# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_blc80
_audit_block_doi                 10.5517/cc11vby5
_database_code_depnum_ccdc_archive 'CCDC 978637'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1007/s11243-014-9865-2 2014
_audit_update_record             
;
2013-12-24 deposited with the CCDC.
2015-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 (5S,5aR,11bS)-3-(2,5-dichlorophenyl)-1,11b-dimethyl-10-nitro-
 5-phenyl-3,5a,6,11b-tetrahydro-5H-chromeno[4',3':4,5]pyrano
 [2,3-c]pyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 Cl2 N3 O4'
_chemical_formula_sum            'C27 H21 Cl2 N3 O4'
_chemical_formula_weight         522.37

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   9.7530(5)
_cell_length_b                   17.2963(8)
_cell_length_c                   14.3658(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.734(4)
_cell_angle_gamma                90.00
_cell_volume                     2422.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2801
_cell_measurement_theta_min      3.7970
_cell_measurement_theta_max      26.9650


_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_min  0.70675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            9854
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4740
_reflns_number_gt                3104
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro,Diff.Ltd,Ver 1.171.34.40'
_computing_cell_refinement       'CrysAlisPro, Diff.Ltd,Ver 1.171.34.40'
_computing_data_reduction        'CrysAlisPro, Diff.Ltd,Ver 1.171.34.40'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'PLATON(Spek,1999)& PARST(1995)'


