# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_599
_database_code_depnum_ccdc_archive 'CCDC 1578030'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2018-04-30 downloaded from the CCDC.
;
_audit_creation_date             2017-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H18 N2 O'
_chemical_formula_sum            'C15 H18 N2 O'
_chemical_formula_weight         242.31
_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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   20.1725(15)
_cell_length_b                   7.0286(5)
_cell_length_c                   8.7880(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.475(7)
_cell_angle_gamma                90
_cell_volume                     1244.84(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9170
_cell_measurement_theta_min      4.1840
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78473
_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            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3388
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.478
_diffrn_reflns_theta_min         3.822
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  12.00   1.00    2.78    --  -11.66 -57.00 150.00   89
  2  ω    -38.00  61.00   1.00    2.78    --  -11.66  57.00 -60.00   99
  3  ω    -15.00  35.00   1.00    2.78    --   11.90  77.00  60.00   50
;
_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      0.0317983000
_diffrn_orient_matrix_UB_12      0.0085156000
_diffrn_orient_matrix_UB_13      -0.0307457000
_diffrn_orient_matrix_UB_21      -0.0145329000
_diffrn_orient_matrix_UB_22      -0.0084906000
_diffrn_orient_matrix_UB_23      -0.0746204000
_diffrn_orient_matrix_UB_31      -0.0039387000
_diffrn_orient_matrix_UB_32      0.1002221000
_diffrn_orient_matrix_UB_33      -0.0037101000
_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                1155
_reflns_number_total             1253
_reflns_odcompleteness_completeness 99.56
_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         0.160
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+0.7220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H9a(0.5) H9b(0.5) H8a(0.5) H8b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C8(H8a,H8b)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C3(H3), C2(H2a)
3.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.20993(3) 0.5000 0.71541(6) 0.02121(15) Uani 1 2 d S T P . .
N1 N 0.27084(3) 0.5000 0.27202(8) 0.01864(17) Uani 1 2 d S T P . .
N2 N 0.37988(3) 0.5000 0.37259(8) 0.02060(18) Uani 1 2 d S T P . .
C7 C 0.22580(4) 0.5000 0.56746(9) 0.01655(19) Uani 1 2 d S T P . .
C5 C 0.20428(4) 0.5000 0.29793(10) 0.01732(19) Uani 1 2 d S T P . .
C11 C 0.31311(4) 0.5000 0.39197(9) 0.01669(19) Uani 1 2 d S T P . .
C10 C 0.29169(4) 0.5000 0.54395(9) 0.01668(19) Uani 1 2 d S T P . .
C6 C 0.17784(4) 0.5000 0.44551(9) 0.01732(19) Uani 1 2 d S T P . .
C4 C 0.15860(4) 0.5000 0.17130(10) 0.0201(2) Uani 1 2 d S T P . .
H4 H 0.1743 0.5000 0.0733 0.024 Uiso 1 2 calc RS T P . .
C12 C 0.41467(4) 0.5000 0.22837(9) 0.0194(2) Uani 1 2 d S T P . .
C1 C 0.10872(4) 0.5000 0.46236(10) 0.0214(2) Uani 1 2 d S T P . .
H1 H 0.0920 0.5000 0.5593 0.026 Uiso 1 2 calc RS T P . .
C9 C 0.32928(4) 0.5000 0.69517(9) 0.0186(2) Uani 1 2 d S T P . .
H9A H 0.3568 0.6126 0.7079 0.022 Uiso 0.5 1 calc R . . . .
H9B H 0.3568 0.3874 0.7079 0.022 Uiso 0.5 1 calc R . . . .
C3 C 0.09134(4) 0.5000 0.19069(10) 0.0227(2) Uani 1 2 d S T P . .
H3 H 0.0622 0.5000 0.1057 0.027 Uiso 1 2 calc RS T P . .
C15 C 0.39760(3) 0.32170(9) 0.13587(7) 0.02581(16) Uani 1 1 d . . . . .
H15A H 0.4101 0.2110 0.1943 0.039 Uiso 1 1 calc GR . . . .
H15B H 0.4212 0.3232 0.0434 0.039 Uiso 1 1 calc GR . . . .
H15C H 0.3507 0.3187 0.1118 0.039 Uiso 1 1 calc GR . . . .
C2 C 0.06600(4) 0.5000 0.33714(11) 0.0234(2) Uani 1 2 d S T P . .
H2A H 0.0204 0.5000 0.3489 0.028 Uiso 1 2 calc RS T P . .
C8 C 0.27200(4) 0.5000 0.80624(10) 0.0220(2) Uani 1 2 d S T P . .
H8A H 0.2747 0.3880 0.8707 0.026 Uiso 0.5 1 calc R . . . .
H8B H 0.2747 0.6120 0.8707 0.026 Uiso 0.5 1 calc R . . . .
C13 C 0.48847(4) 0.5000 0.27394(10) 0.0256(2) Uani 1 2 d S T P . .
H2 H 0.4044(5) 0.5000 0.4530(12) 0.033(3) Uiso 1 2 d S T P . .
H13A H 0.5011(3) 0.3840(11) 0.3377(8) 0.0314(19) Uiso 1 1 d . . . . .
