# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_p21c
_database_code_depnum_ccdc_archive 'CCDC 1041072'
_audit_update_record             
;
2014-12-27 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 Cl8 N2 Nb2 O2'
_chemical_formula_weight         661.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.7734(9)
_cell_length_b                   13.4440(18)
_cell_length_c                   11.9844(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.854(2)
_cell_angle_gamma                90.00
_cell_volume                     1059.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4334
_cell_measurement_theta_min      2.315
_cell_measurement_theta_max      28.544

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.074
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    2.097
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6330
_exptl_absorpt_correction_T_max  0.7438
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.0974 (selected reflections only, before parameter refinement)
 R(int) =  0.0403 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8389
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2315
_reflns_number_gt                2056
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0271P)²+6.6567P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2315
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5423(8) 0.0329(4) 0.5405(4) 0.0288(10) Uani 1 1 d . . .
C2 C 0.4768(7) 0.1368(3) 0.5453(4) 0.0230(9) Uani 1 1 d . . .
C3 C 0.3270(7) 0.2006(4) 0.4656(4) 0.0258(10) Uani 1 1 d . . .
H3A H 0.1871 0.1745 0.4548 0.031 Uiso 1 1 calc R . .
H3B H 0.3603 0.2062 0.3898 0.031 Uiso 1 1 calc R . .
C4 C 0.3515(7) 0.3006(3) 0.5284(4) 0.0251(10) Uani 1 1 d . . .
H4A H 0.3928 0.3530 0.4805 0.030 Uiso 1 1 calc R . .
H4B H 0.2222 0.3208 0.5466 0.030 Uiso 1 1 calc R . .
C5 C 0.5167(7) 0.2846(3) 0.6387(4) 0.0275(10) Uani 1 1 d . . .
H5A H 0.6343 0.3288 0.6404 0.033 Uiso 1 1 calc R . .
H5B H 0.4633 0.2986 0.7071 0.033 Uiso 1 1 calc R . .
Cl1 Cl 0.81094(18) 0.21858(9) 0.88966(10) 0.0296(3) Uani 1 1 d . . .
Cl2 Cl 1.02279(16) -0.03017(8) 0.85688(9) 0.0235(2) Uani 1 1 d . . .
Cl3 Cl 0.52171(18) 0.02936(9) 0.82882(13) 0.0341(3) Uani 1 1 d . . .
Cl4 Cl 1.04449(18) 0.16787(10) 0.68587(11) 0.0309(3) Uani 1 1 d . . .
N1 N 0.5770(5) 0.1791(3) 0.6368(3) 0.0223(8) Uani 1 1 d . . .
Nb1 Nb 0.79980(6) 0.08657(3) 0.76208(4) 0.01969(13) Uani 1 1 d . . .
O1 O 0.7014(5) 0.0059(3) 0.6274(3) 0.0262(7) 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 C1 1.337(10) 3_656 ?
C1 O1 1.357(6) . ?
C1 C2 1.471(7) . ?
C2 N1 1.276(6) . ?
C2 C3 1.488(7) . ?
C3 C4 1.530(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.528(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.477(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
Cl1 Nb1 2.3319(13) . ?
Cl2 Nb1 2.2833(11) . ?
Cl3 Nb1 2.3454(12) . ?
Cl4 Nb1 2.3453(12) . ?
N1 Nb1 2.235(4) . ?
Nb1 O1 1.927(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
C1 C1 O1 120.2(6) 3_656 . ?
C1 C1 C2 125.2(6) 3_656 . ?
O1 C1 C2 114.6(4) . . ?
N1 C2 C1 110.7(4) . . ?
N1 C2 C3 115.8(4) . . ?
C1 C2 C3 133.5(4) . . ?
C2 C3 C4 102.3(4) . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
C4 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C5 C4 C3 105.8(4) . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
N1 C5 C4 105.7(4) . . ?
N1 C5 H5A 110.6 . . ?
C4 C5 H5A 110.6 . . ?
N1 C5 H5B 110.6 . . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
C2 N1 C5 110.4(4) . . ?
C2 N1 Nb1 117.6(3) . . ?
C5 N1 Nb1 132.0(3) . . ?
O1 Nb1 N1 73.03(14) . . ?
O1 Nb1 Cl2 94.86(10) . . ?