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4740
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6225(2) 0.38455(12) -0.06386(13) 0.0334(5) Uani 1 1 d . . .
N2 N 0.53741(16) 0.38354(10) 0.00666(11) 0.0378(4) Uani 1 1 d . . .
N3 N 0.58592(16) 0.32491(10) 0.06397(10) 0.0342(4) Uani 1 1 d . . .
C3A C 0.69892(19) 0.29262(12) 0.02849(12) 0.0286(5) Uani 1 1 d . . .
O4 O 0.76210(13) 0.23451(8) 0.07307(8) 0.0338(4) Uani 1 1 d . . .
C5 C 0.89977(19) 0.22178(12) 0.04008(12) 0.0306(5) Uani 1 1 d . . .
H5 H 0.9604 0.2623 0.0654 0.037 Uiso 1 1 calc R . .
C5A C 0.9004(2) 0.22509(11) -0.06711(12) 0.0312(5) Uani 1 1 d . . .
H5A H 0.8403 0.1839 -0.0914 0.037 Uiso 1 1 calc R . .
C6 C 1.0444(2) 0.20926(14) -0.09940(14) 0.0430(6) Uani 1 1 d . . .
H6A H 1.0732 0.1582 -0.0788 0.052 Uiso 1 1 calc R . .
H6B H 1.0447 0.2102 -0.1669 0.052 Uiso 1 1 calc R . .
O7 O 1.13866(15) 0.26576(10) -0.06292(10) 0.0478(4) Uani 1 1 d . . .
C7A C 1.1010(2) 0.34097(13) -0.07872(13) 0.0351(5) Uani 1 1 d . . .
C8 C 1.2049(2) 0.39550(16) -0.06730(14) 0.0483(6) Uani 1 1 d . . .
H8 H 1.2918 0.3803 -0.0460 0.058 Uiso 1 1 calc R . .
C9 C 1.1792(2) 0.47115(16) -0.08730(14) 0.0488(7) Uani 1 1 d . . .
H9 H 1.2483 0.5080 -0.0809 0.059 Uiso 1 1 calc R . .
C10 C 1.0485(2) 0.49215(13) -0.11724(14) 0.0391(6) Uani 1 1 d . . .
C11 C 0.9439(2) 0.43884(12) -0.12331(12) 0.0343(5) Uani 1 1 d . . .
H11 H 0.8562 0.4550 -0.1413 0.041 Uiso 1 1 calc R . .
C11A C 0.96680(19) 0.36192(12) -0.10323(12) 0.0287(5) Uani 1 1 d . . .
C11B C 0.84900(19) 0.30282(11) -0.10894(12) 0.0277(5) Uani 1 1 d . . .
C11C C 0.72784(19) 0.32886(11) -0.05305(12) 0.0271(4) Uani 1 1 d . . .
C12 C 0.5887(2) 0.44106(14) -0.14031(15) 0.0491(6) Uani 1 1 d . . .
H12A H 0.4913 0.4489 -0.1445 0.074 Uiso 1 1 calc R . .
H12B H 0.6197 0.4210 -0.1984 0.074 Uiso 1 1 calc R . .
H12C H 0.6336 0.4894 -0.1270 0.074 Uiso 1 1 calc R . .
C13 C 0.5296(2) 0.31422(13) 0.15339(14) 0.0344(5) Uani 1 1 d . . .
C14 C 0.4640(2) 0.24615(14) 0.17647(14) 0.0417(6) Uani 1 1 d . . .
C15 C 0.4089(2) 0.23850(16) 0.26386(16) 0.0544(7) Uani 1 1 d . . .
H15 H 0.3649 0.1928 0.2795 0.065 Uiso 1 1 calc R . .
C16 C 0.4187(3) 0.29719(16) 0.32719(16) 0.0571(7) Uani 1 1 d . . .
H16 H 0.3809 0.2918 0.3855 0.069 Uiso 1 1 calc R . .
C17 C 0.4847(2) 0.36447(15) 0.30403(15) 0.0509(6) Uani 1 1 d . . .
C18 C 0.5406(2) 0.37322(13) 0.21717(14) 0.0421(6) Uani 1 1 d . . .
H18 H 0.5854 0.4188 0.2021 0.051 Uiso 1 1 calc R . .
C19 C 0.9459(2) 0.14518(12) 0.07883(12) 0.0333(5) Uani 1 1 d . . .
C20 C 1.0784(2) 0.13562(15) 0.11356(14) 0.0474(6) Uani 1 1 d . . .
H20 H 1.1381 0.1776 0.1158 0.057 Uiso 1 1 calc R . .
C21 C 1.1226(3) 0.06438(16) 0.14478(16) 0.0575(7) Uani 1 1 d . . .
H21 H 1.2127 0.0583 0.1668 0.069 Uiso 1 1 calc R . .
C22 C 1.0361(3) 0.00277(16) 0.14382(16) 0.0563(7) Uani 1 1 d . . .
H22 H 1.0670 -0.0453 0.1646 0.068 Uiso 1 1 calc R . .
C23 C 0.9025(3) 0.01173(14) 0.11191(16) 0.0547(7) Uani 1 1 d . . .
H23 H 0.8423 -0.0300 0.1126 0.066 Uiso 1 1 calc R . .
C24 C 0.8580(2) 0.08264(13) 0.07898(14) 0.0442(6) Uani 1 1 d . . .
H24 H 0.7681 0.0883 0.0567 0.053 Uiso 1 1 calc R . .
N25 N 1.0205(3) 0.57143(13) -0.14519(14) 0.0553(6) Uani 1 1 d . . .
C26 C 0.8048(2) 0.28950(13) -0.21158(12) 0.0405(6) Uani 1 1 d . . .
H26A H 0.7278 0.2550 -0.2147 0.061 Uiso 1 1 calc R . .
H26B H 0.8796 0.2673 -0.2443 0.061 Uiso 1 1 calc R . .
H26C H 0.7795 0.3380 -0.2397 0.061 Uiso 1 1 calc R . .
Cl27 Cl 0.50055(10) 0.43965(5) 0.38351(5) 0.0937(3) Uani 1 1 d . . .
Cl28 Cl 0.45080(7) 0.17116(4) 0.09770(4) 0.0664(2) Uani 1 1 d . . .
O29 O 0.9023(2) 0.59217(11) -0.15795(15) 0.0805(6) Uani 1 1 d . . .
O30 O 1.1186(2) 0.61450(10) -0.15750(12) 0.0779(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.329(2) . ?
C1 C11C 1.414(3) . ?
C1 C12 1.499(3) . ?
N2 N3 1.381(2) . ?
N3 C3A 1.349(2) . ?
N3 C13 1.424(2) . ?
C3A O4 1.333(2) . ?
C3A C11C 1.366(2) . ?
O4 C5 1.454(2) . ?
C5 C19 1.501(3) . ?
C5 C5A 1.541(2) . ?
C5 H5 0.9800 . ?
C5A C6 1.518(3) . ?
C5A C11B 1.550(3) . ?
C5A H5A 0.9800 . ?
C6 O7 1.430(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C7A 1.369(3) . ?
C7A C8 1.390(3) . ?
C7A C11A 1.393(3) . ?
C8 C9 1.361(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(3) . ?
C10 N25 1.452(3) . ?
C11 C11A 1.378(3) . ?
C11 H11 0.9300 . ?
C11A C11B 1.538(3) . ?
C11B C11C 1.517(2) . ?
C11B C26 1.541(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.373(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.387(3) . ?
C14 Cl28 1.723(2) . ?
C15 C16 1.365(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(3) . ?
C17 Cl27 1.734(2) . ?
C18 H18 0.9300 . ?
C19 C24 1.380(3) . ?
C19 C20 1.381(3) . ?
C20 C21 1.376(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.359(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N25 O29 1.217(3) . ?
N25 O30 1.230(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
N2 C1 C11C 112.08(17) . . ?
N2 C1 C12 116.03(18) . . ?
C11C C1 C12 131.86(17) . . ?
C1 N2 N3 104.70(15) . . ?
C3A N3 N2 110.36(14) . . ?
C3A N3 C13 128.95(16) . . ?
N2 N3 C13 119.91(15) . . ?
O4 C3A N3 120.12(15) . . ?
O4 C3A C11C 130.84(17) . . ?
N3 C3A C11C 109.04(17) . . ?
C3A O4 C5 112.06(14) . . ?
O4 C5 C19 106.38(15) . . ?
O4 C5 C5A 110.58(15) . . ?
C19 C5 C5A 113.16(16) . . ?
O4 C5 H5 108.9 . . ?
C19 C5 H5 108.9 . . ?
C5A C5 H5 108.9 . . ?
C6 C5A C5 109.27(17) . . ?
C6 C5A C11B 109.23(16) . . ?
C5 C5A C11B 114.13(15) . . ?
C6 C5A H5A 108.0 . . ?
C5 C5A H5A 108.0 . . ?
C11B C5A H5A 108.0 . . ?
O7 C6 C5A 110.82(17) . . ?
O7 C6 H6A 109.5 . . ?
C5A C6 H6A 109.5 . . ?
O7 C6 H6B 109.5 . . ?
C5A C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C7A O7 C6 115.00(17) . . ?
O7 C7A C8 115.8(2) . . ?
O7 C7A C11A 122.29(19) . . ?
C8 C7A C11A 121.9(2) . . ?
C9 C8 C7A 119.9(2) . . ?
C9 C8 H8 120.1 . . ?
C7A C8 H8 120.1 . . ?
C8 C9 C10 118.7(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 N25 118.9(2) . . ?
C9 C10 N25 119.9(2) . . ?
C10 C11 C11A 121.3(2) . . ?
C10 C11 H11 119.4 . . ?
C11A C11 H11 119.4 . . ?
C11 C11A C7A 116.66(19) . . ?
C11 C11A C11B 120.97(18) . . ?
C7A C11A C11B 122.36(19) . . ?
C11C C11B C11A 111.53(15) . . ?
C11C C11B C26 110.56(16) . . ?
C11A C11B C26 109.71(15) . . ?
C11C C11B C5A 107.47(14) . . ?
C11A C11B C5A 108.89(16) . . ?
C26 C11B C5A 108.61(16) . . ?
C3A C11C C1 103.81(16) . . ?
C3A C11C C11B 120.14(17) . . ?
C1 C11C C11B 136.02(16) . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.95(19) . . ?
C18 C13 N3 118.73(19) . . ?
C14 C13 N3 121.32(19) . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 Cl28 120.55(16) . . ?
C15 C14 Cl28 119.97(18) . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 Cl27 120.52(17) . . ?
C18 C17 Cl27 118.8(2) . . ?
C13 C18 C17 119.7(2) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C24 C19 C20 118.7(2) . . ?
C24 C19 C5 120.9(2) . . ?
C20 C19 C5 120.4(2) . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.7(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
O29 N25 O30 122.5(2) . . ?
O29 N25 C10 119.3(2) . . ?
O30 N25 C10 118.1(2) . . ?
C11B C26 H26A 109.5 . . ?
C11B C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C11B C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
C11C C1 N2 N3 -1.3(2) . . . . ?
C12 C1 N2 N3 176.88(18) . . . . ?
C1 N2 N3 C3A 0.9(2) . . . . ?
C1 N2 N3 C13 171.61(18) . . . . ?
N2 N3 C3A O4 -179.83(17) . . . . ?
C13 N3 C3A O4 10.5(3) . . . . ?
N2 N3 C3A C11C -0.1(2) . . . . ?
C13 N3 C3A C11C -169.77(19) . . . . ?
N3 C3A O4 C5 -163.89(17) . . . . ?
C11C C3A O4 C5 16.5(3) . . . . ?
C3A O4 C5 C19 -167.21(15) . . . . ?
C3A O4 C5 C5A -44.0(2) . . . . ?
O4 C5 C5A C6 -178.34(16) . . . . ?
C19 C5 C5A C6 -59.1(2) . . . . ?
O4 C5 C5A C11B 59.1(2) . . . . ?
C19 C5 C5A C11B 178.28(17) . . . . ?
C5 C5A C6 O7 -60.4(2) . . . . ?
C11B C5A C6 O7 65.1(2) . . . . ?
C5A C6 O7 C7A -52.4(2) . . . . ?
C6 O7 C7A C8 -163.13(16) . . . . ?
C6 O7 C7A C11A 17.9(3) . . . . ?
O7 C7A C8 C9 175.78(18) . . . . ?
C11A C7A C8 C9 -5.2(3) . . . . ?
C7A C8 C9 C10 1.1(3) . . . . ?
C8 C9 C10 C11 2.7(3) . . . . ?
C8 C9 C10 N25 -175.75(18) . . . . ?
C9 C10 C11 C11A -2.5(3) . . . . ?
N25 C10 C11 C11A 175.93(17) . . . . ?
C10 C11 C11A C7A -1.4(3) . . . . ?
C10 C11 C11A C11B 179.20(16) . . . . ?
O7 C7A C11A C11 -175.78(16) . . . . ?
C8 C7A C11A C11 5.3(3) . . . . ?
O7 C7A C11A C11B 3.6(3) . . . . ?
C8 C7A C11A C11B -175.35(17) . . . . ?
C11 C11A C11B C11C -52.3(2) . . . . ?
C7A C11A C11B C11C 128.40(19) . . . . ?
C11 C11A C11B C26 70.6(2) . . . . ?
C7A C11A C11B C26 -108.8(2) . . . . ?
C11 C11A C11B C5A -170.68(15) . . . . ?
C7A C11A C11B C5A 10.0(2) . . . . ?
C6 C5A C11B C11C -162.62(16) . . . . ?
C5 C5A C11B C11C -40.0(2) . . . . ?
C6 C5A C11B C11A -41.7(2) . . . . ?
C5 C5A C11B C11A 80.96(19) . . . . ?
C6 C5A C11B C26 77.7(2) . . . . ?
C5 C5A C11B C26 -159.62(16) . . . . ?
O4 C3A C11C C1 179.0(2) . . . . ?
N3 C3A C11C C1 -0.7(2) . . . . ?
O4 C3A C11C C11B 0.9(3) . . . . ?
N3 C3A C11C C11B -178.82(16) . . . . ?
N2 C1 C11C C3A 1.3(2) . . . . ?
C12 C1 C11C C3A -176.6(2) . . . . ?
N2 C1 C11C C11B 179.0(2) . . . . ?
C12 C1 C11C C11B 1.1(4) . . . . ?
C11A C11B C11C C3A -108.0(2) . . . . ?
C26 C11B C11C C3A 129.67(19) . . . . ?
C5A C11B C11C C3A 11.3(2) . . . . ?
C11A C11B C11C C1 74.6(3) . . . . ?
C26 C11B C11C C1 -47.8(3) . . . . ?
C5A C11B C11C C1 -166.1(2) . . . . ?
C3A N3 C13 C18 107.9(2) . . . . ?
N2 N3 C13 C18 -61.0(3) . . . . ?
C3A N3 C13 C14 -72.5(3) . . . . ?
N2 N3 C13 C14 118.7(2) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?
N3 C13 C14 C15 -179.13(19) . . . . ?
C18 C13 C14 Cl28 -179.31(17) . . . . ?
N3 C13 C14 Cl28 1.1(3) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
Cl28 C14 C15 C16 179.8(2) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C15 C16 C17 Cl27 -179.2(2) . . . . ?
C14 C13 C18 C17 -0.6(3) . . . . ?
N3 C13 C18 C17 179.02(18) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
Cl27 C17 C18 C13 179.77(17) . . . . ?
O4 C5 C19 C24 42.6(2) . . . . ?
C5A C5 C19 C24 -79.0(2) . . . . ?
O4 C5 C19 C20 -138.63(19) . . . . ?
C5A C5 C19 C20 99.8(2) . . . . ?
C24 C19 C20 C21 2.1(3) . . . . ?
C5 C19 C20 C21 -176.74(18) . . . . ?
C19 C20 C21 C22 -1.4(3) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 1.6(4) . . . . ?
C22 C23 C24 C19 -0.9(3) . . . . ?
C20 C19 C24 C23 -1.0(3) . . . . ?
C5 C19 C24 C23 177.85(18) . . . . ?
C11 C10 N25 O29 12.5(3) . . . . ?
C9 C10 N25 O29 -169.0(2) . . . . ?
C11 C10 N25 O30 -165.56(19) . . . . ?
C9 C10 N25 O30 12.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_nagpy1
_database_code_depnum_ccdc_archive 'CCDC 989312'
_audit_update_record             
;
2014-02-28 deposited with the CCDC.
2015-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 1,5,11b-Trimethyl-5-(4-methylpent-3-en-1-yl)-10-nitro-3-
 phenyl-3,5a,6,11b-tetrahydro-5H-chromeno[4',3':4,5]pyrano
 [2,3-c]pyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H31 N3 O4'
_chemical_formula_sum            'C28 H31 N3 O4'
_chemical_formula_weight         473.56

