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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1404269'
_audit_update_record             
;
2015-06-01 deposited with the CCDC.
2015-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        (Naphtylpyridine)Chloro(p-cymene)(ruthenium)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 Cl N Ru'
_chemical_formula_sum            'C25 H24 Cl N Ru'
_chemical_formula_weight         474.97

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'
Ru Ru -1.2594 0.8363 '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'

_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                   7.9093(4)
_cell_length_b                   16.4319(8)
_cell_length_c                   16.0856(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.852(6)
_cell_angle_gamma                90
_cell_volume                     2029.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4682
_cell_measurement_theta_min      2.4740
_cell_measurement_theta_max      28.8652

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.914
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.66264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1829
_diffrn_reflns_number            14971
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.479
_diffrn_reflns_theta_max         28.929
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4668
_reflns_number_gt                3542
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    SIR-92
_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)+(0.0487P)²] 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         4668
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 1.1895(5) 0.3895(2) 0.2231(3) 0.0423(10) Uani 1 1 d . . . . .
H1 H 1.2355 0.4266 0.1907 0.051 Uiso 1 1 calc R U . . .
C2 C 1.1845(6) 0.4106(3) 0.3049(3) 0.0525(12) Uani 1 1 d . . . . .
H2 H 1.2297 0.4599 0.3287 0.063 Uiso 1 1 calc R U . . .
C3 C 1.1097(6) 0.3559(3) 0.3508(3) 0.0534(12) Uani 1 1 d . . . . .
H3 H 1.0999 0.3691 0.4057 0.064 Uiso 1 1 calc R U . . .
C4 C 1.0499(6) 0.2820(3) 0.3158(3) 0.0459(11) Uani 1 1 d . . . . .
H4 H 0.9970 0.2463 0.3466 0.055 Uiso 1 1 calc R U . . .
C5 C 1.0675(5) 0.2599(2) 0.2346(2) 0.0316(8) Uani 1 1 d . . . . .
C6 C 1.0144(5) 0.1829(2) 0.1875(2) 0.0297(8) Uani 1 1 d . . . . .
C7 C 1.0114(4) 0.1892(2) 0.1001(3) 0.0297(8) Uani 1 1 d . . . . .
C8 C 0.9423(5) 0.1229(2) 0.0458(3) 0.0362(9) Uani 1 1 d . . . . .
H8 H 0.9390 0.1262 -0.0123 0.043 Uiso 1 1 calc R U . . .
C9 C 0.8802(5) 0.0538(2) 0.0770(3) 0.0406(10) Uani 1 1 d . . . . .
H9 H 0.8310 0.0126 0.0392 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8902(5) 0.0445(2) 0.1652(3) 0.0360(9) Uani 1 1 d . . . . .
C11 C 0.8234(5) -0.0267(2) 0.1969(3) 0.0477(11) Uani 1 1 d . . . . .
H11 H 0.7726 -0.0672 0.1587 0.057 Uiso 1 1 calc R U . . .
C12 C 0.8325(6) -0.0367(3) 0.2818(4) 0.0557(13) Uani 1 1 d . . . . .
H12 H 0.7815 -0.0817 0.3010 0.067 Uiso 1 1 calc R U . . .
C13 C 0.9181(6) 0.0208(3) 0.3392(3) 0.0539(13) Uani 1 1 d . . . . .
H13 H 0.9309 0.0122 0.3975 0.065 Uiso 1 1 calc R U . . .
