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#$Date: 2016-03-21 19:09:12 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178837 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/91/4109120.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4109120
loop_
_publ_author_name
'Masaki Kawano'
'Katsuyuki Hirai'
'Hideo Tomioka'
'Yuji Ohashi'
_publ_contact_author             'Masaki Kawano'
_publ_contact_author_email       mkawano@chem.titech.ac.jp
_publ_section_title
;
 Structure Determination of Triplet Diphenylcarbenes by in Situ X-ray
 Crystallographic Analysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2383
_journal_page_last               2391
_journal_paper_doi               10.1021/ja067306b
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C15 H10 Br4 N2'
_chemical_formula_weight         537.89
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.629(1)
_cell_angle_beta                 82.928(1)
_cell_angle_gamma                71.105(1)
_cell_formula_units_Z            2
_cell_length_a                   8.3253(3)
_cell_length_b                   8.5901(3)
_cell_length_c                   12.3494(4)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    80(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     817.50(5)
_computing_cell_refinement       'Siemens SMART'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT & SADABS'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      80(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Siemens SMART CCD area detector system'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36715
_diffrn_reflns_theta_full        42.62
_diffrn_reflns_theta_max         42.62
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    9.839
_exptl_absorpt_correction_T_max  0.3848
_exptl_absorpt_correction_T_min  0.1563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.185
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.462
_refine_diff_density_min         -1.836
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    ride
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         11151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0367P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                7951
_reflns_number_total             11151
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067306bsi20061011_075725_3.cif
_cod_data_source_block           (PhBr2Me)2CN2_(3)
_cod_database_code               4109120
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 0.75500(3) 0.46875(2) 1.073500(14) 0.01991(4) Uani 1 1 d .
Br2 Br 0.64257(2) 1.08660(2) 1.230289(13) 0.01803(4) Uani 1 1 d .
Br3 Br 1.08584(2) 0.59965(2) 1.208528(13) 0.01641(3) Uani 1 1 d .
Br4 Br 0.467285(19) 0.80080(2) 1.478876(13) 0.01599(3) Uani 1 1 d .
N1 N 0.58380(17) 0.60766(17) 1.28323(11) 0.0141(2) Uani 1 1 d .
N2 N 0.4940(2) 0.5290(2) 1.30457(13) 0.0195(3) Uani 1 1 d .
C1 C 0.68835(19) 0.69845(19) 1.25888(12) 0.0127(2) Uani 1 1 d .
C2 C 0.7675(3) 1.0301(2) 0.80325(14) 0.0210(3) Uani 1 1 d .
H2A H 0.7581 1.1470 0.8026 0.032 Uiso 1 1 calc R
H2B H 0.6809 1.0251 0.7582 0.032 Uiso 1 1 calc R
H2C H 0.8808 0.9725 0.7727 0.032 Uiso 1 1 calc R
C3 C 1.0696(2) 0.7536(2) 1.60948(14) 0.0175(3) Uani 1 1 d .
H3A H 0.9919 0.7831 1.6738 0.026 Uiso 1 1 calc R
H3B H 1.1210 0.8425 1.5805 0.026 Uiso 1 1 calc R
H3C H 1.1593 0.6488 1.6316 0.026 Uiso 1 1 calc R
C11 C 0.70136(19) 0.78357(18) 1.14314(12) 0.0127(2) Uani 1 1 d .
C12 C 0.7296(2) 0.70018(19) 1.05170(13) 0.0138(2) Uani 1 1 d .
C13 C 0.7467(2) 0.7794(2) 0.94309(13) 0.0158(3) Uani 1 1 d .
H13A H 0.7624 0.7191 0.8839 0.019 Uiso 1 1 calc R
C14 C 0.7410(2) 0.9468(2) 0.92043(13) 0.0153(3) Uani 1 1 d .
C15 C 0.7129(2) 1.03327(19) 1.00922(13) 0.0154(3) Uani 1 1 d .
H15A H 0.7082 1.1474 0.9959 0.018 Uiso 1 1 calc R
C16 C 0.6916(2) 0.95321(19) 1.11701(13) 0.0144(2) Uani 1 1 d .
C21 C 0.78431(19) 0.70472(18) 1.35023(12) 0.0118(2) Uani 1 1 d .
C22 C 0.96218(19) 0.67262(19) 1.33862(12) 0.0128(2) Uani 1 1 d .
C23 C 1.05434(19) 0.6874(2) 1.42046(13) 0.0140(2) Uani 1 1 d .
