# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_4h
_database_code_depnum_ccdc_archive 'CCDC 1858857'
_audit_update_record             
;
2018-08-25 deposited with the CCDC.
2018-08-29 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         'C17 H18 N4 O'
_chemical_formula_sum            'C17 H18 N4 O'
_chemical_formula_weight         294.35

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.141(3)
_cell_length_b                   11.137(3)
_cell_length_c                   13.176(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.481(8)
_cell_angle_gamma                90
_cell_volume                     1582.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5826
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.77

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15333
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3641
_reflns_number_gt                2414
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0605P)²+0.2851P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3641
_refine_ls_number_parameters     202
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.040
_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 0.22061(17) 0.08783(15) 0.08631(13) 0.0566(4) Uani 1 1 d . . . . .
H1A H 0.2824 0.0424 0.1366 0.068 Uiso 1 1 calc R U . . .
H1B H 0.1547 0.1102 0.1188 0.068 Uiso 1 1 calc R U . . .
C2 C 0.1585(3) -0.10989(18) 0.0131(2) 0.0964(8) Uani 1 1 d . . . . .
H2A H 0.1215 -0.1506 -0.0514 0.145 Uiso 1 1 calc R U . . .
H2B H 0.1066 -0.1193 0.0609 0.145 Uiso 1 1 calc R U . . .
H2C H 0.2387 -0.1436 0.0436 0.145 Uiso 1 1 calc R U . . .
C3 C 0.24865(17) 0.04204(15) -0.07847(14) 0.0564(4) Uani 1 1 d . . . . .
H3A H 0.2107 0.0143 -0.1490 0.068 Uiso 1 1 calc R U . . .
H3B H 0.3304 0.0067 -0.0543 0.068 Uiso 1 1 calc R U . . .
C4 C 0.25351(14) 0.17925(14) -0.07222(11) 0.0457(4) Uani 1 1 d . . . . .
C5 C 0.13280(17) 0.22874(16) -0.12833(13) 0.0550(4) Uani 1 1 d . . . . .
C6 C 0.34798(17) 0.23402(16) -0.11756(13) 0.0582(5) Uani 1 1 d . . . . .
C7 C 0.42066(14) 0.20299(16) 0.09565(12) 0.0500(4) Uani 1 1 d . U . . .
C8 C 0.27904(13) 0.20000(13) 0.05113(11) 0.0425(4) Uani 1 1 d . . . . .
C9 C 0.24173(13) 0.32069(13) 0.08311(10) 0.0389(3) Uani 1 1 d . . . . .
C10 C 0.12750(14) 0.36903(14) 0.07964(11) 0.0461(4) Uani 1 1 d . . . . .
H10 H 0.0558 0.3247 0.0532 0.055 Uiso 1 1 calc R U . . .
C11 C 0.12047(15) 0.48494(15) 0.11618(12) 0.0525(4) Uani 1 1 d . . . . .
H11 H 0.0435 0.5185 0.1144 0.063 Uiso 1 1 calc R U . . .
C12 C 0.22587(17) 0.54994(15) 0.15478(13) 0.0555(4) Uani 1 1 d . . . . .
H12 H 0.2192 0.6284 0.1770 0.067 Uiso 1 1 calc R U . . .
C13 C 0.34238(16) 0.50243(15) 0.16178(12) 0.0531(4) Uani 1 1 d . . . . .
H13 H 0.4139 0.5467 0.1894 0.064 Uiso 1 1 calc R U . . .
C14 C 0.34807(13) 0.38666(14) 0.12610(10) 0.0415(4) Uani 1 1 d . . . . .
C15 C 0.58076(14) 0.35016(19) 0.17662(13) 0.0623(5) Uani 1 1 d . . . . .
H15A H 0.6253 0.2815 0.2130 0.075 Uiso 1 1 calc R U . . .
H15B H 0.5821 0.4129 0.2280 0.075 Uiso 1 1 calc R U . . .
C16 C 0.64546(16) 0.3940(2) 0.09727(15) 0.0685(5) Uani 1 1 d . . . . .
H16A H 0.6046 0.4663 0.0649 0.082 Uiso 1 1 calc R U . . .
H16B H 0.6380 0.3338 0.0429 0.082 Uiso 1 1 calc R U . . .
C17 C 0.78020(17) 0.4207(2) 0.14274(17) 0.0821(6) Uani 1 1 d . . . . .
H17A H 0.7882 0.4838 0.1937 0.123 Uiso 1 1 calc R U . . .
H17B H 0.8174 0.4456 0.0878 0.123 Uiso 1 1 calc R U . . .
H17C H 0.8212 0.3499 0.1758 0.123 Uiso 1 1 calc R U . . .
N1 N 0.17142(13) 0.01692(12) -0.00757(12) 0.0599(4) Uani 1 1 d . . . . .
N2 N 0.04045(17) 0.26612(17) -0.17503(14) 0.0811(5) Uani 1 1 d . . . . .
N3 N 0.41948(18) 0.27832(18) -0.15308(13) 0.0882(6) Uani 1 1 d . . . . .
N4 N 0.45315(11) 0.31582(13) 0.13002(10) 0.0493(3) Uani 1 1 d . U . . .
O1 O 0.49057(11) 0.11938(12) 0.09859(11) 0.0747(4) 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 N1 1.454(2) . ?
C1 C8 1.533(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.452(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.447(2) . ?
C3 C4 1.531(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.467(2) . ?
C4 C5 1.470(2) . ?
C4 C8 1.595(2) . ?
C5 N2 1.137(2) . ?
C6 N3 1.133(2) . ?
C7 O1 1.2084(19) . ?
C7 N4 1.354(2) . ?
C7 C8 1.540(2) . ?
C8 C9 1.498(2) . ?
C9 C10 1.372(2) . ?
C9 C14 1.389(2) . ?
C10 C11 1.387(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(2) . ?
C13 H13 0.9300 . ?
C14 N4 1.4020(19) . ?
C15 N4 1.452(2) . ?
C15 C16 1.493(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.500(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
N1 C1 C8 106.47(13) . . ?
N1 C1 H1A 110.4 . . ?
C8 C1 H1A 110.4 . . ?
N1 C1 H1B 110.4 . . ?
C8 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 100.20(12) . . ?
N1 C3 H3A 111.7 . . ?
C4 C3 H3A 111.7 . . ?
N1 C3 H3B 111.7 . . ?
C4 C3 H3B 111.7 . . ?
H3A C3 H3B 109.5 . . ?
C6 C4 C5 107.37(14) . . ?
C6 C4 C3 114.37(14) . . ?
C5 C4 C3 109.37(13) . . ?
C6 C4 C8 113.04(12) . . ?
C5 C4 C8 111.45(12) . . ?
C3 C4 C8 101.21(12) . . ?
N2 C5 C4 177.55(18) . . ?
N3 C6 C4 178.6(2) . . ?
O1 C7 N4 126.03(16) . . ?
O1 C7 C8 125.89(16) . . ?
N4 C7 C8 108.08(13) . . ?
C9 C8 C1 118.52(12) . . ?
C9 C8 C7 101.73(12) . . ?
C1 C8 C7 111.99(13) . . ?
C9 C8 C4 115.16(12) . . ?
C1 C8 C4 102.07(12) . . ?
C7 C8 C4 107.22(11) . . ?
C10 C9 C14 119.71(14) . . ?
C10 C9 C8 131.52(14) . . ?
C14 C9 C8 108.73(12) . . ?
C9 C10 C11 119.08(14) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 120.34(15) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.83(15) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 117.21(15) . . ?
C14 C13 H13 121.4 . . ?
C12 C13 H13 121.4 . . ?
C13 C14 C9 121.76(14) . . ?
C13 C14 N4 128.51(14) . . ?
C9 C14 N4 109.67(13) . . ?
N4 C15 C16 112.54(14) . . ?
N4 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N4 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 113.29(16) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 N1 C2 114.35(15) . . ?
C3 N1 C1 106.60(13) . . ?
C2 N1 C1 113.72(17) . . ?
C7 N4 C14 111.04(13) . . ?
C7 N4 C15 122.52(14) . . ?
C14 N4 C15 125.99(14) . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_6c
_database_code_depnum_ccdc_archive 'CCDC 1858860'
_audit_update_record             
;
2018-08-25 deposited with the CCDC.
2018-08-29 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         'C17 H18 F N3 O3'
_chemical_formula_sum            'C17 H18 F N3 O3'
_chemical_formula_weight         331.34

