#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/54/4025498.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_4025498
loop_
_publ_author_name
'Chunhui Jiang'
'Min Xu'
'Shaozhong Wang'
'Huaqin Wang'
'Zhu-Jun Yao'
_publ_section_title
;
 Azaanthraquinone Assembly fromN-Propargylamino Quinone via a
 Au(I)-Catalyzed 6-endo-digCycloisomerization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4323
_journal_page_last               4325
_journal_paper_doi               10.1021/jo1006637
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C20 H13 N O2'
_chemical_formula_weight         299.31
_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                 104.59(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6310(17)
_cell_length_b                   13.985(3)
_cell_length_c                   12.831(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1498.8(6)
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_collection       'CAD4 EXPRESS(Enraf-Nonius,1994)'
_computing_data_reduction        'XCAD4(Harms & Wocadlo,1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2913
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.083(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0572
_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)+(0.0700P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1710
_reflns_number_gt                1847
_reflns_number_total             2726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1006637_si_001.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1498.8(5)
_cod_database_code               4025498
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.1509(3) 0.47268(18) 0.30714(18) 0.0540(6) Uani 1 1 d . . .
O1 O -0.2166(3) 0.33520(15) 0.00405(16) 0.0782(8) Uani 1 1 d . . .
C1 C -0.2777(4) -0.0702(2) 0.0837(3) 0.0737(10) Uani 1 1 d . . .
H1A H -0.1932 -0.1123 0.0765 0.111 Uiso 1 1 calc R . .
H1B H -0.3560 -0.0656 0.0159 0.111 Uiso 1 1 calc R . .
H1C H -0.3273 -0.0950 0.1372 0.111 Uiso 1 1 calc R . .
O2 O 0.0630(3) 0.64366(15) 0.21502(18) 0.0690(7) Uani 1 1 d . . .
C2 C -0.2098(4) 0.0273(2) 0.1174(2) 0.0532(7) Uani 1 1 d . . .
C3 C -0.3046(3) 0.1030(2) 0.1340(2) 0.0539(7) Uani 1 1 d . . .
H3A H -0.4135 0.0931 0.1261 0.065 Uiso 1 1 calc R . .
C4 C -0.2411(3) 0.1923(2) 0.1620(2) 0.0504(7) Uani 1 1 d . . .
H4A H -0.3080 0.2417 0.1722 0.060 Uiso 1 1 calc R . .
C5 C -0.0784(3) 0.21027(18) 0.1754(2) 0.0448(7) Uani 1 1 d . . .
C6 C 0.0177(3) 0.1342(2) 0.1607(2) 0.0528(7) Uani 1 1 d . . .
H6A H 0.1271 0.1435 0.1706 0.063 Uiso 1 1 calc R . .
C7 C -0.0476(3) 0.0453(2) 0.1315(2) 0.0560(8) Uani 1 1 d . . .
H7A H 0.0189 -0.0041 0.1209 0.067 Uiso 1 1 calc R . .
C8 C -0.0033(3) 0.30378(19) 0.2137(2) 0.0453(7) Uani 1 1 d . . .
C9 C -0.0463(3) 0.39411(18) 0.1654(2) 0.0426(6) Uani 1 1 d . . .
C10 C -0.1661(3) 0.4042(2) 0.0588(2) 0.0479(7) Uani 1 1 d . . .
C11 C -0.2170(3) 0.50198(19) 0.0190(2) 0.0471(7) Uani 1 1 d . . .
C12 C -0.3396(3) 0.5127(2) -0.0742(2) 0.0585(8) Uani 1 1 d . . .
H12A H -0.3909 0.4590 -0.1096 0.070 Uiso 1 1 calc R . .
C13 C -0.3852(4) 0.6025(2) -0.1142(3) 0.0723(10) Uani 1 1 d . . .
H13A H -0.4681 0.6092 -0.1761 0.087 Uiso 1 1 calc R . .
C14 C -0.3087(4) 0.6825(2) -0.0631(3) 0.0780(10) Uani 1 1 d . . .
H14A H -0.3394 0.7429 -0.0909 0.094 Uiso 1 1 calc R . .
C15 C -0.1872(4) 0.6730(2) 0.0289(3) 0.0668(9) Uani 1 1 d . . .
H15A H -0.1360 0.7272 0.0631 0.080 Uiso 1 1 calc R . .
C16 C -0.1403(3) 0.58286(19) 0.0714(2) 0.0484(7) Uani 1 1 d . . .
C17 C -0.0076(3) 0.5741(2) 0.1706(2) 0.0508(7) Uani 1 1 d . . .
C18 C 0.0330(3) 0.47560(19) 0.2158(2) 0.0455(7) Uani 1 1 d . . .
C19 C 0.1915(4) 0.3870(2) 0.3495(2) 0.0577(8) Uani 1 1 d . . .
H19A H 0.2737 0.3835 0.4122 0.069 Uiso 1 1 calc R . .
C20 C 0.1201(3) 0.3027(2) 0.3070(2) 0.0543(8) Uani 1 1 d . . .
H20A H 0.1547 0.2450 0.3409 0.065 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'
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
C19 N C18 116.6(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.1(3) . . ?
C3 C2 C1 122.3(3) . . ?
C7 C2 C1 120.6(3) . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4A 119.4 . . ?
C5 C4 H4A 119.4 . . ?
