# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_dd18130_0m
_database_code_depnum_ccdc_archive 'CCDC 1867064'
loop_
_audit_author_name
_audit_author_address
'Mingming Chu' 'Zhejiang University of Technology'
_audit_update_record             
;
2018-09-11 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
3-(4-chlorophenyl)-7-methoxy-3'-methyl-1'-phenyl-3H-spiro[benzofuran-2,4'-pyrazol]-5'(1'H)-one
_chemical_name_common            4-spiropyrazolone
_chemical_melting_point          412
_chemical_formula_moiety         'pyrazolone, phenyl'
_chemical_formula_sum            'C24 H19 Cl N2 O3'
_chemical_formula_weight         418.86

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

_cell_length_a                   5.9309(6)
_cell_length_b                   17.470(2)
_cell_length_c                   19.675(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2038.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7745
_cell_measurement_theta_min      4.663
_cell_measurement_theta_max      53.756

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5341
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19157
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.376
_diffrn_reflns_theta_max         25.493
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3774
_reflns_number_gt                3301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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-2013 (Sheldrick, 2013)'
_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)+(0.0770P)²+0.8588P] 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
_refine_ls_extinction_coef       0.019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.10(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3774
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1624
_refine_ls_wR_factor_gt          0.1544
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
Cl1 Cl -0.0275(3) 0.51352(10) 0.48179(8) 0.0765(6) Uani 1 1 d . . . . .
O1 O 0.3985(7) 0.5244(2) 0.2053(2) 0.0742(13) Uani 1 1 d . . . . .
O2 O 0.3550(6) 0.67204(19) 0.1330(2) 0.0671(12) Uani 1 1 d . . . . .
O3 O 0.6316(6) 0.7996(2) 0.1184(3) 0.0684(12) Uani 1 1 d . . . . .
N1 N 0.0192(7) 0.5333(2) 0.07028(19) 0.0443(9) Uani 1 1 d . . . . .
N2 N 0.1573(6) 0.4938(2) 0.11781(19) 0.0422(9) Uani 1 1 d . . . . .
C1 C 0.2618(7) 0.5416(3) 0.1617(3) 0.0480(12) Uani 1 1 d . . . . .
C2 C 0.1685(8) 0.6209(3) 0.1467(3) 0.0477(11) Uani 1 1 d . . . . .
C3 C 0.0314(8) 0.6052(2) 0.0839(2) 0.0435(10) Uani 1 1 d . . . . .
C4 C -0.0885(12) 0.6631(3) 0.0430(3) 0.0648(16) Uani 1 1 d . . . . .
H4A H -0.1612 0.6382 0.0041 0.097 Uiso 1 1 calc R U . . .
H4B H 0.0193 0.7014 0.0266 0.097 Uiso 1 1 calc R U . . .
H4C H -0.2033 0.6882 0.0711 0.097 Uiso 1 1 calc R U . . .
C5 C 0.0222(8) 0.6596(3) 0.2050(2) 0.0455(11) Uani 1 1 d . . . . .
H5 H -0.1366 0.6641 0.1884 0.055 Uiso 1 1 calc R U . . .
C6 C 0.1238(8) 0.7382(3) 0.2068(2) 0.0456(11) Uani 1 1 d . . . . .
C7 C 0.0637(12) 0.8026(3) 0.2449(2) 0.0609(16) Uani 1 1 d . . . . .
H7 H -0.0639 0.8017 0.2741 0.073 Uiso 1 1 calc R U . . .
C8 C 0.1937(13) 0.8667(3) 0.2390(3) 0.0680(18) Uani 1 1 d . . . . .
H8 H 0.1525 0.9114 0.2635 0.082 Uiso 1 1 calc R U . . .
C9 C 0.3849(12) 0.8684(3) 0.1979(3) 0.0643(17) Uani 1 1 d . . . . .
H9 H 0.4738 0.9136 0.1959 0.077 Uiso 1 1 calc R U . . .
C10 C 0.4475(9) 0.8046(3) 0.1597(3) 0.0524(12) Uani 1 1 d . . . . .
C11 C 0.3123(9) 0.7402(3) 0.1664(3) 0.0499(12) Uani 1 1 d . . . . .
C12 C 0.7524(11) 0.8681(3) 0.1042(4) 0.081(2) Uani 1 1 d . . . . .