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.0801(7)
_cell_length_b                   15.4384(13)
_cell_length_c                   15.7805(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.780(7)
_cell_angle_gamma                90.00
_cell_volume                     2443.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2317
_cell_measurement_theta_min      4.0640
_cell_measurement_theta_max      26.9880

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_min  0.78186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            9679
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0848
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4774
_reflns_number_gt                2542
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro,Diff.Ltd,Ver 1.171.34.40'
_computing_cell_refinement       'CrysAlisPro, Diff.Ltd,Ver 1.171.34.40'
_computing_data_reduction        'CrysAlisPro, Diff.Ltd,Ver 1.171.34.40'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'PLATON(Spek,1999)& PARST(1995)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0504P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0079(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4774
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5623(2) 0.49064(16) 0.1023(2) 0.1206(10) Uani 1 1 d . . .
O2 O 0.7658(3) 0.47894(14) 0.0762(2) 0.1141(10) Uani 1 1 d . . .
C1 C 1.0638(2) 0.24220(16) 0.04791(16) 0.0446(6) Uani 1 1 d . . .
N2 N 1.16481(17) 0.21973(13) 0.10437(14) 0.0486(6) Uani 1 1 d . . .
N3 N 1.12836(16) 0.14237(13) 0.13816(13) 0.0438(5) Uani 1 1 d . . .
C3A C 1.00538(19) 0.11847(15) 0.10144(15) 0.0394(6) Uani 1 1 d . . .
O4 O 0.95102(13) 0.04276(10) 0.12077(11) 0.0452(4) Uani 1 1 d . . .
C5 C 0.80845(19) 0.03696(15) 0.09088(16) 0.0403(6) Uani 1 1 d . . .
C5A C 0.7904(2) 0.07039(15) -0.00181(15) 0.0401(6) Uani 1 1 d . . .
H5A H 0.8515 0.0361 -0.0329 0.048 Uiso 1 1 calc R . .
C6 C 0.6527(2) 0.05564(16) -0.04747(17) 0.0499(7) Uani 1 1 d . . .
H6A H 0.6552 0.0672 -0.1077 0.060 Uiso 1 1 calc R . .
H6B H 0.6285 -0.0047 -0.0414 0.060 Uiso 1 1 calc R . .
O7 O 0.55209(14) 0.10912(11) -0.01575(12) 0.0562(5) Uani 1 1 d . . .
C7A C 0.5858(2) 0.19214(16) 0.00554(16) 0.0442(6) Uani 1 1 d . . .
C8 C 0.4808(2) 0.24314(19) 0.02809(18) 0.0576(8) Uani 1 1 d . . .
H8 H 0.3957 0.2196 0.0267 0.069 Uiso 1 1 calc R . .
C9 C 0.5019(2) 0.32681(19) 0.05199(18) 0.0599(8) Uani 1 1 d . . .
H9 H 0.4321 0.3612 0.0669 0.072 Uiso 1 1 calc R . .
C10 C 0.6286(3) 0.35951(17) 0.05363(17) 0.0553(7) Uani 1 1 d . . .
C11 C 0.7344(2) 0.30937(17) 0.03304(17) 0.0503(7) Uani 1 1 d . . .
H11 H 0.8194 0.3333 0.0354 0.060 Uiso 1 1 calc R . .
C11A C 0.7149(2) 0.22432(15) 0.00907(15) 0.0399(6) Uani 1 1 d . . .
C11B C 0.8302(2) 0.16651(15) -0.01353(15) 0.0386(6) Uani 1 1 d . . .
C11C C 0.9585(2) 0.18073(15) 0.04320(15) 0.0396(6) Uani 1 1 d . . .
C12 C 1.0766(2) 0.32553(17) 0.00214(19) 0.0578(7) Uani 1 1 d . . .
H12A H 1.0256 0.3694 0.0273 0.087 Uiso 1 1 calc R . .
H12B H 1.0437 0.3185 -0.0567 0.087 Uiso 1 1 calc R . .
H12C H 1.1686 0.3425 0.0063 0.087 Uiso 1 1 calc R . .
C13 C 1.2164(2) 0.10219(17) 0.20218(16) 0.0449(6) Uani 1 1 d . . .
C14 C 1.1741(3) 0.0386(2) 0.2531(2) 0.0751(10) Uani 1 1 d . . .
H14 H 1.0861 0.0197 0.2457 0.090 Uiso 1 1 calc R . .
C15 C 1.2627(3) 0.0026(2) 0.3156(2) 0.0970(12) Uani 1 1 d . . .
H15 H 1.2340 -0.0413 0.3498 0.116 Uiso 1 1 calc R . .
C16 C 1.3926(3) 0.0303(2) 0.3282(2) 0.0767(10) Uani 1 1 d . . .
H16 H 1.4515 0.0058 0.3706 0.092 Uiso 1 1 calc R . .
C17 C 1.4333(2) 0.0935(2) 0.27817(19) 0.0674(9) Uani 1 1 d . . .
H17 H 1.5213 0.1125 0.2863 0.081 Uiso 1 1 calc R . .
C18 C 1.3468(2) 0.1306(2) 0.21490(17) 0.0591(8) Uani 1 1 d . . .
H18 H 1.3762 0.1746 0.1811 0.071 Uiso 1 1 calc R . .
C19 C 0.7320(2) 0.08597(16) 0.15392(16) 0.0490(7) Uani 1 1 d . . .
H19A H 0.7542 0.0629 0.2101 0.073 Uiso 1 1 calc R . .
H19B H 0.6380 0.0797 0.1382 0.073 Uiso 1 1 calc R . .
H19C H 0.7556 0.1462 0.1533 0.073 Uiso 1 1 calc R . .
N20 N 0.6544(3) 0.44895(18) 0.07891(19) 0.0820(9) Uani 1 1 d . . .
C21 C 0.8540(2) 0.18373(19) -0.10624(17) 0.0579(8) Uani 1 1 d . . .
H21A H 0.8805 0.2429 -0.1123 0.087 Uiso 1 1 calc R . .
H21B H 0.7732 0.1730 -0.1424 0.087 Uiso 1 1 calc R . .
H21C H 0.9231 0.1461 -0.1222 0.087 Uiso 1 1 calc R . .
C22 C 0.7785(2) -0.05995(15) 0.09385(17) 0.0470(6) Uani 1 1 d . . .
H22A H 0.8305 -0.0889 0.0538 0.056 Uiso 1 1 calc R . .
H22B H 0.6852 -0.0684 0.0740 0.056 Uiso 1 1 calc R . .
C23 C 0.8061(2) -0.10497(17) 0.18042(19) 0.0604(8) Uani 1 1 d . . .
H23A H 0.9015 -0.1082 0.1962 0.073 Uiso 1 1 calc R . .
H23B H 0.7665 -0.0719 0.2237 0.073 Uiso 1 1 calc R . .
C24 C 0.7482(3) -0.19432(18) 0.1752(2) 0.0691(8) Uani 1 1 d . . .
H24 H 0.7990 -0.2370 0.1521 0.083 Uiso 1 1 calc R . .
C25 C 0.6341(3) -0.21865(19) 0.19950(19) 0.0613(8) Uani 1 1 d . . .
C26 C 0.5465(3) -0.1622(3) 0.2466(2) 0.1014(13) Uani 1 1 d . . .
H26A H 0.5682 -0.1699 0.3067 0.152 Uiso 1 1 calc R . .
H26B H 0.4550 -0.1777 0.2314 0.152 Uiso 1 1 calc R . .
H26C H 0.5600 -0.1028 0.2319 0.152 Uiso 1 1 calc R . .
C27 C 0.5780(4) -0.3067(2) 0.1811(2) 0.1126(14) Uani 1 1 d . . .
H27A H 0.6385 -0.3397 0.1506 0.169 Uiso 1 1 calc R . .
H27B H 0.4938 -0.3018 0.1470 0.169 Uiso 1 1 calc R . .
H27C H 0.5654 -0.3355 0.2336 0.169 Uiso 1 1 calc R . .


