# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_3aa
_database_code_depnum_ccdc_archive 'CCDC 1892976'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO, UMR CNRS 8182, Universit? Paris-Sud 11, Universit? Paris-Saclay, FRANCE.
France
;
_audit_update_record             
;
2019-01-23 deposited with the CCDC.	2019-04-04 downloaded from the CCDC.
;




_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H17 N O2'
_chemical_formula_sum            'C19 H17 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         291.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0096 '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 0.0310 0.0189 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_chemical_absolute_configuration ad

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

_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.
;

_cell_length_a                   9.358(2)
_cell_length_b                   5.3966(14)
_cell_length_c                   15.126(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.380(16)
_cell_angle_gamma                90
_cell_volume                     729.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    4032
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      66.81
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.686
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   'apex3 Bruker'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8823
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         66.928
_diffrn_reflns_theta_full        66.928
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             2488
_reflns_number_gt                2081
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.915
_reflns_Friedel_fraction_full    0.915

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²+0.3502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_number_reflns         2488
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1002
_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 0.3365(4) 0.4694(8) 0.0565(3) 0.0216(9) Uani 1 1 d . . . . .
H1 H 0.291266 0.301023 0.054992 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2138(4) 0.6523(8) 0.0144(3) 0.0256(10) Uani 1 1 d . . . . .
H2 H 0.155932 0.650671 -0.048962 0.031 Uiso 1 1 calc R U . . .
C3 C 0.1951(4) 0.8161(9) 0.0754(3) 0.0279(11) Uani 1 1 d . . . . .
H3 H 0.122848 0.945274 0.062187 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3041(4) 0.7666(9) 0.1671(3) 0.0247(10) Uani 1 1 d . . . . .
C5 C 0.3924(4) 0.5565(8) 0.1561(3) 0.0212(9) Uani 1 1 d . . . . .
C6 C 0.4982(4) 0.4422(8) 0.2278(3) 0.0200(9) Uani 1 1 d . . . . .
C7 C 0.5868(4) 0.2233(8) 0.2131(3) 0.0202(9) Uani 1 1 d . . . . .
H7A H 0.535340 0.148177 0.152165 0.024 Uiso 1 1 calc R U . . .
H7B H 0.589786 0.097832 0.261343 0.024 Uiso 1 1 calc R U . . .
C8 C 0.7468(4) 0.2892(8) 0.2163(3) 0.0186(9) Uani 1 1 d . . . . .
C9 C 0.8607(4) 0.1203(8) 0.2558(3) 0.0226(9) Uani 1 1 d . . . . .
H9 H 0.838964 -0.025113 0.284754 0.027 Uiso 1 1 calc R U . . .
C10 C 1.0054(4) 0.1630(8) 0.2531(3) 0.0248(10) Uani 1 1 d . . . . .
H10 H 1.081944 0.044775 0.278245 0.030 Uiso 1 1 calc R U . . .
C11 C 1.0379(4) 0.3802(8) 0.2133(3) 0.0260(10) Uani 1 1 d . . . . .
H11 H 1.137197 0.411237 0.211909 0.031 Uiso 1 1 calc R U . . .
C12 C 0.9261(4) 0.5506(8) 0.1757(3) 0.0251(9) Uani 1 1 d . . . . .
H12 H 0.948612 0.698668 0.148632 0.030 Uiso 1 1 calc R U . . .
C13 C 0.7809(4) 0.5060(8) 0.1774(3) 0.0226(9) Uani 1 1 d . . . . .
H13 H 0.704545 0.624218 0.151875 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6316(4) 0.4267(8) 0.3955(3) 0.0230(9) Uani 1 1 d . . . . .
C15 C 0.5929(4) 0.2145(9) 0.4345(3) 0.0268(10) Uani 1 1 d . . . . .
H15 H 0.499214 0.136837 0.406306 0.032 Uiso 1 1 calc R U . . .
C16 C 0.6902(5) 0.1149(9) 0.5144(3) 0.0317(11) Uani 1 1 d . . . . .
H16 H 0.663645 -0.030503 0.541187 0.038 Uiso 1 1 calc R U . . .