H13B H 0.5133(5) 0.5000 0.1830(11) 0.028(3) Uiso 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0187(3) 0.0292(3) 0.0159(3) 0.000 0.0031(2) 0.000
N1 0.0173(3) 0.0208(3) 0.0178(3) 0.000 0.0010(3) 0.000
N2 0.0155(3) 0.0310(4) 0.0152(3) 0.000 0.0004(3) 0.000
C7 0.0202(4) 0.0125(3) 0.0171(4) 0.000 0.0031(3) 0.000
C5 0.0180(4) 0.0124(3) 0.0215(4) 0.000 0.0000(3) 0.000
C11 0.0169(3) 0.0141(3) 0.0191(4) 0.000 0.0014(3) 0.000
C10 0.0184(4) 0.0135(3) 0.0181(4) 0.000 0.0004(3) 0.000
C6 0.0179(4) 0.0127(3) 0.0214(4) 0.000 0.0013(3) 0.000
C4 0.0231(4) 0.0191(4) 0.0179(4) 0.000 -0.0008(3) 0.000
C12 0.0170(4) 0.0228(4) 0.0187(4) 0.000 0.0044(3) 0.000
C1 0.0192(4) 0.0207(4) 0.0246(4) 0.000 0.0047(3) 0.000
C9 0.0195(4) 0.0182(4) 0.0181(4) 0.000 0.0007(3) 0.000
C3 0.0225(4) 0.0190(4) 0.0261(4) 0.000 -0.0072(4) 0.000
C15 0.0274(3) 0.0269(3) 0.0235(3) -0.0032(3) 0.0051(2) -0.0016(3)
C2 0.0147(4) 0.0216(4) 0.0337(5) 0.000 -0.0003(3) 0.000
C8 0.0210(4) 0.0288(4) 0.0160(4) 0.000 -0.0013(3) 0.000
C13 0.0181(4) 0.0332(4) 0.0257(4) 0.000 0.0045(3) 0.000

_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 C7 1.3523(10) . ?
O1 C8 1.4554(10) . ?
N1 C5 1.3716(10) . ?
N1 C11 1.3269(10) . ?
N2 C11 1.3648(10) . ?
N2 C12 1.4750(11) . ?
N2 H2 0.845(10) . ?
C7 C10 1.3540(11) . ?
C7 C6 1.4124(11) . ?
C5 C6 1.4234(12) . ?
C5 C4 1.4139(12) . ?
C11 C10 1.4214(12) . ?
C10 C9 1.5014(11) . ?
C6 C1 1.4085(11) . ?
C4 H4 0.9300 . ?
C4 C3 1.3747(12) . ?
C12 C15 1.5250(8) . ?
C12 C15 1.5251(8) 6_565 ?
C12 C13 1.5250(12) . ?
C1 H1 0.9300 . ?
C1 C2 1.3681(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.5445(12) . ?
C3 H3 0.9300 . ?
C3 C2 1.4052(13) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C2 H2A 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C13 H13A 1.016(7) . ?
C13 H13B 0.961(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C8 107.08(6) . . ?
C11 N1 C5 117.92(7) . . ?
C11 N2 C12 128.02(7) . . ?
C11 N2 H2 116.1(7) . . ?
C12 N2 H2 115.8(7) . . ?
O1 C7 C10 114.92(7) . . ?
O1 C7 C6 123.14(7) . . ?
C10 C7 C6 121.94(8) . . ?
N1 C5 C6 124.00(7) . . ?
N1 C5 C4 118.60(8) . . ?
C4 C5 C6 117.39(7) . . ?
N1 C11 N2 120.31(7) . . ?
N1 C11 C10 122.37(7) . . ?
N2 C11 C10 117.32(7) . . ?
C7 C10 C11 118.92(7) . . ?
C7 C10 C9 109.06(7) . . ?
C11 C10 C9 132.02(7) . . ?
C7 C6 C5 114.84(7) . . ?
C1 C6 C7 124.68(8) . . ?
C1 C6 C5 120.48(7) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.04(8) . . ?
C3 C4 H4 119.5 . . ?
N2 C12 C15 110.68(4) . 6_565 ?
N2 C12 C15 110.68(4) . . ?
N2 C12 C13 105.65(7) . . ?
C15 C12 C15 110.52(7) . 6_565 ?
C13 C12 C15 109.59(4) . . ?
C13 C12 C15 109.60(4) . 6_565 ?
C6 C1 H1 119.8 . . ?
C2 C1 C6 120.50(8) . . ?
C2 C1 H1 119.8 . . ?
C10 C9 H9A 111.5 . . ?
C10 C9 H9B 111.5 . . ?
C10 C9 C8 101.32(6) . . ?
H9A C9 H9B 109.3 . . ?
C8 C9 H9A 111.5 . . ?
C8 C9 H9B 111.5 . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 120.91(8) . . ?
C2 C3 H3 119.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C2 C3 119.68(8) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
O1 C8 C9 107.62(6) . . ?
O1 C8 H8A 110.2 . . ?
O1 C8 H8B 110.2 . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C12 C13 H13A 111.4(4) . . ?
C12 C13 H13B 108.6(6) . . ?
H13A C13 H13B 109.4(5) . . ?

_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 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.620
