# 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. 
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data_cd17337
_database_code_depnum_ccdc_archive 'CCDC 1553767'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(2R,3S)-3-(3-chlorophenyl)-3'-methyl-1'-phenyl-3H,4H-spiro[furo[3,2-c]chromene-2,4'-pyrazole]-4,5'(1'H)-dione
_chemical_name_common            
(2R,3S)-3-(3-chlorophenyl)-3'-methyl-1'-phenyl-3H,4H-spiro[furo[3,2-c]chromene-2,4'-pyrazole]-4,5'(1'H)-dione
_chemical_melting_point          130
_chemical_formula_moiety         'C26 H17 Cl N2 O4'
_chemical_formula_sum            'C26 H17 Cl N2 O4'
_chemical_formula_weight         456.86

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.624(3)
_cell_length_b                   9.752(4)
_cell_length_c                   26.737(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2248.6(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2048
_cell_measurement_theta_min      4.444
_cell_measurement_theta_max      40.069

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5280
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11850
_diffrn_reflns_av_unetI/netI     0.0980
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.523
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3970
_reflns_number_gt                2937
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.976

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ', Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1266P)²+9.1062P] 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       0.051(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 939 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.21(9)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3970
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.1238
_refine_ls_wR_factor_ref         0.3136
_refine_ls_wR_factor_gt          0.2984
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.002
_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 -0.6004(5) 0.6293(5) 0.91776(18) 0.0783(16) Uani 1 1 d . . . . .
N1 N 0.0338(12) 0.5142(11) 0.9267(4) 0.042(3) Uani 1 1 d . . . . .
N2 N 0.0859(13) 0.3954(11) 0.9020(4) 0.044(3) Uani 1 1 d . . . . .
O1 O -0.2358(12) 0.4686(11) 0.7013(4) 0.061(3) Uani 1 1 d . . . . .
O2 O -0.0122(8) 0.5397(9) 0.6694(3) 0.036(2) Uani 1 1 d . . . . .
O3 O 0.1410(8) 0.6291(8) 0.8101(3) 0.0322(19) Uani 1 1 d . . . . .
O4 O 0.1605(12) 0.3294(10) 0.8237(3) 0.051(2) Uani 1 1 d . . . . .
C1 C 0.1322(12) 0.6032(12) 0.6740(5) 0.035(3) Uani 1 1 d . . . . .
C2 C 0.2125(16) 0.6245(16) 0.6299(5) 0.048(3) Uani 1 1 d . . . . .
H2 H 0.1714 0.5975 0.5993 0.058 Uiso 1 1 calc R U . . .
C3 C 0.352(2) 0.6855(18) 0.6329(7) 0.072(5) Uani 1 1 d . . . . .
H3 H 0.4059 0.7040 0.6035 0.087 Uiso 1 1 calc R U . . .
C4 C 0.4211(17) 0.7232(16) 0.6802(6) 0.057(4) Uani 1 1 d . . . . .
H4 H 0.5186 0.7635 0.6818 0.068 Uiso 1 1 calc R U . . .
C5 C 0.3380(17) 0.6973(15) 0.7222(5) 0.049(4) Uani 1 1 d . . . . .
H5 H 0.3807 0.7194 0.7531 0.058 Uiso 1 1 calc R U . . .
C6 C 0.1909(12) 0.6386(11) 0.7206(4) 0.029(3) Uani 1 1 d . . . . .
C7 C 0.0984(14) 0.6050(11) 0.7627(4) 0.034(3) Uani 1 1 d . . . . .
C8 C -0.0455(13) 0.5465(13) 0.7574(5) 0.037(3) Uani 1 1 d . . . . .
C9 C -0.1079(14) 0.5176(13) 0.7105(5) 0.039(3) Uani 1 1 d . . . . .
C10 C -0.1169(14) 0.5289(11) 0.8090(5) 0.036(3) Uani 1 1 d . . . . .
H10 H -0.1517 0.4338 0.8128 0.044 Uiso 1 1 calc R U . . .
C11 C 0.0380(15) 0.5502(11) 0.8407(4) 0.035(3) Uani 1 1 d . . . . .
C12 C 0.1058(15) 0.4100(12) 0.8528(4) 0.036(3) Uani 1 1 d . . . . .
C13 C 0.0148(15) 0.6040(14) 0.8925(4) 0.039(3) Uani 1 1 d . . . . .
C14 C -0.029(2) 0.7492(15) 0.9062(5) 0.062(5) Uani 1 1 d . . . . .
H14A H -0.0706 0.7508 0.9395 0.093 Uiso 1 1 calc R U . . .
H14B H -0.1064 0.7822 0.8832 0.093 Uiso 1 1 calc R U . . .
H14C H 0.0607 0.8068 0.9045 0.093 Uiso 1 1 calc R U . . .
C15 C -0.2485(12) 0.6226(12) 0.8209(4) 0.029(2) Uani 1 1 d . . . . .
C16 C -0.3546(13) 0.5887(14) 0.8590(5) 0.041(3) Uani 1 1 d . . . . .
H16 H -0.3461 0.5045 0.8750 0.049 Uiso 1 1 calc R U . . .
C17 C -0.4691(14) 0.6767(14) 0.8728(5) 0.044(3) Uani 1 1 d . . . . .
C18 C -0.4895(16) 0.7999(13) 0.8473(6) 0.049(3) Uani 1 1 d . . . . .
H18 H -0.5680 0.8601 0.8566 0.059 Uiso 1 1 calc R U . . .
