# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_exp_3321
_database_code_depnum_ccdc_archive 'CCDC 1556054'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 N2 O2'
_chemical_formula_weight         360.44

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           18
_space_group_name_H-M_alt        'P 2 21 21'
_space_group_name_Hall           'P 2bc 2'

_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                   5.7189(11)
_cell_length_b                   12.5306(17)
_cell_length_c                   26.957(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1931.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4688
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4405
_diffrn_reflns_av_unetI/netI     0.1850
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.023
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.845
_reflns_number_total             2871
_reflns_number_gt                1174
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.474
_reflns_Friedel_fraction_max     0.659
_reflns_Friedel_fraction_full    0.659

_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)+10.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 157 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2183
_refine_ls_R_factor_gt           0.1268
_refine_ls_wR_factor_ref         0.3032
_refine_ls_wR_factor_gt          0.2270
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2680(19) 1.0050(6) 0.3083(4) 0.048(3) Uani 1 1 d . . . . .
N1 N 0.450(2) 0.7719(8) 0.2465(5) 0.050(3) Uani 1 1 d . . . . .
O2 O 0.612(2) 1.0992(7) 0.3251(4) 0.056(3) Uani 1 1 d . . . . .
H2 H 0.5812 1.1425 0.3033 0.084 Uiso 1 1 calc R U . . .
N2 N 0.308(2) 0.8615(8) 0.2540(4) 0.046(3) Uani 1 1 d . . . . .
C1 C 0.588(3) 0.7701(10) 0.2878(4) 0.038(4) Uani 1 1 d . . . . .
C4 C 0.405(3) 1.0614(11) 0.3462(5) 0.055(5) Uani 1 1 d . . . . .
C3 C 0.371(3) 0.9102(9) 0.2944(5) 0.043(4) Uani 1 1 d . . . . .
C11 C 0.665(3) 0.8047(11) 0.4067(5) 0.047(4) Uani 1 1 d . . . . .
C2 C 0.540(3) 0.8548(9) 0.3175(5) 0.037(3) Uani 1 1 d . . . . .
C17 C 0.159(3) 0.8960(11) 0.2132(6) 0.044(4) Uani 1 1 d . . . . .
C16 C 0.502(4) 0.7287(12) 0.4134(6) 0.067(6) Uani 1 1 d . . . . .
H16 H 0.3713 0.7280 0.3929 0.081 Uiso 1 1 calc R U . . .
C8 C 0.569(3) 1.0414(11) 0.4326(5) 0.062(5) Uani 1 1 d . . . . .
H8A H 0.6054 0.9904 0.4585 0.075 Uiso 1 1 calc R U . . .
H8B H 0.7117 1.0782 0.4236 0.075 Uiso 1 1 calc R U . . .
C18 C -0.059(3) 0.9435(13) 0.2279(5) 0.055(4) Uani 1 1 d . . . . .
H18 H -0.1036 0.9477 0.2610 0.066 Uiso 1 1 calc R U . . .
C6 C 0.332(4) 1.2035(11) 0.4116(5) 0.076(7) Uani 1 1 d . . . . .
H6A H 0.2130 1.2520 0.4237 0.092 Uiso 1 1 calc R U . . .
H6B H 0.4709 1.2450 0.4040 0.092 Uiso 1 1 calc R U . . .
C21 C 0.065(4) 0.9220(14) 0.1277(6) 0.075(6) Uani 1 1 d . . . . .
H21 H 0.1073 0.9164 0.0945 0.090 Uiso 1 1 calc R U . . .
C22 C 0.213(3) 0.8816(12) 0.1662(5) 0.054(4) Uani 1 1 d . . . . .
H22 H 0.3484 0.8448 0.1580 0.065 Uiso 1 1 calc R U . . .
C10 C 0.635(3) 0.8934(11) 0.3674(5) 0.050(4) Uani 1 1 d . . . . .
H10 H 0.7884 0.9257 0.3615 0.060 Uiso 1 1 calc R U . . .
