#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:36:15 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180307 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/21/7152143.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_7152143
loop_
_publ_author_name
'Xia, Ziming'
'Wang, Kuo'
'Zheng, Jiening'
'Ma, Zheyong'
'Jiang, Zhanguo'
'Wang, Xiaoxia'
'Lv, Xin'
_publ_section_title
;
 Copper-catalyzed domino intramolecular cyclization: a facile and
 efficient approach to polycyclic indole derivatives.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1602
_journal_page_last               1611
_journal_paper_doi               10.1039/c1ob06488f
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C15 H9 N O2'
_chemical_formula_weight         235.23
_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                 108.92
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2370(13)
_cell_length_b                   7.6556(8)
_cell_length_c                   12.2370(13)
_cell_measurement_temperature    296(2)
_cell_volume                     1084.4(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker P4'
_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  0.1583
_diffrn_reflns_av_sigmaI/netI    0.0991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9119
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.901
_refine_ls_R_factor_all          0.1756
_refine_ls_R_factor_gt           0.0983
_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)+(0.1000P)²+3.4650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2342
_refine_ls_wR_factor_ref         0.3158
_reflns_number_gt                1074
_reflns_number_total             2452
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06488f.txt
_cod_data_source_block           a
_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_cell_volume        1084.5(2)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7152143
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
O2 O 0.0811(3) 0.2356(4) 0.5210(3) 0.0648(10) Uani 1 1 d .
O1 O -0.0215(3) 0.5385(5) 0.2297(3) 0.0683(10) Uani 1 1 d .
N1 N -0.0637(3) 0.3735(5) 0.3655(3) 0.0573(10) Uani 1 1 d .
C9 C 0.0122(4) 0.4490(6) 0.3148(3) 0.0548(11) Uani 1 1 d .
C11 C 0.1624(4) 0.3031(6) 0.4750(4) 0.0577(11) Uani 1 1 d .
C8 C -0.0313(4) 0.2644(6) 0.4613(4) 0.0543(11) Uani 1 1 d .
C10 C 0.1312(4) 0.4026(6) 0.3779(4) 0.0574(11) Uani 1 1 d .
C5 C -0.1856(4) 0.3772(6) 0.3243(4) 0.0584(11) Uani 1 1 d .
C7 C -0.1222(4) 0.2004(7) 0.4862(4) 0.0648(12) Uani 1 1 d .
H7A H -0.1212 0.1277 0.5474 0.078 Uiso 1 1 calc R
C15 C 0.2189(4) 0.4666(7) 0.3368(5) 0.0690(13) Uani 1 1 d .
H15A H 0.2005 0.5343 0.2702 0.083 Uiso 1 1 calc R
C6 C -0.2585(4) 0.4619(7) 0.2297(4) 0.0664(13) Uani 1 1 d .
H6A H -0.2311 0.5337 0.1830 0.080 Uiso 1 1 calc R
C12 C 0.2759(5) 0.2608(7) 0.5360(5) 0.0721(14) Uani 1 1 d .
H12A H 0.2946 0.1918 0.6021 0.086 Uiso 1 1 calc R
C14 C 0.3317(5) 0.4271(8) 0.3970(5) 0.0796(16) Uani 1 1 d .
H14A H 0.3902 0.4700 0.3713 0.096 Uiso 1 1 calc R
C13 C 0.3598(5) 0.3253(8) 0.4945(5) 0.0799(16) Uani 1 1 d .
H13A H 0.4369 0.2995 0.5332 0.096 Uiso 1 1 calc R
C4 C -0.2214(4) 0.2679(7) 0.3982(4) 0.0652(13) Uani 1 1 d .
C2 C -0.4146(5) 0.3261(9) 0.2806(5) 0.0858(18) Uani 1 1 d .
H2A H -0.4935 0.3089 0.2641 0.103 Uiso 1 1 calc R
C3 C -0.3399(5) 0.2453(8) 0.3750(5) 0.0783(16) Uani 1 1 d .
H3A H -0.3675 0.1765 0.4229 0.094 Uiso 1 1 calc R
C1 C -0.3763(5) 0.4333(9) 0.2083(5) 0.0837(18) Uani 1 1 d .
