# Electronic Supplementary Material (ESI) for ChemComm.
# 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_f:\arbeit\diamond\ocb\ocb
_database_code_depnum_ccdc_archive 'CCDC 1041114'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-12-23
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   5.018(4)
_cell_length_b                   11.717(9)
_cell_length_c                   18.072(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1062.6(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1281
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.47
_cell_measurement_theta_min      2.76
_exptl_absorpt_coefficient_mu    0.079
_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_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_exptl_special_details           
;
The crystal used for this measurement owas exceptionally small and not diffracting well to higher
angles.
;
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4797
_diffrn_reflns_theta_full        21.25
_diffrn_reflns_theta_max         21.25
_diffrn_reflns_theta_min         2.01
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  ?
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_source                   'Diamond light source, Didcot. UK'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                915
_reflns_number_total             1292
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       0.040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1085
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.059) H3A(0.066) H3B(0.066) H10(0.066) H9(0.067) H13A(0.085)
 H13B(0.085) H13C(0.085) H5A(0.064) H5B(0.064) H8(0.063) H4A(0.069) H4B(0.069)
 Fixed X: H1(0.2438) H3A(-0.5076) H3B(-0.3172) H10(0.3506) H9(0.0204)
 H13A(0.6453) H13B(0.5896) H13C(0.4218) H5A(-0.3535) H5B(-0.5607) H8(-0.2303)
 H4A(-0.2065) H4B(-0.5242)
 Fixed Y: H1(0.6463) H3A(0.6185) H3B(0.6135) H10(0.3809) H9(0.2433)
 H13A(0.5438) H13B(0.6081) H13C(0.641) H5A(0.3171) H5B(0.4146) H8(0.264)
 H4A(0.421) H4B(0.4315)
 Fixed Z: H1(-0.0778) H3A(0.0683) H3B(0.1392) H10(-0.2824) H9(-0.25) H13A(-
 0.247) H13B(-0.1704) H13C(-0.2426) H5A(0.013) H5B(-0.0108) H8(-0.142)
 H4A(0.1146) H4B(0.1172)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0104(5) 0.7217(2) 0.05583(14) 0.0557(9) Uani 1 1 d . . .
N1 N 0.1421(6) 0.5851(3) -0.07729(19) 0.0492(9) Uani 1 1 d . . .
H1 H 0.2438 0.6463 -0.0778 0.059 Uiso 1 1 calc R . .
C11 C 0.2987(7) 0.4882(4) -0.1956(2) 0.0494(12) Uani 1 1 d . . .
C12 C 0.1413(7) 0.4990(3) -0.1311(2) 0.0446(11) Uani 1 1 d . . .
C3 C -0.3395(7) 0.5860(4) 0.0878(2) 0.0550(12) Uani 1 1 d . . .
H3A H -0.5076 0.6185 0.0683 0.066 Uiso 1 1 calc R . .
H3B H -0.3172 0.6135 0.1392 0.066 Uiso 1 1 calc R . .
C7 C -0.0560(7) 0.4155(3) -0.1086(2) 0.0467(11) Uani 1 1 d . . .
C10 C 0.2496(7) 0.3919(4) -0.2385(2) 0.0550(12) Uani 1 1 d . . .
H10 H 0.3506 0.3809 -0.2824 0.066 Uiso 1 1 calc R . .
C9 C 0.0491(7) 0.3073(4) -0.2187(3) 0.0559(12) Uani 1 1 d . . .
H9 H 0.0204 0.2433 -0.2500 0.067 Uiso 1 1 calc R . .
C6 C -0.1698(7) 0.4540(3) -0.0401(2) 0.0463(11) Uani 1 1 d . . .
C1 C -0.0455(7) 0.5580(3) -0.0224(2) 0.0453(11) Uani 1 1 d . . .
C13 C 0.5077(7) 0.5784(4) -0.2157(2) 0.0567(12) Uani 1 1 d . . .
H13A H 0.6453 0.5438 -0.2470 0.085 Uiso 1 1 calc R . .
H13B H 0.5896 0.6081 -0.1704 0.085 Uiso 1 1 calc R . .
H13C H 0.4218 0.6410 -0.2426 0.085 Uiso 1 1 calc R . .
C2 C -0.1096(7) 0.6295(4) 0.0415(2) 0.0519(12) Uani 1 1 d . . .
C5 C -0.3813(7) 0.4006(4) 0.0101(2) 0.0533(11) Uani 1 1 d . . .
H5A H -0.3535 0.3171 0.0130 0.064 Uiso 1 1 calc R . .
H5B H -0.5607 0.4146 -0.0108 0.064 Uiso 1 1 calc R . .
C8 C -0.1000(8) 0.3194(4) -0.1548(3) 0.0525(11) Uani 1 1 d . . .
H8 H -0.2303 0.2640 -0.1420 0.063 Uiso 1 1 calc R . .
C4 C -0.3634(8) 0.4533(3) 0.0888(2) 0.0577(12) Uani 1 1 d . . .
H4A H -0.2065 0.4210 0.1146 0.069 Uiso 1 1 calc R . .
H4B H -0.5242 0.4315 0.1172 0.069 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.264(4) . ?
N1 H1 0.8800 . ?
N1 C12 1.400(5) . ?
N1 C1 1.404(5) . ?
C11 C12 1.414(6) . ?
C11 C10 1.391(6) . ?
C11 C13 1.533(6) . ?
C12 C7 1.450(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.514(5) . ?
C3 C4 1.559(5) . ?
C7 C6 1.436(5) . ?
C7 C8 1.420(6) . ?
C10 H10 0.9500 . ?
C10 C9 1.457(6) . ?
C9 H9 0.9500 . ?
C9 C8 1.384(6) . ?
C6 C1 1.406(5) . ?
C6 C5 1.529(5) . ?
C1 C2 1.462(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.553(6) . ?
C8 H8 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
C12 N1 H1 125.5 . . ?
C12 N1 C1 109.0(3) . . ?
C1 N1 H1 125.5 . . ?
C12 C11 C13 121.1(4) . . ?
C10 C11 C12 115.7(4) . . ?
C10 C11 C13 123.2(4) . . ?
N1 C12 C11 129.4(4) . . ?
N1 C12 C7 107.1(3) . . ?
C11 C12 C7 123.5(4) . . ?
H3A C3 H3B 107.7 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C2 C3 C4 113.7(3) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C6 C7 C12 107.6(3) . . ?
C8 C7 C12 118.5(4) . . ?
C8 C7 C6 134.0(4) . . ?
C11 C10 H10 118.8 . . ?
C11 C10 C9 122.5(4) . . ?
C9 C10 H10 118.8 . . ?
C10 C9 H9 119.7 . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C7 C6 C5 131.2(4) . . ?
C1 C6 C7 106.9(3) . . ?
C1 C6 C5 121.9(4) . . ?
N1 C1 C6 109.5(4) . . ?
N1 C1 C2 125.2(4) . . ?
C6 C1 C2 125.3(4) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C2 C3 122.5(4) . . ?
O1 C2 C1 123.2(4) . . ?
C1 C2 C3 114.3(4) . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C6 C5 C4 109.9(3) . . ?
H5A C5 H5B 108.2 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.2(4) . . ?
C9 C8 H8 120.4 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 C3 112.9(4) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.88 2.08 2.948(4) 167.2 3_565

