13) . . ?
F2 C22 C21 121.04(15) . . ?
C23 C22 C21 117.64(13) . . ?
C5 C4 C9 118.74(15) . . ?
C5 C4 C3 124.20(15) . . ?
C9 C4 C3 117.07(13) . . ?
C17 C12 C13 117.86(13) . . ?
C17 C12 C11 120.48(12) . . ?
C13 C12 C11 121.61(12) . . ?
C21 C20 C19 119.07(12) . . ?
C20 C19 C24 119.37(13) . . ?
C20 C19 N2 123.12(12) . . ?
C24 C19 N2 117.48(12) . . ?
F1 C21 C22 118.25(13) . . ?
F1 C21 C20 119.35(13) . . ?
C22 C21 C20 122.39(14) . . ?
N1 C9 C8 118.09(13) . . ?
N1 C9 C4 122.43(13) . . ?
C8 C9 C4 119.48(14) . . ?
F3 C23 C24 119.67(15) . . ?
F3 C23 C22 118.02(13) . . ?
C24 C23 C22 122.29(13) . . ?
C10 C11 N2 120.43(13) . . ?
C10 C11 C12 122.02(12) . . ?
N2 C11 C12 117.24(12) . . ?
C7 C8 C9 120.21(15) . . ?
C11 C10 C1 126.39(12) . . ?
C23 C24 C19 119.22(14) . . ?
C2 C3 C4 120.00(13) . . ?
C8 C7 C6 120.65(16) . . ?
C14 C13 C12 120.65(13) . . ?
C3 C2 C1 119.85(13) . . ?
C17 C16 C15 121.27(14) . . ?
C16 C17 C12 121.00(13) . . ?
C13 C14 C15 121.54(13) . . ?
C5 C6 C7 120.14(16) . . ?
C6 C5 C4 120.78(16) . . ?
C16 C15 C14 117.66(14) . . ?
C16 C15 C18 121.39(15) . . ?
C14 C15 C18 120.95(14) . . ?

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 1560695'
_audit_update_record             
;
2017-07-11 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H45 Al N2 O'
_chemical_formula_weight         548.72

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'
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                   9.6198(4)
_cell_length_b                   9.7898(4)
_cell_length_c                   19.6770(9)
_cell_angle_alpha                91.563(2)
_cell_angle_beta                 103.7970(10)
_cell_angle_gamma                116.9830(10)
_cell_volume                     1583.95(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.9415
_cell_measurement_theta_max      27.482

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22564
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7250
_reflns_number_gt                5654
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+1.2358P] 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         7250
_refine_ls_number_parameters     368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Al1 Al 0.89431(6) 0.44998(6) 0.16450(3) 0.02236(14) Uani 1 1 d . . . . .
C9 C 0.5804(2) 0.3492(2) 0.05783(10) 0.0272(4) Uani 1 1 d . . . . .
C1 C 0.6394(2) 0.5282(2) 0.15776(9) 0.0258(4) Uani 1 1 d . . . . .
C4 C 0.4213(2) 0.3301(2) 0.03236(10) 0.0293(4) Uani 1 1 d . . . . .
C3 C 0.3729(2) 0.4143(2) 0.07280(11) 0.0344(4) Uani 1 1 d . . . . .
H3 H 0.2667 0.4039 0.0571 0.041 Uiso 1 1 calc R U . . .
C2 C 0.4772(2) 0.5085(2) 0.13328(10) 0.0329(4) Uani 1 1 d . . . . .
H2 H 0.4432 0.5631 0.1604 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3169(2) 0.2297(2) -0.03106(11) 0.0380(5) Uani 1 1 d . . . . .
H5 H 0.2107 0.2186 -0.0484 0.046 Uiso 1 1 calc R U . . .
C8 C 0.6263(3) 0.2626(3) 0.01888(11) 0.0405(5) Uani 1 1 d . . . . .
H8 H 0.7320 0.2722 0.0352 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3649(3) 0.1479(3) -0.06811(12) 0.0450(5) Uani 1 1 d . . . . .
H6 H 0.2930 0.0805 -0.1110 0.054 Uiso 1 1 calc R U . . .
C7 C 0.5202(3) 0.1640(3) -0.04259(12) 0.0490(6) Uani 1 1 d . . . . .
H7 H 0.5535 0.1059 -0.0680 0.059 Uiso 1 1 calc R U . . .
N2 N 0.99842(16) 0.64406(16) 0.22531(7) 0.0215(3) Uani 1 1 d . . . . .
N1 N 0.68823(17) 0.44898(17) 0.12015(8) 0.0250(3) Uani 1 1 d . . . . .
C11 C 0.9090(2) 0.6986(2) 0.24916(9) 0.0237(3) Uani 1 1 d . . . . .
C12 C 0.9854(2) 0.8293(2) 0.30940(9) 0.0263(4) Uani 1 1 d . . . . .