_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 N20 1.217(3) . ?
O2 N20 1.219(3) . ?
C1 N2 1.329(3) . ?
C1 C11C 1.420(3) . ?
C1 C12 1.487(3) . ?
N2 N3 1.373(3) . ?
N3 C3A 1.365(2) . ?
N3 C13 1.419(3) . ?
C3A O4 1.339(3) . ?
C3A C11C 1.380(3) . ?
O4 C5 1.469(2) . ?
C5 C19 1.520(3) . ?
C5 C22 1.528(3) . ?
C5 C5A 1.544(3) . ?
C5A C6 1.515(3) . ?
C5A C11B 1.553(3) . ?
C5A H5A 0.9800 . ?
C6 O7 1.436(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C7A 1.359(3) . ?
C7A C11A 1.389(3) . ?
C7A C8 1.393(3) . ?
C8 C9 1.356(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(3) . ?
C10 N20 1.453(4) . ?
C11 C11A 1.375(3) . ?
C11 H11 0.9300 . ?
C11A C11B 1.536(3) . ?
C11B C11C 1.513(3) . ?
C11B C21 1.529(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.364(4) . ?
C13 C18 1.380(3) . ?
C14 C15 1.379(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.344(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.533(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.497(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.304(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.490(4) . ?
C25 C27 1.490(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
N2 C1 C11C 112.2(2) . . ?
N2 C1 C12 117.0(2) . . ?
C11C C1 C12 130.8(2) . . ?
C1 N2 N3 105.69(17) . . ?
C3A N3 N2 109.71(18) . . ?
C3A N3 C13 131.3(2) . . ?
N2 N3 C13 118.95(18) . . ?
O4 C3A N3 120.9(2) . . ?
O4 C3A C11C 129.73(18) . . ?
N3 C3A C11C 109.3(2) . . ?
C3A O4 C5 112.92(16) . . ?
O4 C5 C19 107.65(18) . . ?
O4 C5 C22 103.86(17) . . ?
C19 C5 C22 110.7(2) . . ?
O4 C5 C5A 107.57(17) . . ?
C19 C5 C5A 115.74(19) . . ?
C22 C5 C5A 110.58(19) . . ?
C6 C5A C5 114.53(19) . . ?
C6 C5A C11B 108.82(18) . . ?
C5 C5A C11B 115.14(18) . . ?
C6 C5A H5A 105.8 . . ?
C5 C5A H5A 105.8 . . ?
C11B C5A H5A 105.8 . . ?
O7 C6 C5A 113.13(19) . . ?
O7 C6 H6A 109.0 . . ?
C5A C6 H6A 109.0 . . ?
O7 C6 H6B 109.0 . . ?
C5A C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7A O7 C6 117.44(17) . . ?
O7 C7A C11A 123.8(2) . . ?
O7 C7A C8 114.8(2) . . ?
C11A C7A C8 121.3(2) . . ?
C9 C8 C7A 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C7A C8 H8 119.8 . . ?
C8 C9 C10 118.4(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C11 121.9(3) . . ?
C9 C10 N20 119.7(3) . . ?
C11 C10 N20 118.4(2) . . ?
C11A C11 C10 120.4(2) . . ?
C11A C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C11A C7A 117.4(2) . . ?
C11 C11A C11B 121.86(19) . . ?
C7A C11A C11B 120.7(2) . . ?
C11C C11B C21 109.53(17) . . ?
C11C C11B C11A 113.59(18) . . ?
C21 C11B C11A 108.43(19) . . ?
C11C C11B C5A 106.50(18) . . ?
C21 C11B C5A 110.32(19) . . ?
C11A C11B C5A 108.45(17) . . ?
C3A C11C C1 103.1(2) . . ?
C3A C11C C11B 120.5(2) . . ?
C1 C11C C11B 135.9(2) . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.5(2) . . ?
C14 C13 N3 121.6(2) . . ?
C18 C13 N3 118.9(2) . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C17 119.7(3) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C5 C19 H19A 109.5 . . ?
C5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 N20 O2 122.9(3) . . ?
O1 N20 C10 117.7(3) . . ?
O2 N20 C10 119.4(3) . . ?
C11B C21 H21A 109.5 . . ?
C11B C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C11B C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 C22 C23 116.9(2) . . ?
C5 C22 H22A 108.1 . . ?
C23 C22 H22A 108.1 . . ?
C5 C22 H22B 108.1 . . ?
C23 C22 H22B 108.1 . . ?
H22A C22 H22B 107.3 . . ?
C24 C23 C22 109.5(2) . . ?
C24 C23 H23A 109.8 . . ?
C22 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
C22 C23 H23B 109.8 . . ?
H23A C23 H23B 108.2 . . ?
C25 C24 C23 126.8(3) . . ?
C25 C24 H24 116.6 . . ?
C23 C24 H24 116.6 . . ?
C24 C25 C26 124.2(3) . . ?
C24 C25 C27 122.3(3) . . ?
C26 C25 C27 113.5(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
C11C C1 N2 N3 0.2(3) . . . . ?
C12 C1 N2 N3 179.1(2) . . . . ?
C1 N2 N3 C3A 0.2(3) . . . . ?
C1 N2 N3 C13 -179.05(19) . . . . ?
N2 N3 C3A O4 176.51(19) . . . . ?
C13 N3 C3A O4 -4.3(4) . . . . ?
N2 N3 C3A C11C -0.6(3) . . . . ?
C13 N3 C3A C11C 178.6(2) . . . . ?
N3 C3A O4 C5 166.9(2) . . . . ?
C11C C3A O4 C5 -16.7(3) . . . . ?
C3A O4 C5 C19 -79.7(2) . . . . ?
C3A O4 C5 C22 162.97(19) . . . . ?
C3A O4 C5 C5A 45.7(2) . . . . ?
O4 C5 C5A C6 170.67(18) . . . . ?
C19 C5 C5A C6 -68.9(3) . . . . ?
C22 C5 C5A C6 57.9(2) . . . . ?
O4 C5 C5A C11B -62.0(2) . . . . ?
C19 C5 C5A C11B 58.3(2) . . . . ?
C22 C5 C5A C11B -174.83(17) . . . . ?
C5 C5A C6 O7 70.4(3) . . . . ?
C11B C5A C6 O7 -60.1(3) . . . . ?
C5A C6 O7 C7A 39.0(3) . . . . ?
C6 O7 C7A C11A -8.8(4) . . . . ?
C6 O7 C7A C8 174.1(2) . . . . ?
O7 C7A C8 C9 178.9(2) . . . . ?
C11A C7A C8 C9 1.8(4) . . . . ?
C7A C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C8 C9 C10 N20 180.0(3) . . . . ?
C9 C10 C11 C11A 0.7(4) . . . . ?
N20 C10 C11 C11A 179.8(3) . . . . ?
C10 C11 C11A C7A 0.8(4) . . . . ?
C10 C11 C11A C11B -179.5(2) . . . . ?
O7 C7A C11A C11 -178.9(2) . . . . ?
C8 C7A C11A C11 -2.1(4) . . . . ?
O7 C7A C11A C11B 1.4(4) . . . . ?
C8 C7A C11A C11B 178.2(2) . . . . ?
C11 C11A C11B C11C 39.2(3) . . . . ?
C7A C11A C11B C11C -141.1(2) . . . . ?
C11 C11A C11B C21 -82.8(3) . . . . ?
C7A C11A C11B C21 96.9(3) . . . . ?
C11 C11A C11B C5A 157.4(2) . . . . ?
C7A C11A C11B C5A -22.9(3) . . . . ?
C6 C5A C11B C11C 172.13(18) . . . . ?
C5 C5A C11B C11C 42.0(2) . . . . ?
C6 C5A C11B C21 -69.1(2) . . . . ?
C5 C5A C11B C21 160.79(18) . . . . ?
C6 C5A C11B C11A 49.5(2) . . . . ?
C5 C5A C11B C11A -80.6(2) . . . . ?
O4 C3A C11C C1 -176.1(2) . . . . ?
N3 C3A C11C C1 0.6(2) . . . . ?
O4 C3A C11C C11B -3.0(4) . . . . ?
N3 C3A C11C C11B 173.74(19) . . . . ?
N2 C1 C11C C3A -0.5(3) . . . . ?
C12 C1 C11C C3A -179.3(3) . . . . ?
N2 C1 C11C C11B -172.0(2) . . . . ?
C12 C1 C11C C11B 9.3(5) . . . . ?
C21 C11B C11C C3A -129.1(2) . . . . ?
C11A C11B C11C C3A 109.5(2) . . . . ?
C5A C11B C11C C3A -9.8(3) . . . . ?
C21 C11B C11C C1 41.2(4) . . . . ?
C11A C11B C11C C1 -80.2(3) . . . . ?
C5A C11B C11C C1 160.5(3) . . . . ?
C3A N3 C13 C14 -16.0(4) . . . . ?
N2 N3 C13 C14 163.1(3) . . . . ?
C3A N3 C13 C18 166.3(2) . . . . ?
N2 N3 C13 C18 -14.6(3) . . . . ?
C18 C13 C14 C15 -1.1(5) . . . . ?
N3 C13 C14 C15 -178.7(3) . . . . ?
C13 C14 C15 C16 0.8(6) . . . . ?
C14 C15 C16 C17 -0.2(6) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C14 C13 C18 C17 1.0(4) . . . . ?
N3 C13 C18 C17 178.7(2) . . . . ?
C16 C17 C18 C13 -0.5(5) . . . . ?
C9 C10 N20 O1 3.8(5) . . . . ?
C11 C10 N20 O1 -175.2(3) . . . . ?
C9 C10 N20 O2 -176.4(3) . . . . ?
C11 C10 N20 O2 4.6(5) . . . . ?
O4 C5 C22 C23 58.6(3) . . . . ?
C19 C5 C22 C23 -56.6(3) . . . . ?
C5A C5 C22 C23 173.77(19) . . . . ?
C5 C22 C23 C24 169.6(2) . . . . ?
C22 C23 C24 C25 -98.1(4) . . . . ?
C23 C24 C25 C26 -7.2(5) . . . . ?
C23 C24 C25 C27 171.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_capio
_database_code_depnum_ccdc_archive 'CCDC 1024805'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
10-Chloro-5,5,11b-trimethyl-1-phenyl-5,5a,6,
11b-tetrahydrochromeno[4',3':4,5]pyrano[3,2-d]isoxazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 Cl N O3'
_chemical_formula_sum            'C22 H20 Cl N O3'
_chemical_formula_weight         381.84