N1 Nb1 Cl2 167.62(11) . . ?
O1 Nb1 Cl1 158.18(10) . . ?
N1 Nb1 Cl1 85.84(11) . . ?
Cl2 Nb1 Cl1 106.45(5) . . ?
O1 Nb1 Cl4 94.08(11) . . ?
N1 Nb1 Cl4 84.57(10) . . ?
Cl2 Nb1 Cl4 93.96(4) . . ?
Cl1 Nb1 Cl4 89.18(5) . . ?
O1 Nb1 Cl3 87.48(11) . . ?
N1 Nb1 Cl3 86.76(10) . . ?
Cl2 Nb1 Cl3 95.42(4) . . ?
Cl1 Nb1 Cl3 85.90(5) . . ?
Cl4 Nb1 Cl3 170.32(5) . . ?
C1 O1 Nb1 122.9(3) . . ?

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
C1 C1 C2 N1 175.4(6) 3_656 . . . ?
O1 C1 C2 N1 -4.4(6) . . . . ?
C1 C1 C2 C3 -6.9(10) 3_656 . . . ?
O1 C1 C2 C3 173.3(4) . . . . ?
N1 C2 C3 C4 -0.1(5) . . . . ?
C1 C2 C3 C4 -177.7(5) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 N1 -1.0(5) . . . . ?
C1 C2 N1 C5 177.6(4) . . . . ?
C3 C2 N1 C5 -0.6(5) . . . . ?
C1 C2 N1 Nb1 -3.1(5) . . . . ?
C3 C2 N1 Nb1 178.7(3) . . . . ?
C4 C5 N1 C2 1.0(5) . . . . ?
C4 C5 N1 Nb1 -178.2(3) . . . . ?
C2 N1 Nb1 O1 7.0(3) . . . . ?
C5 N1 Nb1 O1 -173.9(4) . . . . ?
C2 N1 Nb1 Cl2 19.2(7) . . . . ?
C5 N1 Nb1 Cl2 -161.7(4) . . . . ?
C2 N1 Nb1 Cl1 -167.5(3) . . . . ?
C5 N1 Nb1 Cl1 11.6(4) . . . . ?
C2 N1 Nb1 Cl4 102.9(3) . . . . ?
C5 N1 Nb1 Cl4 -78.0(4) . . . . ?
C2 N1 Nb1 Cl3 -81.4(3) . . . . ?
C5 N1 Nb1 Cl3 97.7(4) . . . . ?
C1 C1 O1 Nb1 -168.1(5) 3_656 . . . ?
C2 C1 O1 Nb1 11.7(6) . . . . ?
N1 Nb1 O1 C1 -9.9(3) . . . . ?
Cl2 Nb1 O1 C1 172.7(3) . . . . ?
Cl1 Nb1 O1 C1 5.1(6) . . . . ?
Cl4 Nb1 O1 C1 -92.9(3) . . . . ?
Cl3 Nb1 O1 C1 77.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.092
_refine_diff_density_min         -1.392
_refine_diff_density_rms         0.132
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1518994'
_audit_update_record             
;
2016-11-24 deposited with the CCDC.
2017-01-30 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            'C11 H15 Cl7 N Nb O'
_chemical_formula_weight         518.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.9864(4)
_cell_length_b                   12.7821(7)
_cell_length_c                   20.9934(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1874.73(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.511
_cell_measurement_theta_max      33.820

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.635
_shelx_estimated_absorpt_T_min   0.803
_shelx_estimated_absorpt_T_max   0.880
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CMOS detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23104
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.865
_diffrn_reflns_theta_max         25.043
_diffrn_reflns_theta_full        25.043
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3338
_reflns_number_gt                3197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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)+(0.0247P)²+1.3304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0570
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_restrained_S_all      1.214
_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 0.3747(7) 0.5086(4) 0.6753(2) 0.0177(10) Uani 1 1 d . . . . .
C2 C 0.5635(7) 0.5352(3) 0.6436(2) 0.0126(9) Uani 1 1 d . . . . .
H2 H 0.5433 0.5329 0.5964 0.015 Uiso 1 1 calc R U . . .
C3 C 0.7315(7) 0.4603(3) 0.6597(2) 0.0162(9) Uani 1 1 d . . . . .