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'
F F 0.0171 0.0103 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.9286(16)
_cell_length_b                   12.5329(18)
_cell_length_c                   14.6928(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.562(3)
_cell_angle_gamma                90
_cell_volume                     1644.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4925
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13403
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.281
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3203
_reflns_number_gt                2243
_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)+(0.0641P)²+0.3695P] 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         3203
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.7250(3) 0.68131(17) 0.62557(17) 0.0745(7) Uani 1 1 d . . . . .
H1A H 0.6824 0.7050 0.6818 0.112 Uiso 1 1 calc R U . . .
H1B H 0.6649 0.7067 0.5755 0.112 Uiso 1 1 calc R U . . .
H1C H 0.8249 0.7088 0.6204 0.112 Uiso 1 1 calc R U . . .
C2 C 0.8579(2) 0.50795(15) 0.62758(12) 0.0445(5) Uani 1 1 d . . . . .
C3 C 0.81555(18) 0.38960(13) 0.63036(11) 0.0384(4) Uani 1 1 d . . . . .
C4 C 0.64721(19) 0.39401(14) 0.62269(11) 0.0415(4) Uani 1 1 d . . . . .
C5 C 0.5415(2) 0.31449(17) 0.61872(14) 0.0546(5) Uani 1 1 d . . . . .
H5 H 0.5684 0.2428 0.6193 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3937(2) 0.3457(2) 0.61387(15) 0.0662(6) Uani 1 1 d . . . . .
C7 C 0.3478(2) 0.4493(2) 0.61226(15) 0.0694(7) Uani 1 1 d . . . . .
H7 H 0.2464 0.4660 0.6094 0.083 Uiso 1 1 calc R U . . .
C8 C 0.4541(2) 0.5288(2) 0.61487(14) 0.0615(6) Uani 1 1 d . . . . .
H8 H 0.4262 0.6002 0.6130 0.074 Uiso 1 1 calc R U . . .
C9 C 0.6028(2) 0.49975(15) 0.62032(12) 0.0448(5) Uani 1 1 d . . . . .
C10 C 0.87143(19) 0.33006(14) 0.72010(11) 0.0410(4) Uani 1 1 d . . . . .
C11 C 1.0052(2) 0.37972(15) 0.76171(12) 0.0467(5) Uani 1 1 d . . . . .
C12 C 0.7507(2) 0.33150(19) 0.79307(14) 0.0592(6) Uani 1 1 d . . . . .
C13 C 0.6289(5) 0.4580(4) 0.8950(3) 0.0761(11) Uani 0.655(4) 1 d . . P A 1
H13A H 0.6697 0.5184 0.9282 0.091 Uiso 0.655(4) 1 calc R U P A 1
H13B H 0.6205 0.3982 0.9366 0.091 Uiso 0.655(4) 1 calc R U P A 1
C14 C 0.4778(6) 0.4856(6) 0.8561(3) 0.1009(18) Uani 0.655(4) 1 d . . P A 1
H14A H 0.4871 0.5450 0.8153 0.151 Uiso 0.655(4) 1 calc R U P A 1
H14B H 0.4113 0.5040 0.9045 0.151 Uiso 0.655(4) 1 calc R U P A 1
H15C H 0.4383 0.4253 0.8234 0.151 Uiso 0.655(4) 1 calc R U P A 1
C13' C 0.5599(10) 0.4181(8) 0.8634(6) 0.0761(11) Uani 0.345(4) 1 d . . P A 2
H13C H 0.4870 0.3898 0.8203 0.091 Uiso 0.345(4) 1 calc R U P A 2
H13D H 0.5594 0.3769 0.9193 0.091 Uiso 0.345(4) 1 calc R U P A 2
C14' C 0.5431(11) 0.5343(12) 0.8789(7) 0.1009(18) Uani 0.345(4) 1 d . . P A 2
H14D H 0.6310 0.5613 0.9092 0.151 Uiso 0.345(4) 1 calc R U P A 2
H14E H 0.4571 0.5470 0.9161 0.151 Uiso 0.345(4) 1 calc R U P A 2
H15F H 0.5303 0.5699 0.8215 0.151 Uiso 0.345(4) 1 calc R U P A 2
C15 C 0.8896(2) 0.32201(15) 0.55743(12) 0.0460(5) Uani 1 1 d . . . . .
H15A H 0.8415 0.3321 0.4986 0.055 Uiso 1 1 calc R U . . .
H15B H 0.9953 0.3385 0.5525 0.055 Uiso 1 1 calc R U . . .
C16 C 0.9469(3) 0.13306(18) 0.54024(16) 0.0711(7) Uani 1 1 d . . . . .
H16A H 1.0528 0.1451 0.5458 0.107 Uiso 1 1 calc R U . . .
H16B H 0.9177 0.1364 0.4773 0.107 Uiso 1 1 calc R U . . .
H16C H 0.9230 0.0639 0.5642 0.107 Uiso 1 1 calc R U . . .
C17 C 0.9119(3) 0.21730(15) 0.68611(14) 0.0572(5) Uani 1 1 d . . . . .
H17A H 1.0186 0.2046 0.6925 0.069 Uiso 1 1 calc R U . . .
H17B H 0.8587 0.1634 0.7204 0.069 Uiso 1 1 calc R U . . .
F1 F 0.28758(15) 0.26720(14) 0.61109(12) 0.1026(6) Uani 1 1 d . . . . .
N1 N 0.72922(18) 0.56579(12) 0.62403(10) 0.0484(4) Uani 1 1 d . . . . .
N2 N 1.1085(2) 0.41204(16) 0.79840(13) 0.0720(6) Uani 1 1 d . . . . .
N3 N 0.86686(17) 0.21462(12) 0.59109(10) 0.0485(4) Uani 1 1 d . . . . .
O1 O 0.98381(15) 0.54416(11) 0.62764(10) 0.0613(4) Uani 1 1 d . . . . .
O2 O 0.6883(2) 0.25493(16) 0.82021(14) 0.1050(7) Uani 1 1 d . . . . .
O3 O 0.72652(18) 0.43021(14) 0.82031(10) 0.0767(5) 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 N1 1.449(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.212(2) . ?
C2 N1 1.359(2) . ?
C2 C3 1.531(3) . ?
C3 C4 1.507(2) . ?
C3 C15 1.522(2) . ?
C3 C10 1.591(2) . ?
C4 C5 1.374(3) . ?
C4 C9 1.384(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.362(3) . ?
C6 F1 1.366(3) . ?
C7 C8 1.376(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 N1 1.400(2) . ?
C10 C11 1.474(3) . ?
C10 C12 1.528(3) . ?
C10 C17 1.543(3) . ?
C11 N2 1.138(2) . ?
C12 O2 1.181(3) . ?
C12 O3 1.319(3) . ?
C13 O3 1.450(4) . ?
C13 C14 1.501(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H15C 0.9600 . ?
C13' C14' 1.482(19) . ?
C13' O3 1.629(8) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C14' H14D 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H15F 0.9600 . ?
C15 N3 1.449(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N3 1.458(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N3 1.449(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 125.73(18) . . ?
O1 C2 C3 126.29(17) . . ?
N1 C2 C3 107.97(15) . . ?
C4 C3 C15 114.05(14) . . ?
C4 C3 C2 102.06(14) . . ?
C15 C3 C2 114.28(14) . . ?
C4 C3 C10 112.55(14) . . ?
C15 C3 C10 100.82(13) . . ?
C2 C3 C10 113.63(13) . . ?
C5 C4 C9 119.81(17) . . ?
C5 C4 C3 131.38(17) . . ?
C9 C4 C3 108.80(15) . . ?
C4 C5 C6 117.0(2) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
C7 C6 F1 118.5(2) . . ?
C7 C6 C5 124.0(2) . . ?
F1 C6 C5 117.5(2) . . ?
C6 C7 C8 118.9(2) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C9 118.3(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C4 121.98(18) . . ?
C8 C9 N1 128.48(19) . . ?
C4 C9 N1 109.54(15) . . ?
C11 C10 C12 106.16(15) . . ?
C11 C10 C17 109.25(15) . . ?
C12 C10 C17 114.01(17) . . ?
C11 C10 C3 113.07(14) . . ?
C12 C10 C3 110.99(14) . . ?
C17 C10 C3 103.52(13) . . ?
N2 C11 C10 174.9(2) . . ?
O2 C12 O3 125.5(2) . . ?
O2 C12 C10 124.4(2) . . ?
O3 C12 C10 110.03(18) . . ?
O3 C13 C14 108.2(3) . . ?
O3 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
O3 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H15C 109.5 . . ?
H14A C14 H15C 109.5 . . ?
H14B C14 H15C 109.5 . . ?
C14' C13' O3 93.6(7) . . ?
C14' C13' H13C 113.0 . . ?
O3 C13' H13C 113.0 . . ?
C14' C13' H13D 113.0 . . ?
O3 C13' H13D 113.0 . . ?
H13C C13' H13D 110.4 . . ?
C13' C14' H14D 109.5 . . ?
C13' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C13' C14' H15F 109.5 . . ?
H14D C14' H15F 109.5 . . ?
H14E C14' H15F 109.5 . . ?
N3 C15 C3 102.33(14) . . ?
N3 C15 H15A 111.3 . . ?
C3 C15 H15A 111.3 . . ?
N3 C15 H15B 111.3 . . ?
C3 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C10 105.63(14) . . ?
N3 C17 H17A 110.6 . . ?
C10 C17 H17A 110.6 . . ?
N3 C17 H17B 110.6 . . ?
C10 C17 H17B 110.6 . . ?
H17A C17 H17B 108.7 . . ?
C2 N1 C9 111.54(15) . . ?
C2 N1 C1 123.67(18) . . ?
C9 N1 C1 124.78(17) . . ?
C15 N3 C17 105.59(14) . . ?
C15 N3 C16 113.92(16) . . ?
C17 N3 C16 112.16(16) . . ?
C12 O3 C13 123.8(3) . . ?
C12 O3 C13' 100.5(4) . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_8j
_database_code_depnum_ccdc_archive 'CCDC 1858865'
_audit_update_record             
;
2018-08-25 deposited with the CCDC.
2018-08-29 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         'C25 H30 N2 O2'
_chemical_formula_sum            'C25 H30 N2 O2'
_chemical_formula_weight         390.51