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0838(7)
_cell_length_b                   9.2619(9)
_cell_length_c                   11.2639(7)
_cell_angle_alpha                98.859(7)
_cell_angle_beta                 93.035(6)
_cell_angle_gamma                96.981(7)
_cell_volume                     926.94(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1697
_cell_measurement_theta_min      4.0930
_cell_measurement_theta_max      27.7080

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Crys Alis RED'

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6553
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3628
_reflns_number_gt                2564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0474P)²+0.1623P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3628
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl20 Cl 0.33155(7) 0.32406(8) 0.05831(6) 0.0661(2) Uani 1 1 d . . .
O4 O 0.79775(17) 0.63199(17) 0.59929(12) 0.0445(4) Uani 1 1 d . . .
O3 O 0.82296(16) 0.39304(17) 0.55217(12) 0.0424(4) Uani 1 1 d . . .
C11 C 0.5511(2) 0.5001(2) 0.19899(18) 0.0365(5) Uani 1 1 d . . .
H11 H 0.5996 0.4167 0.1922 0.044 Uiso 1 1 calc R . .
O7 O 0.59720(19) 0.88595(17) 0.34236(15) 0.0554(5) Uani 1 1 d . . .
C3A C 0.8026(2) 0.5188(2) 0.51315(18) 0.0344(5) Uani 1 1 d . . .
C11B C 0.7744(2) 0.6385(2) 0.33182(17) 0.0332(5) Uani 1 1 d . . .
C11A C 0.6194(2) 0.6300(2) 0.26815(18) 0.0345(5) Uani 1 1 d . . .
N2 N 0.8304(2) 0.2864(2) 0.44764(16) 0.0432(5) Uani 1 1 d . . .
C1 C 0.8129(2) 0.3559(2) 0.35568(18) 0.0336(5) Uani 1 1 d . . .
C7A C 0.5446(2) 0.7524(2) 0.2746(2) 0.0438(6) Uani 1 1 d . . .
C12 C 0.8144(2) 0.2654(2) 0.23451(18) 0.0375(5) Uani 1 1 d . . .
C5A C 0.8012(2) 0.7763(2) 0.43248(19) 0.0404(5) Uani 1 1 d . . .
H5A H 0.9093 0.7987 0.4487 0.048 Uiso 1 1 calc R . .
C11C C 0.7930(2) 0.5066(2) 0.39220(17) 0.0307(5) Uani 1 1 d . . .
C10 C 0.4131(2) 0.4918(3) 0.1403(2) 0.0438(6) Uani 1 1 d . . .
C8 C 0.4055(3) 0.7430(3) 0.2142(2) 0.0579(7) Uani 1 1 d . . .
H8 H 0.3567 0.8261 0.2195 0.069 Uiso 1 1 calc R . .
C17 C 0.9305(3) 0.2875(3) 0.1620(2) 0.0503(6) Uani 1 1 d . . .
H17 H 1.0089 0.3621 0.1875 0.060 Uiso 1 1 calc R . .
C13 C 0.7008(3) 0.1520(3) 0.1962(2) 0.0474(6) Uani 1 1 d . . .
H13 H 0.6230 0.1354 0.2449 0.057 Uiso 1 1 calc R . .
C5 C 0.7381(3) 0.7568(2) 0.5549(2) 0.0449(6) Uani 1 1 d . . .
C14 C 0.7017(3) 0.0626(3) 0.0857(2) 0.0604(7) Uani 1 1 d . . .
H14 H 0.6248 -0.0136 0.0603 0.072 Uiso 1 1 calc R . .
C9 C 0.3390(3) 0.6134(3) 0.1470(2) 0.0561(7) Uani 1 1 d . . .
H9 H 0.2458 0.6077 0.1069 0.067 Uiso 1 1 calc R . .
C16 C 0.9298(3) 0.1982(3) 0.0516(2) 0.0629(8) Uani 1 1 d . . .
H16 H 1.0072 0.2141 0.0024 0.075 Uiso 1 1 calc R . .
C15 C 0.8159(3) 0.0867(3) 0.0144(2) 0.0656(8) Uani 1 1 d . . .
H15 H 0.8164 0.0271 -0.0600 0.079 Uiso 1 1 calc R . .
C21 C 0.8909(2) 0.6552(3) 0.2385(2) 0.0470(6) Uani 1 1 d . . .
H21A H 0.9886 0.6578 0.2765 0.071 Uiso 1 1 calc R . .
H21B H 0.8845 0.7450 0.2071 0.071 Uiso 1 1 calc R . .
H21C H 0.8722 0.5731 0.1740 0.071 Uiso 1 1 calc R . .
C19 C 0.5707(3) 0.7240(3) 0.5539(2) 0.0599(7) Uani 1 1 d . . .
H19A H 0.5354 0.6414 0.4924 0.090 Uiso 1 1 calc R . .
H19B H 0.5264 0.8086 0.5377 0.090 Uiso 1 1 calc R . .
H19C H 0.5440 0.7013 0.6309 0.090 Uiso 1 1 calc R . .
C18 C 0.7991(4) 0.8859(3) 0.6523(2) 0.0735(9) Uani 1 1 d . . .
H18A H 0.7685 0.8657 0.7290 0.110 Uiso 1 1 calc R . .
H18B H 0.7616 0.9735 0.6349 0.110 Uiso 1 1 calc R . .
H18C H 0.9057 0.9000 0.6544 0.110 Uiso 1 1 calc R . .
C6 C 0.7518(3) 0.9068(3) 0.3838(2) 0.0541(6) Uani 1 1 d . . .
H6A H 0.7708 0.9926 0.4465 0.065 Uiso 1 1 calc R . .
H6B H 0.8111 0.9266 0.3175 0.065 Uiso 1 1 calc R . .