H3A H 0.8530 0.4947 0.6475 0.019 Uiso 1 1 calc R U . . .
H3B H 0.7345 0.4495 0.7064 0.019 Uiso 1 1 calc R U . . .
C4 C 0.7287(7) 0.6979(3) 0.6105(2) 0.0166(9) Uani 1 1 d . . . . .
H4A H 0.7602 0.7694 0.6238 0.025 Uiso 1 1 calc R U . . .
H4B H 0.6554 0.7002 0.5707 0.025 Uiso 1 1 calc R U . . .
H4C H 0.8470 0.6583 0.6038 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7010(8) 0.6588(3) 0.7258(2) 0.0208(11) Uani 1 1 d . . . . .
H5A H 0.6235 0.6221 0.7577 0.031 Uiso 1 1 calc R U . . .
H5B H 0.7073 0.7333 0.7366 0.031 Uiso 1 1 calc R U . . .
H5C H 0.8306 0.6294 0.7254 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7225(7) 0.3542(3) 0.6276(2) 0.0155(9) Uani 1 1 d . . . . .
C7 C 0.7116(8) 0.3440(4) 0.5619(2) 0.0235(11) Uani 1 1 d . . . . .
H7 H 0.7074 0.4046 0.5357 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7070(8) 0.2462(4) 0.5344(2) 0.0271(11) Uani 1 1 d . . . . .
H8 H 0.6978 0.2398 0.4894 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7155(8) 0.1577(4) 0.5716(2) 0.0259(11) Uani 1 1 d . . . . .
H9 H 0.7122 0.0905 0.5523 0.031 Uiso 1 1 calc R U . . .
C10 C 0.7290(8) 0.1667(3) 0.6370(2) 0.0249(11) Uani 1 1 d . . . . .
H10 H 0.7360 0.1056 0.6627 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7322(7) 0.2642(3) 0.6651(2) 0.0213(10) Uani 1 1 d . . . . .
H11 H 0.7411 0.2702 0.7102 0.026 Uiso 1 1 calc R U . . .
Cl1 Cl 0.44653(15) 0.91922(11) 0.52319(5) 0.0204(2) Uani 1 1 d . . . . .
Cl2 Cl -0.03103(14) 0.91350(11) 0.53258(5) 0.0169(2) Uani 1 1 d . . . . .
Cl3 Cl 0.22259(16) 1.09683(8) 0.61174(5) 0.0195(2) Uani 1 1 d . . . . .
Cl4 Cl 0.00521(15) 0.90601(11) 0.69042(5) 0.0185(3) Uani 1 1 d . . . . .
Cl5 Cl 0.47585(15) 0.90377(10) 0.68059(5) 0.0171(3) Uani 1 1 d . . . . .
Cl6 Cl 0.22579(16) 0.72874(8) 0.59901(5) 0.0189(2) Uani 1 1 d . . . . .
Cl7 Cl 0.26954(18) 0.39255(9) 0.64707(6) 0.0286(3) Uani 1 1 d . . . . .
N1 N 0.6115(6) 0.6459(3) 0.66129(17) 0.0119(8) Uani 1 1 d . . . . .
H1 H 0.502(7) 0.675(4) 0.662(2) 0.014 Uiso 1 1 d . U . . .
Nb1 Nb 0.22180(5) 0.91783(3) 0.60523(2) 0.01191(11) Uani 1 1 d . . . . .
O1 O 0.2963(5) 0.5602(2) 0.71377(15) 0.0245(8) 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 O1 1.178(5) . ?
C1 C2 1.516(7) . ?
C1 Cl7 1.758(5) . ?
C2 N1 1.500(6) . ?
C2 C3 1.553(6) . ?
C2 H2 1.0000 . ?
C3 C6 1.516(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.499(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N1 1.501(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.387(6) . ?
C6 C11 1.396(6) . ?
C7 C8 1.377(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
Cl1 Nb1 2.3305(11) . ?
Cl2 Nb1 2.3344(11) . ?
Cl3 Nb1 2.2921(11) . ?
Cl4 Nb1 2.3475(11) . ?
Cl5 Nb1 2.3844(11) . ?
Cl6 Nb1 2.4206(11) . ?
N1 H1 0.85(5) . ?

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 C1 C2 125.4(4) . . ?
O1 C1 Cl7 120.6(4) . . ?