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.3608(8)
_cell_length_b                   15.3765(14)
_cell_length_c                   19.0562(14)
_cell_angle_alpha                90
_cell_angle_beta                 114.853(4)
_cell_angle_gamma                90
_cell_volume                     2223.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7580
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      23.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24179
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.649
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5077
_reflns_number_gt                3088
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0655P)²+0.6047P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5077
_refine_ls_number_parameters     296
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.050
_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
C1 C 1.3267(16) 0.5012(5) 1.0477(6) 0.097(2) Uani 0.621(6) 1 d D U P A 1
H1A H 1.4432 0.4945 1.0503 0.146 Uiso 0.621(6) 1 calc R U P A 1
H1B H 1.2681 0.4458 1.0371 0.146 Uiso 0.621(6) 1 calc R U P A 1
H1C H 1.3342 0.5229 1.0962 0.146 Uiso 0.621(6) 1 calc R U P A 1
C2 C 1.2223(6) 0.5653(2) 0.9831(3) 0.0814(14) Uani 0.621(6) 1 d D U P A 1
H2A H 1.2100 0.5418 0.9339 0.098 Uiso 0.621(6) 1 calc R U P A 1
H2B H 1.1051 0.5723 0.9811 0.098 Uiso 0.621(6) 1 calc R U P A 1
C3 C 1.3117(5) 0.6531(2) 0.9958(3) 0.0744(14) Uani 0.621(6) 1 d D U P A 1
H3A H 1.4304 0.6452 0.9998 0.089 Uiso 0.621(6) 1 calc R U P A 1
H3B H 1.3209 0.6768 1.0445 0.089 Uiso 0.621(6) 1 calc R U P A 1
C1' C 1.303(3) 0.5089(7) 1.0436(9) 0.101(3) Uani 0.379(6) 1 d D U P A 2
H1D H 1.2222 0.4757 1.0007 0.152 Uiso 0.379(6) 1 calc R U P A 2
H1E H 1.2844 0.4961 1.0888 0.152 Uiso 0.379(6) 1 calc R U P A 2
H1F H 1.4218 0.4939 1.0528 0.152 Uiso 0.379(6) 1 calc R U P A 2
C2' C 1.2730(13) 0.6060(6) 1.0250(4) 0.098(3) Uani 0.379(6) 1 d D U P A 2
H2C H 1.3723 0.6388 1.0614 0.118 Uiso 0.379(6) 1 calc R U P A 2
H2D H 1.1680 0.6248 1.0304 0.118 Uiso 0.379(6) 1 calc R U P A 2
C3' C 1.2514(10) 0.6242(3) 0.9425(4) 0.077(2) Uani 0.379(6) 1 d D U P A 2
H3C H 1.3585 0.6097 0.9370 0.092 Uiso 0.379(6) 1 calc R U P A 2
H3D H 1.1549 0.5904 0.9054 0.092 Uiso 0.379(6) 1 calc R U P A 2
C4 C 1.2130(3) 0.72041(14) 0.92974(15) 0.0740(7) Uani 1 1 d D U . . .
H4A H 1.2860 0.7717 0.9372 0.089 Uiso 0.621(6) 1 calc R U P A 1
H4B H 1.1930 0.6950 0.8801 0.089 Uiso 0.621(6) 1 calc R U P A 1
H4C H 1.3065 0.7524 0.9702 0.089 Uiso 0.379(6) 1 calc R U P A 2
H4D H 1.2136 0.7369 0.8807 0.089 Uiso 0.379(6) 1 calc R U P A 2
C5 C 1.0303(3) 0.81009(13) 0.97552(11) 0.0506(5) Uani 1 1 d . . . . .
C6 C 0.8358(2) 0.81910(11) 0.95926(10) 0.0411(4) Uani 1 1 d . . . . .
C7 C 0.7479(2) 0.75405(11) 0.89555(10) 0.0407(4) Uani 1 1 d . . . . .
C8 C 0.5727(3) 0.73437(11) 0.85325(10) 0.0471(5) Uani 1 1 d . . . . .
H8 H 0.4866 0.7620 0.8640 0.057 Uiso 1 1 calc R U . . .
C9 C 0.5249(3) 0.67281(12) 0.79426(11) 0.0567(5) Uani 1 1 d . . . . .
C10 C 0.3327(4) 0.65133(16) 0.74661(15) 0.0857(8) Uani 1 1 d . . . . .
H10A H 0.2991 0.6035 0.7699 0.129 Uiso 1 1 calc R U . . .
H10B H 0.3155 0.6357 0.6951 0.129 Uiso 1 1 calc R U . . .
H10C H 0.2617 0.7011 0.7446 0.129 Uiso 1 1 calc R U . . .
C11 C 0.6574(4) 0.63285(13) 0.78023(12) 0.0640(6) Uani 1 1 d . . . . .
H11 H 0.6264 0.5915 0.7411 0.077 Uiso 1 1 calc R U . . .
C12 C 0.8332(3) 0.65205(13) 0.82198(13) 0.0622(6) Uani 1 1 d . . . . .
H12 H 0.9195 0.6245 0.8113 0.075 Uiso 1 1 calc R U . . .
C13 C 0.8776(3) 0.71313(11) 0.87988(11) 0.0480(5) Uani 1 1 d . . . . .
C14 C 0.7661(2) 0.91451(11) 0.93958(11) 0.0448(5) Uani 1 1 d . . . . .
H14 H 0.8665 0.9543 0.9622 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6777(3) 0.92999(11) 0.85292(11) 0.0489(5) Uani 1 1 d . . . . .
C16 C 0.7875(3) 0.92260(11) 0.80828(11) 0.0479(5) Uani 1 1 d . . . . .
C17 C 0.9662(3) 0.93990(14) 0.83980(12) 0.0609(6) Uani 1 1 d . . . . .
H17 H 1.0227 0.9571 0.8912 0.073 Uiso 1 1 calc R U . . .
C18 C 1.0621(3) 0.93211(15) 0.79644(13) 0.0655(6) Uani 1 1 d . . . . .
H18 H 1.1820 0.9447 0.8190 0.079 Uiso 1 1 calc R U . . .
C19 C 0.9841(3) 0.90613(13) 0.72060(13) 0.0615(6) Uani 1 1 d . . . . .
C20 C 1.0894(4) 0.89612(19) 0.67335(15) 0.0852(8) Uani 1 1 d . . . . .
H20A H 1.1970 0.9286 0.6970 0.128 Uiso 1 1 calc R U . . .
H20B H 1.0219 0.9176 0.6220 0.128 Uiso 1 1 calc R U . . .
H20C H 1.1163 0.8358 0.6710 0.128 Uiso 1 1 calc R U . . .
C21 C 0.8044(3) 0.88934(16) 0.68865(13) 0.0722(7) Uani 1 1 d . . . . .
H21 H 0.7481 0.8722 0.6372 0.087 Uiso 1 1 calc R U . . .
C22 C 0.7078(3) 0.89757(15) 0.73165(12) 0.0642(6) Uani 1 1 d . . . . .
H22 H 0.5874 0.8861 0.7088 0.077 Uiso 1 1 calc R U . . .
C23 C 0.6480(3) 0.92706(13) 0.98163(12) 0.0567(5) Uani 1 1 d . . . . .
H23A H 0.6971 0.9708 1.0217 0.068 Uiso 1 1 calc R U . . .
H23B H 0.5312 0.9456 0.9457 0.068 Uiso 1 1 calc R U . . .
C24 C 0.6036(3) 0.85055(17) 1.08379(14) 0.0777(7) Uani 1 1 d . . . . .
H24A H 0.6006 0.7936 1.1039 0.117 Uiso 1 1 calc R U . . .
H24B H 0.4919 0.8786 1.0700 0.117 Uiso 1 1 calc R U . . .
H24C H 0.6948 0.8844 1.1224 0.117 Uiso 1 1 calc R U . . .
C25 C 0.8071(3) 0.80204(14) 1.03195(11) 0.0529(5) Uani 1 1 d . . . . .
H25A H 0.8025 0.7401 1.0408 0.063 Uiso 1 1 calc R U . . .
H25B H 0.9004 0.8280 1.0770 0.063 Uiso 1 1 calc R U . . .
N1 N 1.0444(2) 0.74563(10) 0.92946(10) 0.0529(4) Uani 1 1 d . . . . .
N2 N 0.6394(2) 0.84297(11) 1.01544(9) 0.0566(5) Uani 1 1 d . . . . .
O1 O 1.15117(18) 0.85275(11) 1.02187(9) 0.0709(5) Uani 1 1 d . . . . .
O2 O 0.52127(19) 0.94522(10) 0.81997(9) 0.0664(4) 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 1.531(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.513(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.570(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1' C2' 1.531(5) . ?
C1' H1D 0.9600 . ?
C1' H1E 0.9600 . ?
C1' H1F 0.9600 . ?
C2' C3' 1.532(5) . ?
C2' H2C 0.9700 . ?
C2' H2D 0.9700 . ?
C3' C4 1.511(4) . ?
C3' H3C 0.9700 . ?
C3' H3D 0.9700 . ?
C4 N1 1.460(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C5 O1 1.217(2) . ?
C5 N1 1.361(2) . ?
C5 C6 1.529(3) . ?
C6 C7 1.505(2) . ?
C6 C25 1.524(2) . ?
C6 C14 1.565(2) . ?
C7 C8 1.377(3) . ?
C7 C13 1.390(2) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.388(3) . ?
C9 C10 1.513(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C13 N1 1.407(3) . ?
C14 C15 1.518(3) . ?
C14 C23 1.522(3) . ?
C14 H14 0.9800 . ?
C15 O2 1.212(2) . ?
C15 C16 1.495(3) . ?
C16 C22 1.381(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(3) . ?
C18 H18 0.9300 . ?
C19 C21 1.387(3) . ?
C19 C20 1.509(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 N2 1.460(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N2 1.458(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 N2 1.446(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 111.7(5) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 113.8(3) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C2' C1' H1D 109.5 . . ?
C2' C1' H1E 109.5 . . ?
H1D C1' H1E 109.5 . . ?
C2' C1' H1F 109.5 . . ?
H1D C1' H1F 109.5 . . ?
H1E C1' H1F 109.5 . . ?
C1' C2' C3' 110.6(7) . . ?
C1' C2' H2C 109.5 . . ?
C3' C2' H2C 109.5 . . ?
C1' C2' H2D 109.5 . . ?
C3' C2' H2D 109.5 . . ?
H2C C2' H2D 108.1 . . ?
C4 C3' C2' 105.6(5) . . ?
C4 C3' H3C 110.6 . . ?
C2' C3' H3C 110.6 . . ?
C4 C3' H3D 110.6 . . ?
C2' C3' H3D 110.6 . . ?
H3C C3' H3D 108.7 . . ?
N1 C4 C3' 113.6(3) . . ?
N1 C4 C3 111.1(2) . . ?
N1 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
N1 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N1 C4 H4C 108.8 . . ?
C3' C4 H4C 108.8 . . ?
N1 C4 H4D 108.8 . . ?
C3' C4 H4D 108.8 . . ?
H4C C4 H4D 107.7 . . ?
O1 C5 N1 126.14(18) . . ?
O1 C5 C6 125.91(17) . . ?
N1 C5 C6 107.95(16) . . ?
C7 C6 C25 114.15(15) . . ?
C7 C6 C5 102.71(14) . . ?
C25 C6 C5 111.11(15) . . ?
C7 C6 C14 115.06(14) . . ?
C25 C6 C14 101.19(14) . . ?
C5 C6 C14 113.01(15) . . ?
C8 C7 C13 120.60(17) . . ?
C8 C7 C6 131.05(16) . . ?
C13 C7 C6 108.30(16) . . ?
C7 C8 C9 119.68(18) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C11 C9 C8 118.4(2) . . ?
C11 C9 C10 121.3(2) . . ?
C8 C9 C10 120.3(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 122.56(19) . . ?
C12 C11 H11 118.7 . . ?
C9 C11 H11 118.7 . . ?
C13 C12 C11 118.20(19) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C7 120.6(2) . . ?
C12 C13 N1 129.67(18) . . ?
C7 C13 N1 109.71(16) . . ?
C15 C14 C23 115.22(16) . . ?
C15 C14 C6 111.69(14) . . ?
C23 C14 C6 104.55(15) . . ?
C15 C14 H14 108.4 . . ?
C23 C14 H14 108.4 . . ?
C6 C14 H14 108.4 . . ?
O2 C15 C16 120.46(18) . . ?
O2 C15 C14 121.29(18) . . ?
C16 C15 C14 118.21(16) . . ?
C22 C16 C17 117.81(19) . . ?
C22 C16 C15 118.94(18) . . ?
C17 C16 C15 123.24(18) . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C21 117.7(2) . . ?
C18 C19 C20 121.3(2) . . ?
C21 C19 C20 121.0(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C19 121.3(2) . . ?
C22 C21 H21 119.3 . . ?
C19 C21 H21 119.3 . . ?
C21 C22 C16 120.8(2) . . ?
C21 C22 H22 119.6 . . ?
C16 C22 H22 119.6 . . ?
N2 C23 C14 106.45(15) . . ?
N2 C23 H23A 110.4 . . ?
C14 C23 H23A 110.4 . . ?
N2 C23 H23B 110.4 . . ?
C14 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C25 C6 103.63(15) . . ?
N2 C25 H25A 111.0 . . ?
C6 C25 H25A 111.0 . . ?
N2 C25 H25B 111.0 . . ?
C6 C25 H25B 111.0 . . ?
H25A C25 H25B 109.0 . . ?
C5 N1 C13 111.21(15) . . ?
C5 N1 C4 122.41(19) . . ?
C13 N1 C4 126.23(17) . . ?
C25 N2 C24 112.62(17) . . ?
C25 N2 C23 104.96(16) . . ?
C24 N2 C23 112.96(17) . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_6g
_database_code_depnum_ccdc_archive 'CCDC 1858861'
_audit_update_record             
;
2018-08-25 deposited with the CCDC.
2018-08-29 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         'C23 H23 N3 O3'
_chemical_formula_sum            'C23 H23 N3 O3'
_chemical_formula_weight         389.44

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           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

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

_cell_length_a                   25.3390(12)
_cell_length_b                   10.4719(7)
_cell_length_c                   15.6589(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4155.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29368
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4071
_reflns_number_gt                3095
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.995