H23A H 1.1738 0.6668 1.4082 0.017 Uiso 1 1 calc R
C24 C 0.97224(19) 0.73255(19) 1.52106(13) 0.0135(2) Uani 1 1 d .
C25 C 0.79670(19) 0.75871(19) 1.53676(12) 0.0135(2) Uani 1 1 d .
H25A H 0.7386 0.7846 1.6053 0.016 Uiso 1 1 calc R
C26 C 0.70689(19) 0.74701(19) 1.45244(12) 0.0126(2) Uani 1 1 d .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 C1 179.73(19)
N1 C1 C21 116.71(13)
N1 C1 C11 117.71(14)
C21 C1 C11 125.58(13)
C16 C11 C12 115.24(13)
C16 C11 C1 121.98(13)
C12 C11 C1 122.75(13)
C13 C12 C11 122.62(14)
C13 C12 Br1 116.97(11)
C11 C12 Br1 120.36(11)
C12 C13 C14 120.58(14)
C13 C14 C15 118.24(14)
C13 C14 C2 120.48(14)
C15 C14 C2 121.27(14)
C16 C15 C14 120.39(14)
C15 C16 C11 122.89(14)
C15 C16 Br2 116.58(11)
C11 C16 Br2 120.52(11)
C26 C21 C22 115.15(13)
C26 C21 C1 123.32(13)
C22 C21 C1 121.50(13)
C23 C22 C21 122.78(14)
C23 C22 Br3 117.43(11)
C21 C22 Br3 119.76(11)
C22 C23 C24 120.48(14)
C25 C24 C23 118.05(14)
C25 C24 C3 120.82(14)
C23 C24 C3 121.13(14)
C26 C25 C24 120.26(14)
C25 C26 C21 123.21(14)
C25 C26 Br4 116.61(11)
C21 C26 Br4 120.13(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.8974(15)
Br2 C16 1.9039(15)
Br3 C22 1.8989(15)
Br4 C26 1.8978(15)
N1 N2 1.137(2)
N1 C1 1.319(2)
C1 C21 1.479(2)
C1 C11 1.480(2)
C2 C14 1.507(2)
C3 C24 1.507(2)
C11 C16 1.407(2)
C11 C12 1.410(2)
C12 C13 1.392(2)
C13 C14 1.396(2)
C14 C15 1.398(2)
C15 C16 1.391(2)
C21 C26 1.403(2)
C21 C22 1.410(2)
C22 C23 1.390(2)
C23 C24 1.404(2)
C24 C25 1.399(2)
C25 C26 1.391(2)
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
N2 N1 C1 C21 -23(52)
N2 N1 C1 C11 156(100)
N1 C1 C11 C16 131.82(17)
C21 C1 C11 C16 -48.9(2)
N1 C1 C11 C12 -50.2(2)
C21 C1 C11 C12 129.09(17)
C16 C11 C12 C13 0.0(2)
C1 C11 C12 C13 -178.07(15)
C16 C11 C12 Br1 177.44(12)
C1 C11 C12 Br1 -0.6(2)
C11 C12 C13 C14 1.8(3)
Br1 C12 C13 C14 -175.75(13)
C12 C13 C14 C15 -1.8(3)
C12 C13 C14 C2 177.23(16)
C13 C14 C15 C16 0.2(3)
C2 C14 C15 C16 -178.88(17)
C14 C15 C16 C11 1.7(3)
C14 C15 C16 Br2 -176.90(13)
C12 C11 C16 C15 -1.7(2)
C1 C11 C16 C15 176.37(15)
C12 C11 C16 Br2 176.80(12)
C1 C11 C16 Br2 -5.1(2)
N1 C1 C21 C26 -52.4(2)
C11 C1 C21 C26 128.28(17)
N1 C1 C21 C22 129.49(16)
C11 C1 C21 C22 -49.8(2)
C26 C21 C22 C23 -2.2(2)
C1 C21 C22 C23 176.00(14)
C26 C21 C22 Br3 175.86(11)
C1 C21 C22 Br3 -5.89(19)
C21 C22 C23 C24 1.4(2)
Br3 C22 C23 C24 -176.78(12)
C22 C23 C24 C25 1.2(2)
C22 C23 C24 C3 -178.37(15)
C23 C24 C25 C26 -2.8(2)
C3 C24 C25 C26 176.81(15)
C24 C25 C26 C21 1.9(2)
C24 C25 C26 Br4 -175.55(12)
C22 C21 C26 C25 0.6(2)
C1 C21 C26 C25 -177.59(14)
C22 C21 C26 Br4 177.96(11)
C1 C21 C26 Br4 -0.3(2)
