
data_AB1608b

_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C17 H14 Br4 N2'
_chemical_formula_sum
 'C17 H14 Br4 N2'
_chemical_formula_weight          565.94

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'

_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'

_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.
;

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

_cell_length_a                    8.7964(3)
_cell_length_b                    12.5727(4)
_cell_length_c                    15.8234(5)
_cell_angle_alpha                 90
_cell_angle_beta                  100.818(3)
_cell_angle_gamma                 90
_cell_volume                      1718.88(10)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     2390
_cell_measurement_theta_min       4.5200
_cell_measurement_theta_max       73.1520

_exptl_crystal_description        tablets
_exptl_crystal_colour             Colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     2.187
_exptl_crystal_F_000              1080
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.09
_exptl_crystal_size_min           0.08
_exptl_absorpt_coefficient_mu     11.422
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    analytical
_exptl_absorpt_correction_T_min   0.257
_exptl_absorpt_correction_T_max   0.533
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source                    'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type   'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method        'omega scans'
_diffrn_detector_area_resol_mean  10.4115
_diffrn_reflns_number             5495
_diffrn_reflns_av_unetI/netI      0.0437
_diffrn_reflns_av_R_equivalents   0.0295
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          4.523
_diffrn_reflns_theta_max          73.815
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.956
_diffrn_measured_fraction_theta_full  0.986
_diffrn_reflns_Laue_measured_fraction_max    0.956
_diffrn_reflns_Laue_measured_fraction_full   0.986
_diffrn_reflns_point_group_measured_fraction_max   0.956
_diffrn_reflns_point_group_measured_fraction_full  0.986
_reflns_number_total              3310
_reflns_number_gt                 2760
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .

_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.
;