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0500P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1175 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4071
_refine_ls_number_parameters     274
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.025
_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 0.69043(12) 0.2296(3) 0.45955(18) 0.0639(8) Uani 1 1 d . . . . .
H1 H 0.6723 0.1770 0.4218 0.077 Uiso 1 1 calc R U . . .
C2 C 0.68098(16) 0.2199(4) 0.5467(2) 0.0820(10) Uani 1 1 d . . . . .
H2 H 0.6569 0.1601 0.5669 0.098 Uiso 1 1 calc R U . . .
C3 C 0.70653(15) 0.2968(4) 0.6024(2) 0.0844(11) Uani 1 1 d . . . . .
H3 H 0.7001 0.2898 0.6607 0.101 Uiso 1 1 calc R U . . .
C4 C 0.74175(15) 0.3844(4) 0.5729(2) 0.0802(11) Uani 1 1 d . . . . .
H4 H 0.7591 0.4378 0.6112 0.096 Uiso 1 1 calc R U . . .
C5 C 0.75185(12) 0.3947(3) 0.48655(19) 0.0627(8) Uani 1 1 d . . . . .
H5 H 0.7761 0.4548 0.4671 0.075 Uiso 1 1 calc R U . . .
C6 C 0.72637(10) 0.3165(2) 0.42872(16) 0.0456(6) Uani 1 1 d . . . . .
C7 C 0.73998(9) 0.3239(3) 0.33485(15) 0.0481(6) Uani 1 1 d . . . . .
H7A H 0.7536 0.4085 0.3224 0.058 Uiso 1 1 calc R U . . .
H7B H 0.7677 0.2628 0.3226 0.058 Uiso 1 1 calc R U . . .
C8 C 0.68790(8) 0.1854(2) 0.23892(15) 0.0386(5) Uani 1 1 d . . . . .
C9 C 0.63721(8) 0.1943(2) 0.18590(14) 0.0375(5) Uani 1 1 d . . . . .
C10 C 0.61977(8) 0.3301(2) 0.20217(15) 0.0382(5) Uani 1 1 d . . . . .
C11 C 0.57938(10) 0.4018(3) 0.16834(18) 0.0513(7) Uani 1 1 d . . . . .
H11 H 0.5554 0.3652 0.1306 0.062 Uiso 1 1 calc R U . . .
C12 C 0.57492(12) 0.5291(3) 0.1912(2) 0.0606(8) Uani 1 1 d . . . . .
H12 H 0.5475 0.5781 0.1693 0.073 Uiso 1 1 calc R U . . .
C13 C 0.61092(12) 0.5833(3) 0.24593(19) 0.0586(7) Uani 1 1 d . . . . .
H13 H 0.6072 0.6687 0.2611 0.070 Uiso 1 1 calc R U . . .
C14 C 0.65251(10) 0.5136(2) 0.27884(17) 0.0505(6) Uani 1 1 d . . . . .
H14 H 0.6773 0.5511 0.3148 0.061 Uiso 1 1 calc R U . . .
C15 C 0.65602(8) 0.3872(2) 0.25658(14) 0.0370(5) Uani 1 1 d . . . . .
C16 C 0.59499(8) 0.0853(2) 0.20959(15) 0.0403(6) Uani 1 1 d . . . . .
C17 C 0.61525(10) -0.0115(2) 0.26867(18) 0.0488(6) Uani 1 1 d . . . . .
C18 C 0.54623(9) 0.1451(2) 0.25155(17) 0.0468(6) Uani 1 1 d . . . . .
C19 C 0.51425(12) 0.2365(4) 0.3798(2) 0.0823(10) Uani 1 1 d D . . . .
H19C H 0.4852 0.2576 0.3420 0.099 Uiso 0.3 1 calc R U P A 2
H19D H 0.5271 0.3147 0.4056 0.099 Uiso 0.3 1 calc R U P A 2
H19A H 0.4807 0.1962 0.3670 0.099 Uiso 0.7 1 calc R U P B 1
H19B H 0.5120 0.3260 0.3645 0.099 Uiso 0.7 1 calc R U P B 1
C20B C 0.4962(10) 0.148(2) 0.4465(14) 0.079(7) Uani 0.15 1 d D . P C 2
H20A H 0.4684 0.1870 0.4788 0.118 Uiso 0.15 1 calc R U P C 2
H20B H 0.4834 0.0709 0.4205 0.118 Uiso 0.15 1 calc R U P C 2
H20C H 0.5251 0.1278 0.4838 0.118 Uiso 0.15 1 calc R U P C 2
C21 C 0.64703(9) 0.1675(2) 0.09098(15) 0.0468(6) Uani 1 1 d . . . . .
H21A H 0.6574 0.2447 0.0611 0.056 Uiso 1 1 calc R U . . .
H21B H 0.6742 0.1033 0.0835 0.056 Uiso 1 1 calc R U . . .
C22 C 0.59856(13) 0.0753(4) -0.02664(18) 0.0759(9) Uani 1 1 d . . . . .
H22A H 0.6242 0.0081 -0.0309 0.114 Uiso 1 1 calc R U . . .
H22B H 0.6084 0.1441 -0.0640 0.114 Uiso 1 1 calc R U . . .
H22C H 0.5645 0.0433 -0.0428 0.114 Uiso 1 1 calc R U . . .
C23 C 0.58265(9) 0.0248(3) 0.12225(19) 0.0539(7) Uani 1 1 d . . . . .
H23A H 0.6035 -0.0518 0.1135 0.065 Uiso 1 1 calc R U . . .
H23B H 0.5455 0.0030 0.1179 0.065 Uiso 1 1 calc R U . . .
N1 N 0.69537(6) 0.29852(18) 0.27899(12) 0.0385(5) Uani 1 1 d . . . . .
N2 N 0.62773(9) -0.0902(3) 0.31524(19) 0.0708(7) Uani 1 1 d . . . . .
N3 N 0.59651(8) 0.1217(2) 0.06105(13) 0.0519(6) Uani 1 1 d . . . . .
O1 O 0.71688(6) 0.09326(16) 0.24352(12) 0.0535(5) Uani 1 1 d . . . . .
O2 O 0.50522(7) 0.1632(2) 0.21588(13) 0.0681(6) Uani 1 1 d . . . . .
O3 O 0.55646(6) 0.17476(18) 0.33171(11) 0.0593(5) Uani 1 1 d . . . . .
C20A C 0.5264(2) 0.2233(6) 0.4706(3) 0.0988(14) Uani 0.85 1 d D . P C 1
H20D H 0.4994 0.2641 0.5038 0.148 Uiso 0.85 1 calc R U P C 1
H20E H 0.5598 0.2627 0.4825 0.148 Uiso 0.85 1 calc R U P C 1
H20F H 0.5281 0.1343 0.4853 0.148 Uiso 0.85 1 calc R U P C 1


_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 C6 1.375(4) . ?
C1 C2 1.390(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.352(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.512(4) . ?
C7 N1 1.454(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.214(3) . ?
C8 N1 1.354(3) . ?
C8 C9 1.532(3) . ?
C9 C10 1.511(3) . ?
C9 C21 1.533(3) . ?
C9 C16 1.608(3) . ?
C10 C11 1.375(3) . ?
C10 C15 1.388(3) . ?
C11 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.407(3) . ?
C16 C17 1.465(4) . ?
C16 C18 1.533(3) . ?
C16 C23 1.539(4) . ?
C17 N2 1.145(3) . ?
C18 O2 1.195(3) . ?
C18 O3 1.319(3) . ?
C19 O3 1.459(3) . ?
C19 C20A 1.462(6) . ?
C19 C20B 1.470(12) . ?
C19 H19C 0.9700 . ?
C19 H19D 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20B H20A 0.9600 . ?
C20B H20B 0.9600 . ?
C20B H20C 0.9600 . ?
C21 N3 1.445(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N3 1.457(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N3 1.439(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 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
C6 C1 C2 120.5(3) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 121.8(2) . . ?
C5 C6 C7 120.0(3) . . ?
N1 C7 C6 113.47(19) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 N1 125.7(2) . . ?
O1 C8 C9 126.0(2) . . ?
N1 C8 C9 108.35(18) . . ?
C10 C9 C8 102.20(17) . . ?
C10 C9 C21 112.54(19) . . ?
C8 C9 C21 112.21(18) . . ?
C10 C9 C16 115.76(17) . . ?
C8 C9 C16 112.91(18) . . ?
C21 C9 C16 101.65(18) . . ?
C11 C10 C15 119.6(2) . . ?
C11 C10 C9 131.8(2) . . ?
C15 C10 C9 108.38(18) . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 N1 128.3(2) . . ?
C10 C15 N1 109.75(19) . . ?
C17 C16 C18 107.1(2) . . ?
C17 C16 C23 110.3(2) . . ?
C18 C16 C23 112.65(19) . . ?
C17 C16 C9 113.82(17) . . ?
C18 C16 C9 110.20(18) . . ?
C23 C16 C9 102.85(19) . . ?
N2 C17 C16 175.5(3) . . ?
O2 C18 O3 125.3(2) . . ?
O2 C18 C16 124.4(2) . . ?
O3 C18 C16 110.2(2) . . ?
O3 C19 C20A 107.8(3) . . ?
O3 C19 C20B 108.4(10) . . ?
O3 C19 H19C 110.0 . . ?
C20B C19 H19C 110.0 . . ?
O3 C19 H19D 110.0 . . ?
C20B C19 H19D 110.0 . . ?
H19C C19 H19D 108.4 . . ?
O3 C19 H19A 110.1 . . ?
C20A C19 H19A 110.1 . . ?
O3 C19 H19B 110.1 . . ?
C20A C19 H19B 110.1 . . ?
H19A C19 H19B 108.5 . . ?
C19 C20B H20A 109.5 . . ?
C19 C20B H20B 109.5 . . ?
H20A C20B H20B 109.5 . . ?
C19 C20B H20C 109.5 . . ?
H20A C20B H20C 109.5 . . ?
H20B C20B H20C 109.5 . . ?
N3 C21 C9 103.38(19) . . ?
N3 C21 H21A 111.1 . . ?
C9 C21 H21A 111.1 . . ?
N3 C21 H21B 111.1 . . ?
C9 C21 H21B 111.1 . . ?
H21A C21 H21B 109.1 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 C16 104.59(19) . . ?
N3 C23 H23A 110.8 . . ?
C16 C23 H23A 110.8 . . ?
N3 C23 H23B 110.8 . . ?
C16 C23 H23B 110.8 . . ?
H23A C23 H23B 108.9 . . ?
C8 N1 C15 111.27(18) . . ?
C8 N1 C7 123.21(19) . . ?
C15 N1 C7 125.47(19) . . ?
C23 N3 C21 103.56(19) . . ?
C23 N3 C22 113.7(2) . . ?
C21 N3 C22 112.6(2) . . ?
C18 O3 C19 116.9(2) . . ?
C19 C20A H20D 109.5 . . ?
C19 C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19 C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.026

####################################################################### 
# 
# 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_8f
_database_code_depnum_ccdc_archive 'CCDC 1858864'
_audit_update_record             
;
2018-08-25 deposited with the CCDC.
2018-08-29 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         'C27 H25 Cl N2 O2'
_chemical_formula_sum            'C27 H25 Cl N2 O2'
_chemical_formula_weight         444.94

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'
Cl Cl 0.1484 0.1585 '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                   9.624(3)
_cell_length_b                   10.925(3)
_cell_length_c                   11.808(3)
_cell_angle_alpha                85.813(8)
_cell_angle_beta                 81.370(9)
_cell_angle_gamma                71.045(8)
_cell_volume                     1160.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4316
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      24.26