C13 C 0.9413(2) 0.9468(2) 0.30752(11) 0.0341(4) Uani 1 1 d . . . . .
H13 H 0.8665 0.9470 0.2661 0.041 Uiso 1 1 calc R U . . .
C17 C 1.0939(2) 0.8324(2) 0.37096(10) 0.0359(4) Uani 1 1 d . . . . .
H17 H 1.1254 0.7533 0.3739 0.043 Uiso 1 1 calc R U . . .
C15 C 1.1136(3) 1.0668(2) 0.42592(11) 0.0395(5) Uani 1 1 d . . . . .
C14 C 1.0045(3) 1.0634(2) 0.36502(11) 0.0391(5) Uani 1 1 d . . . . .
H14 H 0.9723 1.1420 0.3624 0.047 Uiso 1 1 calc R U . . .
C16 C 1.1567(3) 0.9492(3) 0.42812(11) 0.0433(5) Uani 1 1 d . . . . .
H16 H 1.2308 0.9488 0.4697 0.052 Uiso 1 1 calc R U . . .
C18 C 1.1845(3) 1.1946(3) 0.48853(13) 0.0578(7) Uani 1 1 d . . . . .
H18A H 1.2881 1.2780 0.4852 0.087 Uiso 1 1 calc R U . . .
H18B H 1.2026 1.1528 0.5326 0.087 Uiso 1 1 calc R U . . .
H18C H 1.1087 1.2358 0.4884 0.087 Uiso 1 1 calc R U . . .
C10 C 0.7420(2) 0.6348(2) 0.22061(10) 0.0279(4) Uani 1 1 d . . . . .
H10 H 0.6887 0.6674 0.2471 0.033 Uiso 1 1 calc R U . . .
C20 C 1.2811(2) 0.6993(2) 0.28065(9) 0.0254(4) Uani 1 1 d . . . . .
C19 C 1.17146(19) 0.74159(19) 0.23809(9) 0.0215(3) Uani 1 1 d . . . . .
C24 C 1.2282(2) 0.8710(2) 0.20277(9) 0.0249(4) Uani 1 1 d . . . . .
C21 C 1.4468(2) 0.7899(2) 0.28797(11) 0.0334(4) Uani 1 1 d . . . . .
H21 H 1.5220 0.7623 0.3166 0.040 Uiso 1 1 calc R U . . .
C23 C 1.3954(2) 0.9578(2) 0.21262(11) 0.0331(4) Uani 1 1 d . . . . .
H23 H 1.4355 1.0463 0.1898 0.040 Uiso 1 1 calc R U . . .
C25 C 1.1167(2) 0.9165(2) 0.15167(10) 0.0312(4) Uani 1 1 d . . . . .
H25 H 1.0022 0.8439 0.1509 0.037 Uiso 1 1 calc R U . . .
C28 C 1.2276(2) 0.5579(2) 0.31808(10) 0.0317(4) Uani 1 1 d . . . . .
H28 H 1.1086 0.5144 0.3125 0.038 Uiso 1 1 calc R U . . .
C32 C 1.0280(2) 0.4653(3) 0.10078(11) 0.0371(5) Uani 1 1 d . . . . .
H32A H 0.9952 0.5077 0.0590 0.056 Uiso 1 1 calc R U . . .
H32B H 1.0128 0.3619 0.0859 0.056 Uiso 1 1 calc R U . . .
H32C H 1.1427 0.5339 0.1256 0.056 Uiso 1 1 calc R U . . .
C31 C 0.8218(2) 0.2649(2) 0.21117(12) 0.0373(5) Uani 1 1 d . . . . .
H31A H 0.9144 0.2471 0.2318 0.056 Uiso 1 1 calc R U . . .
H31B H 0.7379 0.1746 0.1763 0.056 Uiso 1 1 calc R U . . .
H31C H 0.7770 0.2808 0.2487 0.056 Uiso 1 1 calc R U . . .
C22 C 1.5039(2) 0.9178(2) 0.25487(11) 0.0373(5) Uani 1 1 d . . . . .
H22 H 1.6173 0.9785 0.2610 0.045 Uiso 1 1 calc R U . . .
C29 C 1.2543(3) 0.4328(2) 0.28374(12) 0.0406(5) Uani 1 1 d . . . . .
H29A H 1.1965 0.4065 0.2331 0.061 Uiso 1 1 calc R U . . .
H29B H 1.2127 0.3399 0.3063 0.061 Uiso 1 1 calc R U . . .
H29C H 1.3707 0.4719 0.2898 0.061 Uiso 1 1 calc R U . . .
C27 C 1.1316(3) 0.9000(3) 0.07634(12) 0.0470(6) Uani 1 1 d . . . . .
H27A H 1.2426 0.9715 0.0756 0.070 Uiso 1 1 calc R U . . .
H27B H 1.0547 0.9248 0.0438 0.070 Uiso 1 1 calc R U . . .
