# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_at98m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '3,5-diphenyl-1-(trifluoromethyl)-3,11-dihydro-
5,11-methanobenzo[7,8][1,3]dioxocino[4,5-c]pyrazole'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 F3 N2 O2'
_chemical_formula_sum            'C25 H17 F3 N2 O2'
_chemical_formula_weight         434.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   12.4985(13)
_cell_length_b                   9.3025(9)
_cell_length_c                   18.0441(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.754(2)
_cell_angle_gamma                90.00
_cell_volume                     2097.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6829
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      23.99

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9598
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany  
;

_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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19513
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3691
_reflns_number_gt                2984
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0621P)²+0.4576P] 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         3691
_refine_ls_number_parameters     316
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.282
_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
C1 C 0.40578(18) 0.2214(2) -0.01200(13) 0.0628(6) Uani 1 1 d . . .
C2 C 0.4896(2) 0.3194(3) -0.01328(17) 0.0781(7) Uani 1 1 d . . .
H2 H 0.5083 0.3711 0.0291 0.094 Uiso 1 1 calc R . .
C3 C 0.5447(2) 0.3390(3) -0.0783(2) 0.0921(9) Uani 1 1 d . . .
H3 H 0.6001 0.4056 -0.0799 0.111 Uiso 1 1 calc R . .
C4 C 0.5186(2) 0.2615(3) -0.14084(19) 0.0924(9) Uani 1 1 d . . .
H4 H 0.5556 0.2763 -0.1846 0.111 Uiso 1 1 calc R . .
C5 C 0.4370(2) 0.1612(3) -0.13834(15) 0.0783(7) Uani 1 1 d . . .
H5 H 0.4202 0.1077 -0.1805 0.094 Uiso 1 1 calc R . .
C6 C 0.37956(17) 0.1393(2) -0.07395(13) 0.0642(6) Uani 1 1 d . . .
C7 C 0.29052(17) 0.0310(2) -0.06599(12) 0.0631(6) Uani 1 1 d . . .
H7 H 0.2974 -0.0466 -0.1024 0.076 Uiso 1 1 calc R . .
C8 C 0.29747(18) -0.0281(2) 0.01326(12) 0.0631(6) Uani 1 1 d . . .
H8A H 0.2434 -0.1015 0.0201 0.076 Uiso 1 1 calc R . .
H8B H 0.3672 -0.0711 0.0221 0.076 Uiso 1 1 calc R . .
C9 C 0.27992(17) 0.0954(2) 0.06766(12) 0.0582(5) Uani 1 1 d . . .
C10 C 0.29146(18) 0.0513(2) 0.14806(12) 0.0605(5) Uani 1 1 d . . .
C11 C 0.38234(19) 0.0860(3) 0.18920(13) 0.0673(6) Uani 1 1 d . . .
H11 H 0.4356 0.1422 0.1682 0.081 Uiso 1 1 calc R . .
C12 C 0.3941(2) 0.0372(3) 0.26168(15) 0.0826(7) Uani 1 1 d . . .
H12 H 0.4549 0.0616 0.2891 0.099 Uiso 1 1 calc R . .
C13 C 0.3168(3) -0.0462(3) 0.29281(16) 0.0922(9) Uani 1 1 d . . .
H13 H 0.3253 -0.0797 0.3411 0.111 Uiso 1 1 calc R . .
C14 C 0.2267(3) -0.0804(4) 0.25243(17) 0.1036(10) Uani 1 1 d . . .
H14 H 0.1735 -0.1362 0.2737 0.124 Uiso 1 1 calc R . .
C15 C 0.2143(2) -0.0321(3) 0.18016(15) 0.0878(8) Uani 1 1 d . . .
H15 H 0.1531 -0.0566 0.1531 0.105 Uiso 1 1 calc R . .
C16 C 0.13320(17) 0.1529(2) -0.01067(11) 0.0563(5) Uani 1 1 d . . .
C17 C 0.18238(17) 0.1020(2) -0.07262(12) 0.0596(5) Uani 1 1 d . . .
C18 C 0.11066(17) 0.1400(3) -0.12994(12) 0.0632(6) Uani 1 1 d . A .
C19 C 0.12277(16) 0.1164(3) -0.21130(13) 0.0820(8) Uani 1 1 d D . .
C20 C -0.04089(16) 0.2852(2) 0.01330(11) 0.0562(5) Uani 1 1 d . . .
C21 C -0.0508(2) 0.2542(3) 0.08765(13) 0.0747(7) Uani 1 1 d . . .
H21 H -0.0069 0.1858 0.1102 0.090 Uiso 1 1 calc R . .
C22 C -0.1274(2) 0.3267(4) 0.12810(15) 0.0933(9) Uani 1 1 d . . .
H22 H -0.1346 0.3067 0.1783 0.112 Uiso 1 1 calc R . .
C23 C -0.1932(2) 0.4279(3) 0.09521(17) 0.0889(8) Uani 1 1 d . . .
H23 H -0.2438 0.4766 0.1230 0.107 Uiso 1 1 calc R . .
C24 C -0.1829(2) 0.4560(3) 0.02082(16) 0.0802(7) Uani 1 1 d . . .
H24 H -0.2275 0.5233 -0.0019 0.096 Uiso 1 1 calc R . .
C25 C -0.10729(19) 0.3851(3) -0.02023(14) 0.0696(6) Uani 1 1 d . . .
H25 H -0.1009 0.4045 -0.0705 0.084 Uiso 1 1 calc R . .