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15418
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.745
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4542
_reflns_number_gt                2573
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1116P)²+0.0413P] 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         4542
_refine_ls_number_parameters     291
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1360
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1796
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.116
_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
C1 C 0.1712(3) 0.6925(3) 0.7549(2) 0.0563(5) Uani 1 1 d . U . . .
H1 H 0.1919 0.6074 0.7824 0.068 Uiso 1 1 calc R U . . .
C2 C 0.1252(4) 0.7943(3) 0.8318(3) 0.0618(5) Uani 1 1 d . U . . .
H2 H 0.1163 0.7765 0.9103 0.074 Uiso 1 1 calc R U . . .
C3 C 0.0940(4) 0.9177(3) 0.7925(3) 0.0623(6) Uani 1 1 d . U . . .
H3 H 0.0626 0.9846 0.8442 0.075 Uiso 1 1 calc R U . . .
C4 C 0.1079(3) 0.9456(3) 0.6782(3) 0.0596(5) Uani 1 1 d . U . . .
H4 H 0.0874 1.0312 0.6520 0.071 Uiso 1 1 calc R U . . .
C5 C 0.1525(3) 0.8467(3) 0.6006(3) 0.0543(5) Uani 1 1 d . U . . .
H5 H 0.1604 0.8665 0.5225 0.065 Uiso 1 1 calc R U . . .
C6 C 0.1857(3) 0.7186(3) 0.6381(2) 0.0508(5) Uani 1 1 d . U . . .
C7 C 0.2406(4) 0.6079(3) 0.5567(2) 0.0516(8) Uani 1 1 d . . . . .
H7A H 0.3442 0.5627 0.5630 0.062 Uiso 1 1 calc R U . . .
H7B H 0.1862 0.5475 0.5804 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3396(3) 0.6585(3) 0.3596(2) 0.0420(7) Uani 1 1 d . . . . .
C9 C 0.2817(3) 0.6986(3) 0.2440(2) 0.0393(7) Uani 1 1 d . . . . .
C10 C 0.1245(3) 0.6955(2) 0.2706(2) 0.0370(6) Uani 1 1 d . . . . .
C11 C 0.0113(3) 0.7208(3) 0.2034(2) 0.0428(7) Uani 1 1 d . . . . .
H11 H 0.0292 0.7397 0.1255 0.051 Uiso 1 1 calc R U . . .
C12 C -0.1288(3) 0.7181(3) 0.2518(3) 0.0499(8) Uani 1 1 d . . . . .
C13 C -0.2519(4) 0.7442(4) 0.1777(3) 0.0812(12) Uani 1 1 d . . . . .
H13A H -0.2983 0.6780 0.1924 0.122 Uiso 1 1 calc R U . . .
H13B H -0.2111 0.7442 0.0984 0.122 Uiso 1 1 calc R U . . .
H13C H -0.3242 0.8270 0.1956 0.122 Uiso 1 1 calc R U . . .
C14 C -0.1528(3) 0.6925(3) 0.3679(3) 0.0547(8) Uani 1 1 d . . . . .
H14 H -0.2468 0.6924 0.4007 0.066 Uiso 1 1 calc R U . . .
C15 C -0.0422(3) 0.6668(3) 0.4378(3) 0.0489(8) Uani 1 1 d . . . . .
H15 H -0.0607 0.6495 0.5158 0.059 Uiso 1 1 calc R U . . .
C16 C 0.0958(3) 0.6680(2) 0.3872(2) 0.0383(7) Uani 1 1 d . . . . .
C17 C 0.3831(3) 0.6153(3) 0.1427(2) 0.0468(7) Uani 1 1 d . . . . .
H17 H 0.4814 0.5724 0.1658 0.056 Uiso 1 1 calc R U . . .
C18 C 0.3217(3) 0.5127(3) 0.1117(3) 0.0492(8) Uani 1 1 d . . . . .
C19 C 0.3241(3) 0.4016(3) 0.1930(2) 0.0447(7) Uani 1 1 d . . . . .
C20 C 0.4223(3) 0.3603(3) 0.2733(3) 0.0559(8) Uani 1 1 d . . . . .
H20 H 0.4853 0.4072 0.2812 0.067 Uiso 1 1 calc R U . . .
C21 C 0.4286(4) 0.2518(3) 0.3415(3) 0.0634(9) Uani 1 1 d . . . . .
H21 H 0.4965 0.2245 0.3938 0.076 Uiso 1 1 calc R U . . .
C22 C 0.3328(4) 0.1834(3) 0.3315(3) 0.0598(9) Uani 1 1 d . . . . .
C23 C 0.2308(4) 0.2241(3) 0.2551(3) 0.0675(10) Uani 1 1 d . . . . .
H23 H 0.1648 0.1792 0.2502 0.081 Uiso 1 1 calc R U . . .
C24 C 0.2276(3) 0.3323(3) 0.1860(3) 0.0587(9) Uani 1 1 d . . . . .
H24 H 0.1597 0.3592 0.1337 0.070 Uiso 1 1 calc R U . . .
C25 C 0.2872(3) 0.8343(3) 0.2057(3) 0.0479(8) Uani 1 1 d . . . . .
H25A H 0.2025 0.9010 0.2429 0.057 Uiso 1 1 calc R U . . .
H25B H 0.3777 0.8467 0.2217 0.057 Uiso 1 1 calc R U . . .
C26 C 0.3087(4) 0.9483(4) 0.0235(3) 0.0798(11) Uani 1 1 d . . . . .
H26A H 0.2291 1.0244 0.0489 0.120 Uiso 1 1 calc R U . . .
H26B H 0.3132 0.9404 -0.0575 0.120 Uiso 1 1 calc R U . . .
H26C H 0.4007 0.9551 0.0397 0.120 Uiso 1 1 calc R U . . .
C27 C 0.3964(3) 0.7141(3) 0.0460(3) 0.0554(8) Uani 1 1 d . . . . .
H27A H 0.4943 0.7237 0.0357 0.067 Uiso 1 1 calc R U . . .
H27B H 0.3786 0.6874 -0.0256 0.067 Uiso 1 1 calc R U . . .
Cl1 Cl 0.33736(13) 0.04795(10) 0.41739(9) 0.0960(4) Uani 1 1 d . . . . .
N1 N 0.2262(3) 0.6453(2) 0.43789(18) 0.0428(6) Uani 1 1 d . . . . .
N2 N 0.2831(3) 0.8350(2) 0.0830(2) 0.0498(7) Uani 1 1 d . . . . .
O1 O 0.4655(2) 0.6433(2) 0.37907(18) 0.0607(6) Uani 1 1 d . . . . .
O2 O 0.2701(3) 0.5202(2) 0.02242(19) 0.0705(7) 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 C6 1.384(4) . ?
C1 C2 1.402(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.345(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(4) . ?
C7 N1 1.447(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.223(3) . ?
C8 N1 1.359(4) . ?
C8 C9 1.533(4) . ?
C9 C10 1.509(4) . ?
C9 C25 1.534(4) . ?
C9 C17 1.563(4) . ?
C10 C11 1.387(4) . ?
C10 C16 1.394(4) . ?
C11 C12 1.393(4) . ?
C11 H11 0.9300 . ?
C12 C14 1.379(4) . ?
C12 C13 1.518(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.389(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 N1 1.412(3) . ?
C17 C18 1.515(4) . ?
C17 C27 1.533(4) . ?
C17 H17 0.9800 . ?
C18 O2 1.218(3) . ?
C18 C19 1.488(4) . ?
C19 C20 1.388(4) . ?
C19 C24 1.390(4) . ?
C20 C21 1.373(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(4) . ?
C22 Cl1 1.724(3) . ?
C23 C24 1.381(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.455(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 N2 1.451(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 N2 1.460(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?

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
C6 C1 C2 120.0(3) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 119.3(3) . . ?
C5 C6 C7 122.5(3) . . ?
N1 C7 C6 114.6(2) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 125.6(3) . . ?
O1 C8 C9 126.1(3) . . ?
N1 C8 C9 108.3(2) . . ?
C10 C9 C8 102.2(2) . . ?
C10 C9 C25 111.8(2) . . ?
C8 C9 C25 110.9(2) . . ?
C10 C9 C17 117.4(2) . . ?
C8 C9 C17 113.3(2) . . ?
C25 C9 C17 101.5(2) . . ?
C11 C10 C16 119.1(2) . . ?
C11 C10 C9 132.0(2) . . ?
C16 C10 C9 108.7(2) . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C14 C12 C11 118.5(3) . . ?
C14 C12 C13 121.3(3) . . ?
C11 C12 C13 120.3(3) . . ?
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 C15 122.7(3) . . ?
C12 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C16 C15 C14 117.5(3) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C10 121.8(2) . . ?
C15 C16 N1 129.0(3) . . ?
C10 C16 N1 109.3(2) . . ?
C18 C17 C27 114.5(2) . . ?
C18 C17 C9 111.7(2) . . ?
C27 C17 C9 104.6(2) . . ?
C18 C17 H17 108.6 . . ?
C27 C17 H17 108.6 . . ?
C9 C17 H17 108.6 . . ?
O2 C18 C19 119.9(3) . . ?
O2 C18 C17 121.2(3) . . ?
C19 C18 C17 118.9(3) . . ?
C20 C19 C24 118.0(3) . . ?
C20 C19 C18 123.1(3) . . ?
C24 C19 C18 118.9(3) . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 119.3(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 Cl1 119.3(3) . . ?
C21 C22 Cl1 120.0(3) . . ?
C22 C23 C24 119.3(3) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C23 C24 C19 121.2(3) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
N2 C25 C9 102.4(2) . . ?
N2 C25 H25A 111.3 . . ?
C9 C25 H25A 111.3 . . ?
N2 C25 H25B 111.3 . . ?
C9 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
N2 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C27 C17 105.0(2) . . ?
N2 C27 H27A 110.7 . . ?
C17 C27 H27A 110.7 . . ?
N2 C27 H27B 110.7 . . ?
C17 C27 H27B 110.7 . . ?
H27A C27 H27B 108.8 . . ?
C8 N1 C16 111.3(2) . . ?
C8 N1 C7 123.7(2) . . ?
C16 N1 C7 125.0(2) . . ?
C26 N2 C25 112.9(2) . . ?
C26 N2 C27 113.1(3) . . ?
C25 N2 C27 103.7(2) . . ?

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_6i
_database_code_depnum_ccdc_archive 'CCDC 1858862'
_audit_update_record             
;
2018-08-25 deposited with the CCDC.
2018-08-29 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         'C20 H24 Cl N3 O3'
_chemical_formula_sum            'C20 H24 Cl N3 O3'
_chemical_formula_weight         389.87

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'
Cl Cl 0.1484 0.1585 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.0048(11)
_cell_length_b                   10.8582(13)
_cell_length_c                   23.772(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.426(6)
_cell_angle_gamma                90
_cell_volume                     2062.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6575
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.14