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
N1 C12 C7 C6 -0.4(4) . . . . ?
N1 C12 C7 C8 178.9(3) . . . . ?
N1 C1 C2 O1 -4.0(6) . . . . ?
N1 C1 C2 C3 174.0(3) . . . . ?
C11 C12 C7 C6 178.6(3) . . . . ?
C11 C12 C7 C8 -2.0(5) . . . . ?
C11 C10 C9 C8 -0.8(6) . . . . ?
C12 N1 C1 C6 0.0(4) . . . . ?
C12 N1 C1 C2 -177.5(3) . . . . ?
C12 C11 C10 C9 0.0(6) . . . . ?
C12 C7 C6 C1 0.5(4) . . . . ?
C12 C7 C6 C5 -178.7(4) . . . . ?
C12 C7 C8 C9 1.2(5) . . . . ?
C7 C6 C1 N1 -0.3(4) . . . . ?
C7 C6 C1 C2 177.2(3) . . . . ?
C7 C6 C5 C4 160.5(4) . . . . ?
C10 C11 C12 N1 -179.8(4) . . . . ?
C10 C11 C12 C7 1.4(5) . . . . ?
C10 C9 C8 C7 0.2(6) . . . . ?
C6 C7 C8 C9 -179.7(4) . . . . ?
C6 C1 C2 O1 178.9(4) . . . . ?
C6 C1 C2 C3 -3.2(5) . . . . ?
C6 C5 C4 C3 46.1(5) . . . . ?
C1 N1 C12 C11 -178.7(4) . . . . ?
C1 N1 C12 C7 0.3(4) . . . . ?
C1 C6 C5 C4 -18.5(5) . . . . ?
C13 C11 C12 N1 -0.1(6) . . . . ?
C13 C11 C12 C7 -178.9(3) . . . . ?
C13 C11 C10 C9 -179.6(3) . . . . ?
C2 C3 C4 C5 -54.9(5) . . . . ?
C5 C6 C1 N1 178.9(3) . . . . ?
C5 C6 C1 C2 -3.6(5) . . . . ?
C8 C7 C6 C1 -178.8(4) . . . . ?
C8 C7 C6 C5 2.1(7) . . . . ?
C4 C3 C2 O1 -150.3(4) . . . . ?
C4 C3 C2 C1 31.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ocb_ii_2
_database_code_depnum_ccdc_archive 'CCDC 1041115'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-11-22
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 S O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.4905(5)
_cell_length_b                   4.9370(2)
_cell_length_c                   21.8359(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.103(5)
_cell_angle_gamma                90.00
_cell_volume                     1019.05(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1366
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.6343
_cell_measurement_theta_min      2.7209
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.6185
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.0395
_exptl_special_details           
;
During the measurement, the diffractometer stopped, and data collection remained unfinished. To grow
a second specimen of this elusive crystal form proved unsuccessful, thus the structure with rather low
completeness is described.
;
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.1065
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6965
_diffrn_reflns_theta_full        32.71
_diffrn_reflns_theta_max         32.71
_diffrn_reflns_theta_min         2.73
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 0.886
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   42.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -      -26.1867   38.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -90.00   21.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -17.0000   14.0000 111

#__ type_ start__ end____ width___ exp.time_
  3 omega  -23.00    5.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -       26.9679  -38.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega   30.00   75.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -113.0000 -178.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   59.00   84.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -       26.9679  179.0000 -180.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0602767000
_diffrn_orient_matrix_UB_12      -0.0053695000
_diffrn_orient_matrix_UB_13      0.0216281000
_diffrn_orient_matrix_UB_21      0.0440003000
_diffrn_orient_matrix_UB_22      0.0323078000
_diffrn_orient_matrix_UB_23      -0.0235788000
_diffrn_orient_matrix_UB_31      -0.0078177000
_diffrn_orient_matrix_UB_32      0.1399109000
_diffrn_orient_matrix_UB_33      0.0062815000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2125
_reflns_number_total             3335
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0860
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.2088
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.018) H8(0.022) H5A(0.021) H5B(0.021) H13A(0.032) H13B(0.032)
 H13C(0.032) H10(0.026) H3A(0.027) H3B(0.027) H9(0.025) H4A(0.027) H4B(0.027)
 Fixed X: H1(0.1408) H8(0.3257) H5A(0.0439) H5B(0.0263) H13A(0.3577)
 H13B(0.5168) H13C(0.3923) H10(0.5818) H3A(-0.2712) H3B(-0.1458) H9(0.5425)
 H4A(-0.1982) H4B(-0.1802)
 Fixed Y: H1(0.9924) H8(0.4715) H5A(0.1785) H5B(0.3822) H13A(1.3861)
 H13B(1.2827) H13C(1.1584) H10(1.0299) H3A(0.4608) H3B(0.2509) H9(0.6935)
 H4A(0.2421) H4B(0.5636)
 Fixed Z: H1(0.4585) H8(0.2769) H5A(0.3294) H5B(0.272) H13A(0.4374)
 H13B(0.4526) H13C(0.4887) H10(0.3657) H3A(0.3973) H3B(0.4148) H9(0.2909)
 H4A(0.3081) H4B(0.3038)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.14932(18) 0.8854(3) 0.42677(8) 0.0147(4) Uani 1 1 d . . .
H1 H 0.1408 0.9924 0.4585 0.018 Uiso 1 1 calc R . .
C12 C 0.2643(2) 0.8699(4) 0.39313(9) 0.0134(4) Uani 1 1 d . . .
C8 C 0.3420(2) 0.6054(4) 0.30797(10) 0.0182(5) Uani 1 1 d . . .
H8 H 0.3257 0.4715 0.2769 0.022 Uiso 1 1 calc R . .
C11 C 0.3931(2) 1.0137(4) 0.40121(11) 0.0167(4) Uani 1 1 d . . .
C6 C 0.0976(2) 0.5696(4) 0.35259(10) 0.0133(4) Uani 1 1 d . . .
O1 O -0.12377(18) 0.7647(3) 0.47154(8) 0.0277(4) Uani 1 1 d . . .
C7 C 0.2364(2) 0.6719(4) 0.34645(9) 0.0139(4) Uani 1 1 d . . .
C2 C -0.0840(2) 0.6474(4) 0.42681(10) 0.0176(4) Uani 1 1 d . . .
C1 C 0.0493(2) 0.7036(4) 0.40215(10) 0.0143(4) Uani 1 1 d . . .
C5 C 0.0125(2) 0.3622(4) 0.31615(10) 0.0172(4) Uani 1 1 d . . .
H5A H 0.0439 0.1785 0.3294 0.021 Uiso 1 1 calc R . .
H5B H 0.0263 0.3822 0.2720 0.021 Uiso 1 1 calc R . .
C13 C 0.4170(2) 1.2287(4) 0.44910(11) 0.0214(5) Uani 1 1 d . . .
H13A H 0.3577 1.3861 0.4374 0.032 Uiso 1 1 calc R . .
H13B H 0.5168 1.2827 0.4526 0.032 Uiso 1 1 calc R . .
H13C H 0.3923 1.1584 0.4887 0.032 Uiso 1 1 calc R . .
C10 C 0.4929(2) 0.9402(5) 0.36187(11) 0.0220(5) Uani 1 1 d . . .
H10 H 0.5818 1.0299 0.3657 0.026 Uiso 1 1 calc R . .
C3 C -0.1695(2) 0.4252(5) 0.39401(11) 0.0224(5) Uani 1 1 d . . .
H3A H -0.2712 0.4608 0.3973 0.027 Uiso 1 1 calc R . .
H3B H -0.1458 0.2509 0.4148 0.027 Uiso 1 1 calc R . .
C9 C 0.4693(2) 0.7379(4) 0.31614(11) 0.0209(5) Uani 1 1 d . . .
H9 H 0.5425 0.6935 0.2909 0.025 Uiso 1 1 calc R . .
C4 C -0.1442(2) 0.3991(5) 0.32594(11) 0.0228(5) Uani 1 1 d . . .
H4A H -0.1982 0.2421 0.3081 0.027 Uiso 1 1 calc R . .
H4B H -0.1802 0.5636 0.3038 0.027 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.371(3) . ?
N1 C1 1.380(3) . ?
C12 C11 1.411(3) . ?
C12 C7 1.420(3) . ?
C8 C7 1.403(3) . ?
C8 C9 1.372(3) . ?
C11 C13 1.493(3) . ?
C11 C10 1.383(3) . ?
C6 C7 1.428(3) . ?
C6 C1 1.381(3) . ?
C6 C5 1.490(3) . ?
O1 C2 1.224(3) . ?
C2 C1 1.445(3) . ?
C2 C3 1.507(3) . ?
C5 C4 1.532(3) . ?
C10 C9 1.416(3) . ?
C3 C4 1.532(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
C12 N1 C1 107.92(17) . . ?
N1 C12 C11 128.83(19) . . ?
N1 C12 C7 108.48(17) . . ?
C11 C12 C7 122.68(19) . . ?
C9 C8 C7 118.6(2) . . ?
C12 C11 C13 121.4(2) . . ?
C10 C11 C12 115.1(2) . . ?
C10 C11 C13 123.47(19) . . ?
C7 C6 C5 130.84(19) . . ?
C1 C6 C7 106.13(18) . . ?
C1 C6 C5 123.03(19) . . ?
C12 C7 C6 106.88(18) . . ?
C8 C7 C12 119.58(19) . . ?
C8 C7 C6 133.4(2) . . ?
O1 C2 C1 123.3(2) . . ?
O1 C2 C3 122.2(2) . . ?
C1 C2 C3 114.51(19) . . ?
N1 C1 C6 110.58(18) . . ?
N1 C1 C2 125.05(19) . . ?
C6 C1 C2 124.26(19) . . ?
C6 C5 C4 109.32(17) . . ?
C11 C10 C9 123.3(2) . . ?
C2 C3 C4 113.44(19) . . ?
C8 C9 C10 120.7(2) . . ?
C5 C4 C3 112.56(19) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 7 2 0.3064 0.0308 7.0061 1.9993 0.0075 0.1806 0.9925
0 -7 -2 0.3064 -0.0308 -7.0061 -1.9993 -0.0075 -0.1806 -0.9925
1 0 -1 0.0285 1.0002 -0.0014 -0.9996 0.0387 0.0675 -0.0143
-11 0 20 0.0255 -10.9991 0.0145 19.9797 -0.2309 -0.9546 0.2135
1 0 3 0.0197 1.0015 -0.0018 2.9935 0.1251 -0.0266 0.0107
-8 0 -24 0.0197 -8.0123 0.0145 -23.9476 -1.0010 0.2126 -0.0858

