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

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

data_exp_559
_database_code_depnum_ccdc_archive 'CCDC 1559763'
_audit_update_record             
;
2017-07-03 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;
_audit_creation_date             2017-05-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 N2 O'
_chemical_formula_sum            'C11 H12 N2 O'
_chemical_formula_weight         188.23
_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'

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

_cell_length_a                   6.2899(4)
_cell_length_b                   7.1826(5)
_cell_length_c                   11.4722(8)
_cell_angle_alpha                85.248(6)
_cell_angle_beta                 82.608(6)
_cell_angle_gamma                72.427(6)
_cell_volume                     489.46(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1569
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.5620
_cell_measurement_theta_min      4.5780
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4215
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.539
_diffrn_reflns_theta_min         3.404
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  67.00   1.00    2.80    --   11.74  37.00 -30.00   27
  2  ω     -1.00  81.00   1.00    2.80    --   11.74  57.00 -90.00   82
  3  ω    -43.00 -16.00   1.00    2.80    --   11.74 -57.00  60.00   27
  4  ω    -57.00  34.00   1.00    2.80    --   11.74 -57.00   0.00   91
  5  ω    -14.00  82.00   1.00    2.80    --   11.74  57.00 150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0872307000
_diffrn_orient_matrix_UB_12      0.0584908000
_diffrn_orient_matrix_UB_13      -0.0323992000
_diffrn_orient_matrix_UB_21      -0.0768272000
_diffrn_orient_matrix_UB_22      0.0091580000
_diffrn_orient_matrix_UB_23      0.0516970000
_diffrn_orient_matrix_UB_31      0.0254761000
_diffrn_orient_matrix_UB_32      0.0851381000
_diffrn_orient_matrix_UB_33      0.0131596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1736
_reflns_number_total             2259
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.1460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1294
_refine_special_details          ?
_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:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C6(H6), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.01498(18) 0.16383(16) 0.66596(10) 0.0245(3) Uani 1 1 d . . . . .
N2 N 0.4127(2) 0.25306(18) 0.52481(11) 0.0178(3) Uani 1 1 d . . . . .
H2 H 0.298370 0.263132 0.576495 0.021 Uiso 1 1 calc R . . . .
N1 N 0.2638(2) 0.3768(2) -0.05255(12) 0.0265(3) Uani 1 1 d . . . . .
C7 C 0.6333(2) 0.2114(2) 0.56326(13) 0.0162(3) Uani 1 1 d . . . . .
H7A H 0.697373 0.315545 0.533816 0.019 Uiso 1 1 calc R . . . .
H7B H 0.729879 0.090734 0.530265 0.019 Uiso 1 1 calc R . . . .
C9 C 0.8527(3) 0.1626(2) 0.73570(13) 0.0174(3) Uani 1 1 d . . . . .
C4 C 0.3157(3) 0.3320(2) 0.16904(13) 0.0166(3) Uani 1 1 d . . . . .
C1 C 0.3823(2) 0.2766(2) 0.40850(13) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.5650(3) 0.2559(2) 0.32060(13) 0.0170(3) Uani 1 1 d . . . . .
H2A H 0.709895 0.224061 0.341880 0.020 Uiso 1 1 calc R . . . .
C6 C 0.1649(2) 0.3253(2) 0.37282(13) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.042068 0.337954 0.429407 0.022 Uiso 1 1 calc R . . . .
C3 C 0.5311(3) 0.2822(2) 0.20347(13) 0.0183(3) Uani 1 1 d . . . . .
H3 H 0.653679 0.266578 0.146493 0.022 Uiso 1 1 calc R . . . .
C8 C 0.6260(2) 0.1924(2) 0.69591(12) 0.0167(3) Uani 1 1 d . . . . .
H8A H 0.521685 0.309680 0.729227 0.020 Uiso 1 1 calc R . . . .
H8B H 0.571483 0.082632 0.724969 0.020 Uiso 1 1 calc R . . . .
C5 C 0.1317(3) 0.3544(2) 0.25573(13) 0.0183(3) Uani 1 1 d . . . . .
H5 H -0.012984 0.389083 0.233890 0.022 Uiso 1 1 calc R . . . .
C11 C 0.2841(3) 0.3579(2) 0.04633(14) 0.0197(3) Uani 1 1 d . . . . .
C10 C 0.8716(3) 0.1287(2) 0.86559(14) 0.0236(4) Uani 1 1 d . . . . .
H10A H 0.878658 -0.004508 0.888476 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.742975 0.214775 0.908142 0.035 Uiso 1 1 calc GR . . . .
H10C H 1.005193 0.154071 0.883065 0.035 Uiso 1 1 calc GR . . . .


_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 C9 1.2148(17) . ?
N2 H2 0.8600 . ?
N2 C7 1.447(2) . ?
N2 C1 1.3617(19) . ?
N1 C11 1.150(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.513(2) . ?
C9 C8 1.502(2) . ?
C9 C10 1.504(2) . ?
C4 C3 1.393(2) . ?
C4 C5 1.404(2) . ?
C4 C11 1.436(2) . ?
C1 C2 1.4080(19) . ?
C1 C6 1.411(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.376(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.375(2) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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 N2 H2 119.3 . . ?
C1 N2 H2 119.3 . . ?
C1 N2 C7 121.36(12) . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
N2 C7 C8 112.04(12) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O1 C9 C8 121.52(14) . . ?
O1 C9 C10 121.24(14) . . ?
C8 C9 C10 117.24(12) . . ?
C3 C4 C5 119.08(14) . . ?
C3 C4 C11 120.06(13) . . ?
C5 C4 C11 120.86(14) . . ?
N2 C1 C2 121.38(13) . . ?
N2 C1 C6 120.55(12) . . ?
C2 C1 C6 118.07(14) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 C1 120.61(14) . . ?
C3 C2 H2A 119.7 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.06(13) . . ?
C5 C6 H6 119.5 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 120.96(13) . . ?
C2 C3 H3 119.5 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 C7 111.89(12) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.21(14) . . ?
C6 C5 H5 119.9 . . ?
N1 C11 C4 178.49(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O1 C9 C8 C7 3.10(19) . . . . ?
N2 C7 C8 C9 -176.19(11) . . . . ?
N2 C1 C2 C3 -179.31(13) . . . . ?
N2 C1 C6 C5 178.30(13) . . . . ?
C7 N2 C1 C2 1.9(2) . . . . ?
C7 N2 C1 C6 -177.30(13) . . . . ?
C1 N2 C7 C8 179.67(12) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C1 C6 C5 C4 1.3(2) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C5 C4 C3 C2 -0.3(2) . . . . ?
C11 C4 C3 C2 -179.68(13) . . . . ?
C11 C4 C5 C6 178.67(13) . . . . ?
C10 C9 C8 C7 -176.19(12) . . . . ?

_olex2_date_sample_data_collection 2017-05-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.658