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19757
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.063
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_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             4053
_reflns_number_gt                2703
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0869P)²+0.3902P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4053
_refine_ls_number_parameters     276
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1663
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.108
_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 0.0765(3) 0.9006(2) 0.41413(11) 0.0612(7) Uani 1 1 d . . . . .
H1A H -0.0136 0.9592 0.4180 0.073 Uiso 0.776(9) 1 calc R U P A 1
H1B H 0.0292 0.8215 0.4028 0.073 Uiso 0.776(9) 1 calc R U P A 1
H1C H 0.0428 0.9679 0.4378 0.073 Uiso 0.224(9) 1 calc R U P A 2
H1D H -0.0227 0.8667 0.3944 0.073 Uiso 0.224(9) 1 calc R U P A 2
C3 C 0.3368(4) 0.8371(3) 0.45115(12) 0.0827(9) Uani 1 1 d . . . . .
H3A H 0.3378 0.7492 0.4583 0.099 Uiso 0.776(9) 1 calc R U P A 1
H3B H 0.4273 0.8750 0.4740 0.099 Uiso 0.776(9) 1 calc R U P A 1
H3C H 0.4098 0.7710 0.4649 0.099 Uiso 0.224(9) 1 calc R U P A 2
H3D H 0.3582 0.9101 0.4740 0.099 Uiso 0.224(9) 1 calc R U P A 2
C4 C 0.3560(3) 0.86309(18) 0.38831(9) 0.0487(5) Uani 1 1 d . . . . .
C5 C 0.3470(3) 0.7450(2) 0.35786(12) 0.0644(7) Uani 1 1 d . . . . .
C6 C 0.5221(3) 0.9242(2) 0.37625(12) 0.0582(6) Uani 1 1 d . . . . .
C7 C 0.6744(3) 1.0133(3) 0.30275(16) 0.0887(10) Uani 1 1 d . . . . .
H7A H 0.7732 0.9745 0.3205 0.106 Uiso 1 1 calc R U . . .
H7B H 0.6778 1.0025 0.2623 0.106 Uiso 1 1 calc R U . . .
C8 C 0.6771(4) 1.1451(3) 0.31597(17) 0.1038(11) Uani 1 1 d . . . . .
H8A H 0.5745 1.1823 0.3016 0.156 Uiso 1 1 calc R U . . .
H8B H 0.7697 1.1832 0.2989 0.156 Uiso 1 1 calc R U . . .
H8C H 0.6890 1.1560 0.3561 0.156 Uiso 1 1 calc R U . . .
C9 C 0.1316(3) 0.93191(18) 0.31073(10) 0.0482(5) Uani 1 1 d . . . . .
C10 C 0.1994(2) 0.94638(17) 0.37198(9) 0.0422(5) Uani 1 1 d . . . . .
C11 C 0.2374(2) 1.08283(17) 0.37521(9) 0.0420(5) Uani 1 1 d . . . . .
C12 C 0.2945(3) 1.1565(2) 0.41947(10) 0.0527(6) Uani 1 1 d . . . . .
H12 H 0.3201 1.1236 0.4551 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3126(3) 1.2813(2) 0.40915(10) 0.0595(6) Uani 1 1 d . . . . .
C14 C 0.2763(3) 1.3313(2) 0.35695(12) 0.0666(7) Uani 1 1 d . . . . .
H14 H 0.2921 1.4151 0.3513 0.080 Uiso 1 1 calc R U . . .
C15 C 0.2161(3) 1.25788(19) 0.31250(10) 0.0587(6) Uani 1 1 d . . . . .
H15 H 0.1890 1.2913 0.2771 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1978(2) 1.13383(17) 0.32256(9) 0.0449(5) Uani 1 1 d . . . . .
C17 C 0.0924(3) 1.0593(2) 0.22487(10) 0.0621(7) Uani 1 1 d . U . . .
H17A H 0.0396 1.1391 0.2189 0.075 Uiso 1 1 calc R U . . .
H17B H 0.0123 0.9966 0.2124 0.075 Uiso 1 1 calc R U . . .
C18 C 0.2450(5) 1.0511(4) 0.18978(14) 0.1132(12) Uani 1 1 d . U . . .
H18A H 0.3296 1.1075 0.2054 0.136 Uiso 1 1 calc R U . . .
H18B H 0.2905 0.9685 0.1932 0.136 Uiso 1 1 calc R U . . .
C19 C 0.2118(7) 1.0804(5) 0.12769(17) 0.1437(16) Uani 1 1 d D U . . .
H19A H 0.1086 1.1261 0.1206 0.172 Uiso 0.4 1 calc R U P B 1
H19B H 0.3038 1.1253 0.1126 0.172 Uiso 0.4 1 calc R U P B 1
H19C H 0.1651 1.1627 0.1246 0.172 Uiso 0.6 1 calc R U P C 2
H19D H 0.3182 1.0817 0.1102 0.172 Uiso 0.6 1 calc R U P C 2
C20 C 0.198(3) 0.9514(9) 0.1048(8) 0.202(9) Uani 0.4 1 d D U P D 1
H20A H 0.1769 0.9543 0.0647 0.303 Uiso 0.4 1 calc R U P D 1
H20B H 0.3015 0.9084 0.1136 0.303 Uiso 0.4 1 calc R U P D 1
H20C H 0.1085 0.9092 0.1216 0.303 Uiso 0.4 1 calc R U P D 1
C20' C 0.0982(12) 0.9954(8) 0.0950(3) 0.138(3) Uani 0.6 1 d D U P D 2
H20D H 0.0861 1.0224 0.0565 0.207 Uiso 0.6 1 calc R U P D 2
H20E H 0.1443 0.9138 0.0965 0.207 Uiso 0.6 1 calc R U P D 2
H20F H -0.0093 0.9951 0.1109 0.207 Uiso 0.6 1 calc R U P D 2
Cl1 Cl 0.37975(12) 1.37785(6) 0.46455(4) 0.1018(4) Uani 1 1 d . . . . .
C2 C 0.1023(8) 0.8238(6) 0.5096(2) 0.0973(15) Uani 0.776(9) 1 d . U P A 1
H2A H -0.0103 0.8520 0.5132 0.146 Uiso 0.776(9) 1 calc R U P A 1
H2B H 0.1670 0.8384 0.5443 0.146 Uiso 0.776(9) 1 calc R U P A 1
H2C H 0.1013 0.7373 0.5014 0.146 Uiso 0.776(9) 1 calc R U P A 1
N1 N 0.1763(4) 0.8904(4) 0.46416(12) 0.0674(12) Uani 0.776(9) 1 d . U P A 1
C2' C 0.079(3) 0.7635(18) 0.4991(7) 0.086(5) Uani 0.224(9) 1 d . U P A 2
H2D H 0.0172 0.6894 0.4905 0.130 Uiso 0.224(9) 1 calc R U P A 2
H2E H 0.0034 0.8273 0.5093 0.130 Uiso 0.224(9) 1 calc R U P A 2
H2F H 0.1594 0.7485 0.5299 0.130 Uiso 0.224(9) 1 calc R U P A 2
N1' N 0.1658(16) 0.8021(15) 0.4497(5) 0.080(5) Uani 0.224(9) 1 d . U P A 2
N2 N 0.3472(3) 0.6511(2) 0.33673(14) 0.1017(9) Uani 1 1 d . . . . .
N3 N 0.1366(2) 1.04290(15) 0.28479(7) 0.0476(5) Uani 1 1 d . . . . .
O1 O 0.6322(2) 0.9425(2) 0.41147(10) 0.0955(7) Uani 1 1 d . . . . .
O2 O 0.52412(19) 0.95250(15) 0.32218(8) 0.0638(5) Uani 1 1 d . . . . .
O3 O 0.0772(2) 0.83808(15) 0.28914(7) 0.0729(5) 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 N1 1.397(4) . ?
C1 N1' 1.515(12) . ?
C1 C10 1.529(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C3 N1' 1.419(13) . ?
C3 N1 1.459(4) . ?
C3 C4 1.537(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C4 C5 1.472(3) . ?
C4 C6 1.529(3) . ?
C4 C10 1.575(3) . ?
C5 N2 1.137(3) . ?
C6 O1 1.195(3) . ?
C6 O2 1.323(3) . ?
C7 C8 1.465(4) . ?
C7 O2 1.470(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O3 1.210(2) . ?
C9 N3 1.355(3) . ?
C9 C10 1.532(3) . ?
C10 C11 1.514(3) . ?
C11 C12 1.377(3) . ?
C11 C16 1.388(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(3) . ?
C13 Cl1 1.743(2) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 N3 1.403(3) . ?
C17 N3 1.458(3) . ?
C17 C18 1.522(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.518(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20' 1.482(4) . ?
C19 C20 1.504(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C19 H19D 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20' H20D 0.9600 . ?
C20' H20E 0.9600 . ?
C20' H20F 0.9600 . ?
C2 N1 1.456(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2' N1' 1.462(19) . ?
C2' H2D 0.9600 . ?
C2' H2E 0.9600 . ?
C2' H2F 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
N1 C1 C10 103.0(2) . . ?
N1' C1 C10 107.1(4) . . ?
N1 C1 H1A 111.2 . . ?
C10 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
C10 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
N1' C1 H1C 110.3 . . ?
C10 C1 H1C 110.3 . . ?
N1' C1 H1D 110.3 . . ?
C10 C1 H1D 110.3 . . ?
H1C C1 H1D 108.6 . . ?
N1' C3 C4 100.2(5) . . ?
N1 C3 C4 105.9(2) . . ?
N1 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
N1 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
N1' C3 H3C 111.7 . . ?
C4 C3 H3C 111.7 . . ?
N1' C3 H3D 111.7 . . ?
C4 C3 H3D 111.7 . . ?
H3C C3 H3D 109.5 . . ?
C5 C4 C6 107.65(19) . . ?
C5 C4 C3 108.3(2) . . ?
C6 C4 C3 113.6(2) . . ?
C5 C4 C10 111.35(18) . . ?
C6 C4 C10 113.14(16) . . ?
C3 C4 C10 102.76(19) . . ?
N2 C5 C4 175.8(3) . . ?
O1 C6 O2 126.2(2) . . ?
O1 C6 C4 123.6(3) . . ?
O2 C6 C4 110.1(2) . . ?
C8 C7 O2 111.9(2) . . ?
C8 C7 H7A 109.2 . . ?
O2 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O2 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 N3 125.1(2) . . ?
O3 C9 C10 126.01(19) . . ?
N3 C9 C10 108.83(16) . . ?
C11 C10 C1 114.86(17) . . ?
C11 C10 C9 101.97(16) . . ?
C1 C10 C9 112.58(17) . . ?
C11 C10 C4 113.27(16) . . ?
C1 C10 C4 100.69(17) . . ?
C9 C10 C4 114.03(17) . . ?
C12 C11 C16 120.32(18) . . ?
C12 C11 C10 131.56(19) . . ?
C16 C11 C10 108.08(17) . . ?
C11 C12 C13 117.8(2) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C14 C13 C12 121.9(2) . . ?
C14 C13 Cl1 119.03(18) . . ?
C12 C13 Cl1 119.02(19) . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 C16 C11 121.7(2) . . ?
C15 C16 N3 127.9(2) . . ?
C11 C16 N3 110.40(17) . . ?
N3 C17 C18 111.9(2) . . ?
N3 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N3 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 114.9(3) . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20' C19 C18 116.5(5) . . ?
C20 C19 C18 99.3(8) . . ?
C20 C19 H19A 111.9 . . ?
C18 C19 H19A 111.9 . . ?
C20 C19 H19B 111.9 . . ?
C18 C19 H19B 111.9 . . ?
H19A C19 H19B 109.6 . . ?
C20' C19 H19C 108.2 . . ?
C18 C19 H19C 108.2 . . ?
C20' C19 H19D 108.2 . . ?
C18 C19 H19D 108.2 . . ?
H19C C19 H19D 107.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20' H20D 109.5 . . ?
C19 C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C19 C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N1 C2 115.7(3) . . ?
C1 N1 C3 108.5(3) . . ?
C2 N1 C3 111.3(4) . . ?
N1' C2' H2D 109.5 . . ?
N1' C2' H2E 109.5 . . ?
H2D C2' H2E 109.5 . . ?
N1' C2' H2F 109.5 . . ?
H2D C2' H2F 109.5 . . ?
H2E C2' H2F 109.5 . . ?
C3 N1' C2' 124.1(11) . . ?
C3 N1' C1 104.3(8) . . ?
C2' N1' C1 114.8(12) . . ?
C9 N3 C16 110.70(17) . . ?
C9 N3 C17 122.76(18) . . ?
C16 N3 C17 126.45(18) . . ?
C6 O2 C7 117.9(2) . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_8a
_database_code_depnum_ccdc_archive 'CCDC 1858863'
_audit_update_record             
;
2018-08-25 deposited with the CCDC.
2018-08-29 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         'C21 H22 N2 O2'
_chemical_formula_sum            'C21 H22 N2 O2'
_chemical_formula_weight         334.40