C2 C1 Cl7 113.9(3) . . ?
N1 C2 C1 107.3(4) . . ?
N1 C2 C3 111.0(4) . . ?
C1 C2 C3 115.1(4) . . ?
N1 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C6 C3 C2 115.1(4) . . ?
C6 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C6 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 119.1(4) . . ?
C7 C6 C3 121.9(4) . . ?
C11 C6 C3 118.9(4) . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.6(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.9(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 120.1(4) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C4 N1 C2 111.4(3) . . ?
C4 N1 C5 111.4(4) . . ?
C2 N1 C5 114.9(3) . . ?
C4 N1 H1 108(3) . . ?
C2 N1 H1 102(3) . . ?
C5 N1 H1 109(3) . . ?
Cl3 Nb1 Cl1 91.99(5) . . ?
Cl3 Nb1 Cl2 93.69(4) . . ?
Cl1 Nb1 Cl2 91.55(4) . . ?
Cl3 Nb1 Cl4 91.17(4) . . ?
Cl1 Nb1 Cl4 176.12(5) . . ?
Cl2 Nb1 Cl4 90.48(4) . . ?
Cl3 Nb1 Cl5 91.94(4) . . ?
Cl1 Nb1 Cl5 89.39(4) . . ?
Cl2 Nb1 Cl5 174.25(5) . . ?
Cl4 Nb1 Cl5 88.25(4) . . ?
Cl3 Nb1 Cl6 179.14(4) . . ?
Cl1 Nb1 Cl6 87.71(5) . . ?
Cl2 Nb1 Cl6 87.12(4) . . ?
Cl4 Nb1 Cl6 89.10(4) . . ?
Cl5 Nb1 Cl6 87.25(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 Cl2 1.00 2.84 3.813(4) 164.1 4_566
C3 H3B Cl4 0.99 2.88 3.710(4) 141.6 3_646
C3 H3B Cl5 0.99 2.85 3.723(5) 147.3 3_646
C4 H4A Cl4 0.98 2.82 3.690(4) 148.9 1_655
C4 H4A Cl5 0.98 2.88 3.494(4) 121.2 .
C4 H4B Cl2 0.98 2.92 3.788(4) 148.4 4_566
C4 H4C Cl1 0.98 2.93 3.527(4) 120.4 4_566
C4 H4C Cl6 0.98 2.80 3.504(5) 129.6 1_655
C5 H5A Cl3 0.98 2.96 3.541(4) 118.9 3_646
C5 H5A O1 0.98 2.59 3.105(6) 113.0 .
C5 H5B Cl5 0.98 2.96 3.631(5) 126.9 .
N1 H1 Cl5 0.85(5) 2.96(5) 3.454(4) 119(4) .
N1 H1 Cl6 0.85(5) 2.44(5) 3.177(4) 147(4) .

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.121

####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1041071'
_audit_update_record             
;
2014-12-27 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H16 Cl6 N Nb'
_chemical_formula_weight         407.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.065(3)
_cell_length_b                   18.492(7)
_cell_length_c                   10.184(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.036(5)
_cell_angle_gamma                90.00
_cell_volume                     1515.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4886
_cell_measurement_theta_min      2.2025
_cell_measurement_theta_max      27.617

_exptl_crystal_description       needle
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7352
_exptl_absorpt_correction_T_max  0.8111
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1161 (selected reflections only, before parameter refinement)
 R(int) =  0.0643 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16015
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.68
_reflns_number_total             3507
_reflns_number_gt                2638
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. The following restraints
 were applied (given as SHELXL lines): 
 DFIX 0.93 0.02 N1 H11  N1 H12
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0257P)²+2.8409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3507
_refine_ls_number_parameters     137
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Nb1 Nb 0.16265(5) 0.38633(2) 0.27325(3) 0.01530(11) Uani 1 1 d . . .
Cl1 Cl 0.34386(13) 0.45417(5) 0.42309(9) 0.0196(2) Uani 1 1 d . . .
Cl2 Cl 0.39933(14) 0.34236(6) 0.16834(11) 0.0278(3) Uani 1 1 d . . .
Cl3 Cl -0.01378(15) 0.32083(6) 0.12895(11) 0.0312(3) Uani 1 1 d . . .