C7 C 0.390(4) 1.1224(11) 0.4521(6) 0.077(7) Uani 1 1 d . . . . .
H7A H 0.2489 1.0855 0.4622 0.092 Uiso 1 1 calc R U . . .
H7B H 0.4538 1.1589 0.4808 0.092 Uiso 1 1 calc R U . . .
C9 C 0.471(3) 0.9812(10) 0.3864(5) 0.047(4) Uani 1 1 d . . . . .
H9 H 0.3259 0.9461 0.3968 0.056 Uiso 1 1 calc R U . . .
C5 C 0.247(3) 1.1494(10) 0.3654(6) 0.063(5) Uani 1 1 d . . . . .
H5A H 0.2290 1.2028 0.3396 0.076 Uiso 1 1 calc R U . . .
H5B H 0.0936 1.1194 0.3719 0.076 Uiso 1 1 calc R U . . .
C20 C -0.142(4) 0.9694(14) 0.1415(8) 0.076(6) Uani 1 1 d . . . . .
H20 H -0.2440 0.9925 0.1169 0.091 Uiso 1 1 calc R U . . .
C13 C 0.875(5) 0.7265(16) 0.4739(7) 0.095(8) Uani 1 1 d . . . . .
H13 H 1.0026 0.7288 0.4953 0.114 Uiso 1 1 calc R U . . .
C19 C -0.203(3) 0.9838(13) 0.1891(8) 0.079(6) Uani 1 1 d . . . . .
H19 H -0.3401 1.0202 0.1967 0.095 Uiso 1 1 calc R U . . .
C12 C 0.861(4) 0.8042(15) 0.4370(7) 0.084(7) Uani 1 1 d . . . . .
H12 H 0.9799 0.8542 0.4329 0.101 Uiso 1 1 calc R U . . .
C14 C 0.718(5) 0.6491(14) 0.4805(7) 0.090(8) Uani 1 1 d . . . . .
H14 H 0.7391 0.5964 0.5044 0.108 Uiso 1 1 calc R U . . .
C15 C 0.524(4) 0.6505(12) 0.4503(6) 0.073(6) Uani 1 1 d . . . . .
H15 H 0.4073 0.5997 0.4545 0.087 Uiso 1 1 calc R U . . .
C23 C 0.777(3) 0.6821(11) 0.2916(6) 0.066(5) Uani 1 1 d . . . . .
H23A H 0.8984 0.6960 0.2679 0.099 Uiso 1 1 calc R U . . .
H23B H 0.7075 0.6139 0.2848 0.099 Uiso 1 1 calc R U . . .
H23C H 0.8418 0.6819 0.3244 0.099 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.377(15) . ?
O1 C4 1.470(18) . ?
N1 C1 1.361(17) . ?
N1 N2 1.401(14) . ?
O2 C4 1.394(19) . ?
N2 C3 1.300(16) . ?
N2 C17 1.459(18) . ?
C1 C2 1.359(17) . ?
C1 C23 1.55(2) . ?
C4 C5 1.518(19) . ?
C4 C9 1.526(19) . ?
C3 C2 1.34(2) . ?
C11 C16 1.34(2) . ?
C11 C12 1.39(2) . ?
C11 C10 1.545(18) . ?
C2 C10 1.528(19) . ?
C17 C22 1.316(18) . ?
C17 C18 1.44(2) . ?
C16 C15 1.40(2) . ?
C8 C7 1.53(2) . ?
C8 C9 1.559(19) . ?
C18 C19 1.43(2) . ?
C6 C5 1.50(2) . ?
C6 C7 1.527(19) . ?
C21 C20 1.38(3) . ?
C21 C22 1.43(2) . ?
C10 C9 1.533(19) . ?
C20 C19 1.34(2) . ?
C13 C14 1.33(3) . ?
C13 C12 1.39(2) . ?
C14 C15 1.38(3) . ?

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
C3 O1 C4 112.1(12) . . ?
C1 N1 N2 103.3(11) . . ?
C3 N2 N1 109.7(12) . . ?
