#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:59:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180283 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/69/7116938.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_7116938
loop_
_publ_author_name
'Ting Li'
'Zhen Wang'
'Mingliang Zhang'
'Hui-Jun Zhang'
'Ting-Bin Wen'
_publ_section_title
;
 Rh/Cu-catalyzed multiple C-H, C-C, and C-N bond cleavage: facile
 synthesis of pyrido[2,1-a]indoles from 1-(pyridin-2-yl)-1H-indoles and
 gamma-substituted propargyl alcohols
;
_journal_name_full               Chem.Commun.
_journal_page_first              6777
_journal_paper_doi               10.1039/C5cc01412C
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C32 H26 N2 O'
_chemical_formula_weight         454.55
_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_block_doi                 10.5517/cc13n9fh
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-03 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.121(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9489(5)
_cell_length_b                   17.1959(6)
_cell_length_c                   14.4905(8)
_cell_measurement_temperature    173(2)
_cell_volume                     2342.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10431
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.80
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.914
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.317
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.317
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0927
_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+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3069
_refine_ls_wR_factor_ref         0.3157
_reflns_number_gt                3659
_reflns_number_total             4431
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01412c2.cif
_cod_data_source_block           tl20140907-2
_cod_original_cell_volume        2342.26(19)
_cod_original_sg_symbol_H-M      p_1_21/c_1
_cod_database_code               7116938
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4790(3) 0.64714(16) 0.2199(2) 0.0471(8) Uani 1 1 d . . .
N1 N 1.0402(3) 0.29890(14) 0.51912(19) 0.0256(7) Uani 1 1 d . . .
C1 C 1.0999(3) 0.35435(17) 0.4715(2) 0.0242(7) Uani 1 1 d . . .
N2 N 0.7917(4) 0.1823(2) 0.6930(3) 0.0481(9) Uani 1 1 d . . .
C2 C 1.2392(3) 0.33513(18) 0.4843(2) 0.0243(7) Uani 1 1 d . . .
C3 C 1.2693(4) 0.26591(18) 0.5419(2) 0.0279(8) Uani 1 1 d . . .
C4 C 1.3919(4) 0.22026(19) 0.5757(3) 0.0311(8) Uani 1 1 d . . .
H4A H 1.4742 0.2343 0.5626 0.037 Uiso 1 1 calc R . .
C5 C 1.3890(4) 0.1533(2) 0.6293(3) 0.0354(9) Uani 1 1 d . . .
H5A H 1.4686 0.1213 0.6503 0.042 Uiso 1 1 calc R . .
C6 C 1.2652(4) 0.1342(2) 0.6518(3) 0.0363(9) Uani 1 1 d . . .
H6A H 1.2660 0.0901 0.6890 0.044 Uiso 1 1 calc R . .
C7 C 1.1442(4) 0.17818(19) 0.6208(3) 0.0305(8) Uani 1 1 d . . .
H7A H 1.0634 0.1647 0.6361 0.037 Uiso 1 1 calc R . .
C8 C 1.1467(3) 0.24416(18) 0.5653(2) 0.0267(8) Uani 1 1 d . . .
C9 C 0.8982(4) 0.30404(18) 0.5093(2) 0.0276(8) Uani 1 1 d . . .
C10 C 0.8161(3) 0.35847(16) 0.4614(2) 0.0173(6) Uani 1 1 d . . .
H10A H 0.7202 0.3585 0.4556 0.021 Uiso 1 1 calc R . .
C11 C 0.8712(3) 0.41739(18) 0.4182(2) 0.0245(7) Uani 1 1 d . . .
C12 C 1.0099(3) 0.41508(18) 0.4222(2) 0.0261(7) Uani 1 1 d . . .
H12A H 1.0455 0.4540 0.3920 0.031 Uiso 1 1 calc R . .
C13 C 1.3428(4) 0.3781(2) 0.4477(3) 0.0341(9) Uani 1 1 d . . .
H13A H 1.2970 0.4228 0.4111 0.051 Uiso 1 1 calc R . .
H13B H 1.3752 0.3445 0.4065 0.051 Uiso 1 1 calc R . .