C17 C 0.8270(5) 0.2299(9) 0.5548(3) 0.0339(11) Uani 1 1 d . . . . .
H17 H 0.894567 0.162605 0.609455 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8651(5) 0.4412(10) 0.5160(3) 0.0333(11) Uani 1 1 d . . . . .
H18 H 0.958336 0.519899 0.544359 0.040 Uiso 1 1 calc R U . . .
C19 C 0.7686(4) 0.5392(9) 0.4361(3) 0.0288(10) Uani 1 1 d . . . . .
H19 H 0.796073 0.683375 0.408989 0.035 Uiso 1 1 calc R U . . .
N1 N 0.5307(4) 0.5376(7) 0.3144(2) 0.0248(8) Uani 1 1 d . . . . .
O1 O 0.3158(3) 0.8858(6) 0.23972(19) 0.0278(7) Uani 1 1 d . . . . .
O2 O 0.4454(3) 0.4608(6) 0.00732(18) 0.0272(7) Uani 1 1 d . . . . .
H20 H 0.479(5) 0.600(9) 0.005(3) 0.041 Uiso 1 1 calc R U . . .
H100 H 0.476(5) 0.674(9) 0.321(3) 0.028(12) Uiso 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 O2 1.430(4) . ?
C1 C2 1.504(6) . ?
C1 C5 1.515(5) . ?
C1 H1 1.0000 . ?
C2 C3 1.326(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.481(6) . ?
C3 H3 0.9500 . ?
C4 O1 1.249(5) . ?
C4 C5 1.441(6) . ?
C5 C6 1.377(5) . ?
C6 N1 1.354(5) . ?
C6 C7 1.498(6) . ?
C7 C8 1.526(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.389(6) . ?
C8 C9 1.394(5) . ?
C9 C10 1.386(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.384(6) . ?
C14 C19 1.386(6) . ?
C14 N1 1.436(5) . ?
C15 C16 1.386(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1 H100 0.92(5) . ?
O2 H20 0.82(5) . ?

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
O2 C1 C2 112.0(3) . . ?
O2 C1 C5 116.1(3) . . ?
C2 C1 C5 102.1(3) . . ?
O2 C1 H1 108.8 . . ?
C2 C1 H1 108.8 . . ?
C5 C1 H1 108.8 . . ?
C3 C2 C1 112.7(4) . . ?
C3 C2 H2 123.6 . . ?
C1 C2 H2 123.6 . . ?
C2 C3 C4 109.5(4) . . ?
C2 C3 H3 125.2 . . ?
C4 C3 H3 125.2 . . ?
O1 C4 C5 127.2(4) . . ?
O1 C4 C3 125.9(4) . . ?
C5 C4 C3 106.9(4) . . ?
C6 C5 C4 124.3(4) . . ?
C6 C5 C1 126.7(4) . . ?
C4 C5 C1 108.7(3) . . ?
N1 C6 C5 119.5(4) . . ?
N1 C6 C7 118.0(3) . . ?
C5 C6 C7 122.4(4) . . ?
C6 C7 C8 113.1(3) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C13 C8 C9 119.3(4) . . ?
C13 C8 C7 122.0(3) . . ?
C9 C8 C7 118.6(4) . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.1(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.3(4) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C15 C14 C19 119.9(4) . . ?
C15 C14 N1 121.3(4) . . ?
C19 C14 N1 118.8(4) . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 119.8(4) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C6 N1 C14 124.6(4) . . ?
C6 N1 H100 116(3) . . ?
C14 N1 H100 119(3) . . ?
C1 O2 H20 109.5 . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 1892977'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO, UMR CNRS 8182, Universit? Paris-Sud 11, Universit? Paris-Saclay, FRANCE.
