# 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_mk1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O'
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14

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

_cell_length_a                   8.856(1)
_cell_length_b                   13.861(1)
_cell_length_c                   10.868(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.41(1)
_cell_angle_gamma                90.00
_cell_volume                     1332.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    55
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      19.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick, Bruker AXS Inc.,2002)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       φ
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18034
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2165
_reflns_number_gt                1752
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2005)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997), SCHAKAL99 (Keller & Pierrard, 1999)'
_computing_publication_material  
'WinGX (Farrugia, 1999), enCIFer (Allen et al., 2004)'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0773P)²+0.1887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2165
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.17524(18) 0.05932(10) 0.21289(12) 0.0600(4) Uani 1 1 d . . .
O O 0.21610(16) 0.35802(9) -0.01318(10) 0.0710(4) Uani 1 1 d . . .
C1 C 0.22429(17) 0.10960(11) 0.10796(11) 0.0450(4) Uani 1 1 d . . .
C2 C 0.18903(17) 0.20813(11) 0.10054(12) 0.0475(4) Uani 1 1 d . . .
H2 H 0.1317 0.2376 0.1596 0.057 Uiso 1 1 calc R . .
C3 C 0.24297(18) 0.26076(11) 0.00134(12) 0.0489(4) Uani 1 1 d . . .
C4 C 0.32983(19) 0.21663(13) -0.09211(12) 0.0571(4) Uani 1 1 d . . .
H4 H 0.3655 0.2533 -0.1564 0.069 Uiso 1 1 calc R . .
C5 C 0.35941(19) 0.11923(13) -0.08497(13) 0.0582(4) Uani 1 1 d . . .
H5 H 0.4138 0.0894 -0.1457 0.070 Uiso 1 1 calc R . .
C6 C 0.30796(19) 0.06511(12) 0.01321(12) 0.0528(4) Uani 1 1 d . . .
H6 H 0.3283 -0.0007 0.0172 0.063 Uiso 1 1 calc R . .
C7 C 0.20862(18) -0.03974(11) 0.23142(12) 0.0489(4) Uani 1 1 d . . .
C8 C 0.30937(19) -0.07091(12) 0.33110(13) 0.0566(4) Uani 1 1 d . . .
H8 H 0.3575 -0.0254 0.3819 0.068 Uiso 1 1 calc R . .
C9 C 0.3349(2) -0.16864(13) 0.35167(16) 0.0643(5) Uani 1 1 d . . .
H9 H 0.3979 -0.1885 0.4175 0.077 Uiso 1 1 calc R . .
C10 C 0.2653(2) -0.23761(12) 0.27278(16) 0.0624(5) Uani 1 1 d . . .
C11 C 0.1655(2) -0.20525(12) 0.17318(16) 0.0618(5) Uani 1 1 d . . .
H11 H 0.1199 -0.2508 0.1209 0.074 Uiso 1 1 calc R . .
C12 C 0.1355(2) -0.10856(12) 0.15289(14) 0.0574(4) Uani 1 1 d . . .
H12 H 0.0689 -0.0891 0.0892 0.069 Uiso 1 1 calc R . .
C13 C 0.2959(3) -0.34355(15) 0.2946(3) 0.0983(8) Uani 1 1 d . . .
H13A H 0.3660 -0.3510 0.3637 0.148 Uiso 1 1 calc R . .
H13B H 0.3380 -0.3712 0.2227 0.148 Uiso 1 1 calc R . .
H13C H 0.2030 -0.3758 0.3113 0.148 Uiso 1 1 calc R . .
C14 C 0.1486(3) 0.40942(14) 0.08581(16) 0.0819(7) Uani 1 1 d . . .
H14A H 0.0491 0.3845 0.0975 0.123 Uiso 1 1 calc R . .
H14B H 0.1422 0.4768 0.0657 0.123 Uiso 1 1 calc R . .
H14C H 0.2097 0.4012 0.1602 0.123 Uiso 1 1 calc R . .
H1N H 0.174(2) 0.0968(16) 0.2809(19) 0.085(6) Uiso 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 0.0961(12) 0.0476(8) 0.0377(7) 0.0019(5) 0.0178(6) 0.0066(7)
O 0.1139(11) 0.0539(7) 0.0462(6) 0.0101(5) 0.0172(6) 0.0111(7)
C1 0.0524(9) 0.0498(8) 0.0330(7) 0.0012(6) 0.0023(6) 0.0032(6)
C2 0.0575(9) 0.0530(9) 0.0325(7) -0.0016(6) 0.0072(6) 0.0064(7)
C3 0.0598(10) 0.0515(9) 0.0352(7) 0.0058(6) 0.0001(6) 0.0038(7)
C4 0.0673(11) 0.0712(11) 0.0336(7) 0.0095(7) 0.0092(7) 0.0063(8)
C5 0.0695(11) 0.0714(11) 0.0344(7) -0.0015(7) 0.0112(7) 0.0179(9)
C6 0.0659(11) 0.0543(9) 0.0386(7) -0.0019(6) 0.0043(7) 0.0126(7)
C7 0.0595(10) 0.0477(8) 0.0404(7) 0.0046(6) 0.0125(6) 0.0027(7)
C8 0.0647(11) 0.0628(10) 0.0425(8) 0.0013(7) 0.0034(7) -0.0029(8)
C9 0.0654(11) 0.0736(12) 0.0537(9) 0.0192(8) -0.0009(8) 0.0082(9)
C10 0.0634(11) 0.0539(10) 0.0708(10) 0.0151(8) 0.0120(8) 0.0046(8)
C11 0.0688(11) 0.0518(10) 0.0647(10) -0.0015(8) 0.0022(8) -0.0048(8)
C12 0.0658(11) 0.0583(10) 0.0476(8) 0.0041(7) -0.0046(7) 0.0030(8)
C13 0.1114(18) 0.0588(13) 0.1253(19) 0.0294(12) 0.0102(15) 0.0092(12)
C14 0.1307(19) 0.0573(11) 0.0590(10) 0.0045(8) 0.0205(11) 0.0238(11)

