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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/84/1518495.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_1518495
loop_
_publ_author_name
'Tang, Hai-Tao'
'Xiong, Kai'
'Li, Ren-Hao'
'Ding, Zong-Cang'
'Zhan, Zhuang-Ping'
_publ_section_title
;
 Synthesis of 5,6-Dihydropyrazolo[1,5-c]quinazolines through
 Gold-Catalyzed Chemoselective Bicyclization of N-Propargylic
 Sulfonylhydrazones.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              326
_journal_page_last               329
_journal_paper_doi               10.1021/ol503437n
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C16 H12 Br N3'
_chemical_formula_sum            'C16 H12 Br N3'
_chemical_formula_weight         326.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           145
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   10.1800(12)
_cell_length_b                   10.1800(12)
_cell_length_c                   10.954(3)
_cell_measurement_temperature    173(2)
_cell_volume                     983.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0955
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5481
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    3.128
_exptl_absorpt_correction_T_max  0.5735
_exptl_absorpt_correction_T_min  0.3676
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.025(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                2416
_reflns_number_total             2546
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503437n_si_002.cif
_cod_data_source_block           hex
_cod_depositor_comments          'Adding full bibliography for 1518495.cif.'
_cod_original_sg_symbol_H-M      P3(2)
_cod_database_code               1518495
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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 0.70617(5) 1.12675(5) 0.17978(4) 0.04210(16) Uani 1 1 d .
N1 N 0.2207(4) 0.8822(4) 0.6967(3) 0.0306(7) Uani 1 1 d .
C1 C 0.2072(4) 0.7124(4) 0.5353(3) 0.0270(8) Uani 1 1 d .
H1 H 0.2498 0.6695 0.5953 0.032 Uiso 1 1 calc R
C2 C -0.0264(4) 0.6085(4) 0.4188(3) 0.0266(8) Uani 1 1 d .
N2 N 0.1442(4) 0.7902(4) 0.6022(2) 0.0254(6) Uani 1 1 d .
N3 N 0.0834(4) 0.5893(4) 0.4733(3) 0.0299(7) Uani 1 1 d .
H3 H 0.0779 0.5003 0.4702 0.036 Uiso 1 1 calc R
C3 C -0.1166(5) 0.5119(5) 0.3254(4) 0.0334(9) Uani 1 1 d .
H3A H -0.0964 0.4365 0.2946 0.040 Uiso 1 1 calc R
C4 C -0.2321(5) 0.5251(5) 0.2787(4) 0.0392(10) Uani 1 1 d .
H4 H -0.2925 0.4581 0.2155 0.047 Uiso 1 1 calc R
C5 C -0.2643(5) 0.6330(5) 0.3202(4) 0.0381(9) Uani 1 1 d .
H5 H -0.3456 0.6413 0.2859 0.046 Uiso 1 1 calc R
C6 C -0.1769(5) 0.7295(5) 0.4128(3) 0.0302(8) Uani 1 1 d .
H6 H -0.1973 0.8052 0.4423 0.036 Uiso 1 1 calc R
C7 C -0.0594(4) 0.7153(4) 0.4623(3) 0.0242(7) Uani 1 1 d .
C8 C 0.0296(4) 0.8073(4) 0.5651(3) 0.0251(7) Uani 1 1 d .
C9 C 0.0263(5) 0.9115(5) 0.6389(3) 0.0304(8) Uani 1 1 d .
H9 H -0.0432 0.9479 0.6369 0.036 Uiso 1 1 calc R
C10 C 0.1462(5) 0.9537(5) 0.7180(3) 0.0345(10) Uani 1 1 d .
H10 H 0.1719 1.0267 0.7810 0.041 Uiso 1 1 calc R
C11 C 0.3330(4) 0.8197(4) 0.4532(3) 0.0242(7) Uani 1 1 d .
C12 C 0.3291(4) 0.9393(5) 0.3961(3) 0.0276(8) Uani 1 1 d .
H12 H 0.2478 0.9575 0.4120 0.033 Uiso 1 1 calc R
C13 C 0.4426(5) 1.0318(5) 0.3165(3) 0.0288(8) Uani 1 1 d .
H13 H 0.4415 1.1154 0.2791 0.035 Uiso 1 1 calc R
C14 C 0.5551(4) 1.0028(4) 0.2922(3) 0.0275(8) Uani 1 1 d .
C15 C 0.5639(5) 0.8876(5) 0.3478(4) 0.0332(8) Uani 1 1 d .
H15 H 0.6456 0.8704 0.3308 0.040 Uiso 1 1 calc R
C16 C 0.4523(4) 0.7973(5) 0.4287(3) 0.0289(8) Uani 1 1 d .
