# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_123_a
_database_code_depnum_ccdc_archive 'CCDC 1944356'
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 N0 O2'
_chemical_formula_weight         219.29

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

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

_cell_length_a                   9.026(2)
_cell_length_b                   11.173(2)
_cell_length_c                   23.919(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2412.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5754
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19432
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.827
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2128
_reflns_number_gt                1866
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²+0.8221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2128
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_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 0.42237(16) 0.68864(11) 0.36106(7) 0.0787(5) Uani 1 1 d . . . . .
C1 C 0.45369(18) 0.58286(14) 0.36720(7) 0.0459(4) Uani 1 1 d . . . . .
C2 C 0.33672(17) 0.48899(15) 0.36099(7) 0.0498(4) Uani 1 1 d . . . . .
H2 H 0.2773 0.4978 0.3270 0.060 Uiso 1 1 calc R U . . .
O2 O 0.57996(12) 0.23110(9) 0.40786(5) 0.0480(3) Uani 1 1 d . . . . .
C3 C 0.39338(16) 0.35896(13) 0.37085(6) 0.0412(4) Uani 1 1 d . . . . .
H3 H 0.3336 0.3005 0.3503 0.049 Uiso 1 1 calc R U . . .
C4 C 0.55635(16) 0.32809(12) 0.36845(6) 0.0358(3) Uani 1 1 d . . . . .
C5 C 0.65316(16) 0.43430(12) 0.38377(6) 0.0380(4) Uani 1 1 d . . . . .
C8 C 0.2412(2) 0.4753(2) 0.41553(9) 0.0750(6) Uani 1 1 d . . . . .
H8A H 0.2481 0.5426 0.4410 0.090 Uiso 1 1 calc R U . . .
H8B H 0.1389 0.4529 0.4088 0.090 Uiso 1 1 calc R U . . .
C7 C 0.81155(19) 0.40909(17) 0.39925(10) 0.0649(5) Uani 1 1 d . . . . .
H7A H 0.8594 0.4824 0.4098 0.097 Uiso 1 1 calc R U . . .
H7B H 0.8621 0.3748 0.3678 0.097 Uiso 1 1 calc R U . . .
H7C H 0.8143 0.3540 0.4300 0.097 Uiso 1 1 calc R U . . .
C6 C 0.60373(17) 0.54701(13) 0.38143(6) 0.0408(4) Uani 1 1 d . . . . .
H6 H 0.6711 0.6075 0.3896 0.049 Uiso 1 1 calc R U . . .
C9 C 0.34089(19) 0.37204(16) 0.43010(7) 0.0546(4) Uani 1 1 d . . . . .
C10 C 0.4130(2) 0.33117(19) 0.47361(7) 0.0652(5) Uani 1 1 d . . . . .
H10 H 0.3821 0.3506 0.5096 0.078 Uiso 1 1 calc R U . . .
C11 C 0.5439(2) 0.25394(19) 0.46509(7) 0.0656(5) Uani 1 1 d . . . . .
H11A H 0.6286 0.2913 0.4829 0.079 Uiso 1 1 calc R U . . .
H11B H 0.5266 0.1780 0.4836 0.079 Uiso 1 1 calc R U . . .
C12 C 0.6068(2) 0.27629(13) 0.31160(6) 0.0493(4) Uani 1 1 d . . . . .
H12 H 0.7127 0.2581 0.3146 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5270(3) 0.16035(16) 0.29655(9) 0.0769(7) Uani 1 1 d . . . . .
H13A H 0.4254 0.1775 0.2877 0.115 Uiso 1 1 calc R U . . .
H13B H 0.5311 0.1063 0.3277 0.115 Uiso 1 1 calc R U . . .
H13C H 0.5742 0.1243 0.2648 0.115 Uiso 1 1 calc R U . . .
C14 C 0.5877(3) 0.36697(17) 0.26468(7) 0.0718(6) Uani 1 1 d . . . . .
H14A H 0.6188 0.3319 0.2300 0.108 Uiso 1 1 calc R U . . .
H14B H 0.6469 0.4364 0.2724 0.108 Uiso 1 1 calc R U . . .
H14C H 0.4854 0.3898 0.2621 0.108 Uiso 1 1 calc R U . . .


_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 C1 1.224(2) . ?
C1 C6 1.453(2) . ?
C1 C2 1.496(2) . ?
C2 C3 1.558(2) . ?
C2 C8 1.571(3) . ?
C2 H2 0.9800 . ?
O2 C11 1.430(2) . ?
O2 C4 1.4520(17) . ?
C3 C9 1.502(2) . ?
C3 C4 1.512(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.5186(19) . ?
C4 C12 1.546(2) . ?
C5 C6 1.337(2) . ?
C5 C7 1.504(2) . ?
C8 C9 1.504(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6 0.9300 . ?
C9 C10 1.310(3) . ?
C10 C11 1.477(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C14 1.522(2) . ?
C12 C13 1.525(2) . ?
C12 H12 0.9800 . ?
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
O1 C1 C6 120.64(15) . . ?
O1 C1 C2 120.15(15) . . ?
C6 C1 C2 119.21(13) . . ?
C1 C2 C3 114.02(13) . . ?
C1 C2 C8 111.91(15) . . ?
C3 C2 C8 87.91(13) . . ?
C1 C2 H2 113.5 . . ?
C3 C2 H2 113.5 . . ?
C8 C2 H2 113.5 . . ?
C11 O2 C4 117.06(13) . . ?
C9 C3 C4 111.41(13) . . ?
C9 C3 C2 87.05(12) . . ?
C4 C3 C2 121.76(13) . . ?
C9 C3 H3 111.4 . . ?
C4 C3 H3 111.4 . . ?
C2 C3 H3 111.4 . . ?
O2 C4 C3 106.76(11) . . ?
O2 C4 C5 110.01(11) . . ?
C3 C4 C5 111.86(12) . . ?
O2 C4 C12 104.38(11) . . ?
C3 C4 C12 113.89(13) . . ?
C5 C4 C12 109.60(12) . . ?
C6 C5 C7 120.26(14) . . ?
C6 C5 C4 122.27(13) . . ?
C7 C5 C4 117.40(13) . . ?
C9 C8 C2 86.50(13) . . ?
C9 C8 H8A 114.2 . . ?
C2 C8 H8A 114.2 . . ?
C9 C8 H8B 114.2 . . ?
C2 C8 H8B 114.2 . . ?
H8A C8 H8B 111.4 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 C1 125.48(14) . . ?
C5 C6 H6 117.3 . . ?
C1 C6 H6 117.3 . . ?
C10 C9 C3 124.00(17) . . ?
C10 C9 C8 138.51(19) . . ?
C3 C9 C8 92.56(15) . . ?
C9 C10 C11 119.44(17) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
O2 C11 C10 114.73(15) . . ?
O2 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
O2 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C14 C12 C13 109.76(16) . . ?
C14 C12 C4 111.48(13) . . ?
C13 C12 C4 112.74(14) . . ?
C14 C12 H12 107.5 . . ?
C13 C12 H12 107.5 . . ?
C4 C12 H12 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.034