Cl4 Cl -0.05923(14) 0.42628(6) 0.38489(11) 0.0272(3) Uani 1 1 d . . .
Cl5 Cl 0.15574(13) 0.48546(6) 0.13178(9) 0.0205(2) Uani 1 1 d . . .
Cl6 Cl 0.20310(16) 0.28711(6) 0.41872(10) 0.0286(3) Uani 1 1 d . . .
N1 N 0.4169(4) 0.14732(19) 0.1944(3) 0.0176(7) Uani 1 1 d D . .
H12 H 0.387(5) 0.129(2) 0.112(2) 0.021 Uiso 1 1 d D . .
H11 H 0.395(5) 0.1960(11) 0.189(4) 0.021 Uiso 1 1 d D . .
C1 C 0.6045(5) 0.1439(2) 0.2115(4) 0.0190(9) Uani 1 1 d . . .
H1 H 0.6391 0.0920 0.2168 0.023 Uiso 1 1 calc R . .
C2 C 0.6655(6) 0.1812(3) 0.3379(4) 0.0252(10) Uani 1 1 d . . .
H2A H 0.7873 0.1805 0.3464 0.038 Uiso 1 1 calc R . .
H2B H 0.6225 0.1559 0.4129 0.038 Uiso 1 1 calc R . .
H2C H 0.6263 0.2314 0.3364 0.038 Uiso 1 1 calc R . .
C3 C 0.6716(5) 0.1771(2) 0.0901(4) 0.0247(10) Uani 1 1 d . . .
H3A H 0.6458 0.2289 0.0873 0.037 Uiso 1 1 calc R . .
H3B H 0.6201 0.1535 0.0113 0.037 Uiso 1 1 calc R . .
H3C H 0.7924 0.1704 0.0933 0.037 Uiso 1 1 calc R . .
C4 C 0.3157(5) 0.1125(2) 0.2975(4) 0.0199(9) Uani 1 1 d . . .
H4 H 0.3367 0.1390 0.3826 0.024 Uiso 1 1 calc R . .
C5 C 0.3684(6) 0.0338(2) 0.3176(4) 0.0258(10) Uani 1 1 d . . .
H5A H 0.3643 0.0091 0.2323 0.039 Uiso 1 1 calc R . .
H5B H 0.2927 0.0097 0.3749 0.039 Uiso 1 1 calc R . .
H5C H 0.4819 0.0319 0.3586 0.039 Uiso 1 1 calc R . .
C6 C 0.1346(5) 0.1203(2) 0.2514(4) 0.0242(10) Uani 1 1 d . . .
H6A H 0.1094 0.1713 0.2336 0.036 Uiso 1 1 calc R . .
H6B H 0.0654 0.1025 0.3199 0.036 Uiso 1 1 calc R . .
H6C H 0.1114 0.0920 0.1708 0.036 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nb1 Cl4 2.3082(13) . ?
Nb1 Cl3 2.3145(13) . ?
Nb1 Cl5 2.3299(12) . ?
Nb1 Cl6 2.3663(13) . ?
Nb1 Cl1 2.3927(12) . ?
Nb1 Cl2 2.3944(13) . ?
N1 C1 1.512(5) . ?
N1 C4 1.518(5) . ?
N1 H12 0.920(19) . ?
N1 H11 0.919(19) . ?
C1 C2 1.512(6) . ?
C1 C3 1.514(6) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C6 1.509(6) . ?
C4 C5 1.526(6) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl4 Nb1 Cl3 90.97(5) . . ?
Cl4 Nb1 Cl5 93.85(4) . . ?
Cl3 Nb1 Cl5 91.85(5) . . ?
Cl4 Nb1 Cl6 90.99(5) . . ?
Cl3 Nb1 Cl6 92.48(5) . . ?
Cl5 Nb1 Cl6 173.45(4) . . ?
Cl4 Nb1 Cl1 88.73(5) . . ?
Cl3 Nb1 Cl1 179.70(5) . . ?
Cl5 Nb1 Cl1 88.21(4) . . ?
Cl6 Nb1 Cl1 87.48(5) . . ?
Cl4 Nb1 Cl2 176.93(4) . . ?
Cl3 Nb1 Cl2 90.73(5) . . ?
Cl5 Nb1 Cl2 88.65(4) . . ?
Cl6 Nb1 Cl2 86.39(5) . . ?