F1A F 0.0339(3) 0.1179(8) -0.2494(2) 0.1161(14) Uani 0.55 1 d PDU A 1
F2A F 0.1773(5) 0.2232(5) -0.2398(3) 0.1389(19) Uani 0.55 1 d PDU A 1
F3A F 0.1788(5) 0.0019(5) -0.2261(3) 0.1174(18) Uani 0.55 1 d PDU A 1
F1B F 0.0552(5) 0.0181(8) -0.2351(3) 0.137(2) Uani 0.45 1 d PDU A 2
F2B F 0.1102(8) 0.2301(6) -0.2522(3) 0.139(2) Uani 0.45 1 d PDU A 2
F3B F 0.2169(3) 0.0671(8) -0.2279(4) 0.111(2) Uani 0.45 1 d PDU A 2
N1 N 0.03787(13) 0.2137(2) -0.03053(9) 0.0578(4) Uani 1 1 d . A .
N2 N 0.02330(14) 0.2058(2) -0.10579(10) 0.0647(5) Uani 1 1 d . . .
O1 O 0.34963(13) 0.21251(16) 0.05400(9) 0.0671(4) Uani 1 1 d . . .
O2 O 0.16946(12) 0.15030(17) 0.06025(8) 0.0647(4) 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 C2 1.389(3) . ?
C1 C6 1.390(3) . ?
C1 O1 1.393(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(3) . ?
C7 C17 1.508(3) . ?
C7 C8 1.534(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.528(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O1 1.419(3) . ?
C9 O2 1.477(3) . ?
C9 C10 1.513(3) . ?
C10 C15 1.372(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.390(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.352(2) . ?
C16 N1 1.363(3) . ?
C16 C17 1.367(3) . ?
C17 C18 1.405(3) . ?
C18 N2 1.330(3) . ?
C18 C19 1.494(3) . ?
C19 F2B 1.297(2) . ?
C19 F1A 1.299(2) . ?
C19 F3B 1.302(2) . ?
C19 F3A 1.304(2) . ?
C19 F1B 1.313(2) . ?
C19 F2A 1.314(2) . ?
C20 C21 1.380(3) . ?
C20 C25 1.380(3) . ?
C20 N1 1.435(3) . ?
C21 C22 1.387(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N1 N2 1.370(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.2(2) . . ?
C2 C1 O1 116.2(2) . . ?
C6 C1 O1 122.6(2) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 124.6(2) . . ?
C1 C6 C7 117.2(2) . . ?
C17 C7 C6 111.20(18) . . ?
C17 C7 C8 105.70(18) . . ?
C6 C7 C8 107.17(18) . . ?
C17 C7 H7 110.9 . . ?
C6 C7 H7 110.9 . . ?
C8 C7 H7 110.9 . . ?
C9 C8 C7 108.83(17) . . ?
C9 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O1 C9 O2 107.11(16) . . ?
O1 C9 C10 108.91(17) . . ?
O2 C9 C10 104.95(17) . . ?
O1 C9 C8 111.83(18) . . ?
O2 C9 C8 110.10(16) . . ?
C10 C9 C8 113.54(18) . . ?
C15 C10 C11 118.8(2) . . ?
C15 C10 C9 120.0(2) . . ?
C11 C10 C9 121.1(2) . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.7(2) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O2 C16 N1 122.51(18) . . ?
O2 C16 C17 128.23(19) . . ?
N1 C16 C17 109.24(18) . . ?
C16 C17 C18 103.03(19) . . ?
C16 C17 C7 119.93(19) . . ?
C18 C17 C7 137.0(2) . . ?
N2 C18 C17 113.15(19) . . ?
N2 C18 C19 118.92(19) . . ?
C17 C18 C19 127.9(2) . . ?
F2B C19 F1A 66.1(4) . . ?
F2B C19 F3B 105.0(5) . . ?
F1A C19 F3B 130.6(4) . . ?
F2B C19 F3A 127.6(5) . . ?
F1A C19 F3A 111.0(4) . . ?
F3B C19 F3A 34.5(3) . . ?
F2B C19 F1B 108.0(5) . . ?
F1A C19 F1B 44.9(3) . . ?
F3B C19 F1B 105.0(5) . . ?
F3A C19 F1B 73.1(4) . . ?
F2B C19 F2A 38.8(4) . . ?
F1A C19 F2A 103.2(4) . . ?
F3B C19 F2A 72.6(4) . . ?
F3A C19 F2A 104.7(4) . . ?
F1B C19 F2A 137.1(4) . . ?
F2B C19 C18 115.2(4) . . ?
F1A C19 C18 114.9(2) . . ?
F3B C19 C18 112.4(4) . . ?
F3A C19 C18 112.5(3) . . ?
F1B C19 C18 110.5(3) . . ?
F2A C19 C18 109.5(3) . . ?
C21 C20 C25 120.4(2) . . ?
C21 C20 N1 120.7(2) . . ?
C25 C20 N1 118.93(19) . . ?
C20 C21 C22 118.8(2) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 121.2(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 119.1(2) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 120.0(2) . . ?
C24 C25 H25 120.0 . . ?
C20 C25 H25 120.0 . . ?
C16 N1 N2 110.07(17) . . ?
C16 N1 C20 130.65(17) . . ?
N2 N1 C20 119.21(16) . . ?
C18 N2 N1 104.49(17) . . ?
C1 O1 C9 120.78(17) . . ?
C16 O2 C9 113.16(16) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 994173'
