# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5

_audit_creation_date             2014-02-24
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_shelxl_version_number           2014-1
_chemical_name_common            2,6-dimethyl-4-(Bpin)-pyridine
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H20 B N O2'
_chemical_formula_sum            'C13 H20 B N O2'
_chemical_formula_weight         233.11
_chemical_melting_point          354
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.9952(15)
_cell_length_b                   6.8431(13)
_cell_length_c                   12.251(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.085(4)
_cell_angle_gamma                90
_cell_volume                     669.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    763
_cell_measurement_theta_min      25.05
_cell_measurement_theta_max      30.08
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             252
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_min         2.971
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_source         
'60W microfocus Bede Microsource with glass polycapillary optics'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'ProteumM APEX CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_reflns_number_gt                1310
_reflns_number_total             1496
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_cell_refinement       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.45 (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelxS (Sheldrick, 2008)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0730P)²+0.2640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1432
_refine_special_details          
;
 The molecule lies on a crystallographic mirror (m) plane, the C₂Me₄ 
group of Bpin is disordered between two oppositely twisted conformation 
related via this plane.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Others
 Fixed Sof: C8(0.5) C9(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C11(0.5)
 H11A(0.5) H11B(0.5) H11C(0.5) C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) H13C(0.5)
3.a Riding coordinates:
 C2(H2), C4(H4), C6(H6A,H6B), C7(H7A,H7B), C10(H10A,H10B,H10C), C11(H11A,H11B,
 H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

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
B B 0.6650(3) 0.2500 0.18104(18) 0.0190(5) Uani 1 2 d S T P A .
O1 O 0.59356(16) 0.2500 0.27963(11) 0.0229(4) Uani 1 2 d S T P . .
O2 O 0.83572(16) 0.2500 0.18837(10) 0.0225(4) Uani 1 2 d S T P . .
N1 N 0.37430(19) 0.2500 -0.13179(12) 0.0182(4) Uani 1 2 d S T P A .
C1 C 0.2983(2) 0.2500 -0.03703(16) 0.0238(5) Uani 1 2 d S T P . .
C2 C 0.3869(2) 0.2500 0.06375(16) 0.0246(5) Uani 1 2 d S T P A .
H2 H 0.3283 0.2500 0.1292 0.030 Uiso 1 2 d RS T P . .
C3 C 0.5601(2) 0.2500 0.06930(15) 0.0185(4) Uani 1 2 d S T P . .
C4 C 0.6369(2) 0.2500 -0.02926(16) 0.0242(5) Uani 1 2 d S T P A .
H4 H 0.7557 0.2500 -0.0298 0.029 Uiso 1 2 d RS T P . .
C5 C 0.5418(2) 0.2500 -0.12761(16) 0.0218(5) Uani 1 2 d S T P . .
C6 C 0.1100(3) 0.2500 -0.04582(19) 0.0567(10) Uani 1 2 d S T P . .
H6A H 0.0705 0.1331 -0.0855 0.085 Uiso 1 1 d R . . . .
H6B H 0.0663 0.2500 0.0274 0.085 Uiso 1 2 d RS T P . .
C7 C 0.6223(3) 0.2500 -0.23591(18) 0.0462(8) Uani 1 2 d S T P A .
H7A H 0.5876 0.1331 -0.2774 0.069 Uiso 1 1 d R . . . .
H7B H 0.7444 0.2500 -0.2234 0.069 Uiso 1 2 d RS T P . .
C8 C 0.8882(3) 0.273(5) 0.30299(19) 0.029(4) Uani 0.5 1 d . . . A -1
C9 C 0.7277(3) 0.229(5) 0.3638(2) 0.027(5) Uani 0.5 1 d . . . A -1
C10 C 1.0404(3) 0.1541(5) 0.3308(2) 0.0306(7) Uani 0.5 1 d . . . A -1
H10A H 1.1331 0.1989 0.2909 0.046 Uiso 0.5 1 d R . . A -1
H10B H 1.0157 0.0208 0.3115 0.046 Uiso 0.5 1 d R . . A -1
H10C H 1.0687 0.1625 0.4078 0.046 Uiso 0.5 1 d R . . A -1
C11 C 0.9322(4) 0.4952(5) 0.3135(2) 0.0288(7) Uani 0.5 1 d . . . A -1
H11A H 1.0253 0.5227 0.2670 0.043 Uiso 0.5 1 d R . . A -1
H11B H 0.9661 0.5256 0.3897 0.043 Uiso 0.5 1 d R . . A -1
H11C H 0.8353 0.5757 0.2904 0.043 Uiso 0.5 1 d R . . A -1
C12 C 0.7200(4) 0.0056(5) 0.3922(2) 0.0308(7) Uani 0.5 1 d . . . A -1
H12A H 0.8087 -0.0280 0.4473 0.046 Uiso 0.5 1 d R . . A -1
H12B H 0.7344 -0.0732 0.3264 0.046 Uiso 0.5 1 d R . . A -1
H12C H 0.6104 -0.0207 0.4213 0.046 Uiso 0.5 1 d R . . A -1
C13 C 0.6933(4) 0.3465(5) 0.4617(2) 0.0294(7) Uani 0.5 1 d . . . A -1
H13A H 0.5896 0.3036 0.4898 0.044 Uiso 0.5 1 d R . . A -1
H13B H 0.7817 0.3338 0.5174 0.044 Uiso 0.5 1 d R . . A -1
H13C H 0.6858 0.4807 0.4391 0.044 Uiso 0.5 1 d R . . A -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B 0.0200(10) 0.0161(11) 0.0208(11) 0.000 -0.0004(8) 0.000
O1 0.0196(7) 0.0311(8) 0.0177(7) 0.000 -0.0020(5) 0.000
O2 0.0208(7) 0.0310(8) 0.0152(7) 0.000 -0.0022(5) 0.000
N1 0.0183(8) 0.0165(8) 0.0194(8) 0.000 -0.0017(6) 0.000
C1 0.0184(10) 0.0317(12) 0.0212(10) 0.000 0.0002(7) 0.000
C2 0.0207(10) 0.0359(12) 0.0173(9) 0.000 0.0024(7) 0.000
C3 0.0209(10) 0.0137(9) 0.0205(9) 0.000 -0.0026(7) 0.000
C4 0.0158(9) 0.0338(12) 0.0227(10) 0.000 -0.0004(7) 0.000
C5 0.0190(9) 0.0254(11) 0.0209(10) 0.000 0.0005(7) 0.000
C6 0.0171(11) 0.130(3) 0.0229(12) 0.000 0.0005(9) 0.000
C7 0.0192(11) 0.097(2) 0.0224(11) 0.000 0.0017(8) 0.000
C8 0.0220(11) 0.049(13) 0.0152(10) 0.003(2) -0.0041(8) 0.010(4)
C9 0.0218(11) 0.041(14) 0.0175(10) -0.006(3) -0.0041(8) -0.002(2)
C10 0.0231(14) 0.0397(18) 0.0284(15) 0.0030(13) -0.0033(11) 0.0080(13)
C11 0.0315(15) 0.0271(17) 0.0272(14) 0.0022(12) -0.0048(11) -0.0075(13)
C12 0.0379(17) 0.0282(17) 0.0257(14) 0.0033(13) -0.0045(12) -0.0048(13)
C13 0.0300(15) 0.0374(17) 0.0209(13) -0.0056(13) 0.0015(11) 0.0009(13)