Cl1 Nb1 Cl2 89.56(5) . . ?
C1 N1 C4 119.0(3) . . ?
C1 N1 H12 106(3) . . ?
C4 N1 H12 111(3) . . ?
C1 N1 H11 104(3) . . ?
C4 N1 H11 110(3) . . ?
H12 N1 H11 106(4) . . ?
C2 C1 N1 110.0(3) . . ?
C2 C1 C3 113.3(4) . . ?
N1 C1 C3 107.5(3) . . ?
C2 C1 H1 108.6 . . ?
N1 C1 H1 108.6 . . ?
C3 C1 H1 108.6 . . ?
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 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 C4 N1 107.4(3) . . ?
C6 C4 C5 112.8(4) . . ?
N1 C4 C5 109.9(3) . . ?
C6 C4 H4 108.9 . . ?
N1 C4 H4 108.9 . . ?
C5 C4 H4 108.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -60.7(5) . . . . ?
C4 N1 C1 C3 175.5(3) . . . . ?
C1 N1 C4 C6 -176.7(3) . . . . ?
C1 N1 C4 C5 -53.7(5) . . . . ?

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
N1 H12 Cl1 0.920(19) 2.47(2) 3.358(4) 162(4) 4_565
N1 H12 Cl6 0.920(19) 2.84(4) 3.412(4) 121(3) 4_565
N1 H11 Cl2 0.919(19) 2.71(2) 3.618(4) 168(4) .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.68
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.891
_refine_diff_density_rms         0.139
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1518993'
_audit_update_record             
;
2016-11-24 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration ad
_chemical_formula_sum            'C7 H16 Cl11 N Nb2 O2'
_chemical_formula_weight         721.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.045(2)
_cell_length_b                   6.9628(17)
_cell_length_c                   16.994(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.428(3)
_cell_angle_gamma                90.00
_cell_volume                     1140.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6141
_cell_measurement_theta_min      2.499
_cell_measurement_theta_max      28.2995

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_absorpt_coefficient_mu    2.297
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6441
_exptl_absorpt_correction_T_max  0.7393
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1337 (selected reflections only, before parameter refinement)
 R(int) =  0.0514 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11566
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.25
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4492
_reflns_number_gt                4290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. The following restraints
 were applied (given as SHELXL lines):  
 DFIX 0.91 0.02 N1 H1A  H1B N1  H1C N1
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0092P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_number_reflns         4492
_refine_ls_number_parameters     217
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0428
_refine_ls_wR_factor_gt          0.0420
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Nb1 Nb 0.80158(3) 0.18439(4) 0.076462(17) 0.01221(7) Uani 1 1 d . . .
Cl1 Cl 0.89682(9) 0.42203(12) 0.17465(5) 0.02027(19) Uani 1 1 d . . .
Cl2 Cl 0.67246(9) 0.42917(12) -0.00719(5) 0.01769(18) Uani 1 1 d . . .
Cl3 Cl 0.61567(8) 0.15690(12) 0.14141(5) 0.01639(18) Uani 1 1 d . . .
Cl4 Cl 0.67856(9) -0.04803(12) -0.01804(5) 0.01842(19) Uani 1 1 d . . .
Cl5 Cl 0.91988(9) -0.05756(12) 0.16416(5) 0.0206(2) Uani 1 1 d . . .
Cl6 Cl 0.97530(8) 0.20531(13) 0.01460(5) 0.01859(18) Uani 1 1 d . . .
Nb2 Nb 0.67173(3) -0.15607(4) 0.656987(17) 0.01433(7) Uani 1 1 d . . .
Cl7 Cl 0.49242(8) -0.36170(12) 0.66917(5) 0.0207(2) Uani 1 1 d . . .
Cl8 Cl 0.79268(10) -0.40091(13) 0.62259(6) 0.0265(2) Uani 1 1 d . . .
Cl9 Cl 0.76377(8) -0.18573(12) 0.79869(5) 0.01869(18) Uani 1 1 d . . .
Cl10 Cl 0.83750(9) 0.07129(13) 0.64995(6) 0.0228(2) Uani 1 1 d . . .
Cl11 Cl 0.53607(9) -0.06978(13) 0.52933(5) 0.0238(2) Uani 1 1 d . . .