C3 N2 C17 130.8(12) . . ?
N1 N2 C17 118.1(11) . . ?
C2 C1 N1 110.7(13) . . ?
C2 C1 C23 131.2(13) . . ?
N1 C1 C23 117.9(11) . . ?
O2 C4 O1 109.5(10) . . ?
O2 C4 C5 113.5(12) . . ?
O1 C4 C5 105.6(15) . . ?
O2 C4 C9 107.7(15) . . ?
O1 C4 C9 108.0(11) . . ?
C5 C4 C9 112.5(11) . . ?
N2 C3 C2 110.1(12) . . ?
N2 C3 O1 121.0(14) . . ?
C2 C3 O1 128.8(13) . . ?
C16 C11 C12 118.6(15) . . ?
C16 C11 C10 121.5(15) . . ?
C12 C11 C10 119.9(16) . . ?
C3 C2 C1 105.9(13) . . ?
C3 C2 C10 120.0(12) . . ?
C1 C2 C10 134.1(14) . . ?
C22 C17 C18 121.8(15) . . ?
C22 C17 N2 123.1(14) . . ?
C18 C17 N2 115.0(13) . . ?
C11 C16 C15 121.9(18) . . ?
C7 C8 C9 110.9(15) . . ?
C19 C18 C17 116.4(15) . . ?
C5 C6 C7 111.3(12) . . ?
C20 C21 C22 117.6(17) . . ?
C17 C22 C21 120.7(17) . . ?
C2 C10 C9 107.7(13) . . ?
C2 C10 C11 114.5(12) . . ?
C9 C10 C11 110.9(11) . . ?
C6 C7 C8 109.9(13) . . ?
C4 C9 C10 112.7(11) . . ?
C4 C9 C8 109.7(11) . . ?
C10 C9 C8 113.3(14) . . ?
C6 C5 C4 114.7(16) . . ?
C19 C20 C21 122.7(19) . . ?
C14 C13 C12 124(2) . . ?
C20 C19 C18 120.3(19) . . ?
C11 C12 C13 118.0(19) . . ?
C13 C14 C15 117.1(16) . . ?
C14 C15 C16 120.0(19) . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_rm-vs-2c
_database_code_depnum_ccdc_archive 'CCDC 1556055'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 Cl N2 O2'
_chemical_formula_weight         394.88

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'
Cl Cl 0.1484 0.1585 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.9545(7)
_cell_length_b                   12.1404(9)
_cell_length_c                   28.388(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2052.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4817
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      24.999

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4400
_diffrn_reflns_av_unetI/netI     0.1576
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.356
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_point_group_measured_fraction_full 0.814
_reflns_number_total             2939
_reflns_number_gt                1581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.441
_reflns_Friedel_fraction_max     0.602
_reflns_Friedel_fraction_full    0.602

_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)+(0.0500P)²+20.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2939
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2029
_refine_ls_R_factor_gt           0.1216
_refine_ls_wR_factor_ref         0.3503
_refine_ls_wR_factor_gt          0.2518
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
Cl1 Cl 0.1536(14) 0.0631(4) 0.5136(2) 0.111(3) Uani 1 1 d . . . . .
O1 O 0.7195(19) 0.5688(7) 0.6877(3) 0.045(3) Uani 1 1 d . . . . .
O2 O 0.384(2) 0.6671(8) 0.6758(4) 0.055(3) Uani 1 1 d . . . . .
H2 H 0.4084 0.6706 0.7041 0.082 Uiso 1 1 calc R U . . .
N1 N 0.552(3) 0.3392(9) 0.7546(6) 0.057(4) Uani 1 1 d . . . . .
C2 C 0.449(3) 0.4207(11) 0.6875(5) 0.039(4) Uani 1 1 d . . . . .
C3 C 0.634(3) 0.4775(10) 0.7033(5) 0.039(4) Uani 1 1 d . . . . .
N2 N 0.693(3) 0.4292(9) 0.7431(5) 0.057(4) Uani 1 1 d . . . . .