C19 C -0.3923(15) 0.8314(12) 0.8083(5) 0.040(3) Uani 1 1 d . . . . .
H19 H -0.4092 0.9106 0.7897 0.048 Uiso 1 1 calc R U . . .
C20 C -0.2678(14) 0.7451(13) 0.7963(4) 0.036(3) Uani 1 1 d . . . . .
H20 H -0.1979 0.7709 0.7715 0.043 Uiso 1 1 calc R U . . .
C21 C 0.1168(17) 0.2769(13) 0.9332(5) 0.045(3) Uani 1 1 d . . . . .
C22 C 0.2173(14) 0.1763(13) 0.9167(4) 0.037(3) Uani 1 1 d . . . . .
H22 H 0.2708 0.1872 0.8868 0.045 Uiso 1 1 calc R U . . .
C23 C 0.238(2) 0.0573(14) 0.9456(5) 0.061(5) Uani 1 1 d . . . . .
H23 H 0.3013 -0.0131 0.9341 0.074 Uiso 1 1 calc R U . . .
C24 C 0.165(3) 0.0458(17) 0.9901(7) 0.087(7) Uani 1 1 d . . . . .
H24 H 0.1855 -0.0295 1.0104 0.104 Uiso 1 1 calc R U . . .
C25 C 0.057(2) 0.147(2) 1.0066(6) 0.076(5) Uani 1 1 d . . . . .
H25 H 0.0018 0.1362 1.0362 0.091 Uiso 1 1 calc R U . . .
C26 C 0.038(2) 0.2611(15) 0.9773(5) 0.059(4) Uani 1 1 d . . . . .
H26 H -0.0298 0.3294 0.9876 0.071 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 C17 1.715(13) . ?
N1 C13 1.278(16) . ?
N1 N2 1.408(14) . ?
N2 C12 1.334(15) . ?
N2 C21 1.450(16) . ?
O1 C9 1.227(15) . ?
O2 C9 1.391(14) . ?
O2 C1 1.396(14) . ?
O3 C7 1.341(13) . ?
O3 C11 1.431(14) . ?
O4 C12 1.201(14) . ?
C1 C2 1.382(18) . ?
C1 C6 1.389(16) . ?
C2 C3 1.34(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.45(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.418(16) . ?
C7 C8 1.374(17) . ?
C8 C9 1.395(17) . ?
C8 C10 1.519(17) . ?
C10 C15 1.492(16) . ?
C10 C11 1.596(17) . ?
C10 H10 0.9800 . ?
C11 C13 1.495(17) . ?
C11 C12 1.522(16) . ?
C13 C14 1.511(18) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.374(17) . ?
C15 C16 1.408(16) . ?
C16 C17 1.359(17) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(19) . ?
C18 C19 1.373(19) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(17) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.37(2) . ?
C21 C22 1.382(17) . ?
C22 C23 1.405(18) . ?
C22 H22 0.9300 . ?
C23 C24 1.35(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.43(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.37(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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
C13 N1 N2 105.5(9) . . ?
C12 N2 N1 114.6(10) . . ?
C12 N2 C21 129.0(11) . . ?
N1 N2 C21 116.3(10) . . ?
C9 O2 C1 121.8(9) . . ?
C7 O3 C11 106.0(9) . . ?
C2 C1 C6 123.0(11) . . ?
C2 C1 O2 115.9(11) . . ?
C6 C1 O2 121.0(10) . . ?
C3 C2 C1 117.7(14) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 122.1(15) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 117.4(14) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C4 C5 C6 122.3(14) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 117.4(11) . . ?
C1 C6 C7 116.7(10) . . ?
C5 C6 C7 125.8(11) . . ?
O3 C7 C8 114.7(10) . . ?
O3 C7 C6 123.8(11) . . ?
C8 C7 C6 121.5(11) . . ?
C7 C8 C9 121.7(11) . . ?
C7 C8 C10 108.6(11) . . ?
C9 C8 C10 129.6(11) . . ?
O1 C9 O2 115.9(11) . . ?
O1 C9 C8 127.2(12) . . ?
O2 C9 C8 116.8(10) . . ?
C15 C10 C8 115.6(10) . . ?
C15 C10 C11 116.3(9) . . ?
C8 C10 C11 97.4(9) . . ?
C15 C10 H10 109.0 . . ?
C8 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
O3 C11 C13 115.0(11) . . ?
O3 C11 C12 111.5(9) . . ?
C13 C11 C12 99.8(9) . . ?
O3 C11 C10 106.7(8) . . ?
C13 C11 C10 115.2(10) . . ?
C12 C11 C10 108.5(10) . . ?
O4 C12 N2 128.2(12) . . ?
O4 C12 C11 126.9(11) . . ?
N2 C12 C11 104.8(10) . . ?
N1 C13 C11 114.0(11) . . ?
N1 C13 C14 120.1(10) . . ?
C11 C13 C14 125.9(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.1(11) . . ?
C20 C15 C10 121.5(10) . . ?
C16 C15 C10 120.3(10) . . ?
C17 C16 C15 121.4(12) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.3(12) . . ?
C16 C17 Cl1 120.0(11) . . ?
C18 C17 Cl1 119.4(10) . . ?
C19 C18 C17 119.2(11) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 120.5(11) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 120.4(11) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C26 C21 C22 120.4(12) . . ?
C26 C21 N2 119.7(12) . . ?
C22 C21 N2 119.8(11) . . ?
C21 C22 C23 119.3(12) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 119.6(15) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 121.2(14) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 117.6(16) . . ?
C26 C25 H25 121.2 . . ?
C24 C25 H25 121.2 . . ?
C21 C26 C25 121.7(16) . . ?
C21 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?