H1A H -0.4299 0.4864 0.1450 0.100 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.065(2) 0.069(2) 0.0527(17) 0.0114(15) 0.0087(15) 0.0043(16)
O1 0.072(2) 0.070(2) 0.0580(19) 0.0134(17) 0.0131(15) 0.0020(17)
N1 0.058(2) 0.061(2) 0.0450(18) 0.0007(17) 0.0054(15) 0.0011(17)
C9 0.065(3) 0.053(2) 0.041(2) 0.0020(18) 0.0082(18) 0.000(2)
C11 0.059(2) 0.059(2) 0.049(2) -0.004(2) 0.0080(18) 0.000(2)
C8 0.057(2) 0.055(2) 0.046(2) 0.0008(19) 0.0088(18) 0.0039(19)
C10 0.061(3) 0.055(2) 0.049(2) -0.004(2) 0.0079(19) -0.002(2)
C5 0.058(2) 0.063(3) 0.046(2) -0.005(2) 0.0048(18) 0.006(2)
C7 0.075(3) 0.063(3) 0.055(3) 0.006(2) 0.020(2) -0.003(2)
C15 0.071(3) 0.067(3) 0.065(3) 0.000(2) 0.017(2) -0.006(2)
C6 0.064(3) 0.069(3) 0.058(3) 0.001(2) 0.008(2) 0.005(2)
C12 0.069(3) 0.071(3) 0.060(3) -0.002(2) -0.001(2) 0.006(3)
C14 0.062(3) 0.090(4) 0.085(4) -0.009(3) 0.021(3) -0.009(3)
C13 0.063(3) 0.085(4) 0.079(4) -0.014(3) 0.005(3) -0.003(3)
C4 0.070(3) 0.065(3) 0.055(3) -0.012(2) 0.013(2) 0.000(2)
C2 0.068(3) 0.104(5) 0.081(4) -0.019(4) 0.018(3) -0.003(3)
C3 0.068(3) 0.087(4) 0.077(3) -0.013(3) 0.021(3) -0.009(3)
C1 0.063(3) 0.097(4) 0.074(3) -0.011(3) -0.001(3) 0.016(3)
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
C8 O2 C11 117.2(4)
C8 N1 C9 125.0(4)
C8 N1 C5 107.0(4)
C9 N1 C5 127.6(4)
O1 C9 N1 121.9(4)
O1 C9 C10 127.1(4)
N1 C9 C10 111.0(4)
C10 C11 C12 123.4(5)
C10 C11 O2 121.8(4)
C12 C11 O2 114.7(4)
C7 C8 O2 126.4(4)
C7 C8 N1 112.4(4)
O2 C8 N1 121.2(4)
C11 C10 C15 118.4(4)
C11 C10 C9 123.4(4)
C15 C10 C9 118.1(4)
C6 C5 C4 124.9(5)
C6 C5 N1 129.3(5)
C4 C5 N1 105.8(4)
C8 C7 C4 105.1(4)
C14 C15 C10 118.7(5)
C5 C6 C1 115.7(5)
C13 C12 C11 117.0(5)
C15 C14 C13 121.1(5)
C14 C13 C12 121.2(5)
C3 C4 C5 117.6(5)
C3 C4 C7 132.8(5)
C5 C4 C7 109.5(4)
C3 C2 C1 122.2(6)
C2 C3 C4 118.9(6)
C2 C1 C6 120.8(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C8 1.350(5)
O2 C11 1.392(6)
O1 C9 1.202(5)
N1 C8 1.388(6)
N1 C9 1.398(6)
N1 C5 1.411(6)
C9 C10 1.454(6)
C11 C10 1.357(6)
C11 C12 1.386(6)
C8 C7 1.338(6)
C10 C15 1.412(7)
C5 C6 1.373(6)
C5 C4 1.403(7)
C7 C4 1.432(7)
C15 C14 1.371(7)
C6 C1 1.397(7)
C12 C13 1.376(8)
C14 C13 1.372(8)
C4 C3 1.395(7)
C2 C3 1.367(9)
C2 C1 1.395(9)