C4 C 0.561(3) 0.6271(11) 0.6542(6) 0.048(5) Uani 1 1 d . . . . .
C17 C 0.854(2) 0.4637(10) 0.7781(6) 0.038(4) Uani 1 1 d . . . . .
C1 C 0.413(3) 0.3339(10) 0.7174(6) 0.042(4) Uani 1 1 d . . . . .
C14 C 0.212(5) 0.1771(15) 0.5482(9) 0.088(9) Uani 1 1 d . . . . .
C22 C 0.818(4) 0.4464(12) 0.8255(6) 0.063(6) Uani 1 1 d . . . . .
H22 H 0.6871 0.4126 0.8362 0.075 Uiso 1 1 calc R U . . .
C11 C 0.301(3) 0.3547(12) 0.6072(6) 0.047(4) Uani 1 1 d . . . . .
C18 C 1.059(3) 0.5150(12) 0.7639(7) 0.059(5) Uani 1 1 d . . . . .
H18 H 1.0887 0.5232 0.7319 0.071 Uiso 1 1 calc R U . . .
C8 C 0.368(4) 0.6018(12) 0.5757(5) 0.060(6) Uani 1 1 d . . . . .
H8A H 0.3187 0.5489 0.5523 0.072 Uiso 1 1 calc R U . . .
H8B H 0.2368 0.6404 0.5875 0.072 Uiso 1 1 calc R U . . .
C10 C 0.334(3) 0.4536(11) 0.6403(5) 0.045(4) Uani 1 1 d . . . . .
H10 H 0.1876 0.4865 0.6472 0.054 Uiso 1 1 calc R U . . .
C21 C 0.979(4) 0.4803(14) 0.8565(7) 0.066(6) Uani 1 1 d . . . . .
H21 H 0.9604 0.4662 0.8884 0.079 Uiso 1 1 calc R U . . .
C12 C 0.098(3) 0.3453(15) 0.5835(7) 0.060(5) Uani 1 1 d . . . . .
H12 H -0.0103 0.3995 0.5874 0.072 Uiso 1 1 calc R U . . .
C16 C 0.456(4) 0.2780(13) 0.6004(6) 0.059(5) Uani 1 1 d . . . . .
H16 H 0.5964 0.2854 0.6142 0.070 Uiso 1 1 calc R U . . .
C19 C 1.205(3) 0.5507(14) 0.7947(6) 0.060(5) Uani 1 1 d . . . . .
H19 H 1.3346 0.5871 0.7850 0.072 Uiso 1 1 calc R U . . .
C15 C 0.408(4) 0.1858(13) 0.5724(7) 0.061(5) Uani 1 1 d . . . . .
H15 H 0.5137 0.1295 0.5703 0.073 Uiso 1 1 calc R U . . .
C5 C 0.721(4) 0.7174(13) 0.6304(6) 0.073(7) Uani 1 1 d . . . . .
H5A H 0.7652 0.7714 0.6538 0.088 Uiso 1 1 calc R U . . .
H5B H 0.8566 0.6820 0.6188 0.088 Uiso 1 1 calc R U . . .
C9 C 0.486(3) 0.5416(11) 0.6164(5) 0.049(4) Uani 1 1 d . . . . .
H9 H 0.6200 0.5049 0.6040 0.059 Uiso 1 1 calc R U . . .
C23 C 0.225(3) 0.2508(12) 0.7199(6) 0.057(5) Uani 1 1 d . . . . .
H23A H 0.2352 0.2106 0.7490 0.086 Uiso 1 1 calc R U . . .
H23B H 0.2374 0.2005 0.6939 0.086 Uiso 1 1 calc R U . . .
H23C H 0.0833 0.2882 0.7184 0.086 Uiso 1 1 calc R U . . .
C7 C 0.531(4) 0.6841(13) 0.5533(6) 0.079(8) Uani 1 1 d . . . . .
H7A H 0.4593 0.7204 0.5269 0.095 Uiso 1 1 calc R U . . .
H7B H 0.6624 0.6453 0.5416 0.095 Uiso 1 1 calc R U . . .
