data_n2792
_audit_creation_date              2013-05-30
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_chemical_name_common             ?
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety          'C Br3 N O2, C10 H16 N2'
_chemical_formula_sum             'C11 H16 Br3 N3 O2'
_chemical_formula_weight          462.00
_chemical_melting_point           ?
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'
 'Br' 'Br' -0.2901 2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       'monoclinic'
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 1 21/n 1'
_space_group_name_Hall            '-P 2yn'
loop_
  _space_group_symop_operation_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                    5.8059(2)
_cell_length_b                    19.4214(8)
_cell_length_c                    13.5907(6)
_cell_angle_alpha                 90
_cell_angle_beta                  96.284(2)
_cell_angle_gamma                 90
_cell_volume                      1523.26(11)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     9989
_cell_measurement_temperature     100(2)
_cell_measurement_theta_max       30.14
_cell_measurement_theta_min       2.58
_exptl_absorpt_coefficient_mu     7.946
_exptl_absorpt_correction_T_max   0.7460
_exptl_absorpt_correction_T_min   0.4254
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1028 before and 0.0618 after correction.
The Ratio of minimum to maximum transmission is 0.5702.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour             orange
_exptl_crystal_colour_primary     orange
_exptl_crystal_density_diffrn     2.015
_exptl_crystal_density_meas       .
_exptl_crystal_density_method     ?
_exptl_crystal_description        'needle'
_exptl_crystal_F_000              896
_exptl_crystal_size_max           0.462
_exptl_crystal_size_mid           0.254
_exptl_crystal_size_min           0.033
_exptl_special_details
;
 ?
;
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0512
_diffrn_reflns_av_unetI/netI      0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_k_max        27
_diffrn_reflns_limit_k_min        -27
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_number             22814
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          30.188
_diffrn_reflns_theta_min          2.583
_diffrn_ambient_temperature       99.99
_diffrn_detector_area_resol_mean  8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type   'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method        'ω and φ scans'
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'sealed tube'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 3864
_reflns_number_total              4483
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection        'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction         'Bruker SAINT'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max          0.881
_refine_diff_density_min          -0.698
_refine_diff_density_rms          0.104
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.037
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      176
_refine_ls_number_reflns          4483
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0320
_refine_ls_R_factor_gt            0.0240
_refine_ls_restrained_S_all       1.037
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0241P)²+0.4000P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0547
_refine_ls_wR_factor_ref          0.0577
_refine_special_details
;
 ?
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Br1 Br 0.41531(3) 0.18492(2) 0.17924(2) 0.01578(6) Uani 1 1 d . . . . .
 Br2 Br 0.34165(3) 0.02252(2) 0.18645(2) 0.01376(5) Uani 1 1 d . . . . .
 Br3 Br 0.05035(3) 0.12182(2) 0.31497(2) 0.01291(5) Uani 1 1 d . . . . .
 O1 O -0.0524(3) 0.17541(7) 0.07671(11) 0.0222(3) Uani 1 1 d . . . . .
 O2 O -0.1099(3) 0.06603(8) 0.08489(12) 0.0284(4) Uani 1 1 d . . . . .
 N1 N -0.0044(3) 0.11830(8) 0.10950(12) 0.0142(3) Uani 1 1 d . . . . .
 C1 C 0.1976(4) 0.11180(10) 0.19320(14) 0.0131(4) Uani 1 1 d . . . . .
 N2 N 0.4683(3) 0.10651(8) 0.82054(12) 0.0139(3) Uani 1 1 d . . . . .
 N3 N -0.1705(3) 0.13209(8) 0.47527(11) 0.0132(3) Uani 1 1 d . . . . .
 C2 C 0.3097(4) 0.11522(10) 0.73417(14) 0.0130(4) Uani 1 1 d . . . . .
 C3 C 0.1396(4) 0.06566(10) 0.71102(14) 0.0158(4) Uani 1 1 d . . . . .
 H3 H 0.1327 0.0270 0.7534 0.019 Uiso 1 1 calc R U . . .
 C4 C -0.0197(4) 0.07102(10) 0.62798(14) 0.0150(4) Uani 1 1 d . . . . .
 H4 H -0.1351 0.0365 0.6151 0.018 Uiso 1 1 calc R U . . .
