#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/23/1502320.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_1502320
loop_
_publ_author_name
'Fei, Na'
'Yin, Hao'
'Wang, Shaozhong'
'Wang, Huaqin'
'Yao, Zhu-Jun'
_publ_section_title
;
 CuCl2-promoted 6-endo-dig chlorocyclization and oxidative aromatization
 cascade: efficient construction of 1-azaanthraquinones from
 N-propargylaminoquinones.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4208
_journal_page_last               4211
_journal_paper_doi               10.1021/ol201542h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C20 H12 Cl N O2'
_chemical_formula_weight         333.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 103.68(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2650(17)
_cell_length_b                   6.7530(14)
_cell_length_c                   14.254(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     773.0(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2988
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         1.47
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_correction_T_min  0.9501
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.066(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0533
_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)+(0.0950P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                1084
_reflns_number_total             1522
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201542h_si_002.cif
_cod_data_source_block           w
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/M
_cod_database_code               1502320
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl Cl -0.32245(13) 0.2500 0.16050(7) 0.0725(5) Uani 1 2 d S
N N -0.2221(3) 0.2500 0.4431(2) 0.0483(8) Uani 1 2 d S
O1 O 0.3186(3) 0.2500 0.37769(17) 0.0763(9) Uani 1 2 d S
C1 C 0.0434(4) 0.2500 0.3997(2) 0.0390(8) Uani 1 2 d S
C2 C 0.2297(4) 0.2500 0.4344(2) 0.0459(8) Uani 1 2 d S
O2 O -0.0685(3) 0.2500 0.63036(17) 0.0610(7) Uani 1 2 d S
C3 C 0.3032(4) 0.2500 0.5398(2) 0.0424(8) Uani 1 2 d S
C4 C 0.4750(4) 0.2500 0.5735(2) 0.0572(10) Uani 1 2 d S
H4A H 0.5424 0.2500 0.5297 0.069 Uiso 1 2 calc SR
C5 C 0.5460(5) 0.2500 0.6702(3) 0.0762(13) Uani 1 2 d S
H5A H 0.6614 0.2500 0.6919 0.091 Uiso 1 2 calc SR
C6 C 0.4461(5) 0.2500 0.7365(3) 0.0762(13) Uani 1 2 d S
H6A H 0.4945 0.2500 0.8024 0.091 Uiso 1 2 calc SR
C7 C 0.2762(5) 0.2500 0.7042(2) 0.0567(10) Uani 1 2 d S
H7A H 0.2096 0.2500 0.7484 0.068 Uiso 1 2 calc SR
C8 C 0.2030(4) 0.2500 0.6064(2) 0.0437(8) Uani 1 2 d S
C9 C 0.0198(4) 0.2500 0.5735(2) 0.0413(8) Uani 1 2 d S
C10 C -0.0548(4) 0.2500 0.4672(2) 0.0395(7) Uani 1 2 d S
C11 C -0.2955(4) 0.2500 0.3512(3) 0.0548(9) Uani 1 2 d S
H11A H -0.4112 0.2500 0.3333 0.066 Uiso 1 2 calc SR
C12 C -0.2073(4) 0.2500 0.2785(2) 0.0500(9) Uani 1 2 d S
C13 C -0.0352(4) 0.2500 0.3007(2) 0.0433(8) Uani 1 2 d S
C14 C 0.0547(4) 0.2500 0.2205(2) 0.0432(8) Uani 1 2 d S
C15 C 0.0916(3) 0.0750(4) 0.18156(18) 0.0617(8) Uani 1 1 d .
H15A H 0.0659 -0.0448 0.2068 0.074 Uiso 1 1 calc R
C16 C 0.1675(4) 0.0767(5) 0.10437(17) 0.0681(8) Uani 1 1 d .
H16A H 0.1928 -0.0429 0.0787 0.082 Uiso 1 1 calc R
C17 C 0.2056(5) 0.2500 0.0654(2) 0.0582(10) Uani 1 2 d S
C18 C 0.2856(6) 0.2500 -0.0208(3) 0.0789(14) Uani 1 2 d S
H18B H 0.4046 0.2500 0.0018 0.095 Uiso 1 2 calc SR
H18A H 0.2512 0.3661 -0.0593 0.095 Uiso 0.50 1 calc PR
H18C H 0.2512 0.1339 -0.0593 0.095 Uiso 0.50 1 calc PR
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C11 N C10 117.5(3) . .
C10 C1 C13 119.0(3) . .
C10 C1 C2 119.4(3) . .
C13 C1 C2 121.6(3) . .
O1 C2 C3 120.5(3) . .
O1 C2 C1 121.1(3) . .
C3 C2 C1 118.5(3) . .
C4 C3 C8 119.1(3) . .
C4 C3 C2 119.5(3) . .
C8 C3 C2 121.4(3) . .
C5 C4 C3 120.7(3) . .
C5 C4 H4A 119.7 . .
C3 C4 H4A 119.7 . .
C4 C5 C6 120.1(4) . .
C4 C5 H5A 119.9 . .
C6 C5 H5A 119.9 . .
C7 C6 C5 119.8(4) . .
C7 C6 H6A 120.1 . .
C5 C6 H6A 120.1 . .
C6 C7 C8 120.6(3) . .
C6 C7 H7A 119.7 . .
C8 C7 H7A 119.7 . .
C7 C8 C3 119.7(3) . .
