#------------------------------------------------------------------------------
#$Date: 2016-08-12 16:33:26 +0300 (Fri, 12 Aug 2016) $
#$Revision: 185777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119140.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_7119140
loop_
_publ_author_name
'Yuan-Ming Sun'
'Peng Gu'
'Yu-Ning Gao'
'Qin Xu'
'Min Shi'
_publ_section_title
;
 Gold(I) catalyzed tandem cyclization of propargylic esters to
 4-acyloxy-1,2-dihydroquinolines
;
_journal_name_full               Chem.Commun.
_journal_page_first              6942
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-11-06 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6053(10)
_cell_length_b                   11.6403(14)
_cell_length_c                   17.468(2)
_cell_measurement_reflns_used    4360
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.145
_cell_measurement_theta_min      5.277
_cell_volume                     1749.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10517
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.102
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0701P)²+0.0824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3189
_reflns_number_total             3444
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc03132c2.cif
_cod_data_source_block           cd15218
_cod_database_code               7119140
_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. 
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.8531(2) 0.95531(15) 0.30430(9) 0.0362(4) Uani 1 1 d . . . . .
O1 O 1.2477(2) 1.12764(16) 0.36932(11) 0.0597(5) Uani 1 1 d . . . . .
H1 H 1.2642 1.1892 0.3480 0.090 Uiso 1 1 calc R U . . .
O2 O 0.7705(2) 0.83527(15) 0.21133(10) 0.0559(5) Uani 1 1 d . . . . .
O3 O 0.67416(18) 1.01548(13) 0.22209(8) 0.0430(4) Uani 1 1 d . . . . .
C1 C 0.8322(3) 1.05736(17) 0.34814(10) 0.0357(4) Uani 1 1 d . . . . .
C2 C 0.6882(3) 1.0879(2) 0.37751(12) 0.0450(5) Uani 1 1 d . . . . .
H2 H 0.6011 1.0429 0.3678 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6763(4) 1.1860(2) 0.42131(13) 0.0562(6) Uani 1 1 d . . . . .
H3 H 0.5802 1.2080 0.4407 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8058(4) 1.2516(2) 0.43652(14) 0.0627(8) Uani 1 1 d . . . . .
H4 H 0.7965 1.3176 0.4662 0.075 Uiso 1 1 calc R U . . .
C5 C 0.9482(3) 1.2203(2) 0.40822(13) 0.0515(6) Uani 1 1 d . . . . .
H5 H 1.0350 1.2651 0.4189 0.062 Uiso 1 1 calc R U . . .
C6 C 0.9638(3) 1.12227(18) 0.36377(11) 0.0392(5) Uani 1 1 d . . . . .
C7 C 1.1166(2) 1.07472(19) 0.33619(12) 0.0426(5) Uani 1 1 d . . . . .
H7 H 1.1225 1.0800 0.2803 0.051 Uiso 1 1 calc R U . . .
C8 C 1.1171(2) 0.94950(19) 0.36066(12) 0.0416(5) Uani 1 1 d . . . . .
H8A H 1.1039 0.9452 0.4157 0.050 Uiso 1 1 calc R U . . .
H8B H 1.2169 0.9157 0.3481 0.050 Uiso 1 1 calc R U . . .
C9 C 0.9875(2) 0.88005(18) 0.32161(11) 0.0375(4) Uani 1 1 d . . . . .
H9 H 1.0282 0.8506 0.2730 0.045 Uiso 1 1 calc R U . . .
C10 C 0.9451(2) 0.77840(17) 0.37126(11) 0.0365(4) Uani 1 1 d . . . . .
C11 C 1.0161(3) 0.6737(2) 0.35967(14) 0.0490(5) Uani 1 1 d . . . . .
H11 H 1.0832 0.6638 0.3185 0.059 Uiso 1 1 calc R U . . .
C12 C 0.9877(4) 0.5830(2) 0.40936(16) 0.0621(7) Uani 1 1 d . . . . .
H12 H 1.0360 0.5125 0.4013 0.075 Uiso 1 1 calc R U . . .
C13 C 0.8893(3) 0.5967(2) 0.46998(16) 0.0618(7) Uani 1 1 d . . . . .