 C5 C -0.0134(4) 0.12626(10) 0.56301(14) 0.0130(4) Uani 1 1 d . . . . .
 C6 C 0.1602(4) 0.17534(10) 0.58476(14) 0.0145(4) Uani 1 1 d . . . . .
 H6 H 0.1707 0.2130 0.5409 0.017 Uiso 1 1 calc R U . . .
 C7 C 0.3176(4) 0.17043(10) 0.66882(14) 0.0140(4) Uani 1 1 d . . . . .
 H7 H 0.4323 0.2051 0.6821 0.017 Uiso 1 1 calc R U . . .
 C8 C 0.6621(4) 0.15515(11) 0.83275(15) 0.0192(4) Uani 1 1 d . . . . .
 H8A H 0.7425 0.1550 0.7730 0.029 Uiso 1 1 calc R U . . .
 H8B H 0.7704 0.1415 0.8898 0.029 Uiso 1 1 calc R U . . .
 H8C H 0.6033 0.2015 0.8436 0.029 Uiso 1 1 calc R U . . .
 C9 C 0.3598(4) 0.09933(10) 0.91225(15) 0.0197(5) Uani 1 1 d . . . . .
 H9A H 0.2849 0.1428 0.9269 0.030 Uiso 1 1 calc R U . . .
 H9B H 0.4783 0.0878 0.9667 0.030 Uiso 1 1 calc R U . . .
 H9C H 0.2435 0.0626 0.9045 0.030 Uiso 1 1 calc R U . . .
 C10 C -0.2784(4) 0.20032(10) 0.45985(15) 0.0176(4) Uani 1 1 d . . . . .
 H10A H -0.3780 0.2093 0.5122 0.026 Uiso 1 1 calc R U . . .
 H10B H -0.3717 0.2015 0.3953 0.026 Uiso 1 1 calc R U . . .
 H10C H -0.1573 0.2356 0.4619 0.026 Uiso 1 1 calc R U . . .
 C11 C -0.3446(4) 0.07757(11) 0.45931(15) 0.0185(4) Uani 1 1 d . . . . .
 H11A H -0.4479 0.0794 0.5117 0.028 Uiso 1 1 calc R U . . .
 H11B H -0.2673 0.0327 0.4608 0.028 Uiso 1 1 calc R U . . .
 H11C H -0.4352 0.0841 0.3948 0.028 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br1 C1 1.924(2) . ?
 Br2 C1 1.9318(19) . ?
 Br3 C1 1.954(2) . ?
 O1 N1 1.216(2) . ?
 O2 N1 1.214(2) . ?
 N1 C1 1.547(2) . ?
 N2 C2 1.421(2) . ?
 N2 C8 1.465(3) . ?
 N2 C9 1.463(3) . ?
 N3 C5 1.424(2) . ?
 N3 C10 1.471(2) . ?
 N3 C11 1.464(3) . ?
 C2 C3 1.390(3) . ?
 C2 C7 1.396(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.383(3) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.393(3) . ?
 C5 C6 1.395(3) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.386(3) . ?
 C7 H7 0.9500 . ?
 C8 H8A 0.9800 . ?
 C8 H8B 0.9800 . ?
 C8 H8C 0.9800 . ?
 C9 H9A 0.9800 . ?
 C9 H9B 0.9800 . ?
 C9 H9C 0.9800 . ?
 C10 H10A 0.9800 . ?
 C10 H10B 0.9800 . ?
 C10 H10C 0.9800 . ?
 C11 H11A 0.9800 . ?
 C11 H11B 0.9800 . ?
 C11 H11C 0.9800 . ?

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
 O1 N1 C1 117.94(16) . . ?
 O2 N1 O1 125.00(17) . . ?
 O2 N1 C1 116.96(16) . . ?
 Br1 C1 Br2 111.41(10) . . ?
 Br1 C1 Br3 111.29(9) . . ?
 Br2 C1 Br3 111.19(9) . . ?
 N1 C1 Br1 108.69(12) . . ?
 N1 C1 Br2 109.61(12) . . ?
 N1 C1 Br3 104.36(13) . . ?
 C2 N2 C8 115.94(16) . . ?
