#------------------------------------------------------------------------------
#$Date: 2016-05-04 19:25:39 +0300 (Wed, 04 May 2016) $
#$Revision: 182527 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/29/1542971.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_1542971
loop_
_publ_author_name
'Gade, Amol B.'
'Patil, Nitin T.'
_publ_section_title
;
 Gold(I)-Catalyzed Hydroaminaloxylation and Petasis-Ferrier Rearrangement
 Cascade of Aminaloalkynes.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1844
_journal_page_last               1847
_journal_paper_doi               10.1021/acs.orglett.6b00585
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C14 H14 Br N O2'
_chemical_formula_sum            'C14 H14 Br N O2'
_chemical_formula_weight         308.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 115.977(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2913(17)
_cell_length_b                   9.9716(15)
_cell_length_c                   12.7496(19)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.57
_cell_measurement_theta_min      2.71
_cell_volume                     1290.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13009
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    3.178
_exptl_absorpt_correction_T_max  0.4807
_exptl_absorpt_correction_T_min  0.3941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0419P)²+1.1610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                1409
_reflns_number_total             2269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00585_si_002.cif
_cod_data_source_block           abg09pbr_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1542971.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               1542971
loop_
_symmetry_equiv_pos_as_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'
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 0.75755(7) 0.00949(6) -0.10449(4) 0.1015(3) Uani 1 1 d .
O1 O 0.9228(3) -0.1528(3) 0.4541(3) 0.0703(8) Uani 1 1 d .
O2 O 0.5521(3) 0.1536(4) 0.5922(3) 0.0939(11) Uani 1 1 d .
N6 N 0.6911(3) 0.0999(4) 0.5116(3) 0.0586(9) Uani 1 1 d .
C1 C 0.7002(4) 0.1061(4) 0.4019(3) 0.0494(10) Uani 1 1 d .
H1 H 0.7759 0.1615 0.4115 0.059 Uiso 1 1 calc R
C2 C 0.7163(4) -0.0353(4) 0.3605(3) 0.0456(9) Uani 1 1 d .
H2 H 0.6352 -0.0851 0.3441 0.055 Uiso 1 1 calc R
C3 C 0.8283(4) -0.1065(4) 0.4612(4) 0.0532(10) Uani 1 1 d .
C4 C 0.8090(4) -0.1117(5) 0.5705(4) 0.0646(12) Uani 1 1 d .
H4A H 0.8843 -0.1548 0.6323 0.077 Uiso 1 1 calc R
H4B H 0.7312 -0.1644 0.5565 0.077 Uiso 1 1 calc R
C5 C 0.7930(5) 0.0294(5) 0.6082(4) 0.0756(14) Uani 1 1 d .
H5A H 0.7697 0.0246 0.6729 0.091 Uiso 1 1 calc R
H5B H 0.8756 0.0776 0.6342 0.091 Uiso 1 1 calc R
C7 C 0.5799(4) 0.1531(5) 0.5098(4) 0.0663(12) Uani 1 1 d .
C8 C 0.5018(5) 0.2123(5) 0.3911(4) 0.0800(15) Uani 1 1 d .
H8A H 0.4133 0.1755 0.3560 0.096 Uiso 1 1 calc R
H8B H 0.4959 0.3089 0.3964 0.096 Uiso 1 1 calc R
C9 C 0.5729(4) 0.1768(4) 0.3196(4) 0.0614(11) Uani 1 1 d .
H9A H 0.5928 0.2570 0.2873 0.074 Uiso 1 1 calc R
H9B H 0.5193 0.1179 0.2558 0.074 Uiso 1 1 calc R
C10 C 0.7301(4) -0.0279(3) 0.2483(3) 0.0430(9) Uani 1 1 d .
C11 C 0.8294(4) 0.0465(4) 0.2401(3) 0.0519(10) Uani 1 1 d .
H11 H 0.8912 0.0892 0.3063 0.062 Uiso 1 1 calc R
C12 C 0.8390(4) 0.0589(4) 0.1368(4) 0.0572(11) Uani 1 1 d .
H12 H 0.9060 0.1096 0.1328 0.069 Uiso 1 1 calc R
C13 C 0.7480(4) -0.0049(4) 0.0397(3) 0.0533(10) Uani 1 1 d .
C14 C 0.6481(4) -0.0794(4) 0.0445(3) 0.0520(10) Uani 1 1 d .
H14 H 0.5870 -0.1227 -0.0217 0.062 Uiso 1 1 calc R
C15 C 0.6398(4) -0.0890(4) 0.1489(3) 0.0467(9) Uani 1 1 d .