_olex2_date_sample_data_collection 1302517750.72
_olex2_exptl_crystal_mounting_method 'on loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_11srv080
_database_code_depnum_ccdc_archive 'CCDC 1041116'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-12-23
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.25
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   10.5236(3)
_cell_length_b                   7.1700(2)
_cell_length_c                   13.5856(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.912(3)
_cell_angle_gamma                90
_cell_volume                     1022.70(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_density_diffrn    1.2940
_exptl_crystal_F_000             424.1847
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17019
_diffrn_reflns_theta_full        26.000000
_diffrn_reflns_theta_max         32.63
_diffrn_reflns_theta_min         2.84
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999002
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -15
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -11
_reflns_number_gt                2833
_reflns_number_total             3510
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.479216
_refine_diff_density_min         -0.334646
_refine_diff_density_rms         0.071478
_refine_ls_d_res_high            0.659033
_refine_ls_d_res_low             6.776947
_refine_ls_goodness_of_fit_ref   1.043296
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     143
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.062341
_refine_ls_R_factor_gt           0.047219
_refine_ls_restrained_S_all      1.043296
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.3164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.125187
_olex2_refinement_description    
;
;
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
O1 O 1.14140(8) 0.06540(12) 0.44321(6) 0.02454(19) Uani 1.000000
N1 N 0.88936(8) 0.23659(13) 0.42290(7) 0.01727(18) Uani 1.000000
C6 C 0.98227(10) 0.49051(14) 0.35831(7) 0.01596(19) Uani 1.000000
C12 C 0.79432(9) 0.36366(14) 0.40049(7) 0.01592(19) Uani 1.000000
C7 C 0.84870(10) 0.52552(14) 0.36012(7) 0.01634(19) Uani 1.000000
C2 C 1.12555(10) 0.22398(15) 0.40985(7) 0.0171(2) Uani 1.000000
C3 C 1.23532(10) 0.34241(15) 0.38009(8) 0.0179(2) Uani 1.000000
H3a H 1.2695(8) 0.4115(7) 0.43730(9) 0.0214(2) Uiso 1.000000
H3b H 1.3018(6) 0.2610(5) 0.3589(6) 0.0214(2) Uiso 1.000000
C1 C 1.00276(9) 0.31417(14) 0.39751(7) 0.01602(19) Uani 1.000000
C10 C 0.58901(10) 0.49901(16) 0.38091(8) 0.0204(2) Uani 1.000000
H10 H 0.50156(10) 0.49402(16) 0.38687(8) 0.0245(3) Uiso 1.000000
C11 C 0.66247(10) 0.34739(15) 0.41214(8) 0.0180(2) Uani 1.000000
C8 C 0.77011(10) 0.67685(15) 0.33002(8) 0.0198(2) Uani 1.000000
H8 H 0.80418(10) 0.78428(15) 0.30392(8) 0.0237(3) Uiso 1.000000
C4 C 1.19850(10) 0.48072(15) 0.29690(8) 0.0204(2) Uani 1.000000
H4a H 1.27166(11) 0.5565(5) 0.2834(7) 0.0245(3) Uiso 1.000000
H4b H 1.1760(7) 0.4133(7) 0.2363(3) 0.0245(3) Uiso 1.000000
C5 C 1.08747(10) 0.60703(15) 0.32203(8) 0.0196(2) Uani 1.000000
H5a H 1.0568(2) 0.6776(12) 0.2643(4) 0.0235(2) Uiso 1.000000
H5b H 1.1161(3) 0.6974(10) 0.3719(5) 0.0235(2) Uiso 1.000000
C9 C 0.64115(11) 0.66105(16) 0.34039(8) 0.0216(2) Uani 1.000000
H9 H 0.58747(11) 0.75893(16) 0.32031(8) 0.0259(3) Uiso 1.000000
C13 C 0.60759(11) 0.17452(16) 0.45554(10) 0.0263(2) Uani 1.000000
H13a H 0.6219(9) 0.0697(3) 0.4138(4) 0.0395(4) Uiso 1.000000
H13b H 0.6481(7) 0.1527(8) 0.5200(3) 0.0395(4) Uiso 1.000000
H13c H 0.5177(2) 0.1909(6) 0.4606(7) 0.0395(4) Uiso 1.000000
H1 H 0.8809(16) 0.128(2) 0.4545(13) 0.040(5) Uiso 1.000000