H27C H 1.1069 0.7932 0.0615 0.070 Uiso 1 1 calc R U . . .
C30 C 1.3158(3) 0.5968(3) 0.39733(12) 0.0510(6) Uani 1 1 d . . . . .
H30A H 1.4309 0.6275 0.4040 0.076 Uiso 1 1 calc R U . . .
H30B H 1.2670 0.5054 0.4200 0.076 Uiso 1 1 calc R U . . .
H30C H 1.3059 0.6824 0.4187 0.076 Uiso 1 1 calc R U . . .
C26 C 1.1508(3) 1.0819(3) 0.17504(15) 0.0544(6) Uani 1 1 d . . . . .
H26A H 1.1476 1.0930 0.2242 0.082 Uiso 1 1 calc R U . . .
H26B H 1.0682 1.1025 0.1444 0.082 Uiso 1 1 calc R U . . .
H26C H 1.2586 1.1561 0.1715 0.082 Uiso 1 1 calc R U . . .
C33 C 0.2294(6) 0.7288(6) 0.5624(3) 0.1116(16) Uani 1 1 d . . . . .
H33A H 0.1897 0.7097 0.5100 0.134 Uiso 1 1 calc R U . . .
H33B H 0.1787 0.7846 0.5806 0.134 Uiso 1 1 calc R U . . .
C35 C 0.3910(8) 0.8171(5) 0.5826(2) 0.1231(19) Uani 1 1 d . . . . .
H35A H 0.4213 0.9143 0.6129 0.148 Uiso 1 1 calc R U . . .
H35B H 0.4316 0.8446 0.5405 0.148 Uiso 1 1 calc R U . . .
C36 C 0.3314(6) 0.5771(6) 0.6172(3) 0.1196(16) Uani 1 1 d . . . . .
H36A H 0.3317 0.5444 0.6644 0.144 Uiso 1 1 calc R U . . .
H36B H 0.3368 0.4997 0.5860 0.144 Uiso 1 1 calc R U . . .
C34 C 0.1846(5) 0.5924(8) 0.5865(3) 0.136(2) Uani 1 1 d . . . . .
H34A H 0.1092 0.5061 0.5471 0.163 Uiso 1 1 calc R U . . .
H34B H 0.1281 0.5882 0.6229 0.163 Uiso 1 1 calc R U . . .
O1 O 0.4647(6) 0.7273(6) 0.6230(3) 0.223(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
Al1 N2 1.9033(15) . ?
Al1 N1 1.9618(15) . ?
Al1 C32 1.9629(19) . ?
Al1 C31 1.965(2) . ?
C9 N1 1.394(2) . ?
C9 C8 1.402(3) . ?
C9 C4 1.413(2) . ?
C1 N1 1.354(2) . ?
C1 C10 1.416(3) . ?
C1 C2 1.438(2) . ?
C4 C5 1.404(3) . ?
C4 C3 1.421(3) . ?
C3 C2 1.344(3) . ?
C5 C6 1.360(3) . ?
C8 C7 1.375(3) . ?
C6 C7 1.390(3) . ?
N2 C11 1.357(2) . ?
N2 C19 1.446(2) . ?
C11 C10 1.388(2) . ?
C11 C12 1.494(2) . ?
C12 C17 1.387(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.387(3) . ?
C17 C16 1.384(3) . ?
C15 C14 1.380(3) . ?
C15 C16 1.388(3) . ?
C15 C18 1.513(3) . ?
C20 C21 1.396(2) . ?
C20 C19 1.407(2) . ?
C20 C28 1.521(2) . ?
C19 C24 1.410(2) . ?
C24 C23 1.396(2) . ?
C24 C25 1.518(2) . ?
C21 C22 1.373(3) . ?
C23 C22 1.381(3) . ?
C25 C26 1.532(3) . ?
C25 C27 1.534(3) . ?
C28 C30 1.530(3) . ?
C28 C29 1.531(3) . ?
C33 C35 1.338(6) . ?
C33 C34 1.343(7) . ?
C35 O1 1.497(6) . ?
C36 O1 1.424(6) . ?
C36 C34 1.473(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
N2 Al1 N1 97.93(6) . . ?
N2 Al1 C32 107.32(8) . . ?
N1 Al1 C32 115.18(8) . . ?
N2 Al1 C31 115.77(8) . . ?
N1 Al1 C31 101.79(8) . . ?
C32 Al1 C31 117.33(9) . . ?
N1 C9 C8 120.69(16) . . ?
N1 C9 C4 121.43(16) . . ?
C8 C9 C4 117.88(17) . . ?
N1 C1 C10 123.33(15) . . ?
N1 C1 C2 119.87(16) . . ?
C10 C1 C2 116.78(16) . . ?
C5 C4 C9 119.69(18) . . ?
C5 C4 C3 122.29(17) . . ?
C9 C4 C3 118.02(17) . . ?
