# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
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#######################################################################

data_20180516CZ_CJ_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1848812'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   6.8817(10)
_cell_length_b                   9.3770(11)
_cell_length_c                   13.0597(15)
_cell_angle_alpha                84.642(4)
_cell_angle_beta                 75.196(4)
_cell_angle_gamma                78.648(4)
_cell_volume                     798.00(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3904
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      28.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(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            5120
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             2677
_reflns_number_gt                2242
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+5.0000P] 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         2677
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0920
_refine_ls_wR_factor_ref         0.2452
_refine_ls_wR_factor_gt          0.2248
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
C1 C 0.1750(7) 0.5602(5) 0.6760(4) 0.0223(10) Uani 1 1 d . . . . .
C2 C 0.1581(7) 0.5114(5) 0.7823(4) 0.0262(10) Uani 1 1 d . . . . .
H2 H 0.193203 0.410947 0.800892 0.031 Uiso 1 1 calc R U . . .
C3 C 0.0892(8) 0.6132(5) 0.8589(4) 0.0292(11) Uani 1 1 d . . . . .
H3 H 0.075031 0.582254 0.931383 0.035 Uiso 1 1 calc R U . . .
C4 C 0.0399(8) 0.7611(5) 0.8319(4) 0.0300(11) Uani 1 1 d . . . . .
H4 H -0.006637 0.828472 0.886773 0.036 Uiso 1 1 calc R U . . .
C5 C 0.0565(8) 0.8127(5) 0.7280(4) 0.0307(11) Uani 1 1 d . . . . .
H5 H 0.023900 0.913620 0.710175 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1232(7) 0.7098(5) 0.6511(4) 0.0245(10) Uani 1 1 d . . . . .
C7 C 0.2153(7) 0.5971(5) 0.4966(4) 0.0203(9) Uani 1 1 d . . . . .
C8 C 0.2345(7) 0.4887(5) 0.5762(4) 0.0209(9) Uani 1 1 d . . . . .
C9 C 0.3079(7) 0.3448(5) 0.5490(3) 0.0209(10) Uani 1 1 d . . . . .
C10 C 0.3449(7) 0.3122(5) 0.4421(3) 0.0202(9) Uani 1 1 d . . . . .
C11 C 0.3252(6) 0.4231(5) 0.3596(3) 0.0198(9) Uani 1 1 d . . . . .
C12 C 0.2615(7) 0.5680(5) 0.3867(3) 0.0202(9) Uani 1 1 d . . . . .
C13 C 0.2398(7) 0.6960(5) 0.3124(4) 0.0237(10) Uani 1 1 d . . . . .
C14 C 0.3434(9) 0.7850(5) 0.1280(4) 0.0347(13) Uani 1 1 d . . . . .
C15 C 0.4797(11) 0.7044(6) 0.0320(4) 0.0466(16) Uani 1 1 d . . . . .
H15A H 0.613163 0.663054 0.046071 0.070 Uiso 1 1 calc R U . . .
H15B H 0.497745 0.772350 -0.030008 0.070 Uiso 1 1 calc R U . . .
H15C H 0.415925 0.625861 0.018093 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1284(10) 0.8368(6) 0.1136(4) 0.0419(14) Uani 1 1 d . . . . .
H16A H 0.073651 0.753569 0.099767 0.063 Uiso 1 1 calc R U . . .
H16B H 0.131580 0.907985 0.053531 0.063 Uiso 1 1 calc R U . . .
H16C H 0.041244 0.882256 0.178124 0.063 Uiso 1 1 calc R U . . .
C17 C 0.4388(10) 0.9057(6) 0.1526(4) 0.0422(14) Uani 1 1 d . . . . .
H17A H 0.348554 0.956086 0.214376 0.063 Uiso 1 1 calc R U . . .
H17B H 0.458365 0.974933 0.091397 0.063 Uiso 1 1 calc R U . . .
H17C H 0.571221 0.864290 0.167815 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4095(8) 0.1642(5) 0.4149(4) 0.0281(11) Uani 1 1 d . . . . .
C19 C 0.3697(7) 0.3726(5) 0.2483(3) 0.0229(10) Uani 1 1 d . . . . .
H19A H 0.266630 0.426965 0.212748 0.034 Uiso 1 1 calc R U . . .
H19B H 0.365813 0.268403 0.250924 0.034 Uiso 1 1 calc R U . . .
H19C H 0.505413 0.389693 0.209034 0.034 Uiso 1 1 calc R U . . .
N1 N 0.4595(9) 0.0437(5) 0.3951(4) 0.0446(13) Uani 1 1 d . . . . .
N2 N 0.1498(6) 0.7284(4) 0.5418(3) 0.0222(9) Uani 1 1 d . . . . .
H2A H 0.127564 0.812676 0.507085 0.027 Uiso 1 1 calc R U . . .
O1 O 0.3343(5) 0.2448(3) 0.6284(2) 0.0285(8) Uani 1 1 d . . . . .
H1 H 0.383774 0.162712 0.602998 0.043 Uiso 1 1 calc R U . . .
O2 O 0.1443(5) 0.8146(3) 0.3421(3) 0.0309(8) Uani 1 1 d . . . . .
O3 O 0.3404(5) 0.6687(3) 0.2125(3) 0.0295(8) Uani 1 1 d . . . . .