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 C2 1.2312(13) . ?
N1 C12 1.3717(13) . ?
N1 C1 1.3815(13) . ?
N1 H1 0.894(18) . ?
C6 C7 1.4297(14) . ?
C6 C1 1.3832(14) . ?
C6 C5 1.4970(14) . ?
C12 C7 1.4206(14) . ?
C12 C11 1.4120(14) . ?
C7 C8 1.4080(14) . ?
C2 C3 1.5108(14) . ?
C2 C1 1.4445(14) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 C4 1.5334(15) . ?
C10 H10 0.9300 . ?
C10 C11 1.3838(15) . ?
C10 C9 1.4126(16) . ?
C11 C13 1.5047(15) . ?
C8 H8 0.9300 . ?
C8 C9 1.3785(15) . ?
C4 H4a 0.9700 . ?
C4 H4b 0.9700 . ?
C4 C5 1.5351(15) . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C9 H9 0.9300 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?

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 N1 C12 107.84(8) . . ?
H1 N1 C12 126.0(11) . . ?
H1 N1 C1 125.8(11) . . ?
C1 C6 C7 106.35(9) . . ?
C5 C6 C7 131.13(9) . . ?
C5 C6 C1 122.52(9) . . ?
C7 C12 N1 108.75(9) . . ?
C11 C12 N1 128.86(9) . . ?
C11 C12 C7 122.38(9) . . ?
C12 C7 C6 106.60(9) . . ?
C8 C7 C6 133.55(10) . . ?
C8 C7 C12 119.84(9) . . ?
C3 C2 O1 122.06(9) . . ?
C1 C2 O1 123.63(10) . . ?
C1 C2 C3 114.31(9) . . ?
H3a C3 C2 108.8(3) . . ?
H3b C3 C2 108.8(3) . . ?
H3b C3 H3a 108.0(12) . . ?
C4 C3 C2 113.66(8) . . ?
C4 C3 H3a 108.8(3) . . ?
C4 C3 H3b 108.8(3) . . ?
C6 C1 N1 110.46(9) . . ?
C2 C1 N1 124.89(9) . . ?
C2 C1 C6 124.65(9) . . ?
C11 C10 H10 118.59(6) . . ?
C9 C10 H10 118.59(6) . . ?
C9 C10 C11 122.81(10) . . ?
C10 C11 C12 115.69(10) . . ?
C13 C11 C12 121.22(9) . . ?
C13 C11 C10 123.09(10) . . ?
H8 C8 C7 120.99(6) . . ?
C9 C8 C7 118.03(10) . . ?
C9 C8 H8 120.99(6) . . ?
H4a C4 C3 109.7(3) . . ?
H4b C4 C3 109.7(3) . . ?
H4b C4 H4a 105.6(12) . . ?
C5 C4 C3 112.06(9) . . ?
C5 C4 H4a 109.7(3) . . ?
C5 C4 H4b 109.7(3) . . ?
C4 C5 C6 109.58(9) . . ?
H5a C5 C6 110.2(3) . . ?
H5a C5 C4 110.2(3) . . ?
H5b C5 C6 110.2(3) . . ?
H5b C5 C4 110.2(3) . . ?
H5b C5 H5a 106.6(12) . . ?
C8 C9 C10 121.25(10) . . ?
H9 C9 C10 119.38(6) . . ?
H9 C9 C8 119.38(6) . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.894(18) 1.990(18) 2.8604(12) 164.0(16) 3_756