_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 C7 1.417(2) . ?
N C1 1.4201(18) . ?
N H1N 0.90(2) . ?
O C3 1.3770(19) . ?
O C14 1.441(2) . ?
C1 C2 1.402(2) . ?
C1 C6 1.4332(19) . ?
C2 C3 1.4021(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.436(2) . ?
C4 C5 1.377(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.418(2) . ?
C7 C8 1.441(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.440(2) . ?
C10 C13 1.510(2) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C7 N C1 121.38(12) . . ?
C7 N H1N 116.8(13) . . ?
C1 N H1N 112.9(14) . . ?
C3 O C14 118.27(12) . . ?
C2 C1 N 116.69(12) . . ?
C2 C1 C6 119.89(12) . . ?
N C1 C6 123.41(13) . . ?
C3 C2 C1 117.94(13) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
O C3 C2 122.32(13) . . ?
O C3 C4 115.53(12) . . ?
C2 C3 C4 122.15(14) . . ?
C5 C4 C3 118.95(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.16(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.86(14) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
N C7 C12 118.61(14) . . ?
N C7 C8 121.09(14) . . ?
C12 C7 C8 120.24(14) . . ?
C9 C8 C7 120.31(15) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.96(16) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 119.02(15) . . ?
C9 C10 C13 119.56(18) . . ?
C11 C10 C13 121.42(18) . . ?
C12 C11 C10 122.00(16) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C7 118.43(15) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O C14 H14A 109.5 . . ?
O C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N C1 C2 -178.13(14) . . . . ?
C7 N C1 C6 0.9(2) . . . . ?
N C1 C2 C3 176.67(14) . . . . ?
C6 C1 C2 C3 -2.4(2) . . . . ?
C14 O C3 C2 8.8(2) . . . . ?
C14 O C3 C4 -171.32(17) . . . . ?
C1 C2 C3 O -179.14(14) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
O C3 C4 C5 -179.02(15) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C2 C1 C6 C5 2.1(2) . . . . ?
N C1 C6 C5 -176.94(15) . . . . ?
C1 N C7 C12 -70.1(2) . . . . ?
C1 N C7 C8 112.65(17) . . . . ?
N C7 C8 C9 176.75(15) . . . . ?
C12 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C8 C9 C10 C13 178.97(18) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C13 C10 C11 C12 179.38(18) . . . . ?
C10 C11 C12 C7 1.5(2) . . . . ?
N C7 C12 C11 -178.44(14) . . . . ?
C8 C7 C12 C11 -1.2(2) . . . . ?

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
N H1N O 0.90(2) 2.34(2) 3.1963(17) 158.3(18) 4_566

_diffrn_measured_fraction_theta_max 0.885
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.885
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.030
_chemical_compound_source        synthesis

_database_code_depnum_ccdc_archive 'CCDC 1000251'