France
;
_audit_update_record             
;
2019-01-23 deposited with the CCDC.	2019-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N O3'
_chemical_formula_sum            'C23 H21 N O3'
_chemical_formula_weight         359.41

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                   8.1794(2)
_cell_length_b                   10.7510(2)
_cell_length_c                   11.9840(3)
_cell_angle_alpha                74.5430(10)
_cell_angle_beta                 70.1210(10)
_cell_angle_gamma                76.3680(10)
_cell_volume                     942.88(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      36.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9618
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_process_details   'SADABS apex2'
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24636
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.846
_diffrn_reflns_theta_max         36.381
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8644
_reflns_number_gt                7160
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²+0.1554P] 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         8644
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.050
_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 1.06405(13) 0.69958(9) 0.96388(9) 0.02876(18) Uani 1 1 d . . . . .
H1A H 0.972587 0.724073 1.035729 0.043 Uiso 1 1 calc R U . . .
H1B H 1.164360 0.744419 0.945385 0.043 Uiso 1 1 calc R U . . .
H1C H 1.102907 0.604812 0.979566 0.043 Uiso 1 1 calc R U . . .
C2 C 0.83990(10) 0.69850(7) 0.88155(7) 0.01798(12) Uani 1 1 d . . . . .
C3 C 0.77831(9) 0.73982(7) 0.77232(6) 0.01482(11) Uani 1 1 d . . . . .
C4 C 0.61353(9) 0.71488(7) 0.78152(6) 0.01631(12) Uani 1 1 d . . . . .
H4 H 0.544449 0.671863 0.856894 0.020 Uiso 1 1 calc R U . . .
C5 C 0.54947(9) 0.75203(7) 0.68219(6) 0.01490(11) Uani 1 1 d . . . . .
H5 H 0.436568 0.735516 0.690027 0.018 Uiso 1 1 calc R U . . .
C6 C 0.65164(8) 0.81405(6) 0.57005(6) 0.01165(10) Uani 1 1 d . . . . .
C7 C 0.71051(8) 0.88743(6) 0.34472(6) 0.01297(11) Uani 1 1 d . . . . .
H7 H 0.758641 0.967426 0.337667 0.016 Uiso 1 1 calc R U . . .
C8 C 0.86158(8) 0.77641(6) 0.30818(6) 0.01270(10) Uani 1 1 d . . . . .
C9 C 1.03535(8) 0.80767(6) 0.22688(6) 0.01271(10) Uani 1 1 d . . . . .
C10 C 1.17992(9) 0.70664(7) 0.20487(6) 0.01608(12) Uani 1 1 d . . . . .
H10 H 1.166375 0.619287 0.246038 0.019 Uiso 1 1 calc R U . . .
C11 C 1.34153(9) 0.73238(7) 0.12425(7) 0.01824(12) Uani 1 1 d . . . . .
H11 H 1.437816 0.663022 0.111092 0.022 Uiso 1 1 calc R U . . .
C12 C 1.36315(9) 0.85997(8) 0.06235(7) 0.01893(13) Uani 1 1 d . . . . .
H12 H 1.473303 0.877679 0.006016 0.023 Uiso 1 1 calc R U . . .
C13 C 0.87942(9) 0.80219(7) 0.66096(6) 0.01489(11) Uani 1 1 d . . . . .
H13 H 0.991253 0.820171 0.653780 0.018 Uiso 1 1 calc R U . . .
C14 C 0.81742(8) 0.83805(6) 0.56073(6) 0.01369(11) Uani 1 1 d . . . . .
H14 H 0.887994 0.879263 0.485048 0.016 Uiso 1 1 calc R U . . .
C15 C 0.42130(9) 0.86003(6) 0.46443(6) 0.01381(11) Uani 1 1 d . . . . .
C16 C 0.42668(10) 0.89836(7) 0.33547(7) 0.01756(12) Uani 1 1 d . . . . .
H16 H 0.329758 0.907719 0.305629 0.021 Uiso 1 1 calc R U . . .
C17 C 0.58887(10) 0.91766(7) 0.26782(7) 0.01727(12) Uani 1 1 d . . . . .
H17 H 0.623210 0.946696 0.182263 0.021 Uiso 1 1 calc R U . . .
C18 C 1.22248(10) 0.96072(7) 0.08373(7) 0.01911(13) Uani 1 1 d . . . . .
H18 H 1.236946 1.047845 0.042258 0.023 Uiso 1 1 calc R U . . .