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.3445(8)
_cell_length_b                   18.8273(19)
_cell_length_c                   11.5601(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.495(3)
_cell_angle_gamma                90
_cell_volume                     1816.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5345
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11847
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.067
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3502
_reflns_number_gt                2134
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0701P)²+0.1698P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3502
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.2484(2) 0.22165(12) 0.30418(18) 0.0517(5) Uani 1 1 d . . . . .
C2 C 0.2763(2) 0.15078(11) 0.36710(16) 0.0489(5) Uani 1 1 d . . . . .
C3 C 0.2968(2) 0.09979(11) 0.26823(15) 0.0456(5) Uani 1 1 d . . . . .
C4 C 0.3293(2) 0.02796(11) 0.26653(16) 0.0525(5) Uani 1 1 d . . . . .
H4 H 0.3441 0.0034 0.3356 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3399(2) -0.00784(11) 0.16161(18) 0.0557(6) Uani 1 1 d . . . . .
C6 C 0.3814(4) -0.08585(13) 0.1585(2) 0.0862(8) Uani 1 1 d . . . . .
H6A H 0.3751 -0.1027 0.0802 0.129 Uiso 1 1 calc R U . . .
H6B H 0.3073 -0.1118 0.2053 0.129 Uiso 1 1 calc R U . . .
H6C H 0.4883 -0.0926 0.1879 0.129 Uiso 1 1 calc R U . . .
C7 C 0.3144(3) 0.03050(13) 0.06054(18) 0.0617(6) Uani 1 1 d . . . . .
H7 H 0.3209 0.0069 -0.0099 0.074 Uiso 1 1 calc R U . . .
C8 C 0.2797(2) 0.10217(12) 0.06010(17) 0.0553(6) Uani 1 1 d . . . . .
H8 H 0.2621 0.1266 -0.0088 0.066 Uiso 1 1 calc R U . . .
C9 C 0.2721(2) 0.13600(10) 0.16479(16) 0.0451(5) Uani 1 1 d . . . . .
C10 C 0.4143(2) 0.15679(11) 0.46000(16) 0.0508(5) Uani 1 1 d . . . . .
H10 H 0.4353 0.2074 0.4728 0.061 Uiso 1 1 calc R U . . .
C11 C 0.5711(2) 0.12232(12) 0.42712(18) 0.0564(6) Uani 1 1 d . . . . .
C12 C 0.6530(2) 0.14509(12) 0.31935(17) 0.0519(5) Uani 1 1 d . . . . .
C13 C 0.6306(2) 0.21129(13) 0.26973(19) 0.0608(6) Uani 1 1 d . . . . .
H13 H 0.5619 0.2438 0.3040 0.073 Uiso 1 1 calc R U . . .
C14 C 0.7097(3) 0.22924(13) 0.1699(2) 0.0692(7) Uani 1 1 d . . . . .
H14 H 0.6942 0.2742 0.1382 0.083 Uiso 1 1 calc R U . . .
C15 C 0.8111(2) 0.18232(15) 0.1156(2) 0.0668(7) Uani 1 1 d . . . . .
C16 C 0.8951(3) 0.20235(17) 0.0051(2) 0.0951(10) Uani 1 1 d . . . . .
H16A H 0.9805 0.2349 0.0223 0.143 Uiso 1 1 calc R U . . .
H16B H 0.8200 0.2244 -0.0470 0.143 Uiso 1 1 calc R U . . .
H16C H 0.9382 0.1604 -0.0303 0.143 Uiso 1 1 calc R U . . .
C17 C 0.8342(3) 0.11619(15) 0.1651(2) 0.0708(7) Uani 1 1 d . . . . .
H17 H 0.9024 0.0837 0.1301 0.085 Uiso 1 1 calc R U . . .
C18 C 0.7564(3) 0.09796(13) 0.2665(2) 0.0653(6) Uani 1 1 d . . . . .
H18 H 0.7740 0.0535 0.2994 0.078 Uiso 1 1 calc R U . . .
C19 C 0.1294(2) 0.13108(12) 0.44279(17) 0.0601(6) Uani 1 1 d . . . . .
H19A H 0.0352 0.1572 0.4178 0.072 Uiso 1 1 calc R U . . .
H19B H 0.1068 0.0806 0.4375 0.072 Uiso 1 1 calc R U . . .
C20 C 0.0689(3) 0.11563(14) 0.64570(19) 0.0793(7) Uani 1 1 d . . . . .
H20A H -0.0393 0.1315 0.6341 0.119 Uiso 1 1 calc R U . . .
H20B H 0.1037 0.1275 0.7227 0.119 Uiso 1 1 calc R U . . .
H20C H 0.0738 0.0651 0.6354 0.119 Uiso 1 1 calc R U . . .
C21 C 0.3406(3) 0.12722(12) 0.56999(17) 0.0617(6) Uani 1 1 d . . . . .
H21A H 0.3480 0.0758 0.5723 0.074 Uiso 1 1 calc R U . . .
H21B H 0.3926 0.1467 0.6383 0.074 Uiso 1 1 calc R U . . .
N1 N 0.24035(19) 0.20799(9) 0.18900(14) 0.0518(5) Uani 1 1 d . . . . .
H1 H 0.2186 0.2394 0.1372 0.062 Uiso 1 1 calc R U . . .
N2 N 0.1740(2) 0.15048(9) 0.56124(14) 0.0582(5) Uani 1 1 d . . . . .
O1 O 0.23705(19) 0.27958(9) 0.34997(13) 0.0696(5) Uani 1 1 d . . . . .
O2 O 0.6305(2) 0.07682(10) 0.48821(14) 0.0883(6) 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 O1 1.216(2) . ?
C1 N1 1.357(3) . ?
C1 C2 1.537(3) . ?
C2 C3 1.503(3) . ?
C2 C19 1.557(3) . ?
C2 C10 1.572(3) . ?
C3 C4 1.380(3) . ?
C3 C9 1.390(3) . ?
C4 C5 1.391(3) . ?
C4 H4 0.9300 . ?
C5 C7 1.388(3) . ?
C5 C6 1.509(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C9 N1 1.410(2) . ?
C10 C11 1.512(3) . ?
C10 C21 1.523(3) . ?
C10 H10 0.9800 . ?
C11 O2 1.213(2) . ?
C11 C12 1.489(3) . ?
C12 C18 1.383(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 C17 1.383(3) . ?
C15 C16 1.511(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N2 1.462(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N2 1.472(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N2 1.460(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
N1 H1 0.8600 . ?

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 N1 126.4(2) . . ?
O1 C1 C2 125.78(18) . . ?
N1 C1 C2 107.81(17) . . ?
C3 C2 C1 102.26(15) . . ?
C3 C2 C19 111.74(16) . . ?
C1 C2 C19 110.86(16) . . ?
C3 C2 C10 118.55(15) . . ?
C1 C2 C10 111.59(16) . . ?
C19 C2 C10 102.06(14) . . ?
C4 C3 C9 119.74(17) . . ?
C4 C3 C2 131.33(17) . . ?
C9 C3 C2 108.90(17) . . ?
C3 C4 C5 120.09(18) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C7 C5 C4 118.1(2) . . ?
C7 C5 C6 121.28(19) . . ?
C4 C5 C6 120.58(19) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 122.83(19) . . ?
C8 C7 H7 118.6 . . ?
C5 C7 H7 118.6 . . ?
C9 C8 C7 117.56(19) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C8 C9 C3 121.64(19) . . ?
C8 C9 N1 129.25(18) . . ?
C3 C9 N1 109.11(16) . . ?
C11 C10 C21 114.18(18) . . ?
C11 C10 C2 115.33(15) . . ?
C21 C10 C2 104.20(16) . . ?
C11 C10 H10 107.6 . . ?
C21 C10 H10 107.6 . . ?
C2 C10 H10 107.6 . . ?
O2 C11 C12 120.13(19) . . ?
O2 C11 C10 120.45(18) . . ?
C12 C11 C10 119.42(19) . . ?
C18 C12 C13 118.5(2) . . ?
C18 C12 C11 118.5(2) . . ?
C13 C12 C11 123.01(19) . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 121.7(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C17 118.2(2) . . ?
C14 C15 C16 121.1(3) . . ?
C17 C15 C16 120.7(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 120.5(2) . . ?
C15 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C12 C18 C17 120.8(2) . . ?
C12 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
N2 C19 C2 105.77(16) . . ?
N2 C19 H19A 110.6 . . ?
C2 C19 H19A 110.6 . . ?
N2 C19 H19B 110.6 . . ?
C2 C19 H19B 110.6 . . ?
H19A C19 H19B 108.7 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C10 102.93(16) . . ?
N2 C21 H21A 111.2 . . ?
C10 C21 H21A 111.2 . . ?
N2 C21 H21B 111.2 . . ?
C10 C21 H21B 111.2 . . ?
H21A C21 H21B 109.1 . . ?
C1 N1 C9 111.66(16) . . ?
C1 N1 H1 124.2 . . ?
C9 N1 H1 124.2 . . ?
C21 N2 C19 102.96(15) . . ?
C21 N2 C20 113.12(18) . . ?
C19 N2 C20 111.20(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.86 2.28 3.094(2) 157.8 4_565

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_4n
_database_code_depnum_ccdc_archive 'CCDC 1858859'
_audit_update_record             
;
2018-08-25 deposited with the CCDC.
2018-08-29 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         'C19 H20 N4 O3'
_chemical_formula_sum            'C19 H20 N4 O3'
_chemical_formula_weight         352.39

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.5941(10)
_cell_length_b                   7.5500(6)
_cell_length_c                   22.5636(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.250(3)
_cell_angle_gamma                90
_cell_volume                     1959.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8163
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20478
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.374
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4466
_reflns_number_gt                3161
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0614P)²+0.5938P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4466
_refine_ls_number_parameters     240
_refine_ls_number_restraints     219
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.3395(3) 0.0352(10) 0.23809(13) 0.214(3) Uani 1 1 d . U . . .
H1A H 0.3524 0.0283 0.2809 0.322 Uiso 1 1 calc R U . . .
H1B H 0.3921 0.1198 0.2245 0.322 Uiso 1 1 calc R U . . .
H1C H 0.3527 -0.0790 0.2214 0.322 Uiso 1 1 calc R U . . .
C2 C 0.1970(4) 0.2788(6) 0.23937(14) 0.1453(15) Uani 1 1 d . U . . .
H2A H 0.2122 0.2843 0.2822 0.218 Uiso 1 1 calc R U . . .
H2B H 0.1177 0.3116 0.2268 0.218 Uiso 1 1 calc R U . . .
H2C H 0.2479 0.3590 0.2222 0.218 Uiso 1 1 calc R U . . .
C3 C 0.1274(3) -0.0325(6) 0.23648(12) 0.1337(14) Uani 1 1 d . U . . .
H3A H 0.1370 -0.1470 0.2193 0.201 Uiso 1 1 calc R U . . .
H3B H 0.0515 0.0126 0.2224 0.201 Uiso 1 1 calc R U . . .
H3C H 0.1358 -0.0424 0.2792 0.201 Uiso 1 1 calc R U . . .
C4 C 0.2179(2) 0.0914(5) 0.21865(9) 0.0970(10) Uani 1 1 d . U . . .
C5 C 0.12153(16) 0.1449(3) 0.11826(8) 0.0536(5) Uani 1 1 d . U . . .
C6 C 0.24015(13) 0.0894(2) 0.03380(7) 0.0395(4) Uani 1 1 d . U . . .
C7 C 0.22840(13) 0.1484(2) -0.03190(7) 0.0369(4) Uani 1 1 d . U . . .
C8 C 0.10619(13) 0.2183(2) -0.04218(7) 0.0388(4) Uani 1 1 d . U . . .
C9 C 0.04063(15) 0.2709(2) -0.09422(8) 0.0507(4) Uani 1 1 d . U . . .
H9 H 0.0717 0.2688 -0.1303 0.061 Uiso 1 1 calc R U . . .
C10 C -0.07275(16) 0.3270(3) -0.09204(10) 0.0602(5) Uani 1 1 d . U . . .
H10 H -0.1183 0.3629 -0.1269 0.072 Uiso 1 1 calc R U . . .
C11 C -0.11783(15) 0.3299(2) -0.03871(10) 0.0573(5) Uani 1 1 d . U . . .
H11 H -0.1937 0.3690 -0.0381 0.069 Uiso 1 1 calc R U . . .
C12 C -0.05411(14) 0.2765(2) 0.01385(9) 0.0498(4) Uani 1 1 d . U . . .
H12 H -0.0856 0.2790 0.0498 0.060 Uiso 1 1 calc R U . . .
C13 C 0.05881(13) 0.2189(2) 0.01142(7) 0.0391(4) Uani 1 1 d . U . . .
C14 C 0.32816(13) 0.2921(2) -0.03867(7) 0.0386(4) Uani 1 1 d . U . . .
C15 C 0.37951(15) 0.3703(2) 0.01886(8) 0.0494(4) Uani 1 1 d . U . . .
C16 C 0.28403(14) 0.4392(2) -0.07778(8) 0.0430(4) Uani 1 1 d . U . . .
C17 C 0.25908(14) -0.0001(2) -0.07410(8) 0.0440(4) Uani 1 1 d . U . . .
H17A H 0.2959 -0.0987 -0.0515 0.053 Uiso 1 1 calc R U . . .
H17B H 0.1899 -0.0426 -0.0986 0.053 Uiso 1 1 calc R U . . .
C18 C 0.3975(2) -0.0472(3) -0.14534(10) 0.0694(6) Uani 1 1 d . U . . .
H18A H 0.4490 0.0138 -0.1686 0.104 Uiso 1 1 calc R U . . .
H18B H 0.3406 -0.1115 -0.1715 0.104 Uiso 1 1 calc R U . . .
H18C H 0.4414 -0.1283 -0.1185 0.104 Uiso 1 1 calc R U . . .
C19 C 0.41660(14) 0.1848(2) -0.06970(8) 0.0494(4) Uani 1 1 d . U . . .
H19A H 0.4657 0.2613 -0.0903 0.059 Uiso 1 1 calc R U . . .
H19B H 0.4649 0.1104 -0.0416 0.059 Uiso 1 1 calc R U . . .
N1 N 0.14127(11) 0.15029(18) 0.05780(6) 0.0417(3) Uani 1 1 d . U . . .
N2 N 0.41829(17) 0.4321(3) 0.06236(9) 0.0766(6) Uani 1 1 d . U . . .
N3 N 0.25284(15) 0.5550(2) -0.10787(7) 0.0603(4) Uani 1 1 d . U . . .
N4 N 0.33903(12) 0.08131(18) -0.11093(6) 0.0454(4) Uani 1 1 d . U . . .
O1 O 0.21451(13) 0.0947(3) 0.15228(6) 0.0873(6) Uani 1 1 d . U . . .
O2 O 0.02994(13) 0.1831(3) 0.13303(7) 0.0881(6) Uani 1 1 d . U . . .
O3 O 0.32062(11) 0.00795(18) 0.05884(5) 0.0551(4) Uani 1 1 d . 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
C1 C4 1.485(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.520(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.498(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O1 1.493(2) . ?
C5 O2 1.188(2) . ?
C5 O1 1.299(2) . ?
C5 N1 1.412(2) . ?
C6 O3 1.1979(19) . ?
C6 N1 1.4055(19) . ?
C6 C7 1.537(2) . ?
C7 C8 1.502(2) . ?
C7 C17 1.541(2) . ?
C7 C14 1.607(2) . ?
C8 C9 1.374(2) . ?
C8 C13 1.390(2) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9300 . ?
C13 N1 1.423(2) . ?
C14 C16 1.470(2) . ?
C14 C15 1.481(2) . ?
C14 C19 1.542(2) . ?
C15 N2 1.128(2) . ?
C16 N3 1.138(2) . ?
C17 N4 1.457(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N4 1.462(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N4 1.440(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 O1 101.83(19) . . ?
C1 C4 C3 114.4(4) . . ?
O1 C4 C3 110.4(2) . . ?
C1 C4 C2 111.0(4) . . ?
O1 C4 C2 107.9(3) . . ?
C3 C4 C2 110.7(3) . . ?
O2 C5 O1 127.58(18) . . ?
O2 C5 N1 121.58(19) . . ?
O1 C5 N1 110.84(15) . . ?
O3 C6 N1 127.63(15) . . ?
O3 C6 C7 124.93(14) . . ?
N1 C6 C7 107.43(13) . . ?
C8 C7 C6 102.57(12) . . ?
C8 C7 C17 116.56(13) . . ?
C6 C7 C17 112.69(13) . . ?
C8 C7 C14 115.10(13) . . ?
C6 C7 C14 108.05(12) . . ?
C17 C7 C14 101.96(11) . . ?
C9 C8 C13 120.38(15) . . ?
C9 C8 C7 129.97(14) . . ?
C13 C8 C7 109.60(14) . . ?
C8 C9 C10 118.82(17) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 120.24(18) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.94(17) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C12 C13 117.66(17) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C12 C13 C8 120.94(16) . . ?
C12 C13 N1 129.40(15) . . ?
C8 C13 N1 109.64(13) . . ?
C16 C14 C15 107.21(14) . . ?
C16 C14 C19 108.98(13) . . ?
C15 C14 C19 112.99(14) . . ?
C16 C14 C7 111.53(12) . . ?
C15 C14 C7 113.61(13) . . ?
C19 C14 C7 102.50(12) . . ?
N2 C15 C14 179.0(2) . . ?
N3 C16 C14 178.13(18) . . ?
N4 C17 C7 104.99(13) . . ?
N4 C17 H17A 110.7 . . ?
C7 C17 H17A 110.7 . . ?
N4 C17 H17B 110.7 . . ?
C7 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 C14 100.45(12) . . ?
N4 C19 H19A 111.7 . . ?
C14 C19 H19A 111.7 . . ?
N4 C19 H19B 111.7 . . ?
C14 C19 H19B 111.7 . . ?
H19A C19 H19B 109.5 . . ?
C6 N1 C5 127.04(15) . . ?
C6 N1 C13 109.91(12) . . ?
C5 N1 C13 123.04(14) . . ?
C19 N4 C17 104.53(13) . . ?
C19 N4 C18 114.16(15) . . ?
C17 N4 C18 113.22(14) . . ?
C5 O1 C4 120.84(16) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_4i
_database_code_depnum_ccdc_archive 'CCDC 1858858'
_audit_update_record             
;
2018-08-25 deposited with the CCDC.
2018-08-29 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         'C16 H16 N4 O'
_chemical_formula_sum            'C16 H16 N4 O'
_chemical_formula_weight         280.33

