data_global

# 1. SUBMISSION DETAILS

_publ_contact_author_name         'Dr. Viktor A. Tafeenko'
_publ_contact_author_address
;
      Chemistry Department,
      Moscow State University,
      119899 Moscow,
      Russia
;
_publ_contact_author_email        'tafeenko-victor@yandex.ru'
_publ_contact_author_fax          '+ 7-095-9390898'
_publ_contact_author_phone        '+ 7-095-9393654'


_publ_contact_letter
;
 Please consider this CIF file for deposition in the CSD 
(Cambridge Structural Database)
 The paper will be submitted in the  journal 
Angew. Chem. Int., 2013 
;
_journal_name_full     
' Angewandte Chemie international edition'

loop_
_publ_author_name
_publ_author_address
    'Kovalev, Vladimir'
;     Chemistry Department,
    Moscow State University,
      119899 Moscow,
      Russia
;
    'Shokova, Elvira'
;     Chemistry Department,
    Moscow State University,
      119899 Moscow,
      Russia
; 
    'Kim, J.'
;     Chemistry Department,
    Moscow State University,
      119899 Moscow,
      Russia
; 

     'Tafeenko, Viktor'
;     Chemistry Department,
      Moscow State University,
      119899 Moscow,
      Russia
;      
data_jk113a
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             
'7-bromo-3-(bromphenyl)-2,4-dihydro-indeno[1,2-c]pyrazole'
_chemical_melting_point           420
_chemical_formula_moiety          'C18 H14 Br2 N2'
_chemical_formula_sum
 'C18 H14 Br2 N2'
_chemical_formula_weight          418.13
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'
 'Br'  'Br'  -0.6763   1.2805
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0311   0.0180
 '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                    4.77210(10)
_cell_length_b                    11.6674(4)
_cell_length_c                    28.3435(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.5770(10)
_cell_angle_gamma                 90.00
_cell_volume                      1577.51(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     295(2)
_cell_measurement_reflns_used     22576
_cell_measurement_theta_min       3.79
_cell_measurement_theta_max       72.41
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           .2
_exptl_crystal_size_mid           .06
_exptl_crystal_size_min           .03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.761
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              824
_exptl_absorpt_coefficient_mu     6.484
_exptl_absorpt_correction_type  multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min   0.27
_exptl_absorpt_correction_T_max   0.72

_exptl_special_details
;
 ?
;
_diffrn_detector                   'Pilatus100K'
_diffrn_detector_type              'STOE'
_diffrn_source           'Cu GeniX 3D'
_diffrn_source_voltage             50
_diffrn_source_current             0.600
_diffrn_source_power               0.030
_diffrn_radiation_type             'Cu K\a'
_diffrn_radiation_wavelength       1.54186
_diffrn_radiation_monochromator    'none'
_diffrn_radiation_polarisn_norm    0
_diffrn_radiation_collimation      'focusing mirrors' 
_diffrn_ambient_temperature       295(2)
_diffrn_standards_decay_%         0
_diffrn_reflns_number             7328
_diffrn_reflns_av_R_equivalents   0.0540
_diffrn_reflns_av_sigmaI/netI     0.0504
_diffrn_reflns_limit_h_min        -4
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -30
_diffrn_reflns_limit_l_max        34
_diffrn_reflns_theta_min          4.10
_diffrn_reflns_theta_max          70.98
_reflns_number_total              3049
_reflns_number_gt                 2197
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
 