C2 C3 C4 119.99(17) . . ?
C3 C2 C1 121.17(18) . . ?
C6 C5 C4 121.24(18) . . ?
C7 C8 C9 120.84(19) . . ?
C5 C6 C7 119.3(2) . . ?
C8 C7 C6 121.0(2) . . ?
C11 N2 C19 120.16(14) . . ?
C11 N2 Al1 120.34(11) . . ?
C19 N2 Al1 118.99(10) . . ?
C1 N1 C9 119.51(15) . . ?
C1 N1 Al1 117.90(12) . . ?
C9 N1 Al1 121.63(12) . . ?
N2 C11 C10 122.49(16) . . ?
N2 C11 C12 121.36(15) . . ?
C10 C11 C12 116.13(15) . . ?
C17 C12 C13 117.68(18) . . ?
C17 C12 C11 121.27(16) . . ?
C13 C12 C11 120.90(16) . . ?
C14 C13 C12 121.17(19) . . ?
C16 C17 C12 120.87(19) . . ?
C14 C15 C16 117.96(19) . . ?
C14 C15 C18 121.3(2) . . ?
C16 C15 C18 120.8(2) . . ?
C15 C14 C13 120.95(19) . . ?
C17 C16 C15 121.4(2) . . ?
C11 C10 C1 129.42(16) . . ?
C21 C20 C19 118.50(16) . . ?
C21 C20 C28 118.35(16) . . ?
C19 C20 C28 123.13(15) . . ?
C20 C19 C24 120.45(15) . . ?
C20 C19 N2 119.86(15) . . ?
C24 C19 N2 119.47(14) . . ?
C23 C24 C19 118.39(16) . . ?
C23 C24 C25 118.06(16) . . ?
C19 C24 C25 123.48(15) . . ?
C22 C21 C20 121.61(17) . . ?
C22 C23 C24 121.45(18) . . ?
C24 C25 C26 111.82(17) . . ?
C24 C25 C27 110.79(16) . . ?
C26 C25 C27 110.15(18) . . ?
C20 C28 C30 112.75(17) . . ?
C20 C28 C29 110.40(16) . . ?
C30 C28 C29 109.33(17) . . ?
C21 C22 C23 119.59(17) . . ?
C35 C33 C34 111.4(4) . . ?
C33 C35 O1 108.3(4) . . ?
O1 C36 C34 105.4(4) . . ?
C33 C34 C36 108.6(4) . . ?
C36 O1 C35 104.8(4) . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1560693'
_audit_update_record             
;
2017-07-11 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 Al F N2'
_chemical_formula_weight         410.45

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'

_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                   9.2397(5)
_cell_length_b                   10.9749(5)
_cell_length_c                   12.4644(6)
_cell_angle_alpha                113.9750(10)
_cell_angle_beta                 102.9400(10)
_cell_angle_gamma                95.3410(10)
_cell_volume                     1101.26(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5041
_cell_measurement_theta_min      3.038
_cell_measurement_theta_max      28.2775

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10904
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.038
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             5303
_reflns_number_gt                4012
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.4551P] 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         5303
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Al1 Al 0.76746(5) 0.06965(5) 0.30204(5) 0.02790(14) Uani 1 1 d . . . . .
N2 N 0.86273(15) 0.20220(14) 0.46612(12) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.95379(15) 0.02903(14) 0.25622(12) 0.0282(3) Uani 1 1 d . . . . .
F1 F 0.51430(12) 0.55971(12) 0.68289(11) 0.0491(3) Uani 1 1 d . . . . .
C20 C 0.79596(19) 0.42560(18) 0.53534(15) 0.0307(4) Uani 1 1 d . . . . .
H20 H 0.8732 0.4546 0.5067 0.037 Uiso 1 1 calc R U . . .
C11 C 1.01324(18) 0.23299(17) 0.52289(14) 0.0270(3) Uani 1 1 d . . . . .
C12 C 1.07554(18) 0.32658(17) 0.65696(14) 0.0261(3) Uani 1 1 d . . . . .
C24 C 0.65684(19) 0.25076(19) 0.56310(16) 0.0330(4) Uani 1 1 d . . . . .
H24 H 0.6373 0.1594 0.5524 0.040 Uiso 1 1 calc R U . . .
C9 C 0.9424(2) -0.06112(17) 0.13538(15) 0.0312(4) Uani 1 1 d . . . . .
C10 C 1.11711(18) 0.17648(18) 0.46343(15) 0.0309(4) Uani 1 1 d . . . . .
H10 H 1.2193 0.2024 0.5134 0.037 Uiso 1 1 calc R U . . .
C19 C 0.77243(18) 0.29394(17) 0.52382(14) 0.0272(3) Uani 1 1 d . . . . .
C1 C 1.09329(19) 0.08538(17) 0.33862(15) 0.0290(3) Uani 1 1 d . . . . .