H13C H 1.4225 0.3946 0.5022 0.051 Uiso 1 1 calc R . .
C21 C 0.7696(4) 0.47773(18) 0.3668(2) 0.0260(7) Uani 1 1 d . . .
C22 C 0.8140(4) 0.54345(18) 0.3268(2) 0.0285(8) Uani 1 1 d . . .
H22A H 0.9100 0.5494 0.3344 0.034 Uiso 1 1 calc R . .
C23 C 0.7185(4) 0.59954(19) 0.2764(3) 0.0320(8) Uani 1 1 d . . .
H23A H 0.7508 0.6415 0.2489 0.038 Uiso 1 1 calc R . .
C24 C 0.5767(4) 0.59403(19) 0.2663(3) 0.0339(8) Uani 1 1 d . . .
C25 C 0.5300(4) 0.5284(2) 0.3064(3) 0.0392(9) Uani 1 1 d . . .
H25A H 0.4343 0.5234 0.3000 0.047 Uiso 1 1 calc R . .
C26 C 0.6251(4) 0.4720(2) 0.3549(3) 0.0332(8) Uani 1 1 d . . .
H26A H 0.5923 0.4291 0.3802 0.040 Uiso 1 1 calc R . .
C31 C 0.8378(3) 0.24027(19) 0.5554(3) 0.0300(8) Uani 1 1 d . . .
C32 C 0.7912(4) 0.1744(2) 0.5022(3) 0.0355(9) Uani 1 1 d . . .
H32A H 0.7926 0.1718 0.4384 0.043 Uiso 1 1 calc R . .
C33 C 0.7409(4) 0.1101(2) 0.5417(3) 0.0380(9) Uani 1 1 d . . .
C34 C 0.7456(4) 0.1162(2) 0.6384(3) 0.0370(9) Uani 1 1 d . . .
H34A H 0.7165 0.0740 0.6672 0.044 Uiso 1 1 calc R . .
C35 C 0.8384(3) 0.2470(2) 0.6529(3) 0.0315(9) Uani 1 1 d . . .
C41 C 0.8882(4) 0.31691(19) 0.7131(3) 0.0329(9) Uani 1 1 d . . .
C42 C 0.9963(4) 0.3128(2) 0.8028(3) 0.0375(9) Uani 1 1 d . . .
H42A H 1.0406 0.2652 0.8235 0.045 Uiso 1 1 calc R . .
C43 C 1.0400(5) 0.3772(2) 0.8622(3) 0.0415(10) Uani 1 1 d . . .
H43A H 1.1125 0.3722 0.9217 0.050 Uiso 1 1 calc R . .
C44 C 0.9767(5) 0.4494(2) 0.8340(3) 0.0440(10) Uani 1 1 d . . .
H44A H 1.0060 0.4930 0.8734 0.053 Uiso 1 1 calc R . .
C45 C 0.8682(4) 0.4540(2) 0.7448(3) 0.0380(9) Uani 1 1 d . . .
H45A H 0.8241 0.5017 0.7248 0.046 Uiso 1 1 calc R . .
C46 C 0.8236(4) 0.3901(2) 0.6848(3) 0.0353(9) Uani 1 1 d . . .
H46A H 0.7506 0.3954 0.6255 0.042 Uiso 1 1 calc R . .
C51 C 0.5240(5) 0.7120(2) 0.1763(3) 0.0490(10) Uani 1 1 d . . .
H51A H 0.4440 0.7451 0.1459 0.074 Uiso 1 1 calc R . .
H51D H 0.5635 0.6940 0.1279 0.074 Uiso 1 1 calc R . .
H51B H 0.5949 0.7407 0.2256 0.074 Uiso 1 1 calc R . .
C61 C 0.6879(5) 0.0386(2) 0.4817(4) 0.0527(11) Uani 1 1 d . . .
H61A H 0.6589 0.0008 0.5202 0.079 Uiso 1 1 calc R . .
H61B H 0.7625 0.0173 0.4610 0.079 Uiso 1 1 calc R . .
