#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/21/1512115.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_1512115
loop_
_publ_author_name
'Gao, Peng'
'Liu, Jinjian'
'Wei, Yunyang'
_publ_section_title
;
 Hypervalent Iodine(III)-Mediated Benzannulation of Enamines with Alkynes
 for the Synthesis of Polysubstituted Naphthalene Derivatives.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2872
_journal_page_last               2875
_journal_paper_doi               10.1021/ol401206g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.488(3)
_cell_length_b                   7.5150(15)
_cell_length_c                   13.547(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1418.2(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0734
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2718
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.46
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0694
_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)+(0.0850P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                1358
_reflns_number_total             2596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401206g_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 /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1418.2(5)
_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               1512115
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N N 0.57762(19) 0.3179(4) 0.28794(19) 0.0774(10) Uani 1 1 d .
H0A H 0.5447 0.4144 0.2823 0.093 Uiso 1 1 calc R
H0B H 0.5683 0.2457 0.2369 0.093 Uiso 1 1 calc R
O1 O 0.63443(16) 0.6547(3) 0.54402(16) 0.0648(7) Uani 1 1 d .
C1 C 0.9597(2) 0.1346(4) 0.6646(2) 0.0593(9) Uani 1 1 d .
H1A H 0.9780 0.1360 0.6040 0.071 Uiso 1 1 calc R
O2 O 0.53752(17) 0.6000(3) 0.38826(17) 0.0807(8) Uani 1 1 d .
C2 C 1.0283(2) 0.1043(5) 0.7565(3) 0.0721(10) Uani 1 1 d .
H2A H 1.0916 0.0839 0.7566 0.086 Uiso 1 1 calc R
C3 C 1.0042(3) 0.1040(5) 0.8470(3) 0.0747(11) Uani 1 1 d .
H3A H 1.0505 0.0831 0.9087 0.090 Uiso 1 1 calc R
C4 C 0.9103(3) 0.1352(5) 0.8452(2) 0.0700(10) Uani 1 1 d .
H4A H 0.8933 0.1388 0.9066 0.084 Uiso 1 1 calc R
C5 C 0.8408(2) 0.1612(4) 0.7532(2) 0.0574(9) Uani 1 1 d .
H5A H 0.7773 0.1780 0.7534 0.069 Uiso 1 1 calc R
C6 C 0.8645(2) 0.1627(4) 0.6609(2) 0.0486(8) Uani 1 1 d .
C7 C 0.7891(2) 0.1973(4) 0.5632(2) 0.0462(8) Uani 1 1 d .
C8 C 0.7354(2) 0.3492(4) 0.5527(2) 0.0512(8) Uani 1 1 d .
H8A H 0.7474 0.4284 0.6075 0.061 Uiso 1 1 calc R
C9 C 0.6621(2) 0.3923(4) 0.4620(2) 0.0514(8) Uani 1 1 d .
C10 C 0.6442(2) 0.2798(5) 0.3771(2) 0.0544(9) Uani 1 1 d .
C11 C 0.6982(2) 0.1166(5) 0.3862(2) 0.0539(9) Uani 1 1 d .
C12 C 0.6807(2) -0.0076(5) 0.3037(2) 0.0645(10) Uani 1 1 d .
H12A H 0.6348 0.0180 0.2424 0.077 Uiso 1 1 calc R
C13 C 0.7303(3) -0.1633(6) 0.3134(3) 0.0779(11) Uani 1 1 d .
H13A H 0.7184 -0.2425 0.2586 0.093 Uiso 1 1 calc R
C14 C 0.7989(3) -0.2050(5) 0.4049(3) 0.0777(11) Uani 1 1 d .
H14A H 0.8319 -0.3124 0.4110 0.093 Uiso 1 1 calc R
C15 C 0.8178(2) -0.0902(5) 0.4850(3) 0.0642(9) Uani 1 1 d .
H15A H 0.8633 -0.1206 0.5457 0.077 Uiso 1 1 calc R
C16 C 0.7697(2) 0.0755(4) 0.4784(2) 0.0495(8) Uani 1 1 d .
C17 C 0.6060(2) 0.5564(5) 0.4589(2) 0.0569(9) Uani 1 1 d .
C18 C 0.5833(3) 0.8183(5) 0.5447(3) 0.0770(11) Uani 1 1 d .