C23 C 0.56954(19) 0.3406(2) 0.61799(16) 0.0357(4) Uani 1 1 d . . . . .
H23 H 0.4923 0.3126 0.6472 0.043 Uiso 1 1 calc R U . . .
C14 C 1.2712(2) 0.50735(18) 0.82431(16) 0.0346(4) Uani 1 1 d . . . . .
H14 H 1.3581 0.5775 0.8514 0.042 Uiso 1 1 calc R U . . .
C21 C 0.7084(2) 0.51586(19) 0.58817(16) 0.0340(4) Uani 1 1 d . . . . .
H21 H 0.7245 0.6062 0.5961 0.041 Uiso 1 1 calc R U . . .
C18 C 1.01651(19) 0.30500(18) 0.74290(15) 0.0308(4) Uani 1 1 d . . . . .
H18 H 0.9283 0.2363 0.7159 0.037 Uiso 1 1 calc R U . . .
C4 C 1.0726(2) -0.09335(18) 0.09715(16) 0.0348(4) Uani 1 1 d . . . . .
C15 C 1.2148(2) 0.48440(18) 0.91043(15) 0.0335(4) Uani 1 1 d . . . . .
C3 C 1.2172(2) -0.0313(2) 0.18505(17) 0.0387(4) Uani 1 1 d . . . . .
H3 H 1.3068 -0.0499 0.1617 0.046 Uiso 1 1 calc R U . . .
C17 C 1.0854(2) 0.38282(19) 0.86741(16) 0.0340(4) Uani 1 1 d . . . . .
H17 H 1.0434 0.3665 0.9245 0.041 Uiso 1 1 calc R U . . .
C26 C 0.6474(2) -0.0919(2) 0.29587(19) 0.0430(5) Uani 1 1 d . . . . .
H26A H 0.7136 -0.1545 0.3034 0.064 Uiso 1 1 calc R U . . .
H26B H 0.5673 -0.1379 0.2176 0.064 Uiso 1 1 calc R U . . .
H26C H 0.6013 -0.0638 0.3635 0.064 Uiso 1 1 calc R U . . .
C25 C 0.6565(2) 0.1594(2) 0.21174(18) 0.0427(5) Uani 1 1 d . . . . .
H25A H 0.5773 0.1953 0.2487 0.064 Uiso 1 1 calc R U . . .
H25B H 0.6098 0.0933 0.1260 0.064 Uiso 1 1 calc R U . . .
H25C H 0.7271 0.2345 0.2155 0.064 Uiso 1 1 calc R U . . .
C2 C 1.2271(2) 0.0538(2) 0.30135(16) 0.0363(4) Uani 1 1 d . . . . .
H2 H 1.3241 0.0938 0.3600 0.044 Uiso 1 1 calc R U . . .
C8 C 0.7994(2) -0.12358(19) 0.04953(17) 0.0400(4) Uani 1 1 d . . . . .
H8 H 0.7106 -0.1030 0.0734 0.048 Uiso 1 1 calc R U . . .
C13 C 1.20333(19) 0.42997(18) 0.69976(15) 0.0307(4) Uani 1 1 d . . . . .
H13 H 1.2443 0.4476 0.6428 0.037 Uiso 1 1 calc R U . . .
C5 C 1.0554(3) -0.1863(2) -0.02495(17) 0.0449(5) Uani 1 1 d . . . . .
H5 H 1.1429 -0.2072 -0.0509 0.054 Uiso 1 1 calc R U . . .
C16 C 1.2928(3) 0.5652(2) 1.04639(17) 0.0500(5) Uani 1 1 d . . . . .
H16A H 1.2726 0.5104 1.0889 0.075 Uiso 1 1 calc R U . . .
H16B H 1.2538 0.6489 1.0783 0.075 Uiso 1 1 calc R U . . .
H16C H 1.4024 0.5888 1.0600 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7865(3) -0.2145(2) -0.06910(18) 0.0496(5) Uani 1 1 d . . . . .
H7 H 0.6887 -0.2559 -0.1263 0.059 Uiso 1 1 calc R U . . .
C6 C 0.9150(3) -0.2465(2) -0.10633(18) 0.0519(6) Uani 1 1 d . . . . .
H6 H 0.9048 -0.3101 -0.1882 0.062 Uiso 1 1 calc R U . . .
C22 C 0.59784(18) 0.47046(19) 0.62873(15) 0.0335(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
Al1 N2 1.9003(14) . ?
Al1 C25 1.9648(19) . ?
Al1 C26 1.966(2) . ?
Al1 N1 1.9661(15) . ?
N2 C11 1.351(2) . ?
N2 C19 1.437(2) . ?
N1 C1 1.357(2) . ?
N1 C9 1.399(2) . ?
F1 C22 1.3593(19) . ?
C20 C19 1.384(2) . ?
C20 C21 1.388(2) . ?
C11 C10 1.382(2) . ?