C7 C8 C9 119.5(3) . .
C3 C8 C9 120.8(3) . .
O2 C9 C8 121.5(3) . .
O2 C9 C10 120.6(3) . .
C8 C9 C10 117.9(3) . .
N C10 C1 123.7(3) . .
N C10 C9 114.3(3) . .
C1 C10 C9 122.0(3) . .
N C11 C12 122.8(3) . .
N C11 H11A 118.6 . .
C12 C11 H11A 118.6 . .
C13 C12 C11 121.2(3) . .
C13 C12 Cl 121.5(3) . .
C11 C12 Cl 117.2(3) . .
C12 C13 C1 115.8(3) . .
C12 C13 C14 119.6(3) . .
C1 C13 C14 124.6(3) . .
C15 C14 C15 119.2(3) . 4_565
C15 C14 C13 120.36(15) . .
C15 C14 C13 120.36(15) 4_565 .
C14 C15 C16 120.0(2) . .
C14 C15 H15A 120.0 . .
C16 C15 H15A 120.0 . .
C17 C16 C15 121.4(3) . .
C17 C16 H16A 119.3 . .
C15 C16 H16A 119.3 . .
C16 C17 C16 118.2(3) 4_565 .
C16 C17 C18 120.91(15) 4_565 .
C16 C17 C18 120.91(15) . .
C17 C18 H18B 109.5 . .
C17 C18 H18A 109.5 . .
H18B C18 H18A 109.5 . .
C17 C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl C12 1.726(4) .
N C11 1.307(4) .
N C10 1.344(4) .
O1 C2 1.214(4) .
C1 C10 1.398(4) .
C1 C13 1.407(4) .
C1 C2 1.502(5) .
C2 C3 1.482(5) .
O2 C9 1.213(3) .
C3 C4 1.387(5) .
C3 C8 1.399(4) .
C4 C5 1.364(5) .
C4 H4A 0.9300 .
C5 C6 1.395(5) .
C5 H5A 0.9300 .
C6 C7 1.370(5) .
C6 H6A 0.9300 .
C7 C8 1.382(4) .
C7 H7A 0.9300 .
C8 C9 1.476(5) .
C9 C10 1.494(4) .
C11 C12 1.400(5) .
C11 H11A 0.9300 .
C12 C13 1.382(5) .
C13 C14 1.503(4) .
C14 C15 1.370(3) .
C14 C15 1.370(3) 4_565
C15 C16 1.389(3) .
C15 H15A 0.9300 .
C16 C17 1.364(3) .
C16 H16A 0.9300 .
C17 C16 1.364(3) 4_565
C17 C18 1.527(5) .
C18 H18B 0.9600 .
C18 H18A 0.9600 .
C18 H18C 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_4
C10 C1 C2 O1 180.0 . .
C13 C1 C2 O1 0.0 . .
C10 C1 C2 C3 0.0 . .
C13 C1 C2 C3 180.0 . .
O1 C2 C3 C4 0.000(1) . .
C1 C2 C3 C4 180.000(1) . .
O1 C2 C3 C8 180.000(1) . .
C1 C2 C3 C8 0.000(1) . .
C8 C3 C4 C5 0.000(1) . .
C2 C3 C4 C5 180.000(1) . .
C3 C4 C5 C6 0.000(2) . .
C4 C5 C6 C7 0.000(2) . .
C5 C6 C7 C8 0.000(2) . .
C6 C7 C8 C3 0.000(2) . .
C6 C7 C8 C9 180.000(2) . .
C4 C3 C8 C7 0.000(2) . .
C2 C3 C8 C7 180.000(1) . .
C4 C3 C8 C9 180.000(1) . .
C2 C3 C8 C9 0.000(1) . .
C7 C8 C9 O2 0.000(1) . .
C3 C8 C9 O2 180.000(1) . .
C7 C8 C9 C10 180.000(1) . .
C3 C8 C9 C10 0.0 . .
C11 N C10 C1 0.000(1) . .
C11 N C10 C9 180.0 . .
C13 C1 C10 N 0.0 . .
C2 C1 C10 N 180.0 . .
C13 C1 C10 C9 180.0 . .
C2 C1 C10 C9 0.000(1) . .
O2 C9 C10 N 0.0 . .
C8 C9 C10 N 180.0 . .
O2 C9 C10 C1 180.000(1) . .
C8 C9 C10 C1 0.000(1) . .
C10 N C11 C12 0.0 . .
N C11 C12 C13 0.0 . .
N C11 C12 Cl 180.0 . .
C11 C12 C13 C1 0.0 . .
Cl C12 C13 C1 180.0 . .
C11 C12 C13 C14 180.0 . .
Cl C12 C13 C14 0.0 . .
C10 C1 C13 C12 0.0 . .
C2 C1 C13 C12 180.0 . .
C10 C1 C13 C14 180.0 . .
C2 C1 C13 C14 0.0 . .
C12 C13 C14 C15 -88.0(3) . .
C1 C13 C14 C15 92.0(3) . .
C12 C13 C14 C15 88.0(3) . 4_565
C1 C13 C14 C15 -92.0(3) . 4_565
C15 C14 C15 C16 0.9(5) 4_565 .
C13 C14 C15 C16 176.9(3) . .
C14 C15 C16 C17 -0.5(5) . .
C15 C16 C17 C16 0.1(6) . 4_565
C15 C16 C17 C18 -178.7(3) . .