_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
B O1 1.364(3) . ?
B O2 1.363(2) . ?
B C3 1.567(3) . ?
O1 C9 1.455(5) . ?
O2 C8 1.452(4) . ?
N1 C1 1.339(2) . ?
N1 C5 1.337(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.504(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.390(3) . ?
C5 C7 1.506(3) . ?
C8 C9 1.548(11) . ?
C8 C10 1.489(18) . ?
C8 C11 1.56(3) . ?
C9 C12 1.57(4) . ?
C9 C13 1.48(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
O1 B C3 122.94(17) . . ?
O2 B O1 114.05(16) . . ?
O2 B C3 123.01(17) . . ?
B O1 C9 107.43(17) . . ?
B O2 C8 107.44(17) . . ?
C5 N1 C1 117.84(16) . . ?
N1 C1 C2 122.45(18) . . ?
N1 C1 C6 115.93(17) . . ?
C2 C1 C6 121.62(18) . . ?
C3 C2 C1 120.33(18) . . ?
C2 C3 B 122.06(17) . . ?
C2 C3 C4 116.60(17) . . ?
C4 C3 B 121.35(17) . . ?
C3 C4 C5 120.54(18) . . ?
N1 C5 C4 122.24(18) . . ?
N1 C5 C7 116.16(17) . . ?
C4 C5 C7 121.60(18) . . ?
O2 C8 C9 103.9(6) . . ?
O2 C8 C10 110.6(12) . . ?
O2 C8 C11 103.7(14) . . ?
C9 C8 C11 110(2) . . ?
C10 C8 C9 118.1(19) . . ?
C10 C8 C11 109.6(8) . . ?
O1 C9 C8 103.8(6) . . ?
O1 C9 C12 102.7(16) . . ?
O1 C9 C13 110.9(14) . . ?
C8 C9 C12 110(2) . . ?
C13 C9 C8 118(2) . . ?
C13 C9 C12 109.8(9) . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_database_code_depnum_ccdc_archive 'CCDC 988600'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_39e

_audit_creation_date             2014-02-24
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_shelxl_version_number           2014-1
_chemical_name_common            2,3-Dichloro-5-(Bpin)-pyridine
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H14 B Cl2 N O2'
_chemical_formula_sum            'C11 H14 B Cl2 N O2'
_chemical_formula_weight         273.94
_chemical_melting_point          322
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.5381(4)
_cell_length_b                   21.3579(12)
_cell_length_c                   9.4192(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.137(2)
_cell_angle_gamma                90
_cell_volume                     1313.33(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    974
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      2.88
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombohedron
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18635
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_min         2.366
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SMART 6000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3283
_reflns_number_total             4008
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_cell_refinement       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.45 (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.2801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          
; Methyl groups were refined as rigid bodies rotating around C---C bonds, 
 with a common refined U for three H atoms. Other H atoms: riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H8A)=Uiso(H8B)=Uiso(H8C)=FVAR(1)
 Uiso(H9A)=Uiso(H9B)=Uiso(H9C)=FVAR(2)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(3)
 Uiso(H11A)=Uiso(H11B)=Uiso(H11C)=FVAR(4)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.15047(5) 1.14081(2) 0.52649(3) 0.02851(8) Uani 1 1 d . . . . .
Cl2 Cl 0.31112(5) 1.10773(2) 0.47458(4) 0.03210(9) Uani 1 1 d . . . . .
O1 O 0.13112(12) 0.87948(4) 0.90842(9) 0.02309(17) Uani 1 1 d . . . . .
O2 O 0.44678(12) 0.90714(4) 0.83368(9) 0.02157(16) Uani 1 1 d . . . . .
B B 0.2429(2) 0.92040(6) 0.83270(13) 0.0204(2) Uani 1 1 d . . . . .
C1 C -0.03213(18) 1.07733(5) 0.61177(12) 0.0211(2) Uani 1 1 d . . . . .
C2 C 0.17194(17) 1.06413(5) 0.58920(12) 0.0208(2) Uani 1 1 d . . . . .
C3 C 0.26265(17) 1.01373(5) 0.66135(12) 0.0211(2) Uani 1 1 d . . . . .
H3 H 0.4023 1.0038 0.6497 0.025 Uiso 1 1 calc R . . . .
C4 C 0.14644(17) 0.97779(5) 0.75137(12) 0.0203(2) Uani 1 1 d . . . . .
C5 C -0.05747(18) 0.99537(5) 0.76337(13) 0.0241(2) Uani 1 1 d . . . . .
H5 H -0.1385 0.9710 0.8232 0.029 Uiso 1 1 calc R . . . .
N N -0.14682(16) 1.04442(5) 0.69601(11) 0.0250(2) Uani 1 1 d . . . . .
C6 C 0.26782(17) 0.82679(5) 0.94563(12) 0.0209(2) Uani 1 1 d . . . . .
C7 C 0.48432(17) 0.85690(5) 0.93806(12) 0.0197(2) Uani 1 1 d . . . . .
C8 C 0.22418(19) 0.77625(6) 0.83404(14) 0.0278(3) Uani 1 1 d . . . . .
H8A H 0.0787 0.7650 0.8319 0.037(2) Uiso 1 1 calc GR . . . .
H8B H 0.3076 0.7392 0.8579 0.037(2) Uiso 1 1 calc GR . . . .
H8C H 0.2582 0.7920 0.7405 0.037(2) Uiso 1 1 calc GR . . . .
C9 C 0.2179(2) 0.80296(7) 1.09152(14) 0.0324(3) Uani 1 1 d . . . . .
H9A H 0.2315 0.8373 1.1605 0.042(3) Uiso 1 1 calc GR . . . .
H9B H 0.3128 0.7692 1.1203 0.042(3) Uiso 1 1 calc GR . . . .
H9C H 0.0771 0.7870 1.0879 0.042(3) Uiso 1 1 calc GR . . . .
C10 C 0.5613(2) 0.88833(6) 1.07598(14) 0.0316(3) Uani 1 1 d . . . . .
H10A H 0.6842 0.9129 1.0591 0.045(3) Uiso 1 1 calc GR . . . .
H10B H 0.5946 0.8563 1.1480 0.045(3) Uiso 1 1 calc GR . . . .
H10C H 0.4546 0.9160 1.1096 0.045(3) Uiso 1 1 calc GR . . . .
C11 C 0.64764(19) 0.81402(6) 0.88421(15) 0.0272(2) Uani 1 1 d . . . . .
H11A H 0.6051 0.7992 0.7887 0.038(3) Uiso 1 1 calc GR . . . .
H11B H 0.6665 0.7781 0.9484 0.038(3) Uiso 1 1 calc GR . . . .
H11C H 0.7769 0.8370 0.8807 0.038(3) Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.03247(16) 0.02131(13) 0.03140(15) 0.00410(11) -0.00148(12) 0.00477(10)
Cl2 0.03123(16) 0.02903(15) 0.03676(17) 0.01003(12) 0.00845(12) -0.00418(11)
O1 0.0195(4) 0.0225(4) 0.0274(4) 0.0054(3) 0.0027(3) 0.0025(3)
O2 0.0206(4) 0.0195(4) 0.0248(4) 0.0042(3) 0.0037(3) 0.0003(3)
B 0.0219(6) 0.0195(5) 0.0199(5) -0.0011(4) 0.0017(4) 0.0004(4)
C1 0.0251(5) 0.0169(5) 0.0211(5) -0.0006(4) -0.0013(4) 0.0012(4)
C2 0.0237(5) 0.0181(5) 0.0208(5) -0.0002(4) 0.0023(4) -0.0037(4)
C3 0.0208(5) 0.0190(5) 0.0234(5) -0.0014(4) 0.0010(4) -0.0002(4)
C4 0.0235(5) 0.0175(5) 0.0201(5) -0.0012(4) 0.0009(4) 0.0003(4)
C5 0.0245(5) 0.0225(5) 0.0259(5) 0.0029(4) 0.0049(4) 0.0007(4)
N 0.0248(5) 0.0232(5) 0.0272(5) 0.0024(4) 0.0042(4) 0.0029(4)
C6 0.0195(5) 0.0203(5) 0.0228(5) 0.0044(4) 0.0008(4) 0.0012(4)
C7 0.0197(5) 0.0185(5) 0.0210(5) 0.0018(4) 0.0004(4) -0.0003(4)
C8 0.0269(6) 0.0205(5) 0.0354(6) 0.0009(5) -0.0055(5) -0.0027(4)
C9 0.0281(6) 0.0404(7) 0.0292(6) 0.0144(5) 0.0058(5) 0.0008(5)
C10 0.0324(6) 0.0341(7) 0.0275(6) -0.0049(5) -0.0060(5) -0.0028(5)
C11 0.0214(5) 0.0226(5) 0.0380(7) 0.0010(5) 0.0044(5) 0.0026(4)