C13 C 0.053(4) 0.2550(19) 0.5533(9) 0.096(8) Uani 1 1 d . . . . .
H13 H -0.0832 0.2497 0.5375 0.115 Uiso 1 1 calc R U . . .
C6 C 0.606(5) 0.7734(14) 0.5910(6) 0.093(9) Uani 1 1 d . . . . .
H6A H 0.7068 0.8263 0.5765 0.112 Uiso 1 1 calc R U . . .
H6B H 0.4758 0.8126 0.6027 0.112 Uiso 1 1 calc R U . . .
C20 C 1.161(4) 0.5329(15) 0.8419(7) 0.072(6) Uani 1 1 d . . . . .
H20 H 1.2631 0.5587 0.8641 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.732(19) . ?
O1 C3 1.299(17) . ?
O1 C4 1.52(2) . ?
O2 C4 1.31(2) . ?
N1 C1 1.34(2) . ?
N1 N2 1.418(18) . ?
C2 C1 1.371(19) . ?
C2 C3 1.38(2) . ?
C2 C10 1.55(2) . ?
C3 N2 1.321(19) . ?
N2 C17 1.44(2) . ?
C4 C9 1.56(2) . ?
C4 C5 1.60(2) . ?
C17 C22 1.38(2) . ?
C17 C18 1.43(2) . ?
C1 C23 1.51(2) . ?
C14 C13 1.34(3) . ?
C14 C15 1.36(3) . ?
C22 C21 1.36(3) . ?
C11 C16 1.32(2) . ?
C11 C12 1.39(2) . ?
C11 C10 1.538(19) . ?
C18 C19 1.31(2) . ?
C8 C7 1.53(3) . ?
C8 C9 1.54(2) . ?
C10 C9 1.56(2) . ?
C21 C20 1.33(3) . ?
C12 C13 1.42(3) . ?
C16 C15 1.40(2) . ?
C19 C20 1.38(2) . ?
C5 C6 1.48(3) . ?
C7 C6 1.59(2) . ?

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
C3 O1 C4 111.7(12) . . ?
C1 N1 N2 103.0(14) . . ?
C1 C2 C3 107.9(13) . . ?
C1 C2 C10 131.5(14) . . ?
C3 C2 C10 120.4(13) . . ?
O1 C3 N2 124.5(15) . . ?
O1 C3 C2 129.0(13) . . ?
N2 C3 C2 105.8(13) . . ?
C3 N2 N1 112.2(15) . . ?
C3 N2 C17 129.7(13) . . ?
N1 N2 C17 117.5(14) . . ?
O2 C4 O1 112.3(13) . . ?
O2 C4 C9 109.7(15) . . ?
O1 C4 C9 107.4(12) . . ?
O2 C4 C5 115.0(14) . . ?
O1 C4 C5 102.3(14) . . ?
C9 C4 C5 109.7(13) . . ?
C22 C17 C18 118.3(16) . . ?
C22 C17 N2 121.8(16) . . ?
C18 C17 N2 119.9(15) . . ?
N1 C1 C2 110.7(13) . . ?
N1 C1 C23 116.9(15) . . ?
C2 C1 C23 131.3(16) . . ?
C13 C14 C15 119.6(19) . . ?
C13 C14 Cl1 119(2) . . ?
C15 C14 Cl1 121.3(19) . . ?
C21 C22 C17 118(2) . . ?
C16 C11 C12 118.4(15) . . ?
C16 C11 C10 123.3(17) . . ?
C12 C11 C10 118.3(16) . . ?
C19 C18 C17 121.7(19) . . ?
C7 C8 C9 109.3(17) . . ?
C11 C10 C2 112.4(12) . . ?
C11 C10 C9 110.1(13) . . ?
C2 C10 C9 107.3(13) . . ?
C20 C21 C22 121.3(19) . . ?
C11 C12 C13 121.6(18) . . ?
C11 C16 C15 120.4(18) . . ?
C18 C19 C20 118(2) . . ?
