#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:59:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180283 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/69/7116937.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_7116937
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_moiety         'C30 H21 Cl N2'
_chemical_formula_sum            'C30 H21 Cl N2'
_chemical_formula_weight         444.94
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc13n9dg
_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                67.401(9)
_cell_angle_beta                 89.113(7)
_cell_angle_gamma                83.151(6)
_cell_formula_units_Z            2
_cell_length_a                   8.8053(4)
_cell_length_b                   11.2771(10)
_cell_length_c                   12.0975(13)
_cell_measurement_reflns_used    3406
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.0080
_cell_measurement_theta_min      3.9480
_cell_volume                     1100.51(18)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8275
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41053
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0852P)²+1.1871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1778
_reflns_number_gt                3521
_reflns_number_total             4304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01412c2.cif
_cod_data_source_block           p2
_cod_original_cell_volume        1100.51(16)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7116937
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 1.14884(8) 0.37852(6) 0.10019(6) 0.0276(2) Uani 1 1 d . . .
N1 N 0.8305(2) 0.61229(19) 0.41087(19) 0.0171(5) Uani 1 1 d . . .
C1 C 0.7494(3) 0.5076(2) 0.4790(2) 0.0204(6) Uani 1 1 d . . .
N2 N 0.8970(3) 1.0013(3) 0.1455(3) 0.0379(7) Uani 1 1 d . . .
C2 C 0.7851(3) 0.4079(2) 0.4418(2) 0.0213(6) Uani 1 1 d . . .
H2B H 0.7467 0.3286 0.4719 0.026 Uiso 1 1 calc R . .
C3 C 0.8913(3) 0.4471(2) 0.3490(2) 0.0192(5) Uani 1 1 d . . .
C4 C 0.9642(3) 0.3852(2) 0.2780(2) 0.0214(6) Uani 1 1 d . . .
H4A H 0.9471 0.3017 0.2888 0.026 Uiso 1 1 calc R . .
C5 C 1.0607(3) 0.4502(3) 0.1930(2) 0.0217(6) Uani 1 1 d . . .
C6 C 1.0916(3) 0.5762(3) 0.1760(3) 0.0226(6) Uani 1 1 d . . .
H6A H 1.1589 0.6172 0.1177 0.027 Uiso 1 1 calc R . .
C7 C 1.0230(3) 0.6382(2) 0.2449(2) 0.0213(6) Uani 1 1 d . . .
H7A H 1.0443 0.7204 0.2351 0.026 Uiso 1 1 calc R . .
C8 C 0.9200(3) 0.5745(2) 0.3304(2) 0.0185(5) Uani 1 1 d . . .
C9 C 0.8033(3) 0.7279(2) 0.4271(2) 0.0186(5) Uani 1 1 d . . .
C10 C 0.7172(2) 0.7424(2) 0.5090(2) 0.0092(4) Uani 1 1 d . . .
H10A H 0.7054 0.8208 0.5189 0.011 Uiso 1 1 calc R . .
C11 C 0.6416(3) 0.6403(2) 0.5827(2) 0.0201(6) Uani 1 1 d . . .
C12 C 0.6539(3) 0.5262(2) 0.5677(2) 0.0202(6) Uani 1 1 d . . .
H12A H 0.5995 0.4603 0.6157 0.024 Uiso 1 1 calc R . .
C31 C 0.8731(3) 0.8408(2) 0.3429(2) 0.0180(5) Uani 1 1 d . . .
C32 C 0.8202(3) 0.9014(2) 0.2226(2) 0.0187(5) Uani 1 1 d . . .
C33 C 1.0194(3) 1.0417(3) 0.1883(3) 0.0243(6) Uani 1 1 d . . .
H33A H 1.0694 1.1079 0.1352 0.029 Uiso 1 1 calc R . .
C34 C 1.0688(3) 0.9858(2) 0.3081(3) 0.0228(6) Uani 1 1 d . . .
C35 C 0.9935(3) 0.8845(2) 0.3843(2) 0.0211(6) Uani 1 1 d . . .
H35A H 1.0244 0.8450 0.4647 0.025 Uiso 1 1 calc R . .
C36 C 1.2002(3) 1.0308(3) 0.3531(3) 0.0291(7) Uani 1 1 d . . .
H36A H 1.2155 0.9830 0.4379 0.044 Uiso 1 1 calc R . .
H36B H 1.1774 1.1214 0.3373 0.044 Uiso 1 1 calc R . .
H36C H 1.2914 1.0168 0.3131 0.044 Uiso 1 1 calc R . .
C41 C 0.5401(3) 0.6669(3) 0.6710(2) 0.0209(6) Uani 1 1 d . . .
C42 C 0.4982(3) 0.5677(3) 0.7724(2) 0.0252(6) Uani 1 1 d . . .
H42A H 0.5404 0.4829 0.7882 0.030 Uiso 1 1 calc R . .
C43 C 0.3946(3) 0.5927(3) 0.8505(3) 0.0286(7) Uani 1 1 d . . .
H43A H 0.3677 0.5251 0.9182 0.034 Uiso 1 1 calc R . .
C44 C 0.3315(3) 0.7186(3) 0.8272(3) 0.0287(6) Uani 1 1 d . . .
H44A H 0.2609 0.7357 0.8789 0.034 Uiso 1 1 calc R . .
C45 C 0.3731(3) 0.8192(3) 0.7273(3) 0.0284(6) Uani 1 1 d . . .