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
C13 N1 N2 C12 2.4(15) . . . . ?
C13 N1 N2 C21 179.8(12) . . . . ?
C9 O2 C1 C2 -177.2(11) . . . . ?
C9 O2 C1 C6 4.4(15) . . . . ?
C6 C1 C2 C3 -2(2) . . . . ?
O2 C1 C2 C3 180.0(12) . . . . ?
C1 C2 C3 C4 3(2) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
C2 C1 C6 C5 -0.4(17) . . . . ?
O2 C1 C6 C5 177.8(11) . . . . ?
C2 C1 C6 C7 -177.2(12) . . . . ?
O2 C1 C6 C7 1.1(15) . . . . ?
C4 C5 C6 C1 1.8(19) . . . . ?
C4 C5 C6 C7 178.2(13) . . . . ?
C11 O3 C7 C8 15.8(13) . . . . ?
C11 O3 C7 C6 -165.4(10) . . . . ?
C1 C6 C7 O3 178.1(10) . . . . ?
C5 C6 C7 O3 1.7(19) . . . . ?
C1 C6 C7 C8 -3.2(16) . . . . ?
C5 C6 C7 C8 -179.6(12) . . . . ?
O3 C7 C8 C9 178.6(11) . . . . ?
C6 C7 C8 C9 -0.2(18) . . . . ?
O3 C7 C8 C10 1.2(14) . . . . ?
C6 C7 C8 C10 -177.6(10) . . . . ?
C1 O2 C9 O1 175.7(11) . . . . ?
C1 O2 C9 C8 -7.6(16) . . . . ?
C7 C8 C9 O1 -178.3(13) . . . . ?
C10 C8 C9 O1 -1(2) . . . . ?
C7 C8 C9 O2 5.4(18) . . . . ?
C10 C8 C9 O2 -177.6(11) . . . . ?
C7 C8 C10 C15 108.6(12) . . . . ?
C9 C8 C10 C15 -68.6(16) . . . . ?
C7 C8 C10 C11 -15.3(11) . . . . ?
C9 C8 C10 C11 167.5(13) . . . . ?
C7 O3 C11 C13 -154.3(10) . . . . ?
C7 O3 C11 C12 93.0(11) . . . . ?
C7 O3 C11 C10 -25.2(11) . . . . ?
C15 C10 C11 O3 -99.2(11) . . . . ?
C8 C10 C11 O3 24.2(11) . . . . ?
C15 C10 C11 C13 29.8(14) . . . . ?
C8 C10 C11 C13 153.2(10) . . . . ?
C15 C10 C11 C12 140.6(10) . . . . ?
C8 C10 C11 C12 -96.0(10) . . . . ?
N1 N2 C12 O4 173.4(13) . . . . ?
C21 N2 C12 O4 -4(2) . . . . ?
N1 N2 C12 C11 -8.7(14) . . . . ?
C21 N2 C12 C11 174.3(13) . . . . ?
O3 C11 C12 O4 -49.7(17) . . . . ?
C13 C11 C12 O4 -171.7(13) . . . . ?
C10 C11 C12 O4 67.4(16) . . . . ?
O3 C11 C12 N2 132.4(11) . . . . ?
C13 C11 C12 N2 10.4(13) . . . . ?
C10 C11 C12 N2 -110.5(11) . . . . ?
N2 N1 C13 C11 5.4(15) . . . . ?
N2 N1 C13 C14 -175.3(13) . . . . ?
O3 C11 C13 N1 -129.4(12) . . . . ?
C12 C11 C13 N1 -10.1(15) . . . . ?
C10 C11 C13 N1 105.9(12) . . . . ?
O3 C11 C13 C14 51.4(18) . . . . ?
C12 C11 C13 C14 170.8(14) . . . . ?
C10 C11 C13 C14 -73.3(17) . . . . ?
C8 C10 C15 C20 -22.5(15) . . . . ?
C11 C10 C15 C20 90.8(13) . . . . ?
C8 C10 C15 C16 159.2(11) . . . . ?
C11 C10 C15 C16 -87.5(13) . . . . ?
C20 C15 C16 C17 -2.8(18) . . . . ?
C10 C15 C16 C17 175.5(12) . . . . ?
C15 C16 C17 C18 4(2) . . . . ?
C15 C16 C17 Cl1 177.7(10) . . . . ?
C16 C17 C18 C19 0(2) . . . . ?
Cl1 C17 C18 C19 -174.1(11) . . . . ?
C17 C18 C19 C20 -4(2) . . . . ?
C16 C15 C20 C19 -1.5(17) . . . . ?
C10 C15 C20 C19 -179.8(11) . . . . ?
C18 C19 C20 C15 5.0(19) . . . . ?
C12 N2 C21 C26 -155.3(15) . . . . ?
N1 N2 C21 C26 27.8(19) . . . . ?
C12 N2 C21 C22 20(2) . . . . ?
N1 N2 C21 C22 -156.7(12) . . . . ?
C26 C21 C22 C23 0(2) . . . . ?
N2 C21 C22 C23 -175.4(13) . . . . ?
C21 C22 C23 C24 -3(2) . . . . ?
C22 C23 C24 C25 5(3) . . . . ?
C23 C24 C25 C26 -4(3) . . . . ?
C22 C21 C26 C25 1(3) . . . . ?
N2 C21 C26 C25 176.2(16) . . . . ?
C24 C25 C26 C21 1(3) . . . . ?