C14 C15 C16 121.4(19) . . ?
C6 C5 C4 110.9(19) . . ?
C8 C9 C10 112.8(15) . . ?
C8 C9 C4 109.4(12) . . ?
C10 C9 C4 108.9(12) . . ?
C8 C7 C6 110.1(14) . . ?
C14 C13 C12 118(2) . . ?
C5 C6 C7 109.1(15) . . ?
C21 C20 C19 122(2) . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.126

####################################################################### 
# 
# 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_v-1-4r-100k
_database_code_depnum_ccdc_archive 'CCDC 1556056'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_audit_creation_date             2017-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N2 O3'
_chemical_formula_sum            'C23 H24 N2 O3'
_chemical_formula_weight         376.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H24 N2 O3'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.6633(19)
_cell_length_b                   16.796(2)
_cell_length_c                   9.3590(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.449(16)
_cell_angle_gamma                90
_cell_volume                     1927.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1858
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.3360
_cell_measurement_theta_min      2.7060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.1215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22212
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.859
_diffrn_reflns_theta_min         2.554
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.20   0.30   30.00    --   29.89  54.00 -60.00  624
  2  ω    -69.00 118.20   0.30   30.00    --   29.89  54.00-150.00  624
  3  ω    -69.00  12.00   0.30   30.00    --   29.89  54.00  60.00  270
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0570396000
_diffrn_orient_matrix_UB_12      -0.0029454000
_diffrn_orient_matrix_UB_13      -0.0077253000
_diffrn_orient_matrix_UB_21      0.0085721000
_diffrn_orient_matrix_UB_22      0.0028618000
_diffrn_orient_matrix_UB_23      0.0776813000
_diffrn_orient_matrix_UB_31      -0.0046005000
_diffrn_orient_matrix_UB_32      0.0420190000
_diffrn_orient_matrix_UB_33      -0.0057128000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3391
_reflns_number_total             6770
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         6770
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0664P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1859
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C17(H17), C14(H14), C23(H23), C15(H15), C19(H19), C16(H16),
 C22(H22), C21(H21), C20(H20)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31349(11) 0.39604(8) 0.54188(15) 0.0238(3) Uani 1 1 d . . . . .
O2 O 0.44410(11) 0.54433(8) 0.61858(15) 0.0248(3) Uani 1 1 d . . . . .
O3 O 0.36104(11) 0.36905(8) 0.32266(17) 0.0278(3) Uani 1 1 d . . . . .
H3 H 0.4130 0.3996 0.3475 0.042 Uiso 1 1 calc GR . . . .
N1 N 0.35250(13) 0.54154(9) 0.80614(18) 0.0215(4) Uani 1 1 d . . . . .
N2 N 0.26928(13) 0.49462(10) 0.84158(19) 0.0251(4) Uani 1 1 d . . . . .
C10 C 0.37093(16) 0.52154(11) 0.6728(2) 0.0208(4) Uani 1 1 d . . . . .
C18 C 0.18511(15) 0.59733(11) 0.4925(2) 0.0225(4) Uani 1 1 d . . . . .
C13 C 0.42279(16) 0.57557(11) 1.0659(2) 0.0223(4) Uani 1 1 d . . . . .
H13 H 0.3871 0.5316 1.0921 0.027 Uiso 1 1 calc R . . . .
C9 C 0.22819(16) 0.45013(11) 0.7292(2) 0.0236(4) Uani 1 1 d . . . . .
C2 C 0.24204(16) 0.48208(11) 0.3398(2) 0.0218(4) Uani 1 1 d . . . . .
H2 H 0.3083 0.5131 0.3438 0.026 Uiso 1 1 calc R . . . .
C12 C 0.41541(15) 0.59201(11) 0.9180(2) 0.0208(4) Uani 1 1 d . . . . .
C17 C 0.46698(16) 0.65849(12) 0.8776(2) 0.0249(4) Uani 1 1 d . . . . .
H17 H 0.4597 0.6704 0.7785 0.030 Uiso 1 1 calc R . . . .