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_description       plate
####################################################################### 
# 
# 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_11srv079
_database_code_depnum_ccdc_archive 'CCDC 1041117'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-11-22
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   4.9180(5)
_cell_length_b                   17.5881(19)
_cell_length_c                   11.9750(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.432(3)
_cell_angle_gamma                90.00
_cell_volume                     1027.11(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1455
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.32
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.801513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8627
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         2.07
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1865
_reflns_number_total             2999
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2999
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0582P)²+0.2171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1405
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H5A(0.031) H5B(0.031) H10(0.032) H9(0.034) H3A(0.035) H3B(0.035)
 H13A(0.044) H13B(0.044) H13C(0.044) H8(0.032) H4A(0.036) H4B(0.036)
 Fixed X: H5A(-0.4058) H5B(-0.2188) H10(0.569) H9(0.2116) H3A(-0.1319) H3B(-
 0.3206) H13A(0.6556) H13B(0.8361) H13C(0.8592) H8(-0.0741) H4A(-0.0492) H4B(-
 0.3735) H1(0.4835)
 Fixed Y: H5A(0.4915) H5B(0.5175) H10(0.2315) H9(0.2632) H3A(0.6451)
 H3B(0.571) H13A(0.2677) H13B(0.3374) H13C(0.2561) H8(0.3664) H4A(0.6211)
 H4B(0.6227) H1(0.4309)
 Fixed Z: H5A(0.6662) H5B(0.5728) H10(0.6318) H9(0.4925) H3A(0.8638)
 H3B(0.8634) H13A(0.897) H13B(0.8622) H13C(0.8044) H8(0.5147) H4A(0.6784)
 H4B(0.6814) H1(0.8989)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3461(3) 0.42781(8) 0.84216(11) 0.0229(3) Uani 1 1 d . . .
O1 O 0.2311(3) 0.56233(7) 0.97075(10) 0.0312(3) Uani 1 1 d . . .
C11 C 0.5094(3) 0.31340(9) 0.74399(14) 0.0230(4) Uani 1 1 d . . .
C6 C 0.0015(3) 0.46517(9) 0.70903(14) 0.0226(3) Uani 1 1 d . . .
C2 C 0.0905(4) 0.54616(9) 0.88159(14) 0.0238(4) Uani 1 1 d . . .
C7 C 0.1230(3) 0.39788(9) 0.67050(13) 0.0219(3) Uani 1 1 d . . .
C1 C 0.1440(4) 0.48132(9) 0.81305(14) 0.0226(3) Uani 1 1 d . . .
C5 C -0.2273(4) 0.51425(9) 0.65479(14) 0.0255(4) Uani 1 1 d . . .
H5A H -0.4058 0.4915 0.6662 0.031 Uiso 1 1 calc R . .
H5B H -0.2188 0.5175 0.5728 0.031 Uiso 1 1 calc R . .
C10 C 0.4558(4) 0.27367(9) 0.64397(15) 0.0268(4) Uani 1 1 d . . .
H10 H 0.5690 0.2315 0.6318 0.032 Uiso 1 1 calc R . .
C12 C 0.3375(3) 0.37650(9) 0.75482(13) 0.0227(4) Uani 1 1 d . . .
C9 C 0.2409(4) 0.29288(10) 0.55925(15) 0.0287(4) Uani 1 1 d . . .
H9 H 0.2116 0.2632 0.4925 0.034 Uiso 1 1 calc R . .
C3 C -0.1560(4) 0.59239(10) 0.83534(15) 0.0291(4) Uani 1 1 d . . .
H3A H -0.1319 0.6451 0.8638 0.035 Uiso 1 1 calc R . .
H3B H -0.3206 0.5710 0.8634 0.035 Uiso 1 1 calc R . .
C13 C 0.7345(4) 0.29179(10) 0.83472(15) 0.0291(4) Uani 1 1 d . . .
H13A H 0.6556 0.2677 0.8970 0.044 Uiso 1 1 calc R . .
H13B H 0.8361 0.3374 0.8622 0.044 Uiso 1 1 calc R . .
H13C H 0.8592 0.2561 0.8044 0.044 Uiso 1 1 calc R . .
C8 C 0.0724(4) 0.35407(10) 0.57149(14) 0.0264(4) Uani 1 1 d . . .
H8 H -0.0741 0.3664 0.5147 0.032 Uiso 1 1 calc R . .
C4 C -0.2033(4) 0.59400(10) 0.70643(15) 0.0300(4) Uani 1 1 d . . .
H4A H -0.0492 0.6211 0.6784 0.036 Uiso 1 1 calc R . .
H4B H -0.3735 0.6227 0.6814 0.036 Uiso 1 1 calc R . .
H1 H 0.4835 0.4309 0.8989 0.023(5) Uiso 1 1 d R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.381(2) . ?
N1 C12 1.378(2) . ?
O1 C2 1.228(2) . ?
C11 C10 1.382(2) . ?
C11 C12 1.411(2) . ?
C11 C13 1.496(3) . ?
C6 C7 1.429(2) . ?
C6 C1 1.378(2) . ?
C6 C5 1.498(2) . ?
C2 C1 1.449(2) . ?
C2 C3 1.504(3) . ?
C7 C12 1.414(2) . ?
C7 C8 1.409(2) . ?
C5 C4 1.531(2) . ?
C10 C9 1.408(3) . ?
C9 C8 1.378(3) . ?
C3 C4 1.531(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
C12 N1 C1 107.72(14) . . ?
C10 C11 C12 115.34(16) . . ?
C10 C11 C13 122.75(15) . . ?
C12 C11 C13 121.91(15) . . ?
C7 C6 C5 131.24(15) . . ?
C1 C6 C7 106.13(15) . . ?
C1 C6 C5 122.61(15) . . ?
O1 C2 C1 123.47(16) . . ?
O1 C2 C3 122.09(15) . . ?
C1 C2 C3 114.43(15) . . ?
C12 C7 C6 107.11(14) . . ?
C8 C7 C6 133.53(17) . . ?
C8 C7 C12 119.35(15) . . ?
N1 C1 C2 124.84(15) . . ?
C6 C1 N1 110.68(14) . . ?
C6 C1 C2 124.48(16) . . ?
C6 C5 C4 109.77(15) . . ?
C11 C10 C9 122.97(16) . . ?
N1 C12 C11 128.68(16) . . ?
N1 C12 C7 108.35(14) . . ?
C11 C12 C7 122.95(15) . . ?
C8 C9 C10 121.10(16) . . ?
C2 C3 C4 113.04(14) . . ?
C9 C8 C7 118.25(17) . . ?
C3 C4 C5 112.57(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_KF011
_database_code_depnum_ccdc_archive 'CCDC 1041118'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.25
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.3763(6)
_cell_length_b                   6.5586(4)
_cell_length_c                   16.7932(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.558(2)
_cell_angle_gamma                90
_cell_volume                     1008.00(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6387
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.30
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5154
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1464 before and 0.1190 after correction.
The Ratio of minimum to maximum transmission is 0.5154.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3129
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             424.1847
_exptl_crystal_preparation       'cut from a larger crystal'
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.156
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12395
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.30
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -11
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -8
_reflns_number_gt                1713
_reflns_number_total             1974
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.6048
_refine_diff_density_min         -0.3161
_refine_diff_density_rms         0.1226
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             8.8519
_refine_ls_goodness_of_fit_ref   1.0606
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1974
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      1.0606
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1262P)²+0.2476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1793
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C10(H10a,H10b), C9(H9a,H9b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.14805(14) 0.15061(19) 0.45925(7) 0.0240(4) Uani 1.000000 .
N1 N 0.03361(15) 0.1841(2) 0.60696(9) 0.0184(4) Uani 1.000000 .
H1 H 0.00644(15) 0.0641(2) 0.58543(9) 0.0221(5) Uiso 1.000000 R
C6 C 0.06433(17) 0.4600(3) 0.69021(10) 0.0166(4) Uani 1.000000 .
C2 C -0.08662(19) 0.1827(3) 0.72657(11) 0.0194(4) Uani 1.000000 .
H2 H -0.13001(19) 0.0516(3) 0.71682(11) 0.0233(5) Uiso 1.000000 R
C4 C -0.04026(18) 0.4944(3) 0.80835(10) 0.0188(4) Uani 1.000000 .
C12 C 0.11798(18) 0.3249(3) 0.57717(10) 0.0170(4) Uani 1.000000 .
C7 C 0.14019(17) 0.4954(3) 0.62663(10) 0.0171(4) Uani 1.000000 .
C3 C -0.10600(18) 0.3006(3) 0.79112(10) 0.0195(4) Uani 1.000000 .
H3 H -0.16598(18) 0.2499(3) 0.82554(10) 0.0234(5) Uiso 1.000000 R
C11 C 0.17341(18) 0.3003(3) 0.50406(10) 0.0179(4) Uani 1.000000 .
C1 C -0.00047(17) 0.2634(3) 0.67584(10) 0.0171(4) Uani 1.000000 .
C8 C 0.22685(19) 0.6747(3) 0.60910(11) 0.0189(5) Uani 1.000000 .
H8a H 0.16040(19) 0.7793(3) 0.57875(11) 0.0227(5) Uiso 1.000000 R
H8b H 0.28021(19) 0.7359(3) 0.66094(11) 0.0227(5) Uiso 1.000000 R
C10 C 0.26315(19) 0.4778(3) 0.48451(10) 0.0191(4) Uani 1.000000 .
H10a H 0.34031(19) 0.4245(3) 0.45820(10) 0.0229(5) Uiso 1.000000 R
H10b H 0.19912(19) 0.5674(3) 0.44458(10) 0.0229(5) Uiso 1.000000 R
C5 C 0.04441(18) 0.5738(3) 0.75801(10) 0.0183(4) Uani 1.000000 .
H5 H 0.08878(18) 0.7039(3) 0.76904(10) 0.0220(5) Uiso 1.000000 R
C9 C 0.33534(19) 0.6061(3) 0.55849(11) 0.0195(4) Uani 1.000000 .
H9a H 0.38082(19) 0.7279(3) 0.53950(11) 0.0234(5) Uiso 1.000000 R
H9b H 0.41386(19) 0.5252(3) 0.59345(11) 0.0234(5) Uiso 1.000000 R
C13 C -0.0609(2) 0.6104(3) 0.88300(11) 0.0239(5) Uani 1.000000 .
H13a H 0.0323(4) 0.6166(18) 0.9230(4) 0.0359(7) Uiso 1.000000 GR
H13b H -0.0945(14) 0.7490(7) 0.86719(17) 0.0359(7) Uiso 1.000000 GR
H13c H -0.1337(11) 0.5406(12) 0.9071(5) 0.0359(7) Uiso 1.000000 GR