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
C18 H18 O1 0.93 2.53 3.164(17) 126.0 4_456
C22 H22 O4 0.93 2.38 2.942(15) 118.6 .

_refine_diff_density_max         0.589
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.158

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
_chemical_compound_source        'organic synthesis'
_chemical_properties_physical    ', Heat-sensitive'
_exptl_crystal_preparation       ', Magnetic properties'
####################################################################### 
# 
# 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_cd16536
_database_code_depnum_ccdc_archive 'CCDC 1509834'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(2R,3S)-3-(3-bromophenyl)-3'-methyl-1'-phenyl-3H,4H-spiro[furo[3,2-c]chromene-2,4'-pyrazole]-4,5'(1'H)-dione
_chemical_name_common            'Annulated hydroxycoumarin'
_chemical_melting_point          165.4
_chemical_formula_moiety         C26H17BrN2O4
_chemical_formula_sum            'C27 H19 Br Cl2 N2 O4'
_chemical_formula_weight         586.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_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'

_cell_length_a                   8.743(2)
_cell_length_b                   9.675(3)
_cell_length_c                   15.147(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.291(6)
_cell_angle_gamma                90
_cell_volume                     1277.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1185
_cell_measurement_theta_min      5.000
_cell_measurement_theta_max      40.736

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.855
_shelx_estimated_absorpt_T_min   0.708
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5635
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7093
_diffrn_reflns_av_unetI/netI     0.1144
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.336
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.922
_reflns_number_total             4277
_reflns_number_gt                2752
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    0.864