_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
Cl20 C10 1.738(2) . ?
O4 C3A 1.321(2) . ?
O4 C5 1.477(3) . ?
O3 C3A 1.336(2) . ?
O3 N2 1.426(2) . ?
C11 C10 1.374(3) . ?
C11 C11A 1.385(3) . ?
C11 H11 0.9300 . ?
O7 C7A 1.367(3) . ?
O7 C6 1.437(3) . ?
C3A C11C 1.347(3) . ?
C11B C11C 1.509(3) . ?
C11B C11A 1.533(3) . ?
C11B C21 1.542(3) . ?
C11B C5A 1.557(3) . ?
C11A C7A 1.386(3) . ?
N2 C1 1.313(3) . ?
C1 C11C 1.430(3) . ?
C1 C12 1.489(3) . ?
C7A C8 1.390(3) . ?
C12 C13 1.380(3) . ?
C12 C17 1.382(3) . ?
C5A C6 1.508(3) . ?
C5A C5 1.549(3) . ?
C5A H5A 0.9800 . ?
C10 C9 1.375(3) . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C17 C16 1.383(3) . ?
C17 H17 0.9300 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C5 C19 1.513(3) . ?
C5 C18 1.520(3) . ?
C14 C15 1.363(4) . ?
C14 H14 0.9300 . ?
C9 H9 0.9300 . ?
C16 C15 1.369(4) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 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
C3A O4 C5 112.96(15) . . ?
C3A O3 N2 106.55(15) . . ?
C10 C11 C11A 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C11A C11 H11 119.3 . . ?
C7A O7 C6 116.10(17) . . ?
O4 C3A O3 114.72(17) . . ?
O4 C3A C11C 131.9(2) . . ?
O3 C3A C11C 113.42(18) . . ?
C11C C11B C11A 113.09(16) . . ?
C11C C11B C21 110.46(17) . . ?
C11A C11B C21 108.39(16) . . ?
C11C C11B C5A 106.72(16) . . ?
C11A C11B C5A 109.26(16) . . ?
C21 C11B C5A 108.83(18) . . ?
C11 C11A C7A 117.57(19) . . ?
C11 C11A C11B 120.94(18) . . ?
C7A C11A C11B 121.46(19) . . ?
C1 N2 O3 105.54(16) . . ?
N2 C1 C11C 112.47(18) . . ?
N2 C1 C12 115.62(18) . . ?
C11C C1 C12 131.89(19) . . ?
O7 C7A C11A 123.60(19) . . ?
O7 C7A C8 115.9(2) . . ?
C11A C7A C8 120.5(2) . . ?
C13 C12 C17 119.2(2) . . ?
C13 C12 C1 119.2(2) . . ?
C17 C12 C1 121.6(2) . . ?
C6 C5A C5 112.63(19) . . ?
C6 C5A C11B 109.32(18) . . ?
C5 C5A C11B 116.21(18) . . ?
C6 C5A H5A 106.0 . . ?
C5 C5A H5A 106.0 . . ?
C11B C5A H5A 106.0 . . ?
C3A C11C C1 102.00(18) . . ?
C3A C11C C11B 120.91(18) . . ?
C1 C11C C11B 137.00(18) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 Cl20 119.03(18) . . ?
C9 C10 Cl20 120.10(18) . . ?
C9 C8 C7A 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C7A C8 H8 119.4 . . ?
C12 C17 C16 119.8(2) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
O4 C5 C19 105.86(19) . . ?
O4 C5 C18 102.28(18) . . ?
C19 C5 C18 111.3(2) . . ?
O4 C5 C5A 109.23(17) . . ?
C19 C5 C5A 116.09(19) . . ?
C18 C5 C5A 111.0(2) . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C8 C9 C10 118.5(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11B C21 H21A 109.5 . . ?
C11B C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C11B C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 C19 H19A 109.5 . . ?
C5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C6 C5A 113.60(19) . . ?
O7 C6 H6A 108.8 . . ?
C5A C6 H6A 108.8 . . ?
O7 C6 H6B 108.8 . . ?
C5A C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?

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
C5 O4 C3A O3 -165.43(17) . . . . ?
C5 O4 C3A C11C 15.7(3) . . . . ?
N2 O3 C3A O4 -178.00(15) . . . . ?
N2 O3 C3A C11C 1.1(2) . . . . ?
C10 C11 C11A C7A -1.0(3) . . . . ?
C10 C11 C11A C11B -179.13(19) . . . . ?
C11C C11B C11A C11 -43.5(3) . . . . ?
C21 C11B C11A C11 79.4(2) . . . . ?
C5A C11B C11A C11 -162.17(19) . . . . ?
C11C C11B C11A C7A 138.4(2) . . . . ?
C21 C11B C11A C7A -98.7(2) . . . . ?
C5A C11B C11A C7A 19.7(3) . . . . ?
C3A O3 N2 C1 -0.5(2) . . . . ?
O3 N2 C1 C11C -0.2(2) . . . . ?
O3 N2 C1 C12 -179.19(15) . . . . ?
C6 O7 C7A C11A 15.3(3) . . . . ?
C6 O7 C7A C8 -167.1(2) . . . . ?
C11 C11A C7A O7 178.0(2) . . . . ?
C11B C11A C7A O7 -3.8(3) . . . . ?
C11 C11A C7A C8 0.5(3) . . . . ?
C11B C11A C7A C8 178.7(2) . . . . ?
N2 C1 C12 C13 66.4(2) . . . . ?
C11C C1 C12 C13 -112.3(3) . . . . ?
N2 C1 C12 C17 -110.3(2) . . . . ?
C11C C1 C12 C17 71.0(3) . . . . ?
C11C C11B C5A C6 -167.69(17) . . . . ?
C11A C11B C5A C6 -45.1(2) . . . . ?
C21 C11B C5A C6 73.1(2) . . . . ?
C11C C11B C5A C5 -38.9(2) . . . . ?
C11A C11B C5A C5 83.7(2) . . . . ?
C21 C11B C5A C5 -158.07(18) . . . . ?
O4 C3A C11C C1 177.7(2) . . . . ?
O3 C3A C11C C1 -1.2(2) . . . . ?
O4 C3A C11C C11B 0.6(3) . . . . ?
O3 C3A C11C C11B -178.24(16) . . . . ?
N2 C1 C11C C3A 0.8(2) . . . . ?
C12 C1 C11C C3A 179.6(2) . . . . ?
N2 C1 C11C C11B 177.2(2) . . . . ?
C12 C1 C11C C11B -4.1(4) . . . . ?
C11A C11B C11C C3A -109.3(2) . . . . ?
C21 C11B C11C C3A 129.0(2) . . . . ?
C5A C11B C11C C3A 10.8(3) . . . . ?
C11A C11B C11C C1 74.9(3) . . . . ?
C21 C11B C11C C1 -46.8(3) . . . . ?
C5A C11B C11C C1 -165.0(2) . . . . ?
C11A C11 C10 C9 0.9(3) . . . . ?
C11A C11 C10 Cl20 -178.27(17) . . . . ?
O7 C7A C8 C9 -177.7(2) . . . . ?
C11A C7A C8 C9 0.0(4) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?
C1 C12 C17 C16 178.1(2) . . . . ?
C17 C12 C13 C14 -0.9(3) . . . . ?
C1 C12 C13 C14 -177.7(2) . . . . ?
C3A O4 C5 C19 84.9(2) . . . . ?
C3A O4 C5 C18 -158.50(19) . . . . ?
C3A O4 C5 C5A -40.8(2) . . . . ?
C6 C5A C5 O4 -177.06(17) . . . . ?
C11B C5A C5 O4 55.7(2) . . . . ?
C6 C5A C5 C19 63.4(3) . . . . ?
C11B C5A C5 C19 -63.8(3) . . . . ?
C6 C5A C5 C18 -65.0(3) . . . . ?
C11B C5A C5 C18 167.77(19) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C7A C8 C9 C10 -0.1(4) . . . . ?
C11 C10 C9 C8 -0.3(4) . . . . ?
Cl20 C10 C9 C8 178.8(2) . . . . ?
C12 C17 C16 C15 -1.0(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C17 C16 C15 C14 0.1(4) . . . . ?
C7A O7 C6 C5A -44.1(3) . . . . ?
C5 C5A C6 O7 -71.1(3) . . . . ?
C11B C5A C6 O7 59.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.047
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_acyp1
_database_code_depnum_ccdc_archive 'CCDC 1025475'
_audit_update_record             
;
2014-09-22 deposited with the CCDC.
2015-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,12b-dimethyl-3-phenyl 3,4a,5,6,7,7a,7b,12b
octahydrochromeno[4',3',2':4,5]chromeno[2,3-c]pyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 N2 O2'
_chemical_formula_sum            'C24 H24 N2 O2'
_chemical_formula_weight         372.45