C19 C 1.05987(9) 0.93531(7) 0.16562(7) 0.01623(12) Uani 1 1 d . . . . .
H19 H 0.964942 1.005401 0.179883 0.019 Uiso 1 1 calc R U . . .
C20 C 0.82660(9) 0.65611(6) 0.34531(6) 0.01561(12) Uani 1 1 d . . . . .
C21 C 0.78025(9) 0.54007(7) 0.38290(7) 0.01921(13) Uani 1 1 d . . . . .
C22 C 0.71240(11) 0.48639(8) 0.30594(10) 0.02820(18) Uani 1 1 d . . . . .
H22A H 0.712637 0.550085 0.230226 0.042 Uiso 1 1 calc R U . . .
H22B H 0.592045 0.469571 0.350060 0.042 Uiso 1 1 calc R U . . .
H22C H 0.788442 0.404643 0.287516 0.042 Uiso 1 1 calc R U . . .
C23 C 0.79405(12) 0.45452(8) 0.50241(9) 0.02778(17) Uani 1 1 d . . . . .
H23A H 0.886388 0.378762 0.487847 0.042 Uiso 1 1 calc R U . . .
H23B H 0.681203 0.424569 0.548781 0.042 Uiso 1 1 calc R U . . .
H23C H 0.823549 0.504567 0.548362 0.042 Uiso 1 1 calc R U . . .
N1 N 0.59226(7) 0.85093(5) 0.46694(5) 0.01216(10) Uani 1 1 d . . . . .
O1 O 0.99376(8) 0.73710(6) 0.86209(5) 0.02108(11) Uani 1 1 d . . . . .
O2 O 0.76154(9) 0.63772(8) 0.97822(6) 0.02980(14) Uani 1 1 d . . . . .
O3 O 0.29205(7) 0.84292(5) 0.55268(5) 0.01879(11) 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 1.4445(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.2119(10) . ?
C2 O1 1.3437(9) . ?
C2 C3 1.4824(10) . ?
C3 C13 1.3959(10) . ?
C3 C4 1.3979(10) . ?
C4 C5 1.3868(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.4036(9) . ?
C5 H5 0.9500 . ?
C6 C14 1.4015(9) . ?
C6 N1 1.4058(8) . ?
C7 N1 1.4642(8) . ?
C7 C17 1.5021(10) . ?
C7 C8 1.5359(9) . ?
C7 H7 1.0000 . ?
C8 C20 1.3168(9) . ?
C8 C9 1.4803(9) . ?
C9 C19 1.3982(9) . ?
C9 C10 1.4081(9) . ?
C10 C11 1.3852(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.3949(11) . ?
C11 H11 0.9500 . ?
C12 C18 1.3866(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.3870(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O3 1.2237(8) . ?
C15 N1 1.3887(8) . ?
C15 C16 1.4776(10) . ?
C16 C17 1.3299(11) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.3955(10) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.3077(9) . ?
C21 C23 1.5062(12) . ?
C21 C22 1.5082(12) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.09(7) . . ?
O2 C2 C3 124.65(7) . . ?
O1 C2 C3 112.26(6) . . ?
C13 C3 C4 119.10(6) . . ?
C13 C3 C2 122.24(6) . . ?
C4 C3 C2 118.66(6) . . ?
C5 C4 C3 120.95(6) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.92(6) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C14 C6 C5 119.06(6) . . ?
C14 C6 N1 119.46(6) . . ?
C5 C6 N1 121.47(6) . . ?
N1 C7 C17 102.24(5) . . ?
N1 C7 C8 112.79(5) . . ?
C17 C7 C8 110.90(5) . . ?
N1 C7 H7 110.2 . . ?
C17 C7 H7 110.2 . . ?
C8 C7 H7 110.2 . . ?
C20 C8 C9 122.43(6) . . ?
C20 C8 C7 117.64(6) . . ?
C9 C8 C7 119.79(5) . . ?
C19 C9 C10 118.05(6) . . ?
C19 C9 C8 121.90(6) . . ?
C10 C9 C8 119.98(6) . . ?
C11 C10 C9 121.16(6) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.11(7) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C18 C12 C11 119.44(7) . . ?
