#------------------------------------------------------------------------------
#$Date: 2016-08-05 06:41:07 +0300 (Fri, 05 Aug 2016) $
#$Revision: 184979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/29/1542972.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_1542972
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         'C17 H20 Cl N O2'
_chemical_formula_sum            'C17 H20 Cl N O2'
_chemical_formula_weight         305.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.28530(10)
_cell_length_b                   10.2495(2)
_cell_length_c                   23.3386(5)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.78
_cell_measurement_theta_min      2.65
_cell_volume                     1503.50(5)
_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      150(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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22152
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.9478
_exptl_absorpt_correction_T_min  0.8883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.19(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0236
_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/[σ²(Fo²)+(0.0156P)²+0.5256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0533
_reflns_number_gt                2642
_reflns_number_total             2665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00585_si_003.cif
_cod_data_source_block           abg_18_c_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 1542972.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               1542972
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -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
Cl1 Cl 1.07913(8) 0.93836(4) 0.982136(18) 0.03750(11) Uani 1 1 d .
O1 O 0.85116(17) 0.68005(10) 0.74087(4) 0.0264(2) Uani 1 1 d .
O2 O 0.65698(16) 0.10709(9) 0.75130(4) 0.0250(2) Uani 1 1 d .
N6 N 0.69549(19) 0.31589(11) 0.78148(5) 0.0187(2) Uani 1 1 d .
C1 C 0.7102(2) 0.41726(13) 0.82605(6) 0.0178(3) Uani 1 1 d .
H1 H 0.5756 0.4692 0.8257 0.021 Uiso 1 1 calc R
C2 C 0.8991(2) 0.51030(13) 0.81162(6) 0.0197(3) Uani 1 1 d .
H2 H 1.0304 0.4553 0.8105 0.024 Uiso 1 1 calc R
C3 C 0.8680(2) 0.56521(14) 0.75123(6) 0.0217(3) Uani 1 1 d .
C4 C 0.8512(3) 0.45887(15) 0.70707(6) 0.0249(3) Uani 1 1 d .
H4A H 0.9875 0.4106 0.7049 0.030 Uiso 1 1 calc R
H4B H 0.8227 0.4977 0.6690 0.030 Uiso 1 1 calc R
C5 C 0.6715(2) 0.36491(14) 0.72292(6) 0.0226(3) Uani 1 1 d .
H5A H 0.5333 0.4104 0.7193 0.027 Uiso 1 1 calc R
H5B H 0.6715 0.2905 0.6959 0.027 Uiso 1 1 calc R
C7 C 0.6722(2) 0.18592(14) 0.79080(6) 0.0193(3) Uani 1 1 d .
C8 C 0.6702(2) 0.13881(14) 0.85218(6) 0.0224(3) Uani 1 1 d .
H8A H 0.8149 0.1082 0.8621 0.027 Uiso 1 1 calc R
H8B H 0.5734 0.0628 0.8548 0.027 Uiso 1 1 calc R
C9 C 0.6012(2) 0.23973(14) 0.89666(6) 0.0199(3) Uani 1 1 d .
C10 C 0.7400(2) 0.35965(14) 0.88575(6) 0.0205(3) Uani 1 1 d .
H10A H 0.7058 0.4272 0.9146 0.025 Uiso 1 1 calc R
H10B H 0.8912 0.3352 0.8908 0.025 Uiso 1 1 calc R
C11 C 0.6429(3) 0.18766(15) 0.95715(6) 0.0268(3) Uani 1 1 d .
H11A H 0.5557 0.1098 0.9638 0.040 Uiso 1 1 calc R
H11B H 0.6059 0.2548 0.9853 0.040 Uiso 1 1 calc R
H11C H 0.7937 0.1650 0.9610 0.040 Uiso 1 1 calc R
C12 C 0.3636(2) 0.27164(15) 0.89044(6) 0.0244(3) Uani 1 1 d .
H12A H 0.3333 0.2962 0.8507 0.037 Uiso 1 1 calc R
H12B H 0.3270 0.3443 0.9159 0.037 Uiso 1 1 calc R
H12C H 0.2790 0.1949 0.9008 0.037 Uiso 1 1 calc R
C13 C 0.9364(2) 0.61448(13) 0.85608(6) 0.0195(3) Uani 1 1 d .
C14 C 1.1332(2) 0.62388(14) 0.88279(6) 0.0227(3) Uani 1 1 d .
H14 H 1.2407 0.5619 0.8739 0.027 Uiso 1 1 calc R
C15 C 1.1763(3) 0.72173(14) 0.92220(6) 0.0254(3) Uani 1 1 d .
H15 H 1.3118 0.7270 0.9401 0.030 Uiso 1 1 calc R
C16 C 1.0200(3) 0.81086(14) 0.93486(6) 0.0241(3) Uani 1 1 d .
C17 C 0.8205(3) 0.80355(14) 0.91003(6) 0.0257(3) Uani 1 1 d .
H17 H 0.7128 0.8645 0.9199 0.031 Uiso 1 1 calc R
C18 C 0.7804(2) 0.70557(14) 0.87039(6) 0.0238(3) Uani 1 1 d .