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0432P)²+0.0569P] 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 918 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.041(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4277
_refine_ls_number_parameters     326
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
Br1 Br 0.36240(10) 0.44272(17) 0.19306(8) 0.0935(5) Uani 1 1 d . . . . .
Cl1 Cl 0.4128(7) 0.2239(10) 0.9397(4) 0.196(3) Uani 1 1 d . . . . .
Cl2 Cl 0.6341(10) 0.1227(9) 1.0666(5) 0.237(4) Uani 1 1 d . . . . .
N1 N 1.0475(7) 0.6661(7) 0.2320(4) 0.0430(17) Uani 1 1 d . . . . .
N2 N 0.9909(7) 0.5445(8) 0.1900(5) 0.0466(18) Uani 1 1 d . . . . .
O1 O 0.7806(8) 0.5875(8) 0.5897(4) 0.0666(19) Uani 1 1 d . . . . .
O2 O 1.0083(6) 0.5141(6) 0.6445(3) 0.0482(15) Uani 1 1 d . . . . .
O3 O 1.1237(5) 0.4297(6) 0.3946(3) 0.0417(12) Uani 1 1 d . . . . .
O4 O 1.1433(7) 0.7290(6) 0.3730(4) 0.0549(16) Uani 1 1 d . . . . .
C1 C 1.1485(8) 0.4506(11) 0.6352(5) 0.0440(18) Uani 1 1 d . . . . .
C2 C 1.2406(9) 0.4291(12) 0.7112(5) 0.055(2) Uani 1 1 d . . . . .
H2 H 1.2076 0.4528 0.7662 0.066 Uiso 1 1 calc R U . . .
C3 C 1.3832(10) 0.3715(11) 0.7041(6) 0.060(3) Uani 1 1 d . . . . .
H3 H 1.4473 0.3566 0.7550 0.072 Uiso 1 1 calc R U . . .
C4 C 1.4326(10) 0.3357(11) 0.6233(7) 0.058(3) Uani 1 1 d . . . . .
H4 H 1.5287 0.2958 0.6200 0.070 Uiso 1 1 calc R U . . .
C5 C 1.3406(9) 0.3586(10) 0.5473(6) 0.050(2) Uani 1 1 d . . . . .
H5 H 1.3743 0.3347 0.4925 0.060 Uiso 1 1 calc R U . . .
C6 C 1.1971(8) 0.4176(9) 0.5527(5) 0.041(2) Uani 1 1 d . . . . .
C7 C 1.0905(7) 0.4520(10) 0.4801(4) 0.0369(17) Uani 1 1 d . . . . .
C8 C 0.9555(9) 0.5108(9) 0.4882(5) 0.0401(19) Uani 1 1 d . . . . .
C9 C 0.9009(10) 0.5414(9) 0.5732(6) 0.048(2) Uani 1 1 d . . . . .
C10 C 0.8722(8) 0.5337(9) 0.3994(5) 0.0403(19) Uani 1 1 d . . . . .
H10 H 0.8398 0.6305 0.3940 0.048 Uiso 1 1 calc R U . . .
C11 C 1.0119(8) 0.5079(8) 0.3408(5) 0.0361(19) Uani 1 1 d . . . . .
C12 C 1.0800(9) 0.6494(9) 0.3203(5) 0.0402(19) Uani 1 1 d . . . . .
C13 C 0.9773(7) 0.4532(11) 0.2499(5) 0.0418(18) Uani 1 1 d . . . . .
C14 C 0.9389(12) 0.3068(11) 0.2289(7) 0.063(3) Uani 1 1 d . . . . .
H14A H 0.9324 0.2939 0.1658 0.094 Uiso 1 1 calc R U . . .
H14B H 0.8421 0.2841 0.2512 0.094 Uiso 1 1 calc R U . . .
H14C H 1.0173 0.2477 0.2559 0.094 Uiso 1 1 calc R U . . .
C15 C 1.0786(10) 0.7837(9) 0.1785(6) 0.046(2) Uani 1 1 d . . . . .
C16 C 1.1873(11) 0.8786(10) 0.2077(6) 0.056(2) Uani 1 1 d . . . . .
H16 H 1.2431 0.8679 0.2620 0.067 Uiso 1 1 calc R U . . .
C17 C 1.2113(15) 0.9906(12) 0.1540(9) 0.088(4) Uani 1 1 d . . . . .
H17 H 1.2823 1.0573 0.1738 0.105 Uiso 1 1 calc R U . . .
C18 C 1.136(2) 1.0067(15) 0.0744(10) 0.107(5) Uani 1 1 d . . . . .
H18 H 1.1569 1.0820 0.0390 0.128 Uiso 1 1 calc R U . . .
C19 C 1.0274(17) 0.9105(17) 0.0454(7) 0.100(5) Uani 1 1 d . . . . .
H19 H 0.9726 0.9221 -0.0091 0.120 Uiso 1 1 calc R U . . .
C20 C 0.9994(12) 0.7963(12) 0.0972(7) 0.071(3) Uani 1 1 d . . . . .
H20 H 0.9284 0.7296 0.0772 0.085 Uiso 1 1 calc R U . . .
C21 C 0.7346(7) 0.4390(10) 0.3762(5) 0.0393(17) Uani 1 1 d . . . . .
C22 C 0.6286(8) 0.4755(10) 0.3089(5) 0.048(2) Uani 1 1 d . . . . .
H22 H 0.6389 0.5585 0.2790 0.057 Uiso 1 1 calc R U . . .
C23 C 0.5076(9) 0.3897(10) 0.2857(6) 0.052(3) Uani 1 1 d . . . . .
C24 C 0.4899(10) 0.2658(10) 0.3281(6) 0.055(2) Uani 1 1 d . . . . .
H24 H 0.4086 0.2071 0.3114 0.066 Uiso 1 1 calc R U . . .
C25 C 0.5955(10) 0.2315(10) 0.3955(7) 0.056(2) Uani 1 1 d . . . . .
H25 H 0.5839 0.1490 0.4259 0.068 Uiso 1 1 calc R U . . .
C26 C 0.7174(9) 0.3144(9) 0.4198(6) 0.048(2) Uani 1 1 d . . . . .
H26 H 0.7887 0.2877 0.4652 0.057 Uiso 1 1 calc R U . . .
C27 C 0.582(2) 0.247(2) 0.9966(14) 0.161(8) Uani 1 1 d . . . . .
H27A H 0.6598 0.2576 0.9549 0.193 Uiso 1 1 calc R U . . .
H27B H 0.5776 0.3332 1.0294 0.193 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
Br1 C23 1.891(9) . ?
Cl1 C27 1.67(2) . ?
Cl2 C27 1.65(2) . ?
N1 C12 1.356(10) . ?
N1 N2 1.410(10) . ?
N1 C15 1.435(11) . ?
N2 C13 1.278(11) . ?
O1 C9 1.186(10) . ?
O2 C1 1.387(10) . ?
O2 C9 1.403(10) . ?
O3 C7 1.366(8) . ?
O3 C11 1.440(9) . ?
O4 C12 1.213(10) . ?
C1 C2 1.370(10) . ?
C1 C6 1.387(10) . ?
C2 C3 1.377(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.427(10) . ?
C7 C8 1.324(10) . ?
C8 C9 1.437(12) . ?
C8 C10 1.497(11) . ?
C10 C21 1.532(11) . ?
C10 C11 1.582(10) . ?
C10 H10 0.9800 . ?
C11 C13 1.484(11) . ?
C11 C12 1.534(12) . ?
C13 C14 1.485(15) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.371(13) . ?
C15 C20 1.372(12) . ?
C16 C17 1.380(14) . ?
C16 H16 0.9300 . ?
C17 C18 1.339(18) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(19) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(17) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.371(10) . ?
C21 C26 1.387(13) . ?
C22 C23 1.369(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(13) . ?
C24 C25 1.365(13) . ?
C24 H24 0.9300 . ?
C25 C26 1.362(13) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 N2 112.7(7) . . ?
C12 N1 C15 128.1(7) . . ?
N2 N1 C15 118.8(7) . . ?
C13 N2 N1 107.7(7) . . ?
C1 O2 C9 123.4(6) . . ?
C7 O3 C11 105.7(5) . . ?
C2 C1 C6 121.4(8) . . ?
C2 C1 O2 116.7(7) . . ?
C6 C1 O2 121.7(6) . . ?
C1 C2 C3 118.3(8) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 121.3(8) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.3(8) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.5(8) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.2(7) . . ?
C5 C6 C7 126.3(7) . . ?
C1 C6 C7 114.4(7) . . ?
C8 C7 O3 114.2(6) . . ?
C8 C7 C6 124.4(7) . . ?
O3 C7 C6 121.4(6) . . ?
C7 C8 C9 122.0(8) . . ?
C7 C8 C10 111.0(7) . . ?
C9 C8 C10 127.0(7) . . ?
O1 C9 O2 117.5(8) . . ?
O1 C9 C8 128.8(9) . . ?
O2 C9 C8 113.7(7) . . ?
C8 C10 C21 116.0(7) . . ?
C8 C10 C11 97.9(6) . . ?
C21 C10 C11 113.8(6) . . ?
C8 C10 H10 109.6 . . ?
C21 C10 H10 109.6 . . ?
C11 C10 H10 109.6 . . ?
O3 C11 C13 114.8(7) . . ?
O3 C11 C12 109.0(6) . . ?
C13 C11 C12 100.7(6) . . ?
O3 C11 C10 106.6(6) . . ?
C13 C11 C10 117.7(6) . . ?
C12 C11 C10 107.4(6) . . ?
O4 C12 N1 128.7(8) . . ?
O4 C12 C11 126.8(7) . . ?
N1 C12 C11 104.5(7) . . ?
N2 C13 C11 112.9(8) . . ?
N2 C13 C14 122.5(8) . . ?
C11 C13 C14 124.5(8) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 121.4(9) . . ?
C16 C15 N1 120.3(8) . . ?
C20 C15 N1 118.3(8) . . ?
C15 C16 C17 117.9(10) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C18 C17 C16 122.5(13) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 C19 119.2(12) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 120.4(11) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 118.6(12) . . ?
C15 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C21 C26 119.1(8) . . ?
C22 C21 C10 119.5(8) . . ?
C26 C21 C10 121.4(7) . . ?
C23 C22 C21 120.1(9) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 121.3(8) . . ?
C22 C23 Br1 119.3(7) . . ?
C24 C23 Br1 119.4(7) . . ?
C25 C24 C23 117.9(8) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
C26 C25 C24 122.0(9) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C25 C26 C21 119.6(8) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
Cl2 C27 Cl1 115.2(13) . . ?
Cl2 C27 H27A 108.5 . . ?
Cl1 C27 H27A 108.5 . . ?
Cl2 C27 H27B 108.5 . . ?
Cl1 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?