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                   7.8537(7)
_cell_length_b                   10.0186(8)
_cell_length_c                   10.4353(9)
_cell_angle_alpha                73.180(3)
_cell_angle_beta                 70.237(3)
_cell_angle_gamma                72.218(3)
_cell_volume                     719.76(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5425
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10797
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.120
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3261
_reflns_number_gt                2507
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0645P)²+0.1169P] 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         3261
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.5704(2) 0.17813(18) 0.43259(16) 0.0513(4) Uani 1 1 d . . . . .
H1A H 0.6574 0.0952 0.4654 0.077 Uiso 1 1 calc R U . . .
H1B H 0.6368 0.2444 0.3624 0.077 Uiso 1 1 calc R U . . .
H1C H 0.4955 0.1497 0.3938 0.077 Uiso 1 1 calc R U . . .
C2 C 0.32877(17) 0.38265(14) 0.53363(13) 0.0356(3) Uani 1 1 d . . . . .
C3 C 0.2958(2) 0.47410(16) 0.41335(14) 0.0441(3) Uani 1 1 d . . . . .
H3 H 0.3494 0.4471 0.3277 0.053 Uiso 1 1 calc R U . . .
C4 C 0.1796(2) 0.60797(16) 0.42488(15) 0.0458(4) Uani 1 1 d . . . . .
H4 H 0.1557 0.6715 0.3448 0.055 Uiso 1 1 calc R U . . .
C5 C 0.09758(19) 0.65098(15) 0.55113(15) 0.0431(3) Uani 1 1 d . . . . .
C6 C -0.0225(2) 0.80017(17) 0.5554(2) 0.0610(5) Uani 1 1 d . . . . .
H6A H -0.1454 0.8025 0.5550 0.091 Uiso 1 1 calc R U . . .
H6B H 0.0301 0.8664 0.4754 0.091 Uiso 1 1 calc R U . . .
H6C H -0.0286 0.8266 0.6385 0.091 Uiso 1 1 calc R U . . .
C7 C 0.13005(19) 0.55460(15) 0.67159(14) 0.0401(3) Uani 1 1 d . . . . .
H7 H 0.0748 0.5807 0.7576 0.048 Uiso 1 1 calc R U . . .
C8 C 0.24466(17) 0.42012(14) 0.66271(13) 0.0348(3) Uani 1 1 d . . . . .
C9 C 0.31469(17) 0.29953(14) 0.77083(13) 0.0357(3) Uani 1 1 d . . . . .
C10 C 0.46060(18) 0.19467(15) 0.68119(14) 0.0409(3) Uani 1 1 d . . . . .
C11 C 0.16705(18) 0.21406(14) 0.88164(13) 0.0362(3) Uani 1 1 d . . . . .
C12 C 0.1424(2) 0.09949(16) 0.83185(15) 0.0445(3) Uani 1 1 d . . . . .
C13 C -0.0176(2) 0.30957(16) 0.92156(15) 0.0457(4) Uani 1 1 d . . . . .
C14 C 0.3980(2) 0.33833(17) 0.86623(14) 0.0442(3) Uani 1 1 d . . . . .
H14A H 0.5305 0.2960 0.8475 0.053 Uiso 1 1 calc R U . . .
H14B H 0.3789 0.4414 0.8506 0.053 Uiso 1 1 calc R U . . .
C15 C 0.2507(2) 0.15645(15) 1.00613(14) 0.0432(3) Uani 1 1 d . . . . .
H15A H 0.1596 0.1268 1.0916 0.052 Uiso 1 1 calc R U . . .
H15B H 0.3578 0.0771 0.9903 0.052 Uiso 1 1 calc R U . . .
C16 C 0.4107(3) 0.2587(2) 1.10447(17) 0.0636(5) Uani 1 1 d . . . . .
H16A H 0.3431 0.2206 1.1968 0.095 Uiso 1 1 calc R U . . .
H16B H 0.4335 0.3481 1.1028 0.095 Uiso 1 1 calc R U . . .
H16C H 0.5271 0.1922 1.0775 0.095 Uiso 1 1 calc R U . . .
N1 N 0.45149(15) 0.24639(12) 0.54800(11) 0.0397(3) Uani 1 1 d . . . . .
N2 N 0.1216(2) 0.01090(17) 0.79510(16) 0.0683(4) Uani 1 1 d . . . . .
N3 N -0.1635(2) 0.37856(17) 0.95335(19) 0.0751(5) Uani 1 1 d . . . . .
N4 N 0.30282(17) 0.28169(13) 1.00833(12) 0.0443(3) Uani 1 1 d . . . . .
O1 O 0.56332(15) 0.08466(12) 0.72370(12) 0.0603(3) 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 N1 1.4547(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.3753(19) . ?
C2 C8 1.3896(18) . ?
C2 N1 1.4109(17) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9300 . ?
C5 C7 1.393(2) . ?
C5 C6 1.508(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.3817(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.5033(18) . ?
C9 C14 1.5461(18) . ?
C9 C10 1.5493(19) . ?
C9 C11 1.5943(17) . ?
C10 O1 1.2159(17) . ?
C10 N1 1.3539(18) . ?
C11 C13 1.472(2) . ?
C11 C12 1.474(2) . ?
C11 C15 1.5374(19) . ?
C12 N2 1.135(2) . ?
C13 N3 1.1374(19) . ?
C14 N4 1.4499(17) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.4420(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N4 1.449(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C8 121.80(13) . . ?
C3 C2 N1 128.11(12) . . ?
C8 C2 N1 110.03(11) . . ?
C2 C3 C4 117.32(13) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C3 C4 C5 122.59(13) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C7 118.70(14) . . ?
C4 C5 C6 119.76(14) . . ?
C7 C5 C6 121.54(14) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 119.71(13) . . ?
C8 C7 H7 120.1 . . ?
C5 C7 H7 120.1 . . ?
C7 C8 C2 119.82(12) . . ?
C7 C8 C9 131.58(12) . . ?
C2 C8 C9 108.41(11) . . ?
C8 C9 C14 116.89(11) . . ?
C8 C9 C10 102.19(10) . . ?
C14 C9 C10 111.88(11) . . ?
C8 C9 C11 116.63(10) . . ?
C14 C9 C11 101.71(10) . . ?
C10 C9 C11 107.52(10) . . ?
O1 C10 N1 126.26(13) . . ?
O1 C10 C9 125.84(13) . . ?
N1 C10 C9 107.89(11) . . ?
C13 C11 C12 107.08(12) . . ?
C13 C11 C15 109.90(12) . . ?
C12 C11 C15 112.86(12) . . ?
C13 C11 C9 111.78(11) . . ?
C12 C11 C9 113.47(11) . . ?
C15 C11 C9 101.77(10) . . ?
N2 C12 C11 179.07(16) . . ?
N3 C13 C11 177.05(16) . . ?
N4 C14 C9 106.69(11) . . ?
N4 C14 H14A 110.4 . . ?
C9 C14 H14A 110.4 . . ?
N4 C14 H14B 110.4 . . ?
C9 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
N4 C15 C11 100.57(11) . . ?
N4 C15 H15A 111.7 . . ?
C11 C15 H15A 111.7 . . ?
N4 C15 H15B 111.7 . . ?
C11 C15 H15B 111.7 . . ?
H15A C15 H15B 109.4 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 N1 C2 111.09(11) . . ?
C10 N1 C1 123.96(12) . . ?
C2 N1 C1 124.53(12) . . ?
C15 N4 C16 115.07(12) . . ?
C15 N4 C14 106.89(11) . . ?
C16 N4 C14 112.32(12) . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034