H12A H 0.8694 0.8576 0.0703 0.121 Uiso 1 1 calc R U . . .
H12B H 0.8227 0.8870 0.1461 0.121 Uiso 1 1 calc R U . . .
H12C H 0.6483 0.9068 0.0866 0.121 Uiso 1 1 calc R U . . .
C13 C 0.1859(8) 0.4137(2) 0.1088(2) 0.0388(9) Uani 1 1 d . . . . .
C14 C 0.3807(8) 0.3779(3) 0.1316(3) 0.0523(12) Uani 1 1 d . . . . .
H14 H 0.4950 0.4066 0.1539 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4071(10) 0.2995(3) 0.1216(3) 0.0600(14) Uani 1 1 d . . . . .
H15 H 0.5410 0.2748 0.1365 0.072 Uiso 1 1 calc R U . . .
C16 C 0.2403(11) 0.2576(3) 0.0902(3) 0.0592(15) Uani 1 1 d . . . . .
H16 H 0.2583 0.2040 0.0840 0.071 Uiso 1 1 calc R U . . .
C17 C 0.0468(10) 0.2935(3) 0.0678(2) 0.0543(13) Uani 1 1 d . . . . .
H17 H -0.0678 0.2645 0.0461 0.065 Uiso 1 1 calc R U . . .
C18 C 0.0184(8) 0.3719(3) 0.0767(2) 0.0441(10) Uani 1 1 d . . . . .
H18 H -0.1145 0.3965 0.0609 0.053 Uiso 1 1 calc R U . . .
C19 C 0.0182(7) 0.6198(2) 0.2739(2) 0.0428(10) Uani 1 1 d . . . . .
C20 C 0.1974(8) 0.6257(3) 0.3187(3) 0.0465(11) Uani 1 1 d . . . . .
H20 H 0.3293 0.6526 0.3053 0.056 Uiso 1 1 calc R U . . .
C21 C 0.1875(9) 0.5931(3) 0.3831(3) 0.0490(11) Uani 1 1 d . . . . .
H21 H 0.3110 0.5972 0.4136 0.059 Uiso 1 1 calc R U . . .
C22 C -0.0056(9) 0.5545(3) 0.4015(3) 0.0533(12) Uani 1 1 d . . . . .
C23 C -0.1844(9) 0.5474(3) 0.3580(3) 0.0590(14) Uani 1 1 d . . . . .
H23 H -0.3156 0.5202 0.3715 0.071 Uiso 1 1 calc R U . . .
C24 C -0.1724(8) 0.5802(3) 0.2943(3) 0.0548(13) Uani 1 1 d . . . . .
H24 H -0.2966 0.5755 0.2641 0.066 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 C22 1.739(6) . ?
O1 C1 1.217(6) . ?
O2 C11 1.383(5) . ?
O2 C2 1.448(6) . ?
O3 C10 1.365(7) . ?
O3 C12 1.422(7) . ?
N1 C3 1.286(6) . ?
N1 N2 1.422(5) . ?
N2 C1 1.352(6) . ?
N2 C13 1.422(5) . ?
C1 C2 1.520(7) . ?
C2 C3 1.503(7) . ?
C2 C5 1.590(6) . ?
C3 C4 1.476(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.500(7) . ?
C5 C19 1.523(7) . ?
C5 H5 1.0000 . ?
C6 C11 1.372(8) . ?
C6 C7 1.399(6) . ?
C7 C8 1.365(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.385(6) . ?
C13 C14 1.389(7) . ?
C14 C15 1.392(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(7) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.385(7) . ?
C19 C20 1.385(6) . ?
C20 C21 1.389(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.369(8) . ?
C23 C24 1.379(8) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
C11 O2 C2 107.7(4) . . ?
C10 O3 C12 117.8(5) . . ?
C3 N1 N2 107.7(4) . . ?
C1 N2 N1 112.7(4) . . ?
C1 N2 C13 129.3(4) . . ?
N1 N2 C13 117.7(3) . . ?
O1 C1 N2 127.1(5) . . ?
O1 C1 C2 127.2(4) . . ?
N2 C1 C2 105.7(4) . . ?
O2 C2 C3 111.9(4) . . ?
O2 C2 C1 108.7(4) . . ?
C3 C2 C1 101.0(3) . . ?
O2 C2 C5 106.8(3) . . ?
C3 C2 C5 112.1(4) . . ?
C1 C2 C5 116.4(4) . . ?
N1 C3 C4 121.9(4) . . ?
N1 C3 C2 112.3(4) . . ?
C4 C3 C2 125.7(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C19 113.8(4) . . ?
C6 C5 C2 100.8(4) . . ?
C19 C5 C2 117.2(4) . . ?
C6 C5 H5 108.2 . . ?
C19 C5 H5 108.2 . . ?
C2 C5 H5 108.2 . . ?
C11 C6 C7 119.8(5) . . ?
C11 C6 C5 109.7(4) . . ?
C7 C6 C5 130.3(5) . . ?
C8 C7 C6 118.1(6) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C9 121.8(5) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 120.8(5) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
O3 C10 C11 117.8(4) . . ?
O3 C10 C9 125.8(5) . . ?
C11 C10 C9 116.3(5) . . ?
C6 C11 O2 113.7(4) . . ?
C6 C11 C10 123.1(4) . . ?
O2 C11 C10 123.2(5) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 120.4(4) . . ?
C18 C13 N2 119.4(4) . . ?
C14 C13 N2 120.2(4) . . ?