H61C H 0.6082 0.0519 0.4255 0.079 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C24 O1 C51 118.3(3) . .
C9 N1 C8 132.7(3) . .
C9 N1 C1 119.1(3) . .
C8 N1 C1 108.1(2) . .
C2 C1 C12 133.7(3) . .
C2 C1 N1 109.7(3) . .
C12 C1 N1 116.7(3) . .
C34 N2 C35 120.7(3) . .
C1 C2 C3 106.7(3) . .
C1 C2 C13 127.8(3) . .
C3 C2 C13 125.5(3) . .
C4 C3 C8 119.2(3) . .
C4 C3 C2 131.7(3) . .
C8 C3 C2 109.1(3) . .
C5 C4 C3 118.9(3) . .
C4 C5 C6 120.0(3) . .
C7 C6 C5 122.5(3) . .
C6 C7 C8 117.3(3) . .
C7 C8 N1 131.5(3) . .
C7 C8 C3 122.1(3) . .
N1 C8 C3 106.3(3) . .
C10 C9 N1 123.5(3) . .
C10 C9 C31 119.6(3) . .
N1 C9 C31 116.9(3) . .
C9 C10 C11 119.9(3) . .
C12 C11 C10 120.1(3) . .
C12 C11 C21 124.1(3) . .
C10 C11 C21 115.8(3) . .
C11 C12 C1 120.6(3) . .
C26 C21 C22 117.1(3) . .
C26 C21 C11 121.5(3) . .
C22 C21 C11 121.3(3) . .
C23 C22 C21 121.7(3) . .
C24 C23 C22 120.8(3) . .
O1 C24 C23 123.8(3) . .
O1 C24 C25 117.8(3) . .
C23 C24 C25 118.4(3) . .
C26 C25 C24 120.5(3) . .
C25 C26 C21 121.5(3) . .
C32 C31 C35 121.4(3) . .
C32 C31 C9 117.7(3) . .
C35 C31 C9 120.7(3) . .
C31 C32 C33 121.5(3) . .
C34 C33 C32 116.7(3) . .
C34 C33 C61 122.5(3) . .
C32 C33 C61 120.8(3) . .
N2 C34 C33 122.6(3) . .
N2 C35 C31 117.1(3) . .
N2 C35 C41 119.7(3) . .
C31 C35 C41 123.2(3) . .
C42 C41 C46 117.2(3) . .
C42 C41 C35 121.2(3) . .
C46 C41 C35 121.5(3) . .
C43 C42 C41 122.0(3) . .
C42 C43 C44 120.9(4) . .
C45 C44 C43 117.5(4) . .
C46 C45 C44 122.2(3) . .
C45 C46 C41 120.3(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C24 1.342(4) .
O1 C51 1.425(4) .
N1 C9 1.376(4) .
N1 C8 1.411(4) .
N1 C1 1.416(4) .
C1 C2 1.377(4) .
C1 C12 1.408(5) .
N2 C34 1.375(5) .
N2 C35 1.402(4) .
C2 C3 1.428(4) .
C2 C13 1.499(4) .
C3 C4 1.398(5) .
C3 C8 1.419(4) .
C4 C5 1.395(5) .
C5 C6 1.412(5) .
C6 C7 1.367(5) .
C7 C8 1.396(4) .
C9 C10 1.286(4) .
C9 C31 1.507(4) .
C10 C11 1.394(4) .
C11 C12 1.363(4) .
C11 C21 1.469(5) .
C21 C26 1.394(5) .
C21 C22 1.405(4) .
C22 C23 1.383(5) .
C23 C24 1.374(5) .
C24 C25 1.416(5) .
C25 C26 1.376(5) .
C31 C32 1.363(5) .
C31 C35 1.417(5) .
C32 C33 1.411(5) .
C33 C34 1.389(5) .
C33 C61 1.498(6) .
C35 C41 1.473(5) .
C41 C42 1.391(5) .
C41 C46 1.412(5) .
C42 C43 1.382(6) .
C43 C44 1.393(5) .
C44 C45 1.388(6) .
C45 C46 1.381(5) .