_computing_data_collection        'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement        'CrysAlisPro, Agilent Technologies'
_computing_data_reduction         'CrysAlisPro, Agilent Technologies'
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2014)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0247P)²+3.0885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.00015(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3310
_refine_ls_number_parameters      217
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0469
_refine_ls_R_factor_gt            0.0354
_refine_ls_wR_factor_ref          0.0846
_refine_ls_wR_factor_gt           0.0790
_refine_ls_goodness_of_fit_ref    1.097
_refine_ls_restrained_S_all       1.097
_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_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
N1 N 0.4785(3) 0.3506(3) 0.3642(2) 0.0276(9) Uani 1 1 d D . . . .
H1 H 0.3912(4) 0.3795(7) 0.3759(6) 0.05(2) Uiso 1 1 d D . . . .
C2 C 0.6041(6) 0.4186(4) 0.3718(3) 0.0250(10) Uani 1 1 d . . . . .
C3 C 0.5874(5) 0.5284(4) 0.3883(3) 0.0239(10) Uani 1 1 d . . . . .
Br3 Br 0.38903(6) 0.57749(4) 0.40175(3) 0.02786(14) Uani 1 1 d . . . . .
C4 C 0.7065(6) 0.5988(4) 0.3949(3) 0.0276(11) Uani 1 1 d . . . . .
H4A H 0.6918 0.6718 0.4066 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8501(6) 0.5614(5) 0.3840(3) 0.0315(11) Uani 1 1 d . . . . .
Br5 Br 1.01397(7) 0.66032(5) 0.38712(5) 0.04486(18) Uani 1 1 d . . . . .
C6 C 0.8710(6) 0.4551(5) 0.3663(3) 0.0305(11) Uani 1 1 d . . . . .
H6A H 0.9697 0.4309 0.3583 0.037 Uiso 1 1 calc R U . . .
C7 C 0.7498(6) 0.3836(4) 0.3603(3) 0.0267(11) Uani 1 1 d . . . . .
C8 C 0.7719(6) 0.2659(4) 0.3414(3) 0.0322(12) Uani 1 1 d . . . . .
H8A H 0.8426 0.2591 0.2998 0.039 Uiso 1 1 calc R U . . .
H8B H 0.8199 0.2292 0.3951 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6184(6) 0.2138(4) 0.3046(3) 0.0312(12) Uani 1 1 d . . . . .
H9A H 0.6340 0.1361 0.3004 0.037 Uiso 1 1 calc R U . . .
H9B H 0.5808 0.2412 0.2457 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4967(6) 0.2344(4) 0.3590(3) 0.0272(11) Uani 1 1 d . . . . .
C11 C 0.3401(6) 0.1871(4) 0.3197(3) 0.0301(11) Uani 1 1 d . . . . .
H11A H 0.3534 0.1109 0.3070 0.036 Uiso 1 1 calc R U . . .
H11B H 0.2993 0.2236 0.2647 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2232(6) 0.1976(4) 0.3793(3) 0.0303(11) Uani 1 1 d . . . . .
H12A H 0.1935 0.2733 0.3823 0.036 Uiso 1 1 calc R U . . .
H12B H 0.1288 0.1568 0.3549 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2863(6) 0.1579(4) 0.4684(3) 0.0263(10) Uani 1 1 d . . . . .
C14 C 0.1887(6) 0.1217(4) 0.5228(3) 0.0260(10) Uani 1 1 d . . . . .
H14A H 0.0798 0.1200 0.5029 0.031 Uiso 1 1 calc R U . . .
C15 C 0.2509(6) 0.0881(4) 0.6059(3) 0.0269(10) Uani 1 1 d . . . . .
Br15 Br 0.11744(7) 0.04067(5) 0.67950(4) 0.03745(16) Uani 1 1 d . . . . .
C16 C 0.4085(6) 0.0875(4) 0.6344(3) 0.0242(10) Uani 1 1 d . . . . .
H16A H 0.4504 0.0643 0.6911 0.029 Uiso 1 1 calc R U . . .
C17 C 0.5055(5) 0.1205(4) 0.5809(3) 0.0221(9) Uani 1 1 d . . . . .
Br17 Br 0.72249(6) 0.11359(4) 0.61966(3) 0.02784(14) Uani 1 1 d . . . . .
C18 C 0.4486(6) 0.1557(4) 0.4968(3) 0.0240(10) Uani 1 1 d . . . . .
N19 N 0.5480(3) 0.1857(3) 0.4440(2) 0.0277(9) Uani 1 1 d D . . . .
H19 H 0.6456(4) 0.2004(13) 0.4703(7) 0.041(17) Uiso 1 1 d 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
N1 0.028(2) 0.026(2) 0.030(2) -0.0039(18) 0.0053(17) 0.0002(18)
C2 0.031(3) 0.024(3) 0.019(2) 0.0043(19) 0.0019(18) 0.001(2)
C3 0.025(2) 0.030(3) 0.017(2) 0.0031(19) 0.0049(17) 0.003(2)
Br3 0.0301(3) 0.0256(3) 0.0291(3) 0.0016(2) 0.00870(19) 0.0050(2)
C4 0.030(3) 0.030(3) 0.023(2) 0.001(2) 0.0065(19) 0.005(2)
C5 0.032(3) 0.027(3) 0.035(3) 0.003(2) 0.007(2) -0.001(2)
Br5 0.0300(3) 0.0341(3) 0.0713(4) 0.0014(3) 0.0116(3) -0.0026(3)
C6 0.029(3) 0.034(3) 0.030(2) 0.005(2) 0.009(2) 0.007(2)
C7 0.039(3) 0.023(3) 0.020(2) 0.0017(19) 0.0072(19) 0.004(2)
C8 0.039(3) 0.027(3) 0.034(3) 0.002(2) 0.015(2) 0.010(2)
C9 0.045(3) 0.025(3) 0.026(2) -0.005(2) 0.011(2) 0.004(2)
C10 0.035(3) 0.025(3) 0.021(2) 0.003(2) 0.0027(19) -0.002(2)
C11 0.040(3) 0.026(3) 0.022(2) -0.002(2) 0.000(2) -0.006(2)
C12 0.031(3) 0.027(3) 0.030(2) 0.003(2) -0.002(2) 0.000(2)
C13 0.028(2) 0.024(3) 0.024(2) -0.006(2) -0.0007(19) 0.001(2)
C14 0.027(2) 0.022(3) 0.028(2) -0.001(2) 0.0025(19) -0.002(2)
C15 0.028(3) 0.026(3) 0.028(2) -0.003(2) 0.0070(19) -0.001(2)
Br15 0.0302(3) 0.0431(4) 0.0409(3) 0.0098(3) 0.0115(2) 0.0002(2)
C16 0.031(3) 0.020(3) 0.021(2) -0.0051(18) 0.0023(18) -0.001(2)
C17 0.023(2) 0.017(2) 0.025(2) -0.0017(19) 0.0000(17) 0.0007(18)
Br17 0.0243(3) 0.0299(3) 0.0281(2) 0.0015(2) 0.00175(18) 0.0004(2)
C18 0.030(2) 0.019(2) 0.024(2) -0.0014(19) 0.0076(19) 0.003(2)
N19 0.026(2) 0.029(2) 0.027(2) 0.0032(18) 0.0018(16) 0.0005(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
N1 C2 1.384(6) . ?
N1 C10 1.474(6) . ?
C2 C7 1.399(7) . ?
C2 C3 1.418(7) . ?
C3 C4 1.360(7) . ?
C3 Br3 1.900(5) . ?
C4 C5 1.389(7) . ?
C5 C6 1.385(8) . ?
C5 Br5 1.897(5) . ?
C6 C7 1.384(8) . ?
C7 C8 1.529(7) . ?
C8 C9 1.515(8) . ?
C9 C10 1.516(7) . ?
C10 N19 1.470(6) . ?
C10 C11 1.522(7) . ?
C11 C12 1.525(7) . ?
C12 C13 1.501(7) . ?
C13 C14 1.401(7) . ?
C13 C18 1.414(7) . ?
C14 C15 1.392(7) . ?
C15 C16 1.375(7) . ?
C15 Br15 1.898(5) . ?
C16 C17 1.373(7) . ?
C17 C18 1.403(6) . ?
C17 Br17 1.894(5) . ?
C18 N19 1.371(6) . ?

