# 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. 
# 
#######################################################################

data_20170519CZ_XGHKN9_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1575768'
_audit_update_record             
;
2017-09-21 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N3 O2'
_chemical_formula_weight         343.38

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.8340(6)
_cell_length_b                   36.798(4)
_cell_length_c                   8.5249(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.941(3)
_cell_angle_gamma                90
_cell_volume                     1776.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3206
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      21.90
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.986
_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      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            12592
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3113
_reflns_number_gt                2032
_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-2016/6 (Sheldrick, 2016)'
_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)+3.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3113
_refine_ls_number_parameters     257
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.1017
_refine_ls_wR_factor_ref         0.2301
_refine_ls_wR_factor_gt          0.2102
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.001
_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
C3 C 0.5831(18) 0.6551(3) 1.1200(10) 0.138(3) Uani 1 1 d . . . . .
H3A H 0.609313 0.649649 1.233061 0.166 Uiso 1 1 d R U . A .
C4 C 0.3863(17) 0.6468(2) 1.0207(10) 0.119(2) Uani 1 1 d . . . . .
H4A H 0.266274 0.636001 1.059104 0.143 Uiso 1 1 calc R U . . .
C5 C 0.3542(12) 0.65345(16) 0.8647(8) 0.0956(18) Uani 1 1 d . . . . .
H5A H 0.206019 0.648536 0.798348 0.115 Uiso 1 1 calc R U . . .
C6 C 0.5172(9) 0.66663(14) 0.7957(7) 0.0729(14) Uani 1 1 d . . . . .
C7 C 0.4615(8) 0.67247(13) 0.6144(6) 0.0670(13) Uani 1 1 d . . . . .
H7A H 0.307059 0.684433 0.583537 0.080 Uiso 1 1 calc R U . . .
C8 C 0.6355(11) 0.69699(13) 0.5634(8) 0.0871(18) Uani 1 1 d . . . . .
C9 C 0.752(2) 0.7529(3) 0.4893(17) 0.311(8) Uani 1 1 d . U . . .
H9A H 0.689981 0.776812 0.460388 0.467 Uiso 1 1 calc R U . . .
H9B H 0.880347 0.754358 0.583620 0.467 Uiso 1 1 calc R U . . .
H9C H 0.807145 0.742735 0.401445 0.467 Uiso 1 1 calc R U . . .
C10 C 0.4379(7) 0.63594(12) 0.5261(5) 0.0591(12) Uani 1 1 d . . . . .
C11 C 0.6259(8) 0.61202(13) 0.5517(6) 0.0762(15) Uani 1 1 d . . . . .
H11A H 0.765599 0.618215 0.625546 0.091 Uiso 1 1 calc R U . . .
C12 C 0.6132(8) 0.57913(12) 0.4712(6) 0.0775(16) Uani 1 1 d . . . . .
H12A H 0.743078 0.563683 0.488427 0.093 Uiso 1 1 calc R U . . .
C13 C 0.4030(7) 0.56978(11) 0.3645(5) 0.0515(10) Uani 1 1 d . . . . .
C14 C 0.2121(7) 0.59343(13) 0.3385(5) 0.0596(12) Uani 1 1 d . . . . .
C15 C 0.2305(8) 0.62652(13) 0.4208(5) 0.0637(13) Uani 1 1 d . . . . .
H15A H 0.101610 0.642144 0.403923 0.076 Uiso 1 1 calc R U . . .
C16 C 0.1067(8) 0.54474(15) 0.1802(6) 0.0789(16) Uani 1 1 d . . . . .
H16A H 0.019285 0.528579 0.105195 0.095 Uiso 1 1 calc R U . . .
C17 C 0.0271(9) 0.57663(17) 0.2208(7) 0.0946(19) Uani 1 1 d . . . . .
H17A H -0.122909 0.586184 0.179440 0.114 Uiso 1 1 calc R U . . .
C18 C 0.4654(8) 0.50778(11) 0.2543(5) 0.0568(11) Uani 1 1 d . . . . .
C19 C 0.4901(11) 0.45409(14) 0.1347(7) 0.0909(18) Uani 1 1 d . . . . .
H19A H 0.423975 0.436160 0.060672 0.109 Uiso 1 1 calc R U . . .
C20 C 0.7118(11) 0.44913(14) 0.2242(7) 0.0933(18) Uani 1 1 d . . . . .
H20A H 0.799530 0.428598 0.213201 0.112 Uiso 1 1 calc R U . . .
C21 C 0.7993(10) 0.47586(14) 0.3313(7) 0.097(2) Uani 1 1 d . . . . .
H21A H 0.952081 0.473304 0.394946 0.117 Uiso 1 1 calc R U . . .
N1 N 0.3365(6) 0.53927(9) 0.2652(4) 0.0557(9) Uani 1 1 d . . . . .
N2 N 0.6784(7) 0.50565(10) 0.3503(5) 0.0780(13) Uani 1 1 d . . . . .
N3 N 0.3594(7) 0.48354(11) 0.1466(5) 0.0755(12) Uani 1 1 d . . . . .
O1 O 0.8316(10) 0.68968(13) 0.5542(7) 0.139(2) Uani 1 1 d . . . . .
O2 O 0.5571(12) 0.72871(18) 0.5249(14) 0.284(6) Uani 1 1 d . . . . .
C1 C 0.732(3) 0.6616(9) 0.885(2) 0.114(7) Uani 0.61(3) 1 d . . P A 1
H1A H 0.866737 0.661969 0.838615 0.136 Uiso 0.61(3) 1 d R U P A 1
C2 C 0.766(3) 0.6592(9) 1.050(2) 0.146(11) Uani 0.61(3) 1 d . . P A 1
H2B H 0.922642 0.659035 1.118983 0.175 Uiso 0.61(3) 1 d R U P A 1
C2' C 0.745(5) 0.6888(13) 1.063(4) 0.150(13) Uani 0.39(3) 1 d . . P A 2
H2'A H 0.840359 0.706250 1.133968 0.180 Uiso 0.39(3) 1 d R U P A 2
C1' C 0.695(5) 0.6875(13) 0.903(2) 0.107(10) Uani 0.39(3) 1 d . . P A 2
H1'A H 0.786005 0.702830 0.849808 0.129 Uiso 0.39(3) 1 d R U P A 2