_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
Cl1 C1 1.7363(11) . ?
Cl2 C2 1.7230(11) . ?
O1 B 1.3651(15) . ?
O1 C6 1.4676(13) . ?
O2 B 1.3623(15) . ?
O2 C7 1.4670(13) . ?
B C4 1.5601(17) . ?
C1 C2 1.3914(16) . ?
C1 N 1.3232(15) . ?
C2 C3 1.3886(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3986(16) . ?
C4 C5 1.3956(16) . ?
C5 H5 0.9500 . ?
C5 N 1.3420(15) . ?
C6 C7 1.5600(16) . ?
C6 C8 1.5227(17) . ?
C6 C9 1.5176(16) . ?
C7 C10 1.5231(16) . ?
C7 C11 1.5151(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
B O1 C6 106.22(9) . . ?
B O2 C7 106.52(8) . . ?
O1 B C4 123.09(10) . . ?
O2 B O1 114.52(10) . . ?
O2 B C4 122.40(10) . . ?
C2 C1 Cl1 119.62(9) . . ?
N C1 Cl1 116.07(9) . . ?
N C1 C2 124.31(10) . . ?
C1 C2 Cl2 122.01(9) . . ?
C3 C2 Cl2 119.98(9) . . ?
C3 C2 C1 118.02(10) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.38(10) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 B 120.70(10) . . ?
C5 C4 B 122.27(10) . . ?
C5 C4 C3 117.04(10) . . ?
C4 C5 H5 117.8 . . ?
N C5 C4 124.39(11) . . ?
N C5 H5 117.8 . . ?
C1 N C5 116.87(10) . . ?
O1 C6 C7 102.43(8) . . ?
O1 C6 C8 106.86(9) . . ?
O1 C6 C9 108.37(10) . . ?
C8 C6 C7 113.39(9) . . ?
C9 C6 C7 114.86(10) . . ?
C9 C6 C8 110.23(10) . . ?
O2 C7 C6 102.31(8) . . ?
O2 C7 C10 106.54(9) . . ?
O2 C7 C11 108.23(9) . . ?
C10 C7 C6 113.64(10) . . ?
C11 C7 C6 115.08(9) . . ?
C11 C7 C10 110.24(10) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_database_code_depnum_ccdc_archive 'CCDC 988601'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_S3

_audit_creation_date             2014-02-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 2-methyl-4-phenyl-pyridine
;
_chemical_formula_moiety         'C12 H11 N'
_chemical_formula_sum            'C12 H11 N'
_chemical_formula_weight         169.22
_chemical_melting_point          316

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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   7.4760(6)
_cell_length_b                   20.8897(14)
_cell_length_c                   23.5283(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3674.4(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4735
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.6
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0400 before and 0.0374 after correction.
The Ratio of minimum to maximum transmission is 0.7988.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_exptl_special_details           
;The data collection nominally covered full sphere of reciprocal 
space, by a combination of 3 sets of ω scans; each set at different 
φ angles and each scan (30 sec exposure) covering 0.3° in ω. 
Crystal to detector distance 4.87 cm. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30673
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.731
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2868
_reflns_number_total             4220
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT version 6.02A (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.3390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          
; Methyl groups were refined as rigid bodies rotating around C---C bonds, 
 with a common refined U for three H atoms. Other H atoms: riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H1A)=Uiso(H1B)=Uiso(H1C)=FVAR(1)
 Uiso(H1'A)=Uiso(H1'B)=Uiso(H1'C)=FVAR(2)
3.a Riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C3'(H3'), C5'(H5'), C6'(H6'), C8'(H8'), C9'(H9'), C10'(H10'), C11'(H11'),
 C12'(H12')
3.b Rotating group:
 C1(H1A,H1B,H1C), C1'(H1'A,H1'B,H1'C)
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