C11 C12 1.498(2) . ?
C12 C13 1.394(2) . ?
C12 C18 1.395(2) . ?
C24 C19 1.391(2) . ?
C24 C23 1.392(2) . ?
C9 C8 1.401(2) . ?
C9 C4 1.413(3) . ?
C10 C1 1.418(2) . ?
C1 C2 1.439(2) . ?
C23 C22 1.370(3) . ?
C14 C13 1.385(2) . ?
C14 C15 1.390(3) . ?
C21 C22 1.374(3) . ?
C18 C17 1.386(2) . ?
C4 C5 1.408(2) . ?
C4 C3 1.421(3) . ?
C15 C17 1.393(3) . ?
C15 C16 1.513(2) . ?
C3 C2 1.344(2) . ?
C8 C7 1.377(3) . ?
C5 C6 1.362(3) . ?
C7 C6 1.393(3) . ?

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 Al1 C25 108.34(8) . . ?
N2 Al1 C26 111.60(8) . . ?
C25 Al1 C26 115.57(9) . . ?
N2 Al1 N1 97.15(6) . . ?
C25 Al1 N1 111.79(8) . . ?
C26 Al1 N1 110.85(8) . . ?
C11 N2 C19 117.46(13) . . ?
C11 N2 Al1 124.96(11) . . ?
C19 N2 Al1 116.31(10) . . ?
C1 N1 C9 118.96(14) . . ?
C1 N1 Al1 121.89(11) . . ?
C9 N1 Al1 119.14(11) . . ?
C19 C20 C21 120.97(16) . . ?
N2 C11 C10 122.71(15) . . ?
N2 C11 C12 121.00(14) . . ?
C10 C11 C12 116.23(14) . . ?
C13 C12 C18 118.19(15) . . ?
C13 C12 C11 120.49(15) . . ?
C18 C12 C11 121.05(15) . . ?
C19 C24 C23 120.39(17) . . ?
N1 C9 C8 120.00(16) . . ?
N1 C9 C4 121.57(16) . . ?
C8 C9 C4 118.42(16) . . ?
C11 C10 C1 129.37(15) . . ?
C20 C19 C24 119.34(16) . . ?
C20 C19 N2 119.52(15) . . ?
C24 C19 N2 121.07(16) . . ?
N1 C1 C10 123.42(15) . . ?
N1 C1 C2 120.24(15) . . ?
C10 C1 C2 116.33(15) . . ?
C22 C23 C24 118.27(16) . . ?
C13 C14 C15 121.29(17) . . ?
C22 C21 C20 117.97(17) . . ?
C17 C18 C12 120.64(16) . . ?
C5 C4 C9 119.53(18) . . ?
C5 C4 C3 122.27(18) . . ?
C9 C4 C3 118.19(15) . . ?
C14 C15 C17 117.79(15) . . ?
C14 C15 C16 121.25(17) . . ?
C17 C15 C16 120.96(17) . . ?
C2 C3 C4 119.87(16) . . ?
C18 C17 C15 121.29(16) . . ?
C3 C2 C1 121.15(17) . . ?
C7 C8 C9 120.6(2) . . ?
C14 C13 C12 120.78(16) . . ?
C6 C5 C4 120.9(2) . . ?
C8 C7 C6 120.8(2) . . ?
C5 C6 C7 119.73(18) . . ?
F1 C22 C23 118.99(16) . . ?
F1 C22 C21 117.98(17) . . ?
C23 C22 C21 123.03(16) . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1560694'
_audit_update_record             
;
2017-07-11 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Al F3 N2'
_chemical_formula_weight         446.43

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'

_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                   11.2604(8)
_cell_length_b                   17.9382(13)
_cell_length_c                   12.3473(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.366(2)
_cell_angle_gamma                90
_cell_volume                     2306.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9463
_cell_measurement_theta_min      2.888
_cell_measurement_theta_max      28.243

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22190
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         28.265
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5676
_reflns_number_gt                4341
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0646P)²+0.7364P] 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         5676
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.078
_refine_ls_shift/su_mean         0.001

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
Al1 Al 0.94169(4) 0.24168(2) -0.00544(4) 0.02642(12) Uani 1 1 d . . . . .
C9 C 0.85957(14) 0.08894(8) -0.08318(13) 0.0278(3) Uani 1 1 d . . . . .
C11 C 0.94256(14) 0.23317(9) 0.22616(13) 0.0295(3) Uani 1 1 d . . . . .
C12 C 0.96742(15) 0.26854(9) 0.34222(14) 0.0321(3) Uani 1 1 d . . . . .
C4 C 0.82860(15) 0.01350(8) -0.07233(15) 0.0322(3) Uani 1 1 d . . . . .
C2 C 0.88707(16) 0.03397(9) 0.13298(15) 0.0350(4) Uani 1 1 d . . . . .
H2 H 0.9008 0.0155 0.2089 0.042 Uiso 1 1 calc R U . . .