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
C12 N1 N2 C13 4.0(9) . . . . ?
C15 N1 N2 C13 177.7(7) . . . . ?
C9 O2 C1 C2 -179.1(8) . . . . ?
C9 O2 C1 C6 4.5(12) . . . . ?
C6 C1 C2 C3 -0.9(15) . . . . ?
O2 C1 C2 C3 -177.4(9) . . . . ?
C1 C2 C3 C4 -0.3(16) . . . . ?
C2 C3 C4 C5 0.9(15) . . . . ?
C3 C4 C5 C6 -0.3(14) . . . . ?
C4 C5 C6 C1 -0.9(12) . . . . ?
C4 C5 C6 C7 177.8(8) . . . . ?
C2 C1 C6 C5 1.5(13) . . . . ?
O2 C1 C6 C5 177.8(8) . . . . ?
C2 C1 C6 C7 -177.3(9) . . . . ?
O2 C1 C6 C7 -1.1(12) . . . . ?
C11 O3 C7 C8 12.9(9) . . . . ?
C11 O3 C7 C6 -165.3(7) . . . . ?
C5 C6 C7 C8 -178.7(9) . . . . ?
C1 C6 C7 C8 0.1(12) . . . . ?
C5 C6 C7 O3 -0.7(13) . . . . ?
C1 C6 C7 O3 178.1(7) . . . . ?
O3 C7 C8 C9 179.6(7) . . . . ?
C6 C7 C8 C9 -2.3(13) . . . . ?
O3 C7 C8 C10 1.6(10) . . . . ?
C6 C7 C8 C10 179.7(8) . . . . ?
C1 O2 C9 O1 175.0(8) . . . . ?
C1 O2 C9 C8 -6.2(10) . . . . ?
C7 C8 C9 O1 -176.2(10) . . . . ?
C10 C8 C9 O1 1.5(15) . . . . ?
C7 C8 C9 O2 5.0(11) . . . . ?
C10 C8 C9 O2 -177.2(7) . . . . ?
C7 C8 C10 C21 107.7(8) . . . . ?
C9 C8 C10 C21 -70.2(10) . . . . ?
C7 C8 C10 C11 -13.6(8) . . . . ?
C9 C8 C10 C11 168.5(8) . . . . ?
C7 O3 C11 C13 -153.1(6) . . . . ?
C7 O3 C11 C12 94.7(7) . . . . ?
C7 O3 C11 C10 -21.0(8) . . . . ?
C8 C10 C11 O3 20.5(7) . . . . ?
C21 C10 C11 O3 -102.4(7) . . . . ?
C8 C10 C11 C13 151.1(7) . . . . ?
C21 C10 C11 C13 28.2(10) . . . . ?
C8 C10 C11 C12 -96.2(7) . . . . ?
C21 C10 C11 C12 140.8(7) . . . . ?
N2 N1 C12 O4 172.2(8) . . . . ?
C15 N1 C12 O4 -0.8(14) . . . . ?
N2 N1 C12 C11 -10.2(8) . . . . ?
C15 N1 C12 C11 176.8(7) . . . . ?
O3 C11 C12 O4 -49.5(10) . . . . ?
C13 C11 C12 O4 -170.7(8) . . . . ?
C10 C11 C12 O4 65.6(10) . . . . ?
O3 C11 C12 N1 132.8(6) . . . . ?
C13 C11 C12 N1 11.7(7) . . . . ?
C10 C11 C12 N1 -112.0(7) . . . . ?
N1 N2 C13 C11 4.7(8) . . . . ?
N1 N2 C13 C14 -172.2(7) . . . . ?
O3 C11 C13 N2 -127.3(7) . . . . ?
C12 C11 C13 N2 -10.3(8) . . . . ?
C10 C11 C13 N2 106.0(8) . . . . ?
O3 C11 C13 C14 49.6(10) . . . . ?
C12 C11 C13 C14 166.6(7) . . . . ?
C10 C11 C13 C14 -77.1(10) . . . . ?
C12 N1 C15 C16 19.8(12) . . . . ?
N2 N1 C15 C16 -152.9(8) . . . . ?
C12 N1 C15 C20 -161.7(8) . . . . ?
N2 N1 C15 C20 25.7(11) . . . . ?
C20 C15 C16 C17 2.2(14) . . . . ?
N1 C15 C16 C17 -179.3(8) . . . . ?
C15 C16 C17 C18 -2.1(17) . . . . ?
C16 C17 C18 C19 2(2) . . . . ?
C17 C18 C19 C20 -2(2) . . . . ?
C16 C15 C20 C19 -2.2(15) . . . . ?
N1 C15 C20 C19 179.3(9) . . . . ?
C18 C19 C20 C15 1.9(18) . . . . ?
C8 C10 C21 C22 162.5(7) . . . . ?
C11 C10 C21 C22 -85.1(9) . . . . ?
C8 C10 C21 C26 -19.8(10) . . . . ?
C11 C10 C21 C26 92.6(8) . . . . ?
C26 C21 C22 C23 0.2(11) . . . . ?
C10 C21 C22 C23 178.0(7) . . . . ?
C21 C22 C23 C24 -0.5(12) . . . . ?
C21 C22 C23 Br1 179.7(6) . . . . ?
C22 C23 C24 C25 1.1(13) . . . . ?
Br1 C23 C24 C25 -179.1(6) . . . . ?
C23 C24 C25 C26 -1.5(13) . . . . ?
C24 C25 C26 C21 1.2(13) . . . . ?
C22 C21 C26 C25 -0.5(12) . . . . ?
C10 C21 C26 C25 -178.3(7) . . . . ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_chemical_compound_source        'organic synthesis'
_chemical_properties_physical    ', Heat-sensitive'
####################################################################### 
# 
# 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_cd17335
_database_code_depnum_ccdc_archive 'CCDC 1553766'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(2R,3S)-3'-ethyl-1',3-diphenyl-3H,4H-spiro[furo[3,2-c]chromene-2,4'-pyrazole]-4,5'(1'H)-dione
_chemical_name_common            
(2R,3S)-3'-ethyl-1',3-diphenyl-3H,4H-spiro[furo[3,2-c]chromene-2,4'-pyrazole]-4,5'(1'H)-dione
_chemical_melting_point          147
_chemical_formula_moiety         'C27 H20 N2 O4'
_chemical_formula_sum            'C27 H20 N2 O4'
_chemical_formula_weight         436.45