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
N1 N 0.48981(16) 0.07433(5) 0.31270(5) 0.0317(3) Uani 1 1 d . . . . .
C1 C 0.4490(2) 0.06270(7) 0.21149(7) 0.0372(4) Uani 1 1 d . . . . .
H1A H 0.5714 0.0620 0.1966 0.062(3) Uiso 1 1 d GR . . . .
H1B H 0.3684 0.0805 0.1827 0.062(3) Uiso 1 1 d GR . . . .
H1C H 0.4114 0.0190 0.2209 0.062(3) Uiso 1 1 d GR . . . .
C2 C 0.44227(17) 0.10340(6) 0.26400(6) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.39449(17) 0.16788(6) 0.26217(6) 0.0253(3) Uani 1 1 d . . . . .
H3 H 0.3608 0.1867 0.2270 0.030 Uiso 1 1 d R . . . .
C4 C 0.39564(17) 0.20498(6) 0.31137(6) 0.0235(3) Uani 1 1 d . . . . .
C5 C 0.44781(18) 0.17431(7) 0.36140(6) 0.0295(3) Uani 1 1 d . . . . .
H5 H 0.4525 0.1973 0.3962 0.035 Uiso 1 1 d R . . . .
C6 C 0.4924(2) 0.11032(7) 0.35969(6) 0.0332(3) Uani 1 1 d . . . . .
H6 H 0.5274 0.0904 0.3943 0.040 Uiso 1 1 d R . . . .
C7 C 0.34546(17) 0.27411(6) 0.31134(5) 0.0228(3) Uani 1 1 d . . . . .
C8 C 0.23278(17) 0.29919(6) 0.26970(6) 0.0257(3) Uani 1 1 d . . . . .
H8 H 0.1900 0.2721 0.2402 0.031 Uiso 1 1 d R . . . .
C9 C 0.18221(18) 0.36311(6) 0.27068(6) 0.0288(3) Uani 1 1 d . . . . .
H9 H 0.1046 0.3794 0.2421 0.035 Uiso 1 1 d R . . . .
C10 C 0.24455(19) 0.40338(7) 0.31317(6) 0.0314(3) Uani 1 1 d . . . . .
H10 H 0.2088 0.4470 0.3142 0.038 Uiso 1 1 d R . . . .
C11 C 0.35946(19) 0.37922(7) 0.35401(6) 0.0323(3) Uani 1 1 d . . . . .
H11 H 0.4047 0.4067 0.3828 0.039 Uiso 1 1 d R . . . .
C12 C 0.40909(18) 0.31533(7) 0.35335(6) 0.0284(3) Uani 1 1 d . . . . .
H12 H 0.4874 0.2994 0.3819 0.034 Uiso 1 1 d R . . . .
N1' N 0.28125(16) 0.00826(5) 0.56094(5) 0.0312(3) Uani 1 1 d . . . . .
C1' C 0.2287(2) 0.00344(7) 0.45969(7) 0.0360(4) Uani 1 1 d . . . . .
H1'A H 0.3281 -0.0260 0.4525 0.075(4) Uiso 1 1 d GR . . . .
H1'B H 0.2150 0.0325 0.4273 0.075(4) Uiso 1 1 d GR . . . .
H1'C H 0.1181 -0.0211 0.4649 0.075(4) Uiso 1 1 d GR . . . .
C2' C 0.26672(17) 0.04173(6) 0.51246(6) 0.0270(3) Uani 1 1 d . . . . .
C3' C 0.28532(17) 0.10808(6) 0.51079(6) 0.0241(3) Uani 1 1 d . . . . .
H3' H 0.2750 0.1300 0.4756 0.029 Uiso 1 1 d R . . . .
C4' C 0.31892(16) 0.14247(6) 0.56032(5) 0.0219(3) Uani 1 1 d . . . . .
C5' C 0.33340(17) 0.10729(6) 0.61037(6) 0.0259(3) Uani 1 1 d . . . . .
H5' H 0.3560 0.1283 0.6455 0.031 Uiso 1 1 d R . . . .
C6' C 0.31461(19) 0.04150(6) 0.60843(6) 0.0305(3) Uani 1 1 d . . . . .
H6' H 0.3260 0.0184 0.6430 0.037 Uiso 1 1 d R . . . .
C7' C 0.33845(16) 0.21335(6) 0.56003(5) 0.0216(3) Uani 1 1 d . . . . .
C8' C 0.25121(17) 0.25076(6) 0.51959(6) 0.0252(3) Uani 1 1 d . . . . .
H8' H 0.1788 0.2308 0.4916 0.030 Uiso 1 1 d R . . . .
C9' C 0.26884(18) 0.31695(6) 0.51978(6) 0.0297(3) Uani 1 1 d . . . . .
H9' H 0.2082 0.3419 0.4921 0.036 Uiso 1 1 d R . . . .
C10' C 0.37488(18) 0.34659(6) 0.56032(6) 0.0297(3) Uani 1 1 d . . . . .
H10' H 0.3867 0.3919 0.5606 0.036 Uiso 1 1 d R . . . .
C11' C 0.46336(18) 0.30983(6) 0.60036(6) 0.0277(3) Uani 1 1 d . . . . .
H11' H 0.5372 0.3300 0.6279 0.033 Uiso 1 1 d R . . . .
C12' C 0.44509(17) 0.24377(6) 0.60057(6) 0.0243(3) Uani 1 1 d . . . . .
H12' H 0.5056 0.2191 0.6285 0.029 Uiso 1 1 d R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0319(6) 0.0281(6) 0.0352(7) 0.0051(5) -0.0038(5) 0.0002(5)
C1 0.0462(9) 0.0272(8) 0.0384(9) -0.0027(6) -0.0064(7) 0.0014(7)
C2 0.0245(7) 0.0255(7) 0.0302(8) 0.0024(6) -0.0016(6) -0.0025(5)
C3 0.0233(6) 0.0268(7) 0.0257(7) 0.0041(5) -0.0021(5) -0.0014(5)
C4 0.0176(6) 0.0262(7) 0.0268(7) 0.0019(5) 0.0010(5) -0.0022(5)
C5 0.0308(7) 0.0325(8) 0.0254(7) 0.0011(6) -0.0018(6) 0.0006(6)
C6 0.0360(8) 0.0339(8) 0.0297(8) 0.0088(6) -0.0047(6) 0.0009(6)
C7 0.0196(6) 0.0268(7) 0.0220(7) 0.0009(5) 0.0030(5) -0.0003(5)
C8 0.0240(6) 0.0286(7) 0.0244(7) -0.0005(5) -0.0006(5) -0.0020(5)
C9 0.0249(7) 0.0291(7) 0.0324(8) 0.0033(6) -0.0010(6) 0.0021(6)
C10 0.0283(7) 0.0267(7) 0.0392(8) -0.0006(6) 0.0064(6) 0.0033(6)
C11 0.0319(8) 0.0341(8) 0.0309(8) -0.0096(6) 0.0022(6) 0.0007(6)
C12 0.0264(7) 0.0344(8) 0.0245(7) -0.0019(6) -0.0009(6) 0.0018(6)
N1' 0.0307(6) 0.0234(6) 0.0394(7) 0.0031(5) 0.0000(5) 0.0000(5)
C1' 0.0376(8) 0.0292(8) 0.0413(9) -0.0081(7) -0.0003(7) -0.0036(6)
C2' 0.0229(6) 0.0244(7) 0.0337(8) -0.0018(6) -0.0003(6) 0.0001(5)
C3' 0.0244(6) 0.0237(7) 0.0240(7) 0.0018(5) -0.0012(5) 0.0003(5)
C4' 0.0180(6) 0.0223(7) 0.0253(7) 0.0015(5) 0.0005(5) 0.0004(5)
C5' 0.0267(7) 0.0264(7) 0.0247(7) 0.0018(6) -0.0008(6) 0.0013(6)
C6' 0.0321(7) 0.0276(7) 0.0318(8) 0.0094(6) 0.0006(6) 0.0008(6)
C7' 0.0213(6) 0.0218(7) 0.0217(7) 0.0009(5) 0.0031(5) -0.0006(5)
C8' 0.0267(7) 0.0239(7) 0.0251(7) 0.0011(6) -0.0025(6) -0.0007(5)
C9' 0.0311(7) 0.0256(7) 0.0322(8) 0.0066(6) -0.0010(6) 0.0037(6)
C10' 0.0306(7) 0.0199(6) 0.0385(8) -0.0014(6) 0.0074(6) -0.0009(6)
C11' 0.0264(7) 0.0282(7) 0.0285(8) -0.0062(6) 0.0023(6) -0.0037(6)
C12' 0.0242(6) 0.0273(7) 0.0214(7) 0.0004(5) 0.0004(5) 0.0005(5)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3446(17) . ?
N1 C6 1.3371(18) . ?
C1 C2 1.5006(19) . ?
C2 C3 1.3943(18) . ?
C3 C4 1.3931(18) . ?
C4 C5 1.3958(19) . ?
C4 C7 1.4921(18) . ?
C5 C6 1.3783(19) . ?
C7 C8 1.3943(18) . ?
C7 C12 1.3945(18) . ?
C8 C9 1.3880(18) . ?
C9 C10 1.3872(19) . ?
C10 C11 1.384(2) . ?
C11 C12 1.3852(19) . ?
N1' C2' 1.3424(18) . ?
N1' C6' 1.3390(18) . ?
C1' C2' 1.504(2) . ?
C2' C3' 1.3935(18) . ?
C3' C4' 1.3920(17) . ?
C4' C5' 1.3922(17) . ?
C4' C7' 1.4879(17) . ?
C5' C6' 1.3822(18) . ?
C7' C8' 1.3936(18) . ?
C7' C12' 1.3961(18) . ?
C8' C9' 1.3889(18) . ?
C9' C10' 1.386(2) . ?
C10' C11' 1.384(2) . ?
C11' C12' 1.3867(18) . ?

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
C6 N1 C2 117.04(12) . . ?
N1 C2 C1 115.90(12) . . ?
N1 C2 C3 122.03(13) . . ?
C3 C2 C1 122.04(12) . . ?
C4 C3 C2 120.67(12) . . ?
C3 C4 C5 116.56(12) . . ?
C3 C4 C7 122.45(12) . . ?
C5 C4 C7 120.99(12) . . ?
C6 C5 C4 119.22(13) . . ?
N1 C6 C5 124.47(13) . . ?
C8 C7 C4 121.05(12) . . ?
C8 C7 C12 118.18(12) . . ?
C12 C7 C4 120.77(12) . . ?
C9 C8 C7 120.95(13) . . ?
C10 C9 C8 120.25(13) . . ?
C11 C10 C9 119.20(13) . . ?
C10 C11 C12 120.64(13) . . ?
C11 C12 C7 120.76(13) . . ?
C6' N1' C2' 117.00(12) . . ?
N1' C2' C1' 116.09(12) . . ?
N1' C2' C3' 122.28(13) . . ?
C3' C2' C1' 121.64(13) . . ?
C4' C3' C2' 120.51(12) . . ?
C3' C4' C5' 116.73(12) . . ?
C3' C4' C7' 121.84(12) . . ?
C5' C4' C7' 121.43(12) . . ?
C6' C5' C4' 119.27(13) . . ?
N1' C6' C5' 124.21(13) . . ?
C8' C7' C4' 121.02(12) . . ?
C8' C7' C12' 118.58(12) . . ?
C12' C7' C4' 120.40(11) . . ?
C9' C8' C7' 120.78(13) . . ?
C10' C9' C8' 120.08(13) . . ?
C11' C10' C9' 119.60(12) . . ?
C10' C11' C12' 120.50(13) . . ?
C11' C12' C7' 120.46(12) . . ?