H13 H 0.8708 0.5358 0.5032 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8177(4) 0.7006(2) 0.48168(15) 0.0600(7) Uani 1 1 d . . . . .
H14 H 0.7512 0.7103 0.5231 0.072 Uiso 1 1 calc R U . . .
C15 C 0.8441(3) 0.79013(19) 0.43225(13) 0.0490(5) Uani 1 1 d . . . . .
H15 H 0.7932 0.8597 0.4399 0.059 Uiso 1 1 calc R U . . .
C16 C 0.7630(2) 0.92784(17) 0.24287(12) 0.0371(4) Uani 1 1 d . . . . .
C17 C 0.5372(3) 1.0013(2) 0.17196(13) 0.0498(6) Uani 1 1 d . . . . .
C18 C 0.5849(4) 0.9676(3) 0.09179(13) 0.0693(8) Uani 1 1 d . . . . .
H18A H 0.6242 0.8904 0.0921 0.104 Uiso 1 1 calc R U . . .
H18B H 0.6643 1.0189 0.0739 0.104 Uiso 1 1 calc R U . . .
H18C H 0.4965 0.9720 0.0584 0.104 Uiso 1 1 calc R U . . .
C19 C 0.4297(3) 0.9146(3) 0.20799(18) 0.0777(9) Uani 1 1 d . . . . .
H19A H 0.4759 0.8397 0.2053 0.117 Uiso 1 1 calc R U . . .
H19B H 0.3325 0.9142 0.1810 0.117 Uiso 1 1 calc R U . . .
H19C H 0.4121 0.9347 0.2606 0.117 Uiso 1 1 calc R U . . .
C20 C 0.4679(4) 1.1202(3) 0.1739(2) 0.0907(12) Uani 1 1 d . . . . .
H20A H 0.3737 1.1212 0.1445 0.136 Uiso 1 1 calc R U . . .
H20B H 0.5405 1.1740 0.1526 0.136 Uiso 1 1 calc R U . . .
H20C H 0.4454 1.1410 0.2259 0.136 Uiso 1 1 calc R U . . .
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'
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
C16 N1 C1 123.17(16) . .
C16 N1 C9 117.78(15) . .
C1 N1 C9 118.82(16) . .
C7 O1 H1 109.5 . .
C16 O3 C17 122.43(17) . .
C6 C1 C2 121.09(18) . .
C6 C1 N1 117.12(19) . .
C2 C1 N1 121.7(2) . .
C3 C2 C1 118.9(2) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C4 C3 C2 120.5(2) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 C5 120.4(2) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C4 C5 C6 120.5(3) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C5 C6 C1 118.6(2) . .
C5 C6 C7 124.5(2) . .
C1 C6 C7 116.71(18) . .
O1 C7 C6 114.00(19) . .
O1 C7 C8 107.55(17) . .
C6 C7 C8 105.38(18) . .
O1 C7 H7 109.9 . .
C6 C7 H7 109.9 . .
C8 C7 H7 109.9 . .
C7 C8 C9 112.19(17) . .
C7 C8 H8A 109.2 . .
C9 C8 H8A 109.2 . .
C7 C8 H8B 109.2 . .
C9 C8 H8B 109.2 . .
H8A C8 H8B 107.9 . .
N1 C9 C10 113.04(17) . .
N1 C9 C8 110.23(17) . .
C10 C9 C8 109.40(17) . .
N1 C9 H9 108.0 . .
C10 C9 H9 108.0 . .
C8 C9 H9 108.0 . .
C11 C10 C15 118.7(2) . .
C11 C10 C9 120.06(19) . .
C15 C10 C9 121.11(19) . .
C10 C11 C12 120.2(2) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C13 C12 C11 120.3(2) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C14 119.8(2) . .
C12 C13 H13 120.1 . .
C14 C13 H13 120.1 . .
C15 C14 C13 120.1(2) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C14 C15 C10 120.9(2) . .
C14 C15 H15 119.5 . .
C10 C15 H15 119.5 . .
O2 C16 O3 126.17(19) . .
O2 C16 N1 122.47(19) . .
O3 C16 N1 111.32(16) . .
O3 C17 C19 108.5(2) . .
O3 C17 C20 101.5(2) . .
C19 C17 C20 111.3(3) . .