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           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                   8.3497(11)
_cell_length_b                   9.7735(13)
_cell_length_c                   27.653(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2256.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2433
_cell_measurement_theta_min      5.096
_cell_measurement_theta_max      44.308

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6042
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12988
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.210
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4193
_reflns_number_gt                3241
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ', Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1150 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(9)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4193
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
N1 N 0.6685(3) 1.0908(3) 0.60073(8) 0.0467(6) Uani 1 1 d . . . . .
N2 N 0.6235(3) 0.9652(3) 0.57924(8) 0.0472(6) Uani 1 1 d . . . . .
O1 O 0.6885(3) 1.1765(2) 0.67839(7) 0.0577(6) Uani 1 1 d . . . . .
O2 O 0.6650(2) 0.8795(2) 0.69451(6) 0.0456(5) Uani 1 1 d . . . . .
O3 O 0.2468(3) 1.0438(2) 0.78751(8) 0.0678(7) Uani 1 1 d . . . . .
O4 O 0.4641(2) 0.9690(2) 0.82461(7) 0.0489(5) Uani 1 1 d . . . . .
C1 C 0.6494(3) 1.0895(3) 0.64961(9) 0.0429(7) Uani 1 1 d . . . . .
C2 C 0.5658(3) 0.9543(3) 0.66066(9) 0.0398(7) Uani 1 1 d . . . . .
C3 C 0.5671(3) 0.8871(3) 0.61169(10) 0.0438(7) Uani 1 1 d . . . . .
C4 C 0.5211(4) 0.7431(4) 0.60116(11) 0.0582(9) Uani 1 1 d . . . . .
H4A H 0.4162 0.7257 0.6149 0.070 Uiso 1 1 calc R U . . .
H4B H 0.5967 0.6825 0.6169 0.070 Uiso 1 1 calc R U . . .
C5 C 0.5164(6) 0.7095(4) 0.54801(14) 0.1032(16) Uani 1 1 d . . . . .
H5A H 0.4272 0.7552 0.5332 0.155 Uiso 1 1 calc R U . . .
H5B H 0.5051 0.6124 0.5439 0.155 Uiso 1 1 calc R U . . .
H5C H 0.6140 0.7394 0.5330 0.155 Uiso 1 1 calc R U . . .
C6 C 0.4021(3) 0.9834(3) 0.68733(9) 0.0412(7) Uani 1 1 d . . . . .
H6 H 0.3731 1.0798 0.6828 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4588(3) 0.9627(3) 0.73857(9) 0.0392(7) Uani 1 1 d . . . . .
C8 C 0.6024(3) 0.9045(3) 0.73886(9) 0.0374(6) Uani 1 1 d . . . . .
C9 C 0.6890(3) 0.8707(3) 0.78204(10) 0.0401(6) Uani 1 1 d . . . . .
C10 C 0.8401(3) 0.8110(3) 0.78430(11) 0.0514(8) Uani 1 1 d . . . . .
H10 H 0.8933 0.7865 0.7561 0.062 Uiso 1 1 calc R U . . .
C11 C 0.9097(4) 0.7887(4) 0.82844(13) 0.0643(10) Uani 1 1 d . . . . .
H11 H 1.0108 0.7490 0.8302 0.077 Uiso 1 1 calc R U . . .
C12 C 0.8309(5) 0.8248(4) 0.87024(12) 0.0684(10) Uani 1 1 d . . . . .
H12 H 0.8792 0.8088 0.9000 0.082 Uiso 1 1 calc R U . . .
C13 C 0.6822(4) 0.8839(4) 0.86870(11) 0.0601(9) Uani 1 1 d . . . . .
H13 H 0.6298 0.9081 0.8971 0.072 Uiso 1 1 calc R U . . .
C14 C 0.6119(3) 0.9071(3) 0.82464(10) 0.0433(7) Uani 1 1 d . . . . .
C15 C 0.3768(4) 0.9955(3) 0.78249(11) 0.0457(7) Uani 1 1 d . . . . .
C16 C 0.2626(3) 0.8941(3) 0.67193(11) 0.0460(7) Uani 1 1 d . . . . .
C17 C 0.2233(4) 0.7754(3) 0.69651(11) 0.0559(9) Uani 1 1 d . . . . .
H17 H 0.2820 0.7503 0.7237 0.067 Uiso 1 1 calc R U . . .
C18 C 0.0983(4) 0.6937(4) 0.68124(16) 0.0725(11) Uani 1 1 d . . . . .
H18 H 0.0744 0.6133 0.6977 0.087 Uiso 1 1 calc R U . . .
C19 C 0.0107(5) 0.7307(5) 0.64238(19) 0.0873(14) Uani 1 1 d . . . . .
H19 H -0.0744 0.6761 0.6324 0.105 Uiso 1 1 calc R U . . .
C20 C 0.0463(5) 0.8485(5) 0.61738(18) 0.0905(14) Uani 1 1 d . . . . .
H20 H -0.0140 0.8731 0.5905 0.109 Uiso 1 1 calc R U . . .
C21 C 0.1728(4) 0.9309(4) 0.63247(14) 0.0682(10) Uani 1 1 d . . . . .
H21 H 0.1964 1.0110 0.6158 0.082 Uiso 1 1 calc R U . . .
C22 C 0.7474(3) 1.1889(3) 0.57161(10) 0.0446(7) Uani 1 1 d . . . . .
C23 C 0.8194(4) 1.1499(4) 0.52897(12) 0.0701(11) Uani 1 1 d . . . . .
H23 H 0.8183 1.0588 0.5193 0.084 Uiso 1 1 calc R U . . .
C24 C 0.8929(6) 1.2477(6) 0.50087(14) 0.0932(14) Uani 1 1 d . . . . .
H24 H 0.9416 1.2215 0.4721 0.112 Uiso 1 1 calc R U . . .
C25 C 0.8962(5) 1.3813(4) 0.51416(13) 0.0807(12) Uani 1 1 d . . . . .
H25 H 0.9458 1.4461 0.4946 0.097 Uiso 1 1 calc R U . . .
C26 C 0.8259(4) 1.4193(4) 0.55651(12) 0.0648(10) Uani 1 1 d . . . . .
H26 H 0.8281 1.5108 0.5658 0.078 Uiso 1 1 calc R U . . .
C27 C 0.7514(4) 1.3245(3) 0.58587(11) 0.0512(8) Uani 1 1 d . . . . .
H27 H 0.7044 1.3514 0.6148 0.061 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
N1 C1 1.361(3) . ?
N1 C22 1.415(4) . ?
N1 N2 1.415(3) . ?
N2 C3 1.269(4) . ?
O1 C1 1.210(3) . ?
O2 C8 1.355(3) . ?
O2 C2 1.448(3) . ?
O3 C15 1.192(3) . ?
O4 C14 1.375(3) . ?
O4 C15 1.398(4) . ?
C1 C2 1.525(4) . ?
C2 C3 1.505(4) . ?
C2 C6 1.579(4) . ?
C3 C4 1.488(5) . ?
C4 C5 1.506(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.508(4) . ?
C6 C16 1.517(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.327(4) . ?
C7 C15 1.430(4) . ?
C8 C9 1.434(4) . ?
C9 C14 1.389(4) . ?
C9 C10 1.391(4) . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C16 C21 1.372(4) . ?
C16 C17 1.384(4) . ?
C17 C18 1.380(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.349(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.377(4) . ?
C22 C27 1.383(4) . ?
C23 C24 1.376(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.362(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.380(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

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
C1 N1 C22 128.8(3) . . ?
C1 N1 N2 112.2(2) . . ?
C22 N1 N2 118.2(2) . . ?
C3 N2 N1 108.9(2) . . ?
C8 O2 C2 105.9(2) . . ?
C14 O4 C15 123.4(2) . . ?
O1 C1 N1 128.0(3) . . ?
O1 C1 C2 126.9(2) . . ?
N1 C1 C2 105.1(2) . . ?
O2 C2 C3 110.9(2) . . ?
O2 C2 C1 107.8(2) . . ?
C3 C2 C1 101.2(2) . . ?
O2 C2 C6 106.5(2) . . ?
C3 C2 C6 120.3(2) . . ?
C1 C2 C6 109.5(2) . . ?
N2 C3 C4 121.8(3) . . ?
N2 C3 C2 112.1(3) . . ?
C4 C3 C2 126.0(3) . . ?
C3 C4 C5 113.8(3) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C16 115.3(2) . . ?
C7 C6 C2 98.2(2) . . ?
C16 C6 C2 115.5(2) . . ?
C7 C6 H6 109.1 . . ?
C16 C6 H6 109.1 . . ?
C2 C6 H6 109.1 . . ?
C8 C7 C15 121.6(3) . . ?
C8 C7 C6 110.3(2) . . ?
C15 C7 C6 128.1(3) . . ?
C7 C8 O2 114.8(2) . . ?
C7 C8 C9 124.0(2) . . ?
O2 C8 C9 121.2(2) . . ?
C14 C9 C10 119.3(3) . . ?
C14 C9 C8 114.4(2) . . ?
C10 C9 C8 126.2(3) . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 O4 117.2(3) . . ?
C13 C14 C9 120.9(3) . . ?
O4 C14 C9 121.9(2) . . ?
O3 C15 O4 116.8(3) . . ?
O3 C15 C7 128.6(3) . . ?
O4 C15 C7 114.6(3) . . ?
C21 C16 C17 118.8(3) . . ?
C21 C16 C6 119.5(3) . . ?
C17 C16 C6 121.8(3) . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 119.8(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 120.1(4) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C27 119.9(3) . . ?
C23 C22 N1 120.2(3) . . ?
C27 C22 N1 119.9(3) . . ?
C24 C23 C22 119.1(4) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 121.6(4) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 119.2(4) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C27 121.1(4) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C22 119.1(3) . . ?
C26 C27 H27 120.4 . . ?
C22 C27 H27 120.4 . . ?