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 C11 1.229(2) . ?
N1 H1 0.8800 . ?
N1 C12 1.379(2) . ?
N1 C1 1.368(2) . ?
C6 C7 1.425(2) . ?
C6 C1 1.423(2) . ?
C6 C5 1.407(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(3) . ?
C2 C1 1.399(2) . ?
C4 C3 1.415(3) . ?
C4 C5 1.381(2) . ?
C4 C13 1.514(2) . ?
C12 C7 1.381(2) . ?
C12 C11 1.443(3) . ?
C7 C8 1.495(2) . ?
C3 H3 0.9500 . ?
C11 C10 1.514(2) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.528(2) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C9 1.531(2) . ?
C5 H5 0.9500 . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 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
C12 N1 H1 125.98(9) . . ?
C1 N1 H1 125.98(9) . . ?
C1 N1 C12 108.04(14) . . ?
C1 C6 C7 106.55(15) . . ?
C5 C6 C7 134.07(16) . . ?
C5 C6 C1 119.38(15) . . ?
C3 C2 H2 121.32(10) . . ?
C1 C2 H2 121.32(10) . . ?
C1 C2 C3 117.36(16) . . ?
C5 C4 C3 119.75(15) . . ?
C13 C4 C3 119.49(16) . . ?
C13 C4 C5 120.74(16) . . ?
C7 C12 N1 110.33(15) . . ?
C11 C12 N1 125.11(15) . . ?
C11 C12 C7 124.54(16) . . ?
C12 C7 C6 106.51(15) . . ?
C8 C7 C6 131.09(15) . . ?
C8 C7 C12 122.39(15) . . ?
C4 C3 C2 122.69(16) . . ?
H3 C3 C2 118.66(10) . . ?
H3 C3 C4 118.66(10) . . ?
C12 C11 O1 123.57(16) . . ?
C10 C11 O1 121.64(15) . . ?
C10 C11 C12 114.76(14) . . ?
C6 C1 N1 108.56(14) . . ?
C2 C1 N1 129.99(16) . . ?
C2 C1 C6 121.42(15) . . ?
H8a C8 C7 109.77(9) . . ?
H8b C8 C7 109.77(9) . . ?
H8b C8 H8a 108.2 . . ?
C9 C8 C7 109.52(14) . . ?
C9 C8 H8a 109.77(9) . . ?
C9 C8 H8b 109.77(9) . . ?
H10a C10 C11 108.63(9) . . ?
H10b C10 C11 108.63(9) . . ?
H10b C10 H10a 107.6 . . ?
C9 C10 C11 114.53(14) . . ?
C9 C10 H10a 108.63(9) . . ?
C9 C10 H10b 108.63(9) . . ?
C4 C5 C6 119.37(16) . . ?
H5 C5 C6 120.32(10) . . ?
H5 C5 C4 120.32(10) . . ?
C10 C9 C8 112.50(14) . . ?
H9a C9 C8 109.10(9) . . ?
H9a C9 C10 109.10(9) . . ?
H9b C9 C8 109.10(9) . . ?
H9b C9 C10 109.10(9) . . ?
H9b C9 H9a 107.8 . . ?
H13a C13 C4 109.5 . . ?
H13b C13 C4 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C4 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?

_olex2_exptl_crystal_mounting_method 
'mounted on a MiTeGen sample holder with perfluoro polyether oil and placed directly into the pre-cooled cryostream'
_olex2_submission_original_sample_id KF011
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_KF012
_database_code_depnum_ccdc_archive 'CCDC 1041119'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.25
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   12.7256(11)
_cell_length_b                   5.4479(5)
_cell_length_c                   14.7930(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.039(3)
_cell_angle_gamma                90
_cell_volume                     999.12(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4876
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      2.40
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1522 before and 0.1248 after correction.
The Ratio of minimum to maximum transmission is 0.6318.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3245
_exptl_crystal_density_meas      .
_exptl_crystal_description       plate
_exptl_crystal_F_000             424.1847
_exptl_crystal_preparation       'cut from a larger plate'
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.133
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_unetI/netI     0.0845
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15697
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.40
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -15
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                1568
_reflns_number_total             1967
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.5582
_refine_diff_density_min         -0.3439
_refine_diff_density_rms         0.1097
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             8.4982
_refine_ls_goodness_of_fit_ref   1.0528
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1967
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.0528
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1219P)²+0.1575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1807
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10b,H10a), C9(H9a,H9b), C8(H8b,H8a)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), N1(H1)
2.c Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.09724(12) 0.1519(3) 0.61773(10) 0.0276(4) Uani 1.000000 .
N1 N 0.05827(13) 0.2368(3) 0.41784(11) 0.0218(4) Uani 1.000000 .
C11 C 0.14001(15) 0.3236(4) 0.58590(13) 0.0207(5) Uani 1.000000 .
C5 C 0.14417(16) 0.6940(4) 0.27578(14) 0.0220(5) Uani 1.000000 .
C12 C 0.12365(15) 0.3717(4) 0.48739(14) 0.0201(5) Uani 1.000000 .
C6 C 0.12966(14) 0.5506(4) 0.35138(13) 0.0195(5) Uani 1.000000 .
C7 C 0.16965(14) 0.5643(4) 0.44965(13) 0.0200(5) Uani 1.000000 .
C3 C 0.02485(16) 0.4189(4) 0.17315(14) 0.0234(5) Uani 1.000000 .
C10 C 0.21324(15) 0.5053(4) 0.64707(14) 0.0236(5) Uani 1.000000 .
C4 C 0.09115(16) 0.6307(4) 0.18691(14) 0.0221(5) Uani 1.000000 .
C13 C 0.10269(18) 0.7817(4) 0.10444(15) 0.0280(5) Uani 1.000000 .
C2 C 0.00917(15) 0.2736(4) 0.24474(13) 0.0227(5) Uani 1.000000 .
C1 C 0.06165(15) 0.3429(4) 0.33477(14) 0.0200(5) Uani 1.000000 .
C9 C 0.29902(16) 0.6146(4) 0.60098(14) 0.0238(5) Uani 1.000000 .
C8 C 0.24871(16) 0.7370(4) 0.50780(13) 0.0229(5) Uani 1.000000 .
H2 H -0.03541(15) 0.1319(4) 0.23369(13) 0.0273(6) Uiso 1.000000 R
H3 H -0.01037(16) 0.3755(4) 0.11157(14) 0.0280(6) Uiso 1.000000 R
H5 H 0.19018(16) 0.8334(4) 0.28600(14) 0.0264(6) Uiso 1.000000 R
H1 H 0.02095(13) 0.1056(3) 0.42559(11) 0.0262(5) Uiso 1.000000 R
H10b H 0.16889(15) 0.6401(4) 0.66359(14) 0.0283(6) Uiso 1.000000 R
H10a H 0.24958(15) 0.4222(4) 0.70525(14) 0.0283(6) Uiso 1.000000 R
H13a H 0.1320(11) 0.9434(10) 0.12552(17) 0.0421(8) Uiso 1.000000 GR
H13b H 0.1517(9) 0.6984(13) 0.0720(6) 0.0421(8) Uiso 1.000000 GR
H13c H 0.0319(3) 0.802(2) 0.0622(5) 0.0421(8) Uiso 1.000000 GR
H9a H 0.34179(16) 0.7376(4) 0.64306(14) 0.0285(6) Uiso 1.000000 R
H9b H 0.34866(16) 0.4828(4) 0.59078(14) 0.0285(6) Uiso 1.000000 R
H8b H 0.30595(16) 0.7796(4) 0.47497(13) 0.0275(6) Uiso 1.000000 R
H8a H 0.21154(16) 0.8902(4) 0.51864(13) 0.0275(6) Uiso 1.000000 R