C18 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C3 120.33(6) . . ?
C14 C13 H13 119.8 . . ?
C3 C13 H13 119.8 . . ?
C13 C14 C6 120.63(6) . . ?
C13 C14 H14 119.7 . . ?
C6 C14 H14 119.7 . . ?
O3 C15 N1 126.12(6) . . ?
O3 C15 C16 127.39(6) . . ?
N1 C15 C16 106.46(6) . . ?
C17 C16 C15 109.13(6) . . ?
C17 C16 H16 125.4 . . ?
C15 C16 H16 125.4 . . ?
C16 C17 C7 110.97(6) . . ?
C16 C17 H17 124.5 . . ?
C7 C17 H17 124.5 . . ?
C12 C18 C19 120.61(7) . . ?
C12 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C9 120.62(6) . . ?
C18 C19 H19 119.7 . . ?
C9 C19 H19 119.7 . . ?
C21 C20 C8 175.98(7) . . ?
C20 C21 C23 122.04(8) . . ?
C20 C21 C22 120.49(8) . . ?
C23 C21 C22 117.47(7) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 N1 C6 126.83(6) . . ?
C15 N1 C7 111.10(5) . . ?
C6 N1 C7 122.07(5) . . ?
C2 O1 C1 115.80(7) . . ?

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1892978'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO, UMR CNRS 8182, Universit? Paris-Sud 11, Universit? Paris-Saclay, FRANCE.
France
;
_audit_update_record             
;
2019-01-23 deposited with the CCDC.	2019-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 N O2, C H2 Cl2'
_chemical_formula_sum            'C27 H25 Cl2 N O2'
_chemical_formula_weight         466.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1480 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                   8.3898(6)
_cell_length_b                   14.8000(9)
_cell_length_c                   18.8914(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.871(2)
_cell_angle_gamma                90
_cell_volume                     2344.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9836
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      35.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.301
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9178
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_process_details   'apex3 BRUKER'
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            102888
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.429
_diffrn_reflns_theta_max         36.436
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11417
_reflns_number_gt                8149
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+1.3625P] 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         11417
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.40239(12) 0.65433(7) 0.43719(5) 0.00920(16) Uani 1 1 d . . . . .
H1 H 0.357110 0.645351 0.484994 0.011 Uiso 1 1 calc R U . . .
C2 C 0.30968(12) 0.59638(7) 0.38138(5) 0.01094(17) Uani 1 1 d . . . . .
H2 H 0.254699 0.547069 0.407313 0.013 Uiso 1 1 calc R U . . .
C3 C 0.44011(13) 0.55267(7) 0.33867(6) 0.01167(17) Uani 1 1 d . . . . .
C4 C 0.59019(12) 0.55845(7) 0.37890(5) 0.01008(16) Uani 1 1 d . . . . .
C5 C 0.56987(12) 0.61511(7) 0.43573(5) 0.00920(16) Uani 1 1 d . . . . .
C6 C 0.73605(12) 0.50925(7) 0.36060(5) 0.01050(17) Uani 1 1 d . . . . .
C7 C 0.77801(14) 0.49943(8) 0.28983(6) 0.0159(2) Uani 1 1 d . . . . .
H7 H 0.713642 0.526509 0.253361 0.019 Uiso 1 1 calc R U . . .
C8 C 0.91277(16) 0.45051(9) 0.27227(7) 0.0204(2) Uani 1 1 d . . . . .
H8 H 0.940007 0.444953 0.224046 0.024 Uiso 1 1 calc R U . . .
C9 C 1.00772(15) 0.40978(9) 0.32472(7) 0.0198(2) Uani 1 1 d . . . . .
H9 H 1.100034 0.376724 0.312671 0.024 Uiso 1 1 calc R U . . .
C10 C 0.96606(14) 0.41793(8) 0.39516(6) 0.0169(2) Uani 1 1 d . . . . .
H10 H 1.029523 0.389594 0.431333 0.020 Uiso 1 1 calc R U . . .
C11 C 0.83228(13) 0.46724(7) 0.41288(6) 0.01283(18) Uani 1 1 d . . . . .