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
C3 C4 C7 C8 24.96(19) . . . . ?
C3' C4' C7' C8' 28.69(18) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 988602'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_S12

_audit_creation_date             2014-02-24
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 2,6-Dimethyl-4-naphthalen-1-yl-pyridine
;
_chemical_formula_moiety         'C17 H15 N'
_chemical_formula_sum            'C17 H15 N'
_chemical_formula_weight         233.30
_chemical_melting_point          364
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.2252(16)
_cell_length_b                   15.438(2)
_cell_length_c                   7.6917(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.874(4)
_cell_angle_gamma                90
_cell_volume                     1268.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1176
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      21.0
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_special_details           
; The data collection nominally covered full sphere of reciprocal 
space, by a combination of 3 sets of ω scans; each set at different 
φ angles and each scan (10 sec exposure) covering 0.3° in ω. 
Crystal to detector distance 4.86 cm. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11358
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.242
_diffrn_reflns_theta_min         1.906
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1286
_reflns_number_total             2236
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT version 6.02A (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelxS (Sheldrick, 2008)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      0.905
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1215
_refine_special_details          
; Methyl groups were refined as rigid bodies rotating around 
C---C bonds, with a common refined U for three H atoms. Other H atoms: 
riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H1A)=Uiso(H1B)=Uiso(H1C)=FVAR(1)
 Uiso(H7A)=Uiso(H7B)=Uiso(H7C)=FVAR(2)
3.a Rotating group:
 C1(H1A,H1B,H1C)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

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
N N 0.00107(15) 0.87587(11) 0.1104(2) 0.0333(5) Uani 1 1 d . . . . .
C1 C -0.1426(2) 0.77031(15) -0.0747(3) 0.0471(7) Uani 1 1 d . . . . .
H1A H -0.2010 0.7848 -0.0070 0.097(6) Uiso 1 1 d GR . . . .
H1B H -0.1456 0.7079 -0.0986 0.097(6) Uiso 1 1 d GR . . . .
H1C H -0.1663 0.8018 -0.1910 0.097(6) Uiso 1 1 d GR . . . .
C2 C -0.01157(19) 0.79574(14) 0.0366(3) 0.0333(5) Uani 1 1 d . . . . .
C3 C 0.08930(19) 0.74090(14) 0.0574(3) 0.0336(5) Uani 1 1 d . . . . .
H3 H 0.0767 0.6848 0.0041 0.040 Uiso 1 1 calc R . . . .
C4 C 0.20964(18) 0.76800(13) 0.1569(3) 0.0299(5) Uani 1 1 d . . . . .
C5 C 0.22125(19) 0.85015(13) 0.2317(3) 0.0303(5) Uani 1 1 d . . . . .
H5 H 0.3015 0.8712 0.2998 0.036 Uiso 1 1 calc R . . . .
C6 C 0.11708(19) 0.90182(13) 0.2081(3) 0.0313(5) Uani 1 1 d . . . . .
C7 C 0.1264(2) 0.99120(13) 0.2891(3) 0.0405(6) Uani 1 1 d . . . . .
H7A H 0.1152 1.0345 0.1922 0.068(5) Uiso 1 1 calc GR . . . .
H7B H 0.2090 0.9987 0.3797 0.068(5) Uiso 1 1 calc GR . . . .
H7C H 0.0613 0.9987 0.3484 0.068(5) Uiso 1 1 calc GR . . . .
C11 C 0.32170(18) 0.71329(13) 0.1706(3) 0.0289(5) Uani 1 1 d . . . . .
C12 C 0.42032(18) 0.74891(13) 0.1269(3) 0.0311(5) Uani 1 1 d . . . . .
H12 H 0.4183 0.8090 0.0993 0.037 Uiso 1 1 calc R . . . .
C13 C 0.52464(19) 0.69991(14) 0.1213(3) 0.0354(6) Uani 1 1 d . . . . .
H13 H 0.5909 0.7265 0.0883 0.043 Uiso 1 1 calc R . . . .
C14 C 0.5301(2) 0.61350(15) 0.1636(3) 0.0400(6) Uani 1 1 d . . . . .
H14 H 0.6002 0.5802 0.1590 0.048 Uiso 1 1 calc R . . . .
C15 C 0.4362(2) 0.48470(14) 0.2596(3) 0.0413(6) Uani 1 1 d . . . . .
H15 H 0.5051 0.4507 0.2524 0.050 Uiso 1 1 calc R . . . .
C16 C 0.3442(2) 0.44704(15) 0.3133(3) 0.0451(6) Uani 1 1 d . . . . .
H16 H 0.3480 0.3869 0.3404 0.054 Uiso 1 1 calc R . . . .
C17 C 0.2435(2) 0.49677(14) 0.3287(3) 0.0376(6) Uani 1 1 d . . . . .
H17 H 0.1811 0.4705 0.3712 0.045 Uiso 1 1 calc R . . . .
C18 C 0.23397(19) 0.58245(13) 0.2835(3) 0.0327(5) Uani 1 1 d . . . . .
H18 H 0.1647 0.6150 0.2941 0.039 Uiso 1 1 calc R . . . .
C19 C 0.32685(19) 0.62398(13) 0.2205(3) 0.0315(5) Uani 1 1 d . . . . .
C20 C 0.43175(18) 0.57334(13) 0.2143(3) 0.0309(5) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N 0.0307(10) 0.0348(11) 0.0334(10) 0.0006(9) 0.0080(8) 0.0042(9)
C1 0.0361(14) 0.0522(16) 0.0488(16) -0.0076(12) 0.0068(12) 0.0009(12)
C2 0.0308(13) 0.0378(13) 0.0310(12) 0.0000(10) 0.0091(10) 0.0009(11)
C3 0.0368(13) 0.0333(13) 0.0318(12) -0.0035(10) 0.0118(10) 0.0008(11)
C4 0.0312(12) 0.0336(12) 0.0254(11) 0.0027(10) 0.0095(9) 0.0029(10)
C5 0.0283(12) 0.0349(13) 0.0275(12) 0.0038(9) 0.0084(9) -0.0015(10)
C6 0.0313(12) 0.0349(12) 0.0287(12) 0.0037(10) 0.0105(10) 0.0031(10)
C7 0.0441(14) 0.0336(13) 0.0415(14) 0.0034(11) 0.0099(11) 0.0045(11)
C11 0.0271(12) 0.0318(12) 0.0254(11) -0.0034(9) 0.0046(9) -0.0014(10)
C12 0.0290(11) 0.0338(12) 0.0292(12) 0.0001(10) 0.0072(9) -0.0022(10)
C13 0.0277(12) 0.0407(14) 0.0391(13) -0.0029(11) 0.0119(10) -0.0041(10)
C14 0.0302(13) 0.0462(15) 0.0419(14) -0.0038(11) 0.0083(11) 0.0065(11)
C15 0.0380(14) 0.0372(14) 0.0456(15) 0.0012(11) 0.0084(11) 0.0063(11)
C16 0.0498(16) 0.0311(13) 0.0520(16) 0.0030(11) 0.0120(13) 0.0005(12)
C17 0.0384(13) 0.0363(13) 0.0377(13) 0.0032(11) 0.0109(11) -0.0034(11)
C18 0.0324(12) 0.0337(13) 0.0315(12) -0.0023(10) 0.0092(10) -0.0018(10)
C19 0.0336(12) 0.0333(12) 0.0247(11) -0.0042(9) 0.0046(10) 0.0013(10)
C20 0.0293(12) 0.0309(12) 0.0305(12) -0.0014(10) 0.0064(10) 0.0033(10)

_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
N C2 1.350(3) . ?
N C6 1.349(3) . ?
C1 H1A 0.9801 . ?
C1 H1B 0.9799 . ?
C1 H1C 0.9800 . ?
C1 C2 1.509(3) . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C4 C5 1.382(3) . ?
C4 C11 1.492(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(3) . ?
C6 C7 1.505(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 C12 1.367(3) . ?
C11 C19 1.428(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.406(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.370(3) . ?
C14 H14 0.9500 . ?
C14 C20 1.421(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.355(3) . ?
C15 C20 1.409(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.402(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.363(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.429(3) . ?
C19 C20 1.426(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
C6 N C2 117.71(17) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N C2 C1 115.80(18) . . ?
N C2 C3 122.38(19) . . ?
C3 C2 C1 121.8(2) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C11 121.45(18) . . ?
C5 C4 C3 117.04(19) . . ?
C5 C4 C11 121.36(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
N C6 C5 122.37(19) . . ?
N C6 C7 115.84(18) . . ?
C5 C6 C7 121.8(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C11 C4 118.94(18) . . ?
C12 C11 C19 119.05(19) . . ?
C19 C11 C4 121.96(18) . . ?
C11 C12 H12 118.8 . . ?
C11 C12 C13 122.4(2) . . ?
C13 C12 H12 118.8 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C20 120.5(2) . . ?
C20 C14 H14 119.7 . . ?
C16 C15 H15 119.3 . . ?
C16 C15 C20 121.3(2) . . ?
C20 C15 H15 119.3 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.9(2) . . ?
C19 C18 H18 119.6 . . ?
C11 C19 C18 123.42(19) . . ?
C20 C19 C11 119.08(19) . . ?
C20 C19 C18 117.46(19) . . ?
C14 C20 C19 119.27(19) . . ?
C15 C20 C14 121.33(19) . . ?
C15 C20 C19 119.40(19) . . ?