C1 C 0.5287(3) 0.1544(5) 0.75490(18) 0.0131(7) Uani 1 1 d . . .
O1 O 0.5609(2) 0.0826(3) 0.69669(13) 0.0154(5) Uani 1 1 d . . .
O2 O 0.6066(2) 0.2657(3) 0.80967(13) 0.0137(5) Uani 1 1 d . . .
C2 C 0.3878(3) 0.1218(5) 0.76633(19) 0.0143(7) Uani 1 1 d . . .
H2 H 0.3634 -0.0172 0.7570 0.017 Uiso 1 1 calc R . .
N1 N 0.3906(3) 0.1738(5) 0.85281(16) 0.0153(6) Uani 1 1 d D . .
H1A H 0.460(3) 0.109(4) 0.8903(18) 0.023 Uiso 1 1 d D . .
H1B H 0.305(2) 0.137(5) 0.857(2) 0.023 Uiso 1 1 d D . .
H1C H 0.401(3) 0.298(3) 0.865(2) 0.023 Uiso 1 1 d D . .
C3 C 0.2753(3) 0.2424(5) 0.70713(18) 0.0149(7) Uani 1 1 d . . .
H3A H 0.1881 0.2280 0.7228 0.018 Uiso 1 1 calc R . .
H3B H 0.3029 0.3791 0.7149 0.018 Uiso 1 1 calc R . .
C4 C 0.2448(3) 0.1944(6) 0.61575(18) 0.0193(7) Uani 1 1 d . . .
H4 H 0.3326 0.2085 0.5996 0.023 Uiso 1 1 calc R . .
C5 C 0.1392(3) 0.3402(6) 0.56714(19) 0.0281(9) Uani 1 1 d . . .
H5A H 0.1759 0.4704 0.5800 0.042 Uiso 1 1 calc R . .
H5B H 0.0522 0.3275 0.5820 0.042 Uiso 1 1 calc R . .
H5C H 0.1218 0.3160 0.5083 0.042 Uiso 1 1 calc R . .
C6 C 0.1924(4) -0.0102(6) 0.5977(2) 0.0270(9) Uani 1 1 d . . .
H6A H 0.1744 -0.0363 0.5389 0.040 Uiso 1 1 calc R . .
H6B H 0.1064 -0.0263 0.6133 0.040 Uiso 1 1 calc R . .
H6C H 0.2627 -0.1000 0.6290 0.040 Uiso 1 1 calc R . .
C7 C 0.7475(3) 0.3140(5) 0.8061(2) 0.0179(8) Uani 1 1 d . . .
H7A H 0.7917 0.3999 0.8517 0.027 Uiso 1 1 calc R . .
H7B H 0.7421 0.3782 0.7540 0.027 Uiso 1 1 calc R . .
H7C H 0.8024 0.1962 0.8103 0.027 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nb1 Cl6 2.2825(9) . ?
Nb1 Cl5 2.3388(9) . ?
Nb1 Cl1 2.3526(9) . ?
Nb1 Cl2 2.3591(9) . ?
Nb1 Cl4 2.3670(9) . ?
Nb1 Cl3 2.4307(9) . ?
Nb2 O1 2.209(2) . ?
Nb2 Cl8 2.2641(10) . ?
Nb2 Cl11 2.2918(9) . ?
Nb2 Cl10 2.3250(10) . ?
Nb2 Cl9 2.3318(10) . ?
Nb2 Cl7 2.3555(9) . ?
C1 O1 1.231(4) . ?
C1 O2 1.291(4) . ?
C1 C2 1.499(4) . ?
O2 C7 1.473(3) . ?
C2 N1 1.506(4) . ?
C2 C3 1.534(4) . ?
C2 H2 1.0000 . ?
N1 H1A 0.915(18) . ?
N1 H1B 0.913(17) . ?
N1 H1C 0.892(18) . ?
C3 C4 1.532(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.520(5) . ?
C4 C5 1.531(5) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl6 Nb1 Cl5 91.29(3) . . ?
Cl6 Nb1 Cl1 94.08(3) . . ?
Cl5 Nb1 Cl1 91.33(3) . . ?
Cl6 Nb1 Cl2 92.18(3) . . ?
Cl5 Nb1 Cl2 176.49(3) . . ?
Cl1 Nb1 Cl2 87.90(4) . . ?