_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
C1 C2 1.403(7) . ?
C1 C6 1.407(6) . ?
C1 C8 1.448(6) . ?
C2 C3 1.376(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(7) . ?
C5 H5 0.9500 . ?
C6 N2 1.390(6) . ?
C7 N2 1.360(6) . ?
C7 C8 1.397(6) . ?
C7 C12 1.429(6) . ?
C8 C9 1.390(6) . ?
C9 O1 1.354(5) . ?
C9 C10 1.406(6) . ?
C10 C18 1.421(6) . ?
C10 C11 1.438(6) . ?
C11 C12 1.393(6) . ?
C11 C19 1.507(6) . ?
C12 C13 1.480(6) . ?
C13 O2 1.217(5) . ?
C13 O3 1.333(6) . ?
C14 O3 1.476(5) . ?
C14 C17 1.511(8) . ?
C14 C16 1.517(8) . ?
C14 C15 1.523(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.148(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N2 H2A 0.8800 . ?
O1 H1 0.8400 . ?

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
C2 C1 C6 119.5(4) . . ?
C2 C1 C8 134.3(4) . . ?
C6 C1 C8 106.2(4) . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.1(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 122.1(4) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 116.7(4) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
C5 C6 N2 129.6(4) . . ?
C5 C6 C1 122.4(5) . . ?
N2 C6 C1 108.0(4) . . ?
N2 C7 C8 108.8(4) . . ?
N2 C7 C12 127.9(4) . . ?
C8 C7 C12 123.4(4) . . ?
C9 C8 C7 119.5(4) . . ?
C9 C8 C1 133.3(4) . . ?
C7 C8 C1 107.1(4) . . ?
O1 C9 C8 117.4(4) . . ?
O1 C9 C10 124.5(4) . . ?
C8 C9 C10 118.1(4) . . ?
C9 C10 C18 118.2(4) . . ?
C9 C10 C11 122.5(4) . . ?
C18 C10 C11 119.2(4) . . ?
C12 C11 C10 119.0(4) . . ?
C12 C11 C19 124.1(4) . . ?
C10 C11 C19 116.9(4) . . ?
C11 C12 C7 117.3(4) . . ?
C11 C12 C13 126.3(4) . . ?
C7 C12 C13 116.4(4) . . ?
O2 C13 O3 124.5(4) . . ?
O2 C13 C12 122.2(4) . . ?
O3 C13 C12 113.3(4) . . ?
O3 C14 C17 110.2(4) . . ?
O3 C14 C16 109.2(5) . . ?
C17 C14 C16 113.3(4) . . ?
O3 C14 C15 101.7(4) . . ?
C17 C14 C15 110.9(5) . . ?
C16 C14 C15 110.9(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C10 178.6(6) . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 N2 C6 109.9(4) . . ?
C7 N2 H2A 125.0 . . ?
C6 N2 H2A 125.0 . . ?
C9 O1 H1 109.5 . . ?
C13 O3 C14 121.0(3) . . ?

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.113