 C2 N2 C9 114.48(18) . . ?
 C9 N2 C8 111.23(16) . . ?
 C5 N3 C10 114.49(15) . . ?
 C5 N3 C11 115.81(15) . . ?
 C11 N3 C10 110.74(16) . . ?
 C3 C2 N2 119.00(17) . . ?
 C3 C2 C7 117.37(17) . . ?
 C7 C2 N2 123.61(18) . . ?
 C2 C3 H3 119.1 . . ?
 C4 C3 C2 121.86(18) . . ?
 C4 C3 H3 119.1 . . ?
 C3 C4 H4 119.5 . . ?
 C3 C4 C5 120.92(18) . . ?
 C5 C4 H4 119.5 . . ?
 C4 C5 N3 122.22(17) . . ?
 C4 C5 C6 117.43(17) . . ?
 C6 C5 N3 120.31(17) . . ?
 C5 C6 H6 119.2 . . ?
 C7 C6 C5 121.56(18) . . ?
 C7 C6 H6 119.2 . . ?
 C2 C7 H7 119.6 . . ?
 C6 C7 C2 120.84(18) . . ?
 C6 C7 H7 119.6 . . ?
 N2 C8 H8A 109.5 . . ?
 N2 C8 H8B 109.5 . . ?
 N2 C8 H8C 109.5 . . ?
 H8A C8 H8B 109.5 . . ?
 H8A C8 H8C 109.5 . . ?
 H8B C8 H8C 109.5 . . ?
 N2 C9 H9A 109.5 . . ?
 N2 C9 H9B 109.5 . . ?
 N2 C9 H9C 109.5 . . ?
 H9A C9 H9B 109.5 . . ?
 H9A C9 H9C 109.5 . . ?
 H9B C9 H9C 109.5 . . ?
 N3 C10 H10A 109.5 . . ?
 N3 C10 H10B 109.5 . . ?
 N3 C10 H10C 109.5 . . ?
 H10A C10 H10B 109.5 . . ?
 H10A C10 H10C 109.5 . . ?
 H10B C10 H10C 109.5 . . ?
 N3 C11 H11A 109.5 . . ?
 N3 C11 H11B 109.5 . . ?
 N3 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 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
 O1 N1 C1 Br1 -28.9(2) . . . . ?
 O1 N1 C1 Br2 -150.86(15) . . . . ?
 O1 N1 C1 Br3 89.97(18) . . . . ?
 O2 N1 C1 Br1 154.49(16) . . . . ?
 O2 N1 C1 Br2 32.5(2) . . . . ?
 O2 N1 C1 Br3 -86.68(18) . . . . ?
 N2 C2 C3 C4 -179.89(19) . . . . ?
 N2 C2 C7 C6 178.82(19) . . . . ?
 N3 C5 C6 C7 -179.02(19) . . . . ?
 C2 C3 C4 C5 1.0(3) . . . . ?
 C3 C2 C7 C6 0.4(3) . . . . ?
 C3 C4 C5 N3 177.98(19) . . . . ?
 C3 C4 C5 C6 0.4(3) . . . . ?
 C4 C5 C6 C7 -1.4(3) . . . . ?
 C5 C6 C7 C2 1.0(3) . . . . ?
 C7 C2 C3 C4 -1.4(3) . . . . ?
 C8 N2 C2 C3 171.56(19) . . . . ?
 C8 N2 C2 C7 -6.8(3) . . . . ?
 C9 N2 C2 C3 -56.8(2) . . . . ?
 C9 N2 C2 C7 124.8(2) . . . . ?
 C10 N3 C5 C4 132.8(2) . . . . ?
 C10 N3 C5 C6 -49.7(3) . . . . ?
 C11 N3 C5 C4 2.1(3) . . . . ?
 C11 N3 C5 C6 179.58(18) . . . . ?

# end Validation Reply Form
_shelx_estimated_absorpt_T_max    0.779
_shelx_estimated_absorpt_T_min    0.120
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number            2012-9
_vrf_PLAT431_I
;
PROBLEM: Short Inter HL..A  Contact  Br2    ..  N2      .       2.74 Ang. 
RESPONSE: Short contact is related to the strong Br ...N halogen bond.
;
