#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:17:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178464 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/85/4028598.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_4028598
loop_
_publ_author_name
'Shugao Zhu'
'Luling Wu'
'Xian Huang'
_publ_section_title
;
 Gold-Catalyzed Cyclization of 3-(2'-Azidoaryl)-1-arylpropargyl Carbonates
 or 3-Aryl-1-(2'-azidoaryl)propargyl Carbonates to Produce Quinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9120
_journal_page_last               9126
_journal_paper_doi               10.1021/jo401324k
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C15 H10 F N O'
_chemical_formula_weight         239.24
_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                 92.215(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7400(5)
_cell_length_b                   7.1758(3)
_cell_length_c                   13.2748(7)
_cell_measurement_reflns_used    2340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5226
_cell_measurement_theta_min      2.8329
_cell_volume                     1117.49(9)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '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  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4857
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Oxford Diffraction, 2010) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0348
_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)+(0.0467P)²+0.2338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                1738
_reflns_number_total             2047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401324k_si_003.cif
_cod_data_source_block           110712_zsg_110630
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028598
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
F1 F -0.47593(8) 0.19247(16) 0.19990(8) 0.0744(4) Uani 1 1 d .
O1 O 0.07208(8) 0.32184(15) 0.65611(7) 0.0496(3) Uani 1 1 d .
N1 N 0.03808(9) 0.17672(14) 0.36075(7) 0.0329(3) Uani 1 1 d .
H1 H 0.0309 0.1538 0.2972 0.039 Uiso 1 1 calc R
C1 C 0.23824(11) 0.11358(19) 0.35202(10) 0.0394(3) Uani 1 1 d .
H1A H 0.2282 0.0792 0.2847 0.047 Uiso 1 1 calc R
C2 C 0.34415(11) 0.1084(2) 0.39822(11) 0.0449(4) Uani 1 1 d .
H2 H 0.4061 0.0698 0.3620 0.054 Uiso 1 1 calc R
C3 C 0.36071(12) 0.1604(2) 0.49923(11) 0.0450(4) Uani 1 1 d .
H3 H 0.4335 0.1581 0.5295 0.054 Uiso 1 1 calc R
C4 C 0.27000(11) 0.21426(19) 0.55325(10) 0.0393(3) Uani 1 1 d .
H4 H 0.2813 0.2473 0.6206 0.047 Uiso 1 1 calc R
C5 C 0.15979(11) 0.22057(17) 0.50859(9) 0.0319(3) Uani 1 1 d .
C6 C 0.14471(10) 0.17112(16) 0.40680(9) 0.0305(3) Uani 1 1 d .
C7 C -0.05609(10) 0.21723(16) 0.41209(9) 0.0308(3) Uani 1 1 d .
C8 C -0.04606(11) 0.26047(18) 0.51251(9) 0.0352(3) Uani 1 1 d .
H8 H -0.1120 0.2829 0.5472 0.042 Uiso 1 1 calc R
C9 C 0.06078(11) 0.27237(18) 0.56569(9) 0.0344(3) Uani 1 1 d .
C10 C -0.16667(11) 0.20961(17) 0.35504(9) 0.0337(3) Uani 1 1 d .
C11 C -0.18134(11) 0.10306(19) 0.26777(10) 0.0407(3) Uani 1 1 d .
H11 H -0.1202 0.0354 0.2444 0.049 Uiso 1 1 calc R
C12 C -0.28532(12) 0.0964(2) 0.21540(11) 0.0485(4) Uani 1 1 d .
H12 H -0.2949 0.0256 0.1570 0.058 Uiso 1 1 calc R
C13 C -0.37352(12) 0.1965(2) 0.25167(12) 0.0492(4) Uani 1 1 d .
C14 C -0.36388(12) 0.3017(2) 0.33732(13) 0.0517(4) Uani 1 1 d .
H14 H -0.4260 0.3673 0.3604 0.062 Uiso 1 1 calc R
C15 C -0.25965(12) 0.30793(19) 0.38868(11) 0.0427(3) Uani 1 1 d .
H15 H -0.2515 0.3794 0.4470 0.051 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'
F F 0.0171 0.0103 '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
C7 N1 C6 122.09(10)
C7 N1 H1 119.0
C6 N1 H1 119.0
C2 C1 C6 119.53(12)
C2 C1 H1A 120.2
C6 C1 H1A 120.2
C1 C2 C3 120.93(13)
C1 C2 H2 119.5
C3 C2 H2 119.5
C4 C3 C2 119.85(13)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.90(12)
C3 C4 H4 119.5
C5 C4 H4 119.5
C6 C5 C4 118.63(12)
C6 C5 C9 119.44(11)
C4 C5 C9 121.91(11)
N1 C6 C5 120.06(11)
N1 C6 C1 119.79(11)
C5 C6 C1 120.14(11)
N1 C7 C8 119.86(11)
N1 C7 C10 116.91(11)
C8 C7 C10 123.22(11)
C7 C8 C9 122.65(12)
C7 C8 H8 118.7
C9 C8 H8 118.7
O1 C9 C8 123.54(12)
O1 C9 C5 120.81(12)
C8 C9 C5 115.65(11)
C15 C10 C11 118.23(12)
C15 C10 C7 120.15(12)
C11 C10 C7 121.61(12)
C12 C11 C10 121.04(13)
C12 C11 H11 119.5
C10 C11 H11 119.5
C13 C12 C11 118.19(14)
C13 C12 H12 120.9
C11 C12 H12 120.9
F1 C13 C12 118.59(14)
F1 C13 C14 118.34(14)
C12 C13 C14 123.06(13)
C13 C14 C15 118.24(14)
C13 C14 H14 120.9
C15 C14 H14 120.9
C14 C15 C10 121.24(14)
C14 C15 H15 119.4
C10 C15 H15 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C13 1.3619(15)
O1 C9 1.2538(15)
N1 C7 1.3526(16)
N1 C6 1.3723(15)
N1 H1 0.8600
C1 C2 1.3655(18)
C1 C6 1.4023(17)
C1 H1A 0.9300
C2 C3 1.398(2)
C2 H2 0.9300
C3 C4 1.363(2)
C3 H3 0.9300
C4 C5 1.4030(17)
C4 H4 0.9300
C5 C6 1.4017(17)
C5 C9 1.4600(17)
C7 C8 1.3692(17)
C7 C10 1.4785(17)
C8 C9 1.4179(17)
C8 H8 0.9300
C10 C15 1.3879(19)
C10 C11 1.3932(18)
C11 C12 1.3820(18)
C11 H11 0.9300
C12 C13 1.363(2)
C12 H12 0.9300
C13 C14 1.366(2)
C14 C15 1.3783(19)
C14 H14 0.9300
C15 H15 0.9300