Cl6 Nb1 Cl4 92.96(3) . . ?
Cl5 Nb1 Cl4 90.78(4) . . ?
Cl1 Nb1 Cl4 172.60(3) . . ?
Cl2 Nb1 Cl4 89.57(3) . . ?
Cl6 Nb1 Cl3 179.07(4) . . ?
Cl5 Nb1 Cl3 88.34(3) . . ?
Cl1 Nb1 Cl3 86.78(3) . . ?
Cl2 Nb1 Cl3 88.19(3) . . ?
Cl4 Nb1 Cl3 86.19(3) . . ?
O1 Nb2 Cl8 177.18(6) . . ?
O1 Nb2 Cl11 82.87(6) . . ?
Cl8 Nb2 Cl11 99.89(4) . . ?
O1 Nb2 Cl10 86.20(6) . . ?
Cl8 Nb2 Cl10 93.15(4) . . ?
Cl11 Nb2 Cl10 90.90(4) . . ?
O1 Nb2 Cl9 80.68(6) . . ?
Cl8 Nb2 Cl9 96.60(3) . . ?
Cl11 Nb2 Cl9 163.09(3) . . ?
Cl10 Nb2 Cl9 91.88(3) . . ?
O1 Nb2 Cl7 88.07(6) . . ?
Cl8 Nb2 Cl7 92.55(4) . . ?
Cl11 Nb2 Cl7 88.73(3) . . ?
Cl10 Nb2 Cl7 174.26(3) . . ?
Cl9 Nb2 Cl7 86.85(3) . . ?
O1 C1 O2 125.5(3) . . ?
O1 C1 C2 121.0(3) . . ?
O2 C1 C2 113.5(3) . . ?
C1 O1 Nb2 145.2(2) . . ?
C1 O2 C7 120.1(2) . . ?
C1 C2 N1 109.4(2) . . ?
C1 C2 C3 112.3(3) . . ?
N1 C2 C3 108.4(3) . . ?
C1 C2 H2 108.9 . . ?
N1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C2 N1 H1A 111(2) . . ?
C2 N1 H1B 104(2) . . ?
H1A N1 H1B 111(3) . . ?
C2 N1 H1C 116(2) . . ?
H1A N1 H1C 107(3) . . ?
H1B N1 H1C 108(3) . . ?
C4 C3 C2 116.4(3) . . ?
C4 C3 H3A 108.2 . . ?
C2 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
C2 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
C6 C4 C5 111.4(3) . . ?
C6 C4 C3 111.6(3) . . ?
C5 C4 C3 108.2(3) . . ?
C6 C4 H4 108.5 . . ?
C5 C4 H4 108.5 . . ?
C3 C4 H4 108.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 O1 Nb2 82.6(5) . . . . ?
C2 C1 O1 Nb2 -99.2(4) . . . . ?
Cl8 Nb2 O1 C1 -30.9(15) . . . . ?
Cl11 Nb2 O1 C1 160.8(4) . . . . ?
Cl10 Nb2 O1 C1 -107.8(4) . . . . ?
Cl9 Nb2 O1 C1 -15.2(4) . . . . ?
Cl7 Nb2 O1 C1 71.9(4) . . . . ?
O1 C1 O2 C7 -0.9(5) . . . . ?
C2 C1 O2 C7 -179.1(3) . . . . ?
O1 C1 C2 N1 163.3(3) . . . . ?
O2 C1 C2 N1 -18.4(4) . . . . ?
O1 C1 C2 C3 -76.3(4) . . . . ?
O2 C1 C2 C3 102.0(3) . . . . ?
C1 C2 C3 C4 65.6(4) . . . . ?
N1 C2 C3 C4 -173.3(3) . . . . ?
C2 C3 C4 C6 61.7(4) . . . . ?
C2 C3 C4 C5 -175.4(3) . . . . ?

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
N1 H1A Cl4 0.915(18) 2.555(19) 3.461(3) 171(3) 1_556
N1 H1B Cl1 0.913(17) 2.46(2) 3.296(3) 153(3) 2_646
N1 H1B Cl2 0.913(17) 2.89(3) 3.335(3) 111(2) 2_646
N1 H1C Cl3 0.892(18) 2.50(2) 3.366(3) 163(3) 2_656

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.069