C6 C5 C4 117.5(3) . . ?
C6 C5 C8 119.5(2) . . ?
C4 C5 C8 122.8(2) . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C2 121.9(3) . . ?
C6 C7 H7A 119.0 . . ?
C2 C7 H7A 119.0 . . ?
C20 C8 C9 116.6(2) . . ?
C20 C8 C5 116.9(2) . . ?
C9 C8 C5 126.6(2) . . ?
C18 C9 C8 118.7(2) . . ?
C18 C9 C10 119.3(2) . . ?
C8 C9 C10 121.9(2) . . ?
O1 C10 C11 120.1(2) . . ?
O1 C10 C9 121.4(2) . . ?
C11 C10 C9 118.5(2) . . ?
C12 C11 C16 119.5(3) . . ?
C12 C11 C10 119.3(2) . . ?
C16 C11 C10 121.1(2) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 119.3(3) . . ?
C15 C16 C17 119.6(3) . . ?
C11 C16 C17 121.0(2) . . ?
O2 C17 C16 121.6(3) . . ?
O2 C17 C18 120.9(3) . . ?
C16 C17 C18 117.4(2) . . ?
N C18 C9 123.5(3) . . ?
N C18 C17 114.6(2) . . ?
C9 C18 C17 121.9(2) . . ?
N C19 C20 124.4(2) . . ?
N C19 H19A 117.8 . . ?
C20 C19 H19A 117.8 . . ?
C19 C20 C8 120.1(3) . . ?
C19 C20 H20A 119.9 . . ?
C8 C20 H20A 119.9 . . ?
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
N C19 1.327(4) . ?
N C18 1.345(3) . ?
O1 C10 1.209(3) . ?
C1 C2 1.504(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O2 C17 1.212(3) . ?
C2 C3 1.386(4) . ?
C2 C7 1.389(4) . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.394(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.390(4) . ?
C5 C8 1.487(4) . ?
C6 C7 1.377(4) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C20 1.388(4) . ?
C8 C9 1.415(4) . ?
C9 C18 1.401(3) . ?
C9 C10 1.499(4) . ?
C10 C11 1.487(4) . ?
C11 C12 1.390(4) . ?
C11 C16 1.395(4) . ?
C12 C13 1.376(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.378(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.392(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.487(4) . ?
C17 C18 1.502(4) . ?
C19 C20 1.377(4) . ?
C19 H19A 0.9300 . ?
C20 H20A 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 0.8(4) . . . . ?
C1 C2 C3 C4 -178.2(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C8 -175.2(2) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
C8 C5 C6 C7 176.1(2) . . . . ?
C5 C6 C7 C2 -1.1(4) . . . . ?
C3 C2 C7 C6 0.0(4) . . . . ?
C1 C2 C7 C6 179.0(3) . . . . ?
C6 C5 C8 C20 -52.9(4) . . . . ?
C4 C5 C8 C20 121.4(3) . . . . ?
C6 C5 C8 C9 127.9(3) . . . . ?
C4 C5 C8 C9 -57.8(4) . . . . ?
C20 C8 C9 C18 -2.2(4) . . . . ?
C5 C8 C9 C18 176.9(3) . . . . ?
C20 C8 C9 C10 173.8(2) . . . . ?
C5 C8 C9 C10 -7.0(4) . . . . ?
C18 C9 C10 O1 167.2(3) . . . . ?
C8 C9 C10 O1 -8.9(4) . . . . ?
C18 C9 C10 C11 -10.2(4) . . . . ?
C8 C9 C10 C11 173.8(2) . . . . ?
O1 C10 C11 C12 9.0(4) . . . . ?
C9 C10 C11 C12 -173.6(3) . . . . ?
O1 C10 C11 C16 -168.7(3) . . . . ?
C9 C10 C11 C16 8.7(4) . . . . ?
C16 C11 C12 C13 -0.2(5) . . . . ?
C10 C11 C12 C13 -178.0(3) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C11 0.5(5) . . . . ?
C14 C15 C16 C17 179.5(3) . . . . ?
C12 C11 C16 C15 -0.4(4) . . . . ?
C10 C11 C16 C15 177.4(3) . . . . ?
C12 C11 C16 C17 -179.4(3) . . . . ?
C10 C11 C16 C17 -1.6(4) . . . . ?
C15 C16 C17 O2 -1.1(4) . . . . ?
C11 C16 C17 O2 177.8(3) . . . . ?
C15 C16 C17 C18 177.2(3) . . . . ?
C11 C16 C17 C18 -3.9(4) . . . . ?
C19 N C18 C9 0.1(4) . . . . ?
C19 N C18 C17 -179.5(2) . . . . ?
C8 C9 C18 N 1.5(4) . . . . ?
C10 C9 C18 N -174.7(2) . . . . ?
C8 C9 C18 C17 -179.0(2) . . . . ?
C10 C9 C18 C17 4.8(4) . . . . ?
O2 C17 C18 N 0.1(4) . . . . ?
C16 C17 C18 N -178.3(2) . . . . ?
O2 C17 C18 C9 -179.5(3) . . . . ?
C16 C17 C18 C9 2.2(4) . . . . ?
C18 N C19 C20 -0.8(4) . . . . ?
N C19 C20 C8 -0.1(5) . . . . ?
C9 C8 C20 C19 1.6(4) . . . . ?
C5 C8 C20 C19 -177.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659224