C1 C 0.91190(14) 0.11087(8) 0.11881(13) 0.0289(3) Uani 1 1 d . . . . .
C13 C 0.91856(17) 0.23892(10) 0.42080(15) 0.0398(4) Uani 1 1 d . . . . .
H13 H 0.8656 0.1958 0.3999 0.048 Uiso 1 1 calc R U . . .
C24 C 0.91984(18) 0.41211(9) 0.10384(15) 0.0376(4) Uani 1 1 d . . . . .
H24 H 1.0008 0.4095 0.0967 0.045 Uiso 1 1 calc R U . . .
C3 C 0.84449(16) -0.01286(9) 0.04039(15) 0.0369(4) Uani 1 1 d . . . . .
H3 H 0.8253 -0.0633 0.0509 0.044 Uiso 1 1 calc R U . . .
C10 C 0.94694(15) 0.15692(9) 0.22039(13) 0.0324(3) Uani 1 1 d . . . . .
H10 H 0.9772 0.1315 0.2934 0.039 Uiso 1 1 calc R U . . .
C19 C 0.86300(16) 0.34814(8) 0.12607(14) 0.0321(3) Uani 1 1 d . . . . .
C8 C 0.85342(17) 0.11432(9) -0.19299(14) 0.0360(4) Uani 1 1 d . . . . .
H8 H 0.8766 0.1643 -0.2013 0.043 Uiso 1 1 calc R U . . .
C20 C 0.74367(17) 0.35288(10) 0.13543(16) 0.0408(4) Uani 1 1 d . . . . .
H20 H 0.7037 0.3096 0.1502 0.049 Uiso 1 1 calc R U . . .
C5 C 0.78794(18) -0.03277(9) -0.17203(16) 0.0427(4) Uani 1 1 d . . . . .
H5 H 0.7654 -0.0831 -0.1654 0.051 Uiso 1 1 calc R U . . .
C17 C 1.04565(16) 0.33151(10) 0.37595(15) 0.0386(4) Uani 1 1 d . . . . .
H17 H 1.0805 0.3525 0.3238 0.046 Uiso 1 1 calc R U . . .
C22 C 0.7403(2) 0.48488(11) 0.10149(16) 0.0519(5) Uani 1 1 d . . . . .
C16 C 1.07280(17) 0.36359(12) 0.48447(17) 0.0466(5) Uani 1 1 d . . . . .
H16 H 1.1260 0.4065 0.5059 0.056 Uiso 1 1 calc R U . . .
C14 C 0.94651(18) 0.27171(13) 0.52966(16) 0.0476(5) Uani 1 1 d . . . . .
H14 H 0.9119 0.2508 0.5821 0.057 Uiso 1 1 calc R U . . .
C15 C 1.02362(17) 0.33412(13) 0.56301(16) 0.0484(5) Uani 1 1 d . . . . .
C6 C 0.7805(2) -0.00632(10) -0.27786(17) 0.0486(5) Uani 1 1 d . . . . .
H6 H 0.7525 -0.0381 -0.3445 0.058 Uiso 1 1 calc R U . . .
C7 C 0.81427(19) 0.06768(10) -0.28839(16) 0.0441(4) Uani 1 1 d . . . . .
H7 H 0.8100 0.0858 -0.3621 0.053 Uiso 1 1 calc R U . . .
C23 C 0.8573(2) 0.47914(10) 0.09233(16) 0.0466(5) Uani 1 1 d . . . . .
C21 C 0.68488(19) 0.42130(12) 0.12291(17) 0.0503(5) Uani 1 1 d . . . . .
C18 C 1.0552(3) 0.37009(18) 0.6819(2) 0.0764(8) Uani 1 1 d . . . . .
H18A H 1.1481 0.3781 0.7193 0.115 Uiso 1 1 calc R U . . .
H18B H 1.0272 0.3373 0.7312 0.115 Uiso 1 1 calc R U . . .
H18C H 1.0107 0.4181 0.6721 0.115 Uiso 1 1 calc R U . . .
N1 N 0.89873(12) 0.13716(7) 0.01212(11) 0.0266(3) Uani 1 1 d . . . . .
N2 N 0.92162(12) 0.27747(7) 0.13085(11) 0.0292(3) Uani 1 1 d . . . . .
F3 F 0.91132(16) 0.54204(6) 0.07137(11) 0.0683(4) Uani 1 1 d . . . . .
F2 F 0.68051(15) 0.55119(7) 0.08906(12) 0.0782(5) Uani 1 1 d . . . . .
F1 F 0.56875(12) 0.42673(9) 0.13010(13) 0.0790(5) Uani 1 1 d . . . . .
C25 C 1.12029(18) 0.24388(11) 0.00742(18) 0.0437(4) Uani 1 1 d . . . . .
H25A H 1.1484 0.2958 0.0095 0.066 Uiso 1 1 calc R U . . .
