#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:33:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178875 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/04/4110491.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_4110491
loop_
_publ_author_name
'Kai-Tai Yip'
'Min Yang'
'Ka-Lun Law'
'Nian-Yong Zhu'
'Dan Yang'
_publ_section_title
;
 Pd(II)-Catalyzed Enantioselective Oxidative Tandem Cyclization Reactions.
 Synthesis of Indolines through C-N and C-C Bond Formation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3130
_journal_page_last               3131
_journal_paper_doi               10.1021/ja060291x
_journal_volume                  128
_journal_year                    2006
_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                   5.6050(11)
_cell_length_b                   11.220(2)
_cell_length_c                   22.945(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1443.0(5)
_computing_cell_refinement       Scalepack
_computing_data_collection       Marcontrol
_computing_data_reduction        Denzo
_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 0.800
_diffrn_measured_fraction_theta_max 0.800
_diffrn_measurement_device_type  mar300
_diffrn_measurement_method       oscillation
_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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5421
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0330
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0742
_reflns_number_gt                1335
_reflns_number_total             1980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja060291xsi20060125_113920.cif
_cod_data_source_block           mar1620
_cod_database_code               4110491
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
Cl1 Cl 0.08861(18) 0.47779(7) 0.04163(3) 0.0862(3) Uani 1 1 d .
O1 O 0.2885(3) 0.39800(16) 0.23808(8) 0.0671(6) Uani 1 1 d .
N1 N 0.4183(4) 0.26064(18) 0.30512(9) 0.0506(6) Uani 1 1 d .
C1 C 0.2680(5) 0.3010(3) 0.26257(12) 0.0538(7) Uani 1 1 d .
C2 C 0.0777(6) 0.2079(2) 0.25710(11) 0.0521(7) Uani 1 1 d .
C3 C 0.0942(5) 0.1287(2) 0.31036(12) 0.0627(8) Uani 1 1 d .
H3A H 0.0613 0.0463 0.3004 0.075 Uiso 1 1 calc R
H3B H -0.0169 0.1542 0.3403 0.075 Uiso 1 1 calc R
C4 C 0.3521(5) 0.1440(2) 0.33069(11) 0.0558(8) Uani 1 1 d .
H4 H 0.4523 0.0808 0.3142 0.067 Uiso 1 1 calc R
C5 C 0.4082(6) 0.1601(2) 0.39564(12) 0.0688(8) Uani 1 1 d .
H5A H 0.2658 0.1807 0.4174 0.083 Uiso 1 1 calc R
H5B H 0.4774 0.0883 0.4120 0.083 Uiso 1 1 calc R
C6 C 0.5856(5) 0.2615(2) 0.39579(12) 0.0549(7) Uani 1 1 d .
C7 C 0.7354(6) 0.3002(3) 0.43872(12) 0.0698(9) Uani 1 1 d .
H7 H 0.7396 0.2622 0.4747 0.084 Uiso 1 1 calc R
C8 C 0.8821(6) 0.3979(3) 0.42733(15) 0.0763(9) Uani 1 1 d .
H8 H 0.9859 0.4251 0.4560 0.092 Uiso 1 1 calc R
C9 C 0.8749(6) 0.4545(3) 0.37409(15) 0.0761(9) Uani 1 1 d .
H9 H 0.9740 0.5195 0.3674 0.091 Uiso 1 1 calc R
C10 C 0.7230(6) 0.4165(3) 0.33025(13) 0.0659(9) Uani 1 1 d .
H10 H 0.7172 0.4553 0.2945 0.079 Uiso 1 1 calc R
C11 C 0.5802(6) 0.3187(2) 0.34162(11) 0.0517(7) Uani 1 1 d .
C12 C -0.0914(6) 0.1922(2) 0.21681(11) 0.0572(7) Uani 1 1 d .
H12 H -0.1957 0.1310 0.2267 0.069 Uiso 1 1 calc R
C13 C -0.1537(5) 0.2472(3) 0.16104(12) 0.0552(7) Uani 1 1 d .
C14 C -0.0138(5) 0.3320(2) 0.13185(13) 0.0557(8) Uani 1 1 d .
H14 H 0.1264 0.3603 0.1485 0.067 Uiso 1 1 calc R
C15 C -0.0872(6) 0.3729(2) 0.07798(13) 0.0606(8) Uani 1 1 d .
C16 C -0.2942(7) 0.3373(3) 0.05152(14) 0.0705(9) Uani 1 1 d .
H16 H -0.3397 0.3676 0.0155 0.085 Uiso 1 1 calc R
C17 C -0.4322(6) 0.2548(3) 0.08051(14) 0.0776(9) Uani 1 1 d .
H17 H -0.5731 0.2281 0.0635 0.093 Uiso 1 1 calc R
C18 C -0.3654(6) 0.2114(3) 0.13401(14) 0.0704(9) Uani 1 1 d .
H18 H -0.4637 0.1567 0.1528 0.084 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
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C11 132.4(2)
C1 N1 C4 114.9(2)
C11 N1 C4 109.7(2)
O1 C1 N1 124.2(3)
O1 C1 C2 130.2(3)
N1 C1 C2 105.5(2)
C12 C2 C1 130.9(2)
C12 C2 C3 121.7(3)
C1 C2 C3 107.3(2)
C2 C3 C4 103.8(2)
N1 C4 C3 102.4(2)
N1 C4 C5 103.3(2)
C3 C4 C5 120.2(2)
C6 C5 C4 103.0(2)
C7 C6 C11 120.6(3)
C7 C6 C5 130.2(3)
C11 C6 C5 109.2(2)
C6 C7 C8 118.5(3)
C9 C8 C7 120.7(3)
C8 C9 C10 121.4(3)
C11 C10 C9 117.6(3)
C10 C11 N1 129.3(3)
C10 C11 C6 121.3(3)
N1 C11 C6 109.5(3)
C2 C12 C13 136.0(3)
C18 C13 C14 117.2(3)
C18 C13 C12 118.0(3)
C14 C13 C12 124.8(3)
C15 C14 C13 119.1(3)
C16 C15 C14 123.6(3)
C16 C15 Cl1 117.6(3)
C14 C15 Cl1 118.9(3)
C15 C16 C17 117.2(3)
C18 C17 C16 121.1(3)
C17 C18 C13 121.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C15 1.747(3)
O1 C1 1.230(3)
N1 C1 1.367(3)
N1 C11 1.396(3)
N1 C4 1.481(3)
C1 C2 1.498(4)
C2 C12 1.335(4)
C2 C3 1.514(3)
C3 C4 1.529(4)
C4 C5 1.534(4)
C5 C6 1.511(4)
C6 C7 1.365(4)
C6 C11 1.399(3)
C7 C8 1.396(4)
C8 C9 1.377(4)
C9 C10 1.385(4)
C10 C11 1.383(4)
C12 C13 1.463(4)
C13 C18 1.398(4)
C13 C14 1.404(4)
C14 C15 1.381(4)
C15 C16 1.369(4)
C16 C17 1.378(4)
C17 C18 1.373(4)