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 N1 C10 121.6(4) . . ?
N1 C2 C7 122.0(5) . . ?
N1 C2 C3 120.6(4) . . ?
C7 C2 C3 117.3(5) . . ?
C4 C3 C2 122.9(5) . . ?
C4 C3 Br3 119.4(4) . . ?
C2 C3 Br3 117.8(4) . . ?
C3 C4 C5 118.4(5) . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 Br5 120.6(4) . . ?
C4 C5 Br5 118.6(4) . . ?
C7 C6 C5 120.7(5) . . ?
C6 C7 C2 120.0(5) . . ?
C6 C7 C8 121.1(5) . . ?
C2 C7 C8 118.9(5) . . ?
C9 C8 C7 110.9(4) . . ?
C8 C9 C10 112.4(4) . . ?
N19 C10 N1 112.3(4) . . ?
N19 C10 C9 108.7(4) . . ?
N1 C10 C9 107.3(4) . . ?
N19 C10 C11 108.1(4) . . ?
N1 C10 C11 108.1(4) . . ?
C9 C10 C11 112.5(4) . . ?
C10 C11 C12 112.2(4) . . ?
C13 C12 C11 112.2(4) . . ?
C14 C13 C18 119.8(4) . . ?
C14 C13 C12 121.6(5) . . ?
C18 C13 C12 118.6(5) . . ?
C15 C14 C13 120.1(5) . . ?
C16 C15 C14 120.4(5) . . ?
C16 C15 Br15 119.9(4) . . ?
C14 C15 Br15 119.7(4) . . ?
C17 C16 C15 120.0(4) . . ?
C16 C17 C18 121.9(4) . . ?
C16 C17 Br17 119.4(4) . . ?
C18 C17 Br17 118.7(4) . . ?
N19 C18 C17 120.7(4) . . ?
N19 C18 C13 121.5(4) . . ?
C17 C18 C13 117.8(4) . . ?
C18 N19 C10 123.4(4) . . ?

loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N1 H1 Br3  0.9000(1) 2.523(8) 3.047(4) 117.7(6) .
N19 H19 Br17  0.9000(1) 2.576(14) 3.050(4) 113.7(11) .

_refine_diff_density_max    0.447
_refine_diff_density_min   -0.575
_refine_diff_density_rms    0.111



#===END