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   15.0693(8)
_cell_length_b                   7.8825(5)
_cell_length_c                   16.1470(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.896(6)
_cell_angle_gamma                90.00
_cell_volume                     1915.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2030
_cell_measurement_theta_min      3.9790
_cell_measurement_theta_max      28.1210

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84391
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Crys Alis RED'

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7489
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3744
_reflns_number_gt                2388
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0391P)²+0.1463P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0155(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3744
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.97668(8) 0.32807(17) 0.21721(8) 0.0443(4) Uani 1 1 d . . .
N3 N 0.97312(9) 0.5822(2) 0.29270(9) 0.0369(4) Uani 1 1 d . . .
O8 O 1.25489(8) 0.17906(19) 0.24939(9) 0.0525(4) Uani 1 1 d . . .
N2 N 1.01152(10) 0.6523(2) 0.36452(9) 0.0401(4) Uani 1 1 d . . .
C12B C 1.10159(11) 0.2058(2) 0.35557(11) 0.0366(5) Uani 1 1 d . . .
C12C C 1.06212(10) 0.3824(2) 0.34811(11) 0.0328(4) Uani 1 1 d . . .
C12A C 1.19915(12) 0.2012(2) 0.38736(12) 0.0395(5) Uani 1 1 d . . .
C7B C 1.09736(11) 0.1333(2) 0.26643(11) 0.0372(5) Uani 1 1 d . . .
H7B H 1.1113 0.0120 0.2704 0.045 Uiso 1 1 calc R . .
C3A C 1.00334(11) 0.4214(2) 0.28377(11) 0.0340(4) Uani 1 1 d . . .
C14 C 0.90555(11) 0.6723(2) 0.24695(11) 0.0354(5) Uani 1 1 d . . .
C1 C 1.06469(11) 0.5323(3) 0.39659(11) 0.0353(5) Uani 1 1 d . . .
C8A C 1.26766(12) 0.1854(3) 0.33320(13) 0.0430(5) Uani 1 1 d . . .
C15 C 0.88762(12) 0.6421(3) 0.16366(12) 0.0452(5) Uani 1 1 d . . .
H15 H 0.9210 0.5633 0.1357 0.054 Uiso 1 1 calc R . .
C7A C 1.16715(11) 0.2155(3) 0.21534(11) 0.0398(5) Uani 1 1 d . . .
H7A H 1.1582 0.3387 0.2157 0.048 Uiso 1 1 calc R . .
C4A C 1.00563(12) 0.1502(3) 0.22270(12) 0.0429(5) Uani 1 1 d . . .
H4A H 0.9627 0.0856 0.2536 0.051 Uiso 1 1 calc R . .
C9 C 1.35534(13) 0.1700(3) 0.36273(16) 0.0577(6) Uani 1 1 d . . .
H9 H 1.3999 0.1578 0.3254 0.069 Uiso 1 1 calc R . .
C5 C 1.00319(13) 0.0872(3) 0.13450(13) 0.0541(6) Uani 1 1 d . . .
H5A H 0.9448 0.1088 0.1085 0.065 Uiso 1 1 calc R . .
H5B H 1.0130 -0.0344 0.1345 0.065 Uiso 1 1 calc R . .
C7 C 1.16474(13) 0.1552(3) 0.12664(12) 0.0543(6) Uani 1 1 d . . .
H7D H 1.1826 0.0371 0.1254 0.065 Uiso 1 1 calc R . .
H7E H 1.2070 0.2203 0.0962 0.065 Uiso 1 1 calc R . .
C13 C 1.11625(12) 0.5697(3) 0.47556(11) 0.0491(6) Uani 1 1 d . . .
H13A H 1.1090 0.6871 0.4896 0.074 Uiso 1 1 calc R . .
H13B H 1.1780 0.5463 0.4689 0.074 Uiso 1 1 calc R . .
H13C H 1.0950 0.4999 0.5190 0.074 Uiso 1 1 calc R . .
C19 C 0.85697(12) 0.7922(3) 0.28760(13) 0.0505(6) Uani 1 1 d . . .
H19 H 0.8691 0.8132 0.3437 0.061 Uiso 1 1 calc R . .
C20 C 1.04508(13) 0.0964(3) 0.41197(13) 0.0540(6) Uani 1 1 d . . .
H20A H 1.0469 0.1442 0.4667 0.081 Uiso 1 1 calc R . .
H20B H 1.0684 -0.0169 0.4145 0.081 Uiso 1 1 calc R . .
H20C H 0.9848 0.0937 0.3899 0.081 Uiso 1 1 calc R . .
C6 C 1.07322(14) 0.1732(3) 0.08442(13) 0.0584(6) Uani 1 1 d . . .
H6A H 1.0731 0.1228 0.0296 0.070 Uiso 1 1 calc R . .
H6B H 1.0589 0.2926 0.0780 0.070 Uiso 1 1 calc R . .
C12 C 1.22349(14) 0.2016(3) 0.47145(13) 0.0573(6) Uani 1 1 d . . .
H12 H 1.1794 0.2108 0.5094 0.069 Uiso 1 1 calc R . .
C17 C 0.77139(15) 0.8490(4) 0.16222(17) 0.0733(8) Uani 1 1 d . . .
H17 H 0.7259 0.9078 0.1337 0.088 Uiso 1 1 calc R . .
C16 C 0.81985(14) 0.7298(3) 0.12205(14) 0.0606(7) Uani 1 1 d . . .
H16 H 0.8068 0.7080 0.0662 0.073 Uiso 1 1 calc R . .
C10 C 1.37710(16) 0.1725(3) 0.44590(18) 0.0685(7) Uani 1 1 d . . .
H10 H 1.4361 0.1632 0.4652 0.082 Uiso 1 1 calc R . .
C11 C 1.31101(17) 0.1888(3) 0.50062(16) 0.0718(7) Uani 1 1 d . . .
H11 H 1.3251 0.1912 0.5574 0.086 Uiso 1 1 calc R . .
C18 C 0.79050(15) 0.8807(3) 0.24470(16) 0.0701(7) Uani 1 1 d . . .
H18 H 0.7584 0.9626 0.2719 0.084 Uiso 1 1 calc R . .