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 C11 1.228(2) . ?
N1 C12 1.380(3) . ?
N1 C1 1.367(3) . ?
N1 H1 0.8800 . ?
C11 C12 1.449(3) . ?
C11 C10 1.512(3) . ?
C5 C6 1.410(3) . ?
C5 C4 1.379(3) . ?
C5 H5 0.9500 . ?
C12 C7 1.379(3) . ?
C6 C7 1.430(3) . ?
C6 C1 1.412(3) . ?
C7 C8 1.499(3) . ?
C3 C4 1.417(3) . ?
C3 C2 1.372(3) . ?
C3 H3 0.9500 . ?
C10 C9 1.532(3) . ?
C10 H10b 0.9900 . ?
C10 H10a 0.9900 . ?
C4 C13 1.506(3) . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
C2 C1 1.400(3) . ?
C2 H2 0.9500 . ?
C9 C8 1.535(3) . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C8 H8b 0.9900 . ?
C8 H8a 0.9900 . ?

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 N1 C12 108.01(16) . . ?
H1 N1 C12 126.00(11) . . ?
H1 N1 C1 126.00(11) . . ?
C12 C11 O1 123.22(18) . . ?
C10 C11 O1 122.40(18) . . ?
C10 C11 C12 114.38(17) . . ?
C4 C5 C6 119.59(19) . . ?
H5 C5 C6 120.21(12) . . ?
H5 C5 C4 120.21(12) . . ?
C11 C12 N1 125.40(18) . . ?
C7 C12 N1 110.05(17) . . ?
C7 C12 C11 124.54(18) . . ?
C7 C6 C5 134.19(18) . . ?
C1 C6 C5 119.40(18) . . ?
C1 C6 C7 106.40(17) . . ?
C6 C7 C12 106.59(17) . . ?
C8 C7 C12 122.43(17) . . ?
C8 C7 C6 130.94(18) . . ?
C2 C3 C4 122.99(18) . . ?
H3 C3 C4 118.51(11) . . ?
H3 C3 C2 118.51(12) . . ?
C9 C10 C11 113.14(16) . . ?
H10b C10 C11 108.95(10) . . ?
H10b C10 C9 108.95(11) . . ?
H10a C10 C11 108.95(11) . . ?
H10a C10 C9 108.95(10) . . ?
H10a C10 H10b 107.8 . . ?
C3 C4 C5 119.22(18) . . ?
C13 C4 C5 121.28(19) . . ?
C13 C4 C3 119.50(18) . . ?
H13a C13 C4 109.5 . . ?
H13b C13 C4 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C4 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
C1 C2 C3 117.21(19) . . ?
H2 C2 C3 121.39(12) . . ?
H2 C2 C1 121.39(12) . . ?
C6 C1 N1 108.94(17) . . ?
C2 C1 N1 129.48(18) . . ?
C2 C1 C6 121.57(18) . . ?
C8 C9 C10 111.95(16) . . ?
H9a C9 C10 109.22(11) . . ?
H9a C9 C8 109.22(11) . . ?
H9b C9 C10 109.22(11) . . ?
H9b C9 C8 109.22(11) . . ?
H9b C9 H9a 107.9 . . ?
C9 C8 C7 109.44(16) . . ?
H8b C8 C7 109.79(10) . . ?
H8b C8 C9 109.79(11) . . ?
H8a C8 C7 109.79(10) . . ?
H8a C8 C9 109.79(11) . . ?
H8a C8 H8b 108.2 . . ?

_olex2_exptl_crystal_mounting_method 
'mounted on a MiTeGen sample hoder with perfluoro polyether oil and placed directly into the pre-cooled cryostream'
_olex2_submission_original_sample_id KF012
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_PCB_DMSO
_database_code_depnum_ccdc_archive 'CCDC 1041120'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-12-23
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.25
_chemical_oxdiff_formula         'C13 H13 N O'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   14.6822(18)
_cell_length_b                   6.6231(8)
_cell_length_c                   20.970(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2039.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    613
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.9640
_cell_measurement_theta_min      2.7689
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.2980
_exptl_crystal_description       prism
_exptl_crystal_F_000             848.3694
_exptl_crystal_size_max          0.2674
_exptl_crystal_size_mid          0.1587
_exptl_crystal_size_min          0.0492
_diffrn_reflns_av_R_equivalents  0.1753
_diffrn_reflns_av_unetI/netI     0.1680
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12113
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         2.77
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9178
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00   41.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9366    0.0000   60.0000 116