C8 C 0.27687(15) 0.46548(11) 0.6007(2) 0.0215(4) Uani 1 1 d . . . . .
C14 C 0.48367(16) 0.62516(12) 1.1739(2) 0.0246(4) Uani 1 1 d . . . . .
H14 H 0.4883 0.6148 1.2729 0.030 Uiso 1 1 calc R . . . .
C1 C 0.27668(16) 0.39519(11) 0.3807(2) 0.0225(4) Uani 1 1 d . . . . .
C7 C 0.19599(15) 0.50879(11) 0.4685(2) 0.0213(4) Uani 1 1 d . . . . .
H7 H 0.1238 0.4846 0.4557 0.026 Uiso 1 1 calc R . . . .
C23 C 0.24575(17) 0.65418(12) 0.4408(2) 0.0278(5) Uani 1 1 d . . . . .
H23 H 0.2930 0.6385 0.3844 0.033 Uiso 1 1 calc R . . . .
C15 C 0.53778(17) 0.69025(12) 1.1347(2) 0.0259(4) Uani 1 1 d . . . . .
H15 H 0.5797 0.7228 1.2074 0.031 Uiso 1 1 calc R . . . .
C6 C 0.18470(16) 0.33526(12) 0.3357(2) 0.0240(4) Uani 1 1 d . . . . .
H6A H 0.1334 0.3428 0.3961 0.029 Uiso 1 1 calc R . . . .
H6B H 0.2142 0.2818 0.3531 0.029 Uiso 1 1 calc R . . . .
C19 C 0.11443(17) 0.62314(12) 0.5760(2) 0.0273(5) Uani 1 1 d . . . . .
H19 H 0.0727 0.5860 0.6112 0.033 Uiso 1 1 calc R . . . .
C16 C 0.52937(17) 0.70679(12) 0.9869(2) 0.0261(4) Uani 1 1 d . . . . .
H16 H 0.5658 0.7505 0.9611 0.031 Uiso 1 1 calc R . . . .
C5 C 0.12497(17) 0.34403(12) 0.1730(2) 0.0273(5) Uani 1 1 d . . . . .
H5A H 0.1752 0.3344 0.1119 0.033 Uiso 1 1 calc R . . . .
H5B H 0.0668 0.3051 0.1475 0.033 Uiso 1 1 calc R . . . .
C22 C 0.23669(19) 0.73472(12) 0.4725(3) 0.0321(5) Uani 1 1 d . . . . .
H22 H 0.2778 0.7722 0.4370 0.038 Uiso 1 1 calc R . . . .
C4 C 0.07753(17) 0.42787(12) 0.1442(2) 0.0276(5) Uani 1 1 d . . . . .
H4A H 0.0248 0.4364 0.2022 0.033 Uiso 1 1 calc R . . . .
H4B H 0.0399 0.4331 0.0408 0.033 Uiso 1 1 calc R . . . .
C3 C 0.16731(17) 0.49083(12) 0.1845(2) 0.0265(5) Uani 1 1 d . . . . .
H3A H 0.1336 0.5431 0.1760 0.032 Uiso 1 1 calc R . . . .
H3B H 0.2115 0.4882 0.1136 0.032 Uiso 1 1 calc R . . . .
C21 C 0.16665(18) 0.75900(12) 0.5566(3) 0.0333(5) Uani 1 1 d . . . . .
H21 H 0.1611 0.8126 0.5784 0.040 Uiso 1 1 calc R . . . .
C20 C 0.10536(18) 0.70316(13) 0.6075(3) 0.0336(5) Uani 1 1 d . . . . .
H20 H 0.0577 0.7191 0.6632 0.040 Uiso 1 1 calc R . . . .
C11 C 0.14042(18) 0.39153(13) 0.7305(2) 0.0324(5) Uani 1 1 d . . . . .
H11A H 0.1279 0.3893 0.8274 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.1621 0.3399 0.7041 0.049 Uiso 1 1 calc GR . . . .