H11 H 0.805628 0.472556 0.461194 0.015 Uiso 1 1 calc R U . . .
C12 C 0.66222(12) 0.69615(7) 0.54312(5) 0.01038(17) Uani 1 1 d . . . . .
C13 C 0.75114(14) 0.77448(8) 0.55533(6) 0.0160(2) Uani 1 1 d . . . . .
H13 H 0.825644 0.794195 0.521813 0.019 Uiso 1 1 calc R U . . .
C14 C 0.72956(15) 0.82356(9) 0.61724(7) 0.0211(2) Uani 1 1 d . . . . .
H14 H 0.790816 0.876571 0.626162 0.025 Uiso 1 1 calc R U . . .
C15 C 0.61930(16) 0.79571(9) 0.66608(7) 0.0208(2) Uani 1 1 d . . . . .
H15 H 0.603208 0.830454 0.707530 0.025 Uiso 1 1 calc R U . . .
C16 C 0.53293(15) 0.71705(9) 0.65405(6) 0.0179(2) Uani 1 1 d . . . . .
H16 H 0.458130 0.697525 0.687499 0.021 Uiso 1 1 calc R U . . .
C17 C 0.55570(13) 0.66667(7) 0.59303(6) 0.01274(18) Uani 1 1 d . . . . .
H17 H 0.498326 0.611989 0.585455 0.015 Uiso 1 1 calc R U . . .
C18 C 0.40712(12) 0.75437(7) 0.41929(5) 0.01056(17) Uani 1 1 d . . . . .
C19 C 0.49377(14) 0.78555(8) 0.36243(6) 0.01474(19) Uani 1 1 d . . . . .
H19 H 0.552548 0.743791 0.335392 0.018 Uiso 1 1 calc R U . . .
C20 C 0.49556(16) 0.87660(8) 0.34469(7) 0.0201(2) Uani 1 1 d . . . . .
H20 H 0.554973 0.896855 0.305785 0.024 Uiso 1 1 calc R U . . .
C21 C 0.41013(17) 0.93776(8) 0.38411(7) 0.0231(2) Uani 1 1 d . . . . .
H21 H 0.411792 1.000197 0.372493 0.028 Uiso 1 1 calc R U . . .
C22 C 0.32241(18) 0.90799(9) 0.44037(7) 0.0239(3) Uani 1 1 d . . . . .
H22 H 0.263157 0.950001 0.466970 0.029 Uiso 1 1 calc R U . . .
C23 C 0.32072(15) 0.81639(8) 0.45816(6) 0.0173(2) Uani 1 1 d . . . . .
H23 H 0.260500 0.796312 0.496875 0.021 Uiso 1 1 calc R U . . .
C24 C 0.18476(13) 0.64401(8) 0.33518(6) 0.01323(18) Uani 1 1 d . . . . .
H24A H 0.235454 0.695666 0.311374 0.016 Uiso 1 1 calc R U . . .
H24B H 0.145662 0.601671 0.297947 0.016 Uiso 1 1 calc R U . . .
C25 C 0.04433(13) 0.67828(8) 0.37502(6) 0.01400(19) Uani 1 1 d . . . . .
C26 C -0.06678(16) 0.74096(10) 0.33520(8) 0.0271(3) Uani 1 1 d . . . . .
H26A H -0.103308 0.712301 0.290806 0.041 Uiso 1 1 calc R U . . .
H26B H -0.010802 0.797265 0.324700 0.041 Uiso 1 1 calc R U . . .
H26C H -0.158834 0.754273 0.364079 0.041 Uiso 1 1 calc R U . . .
C27 C 0.23711(18) 0.57836(12) 0.13314(8) 0.0299(3) Uani 1 1 d . . . . .
H27A H 0.274820 0.555534 0.180012 0.036 Uiso 1 1 calc R U . . .
H27B H 0.330870 0.584692 0.103039 0.036 Uiso 1 1 calc R U . . .
N1 N 0.68679(11) 0.64437(6) 0.48114(5) 0.01158(16) Uani 1 1 d . . . . .
H100 H 0.785637 0.630221 0.471535 0.014 Uiso 1 1 calc R U . . .