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
C3 C4 C11 C19 -50.0(3) . . . . ?
C5 C4 C11 C12 -48.1(3) . . . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_database_code_depnum_ccdc_archive 'CCDC 988603'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_S13

_audit_creation_date             2014-02-24
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 4,4'-bis(Bpin)-2,2'-bipyridine
;
_chemical_formula_moiety         'C22 H30 B2 N2 O4'
_chemical_formula_sum            'C22 H30 B2 N2 O4'
_chemical_formula_weight         408.10
_chemical_absolute_configuration unk
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0010 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   20.849(4)
_cell_length_b                   6.6532(12)
_cell_length_c                   15.874(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2201.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    793
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      3.23
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             872
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10891
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.954
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                2515
_reflns_number_total             3720
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'SMART version 4.05 (Siemens, 1995)'
_computing_cell_refinement       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.45 (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 879 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Absolute polarity undeterminable.
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     154
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0693
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0908P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1724
_refine_special_details          
; Methyl groups were refined as rigid bodies rotating around C---C bonds, 
 with a common refined U for three H atoms. Other H atoms: riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Rigid body (RIGU) restrains
 C18, O3, O4, C20, C19, C22, C21, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, C1, C13, C14, C15, C16, B2, N1, C2, C3, C4, C5, C6, B1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Uiso(H9A)=Uiso(H9B)=Uiso(H9C)=FVAR(1)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(2)
 Uiso(H11A)=Uiso(H11B)=Uiso(H11C)=FVAR(3)
 Uiso(H12A)=Uiso(H12B)=Uiso(H12C)=FVAR(4)
 Uiso(H19A)=Uiso(H19B)=Uiso(H19C)=FVAR(5)
 Uiso(H20A)=Uiso(H20B)=Uiso(H20C)=FVAR(6)
 Uiso(H21A)=Uiso(H21B)=Uiso(H21C)=FVAR(7)
 Uiso(H22A)=Uiso(H22B)=Uiso(H22C)=FVAR(8)
5.a Rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,
 H22B,H22C)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C13(H13), C15(H15), C16(H16)
;

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

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
O1 O 0.5708(2) 0.9348(7) 0.1512(3) 0.0250(12) Uani 1 1 d . . . . .
O2 O 0.6167(2) 0.6203(8) 0.1473(3) 0.0271(12) Uani 1 1 d . . . . .
O3 O 0.1732(2) 0.5801(7) 0.4372(3) 0.0220(11) Uani 1 1 d . . . . .
O4 O 0.1352(2) 0.9007(7) 0.4474(3) 0.0253(12) Uani 1 1 d . . . . .
N1 N 0.4016(3) 0.4989(9) 0.3112(4) 0.0209(13) Uani 1 1 d . . . . .
N2 N 0.3467(3) 1.0038(9) 0.2762(3) 0.0214(13) Uani 1 1 d . . . . .
B1 B 0.5667(4) 0.7376(11) 0.1736(6) 0.016(2) Uani 1 1 d . . . . .
B2 B 0.1819(5) 0.7749(13) 0.4173(6) 0.019(2) Uani 1 1 d . . . . .
C1 C 0.3445(3) 0.8125(12) 0.3035(4) 0.0180(14) Uani 1 1 d . . . . .
C2 C 0.4028(3) 0.6899(12) 0.2847(5) 0.0208(15) Uani 1 1 d . . . . .
C3 C 0.4549(4) 0.7679(10) 0.2409(5) 0.0155(18) Uani 1 1 d . . . . .
H3 H 0.4541 0.9039 0.2227 0.019 Uiso 1 1 calc R . . . .
C4 C 0.5080(3) 0.6496(11) 0.2234(4) 0.0200(15) Uani 1 1 d . . . . .
C5 C 0.5061(3) 0.4526(10) 0.2511(4) 0.0206(14) Uani 1 1 d . . . . .
H5 H 0.5412 0.3655 0.2403 0.025 Uiso 1 1 calc R . . . .
C6 C 0.4529(3) 0.3821(11) 0.2946(4) 0.0243(16) Uani 1 1 d . . . . .
H6 H 0.4526 0.2465 0.3134 0.029 Uiso 1 1 calc R . . . .
C7 C 0.6547(4) 0.7467(10) 0.0891(6) 0.019(2) Uani 1 1 d . . . . .
C8 C 0.6354(3) 0.9631(12) 0.1189(5) 0.0249(17) Uani 1 1 d . . . . .
C9 C 0.6764(4) 1.0370(13) 0.1921(5) 0.039(2) Uani 1 1 d . . . . .
H9A H 0.6608 1.1684 0.2110 0.049(13) Uiso 1 1 d GR . . . .
H9B H 0.7211 1.0491 0.1737 0.049(13) Uiso 1 1 d GR . . . .
H9C H 0.6737 0.9408 0.2388 0.049(13) Uiso 1 1 d GR . . . .
C10 C 0.6354(4) 1.1204(13) 0.0507(5) 0.038(2) Uani 1 1 d . . . . .
H10A H 0.6194 1.2476 0.0735 0.033(13) Uiso 1 1 d GR . . . .
H10B H 0.6078 1.0765 0.0043 0.033(13) Uiso 1 1 d GR . . . .
H10C H 0.6793 1.1392 0.0298 0.033(13) Uiso 1 1 d GR . . . .
C11 C 0.6297(4) 0.7026(15) 0.0026(5) 0.037(2) Uani 1 1 d . . . . .
H11A H 0.6345 0.5588 -0.0093 0.046(15) Uiso 1 1 d GR . . . .
H11B H 0.6539 0.7804 -0.0391 0.046(15) Uiso 1 1 d GR . . . .
H11C H 0.5842 0.7394 -0.0004 0.046(15) Uiso 1 1 d GR . . . .
C12 C 0.7247(4) 0.6944(14) 0.0988(6) 0.041(2) Uani 1 1 d . . . . .
H12A H 0.7375 0.7131 0.1577 0.058(15) Uiso 1 1 d GR . . . .
H12B H 0.7506 0.7821 0.0626 0.058(15) Uiso 1 1 d GR . . . .
H12C H 0.7315 0.5540 0.0825 0.058(15) Uiso 1 1 d GR . . . .
C13 C 0.2922(4) 0.7371(10) 0.3468(5) 0.0167(19) Uani 1 1 d . . . . .
H13 H 0.2920 0.6003 0.3639 0.020 Uiso 1 1 calc R . . . .
C14 C 0.2402(3) 0.8583(11) 0.3655(4) 0.0194(14) Uani 1 1 d . . . . .
C15 C 0.2430(3) 1.0575(11) 0.3387(4) 0.0229(15) Uani 1 1 d . . . . .
H15 H 0.2089 1.1477 0.3509 0.027 Uiso 1 1 calc R . . . .
C16 C 0.2962(3) 1.1217(11) 0.2941(5) 0.0239(16) Uani 1 1 d . . . . .
H16 H 0.2970 1.2569 0.2749 0.029 Uiso 1 1 calc R . . . .
C17 C 0.0973(4) 0.7770(11) 0.5062(6) 0.0213(19) Uani 1 1 d . U . . .
C18 C 0.1091(3) 0.5642(11) 0.4735(5) 0.0213(15) Uani 1 1 d . . . . .
C19 C 0.0651(3) 0.5051(14) 0.4016(5) 0.035(2) Uani 1 1 d . . . . .
H19A H 0.0811 0.3819 0.3752 0.048(14) Uiso 1 1 d GR . . . .
H19B H 0.0640 0.6134 0.3598 0.048(14) Uiso 1 1 d GR . . . .
H19C H 0.0217 0.4817 0.4233 0.048(14) Uiso 1 1 d GR . . . .
C20 C 0.1096(3) 0.3997(11) 0.5402(4) 0.0276(17) Uani 1 1 d . . . . .
H20A H 0.1202 0.2708 0.5137 0.044(14) Uiso 1 1 d GR . . . .
H20B H 0.0673 0.3907 0.5667 0.044(14) Uiso 1 1 d GR . . . .
H20C H 0.1419 0.4313 0.5832 0.044(14) Uiso 1 1 d GR . . . .
C21 C 0.0278(3) 0.8497(12) 0.5042(5) 0.0362(19) Uani 1 1 d . . . . .
H21A H 0.0257 0.9879 0.5254 0.027(11) Uiso 1 1 d GR . . . .
H21B H 0.0014 0.7623 0.5398 0.027(11) Uiso 1 1 d GR . . . .
H21C H 0.0117 0.8457 0.4462 0.027(11) Uiso 1 1 d GR . . . .
C22 C 0.1258(4) 0.8156(14) 0.5940(5) 0.0322(19) Uani 1 1 d . . . . .
H22A H 0.1706 0.7710 0.5952 0.045(14) Uiso 1 1 d GR . . . .
H22B H 0.1012 0.7409 0.6362 0.045(14) Uiso 1 1 d GR . . . .
H22C H 0.1238 0.9597 0.6067 0.045(14) Uiso 1 1 d GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.016(2) 0.030(3) 0.029(3) 0.000(2) 0.003(2) 0.002(2)
O2 0.024(3) 0.029(3) 0.028(3) 0.011(3) 0.008(2) -0.001(2)
O3 0.023(2) 0.022(3) 0.021(2) 0.003(2) 0.008(2) -0.001(2)
O4 0.031(3) 0.024(3) 0.021(3) 0.002(2) -0.002(2) 0.000(2)
N1 0.019(3) 0.021(3) 0.023(3) 0.000(2) -0.002(2) -0.002(2)
N2 0.021(3) 0.024(3) 0.019(3) 0.005(2) 0.001(2) -0.004(2)
B1 0.008(4) 0.022(5) 0.018(5) 0.000(3) -0.007(4) 0.000(3)
B2 0.017(5) 0.030(5) 0.010(5) -0.003(3) 0.000(4) -0.002(3)
C1 0.017(3) 0.026(3) 0.011(3) -0.001(3) -0.003(2) -0.002(3)
C2 0.018(3) 0.031(3) 0.014(4) -0.003(3) -0.002(3) -0.004(3)
C3 0.015(4) 0.022(4) 0.010(4) 0.001(3) -0.001(3) -0.002(2)
C4 0.017(3) 0.027(3) 0.016(3) -0.004(3) -0.005(2) -0.004(3)
C5 0.018(3) 0.024(3) 0.019(3) -0.002(3) 0.001(3) 0.003(3)
C6 0.024(4) 0.022(3) 0.027(4) 0.004(3) 0.001(3) -0.003(3)
C7 0.015(4) 0.026(5) 0.015(4) 0.004(3) 0.006(3) -0.001(3)
C8 0.022(4) 0.025(4) 0.028(4) -0.006(3) -0.001(3) 0.006(3)
C9 0.035(4) 0.049(6) 0.032(4) -0.007(4) 0.003(3) -0.010(4)
C10 0.029(4) 0.040(5) 0.047(5) 0.013(4) 0.014(4) 0.003(4)
C11 0.037(5) 0.050(6) 0.024(5) -0.004(4) 0.013(4) -0.008(4)
C12 0.022(4) 0.046(5) 0.055(6) 0.006(5) 0.018(4) 0.009(4)
C13 0.016(4) 0.023(4) 0.011(4) 0.001(3) -0.001(3) -0.001(2)
C14 0.016(3) 0.030(4) 0.012(3) 0.001(3) 0.000(2) 0.000(3)
C15 0.018(3) 0.027(4) 0.024(4) 0.002(3) -0.002(3) -0.001(3)
C16 0.018(3) 0.027(4) 0.027(4) 0.002(3) 0.000(3) 0.000(3)
C17 0.013(4) 0.025(4) 0.026(4) 0.008(3) 0.009(3) 0.000(3)
C18 0.013(3) 0.029(4) 0.022(3) 0.001(3) 0.001(3) -0.001(3)
C19 0.028(4) 0.046(5) 0.032(4) -0.005(4) 0.000(3) -0.013(3)
C20 0.034(4) 0.024(4) 0.025(4) 0.000(3) 0.003(3) -0.005(3)
C21 0.026(4) 0.038(5) 0.044(5) 0.008(4) 0.009(3) 0.002(3)
C22 0.035(5) 0.036(4) 0.025(4) -0.003(4) 0.004(3) 0.001(4)