H11C H 0.0746 0.4075 0.6607 0.049 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.416(2) . ?
O1 C1 1.464(2) . ?
O2 C10 1.224(2) . ?
O3 H3 0.8200 . ?
O3 C1 1.385(2) . ?
N1 N2 1.420(2) . ?
N1 C10 1.367(2) . ?
N1 C12 1.426(2) . ?
N2 C9 1.289(3) . ?
C10 C8 1.536(3) . ?
C18 C7 1.515(3) . ?
C18 C23 1.386(3) . ?
C18 C19 1.396(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.391(3) . ?
C13 C14 1.386(3) . ?
C9 C8 1.505(3) . ?
C9 C11 1.487(3) . ?
C2 H2 0.9800 . ?
C2 C1 1.544(3) . ?
C2 C7 1.531(3) . ?
C2 C3 1.531(3) . ?
C12 C17 1.393(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.388(3) . ?
C8 C7 1.573(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C1 C6 1.517(3) . ?
C7 H7 0.9800 . ?
C23 H23 0.9300 . ?
C23 C22 1.396(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.528(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(3) . ?
C16 H16 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.528(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.386(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.529(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C21 H21 0.9300 . ?
C21 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C8 O1 C1 110.96(14) . . ?
C1 O3 H3 109.5 . . ?
N2 N1 C12 118.02(16) . . ?
C10 N1 N2 112.49(16) . . ?
C10 N1 C12 128.66(16) . . ?
C9 N2 N1 107.66(16) . . ?
O2 C10 N1 128.39(18) . . ?
O2 C10 C8 126.44(18) . . ?
N1 C10 C8 105.14(16) . . ?
C23 C18 C7 123.08(18) . . ?
C23 C18 C19 118.02(19) . . ?
C19 C18 C7 118.83(18) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.57(19) . . ?
N2 C9 C8 112.97(17) . . ?
N2 C9 C11 121.86(19) . . ?
C11 C9 C8 125.16(18) . . ?
C1 C2 H2 107.8 . . ?
C7 C2 H2 107.8 . . ?
C7 C2 C1 102.86(15) . . ?
C7 C2 C3 116.91(17) . . ?
C3 C2 H2 107.8 . . ?
C3 C2 C1 113.32(16) . . ?
C13 C12 N1 119.92(17) . . ?
C13 C12 C17 120.65(18) . . ?
C17 C12 N1 119.41(18) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 C12 119.16(19) . . ?
C16 C17 H17 120.4 . . ?
O1 C8 C10 112.48(15) . . ?
O1 C8 C9 114.13(16) . . ?
O1 C8 C7 106.70(15) . . ?
C10 C8 C7 110.07(15) . . ?
C9 C8 C10 100.44(15) . . ?
C9 C8 C7 113.05(16) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
O1 C1 C2 104.10(14) . . ?
O1 C1 C6 108.52(15) . . ?
O3 C1 O1 109.20(15) . . ?
O3 C1 C2 113.68(16) . . ?
O3 C1 C6 107.14(15) . . ?
C6 C1 C2 114.03(16) . . ?
C18 C7 C2 118.07(16) . . ?
C18 C7 C8 113.76(16) . . ?
C18 C7 H7 108.0 . . ?
C2 C7 C8 100.48(15) . . ?
C2 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C18 C23 H23 119.6 . . ?
C18 C23 C22 120.8(2) . . ?
C22 C23 H23 119.6 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.08(19) . . ?
C16 C15 H15 120.0 . . ?
C1 C6 H6A 109.3 . . ?
C1 C6 H6B 109.3 . . ?
C1 C6 C5 111.55(16) . . ?
H6A C6 H6B 108.0 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.38(19) . . ?
C15 C16 H16 119.8 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C4 C5 C6 109.85(17) . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C5 C4 C3 110.99(16) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 C2 114.38(17) . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C22 C21 H21 120.3 . . ?
C20 C21 C22 119.5(2) . . ?
C20 C21 H21 120.3 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.074
_oxdiff_exptl_absorpt_empirical_full_min 0.944