C14 C 0.9859(5) 0.0916(3) 0.3118(3) 0.0450(10) Uani 1 1 d . . . . .
H14 H 1.0452 0.1285 0.3523 0.054 Uiso 1 1 calc R U . . .
C15 C 0.9663(5) 0.1083(2) 0.2242(3) 0.0331(9) Uani 1 1 d . . . . .
C16 C 1.3581(5) 0.2510(2) 0.0390(3) 0.0341(9) Uani 1 1 d . . . . .
C17 C 1.3661(5) 0.3367(2) 0.0572(3) 0.0380(9) Uani 1 1 d . . . . .
H17 H 1.4476 0.3556 0.1050 0.046 Uiso 1 1 calc R U . . .
C18 C 1.2525(5) 0.3943(2) 0.0041(3) 0.0409(10) Uani 1 1 d . . . . .
H18 H 1.2679 0.4498 0.0148 0.049 Uiso 1 1 calc R U . . .
C19 C 1.1184(5) 0.3671(3) -0.0640(3) 0.0441(10) Uani 1 1 d . . . . .
C20 C 1.1000(6) 0.2813(2) -0.0809(3) 0.0408(10) Uani 1 1 d . . . . .
H20 H 1.0097 0.2622 -0.1247 0.049 Uiso 1 1 calc R U . . .
C21 C 1.2201(5) 0.2255(2) -0.0306(3) 0.0364(9) Uani 1 1 d . . . . .
H21 H 1.2081 0.1703 -0.0436 0.044 Uiso 1 1 calc R U . . .
C22 C 1.4900(5) 0.1924(2) 0.0937(3) 0.0419(10) Uani 1 1 d . . . . .
H22 H 1.5975 0.1971 0.0739 0.050 Uiso 1 1 calc R U . . .
C23 C 1.5358(7) 0.2139(3) 0.1880(3) 0.0662(15) Uani 1 1 d . . . . .
H23A H 1.5720 0.2698 0.1949 0.099 Uiso 1 1 calc R U . . .
H23B H 1.4357 0.2061 0.2110 0.099 Uiso 1 1 calc R U . . .
H23C H 1.6289 0.1795 0.2177 0.099 Uiso 1 1 calc R U . . .
C24 C 1.4317(6) 0.1034(2) 0.0810(4) 0.0656(15) Uani 1 1 d . . . . .
H24A H 1.4031 0.0906 0.0210 0.098 Uiso 1 1 calc R U . . .
H24B H 1.5244 0.0686 0.1104 0.098 Uiso 1 1 calc R U . . .
H24C H 1.3312 0.0951 0.1037 0.098 Uiso 1 1 calc R U . . .
C25 C 0.9902(6) 0.4276(3) -0.1165(3) 0.0610(13) Uani 1 1 d . . . . .
H25A H 0.9074 0.3990 -0.1601 0.091 Uiso 1 1 calc R U . . .
H25B H 0.9300 0.4555 -0.0797 0.091 Uiso 1 1 calc R U . . .
H25C H 1.0522 0.4663 -0.1427 0.091 Uiso 1 1 calc R U . . .
N1 N 1.1301(4) 0.31663(17) 0.1869(2) 0.0315(7) Uani 1 1 d . . . . .
Ru1 Ru 1.10129(4) 0.29406(2) 0.05647(2) 0.02841(12) Uani 1 1 d . . . . .
Cl1 Cl 0.80707(13) 0.34652(6) 0.04040(7) 0.0459(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.364(4) . ?
C1 C2 1.372(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.374(5) . ?
C5 C6 1.483(5) . ?
C6 C7 1.404(5) . ?
C6 C15 1.450(5) . ?
C7 C8 1.421(5) . ?
C7 Ru1 2.051(3) . ?
C8 C9 1.378(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.411(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.427(5) . ?
C10 C15 1.445(5) . ?
C11 C12 1.360(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.396(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.407(5) . ?
C14 H14 0.9300 . ?
C16 C21 1.426(5) . ?
C16 C17 1.437(5) . ?
C16 C22 1.533(5) . ?
C16 Ru1 2.231(4) . ?
C17 C18 1.438(5) . ?
C17 Ru1 2.206(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.403(6) . ?
C18 Ru1 2.310(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.436(5) . ?
C19 C25 1.523(5) . ?
C19 Ru1 2.310(4) . ?
C20 C21 1.425(6) . ?
C20 Ru1 2.217(4) . ?
C20 H20 0.9300 . ?
C21 Ru1 2.178(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.514(6) . ?
C22 C24 1.533(5) . ?
C22 H22 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N1 Ru1 2.088(3) . ?
Ru1 Cl1 2.4367(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.1(4) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 117.5(4) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 118.5(3) . . ?
