#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/42/1504294.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_1504294
loop_
_publ_author_name
'He, Wei'
'Yip, Kai-Tai'
'Zhu, Nian-Yong'
'Yang, Dan'
_publ_section_title
;
 Pd(II)/(t)Bu-quinolineoxazoline: an air-stable and modular chiral
 catalyst system for enantioselective oxidative cascade cyclization.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5626
_journal_page_last               5628
_journal_paper_doi               10.1021/ol902348t
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C18 H14 Cl N O'
_chemical_formula_sum            'C18 H14 Cl N O'
_chemical_formula_weight         295.75
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6210(15)
_cell_length_b                   8.3930(17)
_cell_length_c                   22.728(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1453.8(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.1087
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9763
_diffrn_reflns_theta_full        25.65
_diffrn_reflns_theta_max         25.65
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.720
_refine_ls_hydrogen_treatment    ride-on
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.720
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                1953
_reflns_number_total             2688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902348t_si_001.cif
_cod_data_source_block           mar1940
_cod_database_code               1504294
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C1 C 1.1709(3) 0.1690(3) 0.98819(9) 0.0471(5) Uani 1 1 d .
C2 C 1.1715(3) 0.2138(3) 0.92468(8) 0.0423(5) Uani 1 1 d .
C3 C 1.2157(3) 0.3555(3) 0.90578(10) 0.0608(7) Uani 1 1 d .
H3A H 1.2488 0.4340 0.9324 0.073 Uiso 1 1 calc R
H3B H 1.2140 0.3777 0.8657 0.073 Uiso 1 1 calc R
C4 C 1.1217(3) 0.0677(2) 0.88910(8) 0.0400(5) Uani 1 1 d .
H4 H 1.2302 0.0120 0.8785 0.048 Uiso 1 1 calc R
C5 C 1.0241(3) -0.0349(2) 0.93478(8) 0.0402(5) Uani 1 1 d .
H5 H 0.8980 -0.0127 0.9324 0.048 Uiso 1 1 calc R
C6 C 1.0525(3) -0.2152(2) 0.93931(8) 0.0493(5) Uani 1 1 d .
H6A H 0.9567 -0.2735 0.9213 0.059 Uiso 1 1 calc R
H6B H 1.1622 -0.2469 0.9211 0.059 Uiso 1 1 calc R
C7 C 1.0570(3) -0.2408(3) 1.00543(9) 0.0464(5) Uani 1 1 d .
C8 C 1.0871(3) -0.0961(3) 1.03359(9) 0.0446(5) Uani 1 1 d .
C9 C 1.1073(3) -0.0843(3) 1.09388(9) 0.0578(7) Uani 1 1 d .
H9 H 1.1278 0.0134 1.1119 0.069 Uiso 1 1 calc R
C10 C 1.0959(3) -0.2232(4) 1.12631(11) 0.0687(8) Uani 1 1 d .
H10 H 1.1105 -0.2195 1.1669 0.082 Uiso 1 1 calc R
C11 C 1.0633(3) -0.3665(4) 1.09932(12) 0.0723(9) Uani 1 1 d .
H11 H 1.0536 -0.4579 1.1222 0.087 Uiso 1 1 calc R
C12 C 1.0444(3) -0.3786(3) 1.03852(12) 0.0606(7) Uani 1 1 d .
H12 H 1.0239 -0.4765 1.0207 0.073 Uiso 1 1 calc R
C13 C 1.0195(3) 0.0980(2) 0.83292(8) 0.0396(5) Uani 1 1 d .
C14 C 0.8540(3) 0.1646(2) 0.83492(8) 0.0427(5) Uani 1 1 d .
H14 H 0.8062 0.1966 0.8707 0.051 Uiso 1 1 calc R
C15 C 0.7595(3) 0.1834(3) 0.78336(8) 0.0449(5) Uani 1 1 d .
C16 C 0.8288(3) 0.1425(3) 0.72922(9) 0.0568(6) Uani 1 1 d .
H16 H 0.7640 0.1560 0.6949 0.068 Uiso 1 1 calc R
C17 C 0.9954(4) 0.0816(3) 0.72748(9) 0.0627(7) Uani 1 1 d .
H17 H 1.0452 0.0550 0.6914 0.075 Uiso 1 1 calc R
C18 C 1.0915(3) 0.0591(3) 0.77894(9) 0.0518(6) Uani 1 1 d .
H18 H 1.2046 0.0178 0.7770 0.062 Uiso 1 1 calc R
Cl1 Cl 0.54980(8) 0.26512(10) 0.78633(2) 0.0741(3) Uani 1 1 d .
N1 N 1.0926(2) 0.0251(2) 0.99101(6) 0.0424(4) Uani 1 1 d .
O1 O 1.2308(2) 0.2449(2) 1.02957(6) 0.0696(5) Uani 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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
O1 C1 N1 126.48(19)
O1 C1 C2 127.7(2)
N1 C1 C2 105.83(18)
C3 C2 C1 123.2(2)
C3 C2 C4 128.60(19)
C1 C2 C4 108.17(18)
C2 C4 C13 116.23(16)
C2 C4 C5 102.32(15)
C13 C4 C5 114.38(18)
N1 C5 C6 103.28(16)
N1 C5 C4 102.86(16)
C6 C5 C4 121.96(18)
C7 C6 C5 102.10(17)
C12 C7 C8 119.4(2)
C12 C7 C6 130.9(2)
C8 C7 C6 109.57(19)
C9 C8 C7 122.4(2)
C9 C8 N1 128.9(2)
C7 C8 N1 108.65(17)
C10 C9 C8 117.5(3)
C11 C10 C9 120.8(2)
C10 C11 C12 121.7(2)
C7 C12 C11 118.1(3)
C14 C13 C18 119.15(18)
C14 C13 C4 120.61(17)
C18 C13 C4 120.24(19)
C13 C14 C15 119.57(18)
C16 C15 C14 121.8(2)
C16 C15 Cl1 118.89(16)
C14 C15 Cl1 119.31(15)
C17 C16 C15 118.2(2)
C16 C17 C18 120.9(2)
C13 C18 C17 120.3(2)
C1 N1 C8 133.97(18)
C1 N1 C5 115.02(15)
C8 N1 C5 109.92(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.224(2)
C1 N1 1.349(3)
C1 C2 1.492(3)
C2 C3 1.309(3)
C2 C4 1.517(3)
C4 C13 1.517(3)
C4 C5 1.541(3)
C5 N1 1.469(2)
C5 C6 1.531(3)
C6 C7 1.519(3)
C7 C12 1.383(3)
C7 C8 1.392(3)
C8 C9 1.382(3)
C8 N1 1.404(2)
C9 C10 1.382(4)
C10 C11 1.373(4)
C11 C12 1.393(3)
C13 C14 1.381(3)
C13 C18 1.383(3)
C14 C15 1.384(3)
C15 C16 1.382(3)
C15 Cl1 1.741(2)
C16 C17 1.369(4)
C17 C18 1.393(3)