C13 C14 C15 119.4(5) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.4(5) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.9(5) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.5(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 119.3(5) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C24 C19 C20 118.6(5) . . ?
C24 C19 C5 119.9(4) . . ?
C20 C19 C5 121.3(4) . . ?
C19 C20 C21 121.1(4) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 118.4(5) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C23 C22 C21 121.6(5) . . ?
C23 C22 Cl1 118.3(4) . . ?
C21 C22 Cl1 120.2(4) . . ?
C22 C23 C24 119.4(5) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C19 120.9(5) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C1 -1.0(6) . . . . ?
C3 N1 N2 C13 -174.5(4) . . . . ?
N1 N2 C1 O1 -175.8(5) . . . . ?
C13 N2 C1 O1 -3.2(9) . . . . ?
N1 N2 C1 C2 5.6(5) . . . . ?
C13 N2 C1 C2 178.2(5) . . . . ?
C11 O2 C2 C3 112.2(5) . . . . ?
C11 O2 C2 C1 -137.1(4) . . . . ?
C11 O2 C2 C5 -10.7(5) . . . . ?
O1 C1 C2 O2 56.2(7) . . . . ?
N2 C1 C2 O2 -125.3(4) . . . . ?
O1 C1 C2 C3 174.1(5) . . . . ?
N2 C1 C2 C3 -7.4(5) . . . . ?
O1 C1 C2 C5 -64.3(7) . . . . ?
N2 C1 C2 C5 114.2(4) . . . . ?
N2 N1 C3 C4 178.5(5) . . . . ?
N2 N1 C3 C2 -4.4(5) . . . . ?
O2 C2 C3 N1 122.9(4) . . . . ?
C1 C2 C3 N1 7.4(5) . . . . ?
C5 C2 C3 N1 -117.3(5) . . . . ?
O2 C2 C3 C4 -60.2(6) . . . . ?
C1 C2 C3 C4 -175.7(5) . . . . ?
C5 C2 C3 C4 59.7(7) . . . . ?
O2 C2 C5 C6 11.4(5) . . . . ?
C3 C2 C5 C6 -111.4(4) . . . . ?
C1 C2 C5 C6 133.0(4) . . . . ?
O2 C2 C5 C19 -112.6(4) . . . . ?
C3 C2 C5 C19 124.5(4) . . . . ?
C1 C2 C5 C19 8.9(6) . . . . ?
C19 C5 C6 C11 117.9(4) . . . . ?
C2 C5 C6 C11 -8.4(5) . . . . ?
C19 C5 C6 C7 -57.5(7) . . . . ?
C2 C5 C6 C7 176.2(5) . . . . ?
C11 C6 C7 C8 1.7(7) . . . . ?
C5 C6 C7 C8 176.7(5) . . . . ?
C6 C7 C8 C9 -1.8(8) . . . . ?
C7 C8 C9 C10 1.7(9) . . . . ?
C12 O3 C10 C11 171.6(5) . . . . ?
C12 O3 C10 C9 -10.3(8) . . . . ?
C8 C9 C10 O3 -179.4(5) . . . . ?
C8 C9 C10 C11 -1.3(8) . . . . ?
C7 C6 C11 O2 178.4(4) . . . . ?
C5 C6 C11 O2 2.4(6) . . . . ?
C7 C6 C11 C10 -1.6(7) . . . . ?
C5 C6 C11 C10 -177.5(4) . . . . ?
C2 O2 C11 C6 5.6(6) . . . . ?
C2 O2 C11 C10 -174.4(5) . . . . ?
O3 C10 C11 C6 179.6(4) . . . . ?
C9 C10 C11 C6 1.3(7) . . . . ?
O3 C10 C11 O2 -0.3(7) . . . . ?
C9 C10 C11 O2 -178.6(5) . . . . ?
C1 N2 C13 C18 160.3(5) . . . . ?
N1 N2 C13 C18 -27.4(6) . . . . ?
C1 N2 C13 C14 -20.1(8) . . . . ?
N1 N2 C13 C14 152.2(4) . . . . ?
C18 C13 C14 C15 0.4(8) . . . . ?
N2 C13 C14 C15 -179.2(5) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
C14 C15 C16 C17 0.8(8) . . . . ?
C15 C16 C17 C18 -0.1(8) . . . . ?
C14 C13 C18 C17 0.3(7) . . . . ?
N2 C13 C18 C17 179.9(4) . . . . ?
C16 C17 C18 C13 -0.4(7) . . . . ?
C6 C5 C19 C24 136.7(4) . . . . ?
C2 C5 C19 C24 -106.2(5) . . . . ?
C6 C5 C19 C20 -39.7(6) . . . . ?
C2 C5 C19 C20 77.5(5) . . . . ?
C24 C19 C20 C21 -0.2(7) . . . . ?
C5 C19 C20 C21 176.2(4) . . . . ?
C19 C20 C21 C22 -0.1(7) . . . . ?
C20 C21 C22 C23 0.5(7) . . . . ?
C20 C21 C22 Cl1 -179.3(4) . . . . ?
C21 C22 C23 C24 -0.6(7) . . . . ?
Cl1 C22 C23 C24 179.2(4) . . . . ?
C22 C23 C24 C19 0.3(7) . . . . ?
C20 C19 C24 C23 0.1(7) . . . . ?
C5 C19 C24 C23 -176.3(4) . . . . ?

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
C14 H14 O1 0.95 2.36 2.944(6) 119.0 .
C4 H4C O3 0.98 2.37 3.262(7) 151.1 1_455

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and CH3OH'
_chemical_compound_source        synthesis
_chemical_properties_physical    stable