_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
C3 C4 1.288(10) . ?
C3 C2 1.35(2) . ?
C3 C2' 1.70(5) . ?
C3 H3A 0.9600 . ?
C4 C5 1.321(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.325(7) . ?
C5 H5A 0.9300 . ?
C6 C1 1.315(14) . ?
C6 C1' 1.43(2) . ?
C6 C7 1.516(7) . ?
C7 C8 1.499(8) . ?
C7 C10 1.530(6) . ?
C7 H7A 0.9800 . ?
C8 O1 1.196(7) . ?
C8 O2 1.267(7) . ?
C9 O2 1.530(11) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.366(6) . ?
C10 C11 1.382(6) . ?
C11 C12 1.385(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.383(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.389(6) . ?
C13 N1 1.403(5) . ?
C14 C15 1.397(6) . ?
C14 C17 1.425(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.338(7) . ?
C16 N1 1.377(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 N3 1.322(5) . ?
C18 N2 1.315(6) . ?
C18 N1 1.397(5) . ?
C19 N3 1.343(6) . ?
C19 C20 1.346(7) . ?
C19 H19A 0.9300 . ?
C20 C21 1.355(7) . ?
C20 H20A 0.9300 . ?
C21 N2 1.335(6) . ?
C21 H21A 0.9300 . ?
C1 C2 1.37(2) . ?
C1 H1A 0.9599 . ?
C2 H2B 0.9600 . ?
C2' C1' 1.33(3) . ?
C2' H2'A 0.9601 . ?
C1' H1'A 0.9599 . ?

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
C4 C3 C2 114.2(11) . . ?
C4 C3 C2' 117.1(12) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 121.1 . . ?
C2' C3 H3A 118.2 . . ?
C3 C4 C5 120.3(8) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 125.0(7) . . ?
C4 C5 H5A 117.5 . . ?
C6 C5 H5A 117.5 . . ?
C1 C6 C5 112.2(9) . . ?
C5 C6 C1' 113.6(10) . . ?
C1 C6 C7 123.4(8) . . ?
C5 C6 C7 120.3(5) . . ?
C1' C6 C7 121.3(13) . . ?
C8 C7 C6 112.8(4) . . ?
C8 C7 C10 111.9(4) . . ?
C6 C7 C10 110.4(4) . . ?
C8 C7 H7A 107.1 . . ?
C6 C7 H7A 107.1 . . ?
C10 C7 H7A 107.1 . . ?
O1 C8 O2 118.8(7) . . ?
O1 C8 C7 127.5(5) . . ?
O2 C8 C7 113.7(6) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 119.0(4) . . ?
C15 C10 C7 120.4(4) . . ?
C11 C10 C7 120.5(4) . . ?
C12 C11 C10 122.2(4) . . ?
C12 C11 H11A 118.9 . . ?
C10 C11 H11A 118.9 . . ?
C11 C12 C13 118.5(4) . . ?
C11 C12 H12A 120.8 . . ?
C13 C12 H12A 120.8 . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 N1 131.9(4) . . ?
C14 C13 N1 108.1(4) . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 C17 106.4(4) . . ?
C15 C14 C17 133.2(4) . . ?
C10 C15 C14 120.0(4) . . ?
C10 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C17 C16 N1 110.3(4) . . ?
C17 C16 H16A 124.9 . . ?
N1 C16 H16A 124.9 . . ?
C16 C17 C14 108.1(4) . . ?
C16 C17 H17A 125.9 . . ?
C14 C17 H17A 125.9 . . ?
N3 C18 N2 127.3(4) . . ?
N3 C18 N1 115.9(4) . . ?
N2 C18 N1 116.8(4) . . ?
N3 C19 C20 123.5(5) . . ?
N3 C19 H19A 118.3 . . ?
C20 C19 H19A 118.3 . . ?
C19 C20 C21 116.0(5) . . ?
C19 C20 H20A 122.0 . . ?
C21 C20 H20A 122.0 . . ?
N2 C21 C20 123.6(5) . . ?
N2 C21 H21A 118.2 . . ?
C20 C21 H21A 118.2 . . ?
C16 N1 C18 123.9(4) . . ?
C16 N1 C13 107.1(4) . . ?
C18 N1 C13 129.0(4) . . ?
C18 N2 C21 114.9(4) . . ?
C18 N3 C19 114.7(4) . . ?
C8 O2 C9 110.4(8) . . ?
C6 C1 C2 119.0(13) . . ?
C6 C1 H1A 121.4 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 121.7(13) . . ?
C3 C2 H2B 117.4 . . ?
C1 C2 H2B 120.8 . . ?
C1' C2' C3 105(2) . . ?
C1' C2' H2'A 128.4 . . ?
C3 C2' H2'A 126.0 . . ?
C6 C1' C2' 129(2) . . ?
C6 C1' H1'A 114.6 . . ?
C2' C1' H1'A 116.8 . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.050