#__ type_ start__ end____ width___ exp.time_
  2 omega   33.00   70.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5616 -137.0000 -134.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -43.00   24.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9366   38.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
  4 omega  -88.00   12.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9366  -77.0000    0.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0144012000
_diffrn_orient_matrix_UB_12      0.0993680000
_diffrn_orient_matrix_UB_13      -0.0075901000
_diffrn_orient_matrix_UB_21      -0.0029402000
_diffrn_orient_matrix_UB_22      0.0230555000
_diffrn_orient_matrix_UB_23      0.0329714000
_diffrn_orient_matrix_UB_31      0.0460006000
_diffrn_orient_matrix_UB_32      0.0325879000
_diffrn_orient_matrix_UB_33      -0.0002725000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                1116
_reflns_number_total             2458
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         2.4296
_refine_diff_density_min         -1.1369
_refine_diff_density_rms         0.3230
_refine_ls_d_res_high            0.7345
_refine_ls_d_res_low             7.3411
_refine_ls_goodness_of_fit_ref   1.3261
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2986
_refine_ls_R_factor_gt           0.1958
_refine_ls_restrained_S_all      1.3261
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4158
_refine_ls_wR_factor_ref         0.4813
_olex2_refinement_description    
;
The crystal is highly twinned but could not grown in any other way. Thus the residual electron
density is high and the Rint and final R-values are high as well.
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.5514(3) 0.3554(7) 0.5701(2) 0.0326(14) Uani 1.000000 .
N2 N 0.5721(4) 0.3132(8) 0.4334(3) 0.0282(15) Uani 1.000000 .
C3 C 0.6291(4) 0.0381(10) 0.3832(3) 0.0228(16) Uani 1.000000 .
C4 C 0.5898(4) 0.2342(10) 0.3741(4) 0.0276(18) Uani 1.000000 .
C5 C 0.5866(4) 0.2017(10) 0.5446(3) 0.0236(16) Uani 1.000000 .
C6 C 0.5970(4) 0.1750(10) 0.4793(4) 0.0261(17) Uani 1.000000 .
C7 C 0.6642(5) -0.1750(10) 0.4876(4) 0.0300(18) Uani 1.000000 .
C8 C 0.6525(4) -0.0729(13) 0.3287(3) 0.0324(19) Uani 1.000000 .
C9 C 0.5978(4) 0.1919(10) 0.2617(5) 0.039(2) Uani 1.000000 .
C10 C 0.6335(4) -0.0004(11) 0.4500(3) 0.0252(17) Uani 1.000000 .
C11 C 0.6907(5) -0.1051(10) 0.5552(3) 0.0315(19) Uani 1.000000 .
C12 C 0.6197(5) 0.0264(10) 0.5865(3) 0.0266(17) Uani 1.000000 .
C13 C 0.5756(5) 0.3117(11) 0.3139(4) 0.035(2) Uani 1.000000 .
C14 C 0.6390(5) -0.0035(12) 0.2686(4) 0.0352(19) Uani 1.000000 .
C15 C 0.6665(6) -0.1227(13) 0.2105(4) 0.043(2) Uani 1.000000 .
H13 H 0.5517(5) 0.4406(11) 0.3083(4) 0.042(2) Uiso 1.000000 R
H9 H 0.5856(4) 0.2401(10) 0.2209(5) 0.047(3) Uiso 1.000000 R
H8 H 0.6786(4) -0.1999(13) 0.3339(3) 0.039(2) Uiso 1.000000 R
H2 H 0.5491(4) 0.4304(8) 0.4407(3) 0.0339(18) Uiso 1.000000 R
H7a H 0.6158(5) -0.2743(10) 0.4901(4) 0.036(2) Uiso 1.000000 R
H7b H 0.7163(5) -0.2374(10) 0.4670(4) 0.036(2) Uiso 1.000000 R
H11a H 0.7010(5) -0.2230(10) 0.5816(3) 0.038(2) Uiso 1.000000 R
H11b H 0.7475(5) -0.0307(10) 0.5528(3) 0.038(2) Uiso 1.000000 R
H12a H 0.6448(5) 0.0812(10) 0.6256(3) 0.032(2) Uiso 1.000000 R
H12b H 0.5678(5) -0.0569(10) 0.5979(3) 0.032(2) Uiso 1.000000 R
H15a H 0.7297(11) -0.099(6) 0.2015(15) 0.065(3) Uiso 1.000000 GR
H15b H 0.657(3) -0.2639(14) 0.2183(10) 0.065(3) Uiso 1.000000 GR
H15c H 0.630(3) -0.081(6) 0.1747(7) 0.065(3) Uiso 1.000000 GR


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 C5 1.260(8) . ?
N2 C4 1.374(9) . ?
N2 C6 1.377(9) . ?
N2 H2 0.8600 . ?
C3 C4 1.434(9) . ?
C3 C8 1.402(10) . ?
C3 C10 1.426(10) . ?
C4 C13 1.379(11) . ?
C5 C6 1.391(10) . ?
C5 C12 1.535(9) . ?
C6 C10 1.419(10) . ?
C7 C10 1.470(10) . ?
C7 C11 1.541(10) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C8 C14 1.356(10) . ?
C8 H8 0.9300 . ?
C9 C13 1.390(11) . ?
C9 C14 1.436(10) . ?
C9 H9 0.9300 . ?
C11 C12 1.509(10) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C13 H13 0.9300 . ?
C14 C15 1.506(11) . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?

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 N2 C4 109.2(6) . . ?
H2 N2 C4 125.4(4) . . ?
H2 N2 C6 125.4(4) . . ?
C8 C3 C4 117.8(7) . . ?
C10 C3 C4 108.1(6) . . ?
C10 C3 C8 134.1(7) . . ?
C3 C4 N2 107.5(7) . . ?
C13 C4 N2 131.2(7) . . ?
C13 C4 C3 121.3(7) . . ?
C6 C5 O1 124.5(6) . . ?
C12 C5 O1 119.9(6) . . ?
C12 C5 C6 115.7(6) . . ?
C5 C6 N2 125.1(6) . . ?
C10 C6 N2 110.0(6) . . ?
C10 C6 C5 124.9(6) . . ?
C11 C7 C10 109.5(6) . . ?
H7a C7 C10 109.8(4) . . ?
H7a C7 C11 109.8(4) . . ?
H7b C7 C10 109.8(4) . . ?
H7b C7 C11 109.8(4) . . ?
H7b C7 H7a 108.2 . . ?
C14 C8 C3 122.9(8) . . ?
H8 C8 C3 118.5(4) . . ?
H8 C8 C14 118.5(5) . . ?
C14 C9 C13 122.3(8) . . ?
H9 C9 C13 118.9(5) . . ?
H9 C9 C14 118.9(5) . . ?
C6 C10 C3 105.2(6) . . ?
C7 C10 C3 133.0(6) . . ?
C7 C10 C6 121.8(6) . . ?
C12 C11 C7 113.6(6) . . ?
H11a C11 C7 108.8(3) . . ?
H11a C11 C12 108.8(4) . . ?
H11b C11 C7 108.8(4) . . ?
H11b C11 C12 108.8(4) . . ?
H11b C11 H11a 107.7 . . ?
C11 C12 C5 114.0(6) . . ?
H12a C12 C5 108.8(4) . . ?
H12a C12 C11 108.8(4) . . ?
H12b C12 C5 108.8(3) . . ?
H12b C12 C11 108.8(4) . . ?
H12b C12 H12a 107.7 . . ?
C9 C13 C4 118.2(7) . . ?
H13 C13 C4 120.9(4) . . ?
H13 C13 C9 120.9(5) . . ?
C9 C14 C8 117.5(8) . . ?
C15 C14 C8 122.3(7) . . ?
C15 C14 C9 120.3(8) . . ?
H15a C15 C14 109.5 . . ?
H15b C15 C14 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C14 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
21 0 -1 0.0648 21.0000 -0.0000 -1.0000 -0.2948 -0.0947 0.9663
-12 -8 -3 0.0751 -12.0000 -8.0000 -3.0000 -0.5994 -0.2481 -0.8119
-20 1 2 0.0894 -20.0000 1.0000 2.0000 0.3722 0.1478 -0.8880
-9 8 5 0.1023 -9.0000 8.0000 5.0000 0.8866 0.3758 -0.1547
15 7 2 0.0755 15.0000 7.0000 2.0000 0.4644 0.1832 0.9176
-1 1 29 0.0213 -1.0000 1.0000 29.0000 -0.1063 0.9822 -0.0213
1 -1 -29 0.0279 1.0000 -1.0000 -29.0000 0.1063 -0.9822 0.0213

_olex2_date_sample_data_collection 1336725831.94
_olex2_submission_special_instructions 'No special instructions were received'