H25B H 1.1271 0.2185 -0.0603 0.066 Uiso 1 1 calc R U . . .
H25C H 1.1748 0.2185 0.0795 0.066 Uiso 1 1 calc R U . . .
C26 C 0.8163(2) 0.29392(10) -0.13996(16) 0.0466(4) Uani 1 1 d . . . . .
H26A H 0.7306 0.2890 -0.1379 0.070 Uiso 1 1 calc R U . . .
H26B H 0.8165 0.2721 -0.2127 0.070 Uiso 1 1 calc R U . . .
H26C H 0.8393 0.3468 -0.1366 0.070 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Al1 N2 1.8933(13) . ?
Al1 C25 1.9566(18) . ?
Al1 C26 1.9609(18) . ?
Al1 N1 1.9687(13) . ?
C9 N1 1.3902(19) . ?
C9 C8 1.407(2) . ?
C9 C4 1.416(2) . ?
C11 N2 1.364(2) . ?
C11 C10 1.371(2) . ?
C11 C12 1.493(2) . ?
C12 C13 1.390(2) . ?
C12 C17 1.395(2) . ?
C4 C5 1.409(2) . ?
C4 C3 1.415(2) . ?
C2 C3 1.351(2) . ?
C2 C1 1.431(2) . ?
C1 N1 1.3532(19) . ?
C1 C10 1.426(2) . ?
C13 C14 1.389(3) . ?
C24 C23 1.373(2) . ?
C24 C19 1.391(2) . ?
C19 C20 1.394(2) . ?
C19 N2 1.4202(19) . ?
C8 C7 1.373(2) . ?
C20 C21 1.375(3) . ?
C5 C6 1.363(3) . ?
C17 C16 1.381(2) . ?
C22 F2 1.346(2) . ?
C22 C23 1.369(3) . ?
C22 C21 1.373(3) . ?
C16 C15 1.391(3) . ?
C14 C15 1.380(3) . ?
C15 C18 1.517(3) . ?
C6 C7 1.400(3) . ?
C23 F3 1.353(2) . ?
C21 F1 1.347(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
N2 Al1 C25 112.81(7) . . ?
N2 Al1 C26 107.45(7) . . ?
C25 Al1 C26 116.45(9) . . ?
N2 Al1 N1 96.18(6) . . ?
C25 Al1 N1 107.36(7) . . ?
C26 Al1 N1 114.87(7) . . ?
N1 C9 C8 119.85(13) . . ?
N1 C9 C4 121.65(14) . . ?
C8 C9 C4 118.47(14) . . ?
N2 C11 C10 122.27(14) . . ?
N2 C11 C12 119.22(14) . . ?
C10 C11 C12 118.45(14) . . ?
C13 C12 C17 118.28(15) . . ?
C13 C12 C11 121.87(15) . . ?
C17 C12 C11 119.81(14) . . ?
C5 C4 C3 122.68(15) . . ?
C5 C4 C9 119.34(15) . . ?
C3 C4 C9 117.94(14) . . ?
C3 C2 C1 121.24(15) . . ?
N1 C1 C10 123.05(14) . . ?
N1 C1 C2 120.05(14) . . ?
C10 C1 C2 116.88(14) . . ?
C12 C13 C14 120.62(17) . . ?
C23 C24 C19 119.10(17) . . ?
C2 C3 C4 119.72(15) . . ?
C11 C10 C1 128.31(14) . . ?
C24 C19 C20 119.76(15) . . ?
C24 C19 N2 120.20(15) . . ?
C20 C19 N2 119.89(15) . . ?
C7 C8 C9 120.76(16) . . ?
C21 C20 C19 118.88(18) . . ?
C6 C5 C4 120.92(16) . . ?
C16 C17 C12 120.56(17) . . ?
F2 C22 C23 120.8(2) . . ?
F2 C22 C21 120.8(2) . . ?
C23 C22 C21 118.40(16) . . ?
C17 C16 C15 121.20(18) . . ?
C15 C14 C13 121.15(18) . . ?
C14 C15 C16 118.19(16) . . ?
C14 C15 C18 121.5(2) . . ?
C16 C15 C18 120.3(2) . . ?
C5 C6 C7 119.95(16) . . ?
C8 C7 C6 120.51(17) . . ?
F3 C23 C22 118.04(17) . . ?
F3 C23 C24 120.00(19) . . ?
C22 C23 C24 121.95(18) . . ?
F1 C21 C20 119.7(2) . . ?
F1 C21 C22 118.43(18) . . ?
C20 C21 C22 121.90(19) . . ?
C1 N1 C9 119.28(13) . . ?
C1 N1 Al1 119.91(10) . . ?
C9 N1 Al1 120.77(10) . . ?
C11 N2 C19 118.74(13) . . ?
C11 N2 Al1 121.96(10) . . ?
C19 N2 Al1 118.46(10) . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.047