_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
O1 B1 1.362(9) . ?
O1 C8 1.455(8) . ?
O2 B1 1.367(10) . ?
O2 C7 1.479(9) . ?
O3 B2 1.347(10) . ?
O3 C18 1.458(8) . ?
O4 B2 1.370(11) . ?
O4 C17 1.474(9) . ?
N1 C2 1.338(10) . ?
N1 C6 1.348(9) . ?
N2 C1 1.346(10) . ?
N2 C16 1.345(9) . ?
B1 C4 1.571(11) . ?
B2 C14 1.569(12) . ?
C1 C2 1.493(7) . ?
C1 C13 1.383(10) . ?
C2 C3 1.391(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(10) . ?
C4 C5 1.382(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.568(10) . ?
C7 C11 1.499(13) . ?
C7 C12 1.509(11) . ?
C8 C9 1.523(10) . ?
C8 C10 1.506(11) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9798 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9801 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9801 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.383(10) . ?
C14 C15 1.393(10) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.528(11) . ?
C17 C21 1.529(11) . ?
C17 C22 1.536(12) . ?
C18 C19 1.517(10) . ?
C18 C20 1.523(11) . ?
C19 H19A 0.9799 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9798 . ?
C20 H20C 0.9799 . ?
C21 H21A 0.9801 . ?
C21 H21B 0.9799 . ?
C21 H21C 0.9798 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9802 . ?
C22 H22C 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
B1 O1 C8 105.9(6) . . ?
B1 O2 C7 105.9(6) . . ?
B2 O3 C18 106.7(6) . . ?
B2 O4 C17 105.1(6) . . ?
C2 N1 C6 118.2(6) . . ?
C16 N2 C1 117.2(6) . . ?
O1 B1 O2 115.0(8) . . ?
O1 B1 C4 122.6(7) . . ?
O2 B1 C4 122.4(6) . . ?
O3 B2 O4 114.2(8) . . ?
O3 B2 C14 124.6(7) . . ?
O4 B2 C14 121.2(7) . . ?
N2 C1 C2 115.1(5) . . ?
N2 C1 C13 122.0(7) . . ?
C13 C1 C2 122.9(6) . . ?
N1 C2 C1 116.2(5) . . ?
N1 C2 C3 121.7(7) . . ?
C3 C2 C1 122.1(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(7) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 B1 120.8(6) . . ?
C5 C4 B1 122.4(6) . . ?
C5 C4 C3 116.8(6) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(6) . . ?
C6 C5 H5 119.9 . . ?
N1 C6 C5 122.4(7) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
O2 C7 C8 101.3(6) . . ?
O2 C7 C11 105.9(6) . . ?
O2 C7 C12 108.9(6) . . ?
C11 C7 C8 111.6(7) . . ?
C11 C7 C12 112.6(7) . . ?
C12 C7 C8 115.4(7) . . ?
O1 C8 C7 103.0(6) . . ?
O1 C8 C9 107.0(6) . . ?
O1 C8 C10 110.1(6) . . ?
C9 C8 C7 112.5(6) . . ?
C10 C8 C7 114.9(7) . . ?
C10 C8 C9 108.9(7) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.4 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.4 . . ?
C7 C11 H11B 109.6 . . ?
C7 C11 H11C 109.4 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.4 . . ?
C7 C12 H12B 109.6 . . ?
C7 C12 H12C 109.4 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13 119.6 . . ?
C1 C13 C14 120.9(7) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 B2 120.9(7) . . ?
C13 C14 C15 117.2(6) . . ?
C15 C14 B2 121.9(6) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 118.9(7) . . ?
C16 C15 H15 120.5 . . ?
N2 C16 C15 123.8(7) . . ?
N2 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
O4 C17 C18 102.4(6) . . ?
O4 C17 C21 108.5(7) . . ?
O4 C17 C22 105.9(6) . . ?
C18 C17 C21 116.0(7) . . ?
C18 C17 C22 113.6(7) . . ?
C21 C17 C22 109.5(7) . . ?
O3 C18 C17 102.4(6) . . ?
O3 C18 C19 106.0(6) . . ?
O3 C18 C20 108.7(5) . . ?
C19 C18 C17 113.5(6) . . ?
C19 C18 C20 109.9(6) . . ?
C20 C18 C17 115.5(7) . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.3 . . ?
C18 C20 H20B 109.6 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.4 . . ?
C17 C21 H21B 109.4 . . ?
C17 C21 H21C 109.6 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.6 . . ?
C17 C22 H22B 109.4 . . ?
C17 C22 H22C 109.4 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_database_code_depnum_ccdc_archive 'CCDC 988604'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_S14

