#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/24/8102445.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_8102445
loop_
_publ_author_name
'Zhen Jia'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(4-bromophenyl)-5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitrile,
 C18H14BrN3
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              435
_journal_volume                  224
_journal_year                    2009
_chemical_formula_sum            'C18 H14 Br N3'
_chemical_formula_weight         352.23
_chemical_name_systematic
; 
2-amino-4-(4-bromophenyl)-5,6,7,8-tetrahydronaphthalene-
1,3-dicarbonitrile, C₁₈H₁₄Br₁N₃
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.907(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.840(3)
_cell_length_b                   7.5329(17)
_cell_length_c                   16.373(4)
_cell_measurement_reflns_used    1853
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.632
_cell_measurement_theta_min      2.506
_cell_volume                     1572.1(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7913
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    2.614
_exptl_absorpt_correction_T_max  0.9257
_exptl_absorpt_correction_T_min  0.3668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plan
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.3126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                1951
_reflns_number_total             2911
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2614.cff
_cod_data_source_block           81231dm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1572.2(6)
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               8102445
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
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 1.12738(3) 0.15290(6) 0.33716(3) 0.0742(2) Uani 1 1 d . . .
C1 C 0.9992(3) 0.1752(5) 0.3831(2) 0.0505(9) Uani 1 1 d . . .
C2 C 0.9436(3) 0.0283(5) 0.3978(2) 0.0596(10) Uani 1 1 d . . .
H2 H 0.9690 -0.0837 0.3868 0.071 Uiso 1 1 calc R . .
C3 C 0.8488(3) 0.0451(5) 0.4293(2) 0.0537(9) Uani 1 1 d . . .
H3 H 0.8105 -0.0560 0.4389 0.064 Uiso 1 1 calc R . .
C4 C 0.8105(2) 0.2105(4) 0.4467(2) 0.0432(8) Uani 1 1 d . . .
C5 C 0.8687(3) 0.3580(5) 0.4308(3) 0.0604(11) Uani 1 1 d . . .
H5 H 0.8443 0.4706 0.4421 0.072 Uiso 1 1 calc R . .
C6 C 0.9623(3) 0.3406(5) 0.3984(3) 0.0632(11) Uani 1 1 d . . .
H6 H 1.0002 0.4410 0.3870 0.076 Uiso 1 1 calc R . .
C7 C 0.7075(2) 0.2293(4) 0.4794(2) 0.0417(8) Uani 1 1 d . . .
C8 C 0.6170(3) 0.1858(4) 0.4266(2) 0.0425(8) Uani 1 1 d . . .
C9 C 0.6240(3) 0.1248(5) 0.3452(3) 0.0480(9) Uani 1 1 d . . .
C10 C 0.5159(3) 0.2058(4) 0.4517(2) 0.0433(8) Uani 1 1 d . . .
C11 C 0.5118(2) 0.2698(4) 0.5315(2) 0.0420(8) Uani 1 1 d . . .
C12 C 0.4095(3) 0.2949(4) 0.5561(2) 0.0498(9) Uani 1 1 d . . .
C13 C 0.6016(3) 0.3103(4) 0.5853(2) 0.0434(8) Uani 1 1 d . . .
C14 C 0.5884(3) 0.3690(5) 0.6714(2) 0.0535(9) Uani 1 1 d . . .
H14A H 0.5668 0.2677 0.7019 0.064 Uiso 1 1 calc R . .
H14B H 0.5326 0.4564 0.6686 0.064 Uiso 1 1 calc R . .
C15 C 0.7007(2) 0.2892(4) 0.5596(2) 0.0419(8) Uani 1 1 d . . .
C16 C 0.7981(3) 0.3355(5) 0.6160(2) 0.0551(9) Uani 1 1 d . . .
H16A H 0.8223 0.4517 0.6013 0.066 Uiso 1 1 calc R . .
H16B H 0.8526 0.2503 0.6081 0.066 Uiso 1 1 calc R . .
C17 C 0.7808(3) 0.3366(5) 0.7061(3) 0.0654(11) Uani 1 1 d . . .
H17A H 0.7700 0.2161 0.7243 0.079 Uiso 1 1 calc R . .
H17B H 0.8424 0.3841 0.7390 0.079 Uiso 1 1 calc R . .
C18 C 0.6865(3) 0.4483(5) 0.7182(2) 0.0612(10) Uani 1 1 d . . .
H18A H 0.6966 0.5680 0.6987 0.073 Uiso 1 1 calc R . .
H18B H 0.6786 0.4544 0.7763 0.073 Uiso 1 1 calc R . .
H2A H 0.430(2) 0.124(4) 0.356(2) 0.025(9) Uiso 1 1 d . . .
H2B H 0.369(4) 0.164(5) 0.422(3) 0.067(13) Uiso 1 1 d . . .
N1 N 0.6262(3) 0.0781(5) 0.2792(2) 0.0692(9) Uani 1 1 d . . .
N2 N 0.4280(3) 0.1647(5) 0.4015(2) 0.0568(9) Uani 1 1 d . . .
N3 N 0.3249(3) 0.3121(4) 0.5709(2) 0.0684(10) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.6(3) . . ?
C2 C1 Br1 120.0(3) . . ?