H18A H 0.6096 0.8788 0.6087 0.115 Uiso 1 1 calc R
H18B H 0.5167 0.7930 0.5366 0.115 Uiso 1 1 calc R
H18C H 0.5895 0.8925 0.4892 0.115 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
C10 N H0A 120.0
C10 N H0B 120.0
H0A N H0B 120.0
C17 O1 C18 116.2(3)
C2 C1 C6 121.4(3)
C2 C1 H1A 119.3
C6 C1 H1A 119.3
C3 C2 C1 120.8(3)
C3 C2 H2A 119.6
C1 C2 H2A 119.6
C2 C3 C4 118.7(3)
C2 C3 H3A 120.6
C4 C3 H3A 120.6
C3 C4 C5 120.8(3)
C3 C4 H4A 119.6
C5 C4 H4A 119.6
C4 C5 C6 121.0(3)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C1 C6 C5 117.3(3)
C1 C6 C7 122.7(3)
C5 C6 C7 120.0(3)
C8 C7 C16 117.9(3)
C8 C7 C6 119.7(3)
C16 C7 C6 122.3(3)
C7 C8 C9 123.3(3)
C7 C8 H8A 118.4
C9 C8 H8A 118.4
C10 C9 C8 120.0(3)
C10 C9 C17 120.6(3)
C8 C9 C17 119.4(3)
N C10 C9 122.3(3)
N C10 C11 119.6(3)
C9 C10 C11 118.2(3)
C16 C11 C12 118.5(3)
C16 C11 C10 120.5(3)
C12 C11 C10 121.0(3)
C13 C12 C11 120.8(3)
C13 C12 H12A 119.6
C11 C12 H12A 119.6
C12 C13 C14 120.5(3)
C12 C13 H13A 119.7
C14 C13 H13A 119.7
C15 C14 C13 120.4(4)
C15 C14 H14A 119.8
C13 C14 H14A 119.8
C14 C15 C16 121.4(3)
C14 C15 H15A 119.3
C16 C15 H15A 119.3
C15 C16 C11 118.3(3)
C15 C16 C7 121.6(3)
C11 C16 C7 120.1(3)
O2 C17 O1 121.4(3)
O2 C17 C9 124.9(3)
O1 C17 C9 113.7(3)
O1 C18 H18A 109.5
O1 C18 H18B 109.5
H18A C18 H18B 109.5
O1 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C10 1.353(4)
N H0A 0.8600
N H0B 0.8600
O1 C17 1.336(4)
O1 C18 1.436(4)
C1 C2 1.381(4)
C1 C6 1.383(4)
C1 H1A 0.9300
O2 C17 1.219(3)
C2 C3 1.364(5)
C2 H2A 0.9300
C3 C4 1.374(5)
C3 H3A 0.9300
C4 C5 1.384(4)
C4 H4A 0.9300
C5 C6 1.385(4)
C5 H5A 0.9300
C6 C7 1.489(4)
C7 C8 1.367(4)
C7 C16 1.435(4)
C8 C9 1.423(4)
C8 H8A 0.9300
C9 C10 1.394(4)
C9 C17 1.471(4)
C10 C11 1.442(4)
C11 C16 1.420(4)
C11 C12 1.425(4)
C12 C13 1.360(5)
C12 H12A 0.9300
C13 C14 1.396(5)
C13 H13A 0.9300
C14 C15 1.354(4)
C14 H14A 0.9300
C15 C16 1.418(4)
C15 H15A 0.9300
C18 H18A 0.9600
C18 H18B 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
C6 C1 C2 C3 -1.0(6)
C1 C2 C3 C4 -0.3(6)
C2 C3 C4 C5 1.9(6)
C3 C4 C5 C6 -2.2(5)
C2 C1 C6 C5 0.7(5)
C2 C1 C6 C7 179.4(3)
C4 C5 C6 C1 0.9(5)
C4 C5 C6 C7 -177.8(3)
C1 C6 C7 C8 -122.9(3)
C5 C6 C7 C8 55.8(4)
C1 C6 C7 C16 57.5(4)
C5 C6 C7 C16 -123.9(3)
C16 C7 C8 C9 -0.3(4)
C6 C7 C8 C9 180.0(3)
C7 C8 C9 C10 -2.1(5)
C7 C8 C9 C17 178.1(3)
C8 C9 C10 N -177.6(3)
C17 C9 C10 N 2.2(5)
C8 C9 C10 C11 3.2(4)
C17 C9 C10 C11 -177.0(3)
N C10 C11 C16 178.8(3)
C9 C10 C11 C16 -2.0(4)
N C10 C11 C12 -1.7(4)
C9 C10 C11 C12 177.5(3)
C16 C11 C12 C13 1.0(5)
C10 C11 C12 C13 -178.5(3)
C11 C12 C13 C14 0.5(5)
C12 C13 C14 C15 -0.7(6)
C13 C14 C15 C16 -0.6(5)
C14 C15 C16 C11 2.1(5)
C14 C15 C16 C7 179.7(3)
C12 C11 C16 C15 -2.2(4)
C10 C11 C16 C15 177.3(3)
C12 C11 C16 C7 -179.9(3)
C10 C11 C16 C7 -0.4(4)
C8 C7 C16 C15 -176.1(3)
C6 C7 C16 C15 3.6(4)
C8 C7 C16 C11 1.5(4)
C6 C7 C16 C11 -178.8(3)
C18 O1 C17 O2 -3.4(4)
C18 O1 C17 C9 178.9(3)
C10 C9 C17 O2 5.5(5)
C8 C9 C17 O2 -174.7(3)
C10 C9 C17 O1 -177.0(3)
C8 C9 C17 O1 2.9(4)