_audit_creation_date             2014-02-24
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 2,3-dimethy-5-thiophen-2-yl-pyrazine
;
_chemical_formula_moiety         'C10 H10 N2 S'
_chemical_formula_sum            'C10 H10 N2 S'
_chemical_formula_weight         190.26
_chemical_melting_point          324
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.1352(19)
_cell_length_b                   12.292(3)
_cell_length_c                   11.175(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.168(4)
_cell_angle_gamma                90
_cell_volume                     977.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    868
_cell_measurement_temperature    250
_cell_measurement_theta_max      29.258
_cell_measurement_theta_min      3.303
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7011
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.467
_diffrn_ambient_temperature      250
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1411
_reflns_number_total             1720
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'SMART version 4.05 (Siemens, 1995)'
_computing_cell_refinement       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.45 (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.2351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          
; Methyl groups were refined as rigid bodies rotating around C---C bonds, 
 with a common refined U for three H atoms. Other H atoms: riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H9A)=Uiso(H9B)=Uiso(H9C)=FVAR(1)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(2)
3.a Rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8)
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
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
S1 S 0.51909(8) 0.22601(5) 0.30142(5) 0.0641(2) Uani 1 1 d . . . . .
N1 N -0.0495(3) 0.34521(17) 0.02237(15) 0.0694(5) Uani 1 1 d . . . . .
N2 N 0.1438(2) 0.33077(13) 0.24693(13) 0.0505(4) Uani 1 1 d . . . . .
C1 C 0.6803(3) 0.1371(2) 0.2521(2) 0.0736(7) Uani 1 1 d . . . . .
H1 H 0.7899 0.1154 0.2976 0.088 Uiso 1 1 calc R . . . .
C2 C 0.6312(3) 0.1019(2) 0.1402(2) 0.0766(7) Uani 1 1 d . . . . .
H2 H 0.7031 0.0523 0.0988 0.092 Uiso 1 1 calc R . . . .
C3 C 0.4610(3) 0.14715(19) 0.09139(19) 0.0620(5) Uani 1 1 d . . . . .
H3 H 0.4077 0.1310 0.0140 0.074 Uiso 1 1 calc R . . . .
C4 C 0.3811(3) 0.21716(15) 0.16840(16) 0.0487(5) Uani 1 1 d . . . . .
C5 C 0.2076(3) 0.28003(15) 0.15090(16) 0.0475(4) Uani 1 1 d . . . . .
C6 C -0.0152(3) 0.38772(17) 0.23085(18) 0.0548(5) Uani 1 1 d . . . . .
C7 C -0.1141(3) 0.39453(17) 0.1178(2) 0.0613(5) Uani 1 1 d . . . . .
C8 C 0.1100(3) 0.28852(18) 0.03933(18) 0.0619(6) Uani 1 1 d . . . . .
H8 H 0.1577 0.2532 -0.0266 0.074 Uiso 1 1 calc R . . . .
C9 C -0.2947(3) 0.4571(2) 0.0974(3) 0.0872(8) Uani 1 1 d . . . . .
H9A H -0.2727 0.5329 0.1179 0.132(7) Uiso 1 1 d GR . . . .
H9B H -0.3877 0.4272 0.1473 0.132(7) Uiso 1 1 d GR . . . .
H9C H -0.3401 0.4515 0.0137 0.132(7) Uiso 1 1 d GR . . . .
C10 C -0.0842(3) 0.4433(2) 0.3393(2) 0.0764(7) Uani 1 1 d . . . . .
H10A H -0.0913 0.5211 0.3251 0.118(6) Uiso 1 1 d GR . . . .
H10B H 0.0020 0.4288 0.4086 0.118(6) Uiso 1 1 d GR . . . .
H10C H -0.2079 0.4158 0.3539 0.118(6) Uiso 1 1 d GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0650(4) 0.0787(4) 0.0477(3) -0.0061(3) -0.0012(2) -0.0017(3)
N1 0.0707(12) 0.0841(14) 0.0522(11) 0.0060(10) -0.0040(8) 0.0047(10)
N2 0.0556(9) 0.0516(9) 0.0446(9) -0.0045(7) 0.0056(7) -0.0076(8)
C1 0.0594(13) 0.0927(17) 0.0685(15) 0.0006(13) 0.0019(11) 0.0071(12)
C2 0.0696(15) 0.0913(18) 0.0703(15) -0.0090(13) 0.0148(12) 0.0133(13)
C3 0.0663(13) 0.0720(14) 0.0481(11) -0.0066(10) 0.0076(9) -0.0004(11)
C4 0.0552(11) 0.0523(11) 0.0389(10) 0.0023(8) 0.0061(8) -0.0085(9)
C5 0.0551(11) 0.0473(10) 0.0406(10) 0.0006(8) 0.0065(8) -0.0098(8)
C6 0.0553(11) 0.0496(11) 0.0598(12) -0.0042(9) 0.0067(9) -0.0080(9)
C7 0.0600(12) 0.0570(13) 0.0664(13) 0.0054(10) 0.0024(10) -0.0018(10)
C8 0.0676(14) 0.0740(14) 0.0439(11) -0.0005(10) 0.0034(9) 0.0018(11)
C9 0.0724(16) 0.0890(18) 0.099(2) 0.0116(15) -0.0012(14) 0.0163(14)
C10 0.0680(15) 0.0822(17) 0.0801(16) -0.0249(13) 0.0122(12) 0.0008(12)

_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
S1 C1 1.707(2) . ?
S1 C4 1.7256(19) . ?
N1 C7 1.337(3) . ?
N1 C8 1.336(3) . ?
N2 C5 1.349(2) . ?
N2 C6 1.334(3) . ?
C1 H1 0.9400 . ?
C1 C2 1.346(3) . ?
C2 H2 0.9400 . ?
C2 C3 1.409(3) . ?
C3 H3 0.9400 . ?
C3 C4 1.370(3) . ?
C4 C5 1.461(3) . ?
C5 C8 1.387(3) . ?
C6 C7 1.404(3) . ?
C6 C10 1.504(3) . ?
C7 C9 1.503(3) . ?
C8 H8 0.9400 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9701 . ?
C9 H9C 0.9698 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9699 . ?
C10 H10C 0.9699 . ?

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 S1 C4 92.12(10) . . ?
C8 N1 C7 117.57(19) . . ?
C6 N2 C5 117.94(17) . . ?
S1 C1 H1 124.1 . . ?
C2 C1 S1 111.73(19) . . ?
C2 C1 H1 124.1 . . ?
C1 C2 H2 123.5 . . ?
C1 C2 C3 113.0(2) . . ?
C3 C2 H2 123.5 . . ?
C2 C3 H3 123.5 . . ?
C4 C3 C2 113.0(2) . . ?
C4 C3 H3 123.5 . . ?
C3 C4 S1 110.09(16) . . ?
C3 C4 C5 129.46(18) . . ?
C5 C4 S1 120.45(14) . . ?
N2 C5 C4 118.05(17) . . ?
N2 C5 C8 120.25(19) . . ?
C8 C5 C4 121.70(18) . . ?
N2 C6 C7 121.28(18) . . ?
N2 C6 C10 117.04(19) . . ?
C7 C6 C10 121.7(2) . . ?
N1 C7 C6 120.70(19) . . ?
N1 C7 C9 116.9(2) . . ?
C6 C7 C9 122.4(2) . . ?
N1 C8 C5 122.2(2) . . ?
N1 C8 H8 118.9 . . ?
C5 C8 H8 118.9 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.4 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.4 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.4 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'

#===END
_database_code_depnum_ccdc_archive 'CCDC 988605'