O3 C17 C18 111.2(2) . .
C19 C17 C18 112.3(2) . .
C20 C17 C18 111.5(3) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C17 C20 H20A 109.5 . .
C17 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C17 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C16 1.362(3) .
N1 C1 1.425(3) .
N1 C9 1.482(3) .
O1 C7 1.409(3) .
O1 H1 0.8200 .
O2 C16 1.212(3) .
O3 C16 1.326(3) .
O3 C17 1.478(3) .
C1 C6 1.389(3) .
C1 C2 1.387(3) .
C2 C3 1.378(3) .
C2 H2 0.9300 .
C3 C4 1.376(4) .
C3 H3 0.9300 .
C4 C5 1.371(4) .
C4 H4 0.9300 .
C5 C6 1.387(3) .
C5 H5 0.9300 .
C6 C7 1.505(3) .
C7 C8 1.519(3) .
C7 H7 0.9800 .
C8 C9 1.537(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.512(3) .
C9 H9 0.9800 .
C10 C11 1.378(3) .
C10 C15 1.382(3) .
C11 C12 1.389(4) .
C11 H11 0.9300 .
C12 C13 1.365(4) .
C12 H12 0.9300 .
C13 C14 1.373(4) .
C13 H13 0.9300 .
C14 C15 1.372(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C17 C19 1.507(4) .
C17 C20 1.508(4) .
C17 C18 1.511(3) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
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
C16 N1 C1 C6 -131.9(2) . . . .
C9 N1 C1 C6 42.5(2) . . . .
C16 N1 C1 C2 51.4(3) . . . .
C9 N1 C1 C2 -134.2(2) . . . .
C6 C1 C2 C3 1.6(3) . . . .
N1 C1 C2 C3 178.16(18) . . . .
C1 C2 C3 C4 -0.9(3) . . . .
C2 C3 C4 C5 0.0(4) . . . .
C3 C4 C5 C6 0.2(4) . . . .
C4 C5 C6 C1 0.5(3) . . . .
C4 C5 C6 C7 -174.1(2) . . . .
C2 C1 C6 C5 -1.4(3) . . . .
N1 C1 C6 C5 -178.11(17) . . . .
C2 C1 C6 C7 173.63(19) . . . .
N1 C1 C6 C7 -3.1(2) . . . .
C5 C6 C7 O1 9.7(3) . . . .
C1 C6 C7 O1 -165.05(17) . . . .
C5 C6 C7 C8 127.4(2) . . . .
C1 C6 C7 C8 -47.4(2) . . . .
O1 C7 C8 C9 -174.54(17) . . . .
C6 C7 C8 C9 63.5(2) . . . .
C16 N1 C9 C10 -86.4(2) . . . .
C1 N1 C9 C10 98.9(2) . . . .
C16 N1 C9 C8 150.85(17) . . . .
C1 N1 C9 C8 -23.9(2) . . . .
C7 C8 C9 N1 -29.3(2) . . . .
C7 C8 C9 C10 -154.21(18) . . . .
N1 C9 C10 C11 143.8(2) . . . .
C8 C9 C10 C11 -93.0(2) . . . .
N1 C9 C10 C15 -41.0(3) . . . .
C8 C9 C10 C15 82.2(3) . . . .
C15 C10 C11 C12 -1.0(4) . . . .
C9 C10 C11 C12 174.3(2) . . . .
C10 C11 C12 C13 0.1(4) . . . .
C11 C12 C13 C14 0.2(4) . . . .
C12 C13 C14 C15 0.5(4) . . . .
C13 C14 C15 C10 -1.5(4) . . . .
C11 C10 C15 C14 1.7(4) . . . .
C9 C10 C15 C14 -173.5(2) . . . .
C17 O3 C16 O2 19.2(3) . . . .
C17 O3 C16 N1 -163.10(17) . . . .
C1 N1 C16 O2 -171.6(2) . . . .
C9 N1 C16 O2 14.0(3) . . . .
C1 N1 C16 O3 10.6(3) . . . .
C9 N1 C16 O3 -163.82(17) . . . .
C16 O3 C17 C19 56.2(3) . . . .
C16 O3 C17 C20 173.4(2) . . . .
C16 O3 C17 C18 -67.9(3) . . . .