_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)+(0.0615P)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     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3049
_refine_ls_number_parameters      203
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0521
_refine_ls_R_factor_gt            0.0400
_refine_ls_wR_factor_ref          0.1001
_refine_ls_wR_factor_gt           0.0971
_refine_ls_goodness_of_fit_ref    0.902
_refine_ls_restrained_S_all       0.902
_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
Br1 Br 0.05105(9) 0.63679(3) 0.268950(13) 0.05833(16) Uani 1 1 d . . .
Br2 Br -1.78371(11) -0.02004(4) 0.652426(17) 0.07411(19) Uani 1 1 d . . .
N1 N -0.6771(7) 0.4078(3) 0.47281(10) 0.0534(8) Uani 1 1 d . . .
N2 N -0.5030(7) 0.4720(2) 0.44602(10) 0.0521(8) Uani 1 1 d . . .
C1 C -0.8146(8) 0.3232(3) 0.44906(12) 0.0448(8) Uani 1 1 d . . .
C2 C -1.0139(8) 0.2458(3) 0.47382(12) 0.0503(9) Uani 1 1 d . . .
H2A H -0.9567 0.1668 0.4693 0.060 Uiso 1 1 calc R . .
H2B H -1.2000 0.2548 0.4597 0.060 Uiso 1 1 calc R . .
C3 C -1.0256(9) 0.2703(4) 0.52599(12) 0.0579(10) Uani 1 1 d . . .
H3A H -0.8376 0.2620 0.5394 0.069 Uiso 1 1 calc R . .
H3B H -1.0793 0.3499 0.5298 0.069 Uiso 1 1 calc R . .
C4 C -0.7552(8) 0.2840(3) 0.35386(11) 0.0434(8) Uani 1 1 d . . .
H4A H -0.9461 0.2906 0.3415 0.052 Uiso 1 1 calc R . .
H4B H -0.6973 0.2043 0.3529 0.052 Uiso 1 1 calc R . .
C5 C -0.4880(8) 0.3599(3) 0.28015(12) 0.0506(9) Uani 1 1 d . . .
H5 H -0.5672 0.3054 0.2599 0.061 Uiso 1 1 calc R . .
C6 C -0.3014(8) 0.4405(3) 0.26302(11) 0.0499(9) Uani 1 1 d . . .
H6 H -0.2533 0.4394 0.2314 0.060 Uiso 1 1 calc R . .
C7 C -0.1885(8) 0.5220(3) 0.29317(11) 0.0442(8) Uani 1 1 d . . .
C8 C -0.2464(8) 0.5247(3) 0.34042(11) 0.0439(8) Uani 1 1 d . . .
H8 H -0.1644 0.5790 0.3605 0.053 Uiso 1 1 calc R . .
C9 C -0.4310(7) 0.4439(3) 0.35705(10) 0.0407(7) Uani 1 1 d . . .
C10 C -0.5554(7) 0.3609(3) 0.32716(11) 0.0413(7) Uani 1 1 d . . .
C11 C -0.5380(8) 0.4237(3) 0.40362(10) 0.0423(8) Uani 1 1 d . . .
C12 C -0.7256(8) 0.3326(3) 0.40306(11) 0.0418(8) Uani 1 1 d . . .
C13 C -1.2193(8) 0.1982(3) 0.55457(12) 0.0479(8) Uani 1 1 d . . .
C14 C -1.2883(9) 0.0856(3) 0.54343(13) 0.0581(10) Uani 1 1 d . . .
H14 H -1.2194 0.0529 0.5162 0.070 Uiso 1 1 calc R . .
C15 C -1.4577(10) 0.0208(3) 0.57211(14) 0.0602(11) Uani 1 1 d . . .
H15 H -1.5016 -0.0546 0.5642 0.072 Uiso 1 1 calc R . .
C16 C -1.5591(8) 0.0688(3) 0.61201(12) 0.0500(9) Uani 1 1 d . . .
C17 C -1.4954(9) 0.1795(4) 0.62451(13) 0.0593(10) Uani 1 1 d . . .
H17 H -1.5659 0.2114 0.6518 0.071 Uiso 1 1 calc R . .
C18 C -1.3252(9) 0.2428(3) 0.59593(13) 0.0555(10) Uani 1 1 d . . .
H18 H -1.2798 0.3176 0.6046 0.067 Uiso 1 1 calc R . .
H1 H -0.676(8) 0.428(3) 0.5031(14) 0.052(10) Uiso 1 1 d . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
Br1 0.0685(3) 0.0578(2) 0.0496(2) 0.00966(16) 0.02047(19) -0.00446(19)
Br2 0.0760(4) 0.0812(3) 0.0664(3) 0.0219(2) 0.0247(2) -0.0132(2)
N1 0.074(2) 0.0540(17) 0.0329(14) -0.0058(13) 0.0144(14) -0.0244(16)
N2 0.071(2) 0.0497(16) 0.0365(14) -0.0027(12) 0.0131(14) -0.0227(15)
C1 0.055(2) 0.0417(16) 0.0379(16) -0.0014(14) 0.0069(15) -0.0076(16)
C2 0.062(3) 0.0487(18) 0.0406(18) 0.0007(14) 0.0126(17) -0.0137(17)
C3 0.068(3) 0.066(2) 0.0402(18) 0.0007(17) 0.0089(18) -0.021(2)
C4 0.048(2) 0.0442(17) 0.0384(16) -0.0058(13) 0.0022(15) -0.0059(15)
C5 0.059(2) 0.057(2) 0.0362(16) -0.0095(15) 0.0029(16) -0.0024(18)
C6 0.058(2) 0.059(2) 0.0325(16) -0.0032(15) 0.0075(15) 0.0030(18)
C7 0.048(2) 0.0462(18) 0.0384(17) 0.0052(14) 0.0084(15) 0.0071(16)
C8 0.053(2) 0.0425(17) 0.0367(16) -0.0010(13) 0.0100(15) -0.0022(15)
C9 0.048(2) 0.0420(16) 0.0322(15) -0.0018(12) 0.0061(14) -0.0016(14)
C10 0.046(2) 0.0434(17) 0.0349(15) -0.0046(13) 0.0027(14) 0.0003(15)
C11 0.054(2) 0.0425(17) 0.0305(15) -0.0008(12) 0.0079(14) -0.0085(15)
C12 0.048(2) 0.0417(16) 0.0359(16) -0.0020(13) 0.0057(14) -0.0069(15)
C13 0.050(2) 0.057(2) 0.0374(16) 0.0051(15) 0.0057(15) -0.0082(17)
C14 0.072(3) 0.060(2) 0.0438(19) -0.0048(17) 0.0167(18) -0.014(2)
C15 0.075(3) 0.055(2) 0.051(2) -0.0001(17) 0.009(2) -0.016(2)
C16 0.049(2) 0.059(2) 0.0422(17) 0.0126(16) 0.0068(16) -0.0035(18)
C17 0.071(3) 0.064(2) 0.0440(19) 0.0003(17) 0.0176(18) -0.003(2)
C18 0.069(3) 0.051(2) 0.048(2) -0.0042(15) 0.0131(18) -0.0112(18)
 