O1 O 0.41564(11) 0.51746(6) 0.28041(5) 0.01827(17) Uani 1 1 d . . . . .
O2 O 0.02160(10) 0.65537(6) 0.43585(5) 0.01833(17) Uani 1 1 d . . . . .
Cl1 Cl 0.14637(4) 0.68504(3) 0.14348(2) 0.03162(9) Uani 1 1 d . . . . .
Cl2 Cl 0.10159(5) 0.49966(3) 0.09383(2) 0.03994(11) 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 C18 1.5195(14) . ?
C1 C5 1.5214(14) . ?
C1 C2 1.5488(15) . ?
C1 H1 1.0000 . ?
C2 C24 1.5157(15) . ?
C2 C3 1.5247(14) . ?
C2 H2 1.0000 . ?
C3 O1 1.2289(13) . ?
C3 C4 1.4518(15) . ?
C4 C5 1.3772(14) . ?
C4 C6 1.4748(14) . ?
C5 N1 1.3531(13) . ?
C6 C11 1.4007(15) . ?
C6 C7 1.4011(15) . ?
C7 C8 1.3918(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3886(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3921(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3889(15) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.3904(15) . ?
C12 C13 1.3937(15) . ?
C12 N1 1.4200(13) . ?
C13 C14 1.3937(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3902(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3861(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3913(16) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.3936(15) . ?
C18 C19 1.3950(15) . ?
C19 C20 1.3888(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.3866(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.3970(18) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.5065(15) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O2 1.2192(14) . ?
C25 C26 1.4999(17) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 Cl1 1.7665(17) . ?
C27 Cl2 1.7736(17) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
N1 H100 0.8800 . ?

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
C18 C1 C5 109.69(8) . . ?
C18 C1 C2 113.85(8) . . ?
C5 C1 C2 102.71(8) . . ?
C18 C1 H1 110.1 . . ?
C5 C1 H1 110.1 . . ?
C2 C1 H1 110.1 . . ?
C24 C2 C3 112.79(8) . . ?
C24 C2 C1 117.18(9) . . ?
C3 C2 C1 104.00(8) . . ?
C24 C2 H2 107.5 . . ?
C3 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
O1 C3 C4 127.62(10) . . ?
O1 C3 C2 123.51(10) . . ?
C4 C3 C2 108.85(9) . . ?
C5 C4 C3 108.46(9) . . ?
C5 C4 C6 127.46(10) . . ?
C3 C4 C6 124.07(9) . . ?
N1 C5 C4 125.70(9) . . ?
N1 C5 C1 121.15(9) . . ?
C4 C5 C1 112.60(9) . . ?
C11 C6 C7 118.02(10) . . ?
C11 C6 C4 121.16(9) . . ?
C7 C6 C4 120.75(10) . . ?
C8 C7 C6 120.85(11) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 120.49(11) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.24(11) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.40(11) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 121.00(10) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C17 C12 C13 120.09(10) . . ?
C17 C12 N1 120.24(9) . . ?
C13 C12 N1 119.60(9) . . ?
C12 C13 C14 119.26(11) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.67(11) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.72(11) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.06(11) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.15(10) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C23 C18 C19 118.75(10) . . ?
C23 C18 C1 120.44(9) . . ?
C19 C18 C1 120.78(9) . . ?
C20 C19 C18 121.12(11) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 119.60(11) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 120.11(11) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.23(11) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 120.19(11) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C2 113.97(9) . . ?
C25 C24 H24A 108.8 . . ?
C2 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C2 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
O2 C25 C26 122.07(11) . . ?
O2 C25 C24 121.75(10) . . ?
C26 C25 C24 116.17(10) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
Cl1 C27 Cl2 111.14(8) . . ?
Cl1 C27 H27A 109.4 . . ?
Cl2 C27 H27A 109.4 . . ?
Cl1 C27 H27B 109.4 . . ?
Cl2 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C5 N1 C12 125.01(9) . . ?
C5 N1 H100 117.5 . . ?
C12 N1 H100 117.5 . . ?

_refine_diff_density_max         0.956
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.071