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
C1 N1 N2 C3 4.2(3) . . . . ?
C22 N1 N2 C3 174.6(2) . . . . ?
C22 N1 C1 O1 4.6(5) . . . . ?
N2 N1 C1 O1 173.8(3) . . . . ?
C22 N1 C1 C2 -176.0(3) . . . . ?
N2 N1 C1 C2 -6.8(3) . . . . ?
C8 O2 C2 C3 -152.6(2) . . . . ?
C8 O2 C2 C1 97.4(2) . . . . ?
C8 O2 C2 C6 -20.0(3) . . . . ?
O1 C1 C2 O2 -57.7(4) . . . . ?
N1 C1 C2 O2 123.0(2) . . . . ?
O1 C1 C2 C3 -174.1(3) . . . . ?
N1 C1 C2 C3 6.5(3) . . . . ?
O1 C1 C2 C6 57.8(4) . . . . ?
N1 C1 C2 C6 -121.5(2) . . . . ?
N1 N2 C3 C4 -175.0(3) . . . . ?
N1 N2 C3 C2 0.6(3) . . . . ?
O2 C2 C3 N2 -118.6(3) . . . . ?
C1 C2 C3 N2 -4.5(3) . . . . ?
C6 C2 C3 N2 116.2(3) . . . . ?
O2 C2 C3 C4 56.8(4) . . . . ?
C1 C2 C3 C4 171.0(3) . . . . ?
C6 C2 C3 C4 -68.3(4) . . . . ?
N2 C3 C4 C5 -11.6(5) . . . . ?
C2 C3 C4 C5 173.4(3) . . . . ?
O2 C2 C6 C7 19.3(3) . . . . ?
C3 C2 C6 C7 146.5(3) . . . . ?
C1 C2 C6 C7 -97.0(3) . . . . ?
O2 C2 C6 C16 -103.9(3) . . . . ?
C3 C2 C6 C16 23.3(4) . . . . ?
C1 C2 C6 C16 139.8(2) . . . . ?
C16 C6 C7 C8 110.7(3) . . . . ?
C2 C6 C7 C8 -12.6(3) . . . . ?
C16 C6 C7 C15 -68.2(4) . . . . ?
C2 C6 C7 C15 168.6(3) . . . . ?
C15 C7 C8 O2 180.0(3) . . . . ?
C6 C7 C8 O2 1.0(4) . . . . ?
C15 C7 C8 C9 -0.8(5) . . . . ?
C6 C7 C8 C9 -179.8(3) . . . . ?
C2 O2 C8 C7 12.6(3) . . . . ?
C2 O2 C8 C9 -166.7(2) . . . . ?
C7 C8 C9 C14 -1.5(4) . . . . ?
O2 C8 C9 C14 177.7(3) . . . . ?
C7 C8 C9 C10 -179.3(3) . . . . ?
O2 C8 C9 C10 -0.1(4) . . . . ?
C14 C9 C10 C11 0.3(4) . . . . ?
C8 C9 C10 C11 178.0(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C13 C14 O4 -178.8(3) . . . . ?
C12 C13 C14 C9 0.3(5) . . . . ?
C15 O4 C14 C13 -178.3(3) . . . . ?
C15 O4 C14 C9 2.6(4) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C8 C9 C14 C13 -178.5(3) . . . . ?
C10 C9 C14 O4 178.6(3) . . . . ?
C8 C9 C14 O4 0.6(4) . . . . ?
C14 O4 C15 O3 176.5(3) . . . . ?
C14 O4 C15 C7 -4.7(4) . . . . ?
C8 C7 C15 O3 -177.6(3) . . . . ?
C6 C7 C15 O3 1.1(5) . . . . ?
C8 C7 C15 O4 3.8(4) . . . . ?
C6 C7 C15 O4 -177.5(3) . . . . ?
C7 C6 C16 C21 161.0(3) . . . . ?
C2 C6 C16 C21 -85.4(4) . . . . ?
C7 C6 C16 C17 -19.3(4) . . . . ?
C2 C6 C16 C17 94.3(3) . . . . ?
C21 C16 C17 C18 1.2(4) . . . . ?
C6 C16 C17 C18 -178.5(3) . . . . ?
C16 C17 C18 C19 -1.2(5) . . . . ?
C17 C18 C19 C20 0.8(6) . . . . ?
C18 C19 C20 C21 -0.5(7) . . . . ?
C17 C16 C21 C20 -0.9(5) . . . . ?
C6 C16 C21 C20 178.8(3) . . . . ?
C19 C20 C21 C16 0.6(6) . . . . ?
C1 N1 C22 C23 150.0(3) . . . . ?
N2 N1 C22 C23 -18.7(4) . . . . ?
C1 N1 C22 C27 -30.4(4) . . . . ?
N2 N1 C22 C27 160.9(3) . . . . ?
C27 C22 C23 C24 -0.8(5) . . . . ?
N1 C22 C23 C24 178.9(4) . . . . ?
C22 C23 C24 C25 0.0(7) . . . . ?
C23 C24 C25 C26 0.5(8) . . . . ?
C24 C25 C26 C27 -0.2(7) . . . . ?
C25 C26 C27 C22 -0.5(5) . . . . ?
C23 C22 C27 C26 1.0(5) . . . . ?
N1 C22 C27 C26 -178.6(3) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
_chemical_compound_source        'organic synthesis'
_chemical_properties_physical    ', Heat-sensitive'
_exptl_crystal_preparation       ', Magnetic properties'