N1 C5 C6 112.9(3) . . ?
C4 C5 C6 128.4(4) . . ?
C7 C6 C15 121.8(3) . . ?
C7 C6 C5 112.6(3) . . ?
C15 C6 C5 125.7(3) . . ?
C6 C7 C8 118.1(3) . . ?
C6 C7 Ru1 118.7(3) . . ?
C8 C7 Ru1 123.2(3) . . ?
C9 C8 C7 121.7(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 121.1(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 C15 119.7(3) . . ?
C11 C10 C15 119.4(4) . . ?
C12 C11 C10 121.5(4) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 119.2(4) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C14 121.6(5) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 116.4(3) . . ?
C14 C15 C6 126.6(4) . . ?
C10 C15 C6 117.0(3) . . ?
C21 C16 C17 115.9(3) . . ?
C21 C16 C22 123.6(3) . . ?
C17 C16 C22 120.5(3) . . ?
C21 C16 Ru1 69.1(2) . . ?
C17 C16 Ru1 70.18(19) . . ?
C22 C16 Ru1 129.9(3) . . ?
C18 C17 C16 122.2(4) . . ?
C18 C17 Ru1 75.4(2) . . ?
C16 C17 Ru1 72.03(19) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
Ru1 C17 H17 125.4 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 Ru1 72.3(2) . . ?
C17 C18 Ru1 67.6(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
Ru1 C18 H18 133.4 . . ?
C18 C19 C20 119.0(4) . . ?
C18 C19 C25 120.2(4) . . ?
C20 C19 C25 120.8(4) . . ?
C18 C19 Ru1 72.3(2) . . ?
C20 C19 Ru1 68.0(2) . . ?
C25 C19 Ru1 129.7(3) . . ?
C21 C20 C19 120.0(4) . . ?
C21 C20 Ru1 69.6(2) . . ?
C19 C20 Ru1 75.1(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
Ru1 C20 H20 127.4 . . ?
C20 C21 C16 122.5(4) . . ?
C20 C21 Ru1 72.6(2) . . ?
C16 C21 Ru1 73.2(2) . . ?
C20 C21 H21 118.7 . . ?
C16 C21 H21 118.7 . . ?
Ru1 C21 H21 127.8 . . ?
C23 C22 C24 110.4(4) . . ?
C23 C22 C16 113.3(3) . . ?
C24 C22 C16 112.4(3) . . ?
C23 C22 H22 106.8 . . ?
C24 C22 H22 106.8 . . ?
C16 C22 H22 106.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C25 H25A 109.5 . . ?
C19 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C19 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C5 119.3(3) . . ?
C1 N1 Ru1 121.9(3) . . ?
C5 N1 Ru1 118.3(2) . . ?
C7 Ru1 N1 76.64(13) . . ?
C7 Ru1 C21 91.36(14) . . ?
N1 Ru1 C21 141.03(14) . . ?
C7 Ru1 C17 132.20(14) . . ?
N1 Ru1 C17 93.60(14) . . ?
C21 Ru1 C17 67.21(15) . . ?
C7 Ru1 C20 110.02(15) . . ?
N1 Ru1 C20 172.41(13) . . ?
C21 Ru1 C20 37.83(15) . . ?
C17 Ru1 C20 79.25(16) . . ?
C7 Ru1 C16 100.22(13) . . ?
N1 Ru1 C16 107.40(13) . . ?
C21 Ru1 C16 37.72(14) . . ?
C17 Ru1 C16 37.79(13) . . ?
C20 Ru1 C16 68.38(15) . . ?
C7 Ru1 C19 144.89(16) . . ?
N1 Ru1 C19 137.39(14) . . ?
C21 Ru1 C19 66.95(15) . . ?
C17 Ru1 C19 66.01(15) . . ?
C20 Ru1 C19 36.92(14) . . ?
C16 Ru1 C19 79.69(14) . . ?
C7 Ru1 C18 167.46(14) . . ?
N1 Ru1 C18 107.35(14) . . ?
C21 Ru1 C18 78.08(14) . . ?
C17 Ru1 C18 37.03(14) . . ?
C20 Ru1 C18 65.36(15) . . ?
C16 Ru1 C18 67.28(13) . . ?
C19 Ru1 C18 35.34(15) . . ?
C7 Ru1 Cl1 86.16(10) . . ?
N1 Ru1 Cl1 85.16(9) . . ?
C21 Ru1 Cl1 131.53(11) . . ?
C17 Ru1 Cl1 140.31(10) . . ?
C20 Ru1 Cl1 98.70(11) . . ?
C16 Ru1 Cl1 166.87(11) . . ?
C19 Ru1 Cl1 88.48(10) . . ?
C18 Ru1 Cl1 105.88(10) . . ?