C6 C1 Br1 119.3(3) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C7 120.9(3) . . ?
C3 C4 C7 120.9(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C15 120.8(3) . . ?
C8 C7 C4 117.5(3) . . ?
C15 C7 C4 121.7(3) . . ?
C7 C8 C10 121.1(3) . . ?
C7 C8 C9 120.8(3) . . ?
C10 C8 C9 118.0(3) . . ?
N1 C9 C8 177.6(4) . . ?
N2 C10 C11 121.7(3) . . ?
N2 C10 C8 121.8(3) . . ?
C11 C10 C8 116.5(3) . . ?
C13 C11 C10 122.9(3) . . ?
C13 C11 C12 120.6(3) . . ?
C10 C11 C12 116.6(3) . . ?
N3 C12 C11 175.7(4) . . ?
C15 C13 C11 119.8(3) . . ?
C15 C13 C14 121.6(3) . . ?
C11 C13 C14 118.5(3) . . ?
C13 C14 C18 114.1(3) . . ?
C13 C14 H14A 108.7 . . ?
C18 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C18 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C13 C15 C7 118.7(3) . . ?
C13 C15 C16 120.6(3) . . ?
C7 C15 C16 120.6(3) . . ?
C15 C16 C17 112.9(3) . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 110.1(3) . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 C14 110.3(3) . . ?
C17 C18 H18A 109.6 . . ?
C14 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
C14 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C10 N2 H2A 122(2) . . ?
C10 N2 H2B 118(3) . . ?
H2A N2 H2B 119(4) . . ?
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 1.897(3) . ?
C1 C2 1.355(5) . ?
C1 C6 1.368(5) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 C7 1.491(4) . ?
C5 C6 1.377(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.401(4) . ?
C7 C15 1.402(4) . ?
C8 C10 1.416(4) . ?
C8 C9 1.423(5) . ?
C9 N1 1.140(4) . ?
C10 N2 1.350(5) . ?
C10 C11 1.399(5) . ?
C11 C13 1.398(5) . ?
C11 C12 1.431(4) . ?
C12 N3 1.149(4) . ?
C13 C15 1.396(4) . ?
C13 C14 1.506(5) . ?
C14 C18 1.516(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.503(5) . ?
C16 C17 1.519(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.506(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N2 H2A 0.81(3) . ?
N2 H2B 0.86(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
N2 H2A N1 0.81(3) 2.27(3) 3.028(6) 156(3) 2_655
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
C6 C1 C2 C3 -0.5(6) . . . . ?
Br1 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C2 C3 C4 C7 179.0(4) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C7 C4 C5 C6 -178.1(4) . . . . ?
C2 C1 C6 C5 1.4(7) . . . . ?
Br1 C1 C6 C5 179.2(3) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C5 C4 C7 C8 110.2(4) . . . . ?
C3 C4 C7 C8 -68.0(4) . . . . ?
C5 C4 C7 C15 -69.5(5) . . . . ?
C3 C4 C7 C15 112.4(4) . . . . ?
C15 C7 C8 C10 1.9(5) . . . . ?
C4 C7 C8 C10 -177.7(3) . . . . ?
C15 C7 C8 C9 -180.0(3) . . . . ?
C4 C7 C8 C9 0.4(5) . . . . ?
C7 C8 C9 N1 -155(10) . . . . ?
C10 C8 C9 N1 23(10) . . . . ?
C7 C8 C10 N2 179.9(3) . . . . ?
C9 C8 C10 N2 1.7(5) . . . . ?
C7 C8 C10 C11 -0.4(4) . . . . ?
C9 C8 C10 C11 -178.6(3) . . . . ?
N2 C10 C11 C13 178.8(3) . . . . ?
C8 C10 C11 C13 -1.0(5) . . . . ?
N2 C10 C11 C12 -2.0(5) . . . . ?
C8 C10 C11 C12 178.3(3) . . . . ?
C13 C11 C12 N3 175(5) . . . . ?
C10 C11 C12 N3 -4(5) . . . . ?
C10 C11 C13 C15 0.8(5) . . . . ?
C12 C11 C13 C15 -178.4(3) . . . . ?
C10 C11 C13 C14 -176.8(3) . . . . ?
C12 C11 C13 C14 4.0(5) . . . . ?
C15 C13 C14 C18 15.4(5) . . . . ?
C11 C13 C14 C18 -167.0(3) . . . . ?
C11 C13 C15 C7 0.7(4) . . . . ?
C14 C13 C15 C7 178.2(3) . . . . ?
C11 C13 C15 C16 178.8(3) . . . . ?
C14 C13 C15 C16 -3.8(5) . . . . ?
C8 C7 C15 C13 -2.0(5) . . . . ?
C4 C7 C15 C13 177.6(3) . . . . ?
C8 C7 C15 C16 179.9(3) . . . . ?
C4 C7 C15 C16 -0.5(5) . . . . ?
C13 C15 C16 C17 21.5(5) . . . . ?
C7 C15 C16 C17 -160.5(3) . . . . ?
C15 C16 C17 C18 -50.8(4) . . . . ?
C16 C17 C18 C14 62.8(4) . . . . ?
C13 C14 C18 C17 -44.5(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653963