_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
O4 C3A 1.347(2) . ?
O4 C4A 1.469(2) . ?
N3 C3A 1.357(2) . ?
N3 N2 1.3848(19) . ?
N3 C14 1.418(2) . ?
O8 C8A 1.358(2) . ?
O8 C7A 1.435(2) . ?
N2 C1 1.328(2) . ?
C12B C12C 1.516(2) . ?
C12B C12A 1.533(2) . ?
C12B C20 1.542(2) . ?
C12B C7B 1.547(2) . ?
C12C C3A 1.366(2) . ?
C12C C1 1.417(2) . ?
C12A C12 1.388(3) . ?
C12A C8A 1.392(3) . ?
C7B C7A 1.515(2) . ?
C7B C4A 1.526(2) . ?
C7B H7B 0.9800 . ?
C14 C15 1.379(2) . ?
C14 C19 1.382(3) . ?
C1 C13 1.489(2) . ?
C8A C9 1.387(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C7A C7 1.508(2) . ?
C7A H7A 0.9800 . ?
C4A C5 1.507(2) . ?
C4A H4A 0.9800 . ?
C9 C10 1.366(3) . ?
C9 H9 0.9300 . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C6 1.514(3) . ?
C7 H7D 0.9700 . ?
C7 H7E 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C19 C18 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C12 C11 1.382(3) . ?
C12 H12 0.9300 . ?
C17 C18 1.371(3) . ?
C17 C16 1.372(3) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C18 H18 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
C3A O4 C4A 113.39(14) . . ?
C3A N3 N2 109.49(14) . . ?
C3A N3 C14 130.43(16) . . ?
N2 N3 C14 119.66(15) . . ?
C8A O8 C7A 117.12(14) . . ?
C1 N2 N3 105.09(15) . . ?
C12C C12B C12A 114.45(15) . . ?
C12C C12B C20 109.53(15) . . ?
C12A C12B C20 109.76(15) . . ?
C12C C12B C7B 105.53(15) . . ?
C12A C12B C7B 107.26(14) . . ?
C20 C12B C7B 110.18(16) . . ?
C3A C12C C1 103.38(16) . . ?
C3A C12C C12B 120.24(17) . . ?
C1 C12C C12B 136.23(16) . . ?
C12 C12A C8A 116.55(18) . . ?
C12 C12A C12B 121.93(18) . . ?
C8A C12A C12B 121.39(17) . . ?
C7A C7B C4A 110.37(15) . . ?
C7A C7B C12B 110.57(15) . . ?
C4A C7B C12B 113.07(14) . . ?
C7A C7B H7B 107.5 . . ?
C4A C7B H7B 107.5 . . ?
C12B C7B H7B 107.5 . . ?
O4 C3A N3 120.44(16) . . ?
O4 C3A C12C 129.80(18) . . ?
N3 C3A C12C 109.72(16) . . ?
C15 C14 C19 119.91(18) . . ?
C15 C14 N3 121.47(17) . . ?
C19 C14 N3 118.62(17) . . ?
N2 C1 C12C 112.31(16) . . ?
N2 C1 C13 118.11(17) . . ?
C12C C1 C13 129.58(18) . . ?
O8 C8A C9 115.09(18) . . ?
O8 C8A C12A 123.85(16) . . ?
C9 C8A C12A 121.0(2) . . ?
C14 C15 C16 119.5(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
O8 C7A C7 106.16(14) . . ?
O8 C7A C7B 110.92(15) . . ?
C7 C7A C7B 113.46(16) . . ?
O8 C7A H7A 108.7 . . ?
C7 C7A H7A 108.7 . . ?
C7B C7A H7A 108.7 . . ?
O4 C4A C5 105.32(16) . . ?
O4 C4A C7B 111.76(15) . . ?
C5 C4A C7B 112.75(16) . . ?
O4 C4A H4A 109.0 . . ?
C5 C4A H4A 109.0 . . ?
C7B C4A H4A 109.0 . . ?
C10 C9 C8A 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C8A C9 H9 119.5 . . ?
C4A C5 C6 111.79(17) . . ?
C4A C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4A C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C7A C7 C6 112.07(16) . . ?
C7A C7 H7D 109.2 . . ?
C6 C7 H7D 109.2 . . ?
C7A C7 H7E 109.2 . . ?
C6 C7 H7E 109.2 . . ?
H7D C7 H7E 107.9 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C18 C19 C14 119.8(2) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C12B C20 H20A 109.5 . . ?
C12B C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12B C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 C6 C5 111.08(18) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C11 C12 C12A 122.3(2) . . ?
C11 C12 H12 118.9 . . ?
C12A C12 H12 118.9 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?

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
C3A N3 N2 C1 0.64(19) . . . . ?
C14 N3 N2 C1 173.97(15) . . . . ?
C12A C12B C12C C3A 142.72(17) . . . . ?
C20 C12B C12C C3A -93.55(19) . . . . ?
C7B C12B C12C C3A 25.0(2) . . . . ?
C12A C12B C12C C1 -42.6(3) . . . . ?
C20 C12B C12C C1 81.1(2) . . . . ?
C7B C12B C12C C1 -160.31(19) . . . . ?
C12C C12B C12A C12 85.5(2) . . . . ?
C20 C12B C12A C12 -38.1(3) . . . . ?
C7B C12B C12A C12 -157.76(18) . . . . ?
C12C C12B C12A C8A -98.7(2) . . . . ?
C20 C12B C12A C8A 137.71(19) . . . . ?
C7B C12B C12A C8A 18.0(2) . . . . ?
C12C C12B C7B C7A 73.90(17) . . . . ?
C12A C12B C7B C7A -48.5(2) . . . . ?
C20 C12B C7B C7A -167.94(15) . . . . ?
C12C C12B C7B C4A -50.43(19) . . . . ?
C12A C12B C7B C4A -172.85(15) . . . . ?
C20 C12B C7B C4A 67.7(2) . . . . ?
C4A O4 C3A N3 -172.05(15) . . . . ?
C4A O4 C3A C12C 10.3(3) . . . . ?
N2 N3 C3A O4 -178.58(14) . . . . ?
C14 N3 C3A O4 9.0(3) . . . . ?
N2 N3 C3A C12C -0.51(19) . . . . ?
C14 N3 C3A C12C -172.90(16) . . . . ?
C1 C12C C3A O4 178.01(17) . . . . ?
C12B C12C C3A O4 -5.8(3) . . . . ?
C1 C12C C3A N3 0.17(19) . . . . ?
C12B C12C C3A N3 176.36(14) . . . . ?
C3A N3 C14 C15 -31.7(3) . . . . ?
N2 N3 C14 C15 156.59(17) . . . . ?
C3A N3 C14 C19 148.17(19) . . . . ?
N2 N3 C14 C19 -23.6(2) . . . . ?
N3 N2 C1 C12C -0.54(19) . . . . ?
N3 N2 C1 C13 -179.95(14) . . . . ?
C3A C12C C1 N2 0.2(2) . . . . ?
C12B C12C C1 N2 -175.00(18) . . . . ?
C3A C12C C1 C13 179.56(17) . . . . ?
C12B C12C C1 C13 4.3(3) . . . . ?
C7A O8 C8A C9 -172.39(17) . . . . ?
C7A O8 C8A C12A 9.3(3) . . . . ?
C12 C12A C8A O8 178.49(19) . . . . ?
C12B C12A C8A O8 2.5(3) . . . . ?
C12 C12A C8A C9 0.3(3) . . . . ?
C12B C12A C8A C9 -175.68(18) . . . . ?
C19 C14 C15 C16 -1.4(3) . . . . ?
N3 C14 C15 C16 178.44(18) . . . . ?
C8A O8 C7A C7 -165.20(17) . . . . ?
C8A O8 C7A C7B -41.5(2) . . . . ?
C4A C7B C7A O8 -171.48(15) . . . . ?
C12B C7B C7A O8 62.65(19) . . . . ?
C4A C7B C7A C7 -52.1(2) . . . . ?
C12B C7B C7A C7 -177.97(16) . . . . ?
C3A O4 C4A C5 -158.10(14) . . . . ?
C3A O4 C4A C7B -35.3(2) . . . . ?
C7A C7B C4A O4 -65.7(2) . . . . ?
C12B C7B C4A O4 58.7(2) . . . . ?
C7A C7B C4A C5 52.7(2) . . . . ?
C12B C7B C4A C5 177.16(16) . . . . ?
O8 C8A C9 C10 -179.3(2) . . . . ?
C12A C8A C9 C10 -1.0(3) . . . . ?
O4 C4A C5 C6 67.4(2) . . . . ?
C7B C4A C5 C6 -54.7(2) . . . . ?
O8 C7A C7 C6 175.54(17) . . . . ?
C7B C7A C7 C6 53.5(2) . . . . ?
C15 C14 C19 C18 0.3(3) . . . . ?
N3 C14 C19 C18 -179.55(19) . . . . ?
C7A C7 C6 C5 -53.4(2) . . . . ?
C4A C5 C6 C7 54.2(2) . . . . ?
C8A C12A C12 C11 0.7(3) . . . . ?
C12B C12A C12 C11 176.6(2) . . . . ?
C18 C17 C16 C15 -0.2(4) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
C8A C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C12A C12 C11 C10 -1.0(4) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C14 C19 C18 C17 0.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.034