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.134


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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1404270'
_audit_update_record             
;
2015-06-01 deposited with the CCDC.
2015-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        (naphtylpyridine)borondifluoride
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 B F2 N'
_chemical_formula_sum            'C15 H10 B F2 N'
_chemical_formula_weight         253.05

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.9355(5)
_cell_length_b                   19.5025(11)
_cell_length_c                   8.0301(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.383(7)
_cell_angle_gamma                90
_cell_volume                     1157.21(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4115
_cell_measurement_theta_min      2.7186
_cell_measurement_theta_max      29.9660

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.78291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1829
_diffrn_reflns_number            16901
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.757
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_full        25.000
_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             3388
_reflns_number_gt                2833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0677P)²+0.2195P] 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         3388
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_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
B1 B 0.29126(17) 0.42882(7) 0.77472(18) 0.0377(3) Uani 1 1 d . . . . .
F1 F 0.41978(10) 0.46485(4) 0.72798(13) 0.0579(3) Uani 1 1 d . . . . .
F2 F 0.37210(11) 0.40773(4) 0.95360(10) 0.0549(2) Uani 1 1 d . . . . .
N1 N 0.14031(12) 0.48348(5) 0.77489(12) 0.0347(2) Uani 1 1 d . . . . .
C1 C 0.20564(19) 0.54184(6) 0.86632(18) 0.0456(3) Uani 1 1 d . . . . .
H1 H 0.3301 0.5489 0.9129 0.055 Uiso 1 1 calc R U . . .
C2 C 0.0942(2) 0.59095(7) 0.89263(19) 0.0548(4) Uani 1 1 d . . . . .
H2 H 0.1418 0.6310 0.9547 0.066 Uiso 1 1 calc R U . . .
C3 C -0.0889(2) 0.57958(7) 0.8253(2) 0.0566(4) Uani 1 1 d . . . . .
H3 H -0.1673 0.6116 0.8438 0.068 Uiso 1 1 calc R U . . .
C4 C -0.15590(18) 0.52081(7) 0.73066(19) 0.0505(3) Uani 1 1 d . . . . .
H4 H -0.2802 0.5134 0.6844 0.061 Uiso 1 1 calc R U . . .
C5 C -0.04054(15) 0.47179(6) 0.70244(15) 0.0359(2) Uani 1 1 d . . . . .
C6 C -0.10869(15) 0.40905(6) 0.59563(15) 0.0386(3) Uani 1 1 d . . . . .
C7 C -0.29327(19) 0.39801(9) 0.5179(2) 0.0587(4) Uani 1 1 d . . . . .
H7 H -0.3726 0.4289 0.5390 0.070 Uiso 1 1 calc R U . . .
C8 C -0.3628(2) 0.34087(11) 0.4077(3) 0.0740(5) Uani 1 1 d . . . . .
H8 H -0.4874 0.3348 0.3560 0.089 Uiso 1 1 calc R U . . .
C9 C -0.2517(3) 0.29460(9) 0.3757(2) 0.0683(5) Uani 1 1 d . . . . .
H9 H -0.3006 0.2574 0.3012 0.082 Uiso 1 1 calc R U . . .
C10 C -0.0625(2) 0.30207(7) 0.45400(17) 0.0504(3) Uani 1 1 d . . . . .
C11 C 0.0565(3) 0.25387(8) 0.4257(2) 0.0658(5) Uani 1 1 d . U . . .
H11 H 0.0093 0.2161 0.3529 0.079 Uiso 1 1 calc R U . . .
C12 C 0.2387(3) 0.26137(8) 0.5026(2) 0.0656(4) Uani 1 1 d . U . . .
H12 H 0.3155 0.2290 0.4830 0.079 Uiso 1 1 calc R U . . .
C13 C 0.3102(2) 0.31843(7) 0.6119(2) 0.0527(3) Uani 1 1 d . . . . .
H13 H 0.4352 0.3232 0.6640 0.063 Uiso 1 1 calc R U . . .
C14 C 0.20169(16) 0.36757(6) 0.64451(15) 0.0370(2) Uani 1 1 d . . . . .
C15 C 0.01149(16) 0.36020(6) 0.56541(15) 0.0372(2) 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
B1 F1 1.3977(15) . ?
B1 F2 1.4043(16) . ?
B1 C14 1.5761(18) . ?
B1 N1 1.6039(16) . ?
N1 C1 1.3511(15) . ?
N1 C5 1.3569(14) . ?
C1 C2 1.3710(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3979(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.4788(17) . ?
C6 C7 1.3838(17) . ?
C6 C15 1.4301(17) . ?
C7 C8 1.405(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.350(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.408(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.408(2) . ?
C10 C15 1.4307(16) . ?
C11 C12 1.357(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.402(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.3759(17) . ?
C13 H13 0.9300 . ?
C14 C15 1.4152(17) . ?

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
F1 B1 F2 108.42(10) . . ?
F1 B1 C14 113.55(10) . . ?
F2 B1 C14 112.58(10) . . ?
F1 B1 N1 106.53(9) . . ?
F2 B1 N1 104.87(9) . . ?
C14 B1 N1 110.37(9) . . ?
C1 N1 C5 120.72(10) . . ?
C1 N1 B1 114.93(10) . . ?
C5 N1 B1 124.16(9) . . ?
N1 C1 C2 122.07(13) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 118.46(13) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.63(12) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.15(13) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N1 C5 C4 117.93(11) . . ?
N1 C5 C6 119.58(10) . . ?
C4 C5 C6 122.49(11) . . ?
C7 C6 C15 118.79(12) . . ?
C7 C6 C5 119.57(12) . . ?
C15 C6 C5 121.61(10) . . ?
C6 C7 C8 121.02(16) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 121.11(14) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.65(14) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 121.82(14) . . ?
C11 C10 C15 118.92(14) . . ?
C9 C10 C15 119.26(14) . . ?
C12 C11 C10 121.35(13) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.40(14) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 122.23(15) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 118.88(12) . . ?
C13 C14 B1 119.48(11) . . ?
C15 C14 B1 121.60(10) . . ?
C14 C15 C6 121.62(10) . . ?
C14 C15 C10 119.23(12) . . ?
C6 C15 C10 119.15(12) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM-pentane'