_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 C7 1.901(3) . ?
Br2 C16 1.898(3) . ?
N1 C1 1.354(5) . ?
N1 N2 1.365(4) . ?
N2 C11 1.334(4) . ?
C1 C12 1.387(4) . ?
C1 C2 1.500(5) . ?
C2 C3 1.509(5) . ?
C3 C13 1.503(5) . ?
C4 C12 1.508(4) . ?
C4 C10 1.526(5) . ?
C5 C10 1.379(4) . ?
C5 C6 1.392(5) . ?
C6 C7 1.378(5) . ?
C7 C8 1.375(4) . ?
C8 C9 1.382(5) . ?
C9 C10 1.407(5) . ?
C9 C11 1.448(4) . ?
C11 C12 1.390(5) . ?
C13 C14 1.388(5) . ?
C13 C18 1.391(5) . ?
C14 C15 1.386(5) . ?
C15 C16 1.363(5) . ?
C16 C17 1.372(6) . ?
C17 C18 1.377(5) . ?
 
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 N2 114.7(3) . . ?
C11 N2 N1 101.9(3) . . ?
N1 C1 C12 104.7(3) . . ?
N1 C1 C2 120.8(3) . . ?
C12 C1 C2 134.6(3) . . ?
C1 C2 C3 112.7(3) . . ?
C13 C3 C2 117.5(3) . . ?
C12 C4 C10 101.2(3) . . ?
C10 C5 C6 120.0(3) . . ?
C7 C6 C5 119.5(3) . . ?
C8 C7 C6 122.3(3) . . ?
C8 C7 Br1 118.3(3) . . ?
C6 C7 Br1 119.4(2) . . ?
C7 C8 C9 117.6(3) . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 C11 131.8(3) . . ?
C10 C9 C11 106.5(3) . . ?
C5 C10 C9 118.8(3) . . ?
C5 C10 C4 129.8(3) . . ?
C9 C10 C4 111.4(3) . . ?
N2 C11 C12 113.5(3) . . ?
N2 C11 C9 135.6(3) . . ?
C12 C11 C9 110.9(3) . . ?
C1 C12 C11 105.3(3) . . ?
C1 C12 C4 144.7(3) . . ?
C11 C12 C4 110.0(3) . . ?
C14 C13 C18 117.2(3) . . ?
C14 C13 C3 123.5(3) . . ?
C18 C13 C3 119.2(3) . . ?
C15 C14 C13 121.4(3) . . ?
C16 C15 C14 119.3(4) . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 Br2 119.7(3) . . ?
C17 C16 Br2 118.9(3) . . ?
C16 C17 C18 118.9(3) . . ?
C17 C18 C13 121.9(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              70.98
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.621
_refine_diff_density_min   -0.667
_refine_diff_density_rms    0.084