H45A H 0.3307 0.9037 0.7120 0.034 Uiso 1 1 calc R . .
C46 C 0.4777(3) 0.7942(3) 0.6502(3) 0.0252(6) Uani 1 1 d . . .
H46A H 0.5069 0.8624 0.5840 0.030 Uiso 1 1 calc R . .
C51 C 0.6849(3) 0.8626(2) 0.1784(2) 0.0205(6) Uani 1 1 d . . .
C52 C 0.6922(3) 0.8374(3) 0.0736(3) 0.0291(6) Uani 1 1 d . . .
H52A H 0.7836 0.8416 0.0333 0.035 Uiso 1 1 calc R . .
C53 C 0.5658(4) 0.8063(3) 0.0292(3) 0.0326(7) Uani 1 1 d . . .
H53A H 0.5722 0.7898 -0.0405 0.039 Uiso 1 1 calc R . .
C54 C 0.4294(3) 0.7997(3) 0.0885(3) 0.0311(7) Uani 1 1 d . . .
H54A H 0.3442 0.7788 0.0587 0.037 Uiso 1 1 calc R . .
C55 C 0.4197(3) 0.8242(3) 0.1924(3) 0.0290(7) Uani 1 1 d . . .
H55A H 0.3279 0.8202 0.2320 0.035 Uiso 1 1 calc R . .
C56 C 0.5472(3) 0.8547(2) 0.2373(3) 0.0232(6) Uani 1 1 d . . .
H56A H 0.5404 0.8701 0.3075 0.028 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'
Cl Cl 0.1484 0.1585 '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
C9 N1 C8 132.7(2) . .
C9 N1 C1 119.3(2) . .
C8 N1 C1 107.8(2) . .
C2 C1 C12 134.3(3) . .
C2 C1 N1 109.3(2) . .
C12 C1 N1 116.4(2) . .
C32 N2 C33 120.5(3) . .
C1 C2 C3 107.7(2) . .
C4 C3 C8 119.4(2) . .
C4 C3 C2 132.3(2) . .
C8 C3 C2 108.3(2) . .
C5 C4 C3 118.5(2) . .
C4 C5 C6 122.2(2) . .
C4 C5 Cl1 119.9(2) . .
C6 C5 Cl1 118.0(2) . .
C7 C6 C5 120.4(3) . .
C6 C7 C8 118.3(2) . .
N1 C8 C7 131.9(2) . .
N1 C8 C3 106.9(2) . .
C7 C8 C3 121.1(2) . .
C10 C9 N1 123.0(2) . .
C10 C9 C31 119.1(2) . .
N1 C9 C31 117.9(2) . .
C9 C10 C11 119.7(2) . .
C12 C11 C10 121.1(2) . .
C12 C11 C41 122.6(2) . .
C10 C11 C41 116.2(2) . .
C11 C12 C1 120.1(2) . .
C35 C31 C32 120.5(2) . .
C35 C31 C9 119.0(2) . .
C32 C31 C9 120.5(2) . .
N2 C32 C31 118.0(2) . .
N2 C32 C51 120.5(2) . .
C31 C32 C51 121.5(2) . .
C34 C33 N2 122.0(3) . .
C33 C34 C35 117.3(2) . .
C33 C34 C36 121.4(2) . .
C35 C34 C36 121.3(3) . .
C31 C35 C34 121.7(3) . .
C42 C41 C46 118.5(3) . .
C42 C41 C11 121.5(2) . .
C46 C41 C11 120.0(2) . .
C41 C42 C43 121.1(3) . .
C44 C43 C42 119.7(3) . .
C45 C44 C43 120.1(3) . .
C46 C45 C44 120.2(3) . .
C45 C46 C41 120.4(3) . .
C56 C51 C52 118.3(3) . .
C56 C51 C32 121.2(2) . .
C52 C51 C32 120.5(2) . .
C53 C52 C51 120.9(3) . .
C52 C53 C54 119.9(3) . .
C53 C54 C55 120.1(3) . .
C54 C55 C56 119.9(3) . .
C55 C56 C51 120.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.743(3) .
N1 C9 1.384(3) .
N1 C8 1.401(3) .
N1 C1 1.421(3) .
C1 C2 1.367(4) .
C1 C12 1.416(4) .
N2 C32 1.397(4) .
N2 C33 1.398(4) .
C2 C3 1.420(4) .
C3 C4 1.405(4) .
C3 C8 1.420(3) .
C4 C5 1.363(4) .
C5 C6 1.414(4) .
C6 C7 1.372(4) .
C7 C8 1.401(4) .
C9 C10 1.286(4) .
C9 C31 1.486(4) .
C10 C11 1.393(3) .
C11 C12 1.358(4) .
C11 C41 1.477(4) .
C31 C35 1.395(4) .
C31 C32 1.408(4) .
C32 C51 1.491(4) .
C33 C34 1.391(4) .
C34 C35 1.396(4) .
C34 C36 1.505(4) .
C41 C42 1.386(4) .
C41 C46 1.401(4) .
C42 C43 1.386(4) .
C43 C44 1.384(4) .
C44 C45 1.383(4) .
C45 C46 1.383(4) .
C51 C56 1.392(4) .
C51 C52 1.401(4) .
C52 C53 1.381(4) .
C53 C54 1.385(5) .
C54 C55 1.386(4) .
C55 C56 1.388(4) .