H15 H 0.5715 -0.1381 0.1521 0.056 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N6 C1 115.1(3)
C7 N6 C5 126.1(4)
C1 N6 C5 118.5(3)
N6 C1 C9 103.9(3)
N6 C1 C2 111.1(3)
C9 C1 C2 113.7(3)
N6 C1 H1 109.3
C9 C1 H1 109.3
C2 C1 H1 109.3
C10 C2 C3 115.4(3)
C10 C2 C1 110.9(3)
C3 C2 C1 108.4(3)
C10 C2 H2 107.3
C3 C2 H2 107.3
C1 C2 H2 107.3
O1 C3 C4 123.4(4)
O1 C3 C2 123.5(4)
C4 C3 C2 113.1(4)
C3 C4 C5 110.2(4)
C3 C4 H4A 109.6
C5 C4 H4A 109.6
C3 C4 H4B 109.6
C5 C4 H4B 109.6
H4A C4 H4B 108.1
N6 C5 C4 109.9(4)
N6 C5 H5A 109.7
C4 C5 H5A 109.7
N6 C5 H5B 109.7
C4 C5 H5B 109.7
H5A C5 H5B 108.2
O2 C7 N6 125.0(5)
O2 C7 C8 127.4(4)
N6 C7 C8 107.6(4)
C9 C8 C7 106.7(4)
C9 C8 H8A 110.4
C7 C8 H8A 110.4
C9 C8 H8B 110.4
C7 C8 H8B 110.4
H8A C8 H8B 108.6
C8 C9 C1 106.5(4)
C8 C9 H9A 110.4
C1 C9 H9A 110.4
C8 C9 H9B 110.4
C1 C9 H9B 110.4
H9A C9 H9B 108.6
C15 C10 C11 117.8(3)
C15 C10 C2 120.7(3)
C11 C10 C2 121.4(3)
C12 C11 C10 121.8(4)
C12 C11 H11 119.1
C10 C11 H11 119.1
C13 C12 C11 118.8(4)
C13 C12 H12 120.6
C11 C12 H12 120.6
C12 C13 C14 121.0(4)
C12 C13 Br1 120.2(3)
C14 C13 Br1 118.7(3)
C13 C14 C15 119.0(4)
C13 C14 H14 120.5
C15 C14 H14 120.5
C10 C15 C14 121.6(4)
C10 C15 H15 119.2
C14 C15 H15 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C13 1.894(4)
O1 C3 1.201(5)
O2 C7 1.221(5)
N6 C7 1.355(5)
N6 C1 1.447(5)
N6 C5 1.447(5)
C1 C9 1.531(5)
C1 C2 1.544(5)
C1 H1 0.9800
C2 C10 1.507(5)
C2 C3 1.526(5)
C2 H2 0.9800
C3 C4 1.504(6)
C4 C5 1.523(6)
C4 H4A 0.9700
C4 H4B 0.9700
C5 H5A 0.9700
C5 H5B 0.9700
C7 C8 1.499(6)
C8 C9 1.498(6)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9700
C9 H9B 0.9700
C10 C15 1.373(5)
C10 C11 1.387(5)
C11 C12 1.373(5)
C11 H11 0.9300
C12 C13 1.370(6)
C12 H12 0.9300
C13 C14 1.375(5)
C14 C15 1.377(5)
C14 H14 0.9300
C15 H15 0.9300
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
C7 N6 C1 C9 0.8(5)
C5 N6 C1 C9 175.6(4)
C7 N6 C1 C2 -121.8(4)
C5 N6 C1 C2 53.0(5)
N6 C1 C2 C10 -178.2(3)
C9 C1 C2 C10 65.1(4)
N6 C1 C2 C3 -50.6(4)
C9 C1 C2 C3 -167.3(3)
C10 C2 C3 O1 0.9(6)
C1 C2 C3 O1 -124.1(4)
C10 C2 C3 C4 -179.6(3)
C1 C2 C3 C4 55.4(4)
O1 C3 C4 C5 122.4(5)
C2 C3 C4 C5 -57.1(5)
C7 N6 C5 C4 121.2(5)
C1 N6 C5 C4 -53.1(5)
C3 C4 C5 N6 52.3(5)
C1 N6 C7 O2 177.5(4)
C5 N6 C7 O2 3.1(7)
C1 N6 C7 C8 -3.8(5)
C5 N6 C7 C8 -178.2(4)
O2 C7 C8 C9 -176.1(5)
N6 C7 C8 C9 5.2(5)
C7 C8 C9 C1 -4.7(5)
N6 C1 C9 C8 2.6(5)
C2 C1 C9 C8 123.5(4)
C3 C2 C10 C15 117.4(4)
C1 C2 C10 C15 -118.9(4)
C3 C2 C10 C11 -66.2(5)
C1 C2 C10 C11 57.5(4)
C15 C10 C11 C12 -0.4(6)
C2 C10 C11 C12 -176.9(4)
C10 C11 C12 C13 -0.4(6)
C11 C12 C13 C14 0.4(6)
C11 C12 C13 Br1 180.0(3)
C12 C13 C14 C15 0.3(6)
Br1 C13 C14 C15 -179.3(3)
C11 C10 C15 C14 1.1(5)
C2 C10 C15 C14 177.7(3)
C13 C14 C15 C10 -1.1(6)