H18 H 0.6444 0.7005 0.8527 0.029 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'
Cl Cl 0.1484 0.1585 '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 C5 118.37(12)
C7 N6 C1 125.85(12)
C5 N6 C1 115.07(11)
N6 C1 C10 112.33(11)
N6 C1 C2 109.07(11)
C10 C1 C2 109.92(11)
N6 C1 H1 108.5
C10 C1 H1 108.5
C2 C1 H1 108.5
C13 C2 C3 113.17(11)
C13 C2 C1 113.77(11)
C3 C2 C1 109.07(11)
C13 C2 H2 106.8
C3 C2 H2 106.8
C1 C2 H2 106.8
O1 C3 C4 124.31(13)
O1 C3 C2 123.69(13)
C4 C3 C2 111.94(12)
C3 C4 C5 110.02(11)
C3 C4 H4A 109.7
C5 C4 H4A 109.7
C3 C4 H4B 109.7
C5 C4 H4B 109.7
H4A C4 H4B 108.2
N6 C5 C4 111.46(12)
N6 C5 H5A 109.3
C4 C5 H5A 109.3
N6 C5 H5B 109.3
C4 C5 H5B 109.3
H5A C5 H5B 108.0
O2 C7 N6 122.22(13)
O2 C7 C8 119.99(13)
N6 C7 C8 117.78(12)
C7 C8 C9 115.47(12)
C7 C8 H8A 108.4
C9 C8 H8A 108.4
C7 C8 H8B 108.4
C9 C8 H8B 108.4
H8A C8 H8B 107.5
C8 C9 C10 105.61(11)
C8 C9 C12 110.84(12)
C10 C9 C12 111.59(12)
C8 C9 C11 109.98(12)
C10 C9 C11 109.64(12)
C12 C9 C11 109.14(12)
C1 C10 C9 113.17(12)
C1 C10 H10A 108.9
C9 C10 H10A 108.9
C1 C10 H10B 108.9
C9 C10 H10B 108.9
H10A C10 H10B 107.8
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C14 C13 C18 118.19(13)
C14 C13 C2 119.79(13)
C18 C13 C2 121.99(13)
C13 C14 C15 121.44(14)
C13 C14 H14 119.3
C15 C14 H14 119.3
C16 C15 C14 118.92(14)
C16 C15 H15 120.5
C14 C15 H15 120.5
C15 C16 C17 121.48(14)
C15 C16 Cl1 118.69(12)
C17 C16 Cl1 119.81(12)
C16 C17 C18 118.89(14)
C16 C17 H17 120.6
C18 C17 H17 120.6
C17 C18 C13 121.06(14)
C17 C18 H18 119.5
C13 C18 H18 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C16 1.7502(15)
O1 C3 1.2063(17)
O2 C7 1.2295(17)
N6 C7 1.3577(18)
N6 C5 1.4639(17)
N6 C1 1.4731(17)
C1 C10 1.5247(18)
C1 C2 1.559(2)
C1 H1 1.0000
C2 C13 1.5072(19)
C2 C3 1.5302(19)
C2 H2 1.0000
C3 C4 1.504(2)
C4 C5 1.530(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C7 C8 1.512(2)
C8 C9 1.5282(19)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.529(2)
C9 C12 1.535(2)
C9 C11 1.5319(19)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C14 1.389(2)
C13 C18 1.395(2)
C14 C15 1.388(2)
C14 H14 0.9500
C15 C16 1.374(2)
C15 H15 0.9500
C16 C17 1.383(2)
C17 C18 1.389(2)
C17 H17 0.9500
C18 H18 0.9500
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 C10 11.17(19)
C5 N6 C1 C10 -178.68(12)
C7 N6 C1 C2 133.29(14)
C5 N6 C1 C2 -56.57(15)
N6 C1 C2 C13 -177.11(11)
C10 C1 C2 C13 -53.55(15)
N6 C1 C2 C3 55.51(14)
C10 C1 C2 C3 179.07(11)
C13 C2 C3 O1 -7.8(2)
C1 C2 C3 O1 119.91(14)
C13 C2 C3 C4 174.75(12)
C1 C2 C3 C4 -57.53(14)
O1 C3 C4 C5 -121.47(15)
C2 C3 C4 C5 55.95(15)
C7 N6 C5 C4 -133.35(13)
C1 N6 C5 C4 55.72(16)
C3 C4 C5 N6 -53.22(16)
C5 N6 C7 O2 8.7(2)
C1 N6 C7 O2 178.58(13)
C5 N6 C7 C8 -172.56(13)
C1 N6 C7 C8 -2.7(2)
O2 C7 C8 C9 -156.48(13)
N6 C7 C8 C9 24.78(19)
C7 C8 C9 C10 -52.00(16)
C7 C8 C9 C12 69.01(16)
C7 C8 C9 C11 -170.22(13)
N6 C1 C10 C9 -41.72(16)
C2 C1 C10 C9 -163.35(11)
C8 C9 C10 C1 60.97(15)
C12 C9 C10 C1 -59.55(15)
C11 C9 C10 C1 179.42(12)
C3 C2 C13 C14 -112.57(14)
C1 C2 C13 C14 122.20(14)
C3 C2 C13 C18 65.47(17)
C1 C2 C13 C18 -59.76(17)
C18 C13 C14 C15 -0.8(2)
C2 C13 C14 C15 177.33(13)
C13 C14 C15 C16 0.0(2)
C14 C15 C16 C17 1.2(2)
C14 C15 C16 Cl1 -177.15(11)
C15 C16 C17 C18 -1.6(2)
Cl1 C16 C17 C18 176.70(11)
C16 C17 C18 C13 0.8(2)
C14 C13 C18 C17 0.3(2)
C2 C13 C18 C17 -177.74(13)