H16 H 0.4578 0.7174 0.4687 0.035 Uiso 1 1 calc R
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 0.0364(2) 0.0354(2) 0.0468(2) 0.00129(18) 0.01344(19) 0.01214(19)
N1 0.0280(17) 0.0390(19) 0.0230(14) -0.0048(12) -0.0032(12) 0.0153(15)
C1 0.028(2) 0.029(2) 0.0290(17) 0.0004(14) -0.0019(14) 0.0189(17)
C2 0.0206(17) 0.0219(18) 0.0289(17) 0.0039(14) 0.0026(14) 0.0042(15)
N2 0.0284(16) 0.0291(17) 0.0221(13) -0.0017(12) 0.0005(12) 0.0171(14)
N3 0.0327(19) 0.0182(15) 0.0384(17) 0.0016(13) 0.0008(13) 0.0125(14)
C3 0.032(2) 0.0224(19) 0.036(2) -0.0057(16) -0.0007(16) 0.0066(17)
C4 0.039(2) 0.035(2) 0.033(2) -0.0040(17) -0.0074(17) 0.010(2)
C5 0.035(2) 0.038(2) 0.039(2) 0.0045(18) -0.0076(18) 0.017(2)
C6 0.0277(19) 0.0271(19) 0.0327(18) 0.0053(15) -0.0010(15) 0.0113(17)
C7 0.0226(17) 0.0219(17) 0.0237(15) 0.0046(13) -0.0004(13) 0.0079(14)
C8 0.0244(19) 0.0245(18) 0.0256(17) 0.0041(13) 0.0010(13) 0.0115(16)
C9 0.028(2) 0.033(2) 0.0331(18) 0.0006(16) 0.0020(15) 0.0174(17)
C10 0.037(2) 0.037(2) 0.0282(19) -0.0031(16) 0.0009(16) 0.0172(19)
C11 0.0295(19) 0.0238(18) 0.0236(15) -0.0049(13) -0.0043(14) 0.0167(16)
C12 0.0246(18) 0.0250(19) 0.0365(18) -0.0015(15) 0.0004(14) 0.0150(16)
C13 0.032(2) 0.026(2) 0.0306(18) 0.0024(14) 0.0002(15) 0.0156(17)
C14 0.0242(19) 0.0233(19) 0.0276(17) -0.0038(14) 0.0041(14) 0.0062(15)
C15 0.0248(19) 0.034(2) 0.046(2) -0.0052(17) -0.0023(16) 0.0188(18)
C16 0.029(2) 0.029(2) 0.0340(18) 0.0005(15) -0.0032(15) 0.0187(18)
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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 N1 N2 103.2(3)
N3 C1 N2 106.5(3)
N3 C1 C11 114.4(3)
N2 C1 C11 110.9(3)
N3 C2 C7 120.3(3)
N3 C2 C3 121.0(4)
C7 C2 C3 118.4(4)
C8 N2 N1 112.5(3)
C8 N2 C1 125.3(3)
N1 N2 C1 120.6(3)
C2 N3 C1 120.5(3)
C4 C3 C2 120.4(4)
C3 C4 C5 121.5(4)
C4 C5 C6 119.0(4)
C5 C6 C7 119.7(4)
C2 C7 C6 120.8(3)
C2 C7 C8 117.3(3)
C6 C7 C8 121.9(3)
N2 C8 C9 106.8(3)
N2 C8 C7 117.2(3)
C9 C8 C7 136.0(4)
C8 C9 C10 104.8(4)
N1 C10 C9 112.6(4)
C16 C11 C12 118.3(4)
C16 C11 C1 120.2(3)
C12 C11 C1 121.4(3)
C13 C12 C11 120.2(4)
C14 C13 C12 119.4(4)
C13 C14 C15 122.0(4)
C13 C14 Br1 118.9(3)
C15 C14 Br1 119.1(3)
C14 C15 C16 118.5(4)
C11 C16 C15 121.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.879(4)
N1 C10 1.308(6)
N1 N2 1.351(4)
C1 N3 1.429(5)
C1 N2 1.443(5)
C1 C11 1.497(5)
C2 N3 1.365(5)
C2 C7 1.373(5)
C2 C3 1.398(6)
N2 C8 1.327(5)
C3 C4 1.349(7)
C4 C5 1.372(7)
C5 C6 1.383(6)
C6 C7 1.385(6)
C7 C8 1.455(5)
C8 C9 1.347(6)
C9 C10 1.378(6)
C11 C16 1.370(5)
C11 C12 1.387(5)
C12 C13 1.376(6)
C13 C14 1.344(6)
C14 C15 1.364(6)
C15 C16 1.370(6)